US 12,187,683 B2
Benzoindazolone compound and intermediate thereof
Whee Seong Lee, Seongnam-si (KR); Eun Ju Lee, Suwon-si (KR); and In Seok Ko, Pyoungtaek-si (KR)
Assigned to LMITO THERAPEUTICS INC., Yongin-si (KR)
Appl. No. 17/310,878
Filed by LMITO THERAPEUTICS INC., Yongin-si (KR)
PCT Filed Feb. 20, 2020, PCT No. PCT/KR2020/002459
§ 371(c)(1), (2) Date Aug. 27, 2021,
PCT Pub. No. WO2020/175851, PCT Pub. Date Sep. 3, 2020.
Claims priority of application No. 10-2019-0023942 (KR), filed on Feb. 28, 2019.
Prior Publication US 2022/0144780 A1, May 12, 2022
Int. Cl. C07D 231/54 (2006.01); C07D 405/12 (2006.01)
CPC C07D 231/54 (2013.01) [C07D 405/12 (2013.01)] 14 Claims
 
1. A compound of Chemical Formula 1, or a pharmaceutically acceptable salt, hydrate, solvate, enantiomer, diasteromer, tautomer or prodrug thereof:

OG Complex Work Unit Chemistry
wherein:
R1 is selected from the group consisting of H, C1-6 alkyl, C1-6 alkoxy, substituted or unsubstituted C6-10 aryl, substituted or unsubstituted heteroaryl, halo, cyano, nitro and NR5R6;
R2 and R3 are each independently not present, or selected from the group consisting of H, O, C1-6 alkyl, substituted or unsubstituted C6-10 aryl and C1-6 alkoxy; and R4 is selected from the group consisting of O, unsubstituted C6-10 aryl and C1-6 alkoxy, wherein at least one of R2 and R4 are O or C1-6 alkoxy;
R5 and R6 are each independently H, C1-6 alkyl or C1-6 alkyl carbonyl, or R5 and R6 may be joined together to form a heterocyclyl containing at least one nitrogen atom in ring structure;
X1, X2, X3 and X4 are each independently selected from C and N, wherein two of X1, X2, X3 and X4 are N, provided that X2 and X4 are not simultaneously N, and X1 and X4 are not simultaneously N;
custom character is a single bond or a double bond depending on R2, R3, R4, X1, X2, X3 and X4;
wherein the alkyl is a linear, branched or cyclic alkyl, the heteroaryl is a 5- to 10-membered aromatic ring containing at least one hetero atom selected from the group consisting of N, O and S in the ring, and where the aryl or heteroaryl is substituted, a substituent thereof is C1-6 alkyl, halo, or C1-6 alkyl substituted with 1 to 3 halos.