US 12,252,484 B2
Pyrazolopyridine compounds for the treatment of autoimmune disease
Fabian Dey, Basel (CH); Taishan Hu, Shanghai (CN); Haixia Liu, Shanghai (CN); Hong Shen, Shanghai (CN); Zhiwei Zhang, Shanghai (CN); and Wei Zhu, Shanghai (CN)
Assigned to Hoffmann-La Roche Inc., Little Falls, NJ (US)
Appl. No. 17/274,035
Filed by Hoffmann-La Roche Inc., Little Falls, NJ (US)
PCT Filed Sep. 6, 2018, PCT No. PCT/EP2018/073929
§ 371(c)(1), (2) Date Mar. 5, 2021,
PCT Pub. No. WO2020/048596, PCT Pub. Date Mar. 12, 2020.
Prior Publication US 2021/0355122 A1, Nov. 18, 2021
Int. Cl. C07D 471/04 (2006.01); C07D 471/08 (2006.01); C07D 471/18 (2006.01); C07D 498/18 (2006.01); C07D 519/00 (2006.01)
CPC C07D 471/04 (2013.01) [C07D 471/08 (2013.01); C07D 471/18 (2013.01); C07D 498/18 (2013.01); C07D 519/00 (2013.01)] 17 Claims
 
1. A compound of formula (I),

OG Complex Work Unit Chemistry
wherein:
R1 is cyano, C1-6alkyl, halogen, haloC1-6alkyl or nitro;
R2 is C1-6alkyl or haloC1-6alkyl;
R3 is —NHR3a or —COR3b, wherein:
R3a is H, aminoC1-6alkylcarbonyl, (C1-6alkyl)2aminoC1-6alkylcarbonyl or cyanoC1-6alkyl;
R3b is (heterocyclylcarbonyl)phenylamino, (hydroxyC1-6alkoxy)C1-6alkylamino, adamantylamino, aminoC1-6alkylamino, C1-6alkoxyC1-6alkylamino, C1-6alkylamino, C1-6alkylpyrazolylamino, cyanoC3-7cycloalkylamino, heterocyclyl, heterocyclylamino, heterocyclylC1-6alkylamino, hydroxyC1-6alkylamino, hydroxyC1-6alkylC3-7cycloalkylamino, hydroxyC3-7cycloalkylamino or pyridylamino;
R4 is H or halogen; and
X is O or CH2;
or a pharmaceutically acceptable salt, enantiomer or diastereomer thereof.