Process for the preparation of 4-pyridone-3-carboxylic acids and/or derivatives thereof

Claim 2

A compound of the formula ##STR25## or a salt thereof in which R 1a denotes a cycloalkyl group having 3 to 7 carbon atoms or an amino group --NR 4 R 5 , in which R 4 and R 5 are identical or different, and denote a straight-chain or branched C 1 to C 4 alkyl group or, together with the nitrogen atom which they substitute, form a 5-membered to 7-membered ring, R 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 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 1 to C 6 alkyl, C 1 to C 4 alkoxy, C 1 to C 6 alkylmercapto, trifluoromethyl, halogen, cyano, carboxyl which is esterified by C 1 to C 4 alkyl, benzyl or phenyl each of which is unsubstituted or substituted by C 1 to C 3 alkyl, nitro or halogen, or amino substituted by carbalkoxy.

Claim 3

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 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 4 R 5 , in which R 4 and R 5 are identical or different, and denote a straight-chain or branched C 1 to C 4 alkyl group or, together with the nitrogen atom which they substitute, form a 5-membered to 7-membered ring, R 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 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 1 to C 6 alkyl, C 1 to C 4 alkoxy, C 1 to C 6 alkylmercapto, trifluoromethyl, halogen, cyano, carboxyl which is esterified by C 1 to C 4 alkyl, benzyl or phenyl each of which is unsubstituted or substituted by C 1 to C 3 alkyl, nitro or halogen, or amino substituted by carbalkoxy.

Claim 4

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 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 4 R 5 , in which R 4 and R 5 are identical or different, and denote a straight-chain or branched C 1 to C 4 alkyl group or, together with the nitrogen atom which they substitute, form a 5-membered to 7-membered ring, R 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 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 1 to C 6 alkyl, C 1 to C 4 alkoxy, C 1 to C 6 alkylmercapto, trifluoromethyl, halogen, cyano, carboxyl which is esterified by C 1 to C 4 alkyl, benzyl or phenyl each of which is unsubstituted or substituted by C 1 to C 3 alkyl, nitro or halogen, or amino substituted by carbalkoxy.

Claim 5

A medicated fodder comprising an amount of a compound as claimed in claim 1 effective for promoting growth and improving feed utilization and a nutritious material.

Claim 6

A process according to claim 2 in which the aprotic solvent is dioxane.

Claim 7

A process according to claim 2 in which the first reaction stage is carried out from 10° to 60° C. and the second reaction stage is carried out from 100° to 150° C. and the aprotic solvent is dioxane.

Claim 8

A process according to claim 2 in which R' is cyclopropyl or cyclohexyl.

Claim 9

A process according to claim 2 in which the base in the first reaction stage is triethylamine and the base in the second reaction stage is 1,8-diazabicyclo-[5.4.0]-undec-7-ene.

Claim 10

A process according to claim 2 in which the enamine is of the formula ##STR28## in which R 1' denotes a tert.alkyl, a C 3 , to C 7 cycloalkyl, or a dialkyl amino group --NR 4' --R 5' , in which R 4' and R 5' denote a C 1 or C 2 alkyl group or together complete a morpholinyl radical, R 2' denotes a hydrogen atom or a C 1 to C 4 alkyl group or an optionally substituted benzyl or phenyl radical and R 3 has the same meaning as in claim 2.

Claim 11

A process according to claim 2 in which the enamine is of the formula ##STR29## in which R 1" denotes a tert.-butyl, cyclopropyl, cyclohexyl or dimethylamino group or a N-morpholinyl radical, R 2" denotes a hydrogen atom or a C 1 to C 4 alkyl group and R 3 has the same meaning as in claim 2.

Claim 12

A process according to claim 2 in which the o-halogeno-(hetero-)aryl-carboxylic acid halide is a compound of the formula ##STR30## in which the symbols A, B, D and E have the same meaning as in claim 2, but the heterocyclic radical optionally present contains at most two nitrogen atoms.

Claim 13

A compound according to claim 1 in which R 1a denotes a tert.-butyl, cyclopropyl, cyclohexyl, dimethylamino or N-morpholinyl radical.

Claim 14

A compound according to claim 1 of the formula ##STR31## in which A, B, D and E have the same meanings as in claim 1.

Claim 15

A pharmaceutical composition containing as an active ingredient an antibacterially or antifungally effective amount of a compound according to claim 1 in admixture with a solid or liquefied gaseous diluent or in admixture with a liquid diluent other than a solvent of a molecular weight less than 200 except in the presence of a surface-active agent.

Claim 16

A pharmaceutical composition containing as an active ingredient an antibacterially or antifungally effective amount of a compound according to claim 1 in the form of a sterile or physiologically isotonic aqueous solution.

Claim 17

A composition according to claim 13 containing from 0.5 to 95% by weight of the said active ingredient.

Claim 18

A medicament in dosage unit form comprising an antibacterially or antifungally effective amount of a compound according to claim 1 together with an inert pharmaceutical carrier.

Claim 19

A medicament of claim 16 in the form of tablets, pills, dragees, capsules, ampoules, or suppositories.

Claim 20

A method of combating bacterial diseases in warm-blooded animals which comprises administering to the said animals an effective amount of an active compound according to claim 1 either alone or in admixture with a diluent or in the form of a medicament.