US 12,421,205 B2
GLP-1 receptor agonist
Han Kyu Lee, Suwon-si (KR); Jeong-Un Hwang, Suwon-si (KR); Kyu-Hwan Lee, Yongin-si (KR); Hyung-Ho Choi, Suwon-si (KR); Jung-In Jang, Suwon-si (KR); Hyuck-Joo Lee, Suwon-si (KR); Seung-Tae Kang, Suwon-si (KR); Hyun-Ho Yoon, Suwon-si (KR); Neul Ha, Suwon-si (KR); Hyun-Hwa La, Suwon-si (KR); Jin Woong Kim, Suwon-si (KR); Dae Hoon Kim, Seoul (KR); and Myoung Ki Baek, Seoul (KR)
Assigned to Hyundai Pharm Co., Ltd., Cheonan-si (KR)
Appl. No. 17/780,486
Filed by HYUNDAI PHARM CO., LTD., Cheonan-si (KR)
PCT Filed Dec. 1, 2020, PCT No. PCT/KR2020/017405
§ 371(c)(1), (2) Date May 26, 2022,
PCT Pub. No. WO2021/112538, PCT Pub. Date Jun. 10, 2021.
Claims priority of application No. 10-2019-0158410 (KR), filed on Dec. 2, 2019.
Prior Publication US 2023/0051318 A1, Feb. 16, 2023
Int. Cl. C07D 401/10 (2006.01); C07D 235/12 (2006.01); C07D 401/14 (2006.01); C07D 405/06 (2006.01); C07D 405/14 (2006.01); C07D 409/14 (2006.01); C07D 413/06 (2006.01); C07D 413/14 (2006.01)
CPC C07D 401/10 (2013.01) [C07D 235/12 (2013.01); C07D 401/14 (2013.01); C07D 405/06 (2013.01); C07D 405/14 (2013.01); C07D 409/14 (2013.01); C07D 413/06 (2013.01); C07D 413/14 (2013.01)] 15 Claims
 
1. A compound represented by the following Formula 1, or a pharmaceutically acceptable salt thereof:

OG Complex Work Unit Chemistry
wherein
A is C6-10 aryl; C3-7 cycloalkyl; 5- or 6-membered heteroaryl containing one heteroatom selected from N, O, and S; 5- or 6-membered heterocycloalkyl containing one heteroatom selected from N, O, and S; or 9- or 10-membered fused heteroaryl containing at least one heteroatom selected from N, O, and S,
B is any one of the following (1) to (5),

OG Complex Work Unit Chemistry
L is —(CH2)n-O—, —O—(CH2)n-, —(CH2)n-NH—, —NH—(CH2)n-, —(CH2)n-N(C1-5 alkyl)-, —N(C1-5 alkyl)-(CH2)n-, —CONH—, or —NHCO—, where n is 1 or 2,
X is CH or N,
R1 and R2 are each independently selected from the group consisting of hydrogen, C1-5 alkyl, C1-5 alkoxy, C1-5 haloalkyl, halogen, cyano, and nitro,
R3 is hydrogen or halogen,
R4 and R5 are each independently selected from the group consisting of hydrogen, C1-5 alkyl, C1-5 alkoxy, C1-5 haloalkyl, halogen, cyano, and nitro,
R6 is —(CH2)m—O—(C1-5 alkyl) (where m is 1 or 2); C1-5 haloalkyl; 5- or 6-membered heteroaryl containing one or two heteroatoms selected from N, O, and S, which is unsubstituted or substituted with C1-5 alkyl; or 4- or 5-membered heterocycloalkyl containing one heteroatom selected from N, O, and S, which is unsubstituted or substituted with C1-5 alkyl.