US3932645A
Expired / Lapsed
US
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Pharmaceutical compositions containing unsymmetrical esters of 1,4-dihydropyridine 3,5-dicarboxylic acid
Assignee: Bayer AG
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Filing: 1973-09-20
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Granted: 1976-01-13
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Expires: 1993-09-20
Abstract
Abstract Pharmaceutical compositions containing unsymmetrical esters of 1,4-dihydropyridine 3,5-dicarboxylic acids as the active ingredient and methods of using same. The said ingredients are unsymmetrical 1,4-dihydropyridine 3,5-dicarboxylates which are substituted at position-4 of the dihydropyridine nucleus by phenyl which contains at least one nitro, cyano, azido, alkylthio, or alkylsulphonyl substituent. The compositions have a cardiovascular activity which makes them useful for effecting coronary vascular dilation and, also, they have utility in the treatment of hypertension.
Inventors
- 👤 Horst Meyer
- 👤 Friedrich Bossert
- 👤 Wulf Vater
- 👤 Kurt Stoepel
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 15:45
CPC Classifications
C; C07; C07D; C07D401/00; C07D401/02; C07D401/04
Claims Analysis
Total Claims: 30
Claim 1
Independent Claim
173 words
A pharmaceutical composition useful for effecting coronary vascular dilation and for treating hypertension which comprises a coronary vascular dilating effective amount or an antihypertensive amount of a compound of the formula: ##SPC2## wherein R is mono or disubstituted phenyl in which the substituents are selected from the group consisting of nitro, cyano, azido, --S(O) n -lower alkyl in which n has a value of 0, 1 or 2, lower alkyl, lower alkoxy and halogeno, at least one of said substituents being nitro, cyano, azido or --S(O) n -lower alkyl; or a member selected from the group consisting of naphthyl, pyridyl, methylpyridyl, thenyl, furyl, and pyrryl; each of R 1 and R 3 , independent of the other, is hydrogen or lower alkyl; R 2 is lower alkyl, lower alkenyl, lower alkynyl, or lower alkoxy(lower alkyl); R 4 is lower alkyl, lower alkenyl, lower alkynyl, or lower alkoxy(lower alkyl), R 4 being different from R 2 , or a pharmaceutically acceptable acid addition salt thereof, in combination with a pharmaceutically acceptable non-toxic inert carrier.
Claim 2
Dependent Claim
173 words
A pharmaceutical composition useful for effecting coronary vascular dilation and for treating hypertension which comprises a coronary vascular dilating effective amount or an antihypertensive amount of a compound of the formula: ##SPC2## wherein R is mono or disubstituted phenyl in which the substituents are selected from the group consisting of nitro, cyano, azido, --S(O) n -lower alkyl in which n has a value of 0, 1 or 2, lower alkyl, lower alkoxy and halogeno, at least one of said substituents being nitro, cyano, azido or --S(O) n -lower alkyl; or a member selected from the group consisting of naphthyl, pyridyl, methylpyridyl, thenyl, furyl, and pyrryl; each of R 1 and R 3 , independent of the other, is hydrogen or lower alkyl; R 2 is lower alkyl, lower alkenyl, lower alkynyl, or lower alkoxy(lower alkyl); R 4 is lower alkyl, lower alkenyl, lower alkynyl, or lower alkoxy(lower alkyl), R 4 being different from R 2 , or a pharmaceutically acceptable acid addition salt thereof, in combination with a pharmaceutically acceptable non-toxic inert carrier.
Claim 3
Dependent Claim
24 words
A pharmaceutical composition according to claim 1 wherein each of R 1 and R 3 is lower alkyl and R 2 is lower alkyl.
Claim 4
Dependent Claim
44 words
A pharmaceutical composition according to claim 1 wherein R 1 and R 3 are each methyl, R 2 is methyl, ethyl, propyl or isopropyl and R 4 is different from R 2 and is methyl, ethyl, propyl, isopropyl, allyl, propargyl, propoxyethyl, methoxyethyl or cyclohexyl.
Claim 5
Dependent Claim
24 words
A pharmaceutical composition according to claim 3 wherein R is phenyl substituted by cyano, nitro or methylmercapto and further unsubstituted or substituted by chloro.
Claim 6
Dependent Claim
15 words
A pharmaceutical composition according to claim 3 wherein R is pyridyl, pyrryl, furyl, or pyrimidyl.
Claim 7
Dependent Claim
14 words
A pharmaceutical composition according to claim 3 wherein R is naphthyl, quinolyl or isoquinolyl.
Claim 8
Dependent Claim
11 words
A pharmaceutical composition according to claim 1 in oral administration form.
Claim 9
Dependent Claim
16 words
A pharmaceutical composition according to claim 1 wherein the compound is 2,6-dimethyl-4-(2'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-methyl ester-5-isopropyl ester.
Claim 10
Dependent Claim
16 words
A pharmaceutical composition according to claim 1 wherein the compound is 2,6-dimethyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-methyl ester-5-ethyl ester.
Claim 11
Dependent Claim
16 words
A pharmaceutical composition according to claim 1 wherein the compound is 2,6-dimethyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-methyl ester-5-isopropyl ester.
Claim 12
Dependent Claim
15 words
A pharmaceutical composition according to claim 1 wherein the compound is 2,6-dimethyl-4-(3'-nitrophenyl)-1,4-dihydropyridine 3-β-methoxyethyl ester-5-isopropyl ester.
Claim 13
Dependent Claim
16 words
A pharmaceutical composition according to claim 1 wherein the compound is 2,6-dimethyl-4-(4'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-methyl ester-5-ethyl ester.
Claim 14
Dependent Claim
16 words
A pharmaceutical composition according to claim 1 wherein the compound is 2,6-dimethyl-4-(α-pyridyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-methyl ester-5-isopropyl ester.
Claim 15
Dependent Claim
16 words
A pharmaceutical composition according to claim 1 wherein the compound is 2,6-dimethyl-4-(α-pyridyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-methyl ester-5-propargyl ester.
Claim 16
Independent Claim
166 words
A method of effecting coronary vascular dilation in humans and animals which comprises administering to such human or animal an amount of a compound of the formula: ##SPC3## wherein R is mono or disubstituted phenyl in which the substituents are selected from the group consisting of nitro, cyano, azido, --S(O) n -lower alkyl in which n has a value of 0, 1 or 2, lower alkyl, lower alkoxy and halogeno, at least one of said substituents being nitro, cyano, azido or --S(O) n -lower alkyl; or a member selected from the group consisting of naphthyl, pyridyl, methylpyridyl, thenyl, furyl, and pyrryl; each of R 1 and R 3 , independent of the other, is hydrogen or lower alkyl; R 2 is lower alkyl, lower alkenyl, lower alkynyl, or lower alkoxy(lower alkyl); R 4 is lower alkyl, lower alkenyl, lower alkynyl, or lower alkoxy(lower alkyl), R 4 being different from R 2 , or a pharmaceutically acceptable acid addition salt thereof, sufficient to effect coronary vascular dilation.
Claim 17
Independent Claim
166 words
A method of effecting coronary vascular dilation in humans and animals which comprises administering to such human or animal an amount of a compound of the formula: ##SPC3## wherein R is mono or disubstituted phenyl in which the substituents are selected from the group consisting of nitro, cyano, azido, --S(O) n -lower alkyl in which n has a value of 0, 1 or 2, lower alkyl, lower alkoxy and halogeno, at least one of said substituents being nitro, cyano, azido or --S(O) n -lower alkyl; or a member selected from the group consisting of naphthyl, pyridyl, methylpyridyl, thenyl, furyl, and pyrryl; each of R 1 and R 3 , independent of the other, is hydrogen or lower alkyl; R 2 is lower alkyl, lower alkenyl, lower alkynyl, or lower alkoxy(lower alkyl); R 4 is lower alkyl, lower alkenyl, lower alkynyl, or lower alkoxy(lower alkyl), R 4 being different from R 2 , or a pharmaceutically acceptable acid addition salt thereof, sufficient to effect coronary vascular dilation.
Claim 18
Dependent Claim
23 words
A method according to claim 15 wherein each of R 1 and R 3 is lower alkyl and R 2 is lower alkyl.
Claim 19
Dependent Claim
43 words
A method according to claim 15 wherein R 1 and R 3 are each methyl, R 2 is methyl, ethyl, propyl or isopropyl and R 4 is different from R 2 and is methyl, ethyl, propyl, isopropyl, allyl, propargyl, propoxyethyl, methoxyethyl or cyclohexyl.
Claim 20
Dependent Claim
23 words
A method according to claim 15 wherein R is phenyl substituted by cyano, nitro or methylmercapto and further unsubstituted or substituted by chloro.
Claim 21
Dependent Claim
13 words
A method according to claim 15 wherein R is pyridyl, pyrryl or furyl.
Claim 22
Dependent Claim
10 words
A method according to claim 15 wherein R is naphthyl.
Claim 23
Dependent Claim
11 words
A method according to claim 15 wherein the administration is oral.
Claim 24
Dependent Claim
15 words
The method according to claim 15 wherein the compound is 2,6-dimethyl-4-(2'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-methyl ester-5-isopropyl ester.
Claim 25
Dependent Claim
15 words
The method according to claim 15 wherein the compound is 2,6-dimethyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-methyl ester-5-ethyl ester.
Claim 26
Dependent Claim
15 words
The method according to claim 15 wherein the compound is 2,6-dimethyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-methyl ester-5-isopropyl ester.
Claim 27
Dependent Claim
14 words
The method according to claim 15 wherein the compound is 2,6-dimethyl-4-(3'-nitrophenyl)-1,4-dihydropyridine 3-β-methoxyethyl ester-5-isopropyl ester.
Claim 28
Dependent Claim
15 words
The method according to claim 15 wherein the compound is 2,6-dimethyl-4-(4'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-methyl ester-5-ethyl ester.
Claim 29
Dependent Claim
15 words
The method according to claim 15 wherein the compound is 2,6-dimethyl-4-(α-pyridyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-methyl ester-5-isopropyl ester.
Claim 30
Dependent Claim
15 words
The method according to claim 15 wherein the compound is 2,6-dimethyl-4-(α-pyridyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-methyl ester-5-propargyl ester.
References Cited (Backward Citations)
US3470297A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-01-12 | 1979-07-14 | 1980-01-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-01-12 | 1983-07-14 | 1984-01-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-01-12 | 1987-07-14 | 1988-01-13 | $7700.00 | Window Closed / Lapsed |