US 11,905,276 B2
Bicyclic compound that acts as CRBN protein regulator
Yunfu Luo, Shanghai (CN); Maoyi Lei, Shanghai (CN); Yu Xu, Shanghai (CN); Junmiao Li, Shanghai (CN); Guoli Zhang, Shanghai (CN); Jinghong Dong, Shanghai (CN); and Shuhui Chen, Shanghai (CN)
Assigned to MEDSHINE DISCOVERY INC., Jiangsu (CN)
Appl. No. 17/642,064
Filed by MEDSHINE DISCOVERY INC., Jiangsu (CN)
PCT Filed Sep. 14, 2020, PCT No. PCT/CN2020/115126
§ 371(c)(1), (2) Date Mar. 10, 2022,
PCT Pub. No. WO2021/047674, PCT Pub. Date Mar. 18, 2021.
Claims priority of application No. 201910865754.6 (CN), filed on Sep. 12, 2019; application No. 201910866549.1 (CN), filed on Sep. 12, 2019; and application No. 201910867013.1 (CN), filed on Sep. 12, 2019.
Prior Publication US 2023/0348441 A1, Nov. 2, 2023
Int. Cl. C07D 405/04 (2006.01); C07D 405/14 (2006.01); C07D 491/107 (2006.01); C07D 409/04 (2006.01); C07D 491/048 (2006.01); C07D 487/08 (2006.01); C07D 487/04 (2006.01); C07D 495/04 (2006.01); C07D 498/04 (2006.01); C07D 413/04 (2006.01)
CPC C07D 405/04 (2013.01) [C07D 405/14 (2013.01); C07D 409/04 (2013.01); C07D 413/04 (2013.01); C07D 487/04 (2013.01); C07D 487/08 (2013.01); C07D 491/048 (2013.01); C07D 491/107 (2013.01); C07D 495/04 (2013.01); C07D 498/04 (2013.01)] 11 Claims
 
1. A compound represented by formula (III) or a pharmaceutically acceptable salt thereof,

OG Complex Work Unit Chemistry
wherein,
custom character is selected from a single bond and a double bond;
T1 is selected from C(R4) and N;
ring A is selected from phenyl, pyridyl and thienyl;
R1 is selected from H, F, Cl, Br and I;
R2 is selected from H, F, Cl, Br, I, OH, NH2 and OCH3;
L1 is selected from a bond, —(CR5)n—, —O(CR5)n—, —S(CR5)n—, —NH(CR5)n—, #—NHCO—, —CONHCH2—, —SOCH2—, —SO2CH2—, —NHSO2—, —CH═CH—, —N═C(Ph)-, —O-cyclobutyl-, —O-cyclopentyl-, —CO-piperazinyl-, and —SO2-piperazinyl-;
R3 is selected from H, F, Cl, Br, I, OH, NH2, CN, COOH, NHCOOH, COOC1-4 alkyl, C1-3 alkyl, C1-3 alkoxy, C2-3 alkenyl, phenyl, pyridyl, tetrahydropyranyl,

OG Complex Work Unit Chemistry
and the COOH, NHCOOH, COOC1-4 alkyl, C1-3 alkyl, C1-3 alkoxy, C2-3 alkenyl, phenyl, pyridyl, tetrahydropyranyl,

OG Complex Work Unit Chemistry
are optionally substituted by 1, 2, or 3 Ra;
R4 is selected from H, F, Cl, Br, I and CH3;
R5 is selected from H, F, Cl, Br and I;
Ra is selected from H, F, Cl, Br, I, OH, NRR′, CN, C1-4 alkyl, C1-3 alkoxy, COOCH3, CONH2 and

OG Complex Work Unit Chemistry
R and R′ are each independently selected from H and CH3;
n is selected from 1, 2, 3;
a site with “#” is the site connected with R3 group.