US 7,622,594 B2Granted

Glucocortioid mimetics, methods of making them, pharmaceutical compositions, and uses thereof

AssigneeBoehringer Ingelheim Pharmaceuticals, Inc.

InventorsIngo Andreas Mugge, David S. Thomson, Abdelhakim Hammach, Michael Jason Burke, Mark Stephen Ralph, Jennifer A. Kowalski, Joerg Martin Bentzien

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Abstract

Compounds of Formula (IA) and (IB) wherein R1, R2, R3, A, B, C, D, and E are as defined herein, or a tautomer, prodrug, solvate, or salt thereof; pharmaceutical compositions containing such compounds, and methods of modulating the glucocorticoid receptor function and methods of treating disease-states or conditions mediated by the glucocorticoid receptor function or characterized by inflammatory, allergic, or proliferative processes in a patient using these compounds.

Claims8

Dependent claims

A compound of Formula (IA)

wherein:
R1 is aryl or C3-C7 cycloalkyl, each optionally independently substituted with one to three substituent groups selected from C1-C3 alkyl, hydroxy, halogen, oxo, methoxy, amino wherein the nitrogen atom is optionally independently mono- or disubstituted with a methyl group, or thiomethyl wherein the sulfur atom is optionally oxidized to a sulfoxide or sulfone;
R2 is hydrogen or a halogen;
A is N;
B is CH;
C and E are each a bond;
D is —CR4R5—, where R4 is —CF3 and R5 is —OH;
and
R3 is heteroaryl independently substituted with one to three substituent groups,
wherein each substituent group of R3 is independently aryl, C1-C5 alkyl, C1-C5 alkenyl, cycloalkyl, cycloalkenyl, acyl, alkoxycarbonyl, C1-C5 alkanoyloxy, C1-C5 alkanoyl, aroyl, C1-C5 alkanoylamino, alkylaminocarbonyl, dialkylaminocarbonyl, aminocarbonyloxy, C1-C5 alkylaminocarbonyloxy, C1-C5 dialkylaminocarbonyloxy, C1-C5 alkanoylamino, C1-C5 alkoxycarbonylamino, C1-C5 alkylsulfonylamino, aminosulfonyl, C1-C5 alkylaminosulfonyl, C1-C5 dialkylaminosulfonyl, C1-C5 alkyloxy, aryloxy, halogen, hydroxy, oxo, cyano, trifluoromethyl, nitro, carboxyl, aminocarbonyl, amino wherein the nitrogen atom is optionally independently mono- or disubstituted with a C1-C5 alkyl, or C1-C5 alkylthio wherein the sulfur atom is optionally oxidized to a sulfoxide or sulfone,
wherein each substituent group of R3 is optionally independently substituted with one to three substituents selected from aryl, acyl, C1-C5 alkyl, C1-C5 alkanoyloxy, C1-C5 alkanoyl, C1-C5 alkanoylamino, alkylaminocarbonyl, dialkylaminocarbonyl, C1-C5 alkylsulfonylamino, aminosulfonyl, C1-C5 alkylaminosulfonyl, C1-C5 dialkylaminosulfonyl, C1-C5 alkyloxy, C1-C5 cycloalkyl, aryloxy, halogen, hydroxy, oxo, cyano, trifluoromethyl, nitro, aminocarbonyl, amino wherein the nitrogen atom is optionally independently mono- or disubstituted with a C1-C5 alkyl, or alkylthio wherein the sulfur atom is optionally oxidized to a sulfoxide or sulfone,
or a tautomer ester, amide or salt thereof.

9 more elements

A compound selected from:

4-[2,2,2-Trifluoro-1-hydroxy-1-(1-phenyl-1H-indazol-5-yl)ethyl]quinoline-3-carboxylic acid dimethylamide;
4-[2,2,2-Trifluoro-1-hydroxy-1-(1-phenyl-1H-indazol-5-yl)ethyl]quinoline-3-carboxylic acid methylamide;
4-[2,2,2-Trifluoro-1-hydroxy-1-(1-phenyl-1H-indazol-5-yl)ethyl]quinoline-3-carboxylic acid amide;
4-[2,2,2-Trifluoro-1-hydroxy-1-(1-phenyl-1H-indazol-5-yl)ethyl]quinoline-3-carboxylic acid ethyl ester;
2,2,2-Trifluoro-1-(1-phenyl-1H-indazol-5-yl)-1-quinolin-4-ylethanol;
2,2,2-Trifluoro-1-(2-methylquinolin-4-yl)-1-(1-phenyl-1H-indazol-5-yl)ethanol;
2,2,2-Trifluoro-1-isoquinolin-1-yl-1-(1-phenyl-1H-indazol-5-yl)ethanol;
2,2,2-Trifluoro-1-isoquinolin-4-yl-1-(1-phenyl-1H-indazol-5-yl)ethanol;
2,2,2-Trifluoro-1-(3-methylpyridin-2-yl)-1-(1-phenyl-1H-indazol-5-yl)ethanol;
2,2,2-Trifluoro-1-(4-methylpyridin-2-yl)-1-(1-phenyl-1H-indazol-5-yl)ethanol;
2,2,2-Trifluoro-1-(5-methylpyridin-2-yl)-1-(1-phenyl-1H-indazol-5-yl)ethanol;
2,2,2-Trifluoro-1-(6-methylpyridin-2-yl)-1-(1-phenyl-1H-indazol-5-yl)ethanol;
2,2,2-Trifluoro-1-(1-phenyl-1H-indazol-5-yl)-1-pyridin-2-ylethanol;
1-Benzo[b]thiophen-3-yl-2,2,2-trifluoro-1-(1-phenyl-1H-indazol-5-yl)ethanol;
2,2,2-Trifluoro-1-(1H-indol-4-yl)-1-(1-phenyl-1H-indazol-5-yl)ethanol;
2,2,2-Trifluoro-1-(1H-indol-3-yl)-1-(1-phenyl-1H-indazol-5-yl)ethanol;
4-{2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}quinoline-3-carboxylic acid dimethylamide;
4-{2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}quinoline-3-carboxylic acid methylamide;
4-{2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}quinoline-3-carboxylic acid amide;
4-{2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}quinoline-3-carboxylic acid ethyl ester;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-quinolin-4-ylethanol;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-(2-methylquinolin-4-yl)ethanol;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-isoquinolin-1-ylethanol;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-isoquinolin-4-ylethanol;
1-Benzofuran-5-yl-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
1-Benzofuran-2-yl-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-(1H-indol-4-yl)ethanol;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-(1-methyl-1H-indol-4-yl)ethanol;
1-Benzo[b]thiophen-3-yl-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
2,2,2-Trifluoro-1-(6-fluoropyridin-2-yl)-1-(1-phenyl-1H-indazol-5-yl)ethanol;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-(1H-indol-7-yl)ethanol;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-(1-methyl-1H-indol-7-yl)ethanol;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-(1-methyl-1H-indol-5-yl)ethanol;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-(1-methyl-1H-indol-6-yl)ethanol;
4-{2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}indole-1-carboxylic acid tert-butyl ester;
1-Methyl-4-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-quinolin-2-one;
1-(1-Allyl-1H-indol-4-yl)-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
3-(4-{2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}indol-1-yl)propane-1,2-diol;
3-Hydroxy-4-(4-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}indol-1-yl)butyronitrile;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-[1-(2-hydroxyethyl)-1H-indol-4-yl]ethanol;
2-(4-{2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}indol-1-yl)acetamide;
N-Methyl-2-(4-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}indol-1-yl)acetamide;
1-[1-(2-Cyclopropyl-2-hydroxyethyl)-1H-indol-4-yl]-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
1-(7-Bromo-1-methyl-1H-indol-3-yl)-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
1-Methyl-3-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-indole-7-carboxylic acid methyl ester;
1-Methyl-3-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-indole-7-carboxylic acid;
1-Methyl-3-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-indole-7-carboxylic acid amide;
1-Methyl-3-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-indole-7-carboxylic acid methylamide;
1-Methyl-3-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-indole-7-carboxylic acid (2-cyanoethyl)amide;
1-Methyl-3-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-indole-7-carboxylic acid (2-methoxyethyl)amide;
1-Methyl-3-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-indole-7-carboxylic acid (2-methoxyethyl)methylamide;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-(1-methyl-7-nitro-1H-indol-3-yl)ethanol;
1-(7-Amino-1-methyl-1H-indol-3-yl)-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
1-Methyl-3-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-indole-7-carboxylic acid carbamoylmethylamide;
1-Methyl-3-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-indole-7-carboxylic acid cyanomethylamide;
1-(1-Allyl-1H-indol-3-yl)-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
N-(1-Methyl-3-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-indol-7-yl)methanesulfonamide;
3-(3-{2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}indol-1-yl)propane-1,2-diol;
1-Benzyl-3-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-indole-7-carboxylic acid methyl ester;
2-(3-{2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}indol-1-yl)acetamide;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-[1-(2-hydroxyethyl)-1H-indol-3-yl]ethanol;
N-Methyl-2-(3-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}indol-1-yl)acetamide;
1-Allyl-3-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-indole-7-carboxylic acid methyl ester;
1-(1-Allyl-1H-imidazol-4-yl)-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
3-(4-{2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}imidazol-1-yl)propane-1,2-diol;
1-Allyl-3-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-indole-7-carboxylic acid amide;
1-(2,3-Dihydroxypropyl)-3-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-indole-7-carboxylic acid amide;
1-(1-Allyl-1H-indol-3-yl)-2,2,2-trifluoro-1-(1-p-tolyl-1H-indazol-5-yl)ethanol;
3-{3-[2,2,2-Trifluoro-1-hydroxy-1-(1-p-tolyl-1H-indazol-5-yl)ethyl]indol-1-yl}propane-1,2-diol;
2,2,2-Trifluoro-1-(5-fluoro-1H-indol-3-yl)-1-(1-p-tolyl-1H-indazol-5-yl)ethanol;
2,2,2-Trifluoro-1-(5-fluoro-1H-indol-3-yl)-1-[1-(2-fluorophenyl)-1H-indazol-5-yl]ethanol;
2,2,2-Trifluoro-1-(5-fluoro-1H-indol-3-yl)-1-[1-(4-methoxyphenyl)-1H-indazol-5-yl]ethanol;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-(5-methoxy-4-methyl-1H-indol-3-yl)ethanol;
1-(4-Chloro-1H-indol-3-yl)-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-(6-methoxy-1H-indol-3-yl)ethanol;
1-(2,5-Dimethyl-1H-indol-3-yl)-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-(7-methoxy-1H-indol-3-yl)ethanol;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-(1H-indol-3-yl)ethanol;
1-(6-Bromo-1H-indol-3-yl)-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
1-(7-Bromo-1H-indol-3-yl)-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
1-(5-Bromo-1H-indol-3-yl)-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-(5-methyl-1H-indol-3-yl)ethanol;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-(2-methyl-1H-indol-3-yl)ethanol;
1-(6-Chloro-1H-indol-3-yl)-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
1-(5-Chloro-1H-indol-3-yl)-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
1-(4-Bromo-1H-indol-3-yl)-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
2,2,2-Trifluoro-1-(5-fluoro-1H-indol-3-yl)-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
2,2,2-Trifluoro-1-(4-fluoro-1H-indol-3-yl)-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
2,2,2-Trifluoro-1-(6-fluoro-1H-indol-3-yl)-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-(5-methoxy-1H-indol-3-yl)ethanol;
2,2,2-Trifluoro-1-(7-fluoro-1H-indol-3-yl)-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-(6-methyl-1H-indol-3-yl)ethanol;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-(7-methyl-1H-indol-3-yl)ethanol;
3-{2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-indole-5-carbonitrile;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-(1-methyl-1H-indol-3-yl)ethanol;
1-(6-Bromo-1-methyl-1H-indol-3-yl)-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
1-Methyl-3-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-indole-6-carbonitrile;
1-Methyl-3-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-indole-6-carboxylic acid methyl ester;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-{6-[(2-methoxyethyl)methylamino]-1-methyl-1H-indol-3-yl}ethanol;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-[6-(2-methoxyethylamino)-1-methyl-1H-indol-3-yl]ethanol;
1-{6-[(2-Dimethylaminoethyl)methylamino]-1-methyl-1H-indol-3-yl}-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
1-[6-(2-Dimethylaminoethylamino)-1-methyl-1H-indol-3-yl]-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
1-[5-(2-Dimethylaminoethylamino)-1-methyl-1H-indol-3-yl]-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
N-Methyl-2-{3-[2,2,2-trifluoro-1-hydroxy-1-(1-p-tolyl-1H-indazol-5-yl)ethyl]indol-1-yl}ace tamide;
2-{3-[2,2,2-Trifluoro-1-hydroxy-1-(1-p-tolyl-1H-indazol-5-yl)ethyl]indol-1-yl}acetamide;
2,2,2-Trifluoro-1-[1-(2-hydroxyethyl)-1H-indol-3-yl]-1-(1-p-tolyl-1H-indazol-5-yl)ethanol;
and
3-{3-[2,2,2-Trifluoro-1-hydroxy-1-(1-p-tolyl-1H-indazol-5-yl)ethyl]indol-1-yl}propane-1,2-diol,
or a tautomer ester, amide or salt thereof.

106 more elements

A compound selected from:

2,2,2-Trifluoro-1-(1-phenyl-1H-indazol-5-yl)-1-quinolin-4-ylethanol;
2,2,2-Trifluoro-1-(1H-indol-4-yl)-1-(1-phenyl-1H-indazol-5-yl)ethanol;
1-Benzo[b]thiophen-3-yl-2,2,2-trifluoro-1-(1-phenyl-1H-indazol-5-yl)ethanol;
2,2,2-Trifluoro-1-(1-phenyl-1H-indazol-5-yl)-1-quinolin-4-ylethanol;
2,2,2-Trifluoro-1-isoquinolin-1-yl-1-(1-phenyl-1H-indazol-5-yl)ethanol;
1-Benzo[b]thiophen-3-yl-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-(1-methyl-1H-indol-4-yl)ethanol;
1-Benzo[b]thiophen-3-yl-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
2,2,2-Trifluoro-1-(6-fluoropyridin-2-yl)-1-(1-phenyl-1H-indazol-5-yl)ethanol;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-(1H-indol-7-yl)ethanol;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-(1-methyl-1H-indol-7-yl)ethanol;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-(1-methyl-1H-indol-5-yl)ethanol;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-(1-methyl-1H-indol-6-yl)ethanol;
4-{2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}indole-1-carboxylic acid tert-butyl ester;
1-Methyl-4-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-quinolin-2-one;
1-(1-Allyl-1H-indol-4-yl)-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
3-(4-{2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}indol-1-yl)propane-1,2-diol;
3-Hydroxy-4-(4-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}indol-1-yl)butyronitrile;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-[1-(2-hydroxyethyl)-1H-indol-4-yl]ethanol;
2-(4-{2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}indol-1-yl)acetamide;
N-Methyl-2-(4-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}indol-1-yl)acetamide;
1-[1-(2-Cyclopropyl-2-hydroxyethyl)-1H-indol-4-yl]-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
1-(7-Bromo-1-methyl-1H-indol-3-yl)-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
1-Methyl-3-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-indole-7-carboxylic acid methyl ester;
1-Methyl-3-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-indole-7-carboxylic acid;
1-Methyl-3-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-indole-7-carboxylic acid amide;
1-Methyl-3-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-indole-7-carboxylic acid methylamide;
1-Methyl-3-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-indole-7-carboxylic acid (2-cyanoethyl)amide;
1-Methyl-3-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-indole-7-carboxylic acid (2-methoxyethyl)amide;
1-Methyl-3-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-indole-7-carboxylic acid (2-methoxyethyl)methylamide;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-(1-methyl-7-nitro-1H-indol-3-yl)ethanol;
1-(7-Amino-1-methyl-1H-indol-3-yl)-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
1-Methyl-3-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-indole-7-carboxylic acid carbamoylmethylamide;
1-Methyl-3-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-indole-7-carboxylic acid cyanomethylamide;
1-(1-Allyl-1H-indol-3-yl)-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
N-(1-Methyl-3-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-indol-7-yl)methanesulfonamide;
3-(3-{2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}indol-1-yl)propane-1,2-diol;
1-Benzyl-3-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-indole-7-carboxylic acid methyl ester;
2-(3-{2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}indol-1-yl)acetamide;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-[1-(2-hydroxyethyl)-1H-indol-3-yl]ethanol;
N-Methyl-2-(3-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}indol-1-yl)acetamide;
1-Allyl-3-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-indole-7-carboxylic acid methyl ester;
1-Allyl-3-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-indole-7-carboxylic acid amide;
1-(2,3-Dihydroxypropyl)-3-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-indole-7-carboxylic acid amide;
1-(1-Allyl-1H-indol-3-yl)-2,2,2-trifluoro-1-(1-p-tolyl-1H-indazol-5-yl)ethanol;
3-{3-[2,2,2-Trifluoro-1-hydroxy-1-(1-p-tolyl-1H-indazol-5-yl)ethyl]indol-1-yl}propane-1,2-diol;
2,2,2-Trifluoro-1-(5-fluoro-1H-indol-3-yl)-1-(1-p-tolyl-1H-indazol-5-yl)ethanol;
2,2,2-Trifluoro-1-(5-fluoro-1H-indol-3-yl)-1-[1-(2-fluorophenyl)-1H-indazol-5-yl]ethanol;
2,2,2-Trifluoro-1-(5-fluoro-1H-indol-3-yl)-1-[1-(4-methoxyphenyl)-1H-indazol-5-yl]ethanol;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-(5-methoxy-4-methyl-1H-indol-3-yl)ethanol;
1-(4-Chloro-1H-indol-3-yl)-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-(6-methoxy-1H-indol-3-yl)ethanol;
1-(2,5-Dimethyl-1H-indol-3-yl)-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-(7-methoxy-1H-indol-3-yl)ethanol;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-(1H-indol-3-yl)ethanol;
1-(6-Bromo-1H-indol-3-yl)-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
1-(7-Bromo-1H-indol-3-yl)-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
1-(5-Bromo-1H-indol-3-yl)-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-(5-methyl-1H-indol-3-yl)ethanol;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-(2-methyl-1H-indol-3-yl)ethanol;
1-(6-Chloro-1H-indol-3-yl)-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
1-(5-Chloro-1H-indol-3-yl)-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
1-(4-Bromo-1H-indol-3-yl)-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
2,2,2-Trifluoro-1-(5-fluoro-1H-indol-3-yl)-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
2,2,2-Trifluoro-1-(4-fluoro-1H-indol-3-yl)-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
2,2,2-Trifluoro-1-(6-fluoro-1H-indol-3-yl)-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-(5-methoxy-1H-indol-3-yl)ethanol;
2,2,2-Trifluoro-1-(7-fluoro-1H-indol-3-yl)-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-(6-methyl-1H-indol-3-yl)ethanol;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-(7-methyl-1H-indol-3-yl)ethanol;
3-{2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-indole-5-carbonitrile;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-(1-methyl-1H-indol-3-yl)ethanol;
1-(6-Bromo-1-methyl-1H-indol-3-yl)-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
1-Methyl-3-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-indole-6-carbonitrile;
1-Methyl-3-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-indole-6-carboxylic acid methyl ester;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-{6-[(2-methoxyethyl)methylamino]-1-methyl-1H-indol-3-yl}ethanol;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-[6-(2-methoxyethylamino)-1-methyl-1H-indol-3-yl]ethanol;
1-{6-[(2-Dimethylaminoethyl)methylamino]-1-methyl-1H-indol-3-yl}-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
1-[6-(2-Dimethylaminoethylamino)-1-methyl-1H-indol-3-yl]-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
1-[5-(2-Dimethylaminoethylamino)-1-methyl-1H-indol-3-yl]-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
N-Methyl-2-{3-[2,2,2-trifluoro-1-hydroxy-1-(1-p-tolyl-1H-indazol-5-yl)ethyl]indol-1-yl}ace tamide;
2-{3-[2,2,2-Trifluoro-1-hydroxy-1-(1-p-tolyl-1H-indazol-5-yl)ethyl]indol-1-yl}acetamide;
2,2,2-Trifluoro-1-[1-(2-hydroxyethyl)-1H-indol-3-yl]-1-(1-p-tolyl-1H-indazol-5-yl)ethanol;
and
3-{3-[2,2,2-Trifluoro-1-hydroxy-1-(1-p-tolyl-1H-indazol-5-yl)ethyl]indol-1-yl}propane-1,2-diol,
or a tautomer ester, amide or salt thereof.

83 more elements

A compound selected from:

2,2,2-Trifluoro-1-(1-phenyl-1H-indazol-5-yl)-1-quinolin-4-ylethanol;
2,2,2-Trifluoro-1-(1H-indol-4-yl)-1-(1-phenyl-1H-indazol-5-yl)ethanol;
1-Benzo[b]thiophen-3-yl-2,2,2-trifluoro-1-(1-phenyl-1H-indazol-5-yl)ethanol;
2,2,2-Trifluoro-1-(1-phenyl-1H-indazol-5-yl)-1-quinolin-4-ylethanol;
2,2,2-Trifluoro-1-isoquinolin-1-yl-1-(1-phenyl-1H-indazol-5-yl)ethanol;
1-Benzo[b]thiophen-3-yl-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
1-Benzo[b]thiophen-3-yl-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
2,2,2-Trifluoro-1-(6-fluoropyridin-2-yl)-1-(1-phenyl-1H-indazol-5-yl)ethanol;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-(1H-indol-7-yl)ethanol;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-(1-methyl-1H-indol-7-yl)ethanol;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-(1-methyl-1H-indol-5-yl)ethanol;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-(1-methyl-1H-indol-6-yl)ethanol;
4-{2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}indole-1-carboxylic acid tert-butyl ester;
1-Methyl-4-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-quinolin-2-one;
1-(1-Allyl-1H-indol-4-yl)-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
3-(4-{2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}indol-1-yl)propane-1,2-diol;
3-Hydroxy-4-(4-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}indol-1-yl)butyronitrile;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-[1-(2-hydroxyethyl)-1H-indol-4-yl]ethanol;
2-(4-{2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}indol-1-yl)acetamide;
N-Methyl-2-(4-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}indol-1-yl)acetamide;
1-[1-(2-Cyclopropyl-2-hydroxyethyl)-1H-indol-4-yl]-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
1-(7-Bromo-1-methyl-1H-indol-3-yl)-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
1-Methyl-3-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-indole-7-carboxylic acid methyl ester;
1-Methyl-3-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-indole-7-carboxylic acid;
1-Methyl-3-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-indole-7-carboxylic acid amide;
1-Methyl-3-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-indole-7-carboxylic acid methylamide;
1-Methyl-3-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-indole-7-carboxylic acid (2-cyanoethyl)amide;
1-Methyl-3-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-indole-7-carboxylic acid (2-methoxyethyl)amide;
1-Methyl-3-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-indole-7-carboxylic acid (2-methoxyethyl)methylamide;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-(1-methyl-7-nitro-1H-indol-3-yl)ethanol;
1-(7-Amino-1-methyl-1H-indol-3-yl)-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
1-Methyl-3-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-indole-7-carboxylic acid carbamoylmethylamide;
1-Methyl-3-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-indole-7-carboxylic acid cyanomethylamide;
1-(1-Allyl-1H-indol-3-yl)-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
N-(1-Methyl-3-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-indol-7-yl)methanesulfonamide;
3-(3-{2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}indol-1-yl)propane-1,2-diol;
1-Benzyl-3-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-indole-7-carboxylic acid methyl ester;
2-(3-{2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}indol-1-yl)acetamide;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-[1-(2-hydroxyethyl)-1H-indol-3-yl]ethanol;
N-Methyl-2-(3-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}indol-1-yl)acetamide;
1-Allyl-3-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-indole-7-carboxylic acid methyl ester;
1-Allyl-3-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-indole-7-carboxylic acid amide;
1-(2,3-Dihydroxypropyl)-3-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-indole-7-carboxylic acid amide;
1-(1-Allyl-1H-indol-3-yl)-2,2,2-trifluoro-1-(1-p-tolyl-1H-indazol-5-yl)ethanol;
3-{3-[2,2,2-Trifluoro-1-hydroxy-1-(1-p-tolyl-1H-indazol-5-yl)ethyl]indol-1-yl}propane-1,2-diol;
2,2,2-Trifluoro-1-(5-fluoro-1H-indol-3-yl)-1-(1-p-tolyl-1H-indazol-5-yl)ethanol;
2,2,2-Trifluoro-1-(5-fluoro-1H-indol-3-yl)-1-[1-(2-fluorophenyl)-1H-indazol-5-yl]ethanol;
2,2,2-Trifluoro-1-(5-fluoro-1H-indol-3-yl)-1-[1-(4-methoxyphenyl)-1H-indazol-5-yl]ethanol;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-(5-methoxy-4-methyl-1H-indol-3-yl)ethanol;
1-(4-Chloro-1H-indol-3-yl)-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-(6-methoxy-1H-indol-3-yl)ethanol;
1-(2,5-Dimethyl-1H-indol-3-yl)-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-(7-methoxy-1H-indol-3-yl)ethanol;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-(1H-indol-3-yl)ethanol;
1-(6-Bromo-1H-indol-3-yl)-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
1-(7-Bromo-1H-indol-3-yl)-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
1-(5-Bromo-1H-indol-3-yl)-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-(5-methyl-1H-indol-3-yl)ethanol;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-(2-methyl-1H-indol-3-yl)ethanol;
1-(6-Chloro-1H-indol-3-yl)-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
1-(5-Chloro-1H-indol-3-yl)-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
1-(4-Bromo-1H-indol-3-yl)-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
2,2,2-Trifluoro-1-(5-fluoro-1H-indol-3-yl)-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
2,2,2-Trifluoro-1-(4-fluoro-1H-indol-3-yl)-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
2,2,2-Trifluoro-1-(6-fluoro-1H-indol-3-yl)-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-(5-methoxy-1H-indol-3-yl)ethanol;
2,2,2-Trifluoro-1-(7-fluoro-1H-indol-3-yl)-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-(6-methyl-1H-indol-3-yl)ethanol;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-(7-methyl-1H-indol-3-yl)ethanol;
3-{2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-indole-5-carbonitrile;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-(1-methyl-1H-indol-3-yl)ethanol;
1-(6-Bromo-1-methyl-1H-indol-3-yl)-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
1-Methyl-3-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-indole-6-carbonitrile;
1-Methyl-3-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-indole-6-carboxylic acid methyl ester;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-{6-[(2-methoxyethyl)methylamino]-1-methyl-1H-indol-3-yl}ethanol;
2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-[6-(2-methoxyethylamino)-1-methyl-1H-indol-3-yl]ethanol;
1-{6-[(2-Dimethylaminoethyl)methylamino]-1-methyl-1H-indol-3-yl}-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
1-[6-(2-Dimethylaminoethylamino)-1-methyl-1H-indol-3-yl]-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
1-[5-(2-Dimethylaminoethylamino)-1-methyl-1H-indol-3-yl]-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol;
N-Methyl-2-{3-[2,2,2-trifluoro-1-hydroxy-1-(1-p-tolyl-1H-indazol-5-yl)ethyl]indol-1-yl}ace tamide;
2-{3-[2,2,2-Trifluoro-1-hydroxy-1-(1-p-tolyl-1H-indazol-5-yl)ethyl]indol-1-yl}acetamide;
2,2,2-Trifluoro-1-[1-(2-hydroxyethyl)-1H-indol-3-yl]-1-(1-p-tolyl-1H-indazol-5-yl)ethanol;
and
3-{3-[2,2,2-Trifluoro-1-hydroxy-1-(1-p-tolyl-1H-indazol-5-yl)ethyl]indol-1-yl}propane-1,2-diol,
or a tautomer ester, amide or salt thereof.

82 more elements

Dependencies are inferred from the claim text.

Facts

Application: 11/449,231Filed 8 Jun 2006 · us provisional application
Priority: 10 Jun 2005
Published: US 2007/0060633 A115 Mar 2007
Granted: 24 Nov 2009
Term ends: Not estimatedThe source records don’t support an estimate.

Classification43 codes

C07D 471/04
In which the condensed system contains two hetero rings: ortho-condensed systems
A61P 1/04
Drugs for disorders of the alimentary tract or the digestive system: for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of…
A61P 1/16
Drugs for disorders of the alimentary tract or the digestive system: for liver or gallbladder disorders, e.g. hepatoprotective agents,…
A61P 3/04
Drugs for disorders of the metabolism: anorexiants; Antiobesity agents

Family

Application60/689,412Us provisional application · filed 10 Jun 2005
US 2007/0060633 A1Pre-grant publication · published 15 Mar 2007
US 7,622,594 B2This patent

From the US filing history. Foreign family members aren’t listed.

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Abstract

A compound of Formula (IA)

wherein:
R1 is aryl or C3-C7 cycloalkyl, each optionally independently substituted with one to three substituent groups selected from C1-C3 alkyl, hydroxy, halogen, oxo, methoxy, amino wherein the nitrogen atom is optionally independently mono- or disubstituted with a methyl group, or thiomethyl wherein the sulfur atom is optionally oxidized to a sulfoxide or sulfone;
R2 is hydrogen or a halogen;
A is N;
B is CH;
C and E are each a bond;
D is —CR4R5—, where R4 is —CF3 and R5 is —OH;
and
R3 is heteroaryl independently substituted with one to three substituent groups,
wherein each substituent group of R3 is independently aryl, C1-C5 alkyl, C1-C5 alkenyl, cycloalkyl, cycloalkenyl, acyl, alkoxycarbonyl, C1-C5 alkanoyloxy, C1-C5 alkanoyl, aroyl, C1-C5 alkanoylamino, alkylaminocarbonyl, dialkylaminocarbonyl, aminocarbonyloxy, C1-C5 alkylaminocarbonyloxy, C1-C5 dialkylaminocarbonyloxy, C1-C5 alkanoylamino, C1-C5 alkoxycarbonylamino, C1-C5 alkylsulfonylamino, aminosulfonyl, C1-C5 alkylaminosulfonyl, C1-C5 dialkylaminosulfonyl, C1-C5 alkyloxy, aryloxy, halogen, hydroxy, oxo, cyano, trifluoromethyl, nitro, carboxyl, aminocarbonyl, amino wherein the nitrogen atom is optionally independently mono- or disubstituted with a C1-C5 alkyl, or C1-C5 alkylthio wherein the sulfur atom is optionally oxidized to a sulfoxide or sulfone,
wherein each substituent group of R3 is optionally independently substituted with one to three substituents selected from aryl, acyl, C1-C5 alkyl, C1-C5 alkanoyloxy, C1-C5 alkanoyl, C1-C5 alkanoylamino, alkylaminocarbonyl, dialkylaminocarbonyl, C1-C5 alkylsulfonylamino, aminosulfonyl, C1-C5 alkylaminosulfonyl, C1-C5 dialkylaminosulfonyl, C1-C5 alkyloxy, C1-C5 cycloalkyl, aryloxy, halogen, hydroxy, oxo, cyano, trifluoromethyl, nitro, aminocarbonyl, amino wherein the nitrogen atom is optionally independently mono- or disubstituted with a C1-C5 alkyl, or alkylthio wherein the sulfur atom is optionally oxidized to a sulfoxide or sulfone,
or a tautomer ester, amide or salt thereof.

9 more elements

Facts

Application

11/449,231Filed 8 Jun 2006 · us provisional application

Priority

10 Jun 2005

Published

US 2007/0060633 A115 Mar 2007

Granted

24 Nov 2009

Term ends

Not estimatedThe source records don’t support an estimate.

Classification43 codes

C07D 471/04
In which the condensed system contains two hetero rings: ortho-condensed systems
A61P 1/04
Drugs for disorders of the alimentary tract or the digestive system: for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of…
A61P 1/16
Drugs for disorders of the alimentary tract or the digestive system: for liver or gallbladder disorders, e.g. hepatoprotective agents,…
A61P 3/04
Drugs for disorders of the metabolism: anorexiants; Antiobesity agents