US 12,473,276 B2
Compound having neuroprotective effect, preparation method therefor and use thereof
Bo Liang, Shanghai (CN); Huanming Chen, Shanghai (CN); Gang Liu, Shanghai (CN); Zhijun Zhang, Shanghai (CN); Tian Xia, Shanghai (CN); Bo Hua, Shanghai (CN); and Qiu Jin, Shanghai (CN)
Assigned to SHANGHAI ZHIMENG BIOPHARMA, INC., Shanghai (CN)
Appl. No. 17/783,796
Filed by Shanghai Zhimeng Biopharma, Inc., Shanghai (CN)
PCT Filed Dec. 10, 2020, PCT No. PCT/CN2020/135289
§ 371(c)(1), (2) Date Jun. 9, 2022,
PCT Pub. No. WO2021/115380, PCT Pub. Date Jun. 17, 2021.
Claims priority of application No. 201911261595.5 (CN), filed on Dec. 10, 2019.
Prior Publication US 2023/0054304 A1, Feb. 23, 2023
Int. Cl. C07D 413/04 (2006.01); C07D 263/58 (2006.01); C07D 265/18 (2006.01); C07D 413/14 (2006.01); C07D 493/04 (2006.01); C07D 498/10 (2006.01); C07F 9/6584 (2006.01); C07H 13/10 (2006.01)
CPC C07D 413/04 (2013.01) [C07D 263/58 (2013.01); C07D 265/18 (2013.01); C07D 413/14 (2013.01); C07D 493/04 (2013.01); C07D 498/10 (2013.01); C07F 9/65846 (2013.01); C07H 13/10 (2013.01)] 8 Claims
 
1. The compound of formula I or a stereoisomer, or a pharmaceutically acceptable salt thereof:

OG Complex Work Unit Chemistry
wherein,
R1 and R3 are chlorine;
R2, R4, R5, R5′, R6, R6′, R7, R8 and R9 are hydrogen;
X is

OG Complex Work Unit Chemistry
W is O;
m is 1;
n is 0;
Z is N;
Y is COOR15 or CONR16R17;
R15, R16, and R17 are each independently selected from the group consisting of hydrogen, C1-6 alkyl, C3-8 cycloalkyl, C6-10 aryl, 3-15 membered saturated or unsaturated heterocycloalkyl or heteroaryl containing one or more heteroatoms selected from N, S or O, and —(C1-6 alkylene)(3-15 membered saturated or unsaturated heterocycloalkyl or heteroaryl containing one or more heteroatoms selected from N, S or O); the alkyl, cycloalkyl, aryl, heteroaryl and heterocycloalkyl are optionally substituted by one or more substituents selected from the group consisting of hydroxyl, C1-6 alkylene hydroxyl, —NR20R21, C2-6 alkynyl, C2-6 alkenyl, C1-6 alkyl, C3-8 cycloalkyl, 3-8 membered heterocycloalkyl containing one or more heteroatoms selected from N, S or O unsubstituted or substituted by C1-6 alkyl, halogenated C1-6 alkyl, C1-6 alkyl substituted by amino and carboxyl, C1-6 alkoxy, and —COO(C1-6 alkyl); and
R20 and R21 are independently hydrogen or C1-6 alkyl.