US 12,110,289 B2
Heterocyclic compounds, preparation methods and uses thereof
Xing Dai, Short Hills, NJ (US); Yaolin Wang, Shanghai (CN); Yueheng Jiang, Shanghai (CN); Yanqin Liu, Shanghai (CN); Zhe Shi, Shanghai (CN); Zhenwu Wang, Shanghai (CN); Liangshan Tao, Shanghai (CN); Zixing Han, Shanghai (CN); Haotao Niu, Shanghai (CN); and Jifang Weng, Shanghai (CN)
Assigned to InventisBio Co., Ltd., Shanghai (CN)
Filed by InventisBio Co., Ltd., Shanghai (CN)
Filed on Jul. 1, 2021, as Appl. No. 17/365,503.
Application 17/365,503 is a division of application No. 17/172,988, filed on Feb. 10, 2021, granted, now 11,091,481.
Application 17/172,988 is a continuation of application No. PCT/CN2020/091274, filed on May 20, 2020.
Prior Publication US 2021/0355125 A1, Nov. 18, 2021
Int. Cl. C07D 471/04 (2006.01); A61K 31/282 (2006.01); A61K 31/438 (2006.01); A61K 31/519 (2006.01); A61K 33/243 (2019.01); A61P 35/00 (2006.01); C07D 519/00 (2006.01)
CPC C07D 471/04 (2013.01) [A61K 31/282 (2013.01); A61K 31/438 (2013.01); A61K 31/519 (2013.01); A61K 33/243 (2019.01); A61P 35/00 (2018.01); C07D 519/00 (2013.01)] 17 Claims
 
1. A compound of Formula I-1 or I-2, or a pharmaceutically acceptable salt thereof:

OG Complex Work Unit Chemistry
wherein:
X is O, S, N, or NR10,
wherein R10 is hydrogen, an optionally substituted C1-4 alkyl, optionally substituted C2-4 alkenyl, optionally substituted C2-4 alkynyl, optionally substituted C1-4 heteroalkyl, optionally substituted C3-6 carbocyclic ring, optionally substituted 4 to 7 membered heterocyclic ring, or a nitrogen protecting group;
each of A3, A4, and A5 is independently CR30 or N,
wherein R30 at each occurrence is independently hydrogen, F, Cl, C1-4 alkyl, or C1-4 alkoxy;
R2 and R3 are each independently hydrogen, halogen, —OH, —CN, optionally substituted C1-4 alkyl, optionally substituted C2-4 alkenyl, optionally substituted C2-4 alkynyl, optionally substituted C3-6 carbocyclic ring, optionally substituted 4 to 7 membered heterocyclic ring, or optionally substituted C1-4 alkoxy;
Het is a 4-10 membered heterocyclic ring, optionally substituted with independently selected R4 group(s), (R4)n, wherein n is 0, 1, 2, or 3, and R4 at each occurrence is independently C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl, 3 or 4 membered ring, fluorine substituted C1-4 alkyl, hydroxyl substituted C1-4 alkyl, or cyano substituted C1-4 alkyl;
or two R4 groups can join together to form a 3-6 membered ring structure;
R7 is hydrogen, halogen, CN, a 3-4 membered ring, optionally substituted C1-4 alkyl, optionally substituted C2-4 alkenyl, optionally substituted C2-4 alkynyl, or optionally substituted C1-4 alkoxy;
R8 is an optionally substituted aryl or optionally substituted heteroaryl;
each of J1 and J2 is independently selected from O, S, N, CR40, and NR41, wherein each of R40 and R41 at each occurrence is independently hydrogen, OH, CN, halogen, an optionally substituted C1-4 alkyl, optionally substituted C2-4 alkenyl, optionally substituted C2-4 alkynyl, an optionally substituted C1-4 alkoxy, optionally substituted C1-4 heteroalkyl, optionally substituted C3-6 carbocyclic ring, or optionally substituted 4 to 7 membered heterocyclic ring,
R5 and R6 are each independently hydrogen, halogen, —CN, —COOR23A, —CONR21AR22A, optionally substituted C1-6 alkyl, optionally substituted C2-6 alkenyl, optionally substituted C2-6 alkynyl, optionally substituted C3-6 carbocyclic ring, optionally substituted phenyl, optionally substituted 5 or 6 membered heteroaryl, or optionally substituted 4 to 7 membered heterocyclic ring, or R5 and R6 can join together to form an optionally substituted C3-6 carbocyclic ring, or optionally substituted 4 to 7 membered heterocyclic ring, wherein each of R21A and R22A at each occurrence is independently hydrogen, an optionally substituted C1-4 alkyl, optionally substituted C2-4 alkenyl, optionally substituted C2-4 alkynyl, optionally substituted C1-4 heteroalkyl, optionally substituted C3-6 carbocyclic ring, optionally substituted 4 to 7 membered heterocyclic ring, or a nitrogen protecting group; and R23A at each occurrence is independently hydrogen, an optionally substituted C1-4 alkyl, optionally substituted C2-4 alkenyl, optionally substituted C2-4 alkynyl, optionally substituted C1-4 heteroalkyl, optionally substituted C3-6 carbocyclic ring, optionally substituted 4 to 7 membered heterocyclic ring, or an oxygen protecting group;
wherein the dotted line indicates that the respective connection is a single or double bond, provided that the bicyclic ring as a whole is aromatic.