Indolone-acetamide derivatives, processes for preparing them and their uses

1. A compound of the formula I or a pharmaceutically acceptable salt thereof or stereoisomeric forms thereof,

wherein

R 1 is hydrogen,

R 2 is hydrogen or C 1-20 -alkyl,

R 3 is hydrogen, C 1-20 -alkyl, C 4-8 -cycloalkyl, C 5-8 -cycloalkylenyl, aryl, C 1-20 -alkoxy, or a group of formula —W-R 8 ;

R 3a is hydrogen or C 1-20 -alkyl,

R 4 is hydrogen,

R 5 is halogen or trifluoromethyl,

R 6 is hydrogen, C 1-20 -alkyl or halogen,

R 7 is hydrogen, C 1-20 -alkyl or halogen,

W is C 1-12 -alkylene, —NH— or —NHC(═O)—, and

R 8 is aryl.

2. A compound of the formula I or a pharmaceutically acceptable salt thereof or stereoisomeric forms thereof,

wherein

R 1 is hydrogen,

R 2 is hydrogen or C 1-4 alkyl,

R 3 is hydrogen; C 1-6 -alkyl unsubstituted or substituted by 1 to 5 substituents selected from halogen, hydroxy, alkoxy, alkoxycarbonyl and alkylamino; C 5-7 -cycloalkyl; (hydroxymethyl) cyclohexenyl; phenyl unsubstituted or substituted by 1 to 5 substituents selected from halogen, C 1-4 -alkyl, hydroxy, methoxy, nitro, methylsulfonyl, and trifluoromethylthio; or a group of formula —W-R 8 ,

R 3a is hydrogen, C 1-4 -alkyl,

R 4 is hydrogen,

R 5 is halogen or triflouromethyl,

R 6 is hydrogen, C 1-6 -alkyl or halogen,

R 7 is hydrogen, methyl or halogen,

W is C 1-4 -alkylene unsubstituted or substituted by halogen, hydroxy, C 1-4 -alkyl or alkoxy; —NH—; or —NHC (═O)—, and

R 8 is phenyl unsubstituted or substituted by 1 to 5 substituents selected from halogen, C 1-4 -allyl, hydroxy, methoxy, nitro, methylsulfonyl or triflouromethylthio.

3. A compound of the formula I or a pharmaceutically acceptable salt thereof or stereoisomeric forms thereof,

wherein

R 1 is hydrogen,

R 2 is hydrogen, methyl or ethyl,

R 3 is hydrogen, n-butyl, cycloheptyl, 2-fluoroethyl, 3-hydroxypropyl, 3-hydroxy-2,2-dimethylpropyl, 1-(hydroxymethyl)propyl, 3,3,3-trifluoro-2-hydroxypropyl, 3-ethoxypropyl, 2-ethoxy-2-oxoethyl, 3-(dimethylamino)propyl, 6-(hydroxymethyl) cyclohex-3-en-l-yl, 3-hydroxyphenyl, 3-fluorophenyl, 3-(2-pyridin-2-ylethyl) phenyl, 3,4-dimethylphenyl, 4-tert-butylphenyl, benzyl, 4-hydroxy-3-methoxybenzyl, 4-methylsulfonylbenzyl, 2-nitrobenzyl,2-chloro-6-fluorobenzyl, 2-[(trifluoromethyl) thio]benzyl, 2-hydroxy-2-phenylethyl, 2-(3,4-dimethoxyphenyl)ethyl, 2-(2-chloropheny 1)ethyl, 2-(4-methylphenyl)ethyl, [4-bromophenyl)amino, or methoxy,

R 3a is hydrogen, methyl,

R 4 is hydrogen,

R 5 is halogen,

R 6 is hydrogen, methyl or Cl, and

R 7 is hydrogen, methyl, Br, F or Cl.

4. A compound according to claim 1 wherein R 2 is hydrogen or methyl.

5. A compound according to claim 1 wherein R 3 is hydrogen.

6. A compound according to claim 1 wherein R 3a is hydrogen.

7. A compound according to claim 1 wherein R 6 is hydrogen.

8. A compound according to claim 1 wherein R 7 is hydrogen, Br, or F.

9. A compound according to claim 1 wherein R 2 is C 1-20 -alkyl and the carbon atom to which R 2 is attached is in the “S”-configuration.

10. A compound selected from

2-(5-iodo-2-oxo-2,3-dihydro-1H-indol-1-yl)acetamide;

2-(5-chloro-2-oxo-2,3-dihydro-1H-indol-1-yl)acetamide;

2-(5,7-dibromo-2-oxo-2,3-dihydro-1H-indol-1-yl)acetamide;

2-(5-chloro-2-oxo-2,3-dihydro-1H-indol-1-yl)propanamide;

(2R)-2-(5-chloro-2-oxo-2,3-dihydro-1H-indol-1-yl)propanamide;

(2S)-2-(5-chloro-2-oxo-2,3-dihydro-1H-indol-1-yl)propanamide;

2-(5-fluoro-2-oxo-2,3-dihydro-1H-indol-1-yl)acetamide;

2-(5-bromo-2-oxo-2,3-dihydro-1H-indol-1-yl)acetamide;

2-(2-oxo-5-(trifluoromethyl)-2,3-dihydro-1H-indol-1-yl)acetamide;

2-(5-chloro-2-oxo-2,3-dihydro-1H-indol-1-yl)butanamide;

(+)-2-(5-chloro-2-oxo-2,3-dihydro-1H-indol-l-yl)butanamide;

(−)-2-(5-chloro-2-oxo-2,3-dihydro-1H-indol-1-yl)butanamide;

2-(5-bromo-2-oxo-2,3-dihydro-1H-indol-1-yl)propanamide;

(−)-2-(5-bromo-2-oxo-2,3dihydro-1H-indol-1-yl )propanamide;

(+)-2-(5-bromo-2-oxo-2,3-dihydro-1H-indol-1-yl )propanamide;

2-(5-chloro-7-fluoro-2-oxo-2,3-dihydro-1H-indol-1-yl)acetamide;

2-(5-chloro-2-oxo-2,3-dihydro-1H-indol-1-yl)-N-(3-hydroxyphenyl)acetamide;

2-(5-chloro-2-oxo-2,3-dihydro-1H-indol-1-yl)-N-(3-fluoroplenyl)acetamide;

2-(5-chloro-2-oxo-2,3-dhydro-1H-indol-1-yl)-N-[6-(hydroxymethyl)cyclohex-3-en-1-yl]acetamide;

2-(5-chloro-2-oxo-2,3-dihydro-1H-indol-1-yl)-N-(4-hydroxy-3-methoxybenzyl )acetamide;

2-(5-chloro2-oxo-2,3-dihydro-1H-indol-1-yl)-N-[4-(methylsulfonyl)benzyl]acetamide;

N′-(4-bromophenyl)-2-(5-chloro-2-oxo-2,3-dihydro-1H-indol-1-yl)acetohydrazide;

N-butyl-2-(5-chloro-2-oxo-2,3-dihydro-1H-indol-1-yl) acetamide;

2-(5-chloro-2-oxo-2,3-dihydro-1H-indol-1-yl)-N-(3-hydroxypropyl)acetamide;

2-(5-chloro-2-oxo-2,3-dihydro-1H-indol-1-yl)-N-[3-(dimethylamino)propyl]acetamide;

ethyl {[(5-chloro-2-oxo-2,3-dihydro-1H-indol-1-yl)acetyl]amino}acetate;

2-(5-chloro-2-oxo-2,3-dihydro-1H-indol-1-yl)-N-(3-ethoxypropyl)acetamide;

2-(5-chloro-2-oxo-2,3-dihydro-1H-indol-1-yl)-N-(2-fluoroethyl)acetamide;

2-(5-chloro-2-oxo-2,3-dihydro-1H-indol-1-yl)-N-methoxy-N-methylacetamide;

2-(5-chloro-2-oxo-2,3-dihydro-1H-indol-1-yl)-N-(3,4-dimethylphenyl)acetamide;

N-(4-tert-butylphenyl)-2-(5-chloro-2-oxo-2,3-dihydro-1H-indol-1-yl) acetamide;

2-(5-chloro-2-oxo-2,3-dihydro-1H-indol-1-yl)-N-(3-hydroxy-2,2-dimethylpropyl)acetamide;

2-(5-chloro-2-oxo-2,3-dihydro-1H-indol-1-yl)-N-[1-(hydroxymethyl)propyl]acetamide;

2-(5-chloro-2-oxo-2,3-dihydro-1H-indol-1-yl)-N-(3,3,3-trifluoro-2-hydroxypropyl)acetamide;

2-(5-chloro-2-oxo-2,3-dihydro-1H-indol-1-yl)-N-(2-hydroxy-2-phenylethyl) acetamide;

2-(5-chloro-2-oxo-2,3-dihydro-1H-indol-1-yl)-N-[2-(3,4-dimethoxyphenyl)ethyl]acetamide;

2-(5-chloro-2-oxo-2,3-dihydro-1H-indol-1-yl)-N-[2-(2-chlorophenylethyl]acetamide;

2-(5-chloro-2-oxo-2,3-dihydro-1H-indol-1-yl)-N-[2-(4-methylphenyl)ethyl]acetamide;

2-(5-chloro-2-oxo-2,3-dihydro-1H-indol-1-yl)-N-[2-(3,4,5,6-tetrahydro-1-benzazocin-1(2H)-yl)propyl]acetamide;

2-(5-chloro-2-oxo-2,3-dihydro-1H-indol-1-yl)-N-(2-nitrobenzyl)acetamide;

N-(2-chloro-6-fluorobenzyl)-2-(5-chloro-2-oxo-2,3-dihydro-1H-indol-1-yl) acetamide;

N-benzyl-2-(5-chloro-2-oxo-2,3-dihydro-1H-indol-1-yl)-N-methylacetamide;

2-(5-chloro-2-oxo-2,3-dihydro-1H-indol-1-yl)-N-{2-[(trifluoromethyl)thio]benzyl}acetamide;

2-(5-chloro-2-oxo-2,3-dihydro-1H-indol-1-yl)-N-cycloheptylacetamide; and

pharmaceutically acceptable salts thereof.

11. A pharmaceutical composition comprising an effective amount of a compound according to claim 1 in combination with a pharmaceutically acceptable diluent or carrier.