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US4772612A
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Circulation-active 1,4-dihydropyridines
Assignee: Bayer AG
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Filing: 1986-06-03
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Granted: 1988-09-20
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Expires: 2006-06-03
Abstract
Abstract Novel circulation active dihydropyridines of the formula ##STR1## in which X is CO, SO 2 or CONH, R 4 is H, OH, alkyl, halogen, acyloxy, alkoxyalkoxy, aralkyloxy, or together with R 5 forms a heterocyclic ring, and the other radicals are conventional in the dihydropyridine art, and pharmaceutically acceptable salts thereof.
Inventors
- 👤 Siegfried Goldmann
- 👤 Jurgen Stoltefuss
- 👤 Gerhard Franckowiak
- 👤 Rainer Gross
- 👤 Matthias Schramm
- 👤 Gunter Thomas
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 14:29
CPC Classifications
C; C07; C07D; C07D409/00; C07D409/02; C07D409/12; A; A61; A61P; A61P9/00; A61P9/04; A61P9/08; A61P9/12; C07D211/00; C07D211/04; C07D211/80; C07D211/84; C07D211/90; C07D491/00; C07D491/02; C07D491/04
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
246 words
A dihydropyridine exhibiting a positive inotropic effect of the formula ##STR78## in which R 1 represents straight-chain, branched or cyclic alkyl or alkenyl each of which has up to 8 C atoms and is optionally interrupted in the chain by one oxygen or sulphur atom and is optionally substituted by phenyl, cyano, one or more fluorine atoms or N-benzyl-N-methylamino, R 2 represents methyl, hydroxymethyl or ethyl, or represents cyano, R 3 represents hydrogen, or represents methyl or ethyl, R 4 represents hydrogen or hydroxyl, represents methyl or ethyl, represents chlorine or bromine, or represents --OOC--CH 3 R 5 represents nitro, or represents CO 2 R 9 , wherein R 9 and R 4 together denote a direct bond, X represents >C═O, --SO 2 -- or --CO--NH--, R 6 represents straight-chain, branched or cyclic alkyl or alkenyl each of which has up to 16 C atoms and is optionally substituted by phenyl or one or more fluorine or chlorine atoms, represents thienyl, furyl or pyridyl which is optionally substituted by chlorine or methyl, or represents phenyl or naphthyl each of which optionally carries up to 3 identical or different substituents from the group consisting of fluorine, chlorine, nitro, C 1 -C 4 -alkyl, methoxy, methylthio, trifluoromethoxy, trifluoromethylthio, trifluoromethyl or acetylamino, or represents the radical ##STR79## and R 7 and R 8 are identical or different and represent hydrogen, represent C 1 -C 4 -alkoxy, represent chlorine, represent C 1 -C 4 -alkyl, represent nitro, or represent trifluoromethyl.
Claim 2
Dependent Claim
246 words
A dihydropyridine exhibiting a positive inotropic effect of the formula ##STR78## in which R 1 represents straight-chain, branched or cyclic alkyl or alkenyl each of which has up to 8 C atoms and is optionally interrupted in the chain by one oxygen or sulphur atom and is optionally substituted by phenyl, cyano, one or more fluorine atoms or N-benzyl-N-methylamino, R 2 represents methyl, hydroxymethyl or ethyl, or represents cyano, R 3 represents hydrogen, or represents methyl or ethyl, R 4 represents hydrogen or hydroxyl, represents methyl or ethyl, represents chlorine or bromine, or represents --OOC--CH 3 R 5 represents nitro, or represents CO 2 R 9 , wherein R 9 and R 4 together denote a direct bond, X represents >C═O, --SO 2 -- or --CO--NH--, R 6 represents straight-chain, branched or cyclic alkyl or alkenyl each of which has up to 16 C atoms and is optionally substituted by phenyl or one or more fluorine or chlorine atoms, represents thienyl, furyl or pyridyl which is optionally substituted by chlorine or methyl, or represents phenyl or naphthyl each of which optionally carries up to 3 identical or different substituents from the group consisting of fluorine, chlorine, nitro, C 1 -C 4 -alkyl, methoxy, methylthio, trifluoromethoxy, trifluoromethylthio, trifluoromethyl or acetylamino, or represents the radical ##STR79## and R 7 and R 8 are identical or different and represent hydrogen, represent C 1 -C 4 -alkoxy, represent chlorine, represent C 1 -C 4 -alkyl, represent nitro, or represent trifluoromethyl.
Claim 3
Dependent Claim
22 words
A compound according to claim 1, wherein such compound is methyl 1,4-dihydro-2,6-dimethyl-5-nitro-4-(2-p-tolylsulphonyloxy)phenylpyridine-3-carboxylate of the formula ##STR80## or a pharmaceutically acceptable salt thereof.
Claim 4
Dependent Claim
22 words
A compound according to claim 1, wherein such compound is methyl 1,2-dimethyl-5-oxo-4-(2-phenylsulphonyloxy)phenyl-1,4,5,7-tetrahydrofuro[3,4-b]pyridine-3-carboxylate of the formula ##STR81## or a pharmaceutically acceptable salt thereof.
Claim 5
Dependent Claim
22 words
A compound according to claim 1, wherein such compound is ethyl 4-(2-benzoyloxy-phenyl)-1,4-dihydro-2,6-dimethyl-5-nitro-pyridine-3-carboxylate of the formula ##STR82## or a pharmaceutically acceptable salt thereof.
Claim 6
Dependent Claim
151 words
A compound according to claim 1, in which R 1 represents straight-chain, branched or cyclic alkyl or alkenyl each of which has up to 8 C atoms and is optionally interrupted in the chain by one oxygen atom and is optionally substituted by phenyl or fluorine, R 2 represents methyl, hydroxymethyl or cyano, R 4 represents hydrogen, hydroxyl, chlorine, bromine, or --OOC--CH 3 , R 6 represents straight-chain, branched or cyclic alkyl or alkenyl each of which has up to 12 C atoms and is optioally substituted by phenyl or one or more fluorine or chlorine atoms, represents thienyl or pyridyl which is optionally substituted by chlorine or methyl, or represents phenyl or naphthyl each of which optionally carries up to 3 identical or different substituents from the group consisting of fluorine, chlorine, nitro, C 1 -C 4 -alkyl, methoxy, methylthio, trifluoromethoxy, trifluoromethylthio, trifluoromethyl or acetylamino, or represents the radical ##STR83##
Claim 7
Dependent Claim
22 words
A circulation active composition comprising a positive inotropic effective amount of a compound or salt according to claim 1 and a diluent.
Claim 8
Dependent Claim
19 words
A unit dose of a composition according to claim 6 in the form of a tablet, capsule or ampule.
Claim 9
Dependent Claim
32 words
A method of improving the circulation of a patient in need thereof which comprises administering to said patient a positive inotropic effective amount of a compound or salt according to claim 1.
Claim 10
Dependent Claim
23 words
The method according to claim 8, wherein such compound is methyl 1,4-dihydro-2,6-dimethyl-5-nitro-4-(2-p-tolylsulphonyloxy)phenylpyridine-3-carboxylate, methyl 1,2-dimethyl-5-oxo-4-(2-phenylsulphonyloxy)phenyl-1,4,5,7-tetrahydrofuro[3,4-b]pyridine-3-carboxylate or ethyl 4-(2-benzoyloxy-phenyl)-1,4-dihydro-2,6-dimethyl-5-nitro-pyridine-3-carboxylate, or a pharmaceutically acceptable salt thereof.
References Cited (Backward Citations)
EP0088274A1
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1991-09-20 | 1992-03-21 | 1992-09-20 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-09-20 | 1996-03-21 | 1996-09-20 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-09-20 | 2000-03-21 | 2000-09-20 | $7700.00 | Window Closed / Lapsed |