GB1430961A - 1-substituted-1,4-dihyddrypyridine derivatives - Google Patents

1-substituted-1,4-dihyddrypyridine derivatives

Info

Publication number
GB1430961A
GB1430961A GB61673A GB61673A GB1430961A GB 1430961 A GB1430961 A GB 1430961A GB 61673 A GB61673 A GB 61673A GB 61673 A GB61673 A GB 61673A GB 1430961 A GB1430961 A GB 1430961A
Authority
GB
United Kingdom
Prior art keywords
group
formula
substituted
compound
alkyl
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
GB61673A
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.)
Yamanouchi Pharmaceutical Co Ltd
Original Assignee
Yamanouchi Pharmaceutical Co Ltd
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 JP848272A external-priority patent/JPS4885574A/ja
Priority claimed from JP1845972A external-priority patent/JPS4886875A/ja
Priority claimed from JP7237372A external-priority patent/JPS4930379A/ja
Priority claimed from JP7434372A external-priority patent/JPS4931674A/ja
Application filed by Yamanouchi Pharmaceutical Co Ltd filed Critical Yamanouchi Pharmaceutical Co Ltd
Publication of GB1430961A publication Critical patent/GB1430961A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D211/82—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
    • C07D211/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
    • C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems 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 carbon atoms of the ring system
    • C07D219/06—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond

Abstract

1430961 N-Substituted-1,4-dihydropyridines YAMANOUCHI PHARMACEUTICAL CO Ltd 4 Jan 1973 [22 Jan 1972 24 Feb 1972 19 July 1972 25 July 1972] 616/73 Heading C2C The invention comprises a N-substituted- 1,4-dihydropyridine of the formula wherein R<SP>1</SP> and R<SP>3</SP>, which may be the same or different, each represents a C 1 to C 5 alkyl group or a C 1 to C 5 alkoxyl group which may be substituted by a C 1 to C 5 alkoxy group; R<SP>2</SP> and R<SP>4</SP>, which may be the same or different, each represents a C 1 to C 5 alkyl group; said R<SP>1</SP> and R<SP>2</SP> or said R<SP>3</SP> and R<SP>4</SP> may combine together to form a C 2 to C 5 alkylene group; R<SP>5</SP> represents a hydrogen atom, a nitro group, a halogen atom, an azide group, a C 1 to C 5 alkyl group, a C 1 to C 5 alkoxy group, a cyano group, a C 1 to C 5 alkyl sulphonyl group, or a di or mono C 1 to C 5 alkylamino group; R<SP>6</SP> represents a C 1 to C 6 alkyl group, a C 2 to C 5 alkenyl group, a phenyl group, or an aralkyl group; A represents -CH=CH-, -CH=N-, -S-, or -O-; B represents an alkylene group; and one of m and n is 1 while the other is 0, or m and n each is 1 with the proviso that when m is 1, n is 0 and A is -CH=CH- then R<SP>5</SP> is not a cyano group and when m is 1, n is 0 and A is -CH=N- then R<SP>5</SP> is not a hydrogen atom. They may be prepared by reacting a compound of formula with an equimolar amount of in which X is a halogen atom and R<SP>6</SP>, B, m and n are as defined above. They may also be prepared by subjecting a compound of Formula (IV) and to the Hartzch pyridine synthesis. The starting materials may be made by reacting the compound of Formula (IV) with a compound of formula R<SP>1</SP>COCH 2 COR<SP>1</SP> and ammonia. The products are used as active ingredients in pharmaceutical compositions. Reference has been directed by the Comptroller to Specification 1,239,679.
GB61673A 1972-01-22 1973-01-04 1-substituted-1,4-dihyddrypyridine derivatives Expired GB1430961A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP848272A JPS4885574A (en) 1972-01-22 1972-01-22
JP1845972A JPS4886875A (en) 1972-02-24 1972-02-24
JP7237372A JPS4930379A (en) 1972-07-19 1972-07-19
JP7434372A JPS4931674A (en) 1972-07-25 1972-07-25

Publications (1)

Publication Number Publication Date
GB1430961A true GB1430961A (en) 1976-04-07

Family

ID=27454953

Family Applications (1)

Application Number Title Priority Date Filing Date
GB61673A Expired GB1430961A (en) 1972-01-22 1973-01-04 1-substituted-1,4-dihyddrypyridine derivatives

Country Status (4)

Country Link
DE (1) DE2302866C2 (en)
DK (1) DK139868C (en)
FR (1) FR2169113B1 (en)
GB (1) GB1430961A (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0001054A2 (en) * 1977-08-24 1979-03-21 Bayer Ag 2-Pyridyl-1,4-dihydropyridine derivatives, methods for their preparation and their pharmaceutical use
DE2928022A1 (en) * 1978-07-17 1980-01-31 Ausonia Farma Srl METHOD FOR PRODUCING THE 2-(N-BENZYL-N-METHYLAMINO)-AETHYL ESTER OF 2,6-DIMETHYL-4-(3-NITROPHENYL)-3-METHOXYCARBONYL-1,4-DIHYDROPYRIDINE-5-CARBONIC ACID
US4546186A (en) * 1983-12-14 1985-10-08 American Home Products Corporation 1,4,5,6,7,8-Hexahydro-2-methyl-5-oxo-4-(2-thiazolyl)-3-quinoline carboxylic acid 2-methyl(phenylmethyl)amino ethyl ester and pharmaceutically acceptable salts
EP0330470A2 (en) * 1988-02-24 1989-08-30 Ajinomoto Co., Inc. 1,4-Dihydropyridine derivatives useful against tumour cells
US5216172A (en) * 1988-02-24 1993-06-01 Ajinomoto Co., Inc. 1,4-dihydropyridine-4-aryl-2,6-dimethyl-3,5-dicarboxylates useful as agents against drug resistant tumor cells
EP1108710A1 (en) * 1998-07-23 2001-06-20 Cheng, Ing-Jun Guaiacoxypropanolamines with alpha/beta-adrenergic blocking activity

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3956341A (en) * 1974-02-21 1976-05-11 Smithkline Corporation 1,3,5-Tricarbo-1,4-dihydropyridines
SU706410A1 (en) * 1978-01-11 1979-12-30 Ордена Трудового Красного Знамени Институт Органического Синтеза Ан Латвийской Сср 2,6-dimethyl-3,5-dicarbomethoxy-4-(o-difluoromethoxyphenyl)-1,4-dihydropyridine possessing expressed hypotensive activity and exhibiting action on vegetative nervous system functions
DE2815578C2 (en) * 1978-04-11 1986-01-16 Bayer Ag, 5090 Leverkusen New pharmaceutical use of nimodipine
DE3018259A1 (en) * 1980-05-13 1981-11-19 Bayer Ag, 5090 Leverkusen 1,4-DIHYDROPYRIDINE WITH DIFFERENT SUBSTITUENTS IN 2- AND 6-POSITIONS, METHODS FOR THEIR PRODUCTION AND THEIR USE IN MEDICINAL PRODUCTS
DE4430092A1 (en) 1994-08-25 1996-02-29 Bayer Ag 2,3-Cyclically condensed 1,4-dihydropyridines, process for their preparation and their use as medicaments
DE4444864A1 (en) * 1994-12-16 1996-06-20 Bayer Ag Use of 5-acyl-1,4-dihydropyridines

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3441648A (en) * 1967-02-07 1969-04-29 Smithkline Corp Compositions and methods for lowering blood pressure with 1,4-dihydropyridines
DE1813436C3 (en) * 1968-12-07 1979-01-11 Bayer Ag, 5090 Leverkusen N-substituted 2,6-dimethyl-1,4-dihydropyridines
DE1923990C3 (en) * 1969-05-10 1978-11-23 Bayer Ag Process for the preparation of N-substituted M-dihydropyridine-S.S-dicarboxylic acid esters
DE2013431C3 (en) * 1970-03-20 1979-12-20 Bayer Ag, 5090 Leverkusen 4-Azidophenyl-1,4-dihydropyridine-3,5-dicarboxylic acid ester
DE1963186C3 (en) * 1969-12-17 1979-02-15 Bayer Ag, 5090 Leverkusen Sulfur-containing 1,4-dihydropyridine-33-dicarboxylic acid esters
DE1963188A1 (en) * 1969-12-17 1971-06-24 Bayer Ag New cyanophenyl-1,4-dihydropyridine derivatives
DE1963738A1 (en) * 1969-12-19 1971-06-24 Semikron Gleichrichterbau Method of manufacturing selenium rectifier plates
DE2003146A1 (en) * 1970-01-24 1971-07-29 Bayer Ag New 1,4-dihydropyridine derivatives
DE2005116C3 (en) * 1970-02-05 1980-02-14 Bayer Ag, 5090 Leverkusen Symmetrical 1,4-dihydropyridine-3,5-dicarboxylic acid esters

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0001054A2 (en) * 1977-08-24 1979-03-21 Bayer Ag 2-Pyridyl-1,4-dihydropyridine derivatives, methods for their preparation and their pharmaceutical use
EP0001054A3 (en) * 1977-08-24 1979-04-04 Bayer Ag 2-pyridyl-1,4-dihydropyridine derivatives, methods for their preparation and their pharmaceutical use
DE2928022A1 (en) * 1978-07-17 1980-01-31 Ausonia Farma Srl METHOD FOR PRODUCING THE 2-(N-BENZYL-N-METHYLAMINO)-AETHYL ESTER OF 2,6-DIMETHYL-4-(3-NITROPHENYL)-3-METHOXYCARBONYL-1,4-DIHYDROPYRIDINE-5-CARBONIC ACID
US4546186A (en) * 1983-12-14 1985-10-08 American Home Products Corporation 1,4,5,6,7,8-Hexahydro-2-methyl-5-oxo-4-(2-thiazolyl)-3-quinoline carboxylic acid 2-methyl(phenylmethyl)amino ethyl ester and pharmaceutically acceptable salts
EP0330470A2 (en) * 1988-02-24 1989-08-30 Ajinomoto Co., Inc. 1,4-Dihydropyridine derivatives useful against tumour cells
EP0330470A3 (en) * 1988-02-24 1992-01-02 Ajinomoto Co., Inc. 1,4-dihydropyridine derivatives useful against tumour cells
US5216172A (en) * 1988-02-24 1993-06-01 Ajinomoto Co., Inc. 1,4-dihydropyridine-4-aryl-2,6-dimethyl-3,5-dicarboxylates useful as agents against drug resistant tumor cells
EP1108710A1 (en) * 1998-07-23 2001-06-20 Cheng, Ing-Jun Guaiacoxypropanolamines with alpha/beta-adrenergic blocking activity
EP1108710A4 (en) * 1998-07-23 2001-11-21 Chen Ing Jun Guaiacoxypropanolamines with alpha/beta-adrenergic blocking activity

Also Published As

Publication number Publication date
DK139868B (en) 1979-05-07
DE2302866A1 (en) 1973-08-02
DE2302866C2 (en) 1988-01-28
FR2169113A1 (en) 1973-09-07
FR2169113B1 (en) 1977-02-04
DK139868C (en) 1979-10-08

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee