Patent ID: 6610691
Filing Date: 2003-08-26
Classification: A61P,C07D

Abstract:
A compound of formula I where R is a group â€”(CO)â€”R1 where R1 is:a) a radical â€ƒwhere m is 0 or 1 and R7 and R8, which can be identical or different, have the following meanings: hydrogen, C1-C8-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, C3-C8-cycloalkyl, it being possible for these alkyl, cycloalkyl, alkenyl and alkynyl groups each to carry one to five halogen atoms, and/or one or two of the following groups: C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-haloalkoxy, C3-C6-alkenyloxy, C3-C6-alkenlthio, C3-C6-alkynyloxy, C3-C6-alkynylthio, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl, C3-C6-alkenylcarbonyl, C3-C6-alkynylcarbonyl, C3-C6-alkenyloxycarbonyl and C3-C6-alkynyloxycarbonyl, phenyl, unsubstituted or 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, di-C1-C4-alkylamino, R7 and R8 are furthermore phenyl which is unsubstituted or substituted by one or more of the following radicals: halogen, nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or C1-C4-alkylthio, or R7 and R8 together form a C4-C7-alkylene chain which is closed to form a ring and may contain a hetero atom selected from the group of oxygen, sulfur or nitrogen; b) a group â€ƒin which k assumes the values 0, 1 and 2, p assumes the values 1, 2, 3 and 4, and R9 is C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-alkenyl, C3-C6-alkynyl or phenyl which is unsubstituted or substituted by one or more of the following radicals: halogen, nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or C1-C4-alkylthio; c) a radical â€”OR10 where R10 is: hydrogen, an ammonium ion, the cation of an alkali metal, the cation of an alkaline earth metal or a tertiary C1-C4-alkyl ammonium; C3-C8-cycloalkyl, which can carry one to three C1-C4-alkyl groups; C1-C8-alkyl which can carry one to five halogen atoms and/or one of the following radicals: C1-C4-alkoxy, C1-C4-alkylthio, cyano, C1-C4-alkylcarbonyl, C3-C8-cycloalkyl, C1-C4-alkoxycarbonyl, phenyl, phenoxy or phenylcarbonyl, it being possible for the aromatic radicals in turn each to carry one to five halogen atoms and/or one to three of the following radicals: nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy and/or C1-C4-alkylthio; a C1-C8-alkyl group which can carry one to five halogen atoms and carries a 5-membered heteroaromatic system consisting of one to three nitrogen atoms and two to four carbon atoms, or a 5-membered heteroaromatic system consisting of one nitrogen atom, one oxygen or sulfur atom, and three carbon atoms wherein said 5-membered heteroaromatic system consisting of one to three nitrogen atoms and two to four carbon atoms can carry one to four halogen atoms and/or one or two of the following radicals: nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, phenyl, C1-C4-haloalkoxy and/or C1-C4-alkylthio; a C2-C6-alkyl group which carries in position 2 one of the following radicals: C1-C4-alkoxyimino, C3-C6-alkynyloxyimino, C3-C6-haloalkenyloxyimino or benzyloxyimino; a C3-C6-alkenyl or a C3-C6-alkynyl group, it being possible for these groups in turn to carry one to five halogen atoms; R10 is furthermore 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, C1-C4-alkoxy, C1-C4-haloalkoxy and/or C1-C4-alkylthio; a 5-membered heteroaromatic system which is linked via a nitrogen atom and consists of one to three nitrogen atoms and which can 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 or C1-C4-alkylthio; R10 is furthermore a group â€ƒwhere R11 and R12, which can be identical or different, are: C1-C8-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 which is unsubstituted or substituted by one or more of the following radicals: halogen, nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or C1-C4-alkylthio; phenyl which is unsubstituted or substituted by one or more of the following radicals: halogen, nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or C1-C4-alkylthio, or R11 and R12 together form a C3-C12-alkylene chain which may carry one to three C1-C4-alkyl groups and optionally contains a hetero atom from the group of oxygen, sulfur and nitrogen; d) a radical â€ƒwhere R13 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 phenyl radical; phenyl which is unsubstituted or substituted by one or more of the following: halogen, nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or C1-C4-alkylthio; or e) a radical â€ƒwhere R13 has the abovementioned meaning; R2 is halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or C1-C4-alkylthio; X is nitrogen or CR14, where R14 is hydrogen or C1-5-alkyl, or CR14 forms together with CR3 a 5- or 6-membered alkylene or alkenylene ring which can be substituted by one or two C1-4-alkyl groups and in which in each case one methylene group can be replaced by oxygen, sulfur, â€”NH or â€”NC1-4-alkyl; R3 is halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, â€”NHâ€”Oâ€”C1-4-alkyl, C1-C4-alkylthio or CR3 is linked to CR14 as indicated above to form a 5- or 6-membered ring; R4 and R5, which may be identical or different, are: phenyl or naphthyl, each of 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; or phenyl or naphthyl which are connected together in ortho positions by a direct linkage, a methylene, ethylene or ethenylene group, an oxygen or sulfur atom or SO2, NH or N-alkyl group, or C3-C7-cyloalkyl; R6 is C1-C10-alkyl, C3-C10-alkenyl or C3-C10-alkynyl, the radicals each being substituted one or more times by hydroxyl, mercapto, carboxyl, sulfonyl, guanidino, or â€ƒwhere Ry and Rz are, independently of one another, hydrogen or C1-C5-alkyl; and Z is sulfur or oxygen.