Novel carboxylic acid derivatives, their preparation and use

Abstract

Carboxylic acid derivatives where R—R 6 , X, Y and Z have the meanings stated in the description, and the preparation thereof, are described. The novel compounds are suitable for controlling diseases.

1 . A carboxylic acid derivative of the formula I 
       
         
           
           
               
               
           
         
         where R is formyl, tetrazole [sic], nitrile [sic], a COOH group or a radical which can be hydrolyzed to COOH, and the other substituents have the following meanings: 
         R 2  hydrogen, hydroxyl, NH2, NH(C 1 -C 4 alkyl), N(C 1 -C 4 -alkyl) 2  halogen, C 1 -C 4 -alkyl, C 1 -C 4 -fialoalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy or C 1 -C 4 -alkylthio; 
         X nitrogen or CR 14  where R 14  is hydrogen or C 1-5 -alkyl, or CR 14  forms together with CR 3  a 5- or 6-membered alkylene or alkenylene ring which can be substituted by one or two C 1-4 -alkyl groups and in-which in each case a methylene group can be replaced by oxygen, sulfur, —NH or —NC 1-4 -alkyl; hydrogen, hydroxyl, NH2, NH(C 1 -C 4 -Alkyl), N(C 1 -C 4 -alkyl) 2 , halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, —NH—O—C 1-4 -alkyl, C 1 -C 4 -alkylthio or CR 3  is linked to CR 14  as indicated above to give a 5- or 6-membered ring; 
         R 4  and R 5  (which can be identical or different):
 phenyl or naphthyl, which can be substituted by one or more of the following radicals: halogen, nitro, cyano, hydroxyl, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, phenoxy, C 1 -C 4 -alkylthio, amino, C 1 -C 4 -alkylamino or C 1 -C 4 -dialkylamino; or 
 phenyl or naphthyl, which are connected together in the ortho positions via a direct linkage, a methylene, ethylene or ethenylene group, an oxygen or sulfur atom or an SO 2 , NH or N-alkyl group or C 3 -C 7 -cycloalkyl; 
 
         R 6  hydrogen, C 1 -C 8 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 8 -alkynyl or C 3 -C 8 -cycloalkyl, where each of these radicals can be substituted one or more times by: halogen, nitro, cyano, C 1 -C 4 -alkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 -alkynyloxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxycarbonyl, C 3-8 -alkylcarbonylalkyl, C 1 -C 4 -alkylamino, di-C 1 -C 4 -alkylamino, phenyl or phenyl or phenoxy which is substituted one or more times, eg. one to three times, by halogen, nitro, cyano, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy or C 1 -C 4 -alkylthio;
 phenyl or naphthyl, each of which can be substituted by one or more of the following radicals: halogen, nitro, cyano, hydroxyl, amino, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxyl C 1 -C 4 -haloalkoxy, phenoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylamino, C 1 -C 4 -dialkylamino or dioxomethylene [sic] or dioxoethylene [sic]; 
 a five- or six-membered heteroaromatic moiety containing one to three nitrogen atoms and/or one sulfur or oxygen atom, which can carry one to four halogen atoms and/or one or two of the following radicals: C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -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: C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy and/or C 1 -C 4 -alkylthio; 
 with the proviso that R 6  can be hydrogen only when Z is not a single bond; 
 
         Y sulfur or oxygen or a single bond; 
         z sulfur, oxygen, —SO—, —SO2- or a single bond. 
       
       Novel carboxylic acid derivatives, their preparation and use