US 12,240,836 B2
Compounds as GCN2 inhibitors, pharmaceutical compositions and uses thereof
Cheonhyoung Park, Seoul (KR); Kimoon Ryu, Yongin-si (KR); Tae-Hun Kim, Seoul (KR); Ha Yoon Kim, Hwaseong-si (KR); Eunhye Ju, Suwon-si (KR); Hyung Ki Lee, Hwaseong-si (KR); Youngjee Jeong, Seongnam-si (KR); Doyoung Choi, Seoul (KR); Jun Hwan Moon, Yongin-si (KR); Nayeon Park, Suwon-si (KR); Iksoo Jang, Seongnam-si (KR); Kyu Hwan Kim, Suwon-si (KR); Hyangsoo Lee, Seoul (KR); and Min Jung Lee, Yongin-si (KR)
Assigned to Dong-A ST Co., Ltd., Seoul (KR)
Filed by DONG-A ST CO., LTD., Seoul (KR)
Filed on Jul. 5, 2022, as Appl. No. 17/857,706.
Prior Publication US 2024/0025884 A1, Jan. 25, 2024
Int. Cl. C07D 403/14 (2006.01); A61K 31/506 (2006.01); A61K 31/53 (2006.01); A61K 31/5377 (2006.01); A61K 31/541 (2006.01); A61P 35/00 (2006.01); C07D 401/14 (2006.01); C07D 409/14 (2006.01); C07D 413/14 (2006.01); C07D 417/14 (2006.01); C07D 471/04 (2006.01)
CPC C07D 403/14 (2013.01) [A61K 31/506 (2013.01); A61K 31/53 (2013.01); A61K 31/5377 (2013.01); A61K 31/541 (2013.01); A61P 35/00 (2018.01); C07D 401/14 (2013.01); C07D 409/14 (2013.01); C07D 413/14 (2013.01); C07D 417/14 (2013.01); C07D 471/04 (2013.01)] 7 Claims
 
1. A compound represented by a following Formula (I), a stereoisomer thereof, a pharmaceutically acceptable salt thereof, or a solvate thereof:

OG Complex Work Unit Chemistry
wherein,
L1 and L2 each independently represent H; (C1-5)alkyl; or L1 and L2 may be connected to form a 5 to 6-membered ring,
M represents H; halogen; (C1-5)alkyl; (C3-7)cycloalkyl; or (C1-5)alkoxy,
G represents H; halogen; (C1-5)alkyl; (C1-5)alkoxy; or —NH2, wherein at least one H of —NH2 optionally substituted with (C1-5)alkyl,
Y1 represents H; or (C1-5)alkyl,
Z represents —C(═O)—; or —CH2— optionally substituted with one or more (C1-5)alkyl; and/or Z may be connected to Y1 to form a 5- to 6-membered ring,
Y3 represents 4- to 6-membered heterocycloalkyl which is optionally substituted with W1 and W2; or Y3 may be connected to Z to form an aryl or a heteroaryl in case that Z is connected to Y1 to form the 5- to 6-membered ring,
W1 and W2 each independently represent H; halogen; —OH; (C1-5)alkyl optionally substituted with —OH or —CN; 5- to 7-membered heterocycloalkyl optionally substituted with (C1-5)alkyl; a heteroaryl optionally substituted with (C1-5)alkyl; —COR1; —OR2 or —NH2, wherein at least one H of —NH2 optionally substituted with a heteroaryl,
R1 represents (C1-5)alkoxy; —OH; 5-7 membered heterocycloalkyl optionally substituted with (C1-5)alkyl; or —NH2, wherein at least one H of —NH2 optionally substituted with (C3-7)cycloalkyl,
R2 represents (C1-5)alkyl optionally substituted with a heteroaryl; an aryl; or a heteroaryl, wherein the aryl or the heteroaryl is optionally substituted with one or more R2a,
R2a independently represents halogen, (C1-5)alkyl optionally substituted with an aryl, or 5- to 7-membered heterocycloalkyl substituted with (C1-5)alkyl; (C5-6)cycloalkenyl optionally substituted with (C1-5)alkyl; 5- to 7-membered heterocycloalkyl substituted with C1-5)alkyl or —OH; —CF3; (C1-5)alkoxy optionally substituted with an aryl; an aryl; a heteroaryl optionally substituted with (C1-5)alkyl; thio(C1-5)alkyl; —COR1; or NR3R4,
R3 and R4 each independently represent H; halogen; (C1-5)alkyl optionally substituted with halogen, —CF3, —OH, (C1-5)alkoxy, (C1-5)alkyl-N—(C1-5)alkyl, an aryl or (C3-7)cycloalkyl; (C3-7)cycloalkyl; (C1-5)alkoxy; an aryl; or —C(═O)(C1-5)alkyl.