US 12,331,035 B2
Bicyclic compound and use thereof
Yong Je Shin, Gyeonggi-do (KR); Jin Hee Kim, Gyeonggi-do (KR); Jun Lee, Gyeonggi-do (KR); Hyun Suk Choi, Gyeonggi-do (KR); Se Hyuk Kim, Gyeonggi-do (KR); Eun Ji Kang, Gyeonggi-do (KR); Sook Kyung Park, Gyeonggi-do (KR); Ho Youl Lee, Gyeonggi-do (KR); and Ho Yeon Lee, Gyeonggi-do (KR)
Assigned to SK BIOPHARMACEUTICALS CO., LTD., Gyeonggi-do (KR)
Appl. No. 17/771,114
Filed by SK BIOPHARMACEUTICALS CO., LTD., Gyeonggi-do (KR)
PCT Filed Oct. 22, 2020, PCT No. PCT/KR2020/014530
§ 371(c)(1), (2) Date Apr. 22, 2022,
PCT Pub. No. WO2021/080359, PCT Pub. Date Apr. 29, 2021.
Claims priority of application No. 10-2019-0132452 (KR), filed on Oct. 23, 2019.
Prior Publication US 2023/0023140 A1, Jan. 26, 2023
Int. Cl. C07D 401/14 (2006.01); A61P 35/00 (2006.01); C07D 401/06 (2006.01); C07D 405/14 (2006.01); C07D 413/14 (2006.01); C07D 417/14 (2006.01); C07D 471/04 (2006.01); C07D 471/08 (2006.01); C07D 491/08 (2006.01); C07D 491/107 (2006.01); C07D 498/04 (2006.01)
CPC C07D 401/14 (2013.01) [A61P 35/00 (2018.01); C07D 401/06 (2013.01); C07D 405/14 (2013.01); C07D 413/14 (2013.01); C07D 417/14 (2013.01); C07D 471/04 (2013.01); C07D 471/08 (2013.01); C07D 491/08 (2013.01); C07D 491/107 (2013.01); C07D 498/04 (2013.01)] 15 Claims
 
1. A compound represented by the following Formula 1, or an optical isomer, a stereoisomer or an isotopic variant thereof, or a pharmaceutically acceptable salt thereof:

OG Complex Work Unit Chemistry
wherein
X is CH or N;
n is an integer from 0 to 2;
R1 is -D-R9 or

OG Complex Work Unit Chemistry
 wherein D is a direct bond, —CH2—, —O— or —C≡C—;
R9 is halo, hydroxy, alkyl, hydroxyalkyl, dialkylaminoalkyl, saturated or unsaturated heterocyclyl, or saturated heterocyclyl-alkyl, wherein the saturated or unsaturated heterocyclyl is optionally substituted with one or more substituents selected from halo, alkyl, alkoxy, haloalkyl, hydroxyalkyl, alkoxyalkyl, alkylcarbonyl, alkoxycarbonyl and saturated heterocyclyl;
R10 and R11 are each independently hydrogen, alkyl, cycloalkyl, hydroxyalkyl, cycloalkyl-alkyl, alkylcarbonyl, hydroxyalkylcarbonyl, aralkyl, saturated heterocyclyl, saturated or unsaturated heterocyclyl-alkyl, unsaturated heterocyclyl-carbonyl, or saturated heterocyclyl-alkylcarbonyl; or R10 and R11 together with nitrogen (N) atom to which they are attached may form saturated or unsaturated heterocyclyl; wherein the saturated or unsaturated heterocyclyl is optionally substituted with one or more substituents selected from hydroxy, oxo, formyl (—CHO), cyano, alkyl, alkoxy, hydroxyalkyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, alkylamino, alkylsulfonyl, alkoxyalkyl, aminocarbonyl, alkylcarbonylamino, alkylcarbonylalkylamino, alkoxyalkylalkylamino, dialkylamino, dialkylaminoalkyl, dialkylaminoalkoxy, dialkylaminocarbonyl and 4- to 10-membered, saturated heterocyclyl;
R2 is hydrogen or halo;
R3 is hydrogen, halo or alkyl, or together with carbon (C) atom to which they are attached may form cycloalkyl when n is 2;
R4, R5, R6 and R7 are each independently hydrogen or alkyl; and
R8 is hydrogen, halo, alkyl, alkoxy or amino.