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US 8,785,489 B2Granted
Heteroaryl substituted indole compounds useful as MMP-13 inhibitors
AssigneeBoehringer Ingelheim International GmbH
InventorsAsitha Abeywardane, Bennett Farmer, Neil Alexander Farrow, Donghong Amy Gao, Alexander Heim-Riether, Lana Louise Smith Keenan, Ingo Andreas Mugge, Steven John Taylor, Zhaoming Xiong, Yang Yu, Qiang Zhang
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Abstract
Disclosed are compounds and compositions of the formula I as described herein which are inhibitors of MMP-13. Also disclosed are methods of using and making compounds of the formula I.
Claims11
A compound of the formula (I):
- Het is a ring chosen from phenyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, pyrazolyl, pyrrolyl, imidazolyl, pyridinyl, pyrimidinyl and pyridazinyl each optionally substituted by one to three C1-5 alkyl, C1-5 alkoxy, C1-5 acyl, C1-5 acylamino, amino, cyano, hydroxyl or halogen;
- X is —N(R3)—;
- Y is N or CH;
- Z is H or F;
- R1 is chosen from C1-5 alkoxyC1-5 alkyl, C1-5 alkoxycarbonyl-(CH2)n—, —C(O)NR4R5 and Ar1;
- R2 is chosen from Ar2—(CH2)n—, heterocycle and C1-5 alkyl;
- R3 is chosen from hydrogen and C1-5 alkyl;
- each R4 and R5 is independently chosen from hydrogen, C1-5 acyl, C1-5 alkyl, C1-5 alkoxy, hydroxyl, carbocycle-(CH2)n—, heteroaryl and heterocycle-(CH2)n—;
- Ar1 is chosen from carbocycle, heteroaryl and heterocycle wherein Ar1 is optionally substituted by one to three C1-5 alkyl, C1-5 alkoxy, C1-5 acyl, C1-5 acylamino, amino, cyano, hydroxyl or halogen;
- Ar2 is chosen from carbocycle, heteroaryl and heterocycle wherein Ar2 is optionally substituted by one to three heteroaryl, C1-5 alkyl, C1-5 alkoxy-(CH2)n—, C1-5 alkoxycarbonyl-(CH2)n—, carboxy-(CH2)n—, C1-5 acyl, C1-5 acylamino, amino, cyano, hydroxyl, sulfonyl, sulfoxide, thio, oxo or halogen;
- each n is independently 0-2;
- or a pharmaceutically acceptable salt thereof.
9 more elements
A compound chosen from
- or a pharmaceutically acceptable salt thereof.
Dependencies are inferred from the claim text.