US4048171A
Expired / Lapsed
US
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1,4-Dihydropyridines
Assignee: Bayer AG
•
Filing: 1971-02-05
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Granted: 1977-09-13
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Expires: 1991-02-05
Abstract
Abstract 1,4-Dihydropyridines of the formula: ##STR1## wherein R is hydrogen, straight, branched or cyclic lower alkyl, lower alkenyl, or lower alkinyl, unsubstituted or substituted; or benzyl, or phenethyl, unsubstituted or substituted in the aryl portion; R' is alkyl of 1 to 4 carbon atoms; R" is alkenyl of 2 to 6 carbon atoms, alkinyl of 2 to 6 carbon atoms, cyclic alkenyl of 3 to 6 carbon atoms interrupted by oxygen, alkenyl of 2 to 6 carbon atoms or alkinyl of 2 to 6 carbon atoms interrupted by 1 or 2 oxygen atoms, or alkenyl of 2 to 6 carbon atoms or alkinyl of 2 to 6 carbon atoms substituted by hydroxyl; and R'"is unsubstituted or substituted aryl; cyclohexyl; benzyl; styryl; pyridyl; pyrimidyl; furyl; thienyl; pyrrolyl; pyridyl, pyrrolyl, thienyl or furyl substituted by alkyl of 1 or 2 carbon atoms; or substituted pyrimidyl: ##STR2## are useful for their coronary dilating effect, their nitrite-like effect on the heart, their anti-fibrillation effect, their vascular-spasmolytic effect and muscular-spasmolytic effect, and as anti-hypertensives.
Inventors
- 👤 Friedrich Bossert
- 👤 Wulf Vater
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 02:37
CPC Classifications
C; C07; C07D; C07D401/00; C07D401/02; C07D401/04; C07D211/00; C07D211/04; C07D211/80; C07D211/84; C07D211/90; C07D405/00; C07D405/02; C07D405/04; C07D409/00; C07D409/02; C07D409/04
Claims Analysis
Total Claims: 40
Claim 1
Independent Claim
87 words
A compound of the formula: ##STR7## wherein R is hydrogen, alkyl of 1 to 4 carbon atoms or benzyl; R' is alkyl of 1 to 4 carbon atoms; R" is alkenyl of 3 or 4 carbon atoms or alkinyl of 3 or 4 carbon atoms; and R'" is cyclohexyl; phenyl unsubstituted or substituted by 1 to 3 groups selected from the group consisting of nitro, chlorine, bromine, 1 to 3 methoxy moieties, trifluoromethyl, carbomethoxy, carboxy and 1 or 2 hydroxymethylene moieties; pyridyl; thienyl; pyrrolyl; N-methylpyrrolyl; and dimethoxypyrimidyl.
Claim 2
Dependent Claim
87 words
A compound of the formula: ##STR7## wherein R is hydrogen, alkyl of 1 to 4 carbon atoms or benzyl; R' is alkyl of 1 to 4 carbon atoms; R" is alkenyl of 3 or 4 carbon atoms or alkinyl of 3 or 4 carbon atoms; and R'" is cyclohexyl; phenyl unsubstituted or substituted by 1 to 3 groups selected from the group consisting of nitro, chlorine, bromine, 1 to 3 methoxy moieties, trifluoromethyl, carbomethoxy, carboxy and 1 or 2 hydroxymethylene moieties; pyridyl; thienyl; pyrrolyl; N-methylpyrrolyl; and dimethoxypyrimidyl.
Claim 3
Dependent Claim
16 words
A compound according to claim 1 wherein R'" is alkenyl of 3 or 4 carbon atoms.
Claim 4
Dependent Claim
16 words
A compound according to claim 1 wherein R" is alkenyl of 3 or 4 carbon atoms.
Claim 5
Dependent Claim
12 words
The compound according to claim 2 which is 2,6-dimethyl-4-(α-pyridyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diallyl ester.
Claim 6
Dependent Claim
12 words
The compound according to claim 3 which is 2,6-dimethyl-4-(α-pyridyl)-1,4-dihydropyridine-3,5-dicarboxylic acid dipropargyl ester.
Claim 7
Dependent Claim
12 words
The compound according to claim 2 which is 1,2,6-trimethyl-4-(β-pyridyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diallyl ester.
Claim 8
Dependent Claim
12 words
The compound according to claim 2 which is 1,2,6-trimethyl-4-(α-pyridyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diallyl ester.
Claim 9
Dependent Claim
12 words
The compound according to claim 3 which is 1,2,6-trimethyl-4-(α-pyridyl)-1,4-dihydropyridine-3,5-dicarboxylic acid dipropargyl ester.
Claim 10
Dependent Claim
12 words
The compound according to claim 3 which is 2,6-dimethyl-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylic acid dipropargyl ester.
Claim 11
Dependent Claim
12 words
The compound according to claim 2 which is 2,6-dimethyl-4-(3'-trifluoromethylphenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diallyl ester.
Claim 12
Dependent Claim
12 words
The compound according to claim 3 which is 2,6-dimethyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid dipropargyl ester.
Claim 13
Dependent Claim
12 words
The compound according to claim 2 which is 2,6-dimethyl-4-(3'-nitro-6'-chlorophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diallyl ester.
Claim 14
Dependent Claim
12 words
The compound according to claim 2 which is 2,6-dimethyl-4-(α-thienyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diallyl ester.
Claim 15
Dependent Claim
12 words
The compound according to claim 3 which is 1,2,6-trimethyl-4-(3'-trifluoromethyl-phenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid dipropargyl ester.
Claim 16
Dependent Claim
12 words
The compound according to claim 2 which is 1,2,6-trimethyl-4-(4'-carbomethoxyphenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diallyl ester.
Claim 17
Dependent Claim
12 words
The compound according to claim 2 which is 1,2,6-trimethyl-4-(3'-fluorophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diallyl ester.
Claim 18
Dependent Claim
12 words
The compound according to claim 3 which is 1,2,6-trimethyl-4-(3',4',5'-trimethoxyphenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid dipropargyl ester.
Claim 19
Dependent Claim
12 words
The compound according to claim 3 which is 2,6-dimethyl-4-(4'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid dipropargyl ester.
Claim 20
Dependent Claim
12 words
The compound according to claim 2 which is 2,6-dimethyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diallyl ester.
Claim 21
Dependent Claim
12 words
The compound according to claim 2 which is 2,6-dimethyl-4-(2'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diallyl ester.
Claim 22
Dependent Claim
12 words
The compound according to claim 3 which is 2,6-dimethyl-4-(2'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid dipropargyl ester.
Claim 23
Dependent Claim
12 words
The compound according to claim 3 which is 2,6-dimethyl-4-(2'-trifluoromethylphenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid dipropargyl ester.
Claim 24
Dependent Claim
12 words
The compound according to claim 2 which is 2,6-dimethyl-4-(2'-trifluoromethylphenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diallyl ester.
Claim 25
Dependent Claim
12 words
The compound according to claim 2 which is 2,6-dimethyl-4-(2'-methoxyphenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diallyl ester.
Claim 26
Dependent Claim
12 words
The compound according to claim 3 which is 2,6-dimethyl-4-(3',4'-methylenedioxy-6'-bromophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid dipropargyl ester.
Claim 27
Dependent Claim
12 words
The compound according to claim 3 which is 2,6-dimethyl-4-(4'-carboxyphenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid dipropargyl ester.
Claim 28
Dependent Claim
12 words
The compound according to claim 3 which is 2,6-dimethyl-4-(α-pyrrolyl)-1,4-dihydropyridine-3,5-dicarboxylic acid dipropargyl ester.
Claim 29
Dependent Claim
12 words
The compound according to claim 3 which is 2,6-dimethyl-4-(α-N-methylpyrrolyl)-1,4-dihydropyridine-3,5-dicarboxylic acid dipropargyl ester.
Claim 30
Dependent Claim
12 words
The compound according to claim 2 which is 2,6-dimethyl-4-(4',6'-dimethoxy-5'-pyrimidyl)-1,4-dihydropyridine-3,5-carboxylic acid diallyl ester.
Claim 31
Dependent Claim
12 words
The compound according to claim 3 which is 1,2,6-trimethyl-4-(3',4'-methylenedioxy-6'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid dipropargyl ester.
Claim 32
Dependent Claim
12 words
The compound according to claim 2 which is 1,2,6-trimethyl-4-(3',4'-methylenedioxy-6'-bromophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diallyl ester.
Claim 33
Dependent Claim
12 words
The compound according to claim 3 which is 1,2,6-trimethyl-4-(2'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid dipropargyl ester.
Claim 34
Dependent Claim
12 words
The compound according to claim 2 which is 1,2,6-trimethyl-4-(2'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diallyl ester.
Claim 35
Dependent Claim
12 words
The compound according to claim 2 which is 1,2,6-trimethyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diallyl ester.
Claim 36
Dependent Claim
12 words
The compound according to claim 3 which is 1,2,6-trimethyl-4-(4'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid dipropargyl ester.
Claim 37
Dependent Claim
12 words
The compound according to claim 2 which is 1,2,6-trimethyl-4-(2'-trifluoromethylphenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diallyl ester.
Claim 38
Dependent Claim
12 words
The compound according to claim 3 which is 1,2,6-trimethyl-4-cyclohexyl-1,4-dihydropyridine-3,5-dicarboxylic acid dipropargyl ester.
Claim 39
Dependent Claim
12 words
The compound according to claim 3 which is 1,2,6-trimethyl-4-α-pyrrolyl-1,4-dihydropyridine-3,5-dicarboxylic acid dipropargyl ester.
Claim 40
Dependent Claim
12 words
The compound according to claim 2 which is 1-benzyl-2,6-dimethyl-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylic acid diallyl ester.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-09-12 | 1981-03-14 | 1981-09-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-09-12 | 1985-03-14 | 1985-09-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-09-12 | 1989-03-14 | 1989-09-13 | $7700.00 | Window Closed / Lapsed |