# US 9,434,713 B2 · 5,6-disubstituted oxindole-derivatives and use thereof for treating vasopressin-dependent diseases

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- Number: US 9,434,713 B2
- Document ID: US9434713B2
- Status: Granted
- Kind: B2
- Application number: 14/040,412
- Filed: 2013-09-27
- Published: 2014-07-10
- Granted: 2016-09-06
- Earliest claimed: 2007-12-07
- Assignees: AbbVie Deutschland GmbH & Co. KG
- Applicants: Abbvie Deutschland GmbH & Co KG; Andrea Hager-Wernet
- Inventors: Wilfried Braje; Thorsten Oost; Astrid Netz; Wolfgang Wernet; Liliane Unger; Wilfried Hornberger; Wilfried Lubisch
- Web page: https://patentgrep.com/patent/US9434713B2

## CPC

- C07D 401/14: containing three or more hetero rings
- A61P 1/00: Drugs for disorders of the alimentary tract or the digestive system
- A61P 1/04: for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A61P 1/08: for nausea, cinetosis or vertigo; Antiemetics
- A61P 1/12: Antidiarrhoeals
- A61P 3/10: for hyperglycaemia, e.g. antidiabetics
- A61P 7/00: Drugs for disorders of the blood or the extracellular fluid
- A61P 7/02: Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- A61P 7/10: Antioedematous agents; Diuretics
- A61P 9/00: Drugs for disorders of the cardiovascular system
- A61P 9/10: for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A61P 9/12: Antihypertensives
- A61P 11/00: Drugs for disorders of the respiratory system
- A61P 13/00: Drugs for disorders of the urinary system
- A61P 13/12: of the kidneys
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 25/18: Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- A61P 25/20: Hypnotics; Sedatives
- A61P 25/22: Anxiolytics
- A61P 25/24: Antidepressants
- A61P 25/28: for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A61P 25/30: for treating abuse or dependence
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The present invention relates to novel 5,6-disubstituted oxindole derivatives and pharmaceutically acceptable salts thereof, and pharmaceutical compositions comprising such derivatives, and to the use of such derivatives for the manufacture of a medicament, and methods of treating disorders in a subject in need thereof, such as vasopressin-dependent disorders, using 5,6-disubstituted oxindole derivatives.

## Claims

### Claim 1

A method for the treatment of vasopressin-dependent diseases selected from the group consisting of hypertension, pulmonary hypertension, heart failure, myocardial infarction, Schwartz-Bartter syndrome, hepatocirrhosis, diabetes insipidus, depression, anxiety, and hyperthermia, the method comprising administering a compound of formula (I) or a pharmaceutically acceptable salt thereof to a subject in need thereof;
in which
R1 and R2 are independently of one another hydrogen, C1-C3-alkyl, C1-C3-fluoroalkyl, C1-C3-alkoxy, C1-C3-fluoroalkoxy, halogen or CN;
R3 is hydrogen or C1-C4-alkyl;
R4 is ethoxy, fluorinated ethoxy or isopropoxy;
R5 is hydrogen or methyl;
R6 is Br, Cl, F or CN;
R7 is Cl, F or CN;
R8 and R9 are independently of one another C1-C3-alkyl or C1-C3-fluoroalkyl;
X1 is O, NH or CH2;
X2 and X3 are N or CH, with the proviso that X2 and X3 are not simultaneously N;
X4 is N or CH;
a and b are independently of one another 0, 1 or 2; and
m, n, o and p are independently of one another 1, 2 or 3.

### Claim 2 (depends on 1)

The method of claim 1, wherein the compound of formula (I) has formula I.A
in which
R1 and R2 are independently of one another hydrogen, C1-C3-alkyl, C1-C3-fluoroalkyl, C1-C3-alkoxy, C1-C3-fluoroalkoxy, halogen or CN;
R3 is hydrogen or C1-C4-alkyl;
R4 is ethoxy, fluorinated ethoxy or isopropoxy;
R5 is hydrogen or methyl;
R6 is Br, Cl, F or CN;
R7 is Cl, F or CN;
X1 is O, NH or CH2;
X2 and X3 are N or CH, with the proviso that X2 and X3 are not simultaneously N; and
X4 is N or CH;
or a pharmaceutically acceptable salt thereof.

### Claim 3 (depends on 1)

The method of claim 1, in which R1 is hydrogen, methoxy, ethoxy, fluoromethoxy, difluoromethoxy or trifluoromethoxy.

### Claim 4 (depends on 1)

The method of claim 1, in which R2 is hydrogen or methoxy.

### Claim 5 (depends on 1)

The method of claim 1, in which R1 and R2 are methoxy.

### Claim 6 (depends on 1)

The method of claim 1, in which R3 is hydrogen, methyl or ethyl.

### Claim 7 (depends on 1)

The method of claim 1, in which R4 is ethoxy and R5 is H.

### Claim 8 (depends on 1)

The method of claim 1, in which R4 is 2,2-difluoroethoxy or 2,2,2-trifluoroethoxy and R5 is H.

### Claim 9 (depends on 1)

The method of claim 1, in which R6 and R7 are not simultaneously CN.

### Claim 10 (depends on 1)

The method of claim 1, in which at least one of the radicals R6 and R7 is F.

### Claim 11 (depends on 10)

The method of claim 10, in which R7 is F and R6 is F, Cl, Br or CN.

### Claim 12 (depends on 1)

The method of claim 1, in which X2 is N and X3 is CH.

### Claim 13 (depends on 1)

The method of claim 1, in which X2 is CH and X3 is N.

### Claim 14 (depends on 1)

The method of claim 1, in which X2 is CH and X3 is CH.

### Claim 15 (depends on 1)

The method of claim 1, in which X1 is O.

### Claim 16 (depends on 1)

The method of claim 1, in which X1 is NH.

### Claim 17 (depends on 1)

The method of claim 1, in which X4 is N.

### Claim 18 (depends on 1)

The method of claim 1 in which
R1 is methoxy;
R2 is methoxy;
R3 is methyl or ethyl;
R4 is ethoxy;
R5 is H;
R6 is Cl or CN;
R7 is F;
X1 is NH;
X2 is N;
X3 is CH; and
X4 is N.

### Claim 19 (depends on 1)

The method of claim 1 in which
R1 is methoxy;
R2 is methoxy;
R3 is methyl or ethyl;
R4 is ethoxy;
R5 is H;
R6 is Cl or CN;
R7 is F;
X1 is NH;
X2 is CH;
X3 is N; and
X4 is N.

### Claim 20 (depends on 1)

The method of claim 1 in which
R1 is methoxy;
R2 is methoxy;
R3 is methyl or ethyl;
R4 is ethoxy;
R5 is H;
R6 is Cl or CN;
R7 is F;
X1 is CH2;
X2 is N;
X3 is CH; and
X4 is N.

### Claim 21 (depends on 1)

The method of claim 1 in which
R1 is methoxy;
R2 is methoxy;
R3 is methyl or ethyl;
R4 is ethoxy;
R5 is H;
R6 is Cl or CN;
R7 is F;
X1 is CH2;
X2 is CH;
X3 is N; and
X4 is N.

### Claim 22 (depends on 1)

The method of claim 1 in which
R1 is methoxy or H;
R2 is methoxy;
R3 is methyl or ethyl;
R4 is ethoxy;
R5 is H;
R6 is Cl or CN;
R7 is F;
X1 is O;
X2 is N;
X3 is CH; and
X4 is N.

### Claim 23 (depends on 1)

The method of claim 1 in which
R1 is methoxy or H;
R2 is methoxy;
R3 is methyl or ethyl;
R4 is ethoxy;
R5 is H;
R6 is Cl or CN;
R7 is F;
X1 is O;
X2 is CH;
X3 is N; and
X4 is N.

### Claim 24 (depends on 1)

The method of claim 1 in which
R1 is methoxy;
R2 is methoxy;
R3 is methyl or ethyl;
R4 is ethoxy;
R5 is H;
R6 is Cl or CN;
R7 is F;
X1 is NH;
X2 is N;
X3 is CH; and
X4 is CH.

### Claim 25 (depends on 1)

The method of claim 1, wherein the vasopressin-dependent disease is selected from the group consisting of hepatocirrhosis, diabetes insipidus, hypertension, myocardial infarction, hyperthermia, and Schwartz-Bartter syndrome.

### Claim 26 (depends on 1)

The method of claim 1, wherein the vasopressin-dependent disease is selected from the group consisting of pulmonary hypertension and heart failure.

### Claim 27 (depends on 1)

The method of claim 1, wherein the vasopressin-dependent disease is selected from the group consisting of depression and anxiety.

### Claim 28

A method for the treatment of vasopressin-dependent diseases selected from the group consisting of hypertension, pulmonary hypertension, heart failure, myocardial infarction, Schwartz-Bartter syndrome, hepatocirrhosis, diabetes insipidus, depression, anxiety, and hyperthermia,
the method comprising administering a compound, or a pharmaceutically acceptable salt thereof to a subject in need thereof, the compound selected from the group consisting of:
4-(1-Methylpiperidin-4-yl)piperazin-1-[5-cyano-1-(2,4-dimethoxyphenylsulfonyl)-3-(2-ethoxypyridin-3-yl)-6-fluoro-2-oxo-2,3-dihydro-1H-indol-3-yl]carboxamide;
(+)-4-(1-Methylpiperidin-4-yl)piperazine-1-[5-cyano-1-(2,4-dimethoxyphenylsulfonyl)-3-(2-ethoxypyridin-3-yl)-6-fluoro-2-oxo-2,3-dihydro-1H-indol-3-yl]carboxamide;
(−)-4-(1-Methylpiperidin-4-yl)piperazine-1-[5-cyano-1-(2,4-dimethoxyphenylsulfonyl)-3-(2-ethoxypyridin-3-yl)-6-fluoro-2-oxo-2,3-dihydro-1H-indol-3-yl]carboxamide;
4-(1-Ethylpiperidin-4-yl)piperazine-1-[5-cyano-1-(2,4-dimethoxyphenylsulfonyl)-3-(2-ethoxypyridin-3-yl)-6-fluoro-2-oxo-2,3-dihydro-1H-indol-3-yl]carboxamide;
4-(4-Methylpiperazin-1-yl)piperidine-1-[5-cyano-1-(2,4-dimethoxyphenylsulfonyl)-3-(2-ethoxypyridin-3-yl)-6-fluoro-2-oxo-2,3-dihydro-1H-indol-3-yl]carboxamide;
4-(4-Ethylpiperazin-1-yl)piperidine-1-[5-cyano-1-(2,4-dimethoxyphenylsulfonyl)-3-(2-ethoxypyridin-3-yl)-6-fluoro-2-oxo-2,3-dihydro-1H-indol-3-yl]carboxamide;
4-(1-Methylpiperidin-4-yl)piperazine-1-[5-cyano-3-(2-ethoxypyridin-3-yl)-6-fluoro-1-(4-methoxyphenylsulfonyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]carboxamide;
4-(1-Ethylpiperidin-4-yl)piperazine-1-[5-cyano-3-(2-ethoxypyridin-3-yl)-6-fluoro-1-(4-methoxyphenylsulfonyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]carboxamide;
4-(4-Methylpiperazin-1-yl)piperidine-1-[5-cyano-3-(2-ethoxypyridin-3-yl)-6-fluoro-1-(4-methoxyphenylsulfonyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]carboxamide;
4-(4-Ethylpiperazin-1-yl)piperidine-1-[5-cyano-3-(2-ethoxypyridin-3-yl)-6-fluoro-1-(4-methoxyphenylsulfonyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]carboxamide;
4-(1-Methylpiperidin-4-yl)piperazine-1-[5-cyano-1-(2,4-dimethoxyphenylsulfonyl)-3-(2-ethoxyphenyl)-6-fluoro-2-oxo-2,3-dihydro-1H-indol-3-yl]carboxamide;
4-(1-Methylpiperidin-4-yl)piperazine-1-[5-cyano-3-(2-ethoxyphenyl)-6-fluoro-1-(4-methoxyphenylsulfonyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]carboxamide;
4-(1-Ethylpiperidin-4-yl)piperazine-1-[5-cyano-1-(2,4-dimethoxyphenylsulfonyl)-3-(2-ethoxyphenyl)-6-fluoro-2-oxo-2,3-dihydro-1H-indol-3-yl]carboxamide;
4-(1-Ethylpiperidin-4-yl)piperazine-1-[5-cyano-3-(2-ethoxyphenyl)-6-fluoro-1-(4-methoxyphenylsulfonyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]carboxamide;
4-(1-Ethylpiperidin-4-yl)piperazine-1-[1-phenylsulfonyl-5-cyano-3-(2-ethoxyphenyl)-6-fluoro-2-oxo-2,3-dihydro-1H-indol-3-yl]carb oxamide;
4-(4-Methylpiperazin-1-yl)piperidine-1-[5-cyano-1-(2,4-dimethoxyphenylsulfonyl)-3-(2-ethoxyphenyl)-6-fluoro-2-oxo-2,3-dihydro-1H-indol-3-yl]carboxamide;
4-(4-Methylpiperazin-1-yl)piperidine-1-[5-cyano-3-(2-ethoxyphenyl)-6-fluoro-1-(4-methoxyphenylsulfonyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]carboxamide;
4-(4-Ethylpiperazin-1-yl)piperidine-1-[5-cyano-1-(2,4-dimethoxyphenylsulfonyl)-3-(2-ethoxyphenyl)-6-fluoro-2-oxo-2,3-dihydro-1H-indol-3-yl]carboxamide;
4-(4-Ethylpiperazin-1-yl)piperidine-1-[5-cyano-3-(2-ethoxyphenyl)-6-fluoro-1-(4-methoxyphenylsulfonyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]carboxamide;
4-(4-Ethylpiperazin-1-yl)piperidine-1-[1-phenylsulfonyl-5-cyano-3-(2-ethoxyphenyl)-6-fluoro-2-oxo-2,3-dihydro-1H-indol-3-yl]carb oxamide;
4-(1-Methylpiperidin-4-yl)piperazine-1-[5-chloro-1-(2,4-dimethoxyphenylsulfonyl)-3-(2-ethoxypyridin-3-yl)-6-fluoro-2-oxo-2,3-dihydro-1H-indol-3-yl]carboxamide;
4-(1-Methylpiperidin-4-yl)piperazine-1-[1-phenylsulfonyl-5-chloro-3-(2-ethoxypyridin-3-yl)-6-fluoro-2-oxo-2,3-dihydro-1H-indol-3-yl]carboxamide;
4-(1-Ethylpiperidin-4-yl)piperazine-1-[5-chloro-1-(2,4-dimethoxyphenylsulfonyl)-3-(2-ethoxypyridin-3-yl)-6-fluoro-2-oxo-2,3-dihydro-1H-indol-3-yl]carboxamide;
4-(1-Ethylpiperidin-4-yl)piperazine-1-[1-phenylsulfonyl-5-chloro-3-(2-ethoxypyridin-3-yl)-6-fluoro-2-oxo-2,3-dihydro-1H-indol-3-yl]carboxamide;
4-(4-Methylpiperazin-1-yl)piperidine-1-[5-chloro-1-(2,4-dimethoxyphenylsulfonyl)-3-(2-ethoxypyridin-3-yl)-6-fluoro-2-oxo-2,3-dihydro-1H-indol-3-yl]carboxamide;
4-(4-Methylpiperazin-1-yl)piperidine-1-[1-phenylsulfonyl-5-chloro-3-(2-ethoxypyridin-3-yl)-6-fluoro-2-oxo-2,3-dihydro-1H-indol-3-yl]carboxamide;
4-(4-Ethylpiperazin-1-yl)piperidine-1-[1-phenylsulfonyl-5-chloro-3-(2-ethoxypyridin-3-yl)-6-fluoro-2-oxo-2,3-dihydro-1H-indol-3-yl]carboxamide;
1′-Methyl [4,4′]bipiperidinyl-1-[5-chloro-1-(2,4-dimethoxyphenylsulfonyl)-3-(2-ethoxypyridin-3-yl)-6-fluoro-2-oxo-2,3-dihydro-1H-indol-3-yl]carboxamide;
1′-Ethyl[4,4]bipiperidinyl-1-[5-chloro-1-(2,4-dimethoxyphenylsulfonyl)-3-(2-ethoxypyridin-3-yl)-6-fluoro-2-oxo-2,3-dihydro-1H-indol-3-yl]carboxamide;
4-(4-Methylpiperazin-1-yl)piperidine-1-[5-chloro-3-[2-(2,2-difluoroethoxy)phenyl]-1-(2,4-dimethoxyphenylsulfonyl)-6-fluoro-2-oxo-2,3-dihydro-1H-indol-3-yl]carboxamide;
4-(1-Methylpiperidin-4-yl)piperazine-1-[5-chloro-3-[2-(2,2-difluoroethoxy)phenyl]-1-(2,4-dimethoxyphenylsulfonyl)-6-fluoro-2-oxo-2,3-dihydro-1H-indol-3-yl]carboxamide;
1′-Methyl[4,4′]bipiperidinyl-1-[5-chloro-3-[2-(2,2-difluoroethoxy)phenyl]-1-(2,4-dimethoxyphenylsulfonyl)-6-fluoro-2-oxo-2,3-dihydro-1H-indol-3-yl]carboxamide;
4-(1-Methylpiperidin-4-yl)piperazine-1-[1-(2,4-dimethoxyphenylsulfonyl)-3-(2-ethoxypyridin-3-yl)-5,6-difluoro-2-oxo-2,3-dihydro-1H-indol-3-yl]carb oxamide;
4-(1-Methylpiperidin-4-yl)piperazine-1-[1-phenylsulfonyl-3-(2-ethoxypyridin-3-yl)-5,6-difluoro-2-oxo-2,3-dihydro-1H-indol-3-yl]carboxamide;
4-(1-Ethylpiperidin-4-yl)piperazine-1-[1-(2,4-dimethoxyphenylsulfonyl)-3-(2-ethoxypyridin-3-yl)-5,6-difluoro-2-oxo-2,3-dihydro-1H-indol-3-yl]carb oxamide;
4-(1-Ethylpiperidin-4-yl)piperazine-1-[1-phenylsulfonyl-3-(2-ethoxypyridin-3-yl)-5,6-difluoro-2-oxo-2,3-dihydro-1H-indol-3-yl]carboxamide;
4-(4-Methylpiperazin-1-yl)piperidine-1-[1-(2,4-dimethoxyphenylsulfonyl)-3-(2-ethoxypyridin-3-yl)-5,6-difluoro-2-oxo-2,3-dihydro-1H-indol-3-yl]carb oxamide;
4-(4-Methylpiperazin-1-yl)piperidine-1-[1-phenylsulfonyl-3-(2-ethoxypyridin-3-yl)-5,6-difluoro-2-oxo-2,3-dihydro-1H-indol-3-yl]carboxamide;
4-(4-Ethylpiperazin-1-yl)piperidine-1-[1-(2,4-dimethoxyphenylsulfonyl)-3-(2-ethoxypyridin-3-yl)-5,6-difluoro-2-oxo-2,3-dihydro-1H-indol-3-yl]carb oxamide;
5-Cyano-1-(2,4-dimethoxybenzenesulfonyl)-3-(2-ethoxypyridin-3-yl)-6-fluoro-2-oxo-2,3-dihydro-1H-indol-3-yl 4-(1-methylpiperidin-4-yl)piperazine-1-carboxylate;
5-Cyano-3-(2-ethoxypyridin-3-yl)-6-fluoro-1-(4-methoxyphenylsulfonyl)-2-oxo-2,3-dihydro-1H-indol-3-yl 4-(1-methylpiperidin-4-yl)piperazine-1-carboxylate;
1-Phenylsulfonyl-5-cyano-3-(2-ethoxypyridin-3-yl)-6-fluoro-2-oxo-2,3-dihydro-1H-indol-3-yl 4-(1-methylpiperidin-4-yl)piperazine-1-carboxylate;
5-Chloro-1-(2,4-dimethoxyphenylsulfonyl)-3-(2-ethoxypyridin-3-yl)-6-fluoro-2-oxo-2,3-dihydro-1H-indol-3-yl 4-(1-methylpiperidin-4-yl)piperazine-1-carboxylate;
5-Chloro-3-(2-ethoxypyridin-3-yl)-6-fluoro-1-(4-methoxyphenylsulfonyl)-2-oxo-2,3-dihydro-1H-indol-3-yl 4-(1-methylpiperidin-4-yl)piperazine-1-carboxylate;
5-Chloro-3-(2-ethoxypyridin-3-yl)-6-fluoro-1-(2-methoxyphenylsulfonyl)-2-oxo-2,3-dihydro-1H-indol-3-yl 4-(1-methylpiperidin-4-yl)piperazine-1-carboxylate;
5-Chloro-3-(2-ethoxypyridin-3-yl)-6-fluoro-1-(4-methoxy-2-trifluoromethoxyphenylsulfonyl)-2-oxo-2,3-dihydro-1H-indol-3-yl 4-(1-methylpiperidin-4-yl)piperazine-1-carboxylate;
1-Phenylsulfonyl-5-chloro-3-(2-ethoxypyridin-3-yl)-6-fluoro-2-oxo-2,3-dihydro-1H-indol-3-yl 4-(1-methylpiperidin-4-yl)piperazine-1-carboxylate;
6-Chloro-1-(2,4-dimethoxyphenylsulfonyl)-3-(2-ethoxypyridin-3-yl)-5-fluoro-2-oxo-2,3-dihydro-1H-indol-3-yl 4-(1-methylpiperidin-4-yl)piperazine-1-carboxylate;
6-Chloro-3-(2-ethoxypyridin-3-yl)-5-fluoro-1-(4-methoxyphenylsulfonyl)-2-oxo-2,3-dihydro-1H-indol-3-yl 4-(1-methylpiperidin-4-yl)piperazine-1-carboxylate;
6-Chloro-3-(2-ethoxypyridin-3-yl)-5-fluoro-1-(4-methoxy-2-trifluoromethoxyphenylsulfonyl)-2-oxo-2,3-dihydro-1H-indol-3-yl 4-(1-methylpiperidin-4-yl)piperazine-1-carboxylate;
1-Phenylsulfonyl-6-chloro-3-(2-ethoxypyridin-3-yl)-5-fluoro-2-oxo-2,3-dihydro-1H-indol-3-yl 4-(1-methylpiperidin-4-yl)piperazine-1-carboxylate;
6-Chloro-3-(2-ethoxypyridin-3-yl)-5-fluoro-1-(2-methoxyphenylsulfonyl)-2-oxo-2,3-dihydro-1H-indol-3-yl 4-(1-methylpiperidin-4-yl)piperazine-1-carboxylate;
1-(2,4-dimethoxyphenylsulfonyl)-3-(2-ethoxypyridin-3-yl)-5,6-difluoro-2-oxo-2,3-dihydro-1H-indol-3-yl 4-(1-methylpiperidin-4-yl)piperazine-1-carboxylate;
3-(2-Ethoxypyridin-3-yl)-5,6-difluoro-1-(4-methoxyphenylsulfonyl)-2-oxo-2,3-dihydro-1H-indol-3-yl 4-(1-methylpiperidin-4-yl)piperazine-1-carboxylate;
3-(2-Ethoxypyridin-3-yl)-5,6-difluoro-1-(2-methoxyphenylsulfonyl)-2-oxo-2,3-dihydro-1H-indol-3-yl 4-(1-methylpiperidin-4-yl)piperazine-1-carboxylate;
3-(2-Ethoxypyridin-3-yl)-5,6-difluoro-1-(4-methoxy-2-trifluoromethoxyphenylsulfonyl)-2-oxo-2,3-dihydro-1H-indol-3-yl 4-(1-methylpiperidin-4-yl)piperazine-1-carboxylate;
1-Phenylsulfonyl-3-(2-ethoxypyridin-3-yl)-5,6-difluoro-2-oxo-2,3-dihydro-1H-indol-3-yl 4-(1-methylpiperidin-4-yl)piperazine-1-carboxylate; and
(+)-5-Chloro-1-(2,4-dimethoxyphenylsulfonyl)-3-(2-ethoxypyridin-3-yl)-6-fluoro-3-{2-[4-(1-methylpiperidin-4-yl)piperazin-1-yl]-2-oxo-ethyl}-1,3-dihydroindol-2-one.