Substituted indolinones, preparation thereof and their use as pharmaceutical compositions

1. A compound of the formula I

or a pharmaceutically acceptable salt thereof, wherein:

X is an oxygen or sulphur atom,

R 1 is a hydrogen atom, a C 1-4 -alkoxycarbonyl or C 2-4 -alkanoyl group,

R 2 is a pyridinyl group;

R 3 is a hydrogen atom or a C 1-6 -alkyl group,

a phenyl group optionally substituted by a fluorine, chlorine or bromine atom, by a C 1-3 -alkyl, hydroxy, C 1-3 -alkoxy, C 1-3 -alkylsulphenyl, C 1-3 -alkylsulphinyl, C 1-3 -alkylsulphonyl, phenylsulphenyl, phenylsulphinyl, phenylsulphonyl, nitro, amino, C 1-3 -alkylamino, di-(C 1-3 -alkyl)-amino, C 2-5 -alkanoylamino or N—(C 1-3 -alkylamino)-C 2-5 -alkanoylamino group,

R4 is a phenyl or naphthyl group substituted by R 7 , which may additionally be substituted by a chlorine or bromine atom or a nitro group,

R 5 and R 6 in each case independently of one another are hydrogen atoms or C 1-3 -alkyl groups, and

R 7 is a a C 1-3 -alkyl group which is substituted by a piperidino group, while the abovementioned piperidino group may be substituted by one or two C 1-3 -alkyl groups, which may in turn be terminally substituted by a hydroxy, amino or C 2-4 -alkanoylamino group, or by a C 5-7 -cycloalkyl or phenyl group and by a hydroxy group and in the abovementioned piperidino group a methylene group adjacent to the nitrogen atom may be replaced by a carbonyl group.

2. A compound of formula I according to claim 1 wherein the sulfonylamino group of the formula R 2 —SO 2 NR 6 — is linked to the 5-position of the indolinone group.

3. A compound of formula I according to claim 1 , wherein:

R 3 is a phenyl group optionally substituted by a fluorine, chlorine or bromine atom, by a C 1-3 -alkyl, hydroxy, C 1-3 -alkoxy, C 1-3 -alkylsulphenyl, C 1-3 -alkylsulphinyl, C 1-3 -alkylsulphonyl, phenylsulphenyl, phenylsulphinyl, phenylsulphonyl, nitro, amino, C 1-3 -alkylamino, di-(C 1-3 alkyl)-amino, C 2-5 -alkanoylamino or N—(C 1-3 -alkylamino)-C 2-5 -alkanoylamino group.

4. A compound of formula I according to claim 1 , wherein:

X is an oxygen atom,

R 1 is a hydrogen atom,

R 2 is a pyridinyl group,

R 3 is a hydrogen atom or a C 1-4 -alkyl group, or

a phenyl group optionally substituted by a fluorine, chlorine, bromine or iodine atom, by a C 1-3 alkyl, C 1-3 -alkoxy, nitro or amino group,

R 4 is a phenyl group substituted by R 7 ,

R 5 and R 6 in each case denote a hydrogen atom, and

R 7 is a a C 1-3 -alkyl group which is substituted by a piperidino group, while the abovementioned piperidino group may be substituted by one or two C 1-3 -alkyl groups, which may in turn be terminally substituted by a hydroxy, amino or C 2-4 -alkanoylamino group, and at the same time in the abovementioned piperidino group a methylene group in the 2 position may be replaced by a carbonyl group.

5. A compound of formula I according to claim 1 , wherein:

R 2 is a pyridinyl group,

R 3 is a phenyl group optionally substituted by a fluorine, chlorine, bromine or iodine atom, by a C 1-3 -alkyl, C 1-3 -alkoxy, nitro or amino group,

R 4 is a phenyl group which is substituted by R 7 and additionally by a chlorine atom or a nitro group, while

R 7 is a methyl or ethyl group which is substituted by a piperidino group.

6. A compound of formula I according to claim 1 , wherein R 4 is a phenyl group substituted in the 4 position by R 7 .

7. A compound of formula IB

wherein R 2 and R 7 are defined as in claim 1 , 4 or 5 .

8. A compound of formula IB according to claim 7 wherein:

R 7 is selected from the group consisting of: (2,6-dimethylpiperidino)-methyl and 2-oxopiperidinomethyl; and

R 2 is pyrid-2-yl or pyrid-3-yl.

9. (Z)-3-{1-[4-(piperidinomethyl)-phenylamino]-1-phenyl-methylidene}-5-(pyridin-3-ylsulphonylamino)-2-indolinone, or a pharmaceutically acceptable salt thereof.

10. A pharmaceutical preparation comprising a compound according to claim 1 , 2 , 3 , 4 , 5 , 6 , or 9 and a pharmaceutically acceptable carrier.