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ES446081A1 - Pyridazinyl,pyrimidinyl,pyrazinyl and pyridyl compounds and processes for their manufacture - Google Patents

Pyridazinyl,pyrimidinyl,pyrazinyl and pyridyl compounds and processes for their manufacture

Info

Publication number
ES446081A1
ES446081A1 ES76446081A ES446081A ES446081A1 ES 446081 A1 ES446081 A1 ES 446081A1 ES 76446081 A ES76446081 A ES 76446081A ES 446081 A ES446081 A ES 446081A ES 446081 A1 ES446081 A1 ES 446081A1
Authority
ES
Spain
Prior art keywords
inferior
amino
carbon atoms
alquilo
alcoxi
Prior art date
Legal status (The legal status 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 status listed.)
Expired
Application number
ES76446081A
Other languages
Spanish (es)
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Novartis AG
Original Assignee
Ciba Geigy AG
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.)
Filing date
Publication date
Priority claimed from CH244473A external-priority patent/CH584209A5/en
Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG
Publication of ES446081A1 publication Critical patent/ES446081A1/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/69—Two or more oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Procedure for obtaining 2-hydroxy-3-aminopropane derivatives of beta-receptor activity, of formula ** (See formula) ** where Het means pyridyl , pyrazinyl, pyridazinyl, pyrimidinyl or their N-oxides; stands for hydrogen or methyl; R2 means lower alkyl with up to 7 carbon atoms, phenylalkyl with up to 7 carbon atoms in the alkyl part, optionally substituted by lower alkyl or lower alkoxy groups, in each case with up to 7 carbon atoms, trifluoromethyl or halogen, cyanoalkyl lower or lower carboxyalkyl, in each case with up to 7 carbon atoms in the lower alkyl part, or lower carboxyalkyl with up to 7 carbon atoms in the lower alkyl part, esterified by a cycloalkanol with 3 to 7 ring members, or by a lower alkanol or lower phenylalkanol, in each case with up to 7 carbon atoms in the lower alkyl part, optionally substituted by halogen, lower alkyl or lower alkoxy, in each case with up to 7 carbon atoms, or lower carbamoylalkyl with up to 7 carbon atoms, optionally substituted at the nitrogen atom by one or two lower alkyl residues, in each case with up to 7 carbon atoms in the lower alkyl part, or by lower alkylene with 3-7 carbon atoms in the alkyl chain, or by lower oxaalkylene or lower thiaalkylene, in each case with 4 or 5 carbon atoms in the lower alkylene chain or by lower azaalkylene with 2- 6 carbon atoms in the lower alkylene chain; stands for halogen, cyano, nitro, lower alkyl, hydroxyalkyl lower, lower alkenyl, each containing up to 7 carbon atoms, phenyl, optionally substituted by halogen, trifluoromethyl, lower alkyl, lower alkenyl, lower alkoxy, lower alkenyloxy or alkoxy lower-methyl, in each case with up to 7 carbon atoms in the lower residues, hydroxy, lower alkoxy, lower alkoxy-lower alkyl, lower alkoxy-lower alkenyl, lower alkoxy-lower alkoxy, lower alkylthio-lower alkyl, lower alkenyloxy, lower alkythio, lower alkylthio-lower alkoxy, in each case with up to 7 carbon atoms in the lower residues, lower alkylene-amino, hydroxyalkylene-amino, in each case with 4-8 ring members and 3-7 carbon atoms , oxa-lower alkylene-amino, thiaalkylene-amino with up to 4-5 carbon atoms in the lower alkylene part, azaalkylene-amino with 2-6 carbon atoms in the lower alkylene, lower alkyl-amino, dialkyl-lower amino part, with up to 7 carbon atoms in the lower alkyl part, lower alkanoyl-amino or phenylalkanoyl lower-amino in each case with up to 7 carbon atoms in the lower alkyl part, optionally substituted by halogen, trifluoromethyl, lower alkyl, lower alkenyl, lower alkoxy, lower alkenyloxy or lower alkoxy-methyl, in each case with up to 7 carbon atoms in the lower radicals, or lower alkoxycarbonyl amino with up to 7 atoms of carbon in the lower alkyl, lower alkanoyl-amino-lower alkyl, lower alkanoyl-amino-lower alkylene, or phenylalkanoyl-amino-lower alkyl or phenylalkanoyl-amino-lower alkylene, in each case with up to 7 carbon atoms on the lower residues, optionally substituted by halogen, trifluoromethyl, lower alkyl, lower alkenyl, lower alkoxy, lower alkenyloxy or lower alkoxy-me lime, in each case with up to 7 carbon atoms in the lower residues, lower alkoxy-carbonylamino-lower alkyl, or lower alkoxy-carbonyl amino-lower alkylene in each case with up to 7 carbon atoms in the lower residues, amino-lower alkyl , lower alkyl sulfonyl, in each case with up to 7 carbon atoms, or carbamoyl optionally substituted on the nitrogen atom by one or two lower alkyl residues, in each case with up to 7 carbon atoms in the lower alkyl part , or by lower alkylene with 3-7 carbon atoms in the alkylene chain, by lower oxaalkylene or lower thiaalkylene, in each case with 4 or 5 carbon atoms in the lower alkylene chain or by lower azaalkylene with 2-6 carbon atoms in the lower alkylene chain, or carbamoylalkyl with up to 7 carbon atoms in the lower alkyl part, and n has the values 1, 2 or 3; R4 significa hidrógeno, halógeno, alquilo inferior, alquenilo inferior, alcoxi inferior, alcoxi inferior-alquilo inferior, amino-alquilo inferior, alcoxi inferior-alcoxi inferior, alqueniloxi inferior, alquiltio inferior, alquiltio inferior-alcoxi inferior, alquiltio inferior-alquilo inferior, alquilo inferior-amino, dialquilo inferior-amino, alquilo inferior-sulfonilo o alcoxi inferiorcarbonilo, en cada caso con hasta 7 átomos de carbono en la parte alquilo inferior, hidroxi, alquileno inferior-amino o hidroxialquileno inferior-amino, en cada caso con 4 - 8 miembros de anillo y 3 - 7 átomos de carbono en la cadena alquilo, oxaalquileno inferior-amino o tiaalquileno inferior-amino, en cada caso con 4-5 átomos de carbono en la cadena de alquileno, azaalquileno inferior-amino con 2-6 átomos de carbono en la cadena alquileno, fenilo, en caso dado sustituido por halógeno, trifluormetilo, alquilo inferior, alquenilo inferior, alcoxi inferior-metilo, alcoxi inferior o alqueniloxi inferior, en cada caso con hasta 7 átomos de carbono en los restos inferiores, o feniltio, en caso dado sustituido por halógeno, trifluormetilo, alquilo inferior o alcoxi inferior con hasta 7 átomos de carbono, alcanoilo inferior amino o fenil-alcanoilo inferior-amino en cada caso con hasta 7 átomos de carbono en la parte alquilo inferior, en caso dado sustituido por halógeno, trifluormetilo, alquilo inferior, alquenilo inferior, alcoxi inferior, alqueniloxi inferior o alcoxi inferior-metilo, en cada caso con hasta 7 átomos de carbono en los restos inferiores, o alcoxi inferiorcarbonilamino con hasta 7 átomos de carbono en la parte alquilo inferior, y significa hidrógeno, halógeno, ciano, hidroxi, alquilo inferior, alcoxi inferior-alquilo inferior, amino-alquilo inferior, alcoxi inferior-alquenilo inferior, alquilo inferior-amino, dialquilo inferior-amino o alquilo inferior-sulfonilo en cada caso con hasta 7 átomos de carbono en la parte alquilo inferior, alcanoilo inferior-amino, o fenil-alcanoilo inferior-amino en cada caso con hasta 7 átomos de carbono en la parte alcano inferior, en cago dado sustituído por halógeno, trifluormetilo, alquilo inferior, alquenilo inferior, alcoxi inferior, alqueniloxi inferior o alboxi inferior-metilo, en cada caso con hasta 7 átomos de carbono en los restos inferiores, o alcoxi inferior-carbonilamino con hasta 7 átomos de carbono en la parte alquilo inferior, alcanoilo inferior-amino-alquilo inferior, alcanoilo inferior amino-alquileno inferior o fenil-alcanoilo inferíor-amino-alquilo inferior o fenil-alcanoilo inferior-amino-alquileno inferior, en cada caso con hasta 7 átomos de carbono en los restos inferiores, en caso dado sustituidos por halógeno, trifluormetilo, alquilo inferior, alquenilo inferior, alcoxi inferior, alqueniloxi inferior o alcoxi inferior-metilo, en cada caso con hasta 7 átomos de carbono en los restos inferioras, alcoxi inferior-carbonilamino-alquilo inferior o alcoxiihferior-carbonilamino-alquileno inferior, en cada caso con hasta 7 átomos de carbono en los restos inferiores, bajo la condición de que R4 y R5 signifiquen hidrógeno y n y R3 tengan los significados indicados cuando Het significa piridilo, o que R3 signifique hidrógeno y R4 y R5 tengan el significado indicado cuando Het signifique pirazinilo, piridazinilo o pirimidinilo, así como sus óxidos y sales, especialmente sus sales de adición de ácido terapéuticamente utilizables,caracterizado por que un compuesto de fórmula **(Ver fórmula)** O una sal del mismo, donde Het, R3, n, R4 y R5, tienen los significados de arriba, Z1 significa el grupo hidroxilo y Z2 significa, un grupo hidroxilo esterificado, capaz de reacción, o Z2 y Z2 juntos significan epoxi, o un N-óxido del mismo, se hace reaccionar con un compuesto de fórmula **(Ver fórmula)** donde R1 y R2 tienen el significado arriba indicado, o una sal del mismo, y los compuestos de fórmula I obtenidos se separan como mezclas de isómeros, o isómeros puros o como antípodas ópticos, o como N-óxidos en forma libre o en forma de sus sales, especialmente de sus sales de adición de ácido de aplicación terapéutica. (Machine-translation by Google Translate, not legally binding)
ES76446081A 1973-02-20 1976-03-16 Pyridazinyl,pyrimidinyl,pyrazinyl and pyridyl compounds and processes for their manufacture Expired ES446081A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH244473A CH584209A5 (en) 1973-02-20 1973-02-20 3-amino-2-hydroxypropoxy substd. diazines and pyridines - with beta-adrenergic blocking or stimulating activity
FI193/74A FI60391C (en) 1973-02-20 1974-01-23 ANALOGIFICATION OF FRAMSTATION WITH BETA-RECEPTOR-ACTIVE 1-HETEROCYCLYLOXY-3-AMINO-2-PROPANOLFOERING

Publications (1)

Publication Number Publication Date
ES446081A1 true ES446081A1 (en) 1977-06-16

Family

ID=25690464

Family Applications (2)

Application Number Title Priority Date Filing Date
ES76446081A Expired ES446081A1 (en) 1973-02-20 1976-03-16 Pyridazinyl,pyrimidinyl,pyrazinyl and pyridyl compounds and processes for their manufacture
ES446083A Expired ES446083A1 (en) 1973-02-20 1976-03-16 Pyridazinyl,pyrimidinyl,pyrazinyl and pyridyl compounds and processes for their manufacture

Family Applications After (1)

Application Number Title Priority Date Filing Date
ES446083A Expired ES446083A1 (en) 1973-02-20 1976-03-16 Pyridazinyl,pyrimidinyl,pyrazinyl and pyridyl compounds and processes for their manufacture

Country Status (15)

Country Link
AR (6) AR206801A1 (en)
AT (1) AT335455B (en)
BE (1) BE811274A (en)
CA (1) CA1027131A (en)
CS (1) CS203970B2 (en)
DD (1) DD110041A5 (en)
DE (1) DE2406930A1 (en)
DK (1) DK143501C (en)
ES (2) ES446081A1 (en)
FR (1) FR2218101B1 (en)
GB (1) GB1465946A (en)
IE (1) IE38839B1 (en)
IL (1) IL44202A (en)
LU (1) LU69415A1 (en)
SE (1) SE420834B (en)

Families Citing this family (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4195090A (en) * 1973-02-20 1980-03-25 Ciba-Geigy Corporation 2-(3-Amino-2-hydroxy-propoxy)pyridine derivatives and pharmaceutical compositions therewith
US4000282A (en) * 1974-12-16 1976-12-28 Merck & Co., Inc. 2-(3-tert. butyl or isopropylamino-2-hydroxypropoxy)-3-cyanopyridines
JPS5283759A (en) * 1976-01-01 1977-07-12 Merck & Co Inc Substituted pyridines
US4092419A (en) * 1976-06-15 1978-05-30 Merck & Co., Inc. Substituted (3-loweralkylamino-2-R1 O-propoxy)pyridines, their preparation and use
US4091104A (en) * 1976-06-15 1978-05-23 Merck & Co., Inc. Substituted (3-loweralkylamino-2-R1 O-propoxy)pyridines, their preparation and use
US4060601A (en) * 1976-06-15 1977-11-29 Merck & Co., Inc. Certain lower-alkyl amino-2'-hydroxy-propoxy pyridines
DE2711655A1 (en) * 1977-03-17 1978-09-21 Basf Ag PYRIDINYL-AMINOALKYLAETHER
US4166851A (en) * 1977-05-16 1979-09-04 Merck & Co., Inc. Certain imidazo(1,2a)pyridine derivatives
US4753673A (en) * 1977-07-22 1988-06-28 The Dow Chemical Company Trifluoromethyl pyridinyloxyphenoxy and pyridinylthiophenoxy propanoic acids and propanols and derivatives thereof and methods of herbicidal use
US4144343A (en) * 1978-01-04 1979-03-13 Merck & Co., Inc. Heterocycle substituted (3-loweralkylamino-2-R1 O-propoxy)pyridines
JPS54106476A (en) * 1978-01-04 1979-08-21 Merck & Co Inc Multiisubstituted 22*33lower alkylaminoo22 r100propoxy*pyridine
US4279913A (en) * 1978-01-04 1981-07-21 Merck & Co., Inc. Polysubstituted-2-(3-loweralkylamino-2-R1 O-propoxy)pyridines
US4208416A (en) * 1978-06-27 1980-06-17 Merck & Co., Inc. N-Aralkyl containing cyanopyridines
US4210653A (en) * 1978-06-27 1980-07-01 Merck & Co., Inc. Pyridyloxypropanolamines
DK267779A (en) * 1978-06-27 1979-12-28 Merck & Co Inc PROCEDURE FOR THE PREPARATION OF N-ARALKYLAMINO-PROPOXYCYANOPYRIDINES
US4294969A (en) * 1979-01-29 1981-10-13 Merck & Co., Inc. Process for producing 2-bromo-3,5-disubstituted pyridines
US4393212A (en) * 1979-01-29 1983-07-12 Merck & Co., Inc. Certain nicotinic acid esters and corresponding nicotinonitriles
DD150456A5 (en) * 1979-03-01 1981-09-02 Ciba Geigy Ag PROCESS FOR THE PREPARATION OF DERIVATIVES OF 3-AMINO-1,2-PROPANDIOL
US4281005A (en) 1979-03-05 1981-07-28 Merck & Co., Inc. Novel 2-pyridylimidazole compounds
IT1165040B (en) * 1979-04-23 1987-04-22 Isf Spa ALCOSSIALKILIDENIDRAZINOPIRIDAZIONE AND PROCEDURE FOR THEIR PREPARATION
DE2943774A1 (en) * 1979-10-26 1981-05-14 1000 Berlin Schering Ag Berlin Und Bergkamen SUBSTITUTED PYRIDINE, METHOD FOR THEIR PRODUCTION AND THEIR USE
IL62602A (en) * 1980-05-19 1984-06-29 Labaz Sanofi Nv Pyridoxine derivatives,their preparation and pharmaceutical compositions containing them
FR2502618A1 (en) * 1981-03-25 1982-10-01 Synthelabo PYRIDINE DERIVATIVES, THEIR PREPARATION AND THEIR THERAPEUTIC APPLICATION
US4517188A (en) * 1983-05-09 1985-05-14 Mead Johnson & Company 1-Pyrimidinyloxy-3-hetaryl-alkylamino-2-propanols
US4598149A (en) * 1984-03-02 1986-07-01 Merck & Co., Inc. 3-amino-2-hydroxypropyl of pyrimidin-4-one useful as antihypertensive, cardioprotective, antiarrythmic, and antianginal agents
US6465467B1 (en) 1999-05-21 2002-10-15 Biovitrum Ab Certain aryl-aliphatic and heteroaryl-aliphatic piperazinyl pyrazines and their use in the treatment of serotonin-related diseases
US7361671B2 (en) * 2001-11-15 2008-04-22 The Institute For Pharmaceutical Discovery, Inc. Substituted heteroarylalkanoic acids
MXPA04012711A (en) 2002-06-19 2005-03-23 Biovitrum Ab Novel compounds, their use and preparation.
EP1565472A2 (en) * 2002-11-27 2005-08-24 Artesian Therapeutics, Inc. Compounds with mixed pde-inhibitory and beta-adrenergic antagonist or partial agonist activity for treatment of heart failure
US20080033020A1 (en) * 2004-07-23 2008-02-07 Darren Mansfield 3-Pyridinylethylbenzamide Derivatives as Fungicides
RU2012116124A (en) * 2009-09-21 2013-10-27 Вандербилт Юниверсити O-BENZYL NICOTINAMIDE ANALOGUES AS POSITIVE ALLOGENIC MODULATORS mGluR5

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1001631A (en) * 1972-05-05 1976-12-14 Merck Sharp And Dohme (I.A.) Corp. 2-(3-substituted amino-2-hydroxy-propoxy)-3-substituted pyrazines and method for preparation

Also Published As

Publication number Publication date
DK143501C (en) 1982-02-22
SE420834B (en) 1981-11-02
FR2218101A1 (en) 1974-09-13
AR203878A1 (en) 1975-10-31
AR208043A1 (en) 1976-11-22
DE2406930A1 (en) 1974-08-22
CA1027131A (en) 1978-02-28
AR207133A1 (en) 1976-09-15
IE38839L (en) 1974-08-20
ATA133074A (en) 1976-07-15
AT335455B (en) 1977-03-10
AR206801A1 (en) 1976-08-23
AR208397A1 (en) 1976-12-27
DD110041A5 (en) 1974-12-05
LU69415A1 (en) 1975-12-09
CS203970B2 (en) 1981-03-31
BE811274A (en) 1974-08-19
GB1465946A (en) 1977-03-02
IL44202A (en) 1978-10-31
AR214612A1 (en) 1979-07-13
IL44202A0 (en) 1974-06-30
IE38839B1 (en) 1978-06-07
FR2218101B1 (en) 1977-07-15
ES446083A1 (en) 1977-09-16
DK143501B (en) 1981-08-31

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Legal Events

Date Code Title Description
FD1A Patent lapsed

Effective date: 19840217