US 12,378,268 B2
Heterocyclic THR-β receptor agonist compound and preparation method and use therefor
Shanghai Yu, Suzhou (CN); and Ben Li, Suzhou (CN)
Assigned to Hepagene Therapeutics (HK) Limited, Hong Kong (CN)
Appl. No. 17/636,331
Filed by Hepagene Therapeutics (HK) Limited, Hong Kong (CN)
PCT Filed Oct. 19, 2020, PCT No. PCT/CN2020/121801
§ 371(c)(1), (2) Date Feb. 17, 2022,
PCT Pub. No. WO2021/032218, PCT Pub. Date Feb. 25, 2021.
Claims priority of application No. 201910763932.4 (CN), filed on Aug. 19, 2019; and application No. 202010112084.3 (CN), filed on Feb. 24, 2020.
Prior Publication US 2022/0298187 A1, Sep. 22, 2022
Int. Cl. C07F 9/6574 (2006.01); C07F 9/38 (2006.01); C07F 9/40 (2006.01); C07F 9/44 (2006.01)
CPC C07F 9/65742 (2013.01) [C07F 9/383 (2013.01); C07F 9/4018 (2013.01); C07F 9/4465 (2013.01)] 24 Claims
 
1. A compound shown in formula (I) or a stereoisomer thereof or a pharmaceutically acceptable salt thereof,

OG Complex Work Unit Chemistry
wherein
R1 and R2 are each independently selected from a halogen atom or a C1-6 alkyl group;
R3 and R4 are each independently selected from hydrogen, a C1-6 alkyl group, an unsubstituted phenyl group, a phenyl group substituted with at least one substituent selected from a halogen atom, a trifluoromethyl group, a C1-6 alkyl group, a C1-6 alkoxyl group or a cyano group, an unsubstituted naphthyl group, a naphthyl group substituted with at least one substituent selected from a halogen atom, a trifluoromethyl group, a C1-6 alkyl group, a C1-6 alkoxyl group or a cyano group,

OG Complex Work Unit Chemistry
or R3, R4, and adjacent

OG Complex Work Unit Chemistry
jointly form the following six-membered ring

OG Complex Work Unit Chemistry
wherein V is an unsubstituted five-to ten-membered aryl group, a five-to ten-membered aryl group substituted with at least one substituent selected from a halogen atom, a trifluoromethyl group, a C1-6 alkyl group, a C1-6 alkoxyl group or a cyano group, an unsubstituted five-to ten-membered heteroaryl group containing 1 or 2 heteroatoms selected from N, S and O, or a five-to ten-membered heteroaryl group that is substituted with at least one substituent selected from a halogen atom, a trifluoromethyl group, a
C1-6 alkyl group, a C1-6 alkoxyl group or a cyano group and that contains one or two heteroatoms selected from N, S or O;
R5 is selected from H or a C1-6 alkyl group;
R6, R7, and R5 are each independently a C1-6 alkyl group;
X is selected from —O— or —CH2—;
Y is selected from —O— or —CH2—;
Z and Z′ are each independently selected from —O— or —NH—;
L is selected from —O—, —S— or —CH2—; and
n is 1, 2 or 3;
wherein the halogen atom is selected from F, Cl or Br.