US4728653A
Expired / Lapsed
US
⏱️ 0.0 years remaining
6-heteroaryl quinolone inotropic agents
Assignee: Pfizer Inc
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Filing: 1986-03-26
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Granted: 1988-03-01
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Expires: 2006-03-26
Abstract
Abstract A series of novel heterocyclic-substituted 2-(1H)-quinolone compounds have been prepared, including the 3,4-dihydro derivatives thereof, wherein the heterocyclic ring moiety is a pyrrolyl, imidazolyl, pyrazolyl, triazolyl or tetrazolyl group attached by a nitrogen atom of said group to the 5-, 6-, 7- or 8-positions of the quinolone ring. These particular compounds are useful in therapy as highly potent inotropic agents and therefore, are of value in the treatment of various cardiac conditions. Preferred member compounds include 6-(2,4-dimethylimidazol-1-yl)-8-methyl-2-(1H)-quinolone, 6-(2,4-dimethyl-5-nitroimadazol-1-yl)-8-methyl-2-(1H)-quinolone, 8-methyl-6-(tetrazol-1-yl)-2-(1H)-quinolone, 8-methyl-6-(1,2,4-triazol-4-yl)-2-(1H)-quinolone, and 6-(4-cyano-2-methylimidazol-1-yl)-8-methyl-2-(1H)-quinolone, respectively. Methods for preparing these compounds from known starting materials are provided.
Inventors
- 👤 Simon F. Campbell
- 👤 David A. Roberts
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 06:40
CPC Classifications
C; C07; C07D; C07D257/00; C07D257/02; C07D257/04; C07D231/00; C07D231/02; C07D231/10; C07D231/12; C07D233/00; C07D233/54; C07D233/56; C07D249/00; C07D249/02; C07D249/08; C07D401/00; C07D401/02; C07D401/04
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
116 words
A quinolone compound of the formula: ##STR157## or a pharmaceutically acceptable salt thereof, wherein (a) "Het" is attached to the 6-position of the quinolone ring and is an imidazolyl, pyrazolyl, triazolyl or tetrazolyl group attached by a nitrogen atom of said group to the 6-position of the quinolone ring, said groups being optionally substituted on the available ring carbon atoms with up to three substituents each independently selected from C 1 -C 4 alkyl, trifluoromethyl, halo, cyano, nitro or amino; and (b) R is attached to the 8-position of the quinolone ring and is hydrogen, C 1 -C 4 alkyl, trifluoromethyl or halo; and the dashed line between the 3- and 4-positions represents an optional bond.
Claim 2
Dependent Claim
116 words
A quinolone compound of the formula: ##STR157## or a pharmaceutically acceptable salt thereof, wherein (a) "Het" is attached to the 6-position of the quinolone ring and is an imidazolyl, pyrazolyl, triazolyl or tetrazolyl group attached by a nitrogen atom of said group to the 6-position of the quinolone ring, said groups being optionally substituted on the available ring carbon atoms with up to three substituents each independently selected from C 1 -C 4 alkyl, trifluoromethyl, halo, cyano, nitro or amino; and (b) R is attached to the 8-position of the quinolone ring and is hydrogen, C 1 -C 4 alkyl, trifluoromethyl or halo; and the dashed line between the 3- and 4-positions represents an optional bond.
Claim 3
Dependent Claim
20 words
A compound as claimed in claim 1 wherein there is a double bond in the 3,4-positions of the quinolone ring.
Claim 4
Dependent Claim
46 words
A compound as claimed in claim 1 wherein (a) "Het" is an imidazol-1-yl, 2-methylimidazol-1-yl, 4-methylimidazol-1-yl, 5-methylimidazol-1-yl, 1,2,4-triazol-1-yl, 2,4-dimethylimidazol-1-yl, pyrazol-1-yl, 4-trifluoromethylimidazol-1-yl, tetrazol-1-yl, 3,5-dimethyl-1,2,4-triazol-1-yl, 3,5-dimethyl-1,2,4-triazol-4-yl, tetrazol-2-yl, 1,2,4-triazol-4-yl, 2,4-dimethyl-5-nitroimidazol-1-yl, 5-nitro-4-methylimidazol-1-yl, 5-amino-2,4-dimethylimidazol-1-yl, 5-bromo-2,4-dimethylimidazol-1-yl, 5-iodo-2,4-dimethylimidazol-1-yl, 5-cyano-2,4-dimethylimidazol-1-yl, 2-cyano-4-methylimidazol-1-yl, 4-cyano-2-methylimidazol-1-yl, 2-iodo-4-methylimidazol-1-yl or 4-iodo-2-methylimidazol-1-yl group; and (b) R is hydrogen, methyl, trifuloromethyl or bromine.
Claim 5
Dependent Claim
20 words
A compound as claimed in claim 3 wherein there is a double bond in the 3,4-positions of the quinolone ring.
Claim 6
Dependent Claim
36 words
A compound as claimed in claim 3 wherein (a) "Het" is a 2,4-dimethylimidazol-1-yl, 2,4-dimethyl-5-nitroimidazol-1-yl, tetrazol-1-yl or 1,2,4-triazol-4-yl group; (b) R is methyl, and (c) there is a double bond in the 3,4-positions of the quinolone ring.
Claim 7
Dependent Claim
1 words
6-(2,4-Dimethylimidazol-1-yl)-8-methyl-2-(1H)-quinolone.
Claim 8
Dependent Claim
1 words
6-(2,4-Dimethylimidazol-1-yl)-8-methyl-2-(1H)-quinolone.
Claim 9
Dependent Claim
1 words
6-(4-Cyano-2-methylimidazol-1-yl)-8-methyl-2-(1H)-quinolone.
Claim 10
Dependent Claim
1 words
6-(4-Cyano-2-methylimidazol-1-yl)-8-methyl-2-(1H)-quinolone.
Claim 11
Dependent Claim
24 words
A pharmaceutical composition comprising a pharmaceutically acceptable carrier or diluent and an effective cardiac stimulating amount of a compound as claimed in claim 1.
Claim 12
Dependent Claim
11 words
The composition according to claim 8 wherein the compound is 6-(2,4-dimethylimidazol-1-yl)-8-methyl-2-(1H)-quinolone.
Claim 13
Dependent Claim
11 words
The composition according to claim 8 wherein the compound is 6-(2,4-dimethyl-5-nitroimidazol-1-yl)-8-methyl-2-(1H)-quinolone.
Claim 14
Dependent Claim
11 words
The composition according to claim 8 wherein the compound is 8-methyl-6-(tetrazol-1-yl)-2-(1H)-quinolone.
Claim 15
Dependent Claim
11 words
The composition according to claim 8 wherein the compound is 8-methyl-6-(1,2,4-triazol-4-yl)-2-(1H)-quinolone.
Claim 16
Dependent Claim
11 words
The composition according to claim 8 wherein the compound is 6-(4-cyano-2-methylimidazol-1-yl)-8-methyl-2-(1H)-quinolone.
Claim 17
Dependent Claim
36 words
A method for stimulating cardiac activity in the treatment of a subject afflicted with congestive heart failure, which comprises administering to said subject an effective cardiac stimulating amount of a compound as claimed in claim 1.
Claim 18
Dependent Claim
12 words
The method as claimed in claim 14 wherein said compound is 6-(2,4-dimethylimidazol-1-yl)-8-methyl-2-(1H)-quinolone.
Claim 19
Dependent Claim
12 words
The method as claimed in claim 14 wherein said compound is 6-(2,4-dimethyl-5-nitroimidazol-1-yl)-8-methyl-2-(1H)-quinolone.
Claim 20
Dependent Claim
12 words
The method as claimed in claim 14 wherein said compound is 8-methyl-6-(tetrazol-1-yl)-2-(1H)-quinolone.
Claim 21
Dependent Claim
12 words
The method as claimed in claim 14 wherein said compound is 8-methyl-6-(1,2,4-triazol-4-yl)-2-(1H)-quinolone.
Claim 22
Dependent Claim
12 words
The method as claimed in claim 14 wherein said compound is 6-(4-cyano-2-methylimidazol-1-yl)-8-methyl-2-(1H)-quinolone.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1991-03-01 | 1991-08-31 | 1992-03-01 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-03-01 | 1995-08-31 | 1996-03-01 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-03-01 | 1999-08-31 | 2000-03-01 | $7700.00 | Window Closed / Lapsed |