US 11,891,405 B2
Furo[3,4-b]pyrrole-containing BTK inhibitor
Yinsheng Zhang, Lianyungang (CN); Hongjiang Xu, Lianyungang (CN); Jing Ren, Lianyungang (CN); Qinglin Wang, Lianyungang (CN); Zheyang Wu, Lianyungang (CN); Chao Jin, Lianyungang (CN); Wei Shi, Lianyungang (CN); Xiaojin Wang, Lianyungang (CN); Xiangyi He, Lianyungang (CN); Xiayun Chang, Lianyungang (CN); Jie Wang, Lianyungang (CN); and Tianxiao Zhao, Lianyungang (CN)
Assigned to CHIA TAI TIANQING PHARMACEUTICAL GROUP CO., LTD., Jiangsu (CN)
Appl. No. 17/276,025
Filed by CHIA TAI TIANQING PHARMACEUTICAL GROUP CO., LTD., Lianyungang (CN)
PCT Filed Sep. 12, 2019, PCT No. PCT/CN2019/105584
§ 371(c)(1), (2) Date Mar. 12, 2021,
PCT Pub. No. WO2020/052628, PCT Pub. Date Mar. 19, 2020.
Claims priority of application No. 201811072116.0 (CN), filed on Sep. 14, 2018.
Prior Publication US 2022/0033419 A1, Feb. 3, 2022
Int. Cl. C07D 519/00 (2006.01)
CPC C07D 519/00 (2013.01) 20 Claims
 
1. A compound of formula (I), a stereoisomer thereof or a pharmaceutically acceptable salt thereof,

OG Complex Work Unit Chemistry
wherein,
ring B is selected from the group consisting of 5-10 membered heteroaryl and C6-10 aryl;
R1 is independently selected from the group consisting of halogen, —OH, —NH2, cyano, C1-6 alkyl and C1-6 alkoxy, wherein C1-6 alkyl or C1-6 alkoxy is optionally substituted with halogen;
m is 0, 1, 2, 3 or 4;
L is selected from the group consisting of —C(O)NH—, —NHC(O)—, —O—, —NH—, —S—, —C(O)O—, —OC(O)—, —S(O)2O— and —OS(O)2—;
R2 is independently selected from the group consisting of halogen, —OH, —NH2, cyano, C1-6 alkyl and C1-6 alkoxy, wherein C1-6 alkyl or C1-6 alkoxy is optionally substituted with halogen;
n is 0, 1, 2, 3 or 4;
R3 is selected from the group consisting of H, RaC(O)—, RaS(O)2— and Ra—;
R5 is independently selected from the group consisting of halogen, —OH, —NH2, cyano, C1-6 alkyl and C1-6 alkoxy;
p is 0, 1, 2 or 3;
R4 is selected from the group consisting of hydrogen, RaS(O)2—, (RaO)2P(O)— and RaC(O)—;
wherein Ra is independently selected from the group consisting of C2-6 alkynyl, C2-6 alkenyl, C1-6 alkyl, C3-6 cycloalkyl, (C1-6 alkyl)NH—, (C1-6 alkyl)2N—, 3- to 6-membered heterocycloalkyl, 5- to 10-membered heteroaryl and C6-10 aryl, wherein Ra is optionally substituted with (C1-6 alkyl)2N—, (C1-6 alkyl)NH—, hydroxy, amino, halogen or cyano.