α-hydrdroxylic acid derivatives, their production and use

An α-hydroxy carboxylic acid compound of the formula I

• where R is a group
• where R1 has the following meanings:
• b) a succinylimidoxy group
• c) a 5-membered heteroaromatic ring selected from the group consisting of pyrrolyl, pyrazolyl, imidazolyl and triazolyl, which ring is bonded to CH via a ring nitrogen atom and which may carry one or two halogen atoms or one or two C1-C4-alkyl or one or two C1-C4-alkoxy groups;
• d) a group
• where k can assume the values 0, 1 and 2, p can assume the values 1, 2, 3 and 4, and R9 is C1-C4-alkyl, C3-C7-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl or unsubstituted or substituted phenyl which can be substituted by one or more of the following radicals:
• halogen, nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, hydroxyl, C1-C4-alkoxy, C1-C4-alkylthio, mercapto, amino, C1-C4-alkylamino, C1-C4-dialkylamino;
• e) a radical OR10, where R10 is:
• hydrogen, the cation of an alkali metal lithium, sodium, potassium or the cation of an alkaline earth metal calcium, magnesium and barium, and physiologically tolerated alkylammonium ion or the ammonium ion;
• C3-C8-cycloalkyl,
• C1-C8-alkyl,
• CH2 phenyl which can be substituted on the phenyl radical by one or more of the following radicals:
• halogen, nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, hydroxyl, C1-C4-alkoxy, mercapto, C1-C4-alkylthio, amino, C1-C4-alkylamino, C1-C4-dialkylamino, a C3-C6-alkenyl or C3-C6-alkynyl group, it being possible for this group in turn to carry one to five halogen atoms;
• a phenyl radical which can carry one to five halogen atoms and/or one to three of the following radicals:
• nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, hydroxyl, C1-C4-alkoxymercapto, C1-C4-alkylthio, amino, C1-C4-alkylamino, C1-C4-dialkylamino;
• a 5-membered heteroaromatic system which is linked via a nitrogen atom and has one to three nitrogen atoms, and which may carry one or two halogen atoms and/or one or two of the following radicals:
• C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, phenyl, C1-C4-haloalkoxy and/or C1-C4-alkylthio;
• f) a radical
• where R11 is:
• C1-C4-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, C3-C8-cycloalkyl, it being possible for these radicals to carry a C1-C4-alkoxy, C1-C4-alkylthio, and/or a phenyl radical;
• phenyl which is unsubstituted or substituted by one or more members selected from the group consisting of halogen, nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, hydroxyl, C1-C4-alkoxy, mercapto, C1-C4-alkylthio, amino, C1-C4-alkylamino, and C1-C4-dialkylamino;
• h)
• where R13 and R14 can be identical or different and have the following meanings:
• hydrogen, C1-C7-alkyl, C3-C7-cycloalkyl, C3-C7-alkenyl, C3-C7-alkynyl, benzyl, phenyl, wherein the phenyl radicals are optionally unsubstituted or substituted by one or more members selected from the group consisting of halogen, nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, hydroxyl, C1-C4-alkoxy, mercapto, C1-C4-alkylthio, amino, C1-C4-alkylamino, and C1-C4-dialkylamino,
• or R13 and R14 together form a C4-C7-alkylene chain which is closed to a ring, is unsubstituted or substituted by C1-C4-alkyl and may contain a hetero atom selected from the group consisting of oxygen, sulfur or nitrogen,
• or R is tetrazolyl or cyano;
• W is nitrogen, C—NO2, a CH group when one or more of the substituents R2, R3, R15 and/or R16 are a nitro group, or when X and/or Y are nitrogen;
• R2 and R3 are phenyl, optionally substituted once to three times by halogen, hydroxyl, amino, mono- or dialkyl (C1-C3)-amino, C1-C3-alkyl, C1-C3-alkoxy, mercapto or C1-C3-alkylthio, carboxyl or C1-C3-alkylcarboxyl;
• X is nitrogen or CR15 where R15 is hydrogen or C1-C5-alkyl, optionally substituted once or twice by hydroxyl or carboxyl;
• C1-C6-alkoxy, C1-C6-alkylthio, phenyl, benzyl, hydroxyl, mercapto, nitro, amino, C1-C4-alkylamino, C1-C4-dialkylamino, cyano or carboxyl;
• it is furthermore possible for CR15 to be linked to R2 to give a 5- or 6-membered ring as described above, or CR15 can form with R3 and its adjacent carbon atom a 5- or 6-membered alkylene or alkylidene ring in each of nitrogen, oxygen or sulfur, and the 5- or 6-membered ring may optionally be substituted once to three times by the following radicals:
• halogen, nitro, cyano, hydroxyl, mercapto, C1-C3-alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, C1-C3-alkylthio, amino, C1-C3-alkylamino, C1-C3-dialkylamino or carboxyl;
• nitrogen in the 5-membered ring may also be substituted by a formyl or acetyl group;
• Y is nitrogen or CR16 where R16 is hydrogen, C1-C5-alkyl, C1-C5-alkoxy, C1-C5-alkylthio, nitro, phenyl, hydroxyl, halogen, cyano, amino, C1-C4-alkylamino, C1-C4-dialkylamino, mercapto or carboxyl, or R16 forms together with R3 and its adjacent carbon atom a 5- or 6-membered ring as described above wherein two of X, Y and W are nitrogen and the other is carbon;
• R4 is phenyl, naphthyl, dihydro- or tetrahydronaphthyl, which can be substituted by one or more of the following radicals:
• halogen, nitro, cyano, hydroxyl, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, phenoxy, phenyl, C1-C4-alkylthio, amino, C1-C4-alkylamino or C1-C4-dialkylamino, it being possible for two radicals on adjacent carbon atoms to form, together with the latter, a five- or six-membered ring which is linked by an alkylene or alkylidene group and in which one or more methylene or methylidene groups can be replaced by oxygen;
• R5 can have the same meanings as R4, it being possible for R4 and R5 to be identical or different;
• and
• R6 is hydrogen, C1-C8-alkyl, C3-C8-alkenyl or C3-C8-alkynyl, it being possible for each of these radicals to be substituted one or more times by:
• halogen, nitro, cyano, C1-C4-alkoxy, hydroxyl, C1-C4-alkylthio, mercapto, C1-C4-haloalkoxy, carboxyl, C1-C4-alkylcarboxy, C1-C4-alkylcarbonyl, amino, C1-C4-alkylamino, C1-C4-dialkylamino, a five- or six-membered heteroaromatic system which has one to three nitrogen atoms and/or one sulfur or oxygen atom and which can carry one to four halogen atoms and/or one or two of the following radicals;
• C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, phenyl, phenoxy or phenylcarbonyl, it being possible for the phenyl radicals in turn to carry one to five halogen atoms and/or one to three of the following radicals:
• C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy and/or C1-C4-alkylthio;
• phenyl, naphthyl, which can in turn be substituted one or more times by:
• halogen, nitro, cyano, hydroxyl, C1-C4-alkoxy, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-haloalkoxy, mercapto, C1-C4-alkylthio, amino, C1-C4-alkylamino, C1-C4-dialkyl amino or phenoxy;
• or one of the following radicals: