US4004014A
Expired / Lapsed
US
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2-Amino-6-dialkylaminodihydropyridines, their production, pharmaceutical compositions and methods of use thereof
Assignee: Bayer AG
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Filing: 1975-01-29
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Granted: 1977-01-18
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Expires: 1995-01-29
Abstract
Abstract 2-Amino-6-dialkylaminodihydropyridines exist in tautomeric form and are represented by the formulae <IMAGE> Ia or <IMAGE> Ib WHEREIN R1 and R3 are the same or different and each is straight, branched or cyclic alkyl, alkenyl or alkynyl or said alkyl, alkenyl or alkynyl interrupted by 1 or 2 oxygen atoms; R2 is a saturated, partially unsaturated or unsaturated straight, branched or cyclic hydrocarbon; aryl unsubstituted or substituted by 1, 2 or 3 of the same or different substituents selected from the group consisting of alkyl, alkoxy, azido, halo, cyano, nitro, trifluoromethyl, carbalkoxy and SOn-alkyl wherein n is 0, 1 or 2; naphthyl; quinolyl; isoquinolyl; pyridyl; pyrimidyl; thenyl; or furyl; and R4 and R5 are each lower alkyl; benzyl; or, together with the nitrogen atom to which they are attached, a 4- to 7-membered ring. These compounds are useful for their coronary-vessel-dilating effect, their antihypertensive effect, their anti-fibrillation effect, their vascular-spasmolytic effect and their muscular-spasmolytic effect.
Inventors
- 👤 Horst Meyer
- 👤 Friedrich Bossert
- 👤 Wulf Vater
- 👤 Kurt Stoepel
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 14:58
CPC Classifications
C; C07; C07D; C07D211/00; C07D211/04; C07D211/80; C07D211/84; C07D211/90; A; A61; A61P; A61P1/00; A61P11/00; A61P15/00; A61P15/04; A61P3/00; A61P3/06; A61P9/00; A61P9/06; A61P9/08; A61P9/10; A61P9/12
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
67 words
A compound of the tautomeric formulas: ##STR14##wherein each of R 1 and R 3 is alkyl of 1 to 6 carbon atoms; R 2 is phenyl; phenyl substituted by methyl, methoxy, chloro, bromo, fluoro, nitro, trifluoromethyl, or azido; or pyridyl; and R 4 and R 5 when taken independently are lower alkyl or when taken together, with the nitrogen to which they are attached, pyrrolidino or piperidino.
Claim 2
Dependent Claim
67 words
A compound of the tautomeric formulas: ##STR14##wherein each of R 1 and R 3 is alkyl of 1 to 6 carbon atoms; R 2 is phenyl; phenyl substituted by methyl, methoxy, chloro, bromo, fluoro, nitro, trifluoromethyl, or azido; or pyridyl; and R 4 and R 5 when taken independently are lower alkyl or when taken together, with the nitrogen to which they are attached, pyrrolidino or piperidino.
Claim 3
Dependent Claim
12 words
The compound according to claim 1 which is 2-amino-6-pyrrolidino-4-phenyl-4,5-dihydropyridine-3,5-dicarboxylic acid diethyl ester.
Claim 4
Dependent Claim
12 words
The compound according to claim 1 which is 2-amino-6-dimethylamino-4-(3-nitrophenyl)-4,5-dihydropyridine-3,5-dicarboxylic acid diethyl ester.
Claim 5
Dependent Claim
12 words
The compound according to clam 1 which is 2-amino-6-dimethylamino-4-(pyrid-2-yl)-4,5-dihydropyridine-3,5-dicarboxylic acid diethyl ester.
Claim 6
Dependent Claim
12 words
The compound according to clam 1 which is 2-amino-6-dimethylamino-4-(pyrid-2-yl)-4,5-dihydropyridine-3,5-dicarboxylic acid diethyl ester.
Claim 7
Dependent Claim
12 words
The compound according to claim 1 which is 2-amino-6-piperidino-4-(3-nitrophenyl)-4,5-dihydropyridine-3,5-dicarboxylic acid diethyl ester.
Claim 8
Dependent Claim
51 words
A compound according to claim 1 wherein R 1 is methyl or ethyl; R 2 is phenyl; nitrophenyl; or pyridyl; R 3 is methyl or ethyl; and R 4 and R 5 are each methyl or ethyl; or, together with the nitrogen atoms to which they are attached, pyrrolidino or piperidino.
Claim 9
Dependent Claim
38 words
A compound according to claim 6 wherein R 1 is ethyl; R 3 is ethyl; and R 4 and R 5 are each methyl; or, together with the nitrogen atom to which they are attached, pyrrolidino or piperidino.
Claim 10
Dependent Claim
30 words
The method of effecting coronary vessel dilation and reducing blood pressure in humans and other animals which comprises administering thereto an effective amount of a compound according to claim 1.
Claim 11
Dependent Claim
17 words
A pharmaceutical composition comprising a compound according to claim 1 in combination with a pharmaceutically acceptable carrier.
Claim 12
Dependent Claim
118 words
A process which comprises allowing an acrylate of the formula: ##STR15##wherein R 3 , R 4 and R 5 are as therein defined to react (a) with an aldehyde of the formula R 2 CHO wherein R 2 is as herein defined at a molar ratio of about 2:1 in an inert organic solvent to yield a compound according to claim 1 wherein R 1 is the same as R 3 , or (b) with about an equimolar amount of an ylidene cyanoacetate of the formula: ##STR16##wherein R 1 and R 2 are as herein defined in an inert organic solvent and in the presence of an alkali metal alcoholate to yield a compound according to claim 1.
Claim 13
Dependent Claim
26 words
A process according to claim 10 wherein the inert organic solvent is methanol, ethanol, propanol, dioxan, diethyl ether, glacial acetic acid, pyridine, dimethylformamide, dimethylsulphoxide or acetonitrile.
Claim 14
Dependent Claim
20 words
A process according to claim 10 wherein the reaction is conducted at a temperature of from 20° to 250° C.
Claim 15
Dependent Claim
18 words
A process according to claim 10 wherein the reaction is conducted at the boiling point of the solvent.
References Cited (Backward Citations)
US3887558A
Cited
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1980-01-18 | 1980-07-19 | 1981-01-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-01-18 | 1984-07-19 | 1985-01-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-01-18 | 1988-07-19 | 1989-01-18 | $7700.00 | Window Closed / Lapsed |