US3959296A
Expired / Lapsed
US
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1,4-Dihydropyridines
Assignee: Bayer AG
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Filing: 1974-08-28
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Granted: 1976-05-25
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Expires: 1994-08-28
Abstract
Abstract Derivatives of 4-substituted phenyl 1,4-dihydropyridine 3,5-dicarboxylic acids substituted by lower alkyl groups in the 2- and 6-positions, are cardiovascular agents. The compounds, of which 2,6-dimethyl-4-[2-(diethylaminoethoxy)-phenyl]-1,4-dihydropyridine-3,5-dicarboxylic acid 3,5-diethyl ester is a typical example, can be prepared through condensation of a β-dicarbonyl compound with an amine and an aldehyde, of an ylidene-β-ketocarboxylic acid ester, with a β-ketocarbonyl compound and an amine, of an aldehyde, an enamine and a β-ketocarbonyl compound, or through elaboration of the substituent on the phenyl group.
Inventors
- 👤 Friedrich Bossert
- 👤 Horst Meyer
- 👤 Wulf Vater
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 19:11
CPC Classifications
C; C07; C07D; C07D211/00; C07D211/04; C07D211/80; C07D211/84; C07D211/90
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
186 words
A compound of the formula: ##SPC28## wherein R is hydrogen, lower alkyl or alkenyl of 2 to 4 carbon atoms; each of R 1 and R 4 is hydrogen or alkyl of 1 to 3 carbon atoms; each of R 2 and R 3 is lower alkyl; alkenyl of 2 to 4 carbon atoms; or a member selected from the group consisting of lower alkoxy, alkenyloxy of 2 to 4 carbon atoms and alkynyloxy of 2 to 4 carbon atoms which is unsubstituted, or substituted by hydroxy or lower alkoxy; or R 2 and R 3 are each furfuryloxy; A is oxygen or sulphur; B is ##EQU4## wherein each of R 7 and R 8 , when taken independently, is hydrogen or lower alkyl or, when taken together, are alkylene of 4 to 6 carbon atoms; X is lower alkylene or hydroxy-(lower alkylene); each of R 5 and R 6 is hydrogen, lower alkyl, lower alkoxy, nitro, halogeno, cyano, amino, lower alkylamino, di-(lower alkyl)amino or acetylamino, but only one is cyano, lower alkylamino, di-(lower alkyl)amino or acetylamino, or a nontoxic pharmaceutically acceptable acid addition salt thereof.
Claim 2
Dependent Claim
186 words
A compound of the formula: ##SPC28## wherein R is hydrogen, lower alkyl or alkenyl of 2 to 4 carbon atoms; each of R 1 and R 4 is hydrogen or alkyl of 1 to 3 carbon atoms; each of R 2 and R 3 is lower alkyl; alkenyl of 2 to 4 carbon atoms; or a member selected from the group consisting of lower alkoxy, alkenyloxy of 2 to 4 carbon atoms and alkynyloxy of 2 to 4 carbon atoms which is unsubstituted, or substituted by hydroxy or lower alkoxy; or R 2 and R 3 are each furfuryloxy; A is oxygen or sulphur; B is ##EQU4## wherein each of R 7 and R 8 , when taken independently, is hydrogen or lower alkyl or, when taken together, are alkylene of 4 to 6 carbon atoms; X is lower alkylene or hydroxy-(lower alkylene); each of R 5 and R 6 is hydrogen, lower alkyl, lower alkoxy, nitro, halogeno, cyano, amino, lower alkylamino, di-(lower alkyl)amino or acetylamino, but only one is cyano, lower alkylamino, di-(lower alkyl)amino or acetylamino, or a nontoxic pharmaceutically acceptable acid addition salt thereof.
Claim 3
Dependent Claim
10 words
A compound according to claim 1 wherein A is oxygen.
Claim 4
Dependent Claim
10 words
A compound according to claim 1 wherein A is sulphur.
Claim 5
Dependent Claim
34 words
A compound according to claim 1 wherein R is hydrogen or lower alkyl; each of R 1 and R 4 is lower alkyl, and each of R 2 and R 3 is lower alkoxy.
Claim 6
Dependent Claim
28 words
A compound according to claim 1 wherein each of R 5 and R 6 is hydrogen, lower alkoxy, nitro, halogeno, cyano or amino, but only one is cyano.
Claim 7
Dependent Claim
12 words
The compound according to claim 1 which is 2,6-dimethyl-4-[2-(2-diethylaminoethoxy)-phenyl]-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester.
Claim 8
Dependent Claim
12 words
The compound according to claim 1 which is 2,6-dimethyl-4-[4-(2-diethylaminoethoxy)-phenyl]-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester.
Claim 9
Dependent Claim
12 words
The compound according to claim 1 which is 2,6-dimethyl-4-[4-(2-diethylaminoethoxy)-phenyl]-1,4-dihydropyridine-3,5-dicarboxylic acid diisopropyl ester.
Claim 10
Dependent Claim
12 words
The compound according to claim 1 which is 2,6-dimethyl-4-[3-(3-isopropylamino-2-hydroxypropoxy)-phenyl]-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester.
Claim 11
Dependent Claim
12 words
The compound according to claim 1 which is 1,2,6-trimethyl-4-[4-(3-isopropylamino-2-hydroxypropoxy)-phenyl]-1,4-dihydropyridine-3,5-dicarboxylic acid dimethyl ester.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-05-25 | 1979-11-24 | 1980-05-25 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-05-25 | 1983-11-24 | 1984-05-25 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-05-25 | 1987-11-24 | 1988-05-25 | $7700.00 | Window Closed / Lapsed |