Process for the preparation of 4-pyridone-3-carboxylic acids and/or derivatives thereof
AssigneeBayer Aktiengesellschaft
InventorsKlaus Grohe, Hans-Joachim Zeiler, Karl G. Metzger
Life of this patent
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Abstract
The invention provides 4-pyridone-3-carboxylic acids and derivatives thereof together with a method for their preparation. Also included in the invention are compositions containing said 4-pyridone-3-carboxylic acids and derivatives and the use of said compounds and compositions as antibacterial and/or antifungal agents or for animal growth promotion or improved feed utilization.
Claims18
A compound of the formula ##STR25## or a salt thereof in which R.sup.1a denotes a cycloalkyl group having 3 to 7 carbon atoms or an amino group --NR.sup.4 R.sup.5,
- in which
- R.sup.4 and R.sup.5 are identical or different, and denote a straight-chain or branched C.sub.1 to C.sub.4 alkyl group or, together with the nitrogen atom which they substitute, form a 5-membered to 7-membered ring,
- R.sup.2 denotes a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, an aralkyl group having 1 to 4 carbon atoms in the aliphatic part and 6 to 10 carbon atoms in the aromatic part or an aryl group having 6 to 10 carbon atoms and
- R.sup.3a denotes a carboxyl group or a derivative which is a nitrile, an ester or an acid amide,
- the symbols A and D are nitrogen atoms and the symbols B and E remaining in each case represent a carbon atom which is unsubstituted or substituted by C.sub.1 to C.sub.6 alkyl, C.sub.1 to C.sub.4 alkoxy, C.sub.1 to C.sub.6 alkylmercapto, trifluoromethyl, halogen, cyano, carboxyl which is esterified by C.sub.1 to C.sub.4 alkyl, benzyl or phenyl each of which is unsubstituted or substituted by C.sub.1 to C.sub.3 alkyl, nitro or halogen, or amino substituted by carbalkoxy.
A process for the production of a 4-pyridone-3-carboxylic acid or a derivative thereof which comprises reacting enamine of the formula ##STR26## in which R.sup.1 denotes an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 7 carbon atoms, an aralkyl group having 1 to 4 carbon atoms in the aliphatic part and 6 to 10 carbon atoms in the aromatic part or an aryl group having 6 to 10 carbon atoms or an amino group --NR.sup.4 R.sup.5,
- in which
- R.sup.4 and R.sup.5 are identical or different, and denote a straight-chain or branched C.sub.1 to C.sub.4 alkyl group or, together with the nitrogen atom which they substitute, form a 5-membered to 7-membered ring, R.sup.2 denotes a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, an aralkyl group having 1 to 4 carbon atoms in the aliphatic part and 6 to 10 carbon atoms in the aromatic part or an aryl group having 6 to 10 carbon atoms and
- R.sup.3 denotes an ester or acid amide derivative of the carboxyl group, with an o-halogeno-(hetero)-aryl-carboxylic acid halide of the formula ##STR27## in which the symbols A and D are nitrogen atoms and the symbols B and E remaining in each case denote a carbon atom, and which is unsubstituted or substituted by C.sub.1 to C.sub.6 alkyl, C.sub.1 to C.sub.4 alkoxy, C.sub.1 to C.sub.6 alkylmercapto, trifluoromethyl, halogen, cyano, carboxyl which is esterified by C.sub.1 to C.sub.4 alkyl, benzyl or phenyl each of which is unsubstituted or substituted by C.sub.1 to C.sub.3 alkyl, nitro or halogen, or amino substituted by carbalkoxy.
Dependencies are inferred from the claim text.