US3971796A
Expired / Lapsed
US
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1,4-Dihydropyridine esters
Assignee: Bayer AG
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Filing: 1975-08-29
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Granted: 1976-07-27
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Expires: 1995-08-29
Abstract
Abstract A new class of 1,4-dihydropyridines which are characterized by the presence of ester substitutes at positions 3 and 5 of the nucleus and by the presence of an alkoxyalkyl at position 2. The products exhibit coronary activity and have particular application as coronary dilators, antifibrillators, anti-hypertensives, and as muscular and vascular spasmolytics.
Inventors
- 👤 Friedrich Bossert
- 👤 Egbert Wehinger
- 👤 Wulf Vater
- 👤 Kurt Stoepel
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 06:37
CPC Classifications
C; C07; C07D; C07D401/00; C07D401/02; C07D401/04
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
210 words
A compound selected from the group consisting of a dihydropyridine of the formula: ##SPC31## and the pharmaceutically acceptable nontoxic salts thereof, wherein Y is alkylene of 1 to 4 carbon atoms; Z is alkyl of 1 to 4 carbon atoms; R is hydrogen, alkyl of 1 to 4 carbon atoms, or alkenyl of 2 to 4 carbon atoms; each of R 2 and R 3 , independent of the other, is alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms or cycloalkyl of 3 to 10 carbon atoms; R 4 is hydrogen, alkyl of 1 to 6 carbon atoms or Z--O--Y-- wherein Z and Y are as defined above; and X is phenyl or naphthyl, unsubstituted or substituted by one or two members independently selected from the group consisting of halo, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, trifluoromethyl, cyano, nitro, azido, phenyl, hydroxy, amino, alkylamino of 1 to 4 carbon atoms, dialkylamino of 1 to 4 carbon atoms in each alkyl group, carbalkoxy of 1 to 4 carbon atoms in the alkoxy moiety, acetamido, propionamido, acetoxy, propionyloxy, methyl-S(O) m or ethyl-S(O) m in which m is 0, 1 or 2.
Claim 2
Dependent Claim
210 words
A compound selected from the group consisting of a dihydropyridine of the formula: ##SPC31## and the pharmaceutically acceptable nontoxic salts thereof, wherein Y is alkylene of 1 to 4 carbon atoms; Z is alkyl of 1 to 4 carbon atoms; R is hydrogen, alkyl of 1 to 4 carbon atoms, or alkenyl of 2 to 4 carbon atoms; each of R 2 and R 3 , independent of the other, is alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms or cycloalkyl of 3 to 10 carbon atoms; R 4 is hydrogen, alkyl of 1 to 6 carbon atoms or Z--O--Y-- wherein Z and Y are as defined above; and X is phenyl or naphthyl, unsubstituted or substituted by one or two members independently selected from the group consisting of halo, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, trifluoromethyl, cyano, nitro, azido, phenyl, hydroxy, amino, alkylamino of 1 to 4 carbon atoms, dialkylamino of 1 to 4 carbon atoms in each alkyl group, carbalkoxy of 1 to 4 carbon atoms in the alkoxy moiety, acetamido, propionamido, acetoxy, propionyloxy, methyl-S(O) m or ethyl-S(O) m in which m is 0, 1 or 2.
Claim 3
Dependent Claim
14 words
A compound according to claim 1 wherein R is hydrogen; and Y is methylene.
Claim 4
Dependent Claim
43 words
A compound according to claim 2 wherein X is phenyl or phenyl substituted by one or two members selected from the group consisting of halo, methyl, ethyl, methoxy, ethoxy, trifluoromethyl, nitro, azido, hydroxy, amido, methylamino, ethylamino, dimethylamino, diethylamino, carbomethoxy, carbethoxy, methylthio or methylsulfonyl.
Claim 5
Dependent Claim
37 words
A compound according to claim 3 wherein Z is methyl, ethyl, propyl or isopropyl; each of R 2 and R 3 are independently methyl or ethyl; and R 4 is methyl, ethyl, propyl, isopropyl, methoxymethyl or ethoxymethyl.
Claim 6
Dependent Claim
12 words
A compound according to claim 1 which is 2-ethoxymethyl-6-methyl-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester.
Claim 7
Dependent Claim
12 words
A compound according to claim 1 which is 2-ethoxymethyl-6-methyl-4-(3'-(3'-iodophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester.
Claim 8
Dependent Claim
12 words
A compound according to claim 1 which is 2-ethoxymethyl-6-methyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester.
Claim 9
Dependent Claim
12 words
A compound according to claim 1 which is 2-ethoxymethyl-6-methyl-4-(2'-(2'-chlorophenyl-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester.
Claim 10
Dependent Claim
12 words
A compound according to claim 1 which is 2-ethoxymethyl-6-methyl-4-(3'-fluoro-4'-methoxyphenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester.
Claim 11
Dependent Claim
15 words
A compound according to claim 1 which is 2-methoxymethyl-6-methyl-4-(2'-nitrophenyl)-1,4-dihydropyridine-3,5-carboxylic acid ethyl ester-3,5-dicarboxylic acid methyl ester.
Claim 12
Dependent Claim
12 words
A compound according to claim 1 which is 2-ethoxymethyl-6-methyl-4-(2'-trifluoromethylphenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester.
Claim 13
Dependent Claim
12 words
A compound according to claim 1 which is 2-ethoxymethyl-6-ethyl-4-(3'-cyanophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester.
Claim 14
Dependent Claim
12 words
A compound according to claim 1 which is 2,6-dimethoxymethyl-4-(2'-chlorophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid ethyl ester.
Claim 15
Dependent Claim
12 words
A compound according to claim 1 which is 2,6-dimethoxymethyl-4-(2'-trifluoromethylphenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester.
Claim 16
Dependent Claim
12 words
A compound according to claim 1 which is 2,6-(diethoxymethyl)-4-(2'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester.
Claim 17
Dependent Claim
12 words
A compound according to claim 1 which is 2-methoxymethyl-6-methyl-4-(4'-methylsulphonylphenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester.
Claim 18
Dependent Claim
15 words
A compound according to claim 1 which is 2-methoxymethyl-6-methyl-4-(3'-carbethoxyphenyl)-1,4-dihydropyridine-3-carboxylic acid methyl ester-5-carboxylic acid ethyl ester.
Claim 19
Dependent Claim
12 words
A compound according to claim 1 which is 2,6-dimethoxymethyl-4-(4'-methylmercaptophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester.
Claim 20
Dependent Claim
12 words
A compound according to claim 1 which is 2,6-dimethoxymethyl-4-(3'-methoxy-4'-hydroxyphenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester.
Claim 21
Dependent Claim
12 words
A compound according to claim 1 which is 1-methyl-2,6-dimethoxymethyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester.
References Cited (Backward Citations)
US3917620A
Cited
US3923818A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-07-27 | 1980-01-26 | 1980-07-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-07-27 | 1984-01-26 | 1984-07-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-07-27 | 1988-01-26 | 1988-07-27 | $7700.00 | Window Closed / Lapsed |