IP Library Granted Patent US 8,486,931
Granted Patent B2
US 8,486,931 · App. 12/529,542 · Granted Jul 16, 2013

Substituted oxindole compounds

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Quick Facts
Patent No.
US 8,486,931
App. No.
12/529,542
Granted
Jul 16, 2013
Kind
B2
Abstract

The present invention relates to compounds of the general formula (I) in which A, B, R 1 , R 2 and Het have the meaning given in claim 1; Y is a bivalent group of the formula in which D is C 1 -C 3 -alkylene, where D may have a substituent R 5 ; R 3 is hydrogen, C 1 -C 8 -alkyl or together with R 4 is C 1 -C 3 -alkylene which may have a radical R 5a , or together with R 5 is C 1 -C 3 -alkylene, and R 4 is hydrogen, C 1 -C 8 -alkyl or together with R 3 is C 1 -C 3 -alkylene which may have a radical R 5a , or together with R 5 is C 1 -C 3 -alkylene, where R 5 together with R 5a , where present, are a bond or C 1 -C 3 -alkylene; and where one of the following conditions is satisfied: R 3 together with R 4 is C 1 -C 3 -alkylene which may have a radical R 5a ; or R 3 together with R 5 is C 1 -C 3 -alkylene; or R 4 together with R 5 is C 1 -C 3 -alkylene where the radical A is different from phenyl when the radical B is phenyl or naphthyl; and medicaments which comprise such compounds and the use thereof for the prophylaxis and/or treatment of vasopressin-dependent and/or oxytocin-dependent diseases.

Claims (215)

1. A compound of the formula (I)

in which

A is 2-methoxyphenyl, 2-ethoxyphenyl, 2-ethoxy-5-methylphenyl, 2-ethoxy-5-ethylphenyl, 2-ethoxy-5-isopropylphenyl, 2-ethoxy-5-cyclopropylphenyl, 2-chlorophenyl, 2,3-dimethoxyphenyl, 2,4-dimethoxyphenyl, 2-ethoxy-4-fluorophenyl, 2,5-dimethoxyphenyl, 2-ethoxy-3-methoxyphenyl, 2-ethoxy-4-methoxyphenyl, 2-ethoxy-5-methoxyphenyl, 2-ethoxy-5-ethyl-phenyl, 2-isopropyloxy-5-methoxyphenyl, 2-methoxy-5-methylphenyl, 2-isobutyloxy-5-methoxyphenyl, 2-methoxy-5-(dimethylaminomethyl)phenyl, 2-methoxy-5-(methylaminomethyl)phenyl, 2-methoxypyridin-3-yl, 2-ethoxypyridin-3-yl, 2-ethoxy-5-methylpyridin-3-yl, 2-ethoxy-5-ethylpyridin-3-yl, 2-ethoxy-5-isopropylpyridin-3-yl, 2-ethoxy-5-cyclopropylpyridin-3-yl, 2-ethoxy-6-methoxypyridin-3-yl, 2-ethoxy-6-dimethylaminopyridin-3-yl, pyridin-2-yl, 3-methylpyridin-2-yl, 6-chloro-2-methoxypyridin-3-yl, 6-chloro-2-ethoxypyridin-3-yl or 2,6-difluoropyridin-3yl;

B is phenyl, pyridin-2-yl, quinolin-5-yl, quinolin-8-yl, or thienyl, where the aforementioned radicals are unsubstituted or have one, two, three or four substituents

R B where

R B is selected independently of one another from halogen, CN, NO 2 , hydroxy, C 1 -C 6 -alkyl, C 3 -C 7 -cycloalkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, amino, C 1 -C 4 alkylamino, and di(C 1 -C 4 -alkyl)amino,

R 1 is hydrogen, halogen, CN, NO 2 , C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy or C 1 C 6 -haloalkoxy,

R 2 is hydrogen, halogen, CN, NO 2 , C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy or C 1 -C 6 -haloalkoxy,

Y is selected from the groups

in which

* is the linkage to the oxindole unit,

#is the linkage to the Het group,

and

Het is selected from a 2-pyridyl, 3-pyridyl, 4-pyridyl, 4-pyrimidinyl, 2-triazinyl, 1,3-thiazol-2-yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, piperazin-1-yl or piperazin-2-yl radical, where the radical is unsubstituted or has one, two or three identical or different substituents R Het which are selected independently of one another from halogen, CN, NO 2 , C 1 -C 6 -alkyl, C 3 -C 7 -cycloalkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkyloxy, C 1 -C 6 -haloalkoxy, C 3 -C 7 -cycloalkoxy, di(C 1 -C 6 -alkyl)amino, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulfonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -alkenyloxy and C 2 -C 6 -alkynyloxy,

where the radical A is different from 2-methoxyphenyl, 2-ethoxyphenyl, 2-ethoxy-5-methylphenyl, 2-ethoxy-5-ethylphenyl, 2-ethoxy-5-isopropylphenyl, 2-ethoxy-5-cyclopropylphenyl, 2-chlorophenyl, 2,3-dimethoxyphenyl, 2,4-dimethoxyphenyl, 2-ethoxy-4-fluorophenyl, 2,5-dimethoxyphenyl, 2-ethoxy-3-methoxyphenyl, 2-ethoxy-4-methoxyphenyl, 2-ethoxy-5-methoxyphenyl, 2-ethoxy-5-ethyl-phenyl, 2-isopropyloxy-5-methoxyphenyl, 2-methoxy-5-methylphenyl 2-isobutyloxy-5-methoxyphenyl 2-methoxy-5-(dimethyl-aminomethyl)phenyl, and 2-methoxy-5-(methylaminomethyl)phenyl when the radical B is phenyl which is unsubstituted or has one, two, three or four substituents R B ,

or a tautomeric, enantiomeric and/or diastereomeric form thereof, or a physiologically tolerated salt or N-oxide of said compound.

2. The compound of the formula (I) according to claim 1 , in which A is 2-methoxy-phenyl, 2-ethoxyphenyl, 2,5-dimethoxyphenyl or 2-ethoxy-5-methoxyphenyl.

3. The compound of the formula (I) as claimed in claim 1 , in which B is pyridin-2-yl or quinolin-8-yl which is unsubstituted or has one, two, three or four substituents R B .

4. The compound of the formula (I) as claimed in claim 3 , in which B is pyridin-2-yl or quinolin-8-yl which is unsubstituted or has a substituent R B in position 5.

5. The compound of the formula (I) as claimed in claim 3 , in which B is pyridin-2-yl, 5-methylpyridin-2-yl, 5-methoxypyridin-2-yl, quinolin-8-yl, 3-methylquinolin-8-yl, 4-methylquinolin-8-yl, 5-methylquinolin-8-yl, 5-methoxyquinolin-8-yl, 4-ethyl-8-quinolinyl, 5-ethoxyquinolin-8-yl, 5-chloroquinolin-8-yl, or 5-fluoroquinolin-8-yl.

6. The compound of the formula (I) as claimed in claim 5 , in which B is 5-methoxy-pyridin-2-yl, quinolin-8-yl or 5-methoxyquinolin-8-yl.

7. The compound of the formula (I) as claimed in claim 1 , in which

B is phenyl and is unsubstituted or has one, two, three or four substituents R B .

8. The compound of the formula (I) as claimed in claim 7 , in which A is 6-chloro-2-ethoxypyridin-3-yl.

9. The compound of the formula (I) as claimed in claim 7 , in which B is 2,3-dimethoxyphenyl, 2,4-dimethoxyphenyl, 3,5-dimethoxyphenyl, 2-ethoxy-4-methoxyphenyl, 4-amino-2-methoxyphenyl, 4-methoxy-2-nitrophenyl, or 2-trifluoromethyl-4-cyanophenyl.

10. The compound of the formula (I) as claimed in claim 9 , in which B is 2,4-dimethoxyphenyl.

11. The compound of the formula (I) as claimed in claim 1 , in which R 1 is CN, chlorine, methyl or methoxy.

12. The compound of the formula (I) as claimed in claim 1 , in which R 2 is hydrogen.

13. The compound of the formula (I) as claimed in claim 1 , in which Y is selected from the groups

14. The compound of the formula (I) as claimed in claim 13 , in which Y is piperazine-1,4-diyl, piperidine-1,4-diyl or homopiperazine-1,4-diyl.

15. The compound of the formula (I) as claimed in claim 1 , in which

Het is selected from pyridin-4-yl, pyridin-3-yl, pyridin-2-yl, 2-methylpyridin-4-yl, 3-methylpyridin-4-yl, 3-ethylpyridin-4-yl, 3-cyclopropylpyridin-4-yl, 2-ethoxypyridin-4-yl, 2-fluoropyridin-4-yl, 2-chloropyridin-4-yl, 2-isopropylpyridin-4-yl, 3-isopropylpyridin-4-yl and 3-fluoropyridin-4-yl.

16. The compound of the formula (I) as claimed in claim 15 , in which Het is pyridin-4-yl which is unsubstituted or has a substituent R Het .

17. The compound of the formula (I) as claimed claim 1 , in which

Het is a piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, piperazin-1-yl or piperazin-2-yl radical which is unsubstituted or has one, two or three identical or different substituents R Het which are selected independently of one another from halogen, CN, NO 2 , C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkyloxy, C 1 -C 6 -haloalkoxy and C 3 -C 7 -cycloalkyl.

18. The compound of the formula (I) as claimed in claim 1 , in which the group Y-Het is one of the following radicals:

in which * indicates the linkage to the oxindole unit, R Het-1 is hydrogen, methyl or isopropyl, and in which R Het-2 is hydrogen or methyl.

19. A pharmaceutical composition comprising a compound according to claim 1 or pharmaceutically acceptable salt thereof, and a pharmaceutical carrier.

20. A compound according to claim 1 , or a pharmaceutically acceptable salt thereof, wherein the compound is selected from the group consisting of 5-Chloro-3-(2,4-dimethoxyphenyl)-3-(4-pyridin-4-ylpiperazin-1-yl)-1-(quinoline-8-sulfonyl)-1,3-dihydroindol -2-one;

5-Chloro-3-(2,3-dimethoxyphenyl)-3-(4-pyridin-4-ylpiperazin-1-yl)-1-(quinoline-8-sulfonyl)-1,3-dihydroindol -2-one (hydrochloride);

5-Cyano-1-(2,4-dimethoxybenzenesulfonyl)-3-(2-ethoxypyridin-3-yl)-3-(4-pyridin-4-ylpiperazin-1-yl)-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(2-methoxypyridin-3-yl)-3-(4-pyridin-4-ylpiperazin-1-yl)-1-(quinoline-8-sulfonyl)-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(2-ethoxypyridin-3-yl)-3-(4-pyridin-4-ylpiperazin-1-yl)-1-(quinoline-8-sulfonyl)-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(2-ethoxyphenyl)-3-(2-methyl-4-pyridin-4-ylpiperazin-1-yl)-1-(quinoline-8-sulfonyl)-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(2-ethoxyphenyl)-1-(3-methylquinoline-8-sulfonyl)-3-(4-pyridin-4-yl-piperazin-1-yl)-2,3-dihydro-1H-indol -2-one;

5-Chloro-3-pyridin-2-yl-3-(4-pyridin-4-ylpiperazin-1-yl)-1-(quinoline-8-sulfonyl)-1,3-dihydroindol-2-one;

5-Chloro-3-(3-methylpyridin-2-yl)-3-(4-pyridin-4-ylpiperazin-1-yl)-1-(quinoline-8-sulfonyl)-1,3-dihydroindol -2-one;

5-Chloro-3-(6-chloro-2-methoxypyridin-3-yl)-3-(4-pyridin-4-ylpiperazin-1-yl)-1-(quinoline-8-sulfonyl)-1,3-dihydroindol -2-one;

5-Cyano-3-(2-ethoxyphenyl)-1-(5-methylpyridine-2-sulfonyl)-3-(4-pyridin-4-yl-piperazin-1-yl)-2,3-dihydro-1H-indol -2-one;

5-Cyano-1-(5-chloroquinoline-8-sulfonyl)-3-(2-ethoxyphenyl)-3-(4-pyridin-4-yl-piperazin-1-yl)-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(2-ethoxy-5-methoxyphenyl)-3-(4-pyridin-4-yl-piperazin-1-yl)-1-(quinoline-8-sulfonyl)-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(2-ethoxyphenyl)-1-(pyridine-2-sulfonyl)-3-(4-pyridin-4-yl-piperazin-1-yl)-2,3-dihydro-1H-indol-2-one;

5-Cyano-3-(2-ethoxyphenyl)-3-[4-(3-methylpyridin-4-yl)-piperazin-1-yl]-1-(quinoline-8-sulfonyl)-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(2-ethoxyphenyl)-1-(4-methylquinoline-8-sulfonyl)-3-(4-pyridin-4-yl-piperazin-1-yl)-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(2-ethoxyphenyl)-3-(3-methyl-4-pyridin-4-ylpiperazin-1-yl)-1-(quinoline-8-sulfonyl)-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(2-ethoxy-5-methoxyphenyl)-3-[4-(2-methylpyridin-4-yl)piperazin-1-yl]-1-(4-methylquinoline-8-sulfonyl)-2,3-dihydro-1H-indol-2-one;

5-Cyano-3-(6-chloro-2-methoxypyridin-3-yl)-3-(4-pyridin-4-ylpiperazin-1-yl)-1-(quinoline-8-sulfonyl)-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(2-ethoxy-5-methoxyphenyl)-1-(5-methylpyridine-2-sulfonyl)-3-((1S,4S)-5-pyridin-4-yl-2,5-diaz abicyclo [2.2.1]hept-2-yl)-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(2-isopropoxy-5-methoxyphenyl)-1-(5-methylpyridine-2-sulfonyl)-3-(4-pyridin-4-ylpiperazin-1-yl)-2,3-dihydro-1H-indol-2-one;

5-Cyano-3-(2-ethoxyphenyl)-1-(5-methoxypyridine-2-sulfonyl)-3-(4-pyridin-4-yl-piperazin-1-yl)-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(6-chloro-2-ethoxypyridin-3-yl)-1-(5-methylpyridine-2-sulfonyl)-3-(4-pyridin-4-ylpiperazin-1-yl)-2,3-dihydro-1H-indol-2-one;

5-Cyano-3-(6-chloro-2-ethoxypyridin-3-yl)-3-(4-pyridin-4-ylpiperazin-1-yl)-1-(quinoline-8-sulfonyl)-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(2-ethoxyphenyl)-1-(5-methoxyquinoline-8-sulfonyl)-3-(4-pyridin-4-yl-piperazin-1-yl)-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(2-ethoxyphenyl)-1-(5-fluoroquinoline-8-sulfonyl)-3-(4-pyridin-4-yl-piperazin-1-yl)-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(6-chloro-2-ethoxypyridin-3-yl)-3-[4-(2-methylpyridin-4-yl)-piperazin-1-yl]-1-(quinoline-8-sulfonyl)-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(6-chloro-2-ethoxypyridin-3-yl)-1-(2,4-dimethoxybenzenesulfonyl)-3-[4-(2-methylpyridin-4-yl)piperazin-1-yl]-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(6-chloro-2-ethoxypyridin-3-yl)-1-(2,4-dimethoxybenzenesulfonyl)-3-(4-pyridin-4-ylpiperazin-1-yl)-2,3-dihydro-1H-indol-2-one;

5-Cyano-3-(6-chloro-2-ethoxypyridin-3-yl)-1-(4-methylquinoline-8-sulfonyl)-3-(4-pyridin-4-ylpiperazin-1-yl)-2,3-dihydro-1H-indol-2-one;

5-Cyano-3-(2-ethoxy-4-fluorophenyl)-1-(5-methoxyquinoline-8-sulfonyl)-3-(4-pyridin-4-ylpiperazin-1-yl)-2,3-dihydro-1H-indol-2-one;

5-Cyano-3-(2-ethoxy-4-fluorophenyl)-1-(5-methoxypyridine-2-sulfonyl)-3-(4-pyridin-4-ylpiperazin-1-yl)-2,3-dihydro-1H-indol-2-one;

5-Cyano-3-(2-ethoxy-5-methoxyphenyl)-1-(5-methoxyquinoline-8-sulfonyl)-3-[4-(2-methylpyridin-4-yl)piperazin-1-yl]-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(6-chloro-2-ethoxypyridin-3-yl)-1-(5-methoxypyridine-2-sulfonyl)-3-[4-(2-methylpyridin-4-yl)piperazin-1-yl]-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(2-ethoxy-5-methoxyphenyl)-1-(5-methoxypyridine-2-sulfonyl)-3-[4-(2-methylpyridin-4-yl)piperazin-1-yl]-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(6-chloro-2-ethoxypyridin-3-yl)-1-(5-methoxypyridine-2-sulfonyl)-3-(4-pyridin-4-ylpiperazin-1-yl)-2,3-dihydro-1H-indol-2-one;

5-Chloro-3-(2-methoxyphenyl)-3-(4-pyridin-4-ylpiperazin-1-yl)-1-(quinoline-8-sulfonyl)-1,3-dihydroindol-2-one;

5-Cyano-3-(2-ethoxyphenyl)-3-(4-pyridin-4-ylpiperazin-1-yl)-1-(quinoline-8-sulfonyl)-2,3-dihydro-1H-indol -2-one;

3-(2-Methoxyphenyl)-6-methyl-3-(4-pyridin-4-ylpiperazin-1-yl)-1-(quinoline-8-sulfonyl)-1,3-dihydroindol-2-one;

5-Chloro-3-(2-chlorophenyl)-3-(4-pyridin-4-ylpiperazin-1-yl)-1-(quinoline-8-sulfonyl)-1,3-dihydroindol-2-one;

5-Chloro-3-(5-dimethylaminomethyl-2-methoxyphenyl)-3-(4-pyridin-4-ylpiperazin-1-yl)-1-(quinoline-8-sulfonyl)-1,3-dihydroindol -2-one;

5-Chloro-3-(2-methoxypyridin-3-yl)-3-(4-pyridin-4-ylpiperazin-1-yl)-1-(quinoline-8-sulfonyl)-1,3-dihydroindol -2-one;

5-Cyano-3-(2-methoxyphenyl)-3-(4-pyridin-4-ylpiperazin-1-yl)-1-(quinoline-8-sulfonyl)-2,3-dihydro-1H-indol-2-one;

5-Cyano-3-(2-ethoxyphenyl)-3-[4-(2-methylpyridin-4-yl)piperazin-1-yl]-1-(quinoline-8-sulfonyl)-2,3-dihydro-1H-indol -2-one;

5-Chloro-3-(2-methoxy-5-methylaminomethylphenyl)-3-(4-pyridin-4-ylpiperazin-1-yl)-1-(quinoline-8-sulfonyl)-1,3-dihydroindol -2-one;

5-Cyano-3-(2-ethoxy-4-fluorophenyl)-3-(4-pyridin-4-ylpiperazin-1-yl)-1-(quinoline-8-sulfonyl)-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(2-ethoxy-5-methoxyphenyl)-1-(5-methylpyridine-2-sulfonyl)-3-(4-pyridin-4-ylpiperazin-1-yl)-2,3-dihydro-1H-indol-2-one;

5-Cyano-1-(5-chloroquinoline-8-sulfonyl)-3-(2-ethoxy-5-methoxyphenyl)-3-(4-pyridin-4-ylpiperazin-1-yl)-2,3-dihydro-1H-indol-2-one;

5-Cyano-3-(2-ethoxy-4-fluorophenyl)-1-(5-methylpyridine-2-sulfonyl)-3-(4-pyridin-4-ylpiperazin-1-yl)-2,3-dihydro-1H-indol-2-one;

5-Cyano-3-(2,5-dimethoxyphenyl)-1-(4-methylquinoline-8-sulfonyl)-3-(4-pyridin-4-yl-piperazin-1-yl)-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(2-methoxy-5-methylphenyl)-3-(4-pyridin-4-ylpiperazin-1-yl)-1-(quinoline-8-sulfonyl)-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(2-ethoxy-5-methoxyphenyl)-1-(5-methylpyridine-2-sulfonyl)-3-[4-(2-methylpyridin-4-yl)piperazin-1-yl]-2,3-dihydro-1H-indol -2-one;

5-Cyano-1-(5-chloroquinoline-8-sulfonyl)-3-(2-ethoxy-5-methoxyphenyl)-3-[4-(2-methylpyridin-4-yl)piperazin-1-yl]-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(2-ethoxy-5-methoxyphenyl)-3-[4-(2-methylpyridin-4-yl)piperazin-1-yl]-1-(quinoline-8-sulfonyl)-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(2,6-difluoropyridin-3-yl)-1-(2,4-dimethoxybenzenesulfonyl)-3-(4-pyridin-4-ylpiperazin-1-yl)-2,3-dihydro-1H-indol-2-one;

5-Cyano-3-(2-ethoxyphenyl)-3-[4-(2-ethylpyridin-4-yl) piperazin-1-yl]-1-(quinoline-8-sulfonyl)-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(2-ethoxy-5-methoxyphenyl)-3-[4-(2-isopropylpyridin-4-yl) piperazin-1-yl]-1-(quinoline-8-sulfonyl)-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(2-ethoxy-5-methoxyphenyl)-3-[4-(2-ethylpyridin-4-yl)piperazin-1-yl]-1-(quinoline-8-sulfonyl)-2,3-dihydro-1H-indol -2-one;

3-(2,5-Dimethoxyphenyl)-5-methoxy-3-(4-pyridin-4-ylpiperazin-1-yl)-1-(quinoline-8-sulfonyl)-1,3-dihydroindol -2-one;

(+)-5-Cyano-3-(2-ethoxyphenyl)-3-(4-pyridin-4-ylpiperazin-1-yl)-1-(quinoline-8-sulfonyl)-2,3-dihydro-1H-indol-2-one;

(+)-5-Cyano-3-(2-ethoxyphenyl)-1-(5-methylpyridine-2-sulfonyl)-3-(4-pyridin-4-yl-piperazin-1-yl)-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(2-ethoxy-5-methoxyphenyl)-3-[4-(2-methylpyridin-4-yl)-[1,4]diazepan-1-yl]-1-(quinoline-8-sulfonyl)-2,3-dihydro-1H-indol -2-one;

(+)-5-Cyano-3-(2-ethoxyphenyl)-1-(4-methylquinoline-8-sulfonyl)-3-(4-pyridin-4-yl-piperazin-1-yl)-2,3-dihydro-1H-indol -2-one;

(+)-5-Cyano-3-(2-ethoxyphenyl)-1-(5-methoxypyridine-2-sulfonyl)-3-(4-pyridin-4-yl-piperazin-1-yl)-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(2-ethoxy-5-methoxyphenyl)-1-(5-methoxypyridine-2-sulfonyl)-3-[4-(2-methylpyridin-4-yl)-[1,4]diazepan-1-yl]-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-[4-(2-cyclopropylpyridin-4-yl) piperazin-1-yl]-3-(2-ethoxy-5-methoxyphenyl)-1-(quinoline-8-sulfonyl)-2,3-dihydro-1H-indol -2-one;

(+)-5-Cyano-3-(2-ethoxyphenyl)-1-(5-ethoxyquinoline-8-sulfonyl)-3-(4-pyridin-4-yl-piperazin-1-yl)-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(2-ethoxy-5-methoxyphenyl)-1-(5-methoxypyridine-2-sulfonyl)-3-(5-pyridin-4-ylhexahydropyrrolo[3,4-c]pyrrol-2-yl)-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(2-ethoxy-5-methoxyphenyl)-1-(5-methoxyquinoline-8-sulfonyl)-3-(4-piperidin-4-ylpiperazin-1-yl)-2,3-dihydro-1H-indol -2-one hydrochloride;

5-Cyano-3-[4-(2-cyclopropylpyridin-4-yl) piperazin-1-yl]-3-(2-ethoxy-5-methoxyphenyl)-1-(5-methoxyquinoline-8-sulfonyl)-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(6-chloro-2-ethoxypyridin-3-yl)-1-(5-methoxyquinoline-8-sulfonyl)-3-(4-pyridin-4-yl-[1,4]diazepan-1-yl)-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(2-ethoxy-5-methoxyphenyl)-3-[4-(2-ethylpyridin-4-yl) piperazin-1-yl]-1-(5-methoxyquinoline-8-sulfonyl)-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(2-ethoxy-5-methoxyphenyl)-1-(5-methoxyquinoline-8-sulfonyl)-3-[4-(2-methylpyridin-4-yl)-[1,4]diazepan-1-yl]-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(2-ethoxy-5-methoxyphenyl)-1-(5-methoxyquinoline-8-sulfonyl)-3-(5-pyridin-4-ylhexahydropyrrolo[3,4-c]pyrrol-2-yl)-2,3-dihydro-1H-indol -2-one;

(−)5Cyano-3-(2-ethoxy-5-methoxyphenyl)-1-(5-methoxypyridine-2-sulfonyl)-3-[4-(2-methylpyridin-4-yl)piperazin-1-yl]-2,3-dihydro-1H-indol -2-one;

(+)-5-Cyano-3-(2-ethoxy-5-methoxyphenyl)-1-(5-methylpyridine-2-sulfonyl)-3-[4-(2-methylpyridin-4-yl)-piperazin-1-yl]-2,3-dihydro-1H-indol -2-one;

(+)-5-Cyano-3-(2-ethoxy-5-methoxyphenyl)-3-[4-(4-methylpiperazin-1-yl) piperidin-1-yl]-1-(4-methylquinoline-8-sulfonyl)-2,3-dihydro-1H-indol-2-one;

5-Cyano-3-(2-ethoxyphenyl)-1-(5-methoxypyridine-2-sulfonyl)-3-(4-pyridin-4-yl-[1,4]diazepan-1-yl)-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(2-ethoxyphenyl)-1-(5-methoxypyridine-2-sulfonyl)-3-[4-(2-methyl-pyridin-4-yl)piperazin-1-yl]-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(2-ethoxy-5-methoxyphenyl)-1-(5-methoxyquinoline-8-sulfonyl)-3-(4-pyridin-4-ylpiperazin-1-yl)-2,3-dihydro-1H-indol-2-one;

5-Cyano-3-(2-ethoxy-5-methoxyphenyl)-1-(5-fluoroquinoline-8-sulfonyl)-3-(4-pyridin-4-ylpiperazin-1-yl)-2,3-dihydro-1H-indol-2-one;

5-Cyano-3-(2-ethoxy-5-methoxyphenyl)-1-(5-methoxypyridine-2-sulfonyl)-3-(4-pyridin-4-ylpiperazin-1-yl)-2,3-dihydro-1H-indol-2-one;

5-Cyano-3-(2-ethoxyphenyl)-1-(5-methoxypyridine-2-sulfonyl)-3-[4-(1-methyl-piperidin-4-yl)piperazin-1-yl]-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(2-ethoxyphenyl)-1-(4-ethylquinoline-8-sulfonyl)-3-(4-pyridin-4-yl-piperazin-1-yl)-2,3-dihydro-1H-indol-2-one;

5-Cyano-3-(2-ethoxy-5-methoxyphenyl)-1-(5-methoxypyridine-2-sulfonyl)-3-(4-piperazin-1-ylpiperidin-1-yl)-2,3-dihydro-1H-indol-2-one;

5-Cyano-3-(2-ethoxy-5-methoxyphenyl)-1-(5-methoxyquinoline-8-sulfonyl)-3-(4-piperazin-1-ylpiperidin-1-yl)-2,3-dihydro-1H-indol-2-one hydrochloride;

5-Cyano-3-(2-ethoxyphenyl)-1-(5-methylquinoline-8-sulfonyl)-3-(4-pyridin-4-yl-piperazin-1-yl)-2,3-dihydro-1H-indol-2-one;

5-Cyano-3-(2-ethoxy-5-methoxyphenyl)-1-(5-methoxypyridine-2-sulfonyl)-3-[4-(1-methylpiperidin-4-yl)piperazin-1-yl]-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-[4-(2-cyclopropylpyridin-4-yl)piperazin-1-yl]-3-(2-ethoxy-5-methoxyphenyl)-1-(5-methoxypyridine-2-sulfonyl)-2,3-dihydro-1H-indol-2-one;

5-Cyano-3-(2-ethoxy-5-methoxyphenyl)-3-[4-(2isopropylpyridin-4-yl) piperazin-1-yl]-1-(5-methoxypyridine-2-sulfonyl)-2,3-dihydro-1H-indol -2-one;

5-Chloro-1-(4-methoxybenzenesulfonyl)-3-(2-methoxypyridin-3-yl)-3-(4-thiazol-2-yl-piperazin-1-yl)-1,3-dihydroindol -2-one;

5-Chloro-1-(2,4-dimethoxybenzenesulfonyl)-3-(2-methoxypyridin-3-yl)-3-(4-thiazol-2-ylpiperazin-1-yl)-1,3-dihydroindol -2-one;

5-Chloro-1-(2,4-dimethoxybenzenesulfonyl)-3-(2-methoxypyridin-3-yl)-3-(4-pyridin-4-ylpiperazin-1-yl)-1,3-dihydroindol -2-one;

5-Chloro-1-(4-methoxybenzenesulfonyl)-3-(2-methoxypyridin-3-yl)-3-(4-pyridin-4-yl-piperazin-1-yl)-1,3-dihydroindol -2-one;

5-Chloro-1-(2,4-dimethoxybenzenesulfonyl)-3-(2-methoxypyridin-3-yl)-3-[4-(4-cyanopyridin-2-yl)piperazin-1-yl]-1,3-dihydroindol -2-one;

5-Chloro-1-(2-methoxy-4-methylbenzenesulfonyl)-3-(2-methoxypyridin-3-yl)-3-(4-pyridin-4-ylpiperazin-1-yl)-1,3-dihydroindol -2-one;

5-Chloro-1-(4-cyanobenzenesulfonyl)-3-(2-methoxypyridin-3-yl)-3-(4-pyridin-4-yl-piperazin-1-yl)-1,3-dihydroindol -2-one;

5-Chloro-1-(2-methoxybenzenesulfonyl)-3-(2-methoxypyridin-3-yl)-3-(4-pyridin-4-yl-piperazin-1-yl)-1,3-dihydroindol -2-one;

5-Chloro-1-(2,4-dimethoxybenzenesulfonyl)-3-[4-(4-methoxyphenyl)piperazin-1-yl]-3-(2-methoxypyridin-3-yl)-1,3-dihydroindol -2-one;

5-Chloro-1-(2,4-dimethoxybenzenesulfonyl)-3-(2-methoxypyridin-3-yl)-3-(4-pyridin-2-ylpiperazin-1-yl)-1,3-dihydroindol -2-one;

5-Chloro-1-(2-fluorobenzenesulfonyl)-3-(2-methoxypyridin-3-yl)-3-(4-pyridin-4-yl-piperazin-1-yl)-1,3-dihydroindol -2-one;

5-Chloro-1-(4-fluorobenzenesulfonyl)-3-(2-methoxypyridin-3-yl)-3-(4-pyridin-4-yl-piperazin-1-yl)-1,3-dihydroindol -2-one;

5-Chloro-1-(3,4-dimethoxybenzenesulfonyl)-3-(2-methoxypyridin-3-yl)-3-(4-pyridin-2-ylpiperazin-1-yl)-1,3-dihydroindol -2-one;

5-Chloro-3-(3,4-dimethoxyphenyl)-3-(4-pyridin-4-ylpiperazin-1-yl)-1-(quinoline-8-sulfonyl)-1,3-dihydroindol -2-one;

5-Chloro-3-(3-dimethylaminomethylphenyl)-3-(4-pyridin-4-ylpiperazin-1-yl)-1-(quinoline-8-sulfonyl)-1,3-dihydroindol -2-one;

5-Chloro-3-(2-methoxymethylphenyl)-3-(4-pyridin-4-ylpiperazin-1-yl)-1-(quinoline-8-sulfonyl)-1,3-dihydroindol -2-one;

5-Cyano-3-(2-ethoxyphenyl)-3-[4-(2-ethoxypyridin-4-yl)piperazin-1-yl]-1-(quinoline-8-sulfonyl)-1,3-dihydroindol -2-one;

5-Cyano-3-(2-ethoxyphenyl)-3-[4-(2-chloropyridin-4-yl)piperazin-1-yl]-1-(quinoline-8-sulfonyl)-1,3-dihydroindol -2-one;

5-Cyano-3-(2-ethoxyphenyl)-3-[4-(1-oxidopyridin-4-yl)piperazin-1-yl]-1-(quinoline-8-sulfonyl)-1,3-dihydroindol -2-one;

5-Cyano-3-(2-ethoxyphenyl)-3-(4-[1,3,5]triazin-2-ylpiperazin-1-yl)-1-(quinoline-8-sulfonyl)-1,3-dihydroindol -2-one;

5-Cyano-3-(2-ethoxyphenyl)-3-(4-pyrimidin-4-ylpiperazin-1-yl)-1-(quinoline-8-sulfonyl)-1,3-dihydroindol-2-one;

5-Cyano-3-(2-ethoxyphenyl)-3-((1S,4S)-5-pyridin-4-yl-2,5-diazabicyclo [2.2.1]hept-2-yl)-1-(quinoline-8-sulfonyl)-1,3-dihydroindol -2-one;

5-Chloro-3-(2-methoxyphenyl)-3-((1S,4S)-5-pyridin-4-yl-2,5-diaza-bicyclo[2.2.1]hept-2-yl)-1-(quinoline-8-sulfonyl)-1,3-dihydroindol -2-one;

5-Cyano-3-(2-ethoxyphenyl)-1-(2-methylquinoline-8-sulfonyl)-3-(4-pyridin-4-piperazin-1-yl)-1,3-dihydroindol -2-one;

5-Cyano-3-(2-ethoxyphenyl)-3-[4-(3-fluoropyridin-4-yl)piperazin-1-yl]-1-(quinoline-8-sulfonyl)-1,3-dihydroindol -2-one;

5-Cyano-3-(2-ethoxyphenyl)-3-[4-(2-fluoropyridin-4-yl)piperazin-1-yl]-1-(quinoline-8-sulfonyl)-1,3-dihydroindol -2-one;

5-Cyano-1-(2,5-dimethylthiophene-3-sulfonyl)-3-(2-ethoxyphenyl)-3-(4-pyridin-4-yl-piperazin-1-yl)-1,3-dihydroindol -2-one;

5-Cyano-1-(thiophene-2-sulfonyl)-3-(2-ethoxyphenyl)-3-(4-pyridin-4-ylpiperazin-1-yl)-1,3-dihydroindo1-2-one;

5-Cyano-1-(5-chlorothiophene-2-sulfonyl)-3-(2-ethoxyphenyl)-3-(4-pyridin-4-yl-piperazin-1-yl)-1,3-dihydroindol -2-one;

5-Cyano-1-(thiophene-3-sulfonyl)-3-(2-ethoxyphenyl)-3-(4-pyridin-4-ylpiperazin-1-yl)-1,3-dihydroindol-2-one;

5-Cyano-3-(2-ethoxyphenyl)-1-(8-methoxyquinoline-5-sulfonyl)-3-(4-pyridin-4-yl-piperazin-1-yl)-1,3-dihydroindol -2-one;

5-Cyano-3-(2-ethoxyphenyl)-3-(4-pyridin-4-ylpiperazin-1-yl)-1-(6-methylquinoline-8-sulfonyl)-1,3-dihydroindol -2-one;

5-Cyano-3-(2-ethoxyphenyl)-3-(4-pyridin-4-ylpiperazin-1-yl)-1-(7-methylquinoline-8-sulfonyl)-1,3-dihydroindol -2-one;

5-Cyano-3-(6-chloro-2-methoxypyridin-3-yl)-3-(4-pyridin-4-ylpiperazin-1-yl)-1-(2,4-dimethoxybenzenesulfonyl)-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(2-ethoxy-5-methoxyphenyl)-1-(4-methylquinoline-8-sulfonyl)-3-((1S,4S)-5-pyridin-4-yl-2,5-diazabicyclo[2.2.1]hept-2-yl)-2,3-dihydro-1H-indol-2-one;

5-Cyano-3-(2-ethoxy-5-methoxyphenyl)-1-(quinoline-8-sulfonyl)-3-((1S,4S)-5-pyridin-4-yl-2,5-diazabicyclo[2.2.1]hept-2-yl)-2,3-dihydro-1H-indol-2-one;

(3R)-5-Cyano-3-(2-ethoxy-5-methoxyphenyl)-1-(quinoline-8-sulfonyl)-3-((1S,4S)-5-pyridin-4-yl-2,5-diazabicyclo[2.2.1]hept-2-yl)-2,3-dihydro-1H-indol-2-one;

5-Cyano-3-(2,6-dimethoxypyridin-3-yl)-3-(4-pyridin-4-ylpiperazin-1-yl)-1-(quinoline-8-sulfonyl)-1,3-dihydroindol -2-one;

5-Cyano-3-(2,6-dimethoxypyridin-3-yl)-1-(2,4-dimethoxybenzenesulfonyl)-3-(4-pyridin-4-ylpiperazin-1-yl)-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(6-chloro-2-ethoxypyridin-4-yl)-1-(5-methylpyridine-2-sulfonyl)-3-(4-pyridin-4-ylpiperazin-1-yl)-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(6-chloro-2-ethoxypyridin-4-yl)-3-(4-pyridin-4-ylpiperazin-1-yl)-1-(quinoline-8-sulfonyl)-1,3-dihydroindol -2-one;

5-Cyano-3-(2-ethoxyphenyl)-3-[4-(3,5-dichloropyridin-4-yl)piperazin-1-yl]-1-(quinoline-8-sulfonyl)-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(2,5-dimethoxyphenyl)-1-(5-methylpyridine-2-sulfonyl)-3-[4-(2-trifluoromethylpyridin-4-yl)piperazin-1-yl]-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(2,5-dimethoxyphenyl)-1-(5-methylpyridine-2-sulfonyl)-3-[4-(2-trifluoromethylpyridin-4-yl)piperazin-1-yl]-2,3-dihydro-1H-indol -2-one;

(+)-5-Cyano-3-(2-ethoxy-5-methoxy-phenyl)-1-(5-methoxy-pyridine-2-sulfonyl)-3-(4-piperidin-4-yl-piperazin-1-yl)-2,3-dihydro-1H-indol-2-one;

(+)-5-Cyano-3-(2-ethoxy-5-methoxy-phenyl)-1-(5-methoxy-pyridine-2-sulfonyl)-3-[4-(1-methyl-piperidin-4-yl)-piperazin-1-yl]-2,3-dihydro-1H-indol -2-one;

(+)-5-Cyano-3-(2-ethoxy-4-methoxy-phenyl)-1-(5-methoxy-pyridine-2-sulfonyl)-3-(4-piperazin-1-yl-piperidin-1-yl)-2,3-dihydro-1H-indol-2-one;

(+)-5-Cyano-3-(2-ethoxy-5-methoxy-phenyl)-3-[4-(2-isopropyl-pyridin-4-yl)-piperazin-1-yl]-1-(5-methoxy-pyridine-2-sulfonyl)-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(2-ethoxy-4-fluoro-phenyl)-1-(5-methoxy-pyridine-2-sulfonyl)-3-[4-(2-methyl-pyridin-4-yl)-piperazin-1-yl]-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(2-ethoxy-5-methoxy-phenyl)-3-[4-(4-ethyl-piperazin-1-yl)-piperidin-1-yl]-1-(5-methoxy-pyridine-2-sulfonyl)-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(2-ethoxy-5-methoxy-phenyl)-3-[4-(2-ethyl-pyridin-4-yl)-piperazin-1-yl]-1-(5-methoxy-pyridine-2-sulfonyl)-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(2-ethoxy-4-fluoro-phenyl)-1-(5-methoxy-pyridine-2-sulfonyl)-3-(4-pyridin-4-yl-[1,4]diazepan-1-yl)-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(6-chloro-2-ethoxy-pyridin-3-yl)-1-(5-methoxy-pyridine-2-sulfonyl)-3-(5-pyridin-4-yl-hexahydro-pyrrolo[3,4-c]pyrrol-2-yl)-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(6-chloro-2-ethoxy-pyridin-3-yl)-1-(5-methoxy-pyridine-2-sulfonyl)-3-[5-(2-methyl-pyridin-4-yl)-hexahydro-pyrrolo[3,4-c]pyrrol-2-yl]-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(2-ethoxy-phenyl)-3-[4-(2-isopropyl-pyridin-4-yl)-piperazin-1-yl]-1-(5-methoxy-pyridine-2-sulfonyl)-2,3-dihydro-1H-indol -2-one;

(+)-5-Cyano-3-(6-chloro-2-ethoxy-pyridin-3-yl)-1-(5-methoxy-pyridine-2-sulfonyl)-3-[4-(2-methyl-pyridin-4-yl)-piperazin-1-yl]-2,3-dihydro-1H-indol -2-one;

(+)-5-Cyano-3-(6-chloro-2-ethoxy-pyridin-3-yl)-1-(5-methoxy-pyridine-2-sulfonyl)-3-[4-(2-methyl-pyridin-4-yl)-piperazin-1-yl]-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(2-ethoxy-4-fluoro-p henyl)-3-[4-(2-isopropyl-pyridin-4-yl)-piperazin-1-yl]-1-(5-methoxy-pyridine-2-sulfonyl)-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(2-ethoxy-5-methoxy-phenyl)-3-[4-(2-is opropyl-pyridin-4-yl)-[1,4]diazepan-1-yl]-1-(5-methoxy-pyridine-2-sulfonyl)-2,3-dihydro-1H-indol-2-one;

5-Cyano-3-(6-chloro-2-ethoxy-pyridin-3-yl)-1-(5-methoxy-pyridine-2-sulfonyl)-3-((1S,4S)-5-pyridin-4-yl-2,5-diaza-bicyclo [2.2.1]hept-2-yl)-2,3-dihydro-1H-indol -2-one;

(+)-5-Cyano-3-(2-ethoxy-5-methoxy-phenyl)-1-(5-methoxy-pyridine-2-sulfonyl)-3-(4-piperazin-1-yl-piperidin-1-yl)-2,3-dihydro-1H-indol-2-one;

5-Cyano-3-(2-ethoxy-4-methoxy-phenyl)-3-(4-pyridin-4-yl-piperazin-1-yl)-1-(quinoline-8-sulfonyl)-2,3-dihydro-1H-indol -2-one;

(+)-5-Cyano-3-(2-ethoxy-5-methoxy-phenyl)-1-(5-methoxy-pyridine-2-sulfonyl)-3-[4-(4-methyl-piperazin-1-yl)-piperidin-1-yl]-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(2-ethoxy-5-methyl-phenyl)-1-(5-methoxy-quinoline-8-sulfonyl)-3-(4-pyridin-4-yl-piperazin-1-yl)-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(2-ethoxy-5-ethyl-phenyl)-1-(5-methoxy-quinoline-8-sulfonyl)-3-[4-(2-methyl-pyridin-4-yl)-piperazin-1-yl]-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(2-ethoxy-5-methoxy-phenyl)-1-(5-methoxy-quinoline-8-sulfonyl)-3-[4-(1-methyl-piperidin-4-yl)-piperazin-1-yl]-2,3-dihydro-1H-indol -2-one;

(+)-5-Cyano-3-(2-ethoxy-5-methoxy-phenyl)-1-(5-methoxy-quinoline-8-sulfonyl)-3-(4-pyridin-4-yl-piperazin-1-yl)-2,3-dihydro-1H-indol -2-one;

(+)-5-Cyano-3-(2-ethoxy-5-methoxy-phenyl)-1-(5-methoxy-pyridine-2-sulfonyl)-3-(4-pyridin-4-yl-piperazin-1-yl)-2,3-dihydro-1H-indol -2-one;

(+)-5-Cyano-3-(2-ethoxy-5-methoxy-phenyl)-1-(5-methoxy-pyridine-2-sulfonyl)-3-[4-(2-methyl-pyridin-4-yl)-piperazin-1-yl]-2,3-dihydro-1H-indol-2-one;

5-Cyano-3-(2-ethoxy-5-ethyl-phenyl)-1-(5-methoxy-pyridine-2-sulfonyl)-3-[4-(2-methyl-pyridin-4-yl)-piperazin-1-yl]-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(2-ethoxy-5-ethyl-phenyl)-3-[4-(2-isopropyl-pyridin-4-yl)-piperazin-1-yl]-1-(5-methoxy-pyridine-2-sulfonyl)-2,3-dihydro-1H-indol-2-one;

5-Cyano-3-(6-chloro-2-ethoxy-pyridin-3-yl)-3-[4-(2-isopropyl-pyridin-4-yl)-piperazin-1-yl]-1-(5-methoxy-pyridine-2-sulfonyl)-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(6-chloro-2-ethoxy-pyridin-3-yl)-1-(5-methoxy-pyridine-2-sulfonyl)-3-(4-pyridin-4-yl-[1,4]diazepan-1-yl)-2,3-dihydro-1H-indol-2-one;

5-Cyano-3-(2-ethoxy-5-methyl-phenyl)-1-(5-methoxy-pyridine-2-sulfonyl)-3-(4-pyridin-4-yl-piperazin-1-yl)-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(6-chloro-2-ethoxy-pyridin-3-yl)-1-(5-methoxy-pyridine-2-sulfonyl)-3-[4-(4-methyl-piperazin-1-yl)-piperidin-1-yl]-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(2-ethoxy-4-methoxy-phenyl)-1-(5-methoxy-pyridine-2-sulfonyl)-3-[4-(4-methyl-piperazin-1-yl)-piperidin-1-yl]-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(2-ethoxy-5-methoxy-phenyl)-1-(5-methoxy-pyridine-2-sulfonyl)-3-(4-piperidin-4-yl-piperazin-1-yl)-2,3-dihydro-1H-indol -2-one as hydrochloride acid addition;

5-Cyano-3-(2-ethoxy-3-methoxy-phenyl)-3-[4-(2-isopropyl-pyridin-4-yl)-piperazin-1-yl]-1-(5-methoxy-pyridine-2-sulfonyl)-2,3-dihydro-1H-indol-2-one;

5-Cyano-3-(2-ethoxy-4-methoxy-phenyl)-1-(5-methoxy-pyridine-2-sulfonyl)-3-(4-piperazin-1-yl-piperidin-1-yl)-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(2-ethoxy-4-methoxy-phenyl)-3-[4-(2-isopropyl-pyridin-4-yl)-piperazin-1-yl]-1-(5-methoxy-pyridine-2-sulfonyl)-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(6-chloro-2-ethoxy-pyridin-3-yl)-1-(5-methoxy-pyridine-2-sulfonyl)-3-(4-piperidin-4-yl-piperazin-1-yl)-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(6-chloro-2-ethoxy-pyridin-3-yl)-1-(5-methoxy-pyridine-2-sulfonyl)-3-[4-(2-methyl-pyridin-4-yl)-[1,4]diazepan-1-yl]-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(2-ethoxy-4-methoxy-phenyl)-1-(5-methoxy-pyridine-2-sulfonyl)-3-[4-(2-methyl-pyridin-4-yl)-piperazin-1-yl]-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(2-ethoxy-3-methoxy-phenyl)-1-(5-methoxy-pyridine-2-sulfonyl)-3-[4-(2-methyl-pyridin-4-yl)-piperazin-1-yl]-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-(2-ethoxy-5-methyl-phenyl)-1-(5-methoxy-pyridine-2-sulfonyl)-3-[4-(2-methyl-pyridin-4-yl)-piperazin-1-yl]-2,3-dihydro-1H-indol -2-one;

5-Cyano-3-[4,4′]bipiperidinyl-1-yl-3-(2-ethoxy-5-methoxy-phenyl)-1-(5-methoxy-pyridine-2-sulfonyl)-2,3-dihydro-1H-indol -2-one; and

5-Cyano-3-(6-chloro-2-ethoxy-pyridin-3-yl)-1-(5-methoxy-pyridine-2-sulfonyl)-3-(4-piperazin-1-yl-piperidin-1-yl)-2,3-dihydro-1H-indol -2-one.

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 16, 2013
From: ABBOTT GMBH & CO KG
To: ABBVIE DEUTSCHLAND GMBH & CO KG
Reel/Frame 030804/0836 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 17, 2013
From: ABBOTT LABORATORIES
To: ABBVIE INC.
Reel/Frame 030235/0856 →
CORRECTIVE ASSIGNMENT TO CORRECT THE CONVEYING PARTY DATA PREVIOUSLY RECORDED ON REEL 023837 FRAME 0297. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNOR ALFRED HAHN SHOULD BE CHANGED TO ASSIGNOR WOLFGANG WERNET. Recorded Jan 26, 2010
From: GENESTE, HERVE; OOST, THORSTEN; HUTCHINS, CHARLES; UNGER, LILIANE; HORNBERGER, WILFRIED; LUBISCH, WILFRIED; NETZ, ASTRID; WERNET, WOLFGANG
To: ABBOTT GMBH & CO. KG
Reel/Frame 023844/0567 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 25, 2010
From: GENESTE, HERVE; OOST, THORSTEN; HUTCHINS, CHARLES W.; UNGER, LILIANE; HORNBERGER, WILFRIED; LUBISCH, WILFRIED; NETZ, ASTRID; HAHN, ALFRED
To: ABBOTT GMBH & CO. KG
Reel/Frame 023837/0297 →