US4526894A
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US
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Pharmaceutically active 4-hydroxy-3-benzoyl-2-quinolone derivatives
Assignee: Nippon Shinyaku Co Ltd
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Filing: 1983-06-21
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Granted: 1985-07-02
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Expires: 2003-06-21
Abstract
Abstract 4-Hydroxy-2-quinolone derivatives are useful for their anti-inflammatory, anti-allergenic, antitussive and expectorant activity. Pharmaceutical compositions containing said compounds and pharmaceutically acceptable salts thereof and methods of treating humans and animals are described herein.
Inventors
- 👤 Hiroshi Enomoto
- 👤 Tadatoshi Nomura
- 👤 Yoshiaki Aoyagi
- 👤 Shoichi Chokai
- 👤 Tatsuhiko Kono
- 👤 Masao Murase
- 👤 Kichiro Inoue
- 👤 Masahiro Adachi
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 18:50
CPC Classifications
C; C07; C07D; C07D215/00; C07D215/02; C07D215/16; C07D215/20; C07D215/22; A; A61; A61P; A61P11/00; A61P11/10; A61P11/14; A61P37/00; A61P37/08; A61P7/00; A61P7/02; C07D215/48
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
127 words
A compound of the formula (I): ##STR12## or a pharmaceutically acceptable salt thereof wherein R 1 , R 2 and R 3 are each hydrogen, alkyl of 1 to 8 carbon atoms, alkoxy of 1 to 5 carbon atoms, halo, nitro, cyano, halo lower alkyl of 1 to 3 carbon atoms or COOR 6 wherein R 6 is hydrogen or alkyl of 1 to 3 carbon atoms, and R 4 and R 5 are each hydrogen, alkyl of 1 to 8 carbon atoms, halo, nitro, cyano, halo lower alkyl of 1 to 3 carbon atoms or COOR 6 wherein R 6 is as above defined, provided that all of R 1 , R 2 , R 3 , R 4 and R 5 are not simultaneously hydrogen.
Claim 2
Dependent Claim
127 words
A compound of the formula (I): ##STR12## or a pharmaceutically acceptable salt thereof wherein R 1 , R 2 and R 3 are each hydrogen, alkyl of 1 to 8 carbon atoms, alkoxy of 1 to 5 carbon atoms, halo, nitro, cyano, halo lower alkyl of 1 to 3 carbon atoms or COOR 6 wherein R 6 is hydrogen or alkyl of 1 to 3 carbon atoms, and R 4 and R 5 are each hydrogen, alkyl of 1 to 8 carbon atoms, halo, nitro, cyano, halo lower alkyl of 1 to 3 carbon atoms or COOR 6 wherein R 6 is as above defined, provided that all of R 1 , R 2 , R 3 , R 4 and R 5 are not simultaneously hydrogen.
Claim 3
Dependent Claim
73 words
A compound according to claim 1 wherein R 1 , R 2 and R 3 are each hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert butyl, pentyl, hexyl, heptyl, octyl, methoxy, ethoxy, propoxy, isopropoxy, butoxy, tert butoxy, fluoro, chloro, bromo, iodo, nitro, cyano or trifluoromethyl and R 4 and R 5 are each hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, fluoro, chloro, bromo, iodo, nitro, cyano or trifluoromethyl.
Claim 4
Dependent Claim
80 words
A compound according to claim 1 wherein R 1 , R 2 and R 3 are each hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert butyl, methoxy, ethoxy, propoxy, isopropoxy, fluoro, chloro, bromo, nitro, cyano, trifluoromethyl or COOR 6 wherein R 6 is hydrogen, methyl, ethyl or propyl and R 4 and R 5 are each hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, fluoro, chloro, bromo, nitro, cyano, trifluoromethyl or COOR 6 wherein R 6 is as above defined.
Claim 5
Dependent Claim
14 words
A compound according to claim 1 in the form of a pharmaceutically acceptable salt.
Claim 6
Dependent Claim
157 words
A pharmaceutical composition useful for effecting anti-inflammatory, anti-allergenic, antitussive or expectorant action in humans and animals which comprises a therapeutically effective amount of a compound of the formula (I): ##STR13## or a pharmaceutically acceptable salt thereof wherein R 1 , R 2 and R 3 are each hydrogen, alkyl of 1 to 8 carbon atoms, alkoxy of 1 to 5 carbon atoms, halo, nitro, cyano, halo lower alkyl of 1 to 3 carbon atoms or COOR 6 wherein R 6 is hydrogen or alkyl of 1 to 3 carbon atoms, and R 4 and R 5 are each hydrogen, alkyl of 1 to 8 carbon atoms, halo, nitro, cyano, halo lower alkyl of 1 to 3 carbon atoms or COOR 6 wherein R 6 is as above defined, provided that all of R 1 , R 2 , R 3 , R 4 and R 5 are not simultaneously hydrogen, in combination with a pharmaceutically acceptable carrier.
Claim 7
Dependent Claim
157 words
A pharmaceutical composition useful for effecting anti-inflammatory, anti-allergenic, antitussive or expectorant action in humans and animals which comprises a therapeutically effective amount of a compound of the formula (I): ##STR13## or a pharmaceutically acceptable salt thereof wherein R 1 , R 2 and R 3 are each hydrogen, alkyl of 1 to 8 carbon atoms, alkoxy of 1 to 5 carbon atoms, halo, nitro, cyano, halo lower alkyl of 1 to 3 carbon atoms or COOR 6 wherein R 6 is hydrogen or alkyl of 1 to 3 carbon atoms, and R 4 and R 5 are each hydrogen, alkyl of 1 to 8 carbon atoms, halo, nitro, cyano, halo lower alkyl of 1 to 3 carbon atoms or COOR 6 wherein R 6 is as above defined, provided that all of R 1 , R 2 , R 3 , R 4 and R 5 are not simultaneously hydrogen, in combination with a pharmaceutically acceptable carrier.
Claim 8
Dependent Claim
73 words
A composition according to claim 5 wherein R 1 , R 2 and R 3 are each hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert butyl, pentyl, hexyl, heptyl, octyl, methoxy, ethoxy, propoxy, isopropoxy, butoxy, tert butoxy, fluoro, chloro, bromo, iodo, nitro, cyano or trifluoromethyl and R 4 and R 5 are each hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, fluoro, chloro, bromo, iodo, nitro, cyano or trifluoromethyl.
Claim 9
Dependent Claim
80 words
A composition according to claim 5 wherein R 1 , R 2 and R 3 are each hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert butyl, methoxy, ethoxy, propoxy, isopropoxy, fluoro, chloro, bromo, nitro, cyano, trifluoromethyl or COOR 6 wherein R 6 is hydrogen, methyl, ethyl or propyl and R 4 and R 5 are each hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, fluoro, chloro, bromo, nitro, cyano, trifluoromethyl or COOR 6 wherein R 6 is as above defined.
Claim 10
Dependent Claim
18 words
A composition according to claim 5 wherein the compound is in the form of a pharmaceutically acceptable salt.
Claim 11
Independent Claim
164 words
A method of effecting anti-inflammatory, anti-allergenic, antitussive and expectorant action in humans and animals which comprises administering to a human or animal in need thereof a therapeutically effective amount of a compound of the formula (I): ##STR14## or a pharmaceutically acceptable salt thereof wherein R 1 , R 2 and R 3 are each hydrogen, alkyl of 1 to 8 carbon atoms, alkoxy of 1 to 5 carbon atoms, halo, nitro, cyano, halo lower alkyl of 1 to 3 carbon atoms or COOR 6 wherein R 6 is hydrogen or alkyl of 1 to 3 carbon atoms, and R 4 and R 5 are each hydrogen, alkyl of 1 to 8 carbon atoms, halo, nitro, cyano, halo lower alkyl of 1 to 3 carbon atoms or COOR 6 wherein R 6 is as above defined, provided that all of R 1 , R 2 , R 3 , R 4 and R 5 are not simultaneously hydrogen, in combination with a pharmaceutically acceptable carrier.
Claim 12
Independent Claim
164 words
A method of effecting anti-inflammatory, anti-allergenic, antitussive and expectorant action in humans and animals which comprises administering to a human or animal in need thereof a therapeutically effective amount of a compound of the formula (I): ##STR14## or a pharmaceutically acceptable salt thereof wherein R 1 , R 2 and R 3 are each hydrogen, alkyl of 1 to 8 carbon atoms, alkoxy of 1 to 5 carbon atoms, halo, nitro, cyano, halo lower alkyl of 1 to 3 carbon atoms or COOR 6 wherein R 6 is hydrogen or alkyl of 1 to 3 carbon atoms, and R 4 and R 5 are each hydrogen, alkyl of 1 to 8 carbon atoms, halo, nitro, cyano, halo lower alkyl of 1 to 3 carbon atoms or COOR 6 wherein R 6 is as above defined, provided that all of R 1 , R 2 , R 3 , R 4 and R 5 are not simultaneously hydrogen, in combination with a pharmaceutically acceptable carrier.
Claim 13
Dependent Claim
73 words
A method according to claim 9 wherein R 1 , R 2 and R 3 are each hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert butyl, pentyl, hexyl, heptyl, octyl, methoxy, ethoxy, propoxy, isopropoxy, butoxy, tert butoxy, fluoro, chloro, bromo, iodo, nitro, cyano or trifluoromethyl and R 4 and R 5 are each hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, fluoro, chloro, bromo, iodo, nitro, cyano or trifluoromethyl.
Claim 14
Dependent Claim
80 words
A method according to claim 9 wherein R 1 , R 2 and R 3 are each hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert butyl, methoxy, ethoxy, propoxy, isopropoxy, fluoro, chloro, bromo, nitro, cyano, trifluoromethyl or COOR 6 wherein R 6 is hydrogen, methyl, ethyl or propyl and R 4 and R 5 are each hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, fluoro, chloro, bromo, nitro, cyano, trifluoromethyl or COOR 6 wherein R 6 is as above defined.
Claim 15
Dependent Claim
18 words
A method according to claim 9 wherein the compound is in the form of a pharmaceutically acceptable salt.
Claim 16
Dependent Claim
72 words
The compound according to claim 1 which is: 3-benzoyl-6-chloro-4-hydroxy-2-quinolone, 3-benzoyl-7-chloro-4-hydroxy-2-quinolone, 3-benzoyl-8-chloro-4-hydroxy-6-methyl-2-quinolone, 3-benzoyl-6,8-dichloro-4-hydroxy-2-quinolone, 3-benzoyl-4-hydroxy-7-nitro-2-quinolone, 3-benzoyl-6-cyano-4-hydroxy-2-quinolone, methyl 3-benzoyl-4-hydroxy-2-quinolone-5-carboxylate, methyl 3-benzoyl-4-hydroxy-2-quinolone-6-carboxylate, methyl 3-benzoyl-4-hydroxy-2-quinolone-7-carboxylate, 3-benzoyl-4-hydroxy-2-quinolone-5-carboxylic acid, 3-benzoyl-4-hydroxy-2-quinolone-6-carboxylic acid, 3-benzoyl-4-hydroxy-2-quinolone-7-carboxylic acid, 3-benzoyl-4-hydroxy-2-quinolone-8-carboxylic acid, 3-benzoyl-4-hydroxy-6-methyl-2-quinolone, 3-benzoyl-4-hydroxy-7-methyl-2-quinolone, 3-benzoyl-4-hydroxy-8-methyl-2-quinolone, 3-benzoyl-6,7-dimethyl-4-hydroxy-2-quinolone, 3-benzoyl-6,8-dimethyl-4-hydroxy-2-quinolone, 3-benzoyl-6-isopropyl-4-hydroxy-2-quinolone, 3-benzoyl-6-n-butyl-4-hydroxy-2-quinolone, 3-benzoyl-6-n-hexyl-4-hydroxy-2-quinolone, 4-hydroxy-3-(2-methoxybenzoyl)-2-quinolone, 3-(2-ethoxybenzoyl)-4-hydroxy-2-quinolone, 4-hydroxy-3-(2-isopropoxybenzoyl)-2-quinolone, 4-hydroxy-3-(4-methoxybenzoyl)-2-quinolone, 3-(2,4-dimethoxybenzoyl)-4-hydroxy-2-quinolone, 3-(3,4-dimethoxybenzoyl)-4-hydroxy-2-quinolone, 3-(3,4-dimethoxybenzoyl)-4-hydroxy-6-methyl-2-quinolone, 3-(3,4-dimethoxybenzoyl)-4-hydroxy-7-nitro-2-quinolone, 3-(3,4-dimethoxybenzoyl)-4-hydroxy-8-methyl-2-quinolone, 4-hydroxy-3-(2-isopropoxy-5-methoxybenzoyl)-2-quinolone, 4-hydroxy-3-(2,3,4-trimethoxybenzoyl)-2-quinolone, 4-hydroxy-3-(3,4,5-trimethoxybenzoyl)-2-quinolone, 4-hydroxy-3-(2,4,5-trimethoxybenzoyl)-2-quinolone, 3-(2-chlorobenzoyl)-4-hydroxy-2-quinolone, 3-(2-chlorobenzoyl)-4-hydroxy-6-isopropyl-2-quinolone, 3-(2-chlorobenzoyl)-6,8-dimethyl-4-hydroxy-2-quinolone, 3-(3-chlorobenzoyl)-4-hydroxy-2-quinolone, 3-(4-chlorobenzoyl)-4-hydroxy-2-quinolone, 3-(2-bromo-4-cyanobenzoyl)-4-hydroxy-2-quinolone, 3-(3,4-dichlorobenzoyl)-4-hydroxy-2-quinolone, 3-(2,5-dichloro-4-methylbenzoyl)-4-hydroxy-2-quinolone, 4-hydroxy-3-(2-methylbenzoyl)-2-quinolone, 4-hydroxy-3-(4-methylbenzoyl)-2-quinolone, 3-(2,4-dimethylbenzoyl)-4-hydroxy-2-quinolone, 4-hydroxy-3-(3-trifluoromethylbenzoyl)-2-quinolone, 4-hydroxy-3-(4-isopropylbenzoyl)-2-quinolone, 4-hydroxy-3-(4-n-pentylbenzoyl)-2-quinolone, 4-hydroxy-3-(4-nitrobenzoyl)-2-quinolone, 4-hydroxy-6-isopropyl-3-(4-nitrobenzoyl)-2-quinolone, 6,8-dimethyl-4-hydroxy-3-(4-nitrobenzoyl)-2-quinolone, 4-hydroxy-3-(4-methoxycarbonylbenzoyl)-2-quinolone, 3-(4-carboxybenzoyl)-4-hydroxy-2-quinolone, 4-hydroxy-6-methyl-3-(2,3,4-trimethoxybenzoyl-2-quinolone, 4-hydroxy-8-methyl-3-(2,3,4-trimethoxybenzoyl-2-quinolone, or 4-hydroxy-7-nitro-3-(2,3,4-trimethoxybenzoyl-2-quinolone.
Claim 17
Dependent Claim
74 words
A composition according to claim 5 wherein the compound is: 3-benzoyl-6-chloro-4-hydroxy-2-quinolone, 3-benzoyl-7-chloro-4-hydroxy-2-quinolone, 3-benzoyl-8-chloro-4-hydroxy-6-methyl-2-quinolone, 3-benzoyl-6,8-dichloro-4-hydroxy-2-quinolone, 3-benzoyl-4-hydroxy-7-nitro-2-quinolone, 3-benzoyl-6-cyano-4-hydroxy-2-quinolone, methyl 3-benzoyl-4-hydroxy-2-quinolone-5-carboxylate, methyl 3-benzoyl-4-hydroxy-2-quinolone-6-carboxylate, methyl 3-benzoyl-4-hydroxy-2-quinolone-7-carboxylate, 3-benzoyl-4-hydroxy-2-quinolone-5-carboxylic acid, 3-benzoyl-4-hydroxy-2-quinolone-6-carboxylic acid, 3-benzoyl-4-hydroxy-2-quinolone-7-carboxylic acid, 3-benzoyl-4-hydroxy-2-quinolone-8-carboxylic acid, 3-benzoyl-4-hydroxy-6-methyl-2-quinolone, 3-benzoyl-4-hydroxy-7-methyl-2-quinolone, 3-benzoyl-4-hydroxy-8-methyl-2-quinolone, 3-benzoyl-6,7-dimethyl-4-hydroxy-2-quinolone, 3-benzoyl-6,8-dimethyl-4-hydroxy-2-quinolone, 3-benzoyl-6-isopropyl-4-hydroxy-2-quinolone, 3-benzoyl-6-n-butyl-4-hydroxy-2-quinolone, 3-benzoyl-6-n-hexyl-4-hydroxy-2-quinolone, 4-hydroxy-3-(2-methoxybenzoyl)-2-quinolone, 3-(2-ethoxybenzoyl)-4-hydroxy-2-quinolone, 4-hydroxy-3-(2-isopropoxybenzoyl)-2-quinolone, 4-hydroxy-3-(4-methoxybenzoyl)-2-quinolone, 3-(2,4-dimethoxybenzoyl)-4-hydroxy-2-quinolone, 3-(3,4-dimethoxybenzoyl)-4-hydroxy-2-quinolone, 3-(3,4-dimethoxybenzoyl)-4-hydroxy-6-methyl-2-quinolone, 3-(3,4-dimethoxybenzoyl)-4-hydroxy-7-nitro-2-quinolone, 3-(3,4-dimethoxybenzoyl)-4-hydroxy-8-methyl-2-quinolone, 4-hydroxy-3-(2-isopropoxy-5-methoxybenzoyl)-2-quinolone, 4-hydroxy-3-(2,3,4-trimethoxybenzoyl)-2-quinolone, 4-hydroxy-3-(3,4,5-trimethoxybenzoyl)-2-quinolone, 4-hydroxy-3-(2,4,5-trimethoxybenzoyl)-2-quinolone, 3-(2-chlorobenzoyl)-4-hydroxy-2-quinolone, 3-(2-chlorobenzoyl)-4-hydroxy-6-isopropyl-2-quinolone, 3-(2-chlorobenzoyl)-6,8-dimethyl-4-hydroxy-2-quinolone, 3-(3-chlorobenzoyl)-4-hydroxy-2-quinolone, 3-(4-chlorobenzoyl)-4-hydroxy-2-quinolone, 3-(2-bromo-4-cyanobenzoyl)-4-hydroxy-2-quinolone, 3-(3,4-dichlorobenzoyl)-4-hydroxy-2-quinolone, 3-(2,5-dichloro-4-methylbenzoyl)-4-hydroxy-2-quinolone, 4-hydroxy-3-(2-methylbenzoyl)-2-quinolone, 4-hydroxy-3-(4-methylbenzoyl)-2-quinolone, 3-(2,4-dimethylbenzoyl)-4-hydroxy-2-quinolone, 4-hydroxy-3-(3-trifluoromethylbenzoyl)-2-quinolone, 4-hydroxy-3-(4-isopropylbenzoyl)-2-quinolone, 4-hydroxy-3-(4-n-pentylbenzoyl)-2-quinolone, 4-hydroxy-3-(4-nitrobenzoyl)-2-quinolone, 4-hydroxy-6-isopropyl-3-(4-nitrobenzoyl)-2-quinolone, 6,8-dimethyl-4-hydroxy-3-(4-nitrobenzoyl)-2-quinolone, 4-hydroxy-3-(4-methoxycarbonylbenzoyl)-2-quinolone, 3-(4-carboxybenzoyl)-4-hydroxy-2-quinolone, 4-hydroxy-6-methyl-3-(2,3,4-trimethoxybenzoyl-2-quinolone, 4-hydroxy-8-methyl-3-(2,3,4-trimethoxybenzoyl-2-quinolone, or 4-hydroxy-7-nitro-3-(2,3,4-trimethoxybenzoyl-2-quinolone.
Claim 18
Dependent Claim
74 words
A method according to claim 9 wherein the compound is: 3-benzoyl-6-chloro-4-hydroxy-2-quinolone, 3-benzoyl-7-chloro-4-hydroxy-2-quinolone, 3-benzoyl-8-chloro-4-hydroxy-6-methyl-2-quinolone, 3-benzoyl-6,8-dichloro-4-hydroxy-2-quinolone, 3-benzoyl-4-hydroxy-7-nitro-2-quinolone, 3-benzoyl-6-cyano-4-hydroxy-2-quinolone, methyl 3-benzoyl-4-hydroxy-2-quinolone-5-carboxylate, methyl 3-benzoyl-4-hydroxy-2-quinolone-6-carboxylate, methyl 3-benzoyl-4-hydroxy-2-quinolone-7-carboxylate, 3-benzoyl-4-hydroxy-2-quinolone-5-carboxylic acid, 3-benzoyl-4-hydroxy-2-quinolone-6-carboxylic acid, 3-benzoyl-4-hydroxy-2-quinolone-7-carboxylic acid, 3-benzoyl-4-hydroxy-2-quinolone-8-carboxylic acid, 3-benzoyl-4-hydroxy-6-methyl-2-quinolone, 3-benzoyl-4-hydroxy-7-methyl-2-quinolone, 3-benzoyl-4-hydroxy-8-methyl-2-quinolone, 3-benzoyl-6,7-dimethyl-4-hydroxy-2-quinolone, 3-benzoyl-6,8-dimethyl-4-hydroxy-2-quinolone, 3-benzoyl-6-isopropyl-4-hydroxy-2-quinolone, 3-benzoyl-6-n-butyl-4-hydroxy-2-quinolone, 3-benzoyl-6-n-hexyl-4-hydroxy-2-quinolone, 4-hydroxy-3-(2-methoxybenzoyl)-2-quinolone, 3-(2-ethoxybenzoyl)-4-hydroxy-2-quinolone, 4-hydroxy-3-(2-isopropoxybenzoyl)-2-quinolone, 4-hydroxy-3-(4-methoxybenzoyl)-2-quinolone, 3-(2,4-dimethoxybenzoyl)-4-hydroxy-2-quinolone, 3-(3,4-dimethoxybenzoyl)-4-hydroxy-2-quinolone, 3-(3,4-dimethoxybenzoyl)-4-hydroxy-6-methyl-2-quinolone, 3-(3,4-dimethoxybenzoyl)-4-hydroxy-7-nitro-2-quinolone, 3-(3,4-dimethoxybenzoyl)-4-hydroxy-8-methyl-2-quinolone, 4-hydroxy-3-(2-isopropoxy-5-methoxybenzoyl)-2-quinolone, 4-hydroxy-3-(2,3,4-trimethoxybenzoyl)-2-quinolone, 4-hydroxy-3-(3,4,5-trimethoxybenzoyl)-2-quinolone, 4-hydroxy-3-(2,4,5-trimethoxybenzoyl)-2-quinolone, 3-(2-chlorobenzoyl)-4-hydroxy-2-quinolone, 3-(2-chlorobenzoyl)-4-hydroxy-6-isopropyl-2-quinolone, 3-(2-chlorobenzoyl)-6,8-dimethyl-4-hydroxy-2-quinolone, 3-(3-chlorobenzoyl)-4-hydroxy-2-quinolone, 3-(4-chlorobenzoyl)-4-hydroxy-2-quinolone, 3-(2-bromo-4-cyanobenzoyl)-4-hydroxy-2-quinolone, 3-(3,4-dichlorobenzoyl)-4-hydroxy-2-quinolone, 3-(2,5-dichloro-4-methylbenzoyl)-4-hydroxy-2-quinolone, 4-hydroxy-3-(2-methylbenzoyl)-2-quinolone, 4-hydroxy-3-(4-methylbenzoyl)-2-quinolone, 3-(2,4-dimethylbenzoyl)-4-hydroxy-2-quinolone, 4-hydroxy-3-(3-trifluoromethylbenzoyl)-2-quinolone, 4-hydroxy-3-(4-isopropylbenzoyl)-2-quinolone, 4-hydroxy-3-(4-n-pentylbenzoyl)-2-quinolone, 4-hydroxy-3-(4-nitrobenzoyl)-2-quinolone, 4-hydroxy-6-isopropyl-3-(4-nitrobenzoyl)-2-quinolone, 6,8-dimethyl-4-hydroxy-3-(4-nitrobenzoyl)-2-quinolone, 4-hydroxy-3-(4-methoxycarbonylbenzoyl)-2-quinolone, 3-(4-carboxybenzoyl)-4-hydroxy-2-quinolone, 4-hydroxy-6-methyl-3-(2,3,4-trimethoxybenzoyl-2-quinolone, 4-hydroxy-8-methyl-3-(2,3,4-trimethoxybenzoyl-2-quinolone, or 4-hydroxy-7-nitro-3-(2,3,4-trimethoxybenzoyl-2-quinolone.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1988-07-01 | 1988-12-31 | 1989-07-02 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-07-01 | 1992-12-31 | 1993-07-02 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-07-01 | 1996-12-31 | 1997-07-02 | $7700.00 | Window Closed / Lapsed |