US3920823A
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US
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Use of unsymmetrical esters of n-substituted 1,4-dihydropyridine 3,5-dicarboxylic acid as cardio-vascular agents
Assignee: Bayer AG
•
Filing: 1974-05-30
•
Granted: 1975-11-18
•
Expires: 1994-05-30
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 cardio-vascular 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 amine 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
2026-11-05 17:20
CPC Classifications
C; C07; C07D; C07D405/00; C07D405/02; C07D405/04
Claims Analysis
Total Claims: 52
Claim 1
Independent Claim
33 words
THE METHOD OF EFFECTING CORONARY VESSEL DILATION AND A REDUCTION IN BLOOD PRESSURE IN AN ANIMAL IN NEED THEREOF, WHICH COMPRISES ADMINISTERING THERETO AN EFFECTIVE AMOUNT OF A COMPOUND OF THE GENERAL FORMULA:
Claim 2
Independent Claim
33 words
THE METHOD OF EFFECTING CORONARY VESSEL DILATION AND A REDUCTION IN BLOOD PRESSURE IN AN ANIMAL IN NEED THEREOF, WHICH COMPRISES ADMINISTERING THERETO AN EFFECTIVE AMOUNT OF A COMPOUND OF THE GENERAL FORMULA:
Claim 3
Dependent Claim
71 words
The method according to claim 1, in whIch R is phenyl substituted by one or two nitro, cyano, azido or S(O)n-lower alkyl, in which n is 0 or 2 and said lower alkyl has 1 to 4 carbon atoms, lower alkyl of 1 to 4 carbon atoms, lower alkoxy of 1 to 4 carbon atoms or halogeno, at least one of said substituents being said nitro, cyano, azido or S(O)n-lower alkyl.
Claim 4
Dependent Claim
23 words
The method according to claim 1, in which R1 and R3 are independently hydrogen or lower alkyl of 1 to 4 carbon atoms.
Claim 5
Dependent Claim
66 words
The method according to claim 1, in which R2 and R4 are different from one another and are lower alkyl of 1 to 4 carbon atoms, lower alkenyl of 2 to 4 carbon atoms, lower alkynyl of 2 to 4 carbon atoms, lower alkoxy(lower alkyl) with 1 to 4 carbon atoms in said lower alkoxy and lower alkyl moieties or cyclohexyl, unsubstituted or substituted by hydroxy.
Claim 6
Dependent Claim
20 words
The method according to claim 1, in which R5 is lower alkyl of 1 to 4 carbon atoms or benzyl.
Claim 7
Dependent Claim
66 words
The method according to claim 1, in which R is nitrophenyl, halogeno-substituted nitrophenyl, cyanophenyl, or halogeno-substituted cyanophenyl, said halogeno being chlorino or bromino, R1 and R3 are independently hydrogen or lower alkyl, R2 and R4 are different from one another and are lower alkyl, lower alkenyl, lower alkynyl, lower alkoxy(lower alkyl) or lower cycloalkyl, unsubstituted or substituted by hydroxy, and R5 is lower alkyl or benzyl.
Claim 8
Dependent Claim
64 words
The method according to claim 1, in which R is nitrophenyl, nitrophenyl substituted by one or two halogeno selected from the group consisting of chloro and bromo, or cyanophenyl, R1 and R3 are independently hydrogen or lower alkyl, R2 and R4 are different from one another and are lower alkyl, lower alkenyl, lower alkoxy(lower alkyl) or cyclohexyl, and R5 is lower alkyl or benzyl.
Claim 9
Dependent Claim
13 words
The method according to claim 1, wherein said compound is 1-methyl-4-(2''-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-methyl-ester-5-isopropyl-ester.
Claim 10
Dependent Claim
14 words
The method according to claim 1, wherein said compound 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
14 words
The method according to claim 1, wherein said compound 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
14 words
The method according to claim 1, wherein said compound 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
14 words
The method according to claim 1, wherein said compound is 1, 2,6-trimethyl-4-(3''-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-ethyl-ester-5-allyl-ester.
Claim 14
Dependent Claim
16 words
The method according to claim 1, wherein said compound 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
14 words
The method according to claim 1, wherein said compound 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
14 words
The method according to claim 1, wherein said compound 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
14 words
The method according to claim 1, wherein said compound 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
14 words
The method according to claim 1, wherein said compound 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
14 words
The method according to claim 1, wherein said compound 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
14 words
The method according to claim 1, wherein said compound 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
14 words
The method according to claim 1 wherein said compound 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
14 words
The method according to claim 1, wherein said compound 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
15 words
The method according to claim 1, wherein said compound 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
17 words
The method according to claim 1, wherein said compound 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
14 words
The method according to claim 1, wherein said compound 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
15 words
The method according to claim 1, wherein said compound is 1, 2,6-trimethyl-4-(6''-chloro-3''-nitrophenyl)-1,4-dihydropyridine-3, 5-dicarboxylic acid 3-ethyl-ester-5-methyl-ester.
Claim 27
Dependent Claim
28 words
A PHARMACEUTICAL COMPOSITION FOR USE IN EFFECTING CORONARY VESSEL DILATION AND A REDUCTION IN BLOOD PRESSURE, WHICH COMPRISES AN EFFECTIVE AMOUNT OF A COMPOUND OF THE GENERAL FORMULA:
Claim 28
Dependent Claim
28 words
A PHARMACEUTICAL COMPOSITION FOR USE IN EFFECTING CORONARY VESSEL DILATION AND A REDUCTION IN BLOOD PRESSURE, WHICH COMPRISES AN EFFECTIVE AMOUNT OF A COMPOUND OF THE GENERAL FORMULA:
Claim 29
Dependent Claim
71 words
The composition according to claim 26, in which R is phenyl substituted by one or two nitro, cyano, azido or S(O)n-lower alkyl, in which n is 0 or 2 and said lower alkyl has 1 to 4 carbon atoms, lower alkyl of 1 to 4 carbon atoms, lower alkoxy of 1 to 4 carbon atoms or halogeno, at least one of said substituents being said nitro, cyano, azido or S(O)n-lower alkyl.
Claim 30
Dependent Claim
23 words
The composition according to claim 26, in which R1 and R3 are independently hydrogen or lower alkyl of 1 to 4 carbon atoms.
Claim 31
Dependent Claim
66 words
The composition according to claim 26, in which R2 and R4 are different from one another and are lower alkyl of 1 to 4 carbon atoms, lower alkenyl of 2 to 4 carbon atoms, lower alkynyl of 2 to 4 carbon atoms, lower alkoxy(lower alkyl) with 1 to 4 carbon aToms in said lower alkoxy and lower alkyl moieties or cyclohexyl, unsubstituted or substituted by hydroxy.
Claim 32
Dependent Claim
20 words
The composition according to claim 26, in which R5 is lower alkyl of 1 to 4 carbon atoms or benzyl.
Claim 33
Dependent Claim
66 words
The composition according to claim 26, in which R is nitrophenyl, halogeno-substituted nitrophenyl, cyanophenyl, or halogeno-substituted cyanophenyl, said halogeno being chlorino or bromino, R1 and R3 are independently hydrogen or lower alkyl, R2 and R4 are different from one another and are lower alkyl, lower alkenyl, lower alkynyl, lower alkoxy(lower alkyl) or lower cycloalkyl, unsubstituted or substituted by hydroxy, and R5 is lower alkyl or benzyl.
Claim 34
Dependent Claim
64 words
The composition according to claim 26, in which R is nitrophenyl, nitrophenyl substituted by one or two halogeno selected from the group consisting of chloro and bromo, or cyanophenyl, R1 and R3 are independently hydrogen or lower alkyl, R2 and R4 are different from one another and are lower alkyl, lower alkenyl, lower alkoxy(lower alkyl) or cyclohexyl, and R5 is lower alkyl or benzyl.
Claim 35
Dependent Claim
13 words
The composition according to claim 26, wherein said compound is 1-methyl-4-(2''-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-methyl-ester-5-isopropyl-ester.
Claim 36
Dependent Claim
13 words
The composition according to claim 26, wherein said compound is 1,2,6-trimethyl-4-(2''-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-methyl-3-ester-5-isopropyl-ester.
Claim 37
Dependent Claim
11 words
The composition according to claim 26, which is 1,2,6-trimethyl-4-(3''-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-methyl-ester-5-ethyl-ester.
Claim 38
Dependent Claim
11 words
The composition according to claim 26, which is 1,2,6-trimethyl-4-(3''-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-ethyl-ester-5-isopropyl-ester.
Claim 39
Dependent Claim
11 words
The composition according to claim 26, which is 1,2,6-trimethyl-4-(3''-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-ethyl-ester-5-allyl-ester.
Claim 40
Dependent Claim
13 words
The composition according to claim 26, which is 1,2,6-trimethyl-4-(3''-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-methyl-ester-5- Beta -methoxyethylester.
Claim 41
Dependent Claim
12 words
The composition according to claim 26, which is 1-benzyl-2, 6-dimethyl-4-(3''-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-methyl-ester-5-ethyl-ester.
Claim 42
Dependent Claim
11 words
The composition according to claim 26, which is 1,2,6-trimethyl-4-(3''-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-methyl-ester-5-cyclohexyl-ester.
Claim 43
Dependent Claim
11 words
The composition according to claim 26, which is 1,6-dimethyl-2-ethyl-4-(3''-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-ethyl-ester-5-isopropyl-ester.
Claim 44
Dependent Claim
11 words
The composition according to claim 26, which is 1,2,6-trimethyl-4-(2''-cyanophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-methyl-ester-5-ethyl-ester.
Claim 45
Dependent Claim
11 words
The composition according to claim 26, which is 1,2,6-trimethyl-4-(2''-cyanophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-ethyl-ester-5-allyl-ester.
Claim 46
Dependent Claim
11 words
The composition according to claim 26, which is 1,2,6-trimethyl-4-(2''-cyanophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-ethyl-ester-5-isopropyl-ester.
Claim 47
Dependent Claim
11 words
The composition according to claim 26, which is 1,6-dimethyl-2-ethyl-4-(2''-cyanophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-ethyl-ester-5-methyl-ester.
Claim 48
Dependent Claim
12 words
The composition according to claim 26, whicH is 1-benzyl-2, 6-dimethyl-4-(2''-cyanophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-methyl-ester-5-ethyl-ester.
Claim 49
Dependent Claim
12 words
The composition according to claim 26, 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 50
Dependent Claim
14 words
The composition according to claim 26, 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 51
Dependent Claim
11 words
The composition according to claim 26, which is 1,2,6-trimethyl-4-(3''-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-methyl-ester-5-isopropyl-ester.
Claim 52
Dependent Claim
12 words
The composition according to claim 26, 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) | 1978-11-17 | 1979-05-19 | 1979-11-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1982-11-17 | 1983-05-19 | 1983-11-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1986-11-17 | 1987-05-19 | 1987-11-18 | $7700.00 | Window Closed / Lapsed |