US3883540A
Expired / Lapsed
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Unsymmetrical esters of N-substituted 1,4-dihydropyridine 3,5-dicarboxylic acid
Assignee: Bayer AG
•
Filing: 1973-02-28
•
Granted: 1975-05-13
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Expires: 1993-02-28
Abstract
Abstract Unsymmetrical esters of N-substituted 4-substituted-1,4dihydropyridine 3,5-dicarboxylic acid optionally substituted by lower alkyl groups in the 2- and 6-positions are cardiovascular agents. The compounds, of which 1,2,6-trimethyl-4-(3''nitrophenyl)-1,4-dihydropyridine 3,5-dicarboxylic acid 3-methyl5-ethyl ester is a typical example, can be prepared (A) through condensation of an ylidene- Beta -ketocarboxylic acid ester, with a Beta -ketocarboxylic acid ester and an amino or salt thereof, or with an enamino carboxylic acid ester or (B) through condensation of an aldehyde, an enamino carboxylic acid ester and a Beta -ketocarboxylic acid ester.
Inventors
- 👤 Horst Meyer
- 👤 Friedrich Bossert
- 👤 Wulf Vater
- 👤 Kurt Stoepel
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 05:06
CPC Classifications
C; C07; C07D; C07D405/00; C07D405/02; C07D405/04; A; A61; A61P; A61P1/00; A61P11/00; A61P11/08; A61P13/00; A61P13/02; A61P15/00; A61P3/00; A61P3/06; A61P9/00; A61P9/06; A61P9/08; A61P9/10; A61P9/12; C07D211/00; C07D211/04; C07D211/80; C07D211/84; C07D211/90; C07D409/00; C07D409/02; C07D409/04
Claims Analysis
Total Claims: 26
Claim 1
Independent Claim
6 words
A COMPOUND OF THE GENERAL FORMULA:
Claim 2
Dependent Claim
6 words
A COMPOUND OF THE GENERAL FORMULA:
Claim 3
Dependent Claim
69 words
The compound according to claim 1, in which R is phenyl substituted by one or two nitro, cyano, axido or S(O)n-lower alkyl, in which n is 0 or 2 and said lower alkyl has 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms or halo, at least one of said substituents being said nitro, cyano, Azido or S(O)n-lower alkyl.
Claim 4
Dependent Claim
22 words
The compound according to claim 1, in which R1 and R3 are independently hydrogen or alkyl of 1 to 4 carbon atoms.
Claim 5
Dependent Claim
60 words
The compound according to claim 1, in which R2 and R4 are different from one another and are alkyl of 1 to 4 carbon atoms, alkenyl of 2 to 4 carbon atoms, alkynyl of 2 to 4 carbon atoms, alkoxy(lower alkyl) with 1 to 4 carbon atoms in said alkoxy and alkyl moieties or cyclohexyl, unsubstituted or substituted by hydroxy.
Claim 6
Dependent Claim
19 words
The compound according to claim 1, in which R5 is alkyl of 1 to 4 carbon atoms or benzyl.
Claim 7
Dependent Claim
92 words
The compound according to claim 1, in which R is nitrophenyl, halo substituted nitrophenyl, cyanophenyl, halo substituted cyanophenyl, said halo being chloro or bromo, R1 and R3 are independently hydrogen or lower alkyl, R2 and R4 are different from one another and are alkyl of 1 to 4 carbon atoms, alkenyl of 2 to 4 carbon atoms, alkynyl of 2 to 4 carbon atoms, alkoxy(lower alkyl) of 1 to 4 carbon atoms or lower cycloalkyl, unsubstituted or substituted by hydroxy, and R5 is alkyl of 1 to 4 carbon atoms or benzyl.
Claim 8
Dependent Claim
83 words
The compound according to claim 1, in which R is nitrophenyl, nitrophenyl substituted by one or two halo selected from the group consisting of chloro, bromo and cyanophenyl, R1 and R3 are independently hydrogen or lower alkyl, R2 and R4 are different from one another and are alkyl of 1 to 4 carbon atoms, alkenyl of 2 to 4 carbon atoms, alkoxy(lower alkyl) of 1 to 4 carbon atoms or cyclohexyl, and R5 is alkyl of 1 to 4 carbon atoms or benzyl.
Claim 9
Dependent Claim
11 words
The compound according to claim 1, which is 1-methyl-4-(2''-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-methyl-ester-5-isopropyl-ester.
Claim 10
Dependent Claim
11 words
The compound according to claim 1, which is 1,2,6-trimethyl-4-(2''-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-methyl-3-ester-5-isopropyl-ester.
Claim 11
Dependent Claim
11 words
The compound according to claim 1, which is 1,2,6-trimethyl-4-(3''-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-methyl-ester-5-ethyl-ester.
Claim 12
Dependent Claim
11 words
The compound according to claim 1, which is 1,2,6-trimethyl-4-(3''-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-ethyl-ester-5-isopropyl-ester.
Claim 13
Dependent Claim
11 words
The compound according to claim 1, which is 1,2,6-trimethyl-4-(3''-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-ethyl-ester-5-alkyl-ester.
Claim 14
Dependent Claim
13 words
The compound according to claim 1, which is 1,2,6-trimethyl-4-(3''-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-methyl-ester-5- Beta -methoxyethylester.
Claim 15
Dependent Claim
12 words
The compound according to claim 1, which is 1-benzyl-2,6-dimethyl-4-(3''-nitrophenyl)-1,4-dihydropyridine-3,5 -dicarboxylic acid 3-methyl-ester-5-ethyl-ester.
Claim 16
Dependent Claim
11 words
The compound according to claim 1, which is 1,2,6-trimethyl-4-(3''-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-methyl-ester-5-cyclohexyl-ester.
Claim 17
Dependent Claim
11 words
The compound according to claim 1, which is 1,6-dimethyl-2-ethyl-4-(3''-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-ethyl-ester-5-isopropyl-ester.
Claim 18
Dependent Claim
11 words
The compound according to claim 1, which is 1,2,6-trimethyl-4-(2''-cyanophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-methyl-ester-5-ethyl-ester.
Claim 19
Dependent Claim
12 words
The compound according to claim 1, whIch is 1,2,6-trimethyl-4-(2''-cyanophenyl)-1,4-dihydropyridine, 3,5-dicarboxylic acid 3-ethyl-ester-5-allyl-ester.
Claim 20
Dependent Claim
11 words
The compound according to claim 1, which is 1,2,6-trimethyl-4-(2''-cyanophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-ethyl-ester-5-isopropyl-ester.
Claim 21
Dependent Claim
11 words
The compound according to claim 1, which is 1,6-dimethyl-2-ethyl-4-(2''-cyanophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-ethyl-ester-5-methyl-ester.
Claim 22
Dependent Claim
12 words
The compound according to claim 1, which is 1-benzyl-2,6-dimethyl-4-(2''-cyanophenyl)-1,4-dihydropyridine-3,5 -dicarboxylic acid 3-methyl-ester-5-ethyl-ester.
Claim 23
Dependent Claim
12 words
The compound according to claim 1, which is 1,2,6-trimethyl-4-(3''-nitro-6''-chlorophenyl)-1,4-dihydropyridine-3,5 -dicarboxylic acid 3-ethyl-ester-5-isopropyl-ester.
Claim 24
Dependent Claim
14 words
The compound according to claim 1, which is 1,2,6-trimethyl-4-(3''-nitro-6''-chlorophenyl)-1,4-dihydropyridine-3,5 -dicarboxylic acid 3-ethyl-ester-5- Beta -methoxyethyl-ester.
Claim 25
Dependent Claim
11 words
The compound according to claim 1, which is 1,2,6-trimethyl-4-(3''-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-methyl-ester-5-isopropyl-ester.
Claim 26
Dependent Claim
12 words
The compound according to claim 1, which is 1,2,6-trimethyl-4-(6''-chloro-3''-nitrophenyl)-1,4-dihydropyridine-3,5 -dicarboxylic acid 3-ethyl-ester-5-methyl-ester.
References Cited (Backward Citations)
US3799936A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1978-05-12 | 1978-11-11 | 1979-05-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1982-05-12 | 1982-11-11 | 1983-05-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1986-05-12 | 1986-11-11 | 1987-05-13 | $7700.00 | Window Closed / Lapsed |