Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and thereof
AssigneeBoehringer Ingelheim Pharmaceuticals, Inc.
InventorsYounes Bekkali, Rajashehar Betageri, David Thomson, Doris Riether, Christian Hanke Justus Harcken, Daniel Kuzmich, John Proudfoot
Life of this patent
Estimating the term…
Abstract
Compounds of Formula (IA) wherein R1, R2, R3, R4 and R5 are as defined herein for Formula (IA), 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.
Claims19
A compound of Formula (IA)
- wherein:
- R1 is a heteroaryl group optionally substituted with one to three substituent groups,
- wherein each substituent group of R1 is independently C1-C5 alkyl, C2-C5 alkenyl, C2-C5 alkynyl, C3-C8 cycloalkyl, heterocyclyl, aryl, heteroaryl, C1-C5 alkoxy, C2-C5 alkenyloxy, C2-C5 alkynyloxy, aryloxy, acyl, C1-C5 alkoxycarbonyl, C1-C5 alkanoyloxy, C1-C5 alkanoyl, aroyl, aminocarbonyl, 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, halogen, hydroxy, carboxy, cyano, trifluoromethyl, trifluoromethoxy, nitro, or amino wherein the nitrogen atom is optionally independently mono- or di-substituted by C1-C5 alkyl or aryl;
- or ureido wherein either nitrogen atom is optionally independently substituted with C1-C5 alkyl;
- or C1-C5 alkylthio wherein the sulfur atom is optionally oxidized to a sulfoxide or sulfone,
- wherein each substituent group of R1 is optionally independently substituted with one to three substituent groups selected from methyl, methoxy, halogen, hydroxy, oxo, cyano, or amino,
- R2 and R3 are each independently hydrogen or C1-C5 alkyl;
- R4 is C1-C5 alkyl, C2-C5 alkenyl, or C2-C5 alkynyl, each optionally independently substituted with one to three substituent groups,
- wherein each substituent group of R4 is independently C1-C3 alkyl, hydroxy, halogen, amino, or oxo;
- and
- R5 is an azaindolyl group optionally substituted with one to three substituent groups,
- wherein each substituent group of R5 is independently C1-C5 alkyl, C2-C5 alkenyl, C2-C5 alkynyl, C3-C8 cycloalkyl, heterocyclyl, aryl, heteroaryl, C1-C5 alkoxy, C2-C5 alkenyloxy, C2-C5 alkynyloxy, aryloxy, acyl, C1-C5 alkoxycarbonyl, C1-C5 alkanoyloxy, aminocarbonyl, 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, halogen, hydroxy, carboxy, cyano, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, nitro, or amino wherein the nitrogen atom is optionally independently mono- or di-substituted by C1-C5 alkyl;
- or ureido wherein either nitrogen atom is optionally independently substituted with C1-C5 alkyl;
- or C1-C5 alkylthio wherein the sulfur atom is optionally oxidized to a sulfoxide or sulfone,
- wherein each substituent group of R5 is optionally independently substituted with one to three substituent groups selected from C1-C3 alkyl, C1-C3 alkoxy, halogen, hydroxy, oxo, cyano, amino, or trifluoromethyl,
- or a tautomer, prodrug, solvate, or salt thereof.
A compound selected from:
- 4-(2,3-Dihydrobenzofuran-7-yl)-1,1,1-trifluoro-4-methyl-2-(1H-pyrrolo[2,3-c]pyridin-2-ylmethyl)pentan-2-ol;
- 4-(2,3-Dihydrobenzofuran-7-yl)-1,1,1-trifluoro-4-methyl-2-(1H-pyrrolo[3,2-c]pyridin-2-ylmethyl)pentan-2-ol;
- and
- 1,1,1-Trifluoro-4-(5-fluoro-2,3-dihydrobenzofuran-7-yl)-4-methyl-2-(1H-pyrrolo[2,3-c]pyridin-2-ylmethyl)pentan-2-ol,
- or a tautomer, prodrug, solvate, or salt thereof.
A compound selected from:
- 4-(2,3-Dihydrobenzofuran-7-yl)-1,1,1-trifluoro-4-methyl-2-(1H-pyrrolo[2,3-c]pyridin-2-ylmethyl)pentan-2-ol;
- and
- 4-(2,3-Dihydrobenzofuran-7-yl)-1,1,1-trifluoro-4-methyl-2-(1H-pyrrolo[3,2-c]pyridin-2-ylmethyl)pentan-2-ol,
- or a tautomer, prodrug, solvate, or salt thereof.
Dependencies are inferred from the claim text.