Carboxylic acid derivatives, their preparation and use

  • US 5,932,730 A
  • Filed: 03/27/1997
  • Issued: 08/03/1999
  • Est. Priority Date: 10/14/1994
  • Status: Expired due to Term
First Claim
Patent Images

1. A compound of the formula I ##STR16## where R is formyl, tetrazole, nitrile, a COOH group or a radical which can be hydrolyzed to COOH, and the other substituents have the following meanings:

  • R2 hydrogen, hydroxyl, NH2, NH(C1 -C4 -alkyl), N(C1 -C4 -alkyl)2, halogen, C1 -C4 -alkyl, C1 -C4 -haloalkyl, C1 -C4 -alkoxy, C1 -C4 -haloalkoxy or C1 -C4 -alkylthio;

    R3 hydrogen, hydroxyl, NH2, NH(C1 -C4 -alkyl), N(C1 -C4 -alkyl)2, halogen, C1 -C4 -alkyl, C1 -C4 -haloalkyl, C1 -C4 -alkoxy, C1 -C4 -haloalkoxy, NH--O--C1 -C4 -alkyl, C1 -C4 -alkylthio or CR3 is linked to CR14 as indicated above to give a 5- or 6-membered ring;

    R4 and R5 , which can be identical or different, are phenyl or naphthyl, 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, C1 -C4 -alkylthio, amino, C1 -C4 -alkylamino or C1 -C4 -dialkylamino;

    orphenyl or naphthyl, which are connected together in the ortho position via a direct linkage, a methylene, ethylene or ethenylene group, an oxygen or sulfur atom or an SO2, NH or N-alkyl group;

    orC3 -C7 -cycloalkyl;

    R6 hydrogen, C1 -C8 -alkyl, C3 -C6 -alkenyl, C3 -C6 -alkynyl or C3 -C8 -cycloalkyl, where each of these radicals can be substituted one or more times by;

    halogen, nitro, cyano, C1 -C4 -alkoxy, C3 -C6 -alkenyloxy, C3 -C6 -alkynyloxy, C1 -C4 -alkylthio, C1 -C4 -haloalkoxy, C1 -C4 -alkylcarbonyl, C1 -C4 -alkoxycarbonyl, C3 -C8 -alkylcarbonylalkyl, C1 -C4 -alkylamino, di-C1 -C4 -alkylamino, phenyl or phenoxy which is substituted one or more times by halogen, nitro, cyano, C1 -C4 -alkyl, C1 -C4 -haloalkyl, C1 -C4 -alkoxy, C1 -C4 -haloalkoxy or C1 -C4 -alkylthio;

    phenyl or naphthyl, each of which can be substituted by one or more of the following radicals;

    halogen, nitro, cyano, hydroxyl, amino, C1 -C4 -alkyl, C1 -C4 -haloalkyl, C1 -C4 -alkoxy, C1 -C4 -haloalkoxy, phenoxy, C1 -C4 -alkylthio, C1 -C4 -alkylamino, C1 -C4 -dialkylamino or dioxomethylene or dioxoethylene;

    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;

    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;

    Y sulfur or oxygen or a single bond;

    Z sulfur, oxygen, --SO-- or --SO2 --.

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