Substituted indolinones, preparation thereof and their use as pharmaceutical compositions

A compound of the formula I

• or a pharmaceutically acceptable salt thereof, wherein:
• X is an oxygen or sulphur atom,
• R1 is a hydrogen atom, a C1-4-alkoxycarbonyl or C2-4-alkanoyl group,
• R2 is:
• (a) a C1-6-alkyl group optionally substituted by one or more halogen atoms or a phenyl group or a C2-6-alkenyl group optionally substituted by a phenyl group, wherein the phenyl moiety may be substituted in each case by a fluorine, chlorine, bromine or iodine atom, by a C1-3-alkyl or C1-3-alkoxy group,
• (b) phenyl group which may be mono- or disubstituted by fluorine, chlorine, bromine or iodine atoms, by C1-3-alkyl or C1-3-alkoxy groups, wherein the substituents may be identical or different,
• (c) a phenyl group substituted by a trifluoromethyl, carboxy, C1-3-alkoxycarbonyl, aminocarbonyl, cyano, aminomethyl, nitro or amino group,
• (d) a C4-6-alkyl group,
• (e) a C3-7-cycloalkyl group,
• (f) trimethylphenyl group, or
• (g) a naphthyl group,
• R3 is a hydrogen atom or a C1-6-alkyl group,
• a phenyl group optionally substituted by a fluorine, chlorine or bromine atom, by a C1-3-alkyl, hydroxy, C1-3-alkoxy, C1-3-alkylsulphenyl, C1-3-alkylsulphinyl, C1-3-alkylsulphonyl, phenylsulphenyl, phenylsulphinyl, phenylsulphonyl, nitro, amino, C1-3-alkylamino, di-(C1-3-alkyl)-amino, C2-5-alkanoylamino or N-(C1-3-alkylamino)-C2-5alkylamino group,
• R4 is a phenyl or naphthyl group optionally substituted by R7, which may additionally be substituted by a chlorine or bromine atom or a nitro group,
• R5 and R6 in each case independently of one another are hydrogen atoms or C1-3-alkyl groups, and
• R7 is:
• (a) a halogen atom selected from the group consisting of fluorine, chlorine, bromine and iodine,
• (b) a cyano group,
• (c) a methoxy groups,
• (d) a C2-3-alkoxy group, which may be substituted in the 2 or 3 position by an amino, C1-3-alkylamino, or di-(C1-3-alkyl)-amino group, while in each case an alkyl moiety in the abovementioned alkylamino and dialkylamino groups may additionally be substituted by a phenyl group,
• (e) a trifluoromethyl group,
• (f) a nitro grow,
• (g) an amino, C1-3-alkylamino, di-(C1-3-alkyl)-amino, C2-5-alkanoylamino, N-(C1-3-alkyl)-C2-5-alkanoylamino, C1-5-alkylsulphonylamino, N-(C1-3-alkyl)-C1-5-alkylsulphonylamino, phenylsulphonylamino, N-(C1-3-alkyl)-phenylsulphonylamino aminosulphonyl, C1-3-alkylaminosulphonyl or di-(C1-3-alkyl)-aminosulphonyl group, while in each case an alkyl moiety in the abovementioned alkylamino and dialkylamino groups may additionally be substituted by a carboxy, C1-3-alkoxycarbonyl, aminocarbonyl, C1-3-alkylaminocarbonyl, di-(C1-3-alkyl)-aminocarbonyl, 2-dimethylaminoethylaminocarbonyl or N-methyl-(2-dimethylaminoethyl)-aminocarbonyl group and in each case the alkyl moiety of the abovementioned alkanoylamino or alkysulphonylamino groups may additionally be substituted by a phenyl, amino, C1-3-alkylamino, or di-(C1-3-alkyl)-amino group,
• (g) a C2-4-allcylarnino group which is terminally substituted in the 2, 3- or 4 position by an amino, C1-3-alkylamino, di-(C1-3-alkyl)-amino, benzylamino, N-(C1-3-alkyl)-benzylamino, C2-5-alkanoylamino or N-(C1-3-alkyl)-C2-5-alkanoylamino group and wherein additionally the amino-hydrogen atom may be replaced by a C2-5-alkanoyl, benzoyl, C1-5-alkylsulphonyl- or phenylsulphonyl group, while the last-mentioned C2-5-alkanoyl or C1-5-alkylsulphonyl groups in the alkyl moiety may be substituted by a phenyl group,
• (h) a carbonyl group which is substituted by a hydroxy, C1-3-alkoxy, amino, C1-3-alkylamino or;
• N-(C1-5-alkyl)-C1-3-alkylamino group;
• (i) a C1-4-alkyl group which may be substituted by an amino, C1-5-alkylamino;
• or phenyl-C1-3-alkylamino group which may additionally be substituted at the amino nitrogen atom in each case by a C1-4-alkyl, C2-4alkenyl- or C1-4-alkyl group, while
• the abovementioned C1-4-alkyl substituent in each case may additionally be mono-, di- or trisubstituted by a cyano, carboxy, C1-3-alkoxycarbonyl, C2-4-alkanoyl, benzo[1,3]dioxol or phenyl group, while the phenyl group may be substituted by fluorine, chlorine or bromine atoms, by methyl, methoxy, trifluoromethyl, cyano or nitro groups and the substituents may be identical or different, or in the 2, 3 or 4 position by a hydroxy group, or
• (j) a C1-3-alkyl group which is substituted by a hydroxy or carboxy.