Patent US4044141A successfully refreshed from Google Patents.
US4044141A
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1,4-Dihydropyridines
Assignee: Bayer AG
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Filing: 1976-02-02
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Granted: 1977-08-23
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Expires: 1996-02-02
Abstract
Abstract 1,4-Dihydropyridines characterized by a carbo(arylalkoxy) group in the 5-position, an aryl group in the 4-position and a alkanoyl or carbalkoxy group in the 3-position and further optionally substituted in the 1,2 and 6-positions are coronary dilating, spasmolytic and hypotensive agents. The compounds, of which 2,6-dimethyl-3-carbomethoxy-4-(2-nitrophenyl)-5-carbobenzoxy-1,4-dihyd ropyridine is a representative embodiment, are prepared through the reaction of an ylidene- beta -dicarbonyl compound, which may be generated in situ from the corresponding beta -dicarbonyl compound and an aldehyde, and an enaminocarboxylic acid ester, which may also be generated in situ from a beta -dicarbonyl compound and an amine.
Inventors
- 👤 Friedrich Bossert
- 👤 Egbert Wehinger
- 👤 Kurt Stoepel
- 👤 Wulf Vater
- 👤 Stanislav Kazda
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 18:57
CPC Classifications
C; C07; C07D; C07D401/00; C07D401/02; C07D401/04; A; A61; A61P; A61P9/00; A61P9/08; A61P9/12; C07D211/00; C07D211/04; C07D211/80; C07D211/84; C07D211/90
Claims Analysis
Total Claims: 23
Claim 1
Independent Claim
275 words
A compound of the formula: ##STR59## wherein is a phenyl group, unsubstituted or substituted with from one to three sterically permissible substituents selected from the group consisting of lower alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, halo, trifluoromethyl, nitro, azido, cyano, hydroxy, amino, carbo(lower alkoxy) wherein lower alkoxy contains from 1 to 6 carbon atoms, carbamido, sulfonamido, (lower alkyl)thio of 1 to 6 carbon atoms, (lower alkyl)sulfinyl of 1 to 6 carbon atoms or (lower alkyl)sulfonyl of 1 to 6 carbon atoms, or naphthyl; R 1 is lower alkoxy of 1 to 6 carbon atoms, cycloalkoxy of 3 to 7 carbon atoms or (lower alkoxy)lower alkoxy wherein each lower alkoxy contains 1 to 6 carbon atoms; each of R 2 and R 4 , independently of the other is hydrogen or lower alkyl of 1 to 6 carbon atoms; R 3 is hydrogen, lower alkyl of 1 to 6 carbon atoms or (lower alkoxy)lower alkyl wherein each of lower alkoxy and lower alkyl contain 1 to 6 carbon atoms; R 5 is a phenyl, phenoxy or phenylthio group unsubstituted or substituted with from one to three sterically permissible substituents selected from the group consisting of lower alkyl of 1 to 6 carbon atoms, lower alkoxy of 1 to 6 carbon atoms, halo, trifluoromethyl, hydroxy, amino, di(lower alkyl)amino wherein each lower alkyl contains 1 to 6 carbon atoms, nitro, cyano, carbamido, sulfonamido, (lower alkyl)thio of 1 to 6 carbon atoms, (lower alkyl)sulfinyl of 1 to 6 carbon atoms, a (lower alkyl) sulfonyl of 1 to 6 carbon atoms; and X is lower alkylene of 1 to 6 carbon atoms.
Claim 2
Dependent Claim
275 words
A compound of the formula: ##STR59## wherein is a phenyl group, unsubstituted or substituted with from one to three sterically permissible substituents selected from the group consisting of lower alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, halo, trifluoromethyl, nitro, azido, cyano, hydroxy, amino, carbo(lower alkoxy) wherein lower alkoxy contains from 1 to 6 carbon atoms, carbamido, sulfonamido, (lower alkyl)thio of 1 to 6 carbon atoms, (lower alkyl)sulfinyl of 1 to 6 carbon atoms or (lower alkyl)sulfonyl of 1 to 6 carbon atoms, or naphthyl; R 1 is lower alkoxy of 1 to 6 carbon atoms, cycloalkoxy of 3 to 7 carbon atoms or (lower alkoxy)lower alkoxy wherein each lower alkoxy contains 1 to 6 carbon atoms; each of R 2 and R 4 , independently of the other is hydrogen or lower alkyl of 1 to 6 carbon atoms; R 3 is hydrogen, lower alkyl of 1 to 6 carbon atoms or (lower alkoxy)lower alkyl wherein each of lower alkoxy and lower alkyl contain 1 to 6 carbon atoms; R 5 is a phenyl, phenoxy or phenylthio group unsubstituted or substituted with from one to three sterically permissible substituents selected from the group consisting of lower alkyl of 1 to 6 carbon atoms, lower alkoxy of 1 to 6 carbon atoms, halo, trifluoromethyl, hydroxy, amino, di(lower alkyl)amino wherein each lower alkyl contains 1 to 6 carbon atoms, nitro, cyano, carbamido, sulfonamido, (lower alkyl)thio of 1 to 6 carbon atoms, (lower alkyl)sulfinyl of 1 to 6 carbon atoms, a (lower alkyl) sulfonyl of 1 to 6 carbon atoms; and X is lower alkylene of 1 to 6 carbon atoms.
Claim 3
Dependent Claim
88 words
A compound according to claim 1 wherein R is phenyl or phenyl unsubstituted or substituted with lower alkyl, lower alkoxy, halo, trifluoromethyl, nitro, azido or cyano; R 1 is lower alkoxy, cycloalkoxy or (lower alkoxy)lower alkoxy; each of R 2 and R 4 is methyl; R 3 is hydrogen or methyl; R 5 is a phenyl or phenoxy group unsubstituted or substituted with one to three sterically permissible substituents selected from the group consisting of lower alkyl, lower alkoxy, halo, trifluoromethyl and nitro; and X is lower alkylene.
Claim 4
Dependent Claim
65 words
A compound according to claim 1 wherein R is phenyl, nitrophenyl, trifluoromethylphenyl, chlorophenyl or cyanophenyl; R 1 is methoxy, ethoxy, isopropoxy, isobutoxy, cyclopentoxy, cyclohexoxy or methoxyethoxy; each of R 2 and R 4 is methyl; R 3 is hydrogen or methyl; R 5 is phenoxy, phenyl, chlorophenyl, dichlorophenyl, methylphenyl, t.-butylphenyl, methoxyphenyl, dimethoxyphenyl, trimethoxyphenyl, triflouoromethylphenyl or nitrophenyl; and X is methylene, ethylene, ethylidene, trimethylene or 1,2-propylene.
Claim 5
Dependent Claim
42 words
A compound according to claim 1 wherein R is phenyl or nitrophenyl; R 1 is methoxy or isopropoxy; each of R 2 and R 4 is methyl; R 3 is hydrogen; R 5 is phenyl, chlorophenyl or trifluoromethylphenyl; and X is methylene.
Claim 6
Dependent Claim
44 words
A compound according to claim 1 wherein R is 2-nitrophenyl or 3-nitrophenyl; R 1 is methoxy or isopropoxy; each of R 2 and R 4 is methyl; R 3 is hydrogen; R 5 is phenyl, 3-chlorophenyl, 4-chlorophenyl, 3-trifluoromethylphenyl or 4-trifluoromethylphenyl; and X is methylene.
Claim 7
Dependent Claim
12 words
The compound according to claim 1 which is 2,6-dimethyl-3-methoxycarbonyl-4-(2'-nitrophenyl)-1,4-dihydropyridine-5-carboxylic acid benzyl ester.
Claim 8
Dependent Claim
12 words
The compound according to claim 1 which is 2,6-dimethyl-3-methoxycarbonyl-4-(2'-nitrophenyl)-1,4-dihydropyridine-5-carboxylic acid 4-chlorobenzyl ester.
Claim 9
Dependent Claim
12 words
The compound according to claim 1 which is 2,6-dimethyl-3-methoxycarbonyl-4-(2'-nitrophenyl)-1,4-dihydropyridine-5-carboxylic acid 3,4-dichlorobenzyl ester.
Claim 10
Dependent Claim
12 words
The compound according to claim 1 which is 2,6-dimethyl-3-methoxycarbonyl-4-(2'-nitrophenyl)-1,4-dihydropyridine-5-carboxylic acid 4-methylbenzyl ester.
Claim 11
Dependent Claim
12 words
The compound according to claim 1 which is 2,6-dimethyl-3-methoxycarbonyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-5-carboxylic acid 3-chlorobenzyl ester.
Claim 12
Dependent Claim
12 words
The compound according to claim 1 which is 2,6-dimethyl-3-isopropoxycarbonyl-4(3'-nitrophenyl)-1,4-dihydropyridine-5-carboxylic acid benzyl ester.
Claim 13
Dependent Claim
12 words
The compound according to claim 1 which is 2,6-dimethyl-3-isopropoxycarbonyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-5-carboxylic acid 4-chlorobenzyl ester.
Claim 14
Dependent Claim
12 words
The compound according to claim 1 which is 2,6-dimethyl-3-isopropoxycarbonyl-4(3'-nitrophenyl)-1,4-dihydropyridine-5-carboxylic acid 3,4-dichlorobenzyl ester.
Claim 15
Dependent Claim
12 words
The compound according to claim 1 which is 2,6-dimethyl-3-isopropoxycarbonyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-5-carboxylic acid 3-chlorobenzyl ester.
Claim 16
Dependent Claim
12 words
The compound according to claim 1 which is 2,6-dimethyl-3-isopropoxycarbonyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-5-carboxylic acid 2-chlorobenzyl ester.
Claim 17
Dependent Claim
12 words
The compound according to claim 1 which is 2,6-dimethyl-3-(2-methoxyethyloxy)-carbonyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-5-carboxylic acid benzyl ester.
Claim 18
Dependent Claim
12 words
The compound according to claim 1 which is 2,6-dimethyl-3-(2-methoxyethyloxy)-carbonyl-4-(3'-nitroethyl)-5-carboxylic acid 1-phenylethyl ester.
Claim 19
Dependent Claim
12 words
The compound according to claim 1 which is 2,6-dimethyl-3-(2-methoxyethyloxy)-carbonyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-5-carboxylic acid 1-(4-chlorophenyl)-ethyl ester.
Claim 20
Dependent Claim
12 words
The compound according to claim 1 which is 2,6-dimethyl-3-methoxycarbonyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-5-carboxylic acid 4-trifluoromethylbenzyl ester.
Claim 21
Dependent Claim
12 words
The compound according to claim 1 which is 2,6-dimethyl-3-isopropoxycarbonyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-5-carboxylic acid 4-trifluoromethylbenzyl ester.
Claim 22
Dependent Claim
33 words
The method of producing coronary dilating, spasmolytic and hypotensive effects in humans and other animals which comprises orally, parenterally or perlingually administering thereto an effective amount of a compound according to claim 1.
Claim 23
Dependent Claim
37 words
An oral, parenteral or perlingual pharmaceutical composition for producing coronary dilating, spasmolytic and hypotensive effects in humans or other animals comprising an effective amount of a compound according to claim 1 in combination with a pharmaceutical carrier.
References Cited (Backward Citations)
US3996234A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-08-22 | 1981-02-21 | 1981-08-23 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-08-22 | 1985-02-21 | 1985-08-23 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-08-22 | 1989-02-21 | 1989-08-23 | $7700.00 | Window Closed / Lapsed |