US 11,053,208 B2
Compound having oxadiazole and pharmaceutical composition containing the same
Choon Ho Ryu, Gyeonggi-do (KR); Min Soo Han, Gyeonggi-do (KR); Yeo Jin Yoon, Gyeonggi-do (KR); Yu Jin Kim, Gyeonggi-do (KR); Ka Eun Lee, Gyeonggi-do (KR); Ju Young Lee, Gyeonggi-do (KR); Myung Jin Jung, Gyeonggi-do (KR); Eun Hee Baek, Gyeonggi-do (KR); Yu Jin Shin, Gyeonggi-do (KR); Eun Ju Choi, Gyeonggi-do (KR); Young Soon Kang, Gyeonggi-do (KR); Yong Soo Kim, Gyeonggi-do (KR); Yea Mi Song, Gyeonggi-do (KR); Jin Sung Kim, Gyeonggi-do (KR); and Hee Jeong Lim, Gyeonggi-do (KR)
Assigned to SK BIOPHARMACEUTICALS CO., LTD., Gyeonggi-Do (KR)
Appl. No. 16/613,659
Filed by SK BIOPHARMACEUTICALS CO., LTD., Gyeonggi-do (KR)
PCT Filed Sep. 20, 2019, PCT No. PCT/KR2019/012257
§ 371(c)(1), (2) Date Nov. 14, 2019,
PCT Pub. No. WO2020/060299, PCT Pub. Date Mar. 26, 2020.
Claims priority of application No. 10-2018-0113956 (KR), filed on Sep. 21, 2018.
Prior Publication US 2021/0115001 A1, Apr. 22, 2021
Int. Cl. A61P 25/18 (2006.01); A61K 31/41 (2006.01); C07D 271/10 (2006.01); A61P 25/08 (2006.01); A61K 31/4245 (2006.01)
CPC C07D 271/10 (2013.01) [A61K 31/4245 (2013.01); A61P 25/08 (2018.01)] 16 Claims
 
1. A compound represented by the following Chemical Formula 1, or an optical isomer, a stereoisomer or a pharmaceutically acceptable salt thereof:

OG Complex Work Unit Chemistry
wherein
R1 is selected from the group consisting of the following formulas:

OG Complex Work Unit Chemistry
R2 is hydrogen, halo, hydroxy, alkyl, haloalkyl, hydroxyalkyl, alkoxyalkyl, carbamoyloxy, alkoxy, alkylthio, haloalkoxy, or hydroxyalkoxy;
R3 is hydrogen, alkyl, cycloalkyl, haloalkyl, hydroxyalkyl, alkoxyalkyl, carbamoyl, alkylcarbamoyl, dialkylcarbamoyl, carbonyl, or alkylcarbonyl;
R4 is hydrogen, halo, hydroxy, alkyl, haloalkyl, hydroxyalkyl, alkoxyalkyl, carbamoyl, alkylcarbamoyl, or dialkylcarbamoyl;
R5 is hydrogen, halo, hydroxy, alkyl, haloalkyl, hydroxyalkyl, alkoxyalkyl, carbamoyl, alkylcarbamoyl, or dialkylcarbamoyl;
R6, R7, R8 and R9 are each independently hydrogen, halo, alkyl, haloalkyl, hydroxyalkyl, alkoxyalkyl, carbamoyloxyalkyl, alkyl-C(O)O-alkyl, alkoxy, alkylthio, haloalkoxy, hydroxyalkoxy, alkoxy-alkoxy, carbamoyloxyalkoxy, alkyl-C(O)O-alkoxy, amino, dialkylamino, carbonylamino, alkylcarbonylamino, haloalkyl-carbonylamino, or heterocycloalkyl having 1 to 3 nitrogen (N) atoms;
X, Y and Z are each independently selected from the group consisting of nitrogen (N) and oxygen (O), wherein at least one of X, Y or Z is oxygen (O);
m is an integer of 0 to 3;
n, o, and p are each independently an integer of 0 to 5; and
q is an integer of 0 to 2.