US4698353A
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Cardiotonic heterocyclic oxazolones
Assignee: Aventis Pharmaceuticals Inc
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Filing: 1985-11-13
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Granted: 1987-10-06
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Expires: 2005-11-13
Abstract
Abstract Heterocyclic oxazolones enhance myocardial contractile force and cardiac function and are used as cardiotonics in the treatment of heart failure.
Inventors
- 👤 Richard A. Schnettler
- 👤 Winton D. Jones, Jr.
- 👤 George P. Claxton
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 05:31
CPC Classifications
C; C07; C07D; C07D413/00; C07D413/02; C07D413/04; A; A61; A61P; A61P9/00; A61P9/04
Claims Analysis
Total Claims: 24
Claim 1
Independent Claim
150 words
A heterocyclic oxazolone of the formula ##STR5## wherein Y is an oxygen or sulfur group; R 1 is a hydrogen or a (C 1 -C 5 ) alkyl group when R 2 is R; R 2 is a hydrogen or a (C 1 -C 5 ) alkyl group when R 1 is R; and R is a 2-, 3- or 4-pyridyl group optionally substituted with a hydroxy, halogen, (C 1 -C 5 ) alkyl, (C 1 -C 5 ) alkoxy, (C 1 -C 5 ) alkylthio, (C 1 -C 5 )alkylsulfinyl, (C 1 -C 5 )alkylsulfonyl, cyano, carboxy, carb(C 1 -C 5 )alkoxy, carbamido, (C 1 -C 5 )alkanoylamino, or imidazolyl group, or R is a 2- or 3-furanyl, 2- or 3-thienyl or 2- or 3-pyranyl group with the proviso that when either of R 1 or R 2 is a hydrogen, R cannot be a 2- or 3-thienyl group.
Claim 2
Dependent Claim
150 words
A heterocyclic oxazolone of the formula ##STR5## wherein Y is an oxygen or sulfur group; R 1 is a hydrogen or a (C 1 -C 5 ) alkyl group when R 2 is R; R 2 is a hydrogen or a (C 1 -C 5 ) alkyl group when R 1 is R; and R is a 2-, 3- or 4-pyridyl group optionally substituted with a hydroxy, halogen, (C 1 -C 5 ) alkyl, (C 1 -C 5 ) alkoxy, (C 1 -C 5 ) alkylthio, (C 1 -C 5 )alkylsulfinyl, (C 1 -C 5 )alkylsulfonyl, cyano, carboxy, carb(C 1 -C 5 )alkoxy, carbamido, (C 1 -C 5 )alkanoylamino, or imidazolyl group, or R is a 2- or 3-furanyl, 2- or 3-thienyl or 2- or 3-pyranyl group with the proviso that when either of R 1 or R 2 is a hydrogen, R cannot be a 2- or 3-thienyl group.
Claim 3
Dependent Claim
12 words
A heterocyclic oxazolone of claim 1 wherein Y is an oxygen group.
Claim 4
Dependent Claim
21 words
A heterocyclic oxazolone of claim 2 wherein R 1 or R 2 is a (C 1 -C 5 ) alkyl group.
Claim 5
Dependent Claim
17 words
A heterocyclic oxazolone of claim 2 wherein R is an optionally substituted 2-, 3- or 4-pyridyl group.
Claim 6
Dependent Claim
16 words
A heterocyclic oxazolone of claim 2 wherein R 1 is a methyl, ethyl or propyl group.
Claim 7
Dependent Claim
14 words
A heterocyclic oxazolone of claim 2 wherein R 2 is an unsubstituted pyridyl group.
Claim 8
Dependent Claim
16 words
A heterocyclic oxazolone of claim 6 wherein R 1 is a methyl, ethyl or propyl group.
Claim 9
Independent Claim
150 words
A method of treating heart failure in a patient in need thereof which comprises administering to the patient a cardiotonically effective amount of a heterocyclic oxazolone of the formula ##STR6## wherein Y is an oxygen or sulfur group; R 1 is a hydrogen or a (C 1 -C 5 ) alkyl group when R 2 is R; R 2 is a hydrogen or a (C 1 -C 5 ) alkyl group when R 1 is R; and R is a 2-, 3- or 4-pyridyl group optionally substituted with a hydroxy, halogen, (C 1 -C 5 ) alkyl, (C 1 -C 5 ) alkoxy, (C 1 -C 5 ) alkylthio, (C 1 -C 5 )alkylsulfinyl, (C 1 -C 5 )alkylsulfonyl, cyano, carboxy, carb(C 1 -C 5 )alkoxy, carbamido, (C 1 -C 5 )alkanoylamino, or imidazolyl group, or R is a 2- or 3-furanyl, 2- or 3-thienyl or 2- or 3-pyranyl group.
Claim 10
Independent Claim
150 words
A method of treating heart failure in a patient in need thereof which comprises administering to the patient a cardiotonically effective amount of a heterocyclic oxazolone of the formula ##STR6## wherein Y is an oxygen or sulfur group; R 1 is a hydrogen or a (C 1 -C 5 ) alkyl group when R 2 is R; R 2 is a hydrogen or a (C 1 -C 5 ) alkyl group when R 1 is R; and R is a 2-, 3- or 4-pyridyl group optionally substituted with a hydroxy, halogen, (C 1 -C 5 ) alkyl, (C 1 -C 5 ) alkoxy, (C 1 -C 5 ) alkylthio, (C 1 -C 5 )alkylsulfinyl, (C 1 -C 5 )alkylsulfonyl, cyano, carboxy, carb(C 1 -C 5 )alkoxy, carbamido, (C 1 -C 5 )alkanoylamino, or imidazolyl group, or R is a 2- or 3-furanyl, 2- or 3-thienyl or 2- or 3-pyranyl group.
Claim 11
Dependent Claim
11 words
A method of claim 8 wherein Y is an oxygen group.
Claim 12
Dependent Claim
20 words
A method of claim 9 wherein R 1 or R 2 is a (C 1 -C 5 ) alkyl group.
Claim 13
Dependent Claim
16 words
A method of claim 9 wherein R is an optionally substituted 2-, 3- or 4-pyridyl group.
Claim 14
Dependent Claim
15 words
A method of claim 9 wherein R 1 is a methyl, ethyl or propyl group.
Claim 15
Dependent Claim
13 words
A method of claim 9 wherein R 2 is an unsubstituted pyridyl group.
Claim 16
Dependent Claim
15 words
A method of claim 13 wherein R 1 is a methyl, ethyl or propyl group.
Claim 17
Independent Claim
150 words
A method of enhancing myocardial contractile force in a patient in need thereof which comprises administering to the patient an effective amount of an heterocyclic oxazolone of the formula ##STR7## wherein Y is an oxygen or sulfur group; R 1 is a hydrogen or a (C 1 -C 5 ) alkyl group when R 2 is R; R 2 is a hydrogen or a (C 1 -C 5 ) alkyl group when R 1 is R; and R is a 2-, 3- or 4-pyridyl group optionally substituted with a hydroxy, halogen, (C 1 -C 5 ) alkyl, (C 1 -C 5 ) alkoxy, (C 1 -C 5 ) alkylthio, (C 1 -C 5 )alkylsulfinyl, (C 1 -C 5 )alkylsulfonyl, cyano, carboxy, carb(C 1 -C 5 )alkoxy, carbamido, (C 1 -C 5 )alkanoylamino, or imidazolyl group, or R is a 2- or 3-furanyl, 2- or 3-thienyl or 2- or 3-pyranyl group.
Claim 18
Independent Claim
150 words
A method of enhancing myocardial contractile force in a patient in need thereof which comprises administering to the patient an effective amount of an heterocyclic oxazolone of the formula ##STR7## wherein Y is an oxygen or sulfur group; R 1 is a hydrogen or a (C 1 -C 5 ) alkyl group when R 2 is R; R 2 is a hydrogen or a (C 1 -C 5 ) alkyl group when R 1 is R; and R is a 2-, 3- or 4-pyridyl group optionally substituted with a hydroxy, halogen, (C 1 -C 5 ) alkyl, (C 1 -C 5 ) alkoxy, (C 1 -C 5 ) alkylthio, (C 1 -C 5 )alkylsulfinyl, (C 1 -C 5 )alkylsulfonyl, cyano, carboxy, carb(C 1 -C 5 )alkoxy, carbamido, (C 1 -C 5 )alkanoylamino, or imidazolyl group, or R is a 2- or 3-furanyl, 2- or 3-thienyl or 2- or 3-pyranyl group.
Claim 19
Dependent Claim
11 words
A method of claim 15 wherein Y is an oxygen group.
Claim 20
Dependent Claim
21 words
A heterocyclic oxazolone of claim 16 wherein R 1 or R 2 is a (C 1 -C 5 ) alkyl group.
Claim 21
Dependent Claim
16 words
A method of claim 16 wherein R is an optionally substituted 2-, 3- or 4-pyridyl group.
Claim 22
Dependent Claim
15 words
A method of claim 16 wherein R 1 is a methyl, ethyl or propyl group.
Claim 23
Dependent Claim
13 words
A method of claim 16 wherein R 2 is an unsubstituted pyridyl group.
Claim 24
Dependent Claim
15 words
A method of claim 20 wherein R 1 is a methyl, ethyl or propyl group.
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