ZA200507366B - Novel fused triazolones and the uses thereof - Google Patents

Description

INOVEL FUSED TRIAZOLONES AND THE USES THEREOF

Field of the finvention

The present invention relates to novel fused trizolones, their pharmaceutical 5S compositions and methods of use. In addition, the present invention relates to therapeutic methods for the treatment and prevention of cancers.

Background of the invention

Chexmotherapy and radiation exposure are currently the major options for the treatament of cancer, but the utility of both these approaches is severely limited by drastic adverse effects on normal tissue, and the frequent development of tumor cell resistance. It is therefore hi ghly desirable to improve the efficacy of such treatments in a way that does not increase the toxicity associated with them. One way to achieve this is by the use of specific sensitizitag agents sucha as those described herein.

An individual cell replicates by making an exact copy of its chromosomes, and thnen segregating these into separate cells. This cycle of DNA replication, chromosome separation and division is regulated by mechanisms within the cell that maintain the order of the stexps and ensure that each step is precisely carried out. Key to these processes are the cell cycle checkpoints (Hartwell ef al., Science, Nov 3, 1989, 246(4930):629-34) where cells may arrest to ensure IDNA repair mechanisms have time to op erate prior to continuing through the cycle 50 into mitosis. There are two such checkpoints in the cell cycle — the G1/S checkpoint that is regulated by p53 and the G2/M checkpoint that is Tnonitored by the Ser/Thr kinase checkpoint kinase 1 («CHK1).

As the cell cycle arrest induced by these checkpoints is a crucial mechanism by which cells can ©vercome the damage resulting from radio- or chemotherapy, their abrogation. by novel agents should increase the sensitivity of tunnor cells to DNA damaging therapies.

Additionally, the tumor specific abrogation of the G1/S checkpoint by p53 mutations ir the majority ©f tumors can be exploited to provide tumor selective agents. One approach to the design of chemosensitizers that abrogate the G2/M checkpoint is to develop inhibitors of the key G2/M regulatory kinase CHK], and this approach has been shown to work in a number of proof of concept studies. (Koniaras et al., Oncogene, 2001, 20:7453; Luo et al., NeopZ2asia, 2001, 3:<411; Busby et al.,Cancer Res., 2000, 60:2108; Jackson et al., Cancer Res., 2000, 60.566).

Summary of the invention

In accordance with the present invention, the applicants have hereby discovered novel . compounds that are potent inhibitors of the kinase CHK 1 and therefore possess the ability to prevent cell cycle arrest at the G2/M checkpoint in response to DNA damage. These compounds are accordingly useful for their anti-cell-proliferation (such as anti-cancer) activity and are therefore useful in methods of treatment of the human or animal body. The invention also relates to processes for the manufacture of said fused cormpounds, to pharmaceutical compositions containing them and to their use in the manufacture of medicaments of use with the production of anti-cell proliferation effect in warm-blooded animals such as man.

The present invention includes pharmaceutically acceptable salts or prodrugs of such compounds. Also in accordance with the present invention applicants provide pharmaceutical compositions and a method to use such compounds in the treatment of cancer.

Such properties are expected to be of value in the treatment of disease states associated with cell cycle and cell proliferation such as cancers (solid tumors and leukemias), fibroproliferative and diffcrentiative disorders, psoriasis, rheumatoid arthritis, Kaposi’s sarcoma, haermangioma, acute and chronic nephropathies, atheroma, atherosclerosis, arterial restenosis, autoimmune diseases, acute and chronic inflammation, bore diseases and ocular diseases with retinal vessel proliferation.

Definitions

The definitions set forth in this section are intended to clarify terms used throughout this application. The term “herein” means the entire application.

As used in this application, the term "optionally substituted," as used herein, means that substitution is optional and therefore it is possible for the designated atom to be unsubstituted. In the event a substitution is desired then such substittation means that any number of hydrogens on the designated atom is replaced with a selection from the indicated group, provided that the normal valency of the designated atom is not exceeded, and that the substitution results in a stable compound. For example when a substi tuent is keto (i.e., =0), then 2 hydrogens on the atom are replaced. If no selection is provided then the substituent shall be selected from: halogen, nitro, amino, cyano , trifluoromethyl, alkyl, alkenyl, alkyny], haloalkyl, alkoxy, hydroxy, alkythydroxy, carbonyl, -CH(OH)CH, -CH,NH-alkyl-OH, alkyl-(OH)CH, -Oalkyl, -0COalkyl, -NHCHO, -N-(alkyl)-CHO, -NH-CO-amino, -N-(alkyl)-CO-amino, -NH-

COalkyl, -N ~(alkyl)-COalkyl, -carboxy, -amidino, -CO-amino, -CO-alkyl, -COqalkyl, mercapto, -S-alkyl, -SO(alkyD), -S0O, (alkyl), -SO;-amino, -alkylsulfonylamino, phenyl, cycloalkyl, heterocyclic and heteroaryl, -alkly-NH-cycloalkyl, -alkyl-NH-optionally substituted heterocycle, -alkyl-NH-alkyl-OH, -C(=0)OC(CHs)s, -N(CHs)2, -alkyl-NH-alkyl- optionally substituted heterocycle, alkyl-aryl, alkyl-polycyclyl, alkyl-amino, alkyl-hydroxy, -

CH,NH-alk yl-heterocycle, -CH,NHCHI2CH(CH3),, -CH,NHCH2CH(CHs)z, -C(=0)OC(CHs)s, -Cjsalkyl, -0OC,salkyl, -N(CH3)2, -~NCH>NCHj3, -CH,NCH;, -CH,-piperazine, or —CH,-methylpiperazine.

If thne selection is attached to a ring the substituents could also be selected from: vicinal -O(alkyl)O-, vicinal -O(Chaloalkyl)O-, vicinal -CHI;0(alkyl)O-, vicinal -S(alkyl)S- and ~O(alky})S-.

When any variable (e.g., R!, R%, R®% R® etc.) occurs more than one time in any constituent or formula for a compound, its definition at each occurrence is independent of its definition at every other occurrence. Thus, for example, if a group is shown to be substituted with 0-3 R 2, then said group may optionally be substituted with 0,1,2 or 3 R! groups and R® at each occurence is selected independently from the definition of RS. Also, combinations of substituents and/or variables are permissible only if such combinations result in stable compounds.

A variety of compounds in the present invention mraay exist in particular geometric or 70 stercoisomeric forms. The present invention takes into ac count all such compounds, including cis- and trans isomers, R- and S- enantiomers, diastereomers, (D)-isomers, (L)- isomers, thie racemic mixtures thereof, and other mixtures thereof, as being covered within the scope of thais invention. Additional asymmetric carbon atoms may be present in a substituent such as an alkyl group. All such isomers, as well as mixtures thereof, are intended to be included im this invention. The compounds herein described may have asymmetric centers.

Compounds of the present invention containing an asymmnetrically substituted atom may be isolated ire. optically active or racemic forms. It is well known in the art how to prepare optically active forms, such as by resolution of racemic forms or by synthesis from optically active starting materials. When required, separation of the racemic material can be achieved by methocls known in the art. Many geometric isomers of olefins, C=N double bonds, and the like can also be present in the compounds described herein, and all such stable isomers are contemplated in the present invention. Cis and trans geoxmetric isomers of the compounds of the presert invention are described and may be isolated as a mixture of isomers or as separated isomeric forms. All chiral, diastereomeric, racemic forms and all geometric isomeric forms of a structure are intended, unless the specific stereochemistry or isomeric form is specifically indicated.

When a bond to a substituent is shown to cross a bond connecting two atoms in a ring, then such substituent may be bonded to any atom on the ring. When a substituent is listed "without indicating the atom via which such substituent is bond-ed to the rest of the compound of a given formula, then such substituent may be bonded via amy atom in such substituent.

Combinations of substituents and/or variables are permissible «only if such combinations result in stable compounds.

As used herein, "alkyl" or "alkylene" used alone or as & suffix or prefix, is intended to include both branched and straight-chain saturated aliphatic hydrocarbon groups having from 1 to 12 carbon atoms or if a specified number of carbon atomss is provided then that specific number would be intended. For example "C,.¢ alkyl" denotes alkyl having 1,2,3,4,501r6 carbon atoms. Examples of alkyl include, but are not limited t-o, methyl, ethyl, n-propyl, i- propyl, n-butyl, i-butyl, sec-butyl, t-butyl, pentyl, and hexyl. As used herein, "C).3 alkyl", whether a terminal substituent or an alkylene group linking two substituents, is understood to specifically include both branched and straight-chain methyl, ethyl, and propyl.

As used herein “alkylhydroxy” represents an alkyl grosup straight chain or branched as defined above with the indicated number of carbon atoms witlh one or more hydroxy groups attached. One such example of alkylhdroxy would be —-CH,(OH.

As used herein, the term "cycloalkyl" is intended to include saturated ring groups, having the specified number of carbon atoms. These may include fused or bridged polycyclic systems. Preferred cycloalkyls have from 3 to 10 carbon atoms in their ring structure, and more preferably have 3, 4, 5, and 6 carbons in the ring structuare. For example, "Cs cycloalkyl" denotes such groups as cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl.

As used herein, "alkenyl" or "alkenylene" is intended to include from 2 to 12 hydrocarbon atoms of either a straight or branched configuration with one or more carbon- carbon double bonds that may occur at any stable point alongs the chain. Examples of "Cs. alkenyl" include, but are not limited to, 1-propenyl, 2-propemyl, 1-butenyl, 2-butenyl, 3- butenyl, 3-methyl-2-butenyl, 2-pentenyl, 3-penteny), hexenyX.

As used herein, "alkynyl" or "alkynylene" is intended. to include from 2 to 12 hydrocarbon chains of either a straight or branched configuration with one or more carbon- carbon triple bonds that may occur at any stable point along the chain. Examples of alkynyl include but are not limited to ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3- . butynyl.

As used herein, the term "alkylcycloalkyl" is intended to meam an alkyl attached to the formula atom modified with a cycloalkyl. Examples of alkylcycloallkkyl include, but are not limited to cyclopropylmethyl, cyclopentylmethyl, cyclohexylmethyl, cycloheptylmethyl, cyclopropylethyl, cyclopentylethyl, cyclohexylethyl, cycloheptyleths/l, cyclopropylpropyl, cyclopentylpropyl, cyclohexylpropyl, cycloheptylpropyl.

As used herein, “cycloalkenyl” refers to ring-containing hydrocarbyl groups having at least one carbon-carbon double bond in the ring, and having from 3 to 12 carbons atoms.

As used herein, “cycloalkynyl” refers to ring-containing hydwxocarbyl groups having at least one carbon-carbon triple bond in the ring, and having from 7 to 12 carbons atoms.

As used herein, the term “aralkyl” refers to an alkyl group suabstituted with an aryl - group (an aromatic or heteroaromatic group).

As used herein, “aromatic” refers to hydrocarbyl groups having one or more polyunsaturated carbon rings having aromatic character, (e.g., 4n + 2 delocalized electrons) and comprising up to about 14 carbon atoms.

The term “‘ary!l” as used herein includes 5-, 6- and 7-membexred single-ning aromatic groups that may include from zero to four heteroatoms, for examples, benzene, furan, imidazole, isoxazole, nicotinic, isonictinic, oxazole, phenyl, pyrazole, pyrazine, pyridazine, pyridine, pyrimidine, thiazole, thiophene, triazole and the like. Those aryl groups having heteroatoms in the ring structure may also be referred to as “heteroaryl” or “heteroaromatics.”

The aromatic ring can be substituted at one or more ring positions with such substituents as described above. The term “aryl” also includes polycyclic ring systems having two or more cyclic rings in which two or more carbons are common to two adjoining rings (the rings are “fused rings”) wherein at least one of the rings is aromatic, for exarmple, the other cyclic rings can be cycloalkyls, cycloalkenyls, cycloalkynyls, aryls and/or heter-ocyclyls.

The terms ortho, meta and para apply to 1,2, 1,3- and 1,4-disubstituted benzenes, respectively. For example, the names 1,2-dimethylbenzene and ortho-dimethylbenzene are

Synonymous.

As used Therein, the term "heterocycle" or "heterocyclic" or “heterocyclyl” refers to a ring-containing 1monovalent and divalent structures having one or rmore heteroatoms, independently selected from N, O and S, as part of the ring structure and comprising from 3 to 20 atoms in the rings, more preferably 3- to 7- membered rings. H eterocyclic groups may be saturated or unsaturated, containing one or more double bonds, and heterocyclic groups may contain more than one ring as in the case of polycyclic systems. The heterocyclic rings described herein may be substituted on carbon or on 2 heteroatom atom if the resulting compound is stable. If specifically noted, nitrogen in the heterocycle may optionally be quaternized. It is understood that when the total number of S and O atoms in the heterocycle exceeds 1, then these heteroatoms are not adjacent to one another.

Examples of heterocycles include, but are not limited to, 1H-indazole, 2-pyrrolidonyl, 2H, 6H-1, 5,2-dithiazinyl, 2H-pyrrolyl, 3H-indolyl, 4-piperidonyl, 4aH-carbazole, 4H- quinolizinyl, 6H-1, 2,5-thiadiazinyl, acridinyl, azetidine, aziridine, azocinyl, benzimidazoly}, benzofuranyl, benzothiofuranyl, benzothiophenyl, benzoxazolyl, benzthiazolyl, benzotriazolyl, benzotetrazolyl, benzisoxazolyl, benzisothiazolyl, benzimidazalonyl, carbazolyl, 4aH-carbazolyl, b-carboliny}, chromanyl, chromenyl, cinnolinyl, decahydroquinolinyl, 2H,6H-1,5,2-dithiazinyl, dioxolane, furyl, 2,3-dihydrofuran, 2,5- dihydrofuran, dihydrofuro[2,3 -b]tetrahydrofuran, furanyl, furazanyl, homopiperidinyl, imidazolidine, imidazolidinyl, imidazolinyl, imidazolyl, 1H-indazolyl, indolenyl, indolinyl, indolizinyl, indolyl, isobenzofuranyl, isochromanyl, isoindazolyl, isoindolinyl, isoindolyl, isoquinolinyl, isothiazolyl, isoxazolyl, morpholinyl, naphthyridinyl, octahydroisoquinolinyl, oxadiazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,3,4-oxadiazolyl, oxazolidinyl, oxazolyl, oxirane, oxazolidinylperimidinyl, phenanthridinyl, phenanthrolinyl, phenarsazinyl, phenazinyl, phenothiazinyl, phenoxathiinyl, phenoxazinyl, phthalazinyl, piperazinyl, piperidinyl, pteridinyl, piperidonyl, 4-piperidonyl, purinyl, pyranyl, pyrrolidine, pyrroline, pyrrolidine, pyrazinyl, pyrazolidinyl, pyrazolinyl, pyrazolyl, pyridazinyl, pyridooxazole, pyridoimidazole, pyridothiazole, pyridinyl, N-oxide-pyridinyl, pyridyl, pyrimidinyl, pyrrolidinyl, pyrrolinyl, pyrrolyl, pyridine, quinazolinyl, quinolinyl, 4H- quinolizinyl, quinoxalinyl, quinuclidinyl, carbolinyl, tetrahydrofuranyl, tetrahydroisoquinolinyl, thiophane, thiotetrahydroquinolinyl, 6H-1,2,5-thiadiazinyl, 1,2,3- thiadiazolyl, 1,2,4-thiadiazoly}, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, thianthrenyl, thiazolyl, thieny], thienothiazolyl, thienooxazolyl, thienoimidazolyl, thiophenyl, thiirane, triazinyl, 1,2,3-triazolyl, 1,2,4-triazolyl, 1,2,5-triazolyl, 1,3,4-triazolyl, xanthenyl.

The terms “polycyclyl” or “polycyclic group” refer to two or more rings (for example, cycloalkyls, cycloalkenyls, cycloalkynyls, aryls and Jor heterocyclyls) in which two or more carbons are common to two adjoining rings, for example, the rings are “fused rings.” Rings that are joined through non-adjacent atoms are termed “bridged” rings. Each of the rings of the polycycle can be substituted with suck substituents as described above, as for example, halo gen, alkyl, aralkyl, alkenyl, alkynyl, cycloalkyl, hydroxyl, amino, nitro, sulfhydryl, imino, amido, carbonyl, carboxyl, ether, alkylthio, sulfonyl, ketone, aldehyde, ester, a heterocyclyl, an aromatic or heteroaromatic moiety, -CFs, -CN, or the like. Examples of such bridged heterocycles include quinuclidine, diazabicyclo[2.2.1]heptane and 7- oxabicyclo[2.2.1]heptane, substituted piperazine.

As used herein, the term “amine’> or “amino” refers to groups of the general formula —

NR R’, wherein R and R’ are each independently represented by but not limited to hydrogen, alkyl, cycloalkyl, alkenyl, aryl, heteroaryl, aralkyl, or heteroaralkyl. Example of the amino group include, but are not limited to NH», methylamine, ethylamine, dimethy lamine, die thylamine, propylamine, benzylamine and the like.

As used herein, the term “acylamino” is art-recognized and refers to aa moiety that can be represented by the general formula: oO —N—lr

R wherein R and R’ are each independent Ry represented by but not limited to h.ydrogen, alkyl, cycloalkyl, alkenyl, aryl, heteroaryl, heterocyclyl, aralkyl, or heteroaralkyl.

As used herein, the term “amido” is art-recognized as an amino-subs tituted carbonyl an d includes a moiety that can be represented by the general formula:

AR

R wherein R and R’ are each independently represented by but not limited to hydrogen, alkyl, cycloalkyl, alkenyl, aryl, heteroaryl, heterocyclyl, aralkyl, or heteroaralkyl, or R and R’ may form a ring.

As used herein, "alkoxy" or "alkyloxy" represents an alkyl group as defined above writh the indicated number of carbon atoms attached through an oxygen bridge. Examples of alkoxy include, but are not limited to, smethoxy, ethoxy, n-propoxy, isoprop» oxy, n-butoxy, isobutoxy, t-butoxy, n-pentoxy, isoperntoxy, cyclopropylmethoxy, allyloxy and propargyloxy.

Similarly, "alkylthio" or "thioalkoxy" represent an alkyl group as defined above with the iradicated number of carbon atoms atta ched through a sulphur bridge.

As used herein, the term “acyl” refers to groups of the of the general formula ~C(=0)-

R, wherein R is hydrogen, hydrocarbyl radical. Examples of acyl groups include, but are not limited to acetyl, propionyl, benzoyl, phenyl acetyl.

As used herein, the term “carbonyl” is art recognized and includes such moieties as can be represented by the general formula: 0 o)

A xr , or xr wherein X is a bond or represents an oxygen or sulfur, and R represents a hydrogen, an alkyl, an alkenyl, (CHz)»-R”’ or a pharmaceutically acceptable salt, R’ represents a hydrogen, an alkyl, an alkenyl or -(CH;)y-R*’, Where m is an integer less than or equal to ten, and RR’ is alkyl, cycloalkyl, alkenyl, aryl, or heteroaryl. Where X is an oxygen and R and R” is mot hydrogen, the formula represents an “ester”. Where X is an oxygen, and R is as defined above, the moiety is referred to herein as a carboxyl group, and particularly when R* isa hydrogen, the formula represents a “carboxylic acid.” Where X is oxygen, and R’ is a. hydrogen, the formula represents a “formate.” In general, where the oxygen atom of the above formula is replaced by sulfur, the formula represents a “thiolcarbonyl” group. Where X is a sulfur and R and R’ is not hydrogen, the formula represents a “thiolester.” Where X is sulfur and R is hydrogen, the formula represents a thiolcarboxylic acid.” Where X is sulfur and R’ is hydrogen, the formula represents a "thiolformate.” On the other hand, where X is a bond, and R is not a hydrogen, the above formula represents a “ketone” group. Where X is a bond, and R is hydrogen, the above formula is represents an “aldehyde” group.

As used herein, the term ““sulfonylamino” is art-recognized and refers to a moiety that can be represented by the general formula: 9

AR

RO wherein R and R’ are each independently represented by but not limited to hydrogen, alkyl, cycloalkyl, alkenyl, aryl, heteroaryl, heterocyclyl, aralkyl, or heteroaralkyl.

As used herein, the term “‘sulfamoyl” is art-recognized and refers to a moiety” that can be represented by the general formula: f Rr — S§— N] o R wherein R and R’ are each independently represented by but not limited to hydrogen, alkyl, cycloalkyl, alkenyl, aryl, heteroaryl, heterocyclyl, aralkyl, or heteroaralkyl, or R amd R’ may : form a ring.

As used herein, the term “sulfonyl” is art-recognized and refers to a moiety that can be represented by the general formula: 0] ii i wherein R is represented by but not limited to hydrogen, alkyl, cycloalkyl, alkeny/], aryl, heteroaryl, aralkyl, or heteroaralkyl.

As used herein, the term “sulfoxido” is art-recognized and refers to a moiety that can be represented by the general formula: 0 —S—R wherein R is represented by but not limited to hydrogen, alkyl, cycloalkyl, alkenyl, aryl, heteroaryl, aralkyl, or heteroaralkyl.

As used herein, "halo" or "halogen" refers to fluoro, chloro, bromo, and iodo. "Counterion" is used to represent a small, negatively charged species such as chloride, bromide, hydroxide, acetate, sulfate, tosylate, benezensulfonate, and the like.

As used herein, "haloalkyl" is intended to include both branched and straight-chain saturated aliphatic hydrocarbon groups having the specified number of carbon atoms, substituted with 1 or more halogen (for example --C,F, where v=1 to 3 and w=1 to @2v+1)).

Examples of haloalkyl include, but are not limited to, trifluoromethyl, trichlorormethyl, pentafluoroethyl, pentachloroethyl, 2,2,2-trifluoroethyl, 2,2-difluoroethyl, hepta fluoropropyl, and heptachloropropyl. "Haloalkoxy" is intended to mean a haloalkyl group as clefined above with the indicated number of carbon atoms attached through an oxygen bridge; for example trifluoromethoxy, pentafluoroethoxy, 2,2 2-trifluoroethoxy, and the like. "Haloalkylthio" is intended to mean a haloalkyl group as defined above with the indicated number of carbon atoms attached through a sulphur bridge.

As used herein, “moieties” means alkyl; cycloalkyl; alkenyl; alkynyl; alkylcycloalkyl; cycloalkenyl; cycloalkynyl; aralkyl; aryl; heterocycle; polycyclyl; amine;acylarmino; amido; alkoxy; acyl; carbonyl; sulfonylamino; sulfamoyl; sulfonyl; sulfoxido; halo; haloalkyl; haloalkoxy as these terms are defined herein.

As used herein, the phrase ““protecting group” means temporary substituents which protect a potentially reactive functional group from undesired chemical transformations.

Examples of such protecting groups include esters of carboxylic acids, silyl ethers of allcohols, and acetals and ketals of aldehydes and ketones respectively. The field of protecting garoup chemistry has been reviewed (Greene, TW; Wats, P.G.M. Protective Groups in Orga xic

Synthesis, 3" ed.; Wiley: New York, 1999).

As used herein, "pharmaceutically acceptable" is employed herein to refer to timose compounds, materials, compositions, and/or dosage forms which are, within the scope of sound medical judgment, suitable for use in contact with the tissues of human beings and animals without excessive toxicity, irritation, allergic response, or other problem or complication, commensurate with. a reasonable benefit/risk ratio.

As used herein, "pharmaceutically acceptable salts" refer to derivatives of the disclosed compounds wherein the parent compound is modified by making acid or basse salts thereof, Examples of pharmaceutically acceptable salts include, but are not limited to, mineral or organic acid salts of basic residues such as amines; alkali or organic salts of acidic xesidues such as carboxylic acids; and the like. The pharmaceutically acceptable salts include the conventional non-toxic salts or the quaternary ammonium salts of the parent compouxzd formed, for example, from non-toxic inorganic or organic acids. For example, such conventional non-toxic salts include those derived from inorganic acids such as hydrochloric, hydrobromic, sulfuric, sulfamic, phosphoric, nitric and the like; and the salts prepared from organic acids such as acetic, propionic, succinic, glycolic, stearic, lactic, maleic, tarta-xic, citric, ascorbic, palmitic, maleic, hydroxymaleic, phenylacetic, glutamic, benzoic, sal icylic, sulfanilic, 2-acetoxybenzoic, fumaric, toluenesulfonic, methanesulfonic, ethane disul fonic, oxalic, isethionic, and the like.

The pharmaceutically acceptable salts of the present invention can be synthesized from the parent compound that contains a basic or acidic moiety by conventional chemical methods. Generally, such salts can be prepared by reacting the free acid or base forms of these compounds with a stoichiometric amount of the appropriate base or acid in water or in an organic solvent, or in a mixture of the two; generally, nonaqueous media like ether, esthyl acetate, ethanol, isopropanol, or acetonitrile are preferred. Lists of suitable salts are found in

Remington's Pharmaceutical Sciences, 17th ed., Mack Publishing Company, Easton, Pa., 1985, p. 1418, the disclosure of ‘which is hereby incorporated by reference.

"prodrugs" are intended to include any covalently bonded carriers that release the active parent drug according to formul a (D in vivo when such prodrug is adxministered to a mammalian subject. Prodrugs of a connpound of formula (I) are prepared by” modifying functional groups present in the compound in such a way that the modifications are cleaved, either in routine manipulation or in viwo, to the parent compound. Prodrugs include compounds of formula (I) wherein a lnydroxy, amino, or sulfhydryl group is bonded to any group that, when the prodrug or comp ound of formula (I) is administered to a mammalian subject, cleaves to form a free hydrox yl, free amino, or free sulfhydryl group, respectively.

Examples of prodrugs include, but are not limited to, acetate, formate and benzoate derivatives of alcohol and amine functional groups in the compounds of foxmula (I), and the like. "Stable compound" and "stable structure" are meant to indicate a compound that is sufficiently robust to survive isolatiom to a useful degree of purity from a reaction mixture, and formulation into an efficacious therapeutic agent.

Detailed description of the invention

In a first embodiment, the present invention provides novel compounds having formula ®: ik m © AL ,

Ny A n ll rt ~7 NTN

RN

0) H @® wherein: m is independently selected at each occurrence from 0,1 or 2; n is independently selected at each occurrence from 0 or 1;

A is optionally substi tuted phenyl, optionally substituted phenol, optionally substituted ) heterocyclic;

B is optionally substituted phenyl, optionally substituted phenol, optionally substituted heterocyclic;

R! is H, OH, F, Cl, Br, I, NH, -C(=O)R’ -C(=0)NHR®, C(=O)CH:R" -

C(=0)(CH2):R’, C(=0)(CHLz);R’, -C(=O)NH(CH)NH;, -C(=0)NH(CHy):NH_, -

C(=O)NH(CH;);NH,, -C(=O)NH(CHz)N(CHs), -C(=0)NH(CH):N(CHs),, -

C(=0)NH(CH_);N(CHs),, -C(=0)NH(CH,);NHCHs, -C(=0)NH(CH;);0H, -C(=O)NHNH,, -

C(=0)NHCH(CH;)CH;N(CHz),, -C(=0)NH(CH;);NHC(CHs),, (CHy)13OH, -C(=0)OR®, -C(=0)NHNH;, -NH(CH2)1.:R’, -CH,NH(CH,)1 3R?, -

NHC(=0)OR, -(CsHs)NH-cycloalkyl, -(CsH4)NH-optionally substituted heterocycle, - (C¢H4)CH,NH-alkyl-OH, -(CsHs)N(CHs), -O-alkyl-NHa, optionally substituted alkyl, optionally substituted N-alkkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl, optionally substituted cycloalkeny, optionally substituted cycloalkynyl, optionally substituted aryl, optionally substituted alkoxy, optionally substituted heterocycle, or optionally substituted fused heterocycle;

R?is H, OH, F, Cl, Br, I, NH;, (CH2);30H, -C(=0)OR’, -C(=O)NHNH, -NH(CH)):. ;R®, -CH,NH(CH,),3R", -NHC(=0)OR, optionally substituted alkyl, optionally substituted N- alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted cycloalkynyl, optionally substituted aryl, optionally~ substituted alkoxy, optionally substituted heterocycle, or optionally substituted fused heterocycle.

R3 is is H, OH, F, CJ, Br, I, NH, CH,

R*is H, OH, F, Cl, Br, I, NH,, R*, OCH3, -C(=0)OR®, -C(=0)NHNH, -NH(CHo):. 3R®, -CH,NH(CH,),3R?, -INHC(=0)OR’, -(CéH4)CH,NH(CH2),3R?, - (CeHa)CH;N(CH)(CHp)1-3R®, CeHa)(CHa)o sR’, (CHAR)CHR?, -(Csta) CH, NHR®, - (CsHa)C(=O)R® -(CsHy)NEIC(=O)R’, -(CsH4)CH,NH(CH,);5R°R",, -(CeH4)NHSO,CHs, optionally substituted alkyl, optionally substituted N-alkyl, optionally substituted alkenyl, optionally substituted alky/nyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted cycloalkynyl, optionally substituted aryl, optionally substituted alkoxy, option ally substituted heterocycle, or optionally substituted fused heterocycle;

R® is H, OH, F, Cl, Br, I, NH,, OCH, -C(=0)OR", -C(=O)NHNH,, -NH(CH;);3R?, -

CH,NH(CH,)13R?, -NHC(=0)OR®, optionally substituted alkyl, optionally substituted N- alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted cycloalkynyl, optionally substituted aryl, optionally substituted alkoxy, optionally substituted heterocycle, or optionally substituted fused heterocycle; :

RS is H, OH, F, Cl, Br, I, NH;, NHC alkyl, N(Ci.salkyl)s, «(CsH4)CHaR?, -(CsHa)CH;NR’R®, optionally substituted aryl;

R® is H, OH, OCH, Cialkyl, Cialkoxy, NHz, NHCH,, N(CHs)2, CH2C(CHa)2, optionally substititued phenyl, optionally substititued cycloalkyl, optionally substituted 5 or 6 or 7 membered heterocycle having 1 or 2 oxygen or 1 or 2 nitrogen or 1 nitrogen and 1 oxygen or | nitrogen and 1 sulfur or 1 oxygen and 1 sulfur ring atoms;

R® is H, OH, OCHj, C;.¢alkyl, Cy¢alkoxy;

R°® is optionally substituted C4-7 heterocycle;

X is CH, substituted C, N, O, or any combination thereof;

Y is CH, substituted C, N, O, or any combination thereof;

Z is CH, substituted C, N, O, or any combination thereof;

V is CH, substituted C, N, O, or any combination thereof; or a pharmaceutically aceptable salt thereof.

In a particular embodiment the present invention provides a compound having formula (I) as recited above wherein m is 0.

In a particular embodiment the present invention provides a compound having formula (I) as recited above wherein n is 0.

In a particular embodiment the present invention provides a compound having formula (I) as recited above wherein R’ is -C(=O)R® -C(=0)NHR®, C(=0)CH;R" -C(=0)(CH2),R’,

C(=0)(CH2)sR®, -C(=0)NH(CHz) NH, -C(=O)NH(CH2):NHa, -C(=0)NH(CHz):sNHz2, -

C(=0)NH(CH,)N(CH3), -C(=O)NH(CH2),N(CHzs)2, -C(=0)NH(CH,);N(CHa), -

C(=0)NH(CH,),NHCHj3, -C(=O)INH(CH,);OH, -C(=0O)NHNH,, -

C(=0)NHCH(CH3)CH,N(CHs), ~C(=0)NH(CH,),NHC(CHs),.

In a particular embodiment the present invention provides a compound having formula (I) as recited above wherein R! is NH,, CHj, or (CH); 30H, -(CsHs)NHcycloalkyl, O(CHy)s.

3NHj, -(C¢H4)NH-cycloalkyl, -(C¢Hs)NH-optionally substituted heterocycle, - (CsH,)CH,NH-alkeyl-OH, -(CeHy)N(CHa),, -O-alkyl-NHz2.

In a particular embodiment the present invention provide s a compound having formula (I) as recited above wherein R? is H or (CH) 30H.

In a particular embodiment the present invention provides a compound having formula (I) as recited above wherein R® is H.

In a particular embodiment the present invention provides a compound having formula @ as recited above wherein R? is H, OCH, -(CsHs)CH,NEX(CH2)13R", - (CeHs)CH,N(CHL3)(CHz); sR”, -(CsH4)CH2R?, -(CsHL)(R®)CH,R", (CsHa)CH, NHR? - (CsHa)C(=O)R® —(CsHa)NHC(=O)R?, -(CeHy)CHNH(C Hy) 3R°R’, ~(CsH4)NHSO,CH3, optionally substituted aryl, or optionally substituted heterocycle.

In a particular ennbodiment the present invention provid.es a compound having formula (I) as recited above wherein R* is halogen, or an optionally” substituted 5-membered heterocycle wherein said substitution is selected from —IN(CHa),, -NCH,NCHj, -CH,NCHs,

CH,-piperazine, or CHy-methylpiperazine.

In a particular exmbodiment the present invention provicies a compound having formula (I) as recited above wherein R* is halogen or an optionally substituted furan, optionally substituted pyricline, or optionally substituted thiophene.

In a particular exnbodiment the present invention providles a compound having formula (I) as recited above wherein R* is optionally substituted fuxan, optionally substituted pyridine, or optionally substituted thiophene wherein said substitution is selected from —-N(CHa)y, -

NCH,;NCH;, -CH,NCHj3, CH,-piperazine, CH,-methyl piperazine.

In a particular embodiment the present invention provides a compound having formula (1) as recited above wherein R’ is H, OH, or OCHj.

In a particular embodiment the present invention provides a compound having formula (I) as recited above wherein RC is H, -(CsH4)CH2R®, «(CeF1)CHNR'R®.

In a particular embodiment the present invention provides a compound having formula (I) as recited above wherein X is CH or N.

In a particular embodiment the present invention provides a compound having formula (I) as recited above wherein Y is CH or N.

In a particular embodiment the present invention provides a compound having formula (I) as recited above wherein Z is CH or N.

In a particular embodiment the present invention provides a compound having formula (I) as recited above wherein V is an optionally substituted carbo.

In a particular embodiment the present invention provides a compound having formula (I) as recited above wherein: misOorl; nisO0;

R! is NH;, CHa, or (CHy)1.:0H; -(CsHs)NHcycloalkyl, O(CHz)1sNHz, -(C¢H4)NH- cycloalkyl, -(Cets)NH-optionally substituted heterocycle, -(CsHs)CHoNH-alkyl-OH, - (CeH4)N(CHs),, -O-alkyl-NHz;

R? is H or (CH)1.:0H;;

R’isH;

R* is OCHj, «(CsHe) CH;NH(CH)13R?, -(CHa)CHN(CH3)(CH)13R', - (CeHa)CHR?, (CeHaYR")CHR?, (CHa)CH; NHR" -(CeHA)C(=O)R" - (CsH4)NHC(=O)R?, —(C¢H4)CH,NH(CH,),..R°R”, -(C¢H4)NHSO,CHj, optiomally substituted aryl, or optionally substituted heterocycle;

R’ is H, OH, or OCH;

R® is H; -(CsHa)CH2R®, -(CsHy)CHNR'R”;

R® is OH, OCHj, C, _ealkyl, NH,, NHCH3, N(CHj)2, CH2C(CHs), optionally substititued cycloalkyl, optionally substituted 5 or 6 or 7 membered heterocycle having 1 or 2 oxygen, or 1 or 2 nitrogen, or 1 nitrogen and 1 oxygen, or 1 nitrogen and 1 sulfur, or 1 oxygen and 1 sulfur ring atoms;

R® is OH, OCH, C; -calkyl;

X,Y,Z and V are CH.

In a particular embodiment the present invention provides a compound having formula (I) as recited above wherein: mis 1; nis 0;

R! is -C(=0)R° -C(=0)NHR’, C(=0)CH,R’ -C(=0)(CH2);R", C(=0)(CH2)3R", -

C(=0)NH(CH2)NH,, -C(=O)NH(CH2),NH;, -C(=0)NH(CH):NH,, -

C(=O)NH(CHz)N(CHjs),, -C(=O)NH(CH;),N(CHs)s, -C(=0)NH(CH;);N(CHs)y, -

C(=O)NH(CH_;);NHCH3;, -C(=0)NH(CH.)30H, -C(=O)NHNH_, -

C(=0)NHCH(CH;)CH,N(CHjs),, -C(=O)NH(CH),NHC(CHs);

R’is H;

Ris H;

R* is halogen, or an optionally substituted 5-membered heterocycle; .

R’ is H;

Reis H;

S X,Y, Zand V are CH.

In a particular embodiment the present invention provides a compound having formula (I) as recited above wherein: mis 1; nis 0;

R! is -C(=0)R® -C(=0)NHR’, C(=0)CH,R* -C(=0XCH,);R®, C(=0)(CHz)3R’, -

C(=0)NH(CH;)NH,, -C(=0)NH(CH.);NHz, -C(=O)NH(CH,);NH;, -

C(=0)NH(CH;)N(CHa),, -C(=0)NH(CHz);N(CH3)z, -C(=0)NH(CH,)sN(CHa)y, -

C(=0)NH(CH,),NHCH;, -C(=0)NH(CH);OH, -C(=O)NHNIH], -

C(=0)NHCH(CH;)CH:N(CHa)e, -C(=0)NH(CH;,).NHC(CHs),;

Ris H;

R}is H;

R* is halogen, or an optionally substituted 5-membered heterocycle wherein said substitution is selected from —N(CHj),, -NCH;NCHa, -CH,NCH,, -CH,-piperazine or -

CH,-methylpiperazine.

R’is H;

Ris H;

X,Y, Zand V are CH.

In a particular embodiment the present invention provides a compound having formula (I) as recited above selected from: 5-methyl[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 5, 9-dimethyl[1,2,4]triazolo[4,3-a] quinolin-1(2H)-one; 8-methoxy-5-methyl[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 8-fluoro-5-methyl{1,2,4]triazolo[4,3-a}quinolin-1 (2H)-one; 5-bromo-5-(hydroxymethyl)[1,2,4]triazolo[4,3-a] quinolin-1(2H)-one [1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; ethyl-7-bromo-1-0xo-1,2-dihydro[ 1,2,4]triazolo[4,3-a]quinoline-5-carboxylate;

Ethyl-7-methyl-1-oxo-1,2-dihydro[ 12,4] triazolo[4,3-a]quinoline-5-carboxylate; 7-methyl-1-oxo-1,2-dihydro[1,2,4]triazolo[4,3-a] quinoline-5-carbohydrazide;

5-amino[1,2,4]triazolo[4,3-a]quinolin-1 (2H)-one;

S-amino-~7-bromo( 1 2 4]triazol o[4,3-a]quinolin-1(2H)-one; 7-methoxy-5-methyl{1,2,4]triazolo[4,3-a] quinolin-1(2H)-one; 7-hydroxy-5-methyl[1,2 4]triazolo[4,3-a] quinolin-1(2H)-one; 8-hydroxy-5-methyl[1,2,4]triazolo[4,3-a] quinolin-1(2H)-one; 5,7-dimethyl[1,2,4]triazolo[4,3-a]quinolin-1 (2H)-one; 5,8-dimethyl[1,2,4]triazolo[4, 3-a]quinolin-1(2H)-one; 9-hydroxy(1,2,4]triazolo{4,3-a]quinolin-1(2H)-one;

T-butyl-7-bromo-1-o0xo-1,2-dihydro[1 ,2,4]triazolo[4,3-a]quinolin-5- ylcarbamate; 7,8-dihydroxy-5-methyl[1,2,4 ]triazolo[4,3-a]quinolin-1 (2H)-one; 7,8-methoxy-5-methyl[ 1,2,4] triazolo[4,3 -a]quinolin-1(2H)-one; 7,8-methoxy[1,2,4]triazolo[4 ,3-a]quinolin-1(2H)-one; 7,8-dihydroxy[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 5-chloro[1,2,4]triazolo[4,3-a] quinolin-1(2H)-one; l-oxo-1,2-dihydro[1,2,4]triazolo[4,3-alquinoline-5 -carbohydrazide; 7-bromo-5-methyl[ 1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 7-iodo-5-methyl[ 1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 7-(3-aminophenyl)-5-methyl [1,2,4]triazolo[4,3-a] quinolin-1(2H)-orae; 7-(3-hydroxyphenyl)-5-methyl{1 ,2,4]triazolo[4,3-a]quinolin-1(2H)—one; 8-(3-hydroxyphenyl)-5-methyl[1,2,4]triazolof4,3-a] quinolin-1(ZH)—one; 8-[3-(hydroxymethyl)phenyl-5-methyl[1 ,2,4]triazolo[4,3-a]quinolira-1(2H)-one; 8-[4-(hydroxymethyl)pheny}-5-methyl[1,2,4]triazolo[4,3-a] quinolir-1(2H)-one; 8-(3-aminophenyl)-5-methy1[1,2,4]triazolo[4,3-a] quinolin-1(2H)-o=e; 5-(3-aminophenyl)[ 1,2,4]triaizolo[4,3-a]quinolin-1(2H)-one; 5-[4-(hydroxymethyl)pheny1[1,2,4]triazolo[4,3-a] quinolin-1(2H)-o xe,

Ethyl 7-methyl-1-ox0-1,2-dihydro[1,2,4}triazolo[4,3-a] quinoline-5 —carboxylate; 5-amino-7-(3-aminophenyl)[1,2,4]triazolo[4,3-a]quinolin-1(2H)-ox1e; 7-(2-hydroxyphenyl)-5-methyl[1,2 4]triazolo{4,3-a]quinolin-1(2H»-one; 4-amino[ 1,2,4]triazolo[4,3-a]quinolin-1(2H)-one;

S5-amino-7-(3-hydroxyphenyl)[1,2,4]triazolo[4,3-a]quinolin-1(2H)—one; 5-amino-7-[3-(hydroxymethyl)phenyl][1,2,4]triazolo[4,3-a]quinol Axn-1(2H)-one; 5-(1-benzothien-2-y1)[1,2,4 Jtriazolo[4,3-a]quinolin-1(2H)-one; 5-[3-(hydroxymethyl)pheny/1][1,2,41triazolo[4,3-a]quinolin-1(2H)—one;

5-[(E)-2+(4-chlorophenyl)vinyl][1 2 41triazolo[4,3-a]quinolin-1 (2H)-one; 5-(2,4-dihydroxyphenyl)[1 ,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 7-(2-hydroxyphenyl)[1,2,4]triazolo [4,3-a]quinolin-1(2H)-one; 5-(2-furyl)[1 ,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 7-(2,4-dihydroxyphenyl)-5-methyl[1 ,2,4]triazolof4,3-a]quinolin-1 (2H)-oxe; 5-phenyl[1,2,4]triazolo[4,3 -a]quinolin-1(2H)-one; 5-{[2-(3,4-dimethoxyphenyl)ethyl] amino}[1,2,4]triazolo[4,3 -aJquinolin—- 1(2H)-one; 5-[2,6-difluorobenzyl)amino][1 ,2,4]triazolo[4,3-a]quinolin-1(2H)-one;

Ethyl 1-ox0-1,2-dihydro[1 ,2,4]triazolo[4,3-a]quinoline-5-carboxylate; 5-4-4 [(2-pyridin-2-ylethyl)amino]methyl} phenyl} [1,2,4]triazolo[4,3-a] quinolin-1(2H)-one; 5-{4-{[(2-hydroxyethyl)amino]methyl }phenyl}[1,2,4]triazolo[4,3-a] quinolin-1(2H)-one 8-bromo-1-oxo-1,2-dihydro[1,2,4]triazolo[4,3 -a]quinoline-5-carboxylic acid; 7-[(4-hydroxymethyl)phenyl]-5-methyl{1,2 Altriazolo[4,3-a]quinolin-1(2H)-one; 5-{4-[(4-methylpiperazin- 1 -yDmethyl]phenyl}[1 ,2 4]triazolo[4,3-a]quirnolin-1(2H)-one;

S5-(benzylamino)-7-bromo [1,2,4]triazolo[4,3-a]quinolin-1(2H)-one;

Ethyl 7-methoxy-1-oxo-1,2-dihydro[1 ,2,4]triazolo[4,3-a]quinoline-5-caboxylate; 5-[4-{{[3-(dimethylamino)propyl]amino }methyl}phenyl][1,2,4]triazolo {4,3-alquinolin-1(2H)- one; 5-f4-{[(3-morpholin-4-ylpropyl)amino]methyl }phenyl}[1 2, 4]triazolo[4,3-a]quinolin-1(2H)- one; 5-amino-7-methyl[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one;

T-butyl 7-methoxy-1-oxo-1,2-dihydro[1 ,2,4]triazolo[4,3-a]quinolin-5-y71 carbamate; 5-amino-7-methoxy[1,2,4 Jtriazolo[4,3-a]quinolin-1(2H)-one; 8-dimethylamino-5-methyl(1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 5-amino-8-[4-(hydroxymethyl)phenyl][1 ,2,4ltriazolo[4,3-ajquinolin-1(2H)-one; 5-(4-{[(2S)-2-(hydroxymethyl)pyrrolidin-1 -yl]methyl}phenyl)[1,2,4}triazolo[4,3-a] quinolin- 1(2H)-one; 5-[4~({[1-(hydroxymethy1)-2-methylpropyl] amino }methyl)phenyl][1,2 ,4]triazolo[4,3- ajquinolin-1(2H)-one; 5-(4-{[4-(3-methylpheny])piperazin-1-ylJmethyl} phenyD)[1 ,2,4]triazolo[4,3-a]quinolin-1(2H)- one; 7-[4-({ [3-(dimethylamino)propyljamino }methyl)phenyl]-5 -methylf1,2 4]triazolo[4,3- a]quinolin-1(2H)-one;

5-methyl-7-(4-{[(3 -morpholin-4-ylpropyl)amino}me thyl}phenyl)l 1,2 4]triazolo[4,3- : aJquimolin-1(2H)-one; 5-me-thyl-7-(4-{[(2-pyridin-2-ylethy]) amino]methyl ¥phenyl){1 ,2,4]triazolo[4,3-ajquinolin- 1(2HD)-one; 7-4 {[(2-hydroxyethyl)amino}methyl }phenyl)-5-m ethyl[ 1,2,4]triazolo[4,3-a]quinolin-1 (CH)- one; 5-methyl-7-{4-[(4-methylpiperazino-1 -ymethylJphenyl}[1,2,4]triazolo (4,3-a]quinolin-1(2H)— one; 7-(4-{ [(2S)-2-(hydroxymethyl)pyrrolidin-1 -ylJmethyl}phenyl)-5-methyl{1 ,2,4]triazolo[4,3- a]quuinolin-i(2H)-one; 7-[4-({ [1-(hydroxymethyl)-2-methylpropyl] amino } methyl)phenyl]-5- methyl[1,2,4}triazolo[4,3-alquinolin-1 (2H)-one; 7-(B-{ [ethyl(pyridin-4-ylmethyl)amino]methyl }phenyl)-5-methyl[1 ,2,4]triazolo[4,3- a]quinolin-1(2H)-one; 5-maethyl-7-[4-({[3-(2-oxopyrrolidin-1 -yl)propyl] amino }methyl)phenyl][1,2,4]triazolo[4,3 - aJquiinolin-1(2H)-one; 5-methyl-7 -[4-({4-[3-(trifluoromethyl)phenyl]piperazin- 1- y1}amethyl)phenyl]{1,2,4]triazolo[4,3-a] quinolin-1(2H)-one; 7-{ 4-[(isobutylamino)methyl]phenyl}-5-methyl[ 1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 5-[ 3-({[3«(dimethylamino)propyl] amino }methyl)—4-methoxyphenyl][1 ,2,4]triazolo[4,3- a]qquinolin-1(2H)-one; 5-zamino-8-[3-(hydroxymethyl)phenyl][1 2 4)triazolo[4,3-a]quinolin-1(2H)-one; 5-&3- [(dimethylamino)methyl]phenyl}[1 ,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 5-f 4-[(dimethylamino)methyl]phenyl}{1 2, 4]triazolo[4,3-a]quinolin-1(2H)-one;

8-[3-(dimethylamino)phenyl]-5 -methyl[1,2,4]triazolo[4,3-a]quinolin-1 (2H)-one; 5-zmethyl-7-[4-({[2-(1H-pyrrol- 1-yl)phenyljamino}methyl)phenyl}{1 ,2,4]triazolo[4,3- a]«quinolin-1(2H)-one; 3-Thydroxy-2-(1-oxo-1,2-dihydro[1 ,2,4]triazolo[4 ,3 -a]quinolin-5-yl)benzaldehyde;

7- [4-({[3-(1H-imidazol-1-yl)propyl] amino meth yl)phenyl]-5-methyl[1 ,2,4]triazolo[4,3~ a] quinolin-1(2H)-one;

5—(4-methoxy-3-{ [(2-pyridin-2-ylethyl)aminojmethyl }phenyl)[1,2,4]triazolo[4,3-a]quinolimn- 1 (2H)-one;

5-[3-({[1-(hydroxymethyl)-2-methylpropyl] amino }methyl)-4- methoxyphenyl][1,2,4]triazolo[ 43-3] quinolin-1(2H)-one; 5-{4-methoxy-3-[(4-methylpiperazin- 1-yl)methyl]phenyl }[1,2,4]triazolo[4,3 -ajquinolin- 1(2H)-one;

5-3-{[(2R)-2-(hydroxymethyl)pyrrolidin-1 -yljmethyl }-4-methoxyphenyl)[1 ,2,4]triazolo[ 4,3-

a]quinolin-1(ZH)-one;

5-[2-({[3-(dimethylamino)propyl]amino} methyl)-6-methoxyphenyl](1,2,4]triazolo[4,3-

ajquinolin-1(2H)-one;

5-(2-{[(28)-2-(hydroxymethyl)pyrrolidin-1 -ylJmethyl }-6-methoxyphenyl)[ 1,2,4]triazolo[ 4,3- a]quinolin-1(2H)-one;

5-(2-methoxy-6-{[(2-pyridin-2-ylethyl)amino]methy! }phenyl)[1 ,2,4]triazolo[4,3-a]quino Xin-

1(2H)-one;

5-{2-methoxy-6-[(4-methylpiperazin- 1-yl)methyl]phenyl}[1,2,4]triazolo[4,3-a]quinolin-

1(2H)-one;

5-[4-({[3-(1H-imidazol-1-y)propyljamino }methyl)phenyl]{1,2,4]triazolo[4,3-a]quinolin— 1(2H)-on¢; 5-(4-{[ethyl(pyridin-4-ylmethyl)aminojmethyl }phenyl)[1,2,4]triazolo[4,3-a]quinolin-1(2 H)- one; 5-[4-({[3-(2-oxopyrrolidin-1-y1)propylJamino}methyl)phenyl]{ 1,2,4]triazolo[4,3-a] quinolin-

1(2H)-one; 5-[4-({[2-(1H-pyrrol-1-yl)phenyl]amino }methyl)phenyl]{1 ,2,4]triazolo[4,3-a]quinolin-1 2H)- one; 5-(4-hydroxy-3-{[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl}methyl}phenyl)[1 ,2,4]triazoloq 4,3- a]quinolin-1(2H)-one;

5-[4-hydroxy-3-({[1-(hydroxymethyl)-2- methylpropyl]amino}methyl)phenyl][1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 5-(2-hydroxy-6-{[(2S)-2-(hydroxymethyl)pyrrolidin-1-ylJmethyl}phenyl)[1 ,2,4]triazolo[ 4,3- a]quinolin-1(2H)-one; 5-{2-hydroxy-6-[(4-methylpiperazin-1-yl)methyl]phenyl }[1,2,4]triazolo[4,3-a]quinolin-

1(2H)-one; 5-[4-({[4-(4-methylpiperazin-1-yl)phenylJamino } methyl)phenyl][1,2,4]triazolo[4,3- a]quinolin-1(2H)-one;

Sat- 5-(4-{ [rmethyl(2-pyridin-2-ylethyl)amino]methyl }phenyl){ 1,2 4]triazolo[4,3-a}quinolin- 1(2H)-one; 5-(4-§ [(2-furylmethyl)amino]methyl }phenyD)[1 2, 4]triazolo[4,3-a]quinolin-1 (2H)-one; 5-(4-{[@3 ~furylmethyl)amino]methyl }phenyD){1 2 Altriazolo[4,3-aa]quinolin-1(2H)-one; 5- {4-[({2-[({5-[(dimethylamino)methyl]-2- furyl }methyl)thioJethyl} amino)methyl]phenyl} [1 2,A]triazolo[4,3-a]quinolin-1(2H)-one; 5-(4-{ [(2,3-dihydro-1-benzofuran-3 -ylmethyl)amino]methyl }phenyl)[ 1,2,4]triazolo[4,3- aJquinolin-1(2H)-one; 5-[4-({[(1-methyl-1 H-pyrrol-2-yl)methyljamino} methyl)phenyl [1,2,4]triazolo[4,3- ajquinolin-1(2H)-one; 5-[4-({[2-(4-benzylpiperazin-1 -yl)ethyljamino }methyl)phenyl][ 1 2 4]triazolo[4,3-a}quinolin- 1(2H)-one; 5-(4-{ [(pyridin-4-ylmethyl)amino]methyl }phenyl)[1,2,4]triazole[4,3-a] quinolin-1(2H)-one; 5-(4-{ [(4-morpholin-4-ylphenyl)amino]methyl }pheny])[1,2,4]tr-iazolo[4,3 -a]quinolin-1(2H)- one; 5-amino-8-bromo[1,2,4]triazolo[4,3-a}quinolin-1(2H)-one; 7-(4-{ [4-(hydroxymethyl)piperidin-1 -yiJmethyl}phenyl)-5-metlhyl(1,2,4] triazolo[4,3- ajquinolin-1(2H)-one; 5-(4-{ [4-(hydroxymethyl)piperidin- 1-ylJmethyl}phenyl)[1,2,4] triazolo[4,3 -a]quinolin-1(2H)- one; 7-(4-{ [(2-furylmethyl)amino]methyl }phenyl)-5-methyl[1 2,4]tmciazolo[4,3-a]quinolin-1(2H)- one; 5-(4- {[4-(2-hydroxyethyl)piperidin-1 -yl|methyl }phenyl)[1,2,4 triazolo [4,3-a]quinolin-1(2H)- one; 5-{4-[(4-pyridin-2-ylpiperazin-1 -yl)methyl]phenyl}[1 ,2,4]triazzolo[4,3-a]quinolin-1(2H)-one; 5-[4-({4-[4-(trifluoromethyl)pyrimidin-2-yl}-1,4-diazepan- 1- yl}methyl)phenyl][1 ,2,4]triazolof4,3-a]quinolin- 1(2H)-one; 4-[4-(1-0x0-1,2-dihydro[1 2 4]triazolo[4,3-a]quinolin-5-yl)berazyl]piperazine-1 -carbaldehyde; 4-[4-(1-0x0-1,2-dihydrof1 2 4]triazolo[4,3-a]quinolin-5-yl)berazyl]piperazine-1-carboxamide; 5-(4-{[(piperidin-4-ylmethyl)amino}methyl}phenyh[1 ,2,4tria_zolo[4,3-a]quinolin-1(2H)-one; 5-(4-{[4-(2-hydroxyethyl)-1,4-diazepan-1 -ylmethyl}phenyD)[ 1,2,4]triazolof4,3-a]quinolin- 1(2H)-one,

5-[4-({4-[3-chloro-5-(trifluoromethyl)pyridin-2-yl}-1 ,4-diazepan-1- yl}methyl)phenyl][1,2,4]triazolo[4,3-a] quinolin-1(2H)-one; : 5-(4-{[4-(3-nitropyridin-2-y1)-1 ,4-diazepan-1-yl]methyl }phenyl)(1 ,2,4triazolo[4,3- a]quinolin-1(2H)-one; 5S 7-(4-methoxy-3-{[(3 -morpholin-4-ylpropyl)amino]methyl} pheny!)-5- methyl[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 7-(3-{[(2-hydroxyethyl)amino}methyl } -4-methoxyphenyl)-5-methyl[1,2,4]triazolo[4,3- a]quinolin-1(ZH)-one; 7-(4-methoxy-3-{[(2-pyridin-2-ylethyl)amino] methyl }phenyl)-5-methyl[1,2,4]triazolo[4,3- a]quinolin-1(2H)-one; 7-(3-{[4-(2-hydroxyethyl)piperidin-1-ylJmethyl} -4-methoxyphenyl)-5- methyl[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 7-{3-[({2-[({5-[(dimethylamino)methyl}-2-furyl} methyl)thio]ethyl}amino)methyl]-4- methoxyphenyl}-5-methyl[ 1,2 4]triazolo[ 4,3-a]quinolin-1 (2H)-one; 5-{2-[({2-[({5-[(dimethylamino)methyl]-2-furyl} methyl)thio]ethyl }amino)methyl}-6- methoxyphenyl}[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 5-{2-methoxy-6-{(4-pyridin-2-ylpiperazin- 1-yDmethyl]phenyl}{1,2,4}triazolo[4,3-a]quinolin- 1(2H)-one; 5-(3-{[(3-furylmethyl)amino]methyl } -4-methoxyphenyl)[1 ,2,4]triazolo[4,3-a]quinolin-1(2H)- one; 5-{3-[({2-[({5-[(dimethylamino)methyl] -2-furyl}methyl)thio]ethyl }amino)methyl]-4- methoxyphenyl}[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 5-[3-({[2~(4-benzylpiperazin-1-y)ethyl]amino }methyl)-4-methoxyphenyl]{1,2,4]triazolo[4,3- ajquinolin-1(2H)-one; 5-{4-methoxy-3-[(4-pyridin-2-ylpiperazin-1 -yD)methyl]phenyl}[1,2,4]triazolo[4,3-a]quinolin- 1(2H)-one; 8-chloro-7-methoxy-5-methyl[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 7-methoxy-5-methyl-8-pyridin-4-yl[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 8-[3-(benzyloxy)phenyl]-7-methoxy-5-methyl[1 ,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 7-methoxy-8-[4-(methoxymethyl)phenyl]-5-methyl[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one;

Tert-butyl 3-(7-methoxy-S-methyl-1-oxo-1,2-dihydro[1,2,4]triazolo{4,3-a]quinolin-8- yl)benzylcarbamate; 8-[4-(aminomethyl)phenyl]-7-methoxy-5-methyl[1,2,4]triazolo[4,3-a] quinolin-1(2H)-one

4-methoxy-3-(7-methoxy-5-methyl-1 -ox0-1,2-dihydro[ 1,2,4triazolo[4,3 -ajquinolin-8- yl)benzaldehyde; : 8-(3 4-dimethoxyphenyl)-7-methoxy-5-methyl{1,2,4]triazolo[4,3 -a]quinolin-1(2H)-one; 8-(3-chloro-4-fluorophenyl)-7 -methoxy-5-methyl[1 2 4]triazolo[4,3-a]quinolin-1(2H)-ore;

8-[4«(dimethylamino)phenyl] -7-methoxy-5-methyl[1 2 A]triazolo[4,3-a]quinolin-1 (2H)-one; 8-(3-aminophenyl)-7 -methoxy-5-methyl[1 ,2,4]triazolo[4,3-a]quinolin-1 (2H)-one; 8-(2,6-dimethoxyphenyl) -7-methoxy-5-methyl[1,2,4]triazolo[4,3 -a]quinolin-1(2H)-one; 7-methoxy-8-(3 -methoxyphenyl)-5-methyl[1 ,2,4]triazolo[4,3-a]quinolin-1 (2H)-one; 8-(4-chlorophenyl)-7-methoxy-5-methyl[1 ,2,4]triazolo[4,3-a]quinolin-1(2H)-one;

7-methoxy-8-[3-(methoxymethyl)phenyl]-5-methyl[1 ,2,4]triazolo[4,3-a]quinolin-1(2H) —one; 8-[3-(hydroxymethyl)phenyl]-7-methoxy-5 -methyl[1,2,4]triazolo[4,3-a]quinolin-1 (2H)—one;

8-[4-(hydroxymethyl)phenyl] -7-methoxy-5-methyl[1 ,2,4]triazolo[4,3-a]quinolin-1(2H)—one; 8-[3-(aminomethyl)phenyl] -7-methoxy-5-methyl[1,2,4]triazolo[4,3 -a]quinolin-1(2H)-ome; 8-(3-{[(2-hydroxyethyl)amino]methyl }phenyl)-7-methoxy-5-methyl{1 ,2,4]triazolo[4,3—

a]quinolin-1(2H)-one; 7-methoxy-5-methyl-8-[3-({[(1-methyl-1 H-pyrrol-2-yl)methyl]amino }methyl)phenyl] [1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 8-(3-{[4-(2-hydroxyethyl)piperidin-1-yljmethyl }phenyl)-7-methoxy-5- methyl[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one;

7-methoxy-5-methyl-8-(3-{ [(pyridin-4-ylmethyl)aminolmethyl}phenyl)[ 1 ,2,4]triazolo[ 4,3- alquinolin-1(2H)-one;

8-{ 3[(isobutylamino)methyl]phenyl}-7-methoxy-5-methyl[ 1,2,4]triazolo[4,3-a]quinolL in- 1(2H)-one; 7-methoxy-5-methyl-8-(3-{[(3-morpholin-4-

ylpropyl)amino)methyl}phenyl)[1 ,2 4}triazolo[4,3-a]quinolin- 1 (2H)-one; 8-(3-{[4-(hydroxymethyl)piperidin-1 -ylJmethyl}phenyl)-7-methoxy-5- methyl[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 8-[3-({[3-(1H-imidazol- 1-yl)propylJamino }methyl)phenyl}-7-methoxy-5- methyl[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one;

8-(3-{ [(3-chlorobenzyl)amino}methyl} phenyl)-7-methoxy-5 -methyl[1,2,4]triazolo[4,3- alquinolin-1(2H)-one; 7-methoxy-5-methyl-8-[3-({methyl[2-

(methylamino)ethyl]amino }methyl)phenyl][1 ,2,4]triazolo[4,3-a]quinolin-1(2H)-one;

8-(4-methoxyphenyl)-5-methyl[1 ,2 Altriazolo[4,3-a]quinolin- 1(2H)-one; 5-hydroxy-8-[4-(hydroxymethyl)phenyl][ 1,2,4]triazolo[4,3-ajquinolin-1 (2H)-one; 5-methyl-8-pyridin-4-yi{1 2 4]triazolo(4,3-a]quinolin-1(2H)-one; 7 -hydroxy-8- [2-(hydroxymethyl)phenyl]-5 -methyl[1,2,4]triazolo{4,3-a] quinolin-1(2H)-one; 8-[3-(aminomethyl)phenyl]-7 -hydroxy-5-methyl[1 2 4]triazo1o[4,3-a]quinolin-1 (2H)-one; ®-[3-({[3 ~(dimethylamino)propylJamino}methylphenyt]-7 ~-methoxy-5- methyl[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 8-[3-({[3«(dimethylamino)propyljamino }methyl)-4-methoxyphenyl] -7-methoxy-5- methyl[1,2,4]triazolo(4,3-a]quinolin-1 (2H)-one; 7-methoxy-8-{4-methoxy-3-[(4-methylpiperazin- 1-yl)methy/l]phenyl}-5- methyl[1,2,4]triazolo[4,3-a]quinolin-1 (2H)-one; 8-(3-{[(2-hydroxyethyl)amino]methyl} -4-methoxyphenyl)-7-methoxy-5- methyl[1,2,4]triazolo[4,3-a]quinolin-1 (2H)-one; 7-methoxy-5-methyl-8-(1H-pyrrol-2-y1)[1 ,2,4]triazolo[4,3-a]quinolin-1(2H)-one; N-[4-(5-methyl-1-ox0-1,2-dihydro(1 ,2,4]triazolo{4,3 -a]quinolin-8-yl)phenyl]acetamide; 5-methyl-8-thien-2-ylf1 ,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 5.amino-8-thien-2-yl[1,2,4]triazolo[4,3-a]quinolin-1(2H)-omne; 5-amino-8-(2-furyl){1,2,4]triazolo [4,3-alquinolin-1(2H)-one; 5-methyl-8-(1H-pyrrol-2-yl)[1 ,2,4]triazolo[4,3-a]quinolin~- 1(2H)-one; 8-{2-furyl)-5-methyl[1 ,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 5-amino-8-thien-3-yl[1,2 4]triazolo[4,3-a]quinolin- 1(2H)-one; 5-methyl-8-thien-3-yl[1,2,4]triazolo[4,3 -a]quinolin-1(2H)-one.

N,N-dimethyl-3-(5-methyl-1-ox0-1,2-dihydro[1 2,4]triazo1o[4,3-a)quinolin-8-yl)benzamide; 5-{4-[(cyclopentylamino)methyl]phenyl}{1 ,2,4]triazolo[4 ,3-a]quinolin-1(2H)-one; 5-(4-{ [(tetrahydrofuran-2-ylmethyl)amino]methyl }phenyl)[1,2,4]triazolo{4,3-a]quinolin- 1(2H)-one; 5-(4-{[(2-hydroxypropyl)amino]methyl }phenyl)[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one

T-butyl 4-{[4-(1-0x0-1,2-dihydro[1 ,2,4]triazolo[4,3-a]quinolin-5- yl)benzyl]amino}piperidine-1-carboxylate; 7-hydroxy-8-(2-{ [(2-hydroxypropyl)amino]methyl} phenyl)-5-methyl[1 ,2,4]triazolo[4,3- a]quinolin-1(2H)-one; 7-hydroxy-5-methyl-8-phenyl[1,2,4]triazolo[4,3 -a]quinolin-1(2H)-one; 8-(4-chlorophenyl)-7-hydroxy-5-methyl{1,2,4]triazolo[4, 3-a} quinolin-1(2H)-one;

8-(3-chloro-4-fluorophenyl)-7-hydroxy-5-methyi[1 2 Altriazolo[4,3-a]quinolin-1(2H)-one; 8-[4-(dimethylamino)phenyl]-7-hydroxy-5-methyl[1 ,2 Altriazolo[4,3-a]quinolin-1(2H)-one; 8-(3-aminophenyl)-7-hydroxy-5-methyl{1,2 4]triazolo [4,3-a]quinolim-1(2H)-one; 7-hydroxy-8-(2-methoxypyridin-4-yl)-5-methyl[1 2 4)triazolo[4,3-a]quinolin-1(2H)-one;

5-(3-aminopropoxy)[ 1,2,4]triazolo{4,3-a]quinolin-1(2H)-one; 8-(2-aminophenyl)-7-hydroxy-5-methyl[1 ,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 8-{2-[(cyclopentylamino)methyl]phenyl} -7-hydroxy-5-methyl[1,2,<4]triazolo[4.3 -ajquinolin- 1(2H)-one; 7-hydroxy-8-(3-hydroxyphenyl)-5-methyl[1,2,4}triazolo[4,3 -a]quinolin-1(2H)-one;

7-hydroxy-5-methyl-8-[3 -({methyl[2-(methylamino)ethylJamino }methyl)phenyl] [1,2,4]triazolo[4,3-a] quinolin-1(2H)-one; 7-hydroxy-8-{3-({[3-(1H-imidazol- I-yl)propyl] amino }methyl)phenyl]-5- methyl(1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 8-[3-({[3-(dimethylamino)propyljamino}methyl)phenyl}-7-hydrox y-5-

methyl[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 7-hydroxy-S-methyl-8-(3-{[(pyridin-4-ylmethyl)amino]methyl }ph.eny})[1 ,2,4]triazolo[4,3- ajquinolin-1(2H)-one; 4-amino-8-[4-(hydroxymethyl)phenyl][ 1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 7-hydroxy-5-methyl-8-(3-{[(3-morpholin-4-ylpropyl)amino]methy!1} phenyl)

[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 8-(3-{[(3-chlorobenzyl)amino]methyl} phenyl)-7-hydroxy-5 -methyi[1,2 4]triazolo [4,3-a}quinolin-1(2H)-one; 5-[3-({[2-(4-benzylpiperazin-1-yl)ethyi] amino }methyl)-4-hydrox yphenyl] [1,2,4]triazolo[4,3- a)quinolin-1(2H)-one;

5-{2-hydroxy-6-[(4~pyridin-2-ylpiperazin-1-yl)methyl]phenyl} [1 »2,4]triazolo [4,3-a]quinolin- 1 (2H)-one; 5-[2-({[2-(4-benzylpiperazin-1-yl)ethyl]amino}methyl)-6-hydrox yphenyl] [1,2,4]triazolo[4,3- ajquinolin- 1(2H)-one; 4-amino-8-thien-2-yl[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one;

4-amino-8-[3-(hydroxymethyl)phenyl][1,2,4}triazolo[4,3-a]quino lin-1(2H)-one; 6-[3-(aminomethyl)phenyl][1,2,4]triazolo[4,3-a]quinolin-1(2H)-One; 5-(hydroxymethyl)~8-[3-(hydroxymethyl)phenyl]-7-methoxy[ 1,2 ,4]triazolo[4,3-a]quinolin- 1(2H)-one;

8-(3-aminophenyl)-5-(hydroxymethy!)-7-methoxy[ 1 ,2,4]triazolo [4,3-a]quinolin-1(2H)-one; 7-hydroxy- 5-(hydroxymethyl)-8-[2-(hydroxymethyl)phenyl] [1,2,4]triazolo [4,3-a]quinolin-1(2H)-one; 7-hydroxy-5-(hydroxymethyl)-8-[3 -(hydroxymethyl)phenyl][1,2,4] triazolo [4,3-a]quinolin-1(2H)-one; 8-(3-aminophenyl)-7-hydroxy-5 -(hydroxymethyl)[1,2,4]triazolo [4,3-a]quinolin-1(2H)-one; 6-{3-[(cyclohexylamino)methyl]phenyl}[1 ,2 A]triazolo[4,3-a]quinolin-1(2H)-one; 6-{3-[(cyclopentylamino)methyl]phenyl}[1 2 4ltriazolo[4,3-a]quinolin-1(2H)-one; 6-(3-{ [(tetrahydrofuran-2-ylmethyl)amino]methyl } phenyl) 1,2 ,4]triazolo [4,3-a]quinolin-1(2H)-one; 6-(3-{ [4-(hydroxymethyl)piperidin-1 -yl]methyl}phenyl)[1,2,4]triazolo [4,3-alquinolin-1(2H)-one; 4-(hydroxymethyl)-8-pyridin-4-yl[1,2,4]triazolo[4,3-a] quinolin-1(2H)-one; 8-(3-furyl)-S-methyl[1,2,4]triazolo[4,3-a]quinolin- 1(2H)-one; 6-{3-[(isobutylamino)methyl]phenyl}[1,2,4]triazolo[4,3 -a]quinolin-1(2H)-one; 6-(3-{ [4-(2-hydroxyethyl)-1,4-diazepan-1-yljmethyl }phenyl)[1,2,4 Jtriazolo [4,3-a]quinolin-1(2H)-one; 8-(2-aminophenyl)-7-hydroxy-5-(hydroxymethyl)[1 ,2,4]triazolo[4, 3-a]quinolin-1(2H)-one; 6-(4-hydroxy-3-{[(tetrahydrofuran-2-ylmethyl)amino]methyl } phenyl) [1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 6-{4-hydroxy-3-[(isobutylamino)methyl]phenyl}[1 ,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 4-(hydroxymethyl)-8-thien-2-yl[1,2,4]triazolo[4,3-a]quinolin- 1 (2H)-one; 5-(hydroxymethyl)-8-thien-2-yl[1,2,4]triazolo[4,3-a]quinolin-1 (2H)-one; 5-(hydroxymethyl)-8-thien-3-yl[1,2,4]triazolo[4,3-a]quinolin-1 (2H)-one; 7-methoxy-5-methyl-8-thien-3-yl[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 7-hydroxy-5-methyl-8-thien-3-yl[1,2,4]triazolo[4,3-a]quinolin- 1(2H)-one; 5-amino-7-hydroxy-8-thien-3-yl[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one;

N-[3-(5-methyl-1-ox0-1,2-dihydro[1,2,4]triazolo[4,3-a] quinolin-8- yhphenyl]methanesulfonamide; 5-amino-8-(1H-pyrrol-2-yl)[1,2,4]triazolo[4,3-a]quinolin-1(ZH)-ome; 5-(hydroxymethyl)-8-(1H-pyrrol-2-yI)[ 1,2,4]triazolo[4,3-a]quinolin-1(2H)-one;

5-methyl-8-(1H-pyrazol-4-yl)[1 2 4]triazolo[4,3-a]quinolin-1(2H)-one; 5-amino-8-(1H-pyrazol-4-yl)[ 1,2 4]triazolo[4,3 -a]quinolin-1(2H)-one; 5-amino-8-(3-furyl)[1,2,4]triazolo[4,3 -a]quinolin-1(2H)-one; 5.methyl-8-(4-methylthien-2-y1)[1 2,4)triazolo[4,3-a]quinolin-1(2H)-one; 8-[5-(hydroxymethyl)thien-2-yl]-5-methwI[ 1,2,4]triazolo[4,3-a]quinolin-1(21E)-one; 8-[5-(1 -hydroxyethyl)thien-2-y1]-5-meth 31{1 2,4)triazolof4,3-a]quinolin-1(2¥)-one;

Tert-butyl 4-{[(1-oxo-8-thien-3-yl-1 2-dihydro[1,2,4]triazolo[4,3-a] quinolin -5- yl)amino]methyl} piperidine-1 -carboxylate; 8-bromo-5-(hydroxymethyl)[1 ,2,4}triazo10[4,3-a]quinolin-1 (2H)-one; 7-methoxy-8-[4-methoxy-3-({[(1-methy1-1 H-pyrrol-2-yl)methyl] amino}mewthyl)phenyl]-5- methyl[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 7-methoxy-8-(4-methoxy-3-{[(pyridin-4 ~ylmethyl)amino]methyl} phenyl)-5 - methyl[1,2,4]triazolo[4,3-a]quinolin-1(2 H)-one; 8-(3-{[4-(2-hydroxyethyl)piperidin-1 ~yl Jmethyl}-4-methoxyphenyl)-7-mettaoxy-5 - methyl[1,2,4]triazolo[4,3-a]quinolin-1(2 H)-one; 7-methoxy-8-(4-methoxy-3-{ [(2-pyridin -2-ylethyl)amino]methyl }phenyl)-5- methyl[1,2,4]triazolo[4,3-aJquinolin-1(2 H)-one; 8-(3-{[4-(hydroxymethyl)piperidin-1 -yl Jmethyl} -4-methoxyphenyl)-7-metbaoxy-5- methyl([1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 7-methoxy-8-(4-methoxy-3-{ [(2-methoxyethyl)amino}methyl }phenyl)-5- methyl[1,2,4]triazolo[4,3-a]quinolin-1 (2H)-one; 7-methoxy-8-(3-{ [(2-methoxyethyl)amimo]methyl }phenyl)-5-methyl[1,2,4] triazolo [4,3- ajquinolin-1(2H)-one; 8-{3-[(cyclopentylamino)methyl] -4-methoxyphenyl }-7-methoxy-5-methyl[ 1 ,2,4]triazolo[4,3- a]quinolin-1(2H)-one; 8-(3-¢ [(4-fluorobenzyl)amino}methyl}-4-methoxyphenyl)-7-methoxy-5- methyl 1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 8-{3 -[(cyclobutylamino)methyl]-4-methoxyphenyl }-7-methoxy-5-methyl[ 1 ,2,4]triazolo[4,3- a]quinolin-1(2H)-one; 8 3.{(cyclohexylamino)methyl]-4-methoxyphenyl}-7-methoxy-5 -methyl[ 1,2,4]triazolo[4,3- a]quinolin-1(2H)-one; 8-{3-[(cyclopentylamino)methyl]pheny1}-7-methoxy-5 -methyl[ 1,2,4]triazc]o[4,3-a]quinolin- 1(2H)-one;

8-{3-[(cyclobutylamino)methyljphenyl} -7-methoxy-5-methyi[1,2,4]triazolo[4,3 -alJquinolin- 1(2H)-one; 8-{3-[(cyclohexylamino)methyl}phenyl} -7-methoxy-5-methyl[1,2,4]triazolof4,3-a] q uinolin- 1(2H)-one; 8-(3-{[(2-hydroxypropyl)amino] methyl }phenyl)-7-methoxy-5-methyl[1,2 ,4]triazolo [4,3- a]quinolin-1(2H)-one; 8-(3-{[4-(2-hydroxyethyl)-1,4-diazepan-1 -ylJmethyl}phenyl)-7-methoxy-5- methyl[1,2,4]triazolof4,3-a]quinoli n-1(2H)-one; 8-{3-[(cyclopropylamino)methyl}p henyl} -7-methoxy-5-methyl(1,2,4]triazolo[4,3-a7] quinolin- 1(2H)-one; 7-methoxy-S-methyl-8-(3-{[(tetramydrofuran-2- ylmethyl)amino]methyl} phenyD)[1 ,2,4]triazolo [4,3-a]quinolin-1(2H)-one; 7-methoxy-5-methyl-8-(3-{ [(2-phenoxyethyl)amino]methyl} phenyl)[1 ,2,4]triazolo¥ 4,3- a]quinolin-1(2H)-one; 7-methoxy-5-methyl-8-[3-({[2-(2-thienyl)ethyi]amino} methyl)phenyl][1,2,4]triazo 1o[4,3- ajquinolin-1(2H)-one; 8-{3-[(cyclopropylamino)methyl]—4-methoxyphenyl } -7-methoxy-5-methyl[1,2,4]tr-jazolo[4,3- a]quinolin-1(2H)-one;

S-methyl-8-pyridin-3-yl[1,2,4]tria=zolo[4,3-a]quinolin-1(2H)-one; 7-hydroxy-8-{3-[(isobutylamino)tmethyl]phenyl}-5 -methyl[1,2,4]triazolo[4,3-a]quinolin- 1(2H)-one; 7-hydroxy-8-(3-{[4-(2-hydroxyethyl)piperidin-1 -yljmethyl}phenyl)-5- methyl[ 1,2,4]triazolo{4,3-alquino lin- | (2H)-one; 7-hydroxy-5-methyl-8-{3-[(4-methylpiperazin-1 -y)methyllphenyl}[1,2,4]triazolo[4,3- a]quinolin-1(2H)-one; 7-hydroxy-8-(4-hydroxy-3-{ [(pyridin-4-ylmethyl)amino]methyl} phenyl)-5- methyl[1,2,4]triazolo[4,3-a]quino lin-1(2H)-one; 8-{3-[(cyclopentylamino)methyl} phenyl}-7-hydroxy-5-methyl[1 ,2,4]triazolo{4,3-a)quinolin- 1(2H)-one; 8-(3-{[(4-fluorobenzyl)amino]methyl} phenyl)-7-hydroxy-5-methyl[1,2,4]triazolo [4,3- a]quinolin-1(2H)-one; 8-[2-(hydroxymethyl)phenyl]-7-rmethoxy-5-methyl[1,2,4]triazolo[4,3-a]quinolin- k (2H)-one

7-methoxy-5—methyl- 8-[4-(morpholin-4-ylcarb onyl)phenyl]{1,2,4]triazolo [4,3-a]quinolin- 1(2H)-one; 7-methoxy-5 -methyl-8-[4-(pyrrolidin-1 -ylcarbonyl)phenyl][1 ,2,4]triazolo[4,3-alquinol&n- 1(2H)-one; 7-methoxy-S -methyl-8-[4-(piperidin-1 -ylcarbonyl)phenyl][1 ,2,4)triazolo[4,3-a]quinolixy- 1(2H)-one; 8-chloro-7-h ydroxy-5-methyl{1,2 [AJtriazolo[4,3-a]quinolin-1(2H)-one; 8-{3-[(cyclobutylamino)methyl]phenyl} -7-hydroxy-5-methyl[1,2 4]triazolo[4,3 -a]quirnolin- 1(2H)-one; 7-hydroxy-5 -methyl-8-(3-{[(tetrahydrofuran-2- ylmethyl)annino]methyl}phenyl){1,2,4]triazolo[ 4.3 -a]quinolin-1(2H)-one; 7-hydroxy-8&-(3-{[4-(2-hydroxyethyl)-1,4-diazepan-1 -ylJmethyl}phenyl)-5- methyl[1,2,<4]triazolo[4,3-a]quinolin-1(2H)-one; 8-{3-[(cyclopropylamino)methyl}phenyl}-7-hydroxy-5 -methyl[ 1,2,4]triazolo[4,3-a]qu inolin- 1(2H)-one; 8-{3-[(cyclopropylamino)methyl]phenyl} -7-hydroxy-5-methyl[1,2,4]triazolo(4,3-a] quinolin- 1(2H)-one; 8-{3-[(cyclohexylamino)methyl]phenyl}-7 -hydroxy-5-methyl[1,2,4]triazolo[4,3-a]quinolin- 1(2H)-one;

N-cyclohex yl-4-(7-methoxy-5-methyl-1-oxo-1,2-dihydro[ ,2,4]triazolo[4,3-alquinolir-8- yl)benzamide; 8-(2-{[(4-fLuorobenzyl)amino]methyl }phenyl)-7-methoxy-5-methyl[1,2,4]triazolo[4,3- alquinolin- 1(2H)-one; 8-(2-{[(2-h.ydroxyethyl)aminolmethyl }phenyl)-7-methoxy-5-methyl[1 ,2,4]triazolo[4, 3- a]quinolin- 1(2H)-one; 8-(2-{[4-(h.ydroxymethyl)piperidin-1-ylJmethy1}phenyl)-7-methoxy-5- methyl[1,2 ,4]triazolo[4,3-a]quinolin-1(2H)-one; 8-(2-{[4-(Im ydroxymethyl)piperidin-1-ylJmethy1}phenyl)-7-methoxy-5- methyl[1,2 ,4]triazolo[4,3-a]quinolin-1(2H)-one; 7-bromo-NI-(4-methoxybenzyl)-1-oxo-1,2-dihydro[1,2,4]triazolo[4,3-a]quinoline-5- carboxamicie; 8-(benzylaamino)-5-methyl[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one;

N,N-dimethyl-4-(5-methyl-1-oxo-1,2-dihydro[ 1,2,4]triazolo[4,3-a]quinolin-8-yl)benzamide;

5-methyl-8-[4-(pyrrolidin-1 -ylcarbonyl)phenyl][1 2, 4]triazolo[4,3-a]quinolin-1(2 H)-one; 5-methyl-8-[4-(piperidin-1 -ylcarbonyl)phenyl][1 2 A]triazolo[4,3-a]quinolin-1(2Ed)-one; [4-(5-methyl-1-0xo0-1,2-dihydro[ 1 ,2,4]triazolo[4,3-a] quinolin-8-yl)phenyljacetornitrile; 8-[3-(hydroxymethyl)phenyl]-1-oxo-1 ,2-dihydro[ 1,2,4]triazolo[4,3-a] quinoline-S-carboxylic acid; 3-(5-methyl-1-0xo-1,2-dihydro[1 ,2,4]triazolo[4,3-2] quinolin-8-yl)benzonitrile; 5-methyl-8-[4-(morpholin-4-ylcarbonyl)phenyl] [1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 8-[2-(hydroxymethyl)phenyl]-1 -oxo-N-piperidin-4-yl-1,2-dibydro[ ,2 Altriazolo[4,3- ajquinoline-5-carboxamide; 7-[3-(hydroxymethyl)phenyl]-1 -oxo-N-piperidin-4-yl-1,2-dihydro[ 1 2 Altriazolo[4,3- a]quinoline-35 -carboxamide; [3-(7-methoxy-5-methyl-1-o0xo-1,2-dihydro[1 ,2,4]triazolo[4,3-a]quinolin-8- yDphenyl]acetonitrile;

N-(2-cyanoethyl)-3-(7-methoxy-5-methyl-1-oxo- 1,2-dihydro[1,2,4]triazolo[4,3 —a] quinolin-8- ylbenzamide; 6-chloro[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 7-hydroxy-5-methyl-8-[4-(piperidin-1 -ylcarbonyl)phenyl][1,2,4]triazolo[4,3-a] guinolin- 1(2H)-one;

N-cyclohexyl-4-(7-hydroxy-5-methyl-1-oxo-1 ,2-dihydro[ 1,2,4]triazolo[4,3-a]q uinolin-8- yl)benzamide; 6-[4-(hydroxymethyl)phenyl][1,2,4]triazolo[4,3-a] quinolin-1(2H)-one; 6-[3-(hydroxymethyl)phenyl][1 ,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 6-(3-aminopheny!)[ 1,2,4]triazolo[4,3-a]quinolin-1 (2H)-one; 7-methoxy-4-{ [(pyridin-4-ylmethyl)amino]methyl}[1 ,2,4]triazolo[4,3-a]quinoXin-1(2H)-one; 5-amino-8-pyridin-4-yl[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 3-(5-methyl-1-oxo-1,2-dihydro[ 1 ,2,4]triazolo[4,3-a]quinolin-8-yl)benzamide; 2-(5-methyl-1-oxo-1,2-dihydro[1,2,4]triazolo[4,3 -a]quinolin-8-yl)benzamide; 8-chloro-7-(3-chloropropoxy)-5-methylf1 ,24]triazolo[4,3-a]quinolin- 1(2H)-ome; 8-chloro-7-(2-methoxyethoxy)-5-methyl{1,2,4]triazolo[4,3-a]quinolin-1 (2H)-One; 8-[3-(hydroxymethyl)phenyl]-7-(2-methoxyethoxy)-5 -methyl[1,2,4]triazolo[4 ,3-a]quinolin- 1(2H)-one; 7-(3-aminopropoxy)-8-[3 -(hydroxymethyl)phenyl]-5-methyl[1,2,4]triazolo[4,3-a]quinolin- 1(2H)-one;

7-(3-aminopropoxy)-8 [2-(hydroxymethyl)phenyl}-5-methyl{1 .2,4]txiazolo[4,3-a]quinolin- 1(2H)-one; : 7-hydroxy-8-(2-thydroxyphenyl)-5-methyl[1 2, 4]triazolo[4,3-a]quinolin-1(2H)-one; 8-bromo-4-(hydroxymethyl)[1,2,4]triazolo[4,3-a]quinolin- 12H)-one; 5-methyl-8-(2-thienyl)[1,2,4]triazolo[4,3-a]quinolin-1 (2H)-one;

N,N-dimethyl-3 —(5-methyl-1-0x0-1,2-dihydro[ 1 ,2,4]triazolo[4,3-a] quinolin-8-yl)benzamide; 5-{4-[(cyclopentylamino)methyl]phenyl}[1 ,2,4triazolo[4,3-a]quinolin-1(2H)-one; 5-(4-{[(tetrahyd-rofuran-2-ylmethyl)amino]methyl }phenyl)[1 ,2,4]triazolo[4,3-a]quinolin- 1(2H)-one; 5-(4-{[(2-hydroxypropyl)amino]methyl }phenyD[1 ,2,4]triazolo[4,3~a]quinolin-1(2H)-one; tert-butyl 4-{[4~(1-0x0-1,2-dihydro[1 ,2,4]triazolo[4,3-aJquinolin-5- yl)benzyllamino }piperidine-1-carboxylate; 7-hydroxy-8-(2—{ [(2-hydroxypropyl)amino}methyl} phenyl)-5-methyl[ 1,2,4]triazolo[4,3- aJquinolin-1(2H)-one; 8-(2-{[(4-fluorobenzyl)amino]methyl }phenyl)-7-hydroxy-5-methy1[1 ,2,4]triazolo[4,3- a]quinolin-1(2H)-one; 7-hydroxy-8-(2 -{[4-(hydroxymethyl)piperidin- 1-ylJmethyl}phenyk)-5- methyl[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 4-(hydroxymethyl)-8-methoxy[ 1,2,4]triazolo[4,3-a] quinolin-1(2H)-one; 8-{2-[(cyclopentylamino)methyl]phenyl}-7 -methoxy-5-methyl[ 1,2 4]triazolo[4,3-a]quinolin- 1(2H)-one; 4-[(cyclobutylamino)methyl]-7-hydroxy(1,2,4]triazolo[4,3 -a]jquinolin-1(2H)-one; 7-hydroxy-S-muethyl-8-phenyl{1,2,4]triazolo [4,3-a]quinolin-1(2H)-one; 8-(4-chlorophenyl)-7-hydroxy-5-methyl{ 1 ,2,4]triazolo[4,3-a]quinolin- 1(2H)-one; 4-{ [(4-flucrobenzyl)amino]methyl }-7-hydroxy[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 8-[4-(dimethyl amino)phenyl]-7-hydroxy-5-methyl[1 ,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 8-(3-aminophenyl)-7-hydroxy-5-methyl[1 ,2,4)triazolo[4,3-a]quinolin-1(2H)-one; 8-(2-aminophenyl)-7-methoxy-5-methyl[1 ,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 7-hydroxy-8-(2-methoxypyridin-4-yl)-5-methyl[1 ,2,4]triazolo[4,3 -a]quinolin-1(2H)-one; 5-(3-aminopropoxy)[l ,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 8-[2-(hydroxywmethyl)-4-methoxyphenyl]-5-methyl[1 ,2,4]triazolo [4,3-a]quinolin-1(2H)-one; 8-(2-aminophenyl)-7-hydroxy-5-methyl[1,2,4]triazolo[4,3-a] quinolin-1(2H)-one;

8- {2-[(cyclopentylamino)methyl]phenyl} -7 -hydroxy-5-methyl[1 ,2,4]triazolo[4,3-a]qquinolin- 1(2H)-One; 7-hydroxy-8-(3 -hydroxyphenyl)-5-methyl[ 1 2 4]triazolo[4,3-a]quinolin-1 (2H)-one; 7-hydroxy-5-methyl-8-[3-({methyl[2- (methylamino)ethyl]amino}methyl)phenyl] [1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 7-hydreoxy-8-[3-({[3-(1H-imidazol-1 -yl)propyllamino}methyl)phenyl]-5- methyl [1,2,4]triazolo[4,3-a]quinolin-1 (2H)-one; 7-hydroxy-5-methyl-8-(3-{ [(pyridin-4-ylmethyl)amino}methyl }phenyl)[1,2,4]riazeolo[4,3- ajquin«lin-1(2H)-one; 4-amino-8-[4-(hydroxymethyl)phenyl][1,2 4]triazolo [4,3-a]quinolin-1(2H)-one; 8-hydroxy-4-(hydroxymethy!)[1,2,4] triazolo[4,3-a]quinolin-1(2H)-one; 2-(5-ammino-1-oxo-1,2-dihydro[ 1 ,2,4]triazolo[4,3-a] quinolin-8-yl)benzamide; 7-hydxoxy-5-methyl-8-(3-{[(3-morpholin—4- ylpropyl)amino]methyl}phenyD)[1 ,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 8-(3-{ [(3-chlorobenzyl)amino]methyl }phenyl)-7-hydroxy-5-methyl[1 ,2,4]triazolof 4,3- a]quirzolin-1(2H)-one; 5-[3-( {[2-(4-benzylpiperazin-1-yl)ethyl]aznino} methyl)-4-hydroxyphenyl][1,2,4}tr—iazolo[4,3- a]quirolin-1(2H)-one; 5-{2-hydroxy-6-[(4-pyridin-2-ylpiperazin-1 -yl)methyl]phenyl}[1,2,4]triazolo{4,3~ 2] quinolin- 1(2H)»-one; ethyl 8-chloro-7-methoxy-1-oxo-1,2-dihydro[1 ,2,4]triazolo[4,3-a]quinoline-5-cart>oxylate; 2-(5-hydroxy-1-oxo-1,2-dihydro[1,2,4]tri azolo[4,3-a]quinolin-8-yl)benzamide; 5-[2-€ {[2-(4-benzylpiperazin-1-yl)ethylJamino }methyl)-6-hydroxyphenyl][1,2,4]t=xiazolo[4,3- a]quimolin-1(2H)-one; 4-amdino-8-(2-thienyl)[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 8-chl ©ro-7-hydroxy-5-(hydroxymethyl)[ 1,2,4]triazolo[4,3-a] quinolin-1(2H)-one; 5-(hydroxymethyl)-8-[2-(hydroxymethyl Jphenyl]-7-methoxy{ 1,2,4]triazolo[4,3-aJquinolin- 1(2HD)-one; 5-am ino-8-(4-methoxyphenyl)[1,2,4]triazolo[4,3-a]quinolin-1 (2H)-one; S-mesthyl-8-(1H-pyrrol-2-yD[1,2,4]triazolo[4,3-a]quinolin-1 (2H)-one; 6-[4— (aminomethyl)phenyl][1,2,4]triazolo[4,3-a] quinolin-1(2H)-one;

N-[2 —(1-0x0-1,2-dihydro[1,2,4]triazolo[4,3-a]quinolin-6-yl)phenyl] acetamide; 6-[2~(hydroxymethyl)phenyl](1,2,4]triazolo[4,3-a]quinolin-1(2H)-one;

4-amino-8-3-(hydroxymethyl)phenyl}[1,2,4}triazolo[4.3-a] quinolin-1(2H)-one;

4-amino-8-(2-furyl)[1,2,4]triazolo[4,3-a]quinolin-1 (2H)-one;

6-{3-(aminomethyl)phenyl][ 1,2,4]triazolo[4,3-a]quinolin-1 (2H)-one;

5-(hydroxymethyl)-8-[3-(hy droxymethyl)phenyl]-7-methoxy[1,2 4]riazolof4,3-a Jquinolin-

1(2H)-one;

8-(3-aminophenyl)-5-(hydroxymethyl)-7-methoxy] 1,2,4]triazolo[4,3-a]quinolin- 1(2H)-one; 7-hydroxy-5-(hydroxymethyl)-8-[2-(hydroxymethyl)phenyl][1,2 4]triazolo[4,3-a ]quinolin- 1(2H)-one;

7-hydroxy-5-(hydroxymeth yl)-8-[3 -(hydroxymethyl)phenyl][1 ,2,4}triazolo[4,3-a]quinolin-

1(2H)-one; 8-(3-aminophenyl)-7-hydroxy-5-(hydroxymethyl)[ 1,2,4]triazolo[4,3-a]quinolin- 1(2H)-one; 6-{3-[(cyclohexylamino)methyl]-4-methoxyphenyl} [1,2,4]triazolof4,3-a]quinolin-1 (2H)-one; 6-(4-methoxy-3-{ [(tetrahydrofuran-2-ylmethyl)amino]methyl } phenyl){ 1,2,4]triazolo[4,3- a]quinolin-1(2H)-one;

6-{3-[(cyclohexylamino)methyl]phenyl}[1,2,4] triazolo[4,3-a]quinolin-1(2H)-orxe; 6-{3-[(cyclopentylamino)maethyl]phenyl}[1 ,2,4]triazolo[4,3-a]quinolin-1(2H)-ome; 6-(3-{[(tetrahydrofuran-2-yImethyl)amino]methyl }phenyl)[1,2,4]triazolo[4,3-a] quinolin- 1(2H)-one; 6-(3-{[4-(hydroxymethyl)piperidin-1 -ylJmethyl}-4-methoxyphenyl)[1 ,2,4]triazolo[4,3-

ajquinolin-1(2H)-one; 6-(3-{[4-(hydroxymethyl)piperidin-1-ylJmethyl }phenyl)[1,2,4]triazolo[4,3-a]quiinolin-1 (2H)- one; 6-(3-hydroxyphenyl)[1,2,4]triazolo[4,3-a]quinolin- 1 (2H)-one; 4-(hydroxymethyl)-8-pyridin-4-yl[1,2,4]triazolo[4,3-alquinolin-1(2H)-one;

4-methyl-N-[1-0x0-8-(2-thienyl)-1,2-dihydro[1 ,2,4]triazolo[4,3-a]quinolin-4~ yl]benzenesulfonamide;

6-{3-[(isobutylamino)methyl}-4-methoxyphenyl}[1 ,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 6-(3-{[4-(2-hydroxyethyl)-1,4-diazepan- 1-yljmethyl }-4-methoxyphenyl){1,2,4 Jtriazolo{4,3- ajquinolin-1{2H)-one;

6-{3-[(isobutylamino)methyl]phenyl}[1,2,4]triazolo[4,3-a] quinolin-1(2H)-one 3 6-(3-{[4-(2-hydroxyethyl)-1,4-diazepan-1-yl)methyl }phenyl)[1 ,2,4]triazolo[4,3-a]quinolin- 1(2H)-one; 8-(2-aminophenyl)-7-hydroxy-5-(hydroxymethyl)[1,2,4]triazolo[4,3-a]quinolin- 1(2H)-one;

6-(4-hydroxy-3-{ [(tetrahydrofuran-2-ylmethyl)amino}methyl}pheny 1) 1 ,2,4]triazolo[4,3- aJquinolin-1(2H)-one; 6-{4-hydroxy-3 -[(isobutylamino)methyl]phenyl}[1 ,2 A)triazolo[4,3~a]quinolin-1(2H)-one; 6-(4-hydroxy-3-{[4-(hydroxymethyl)piperidin- 1-yllmethyl }phenyl) {1,2,4]triazolo[4,3- 5S a]quinolin-1(2H)-one; 4-(hydroxymethyl)-8-(2-thienyl){ 1 ,2,4]triazolo[4,3-a]quinolin-1 (2HD)-one; 6-(4-hydroxy-3-{[4-(2-hydroxyethyl)-1 ,A-diazepan-1-yl]methyl }phenyl)[1 ,2,4]triazolo[4,3- a]quinolin-1(2H)-one; 5-amino-8-(3-thienyl)[ 1,2,4]triazolo[4,3-a]quinolin-1 (2H)-one; S5-amino-8-chloro-7-hydroxy[1,2,4]triazolo[4,3-a]quinolin-1 (2H)-ome; 7-methoxy-5-methyl-8-(3-thienyl)[1,2,4]triazolo [4,3-a]quinolin-1(2H)-one; 7-hydroxy-5-methyl-8 -(3-thienyl)[ 1,2 4]triazolo[4,3 -a]quinolin-1(ZH)-one; 5-amino-7-hydroxy-8-(3-thienyl){1,2,4]triazolo[4,3 -a]quinolin-1(2¥)-one;

N-[2-(5-methyl-1-0x0-1,2-dihydro[ 1,2,4]triazolo[4,3 -ajquinolin-8- ylphenyl])methanesulfonamide; 8-(1H-indol-3-yl)-5-methyl[ 1,2 4]triazolo[4,3-a]quinolin-1(2H)-ome;

N-[3-(5-methyl-1-0xo0-1,2-dihydro[1,2,4]triazolo [4,3-a]quinolin-8— yl)phenyljmethanesul fonamide; 5-amino-8-(1H-pyrrol-2-yl)[1,2,4]triazolo[4,3-a]quinolin- 1(2H)-one; 5-(hydroxymethyl)-8-(1H-pyrrol-2-y1)[1 ,2,4]triazolof4,3-a]quinolan-1(2H)-one; 5-methyl-8-(1H-pyrazol-4-y1)[1,2,4]triazolo[4,3 -a]jquinolin-1(2H) onc; 5-amino-8-(1H-pyrazol-4-yl)[1,2,4]triazolo[4,3-a]quinolin-1(2H)~one; 5-amino-8-(3-furyl){ 1,2,4]triazolo{4,3-a]quinolin-1(2H)-one; 5-methyl-8-(4-methyl-2-thienyl)[1,2,4]triazolo[4,3-a] quinolin-1(2H)-one; 8-(3-furyl)-5-(hydroxymethyl)[1,2 4]triazolo[4,3-a}quinolin-1(2H )-one; 8-[5-(hydroxymethyl)-2-thienyl]-5-methyl[1,2,4]triazolo[4,3-a] quinolin-1(2H)-one; 8-[5-(1-hydroxyethyl)-2-thienyl}-5-methyl[1,2,4] triazolo[4,3-a]quuinolin-1(2H)-one; 5-(5-methyl-1-oxo0-1,2-dihydrof1,2,4]triazolo[4,3 -a]quinolin-8-yIJthiophene-2-carboxylic acid, tert-butyl 4-({[1-ox0-8-(3-thienyl)-1,2-dihydro[1,2,4]triazolo[4,3 —a]quinolin-5- ylJamino}methyl)piperidine-1-carboxylate; 5-amino-8-[5-(1-hydroxyethyl)-2-thienyl][1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 8-(1H-imidazol-4-yl)-5-methyl[1,2,4]triazolo[4,3-a]quinolin-1(2E])-one;

5-(hydroxymethyl)-8-(1H-pyrazol-4-yD[1 2,4triazolo[4,3-a]quinolin-1 (2H)-one; 8-bromo-5-[(dimethylamino)methyl][1 2,4]triazolo[4,3-a]quinolin-1 (2H)-one; 8-(2-furyl)-5-(hydroxymethyl)[1,2,4)triazolo[4,3-a]quinolin-1(2H)-one; 5-methyl-8-(1,3-thiazol-2-yl)[1 ,2,4ltriazolo[4,3-a] quinolin-1 (2H)-one; 5.[(dimethylamino)methyl]-8-(1H-pyrrol-2-yD[1,2 4 triazolo[4,3-a]quinolin-1(2H)-one; 5-methyl-8-pyrazin-2-ylf1 2 4]triazolo[4,3-a]quinolin-1(2H)-one; 5.(hydroxymethyl)-8-pyridin-4-yl[1,2,4}triazolo[4 3-2] quinolin-1(2H)-one; (5-methyl-1-oxo-1,2-dihydrof1 ,2,4]triazolo[4,3-a] quinolin-8-yl)boronic acid; 8-(2-furyl)-5-phenylf1 2 4]triazolo[4,3-a]quinolin-1(2H)-one; S-phenyl-8-(1H-pyrrol-2-yD[1 2 Altriazolo[4,3-a] quinolin-1(2H)-one; 8-(3-furyl)-5-(morpholin-4-ylmethyl[1 2,4]triazolo[4,3-a]quinolin-1(2H)-one; tert-butyl [2-({[1-0%o0-8-(1H-pyrrol-2-yl)-1,2-dih-ydro[ 1 ,2,A]triazolo[4,3-a]quinolin-5- yl)methyl}amino)ethyljcarbamate; 5-{[(2-aminoethyl)amino]methyl} -8-(1H-pyrrol-2-yl)[1 ,2,4]triazolo[4,3-a]quinolin-1 (2H)- one;

N-(2-aminocthyl)-8-bromo-1-oxo-1,2-dihydro[1 .2, 4]triazolo[4,3-a]quinoline-5-carboxamide; 8-(3-furyl)-1-oxo-1,2-dihydro[1,2,4]triazolo{4,3 —a]quinoline-5-carboxylic acid; 8-[3-(aminomethyl)phenyl}-5-phenyl{ 1,2,4]triazolo[4,3-a]quinolin-1(2H)-one;

N-[2-(dimethylamino)ethyl]-8-(3-furyl)-1-oxo- 1 2-dihydro[1,2,4]triazolo[4,3-a]quinoline-5- carboxamide; 5-methyl-8-[4-(2-morpholin-4-ylethoxy)phenyl] [1,2,4]triazolo[4,3-a]quinolin- 1(2H)-one; 8-{4-[2-(diethylamino)ethoxy]phenyl }-5-methy1[1,2,4]triazolo[4,3 -a]quinolin-1(2H)-one; 8-[3-(dimethylamino)prop-1-yn-1 -yl]-5-methylf1 ,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 7-piperazin-1-yl-5-(2-thienyl){1 2, 4]triazolo{4,3-ajquinolin-1 (2H)-one; 5-methyl-8-[3-(methylamino)prop- 1-yn-1-yl]{1 ,2,4]triazolo[4,3-alquinolin-1(2H)-one; 5-methyl-8-[4-(morpholin-4-ylmethyl)phenyl][ 1,2,4]triazolo[4,3-a]quinolin-1(2H)-one;

N-[2-(dimethylamino)ethyl]-1-oxo-8-(1H-pyrrol-2-y1)-1,2-dihydrof 1,2 4]triazolo[4,3- a]quinoline-5-carboxamide;

N-[2-(dimethylamino)ethy!]-1-ox0-8-(3-thieny1)-1,2-dihydro[1,2 4]triazolo[4,3-alquinoline-5- carboxamide; 5-{[(3R)-piperidin-3 -ylamino]methyl}-8-(1H-pyrrol-2-yD[ 1,2,4]triazolo{4,3-a]quinolin- 1(2H)-one;

5-methyl-8-{4-[(4-methylpiperazin-1 -yDmethylphenyl}[1,2,4]triazolo[4,3 -a]quinolin-1(2H)- one; tert-butyl (3S)-3-({[1-ox0-8-(3-thien yl)-1,2-dihydro[ ,2,4]triazolo[4,3-a]quinolin-5- yl]carbonyl }amino)piperidine- 1-carboxylate;

S-methyl-8-{4-[(methylamino)methyl]phenyl }[1 ,2,4}triazolo[4,3-a]quinolin-1(2H)-one; 8-(3,3-diethoxyprop-1-yn-1-yl)-S-methyl{1 ,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 5-methyl-8-[5-(morpholin-4-ylmethy!)-3-thienyl][1 ,2,4]triazolo[4,3-a]quinolin-1(2H)-one; tert-butyl 4-[4-(5-methyl-1-oxo-1,2-dihydro[1 ,2 4]triazolo[4,3-alquinolin-8- yl)benzyl]piperazine-1-carboxylate; 5-methyl-8-{5-[(methylamino)methyl]-3-thienyl}[1 ,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 5-methyl-8-{5-[(4-methylpiperazin- 1-yl)methyl]-3 -thienyl}[1,2,4]triazolo[4,3-a]quinolin- 1(2H)-one; tert-butyl 4-{[4-(5-methyi-1-oxo-1,2-dihydro[1,2,4]triazolo[4,3 -a]quinolin-8-y1)-2- thienyl]methyl } piperazine-1-carbox ylate; 5-methyl-8-[4-(piperazin-1-ylmethyl)phenyl][1,2,4]triazolo[4,3-a] quinolin-1(2H)-one; 1-ox0-N-[(3S)-piperidin-3-yl]-8-(3~thienyl)- 1,2-dihydro[1 ,2,4]triazolo[4,3-a}quinoline-5- carboxamide; tert-butyl (3S)-3-({[ 1-oxo-8-(1H-py/rrol-2-yl)-1,2-dihydro[ 1,2 ,4]triazolo[4,3-a}quinolin-5- yl]carbonyl }amino)piperidine-1-carboxylate; 5-methyl-8-[5-(piperazin-1-ylmethy/i)-3-thienyl][ 1,2,4]triazolo[4,3-a] quinolin-1(2H)-one;

N-(2-aminoethyl)-1-oxo-8-(3-thienyl)-1,2-dihydro[ 1,2,4]triazolo [4,3-a)quinoline-5- carboxamide; 1-0x0-N-[(3S)-piperidin-3-yl]-8-(1 H-pyrrol-2-yl}-1,2-dihydro[ 1,2,4]triazolo [4,3-a]quinoline-

S-carboxamide; 5-methyl-8-(1H-pyrrol-3-yD)[1,2,4] triazolo[4,3-a]quinolin-1(2H)-one; 5-methyl-8-(3-thienylethynyl)[ 1,2,4]triazolo[4,3-a]quinolin- 1 (2H)-one; 8-[5-({[3-(dimethylamino)propylJamino } methyl)-3 -thienyl]-5-methyl[ 1,2 4]triazolo[4,3- a]quinolin-1(2H)-one; 5-methyl-8-{5-[(methylamino)methyl]-2-thienyl}[1,2,4]triazolo[4,3-a] quinolin-1(2H)-one; 5-(hydroxymethyl)-8-[5-(morpholin-4-ylmethyl)-3-thienyl][1 ,2,4]triazolo[4,3-a]quinolin- 1(2H)-one; 5-(hydroxymethyl)-8-{5-[(methylamino)methyl]-3-thienyl}{1,2,4]triazolo[4,3-a]quinolin- 1(2H)-one;

5-(hydroxymethyl)-8-{5- [(4-methylpiperazin-1-yl)methyl]-3 -thienyl}[1,2,4]triazolo[4,3- a]quinolin-1(2H)-one; 8-{ 5-[(dimethylamino)methyl]-3-thienyl}-5 -(hydroxymethyD[1 2 4]triazolo[4,3-a]quinolin— 1(2H)-one; 5-(hydroxymethyl)-8-[5-(piperazin- 1-ylmethyl)-3-thienyl][1 ,2,4]triazolo[4,3-a]quinolin- 1(2H)-one;

N-[2-(methylamino)ethyl]-1-0x0-8-(3-thienyl)-1 2-dihydro[ 1,2,4]triazolo[4,3-a]quinoline-5- carboxamide;

N-[2-(methylamino)ethyl]-1 -ox0-8-(1H-pyxrol-2-yl)-1,2-dihydro[1 ,2,4\triazolo(4,3- a]quinoline-5-carboxamide; 8-bromo-5-§ [(2-methoxyethyl)(methyl)amino]methyl} [1,2,4]triazolo[4,3-a]quinolin-1 (2H>- one;

N-[2-(dimethylamino)ethyl}-8-{5 -[(4-meth ylpiperazin-1-yD)methyl]-3 -thienyl}-1-o0xo-1,2- dihydro[1,2,4]triazolo{4,3-a] quinoline-5-carboxamide; 8-bromo-5-{[2-(dimethylamino)ethoxy]methyl}[1 ,2,4)triazolo[4,3-2]quinolin-1(2H)-one;

N-(2-morpholin-4-ylethyl)-1-0x0-8-(3 -thienyl)-1,2-dihydro[1 ,2,4]triazolo[4,3-a]quinoline—3- carboxamide; 5-[(4-methylpiperazin-1-yl)methyl]-8-(3 -thienyl)[ 1,2,4]triazolo[4,3-a]quinolin-1 (2H)-ones 8-[5-({[3-(dimethylamino)propyl]amino} methyl)-3-thienyl]-5- (hydroxymethyl)[1,2,4]triazolo[4,3-a] quinolin-1(2H)-one; 5-amino-8-{ 5-[(methylamino)methyl]-3-thienyl}[1 ,2,4)triazolo[4,3-a]quinolin-1(2H)-one 3 5-(hydroxymethyl)-8-[5 ~(morpholin-4-ylmethyl)-2-thienyl][1 ,2,41triazolo[4,3-a]quinolin- 1(2H)-one; 5-(hydroxymethyl)-8-{5- [(methylamino)methyl]-2-thienyl}[1 ,2,4triazolo[4,3-a]quinolin— 1(2H)-one; 5-(hydroxymethyl)-8-{ 5-[(4-methylpiperazin-1-yl)methyl] -2-thienyl}{1,2,4]triazolo[4,3- ajquinolin-1(2H)-one; 8-{5-[(dimethylamino)methyl]-2-thienyl} -5-(hydroxymethyl)[ 1,2 4}triazolo[4,3-a]quinol 3in- 1(2H)-one; S-[(3-hydroxypyrrolidin-1 -yDmethyl]-8-(3 thienyl)[ 1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; : 5-amino-8-{5-[(4-methylpiperazin-1-yl)methyl]-3 -thienyl }[1,2,4]triazolo[4,3-a]quinolin~ 1(2H)-one;

5-(hydroxymethyl)-8-[5-(piperazin-1-ylmethyl)-2-thienylj[1,2,4]triazolo[4,3 -a]quinolin- 1(2H)-one; 5-(morpholin-4-yimethy1)-8-(3-thienyl)[1 2 A}triazolo[4,3-a]quinolin- 1(2H)—one; 5-{[(2-methoxyethyl) (methyl)amino]methyl}-8-(3 -thienyl)[1,2,4]triazolo[4, 3-a]quinolin- 1(2H)-one; 1-ox0-N-(2-piperidin-1-ylethyl)-8-(3-thienyl)-1 ,2-dihydro[1,2,4]triazolo[4,3-a] quinoline-5- carboxamide; 5-{[(2-morpholin-4-ylethyl)amino}jmethyl}-8-(3 -thienyl){1,2,4]triazolo[4,3 —a]quinolin-1(2H)- one; 5-[(dimethylamino)methyl]-8-(3-thienyl){1 ,2,4)triazolo[4,3-a]quinolin-1(2E1)-one;

N-[2-(dimethylamino) ethyl]-8-{4-[(4-methylpiperazin-1 -y)methyl]phenyl } -1-oxo-1,2- dihydro[1,2,4]triazolo[4-,3 -a]quinoline-5-carboxamide; [1-0x0-8-(3-thienyl)-1 ,2-dihydro[1,2,4]triazolo[4,3-a]quinolin-5 -yllmethyl glycinate; 5-{[2-(hydroxymethyl)imorpholin-4-ylJmethyl}-8-(1H-pyrrol-2-yh)[ 1,2,4]triazolo[4,3- a]quinolin-1(2H)-one; 5-[(4-methylpiperazin- 1 -yl)methyl]-8-(1H-pyrrol-2-yD[1 ,2 Atriazolo[4,3-a=]quinolin-1(2H)- one; 5-{[2-(hydroxymethyl)mmorpholin-4-yl]methyl}-8-(3-thienyl)[ 1,2 4]triazolo[4,3-a]quinolin- 1(2H)-one; 5-{[4-(2-hydroxyethyl)piperazin-1-ylJmethyl}-8-(3 -thienyl)[ 1,2,4]triazolo [4,3-a]quinolin- 1(2H)-one;

N° N°-dimethyl-N'-[ 1-oxo-8-(3-thienyl)-1,2-dihydro[ 1,2,4]triazolo[4,3-a] quinolin-5-y1]-beta- alaninamide; 5-{[(3R)-3-hydroxypyrrolidin-1-yljmethyl} -8-(3-thienyl)[1,2,4]triazolo[4,, 3-a}quinolin-1(2H)- one; 5-{[(3R)-3-hydroxypyxrolidin-1-yljmethyl}-8-(3-thienyl)[1 ,2,4]triazolo[4 , 3-a]quinolin-1(2H)- one; 5-{[(2,3-dihydroxypropyl)(methyl)amino]methyl}-8-(3 -thieny1)[1,2,4]tria=20lo[4,3-a]quinolin- 1(2H)-one; 5-({methyl[2-(methylamino)ethylJamino}methyl)-8-(3-thienyl)[1,2,4]tria=olo[4,3-a]quinolin- 1(2H)-one; 5-{[(3-methoxypropyl )amino}methyl}-8-(3-thienyl)[ 1,2,4]triazolo[4,3-a]qquinolin-1(2H)-one;

5-{[(2-hydroxyethyl)(methyl) amino]methyl}-8-(3-thieny})[1 ,2,A]triazolo[4,3-a] quinolin- 1(2H)-one; 5-{I(3 “hydroxypropyl)amino] mnethyl}-8-(3-thienyl)[1 ,2,A]triazolo[4,3-a]quinoli n-1(2H)-one;

N-[2-(dimethylamino)ethyl]-8 -{ 5-[(methylamino)methyl}-3-thienyl}-1-oxo-1,2 - dihydro[1,2,4]triazolo[4,3-ajquinoline-5 -carboxamide;

N-[2-(dimethylamino)ethyl]-8 -[3-(dimethylamino)prop-1-yn- 1-yl]-1-0x0-1,2- dihydro[1,2,4]triazolo[4,3-a]quinoline-5-carboxamide; 5-{[[3-(dimethylamino)propy1)(methyl)amino]methyl} -8-(3-thienyl){ 1,2 ,4]tria=zolo[4,3- a]quinolin-1(2H)-one; 5-({[3-(dimethylamino)propy1]amino }methyl)-8-(3 -thienyl)[1,2,4]triazolo[4,3—a]quinolin- 1(2H)-one;

N-[2-(dimethylamino)ethyl]- 1-oxo0-8-[4-(piperazin-1 -ylmethyl)phenyl]-1,2- dihydro[1,2,4]triazolo[4,3-a] quinoline-5-carboxamide; 5-(aminomethyl)-8-(1H-pyrrol-2-y1)[1,2,4]triazolo[4,3-a]quinolin- 1 (2H)-one; [1-oxo0-8-(3-thienyl)-1,2-dihydro[1,2,4]triazolof4,3 -ajquinolin-5-yljmethyl N- methylglycinate; 5-{[(3-methoxypropyl)aminoJmethyl}-8-{5 -[(methylamino)methyl]-3- thienyl}[1,2,4]triazolo[4,3-a] quinolin-1(2H)-one; 5-{[(2-hydroxyethyl)(methyl)aminojmethyl}-8-{5 -[(methylamino)methyl]-3- thienyl}[1,2,4]triazolo[4,3-a] quinolin-1(2ZH)-one; 5-{[4-(2-hydroxyethyl)piperazin-1-yljmethyl}-8-(1H-pyrrol-2-yl)[1 ,2,4]triazo1o[4,3- ajquinolin-1(2H)-one; 5-{[(2,3-dihydroxypropyl)}(methyl)amino]methyl}-8-{5- [(methylamino)methy~1]-3- thienyl}[1,2,4]triazolo[4,3-a] quinolin-1(2H)-one; 5-{[(3R)-3-hydroxypyrrolidin-1-yl]carbonyl}-8-(3-thienyl){1 ,2,4]triazolo[4,3—a]quinolin- 1(2H)-one; 1-oxo-8-(3-thienyl)-1,2-dihydro[1,2,4]triazolo[4,3-a]quinoline-5-carboxylic acid; 8- { 5-[(methylamino)methyl}-3-thienyl}-5-({methyl[2- (methylamino)ethylJamino} xnethyl)[ 1,2,4]triazolo[4,3-a]quinolin-1 (2H)-one; 5-{[[3-(dimethylamino)prop yi](methyl)amino]methyl}-8- {5-[(methylamino)methyl]-3- thienyl }[1,2,4]triazolo[4,3-aJquinolin-1(2H)-one; 5-{[(3-hydroxypropyl)amino]methyl}-8-{5-[(methylamino)methyl]-3- thienyl}{1,2,4]triazolo[4,3-a ]Jquinolin-1(2H)-one;

5({[3-(dimethylamino)propyljamino }methyl)-8-{5 -[(methylamino)methyl]-3- thienyl}[1,2,4]triazolo[4,3-a] quinolin-1(2H)-one; 5-methyl-8-[3-(piperazin-1 -ylmethyl)phenyl][1 ,2,4]triazolo[4,3-a] quinolin-1(2H)-orme;

N-[2-(dimethylamino)ethyl]-8-{ 5-[(4-methylpiperazin- 1-yl)methyl]-2-thienyl}-1-0X_o- 1,2- dihydro[1,2,4]triazolo [4,3-a]quinoline-5-carboxamide; 5-{[(3R)-3-hydroxypyrrolidin-1 -yl]carbonyl}-8-{ 5-[(methylamino)methyl}-3- thienyl}[1 2, 4ltriazolo[4,3-a]quinolin-1(2H)-one; 5-[(methylamino)methyl]}-8-(3 -thienyl)(1,2,4]triazolo(4,3 -a]quinolin-1(2H)-one; 5-({[2-(methylamino)ethylJamino }methy!)-8-(3-thienyl){1 2 A]triazolo[4,3-a]quinoXin-1(2H)- one; 5-methyl-8-(5-{[(3S)-pyrrolidin-3 -ylamino]methyl}-2-thienyl)[1 ,2,4]triazolo[4,3-a Jquinolin- 1(2H)-one; 5-methyl-8-(5-{ [(3R)-pyrrolidin-3-ylamino]methyl} -2-thienyl)[1,2,4]triazolo[4,3-aa]quinolin- 1(2H)-one;

N-azetidin-3-yl-1-ox0-8-(3-thienyl)-1,2-dihydro{1 ,2 Atriazolo[4,3-a]quinoline-5- carboxamide; 8-{5-[(azetidin-3-ylamino)methyl] -2-thienyl}-5-methyl{1 ,2,4]triazolo[4,3-alquino Yin-1(2H)- one; 5-§ [2-(dimethylamino)ethoxy]methyl} -8-(3-thienyl){1 ,2,4]triazolo[4,3-a]quinolin—1(2H)-one; 5-({[(28)-2,3-dihydroxypropyl] amino} methyl)-8-(3-thienyl)[1 ,2,4]triazolo[4,3-a]qquinolin- 1(2H)-one; 5-{[(3S)-3-hydroxypyrrolidin-1 -yl]methyl}-8-(3-thienyl)[1 ,2,4]triazolo[4,3-a]quixolin- 1 (2H)- one; 5-{[(3 -amino-2-hydroxypropyl)amino]methyl}-8-(3 -thienyl)[1,2,4]triazolo[4,3-ak quinolin- 1(2H)-one; 5-{[(3R)-3-(dimethylamino)pyrrolidin- 1-ylJmethyl}-8-(3-thienyl)[ 1,2,4]triazolo[<4,3- a]quinolin-1(2H)-one; 5-{[(2-hydroxyethyl)amino]methyl}-8-(3 -thienyl)[1,2,4]triazolo[4,3-a]quinolin-1. (2H)-one; 5-(aminomethyl)-8-[4-(methoxymethyl)phenyl]l 1,2,4]triazolo[4,3-g]quinolin-1(2ZH)-one; N-(3-hydroxypropyl)-1-oxo-8-(3 -thienyl)-1,2-dihydro[1 ,2,4]triazolo{4,3-a]quino dine-5- carboxamide; 5-{[(3S)-3-hydroxypyrrolidin-1-yljmethyl}-8-(1 H-pyrrol-2-y1){1,2,4]triazolo[4,3-a]quinolin- 1(2H)-one;

5-{[(3S)-3-hydroxypyrrolidin-1 -y1] carbonyl}-8-(3-thienyl)[ 1 ,2.,4]triazok o[4,3-a]quinolin- 1(2H)-one; 5-({[2-(dimethylamino)ethyl] armino }methyl)-8 -(1H-pyrrol-2-y1)[1,2,4] #riazolo[4,3- a)quinolin-1(2H)-one; 8-{5-[(ethylamino)methyl]-3-thienyl} -5-methyl[1,2,4]triazolo[4,3-a] qu inolin-1 (2H)-one; 8-{5-[(isopropylamino)methyl§-3-thienyl} -5-methyl{1,2 4]triazolo[4,3—a]quinolin-1(2H)-one;

N-azetidin-3-yl-8-{ 5-[(methylamino)methyl}-3-thienyl}-1 -oxo-1,2-dih~ydro[1,2,4]triazolo{4,3- a]quinoline-5-carboxamide; 5-(1H-imidazol-1-ylmethyl)-8 —(1H-pyrrol-2-yl)[1 ,2,4]triazolo[4,3-alquuinolin-1(2H)-one; 5-(1H-imidazol-1-ylmethyl)-8 —(3-thienyD)[1 ,2,4}triazolo[4,3-a]quinolira-1(2H)-one; 5-{[(3-hydroxypropyl)amino]Jrmethyl}-8-(1 H-pyrrol-2-yl)[1,2,4]triazol ©[4,3-a]quinolin-1 (2H)- one; 5-[(pyrrolidin-3-ylamino)metinyl]-8-(3-thienyD[1 ,2,Altriazolo[4,3-a]quinolin-1(2H)-one; 5-{[(3R)-pyrrolidin-3-ylamino methyl} -8-(3-thienyl)[1 2 4]triazolo[4, 3-a]quinolin-1(2H)- one; 5-[(azetidin-3-ylamino)methyi]-8-(3-thienyl)[1 ,2,4]triazolo[4,3-a]quirmolin- 1(2ZH)-one; 5-{[(3S)-3-aminopyrrolidin-1-ylJmethyl}-8-(3 ~thienyl)[1,2,4]triazolo[ 4,3-alquinolin-1(2H)- one; 5-{[(3R)-3-aminopyrrolidin-1 -ylJmethy!}-8-(3 -thienyl)[ 1,2,4]triazolo [ 4,3-a]quinolin-1(2H)- one; 5-{[(3R)-3-(dimethylamino)p yrrolidin-1-yljmethyl}-8-(1 H-pyrrol-2-y#1)[ 1,2 ,4]triazolo[4,3- a]quinolin-1(2H)-one; 5-{[(2-hydroxyethyl)amino}methyl}-8-(1 H-pyrrol-2-y1)[1,2,4]triazolo[4,3-a]quinolin-1 (2H)- one; 5-[(3-aminoazetidin-1-yl)methyl]-8-(3 -thienyl)[1,2,4]triazolo[4,3-a]qwinolin-1(2H)-one; 5-({[2-(dimethylamino)ethyl J amino }methyl)-8-(3 -thieny1)[ 1,2,4]triaz= olo[4,3-a]quinolin- 1(2H)-one; 5-({[2-(1H-imidazol-4-yl)eth.ylJamino} methyl)-8-(3 -thieny1)[1,2,4]triazolo[4,3-a]quinolin- 1(2H)-one; 5-({[3-«(1H-imidazol-4-yDpropyl]amino }methyl)-8-(3-thienyl)[1,2,4] #xiazolo[4,3-a]quinolin- 1(2H)-one; 5-[(isopropylamino)methyl]-8-(3-thienyl)[ 1,2 4]triazolo [4,3-a]quinol 4n-1(2H)-one; 5-[(ethylamino)methyl]-8-(3 ~thienyl)[1,2,4]triazolo[4,3-a] quinolin-12H)-one;

5-[(cyclopropylamino)methyl}-8-(3 -thienyl){1,2,4]txiazolo[4,3-a] quinolin-1(2H)-one; 5-4 [(cyclopropylmethyl)amino]methyl} -8-(3-thienyl)[1,2 4]triazolo[4,3 -ajquinolin-1(2H)- one; 5-(4 [2-(dimethylamino)-1-methylethyl]amino }metthy1)-8-(3 -thienyl)[1,2,4]triazolo[4,3-

S a]quinolin-1(2H)-one;

N-[2-(dimethylamino)-1-methylethyl]-1-ox0-8-(3 ~thienyl)-1,2-dihydro[1,2,4]triazolo[4,3- a]quinoline-5-carboxamide; 5-{[methyl(2-pyridin-4-ylethyl)amino]methyl } -8-3-thienyl)[1 ,2,4]triazolo[4,3-a]quinolin~ 1(2H)-one; 5.[(3-aminoazetidin-1-yl)carbonyl]-8-(3-thienyl)[ 1,2, 4]triazolo[4,3-a]quinolin-1(2H)-one;

N-[2-(1H-imidazol-4-yl)ethyl]-1-oxo-8-(3-thienyl)-1 ,2-dihydrof[1,2,4]triazolo[4,3- a]quinoline-5-carboxamide;

N-[3-(1H-imidazol-4-yl)propyl]-1 -0x0-8-(3-thieny1)-1,2-dihydro[ 1,2,4]triazolo[4,3- a]quinoline-5-carboxamide; 5-({[2-(isopropylamino)cthyl]amino }methyl)-8-(3 -thienyl)(1,2,4]triazolo[4,3-a]quinolin- 1(2H)-one;

N-[2-(isopropylamino)ethyl]-1-ox0-8-(3-thienyl)~1,2-dihydro[ 1,2,4]triazolo{4,3-a]quinoline- 5-carboxamide;

N-[(1-ethylpyrrolidin-2-yl)methyl}-1-ox0-8-(3 -thienyl)-1,2-dihydro[1,2,4]triazolo[4,3- a]quinoline-5-carboxamide; 5~({[3-(dimethylamino)propyl] amino }methy1)-8—(1 H-pyrrol-2-yl)[1,2,4]triazolo[4,3- ajquinolin-1(2H)-one; 5-{[4-(hydroxymethyl)-1H-1 2,3-triazol-1-yljmesthyl}-8-(3-thienyl){1,2,4]triazolo[4,3- aJquinolin-1(2H)-one; 5-{[(pyridin-2-ylmethyl)amino)methyl}-8-(3-thiieny{1 ,2,4]triazolo[4,3-a]quinolin-1(2H)- one; 5-({[(5-methyl-2-furyl)methylJamino Ymethyl)-8-(3-thienyl)[1,2,4]triazolo [4,3-a]quinolin- 1(2H)-one; 5-{[(2-pyridin-2-ylethyl)amino}methyl}-8-(3-thuienyl)(1 ,2,4]triazolo[4,3-a]quinolin-1(2H)- one; 5-(methoxymethyl)-8-(3-thienyl){1,2,4]triazolof 4,3 -a]quinolin-1(2H)-one; 5-({[(5-methylpyrazin-2-yl)methylJamino}methyl)-8-(3-thienyl)[1,2,4]triazolo[4,3- a]quinolin-1(2H)-one;

5-({4-[(methylamino)methyl]-1H-1,2,3-triazol-1 ~yl}methy1)-8-(3-thienyl)[1,2,4]triazolo[4,3- ajquinolin-1 (2H)-one; 5-(aminomethyl)-8-(3-thienyl)[1 ,2,4)triazolo[4,3-a]quinolin-1 (2H)-one; 5-{[(2-aminoethyl)amino}methyl}-8-(3-thienyl)[1 ,2 4]triazolo[43-a]quinolin-1(2H)-one;

S-chloro-2F-[1,2,4]triazolo[4,3-c]quinolin-1-one;

4-(1-oxo-1,2-dihydro-[1 2 A]triazolo[4,3-0]quinolin-5-yl)-benzaldehyde; 3-methoxy—-2-(1-0x0-1,2-dihydro[1 ,2,4]triazolo{4,3 -a]quinolin-5-yl)benzaldehyde; 8-bromo-1-o0xo-1,2-dihydro -{1 2,4]-triazolo[4,3-a]quinoline-5-caroxylic acid; 8-bromo-1—oxo-1,2-dihydro-{1,2,4)-triazolo[4,3-a]quinoline-5 -caroxylic acid ethyl ester;

7-chloro-5-methyl-2H-[1,2,4]triazolo[4,3-c]quinolin-1-one; 4-(5-methyl-1-oxo-1,2-dihydro-[1,2,4] triazolo[4,3-0]quinolin-7-yl)-benzaldehyde; 2-methoxy-5-(5-methyl-1-o0x0-1,2-dihydro[ 1 ,2,4]triazolo[4,3-a]quinolin-7 -yD)benzaldehyde; 3-(7-methoxy-5-methyl-1-0xo-1 ,2-dihydro-[1,2,4]triazolo[4,3-0] quinolin-8-yl)-benzaldehyde; 2-methoxy-5-(7-methoxy-5-methyl-1-oxo-1 ,2-dihydrof{1 ,2,4]triazolo[4,3-a]quinolin-8-

yl)benzaldehyde; 2-(7-methoxy-5-methyl-1-oxo- 1,2-dihydro(1,2,4]triazolo [4,3-a]quinolin-8-yl)benzaldehyde; 8-bromo-5-bromomethyl[1,2[4]triazolo[4,3-a]quinolin-1(2H)-one;

8-bromo-S-hydroxymethyl[1,2[4]triazolo[4,3 -aJquinolin-1(2H)-one; 8-bromo- 1 -oxo-1,2-dihydro[1 2 4]triazolo[4,3-a]quinoline-4-carboxylic acid; 4-amino-8-bromof1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 8-bromo-S-phenyl[1 ,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 8-bromo- S-methoxymethy| 1,2,4]triazolo{4,3-a]quinolin- 1(2H)-one; 8-Bromo-5-(aminomethyl)[ 1,2,4]triazolo[4,3-2a]quinolin-1 (2H)-one; 5-(azidomnethyl)-8-bromo[1,2,4] triazolo[4,3-a]quinolin-1(2H)-one; 7-bromo- S-thien-2-yl[1,2,4]triazolo[4,3-2]quinolin-1 (2H)-one; ethyl 8-chloro-7-methoxy-1-oxo-1 ,2-dihydro[1,2,4]triazolo[4,3-a] quinoline-5-carboxylate; 8-chloro-7-methoxy-1-oxo-1,2-dihydro[1 ,2,4]triazolo[4,3-a]quinoline-5-carboxylic acid; 5-amino- 8-chloro-7-methoxy{ 1,2,4]triazolo[4,3-a]quinolin-1 (2H)-one; 8-chloro~5-(hydroxymethyl)-7-methoxy(1 ,2.4]triazolo[4,3-a] quinolin-1(2H)-one; 2-{3-[(1-oxo0-1,2-dihydro[} ,2,4]triazolo[4,3-a)quinolin-5-yl)oxylpropyl}- 1H-isoindole- 1,3(2H)-dione;

2-{3-[(8-chloro-5-methyl-1-0x0-1 ,2-dihydro[1 2 4]triazolo[4,3-a)quinolin-7-yl)oxy]lpropyl }- 1 H-isoindole-1,3(2H)-dione; 7-(3-aminopropoxy)-8—chloro-5-methyl[ 1 2,4]triazolof4,3-a]quinolin-1(2H)-one.

In a particular embodirment the present invention provides a compound as recited in any of the embodiments above, wherein one or more of the atoms is a radioisotope of the same element.

In a particular embodizment the present invention provides a compound as recited in any of the embodiments above for the use in treatment of cancer.

In a particular embodizment the present invention provides a compound as recited in any of the embodiments above for use in treatment of neoplastic disease such as carcinoma of the breast, ovary, lung, colon, prostate or other tissues, as well as leukemias and lymphomas, tumors of the central and peripheral nervous system, and other tumor types such as melanoma, fibrosarcoma and oste«sarcoma.

In a particular embodiment the present invention provides a compound as recited in any of the embodiments above for use in treatment of proliferative diseases including autoimmune, inflammatory, neurological, and cardiovascular diseases.

Ina particular embodiment the present invention provides a rmethod for treating a human or or animal by limiting cel 1 replication by administering to such human or animal an effective amount of a compoun.d as recited in any of the embodiments above or a pharmaceutically acceptable salt of said compound.

In a particular embodiment the present invention provides a rmethod for treating a human or animal suffering from. cancer by administering to such humam or animal an effective amount of a compound as recited in any of embodiments above or a pharmaceutically acceptable salt of said compound.

In a particular embodiment the present invention provides a ruethod for treating a human or animal suffering from neoplastic disease such as carcinoma Of the breast, ovary, lung, colon, prostate or other tissues, as well as leukemias and lymphomas, tumors of the central and peripheral nervous sy stem, and other tumor types such as melanoma, fibrosarcoma and osteosarcoma by administering to such human or animal an effective amount of a compound as recited in any of exmbodiments above or a pharmaceuticall y acceptable salt of said compound.

In a particular embod iment the present invention provides a xmethod for treating a human or animal suffering from proliferative diseases including autoinnmune, inflammatory, neurological, and cardiovascular diseases by administering to such human or animal an effective amount of a compound as recited in any of embodiments above or a pharmaceutically acceptable salt of said compound.

In a particular embodiment the present invention provides the use of a compound as recited in any of the embodiments above in the preparation of a medicamemt for the treatment of cancer.

In a particular embodiment the present invention provides the us. of a compound as recited in any one of the embodiments above in the preparation of a medicament for the treatment of neoplastic disease such as carcinoma of the breast, ovary, lung, colon, prostate or other tissues, as well as leukemias and lymphomas, tumors of the central and peripheral nervous system, and other: tumor types such as melanoma, fibrosarcoma and osteosarcoma.

In a particular embodiment the present invention provides the usse of a compound as recited in any of the embod iments above in the preparation of a medicament for the treatment of proliferative diseases including autoimmune, inflammatory, nevmrological, and cardiovascular diseases.

In a particular ennbodiment the present invention provides a proscess for preparing a compound of formula (I) as recited in any of the embodiments above or a pharmaceutically acceptable salt or an in vivo hydrolysable ester therof which process comp xises: x o . )

Oy pn ——— a INUE mnt Ae w a No ®) _SocwoMF Eo) NHNHOOOE SN RB(OH), x

Tefiux cl | Aa Microwave. joe! SCaneH counting JO! © ° | ) > , ©)

Diketene (32ml, 32g, 38 1mmol) was added to the suspension Of the appropriately substituted chloro aniline (317.25mmol) in toluene (300ml). The mixture ~was refluxed for 6hr, cooled down and let stand overnight. The precipitated solid was filtered off, washed with ether and dried under vacuum to yield the intermediate (A).

A mixture of the appropriately substituted chloro acetoacetanilide (199.6mmol) and concentrated sulfuric acid (830ml) were heated on an oil-bath zat 70-80°C for 0.5h and for 1.0h at 100°C. The mixture was cooled down and poured into cruashed ice. The precipitated solid was filtered off, and recrystallized from ethanol to obtain intexrmediate (B).

A mixture of the appropriately substituted 4-methyl-1E-quinolin-2-one (134.2mmol),

DMF (10ml) and thionyl chloride (300g) was heated at reflux For 3hr. The mixture was cooled to room temperature and the resultant solid filtered off, washed with acetone and dried under vacuum to give the intermediate dichloroquinoline (C).

To a suspension of the appropriately substituted dichloxo-4-methyl-quinoline (1.5mmol) and ethyl carbazate (173mg 1.66mmol) in 3.7mi of ethanol was added 6 drops of

HCI (4N in dioxane). The reaction mixture was subject to irradliation with microwave at 170°C for 20min. After cooling to room temperature the precipitated solid was filtered off, washed with methanol (3x10 ml) and dried under vacuum to give the desired triazolone (D).

To a 5 ml vial, the appropriately substitutes 5-methyl-2 H-[1,2,4]triazolo[4,3- a quinolin-1-omne (0.5mmol), boronic acid (0.6mmol), cesium carbonate (651mg, 2.0mmol), and tetrakis(trisphenylphosphine)palladium (40mg, 7mol%) w ere added in 4ml of dioxane:water (4:1). The reaction was subject to irradiation w ith microwave at 165°C for 20min. After cooling down, the lower layer was separated and. discarded, the upper layer was evaporated, the residue dissolved in the minimum amount of DMSO and filtered. The crude product was purified by HPLC.

Compounds of the present invention may be administexed orally, parenteral, buccal, vaginal, rectal, inhalation, insufflation, sublingually, intramuscularly, subcutaneously, topically, intranasally, intraperitoneally, intrathoracially, intra wenously, epidurally, intrathecally, intracerebroventricularly and by injection into tine joints.

The dosage will depend on the route of administration, the severity of the disease, age and weight of the patient and other factors normally considered by the attending physician, when determining the individual regimen and dosage level as the most appropriate for a particular patient.

An effective amount of a compound of the present invention for use in therapy of infection is an amount sufficient to symptomatically relieve ira a warm-blooded animal, particularly a human the symptoms of infection, to slow the progression of infection, or to reduce in patients with symptoms of infection the risk of gettimg worse.

For preparing pharmaceutical compositions from the compounds of this invention, inert, pharmaceutically acceptable carriers can be either solid or liquid. Solid form preparations include powders, tablets, dispersible granules, capsules, cachets, and suppositories.

A solid carrier can be one or more substances, which may also act as diluents, flavoring agents, solubilizers., lubricants, suspending agents, binders, or tablet disintegrating agents; it can also be an encapsulating material.

In powders, the carrier is a finely divided solid, which is in a mixture with the finely divided active component. In tablets, the active component is mixed with the carrier having the necessary binding propemties in suitable proportions and compacted in the shape and size desired.

For preparing suppository compositions, a low-melting wax such as a mixture of fatty acid glycerides and cocoa bitter is first melted and the active ingredient is dispersed therein by, for example, stirring. Tine molten homogeneous mixture is then poured into convenient sized molds and allowed to cool and solidify.

Suitable carriers inc ude magnesium carbonate, magnesium stearate, talc, lactose, sugar, pectin, dextrin, starch, tragacanth, methyl cellulose, sodium carboxymethyl cellulose, a low-melting wax, cocoa butter, and the like.

Some of the compounds of the present invention are capable of forming salts with various inorganic and organic acids and bases and such salts are also within the scope of this invention. Examples of such acid addition salts include acetate, adipate, ascorbate, benzoate, benzenesulfonate, bicarbomate, bisulfate, butyrate, camphorate, camphorsulfonate, choline, citrate, cyclohexyl sulfama-te, diethylenediamine, ethanesulfonate, furnarate, glutamate, glycolate, hemisulfate, 2-hydroxyethylsulfonate, heptanoate, hexanoate, hydrochloride, hydrobromide, hydroiodide, hydroxymaleate, lactate, malate, maleate , methanesulfonate, meglumine, 2-naphthalene sulfonate, nitrate, oxalate, pamoate, persulfate, phenylacetate, phosphate, diphosphate, pi crate, pivalate, propionate, quinate, salicylate, stearate, succinate, sulfamate, sulfanilate, sulfate, tartrate, tosylate (p-toluenesulfonate), trifluoroacetate, and undecanoate. Base salts include ammonium salts, alkali metal salts such as sodium, lithium and potassium salts, alkalime earth metal salts such as aluminum, calcium and magnesium salts, salts with organic ba ses such as dicyclohexylamine salts, N-me thyl-D-glucamine, and salts with amino acids such as arginine, lysine, ornithine, and so forth. Also, basic nitrogen- containing groups may be quaternized with such agents as: lower alkyl halides, such as methyl, ethyl, propyl, and butyl halides; dialkyl sulfates like dimethyl], diethyl, dibutyl; diamyl sulfates; long chaim halides such as decyl, lauryl, myristyl and stearyl halides; aralkyl halides like benzyl bromicle and others. Non-toxic physiologically-acceptable salts are preferred, although other salts are also useful, such as in isolating or purifying the product.

The salts may be formed by conventional means, such as by reacting the free basse form of the product with one or more equivalents of the appropriate acid in a solvent or medium in which the salt is insoluble, or in a solvemt such as water, which is removed i72 vacuo or by freeze drying or by exchanging the anions of an existing salt for another anion on asuitable ion-exchange resin.

In order to use a compound of the formula (I) or a pharmaceutically acceptable salt thereof for the therapeutic treatment (including prophylactic treatment) of mammals including humans, it is normally formulated in accordance with standard pharmaceutical practice asa pharmaceutical composition.

In addition to the compounds of the present invention, the pharmaceutical comp» osition of this invention may also contain, or be co-administered (simultaneously or sequentially) with, one or more pharmacological agents of value in treating one or more disease conditions referred to herein.

The term composition is intended to include the formulation of the active comp<nent or a pharmaceutically acceptable salt with a pharmaceutically acceptable carrier. For example this invention may be formulated by means known in the art into the form of, for example, tablets, capsules, aqueous or oily solutions, suspensions, emulsions, creams, ointments, gels, nasal sprays, suppositories, finely divided powders or aerosols or nebulisers for inhalation, and for parenteral use (including intravenous, intramuscular or infusion) sterile aqueous or oily solutions or suspensions or sterile emulsions.

Liquid form compositions include solution s, suspensions, and emulsions. Sterile water or water-propylene glycol solutions of the active compounds may be mentioned as an example of liquid preparations suitable for parenteral administration. Liquid compositi<ons can also be formulated in solution in aqueous polyethylene glycol solution. Aqueous solutk ons for oral administration can be prepared by dissolving the active component in water and adding suitable colorants, flavoring agents, stabilizers, anc thickening agents as desired. Aqueous suspensions for oral use can be made by dispersing the finely divided active componen tin water together with a viscous material such as natural synthetic gums, resins, methyl cellulose, sodium carboxymethyl cellulose, and other suspending agents known to the pharmaceutical formulation art.

The pharmaceutical compositions can be ira unit dosage form. In such form, the composition is divided into unit doses containing appropriate quantities of the active component. The unit dosage form can be a packaged preparation, the package containizg discrete quantities of the preparations, for exaxmple, packeted tablets, capsules, and powders in vials or ampoules. The unit dosage form can also be a capsule, cachet, or tablet itself, or it can be the appropriate number of any of these packaged forms.

Compounds of the present invention can be labeled with a radioisotope including but not limited to tritium. Such radiolabeled compounds can be useful in the discovery of targets, or novel medicinail compounds which bind to and modulate the activity, by agonism, partial agonism, or antagonism, of CHK1. Such labeled compounds may be used in assays that measure the displacement of such compounds to assess the binding of ligand that bind to

CHK receptors. Such radiolabeled compounds can be synthesized either by incorporating radiolabeled starting materials or, in the case of tritium, exchange of hydrogen for tritium by known methods. Known methods include (1) electrophilic halogenation, followed by reduction of the halogen in the presence of a tritium source, for example, by hydrogenation with tritium gas in the presence of a palladium catalyst, or (2) exchange of hydrogen for tritium performed in the presence of tritium gas and a suitable organometallic (e.g. palladium) catalyst.

The anti-cancer treatment defined hewein may be applied as a sole therapy ox may involve, in addition to the compound of the invention, conventional surgery or radiotherapy or chemotherapy. Such chemotherapy may inc lude one or more of the following categories of anti-tumour agents: (3d) antiproliferative/antineoplastic drugs and combinations thereof, as used in medical oncology, such as alkylating agents (for example cis-platin, carboplatin, cyclophosphamide, nitrogen mustard, melphalan, chlorambucil, busulphan and nitrosoureas); antimetabolites (for example antifolates such as fluoropyrimidin es like S-fluorouracil and tegafur, raltitrexed, methotrexate, cytosine arabinoside and hydroxyurea); antitumour antibiotics (for example anthracyclines like adriamycin, bleomycin, doxorubicin, daunomycin, epirubicin, idarubicin, mitomycin-C, dactinomycin and mithramycin); antimitotic agents (for example vinca alkaloids like vincristine, vinblastine, vinde sine and vinorelbine and taxoids like taxol and taxotere); and topoisomerase inhibitors (for example epipodophyllotoxins like etoposide and teniposide, amsacrine, topotecan and camptothecin); (i) cytostatic agents such as antioestrogens (for example tamoxifen, toremifene, raloxifene, droloxifene and iodoxyfene), oestrogen receptor down regulators (for example fulvestrant), antiandrogens (for example bicalutamide, flutamide, nilutamide and cyproterone acetate), LHRH antagonists or LHRH agonists (for example goserelin, leuprorelin and buserelin), progestogens (for example megestrol acetate), aromatase inhibitors (for example as anastrozole, letrozole, vorazole and exernestane) and inhibitors of So-reductase such as finasteride; (iii) agents which inhibit cancer cell invasion (for example metalloproteinase inhibitors like marimastat and inhibitors of urokinase plasminogen activator receptor function); (iv) inhibitors of growth factor function, for example such inhibitors include growth factor antibodies, growth factor receptor antibodies (for example the anti-erbb2 antibody trastuzumab [Herceptin™] and the anti-erbbl antibody cetuximab {C225]) , farnesyl transferase inhibitors, tyrosine kinase inhibitors and serine/threonine kinase inhibitors, for example inhibitors of the epidermal growth factor family (for example EGFR family tyrosine kinase inhibitors such as N-(3-chloro-4-fluorophenyl)-7-methoxy-6-(3- morpholinopropoxy)quinazolin-4-amine, IN-(3-ethynylphenyl)-6,7-bis(2- methoxyethoxy)quinazolin-4-amine (erlotinib, OSI-774) and 6-acrylamido-N-(3-chloro-4- fluorophenyl)-7-(3-morpholinopropoxy)quinazolin-4-amine (CI 1033), for example inhibitoxs of the platelet-derived growth factor family and for example inhibitors of the hepatocyte growth factor family; \2) antiangiogenic agents such as those which inhibit the effects of vascular endothelial growth factor, (for example the anti-vascular endothelial cell growth factor antibody bevacizumab [Avastin™], compounds such as those disclosed in International Patent

Applications WO 97/22596, WO 97/3003 5, WO 97/32856 and WO 98/13354) and compounds that work by other mechanisms (for example linomide, inhibitors of integrin owvP3 function and angiostatin); (vi) vascular damaging agents such as Combretastatin A4 and compounds disclosed in

International Patent Applications WO 99/02166, WO 00/40529, WO 00/41669, WO 01/92224, WO 02/04434 and WO 02/082 13, (vii) antisense therapies, for example those which are directed to the targets listed above, such as ISIS 2503, an anti-ras antisense; (viii) gene therapy approaches, including for example approaches to replace aberrant genes such as aberrant p53 or aberrant BRCA1 or BRCA2, GDEPT (gene-directed enzyme pro-drug therapy) approaches such as those using cytosine deaminase, thymidine kinase or a bacterial nitroreductase enzyme and approaches to increase patient tolerance to chemotherapy or radiotherapy such as multi-drug resistance gene therapy; and

(ix) immunotherapy approaches, including for example ex—vivo and in-vivo approaches to increase the immunogenicity of patient tumour cells, such as transfection with cytokines such as interleukin 2, interleukin 4 or granulocyte-macrophage colony stimulating factor, approaches to decrease T-cell anergy, approaches using transfected immune cells such as cytokine-transfected dendritic cells, approaches using cytokine-transfected tumour cell lines and approaches using anti-idiotypic antibodies.

Such conjoint treatment may be achieved by way of the simultaneous, sequential or separate dosing of the individual components of the treatment. Such combination products employ the compounds of this invention within the dosage range described hereinbefore and the other pharmaceutically-active agent within its approvesd dosage range.

Synthesis "The compounds of the present invention can be prepared in a number of ways well known to one skilled in the art of organic synthesis. The compounds of the present invention can be synthesized using the methods described below, to gether with synthetic methods known in the art of synthetic organic chemistry, or variations thereon as appreciated by those skilled in the art. Such methods include, but are not limited to, those described below. All references cited herein are hereby incorporated in their entirety by reference.

The novel compounds of this invention may be prepared using the reactions and techniques described herein. The reactions are performed in solvents appropriate to the reagents and materials employed and are suitable for the transformations being effected. Also, in the description of the synthetic methods described below, it is to be understood that all proposed reaction conditions, including choice of solvent, reaction atmosphere, reaction temperature, duration of the experiment and workup procedures, are chosen to be the conditions standard for that reaction, which should be readily recognized by one skilled in the art. It is understood by one skilled in the art of organic symthesis that the functionality present on various portions of the molecule must be compatible with the reagents and reactions proposed. Such restrictions to the substituents, which are mot compatible with the reaction conditions, will be readily apparent to one skilled in the axt and alternate methods must then be used.

The starting materials for the Examples contained herein are either commercially available or are readily prepared by standard methods fromm known materials. For example the following reactions are illustrations but not limitations of” the preparation of some of the startinge materials and examples used herein.

A general process for making the compounds of the inventi«on is as follows:

IL + Jug totusne 20 F conHSO, (2) a NH, Trt AI —_— . iS ®) _SockoMF ET NHNHCOOE! 00) RBOH), ron Pg Men of p Som contng 0, © ig ) > d . © Diketene (32ml, 32g, 381mmol) was added to a suspensior of the appropriately substituted chloro aniline (317.25mmol) in toluene (300ml). The mixtwre was refluxed for 6hr, cooled down and let stand overnight. The precipitated solid was filtered off, washed with ether and dried under vacuum to yield the intermediate (A).

A mixture of the appropriately substituted chloro acetoacetanilide (199.6mmol) amd concentrated sulfuric acid (80ml) were heated on an oil-baath at 70-80°C for 0.5h and for 1.<0h at 100°C. The mixture was cooled down and poured into crushed ice. The precipitated solid was filtered off, and recrystallized from ethanol to obtain fintermediate (B).

A mixture of the appropriately substituted 4-metlmyl-1H-quinolin-2-one (134.2mmos]),

DMF (10m) and thionyl chloride (300g) was heated at reflux for 3hr. The mixture was cool ed to room temperature and the resultant solid filtered off, washed with acetone and dried uncler vacuum to give the intermediate dichloroquinoline (C).

To a suspension of the appropriately substituted di. chloro-4-methyl-quinoline (1.5mmol) and ethyl carbazate (173mg 1.66mmol) in 3.7ral of ethanol was added 6 drops o&

HCI (4N in dioxane). The reaction mixture was subject to irradiation with microwave at 170°C for 20min. After cooling to room temperature the precipitated solid was filtered off, washed with methanol (3x10 ml) and dried under vacuunra to give the desired triazolone (D)».

To a 5 ml vial, the appropriately substituted 5-methyl-2H-[1,2,4]triazolo[4-,3- oJquinolin-1-one (0.5mmol), boronic acid (0.6mmol), cesium carbonate (651mg, 2.0mmaol), and tetrakis(trisphenylphosphine)palladium (40mg, Zmol%) were added in 4ml of dioxane:water (4:1). The reaction was subject to microvwave irradiation at 165°C for 20min.

After cooling to room temperature, the lower layer was separated and discarded, the upper

-53 ~ layer was evaporated, the residue dissolved in the minimum amount of DMSO and filtered.

The crude product was purified by HPLC.

Examples:

Examples 1-30

A general procedure for preparation of 5-substituted-2H-[1,2,4]triazolo[4,3- o]jquinolin-1-ones:

To a Sml reaction vial, 5-chloro-2H-[1 ,2,4]triazolo[4,3-0]quinolin-1-one (110 mg, 0.5rmmol), the appropriate boronic acids (of general fomula, RB(OH),) (0.6mmol), cesium carbonate (651mg, 2.0mmol), and tetrakis(trisphenylphosphine)palladium(0) (40mg, Tmol%) were added followed by dioxane:water 4:1 (4m). The reaction mixture was heated with stirring in a microwave synthesizer for 1200 seconds at 165°C. After cooling to ambient temperature, the lower aqueous layer was removed by pipette and discarded. The upper layer was collected and concentrated. The residual solid was dissolved in the minimum amourat of

DMSO (2-4 mL) followed by filtration. The crude product was purified by chroamatography to afford the title compounds.

R

C0) oo o” H

Be] ® [mem@wmovsod : 9.08 (d, 1H), 11.50 (s, 1H), 12.55 (5, 1H) “0” oH 12.42 (s, 1H) © J=7.6Hz, 1H), 12.55 (s, 1 H)

34 2.06 (s, 3H), 7.02-7.75 (m, 8H), 9.08 Cd, 1H), 10.14 (s, 1H), 12.60

Oem 7.15-7.85 (m, 13H), 9.15 (d, 1H), 12.64 (5, 1H)

Co | 3.82 (s, 3H), 7.04-7.70 (im, 8H), 9.10 (d, 1H), 12.60 (s, 1H) ae 2.37 (s, 3H), 7.00-7.63 (m, 8H), 9.02 (d, J=7.6Hz, 1H), 12.65 (5, 1H)

Or 7.25-8.05 (m, 11H), 9.10 (4, 1H), 12. 80 (s, 1H) oo 7.10-7.85 (m, 12H), 9.05 (d, 1H), 12.75 (s, 1H) 7.22-8.27 (mm, 10H), 9.05 (d, 1H), 1255 (s, 1H)

Cor 7.25-7.95 (m, 8H), 9.18 (d, 1H), 12.82 (s, 1H) 14 "2 4.15 (s, 2H), 7.10-7.75 (m, 8H), 8.20 (s, 2H), 9.10 (d, 1H), 12.65 (s, 1H) a 4.20 (s, 2H), 6.75-1.75 (m, 8H), 8.25 (s, 2H), 9.10 (d, 1H), 12.70 (s, 1H) eo] Or | 2.99 (s, 6H), 6.90-7.70 (m, 8H), 9.10 (d, 1H), 12.60 (s, 1H)

NEES 6.96-7.68 (m, 8H), 9.05 (d, J=7.6Hz, 1H), 12.61 (s, 1H) iH, 18 ava 4.65 (s, 2H), 5.35 (t, 1H), 6.90-8.35 (m, 8H), 9.05 (d, 1H), 12.60 (s, 1H) 7.25-8.00 (m, 9H), 9.00 (d, 1H), 12.65 (5, 1H) 3 OQ 6.96-7.43 (m, 8H), 8.90 (d, 1H), 12. 50 (s, 1H) a

HE=S 7.14-7.81 (m, 8H), 9.03 (d, J=7.6Hz, 1H), 12.61 (s, 1H) 4.47 (s, 2H), 6.89-7.56 (m, 8H), 8.93 (d, J=7.6Hz, 1H), 12.46 (s, 1H)

6.12 (s, 2H), 6.91-7.70 (m, 7H), 9.05 (d, 1H), 12.59 (s, 1H) 0 24 N Pp 3.68 (s, 3H), 3.85 (s, 3H), 6.70-7.65 (m, 7TH), 9.00 (d, 1 H), 12.58 ° at (s, 1H) 25 7.25-7.65 (m, 9H), 8.05 (d, J=8.0Hz, 1H), 8.85 (d, 1H), 12.35 (s,

Oy (m, 9H) (d, H) ( ) ( 1H)

HE: 7.10-8.05 (m, 8H), 9.08 (d, 1H), 16.50 (s, 1H) 7.15-8.10 (m, 8H), 9.05 (d, 1H), 10.15 (s, 1H), 12.70 (s, 1H) 28 0 6.80-8.20 (m, 7H), 9.10 (4, 1H), 12.65 (s, 1 7.05-7.75 (m, 9H), 9.12 (d, 1H), 12.70 (s, 1H) 30 fod 4.02 (s, 3H), 7.09-7.83 (m, 7H), 9.06 (d, I=7.6Hz, 1H), 10.43 (s,

H S 1H), 12.60 (s, 1H)

Examples 31-66

A general procedure for preparation of 5-(4’-substituted aminomethylemephenyl)-2H- [1,2,4]triazolo{4,3-ct]quinolin-1-ones: [o] 74 NR

RNH, NaCNBH, ierowae o H i. N

To a suspension of 4-(1-oxo0-1,2-dihydro-[1,2,4]triazolo[4,3-0¢]quinolin-S-yl)- benzaldehyde (0.5mmol) in DMF (4ml), the appropriate amine (Immol) was added. The mixture was stirred overnight at room temperature. To the reaction mixture was added

NaCNBHj; (63mg, lmmol) and 2 drops of AcOH. The reaction mixture was sealed, stirred and heated under microwave conditions for 5 minutes at 150°C. After cooling to ambient temperature, the reaction mixture was quenched with water (1 mL). The cruade product was isolated and purified by chroamatography.

31 2.05 (m, 2H), 2.80 (s, 6H), 3.05-3.25 (m, 4H), 4.32

AA (s, 2H), 7.06-7.75 (m, BH), 9.10 (m, 2H), 12.65 (s, 1H) 32 ~~ 2.10 (m, 2H), 3.05-3.20 (m, 12H), 4.25 (s, 2H), — 7.05-7.70 (m, 8H), 9.05 (d, 1H), 9.15 (s, br, 1H), 12.70 (s, 1H) 33 SUA 3.22-3.26 (t, J=15 2Hz, 7.6Hz, 2H), 3.42-3.44 (d, ¥ Mm J=7.2Hz, 2H), 4.35 (s, 2H), 7.06-7.96 (m, 11H), 8.61-8.62 (d, J=4.4Hz, 1H), 9.06-9.19 (s, d, 2H), 12.64 (s, 1H) 34 HO ~~ 3.05 (m, 2H), 3.70 (m., 2H), 4.30 (s, 2H), 5.30 (s, br, 1H), 7.10-7.70 (m, 8H), 8.90 (s, br, 1H), 9.10 (d, 1H), 12.60 (s, 1H)

IVY 2.81 (s, 3H), 3.17 (m, 8H), 3.83 (s, 2H), 7.03-7.78

C19 ete meen 36 O, 1.75-2.30 (m, 6H), 3.778 (m, 3H), 4.45 (m, 1H), 4.70 (m, 1H), 5.60 (s, 1H), 7.08-7.78 (m, 8H), 9.10 (d, 1H), 12.65 (s, 1H) 37 0.97 (dd, J=6.8Hz, 6E), 2.20 (m, 1H), 3.05 (m, wo L, 1H), 4.20-4.50 (m, 4K), 5.45 (s, 1H), 7.10-7.80 (m, 8H), 8.90 (s, br, 1H), 9.15 (d, 1H), 12.65 (s, 1H) 38 5 3.10 (m, 8H), 4.05 (s, 2H), 7.10-7.70 (m, 12H),

Bo rem 39 ae 1.91 (m, 2H), 3.02 (m0, 2H), 4.26 (s, 2H), 4.32 (m, 2H), 7.03-7.77 (m, 10H), 9.04-9.23 (m, 3H), 12.65

CTT feet 40 or 1.30 (¢, 3H), 2.50 (s, 2H), 3.02 (s, 2H), 4.40 (s, 2H), 7.67-8.00 (m, 10H), 8.75 (m, 2H), 9.10 (d, 1H), 12.70 (s, 1H)

41 1.80-2.20 (m, 4H), 2.25 (m, 2H), 2.95 (m, 2H),

Ln 3.30 (m, 2H), 3.35 (m, 2H), 4.25 (s, 2H), 7.05-7.75 (m, 8H), 8.85 (5, br, 1H), 9.10 (d, 1H), 12.65 (s, 1H) 42 a 4.40 (s, 2H), 6.30-7.70 (m, 16H), 9.10 (d, 1H),

ToD dem 43 N —- 2.51 (s, 3H), 2.85 (m, 4H), 3.14 (m, 4H), 4.39 (s, 2H), 6.77-1.02 (m, 5H), 7.38-7.68 (m, 7H), 9.06 (d,

J=7.6Hz, 1H), 9.67 (s, br, 1H), 12.60 (s, 1H) 44 Ol. | 2.86 (s, 3H), 3.31 (m, 4H), 4.52 (s, 2H), 7.09-7.86 (m, 11H), 8.56 (d, J=4.8Hz, 1H), 9.08 (d, J=8Hz, 1H), 12.64 (s, 1H) 45 Om 4.27 (s, 2H), 4.31 (s, 2H), 6.65-6.75 (m, 2H), 7.05- 7.85 (m, 9H), 9.05 (d, 1H), 9.50 (s, br, 1H), 12.65 (s, 1H) 46 ne 4.13 (s, 2H), 4.26 (s, 2H), 6.67 (s, 1H), 7.05 (s, ( 1H), 7.43-7.85 (m, 9H), 9.05 (d, 1H), 9.30 (s, br, 1H), 12.65 (s, 1H) 47 J | au 2.73 (s, 6H), 2.80 (m, 2H), 3.20 (m, 2H), 3.88 (s, ° 2H), 4.29 (s, 2H), 4.35 (s, 2H), 6.40 (s, 1H), 6.65 (s, 1HD), 7.05 (s, 1H), 7.61-7.67 (m, 7H), 9.10-9.25 (m, 2H), 12.65 (s, 1H) 48 Cr 3.20 (t, J=8.6Hz, 1H), 4.16 (s, 2H), 4.26 (s, 2H),

NH 4.57 (t, J=8.6Hz, 2H), 6.83-7.67 (m, 12H), 9.07 (d,

J=8.4Hz, 1H), 9.30 (s, br, 1H), 12.64 (s, 1H) 49 0 3.64 (s, 3H), 4.25 (s, 2H), 4.31 (s, 2H), 6.04 (s, 1H), 6.30 (s, 1H), 6.84 (s, 1H), 7.06 (s, 1H), 7.43- 7.69 (m, 7H), 9.10 (d, 1H), 9.30 (s, br, 1H), 12.64 (s, 1H) 50 OA) UNH | 2.70-3.30 (m, 16H), 4.29 (s, 2H), 4.33 (s, 2H), 7.06-7.70 (m, 13H), 8.90 (s, br, 1H), 9.07 (d,

J=8.8Hz, 1H), 12.66 (s, 1H)

1H), 9.10 (d, 1H), 9.55 (s, br, 1H), 12.65 (s, 1H)

OC

(m, 12H), 9.05 (d, J=8Hz, 1H), 12.61 (s, 1H) 7.07-7.68 (m, 8H), 9.10 (d, 1H), 12.66 Cs, 1H) 54 SREY 1.36-1.91 (m, 7H), 2.99-3.35 (m, 6H), 4.39 (s, 2H), 7.08-7.71 (m, 8H), 9.07 (d, J=8.4Hz, 1HT), 12.66 (s,

HEE: =n 12H), 9.06 (d, 1H), 12.65 (s, 1H) 56 VN 2.90-3.35 (m, 8H), 4.44 (s, 2H), 7.07-7. 68 (m, 8H),

CU] NO [eemmermem naam 57 3) 1.76 (m, 2H), 1.96 (m, 2H), 2.38 (m, 1 EJ), 2.90- we 3.35 (m, 4H), 4.40 (s, 2H), 6.96 & 7.08 (s,s, 2H), 7.42-7.69 (m, 8H), 9.07 (d, J=8.4Hz, 1E1), 12.64 (s, 1H) 58 RaW 139 (m, 2H), 1.85-1.95 (m, 3H), 2.73-333 (m, 6H), 4.27-4.39 (d, J=48.8Hz, 2H), 7.06—7.87 (m, 9H), 8.99 (s, br, 1H), 9.08 (d, J=8.4Hz, 1H), 12.65 (s, 1H) 59 Os 1.90 (m, 2H), 2.65 (m, 2H), 2.78 (m, 2EJ), 3.71 (5, — WL 2H), 3.78-3.90 (m, 4H), 6.99-7.68 (m, OH), 8.68

OH mma

Oe 2.18 (m, 2H), 3.30-3.75 (m, 12H), 4.40 (s, 2H), — 7.06-7.95 (m, 8H), 9.07 (d, J=8.4Hz, 1¥J), 12.64 (s, 1H)

OF [nme

OL 7.08-7.72 (m, 8H), 8.17 (s, 1H), 8.50 (s, 1H), 9.07 (d, J=8.0Hz, 1H), 12.65 (s, 1H)

62 0.9 1.15-4.47 (m, 10H), 4.60 (s, 2H), 6.94-8.46 (m, rN 0) - =) 11H), 9.08 (d, I=7.6 Hz, 1H), 12.64 (s, 1H) 63 H 135-2.05 (m, 8H), 3.57 (m, 1H), 4.61 (5, 2H), r he 7.10-7.71 (m, 8H), 8.94 (s, br, 1H), 8.09 (d, J = 8.4Hz, 1H), 12.63 (ss, LH).

Or I” 1.61-2.08 (m, 4H), 2.97 (m, 1H), 3.13 (m, 1H),

J HN 3.72-3.87 (m, 2H), <1.15 (m, 1H), 4.28 (s, 2H), 7.08-7.63 (m, 8H), ©.07 (m, 2H), 12.62 (s, 1H). 65 oH 1.13 (d, J = 6.4Hz, 3H), 2.73 (m, 2H), 3.98 (m,

AN 1H), 4.27 (s, 2H), 7 -06-7.70 (m, 8H), 8.92 (s, br, 1H), 9.08 (d, J = 8.4Hz, 1H), 12.63 (s, 1H). ] or 1.46 (m, 11H), 2.12 (m, 2H), 2.81 (m, 2H), 3.35 5d (m, 1H), 4.05 (m, 27H), 4.30 (s, 2H), 7.02-7.96 (m, 8H), 8.96 (s, br, 1H), 9.08 (d, J = 8.4Hz, 1H), 12.63 (s, 1H).

Examples 66-73

The following examples were prepared by the procedure described for examples 31-62 using 3-methoxy-2-(1-oxo-1,2-dihydro[1,2,4]triazolo[4,3-a]lquinolin-5-yl)benz aldehyde (prepared as described for example 27) and the appropriate amine.

Cd = oy &N

I 2.00 (m, 2H), 2.78 (s, s, 6H), 3.00 (m, 2H), 3.10 il dd (m, 2H), 3.73 (s, 3H), 4.18 (s, 2H), 7.10-7.70 (m,

TH), 8.90 (s, br, 1H), 9.10 (d, 1H), 12.65 (s, 1H) 67 [3 1.70-2.20 (m, 4H), 3.20 (m, 2H), 3.58 (zm, 3H),

N OH 3.73 (s, 3H), 4.28 (m, 1H), 4.55 (m, 1H), 7.05-7.68 r mente hn 2.78 (s, 3H), 3.25-3.70 (m, 8H), 3.73 (s. 3H), 3.91 (s, 2H), 7.02-7.63 (m, 7H), 9.01 (d, J=8 .4Hz, 1H),

NEE 12.62, 1H) > 3.17 (m, 2H), 3.35 (m, 2H), 3.72 (5, 3H), 4.24 (s,

N NH 2H), 7.00-7.88 (m, 10H), 8.55 (d, J=4.8 Hz, 1H),

Or memes 70 5 3.73 (s, 3H), 4.06 (s, 2H), 4.17 (s, 2H), 6.63-7.82 » (m, 10H), 9.01 (d, J=8.4Hz, 1H), 9.09 (ss, br, 1H), 12.60 (s, 1H) 71 _ l ADs 2.75 (s, 6H), 3.20 (m, 4H), 3.72 (s, 3H), 3.86 (5, 2H), 4.19 (s, 2H), 4.33 (s, 2H), 6.40-7.64 (m, 9H), 9.02 (s, d, J=7.6Hz, 2H), 12.63 (s, 1H) 72 220 as 2.65 (m, 2H), 3.10 (m, 2H), 3.75 (s, 3H), 4.19 (5, 2H), 4.30 (s, 2H), 7.01-7.65 (m, 12H), 9.02 (5, br, 1H), 9.03 (d, J=8.4Hz, 1H), 12.63 (s, 1H)

73 WAR 3.12 (m, 4H), 3.48 (m, 4H), 3.70 (s, 3H), 4.40 (s,

QO 2H), 6.75-8.17 (m, 11H), 9.03 (d, }=8.0Hz, 1H), 12.61 (s, 1H)

Examples 74-82

The following examples were prepared by the procedure described for examples 3 1-62 using the appropriate aldehyde (example 30) and amine. $ aS

H

74 | 2.10 (m, 2H), 2.80 (s, 6H), 3.05 (m, 4H), 3.95 (s,

AA 3H), 4.23 (s, 2H), 7.03-7.75 (m, TH), 8. 85 (s, br, 1H), 9.10 (d, 1H), 12.62 (s, 1H) 75 Cl. 3.18 (m, 2H), 3.43 (m, 2H), 3.96 (s, 3H), 4.30 (s,

N NH 2H), 7.03-7.86 (m, 10H), 8.57 (s, 1H), 9.00 (s, br, oC 1H), 9.07 (d, J=8.0Hz, 1H), 12.62 (s, 11H) 76 X 1.00 (4, 6H), 2.12 (m, 1H), 3.00-3.25 (xm, 3H),

HO Sn 3.94 (s, 3H), 4.30 (s, 2H), 7.02-7.70 (mm, 7H), 8.50 (s, br, 1H), 9.07 (d, ]=8.4Hz, 1H), 12.62 (s, 1H) 77 J 2.79 (s, 3H), 3.00-3.30 (m, 8H), 3.85 (s, 2H), 3.89 hd (s, 3H), 7.05-7.75 (m, 7H), 9.10 (d, 1HD), 12.65n (s, 7 [Sheena 78 [3 1.70-2.20 (m, 4H), 3.63-3.74 (m, SH), 3.95 (5, 3H),

N OH 4.30 (m, 1H), 4.61 (m, 1H), 7.09-7.70 «m, 7H), oC 9.07 (d, J=8.4Hz, 1H), 12.62 (s, 1H) 79 od 3.95 (s, 3H), 4.11 (d, J=5.2Hz, 2H), 4.15 (4, ( J=.6Hz, 2H), 6.67-7.95 (m, 10H), 9.04 (s, br, 1H), 9.07 (d, 1=8.0Hz, 1H), 12.60 (s, 1H)

2.78 (s, 6H), 2.80 (m, 2H), 3.20 (m, 2H), 3.87 (s,

AY |Z RE ED ° 2H), 3.99 (s, 3H), 4.24 (s, 2H), 4.34 (s, 2H), 6.41- 7.70 (m, 9H), 8.97 (s, br, 1H), 9.08 (d, J=8.0Hz, 1H), 12.61 (5, 1H) 81 CH S\N 2.25-2.65 (m, 14H), 3.81 (s, 2H), 3.91 (s, 3H), — 6.96-7.95 (m, 12H), 9.05 (d, J=8.0Hz, 1H), 12.65 (s, 1H) 82 0) 3.45 (m, 8H), 3.59 (s, 2H), 3.85 (s, 3H), 6.59-8.08

N

=N (m, 11H), 9.04 (d, J=8.4Hz, 1H), 12.65 (s, IH)

Example 83 of

ND

Jd Hi

To the methoxy compound prepared in Example 8, (29.1mg, 0.lmmol) was added

BBr; (IM in CHCl, 3ml). The mixture was stirred at room temperature for 3 hours and quenched with crushed ice. The precipitate was collected by filtration to afford the crude product. The crude product was dissolved in the minimum amount of DMSO (2-4 mL) and purified by chromatography to give the desired compound. 'H NMR (400MHz, DMS Q-d6): 6.85-7.67 (m, 8H), 9.05 (d, J=7.6Hz, 1H), 9.73 (s, 1H, OH), 12.57 (s, 1H)

Examples 84-90

The following examples were prepared by demethylation of the corresponding methoxy analogue using the procedure described in Example 80.

R ge! pS dR

BHR Go Duo 84 a 6.30-7.75 (m, 7H), 9.00 (d, 1H), 9.50-9.75 (s, s, 2H),

HO

Ch 12.50 (s, 1H)

85 7.18-8.22 (m, 7H), 9.10 (d, 1H), 9.88 (s, 1H), 10.75 (s, 1H), 12.65 (5, 1H)

OR

3, 1.82-2.15 (m, 4H), 3.30-3.90 (m, 5H), 4.30 (m, 1H), 4.58

Sor (m, 1H), 5.50 (s, br, 1H), 7.05-7.69 (m1, 7H), 9.07 (4, " J=8.0Hz, 1H), 10.47 (s, 1H), 12.59 (s, 1H) 87 A 0.95 (d, J=6.8Hz, 3H), 1.01 (d, J=6.8Fz, 3H), 2.16 q. or J=6.8Hz, 1H), 3.77-4.12 (m, 3H), 4.28 (s, 2H), 5.38 (s, * 1H), 6.99-7.70 (m, 7H), 9.07 (d, J=8.4Hz, 1H), 10.77 (s, 1H), 12.59 (s, 1H) 88 {O—, 1.79-2.13 (m, 4H), 3.17-3.34 (m, 5H), 4.25 (m, 1H), 447 0 (m, 1H), 5.49 (s, br, 1H), 7.04-7.66 (mm, 7H), 9.03 (4,

J=8.4Hz, 1H), 10.11 (s, 1H), 12.61 (s, 1H) 2) 3.18 (m, 4H), 4.26 (5, 2H), 7.00-7.85 (m, 10H), 8.53 (d, oa "| J=4.4Hz, 1H), 8.95 (s, br, 1H), 9.07 (d, J=8.4Hz, 1H), 10.47 (s, 1H), 12.59 (s, 1H)

A 2.75 (s, 3H), 3.10-3.75 (m, 8H), 3.85 (5, 2H), 7.00-7.65 pe (m, TH), 9.00 (d, 1H), 9.85 (s, 1H), 12.60 (s, 1H)

Examples 90-101

R1 0

RS NTN N

Pa o H

Synthesis of intermediates: 7-Bromo-2-oxo-1,2-dihydroquinoline-4-carboxylic acid:

A mixture of 6-bromoi satin (226 mg, 1 mmol), malonic acid, (114 amg, 1.1 mmols) and sodium acetate (103 mg, 1.25 mmols) and acetic acid (2.5 ml) the was stirred under a nitrogen atmosphere for 5 h. Additional sodium acetate (100 mg) was added and the resultant mixture was heated overnight. The reaction mixture was cooled to room temperature, excess acetic acid was removed under reduced pressure and the resultant pinkish brown solid was washed with copious amounts of water and dried under vacuum to obtain the desired product (234 mg, 88%). 'H NMR(300 MHZ, DMSO-d ¢): 6.88 (s, 1H), 7.44 (d, 1H), 7.58 (s, 1H), 8.18 (d, 1H), 12.11 (brs, 1H), m/z 268 7-Bromo-2-0x0-1,2-dihydroquinoline-4-carboxylic acid ethyl ester: 7-Bromo-2-0x0-1,2-dihydroquinoline-4-carboxylic acid: (1g, 3.74 mmnols), absolute ethanol (4 ml) and conc. sulphuric acid (4 ml) were heated to reflux for 45 mims. The reaction mixture was cooled to room temperature and the ethanol removed under reduced pressure.

The resultant dark brown precipitate was washed with and dried undex vacuum to yield the desired product (0.95 g, 86%). '"H NMR(300 MHZ, DMSO-cly): 1.44 (t, 3H), 4.47 (q, 2H), 7.28 (s, 1), 7.40 (dd, 1H), 7.58 (d, 1H), 8.28 (d, 1H), 11.80 (bor s, 1H), m/z 296 7-bromo-2-chloro-quinoline-<3-carboxylic acid ethyl ester: 7-Bromo-2-oxo-1,2-dihydroquinoline-4-carboxylic acid ethyl ester (3.5 g, 1.69 mmols) phosphorous oxychloride (10 ml) and phosphorous pentoxide (50 mg) were heated at reflux for 1.5 hrs under an inert atm osphere. The reaction mixture was cooled to room temperature, phosphorous oxychloride evaporated under vacuum and dichloromethane (200 ml) added.

The resultant organic solutioxa was washed with sat’d NaHCO; (50 m1), followed by brine (50 ml). The organic layer was separated, dried over Na;SO4 (anhyd.), amd solvent removed. The product was purified by silica gel chromatography using an ethyl ace tate and hexanes gradient to obtain the title compound (408 mg, 76%). 'HNMR(300 MHZ, CDCl): 1.48 (t, 3H), 4.51(q, 2H), 7.74 (dd, 1H), 7.92 (s, 1H), 8.25 (d, 1H), 8.66 (d, 1H), m/z 314 8-bromo-1-oxo0-1,2,-dihydro-[1,2,4]-triazolo[4,3-a]quinoline-5-carboxylic acid ethyl ester:

7-Bromo-2-chloro-quinoline-4-carboxylic acid ethyl ester (305 mg, 1 mmol) ethyl carbazate (1.2 mmols) , 4 M HCl in dioxane (0.2 ml) and abs. ethanol (5 ml) were placed in a pyrex vial and the resultant mixture was heated at 160 °C for 20 minutes in a microwave synthesizer.

The mixture was cooled and the precipitated product filtered off, washed wwith a small amount of methanol followed by hex anes and dried under vacuum to obtain the title compound (193 mg, 57.4%). 'H NMR(300 MHZ, DMSO-de): 1.36 (t, 3H), 4.38 (gq, 2H), 7.68 (d, 1H), 7.77 (s, 1H), 8.30 (d, 1H), 9.17 (s, 1H), 13.03 (s, 1H), m/z 308 8-bromo-1-oxo0-1,2-dihydro-[1,2,4]-triazolo[4,3-a]quinoline-5-caroxylic acid: 8-Bromo-1-ox0-1,2-dihydro-{1,2,4]-triazolo[4,3-a]quinoline-5-caroxylic acid ethyl ester (100 mg, 0.3 mmols) and lithium hydroxide.monohydrate (0.9 mmols, 38 mg) in a mixture of THF, methanol, and water (1:1:1,. 2.3ml) was stirred at room temperature for 2 hours, The solvent was removed to yield a pink solid. Water (5ml) was added, and the pH ofthe resultant solution adjusted to 1-2. The resulting precipitate was washed with water then hexanes and dried to yield the desired product (58.7 mg, 63.5%). 'H NMR(300 MHZ, DMSO-de): 7.68 (dd, 1H), 7.73 (s, 1H), 8.46(d, 1H), 12.99 (s, 1H), m/z 278 5-amino-8-bromo[ 1,2[4]triazolo[4,3-a]quinolin-1(2H)-one (example 90): 8-Bromo- 1-0x0-1,2-dihydro -[1,2,4-triazolo[4,3-a]quinoline-5-carboxylic acid (0.5 g, 1.62 mmols) was dissolved in z-butanol (8 ml), and diisopropylethylamine (0.31 ml, 1.78 mmols) followed by diphenylphosphorylazide (0.39 ml, 1.78 mmols) added. The reaction mixture was heated at reflux for 5 hrs under anhydrous conditions. The solvent was removed to obtain a slurry of the Boc protected analogue of the title compound. 5% trifluoroacetic acid in dichloromethanewas added and the reaction mixture stirred at room temperature for 1 hour.

Additional TFA (1 mL) was added and the resultant precipitate filtered off, washed with hexanes and dried under vacuum to obtain the desired product (0.326 g, 72.4%).

Example 90: 5-methyl-8-pyridin-4-yl[1,2,4]¢riazolo{4,3-a]quinolin-1 (2H)-one: 8-bromo- 5-methyl-[1,2,4]-triazolo[4,3-a-quinolin-1-one (139 mg, 0.5 mmols) , 4-pyridyl-boronic acid (74 mg, 0.6 mmols) , Cs,COs (0.65 g, 2 mmols) and Pd(PPh;)4 (35 mg, 7 mol%) were placed in a pyrex microwave tube and dioxane (4 ml) and water (1 mal)added. The resultant heterogeneous mixture was heated at 165 °C for 10 minutes ix a microwave Synthesizer. At the end of this time, the top organic layer was separated, the crude product isolated and purified by RP-HPLC to yield the desired product following I yophilization.

S Example 91 was prepared by the procedure described above starting with 8-bromo-5-methyl- [1,2,4]-triazolo[4,3-a-quinolin-1-one and coupling with the boronic acid.

Example 92 was synthesized in 6 steps from 6-bromoisatin a s outlined above.

Example 93 was prepared via Suzuki coupling of the appropriate boronic acid starting and 5- amino-8-bromno{1,2,4}triazolo[4,3-a]quinolin- 1 -(2H)-one (exzample 90).

Example 94 was synthesized from (2-chloro-4-methyl-quinodin-7-yl)-dimethyl-amine (which was generated according to a published procedure) and placed in a pyrex microwave tube with ethyl carbazate (1.2 mmols), 4 M HCl in dioxane (0.2 m1) and abs. ethanol (5 ml). The resultant mixture was heated at 160 °C for 20 minutes in a mi crowave synthesizer. The precipitated product was filtered, washed with a small amoun t of methanol followed by heaxnes and dried under vacuum to obtain the title product (1 93 mg, 57.4%).

Examples 93-99

Were prepared as described above for either example 89 (5-maethyl analogs) or example 91 (5- amino analogs).

I EE i u Me 2.55 (s, 3H), 7.14 (d, IH), 8.00 (m, 4H), 8.90 | 276 (d, 2H), 9.43 G, 1H), 12.56 (s, 1H) ee

NZ

Me 2.55(s, 3H), "7.14 (d, 1H), 8.00 (m, 4H), 890 | 332 or (d, 2H), 9.43 (5, 1H), 12.56 (3, 1H)

HN

NE A eve 7.87 (d, 1H), 9.09 (d, 1H), 11.82 (s, IH)

CT EE

Ho (d,2H), 7.72 (4, 2H), 7.76 (dd, 1H), 8.07 (4, 1H), 9.33 (s, 1H), 11.83 (s, IH)

Me 2.36(s, 3H), 3.03 (5, 6H), 6.63 (5, 1H), 6.84 242 _N (dd, 1H), 7.57 (d, 1H), 8.37 (d, 1H), 12.20 G5, be i lo}

Me 7.53 (5, 3H), 6.95 (5, 1H), 720 (m, 1H), 7.73 | 282 (m, 2H), 7.80 (m, 2H), 9.27 (5, 1H)

Oh s

NH, 5.95 (5, [H), 6.30 (5, 2H), 7.18 (m, 1H), 7.60 | 283 { (m, 2H), 7.77 (d, 1H), 8.02 (d, 1H), 9.26 (s, 1H), 11.80 (s, 1H)

NH, 5.96 (5, 1H), 6.64 (q, 1H), 7.20 (m, 1H), 7.14 | 267 rN, (d, 1H), 7.80 (d, 1H), 7.86 (5, 1H), 8.06 (d, ° 1H), 9.35 (s, 1H), 11.83 (brs, 1H)

Me 2.52 (s, 3H), 6.18 (m, 1H), 6.67 (5, 1H), 6.90 | 265 { ds (m, 2H), 7.73 (m, 2H), 9.17 (s, 1H), 11.52 (s,

H 1H)

Me 2.50 (s, 3H), 6.67 (m, 1H), 6.98 (m, 1H), 7.10 | 266 "| 3. (m, 1H), 7.82 (m, 3H), 9.30 (s, 1H)

NH, 5.90 (s, 1H), 6.32 (5, 2H), 7.57 (4, 1H), 7.69 | 283 a (m, 1H), 7.78 (d, 1H), 7.98 (m, 2H), 9.30 (s,

Ss 1H), 11.85 (s, 1H)

Me 2.51 (5, 3H), 6.55 (s, 1H), 7.01 (s, 1H), 7.56 | 282 as (d, 1H), 7.70 (m, 1H), 7.80 (m, 2H), 7.95 (m,

Ss 1H), 9.30 (s, 1H)

Examples 102-126 cl R “OY. NH,NHCOOEt eH _ReoH, _ So! —_— ES Suzuki coupling nN

NZ cl py ho 0 7-chloro-5-methyl-2H-[1,2,4]triazolo[4,3-c¢Jquinolin-1-one :

To a suspension of 2,6-dichloro-4-methylquinoline (212mg, 1.0mmol) and ethyl carbazate (125mg 1.2mmol) in 4ml of ethanol was added 4 drops of HCI (4N in dioxane). The reaction mixture was subject to microwave irradiation at 150°C for 20min. After cooling to room temperature the precipitated yellow solid was filtered off, washed with methanol (3x10 ml) and dried under vacuum to give the title compound as a yellow solid (76.4mg, 32.7%). 7-Substituted-5-methyl-2H-{1,2,4]triazolo[4,3-0]]quinolim-1-ones:

Toa 5 ml vial, 7-chloro-5-methyl-2H-[1,2,4]triazolo[4,3 —0c]quinolin-1-one (117 mg, 0.5mmol), boronic acid (0.6mmol), cesium carbonate (651mg, 2.0mmol), and tetrakis(trisphenylphosphine)palladium (40mg, 7mol%) were added in dioxane:water (4:1, 4m). The reaction was subject to microwave irradiation. at 165°C for 20min. After cooling to room temperature, the lower layer was removed and discarded, solvent was removed from the upper layer and the resulting residue dissolved in minimum amount of DMSO. The solution was and purified by HPLC. age! i dN a Lc 1H), 12.53 (s, 1H)

TA fam ET 1H), 12.23 (s, 1H) 106 Fay 2.55 (5, 3 H), 3.85 (5, 3H), 6.95-8.00 (m, 7H), 9.01 (d, 1H), 12.42

On em m—am { 1H), 12.51 (s, 1H) 1H) 110 0.92 (t, 3 H), 1.35 (m, 2H), 1.58 (m, 2H), 2.55 (5, 3H), 2.65 (,

On [memo mm soa rss m sen 111 Pay 2.56 (s, 3H), 4.16 (d, J=5.6Hz, 2H), 7.12-8.04 (m, 7H), 8.22 (s, br,

UO ferme ma 9.07 (d, 1H), 12.50 (5, 1H)

U3 fy [2456 3H), 296s, 6H), 6.34 (d, J=8Hz, 2H), 7.04 (5, 1H), 7.64 (d, J=8.4 Hz, 2H), 7.88 (m, 2H), 8.96 (d, ]=8.4Hz, 1H), 12.38 (s, ememiiein 114 ee 2.35 (s, 3H), 6.70-7.78 (m, 7H), 8.86 (d, J=8.8Hz, 1H), 12.35 (s,

G [meme (d, 1H), 12.40 (s, 1H)

cl 1H) 117 Or 2.55 (5, 3H), 7.10-8.11 (m, 6H), 9.04 (d, J=8.4Hz, 1H), 12.48 (s,

MR i 118 as 2.48 (s, 3H), 7.08 (4, J=1.2Hz, 1H), 7.76 (m, 2H), 8.07-8.12 (m,

TO [mamma ¢ (d, J=8.8Hz, 1H), 12.53 (s, 1H)

OF ae * | J=8.8Hz, 1H), 12.60 (s, 1H) 9.02 (d, J=8.4Hz, 1H), 12.40 (s, 1H) 1H), 12.49 (s, 1H)

BEcs 12.39 (s, 1H)

RES

(s, 1H) 1H)

Examples 127-141

The following examples were prepared by the following procedure using 4-(5-methyl- 1-0x0-1,2-dihydro-[1,2,4]triazolo[4,3-0jquinolin-7-yl)-t»enzaldehyde and the appropriate amine. 4-(5-methyl-1-oxo-1,2-dihydro-[1,2,4]triazolof4,3-0quinolin-7-yl)-benzaldehyde

HO pe oN FVRn SUT , CL, ° Ho” ® oH pa

To a 5 ml vial, 7-chloro-5-methyl-2H-[1,2,4]tr-iazolo[4,3-0)quinolin-1-one (117 mg, 0.5mmol), 4-formylphenylboronic acid (90mg, 0.6mmol), cesium carbonate (651mg, 2.0mmol), and tetrakis(trisphenylphosphine)palladiukn (40mg, 7mol%) were added in dioxane:water (4:1, 4ml). The reaction was subject te microwave irradiation at 165°C for 20min. After cooling to room temperature, the lower layer was removed and discarded, the solid that precipitated was filtered off, washed with me=thanol and dried under vacuum to give the desired product which was used without further purification. i REN “Od, RNH, NaCNBH,

Cl Microwave NTR yo HH o

To a suspension of 4-(5-methyl-1-ox0-1,2-dihydro-[1,2,4]triazolo[4,3-0)quinolin-7- yl)-benzaldehyde (0.5mmol, 64% pure) in DMF (4m), the appropriate amine (Immol) was : added. The mixture was stirred overnight at room temperature and NaCNBH; (63mg, 1mmol) added, followed by 2 drops of AcOH. The reaction ~was subjected microwave irradiation at 150°C for 5min. Water (Iml)was added, and the caude product isolated and purified by

HPLC.

127 2.03 (m, 2H), 2.55 (s, 3H) , 2.79 (5, 6H), 3.03 (m,

ANA AANH

2H), 3.17 (m, 2H), 4.25 (=, 2H), 7.09-8.03 (m, 7H), 7] A [eee 128 I~ 2.06 (m, 2H), 2.56 (s, 3H3, 3.04 (m, 4H), 3.19 (m, — 4H), 3.70 (m, 2H), 4.00 (xx, 2H), 4.25 (s, 2H), 7.10-8.03 (m, 7H), 9.05 («i, J=8.4Hz, 1H), 9.20 (s, br, 1H), 12.47 (s, 1H) 129 CL 2.55 (5, 3H), 3.17 (m, 2H), 3.38 (m, 2H), 4.31 (s, ) 2H), 7.09-8.04 (m, 10H), 8.60 (s, 1H), 9.10 (d, 130 HO _~ 2.56 (s, 3H), 3.00 (m, 2H), 3.68 (t, J=5Hz, 2H), 4.24 (s, 2H), 5.30 (s, br, 1H), 7.10 (s, 1H), 7.63- 8.04 (m, 6H), 8.91 (s, br, 1H), 9.05 (d, J=8.4Hz, 1H), 12.46 (s, 1H) 131 IVY 2.55 (s, 3H), 2.80 (s, 3H), 3.00-3.40 (m, 8H), 3.88 ~~ (s, 2H), 7.09-8.01 (m, 7K), 9.04 (d, J=8.4Hz, 1H), 12.46 (s, 1H) 132% O—. 2.13-2.34 (m, 6H), 2.60 (5, 3H), 3.80-3.90 (m, 3H), 4.49 (t, J=6.4Hz, 1H), 4_95 (d, J=12.8Hz, 1H), 6.98 (s, 1H), 7.75-8.08 (m, 6), 9.13 (d, J=8.4Hz, 1H), 11.42 (s, 1H) 133 X 0.95 (d,d, J=6.8Hz, 6H), 2.10 (m, 1H), 2.56 (s, 3H),

HOH 2.92 (m, 1H), 3.73 (m, 2H), 4.32 (d, J=18.8Hz, 2H), 5.45 (s, br, 1H), 7. 10 (s, 1H), 7.67-8.04 (m, 6H), 8.90 (s, br, 1H), 9.405 (d, J=8.8Hz, 1H), 12.46 (s, 1H) 134 Ror 2.55 (m, 11H), 4.50 (s, 2H), 7.10-8.15 (m, 10H), ho [em

135 Dw 2.20 (m, 2H), 2.55 (s, 3H), 3.00 (m, 2H), 4.20-4.30 (m, 4H), 7.08 (5, 1H), 7.60-8.05 (m, 9H), 9.08 (m, 2H), 12.50 (s, 1H) 136° Sh 1.41 ¢, d=7.2Hz, 3H), 2.61 (s, 3H), 3.16 (q, ind J=7.2Hz, 2H), 4.41/4.50 (s/s, 4H), 6.99 (s, 1H), 7.72-8.84 (m, 10H), 9.14 (d, J=8.8Hz, 1H), 11.48 (s, 1H) 137 0 1.80-2.00 (m, 4H), 2.50 (s, 3H), 2.55 (m, 6H), 2.90

Cn (m, 2H), 4.23 (s, 2H), 7.10 (s, 1H), 7.61-8.03 (m, 6H), 8.85 (s, br, 1H), 9.05 (d, 1H), 12.45 (s, 1H) 138 N 2.51 (s, 3H), 3.30 (s, 2H), 6.25-8.00 (m, 15H), 9.00

RIE re i 139 OD 2.55 (s, 3H), 4.22 (5, 2H), 4.28 (5, 2H), 6.58-6.68 (m, 2H), 7.10 (s, 1H), 7.88-8.01 (m, 7H), 9.05 (d, 1H), 9.42 (s, br, 1H), 12.45 (s, 1H) 140 Ret 1.30-1.88 (m, 5H), 2.55 (s, 3H), 2.95 (m, 2H), 3.20 (m, 2H), 3.30 (m, 2H), 4.32 (s, 2H), 7.10 (s, 1H),

NEE 7.60-8.00 (m, 6H), 9.02 (d, 1H), 12.45 (s, 1H) 141 1 0.95 (d, J=6.8Hz, 6H), 2.00 (m, 1H), 2.56 (s, 3H),

NH 2.85 (m, 2H), 4.23 (s, 2H), 7.10 (s, 1H), 7.64-8.04 (m, 6H), 8.75 (s, br, 1H), 9.05 (d, 1H), 12.50 (s, 1H) a: Acetone-d6 as solvent

Examples 142-146

The following examples were prepared using the same procedure as that described for examples 120-134 using 2-methoxy-5-(5-methyl-1-0x0-1,2-dihydro[1,2,4]triazolo[4,3- a}quinolin-7-yl)benzaldehyde (prepared as described above) and the appropriate amine.

R

Pa <q g x )e N

J A

NO ON ic ci J 142 NHS 2.11 (m, 2H), 2.54 (s, 3H), 2.14-3.22 (m, 10H),

Lo 3.84-3.97 (m, SH), 4.24 (s, 2H), 7.09 (d, J=12Hz, 1H), 7.24 (t, J=4.5Hz, 1H), 7.88-7.97 (m, 4H), 9.01/9.09 (d/s, J=8.4FK z/br, 2H), 12.46 (s, LH) 143 _. : 2.51 (s, 3H), 3.23 (m, 2H), 3.42 (m, 2H), 3.99 (s,

N NH 3H), 4.31 (s, 2H), 6.9°7-8.57 (m, 10H), 9.00 (s, br,

T mhmesmeinie 144 HO ~~ 2.55 (s, 3H), 3.03 (m, 2H), 3.70 (m, 2H), 3.92 (s, 3H), 4.25 (s, 2H), 7.10 (s, 1H), 7.21 (d, 1H), 7.89- 7.98 (m, 4H), 8.70 (s, br, 1H), 9.03 (d, J=8.8Hz, 1H), 12.45 (s, 1H) 145 HO 1.30-1.85 (m, 7H), 2.5 5 (5, 3H), 3.02 (m, 2H), 3.45

TQ (m, 4H), 3.90 (s, 3H), 4.31 (s, 2H), 7.08 (d,

J=0.8Hz, 1H), 7.26 (d, J=8.4Hz, 1H), 7.90-7.97 (m, 4H), 9.02 (d, J=8.8Hz, 1H), 12.45 (s, IH) 146 J Asn 2.55 (s, 3H), 2.73 (s, 6-H), 2.80 (t, ]=8.0Hz, 2H), 3.19 (m, 2H), 3.88/3.9 2 (s/s, 5H), 4.25 (s, 2H), 4.33 (5, 2H), 6.42 (d, ¥=3.2Hz, 1H), 6.62 (d,

J=3.2Hz, lH), 7.10 (d,. J=0.8Hz, 1H), 7.25 (d,

J=8.8Hz, 1H), 7.88-7.98 (m, 4H), 8.95 (s, br, 1H), 9.04 (d, J=8.8Hz, 1H), 12.46 (s, 1H)

Example 147

OH po o H

The methoxy analogue (example 105) (30.5mg, 0.lmmol) in BBr; (IM in CHCl, 3ml) was stirred for 3 hours at room temperature. Crushed ice was add «ed into the mixture and solvent removed under reduced pressure. The residue was dissolved im the minimum amount of DMSO and purified by HPLC. 'H NMR (400MHz, DMSO-d6): 2.5®0 (s, 3H), 6.85-7.95 (m, 7H), 8.90 (d, 1H), 9.85 (s, 1H), 12.40 (s, 1H)

Examples 148-149

The following examples were prepared using the procedure described for Example 147 using the appropriate methoxy-substituted triazolone. pee!

NN dN oH 2.51 (s, 3H), 6.65-7.90 (m, 6H), 8.95 («d, 1H), 9.82 (s, 1H),

ERE rvs i 12.45 (s, 1H)

Examples 150-184

The following examples were prepared using the procedure desscribed below:

0 © s]

SOL, ame DOU =e oe, es “Or NHNHCOOR “ RB(OH), _o IQ ® c Ng Mowe cr Ny Sumid coupling A

H ST

Diketene (32ml, 32g, 381 mmol) was added to the suspension of 3-chloro-4- methoxyphenylamine (50g, 317.25mmol) in toluene (300ml). The mixture was wefluxed for 6hrs, cooled to room temperature and allowed to stand overnight. The precipitated solid was filtered off, washed with ether and dried under vacuum, to give the desired product as a light yellow solid (48g, 62.9%).

A mixture of 3-chloro-4-methoxy acetoacetanilide (48g, 199.6mmol) armd concentrated sulfuric acid (80ml) was heated on an oil-bath at 70-80°C for 0.5h followed by 1.0h at 100°C.

The mixture was cooled to room temperature and poured onto crushed ice. T he precipitated solid was filtered off and recrystallized from ethanol to give the desired compound as a white solid (30g, 67.26%).

A mixture of 7-chloro-6-methoxy-4-methyl-1H-quinolin-2-one (30gz, 134.2mmol),

DMF (10ml) and thionyl chloride (300g) was refluxed for 3hr. The mixture was cooled to room temperature and the solid that crystallized out filtered off, washed wi th acetone and dried under vacuum. The desired product was obtained as a yellow solid (16.4g=, 50.5%).

To a suspension of 2,7-dicloro-6-methoxy-4-methyl-quinoline (363mg, 1.5mmol) and ethyl carbazate (173mg 1.66mmol) in ethanol (3.7ml) was added 6 drops of HCI (4N in dioxane). The reaction mixture was subject to microwave irradiation at 170°C for 20min.

After cooling to room temperature the orange precipitate was removed by filtraation, washed with methanol (3x10 ml), and dried under vacuum, to give 8-Choloro-7-metho=xy-5-methyl- 2H-[1,2,4]triazolo[4,3-0]quinolin-1-one was obtained (225mg, 57.0%). 'H NMR (400MHz,

DMSO0-d6): 3.37 (s, 3H), 4.04 (s, 3H), 7.07 (5, 1H), 7.35 (s, 1H), 8.98 (s, 1H), 12.46 (s, 1H)

To a 5 ml vial, 8-Choloro-7-methoxy-5-methyl-2H-[1,2,4]triazolo[4,3-&]quinolin-1- one (132 mg, 0.5mmol), the appropriate boronic acid (0.6mmol), cesium carbonate (651mg, 2.0mmol), and tetrakis(trisphenylphosphine)palladium (40mg, 7mol%) were aided in dioxane:water (4:1, 4ml). The reaction was subject to microwave irradiation at 165°C for 20min. The mixture was cooled to room temperature and the lower layer removed and discarded. Solvent was removed from the upper layer, and the residue obtained dissolved in minimum amount of DMSO. The DMSO solution was filtered and purified by HPLC.

Ey & o H a I a 8.80 (m, 2H), 9.06 (s, LH), 12.50 (s, 1H)

NEE (m, 6H), 8.78 (s, 1H), 12.37 (s, 1H) © 1H), 12.39 (s, 1H) 153 | <5 2.53 (s, 3H), 3.13 (s, 3H), 3.85 (5, 3H), 4.03 (d, 2H), 7.08-7.5 1

TE este, 154 Qu 2.51 (s, 3H), 3.88 (s, 3H), 5.16 (s, 2H), 7.00-7.50 (m, 11H), 8.95 [om

N (s, 1H), 12.30 (s, 1H) 6H), 8.93 (s, 1H), 12.40 (s, 1H) (m, 7H), 8.92 (s, 1H), 12.40 (s, 1H) br, 2H), 8.94 (s, 1H), 12.42 (s, 1H) (s, 1H) 4 1H), 12.40 (s, 1H)

161 - 2.50 (s, 3H), 3.79/3.81 (s/s, GH), 3.90 (s, 3H), 7.03-7.32 (m, 5H), :

TD [mn (s, 1H) 1H), 12.36 (s, 1H) 164 ay 2.51 (5, 3H), 4.09 (5, 3H), 6.94-7.61 (m, 6H), 8.99 (s, 1H), 12.41

RE

165 ad 2.51 (s, 3H), 3.70 (s, 3H), 3.82 (s, 6H), 6.61-7.29 (m, 5H), 8.75 (s,

ER

166 De 2.54 (5, 3H), 3.94 (s, 3H), 7.13-7.40 (m, 5H), 8.98 (5, 1H), 12.50 lq femme ome 1H), 12.34 (s, 1H) 168 2.51 (s, 3H), 3.92 (s, 3H), 7.09-7.85 (m, 6H), 8.96 (s, 1H), 12.44

RE i 169 MeG 2.51 (s, 3H), 3.80 (s, 3H), 3.91 (5, 3K), 6.95-7.42 (m, 6H), 8.95 (s,

RE

170 a 2.51 (s, 3H), 3.91 (s, 3H), 7.06-7.56 (m, 6H), 8.94 (s, 1H), 12.40

Gs, 1H) 6H), 8.93 (s, 1H), 12.40 (s, 1H) (m, 6H), 8.92 (s, 1H), 12.39 (s, 1H)

RE Fr 1H), 12.40 (s, 1H) 174 ey 2.53 (s, 3H), 3.90 (5, 3H), 4.13 (s, 2H), 7.10-7.62 (m, 6H), 8.22 (s,

To hmsemngn 175 oa 2.55 (s, 3H), 3.92 (s, 3H), 7.10-8.08 (m, 6H), 9.00 (s, 1H), 10.10

ME

176 1 2.54 (s, 3H), 3.60-3.80 (m, 8H), 3.92 (5, 3H), 7.09-7.63 (m, 6H), 00 men

177 — 1.84-1.91 (m, 4H), 2.54 (s, 3H), 3.45-3.52 (m, 4H), 3.93 (s, 3H),

Bi a eto il 178 1.50-1.65 (m, 6H), 2.52 (s, 3H), 3.40-3.60 (m, 4H), 3.93 (s, 3H), lob 179 HL 1.10-1.90 (m, 10H), 2.52 (s, 3H), 3.80 (m, 1H), 3.92 (s, 3H), 7.05-

ORO Laem eon

BEC Ere

MeO 7.89 (dd, 1H), 8.32 (d, 1H), 8.90 (s, 1H), 12.42 (s, 1H) 181 NG 2.60 (s, 3H), 4.01 (s, 2H), 4.24 (s, 3H), 7.14-7.71 (m, 6H), 9.00 (5,

TL fen EE 3H), 7.14-8.08 (m, €H), 9.03 (m, 2H), 12.49 (s, 1H) 183 2.50 (s, 3H), 3.93 (s, 3H), 7.05-8.84 (m, 6H), 8.88 (s, 1H), 12.42

Ce 184 2.53 (s, 3H), 3.98 (s, 3H), 7.03 (s, 1H), 7.33 (s, 1H), 746 (d,J = as 4.8Hz, 1H), 7.65 (4, J = 2.8Hz, 1H), 7.89 (5, 1H), 9.14 (s, 1H),

G [meme

Examples 185-207

The following examples were prepared using the following procedure. : ~0 XN AC SN

J A RNR. NaChet, J NTN ) po) Microwave ® a x 9) R

To a suspension of 3-(7-methoxy-5-methyl-1-oxo-1,2-dihydro-[1,2,4]triazolo[4,3- ot]quinolin-8-yl)-benzaldehyde (0.5mmol) in DMF (4ml), the appropriate amine (1mmol) was added. The mixture was stirred overnight at room temperature and NaCNB Hj; (63mg, 1 mmol) added, followed by 2 drops of AcOH. The reaction was subjected to the xnicrowave iwxradiation at150°C for 5min. Water (Iml) was added. The crude product was isolated and purified by HPLC.

cc OS 185 HO _~~\H 2.54 (s, 3H), 3.03 (m, 2H), 3.68 (t, J=5.2Hz, 2H), 3.91 (s, 3H), 4.26 (5, 2H), 5.25 (s, br, LH), 7.10- 7.69 (m, 6H), 8.90 (s, br, 13), 8.96 (s, 1H), 12.43 (s, 1H) 186 Dov 2.51 (5, 3H), 3.67 (5, 3H), 3.90 (5, 3H), 4.23 (5, 2H), 4.29 (5, 2H), 6.03 (m, 1H), 6.27 (m, 1H), 6.82 (t, J=2Hz, 1H), 7.09 (d, J=0.8Hz, 1H), 7.38-7.67 (m, SH), 8.96 (s, 1H), 9.15 (s, br, 1H), 12.43 (s, 1H) 187 Aw 1.30-1.90 (m, 7H), 2.54 (s., 3H), 2.93 (m, 2H), 3.40 (m, 4H), 3.90 (s, 3H), 4.37 (s, 2H), 7.09-7.73 (m,

CLT amie 188 or 2.51 (s, 3H), 3.85 (5, 3H), 4.34/4.36 (s/s, 4H), 7.09- 7.68 (m, 8H), 8.86 (m, 2D), 8.96 (s, 1H), 9.59 (s,

CT femme 189 ge 0.95 (4, J=6.8Hz, 6H), 1.99 (m, 1H), 2.51 (5, 35), 2.82 (m, 2H), 3.91 (s, 3H), 4.25 (5, 2H), 7.10-7.69 (m, 6H), 8.78 (s, br, 1H), 8.96 (s, 1H), 12.43 (s, 1H) 190 TN 7.05 (m, 2H), 2.51 (s, 3H), 3.05 (m, 4H), 3.18 (m, hd 4H), 3.68 (m, 2H), 3.91 (ss, 3H), 3.96 (m, 2H), 4.27 (s, 2H), 7.10-7.67 (m, 6H, 8.96 (s, 1H), 9.10 (s, br,

CT seta 191 a 1.18 (m, 2H), 1.35 (m, 1ET), 1.63 (m, 2H), 1.92 (m, 2H), 2.51 (s, 3H), 2.84 (nm, 2H), 3.22 (m, 2H), 3.52 (s, 2H), 3.95 (s, 3H), 4.39 (t, J=5.2Hz, 1H), 7.07- 7.46 (m, 6H), 8.95 (5, LED, 12.38 (s, 1H)

192 Ae 2.20 (m, 2H), 2.51 (s, 3H), 3 .17 (m, 2H), 3.96 (5, 3H), 4.26 (5, 2H), 4.31 (t, ]=6.8Hz, 2H), 7.10-7.95 (m, 8H), 8.96 (s, 1H), 9.07/.11 (s/s, 2H), 12.44 (s, 1H) 193 a 2.54 (s, 3H), 3.91 (5, 3H), 4. 30 (m, 4H), 7.10-7.67n (m, 10H), 8.96 (s, 1H), 9.34 (s, br, 1H), 12.43 (s, 7] PT [eam 194 TNO. 2.50 (s, 3H), 2.62 (5, 6H), 3-17-3.30 (m, 4H), 3.92 (s, 3h), 4.32 (5, 2H), 7.10-7. 68 (m, 6H), 8.70 (s, br, 1H), 8.97 (s, 1H), 12.44 (s, 1H) 195 INP 2.03 (m, 2H), 2.53 (s, 3H), 2.73 (5, 6H), 3.04 (m, 2H), 3.17 (m, 2H), 3.91 (s, 3H), 4.27 (s, 2H), 7.09 (s, 1H), 7.37-7.67 (m, SH), 8.95 (s, 1H), 9.15 (s, br, 1H), 12.45 (s, 1H)

Way 2.12 (s, 3H), 2.30-2.40 (m, BH), 3.35 (5, 3H), 3.50 hd (s, 2H), 3.90 (s, 3H), 7.00-7 .45 (m, 6H), 8.91 (s,

TT pea 197 NT 2.54 (s, 3H), 3.15 (m, 2H), 3.36 (5, 3H), 3.60 (t,

J=5.2Hz, 2H), 3.96 (s, 3H), 4.26 (s, 2H), 7.10-7.69 (m, 6H), 8.96 (s, 1H), 9.00 CG, br, 1H), 12.44 (s, 1H) 198 1.54-1.71 (m, 6H), 2.01 (m 2H), 2.50 (5, 3H), 3.54 (m, 1H), 3.91 (s, 3H), 4.25 (m, 2H), 7.10-7.68 (m, 6H), 8.89 (s, br, 1H), 8.96 Cs, 1H), 12.43 (s, 1H) 199 oo 2.50 (s, 3H), 3.95 (5, 3H), 424/427 (s/s, 4H), 7.10- 7.66 (m, 10H), 8.96 (s, 1H) , 9.32 (s, br, 1H), 12.43 fendi 200 1.80 (m, 2H), 2.17 (m, 4H), 2.51 (5, 3H), 3.74 (m, 1H), 3.91 (s, 3H), 4.13 (s, 2H), 7.10-7.65 (m, 6H),

TT mma

201 1.13-2.14 (m, 10H), 2.50 (s, 3H), 3.06 (m, 1H), 3.90 (s, 3H), 4.27 (s, 2H), 7.10-7.91 (m, 6H), 8.77 (s, br, 1H), 8.95 (s, 1H), 12.43 (s, 1H) 202 x 1.11 (d, J=6.0Hz, 3H), 2.52 (s, 3H), 2.73 (m, 2H),

Me 2.96 (m, 1H), 3.91 (s, 3H), 4.24 (s, 2H), 5.34 (s, br, 1H), 7.09-7.58 (m, 6H), 8.91/8.96 (s/s, 2H), 12.43 (s, 1H) 203 rN 2.21 (m, 2H), 2.59 (s, 3H), 3.23 (m, 4H), 3.78 (m,

Adi 8H), 3.98 (s, 3H), 4.46 (s, 2H), 7.17-7.77 (m, 6H), 9.04 (s, 1H), 12.50 (s, 1H) 204 NH 0.81 (m, 4H), 2.51 (s, 3H), 2.76 (m, 1H), 3.90 (s,

A 3H), 4.34 (s, 2H), 7.10-7.67 (im, 6H), 8.95 (s, 1H), 9.05 (s, br, 1H), 12.43 (s, 1H) 205 Ow 1.83-2.05 (m, 4H), 2.51 (s, 3H), 2.94-3.08 (m, 2H), © 3.73 (m, 2H), 3.95 (s, 3H), 4.12 (m, 1H), 4.27 (s, 2H), 7.09-7.69 (m, 6H), 8.96 (s, 1H), 9.05 (s, br, 1H), 12.43 (5, 1H) 206 Cro 2.54 (s, 3H), 3.40 (m, 2H), 3.98 (s, 3H), 4.26 (1,

J=5.0Hz, 2H), 4.36 (s, 2H), 6.96-7.72 (m, 11H),

TO mmm 207 I~ 2.54 (s, 3H), 3.17-3.36 (m, 4H), 3.91 (s, 3H), 4.30

S (s, 2H), 6.90-7.68 (m, 9H), 8.96 (s, 1H), 9.05 (s, br,

OT fae

Example 208-221

The following examples were prepared using the same procedure as described for examples 185-207 using 2-methoxy-5-(7-methoxy-5-methyl-1-ox0-1,2- dihydro[1,2,4]triazolo[4,3-a]quinolin-8-yl)benzaldehyde and the appropriate amine. © N

SY o o

R

I A 3 co BA 208 Mo MN 2.02 (m, 2H), 2.54 (s, 3H), 2.78 (s, 6H), 3.02 (mn, 2H), 3.12 (m, 2H), 3.91/3.92 (s/s, 6H), 4.23 (s, 2H), 7.10-7.63 (m, 5H), 8.72 (s, br, 1H), 8.95 (s, 1H), 12.43 (s, LH) : 209 yo {Oh 2.54 (s, 3H), 2.68-3.17 (m, 8H), 3.88-4.00 (m, 11H), 7.08-7.95 (m, 5H), 8.96 (s, 1H), 12.42 (s,, 1H) 210 HO ~H 2.52 (s, 3H), 3.02 (m, 2H), 3.68 (t, J=5.0Hz, 2H), 3.91 (s, s, 6H), 4.23 (s, 2H), 5.25 (s, br, 1H), 7.O8- 7.62 (m, SH), 8.65 (s, br, 1H), 8.95 (s, 1H), 12.42 (s, 1H) 211 LY 2.54 (s, 3H), 3.60 (s, 3H), 3.95 (5, 6H), 4.21 (s, s, 4H), 6.03-7.65 (m, 8H), 8.90 (s, br, 1H), 9.05 (s, 1H), 12.42 (s, 1H) 212 Sh 2.52 (s, 3H), 3.90 (s, s, 6H), 4.23 (s, 2H), 4.33 (5, 2H), 7.08-7.62 (m, 7H), 8.70 (m, 2H), 8.95 (s, 1H), 9.28 (s, br, 1H), 12.42 (s, 1H) 213 NO 1.17-1.977 (m, 7H), 2.51 (s, 3H), 2.89 (m, 2H), 3.42 (m, 4H), 3.82 (s, 3H), 3.89 (5, 3H), 4.32 (s, 2H),

HES 7.04-7.54 (m, 5H), 8.94 (s, 1H), 12.37 (s, 1H) 214 Ql, 2.54 (s, 3H), 3.19 (t, J=7.2Hz, 2H), 3.41 (m, 2H), 3.91/3.92 (s/s, 6H), 4.30 (s, 2H), 7.08-7.95 (m, 8H), 8.56 (d, J=4.8Hz, 1H), 8.95 (m, 2H), 12.42 (s, 1H) 215 AS 1.15 (m, 2H), 1.32 (m, 1H), 1.62 (m, 2H), 2.00 (t,

J=6.8Hz, 2H), 2.56 (s, 3H), 2.95 (m, 2H), 3.30 (t,

J=5.6Hz, 2H), 3.52 (s, 2H), 3.89/3.95 (s/s, 6H), 4.45 (t, ¥=5.2Hz, 1H), 7.10-8.02 (m, 5H), 9.01 G, =

216 Meo” NH 2.52 (s, 3H), 3.15 (m, 2H), 3.32 (5, 3H), 3.62 (¢,

J=5.2Hz, 2H), 3.91 (s, s, 6H), 4.22 (s, 2H), 7.08- 7.66 (m, SH), 8.73 (s, br, 1H), 8.95 (s, 1H), 12.42 (s, 1H) 217 1.54-1.71 (m, 8H), 2.51 (ss, 3H), 3.42 (m, 1H), 3.90 (s, s, 6H), 4.18 (s, 2H), 7. 07-7.61 (m, SH), 8.69 (s, br, 1H), 8.94 (s, 1H), 12.441 (5, 1H) 218 or 2.51 (s, 3H), 3.90 (s, s, 6K), 4.24/4.26 (s/s, 4H), ’ 7.07-7.58 (m, 9H), 8.93 (s, 1H), 9.11 (5, br, 1H), 219 1.79 (m, 2H), 2.16 (m, 4H), 2.51 (s, 3H), 3.72 (m, 1H), 3.91 (s, 5, 6H), 4.07 (s, 2H), 7.08-7.62 (m, 5H), 8.85 (s, br, 1H), 8.95 (s, 1H), 12.41 (s, 1H) 220 1.28-2.12 (m, 10H), 2.51 (s, 3H), 3.06 (m, 1H), 3.91 (s, s, 6H), 4.20 (s, 2X), 7.08-7.92 (m, SH),

T| 0 |mmmsemmee 221 NH 0.69 (m, 2H), 0.78 (m, 23H), 2.50 (m, 1H), 2.92 (s,

A 3H). 4.18 (s, 2H), 4.27/4 _31 (s/s, 6H), 7.46-7.91 (m, SH), 9.35 (s, 1H), 12 80 (s, 1H)

Examples 222-225

The following examples were prepared using the same porocedure as described for examples 208-221 using 2-(7-methoxy-5-methyl-1-oxo-1,2-dilnydro[1,2,4]triazolo[4,3- alquinolin-8-yl)benzaldehyde and the appropriate amine. 0 4 N

CU 5 oN

NR

TR (OE, DNSO.40 222 xo 2.49 (s, 3H), 3.85 (s, 3H), 4.00-4._30 (m, 4H), 7.00- 7.70 (m, 10H), 8.74 (s, 1H), 9.34 (5, br, 1H), 12.43 (s, 1H) 223 HO ~nH 2.55 (s, 3H), 2.86 (m, 2H), 3.53 (am, 2H), 3.90 (s, 3H), 4.07 (s, 2H), 5.12 (s, br, 1H), 7.13-7.73 (m, 6H), 8.71 (s, br, 1H), 8.85 (s, 1H), 12.43 (s, 1H) 224 "x 1.33-1.72 (m, 5H), 2.49 (s, 3H), 2.70-3.30 (m, 6H), 3.96 (s, 3H), 4.28 (m, 2H), 5.26 (s, br, 1H), 7.13- 7.79 (m, 6H), 8.77 (s, 1H), 12.44 (s, 1H) 225 I 1.41 (m, 3H), 2.92 (5, 3H), 3.17 (am, 1H), 4.12-4.37 ni (m, TH), 7.55-8.15 (m, 6H), 9.15 (s, br, 1H), 9.24 (s, 1H), 12.86 (s, 1H)

Example 226-272

O

7 jee] BBr, In CH,CL, “or

RI op R2 NSN > &

O H

As previously described, the methoxy analog (0.1mmol) in BBx; (1M in CH;Cl,, 3ml) was stirred for 3 hours at room temperature. Crushed ice was added amad the solvent removed under reduced pressure. The residue was dissolved in minimum axmount of DMSO and purified by HPLC.

FRR (NE DHS 009 226 A Hy 2.38 (s, 3H), 4.36 (s, 2H), 7.03-7.60 (m, 6H), & 8.68 (s, 1H), 9.88 (s, 1H), 12.34 (5, 1H) 227 oH 2.40 (s, 3H), 6.75-7.25 5H), 8.91-9.08 (m,

Aw, Ao 6.35) (2, 58) m 3H), 9.80 (s, 1H), 12.35 (=, 1H) 228 ho 2.45 (s, 3H), 4.20 (s, 2H), 7.10-7.78 (m, 6 =, pa G, 31,420 (5, 20), 7 (x0, 6H), as 8.25 (s, br, 2H), 8.98 (s, 1 H), 10.10 (s, 1H), 12.40 (s, 1H)

9.00 (s, 1H), 1 0.02 (s, 1H), 12.42 (s, 1H) 7.56 (m, 6H), 8.93 (5, 1H), 9.97 Gs, 1H), 12.35 s, 15) i 231 a <5 2.40 (s, 3H), 7.10-7.50 (m, 5H), 8.95 Gs, 1H),

EERE

1H), 10.57 (s, 1H), 12.42 (s, 1H) 233 pa pu 0.94 (d, J=6.4 iz, 6H), 2.01 (wm, 1H), 242 (s, - - Bas - - 3H), 2.82 (m, 2H), 4.44 (5, 2H), 7.05775 (m, { 6H), 8.70 (s, br, 1H), 8.95 (s, 1H), 10.15 (s, 1H), 12.48 (s, 1H) : 234 | Oy a 1.20-1.90 (m, 7H), 2.40 (m, 2H), 2.50 (s, 3H), i 2.77 (m, 4H), 4.38 (s, 2H), 7.05-7.76 (m, 6H), |} 8.94 (s, 1H), 1 0.18 (s, 1H), 12.38 (s, 1H) 235 We! lr 2.41 (s, 3H), 2.79 (s, 3H), 3.20-3.70 (m, 10H), }

O- O 7.04-7.64 (m, 6H), 8.92 (s, 1H), 10.05 (s, 1H), § 12.36 (5, 1H) 236 | WY Wa 2.40 (s, 3H), 3 .02 (m, 2H), 4.20 (m, 4H), 7.00- od od) 7.63 (m, 5H), 8.63 (s, br, 1H), 8.89 (s, 1H), 9.99 237 Oy Oy 1.35-1.85 (m, SH), 2.41 (s, 3H), 2.85 (m, 2H), 3.30 (m, 2H), 3.50 (m, 2H), 4.40 (s, 2H), 7.04- 7.71 (m, 6H), 8.94 (s, 1H), 10.15 (s, 1H), 12.38 (s, 1H) 238 | On OO 2.40 (s, 3H), 4.31/4.35 (s/s, 4H), 7.01-7.84 (m, wD 3 7H), 8.91 (m, 3H), 9.35 (s, 1H), 10.16 (m, 2H), 12.38 (s, 1H) 239 ~~ oN 2.42 (s, 3H), 3 .02 (m, 2H), 3.67 (m, 2H), 4.26

Ty (s, 2H), 5.25 (s, br, 1H), 7.05-7.52 (m, 6H), 8.93 (s, s, 2H), 10.05 (s, 1H), 12.37 (5, 1H)

280 | Oy o- 1.54-2.03 (m, 9H), 2.42 (s, 3H», 4.24 (1,

Ras D- J=5.8Hz, 2H), 7.05-7.75 (m, 6K), 8.88 s, br, 1H), 8.94 (s, 1H), 10.11 (5, 1H), 12.38 (5, 1H)

A Sy Oy [2463 42677 Fs, 4D), 7051.74 10H), 8.94 (s, 1H), 9.28 (s, br, 1H), 10.11 (s, 1H), 12.38 (s, 1H) 242 | Og roo 1.82 (m, 2H), 2.17 (m, 4H), 2.442 (5, 3H), 3.70

O- O- (m, 1H), 4.12 (s, 2H), 7.05-7.7 1 (m, 6H), 8.93 (s, 1H), 9.05 (s, br, 1H), 10.15 (s, 1H), 12.39 Gs, 1H) 243 Try Ty 1.25-2.20 (m, 5H), 2.40 (5, 3H), 2.70-3.00 (m, 4H), 4.45 (m, 2H), 7.00-7.80 (am, 6H), 8.90 (s, 1H), 9.50 (m, 1H), 10.15 (s, 13), 12.40 (s, 1H) 243 | I, x 1.11 (4, J=6.4Hz, 3H), 2.42 (s.. 3H), 2.75 (m, o- O- 2H), 2.95 (m, 1H), 3.95 (m, 1 EJ), 4.26 (s, 2H), 7.04-7.53 (m, 6H), 8.90/8.93 (s/s, 2H), 10.15 (s, 1H), 12.40 (s, 1H) 745 “Oy, On, 2.10 (m, 2H), 2.42 (s, 3H), 3.23 (m, 6H), 3.71 (m, 6H), 4.40 (s, 2H), 7.05-7.78 (m, 6H), 8.95 (s, 1H), 10.20 (s, 1H), 12.40 (ss, 1H) 246 ry aN 0.80 (m, 41), 2.42 (5, 3H), 2.75 (m, 1H), 4.33 (s, 2H), 7.04-7.74 (m, 6H), 8.93 (s, 1H), 9.10 (s,

WS | OF Tr | 226 30,347 (m, 28), 425435 m, 48, 6.90-7.80 (m, 11H), 8.96 (s, 1 H), 9.15 (s, br, 1H), 10.15 (s, 1H), 12.38 (s, 1 H) 743 Sy Sry 1.10-2.12 m, 11H), 2.41 (s, 3 H), 4.25 (5, 2H), 7.03-7.72 (m, 6H), 8.74 (s, br, 1H), 8.92 (s,

TTY em @ @ 7.69 (m, 6H), 8.96 (s, 1H), 10 10 (s, 1H), 12.37 (s, 1H)

250 3 3 1.61-1.70 (xn, 6H), 2.58 (5, 3H), 3.42 (m, 2H), 3 3 3.67 (m, 2E3), 7.09-7.75 (m, 6H), 9.01 (s, 1H), 10.14 (5, 1 EJ), 12.42 (s, 1H) 251° OO OO 1.10-1.90 (am, 10H), 2.40 (s, 3H), 3.85 (m, 13), 6.83 (s, 151), 7.21 (s, 1H), 7.68-7.77 (m, 4H)», 3 on 9.36 (s, 1H), 9.59 (s, 1H), 12.30 (s, 1H). 253 2.41 (s, 3HL), 7.02-7.29 (m, 6H), 8.91 (s, IED»,

TY meme 254 or ol 2.39 (s, 3HL), 3.91 (5, 3H), 6.93-7.31 (m, 31D),

TT] Fn 1H), 10.12 (s, 1H), 12.37 (s, 1H). 255 Or oY 2.43 (s, 37), 7.15 (5, 1H), 7.38 (5, 1H), 7.98 (m,

Ne No 2H), 8.80 Cm, 2H), 9.10 (s, 1H), 10.60 (s, 1 E3),

TT ae mmiten” 256 2.45 (s, 3H), 7.05 (s, 1H), 7.64 (5, 1h), 7.80 (d,] cS aS =4.8Hz, 1 H), 8.23 (d, J = 4.8Hz, 1H), 9.47 (, 1H), 9.73 Gs, br, 1H), 12.45 (s, 1H). 257 Ss 2.40 (s, 3H), 7.03-7.63 (m, 7H), 8.93 (s, 1H,

PTC mam o a 10.11 (s, 1 H), 12.37 (s, 1H). 259 2.41 (s, 3H), 7.06-7.81 (m, 5H), 8.92 (s, 1H),

NEARS ca 260 Cr Cr 2.40 (s, 3H), 7.00-7.40 (m, GH), 8.80 (s, 1FL),

NEA

261 2.42 (s, 3H), 7.05-7.50 (mm, 6H), 8.94 (s, IL),

TEE Em

NH, NH,

262 or or 3.35 (s, 3H), 3.04 (5, 6H), 6.90-7.56 (m, 6H), oN N 8.92 (s, 1H), 9.86 (s, br, 1H), 12.31 (s, 1H). 263 od 142-177 (m, 8H), 2.44 (5, 3H), 3.90 (m, 1H), , 4.12 (s, 2H), 7.09-7.70 (m, 6H), 8.60 (5, br,

HN

© OO | 1m), 881 ms, 1H), 1027 (5, 1H), 12.39 Gs, 1H). 264 Cr $4 1.08 (m, 3H), 2.51 (s, 3H), 2.80 (m, 2H), 3.65— y 4.20 (m, 3H), 7.10-7.72 (m, 6H), 8.80 (m, 2H),

AT "Se (m, 38) (m, 6H), 880 10.25 (s, 1H), 12.40 (s, 1H) 265 CC CC 2.43 (5, 3H), 3.18 (5, 2H), 4.09 (s, 2H), 7.10-

F | 7.70 (m, 10H), 9.10 (s, br, 1H), 10.10 (s, LH),

ACY TAY [770 tm 100,010 br, 1D, 10.10. 1D 12.39 (s, 1H) 266 CC CC 1.10-1.80 (m, 7H), 2.44 (5, 3H), 2.50-2.80 (m., ] 4H), 4.00 (m, 1H), 4.35 (m, 1H), 7.10-7.75 (m3, > 6H), 8.74 (5, 1H), 10.14 (s, 1H), 12.40 (s, 1H).

HO

HO

267 2.42 (5, 3H), 2.60 (5, 6H), 2.85 (m, 2H), 3.30

EN RL | (mi 2H), 4.40 (5, 2H), 7.06 (5, 1H, 7.35 (5, JED,

Y 7.52-7.76 (m, 4H), 8.66 (s, br, 1H), 8.95 (s, 1H), 10.12 (s, br, 1H), 12.38 (s, 1H) 268 2.01 (xm, 2H), 2.50 (5, 3H), 2.78 (5, 6H), 3.04 (m, 2H), 3.13 (m, 2H), 4.27 (5, 2H), 7.06-7.74

NTN NNT y "| (m, 6H), 8.94 (s, 5, 2H), 10.11 (s, LH), 12.38 1H) 260 2.20 (m, J = 6.8Hz, 2H), 2.45 (s, 3H), 2.99 (1, 2h), 4.29 (m, 4H), 7.06 (s, LH), 7.49 (s, LH),

NT oD ND 7.51-7.77 (m, 6H), 9.00 (s, 1H), 9.05 (s, br, 1H), 9.10 (s, 1H), 10.14 (s, 1H), 12.38 (s, 1H)

270 2.10 (m, 2H), 2.42 (s, 3H), 3.04 (m, 4H), 3.17 > (m, 4H), 3.75 (1m, 4H), 4.05 (m, 2H), 428 (5,

ANTS

N NAP! 2H), 7.07-7.74 (m, 6K), 8.94 (s, 5, 28D), 10.12 (s, 1H), 12.39 (5, 1H) 271 7.38 (s, 3H), 4.28 (s, 4H), 7.05-7.80 (m, 10H), 8.95 (s, 1H), 9.31 (s, br, 11), 10.10 (s, 1H),

C| Cl

Of ‘Yl 12.38 (s, 1H). 272 2.42 (s, 3H), 4.33 (5, 4H), 7.06-7.76 (m, 8H), 8.70 (m, 2H), 8.95 (5, 1HD), 9.45 (5, br, 1H),

A! YC 10.08 (s, 1H), 12.38 (s, LF). b: MeOD as solvent

Examples 273-289

Scheme 1 o OL OH O00

CY 0 NaOAc, HOAc .O CN EtOH, cat. H,SO, _0O 1

JUSSSS———— + [ES

Cl N CH,(COOH), a N 0 Reflux cl N 0 0.0

OO o ~~

SOC, DMF oy 170°C, 20min - oS 5% LiOH ag _— ) _——— «al 3 —_— ci NCI NH,NHCOOEt RIN MeOH

Microwave o 04 OH o NH, NH, 4 = Biphenyl Phosphoryl azide ee! SUZUKI YY —_— c SN tBuOH, DIEA ci NSN TT xg NA i) iN a

NH, 41M BBry in CHCl, ee!

J SEA —

Xz & if

Scheme 2

O80" Oy Ow OH “ory 170°C, 20min Sry LiAH, oN rare J Dna

Cli NZ>ci NH,NHCOOEt Ci NT ol) NT

Microwave i iS

OH On

SUZUKI yh 1M BBr, in CH,CI, ey rtm ————

XN ON XxTN ON

N N

OH © n

Scheme 3 0 0

H Ne~~Br ~TN 4 0 No SOCl,, DMF ————————r—

NO K,CO,. DMF No

ANT

OTN ~N NF, 175°C, 30min N oo hydrazinehydrate S

SP © NH,;NHCOOEL N Noo 2 °N

Na i

Microwave JN JN

-02.

Scheme 4 0

No ~~ Br ~0 HO lo i BBr, CHCl, i 0 ? _— Pp —_— N o cl NG cl NT Cl K,CO, x NZ SOP ci Nal

Je) 175°C, 30min Os o Hydredinehydra —_—_— NN y n rat yg

NHNHCOOE! 0 a sory

Microwave YN ct NY fo) Ne 0

SUZUKI H,N 0 x3

J

5S Scheme 5 (e} g 0 BBry, CH, Cl, “Or Br "cl

Ci No TT — a Nc K,CO,, DMF ~ 0} ° XY POSE ~ NN RN N lo} ) 175°C, 30tmin a NA SUZUKI) ) Ny Ny

CI” N">C1 NH;NHCOOE! oN o

Microwave OH

Scheme 6 0 ~ R 175°C, 40min-60min

L + AMINE Reductive amination ROO —_—

Nal — Nal NH,NHCOOEt

Microwave “XY HO. SN

NN 1M BBr, in CH,C, TLL, i —————— ' oh gn

The following examples were prepared as described in Schemes 1-6 above:

X, x; NN

JN

EE ET Eo A LS 273 | AO ANH, H H 1.90 (m, 2H), 2.76 (m, 2H), 4.23 (m, 2H), 6.50-7.66 (m, 3H), 7.93 (d,1=7.2Hz, 1H0,892(d,J = 8.0Hz, 1H). 274 | ~~, OH OMe | Cl H 3.97 (s, 3H), 4.78 (s, 2H), 5.62 (s, br, 1H), 7.15 (s, 1H), 7.35 (s, 1H), 9.01 (s, 1H), 12.5 3 (s, 1H) 275 ,, OH OH [Cl H 4.65 (s, 2H), 5.53 (s, bz, 1H), 7.10 (s, 1H), 7.32 (s, 1), 8.94 (s, 1H), 10.54 (s, 1H), 12.49 (s, 1H). 276 | ,, OH OMe H 3.81 (s, 3H), 4.30 (m, 2H), 4.83 co (s, 2H), 5.02 (s, br, 1H), 5.60 (s, br, 1H), 7.16-7.60 (m, 6H), 8.76 (s, 1H), 12.44 (s, 1H). 277 | ~w,, OH OMe H 3.87 (s, 3H), 4.60 (d, 2H), 4.85 & (d, 2H), 5.25 (t, 1H), 5.63 (t, 1H), - 7.15-7.48 (m, 6H), 8.989 (s, 1H), 12.45 (s, 1H). 278 | ~w, OH OMe of H 3.88 (s, 3H), 4.82 (s, 2H), 7.01-

TE fe (s, 1H).

279 | “w,, OH oH H 4.38 Cs, br, 2H), 4.71 (s, 2H), ) 9.85 Cs, 1H), 12.39 (s, 1H). 280 | ~,, OH OH H 4.58 Cs, 2H), 4.70 (s, 2H), 7.08- ¢ 7.55 (m, 6H), 8.92 (s, 1H), 9.90 or (s, LE), 12.35 (5, 1H). 281 | ™,, OH OH H 2.69 (5, 2H), 7.05-7.35 (m, 6H), ] (s, 1H). 282 | “w,, OH OMe Cr H 371 (5, 3H), 3.81 (5, 3H), 4.82 9 (s, ZH), 5.50 (s, br, 1H), 7.02 7.39 (m, 6H), 8.78 (s, 1H), 12.42 (s, LH).

N 8.82 (s, 1H), 12.42 (s, 1H) 284 | NH2 OMe 3.89 (s, 3H), 6.00 (s, 1H), 7.01- 9s, 1H). 285 | NH2 OH |Cl H 6.40 (s, br, 2H), 7.63 (s, 1H), 9.96 (s, 1H), 10.40 (s, 1H), 12.09 (s, 1H). © 13.18 (s, 1H) 287 | NH2 OH H 6.65 (s, 1H), 7.82 (d, 1H), 8.20 a (s, 1H), 8.29 (d, 1H), 9.55 (5, 1H), 9.80 (s, br, 1H), 12.15 (s, 1H). 288 |H OH |H H 1.24 (m, 2H), 1.76 (m, 4H), 3.82

Ng Na (ma, 1H), 4.10 (5, 2H), 7.12 (d, = 7.2Hz, 2H), 7.63 (s, 1H), 8.74 (4,

J =9.6Hz, 1H), 9.16 (s, br, 1H),

INI 936 br, 15), 12.71 @, LED.

PCT/SE2004/000351 289 | H OH |H H ves 4.24, 4.31 (s,s, 4H), 7.01-7.61 ve (m, TH), 8.74 (t, ] = 4.8Hz, 1H), 9.32 (s, br, 1H), 9.92 (s, 1H), 12.68 (s, 1H).

Examples 290-291 x mS NH,NHC,H,OH 0 Urea ae!

Ne TTT 1 N” “NHN H, ! J

R o H 5-Methyl[1,2,4]triazolo[4,3a]quinolin(2H)one: 5,9-Dimethyl{1,2,4]triazolo[4,3a]quinolin(2H)one:

A solution of the chloroquinoline (0.02mol) and NH,NHC,H,0H (0.02mol) ira cellusolve (10m!) was heated to reflux for four houxs. Ether was added and the resultant precipitate removed by filtration. The crude solid was recrystallized from ethanol to yield thes intermediate hydrazine.

A solution of the intermediate hydrazine (0.01 nnol) and urea (0.01mol) in DMF (10ml) was heated to reflux for two hours. The solution: was cooled and the resultant solid filtered off and recrystallized from DMF to give the pure triazolone. a0

N™SN

RN

0

I a a I

PCT/SE2004/000351

Examples 292-293

CO,H NH, gb! 1.DPPA, 2BuOH gb!

N™SN - N SN pa ba 4-Amino-2H-[1,2 4]triazolo[4,3-a}quinolin(2H) one: 5-Amino-2H-(1,2 4]triazolo[4,3-0]quinolin(2H)one:

A mixture of the starting carboxylic acid (0.2mmol), diphenylphosphoryl azide (0.22mmol), diisopropylethylamine (0.22mmol) -in t-butanol (1m) was heated at 80°C for six hours. Excess t-butanol was removed in vacuo and the residue suspended in CHI,Cl,/MeOH.

The solid was removed by filtration, the filtarate evaporated and purified by silica gel chrormatography.

The BOC protected amine (0.lmmol® was suspended in CH,Cl, €0.5ml) and trifluoroacetic acid (0.5ml) added. The resultant mixture was stirred at room termperature for two hours. The reaction mixture was evaporated and the residue triturated to give a solid.

This solid was filtered off and dried under high vacuum to give the desired amine.

NH, ! a (Ex | Ro ] 1H NMR (400MHz, DMS 0-d6) 292 4- NH, 5.73 (s, 2H), 6.40 (s, 1H), 7.19-7.31 (m, 1H), 7.40-7.50 (m., 1H), 8.76-8.84 (m, 1H), 12.50 Cs, 1H) 5.94 (s, 1H), 7.41 (t, 7H), 7.60 (t, 1H), 7.98 (d, 1H), 8.98 (d, 1H)

Examples 294-296 * R on NH,NHCO,Et jee! ——> R NSN

R Nel, Br Ra (1,2,4]triazolo[4,3a]quinolin(2H)one: 8-Methoxy[1,2,4]triazolo[4,3a]quinolin(2H)one: 8-Fluoro[1,2,4]triazolo{4,3a]quinolin(2H)one:

The starting haloquinoline was dissolved in NMP (1.9ml) in a 20x125 reaction tuabe.

A catalytic quantity of HCI (4M in dioxane) was added and the reactions heated in a block at 135°C until complete as determined by LC MS.

The mixtures were cooled and the precipitated product removed by filtration. If necessary the product was purified by chromatogmraphy.

R

Q

R NSN a a I

Ea A LL a NE

Ei IL TL 7 py I EE

Examples 297-332

The following examples were prepared via Suzuki (previously described),

Sonogashira or Stille coupling as appropriate:

A typical procedure for Sonogashira coupling is as outlined below: 8-bromo-5-methyl{ 1,2[4}triazolo[4,3-a]quinolin -1(2H)-one, (100mg, 0.36mmol), dichloro bistriphenyl phosphine palladium (13mg,0.018m-mol), copper iodide (3.5mg,0.018mmol) were dissolved in dry THF (1 mL), triethylamine (0. 15mL,1.08mmol), alkyne (0.54mmol)

were added, the solution was degassed for 5 minutes, then heated up at 60°C under argon for 2.5 hours. The crude product was purified by prep. HPLC to obtain 6% and 35 % of the desired product,

XN PACL(PPh,),/Cul x + R—=H — 5

Br N SN y 4 3 N

JO ] 0 ° a I. NO Lc io) 2.45(s, 3H), 2.91 (5s, 6H), 4.39(s, 2H), 7.13(s, 1H), wx (5. 3H), 251, 6H), 439(s, 20), T13G, 1D, / 7.63(d, 1H), 7.86 (d, 1H), 9.10(s, 1H) 2.45(s, 3H), 2.69(bs, 3H), 4.22(bs, 2H), 7.12(s, xX (s, 3H) (bs, 3H) (bs, 2H) ( 267 / 1H), 7.57(d, LH), 7.86(d, 1H), 9.10(s, 1H)

BR 0.95(t, 6H), 2.20Cs, 3H), 3.39(q, 2H), 3.47(q, 2H),

BOT le | 5.36(s, 1H), 6.86(s, 1H), 7.33(d, 1H), 7.58(d, 326 1H), 8.78(s, 1H)

Examples using the Stille coupling procedure were prepared as follows:

The appropriate triazolone (1 eq) was placed in a microwave tube containing a stir bar and the desired stannane (1.5 eq) was added together with palladium tetrakistriphenylphosphine (7 mol%) and dioxane (3 mL). A few grains of NaCl were added and the contents were heated in a Smith Synthesizer (microwave) for 1800 secs at 140 OC followed by 1200 secs at 165 °C.

The desired product was isolated by HPLC purification (5-20%).

OH

NY OH Cs,CO R X

Br pu N Dioxane:H,0 17

N

EX HNMR

MS(MH+) 300 A 2.32 (5, 3H), 6.13 (m, TH), 6.51 (s, © H), 6.88 (s, 2H), 265

Da 7.68 (m, 2H), 9.12 (s, 1H), 11.51 (s, TH) 301 y 3.43(m, 5H), 6.48(t, 1H), 6.90(m, 21 H), 7.32(sm, 1H), | _ 265 vg 7.69(d+d, 2H), 9.13(s, 1H) 302 R 2.47 (s, 3H), 6.98(s, 1H), 7.20 (m., 1H), 7.61 (m, 282 <r 2H), 7.80 (s, 2H), 9.28 (s, 1H) 303 5 2.46 (s, 3H), 6.56 (br s, TH), 7.01 Cs, TH), 7.60 (d, 282 , 1H), 7.76 (d, 1H), 7.84 (s, 2H), 7.99 {d, 1H), 9.30 s, 1H) 304 Er 2.46 (5, 3H), 6.68 (m, TH), 7.02 (5, 1H), 7.11 (d, 1H), 266 \_/ 7.82 (m, 3H), 9.30 (s, 1H) 305 ® 2.45(s, 3H), 6.94(s, 1H), 7.00(s, 1H), 7.73(4, 1H), | 266 0 7.83(m, 2H), 8.29(s, 1H), 9.15(s, 1H) 306 i 2.43 (s, 3H), 6.93 (s, 1H), 7.74 (mn, 2H), 8.12 (5, 266 ww 2H), 9.18 (s, 1H) 307 n A 2.46 (s, 3H), 6.55 (or 5, 1H), 7.20 (s, 1H), 8.0 (m, 283

J 2H), 8.10 (m, 2H), 9.64 (s, 1H) 308 , 2.50 (5, 3H), 6.54 (5, 1H), 7.12 (5, 1H), 7.94 (d, TH), 278 [ YY 8.24 (m, 1H), 8.70 (m, 1H), 8.82 (an, 1H), 9.33 (s.

N 1H), 9.78 (s, 1H) 309 2.2(s, 31), 2.4 (s, 3H), 6.8 (d, 1H), 7.0 (5, 1H), 74 4, | 306 1H), 7.5 (s, 1H), 7.7 (d, 1H), 7.9 (d, 1H), 9.25 (s, 1H),

Ho 9.7 (s, 1H) 310 24 (s, 3H), 71 (s, 1H), 7.8 (m, THY, 7.9 (m, 3H), 8.0 | 301

Cr (m, 1H), 8.2 (s, 1H), 9.3 (5, 1H), 12.5 (s, 1H)

CN

311 | 2.4 (5, 3H), 65 (5, 1H), 7.2 (s, 1H), 7.9 (m. 5), 84 (5, | 301 or 1H), 12.6 (s, 1H)

NC

312 2.4 (5,31), 4.1 (5, 3H), 6.6 (s, 1H), 7.0 (5, 1H), 750, | 315 jo) 2H), 7.8 (m, 3H), 7.9 (d, 1H), 9.3 (s, 1H)

CN

313 ~ 2.4 (s, 3H), 7.0 (s, 1H), 7.7 (m, 1H), 7.0 (m, 2H), 82 | 377 - (m, 1H), 8.7 (d, 1H), 8.9 (s, 1H), 9.3 (s, 1H)

314 HO 2.4 (s, 31), 6.8 (1H, 5), 7.25 (d, 1H), 7.4-7.6(m, 4H), } iH or 7.7 (d, 1H), 7.85 (d, 1H), 8.9 (s, 1H) {306

J

{ 315 2.4 (s, 31), 3.8 (5, 3M), 7.0 (5. 1M), 7.1 (@ TH), 7.7 { 306 or (ms, 3H), 7.9 (d, 1H), 9.4 (s, 1H) ) ~o : 316 2.4 (s, 3H), 6.5 (bs, 1H0, 6.9 (m,3H), 7.7(d, 2M), 7.8 | 292 or (d. 1H), 7.9 (d, 1H), 9.2(s, 1H), 9.8 (bs, 1H)

HO

317 AN_O 2.4 (5, 3H), 7.0 (5, 1H), 7.3 (s, 1H), 7.5 (m, 4H), 7.8 319

X (my, 2H), 9.1 (s, 1H) 318 2.4 (5, aH), 6.8 (5, 1H), 7.5 (5, 1H), 7.55-7.9 (m, 4H), 319 8.1 (s, 1H), 8.2 (s, 1H), 9.5 (s, 1H) 07 NH, 319 HO 2.4 (s, 3H), 4.5 (s, 3H), 6.8 (m, 1H), 7.05 (s, 1H), 7.25 336 (2, 3H), 7.5 (d, 1H), 7.8 (d, 1H), 8.8 (s. 1H) ~o 320 0 2.4 (s, 3H), 2.5 (5, 6H), 7.05 (s, 1H), 7.5 (d, 1H) 7.09 295 jug (d, 1H), 8 (s, 1H) 321 2.38 (s, 3H), 2.48 (s, 3H), 3.00(s, 3H), 6.92 (s, 1H), 347 oA 7.56 (d, 2H) 7.72 (m, 4H), 9.50 (s, 1H)

Pa 322 1.85 (t, 4H), 2.34 (5, 3H), 3.42 (t, 4H), 6.92 (s, 1H), 373 o J 7.65 (m, 6H), 9.56 (s, 1H)

O

323 1.50 (m, 6H), 2.45 (s, 3H), 3.32(m, 2H), 3.60(m, 2H), 387 o AT 7.02 (s, 1H), 7.50 (d, 2H) 7.80 (m, 3H), 9.35 (s, 1H)

O

324 2.48 (s, 3H), 3.62 (m, 8H), 7.02 (s, 1H), 7.56 (d, 2H) 389

AT 7.84 (m, 4H), 9.28 (s, 1H) @

0351 325 2 2.48 (s, 3H), 2.90 (s, 3H), 7.05 (s, 1H), 7.45 (m, 5H) 369 ~g=0 7.90 (d, 1H), 8.98(s, 1H), 9.05 (s, 1H) 326 | ~_ 2.48 (s, 3H), 3.00 (s, 3H), 7.05 (s, 1H), 7.28 (d, 1H) 369 208 7.50(m, 3H), 7.71 (d, 1H), 7.90(d, 1H), 9.28 (s, 1H) 327 2.48 (s, 3H), 3.02 (s, 3H), 7.02 (s, 1H), 7.35 (d, 2H) 369 se I 7.70 (m, 3H), 7.88(d, 1H), 9.28 (s, 1H) 328 2.20 (s, 3H), 2.38 (s, 3H), 6.90 (s, 1H), 7.18 (s, 1H), 296 —T 7.40 (s, 1H) 7.68 (d, 1H), 7.74(d, 1H), 9.18 (s, 1H) 329 2.48 (s, 3H), 4.60 (d, 2H), 5.52(t, 1H), 6.95 (m, 2H), 312 hed 7.40 (s, 1H) 7.70 (m, 2H), 9.18 (s, 1H) 330 2.48 (s, 3H), 2.60 (s, 3H), 7.05 (s, 1H), 7.75 (d, 1H) 324 = a 7.90 (m, 2H), 8.00(d, 1H), 9.35 (s, 1H) 0 331 1.38(d, 3H), 2.48 (s, 3H), 4.90 (q, 1H), 6.96 (m, 2H), 326 id 7.40 (s, 1H) 7.65 (m, 2H), 9.18 (s, 1H) 332 2.48 (s, 3H), 7.02 (s, 1H), 7.60 (a, 1H) 7.74 (d, 1H), 326 a 7.82(m, 1H), 9.28 (s, 1H) []

Examples 333-339

Fused triazolones with alkoxy substituents were generated from alkylation of the boronate ester of phenol using the appropriate alkyl chloride (1.1 eq) and heating the reactants 5 in DMF in the presence of cesium carbonate (1.1 eq). The alkylated methyleneaminophenyl substituted triazolones were synthesized via amination of bromomethylphenylboronic acid with the appropriate amine (2M in THF) at reflux (2h to overnight) to yield the corresponding aminated boronic acid.

The alkylated boromic acids prepared as described above were used to synthesize the : following examples using the Suzuki coupling conditions previously described. r e9B>o Ns © i

B~ r

Of © RCI oy 8o\ ° 3d OO NN —_— [ESSN » ROTI

HO Cs,CO/DMF go Pdo(dba)yBuP po HN

Na_CO, ©

DMAE/EtOH/H,0

Ra BL LC 4.69(s, 2H), 5.45(bs, 1H) ,6.88(s, 1H), 333 Q ARNE 7.01(s, 1H), 7.65(d, 1H), 7.71(d, 1H), 405 7.77(s, 1H), 8.22(s, 1H), 9.10(s, 1H) 1.25(t, 6H), 2.47(s, 3H), 3.26(q, 4H), \ - MM 3.57(t, 2H), 4.40(t, 2H), 7.03(s, 1H), - 7.19(d, 2H), 7.76(m, 3H), 7.87(d, 1H), 9.27(s, 1H) : joe ? oo ILA ~ ~OH R,R,NH ~OH py ®

THE _ NTN N

Pd(PPh,),/Cs> CO; R RN PN

Br NR, R, Dioxane/H,0 0 2.43(s, 3H), 3.15(t, 3H), 3. 24(t, 1H), q WN 3.57(t, 1H), 3.89(t, 1H), 4.37(s, 2H), 1s 7.02(s, 1H), 7.61(d, 2H), 7 .79(m, 3H), 7.86(d, 1H), 9.26(s, LH) 2.26(s, 3H), 2.55(bs, 3H), 2.80(m, 2H), - MeN N 3.14(m, 2H), 3.49(m, 6H), 6.83(s, 1H), 188 7.28(d, 2H), 7.53(m, 3H), 7.66(d, 1H), 9.07(s, 1H)

2.31(s, 3H), 2.42(t, 3H), 4.02(t, 2H), 337 6.88(s, 1H), 7.45(d, 2H), 7.63(m, 3H), 319 ]

CH;NH 7.72(d, 1H), 9.13(s, 1H) 1.42(s, 9H), 2.49(s, 3H), 3.10(m, 4H), 238 3.72(m, 2H), 4.08(m,2H), 4.82(s, 2H), 47 7.08(s, 1H), 7.67(d, 2H), 7.84(m, 3H), 7.92(d, 1H), 9.32(s, 1H) 2.46(s, 3H), 3.57(m, 8H), 4.45(s,2H), 339 w{_) 7.07(s, 1H), 7.82(m, 4H), 7.90(d, LH), 374 9.31(s, 1H) 8-bromo-5-bromomethyl[ 1 ,2[4]triazolo[4,3-a}quinolin-1(2H) -one was synthesized using the following proecedure: 8-brormo-5-hydroxymethyl[1,2[4]triazolo[4,3-a]quino 1in-1(2H)-one (5.92 mmols, 1.5 g) was susperaded in DMF (30 mL) and CBr4 (7.11 mmols, 1.2 eq, ,2.36 g) and PhyP (7.11 mmols, 1.2 eq., 1.86 g) added. The resultant mixture was heated with stirring at 80 deg and the reaction progress monitored by LC-MS. After heating for 4 bh, a further 0.6 eq. each of

CBr4 (0.98 g2) and PhyP (0.78 g) were added and heating continued until complete disappearance of the starting alcohol was observed. The reac tion mixture was cooled to room temperature and the precipitated product was filtered off, washed with methanol followed by

DCM followe=d by hexanes to give the required product as a light gray powder (55-58%).

Examples 34 0-364 5-forrmyl 3-thiophene boronic acid (100mg, 0.64mmo1X) was dissolved in DME (3ml), and the appropriate amine (3.2mmol) was added, followed by” a drop of HOAc. The resulting solution was stirred for 5 minutes at room temperature. Sodium triacetoxyborohydride (271mg, 1.28ammol) was added and the resulting solution was heated at 60°C for 5 hours. The solvent and excess amine were evaporated under vacuum and the crude product used without further purifi cation to couple with the appropriate 8-bromotr-iazolone as previously described.

X X

& 0 joo

AS -° R,R;NH Bg ” pe 3 Sy

Is Noa wan AS PUPP, 00, (> JH

X = CHg » NH,, CH,OH, CONE.

For the following examples X=rmethyl 2.47(s, 3H), 3.15(bs, 4H), 3.30(bs, 4H), 4.68(s 2H), 7.05(s, 1H), 7.79(s, 1H), - 7.86(m, 2H), 8.07(s, 13H), 8.20(s, 1H),

NA 9.30(s, 1H) 2.47(s, 3H), 2.62(bs, 2H), 4.44(bs, 2H), 7.05(s, 1H), 7.757(s, 1H), 7.85(m, 2H), 325

CH;NH 8.1 1(s, 1H), 9.29(s, 1H) 2.246(m, SH), 2.80(s, 34H), 3.05(m, 4H), - o [EERmEn |. — 7.47(s, 1H), 7.83(m, 2H), 7.95(s, 1H),

MN 9.26(s, 1H) 1.a1(s, 9H), 2.47(s, 3H), 3.05(m, 2H), -| [EREER |. — 7.05(s, 1H), 7.86(m, 3H), 8.17(s, 1H),

NIA 9.22(s, 1H) 2.47(s, 3H), 3.46(m, 8H), 4.72 (5,25), 344 7.03(s, 1H), 7.85(m, 3H), 8.16(s, 1H), 380

Ho [mms |e 1.00(m,2H), 2.47(s, 3H), 2.78(s, 6H), us 3.2 1(m, 4H), 4.50 (bs, 2H), 7.05(s, 1H), 10 7.77(s, 1H), 7.84(m, 2H), 8.13(s, 1H),

MeN” "NH 9.30(s, 1H)

Claims (20)

PCT/SEZ2004/000351 Claims

1. A compound having formula (I): Him A IS (Al in RY” Vo NAN SI Si 0) H (0 wherein: m is independently selected at each occurrence from 0 or 1; nis 0; R'is H, OH, F, Cl, Br, I, NHa, -C(=O)R", -C(=0)NHR®, C(=0)CH:R", -C(=0)(CH,)2R®, -C(=0)(CH2)3 R", -C(=0)NH(CH,)NHz, -C(=O)NH(CH,):NH2> , -C(=0)NH(CH,)3NH,, -C(=0)NH(CH2)N(CHs)z, ~C(=O)NH(CH2)2N(CHs)2, -C(=0)NH(CH:)3N(CHj3)s, -C(=0)NH(CH2):NHCHj, -C(=O)NH(CH2):0H, -C(=0)NHNHa,, -C(=0)NHCH(CH;3)CH>N(CH3)», -C(=0)NH(CH2);NHCH(CH3):, -(CH2)150H., -C(=0)OR?, -C(=O)NHNHo, NH(CH»):.3R?, -CH,NH(CH,)13R?% -NHC(=O)OR., -(CsHs)NH-cycloalkyl, -(C¢H4)INH-optionally substituted heterocycle, -(C¢Ha)CH,NH-alkyl-OH, -(CsH4)N(CH3)2, -O-alkyl-NH,, optionally substituted alkyl, optionally substituted N-alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted cycloalkynyl, optionally substituted aryl, optionally substituted alkoxy, optional 1y substituted heterocycle, or optionally substituted fused heterocycle; R’is H, OH, F, Cl, Br, I, NH, -(CH);;0H, -C(=0)OR?, -C(=O)NHNH x, -NH(CH3);3R%, -CH,NH(CH,)1 3R?, -NHC(=O)OR, optionally substituted alkyl, optionally substituted N-alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted cycloalkynyl, optionally substituted aryl, optionally substituted alkoxy, optional ly substituted heterocycle, or optionally substituted fused heterocycle. AMENDED SHEET

: PCT/SE2004/000351 R® is H, OH, F, Cl, Br, I, NH,, or CH; R* is OCHj, -(CéHs)CHoNH(CHy)13R?%, -(C¢H4)CHN(CH3)(CHa) 13K, ~(CgHa)CH2R?, ~(CeHa)(R")CH,R?, -(CoHa) CH 2NHR?, -(CsHa)C(=O)R?, (CeHa)NHC(=O)R?, ~(C¢Hy)CHaNH(CH2)13R'R®, <(CsH4)NHSO,CHs, optionally substituted ary 1, or optionally substituted heterocycle; RS is H, OH, F, CL Br, I, NHz, OCHs, —C(=0)OR?, -C(=0)NHNH,, -NH(CH,)13R%, -CH,NH(C H,)1.3R? -NHC(=0)OR?, optionally substituted alkyl, optionally substituted N-alkyl, op tionally substituted alkenyl, optionally substituted alkynyl, optiorally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted cycloaulkynyl, optionally substituted aryl, optionally substituted alkoxy, optionally substituted heterocycle, or optionall y substituted fused heterocycle; R®isH, OH, F, Cl, Br, I, NH,, -NHC .salkyl, -N(C,.¢alkyl), -(CeH4)€C HR, -(CsH4)CH2NR®R®, or optionally substituted aryl; R® is H, OH, OCHj3, C).salkyl, Cy.¢alkoxy, -NHa, -NHCH;, -N(CHs)z -CH,CH(CHs)», optionally substituted phenyl, optionally substi tuted cycloalkyl, optionally suabstituted 5 or 6 or 7 membered heterocycle having 1 or 2 oxygen or 1 or 2 nitrogen or 1 nitrogen and oxygen or 1 nitrogen and 1 sulfur or 1 oxygen and 1 sulfur ring atoms; R® is H, OH, OCHj, C; galkyl, or C ealkoxy; R® is optionally substituted Cs-7heterocycle; Xis C; Yis C; Zis C; Vis CG; or a pharma ceutically acceptable salt thereof.

2. A compound of formula (I) as claimed 1n claim 1 or a pharmaceutical ly acceptable salt thereof wherein m is 0.

3. A compound of formula (I) as claimed in claim 1 or a pharmaceutical ly acceptable salt thereof wherein R! is -C(=0)R’, -C(=0)NHR?, -C(=0)CH,R", -C(=0)(CH:):R", -C(=0)(CH=> sR", -C(=0)NH(CH2)NH,, -C(=ODNH(CHz),NH;, -C(=0)NH(CHz);NHz, -C(=O)NH(CH)N(CHj),, -C(=0)NH(CH2)sN(CHa)a, -C(=0)NH(CH2)sN(CE3)a, AMENDED SHEET

) PCT/SE2004- /000351 -C(=0)NH(CH,);NHCHj, -C(=0)NH(CHz);:0H, -C(=O)NHNH,, -C(=0)NHCH(CH;)CH,N(CHj3)a, or -C(=O)NH(CH;),NHCH(CHj)..

4. A compound of formula (I) as claimed im claim 1 or a pharmaceutically acceptable salt thereof wherein R! is NH,, CH, -(CH,),.30H, -(CsHs)NHcycloalkyl, O(CH>),.3N Ho, -(C¢H4)NH-cycloalkyl, -(CsHs)NH-optionally substituted heterocycle, -(C¢H4)CH,NH-alkyl-OH, -(C¢H4)N(CHz),, or ~O-alkyl-NHa.

5. A compound of formula (I) as claimed in claim 1 or a pharmaceutically acceptable salt thereof wherein R? is H or -(CH,),30H.

6. A compound of formula (I) as claimed in claim 1 or a pharmaceutically acceptable salt thereof wherein R? is H.

7. A compound of formula (I) as claimed in claim 1 or a pharmaceutically acceptable salt thereof wherein R* is optionally substituted furan, optionally substituted pyridine. or optionally substituted thiophene wherein said substitution is selected from ~N(CHs)», -NCH,NCHs, -CH,NCH3, -CH,-piperazine, or —-CH-methylpiperazine.

8. A compound of formula (I) as claimed in claim 1 or a pharmaceutically accep®able salt thereof wherein R® is H, OH, or OCHs.

9. A compound of formula (I) as claimed in claim 1 or a pharmaceutically accep#able salt thereof wherein R® is H, -(CeHs)CHaR?, or ~(C¢Hs)CH,NRR”.

10. A compound of formula (I) as claimed in claim 1 wherein: misOorl; nis 0; R'is NH, CH, -(CH2)1.30H, -(C¢Ha)N Hceycloalkyl, -O(CHz);3NHa, -(C¢H4)NH-cycloalkyl, -(C¢Hs)NH-optionally substituted heterocycle, -(C¢H4)CH,NH-alkyl-OH, -(C¢H4)N(CH3), or -O-alkyl-NHy; R* is H or -(CH)1.30H; R® is H; AMENDED SHEET

. PCT/SE2004/000351 R* is OCH3, -(C¢H. )CHNH(CH,)13R?, -(CeHa)CHaN(CH3)C CHa) 13R?, -(CeHa)CHaR?, ~(CsHANRPICHaR?, -(CHy) CHaNHR?, «(CsHa)C(=0 IR?, -(CsHy)NHC(=O)R’, -(C¢Ha)CH;NH(CH,),3R*R®, -(CsHa)NHSO,CH;, optionally substituted aryl, or optionally substituted heterocycle; . R’ is H, OH, or OCHj; R® is H; -(CsH4)CHLR?, or -(C¢Hs)CHaNRR®; R? is OH, OCH;, C isalkyl, -NH,, -NHCHj;, -N(CHs)a, -CH,&H(CHas),, optionally substituted cycloalkyl, optionally substituted 5 or 6 or 7 membered Eneterocycle having lor2 oxygen, or 1 or 2 nitrogen, or 1 nitrogen and 1 oxygen, or 1 nitrogeraiand 1 sulfur, or 1 oxygen and 1 sulfur ring atoms; R® is OH, OCH3, C 14alkyl; X,Y, Zand V are C; or a pharmaceutically acceptable salt thereof.

11. A compound selected from: 5,9-dimethyl[1,2,4]triazolo[4,3-ajquinolin-1(2H)-one; 8-methoxy-5-methyl[1,2,4 Jtriazolo[4,3-a]quinolin-1(2H)-one; 8-fluoro-5-methyl{1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 5-bromo-3-(hydroxymethy 1)[1,2,4]triazolo[4,3-ajquinolin-1(2H)-orme ethyl-7-bromo-1-oxo0-1,2-dihydro[ 1 ,2,4]triazolo[4,3-a]quinoline-5-carboxylate; ethyl-7-methyl-1-ox0-1,2-dihydro[1 ,2,4]triazolo[4,3-a]quinoline-5-acarboxylate; 7-methyl-1-ox0-1,2-dihydro[1,2,4]triazolo[4,3 -a]quinoline-5-carbolydrazide; 5-amino[1,2,4]triazolo[4,3 -a]quinolin-1(2H)-one; 5-amino-7-bromo(1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 7-methoxy-5-methyl[1,2,4 Jtriazolo[4,3-a]quinolin-1(2H)-one; 7-hydroxy-5-methyl[1,2,4 Jtriazolo[4,3-a]quinolin-1(2H)-one; 8-hydroxy-5-methyl[1,2,4 Jtriazolo[4,3-a]quinolin-1(2H)-one; 5,7-dimethyl[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 5,8-dimethyl[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 9-hydroxy[1,2,4]triazolo[4,3-a]lquinolin-1(2H)-one; t-butyl-7-bromo-1-oxo-1,2-dihydro[1 ,2,4]triazolo[4,3-alquinolin-5- ylcarbamate; 7,8-dihydroxy-5-methyl[1 ,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 7,8-methoxy-5-methyl[1,2 ,4]triazolo[4,3-a]quinolin-1(2H)-one; AMENDED SHEET

: PCT/SE2004/0000351

7,8-methoxy[1,2,4]triazolo[4,3-a]quinolin-1{2H)-one; 7,8-dihydroxy[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 5-chloro[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 1-oxo-1,2-dihydro[1,2,4]triazolo[4,3-a]quinoline-5-carbohydrazide; 7-bromo-5-methyl[1,2,4]triazolo{4,3-a]quinolin-1(2H)-one; 7-iodo-5-methyl[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 7-(3-aminophenyl)-5-methyl[1,2,4]triazolo[4,3-a]quinolin-1 (2H)-one; 7-(3-hydroxyphenyl)-5-methyl[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 8-(3-hydroxyphenyl)-5-methyl[ 1.2,4]triazolo[4,3-a]lquinolin-1(2H)-one; 8-[3-(hydroxymethyl)phenyl-5-methy1[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 8-[4-(hydroxymethyl)phenyl-5-methy1{1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 8-(3-aminophenyl)-5-methyl[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 5-(3-aminophenyl)[1,2,4]triazolo[4,3~a]quinolin-1(2H)-one; 5-[4-(hydroxymethyl)phenyl[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; ethyl 7-methyl-1-oxo-1,2-dihydro[1,2 ,4]triazolo[4,3-a]quinoline-5 -carboxylate; 5-amino-7-(3-aminophenyl)[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 7-(2-hydroxyphenyl)-5-methyl[ 1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 4-amino[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 5-amino-7-(3-hydroxyphenyl)[1,2,4]triazolo[4,3-a]quinolin-1(2H}-one; 5-amino-7-[3-(hydroxymethyl)phenyl](1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 5-(1-benzothien-2-yl)[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 5-[3-(hydroxymethyl)phenyl][1,2,4]triazolo{4,3-a]quinolin-1 (2H)-one; 5-[(E)-2-(4-chlorophenyl)vinyl][1,2,4 Jtriazolo[4,3-a]quinolin-1(2H)-one; 5-(2,4-dihydroxyphenyl)[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 7-(2-hydroxyphenyl)[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 5-(2-furyl)[ 1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 7-(2,4-dihydroxyphenyl)-5-methyl[1 ,2,4]triazolo[4,3-a}quinolin-1(2H)-one; 5-phenyl[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 5-{[2-(3,4-dimethoxyphenyl)ethyl]amino}[1 ,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 5-[2,6-difluorobenzyl)amino][1 ,2,4]triazolo[4,3-a]quinolin-1(2H)-one; ethyl 1-oxo-1,2-dihydro[1l ,2,4]triazolo[4,3-a]quinoline-5-carboxylate; 5-{4-{[(2-pyridin-2-ylethyl)amino]methyl} phenyl }[1 ,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 5-{4-{[(2-hydroxyethyl)amino]methy 1} phenyl }[1 ,2,4]triazolo[4,3-a]quinolin-1(2H)-one AMENDED SHEET

R P<CT/SE2004/000351

8-bromo-1-oxo-1,2-dihydro[1,2,4] triazolo[4,3-a]quinoline-5-carboxylic aci d; 7-[(4-hydroxymethyl)phenyl]-5-methyl[1,2,4]triazolo[4,3-a]quinolin-1(2H» -one; 5-{4-[(4-methylpiperazin-1-yl)methyl]phenyl}[1,2,4]triazolo[4,3-a]quinolir1-1(2H)-one; 5-(benzylamino)-7-bromo[1,2,4]tri azolo[4,3-a]quinolin-1(2H)-one; ethyl 7-methoxy-1-oxo-1,2-dihydro[1,2,4]triazolo[4,3-a]quinoline-5-carboxylate; 5-[4-{{[3-(dimethylamino)propyl]amino} methyl!phenyl][1,2,4]triazolo[4,3 -a]quinolin- 1(2H)-one; 5-{4-{[(3-morpholin-4-ylpropyl)armino]methyl} phenyl }[1,2,4]triazolo[4,3 -a]quinolin-1(2H)- one; 5-amino-7-methyl[1,2,4]triazolo[4, 3-a]quinolin-1(2H)-one; t-butyl 7-methoxy-1-oxo-1,2-dihyd ro[1,2,4]triazolo[4,3-a]quinolin-5-yl cartoamate; 5-amino-7-methoxy[1,2,4]triazolo[ 4,3-a]quinolin-1(2H)-one; 8-dimethylamino-5-methyl[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 5-amino-8-{4-(hydroxymethyl)pherayl][1,2,4]triazolo[4,3-a]quinolin-1(2H)-One; 5-(4-{[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]methyl} phenyl)[1 ,2,4]triazolo[4,3-a]quinolin- 1(2H)-one; 5-[4-({[1-(hydroxymethyl)-2-methy’Ipropyl]amino }methyl)phenyl][ 1 ,2,4]trizazolo |4,3- a]quinolin-1(2H)-one; 5-(4-{[4-(3-methylphenyl)piperazin -1-ylJmethyl} phenyD)[1,2,4]triazolo[4,3- alquinolin- 1(2H)-one; AMENDED SHEET

148. PCT/SE2004/000351 > 7-(3-aminophenyl) -5-methyl[ 1,2 4]triazolo[4,3-a]quinolin-1(2H)-one; 7-(3-hydroxypheny/1)-5-methyl[ 1,2 4]triazolo[4,3-a]quinolin-1(2H)-one; 8-(3-hydroxypheny 1)-5-methyl|1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 8-[3-(hydroxymethx yl)phenyl-5-methyl[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 8-[4-(hydroxymethz yl)phenyl-5-methyl[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; ’ 8-(3-aminophenyl)—5-methyl[1,2,4]triazolo[4.3-a]quinolin-1(2H)-one; 5-(3-aminophenyl) [ 1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; ) 5-[4-(hydroxymeth yl)phenyl| 1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; Ethyl-ethy! 7-methyl-1-oxo0-1,2-dihydro[1,2,4]triazolo[4,3-a]quinoline-5 -carboxylate; 5-amino-7-(3-amin ophenyl)[1,2,4}triazolo[4,3-a]quinolin-1(2H)-one; 7-(2-hydroxypheny~1)-5-methyl[1,2,4|triazolo[4,3-a]quinolin-1(2H)-one; 4-amino(1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 5-amino-7-(3-hydroxyphenyl)[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 5-amino-7-[3-(hydroxymethyl)phenyl][1,2,4|triazolo[4,3-a]quinolin-1(2H)-one; 5-(1-benzothien-2-w1)[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 5-[3-(hydroxymeth yl)phenyl][1,2,4]triazolo[4,3-a]quinolin- 1 (2H)-one; 5-[(E)-2-(4-chloropphenyl)vinyl][1,2,4}triazolo[4,3-a]quinolin-1 (2 H)-one; 5-(2,4-dihydroxypheenyl)[1,2,4]triazolo{4,3-a]quinolin-1(2H)-one; 7-(2-hydroxypheny 1)[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 5-(2-furyl)[1,2,4]tri azolo[4,3-a]quinolin-1(2H)-one; 7-(2,4-dihydroxyphaenyl)-5-methyl| 1,2 4]triazolo|4,3-a]quinolin-1 (2H)-one; 5-phenylf1,2 4|triaz=olo[4,3-a]quinolin-1(2H)-one; 5-{[2-(3,4-dimetho xyphenyl)ethyl Jamino}{1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 5-[2,6-difluorobenzzyl)amino][1.2,4]triazolo|4,3-alquinolin-1(2H)-one; Ethyl-ethyl 1-0xo0-1 ,2-dihydro[1,2,4]triazolo[4,3-a)]quinoline-5-carboxylate; 5-{4-{[(2-pyridin-2 -ylethyl)amino]methyl} phenyl }| 1,2,4]triazolo [ 4,3-a]quinolin-1 (2H)-one; 5-{4-{[(2-hydroxyethyl)amino]methyl} phenyl }[1,2 4]triazolo[4,3 -a]quinolin-1(2H)-one 8-bromo-1-oxo0-1,2—dihydro[1,2,4}triazolo[4,3-a]quinoline-5-carboxylic acid; 7-|(4-hydroxymethy/l)phenyl]-5-methyl| 1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 5-{4-|(4-methylpip erazin-1-yl)methyl |phenyl}[1,2,4]triazolo[4,3 - ajquinolin-1(2H)-one; 5-(benzylamino)-7- bromo] 1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; Ethyl-ethyl 7-methorxy-1-oxo0-1,2-dihydro[1,2,4]triazolo[4,3-a]qui noline-S-carboxylate:; 5-[4-{{[3-(dimethy Ramino)propyl]amino } methyl }phenyl][1,2 4]triazolo[4,3-a]quinolin- 1(2H)-one,

i+ PCT/SE2004/00035 1 RE - 148a - 5-{4-{[(3-morpholin-4-ylpropyl)amino|methyl} phemyl}[1,2,4]triazolo[4,3-a]quinolin— 1(2H)-one; 5-amino-7-methyl[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; Ft-butyl 7-methoxy-1-ox0-1,2-dihydro[1,2 4]triazolo[4,3-a]quinolin-5-yl carbamate; ; 5 S-amino-7-methoxy[1,2,4]triazolo[4,3-a]quinolin-1( 2H)-one; N 8-dimethylamino-5-methyl{ 1,2 4]triazolo[4,3-a]quirnolin-1(2H)-one; 5-amino-8-[4-(hydroxymethyl)phenyl}[ 1,2 4]triazolo[4,3-alquinolin-1(2H)-one; 5-(4-{[ (2S)-2-(hydroxymethyl)pyrrolidin-1-ylJmethy/1} phenyl){ 1,2 4]triazolo[4,3- a]quinolin-1(2H)-one; 5-[4-({[1-(hydroxymethyl)-2-methylpropylJamino } methy)phenyl][ 1,2,4]tnazolo[4,3- ajquinolin-1(2H)-one; 5-(4-{[ 4-(3-methylphenyl)piperazin-1-yl]methyl } phenyl)[ 1.2 4]triazolo[4,3- aJquinolin-1(2H)-one,

7-[4-({[3-(dimethylamino)propyl]amino } methyl)phenyl]-5-methyl[ 1,2,4]triazolo[4,3- a]quinolin-1(2H)-one; 5-methyl-7-(4-{[(3-morpholin-4-ylpropyl)amino]methyl }phenyl)[ 1,2,4]triazolo[4,3- ajquinolin-1(2H)-one; S-methyl-7-(4-{[(2-pyridin-2-ylethyl)amino]methyl } pheny}){ 1,2,4)triazolo[4,3-a}quinolin- 1(2H)-one; 7-(4-{[(2-hydroxyethyl)amino)methyl } phenyl)-5-methyl[ 1,2,4]triazolo[4,3-a]quinolin-1(2H)- one; 5-methyl-7-{4-[(4-methylpiperazin-1-yl)methyl]phenyl }{1,2,4]triazolo[4,3-a]quinolin-1(2H)-

one; 7-(4-{[(28)-2-(hydroxymethyl)pyrrolidin-1-ylJmethyl } phenyl)-5-methyl{1,2,4]triazolo[4,3- a]quinolin-1(2H)-one; 7-[4-({[1-(hydroxymethyl)-2-methylpropyl]amino } methyl)phenyl]-5- methyl[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one;

7-(4-{[ethyl(pyridin-4-ylmethyl)amino)methyl } phenyl)-5-methyl[ 1,2,4]triazolo[4,3- a]quinolin-1(2H)-one; 5-methyl-7-[4-({[3-(2-oxopyrrolidin-1-yl)propyl]amino } methyl)phenyl][ 1,2 4]triazolo[4,3- ajquinolin-1(2H)-one; 5-methyl-7-[4-({4-[3-(trifluoromethyl)phenyl]piperazin-1-

yl}methyl)phenyl][1,2,4]triazolo{4,3-a]quinolin-1(2H)-one; 7-{4-[(isobutylamino)methyl]phenyl}-5-methyl[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 5-[3-({[3-(dimethylamino)propylJamino } methyl)-4-methoxyphenyl][1,2,4]triazolo[4,3- aJquinolin-1(2H)-one; 5-amino-8-[3-(hydroxymethyl)phenyl][1,2,4]triazolo[4,3-a]quinolin-1(2H)-one;

5-{3-{(dimethylamino)methyl]phenyl}[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 5-{4-[(dimethylamino)methyl]phenyl}[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 8-[3-(dimethylamino)phenyl]-5-methyl[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 5-methyl-7-[4-({[2-(1H-pyrrol-1-yl)phenyljamino } methyl)phenyl][1,2,4]triazolo[4,3- aJquinolin-1(2H)-one;

3-hydroxy-2-(1-oxo-1,2-dihydro[1,2,4]triazolo[4,3-a]quinolin-5-yl)benzaldehyde; 7-[4-({[3-(1H-imidazol- 1-yl)propyl]amino} methyl)phenyl]-5-methyl[ 1,2,4]triazolo[4,3- a]quinolin-1(2H)-one;

5-(4—methoxy-3-{[(2-pyridin-2-ylethyl)amino}methyl } phenyl)[ 1,2,4]triazolo[4,3-a]quinolin- 1(2H)-one; 5-[3—({{1-(hydroxymethyl)-2-methylpropylJamino } methyl)-4- methoxyphenyl][1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 5-{4-methoxy-3-[(4-methylpiperazin-1-yl)methyi]phenyl}[1,2,4]triazolo{4,3-a]quinolin- 1(2H)-one; 5-(3 -{[(2R)-2-(hydroxymethyl)pyrrolidin-1-ylJrmethyl} 4-methoxyphenyl)(1,2 4]triazolo[4,3- ajquinolin-1(2H)-one; 5-[2-({[3-(dimethylamino)propyl]amino } methy1)-6-methoxyphenyl][1,2,4]triazolo[4,3- al]quinolin-1(2H)-one; 5-(2-{[(2S)-2-(hydroxymethyl)pyrrolidin- 1 -ylJrmethyl }-6-methoxyphenyl){ 1,2,4]triazolo(4,3- al]quinolin-1(2H)-one; 5-(2-methoxy-6-{[(2-pyridin-2-ylethyl)amino}methyl}phenyli)[ 1,2, 4]triazolo[4,3-a]quinolin- 1(2H)-one; 5-{ 2-methoxy-6-[(4-methylpiperazin-1-yl)methyljphenyl}[1,2,4]triazolo{4,3-a]quinolin- 1(2 H)-one; 5-[4-({[3-(1H-imidazol-1-yl)propyl]amino } methyl)phenyl][ 1,2 ,4]triazolo[4,3-a]quinolin- 1(2 H)-one; 5-(4-{{ethyl(pyridin-4-ylmethyl)amino]methyl }phenyl)[1,2,4]triazolo{4,3-alquinolin- 1 (2H)- one; 5-[4-({[3-(2-oxopyrrolidin-1-yl)propyl]Jamino } methyl)phenyl][ 1,2,41triazolo[4,3-a]lquinolin- 1(2H)-one; 5-[ 4-({[2-(1H-pyrrol-1-yl)phenyl]lamino } meth yl)phenyl}[1,2,4]triazolo[4,3-a]quinolin- 1(2H)- one; 5-C4-hydroxy-3-{[(2R)-2-(hydroxymethyl)pyrrolidin-1-yljmethyl } phenyl)[1,2,4]triazolo[4,3- a)quinolin-1(2H)-one; 5-[4-hydroxy-3-({[1-(hydroxymethyl)-2- methylpropylJamino } methyl)phenyli[1,2,4]tri azolo[4,3-a]quinolin- 1 (2H)-one; 5-q2-hydroxy-6-{[(28)-2-(hydroxymethyl)pyrrolidin-1-ylJmethyl }phenyl)[ 1,2,4]triazolo[4,3- aJquinolin-1(2H)-one; 5- {2-hydroxy-6-[(4-methylpiperazin-1-yl)methyl]phenyl}[1,2,4]triazolo[4,3-a]quinolin- 1(2H)-one;

PCT/SE2004 7000351

5-[4-({[4-(4-methylpiperazin-1-yl)phenyl]amino } methyl)phenyl][ 1,2,4]triazolo[4,3- a]quinolin-1(2H)-one; 5-(4-{[methyl(2-pyridin-2-ylethyl)amino]imethyl } phenyl)[ 1,2,4]triazolo[4,3-a]quino Min- 1(2H)-one;

5-(4-{[(2-furylmethyl)amino]methyl} phen yl)[1,2,4]triazolo[4,3-a]quinolin-1(2H)-omxe; 5-(4-{[(3-furylmethyl)amino]methyl }phen y)[1,2,4]triazolo[4,3-a]quinolin-1(2H)-orme; 5-{4-[({2-[({5-[(dimethylamino)methyl]-2- furyl}methyl)thio]ethyl }amino)methyl]phenyl}[1,2,4]triazolo{4,3-a]quinolin- 1(2H)- one; 5-(4-{[(2,3-dihydro-1-benzofuran-3-ylmethyl)amino]methyl }phenyl)[ 1,2,4]triazolo[4,3-

a]quinolin-1(2H)-one; 5-[4-({{(1-methyl-1H-pyrrol-2-yl)methylJamino } methyl)phenyl][ 1,2,4]triazolo[4,3- ajquinolin-1(2H)-one; 5-[4-({[2-(4-benzylpiperazin-1-yl)ethylJamino} methyl)phenyl][ 1,2,4]triazolo[4,3-a) «quinolin- 1(2H)-one;

5-(4-{[(pyridin-4-ylmethyl)amino]methy] } phenyl)[ 1,2,4]triazolo[4,3-a)quinolin- 1 (2 EH)-one; 5-(4-{[(4-morpholin-4-ylphenyl)amino]methyl} phenyl)[ 1,2,4]triazolo[4,3-a]quinolirs-1 (2H)- one; 5-amino-8-bromo[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 7-(4-{[4-(hydroxymethyl)piperidin-1-ylJmethyl } phenyl)-5-methy][ 1,2 4]triazolo[4,3 -

a]quinolin-1(2H)-one; 5-(4-{[4-(hydroxymethyl)piperidin-1-ylJmethyl} phenyl)[ 1,2,4]triazolo[4,3-a]quinoli 1-1 (2H)- one; 7-(4-{[(2-furylmethyl)amino}methyl } phen yl)-5-methy[ 1,2,4]triazolo[4,3-a]quinolin_-1 (2H)- one;

5-(4-{[4-(2-hydroxyethyl)piperidin- 1-ylJmethyl} phenyl)[ 1,2,4]triazolo[4,3-a]quinol# 1-1 (2H)- one; 5-{4-[(4-pyridin-2-ylpiperazin-1-yl)methy1]phenyl}[1 ,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 5-[4-({4-[4-(trifluoromethy)pyrimidin-2-y1]-1,4-diazepan-1- yl}methylphenyl][1,2,4]triazolo{4,3-a]quinolin-1(2H)-one;

4-[4-(1-oxo0-1,2-dihydro[ 1,2,4]triazolo[4,3 -a]quinolin-5-yl)benzyl]piperazine-1 -carbaaldehyde; 4-[4-(1-ox0-1,2-dihydro[1,2,4]triazolo[4,3 -a]quinolin-5-y1)benzyl]piperazine-1-carb eoxamide; 5-(4-{[(piperidin-4-ylmethyl)amino}methy1}phenyl)[ 1;2,4]triazolo[4,3-a]quinolin-1 (2H)-one;

5-(4-{[4-(2-hydroxyethyl)-1 4-diazepan-1-yljmethyl }phenyl)[ £ ,2,4]triazolo[4,3-a]quinolin- 1(2H)-one; 5-[4-({4-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]}-1,4-diazepan-1- yl}methyl)pheny1][1,2,4}triazolof4,3-a]quinolin-1(2H)-one; 5-(4-{[4-(3-nitropyridin-2-yl)-1,4-diazepan-1-ylJmethyl } phenv1)[ 1,2 ,4]triazolo[4,3- a]quinolin-1(2H)-one; 7-(4-methoxy-3- {[(3-morpholin-4-ylpropyl)amino]methyl }phenyl)-5- methyl[1,2,4]triazolo{4,3-a]quinolin-1{2H)-one; 7-(3-{[(2-hydroxyethyl)amino]methyl }-4-methoxyphenyl)-5-xnethyl[1,2,4]triazolo[4,3-

a]quinolin-1(2H)-one; 7-(4-methoxy-3- {[(2-pyridin-2-ylethyl)amino}methyl } phenyl )-5-methyl[1,2,4]triazolo[4,3- a]quinolin-1(2H)-one; 7-(3-{[4-(2-hydroxyethyl)piperidin-1-yl)methyl } -4-methoxypehenyl)-5- methyl[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one;

7-{3-[({2-[({5-[(dimethylamino)methyl}-2-furyl} methyl)thio_Jethyl }amino)methyl]-4- methoxyphenyl } -5-methyl[1,2,4]triazolo[4,3-a]quinolin-1(213)-one;

5-{2-[({2-[({ 5-[ (dimethylamino)methyl]-2-furyl } methyl)thio jethyl }amino)methyl]-6- methoxypheny! }[1,2,4]triazolo[4,3-a}quinolin-1(2H)-one; 5-{2-methoxy-6-[(4-pyridin-2-ylpiperazin-1-yl)methyljpheny 1} [1,2,4}triazolo[4,3-a]quinolin-

1(2H)-one; 5-(3-{[(3-furylmethyl)amino}methyl } -4-methoxyphenyl)[ 1,2 ,4]triazolo[4,3-a]quinolin-1(2H)- one; 5-{3-[({2-[({5-[(dimethylamino)methyl]-2-furyl} methyl)thice Jethyl } amino )methyl]-4- methoxyphenyl }[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one;

5-[3-({[2-(4-benzylpiperazin-1-yl)ethylJamino} methyl)-4-mesthoxyphenyl]{1,2,4]triazolo[4,3- ajquinolin-1(2H)-one; 5-{4-methoxy-3-[(4-pyridin-2-ylpiperazin-1-yl)methyl}phenyi}[1,2,4]triazolo[4,3-a]quinolin- 1(2H)-one; 8-chloro-7-methoxy-5-methyl[ 1,2,4]triazolo[4,3-a]quinolin- A (2H)-one;

7-methoxy-5-methyl-8-pyridin-4-yl[1,2,4]triazolo[4,3-a}quirolin-1(2H)-one; 8-[3-(benzylox y)phenyl]-7-methoxy-5-methyl[1,2,4]triazolo [4,3-a]quinolin-1(2H)-one; 7-methoxy-8-[4-(methoxymethyl)phenyl]-5-methyl[1,2,4]tri ;azolo[4,3 -a]quinolin-1(2H)-one;

hn PCT/SE2004/000351 tert-butyl 3-(7-methoxy-5-methyl-1-0xo-1,2-dihydro[1,2,4]triazolo[4,3-a]quinolin -8- y Dbenzylcarbamate; 8 -[4-(aminomethyl)phenyl]-7-methoxy-5-methyl[1,2,4]triazolo[4,3-a]quinolin-1(2 H)-one 4 -methoxy-3-(7-methoxy-5-methyl-1-ox0-1,2-dihydro[1,2,4]triazolo[4,3-a]quinol1 n-8- y )benzaldehyde; 8 -(3,4-dimethoxyphenyl)-7-methoxy-5-methyl[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 8 -(3-chloro-4-fluorophenyl)-7-methoxy-5-methyl[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 8 -[4-(dimethylamino)phenyl]-7-methoxy-5-methyl[1,2,4]triazolo{4,3-a]quinolin-1 (2ZH)-one; 8 -(3-aminophenyl)-7-methoxy-5-methy][1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 8 -(2,6-dimethoxyphenyl)-7-methoxy-5-methyl[1,2,4]triazolo[4,3-a]quinolin-1(2H Y-one; 7 -methoxy-8-(3-methoxyphenyl)-5-methyl[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 8 —(4-chlorophenyl)-7-methoxy-3-methyl[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 7 -methoxy-8-[3-(methoxymethyl)pheny!]-5-methyl[1,2,4]triazolo[4,3-a}quinolin- 1 (2H)-one; 8 —[3-(hydroxymethyl)phenyl}-7-methox y-5-methyl[1,2,4]triazolo[4,3-a]quinolin-1 (2H)-one; 8 —[4-(hydroxymethyl)phenyl]-7-methoxy-5-methyl[1,2,4]triazolo[4,3-a]quinolin-1 (2H)-one; 8 —[3-(aminomethyl)phenyl]-7-methoxy-5-methyl[1,2,4]triazolo[4,3-a]quinolin-1(2 H)-one; 8 —(3-{[(2-hydroxyethyl)amino]methyl} phenyl)-7-methoxy-5-methyl{1,2 4]triazolo [4,3- a ]quinolin-1(2H)-one; 7 —methoxy-3-methyl-8-[3-({[(1-methyl- 1H-pyrrol-2-yl)methyl]Jamino } methyl)phenyl] [1 ,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 8 —(3-{[4-(2-hydroxyethyl)piperidin-1-yl]methyl} phenyl)-7-methoxy-5- mxethyl[1,2,4]triazolof4,3-a]quinolin-1(2H)-one; 7 —methoxy-5-methyl-8-(3-{[(pyridin-4-ylmethyl)amino]methyl} phenyl)[1,2,4]triazolo[4,3- aJquinolin-1(2H)-one; 8—{3-[(isobutylamino)methyl]phenyl}-7-methoxy-5-methyl[1,2,4]triazolo[4,3-a]qu inolin- 1(2H)-one; 7—methoxy-5-methyl-8-(3-{[(3-morpholin-4-ylpropyl)amino]methyl} phenyl)[1,2,4 ] triazolo[4,3-a]lquinolin-1(2H)-one; 8—(3-{[4-(hydroxymethyl)piperidin-1-yl Jmethyl} phenyl)-7-methoxy-5- methyl{1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 8—[3-({[3-(1H-imidazol-1-yl)propyljamino } methyl)phenyl]-7-methoxy-5- m ethyl[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; AMENDED SHEET

L : | PCT/SE2004/€000351

8-(3-{[(3-chlorobenzyl)amino]methyl} phenyl)-7-methox y-5-methyl[1 ,2,4)triazolof4,3— aJquinolin-1(2ZH)-oOne; 7-methoxy-S-methyl-8-{3-({methyl[2- (methylamino)ethyl]amino}methyl)phenyl][1,2,4]triazolof4,3-ajquinolin-1(2H)-one; 8-(4-methoxyphen yl)-5-methyl[1,2,4]triazolo[4,3-a}quinolin-1(2H)-one; 5-hydroxy-8-[4-(hydroxymethyl)phenyl][1.2,4]triazolo[4 ,3-a]quinolin-1(2H)-one; 5-methyl-8-pyridin-4-yl{1,2,4]triazolo[4,3-a]quinolin-1(2Z H)-one; 7-hydroxy-8-[2-(hydroxymethyl)phenyl]-5-methyl[1,2,4] triazolo[4,3-a]quinolin-1 (2H)—one; 8-[3-(aminomethyl)phenyl]-7-hydroxy-5-methyl{1,2,4]trL azolo[4,3-a]quinolin-1(2H)-ome; 8-[3-({[3-(dimethy lamino)propylJamino } methyl)phenyl]—7-methoxy-5- methyl[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 8-[3-({[3 -(dimethy lamino)propyl]amino} methyl)-4-methoxyphenyl]-7-methoxy-5- methyl[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 7-methoxy-8-{4-methoxy-3-[(4-methylpiperazin-1 -yl)methyl]phenyl}-5- methyl(1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 8-(3-{[(2-hydroxyethyl)amino]methyl} -4-methoxyphenyl )-7-methoxy-5- methyl[1,2,4]triazolof4,3-a]quinolin-1(2H)-one; 7-methoxy-5-methyl-8-(1H-pyrrol-2-yl)(1,2,4]triazolo [4,3-a]quinolin-1(2H)-one; N-[4-(5-methyl-1-0x0-1,2-dihydro[1,2,4]triazolo [4,3-a]quinolin-8-yl)phenyl]acetamide; 5-methyl-8-thien-2 -yl[1,2,4]triazolo[4,3-a]quinolin-1(2H) -one; 5-amino-8-thien-2-yl[1,2,4]triazolo[4,3-a]quinolin-1(2H)~one; 5-amino-8-(2-furyl)][1,2,4]triazolo[4,3-a]quinolin-1(2H)-0 ne; 5-methyl-8-(1H-pyrrol-2-y1)[1,2,4]triazolo[4,3-a]quinolin—1 (2H)-one; 8-{2-furyl)-5-methyl[1,2,4]triazolo[4,3-a]quinolin-1(2H)- one; 5-amino-8-thien-3-yI[1,2,4]triazolo[4,3-a]quinolin-1(2H)- one; 5-methyl-8-thien-3-yl[1,2,4]triazolo[4,3-a]quinolin-1(2H)—one.

N,N-dimethyl-3-(5-methyl-1-oxo0-1,2-dihydro[1,2,4]triazo lo[4,3-a]quinolin-8-yl)benzamuide; 5-{4-[(cyclopentylamino)methyl]phenyl}[1 ,2,4]triazolo[4 .. 3-a]quinolin-1(2H)-one; 5-(4-{[(tetrahydrofuran-2-ylmethyl)amino]methyl } phenyl 3[1 ,2,4]triazolo[4,3-a]quinolin— 1(2H)-one; : 5-(4-{[(2-hydroxypropyl)amino]methyl}phenyl)[1 ,2,4]tria zolo[4,3-a]quinolin-1(2H)-one t-butyl 4-{[4-(1-ox0-1,2-dihydro[1,2,4]triazolo[4,3-a]quinolin-5- yl)benzyl]amino} pi peridine-1-carboxylate; AMENDED SHEET

7-hydroxy-8-(2-{ [(2-hydroxypropyl)amino]methyl }phenyl)-5-methyl[1 ,2.4triazolo[4,3- a)quinolin-1(2H)-one; 7-hydroxy-5-methyl-8-phenyl(1,2,4]triazolo[4,3-a]quinolin- 1(2H)-one; 8-(4-chlorophenyl)-7-hydroxy-5-methyl{ 3 ,2,4]triazolo[4,3 -ajquinolin-1(2H)-one;

8-(3-chloro-4-fluorophenyl)-7-hydroxy-5 -methyl[1 ,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 8-[4-(dimethylamino)phenyl]-7-hydroxy—>5-methyl[1 ,2 4]triazolo[4,3-a]quinolin-1(ZH)-ome; 8-(3-aminophenyl)-7-hydroxy-5-methyl{ 1,2,4]triazolo[4,3-a]quinolin-1 (2H)-one; 7-hydroxy-8-(2-methoxypyridin-4-yl)-5- methyl{1 ,2,4]triazolo[4,3-a]quinolin-1(2H)-one ; 5-(3-aminopropoxy)[ 1,2,4]triazolo[4,3-a Jquinolin-1(2H)-one;

8-(2-aminophenyl)-7-hydroxy-5-methylf 1,2,4]triazolo[4,3-a]quinolin- 1(2H)-one; 8-{2-[(cyclopentylamino)methyl]phenyl }-7-hydroxy-5-methyl{1 ,2,4]triazolo[4,3-a]quin olin- 1(2H)-one; 7-hydroxy-8-(3-hydroxyphenyl)-S-meth yl[1,2,4]triazolo[4,3-a]quinolin-1 (2H)-one; 7-hydroxy-S-methyl-8-{3-({ methyl[2-(mnethylamino)ethyt]amino }methyl)phenyl]

[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one;

7-hydroxy-8-[3-({[3-(1H-imidazol-1-y1 Jpropyl]amino}methyl)phenyl]-5- methyl[1,2,4]triazolo[4,3-a]quinolin- 1(2H)-one; 8-[3-({[3-(dimethylamino)propyl]amin ©} methyl)phenyl}-7-hydroxy-5- methyl[ 1,2,4]triazolo[4,3-a]quinolin- 1 ( 2H)-one;

7-hydroxy-5-methyl-8-(3-{[(pyridin-4—ylmethyl)amino]methyl }phenyl){1 ,2,4]triazolo[ 4,3-

a)quinolin-1(2H)-one; 4-amino-8-[4-(hydroxymethyl)phenyl] [1,2,4]triazolo{4,3-a]quinolin-1(2H)-one; 7-hydroxy-5-methyl-8-(3-{ [(3-morphcelin-4-ylpropyl)amino}methyl } phenyl) [1,2,4]triazolo[4,3-a]quinolin-1(2H)-ome; 8-(3-{[(3-chlorobenzyl)amino]methyl 3 phenyl)-7-hydroxy-5-methyl{1 ,2,4]triazolo [4,3-a]quinolin-1(2H)-one; 5-[3-({[2-(4-benzylpiperazin-1-yl)ethyl]Jamino jmethyl)-4-hydroxyphenyl] [1,2,4]triazolof4,3- aJquinolin-1(2H)-one; 5-{2-hydroxy-6-[(4-pyridin-2-ylpiperazin-1-yl)methyl}phenyl}[1,2,4]triazolo [4,3-a)quinolin-1(2H)-one; 5-[2-({[2-(4-benzylpiperazin-1-yl)eth ylJamino }methyl)-6-hydroxyphenyl] [1,2,4]tria=zolo[4,3- a]quinolin-1(2H)-one; 4-amino-8-thien-2-yl[1,2,4]triazolo[4-,3-a]quinolin-1(2H)-one;

4-amino-8-[3-(hydroxymethyl)phenyl][1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 6-[3-(aminomethyl)phenyl][ 1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 5-(hydroxymethyl)-8-[3-(hydroxymethyl)phenyl]-7-methoxy[1,2,4]triazolof4,3-a]quinolin- 1(2H)-one;

8-(3-aminophenyl)-5-(hydroxymethyl)-7-methoxy[ 1,2,4]triazolo [4,3-a]quinolin-1(2H)-one; 7-hydroxy-5-(hydroxymethyl)-8-[2-(hydroxymethyl)phenyl]{1,2,4]triazolo [4,3-alquinolin-1(2H)-one; 7-hydroxy-5-(hydroxymethyl)-8-[3-(hydroxymethyl)phenyl][1,2,4]triazolo

[4,3-a]quinolin-1(2H)-one; 8~(3-aminophenyl)-7-hydroxy-5-(hydroxymethyl)[ 1,2,4]triazolo [4,3-a]quinolin-1(2H)-one; 6~{3-[(cyclohexylamino)methyl]phenyl}[1,2,4]triazolo[4,3-a]quinolin- 1(2H)-one; 6-{3-[(cyclopentylamino)methyl]phenyl}[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one;

6-(3-{[(tetrahydrofuran-2-ylmethyl)amino]methyl } phenyl)[ 1,2,4]triazolo {4,3-a]quinolin-1(2H)-one; 6-~(3-{[4-(hydroxymethyl)piperidin-1-yl}methyl } phenyl)[ 1,2 4]triazolo [4,3-a]quinolin-1(2H)-one; 4-(hydroxymethyl)-8-pyridin-4-yl[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one;

8-(3-furyl)-5-methyl[1,2 4]triazolo[4,3-a]quinolin- 1(2H)-one; 6-{3-[(isobutylamino)methyl]phenyl}[1,2,4]triazalo{4,3-a]quinolin-1(2H)-one; 6-(3-{[4-(2-hydroxyethyl)-1,4-diazepan-1-yljmethyl }phenyl)[1,2,4]triazolo [4,3-a]quinolin-1(2H)-one; 8-(2-aminophenyl)-7-hydroxy-5-(hydroxymethyl)[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one;

6-(4-hydroxy-3-{[(tetrahydrofuran-2-ylmethyl)amino]methyl } phenyl) (1,2,4]triazolo[4,3-a]quinolin- 1 (2H)-one; 6-{4-hydroxy-3-[(isobutylamino)methyl]phenyl} [1,2 4]triazolo{4,3-a]quinolin-1(2H)-one; 4-(hydroxymethyl)-8-thien-2-yl[ 1,2 4]triazolo[4,3-a]quinolin-1(2H)-one; 5~(hydroxymethyl)-8-thien-2-yl| 1,2,4]triazolo[4,3-a]quinolin-1(2H)-one;

5-(hydroxymethyl)-8-thien-3-yl[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 7-methoxy-5-methyl-8-thien-3-y1[1,2,4]triazolo[4,3-a]quinolin-1 (2H)-one; 7-hydroxy-5-methyl-8-thien-3-yl[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 5-amino-7-hydroxy-8-thien-3-yl[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one;

Lo - PCT/SE200-4/000351

N-[3-(5-methyl-1-ox0-1,2-dihydro[1,2,4]triazolo[4,3-a]quinolin-8- y l)phenyl}methanesulfonamide; -amino-8-(1H-pyrrol-2-y1)[1,2,4]triazolo[4 .3-a]quinolin-1(2H)-one; S-(hydroxymethyl)-8-(1H-pyrrol-2-y1)[1,2,4 Jtriazolo[4,3-a]quinolin-1(2H)-one; 5S -methyl-8-(1H-pyrazol-4-yl)[1,2,4]triazolo [4,3-a]quinolin- 1 (2H)-one; S-amino-8-(1H-pyrazol-4-y1)[1.2,4]triazolo[ 4,3-a]quinolin-1(2H)-one; S -amino-8-(3-furyl)[ 1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 5 -methyl-8-(4-methylthien-2-y1)[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 8 -[5-(hydroxymethyl)thien-2-yl]-5-methyl[ 1 ,2,4]triazolo[4,3-a]quinolin-1(2H)-one; &-[3-(1-hydroxyethyl)thien-2-y1}-5-methyl[ 1 ,2,4]triazolo[4,3-a]quinolin-1(2H)-one; tert-butyl 4-{[(1-ox0-8-thien-3-yl-1,2-dihydro[1,2,4]triazolo[4,3-a]quinolin-5- yv 1)amino]methyl}piperidine-1-carboxylate;, & -bromo-5-(hydroxymethyl)[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 7 -methoxy-8-[4-methoxy-3-({[(1-methyl-1H-pyrrol-2-yl) methyl jamino } methyl)phen yl]-5- methyl{1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 7 -methoxy-8-(4-methoxy-3-{[(pyridin-4-ylmethyl)amino]methyl} phenyl)-5- rnethyl[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 8-(3-{[4-(2-hydroxyethyl)piperidin-1-ylJmethyl}-4-methoxyphenyl)-7-methoxy-5- methyl[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 7 -methoxy-8-(4-methoxy-3-{[(2-pyridin-2-ylethyl)amino]methyl} phenyl)-5- methyl[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 8-(3-{[4-(hydroxymethyl)piperidin-1-ylJmethyl} -4-methoxyphenyl)-7-methoxy-5- methyl[1,2,4}triazolo[4,3-a]quinolin-1(2H)-oOne; 7 -methoxy-8-(4-methoxy-3-{[(2-methoxyethyl)amino]methyl} phenyl)-5- methyl[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 7 -methoxy-8-(3- {[(2-methoxyethyl)amino methyl } phenyl)-5-methyl[1,2,4]triazolo[4 J 3- a Jquinolin-1(2H)-one; 8 -{3-[(cyclopentylamino)methyl]-4-methoxyphenyl }-7-methoxy-5- methyl[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 8 -(3-{[(4-fluorobenzyl)amino]methyl}-4-methoxyphenyl)-7-methoxy-5- methyl[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; &-{3-[(cyclobutylamino)methyl]-4-methoxy phenyl} -7-methoxy-5-methyl[1,2,4]triazolo[4,3- a ]quinolin-1(2H)-one; AMENDED SHEET

8-{3-[(cyclohexylamino)methyl]-4-methoxyphenyl}-7-methoxy-5-methyl[ 1,2,4]triazolo[4,3-

ajquinolin-1(2H)-one; 8-{3-[(cyclopentylamino)methyl]phenyl}-7-methoxy-5-me thyl[ 1,2,4]triazolo[4,3-a]quinolin- 1(2H)-one;

8-{3-[(cyclobutylamino)methyl}phenyl}-7-methoxy-5-methhyl[1,2,4]triazolo[4,3-a]quinolin- 1(2H)-one; 8-{3-[(cyclohexylamino)methyl]phenyl }-7-methoxy-5-methyl[1,2,4}triazolo[4,3-a]quinolin- 1(2H)-one; 8-(3-{[(2-hydroxypropyl)amino]methyl } phenyl)-7-methox y-5-methyl[1,2,4]triazolo[4,3-

ajquinolin-1(2H)-one; 8-(3-{[4-(2-hydroxyethyl)-1,4-diazepan-1-yl]methyl }phenyl)-7-methoxy-5- methyl[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 8-{3-[(cyclopropylamino)methyl]phenyl }-7-methoxy-5-methyl[1,2,4)triazolo[4,3-a]quinolin- 1(2H)-one;

7-methoxy-5-methyl-8-(3-{[(tetrahydrofuran-2- ylmethyl)aminojmethyl}phenyl)[1,2,4]triazolo[4,3-a]quinclin-1(2H)-one; 7-methoxy-5-methyl-8-(3-{[(2-phenoxyethyl)amino]methy~1} phenyl){1,2,4]triazolo[4,3- a]quinolin-1(2H)-one; 7-methoxy-5-methyl-8-[3-({[2-(2-thienyl)ethyl]Jamino}me&hyl)phenyl][ 1,2,4]triazolo[4,3-

a]quinolin-1(2H)-one; 8-{3-[(cyclopropylamino)methyl]-4-methoxyphenyl }-7-methoxy-5-methyl[ 1,2 4]triazolo[4, 3- a]quinolin-1(2H)-one; 5-methyl-8-pyridin-3-yl[1,2,4]triazolo[4,3-a]quinolin-1 (2X )-one; 7-hydroxy-8-{3-[(isobutylamino)methyl]phenyl}-5-methyl [1,2,4]triazolo[4,3-a]quinolin-

1(2H)-one; . 7-hydroxy-8-(3-{[4-(2-hydroxyethyl)piperidin-1-ylJmethyl }phenyl)-5- methyl[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 7-hydroxy-5-methyl-8-{3-[(4-methylpiperazin- 1-yl)methyl Jphenyl}[1,2,4]triazolo[4,3- a]quinolin-1(2H)-one;

7-hydroxy-8-(4-hydroxy-3-{[(pyridin-4-ylmethyl)amino]m ethyl }phenyl)-S- methyl[1,2,4]triazolo[4,3-a)quinolin-1(2H)-one; 8-{3-[(cyclopentylamino)methyl]phenyl }-7-hydroxy-5 -methyl[1,2,4]triazolo[4,3-a]quinolin- 1(2H)-one;

8-(3-{[(4-fluorobenzyl)amino}methayl } phenyl)-7-hydroxy-5-methyl{1,2 4]tariazolo[4,3- a]quinolin-1(2H)-one; 8-[2-(hydroxymethyl)phenyl]-7-mesthoxy-5-methyl[ 1,2,4]triazolo[4,3-a]qui nolin-1(2H)-one; 7-methoxy-5-methyl-8-[4-(morpho lin-4-ylcarbonyl)phenyl][1,2.4]triazolo[=4,3-a]quinolin- 1(2H)-one; 7-methoxy-5-methyl-8-[4-(pyrrolidin-1-ylcarbonyl)phenyl][ 1,2,4]triazolo[<},3-a]quinolin- 1(2H)-one; 7-methoxy-5-methyl-8-[4-(piperidim- 1-ylcarbonyl)phenyl][ 1,2,4]triazolo[4 . 3-a]quinolin- 1(2H)-one;

8-chloro-7-hydroxy-5-methyl]1,2,4-Jtriazolo[4,3-a]quinolin-1(2H)-one; 8-{3-[(cyclobutylamino)methyllphenyl}-7-hydroxy-5-methyl[ 1,2 ,4]triazolo>[4,3-a}quinolin- 1(2H)-one; 7-hydroxy-5-methyl-8-(3-{[(tetrahy/drofuran-2- ylmethyl)aminoJmethyl} phenyl){ 1,2 4]triazolo[4,3-a]quinolin-1(2H)-one; 7-hydroxy-8-(3-{[4-(2-hydroxyethys1)-1,4-diazepan-1-ylJmethyl }phenyl)-5- methyl[1,2,4]triazolo[4,3-a]quinolixn-1(2H)-one; 8-{3-[(cyclopropylamino)methyljpkenyl }-7-hydroxy-5-methyl[1,2 4]triazoRo[4,3-a]quinolin- 1(2H)-one; 8-{3-[(cyclopropylamino)methyl]phenyl}-7-hydroxy-5-methyl{1,2,4]triazoK o[4,3-a]quinolin-

1(2H)-one; 8-{3-[(cyclohexylamino)methyl]phenyl}-7-hydroxy-5-methyl[ 1,2 4]triazolc»[4,3-a]quinolin- 1(2H)-one;

N-cyclohexyl-4-(7-methoxy-5-methayl-1-oxo-1,2-dihydro[1,2,4]triazolo[4,3 —a]quinolin-8- yDbenzamide;

8-(2-{[(4-fluorobenzyl)amino]meth yl} phenyl)-7-methoxy-5-methyl[1,2,4]tr—iazolo[4,3- a]quinolin-1(2H)-one; 8-(2-{[(2-hydroxyethyl)amino]meth yl} phenyl)-7-methoxy-5-methyl[ 1,2 ,4]tmriazolo[4,3- a]quinolin-1(2H)-one; 8-(2-{[4-(hydroxymethyl)piperidin- 1-yl]methyl}phenyl)-7-methoxy-5-

methylf1,2 4]triazolo[4,3-a]quinolin -1(2H)-one; 8-(2-{[4-(hydroxymethyl)piperidin- 1-ylJmethyl} phenyl)-7-methoxy-5- methyl[1,2,4]triazolo[4,3-a]quinolin—1(2H)-one;

°

7-bromo-N-(4-methoxybenzyl)-1-0x0-1,2-dihydro[1 ,2,4]triazolo[ 4,3-a]quinoline-5-

carboxamide;

8-(benzylamino)-5-nwethyl[1 ,2,4]triazolo[4,3-a]quinolin- 1(2H)-ome; N,N-dimethyl-4-(5-maethyl-1-oxo-1,2-dihydro[ 1,2,4]triazolo [4,3-a]quinolin-8-yl)benzamide;

5-methyl-8-[4-(pyrro lidin-1-ylcarbonyl)phenyl][1,2,4]triazolo[4, 3-a]quinolin-1(2H)-one;

5-methyl-8-[4-(piperddin-1-ylcarbonyl)phenyl][1,2,4]triazolo[4,3-a] quinolin-1(2H)-one; [4-(5-methyl-1-oxo0- 1 ,2-dihydro[1 ,2,A]triazolo[4,3-a]quinolin-8-yl)phenyljacetonitrile; 8-[3-(hydroxymethyl )phenyl]-1-oxo-1,2-dihydro[1,2,4]triazolo{ 4 ,3-a] quinoline-5-carboxylic acid;

3-(5-methyl-1-0x0-1 ,2-dihydro[1,2,4]triazolo[4,3-a]quinolin-8-y1)benzonitrile; 5-methyl-8-[4-(morpeholin-4-ylcarbonyl)phenyl][1,2,4]triazolo[4 ,3-a]quinolin-1(2H)-one; 8-[2-(hydroxymethy®)phenyl]-1-oxo-N-piperidin-4-yl-1,2-dihydro[1,2,4]triazolo[4,3- a]quinoline-5-carboxcamide; 7-[3-(hydroxymethyX)phenyl]-1-oxo-N-piperidin-4-yl-1,2-dihydro[1,2,4]triazolo[4,3-

a]quinoline-5-carboxamide;

[3-(7-methoxy-5-methyl-1-oxo0-1,2-dihydro[ 1,2,4]triazolo[4,3-a] quinolin-8- yDphenyl]acetonitril e;

N-(2-cyanoethyl)-3-7-methoxy-5-methyl-1-oxo-1,2-dihydro[ 1,2 4]triazolo[4,3-a]quinolin-8- ylbenzamide;

6-chloro[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 7-hydroxy-5-methyl —8-[4-(piperidin-1-ylcarbonyl)phenyl][1,2,4 J triazolo[4,3-a]quinolin-

1(2H)-one; N-cyclohexyl-4-(7-lmydroxy-5-methyl-1-oxo-1,2-dihydro[ 1,2,4]triazolo[4,3-a]quinolin-8- yhbenzamide;

6-[4-(hydroxymethy 1)phenyl][1,2,4]triazolo[4,3-a]lquinolin-1(2H)-one; 6-[3-(hydroxymethy1)phenyl][1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 6-(3-aminophenyl)[ 1 ,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 7-methoxy-4-{[(pyridin-4-ylmethyl)amino]methyl}[1,2,4]triazo1o[4,3-a]quinolin-1(2H)-one;

5-amino-8-pyridin-4--yl[1,2 4]triazolo[4,3-a]quinolin-1(2H)-one;

3-(5-methyl-1-ox0-1 ,2-dihydro[1,2,4]triazolo[4,3-a]quinolin-8-yl)benzamide; 2-(5-methyl-1-ox0-1 ,2-dihydro[ 1,2,4]triazolo[4,3-a]quinolin-8-y1)benzamide; 8-chloro-7-(3-chloropropoxy)-5-methyl[1,2,41triazolo[4,3-a]quinolin-1(2H)-one; 8-chloro-7-(2-methaxyethoxy)-5-methyl[1,2,4]triazolo[4,3-alquinolin-1(2H)-one;

8-[3-(hydroxymethyl)phenyl]-7-(2-methoxyethoxy)-5-methyl{1,2 ,A4ltriazolo[4,3-a)quinolin- 1(2H)-one; 7-(3-aminopropoxy)-8-[3 (hydroxymethyl)phenyl]-5-methyl{1 ,2,41triazolo[4,3-a)quinolin- 1(2H)-one; 7-(3-aminopropoxy)-8-[2-(hydroxymethyl)phenyl]-5 -methyl[1,2,4]tria=olo[4,3-a]quinolin- 1(2H)-one; 7-hydroxy-8-(2-hydroxy phenyl)-5-methyl[1,2,4]triazolo[4,3 -a]quinolin-1(2H)-one; 8-bromo-4-(hydroxymethyl)[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 5-methyl-8-(2-thienyl)[ 1 ,2,4]triazolo[4,3-a]quinolin-1(2H)-one; N,N-dimethyl-3-(5-methyl-1-oxo-1,2-dihydro[1,2,4}triazolo[4,3-a] quitnolin-8-yl)benzamide 5-{4-[(cyclopentylamino)methyl]phenyl}[1,2,4]triazolo[4,3 -a]quinolin-1(2H)-one; 5-(4- {[(tetrabydrofuran—2-ylmethyl)aminoJmethyl } phenyD[1 ,2,4)triazolo[4,3-a]quinolin- 1(2H)-one; 5-(4-{[(2-hydroxypropyl)amino]methyl}phenyl)[1,2,4] triazolo[4,3-a] quinolin-1(2H)-one; tert-butyl 4-{[4-(1-0x0~1,2-dihydro[1,2,4]triazolo[4,3-a]quinolin-5- yl)benzylJamino }piperidine-1-carboxylate; 7-hydroxy-8-(2-{[(2-hydroxypropyl)amino]methyl} phenyl)-S-methy3[1,2,4]triazolo[4,3- a]quinolin-1(2H)-one; 8-(2-{[(4-fluorobenzyl )amino}methyl }phenyl)-7-hydroxy-5-methyl[ 1 ,2,4]triazolo[4,3- a]quinolin-1(2H)-one; 7-hydroxy-8-(2-{[4-(h.ydroxymethyl)piperidin-1-yljmethyl }phenyl)- 5- methyl[ 1,2,4]triazolo[<4,3-a]quinolin-1(2H)-one; 4-(hydroxymethy!)-8-umethoxy[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 8-{2-[(cyclopentylamino)methyllphenyl}-7-methoxy-5-methyl[ 1 ,2,4]triazolo[4,3-a]quinolin- 1(2H)-one; 4-[(cyclobutylamino)xmethyl]-7-hydroxy[ 1,2,4]triazolo[4,3-a]quinolin-1 (2H)-one 7-hydroxy-5-methyl-8-phenyl|1,2,4]triazolo[4,3-a}quinolin-1(2H)-one; 8-(4-chlorophenyl)-7~hydroxy-5-methyl[1,2,4]triazolo[4,3-a] quinolin-1(2H)-one; 4-{[(4-fluorobenzyl)amino}methyl}-7-hydroxy[1 ,2,4]triazolo[4,3-aJquinolin-1(2H)-one; 8-[4-(dimethylamino)phenyl]-7-hydroxy-5-methyl[1,2,4]triazolo[4,3-a] quinolin-1(2H)-one; 8-(3-aminophenyl)-7~hydroxy-5-methyl[1,2,4]triazolo[4,3-a]quinol in-1 (2H)-one; 8-(2-aminophenyl)-7 -methoxy-5-methyl[ 1,2,4]triazolo[4,3-a]quino lin-1(2H)-one; 7-hydroxy-8-(2-methoxypyridin-4-yl)-5-methyl[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one;

5-(3-aminopropoxy)[ 1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 8-[2-(hydroxymethy1)-4-methoxyphenyl]-5-methyl(1 ,2,4]triazolo[4,3-a]JquEnolin-1(2H)-one; 8-(2-aminophenyl)-7-hydroxy-5-methyl[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 8-{2-[(cyclopentylamino)methyllphenyl}-7-hydroxy-5-methyl(1,2,4}triazo 1o[4,3-a] quinolin- 1(2H)-one;

7-hydroxy-8-(3-hydroxyphenyl)-5-methyl[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 7-hydroxy-5-methyl-8-[3-({methyl[2- (methylamino)ethyl Jamino }methyl)phenyl}{1,2,4]triazolo[4,3-a]quinolin-1 (2H)-one; 7-hydroxy-8-[3-({[3 -(1 H-imidazol-1-yl)propylJamino } methyl)phenyl]-5-

methyl[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 7-hydroxy-5-methyl-8-(3-{[(pyridin-4-ylmethyl)amino}methyl }phenyl)[ 1,2 4]triazolo[4,3- aJquinolin-1(2H)-one; 4-amino-8-[4-thydroxymethyl)phenyl][1,2,4]triazolo[4,3-a]lquinolin-1(2H®»-one; 8-hydroxy-4-(hydroxymethyl)[ 1,2,4]triazolo[4,3-a]quinolin-1(2H)-one;

2-(5-amino-1-oxo-1,2-dihydro[1,2,4]triazolo[4,3-a]quinolin-8-yl)benzamide; 7-hydroxy-5-methyl-8-(3-{[(3-morpholin-4- ylpropyl)amino]methyl }phenyl)[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 8-(3-{[(3-chlorobenzyl)amino]methyl} phenyl)-7-hydroxy-5-methyl[1,2,4] triazolo[4,3- a]quinolin-1(2H)-one;

5-[3-({[2-(4-benzylpiperazin-1-yl)ethyllamino }methyl)-4-hydroxyphenyl] [1,2,4]triazolo[4,3~ a]quinolin-1(2H)-one; 5-{2-hydroxy-6-[(4-pyridin-2-ylpiperazin-1-yl)methyl]lphenyl }[1,2,4]triaz ©lo[4,3-a]quinolin-

1(2H)-one; ethyl 8-chloro-7-methoxy-1-oxo-1,2-dihydro[1,2,4]triazolo[4,3-a]quinolin e-5-carboxylate;

2-(5-hydroxy-1-oxo-1,2-dihydro[1,2,4]triazolo{4,3-a]quinolin-8-yl)benzarmide; 5-[2-({[2-(4-benzylpiperazin-1-yl)ethylJamino }methyl)-6-hydroxyphenyl] [1,2,4]triazolo[4,3- a]quinolin-1(2H)-one; 4-amino-8-(2-thienyl)[ 1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 8-chloro-7-hydroxy-5-(thydroxymethyl)[1,2,4]triazolo[4,3-a]quinolin- 1 (2Ed)-one;

5-(hydroxymethyl)-8-[2-(hydroxymethyl)phenyl]-7-methoxy[1,2,4]triazol«[4,3-a]quinolin-

1(2H)-one; 5-amino-8-(4-methoxyphenyl)[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 5-methyl-8-(1H-pyrrol-2-yl)[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one;

6-[4-(aminomethyl)phenyl][1 ,2,4]triazolo[4,3-a]quinolin-1(2H)-one; N-[2-(1-0x0-1,2-dihydro[1,2 ,4]triazolo[4,3-a]quinolin-6-yl)phenyl]acetzmmide; 6-[2-(hydroxymethyl)phenylj[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 4-amino-8-[3-(hydroxymethy1)phenyll[1,2,4]triazolo[4,3-a]quinolin-1(2=H)-one; 4-amino-8-(2-furyl)[1,2,4]triazolo[4,3-a]quinolin- 1(2H)-one;

6-[3-(aminomethyl)phenyl][ 1,2,4]triazolo(4,3-a]quinolin-1(2H)-one; 5-(hydroxymethyl)-8-[3-(hydroxymethyl)phenyl}-7-methoxy{ 1,2,4]triaz=olo[4,3-a]quinolin- 1(2H)-one; 8-(3-aminophenyl)-5-(hydroxymethyl)-7-methoxy[1,2,4]triazolo[4,3-a]«quinolin-1(2H)-one;

7-hydroxy-5-(hydroxymethy1)-8-[2-(hydroxymethyl)phenyl][1,2,4]triazolo[4,3-a]quinolin- 1(2H)-one; 7-hydroxy-5-(hydroxymethy1)-8-[3-(hydroxymethyl)phenyl][1,2,4]triazolo[4,3-a]quinolin- 1(2H)-one; 8-(3-aminophenyl)-7-hydroxy-5-Chydroxymethyl)[1,2,4]triazolo[4,3-a] cquinolin-1(2H)-one;

6-{3-[(cyclohexylamino)methyl]-4-methoxyphenyl }{ 1,2,4]triazolo[4,3—a]quinolin- 1 (2H)-one; 6-(4-methoxy-3-{[(tetrahydrofuran-2-ylmethyl)amino]Jmethyl } phenyl){” 1,2,4]triazolo[4,3- a]quinolin-1(2H)-one; 6-{3-[(cyclohexylamino)methyl]phenyl}[1,2,4]triazolo[4,3-alquinolin- 1(2H)-one; 6-{3-[(cyclopentylamino)methyl]phenyl}[1,2,4}triazolo[4,3-a]quinolin—1(2H)-one;

6-(3-{[(tetrahydrofuran-2-ylmethylamino]methyl }phenyl)[1,2,4]triazo- 1o[4,3-a]quinolin- 1(2H)-one; 6-(3-{[4-(hydroxymethyl)piperidin-1-yllmethyl } -4-methoxyphenyl)[ 1,22 ,4]triazolo[4,3- a]quinolin-1(2H)-one; 6-(3-{[4-(hydroxymethyl)piperidin-1-yllmethyl } phenyl)[1,2,4]triazolo § 4,3-a]quinolin-1(2H)-

one; 6-(3-hydroxyphenyl)[1,2,41triazolo[4,3-a]quinolin-1(2H)-one; 4-Chydroxymethyl)-8-pyridin-4-yl[1,2 4]triazolo[4,3-a]quinolin-1(2H)- one; 4-methyl-N-[1-0x0-8-(2-thienyl)-1,2-dihydro[ 1,2 4]triazolo[4,3-a]quin -olin-4- yllbenzenesulfonamide;

6-{3-[(isobutylamino)methy’1]-4-methoxyphenyl}[1,2,4]triazolo{4,3-a] «uinolin-1(2H)-one; 6-(3-{[4-(2-hydroxyethyl)-1 ,4-diazepan-1-yljmethyl } -4-methoxyphenw/1)[1,2,4]triazolo[4,3- a]quinolin-1(2H)-one; 6-{3-[(isobutylamino)methyIjphenyl}[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one;

6—(3-{[4-(2-hydroxyethyl)-1,4-diazepan-1-yljmethyl } phen yl)[1 ,2,4]triazolo[4,3-a]quinolin— 1(2H)-one;

8—(2-aminophenyl)-7-hydroxy-5-(hydroxymethyl)[1,2,4]tri azolo[4,3-a]quinolin-1 (2H)- }phenyl)[ 1,2,4]triazolo[4,3-

a]quinolin-1(2H)-one;

6—{4-hydroxy-3-[(isobutylamino)methyl}phenyl }[1,2,4]triaazolo[4,3-a]quinclin-1(2H)-one; 6-(4-hydroxy-3-{[4-(hydroxymethyl)piperidin-1-ylJmethyl }phenyl)[1,2,4]triazolo[4,3-

a] quinolin-1(2H)-one;

4-(hydroxymethyl)-8-(2-thienyl)[ 1,2,4]triazolo[4,3-a]quinolin-1(2H)-one;

6-(4-hydroxy-3-{[4-(2-hydroxyethyl)-1,4-diazepan-1-yllmethyl }phenyl)(1,2,4]triazolo[4,3— a] quinolin-1(2H)-one; 5-amino-8-(3-thienyl)[ 1,2,4]triazolo[4,3-a]quinolin-1(2H)- one; 5-amino-8-chloro-7-hydroxy[1,2,4]triazolo{4,3-a]quinolin- 1(2H)-one; 7-methoxy-5-methyl-8-(3-thienyl)[1,2,4]triazolo[4,3-a]quinnolin-1(2H)-one;

7-hydroxy-5-methyl-8-(3-thienyl)[ 1,2,4]triazolo[4,3-a]quin olin-1(2H)-one; 5-amino-7-hydroxy-8-(3-thienyl)[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; N-[2-(5-methyl-1-0x0-1,2-dihydro[1,2,4]triazolo[4,3-a)quirolin-8- yDphenyl]methanesulfonamide; 8-(1H-indol-3-yl)-5-methyl[ 1,2 4]triazolo[4,3-a]quinolin- 1 (2H)-one;

N-{[3-(5-methyl-1-0x0-1,2-dihydro[1,2,4]triazolo[4,3-a]quirolin-8- y)phenyllmethanesulfonamide; 5-amino-8-(1H-pyrrol-2-y1)[1,2,4]triazolof4,3-a]quinolin-1 (2H)-one; 5-Chydroxymethy!)-8-(1H-pyrrol-2-yl)[ 1,2,4]triazolo[4,3-a] quinolin-1(2H)-one; 5-methyl-8-(1H-pyrazol-4-yl)(1,2,4]triazolo[4,3-a]quinolin—- 1(2H)-one;

5-amino-8-(1H-pyrazol-4-yl)[1,2,4]triazolo[4,3-a]quinolin- 1 (2H)-one; 5-amino-8-(3-furyl)[1,2,4]triazolo[4,3-a]quinolin-1(2H)-ones; 5-methyl-8-(4-methyl-2-thienyl)[ 1,2 4]triazolo[4,3-a]quinol in- 1(2H)-one; 8-(3-furyl)-5-(hydroxymethyl)[ 1,2,4]triazolo[4,3-a]quinolin—1 (2H)-one;

8-[ 5-(hydroxymethyl)-2-thienyl]-5-methyl[ 1,2,4]triazolo[4,3 -a]quinolin-1(2H)-one;

8-[S-(1-hydroxyethyl)-2-thienyl]-5-methyl[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 5-(5S-methyl-1-oxo-1,2-dihydro[ 1,2,4]triazolo[4,3-a]quinolin -8-yl)thiophene-2-carboxylic acid;

tert-butyl 4-({{1-ox0-8-(3-thienyl)-1,2-dihydro[1,2,4]triazolo[4,3-a] qquinolin-5- yl]amino }methyl)piperidine-1-carboxylate; 5-amino-8-[5-(1-hydrox yethyl)-2-thienyl][1,2,4]triazolof4,3-a]quinolin-1 (2H)-one; 8-(1H-imidazol-4-yl)-5-methyl[1,2,4]triazolo(4,3 -a]quinolin-1(2H)—one;

5-(hydroxymethyl)-8-(1 H-pyrazol-4-y1)[1,2,4]triazolo(4,3 -a]quinol3n-1(2H)-one; 8-bromo-5-[(dimethylamino)methyl][1,2,4]triazolo[4,3-a]quinolin- 1(2H)-one; 8-(2-furyl)-5-(hydroxymethyl)[ 1,2 4]triazolo[4,3-a]quinolin-1(2H)—one; 5-methyl-8-(1,3-thiazol-2-y1)[1,2,4]triazolo[4,3-a]quinolin- 1 (2H)-One; 5-[(dimethylamino)methyl]-8-(1H-pyrrol-2-y1)[1,2,4]triazolo[4,3-a]quinolin-1 (2H)-one;

S-methyl-8-pyrazin-2-y1[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 5-(hydroxymethyl)-8-pyridin-4-yl[1,2,4]triazolo[4,3-a]quinolin-1(22H)-one; (5-methyl-1-oxo0-1,2-dihydro[1,2,4]triazolo[4,3-alquinolin-8-yl)bo-ronic acid, 8-(2-furyl)-5-phenyl[1,2 4]triazolo[4,3-a]quinolin-1(2H)-one; 5-phenyl-8-(1H-pyrrol-2-y1)[ 1,2 ,4]triazolo[4,3-a]quinolin-1(ZH)-One;

8-(3-furyl)-5-(morpholin-4-ylmethyl)[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; tert-butyl [2-({[1-0x0-8-(1H-pyrrol-2-yl)-1,2-dihydro[ 1,2,4]triazo 1o[4,3-a]quinolin-5- ylJmethyl}amino)ethyl]carbamate; 5-{[(2-aminoethyl)am inoJmethyl}-8-(1H-pyrrol-2-y1){ 1,2,4]triazc10[4,3-a]quinolin-1(2H)- one;

N-(2-aminoethyl)-8-bromo-1-oxo0-1,2-dihydro[1,2,4]triazolo[4,3- a]quinoline-5 -carboxamide; 8-(3-furyl)-1-ox0-1,2-dihydro[1,2,4]triazolo[4,3-a]quinoline-5-caarboxylic acid; 8-[3-(aminomethyl)phenyl]-5-phenyl({1,2,4]triazolo{4,3-a]quinoli n-1(2H)-one; N-[2-(dimethylamino)ethyl}-8-(3-furyl)-1-oxo-1,2-dihydro[1,2,4 Jtriazolo[4,3-a]quinoline-5- carboxamide;

5-methyl-8-[4-(2-moxpholin-4-ylethoxy)phenyl][1,2,4]triazolo[4 3-a]quinolin-1(2H)-one; 8-{4-[2-(diethylamino)ethoxy]phenyl}-5-methyl[ 1,2,4]triazolo[4-,3-a]quinolin- 1 (2H)-one; 8-[3«(dimethylamino)prop-1-yn-1-yl]-5-methyl[1,2,4]triazolo[4, 3-a]quinolin-1(2H)-one; 7-piperazin-1-yl-5-(2-thienyl)[ 1,2,4]triazolo[4,3-a}quinolin-1(2F)-one; 5-methyl-8-[3-(methylamino)prop-1-yn-1-yl][1,2,4]triazolo[4,3—a]quinolin-1(2H)-one;

5-methyl-8-[4-(morpholin-4-ylmethyl)phenyl][1,2,4]triazolo[4,3 -a]quinolin-1(2H)-one; N-[2~(dimethylamino)ethyl]-1-ox0-8-(1H-pyrrol-2-y1)-1,2-dihydro[ 1,2,4]triazolo[4,3- a)lquinoline-5-carboxamide;

N-[2-(dimethylamino)ethyl]-1-oxo-8-(3-thienyl)-1 ,2-dihydro[1,2,4]triazolo[4,3-a]quinolimne-5- carboxamide; 5-{ [(3R)-piperidin-3 -ylamino]methyl}-8-(1H-pyrro1-2-yl){1 ,2,4)triazolo[4,3-a]quinolin- 1(2H)-one; 5-methyl-8-{4-[(4-methylpiperazin-1-yl)methyl]phenyl} [1,2,4]triazolo[4,3-a]quinolin-1(2H)- one; tert-butyl (3S)-3-({[1-0x0-8-(3-thienyl)-1,2-dihydro[1,2,4]triazolo[4,3 -a]quinolin-5- yl]carbonyl }amino)piperidine- 1 carboxylate; 5-methyl-8-{4-[(methylamino)methyl]phenyl}[1,2,4}triazolo(4,3 -a]quinolin-1(2H)-one; 8-(3,3-diethoxyprop-1-yn-1-yl)-5-methyl[1,2,4}tria=zolo[4,3 -a]quinolin-1(2H)-one; 5-methyl-8-[5-(morpholin-4-ylmethyl)-3-thienyl][ 1 ,2,4]triazolo[4,3-a] quinolin-1(2H)-orx ¢; tert-butyl 4-[4-(5-methyl-1-oxo-1,2-dihydro[1,2,41triazolo[4,3 -a]quinolin-8- yl)benzyllpiperazine-1-carboxylate; 5-methyl-8-{5-[(methylamino)methyl}-3-thienyl } [ 1 ,2,4]triazolo[4,3-a]quinolin-1 (2H)-ore; S5-rmethyl-8-{5-[(4-methylpiperazin-1-yl)methyl}-3 —thienyl}[1 ,2,4]triazolo[4,3-a]quinolira- 1(2H)-one; tert-butyl 4-{[4-(5-methyl-1-ox0-1,2-dihydro[1,2,4 Jtriazolo[4,3-a] quinolin-8-yl)-2- thienyl]methyl }piperazine- 1 -carboxylate; 5-methyl-8-[4-(piperazin- 1-ylmethyl)phenyl][1,2,4 Jtriazolo[4,3-a]quinolin-1 (2H)-one;

1-oxo-N-[(3S)-piperidin-3-yl]-8-(3-thienyl)-1,2-dihydro( | ,2,4]triazolo[4,3-a]quinoline-5»- carboxamide; tert-butyl (3S)-3-({[1-oxo-8-(1H-pyrrol-2-yl)-1,2-dlihydro[1 ,2 Altriazolo[4,3-a]quinolin- =5- yl] carbonyl }amino)piperidine-1-carboxylate; 5-mnethy!-8-[5-(piperazin-1-ylmethyl)-3-thienyl][1,2,4]triazolo[4,3-a] quinolin-1(2H)-one;

N-(2-aminoethyl)-1-0x0-8-(3-thienyl)-1,2-dihydro[ 1 ,2,4]triazolo[4,3-alquinoline-5- carboxamide; 1-oxo0-N-[(3S)-piperidin-3-yl]-8-(1H-pyrrol-2-yl)- 1,2-dihydro[1 ,2,4]triazolo[4,3-a]quinOline- 5-carboxamide; 5-methyl-8-(1H-pyrrol-3-yl)[ 1,2 4]triazolo[4,3-a]q uinolin-1(2H)-one;

S-methyl-8-(3-thienylethynyl)[1,2,4]triazolo[4,3-a]]quinolin-1(2H)-one 8-[5-({[3-(dimethylamino)propyl]amino } methyl)- 3-thienyl]-5-methyl[1,2,4]triazolo[4,3 - a]quinolin-1(2H)-one; 5-methyl-8-{ 5-[(methylamino)methyl]-2-thienyl} [ 1,2 4]triazolo[4,3-a]quinolin-1(2H)-ome;

5-(hydroxymethyl)-8-[5-(morpholin-4-ylmethyl)-3-thienyl]{1 ,2,4ltriazolo» [4,3-a]quinolin- 1(2H)-one; 5-(hydroxymethyl)-8-{5-[(methylamino)methyl]-3-thienyl}[1 ,2,4]triazolof4,3-a]quinolin- 1(2H)-one; 5-Chydroxymethyl)-8-{5-[(4-methylpiperazin-1-yl)methyl}-3-thienyl}[1 ,=2,4]triazolof4,3- a]quinolin-1(2H)-one; 8-{5-[(dimethylamino)methyl] -3-thienyl}-5-(hydroxymethyl)[1,2,4]triaz olo[4,3-a] quinolin- 1(2H)-one; 5-(hydroxymethyl)-8-[5-(piper-azin-1-ylmethyl)-3-thienyl][1,2,4]triazolo [4,3-a] quinolin-

1(2H)-one; N-[2-(methylamino)ethyl]-1-0x0-8-(3-thienyl)-1,2-dihydro[ 1,2 4}triazol©[4,3-a]quinoline-5- carboxamide; N-[2-(methylamino)ethyl]-1-ox0-8-(1H-pyrrol-2-y})-1,2-dihydro[ 1,2,4]txiazolo[4,3- a]quinoline-5-carboxamide;

8-bromo-5-{[(2-methoxyethyl)(methyl)amino]Jmethyl}{1,2,4]triazolo[4, 3-a]quinolin-1(2H)-

one;

N-[2-(dimethylamino)ethyl]-8 -{ 5-[(4-methylpiperazin-1-yl)methyl]-3-thienyl}-1-oxo0-1,2- dihydro[1,2,4]triazolo[4,3-a]q vinoline-5-carboxamide; 8-bromo-5-{[2-(dimethylamino)ethoxy]methyl}[1,2,4]triazolo[4,3-a]qu inolin-1(2H)-one;

N-(2-morpholin-4-ylethyl)-1-oxo-8-(3-thienyl)-1,2-dihydro[ 1,2,4]triazo» 1o[4,3-a]quinoline-5- carboxamide; 5-[(4-methylpiperazin-1-yl)m ethyl]-8-(3-thienyl)[ 1,2,4]triazolo[4,3-a]q uinolin-1(2H)-one 8-[5-({[3-(dimethylamino)propyljamino } methyl)-3-thienyl]-5-

(hydroxymethyl)[ 1,2,4]triazo10[4,3-a]quinolin-1(2H)-one;

5-amino-8-{5-[(methylamino )methyl]-3-thienyl}[1,2,4]triazolo[4,3-a]q uinolin-1(2H)-one; 5-(hydroxymethyl)-8-[5-(moxpholin-4-ylmethyl)-2-thienyl}[ 1,2,4]triazolo[4,3-a]quinolin- 1(2H)-one; 5-(hydroxymethyl)-8-{5-{(methylamino)methyl]-2-thienyl}(1,2,4]triaz ©lo[4,3-a]quinolin- 1(2H)-one;

5-(hydroxymethyl)-8-{5-[(4-methylpiperazin-1-yl)methyl]-2-thieny! }[ 1,2,4]triazolo[4,3- a]quinolin-1(2H)-one; 8-{5-[(dimethylamino)methy/1]-2-thienyl}-5-(hydroxymethyl)[ 1,2,4]triazolo[4,3-a]quinolin~ 1(2H)-one;

5-[(3-hydrox ypyrrolidin- 1-yl)methyl]-8-(3-thienyl)[ 1 ,2,4)triazolo[4 5 3-alquinolin-1(2H)-one; 5-amino-8- {5-[(4-methylpiperazin-1-yl)methyl]-3 -thienyl}[1,2,4]tri.azolo[4,3-alquinolin- 1(2H)-one; 5-(hydroxymethyl)-8-[S-(piperazin-1-ylmethyl)-2-thienyl}{1 ,2,4]tri;aazolof4,3-a]quinolin- 1(2H)-one; 5-(morpholin-4-ylmethyl)-8-(3-thienyl)[1,2,4]triazolo[4,3-a] quinolin-1(2H)-one; 5-{[(2-methoxyethyl)(methyl)amino}methyl}-8-(3-thienyl)[1,2,4]triazolo[4,3 -a]quinolin- 1(2H)-one; 1-oxo0-N-(2-piperidin-1-ylethyl)-8-(3-thienyl)-1,2-dihydro[ 1,2 4]trizazolo[4,3-a] quinoline-5- carboxamide; 5-{[(2-morpholin-4-ylethyl)amino]methy1}-8-(3-thienyl){ 1 ,2,4]tria=zolo[4,3-a] quinolin-1(2H)- one; 5-[(dimethyl amino)methy!]-8-(3-thienyl)[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; N-[2-(dimethylamino)ethyl]-8-{4-[(4-methylpiperazin-1-yl)methyl Jphenyl}-1-oxo-1,2- dihydro[1,2,4]triazolo[4,3-a]quinoline-5-carboxamide; [1-ox0-8-(3-thienyl)-1,2-dihydro[ 1,2,4]triazolo[4,3-a]quinolin-5-yA Jmethyl glycinate; 5-{[2-(hydroxymethyl)morpholin-4-yljmethyl}-8-(1H-pyrrol-2-yi» {1 ,2,4]triazolo[4,3- a]quinolin-1 (2H)-one; 5-[(4-methylpiperazin- 1-yl)methyl]-8-(1H-pyrrol-2-y)[ 1,2,4]triazolo[4,3-a] quinolin-1(2H)- one; 5-{[2-(hydroxymethyl)morpholin-4-yl]methyl}-8-(3-thienyD)[1,2,4-]triazolo [4,3-alquinolin- 1(2ZH)-one; 5-{[4-(2-hydroxyethyl)piperazin-1-yl}methyl}-8-(3-thienyl)[1,2,41 triazolo[4,3-a]quinolin- 1(2H)-one; N° N3-dimethyl-N'-[1-0x0-8-(3-thienyl)-1,2-dihydro[1,2,4]triazolo[4,3-a] quinolin-5-yl]-beta- alaninamide; 5-{[(3R)-3-hydroxypyrrolidin-1-yl]methyl}-8-(3-thienyl)[1,2,4]tri azolo[4,3-a] quinolin-1(2H)- one; 5-{[(3R)-3-hydroxypyrrolidin-1-ylJmethyl}-8-(3-thienyl)[1,2,4]tri azolo[4,3-a]quinolin-1(2H)- one; 5-{[(2,3-dihydroxypropyl)(methyl)aminoJmethyl} -8-(3-thienyl)[1 ,2,4]triazolo[4,3-a]quinolin- 1(2H)-one;

5-({methyl[2-(methylaminc)ethyl]amino}methyl)-8-(3 -thieny1)[1,2,4]triazolo[4,3-a}quinolin~ 1(2H)-one; 5-{[(3-methoxypropyl)amino]methyl}-8-(3 -thienyl)[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 5-{[(2-hydroxyethyl)(methyl)amino]methyl }-8-(3-thienyl)[ 1 ,2 4]triazolo{4,3-a]quinolin-

1(2H)-one;

5-{[(3-hydroxypropyl)amino]methyl}-8-(3-thienyl){1 ,2,4]triazolo[4,3-a]quinolin-1(2H)-one; N-[2-(dimethylamino)ethy1]-8-{5-[(methylamino)methyl]-3-thienyl }-1-0xo- 1,2- dihydro[1,2,4]triazolo[4,3-a]quinoline-5-carboxamide; N-[2-(dimethylamino)ethyl]-8-[3-(dimethylamino)prop-1-yn-1-yl]-1-0xo0-1,2-

dihydro[1,2,4]triazolo[4,3-a]quinoline-5-carboxamide; 5-{[[3-(dimethylamino)propyl]j(methyl)aminoJmethy1}-8-(3-thienyl)[1 ,2,4]triazolo(4,3- a]quinolin-1(2H)-one; 5-({[3-(dimethylamino)propylJamino }methyl)-8-(3-thienyl)[ 1 ,2,4]triazolo[4,3-a]quinolin- 1(2H)-one;

N-[2-(dimethylamino)ethyl]-1-oxo0-8-[4-(piperazin-1-ylmethyl)phenyl]-1,2- dihydro[1,2,4]triazolo[4,3-a]quinoline-5-carboxamide; 5-(aminomethyl)-8-(1 H-pyrrol-2-y})[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; [1-0x0-8-(3-thienyl)-1,2-dihydro[ 1,2,4]triazolo[4,3-a]quinolin-5-yljmethyl N- methylglycinate;

5-{[(3-methoxypropyl)amino]methyl}-8-{5-[(methylamino)methyl]-3- thienyl}[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 5-{[(2-hydroxyethyl)(methyl)amino]methyl } -8-{ 5-[ (methylamino)methyl]-3- thienyl}(1,2,4]triazolo[4,3-a]quinolin- 1(ZH)-one; 5-{[4~(2-hydroxyethyl)piperazin- 1-yljmethy1}-8-(1 H-pyrrol-2-yi){1,2,4]triazolo[4,3-

a]quinolin-1(2H)-one; 5-{[(2,3-dihydroxypropyl)(methyl)aminoJmethyl}-8-{5-[(methylamino)methyl]-3- thienyl}[1,2,4]triazolo[4,3-a]quinolin- 1(2H)-one; '5-{[(3R)-3-hydroxypyrrolidin-1-yl]carbonyl } -8-(3-thienyl){ 1,2,4]triazolo[4,3-a}quinolin-

1(2H)-one; 1-0x0-8-(3-thienyl)-1,2-dihydro[1,2,4]triazolo[4,3-a]quinoline-5-carboxylic acid; 8-{5-[(methylamino)methyl]-3-thienyl }-5-({ methyl[2- (methylamino)ethylJamino}methyl)[1,2,4]triazolo{4,3-a]quinolin-1(2H)-one;

5-{[[3-(dimethylamino)propyl](methyl)amino]methyl}-8-{5 -[(methylamino)methyl]-3- thienyl}{1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 5-{[(3-hydroxypropyl)amino]methyl}-8-{5-[(methylamino)methyl]-3- thienyl}[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one;

5-({[3-(dimethylamino)propylJamino }methyl)-8-{5-[(methylamino)methyl]-3- thienyl}[1,2,41triazolo[4,3-a]lquinolin-1(2H)-one; 5-methyl-8-[3-(piperazin-1-ylmethyl)phenyl][1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; N-[2-(dimethylamino)e thyl]-8-{ 5-[(4-methylpiperazin-1-yl)methyl] -2-thienyl }-1-oxo-1,2- dihydro[1,2,4]triazolo[4,3-a]quinoline-5-carboxamide;

5-{{(3R)-3-hydroxypyrrolidin-1-yljcarbonyl}-8-{5-[(methylamino)mmethyl}-3- thienyl}[1,2,4]triazolo[4,3-alquinolin-1(2H)-one; 5-[(methylamino)methy/1]-8-(3-thienyl)[1,2,4]triazolo[4,3-a]quinolix3-1(2H)-one; 5-({[2-(methylamino)ethyl]amino} methyl)-8-(3-thienyl){1,2,4]triaz©lo[4,3-a}quinolin-1(2H)- one;

5-methyl-8-(5-{[(3S)-pyrrolidin-3-ylamino)methyl}-2-thienyl)[ 1,2,<¥triazolof4,3-a]quinolin- 1(2H)-one; 5-methyl-8-(5-{[(3R)-pyrrolidin-3-ylamino] methyl } -2-thienyl)[ 1,2,<4]triazolo[4,3-a]quinolin- 1(2H)-one;

N-azetidin-3-yl-1-0x0-8-(3-thienyl)-1,2-dihydro[ 1,2 4]triazolo[4,3-a]quinoline-5-

carboxamide; 8-{5-[(azetidin-3-ylamino)methyl]-2-thienyl}-5-methyl[ 1,2 4]triazo1o[4,3-a]quinolin-1(2H)}- one; 5-{[2-(dimethylamino)ethoxy]methyl }-8-(3-thienyl)[1,2,4]triazolo[<},3-a]quinolin-1(2H)-one; 5-({[(2S)-2,3-dihydroxypropyl]amino } methyl)-8-(3-thienyl)[ 1,2,4]twiazolo[4,3-a] quinolin-

1(2H)-one; 5-{[(3S)-3-hydroxypyrrolidin-1-yljmethyl}-8-(3-thienyl)[ 1,2,4]triaz olo[4,3-a]quinolin- 1(2H)- one; 5-{[(3-amino-2-hydroxy/propyl)amino}methyl } -8-(3-thienyl)[ 1,2,4Jtmriazolo[4,3-a]quinolin-

1(2H)-one;

5-{[(3R)-3-(dimethylamino)pyrrolidin-1-yl}methyl}-8-(3-thienyl)[ 1, 2,4]triazolo[4,3- aJquinolin-1(2H)-one; 5-{[(2-hydroxyethyl)amino]methyl}-8-(3-thienyl)[1,2,4]triazolo[4,3 ~a]quinolin-1(2H)-one; 5-(aminomethyl)-8-[4-(methoxymethyl)phenyl][ 1,2,4]triazolo[4,3-a] quinolin- 1(2H)-one;

N-(3-hydroxypropyl)-1-0xo0-8-(3-thienyl)-1,2-dihydro{1 ,2,4]triazolo[4,3-a]quinoline-5 - carboxamide;

5-{[(3S)-3-hydroxypyrrolidin-1-yljmethyl}-8-(1H-pyrrol-2-y})(1 ,2,4]triazolo[4,3-a]qu dinolin- 1(2H)-one;

5-{[(3S)-3-hydroxypyrrolidin-1-yllcarbony}-8-(3-thienyl)[ 1,2,4]triazolo[4,3-a]quino} -in-

1(2H)-one;

5-({[2-(dimethylamino)ethyl]Jamino} methyl)-8-(1H-pyrrol-2-yl)[1,2,4]triazolo[4,3- a]quinolin-1(2H)-one;

8-{5-[(ethylamino)methyl]-3-thienyl } -5-methyl| 1,2,4]triazolo[4,3-a]quinolin-1(2H)-ome;

8-{5-[(isopropylamino)methyl]-3-thienyl}-5-methyl[1,2,4]triazolo[4,3-a]quinolin-1(2 Bi)-one; N-azetidin-3-yl-8-{5-[(methylamino)methyl]-3-thienyl}-1-0xo-1,2-dihydro[1,2,4]triazzolo[4,3- a]quinoline-5-carboxamide; 5-(1H-imidazol-1-ylmethyl)-8-(1H-pyrrol-2-yl)[1,2,4]triazolo[4,3-a]quinolin- 1 (2H)-o me; 5-(1H-imidazol-1-ylmethyl)-8-(3-thienyl)[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one;

5-{[(3-hydroxypropyl)amino]methyl}-8-(1H-pyrrol-2-yl){1,2,4]triazolo{4,3-a]quinolix1-1(2H)- one; 5-[(pyrrolidin-3-ylamino)methyl]-8-(3-thienyl)[ 1,2,4]triazolo[4,3-a]quinolin- 1 (2H)-oxe; 5-{[(3R)-pyrrolidin-3-ylamino]methy1}-8-(3-thienyl)[ 1,2,4]triazolo[4,3-a]quinolin-1(22H)- one;

5-[(azetidin-3-ylamino)methyl]-8-(3-thienyl){ 1,2,4]triazolo[4,3-a]quinolin- 1(2H)-one 3 5-{[(3S)-3-aminopyrrolidin-1-yljmethyl}-8-(3-thienyl)[1,2,4]triazolo[4,3-a]quinolin- 1 (2H)- one; 5-{[(3R)-3-aminopyrrolidin-1-yljmethyl}-8-(3-thienyl)[1,2,4]triazolo[4,3-a]quinolin- 1(2H)- one;

5-{[(3R)-3~(dimethylamino)pyrrolidin-1-yljmethyl}-8-(1H-pyrrol-2-yD)[ 1,2 4}triazolo[4,3- a]quinolin-1(2H)-one; 5-{[(2-hydroxyethyl)amino]methyl }-8-(1H-pyrrol-2-yl)[1,2 4]triazolo{4,3-a]quinolin—1(2H)- one; 5-[(3-aminoazetidin-1-yl)methyl}-8-(3-thienyl)[ 1,2 ,4]triazolo{4,3-a]quinolin-1(2H)-ome;

5-({ [2-(dimethylamino)ethylJamino }methyl)-8-(3-thienyl)[ 1,2,4]triazolo[4,3-a]quinodin-

1(2H)-one; 5-({[2-(1H-imidazol-4-yl)ethyl]amino }methyl)-8-(3-thienyl)[ 1,2,4]triazolo[4,3-a]quimnolin- 1(2H)-one;

5-({[3-(1H-imidazol-4-yl)propylJamino} methyl)-8-(3-thienyl)[ 1,2,4]triazce10[4,3-a]quinolin- 1(2H)-one; 5-[(isopropylamino)methy!]-8-(3-thienyl)[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 5-[(ethylamino)methyl]-8-(3-thienyl)[ 1,2,4]triazolo[4,3-a]quinolin-1(2H)- one;

5-[(cyclopropylamino)methyl]-8-(3-thienyl)[1,2,4]triazolo[4,3-a]quinolin—1(2H)-one; 5-{{(cyclopropylmethyl)amino]methyl}-8-(3-thienyl)[ 1,2,4]triazolo[4,3-a quinolin-1(2H)- one; 5-({[2-(dimethylamino)-1-methylethyljamino } methyl)-8-(3-thienyl)[1,2,4-]triazolo[4,3- alquinolin-1(2H)-one;

N-[2-(dimethylamino)-1-methylethyl]-1-oxo-8-(3-thienyl)-1,2-dihydro[ 1,2 4}triazolo[4,3- aJquinoline-5-carboxamide; 5-{[methyl(2-pyridin-4-ylethyl)amino]methyl}-8-(3-thienyl){ 1,2,4]triazol o[4,3-a]quinolin- 1(2H)-one; 5-[(3-aminoazetidin-1-yl)carbonyl]-8-(3-thienyl)[ 1,2,4]triazolo[4,3-a]quiznolin-1(2H)-one; N-[2-(1H-imidazol-4-yl)ethyl }-1-ox0-8-(3-thienyl)-1,2-dihydro[1,2,4]tria Zolo[4,3- a]quinoline-5-carboxamide; N-[3-(1H-imidazol-4-yl)propyl}-1-oxo-8-(3-thienyl)-1,2-dihydro[1,2,4]triazolo[4,3- aJquinoline-S-carboxamide; 5-({[2-(isopropylamino)ethyl Jamino} methyl)-8-(3-thienyl)[ 1,2,4]triazolo [4,3-a]quinolin- 1(2H)-one; N-[2-(isopropylamino)ethyl]- 1-0x0-8-(3-thienyl)-1,2-dihydro[1,2,4]triazolo[4,3-a}quinoline- 5-carboxamide; N-{(1-ethylpyrrolidin-2-yl)methyl]-1-oxo0-8-(3-thienyl)-1,2-dihydro[ 1,2,4& Jtriazolo[4,3- aJquinoline-5-carboxamide; 5-({[3-(dimethylamino)propy1]amino }methyl)-8-(1H-pyrrol-2-yl)[1,2,4] txiazolo[4,3- a]quinolin-1(2H)-one; 5-{[4-(hydroxymethyl)-1H-1,2,3-triazol-1-ylJmethyl}-8-(3-thieny})[ 1,2,4 Jtriazolo[4,3- a]quinolin-1(2H)-one; 5-{[(pyridin-2-ylmethyl)amino]methyl}-8-(3-thienyl)[ 1,2 ,4]triazolo[4,3- a]quinolin-1(2H)- one; 5-({[(5-methyl-2-furyl)methy1]amino } methyl)-8-(3-thienyl)[1,2,4]triazoM o[4,3-a]quinolin- 1(2H)-one;

5-{[(2-pyridin-2-ylethyl)amino}methyl}-8-(3-thienyl)[ 1,2,4]trimazolo[4,3-a]quinolin-1 (2H)- one; 5-(methoxymethyl)-8-(3-thienyl)[ 1,2,4]triazolo[4,3-a]quinolin- 1(2H)-one; 5-({[(5-methylpyrazin-2-yl)methyl]amino }methyl)-8-(3-thieny1)[1,2,4]triazolo[4,3-

a]quinolin-1(2H)-one; 5-({4-[(methylamino)methyl]-1H-1,2,3-triazol-1-yl } methyl)-8—(3-thienyl)[ 1,2,4]triazolo[4,3- a]quinolin-1(2H)-one; 5-(aminomethyl)-8-(3-thienyl)[ 1,2,4]triazolo{4,3-a]quinolin-1(22H)-one; 5-{[(2-aminoethyl)aminojmethyl}-8-(3-thienyl)[ 1,2,4]triazolo[ 4,3-a]quinolin-1(2/)-one;

5-chloro-2H-[1,2 4]triazolo[4,3-0]quinolin-1-one; 4-(1-oxo0-1,2-dihydro-[1,2,4]triazolof4,3-0}quinolin-5-yl)-benzzaldehyde; 3-methoxy-2-(1~-oxo-1,2-dihydro[1,2,4}triazolo[4,3-alquinolin—5-yl)benzaldehyde; 8-bromo-1-o0x0-1,2-dihydro -[1,2,4]-triazolo[4,3-a]quinoline-5 —caroxylic acid; 8-bromo-1-o0xo0-1,2-dihydro -[1,2,4]-triazolo[4,3-a]quinoline-5 —caroxylic acid ethyl ester;

7-chloro-5-methyl-2H-[1,2,4}triazolo[4,3-0]quinolin-] -one; 4-(5-methyl-1-0xo0-1,2-dihydro-[1,2,4]triazolo[4,3-0]quinolin-7-yl)-benzaldehyde; 2-methoxy-5-(5 -methyl-1-0x0-1,2-dihydro[ 1,2 4]triazolo[4,3-cz]quinolin-7-yl)benzaldehyde; 3-(7-methoxy-5-methyl-1-ox0-1,2-dihydro-[1,2,4]triazolo[4,3— a}quinolin-8-yl)-benzaldehyde; 2-methoxy-5-(7-methoxy-5-methyl-1-ox0-1,2-dihydrof1,2,4]triazolo[4,3-a]quinolin-8-

yl)benzaldehyde; 2-(7-methoxy-5-methyl-1-0x0-1,2-dihydro[ 1,2,4]triazolo[4,3-cz]quinolin-8-yl)benzaldehyde; 8-bromo-5-bromomethyl( 1,2[4]triazolo[4,3-a]quinolin- 1(2H)-one; 8-bromo-5-hydroxymethyl[1,2[4]triazolo[4,3-a]quinolin-1(2H)-one; 8-bromo-1-oxo0-1,2-dihydro[1,2,4]triazolo[4,3-a]quinoline-4-c arboxylic acid;

4-amino-8-bromol 1,2 4]triazolo[4,3-a]quinolin-1(2H)-one; 8-bromo-5-phenyl[1,2,4]triazolo[4,3-a}quinolin-1(2H)-one; 8-bromo-5-methoxymethy(1,2,4]triazolo[4,3-a]quinolin-1(2H»-one; 8-Bromo-5-(aminomethyl)[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one; 5-(azidomethyl)-8-bromo([1,2,4] triazolo[4,3-a]quinolin-1(2H) —one;

7-bromo-5-thien-2-yl[1,2,4]triazolo[4,3-a]quinolin-1(2H)-one ethyl 8-chloro-7-methoxy-1- oxo-1,2-dihydro[1,2,4]triazolo[4,3-a]lquinoline-S-carboxylate; 8-chloro-7-methoxy-1-oxo-1,2-dihydro[1,2,4]triazolo[4,3-a]quainoline-5-carboxylic acid;

to ; PCT/SE2004/000351 5-amino-8-chloro-7-methoxy[1,2,4]triazolo[4,3-a]quinolin-1 (2H)-one; 8-chloro-5-(hxydroxymethyl)-7-methoxy[1,2,4]triazolo[4,3-a] quinolin-1(2 H)-one; 2-{3-[(1-oxo~-1,2-dihydro[1,2,4]triazolo[4,3-a]quinolin-5-yl)oxy]propyl}-1H-isoindole- 1,3(2H)-dione; 2-{3-[(8-chloro-5-methyl-1-ox0-1,2-dihydro[1,2,4]triazolo[4 ,3-alquinolin-7-yl)oxy]propyl}- 1H-isoindole -1,3(2H)-dione; 7-(3-aminopropoxy)-8-chloro-5-methyl{1,2,4]triazolo[4,3-a] quinolin-1(24)-one; or a pharmaceutically acceptable salt thereof.

12. A cormpound as recited in anyone of claims 1-11 or a pharmaceutically acceptable salt thereof, wherein one or more of the atoms is a radioisoto pe of the same element.

13. The use of a compound as recited in any one of claims 1-11 or a pharmaceutically acceptable salt thereof as a medicament.

14. The use of a compound as recited in any one of claims 1-11 or a pharmaceutically acceptable salt thereof in the preparation of a medicament for the treatment of cancer.

15. The use of a compound as recited in any one of claims 1-11 or a pharmaceutically acceptable salt thereof, in the preparation of a medicament for the treatment of neoplastic disease such as carcinoma of the breast, ovary, lung, colon, prostate or other tissues, as well as leukemias and lymphomas, tumors of the central and peripheral nervous system, and other tumor types such as melanoma, fibrosarcoma and osteosarcoma.

16. The use of a compound as recited in any one of claims 1-11 or a pharmaceutically acceptable salt thereof, in the preparation of a medicament for the treatment of proliferative diseases including autoimmune, inflammatory, neurological, and cardiovascular diseases.

17. The use of a compound as recited in any one of claims 1-11 or a pharmaceutically acceptable salt thereof, in the preparation of a medicament for the inhibition of CHK1 kinase. AMENDED SHEET a . PCT/SE2004/000351 .

18. Use of a compound as recited in any one of claims 1-11 or a pharmaceutically acceptable salt of said compound in the preparation of a m edicament for the treatment of a human or animal by limiting cell replication.

19. A compound as claimed in any one of claims 1, or 11, or 12, substantially as herein described with reference to and as illustrated in any of the examples.

20. Use as claimed in any one of claims 14 to 18, substantially as herein described with reference to and as illustrated in any of the examples. AMENDED SHEET