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EP0049355B1 Expired / Lapsed EP ⏱️ 0.0 years remaining

7-Amino-1-cyclopropyl-4-oxo-1,4-dihydro-(naphthyridine or quinoline)-3-carboxylic acids, process for their preparation and pharmaceutical compositions containing them

Assignee: Bayer AG
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Filing: 1981-08-21
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Granted: 1984-10-10
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Expires: 2001-08-21
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Abstract

No abstract record available.

Inventors

  • 👤 Klaus Dr. Grohe
  • 👤 Hans-Joachim Dr. Zeiler
  • 👤 Karl Georg Dr. Metzger

Bibliographic Details

Application Number —
Jurisdiction EP
Data Source google_patents
Last Synchronized 2026-10-31 05:52
CPC Classifications
C; C07; C07D; C07D471/00; C07D471/02; C07D471/04; A; A61; A61P; A61P31/00; A61P31/04; C07D215/00; C07D215/02; C07D215/16; C07D215/48; C07D215/54; C07D215/56

Claims Analysis

Total Claims: 13
Claim 1
Independent Claim 390 words
7-Amino-1-cyclopropyl-4-oxo-1 A-diphydro-naphthyridine-3-carboxylic acids of the general formula I in which A can be nitrogen or CR 3 wherein R 3 can be hydrogen, nitro, halogen, preferably fluorine or chlorine, or a nitrile, carboxamide, carboxyl or ester group, and B represents nitrogen or C- H, and A and B cannot simultaneously be nitrogen, and R 1 and R 2 are identical or different and represent hydrogen or a branched or straight-chain alkyl, alkenyl or alkinyl radical which has 1-12 carbon atoms and can optionally be substituted by hydroxyl groups, alkoxy, alkylmercapto or dialkylamino groups with 1-3 carbon atoms in each alkyl radical, the nitrile group or an alkoxy-carbonyl group with 1-4 carbon atoms in the alcohol part of furthermore denotes cycloalkyl with 3-6 carbon atoms, or, together with the nitrogen atom which they substitute and, if appropriate, a hetero-atom, such as, for example, oxygen or sulphur, or NR 4 , form a 3-membered to 7-membered ring which can be monosubstituted or polysubstituted by alkyl or alkenyl groups with 1-6 carbon atoms, hydroxyl groups, alkoxy or alkylmercapto groups with 1-3 carbon atoms, an alkoxycarbonyl group with 1-4 carbon atoms in the alcohol part, the nitrile group or a phenyl radical and can furthermore possess a double bond, and R 4 represents hydrogen, or a branched or straightchain alkyl, alkenyl or alkinyl group which has 1-6 carbon atoms and can optionally be substituted by hydroxyl, an alkoxy, alkylmercapto or dialkylamino group with 1-3 carbon atoms per alkyl radical or the alkoxycarbonyl group with 1-4 carbon atoms in the alcohol part, or represents a phenylalkyl group which is optionally substituted in the phenyl radical and has up to 4 carbon atoms in the aliphatic part, or an optionally substituted phenyl or naphthyl group or a heterocyclic radical, such as, for example, a pyridine, pyrimidine, thiazole or benzothiazole nurcleus, or denotes an alkoxycarbonyl group which is optionally substituted by a phenyl radical and has 1 -4 carbon atoms in the alcohol part, an alkanoyl radical with 1-6 carbon atoms, a benzoyl radical, an optionally substituted C1-C6-alkyl or phenylsulphonyl radical or an optionally substituted aminosulphonyl radical, possible substituents of phenyl and naphthyl groups being halogen, alkyl, alkoxy or alkylmercapto groups with 1-3 carbon atoms, phenyloxy, phenylmercapto, trifluoromethyl, nitro, nitrile or carboxylic ester groups with 1-4 carbon atoms in the alcohol part, and pharmaceutically usable salts thereof.
Claim 2
Dependent Claim 390 words
7-Amino-1-cyclopropyl-4-oxo-1 A-diphydro-naphthyridine-3-carboxylic acids of the general formula I in which A can be nitrogen or CR 3 wherein R 3 can be hydrogen, nitro, halogen, preferably fluorine or chlorine, or a nitrile, carboxamide, carboxyl or ester group, and B represents nitrogen or C- H, and A and B cannot simultaneously be nitrogen, and R 1 and R 2 are identical or different and represent hydrogen or a branched or straight-chain alkyl, alkenyl or alkinyl radical which has 1-12 carbon atoms and can optionally be substituted by hydroxyl groups, alkoxy, alkylmercapto or dialkylamino groups with 1-3 carbon atoms in each alkyl radical, the nitrile group or an alkoxy-carbonyl group with 1-4 carbon atoms in the alcohol part of furthermore denotes cycloalkyl with 3-6 carbon atoms, or, together with the nitrogen atom which they substitute and, if appropriate, a hetero-atom, such as, for example, oxygen or sulphur, or NR 4 , form a 3-membered to 7-membered ring which can be monosubstituted or polysubstituted by alkyl or alkenyl groups with 1-6 carbon atoms, hydroxyl groups, alkoxy or alkylmercapto groups with 1-3 carbon atoms, an alkoxycarbonyl group with 1-4 carbon atoms in the alcohol part, the nitrile group or a phenyl radical and can furthermore possess a double bond, and R 4 represents hydrogen, or a branched or straightchain alkyl, alkenyl or alkinyl group which has 1-6 carbon atoms and can optionally be substituted by hydroxyl, an alkoxy, alkylmercapto or dialkylamino group with 1-3 carbon atoms per alkyl radical or the alkoxycarbonyl group with 1-4 carbon atoms in the alcohol part, or represents a phenylalkyl group which is optionally substituted in the phenyl radical and has up to 4 carbon atoms in the aliphatic part, or an optionally substituted phenyl or naphthyl group or a heterocyclic radical, such as, for example, a pyridine, pyrimidine, thiazole or benzothiazole nurcleus, or denotes an alkoxycarbonyl group which is optionally substituted by a phenyl radical and has 1 -4 carbon atoms in the alcohol part, an alkanoyl radical with 1-6 carbon atoms, a benzoyl radical, an optionally substituted C1-C6-alkyl or phenylsulphonyl radical or an optionally substituted aminosulphonyl radical, possible substituents of phenyl and naphthyl groups being halogen, alkyl, alkoxy or alkylmercapto groups with 1-3 carbon atoms, phenyloxy, phenylmercapto, trifluoromethyl, nitro, nitrile or carboxylic ester groups with 1-4 carbon atoms in the alcohol part, and pharmaceutically usable salts thereof.
Claim 3
Dependent Claim 2 words
6-Fluoro-7-piperazino-1-cyclopropyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid.
Claim 4
Dependent Claim 2 words
6-Fluoro-7-piperazino-1-cyclopropyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid.
Claim 5
Dependent Claim 2 words
7-(4-Methylpiperazino)-1-cyclopropyl-4-oxo-1,4-dihydro-naphthyridine-3-carboxylic acid.
Claim 6
Dependent Claim 2 words
7-(4-Methylpiperazino)-1-cyclopropyl-4-oxo-1,4-dihydro-naphthyridine-3-carboxylic acid.
Claim 7
Dependent Claim 2 words
7-Piperazino-1-cyclopropyl-4-oxo-1,4-dihydro-naphthyridine-3-carboxylic acid.
Claim 8
Dependent Claim 2 words
7-Piperazino-1-cyclopropyl-4-oxo-1,4-dihydro-naphthyridine-3-carboxylic acid.
Claim 9
Dependent Claim 4 words
7-(4-Hydroxyethylpiperazino)-1-cyclopropyl-4-oxo-1,4-dihydro-naphthyridine-3-carboxylic acid. 6.7-(4-Formylpiperazino)-1-cyclopropyl-4-oxo-1,4-dihydro-naphthyridine-3-carboxylic acid.
Claim 10
Dependent Claim 4 words
7-(4-Hydroxyethylpiperazino)-1-cyclopropyl-4-oxo-1,4-dihydro-naphthyridine-3-carboxylic acid. 6.7-(4-Formylpiperazino)-1-cyclopropyl-4-oxo-1,4-dihydro-naphthyridine-3-carboxylic acid.
Claim 11
Dependent Claim 123 words
Process for the preparation of 7-amino-1-cycloprophyl-4-oxo-1,4-dihydro-naphthyridine-3-carboxylic acids of the general formule I in Claim 1, characterised in that (a) naphthyridone-3-carboxylic acids of the general formula II (R = H) in which A and B have the abovementioned meaning and X represents a halogen atom or an alkylsulphonyl group with 1-4 carbon atoms, are reacted with amines of the general formula III in which R I and R 2 have the abovementioned meaning, or (b) 7-halogeno-naphthyridone-3-carboxylic acid esters of the general formula II (R = alkyl) are reacted with amines of the general formula III, if appropriate in the presence of an acid-binding agent, such as, for example, triethylamine or pyridine, and the resulting 7-amino-naphthyridine-3-carox- ylic acid esters are then hydrolysed under alkaline conditions.
Claim 12
Dependent Claim 13 words
Medicaments, characterised in that they contain 7-amino-1-cyclopropyl-4-oxo-1,4-dihydro-naph- thyridine-3-carboxylic acids according to Claim 1.
Claim 13
Dependent Claim 24 words
Process for the preparation of antibacterial agents, characterised in that 7-amino-1-cyclopropyl-4-oxo-1,4-dihydro-naphthyridine-3-carboxylic acids according to Claim 1 are mixed with inert, non-toxic pharmaceutically suitable excipients.

References Cited (Backward Citations)

EP0014390A1 Cited

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