ZA200100365B - Process for the synthesis of (1 H)-benzo(C)quinolizin-3-ones derivatives. - Google Patents

Process for the synthesis of (1 H)-benzo(C)quinolizin-3-ones derivatives. Download PDF

Info

Publication number: ZA200100365B
Authority: ZA; South Africa
Prior art keywords: tetrahydro; benzo; quinolizin; dimethyl; chloro
Prior art date: 1998-08-03

Application number

ZA200100365A

Other languages

English (en)

Inventor

Antonio Guarna

Mario Serio

Occhiato Ernesto Giovanni

Original Assignee

Applied Research Systems

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1998-08-03

Filing date

2001-01-12

Publication date

2001-07-26

2001-01-12 Application filed by Applied Research Systems filed Critical Applied Research Systems

2001-07-26 Publication of ZA200100365B publication Critical patent/ZA200100365B/en

Links

238000000034 method Methods 0.000 title claims description 21
230000015572 biosynthetic process Effects 0.000 title description 4
238000003786 synthesis reaction Methods 0.000 title description 4
HHWOCYWGVOSDOP-UHFFFAOYSA-N 1,2-dihydrobenzo[f]quinolizin-3-one Chemical class C1=CC=C2N3CCC(=O)C=C3C=CC2=C1 HHWOCYWGVOSDOP-UHFFFAOYSA-N 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims description 37
WZCXJNBOOQLKKD-UHFFFAOYSA-N 2,4-dihydroquinolizin-3-one Chemical compound C1=CC=CN2CC(=O)CC=C21 WZCXJNBOOQLKKD-UHFFFAOYSA-N 0.000 claims description 18
125000000217 alkyl group Chemical group 0.000 claims description 13
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 11
125000000753 cycloalkyl group Chemical group 0.000 claims description 11
238000006243 chemical reaction Methods 0.000 claims description 10
125000003118 aryl group Chemical group 0.000 claims description 9
125000000623 heterocyclic group Chemical group 0.000 claims description 9
238000002360 preparation method Methods 0.000 claims description 9
238000010992 reflux Methods 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 7
239000002904 solvent Substances 0.000 claims description 7
WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 claims description 6
-1 C. galkinyl Chemical group 0.000 claims description 6
229910052799 carbon Inorganic materials 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 6
125000003342 alkenyl group Chemical group 0.000 claims description 5
125000006193 alkinyl group Chemical group 0.000 claims description 5
AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 claims description 5
150000002367 halogens Chemical class 0.000 claims description 5
230000000269 nucleophilic effect Effects 0.000 claims description 5
150000003839 salts Chemical class 0.000 claims description 5
XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 claims description 4
125000001769 aryl amino group Chemical group 0.000 claims description 4
125000004104 aryloxy group Chemical group 0.000 claims description 4
239000003960 organic solvent Substances 0.000 claims description 4
UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical compound C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 claims description 4
SNEPAAKJPPNOQM-UHFFFAOYSA-N 4,8-dimethyl-1,2,5,6-tetrahydrobenzo[f]quinolizin-3-one Chemical compound C1CC2=CC(C)=CC=C2N2C1=C(C)C(=O)CC2 SNEPAAKJPPNOQM-UHFFFAOYSA-N 0.000 claims description 3
DWGUKGCMIQALCV-UHFFFAOYSA-N 8-chloro-4-methyl-1,2,5,6-tetrahydrobenzo[f]quinolizin-3-one Chemical compound C1CC2=CC(Cl)=CC=C2N2C1=C(C)C(=O)CC2 DWGUKGCMIQALCV-UHFFFAOYSA-N 0.000 claims description 3
125000003282 alkyl amino group Chemical group 0.000 claims description 3
150000002148 esters Chemical class 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
NFTPVKSCTLIKKF-UHFFFAOYSA-N 1,4-dimethyl-1,2,5,6-tetrahydrobenzo[f]quinolizin-3-one Chemical compound C1=CC=C2N3C(C)CC(=O)C(C)=C3CCC2=C1 NFTPVKSCTLIKKF-UHFFFAOYSA-N 0.000 claims description 2
PMVHQTAUPSEQBB-UHFFFAOYSA-N 1,6-dimethyl-1,2,5,6-tetrahydrobenzo[f]quinolizin-3-one Chemical compound C1=CC=C2N3C(C)CC(=O)C=C3CC(C)C2=C1 PMVHQTAUPSEQBB-UHFFFAOYSA-N 0.000 claims description 2
SPMRKOLVFPPPIE-UHFFFAOYSA-N 1-methyl-1,2,5,6-tetrahydrobenzo[f]quinolizin-3-one Chemical compound C1=CC=C2N3C(C)CC(=O)C=C3CCC2=C1 SPMRKOLVFPPPIE-UHFFFAOYSA-N 0.000 claims description 2
LQPRXJUNHPLCCJ-UHFFFAOYSA-N 5-methyl-1,2,5,6-tetrahydrobenzo[f]quinolizin-3-one Chemical compound C1CC(=O)C=C2C(C)CC3=CC=CC=C3N21 LQPRXJUNHPLCCJ-UHFFFAOYSA-N 0.000 claims description 2
BRTGJFMJRRWDTL-UHFFFAOYSA-N 8-chloro-1,2,5,6-tetrahydrobenzo[f]quinolizin-3-one Chemical compound C1CC(=O)C=C2CCC3=CC(Cl)=CC=C3N21 BRTGJFMJRRWDTL-UHFFFAOYSA-N 0.000 claims description 2
MOBQBGBOLOWQDH-UHFFFAOYSA-N 8-chloro-1-methyl-1,2,5,6-tetrahydrobenzo[f]quinolizin-3-one Chemical compound ClC1=CC=C2N3C(C)CC(=O)C=C3CCC2=C1 MOBQBGBOLOWQDH-UHFFFAOYSA-N 0.000 claims description 2
ACIILYWZPSMNPS-UHFFFAOYSA-N 8-chloro-4,5-dimethyl-1,2,5,6-tetrahydrobenzo[f]quinolizin-3-one Chemical compound C1CC(=O)C(C)=C2C(C)CC3=CC(Cl)=CC=C3N21 ACIILYWZPSMNPS-UHFFFAOYSA-N 0.000 claims description 2
125000005129 aryl carbonyl group Chemical group 0.000 claims description 2
150000001540 azides Chemical class 0.000 claims description 2
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 2
239000012022 methylating agents‎ Substances 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
125000004434 sulfur atom Chemical group 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
WXKKGCUAJQVLGT-UHFFFAOYSA-N 4,5,6-trimethyl-1,2,5,6-tetrahydrobenzo[f]quinolizin-3-one Chemical compound C1CC(=O)C(C)=C2C(C)C(C)C3=CC=CC=C3N21 WXKKGCUAJQVLGT-UHFFFAOYSA-N 0.000 claims 1
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KPGSNZSOMIRJNF-UHFFFAOYSA-N 4,6-dimethyl-1,2,5,6-tetrahydrobenzo[f]quinolizin-3-one Chemical compound C1=CC=C2C(C)CC3=C(C)C(=O)CCN3C2=C1 KPGSNZSOMIRJNF-UHFFFAOYSA-N 0.000 claims 1
DIDYGJJHMJNMJM-UHFFFAOYSA-N 8-chloro-5-methyl-1,2,5,6-tetrahydrobenzo[f]quinolizin-3-one Chemical compound C1CC(=O)C=C2C(C)CC3=CC(Cl)=CC=C3N21 DIDYGJJHMJNMJM-UHFFFAOYSA-N 0.000 claims 1
UXLGYJWIWHMDNY-UHFFFAOYSA-N 8-chloro-6-methyl-1,2,5,6-tetrahydrobenzo[f]quinolizin-3-one Chemical compound C1=C(Cl)C=C2C(C)CC3=CC(=O)CCN3C2=C1 UXLGYJWIWHMDNY-UHFFFAOYSA-N 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
230000035484 reaction time Effects 0.000 claims 1
238000007363 ring formation reaction Methods 0.000 claims 1
125000003944 tolyl group Chemical group 0.000 claims 1
JLIDVCMBCGBIEY-UHFFFAOYSA-N 1-penten-3-one Chemical compound CCC(=O)C=C JLIDVCMBCGBIEY-UHFFFAOYSA-N 0.000 description 14
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
239000003921 oil Substances 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
239000000725 suspension Substances 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
239000000460 chlorine Substances 0.000 description 6
239000012299 nitrogen atmosphere Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
239000003208 petroleum Substances 0.000 description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000001816 cooling Methods 0.000 description 3
DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
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XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
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ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
229940125782 compound 2 Drugs 0.000 description 2
229940126214 compound 3 Drugs 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
238000001914 filtration Methods 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
150000003556 thioamides Chemical class 0.000 description 2
OPJKPSOLCGGXEW-UHFFFAOYSA-N 1,2,5,6-tetrahydrobenzo[f]quinolizin-3-one Chemical compound C1=CC=C2N3CCC(=O)C=C3CCC2=C1 OPJKPSOLCGGXEW-UHFFFAOYSA-N 0.000 description 1
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RCYXFHONBSRNES-UHFFFAOYSA-N 1,5-dimethyl-1,2,5,6-tetrahydrobenzo[f]quinolizin-3-one Chemical compound C1=CC=C2N3C(C)CC(=O)C=C3C(C)CC2=C1 RCYXFHONBSRNES-UHFFFAOYSA-N 0.000 description 1
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 1
UMHLZGJTGWFCGD-UHFFFAOYSA-N 3,4-dihydro-1h-quinoline-2-thione Chemical compound C1=CC=C2NC(=S)CCC2=C1 UMHLZGJTGWFCGD-UHFFFAOYSA-N 0.000 description 1
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125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
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CDARSTIBNDQLRM-UHFFFAOYSA-N 8-chloro-4,6-dimethyl-1,2,5,6-tetrahydrobenzo[f]quinolizin-3-one Chemical compound C1=C(Cl)C=C2C(C)CC3=C(C)C(=O)CCN3C2=C1 CDARSTIBNDQLRM-UHFFFAOYSA-N 0.000 description 1
VYSWJAUCIPHIER-UHFFFAOYSA-N 8-chloro-5,6-dimethyl-1,2,5,6-tetrahydrobenzo[f]quinolizin-3-one Chemical compound C1CC(=O)C=C2C(C)C(C)C3=CC(Cl)=CC=C3N21 VYSWJAUCIPHIER-UHFFFAOYSA-N 0.000 description 1
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ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
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229920006395 saturated elastomer Polymers 0.000 description 1
239000007858 starting material Substances 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/03—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/04—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/10—Anti-acne agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/14—Drugs for dermatological disorders for baldness or alopecia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Dermatology (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Carbon And Carbon Compounds (AREA)
Inorganic Compounds Of Heavy Metals (AREA)
Plural Heterocyclic Compounds (AREA)

ZA200100365A 1998-08-03 2001-01-12 Process for the synthesis of (1 H)-benzo(C)quinolizin-3-ones derivatives. ZA200100365B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
EP98114524		1998-08-03

Publications (1)

Publication Number	Publication Date
ZA200100365B true ZA200100365B (en)	2001-07-26

Family

ID=8232396

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ZA200100365A ZA200100365B (en)	1998-08-03	2001-01-12	Process for the synthesis of (1 H)-benzo(C)quinolizin-3-ones derivatives.

Country Status (29)

Country	Link
US (1)	US6723850B1 (xx)
EP (1)	EP1102765B1 (xx)
JP (1)	JP2002522435A (xx)
KR (1)	KR100624239B1 (xx)
CN (1)	CN1128148C (xx)
AT (1)	ATE250057T1 (xx)
AU (1)	AU751873B2 (xx)
BG (1)	BG65062B1 (xx)
BR (1)	BR9912870A (xx)
CA (1)	CA2338498C (xx)
CZ (1)	CZ291648B6 (xx)
DE (1)	DE69911430T2 (xx)
DK (1)	DK1102765T3 (xx)
EA (1)	EA003997B1 (xx)
EE (1)	EE04642B1 (xx)
ES (1)	ES2203169T3 (xx)
HK (1)	HK1037368A1 (xx)
HU (1)	HUP0103241A3 (xx)
IL (2)	IL141212A0 (xx)
NO (1)	NO20010559L (xx)
NZ (1)	NZ509243A (xx)
PL (1)	PL198963B1 (xx)
PT (1)	PT1102765E (xx)
SI (1)	SI1102765T1 (xx)
SK (1)	SK285438B6 (xx)
TR (1)	TR200100286T2 (xx)
UA (1)	UA67787C2 (xx)
WO (1)	WO2000008019A1 (xx)
ZA (1)	ZA200100365B (xx)

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US20100074949A1 (en)	2008-08-13	2010-03-25	William Rowe	Pharmaceutical composition and administration thereof
BR122018075478B8 (pt)	2004-06-24	2023-10-31	Vertex Pharma	moduladores de transportadores de cassete de ligação de atp
US8354427B2 (en)	2004-06-24	2013-01-15	Vertex Pharmaceutical Incorporated	Modulators of ATP-binding cassette transporters
EP1979367A2 (en) *	2005-12-24	2008-10-15	Vertex Pharmaceuticals Incorporated	Quinolin-4-one derivatives as modulators of abc transporters
HUE049976T2 (hu)	2005-12-28	2020-11-30	Vertex Pharma	N-[2,4-bisz(1,1-dimetil-etil)-5-hidroxi-fenil]-1,4-dihidro-4-oxo-kinolin-3-karboxamid amorf alakjának gyógyászati kompozíciói
EP2408750B1 (en)	2009-03-20	2015-08-26	Vertex Pharmaceuticals Incorporated	Process for making modulators of cystic fibrosis transmembrane conductance regulator
US8802700B2 (en)	2010-12-10	2014-08-12	Vertex Pharmaceuticals Incorporated	Modulators of ATP-Binding Cassette transporters
AU2011344442B2 (en) *	2010-12-14	2016-07-07	Syngenta Participations Ag	Strigolactam derivatives and their use as plant growth regulators
JP2015511583A (ja)	2012-02-27	2015-04-20	バーテックスファーマシューティカルズインコーポレイテッドＶｅｒｔｅｘＰｈａｒｍａｃｅｕｔｉｃａｌｓＩｎｃｏｒｐｏｒａｔｅｄ	薬学的組成物およびその投与
ES2702288T3 (es)	2014-10-07	2019-02-28	Vertex Pharma	Co-cristales de moduladores de regulador de conductancia transmembrana de la fibrosis quística
CN105001216B (zh) *	2015-07-08	2017-03-01	中国科学院兰州化学物理研究所	一种喹嗪酮的制备方法

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US5064961A (en) *	1989-12-18	1991-11-12	E. R. Squibb & Sons, Inc.	Process for preparing an optically active cyclobutane nucleoside
FR2696465B1 (fr) *	1992-10-02	1994-12-23	Adir	Nouveaux dérivés d'ellipticine, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent.
IT1286545B1 (it)	1996-02-09	1998-07-15	Antonio Guarna	Derivati benzo(c) chinolizinici,loro preparazione ed uso come inibitori delle 5-alfa-riduttasi
JPH09316076A (ja) *	1996-05-24	1997-12-09	Nippon Paper Ind Co Ltd	９−置換プリン誘導体及びその抗ウイルス剤としての用途

1999
- 1999-07-23 SI SI9930419T patent/SI1102765T1/xx unknown
- 1999-07-23 PT PT99941269T patent/PT1102765E/pt unknown
- 1999-07-23 HU HU0103241A patent/HUP0103241A3/hu unknown
- 1999-07-23 DE DE69911430T patent/DE69911430T2/de not_active Expired - Fee Related
- 1999-07-23 CN CN99809204A patent/CN1128148C/zh not_active Expired - Fee Related
- 1999-07-23 EP EP99941269A patent/EP1102765B1/en not_active Expired - Lifetime
- 1999-07-23 ES ES99941269T patent/ES2203169T3/es not_active Expired - Lifetime
- 1999-07-23 CA CA002338498A patent/CA2338498C/en not_active Expired - Fee Related
- 1999-07-23 NZ NZ509243A patent/NZ509243A/xx not_active IP Right Cessation
- 1999-07-23 CZ CZ2001434A patent/CZ291648B6/cs not_active IP Right Cessation
- 1999-07-23 EE EEP200100060A patent/EE04642B1/xx not_active IP Right Cessation
- 1999-07-23 AU AU63123/99A patent/AU751873B2/en not_active Ceased
- 1999-07-23 IL IL14121299A patent/IL141212A0/xx active IP Right Grant
- 1999-07-23 BR BR9912870-5A patent/BR9912870A/pt not_active Application Discontinuation
- 1999-07-23 TR TR2001/00286T patent/TR200100286T2/xx unknown
- 1999-07-23 PL PL345802A patent/PL198963B1/pl not_active IP Right Cessation
- 1999-07-23 WO PCT/EP1999/005277 patent/WO2000008019A1/en active IP Right Grant
- 1999-07-23 DK DK99941269T patent/DK1102765T3/da active
- 1999-07-23 EA EA200100213A patent/EA003997B1/ru not_active IP Right Cessation
- 1999-07-23 KR KR1020017000325A patent/KR100624239B1/ko not_active IP Right Cessation
- 1999-07-23 UA UA2001020777A patent/UA67787C2/uk unknown
- 1999-07-23 JP JP2000563652A patent/JP2002522435A/ja active Pending
- 1999-07-23 AT AT99941269T patent/ATE250057T1/de not_active IP Right Cessation
- 1999-07-23 SK SK167-2001A patent/SK285438B6/sk not_active IP Right Cessation
- 1999-07-23 US US09/743,373 patent/US6723850B1/en not_active Expired - Fee Related
2001
- 2001-01-12 ZA ZA200100365A patent/ZA200100365B/en unknown
- 2001-01-30 BG BG105198A patent/BG65062B1/bg unknown
- 2001-02-01 IL IL141212A patent/IL141212A/en not_active IP Right Cessation
- 2001-02-01 NO NO20010559A patent/NO20010559L/no not_active Application Discontinuation
- 2001-11-20 HK HK01108153A patent/HK1037368A1/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
BG105198A (en)	2001-12-29
EA003997B1 (ru)	2003-12-25
CN1128148C (zh)	2003-11-19
NZ509243A (en)	2002-11-26
PL198963B1 (pl)	2008-08-29
HUP0103241A2 (hu)	2002-01-28
EE04642B1 (et)	2006-06-15
WO2000008019A1 (en)	2000-02-17
US6723850B1 (en)	2004-04-20
EP1102765B1 (en)	2003-09-17
JP2002522435A (ja)	2002-07-23
CA2338498C (en)	2009-05-19
EP1102765A1 (en)	2001-05-30
NO20010559D0 (no)	2001-02-01
SK285438B6 (sk)	2007-01-04
CA2338498A1 (en)	2000-02-17
EA200100213A1 (ru)	2001-08-27
DK1102765T3 (da)	2004-02-02
AU751873B2 (en)	2002-08-29
SI1102765T1 (en)	2003-12-31
HK1037368A1 (en)	2002-02-08
PL345802A1 (en)	2002-01-02
DE69911430T2 (de)	2004-07-22
HUP0103241A3 (en)	2002-10-28
AU6312399A (en)	2000-02-28
UA67787C2 (uk)	2004-07-15
CZ2001434A3 (cs)	2001-08-15
KR100624239B1 (ko)	2006-09-13
KR20010074684A (ko)	2001-08-09
SK1672001A3 (en)	2001-08-06
IL141212A (en)	2006-12-31
CZ291648B6 (cs)	2003-04-16
BR9912870A (pt)	2001-10-16
PT1102765E (pt)	2003-12-31
EE200100060A (et)	2002-06-17
IL141212A0 (en)	2002-03-10
DE69911430D1 (de)	2003-10-23
BG65062B1 (bg)	2007-01-31
NO20010559L (no)	2001-02-01
ATE250057T1 (de)	2003-10-15
ES2203169T3 (es)	2004-04-01
CN1311788A (zh)	2001-09-05
TR200100286T2 (tr)	2001-07-23

Publication	Publication Date	Title
EP1102765B1 (en)	2003-09-17	PROCESS FOR THE SYNTHESIS OF (1$i(H))-BENZO C]QUINOLIZIN-3-ONES DERIVATIVES
AU711886B2 (en)	1999-10-21	Benzo(C)quinolizine derivatives, their preparation and use as 5alpha-reductases inhibitors
WO1994007873A1 (es)	1994-04-14	Prodedimiento para la obtencion de benzoxazinas utiles para la sintesis de ofloxacina, levofloxacina y derivados
CS203135B2 (en)	1981-02-27	Method of producing racemic or optically active pyrimido/1,2a/heterocyclic compounds
AU744105B2 (en)	2002-02-14	Benzo(c)quinolizine derivatives and their use as 5 alpha-reductases inhibitors
MXPA01000869A (en)	2001-12-13	Process for the synthesis of (1h
CA2245758C (en)	2006-04-11	Benzo[c]quinolizine derivatives, their preparation and use as 5.alpha.-reductases inhibitors