US4038399A
Expired / Lapsed
US
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1,4-dihydropyridine carboxylic acid esters useful as coronary vessel dilators and anti-hypertensives
Assignee: Bayer AG
•
Filing: 1976-01-08
•
Granted: 1977-07-26
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Expires: 1996-01-08
Abstract
Abstract 1,4-DINYDROPYRIDINE CARBOXYLIC ACID ESTERS OF THE FORMULA: ##STR1## or a pharmaceutically acceptable nontoxic salt thereof wherein R, R 1 R 2 R 3 R 4 X and Y are defined hereinafter Are useful for their coronary activity, particularly as coronary vessel dilators and as antihypertensives.
Inventors
- 👤 Friedrich Bossert
- 👤 Horst Meyer
- 👤 Wulf Vater
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 21:49
CPC Classifications
C; C07; C07D; C07D401/00; C07D401/02; C07D401/04; C07D401/14; C07D405/00; C07D405/14; C07D409/00; C07D409/14
Claims Analysis
Total Claims: 24
Claim 1
Independent Claim
170 words
A pharmaceutical composition useful for effecting coronary vessel dilation in humans and animals and for treating hypertension in humans and animals which comprises a coronary vessel dilating amount or an antihypertensive amount of a compound of the formula: ##STR69## or a pharmaceutically acceptable nontoxic salt thereof wherein R is hydrogen, straight- or branched-chain lower alkyl, lower alkenyl or lower alkynyl; R 1 and R 4 are the same or different and are each hydrogen or straight- or branched-chain lower alkyl; X is straight- or branched-chain lower alkylene; Y is the moiety NR'R" wherein R' and R" are the same or different and are each hydrogen or lower alkyl; R 2 is phenyl unsubstituted or substituted by 1, 2 or 3 substituents selected from the group consisting of nitro, cyano, lower alkyl, lower alkoxy, phenyl, trifluoromethyl and halogen; benzyl; phenyl-ethyl; styryl; or naphthyl; and R 3 is alkoxyalkyl of up to 6 carbon atoms in both moieties; lower alkyl; or lower alkoxy; in combination with a pharmaceutically acceptable diluent or carrier.
Claim 2
Dependent Claim
170 words
A pharmaceutical composition useful for effecting coronary vessel dilation in humans and animals and for treating hypertension in humans and animals which comprises a coronary vessel dilating amount or an antihypertensive amount of a compound of the formula: ##STR69## or a pharmaceutically acceptable nontoxic salt thereof wherein R is hydrogen, straight- or branched-chain lower alkyl, lower alkenyl or lower alkynyl; R 1 and R 4 are the same or different and are each hydrogen or straight- or branched-chain lower alkyl; X is straight- or branched-chain lower alkylene; Y is the moiety NR'R" wherein R' and R" are the same or different and are each hydrogen or lower alkyl; R 2 is phenyl unsubstituted or substituted by 1, 2 or 3 substituents selected from the group consisting of nitro, cyano, lower alkyl, lower alkoxy, phenyl, trifluoromethyl and halogen; benzyl; phenyl-ethyl; styryl; or naphthyl; and R 3 is alkoxyalkyl of up to 6 carbon atoms in both moieties; lower alkyl; or lower alkoxy; in combination with a pharmaceutically acceptable diluent or carrier.
Claim 3
Dependent Claim
132 words
A composition according to claim 1 wherein R is hydrogen, straight- or branched-chain alkyl of 1 to 4 carbon atoms or straight- or branched-chain alkenyl of 2 to 4 carbon atoms; R 1 and R 4 are the same or different and are each hydrogen or straight- or branched-chain alkyl of 1 to 4 carbon atoms; X is straight- or branched-chain alkylene of 1 to 4 carbon atoms; R' and R" are the same or different and are each hydrogen or alkyl of 1 to 4 carbon atoms; and R 2 is phenyl unsubstituted or substituted by 1 or 2 nitro, cyano, alkyl of 1 to 4 carbon atoms, chloro, bromo or trifluoromethyl groups, or by 1 to 3 alkoxy groups of 1 to 4 carbon atoms; benzyl; phenyl-ethyl; styryl; or naphthyl.
Claim 4
Dependent Claim
34 words
A composition according to claim 1 wherein the alkyl moiety of R has 1 to 3 carbon atoms and the alkyl moiety of R 1 and R 4 has 1 or 2 carbon atoms.
Claim 5
Dependent Claim
21 words
A composition according to claim 3 wherein R 2 is pbenyl unsubstituted or substituted by nitro, cyano, chloro, bromo or trifluoromethyl.
Claim 6
Dependent Claim
84 words
A composition according to claim 1 wherein R is hydrogen or straight- or branched-chain alkyl of 1 to 4 carbon atoms, R 1 and R 4 are the same or different and are each straight- or branched-chain alkyl of 1 to 4 carbon atoms, X is straight- or branched-chain alkylene of 1 to 4 carbon atoms, Y is dimethylamino or diethylamino; and R 2 is phenyl; phenyl substituted by 1 or 2 substituents selected from the group consisting of nitro, cyano, chloro and trifluoromethyl.
Claim 7
Dependent Claim
100 words
A composition according to claim 1 wherein R is hydrogen or straight- or branched-chain alkyl of 1 to 4 carbon atoms, R 1 is straight- or branched-chain alkyl of 1 to 3 carbon atoms, R 4 is straight- or branched-chain alkyl of 1 to 4 carbon atoms, X is straight- or branched-chain alkylene of 1 to 3 carbon atoms, Y is dimethylamino or diethylamino, R 2 is phenyl; phenyl substituted by nitro, nitro and trifluoromethyl, nitro and chloro, dinitro, trifluoromethyl, di-trifluoromethyl, chloro, dichloro, cyano or fluoro; and R 3 is straight- or branched-chain alkoxy of 1 to 4 carbon atoms.
Claim 8
Dependent Claim
25 words
A composition according to claim 1 wherein R is hydrogen or lower alkyl; and R 2 is phenyl unsubstituted by nitro, cyano, trifluoromethyl or halogen.
Claim 9
Dependent Claim
63 words
A composition according to claim 1 wherein R is hydrogen; R 1 and R 4 are each lower alkyl; R' and R" are different and are selected from the group consisting of hydrogen and lower alkyl; R 2 is phenyl unsubstituted or substituted by nitro, cyano, trifluoromethyl or halogen; and R 3 is alkoxyalkyl of up to 6 carbon atoms in both moieties.
Claim 10
Dependent Claim
16 words
The composition according to claim 1 wherein the compound is 1,2,6-trimethyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-(β-diethylamine)-ethyl ester 5-methyl ester.
Claim 11
Dependent Claim
16 words
The composition according to claim 1 wherein the compound is 1,2,6-trimethyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-(γ-dimethylamino)-propyl ester 5-ethyl ester.
Claim 12
Dependent Claim
16 words
The composition according to claim 1 wherein the compound is 2,6-dimethyl-4-(2'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-(γ-dimethylamino)-propyl ester 5-methyl ester.
Claim 13
Independent Claim
173 words
A method of effecting coronary vessel dilation in humans and animals and of treating hypertension in humans and animals which comprises administering to such human or animal a coronary vessel dilating amount or an antihypertensive amount of a compound of the formula ##STR70## or a pharmaceutically acceptable nontoxic salt thereof wherein R is hydrogen, straight- or branched-chain lower alkyl, lower alkenyl or lower alkynyl; R 1 and R 4 are the same or different and are each hydrogen or straight- or branched-chain lower alkyl; X is straight- or branched-chain lower alkylene; Y is the moiety NR'R" wherein R' and R" are the same or different and are each hydrogen or lower alkyl; R 2 is phenyl unsubstituted or substituted by 1, 2 or 3 substituents selected from the group consisting of nitro, cyano, lower alkyl, lower alkoxy, phenyl, trifluoromethyl and halogen; benzyl; phenyl-ethyl; styryl; and R 3 is alkoxyalkyl of up to 6 carbon atoms in both moieties; lower alkyl; or lower alkoxy; in combination with a pharmaceutically acceptable nontoxic diluent or carrier.
Claim 14
Independent Claim
173 words
A method of effecting coronary vessel dilation in humans and animals and of treating hypertension in humans and animals which comprises administering to such human or animal a coronary vessel dilating amount or an antihypertensive amount of a compound of the formula ##STR70## or a pharmaceutically acceptable nontoxic salt thereof wherein R is hydrogen, straight- or branched-chain lower alkyl, lower alkenyl or lower alkynyl; R 1 and R 4 are the same or different and are each hydrogen or straight- or branched-chain lower alkyl; X is straight- or branched-chain lower alkylene; Y is the moiety NR'R" wherein R' and R" are the same or different and are each hydrogen or lower alkyl; R 2 is phenyl unsubstituted or substituted by 1, 2 or 3 substituents selected from the group consisting of nitro, cyano, lower alkyl, lower alkoxy, phenyl, trifluoromethyl and halogen; benzyl; phenyl-ethyl; styryl; and R 3 is alkoxyalkyl of up to 6 carbon atoms in both moieties; lower alkyl; or lower alkoxy; in combination with a pharmaceutically acceptable nontoxic diluent or carrier.
Claim 15
Dependent Claim
132 words
A method according to claim 12 wherein R is hydrogen, straight- or branched-chain alkyl of 1 to 4 carbon atoms or straight- or branched-chain alkenyl of 2 to 4 carbon atoms; R 1 and R 4 are the same or different and are each hydrogen or straight- or branched-chain alkyl of 1 to 4 carbon atoms; X is straight- or branched-chain alkylene of 1 to 4 carbon atoms; R' and R" are the same or different and are each hydrogen or alkyl of 1 to 4 carbon atoms; and R 2 is phenyl unsubstituted or substituted by 1 or 2 nitro, cyano, alkyl of 1 to 4 carbon atoms, chloro, bromo or trifluoromethyl groups, or by 1 to 3 alkoxy groups of 1 to 4 carbon atoms; benzyl; phenyl-ethyl; styryl; or naphthyl.
Claim 16
Dependent Claim
34 words
A method according to claim 12 wherein the alkyl moiety of R has 1 to 3 carbon atoms and the alkyl moiety of R 1 and R 4 has 1 or 2 carbon atoms.
Claim 17
Dependent Claim
21 words
A method according to claim 12 wherein R 2 is phenyl unsubstituted or substituted by nitro, cyano, chloro, bromo or trifluoromethyl.
Claim 18
Dependent Claim
84 words
A method according to claim 12 wherein R is hydrogen or straight- or branched-chain alkyl of 1 to 4 carbon atoms, R 1 and R 4 are the same or different and are each straight or branched-chain alkyl of 1 to 4 carbon atoms, X is straight- or branched-chain alkylene of 1 to 4 carbon atoms, Y is dimethylamino or diethylamino; and R 2 is phenyl, phenyl substituted by 1 or 2 substituents selected from the group consisting of nitro, cyano, chloro and trifluoromethyl.
Claim 19
Dependent Claim
102 words
A method according to claim 12 wherein R is hydrogen or straight- or branched-chain alkyl of 1 to 4 carbon atoms, R 1 is straight- or branched-chain alkyl of 1 to 3 carbon atoms, R 4 is straight- or branched-chain alkyl of 1 to 4 carbon atoms, X is straight- or branched-chain alkylene of 1 to 3 carbon atoms, Y is dimethylamino or diethylamino, R 2 is phenyl; phenyl substituted by nitro, nitro and trifluoromethyl, nitro and chloro, dinitro, trifluoromethyl, di-trifluoromethyl, chloro, dichloro, cyano or fluoro; and R 3 is straight- or branched-chain alkoxy of 1 to 4 carbon atoms or methoxyethoxy.
Claim 20
Dependent Claim
27 words
A method according to claim 12 wherein R is hydrogen or lower alkyl; and R 2 is phenyl unsubstituted or substituted by nitro, cyano, trifluoromethyl or halogen.
Claim 21
Dependent Claim
63 words
A method according to claim 12 wherein R is hydrogen; R 1 and R 4 are each lower alkyl; R' and R" are different and are selected from the group consisting of hydrogen and lower alkyl; R 2 is phenyl unsubstituted or substituted by nitro, cyano, trifluoromethyl or halogen; and R 3 is alkoxyalkyl of up to 6 carbon atoms in both moieties.
Claim 22
Dependent Claim
17 words
A method according to claim 12 wherein the compound is 1,2,6,-trimethyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-(β -diethylamine)-ethyl ester 5-methyl ester.
Claim 23
Dependent Claim
16 words
A method according to claim 12 wherein the compound is 1,2,6-trimethyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3(γ-dimethylamino)-propyl ester 5-ethyl ester.
Claim 24
Dependent Claim
16 words
A method according to claim 12 wherein the compound is 2,6-dimethyl-4-(2'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-(γ-dimethylamino)-propyl ester 5-methyl ester.
References Cited (Backward Citations)
US3488359A
Cited
US3905970A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-07-25 | 1981-01-24 | 1981-07-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-07-25 | 1985-01-24 | 1985-07-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-07-25 | 1989-01-24 | 1989-07-26 | $7700.00 | Window Closed / Lapsed |