Indolin-2-one derivatives preparation thereof and intermediates for the preparation thereof

Abstract

Abstract The present invention provides indolin-2-one derivatives of the general formula: <IMAGE> (I) wherein R1 is a C1-C6 alkyl radical or a radical of the general formula: <IMAGE> in which A is a straight-chained or branched C2-C4 alkylene radical and Z is an oxygen or sulphur atom, R2 and R3, which can be the same or different, are hydrogen or halogen atoms, hydroxyl groups, C2-C6 alkanoyl radicals, C2-C4 alkenyl radicals, C2-C4 alkynyl radicals, C1-C6 alkyl radicals, C1-C6 alkoxy radicals, C2-C4 alkenyloxy radicals, C2-C4 alkynyloxy radicals, C1-C6 alkylthio radicals, C2-C6 alkanoylamido radicals or radicals of the general formula: <IMAGE> in which R4 and R5, which can be the same or different, are hydrogen atoms, C1-C6 alkyl radicals or C3-C10 cycloalkyl radicals or R4 and R5 together represent a C2-C8 alkylene radical optionally interrupted by an oxygen or sulphur atom or by an >N-R6 group, in which R6 is a hydrogen atom or a C1-C6 alkyl radical, X is a hydrogen atom, Y is a hydrogen atom or a group of the general formula <IMAGE> in which Q is a hydrogen atom or, together with X, can also represent a bond and R7 is a heterocyclic radical which is optionally substituted one or more times by hydroxyl or C1-C6 alkyl or is a phenyl radical which is optionally substituted one or more times by halogen, hydroxyl, mercapto, carboxyl, C1-C6 alkoxycarbonyl, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylsulphinyl, C114 C6 alkylsulphonyl, C2-C6 alkanoylamido, C1-C6 alkylsulphonylamido, methylenedioxy, nitro, cyano or amino, with the proviso that R1 cannot be a C1-C6 alkyl radical when X and Y are both hydrogen atoms; as well as the pharmacologically acceptable salts thereof. The present invention also provides intermediates of the general formula: <IMAGE> (V) in which R7 is a heterocyclic radical which is optionally substituted one or more times by hydroxy or C1-C6 alkyl or is a phenyl radical which is optionally substituted one or more times by hydroxyl, halogen, mercapto, carboxyl, C1-C6 alkoxycarbonyl, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, C114 C6 alkylsulphinyl, cyano C1-C6 alkylsulphonyl, C2-C6 alkanoylamido, C1-C6 alkylsulphonylamido, nitro amino or methylenedioxy. Furthermore, the invention provides processes for the preparation of the above indolin-2-one derivatives and the above intermediates, as well as pharmaceutical compositions containing the above indolin-2-one derivatives.

Inventors

• 👤 Helmut Michel
• 👤 Klaus Marzenell
• 👤 Wolfgang Kampe
• 👤 Wolfgang Bartsch
• 👤 Wolfgang Schaumann

Bibliographic Details