US4599334A
Expired / Lapsed
US
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7-(3-aryl-1-piperazinyl)- and 7-(3-cyclohexyl-1-piperazinyl)-3-quinolonecarboxylic acid antibacterials
Assignee: Bayer AG
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Filing: 1985-05-17
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Granted: 1986-07-08
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Expires: 2005-05-17
Abstract
Abstract Novel 1-cyclopropyl-4-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid antibacterials of the formula ##STR1## in which R 1 is hydrogen, alkyl with 1 to 4 carbon atoms and optionally substituted by hydroxyl, methoxy, amino, dimethylamino, halogen, cyano or alkoxycarbonyl having 1 or 2 carbon atoms in the alkyl moiety, or is oxoalkyl having up to 4 carbon atoms, phenacyl, or acyl having 1 to 4 carbon atoms, phenacyl, or acyl having 1 to 4 carbon atoms, R 2 is phenyl or cyclohexyl optionally substituted up to three times by halogen, methyl, phenyl, cyano, hydroxyl, methoxy, benzyloxy, amino, methylamino, dimethylamino, piperidino or nitro, or is methylenedioxyphenyl, methylenedioxycyclohexyl, furyl, tetrahydrofuryl or thienyl, and X 1 is hydrogen or fluorine, or pharmaceutically ultizable hydrates, acid addition salts, alkali metal salts or alkaline earth metal salts thereof.
Inventors
- 👤 Uwe Petersen
- 👤 Klaus Grohe
- 👤 Hans-Joachim Zeiler
- 👤 Karl G. Metzger
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 03:17
CPC Classifications
C; C07; C07D; C07D215/00; C07D215/02; C07D215/16; C07D215/48; C07D215/54; C07D215/56; A; A61; A61P; A61P3/00; A61P31/00; A61P31/04; C07D401/00; C07D401/02; C07D401/04; C07D409/00; C07D409/14
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
117 words
A 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid of the formula ##STR35## in which R 1 is hydrogen, alkyl with 1 to 4 carbon atoms and optionally substituted by hydroxyl, methoxy, amino, dimethylamino, halogen, cyano or alkoxycarbonyl having 1 or 2 carbon atoms in the alkyl moiety, or is oxoalkyl having up to 4 carbon atoms, phenacyl, or acyl having 1 to 4 carbon atoms, R 2 is phenyl or cyclohexyl optionally substituted up to three times by halogen, methyl, phenyl, cyano, hydroxyl, methoxy, benzyloxy, amino, methylamino, dimethylamino, piperidino or nitro, or is methylenedioxyphenyl, methylenedioxycyclohexyl, furyl, tetrahydrofuryl or thienyl, and X 1 is hydrogen or fluorine, or a pharmaceutically utilizable hydrate, acid addition salt, alkali metal or alkaline earth metal salt thereof.
Claim 2
Dependent Claim
117 words
A 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid of the formula ##STR35## in which R 1 is hydrogen, alkyl with 1 to 4 carbon atoms and optionally substituted by hydroxyl, methoxy, amino, dimethylamino, halogen, cyano or alkoxycarbonyl having 1 or 2 carbon atoms in the alkyl moiety, or is oxoalkyl having up to 4 carbon atoms, phenacyl, or acyl having 1 to 4 carbon atoms, R 2 is phenyl or cyclohexyl optionally substituted up to three times by halogen, methyl, phenyl, cyano, hydroxyl, methoxy, benzyloxy, amino, methylamino, dimethylamino, piperidino or nitro, or is methylenedioxyphenyl, methylenedioxycyclohexyl, furyl, tetrahydrofuryl or thienyl, and X 1 is hydrogen or fluorine, or a pharmaceutically utilizable hydrate, acid addition salt, alkali metal or alkaline earth metal salt thereof.
Claim 3
Dependent Claim
86 words
A 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid, hydrate or salt according to claim 1, in which R 1 is hydrogen, alkyl with 1 to 4 carbon atoms and optionally substituted by hydroxyl, methoxy, halogen, cyano or alkoxycarbonyl having 1 or 2 carbon atoms in the alkyl moiety, or is oxoalkyl having up to 4 carbon atoms, phenacyl, formyl or acetyl, and R 2 is phenyl or cyclohexyl optionally substituted up to three times by chlorine, bromine, fluorine, methyl, phenyl, cyano, hydroxyl, methoxy, benzyloxy, amino, piperidino or nitro, or is thienyl.
Claim 4
Dependent Claim
84 words
A 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid, hydrate or salt according to claim 1, in which R 1 is hydrogen, alkyl with 1 to 3 carbon atoms and optionally substituted by hydroxyl, methoxy, cyano or alkoxy carbonyl having 1 or 2 carbon atoms in the alkyl moiety, or is oxoalkyl having up to 4 carbon atoms, phenacyl, formyl or acetyl, R 2 is phenyl or cyclohexyl optionally substituted up to three times by chlorine, bromine, fluorine, methyl, phenyl, hydroxyl, methoxy, benzyloxy, amino, piperidino or nitro, or is thienyl.
Claim 5
Dependent Claim
32 words
A compound according to claim 1, wherein such compound is 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(3-phenyl-1-piperazinyl)-3-quinolinecarboxylic acid of the formula ##STR36## or a pharmaceutically utilizable hydrate, acid addition salt, alkali metal or alkaline earth metal salt thereof.
Claim 6
Dependent Claim
32 words
A compound according to claim 1, wherein such compound is 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-[3-(4-fluorophenyl)-1-piperazinyl]-3-quinolinecarboxylic acid of the formula ##STR37## or a pharmaceutically utilizable hydrate, acid addition salt, alkali metal or alkaline earth metal salt thereof.
Claim 7
Dependent Claim
32 words
A compound according to claim 1, wherein such compound is 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-{3-[4-(1-piperidinyl)-phenyl]-1-piperazinyl}-3-quinolinecarboxylic acid of the formula ##STR38## or a pharmaceutically utilizable hydrate, acid addition salt, alkali metal or alkaline earth metal salt thereof.
Claim 8
Dependent Claim
32 words
A compound according to claim 1, wherein such compound is 1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-7-[3-(2-thienyl)-1-piperazinyl]-3-quinolinecarboxylic acid of the formula ##STR39## or a pharmaceutically utilizable hydrate, acid addition salt, alkali metal or alkaline earth metal salt thereof.
Claim 9
Dependent Claim
32 words
A compound according to claim 1, wherein such compound is 1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-7-(3-phenyl-1-piperazinyl)-3-quinolinecarboxylic acid of the formula ##STR40## or a pharmaceutically utilizable hydrate, acid addition salt, alkali metal or alkaline earth metal salt thereof.
Claim 10
Dependent Claim
23 words
An antibacterial composition comprising an antibacterially effective amount of a compound, hydrate or salt according to claim 1 in admixture with a diluent.
Claim 11
Dependent Claim
19 words
A unit dose of a composition according to claim 9 in the form of a tablet, capsule or ampule.
Claim 12
Dependent Claim
38 words
A method of combating bacteria which comprises applying to such bacteria or to a host from which it is desired to exclude such bacteria an antibacterially effective amount of a compound, hydrate or salt according to claim 1.
Claim 13
Dependent Claim
37 words
The method according to claim 11, wherein such compound is 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(3-phenyl-1-piperazinyl)-3-quinolinecarboxylic acid, 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-[3-(4-fluorophenyl)-1-piperazinyl]-3-quinolinecarboxylic acid, 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-{3-[4-1-piperidinyl)-phenyl]-1-piperazinyl}-3-quinolinecarboxylic acid, 1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-7-[3-(2-thienyl)-1-piperazinyl]-3-quinolinecarboxylic acid or 1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-7-(3-phenyl-1-piperazinyl)-3-quinolinecarboxylic acid, or a pharmaceutically utilizable hydrate, acid addition salt, alkali metal or alkaline earth metal salt thereof.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1989-07-07 | 1990-01-06 | 1990-07-08 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-07-07 | 1994-01-06 | 1994-07-08 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-07-07 | 1998-01-06 | 1998-07-08 | $7700.00 | Window Closed / Lapsed |