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US4980353A Expired / Lapsed US ⏱️ 0.0 years remaining

1-aryl-4-quinolone-3-carboxylic acids

Assignee: Bayer AG
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Filing: 1986-05-13
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Granted: 1990-12-25
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Expires: 2006-05-13
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Abstract

Abstract Antibacterially active and animal growth promoting novel 1-aryl-4-quinolone-3-carboxylic acids of the formula <IMAGE> in which X is halogen or nitro, X2 is halogen, R is optionally substituted phenyl, and A is halogen or optionally substituted piperazine or pyrrolidine, or pharmaceutically useable hydrates, acid additions salts, alkali metal, alkaline earth metal, silver or guanidinium salts thereof, and/or esters thereof.

Inventors

  • 👤 Klaus Grohe
  • 👤 Hans-Joachim Zeiler
  • 👤 Karl G. Metzger

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-27 12:13
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; C07C; C07C205/00; C07C205/49; C07C205/57; C07C205/58; C07C205/61; C07D401/00; C07D401/02; C07D401/04

Claims Analysis

Total Claims: 10
Claim 1
Independent Claim 248 words
A 1-aryl-4-quinoline-3-carboxylic acid of the formula ##STR85## in which X 1 is chlorine, fluorine or nitro, X 2 is chlorine or fluorine with the proviso that X 1 and X 2 are not simultaneously fluorine, R is phenyl, or phenyl substituted by at least one of halogen, alkyl with 1 to 4 carbon atoms, alkoxy, alkylmercapto or alkylsulphonyl with in each case up to 3 carbon atoms, nitro, cyano, carboxyl, methylenedioxy, a pyridine, thiophene, furan or thiazole radical, or an amine radical of the formula ##STR86## R 5 and R 6 each independently is hydrogen, or alkyl with 1 to 3 carbon atoms, A is ##STR87## or halogen, R 1 is hydrogen, alkyl with 1 to 4 carbon atoms, alkyl with 1 to 4 carbon atoms and substituted by a hydroxyl or methoxy group, phenacyl, phenacyl substituted by hydroxyl, methoxy, chlorine or fluorine, an oxoalkyl radical with 2 to 4 carbon atoms, 4-aminobenzyl, formyl or acetyl, or the radical ##STR88## R 2 is hydrogen, methyl, phenyl, thienyl, or phenyl or thienyl substituted by chlorine, fluorine, methyl, hydroxyl or methoxy, R 3 is hydrogen or methyl, and R 4 is hydrogen, hydroxyl amino, alkyl- or dialkylamino with 1 or 2 carbon atoms in each alkyl group, hydroxymethyl, aminomethyl or alkyl- or dialkylaminomethyl with 1 or 2 carbon atoms in each alkyl group, or a pharmaceutically usable hydrate, acid addition salt, alkali metal, alkaline earth metal, silver or guanidinium salt thereof, and/or an C 1 -C 3 -alkyl ester thereof.
Claim 2
Dependent Claim 248 words
A 1-aryl-4-quinoline-3-carboxylic acid of the formula ##STR85## in which X 1 is chlorine, fluorine or nitro, X 2 is chlorine or fluorine with the proviso that X 1 and X 2 are not simultaneously fluorine, R is phenyl, or phenyl substituted by at least one of halogen, alkyl with 1 to 4 carbon atoms, alkoxy, alkylmercapto or alkylsulphonyl with in each case up to 3 carbon atoms, nitro, cyano, carboxyl, methylenedioxy, a pyridine, thiophene, furan or thiazole radical, or an amine radical of the formula ##STR86## R 5 and R 6 each independently is hydrogen, or alkyl with 1 to 3 carbon atoms, A is ##STR87## or halogen, R 1 is hydrogen, alkyl with 1 to 4 carbon atoms, alkyl with 1 to 4 carbon atoms and substituted by a hydroxyl or methoxy group, phenacyl, phenacyl substituted by hydroxyl, methoxy, chlorine or fluorine, an oxoalkyl radical with 2 to 4 carbon atoms, 4-aminobenzyl, formyl or acetyl, or the radical ##STR88## R 2 is hydrogen, methyl, phenyl, thienyl, or phenyl or thienyl substituted by chlorine, fluorine, methyl, hydroxyl or methoxy, R 3 is hydrogen or methyl, and R 4 is hydrogen, hydroxyl amino, alkyl- or dialkylamino with 1 or 2 carbon atoms in each alkyl group, hydroxymethyl, aminomethyl or alkyl- or dialkylaminomethyl with 1 or 2 carbon atoms in each alkyl group, or a pharmaceutically usable hydrate, acid addition salt, alkali metal, alkaline earth metal, silver or guanidinium salt thereof, and/or an C 1 -C 3 -alkyl ester thereof.
Claim 3
Dependent Claim 156 words
A 1-aryl-4-quinoline-3-carboxylic acid hydrate, salt and/or ester according to claim 1, in which X 1 is chlorine, fluorine or nitro, X 2 is chlorine or fluorine, with the proviso that X 1 and X 2 are not simultaneously fluorine, R is phenyl, phenyl substituted by halogen, alkyl, alkoxy, alkylmercapto or alkylsulphonyl with an each case up to 2 carbon atoms in each alkyl part, nitro or cyano, or is a pyridine, thiophene, furan or thiazole radical, A is ##STR89## or halogen, R 1 is hydrogen, alkyl with 1 to 3 carbon atoms, alkyl with 1 to 3 carbon atoms substituted by a hydroxyl group, phenacyl, phenacyl substituted by chlorine or fluorine, an oxoalkyl radical with 3 or 4 carbon atoms, 4-aminobenzyl, formyl or acetyl, R 2 is hydrogen, methyl, phenyl, phenyl substituted by chlorine or fluorine, R 3 is hydrogen or methyl, and R 4 is hydrogen, hydroxyl, amino, methylamino, ethylamino, aminomethyl, methylaminomethyl, ethylaminomethyl or diethylaminomethyl.
Claim 4
Dependent Claim 78 words
A 1-aryl-4-quinolone-3-carboxylic acid hydrate, salt and/or ester according to claim 1, in which X 1 is chlorine, X 2 is fluorine, R is phenyl, or phenyl substituted by chlorine or fluorine, ethyl, methoxy, methylmercapto, nitro or cyano, A is ##STR90## or halogen, R 1 is hydrogen, methyl, ethyl, 2-hydorxyethyl, phenacyl, 2-oxopropyl, 3-oxobutyl or formyl, R 2 is hydrogen, methyl or phenyl, R 3 is hydrogen or methyl, and R 4 is hydrogen, amino, methylamino, aminomethyl, ethylaminomethyl or diethylaminomethyl.
Claim 5
Dependent Claim 20 words
A 1-aryl-4-quinolone-3-carboxylic acid ester according to claim 1, in the form of the methyl, ethyl, pivaloyloxymethyl, pivaloyl-oxyethyl or (5-methyl-2-oxo-1,3-dioxol-4-yl-methyl) ester.
Claim 6
Dependent Claim 20 words
A compound according to claim 1, selected from the group consisting of 6-fluoro-1,4-dihydro-4-oxo-8-nitro-1-phenyl-7-(4-methyl-1-piperazinyl)-quinoline-3-carboxylic and a hydrate, salt and/or ester thereof.
Claim 7
Dependent Claim 34 words
A compound according to claim 1, selected from the group consisting of 8-chloro-6-fluoro-1,4-dihydro-4-oxo-1-phenyl-7-(1-piperazinyl)-quinoline-3-carboxylic acid, 8-chloro-6-fluoro-1,4-dihydro-4-oxo-1-phenyl-7-(4-methyl-1-piperazinyl)-quinoline-3-carboxylic acid, 8-chloro-6-fluoro-1,4-dihydro-4-oxo-1-phenyl-7-(3-methyl-l-piperazinyl)-quinoline-3-carboxylic acid, 8-chloro-6-fluoro-1,4-dihydro-4-oxo-1-phenyl-7-pyrrolidinyl-quinoline-3-carboxylic acid, 8-chloro-6-fluoro-1,4-dihydro-4-oxo-1-phenyl-7-(3-methylamino-1-pyrrolidinyl)-quinoline-3-carboxylic acid, 8-chloro-6-fluoro-1,4-dihydro-4-oxo-1-phenyl-7-(3-ethylaminomethyl-1-pyrrolidinyl)-quinoline-3-carboxylic acid and 6-fluoro-1,4-dihydro-8-nitro-4-oxo-1-phenyl-7-(4-ethyl-1-piperazinyl)-quinoline-3-carboxylic acid, and a hydrate, salt and/or ester thereof.
Claim 8
Dependent Claim 28 words
An antibacterial composition comprising an antibacterially effective amount of an acid, hydrate, salt and/or ester thereof according to claim 1 in the combination with a pharmaceutically acceptable diluent.
Claim 9
Dependent Claim 19 words
A unit dose of a composition according to claim 7 in the form of a tablet, capsule or ampule.
Claim 10
Dependent Claim 14 words
A composition according to claim 7, wherein the diluent is an animal feed base.

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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) 1993-12-24 1994-06-25 1994-12-25 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1997-12-24 1998-06-25 1998-12-25 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2001-12-24 2002-06-25 2002-12-25 $7700.00 Window Closed / Lapsed

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