US 12,404,249 B2
Heterocyclic derivatives and use thereof
Chan Hee Park, Gyeonggi-do (KR); Jun Hwan Im, Gyeonggi-do (KR); Soon Ok Lee, Gyeonggi-do (KR); Sang Hwi Lee, Gyeonggi-do (KR); Kwang Seok Ko, Gyeonggi-do (KR); Byung Ho Kim, Gyeonggi-do (KR); Hyung Jo Moon, Gyeonggi-do (KR); Jae Ill Kim, Gyeonggi-do (KR); Heon Kyu Park, Gyeonggi-do (KR); and Yeon Ju Hong, Gyeonggi-do (KR)
Assigned to C&C RESEARCH LABORATORIES, Gyeonggi-do (KR)
Appl. No. 17/058,209
Filed by C&C RESEARCH LABORATORIES, Gyeonggi-do (KR)
PCT Filed May 31, 2019, PCT No. PCT/KR2019/006554
§ 371(c)(1), (2) Date Nov. 24, 2020,
PCT Pub. No. WO2019/231271, PCT Pub. Date Dec. 5, 2019.
Claims priority of application No. 10-2018-0062450 (KR), filed on May 31, 2018.
Prior Publication US 2021/0155594 A1, May 27, 2021
Int. Cl. C07D 239/72 (2006.01); C07D 215/38 (2006.01); C07D 215/48 (2006.01); C07D 473/34 (2006.01)
CPC C07D 239/72 (2013.01) [C07D 215/38 (2013.01); C07D 215/48 (2013.01); C07D 473/34 (2013.01)] 17 Claims
 
1. A compound of the following Formula 1, or a pharmaceutically acceptable salt thereof:

OG Complex Work Unit Chemistry
wherein
each of X1, X2 and X3 is independently C or N, provided that at least one of X1, X2 and X3 is N;
R1 is hydrogen, halo, alkyl, haloalkyl, alkoxy or alkylamino;
R2 is hydrogen, hydroxy, halo, carboxy, —C(═O)—NH—NH2, alkyl, alkoxy, haloalkoxy, alkoxy-carbonyl, carboxy-alkoxy, aminocarbonyl-alkoxy, alkoxy-carbonyl-alkoxy, aryl, aryl-oxy, aryl-alkyl-aminosulfonyl, aryl-carbonyl, aminocarbonyl, 5- to 8-membered heterocycloalkyl or 5- to 8-membered heterocycloalkylcarbonyl, wherein the heterocycloalkyl has 1 to 3 heteroatoms selected from N, O and S, and the aryl is optionally substituted with nitro or halo;
R3 is hydrogen or aryl-alkyl;
R4 is nitro, nitroso, amino, alkylsulfonyl-amino, alkylsulfonylhydroxyamino(-N(OH)S(O2)alkyl) or haloalkylsulfonyl-amino; provided that when R1 is alkyl, R4 is not alkylsulfonyl-amino; and when R1 is hydrogen or methyl, R4 is not amino or nitro;
A ring is aryl or 3- to 8-membered saturated or unsaturated heterocycle having 1 to 3 heteroatoms selected from N, O and S;
D is —CH2—;
E is —CH2— optionally substituted with halo;
n is an integer of 0 to 2; and
m is an integer of 2 to 4;
provided that when X1 and X3 are N, X2 is C, and R1 is hydrogen; n is 0, m is 2, R2 is hydrogen or aryl substituted with halo, and R4 is nitro, alkylsulfonyl-amino or haloalkylsulfonyl-amino,
provided that the compound of Formula 1 is not 2-methyl-N-(4-nitrophenethyl)quinoline-4-amine, N-[2-(4-nitrophenyl)ethyl]thieno[2,3-d]pyrimidin-4-amine, or N-[2-(4-nitrophenyl)ethyl]thieno[3,2-d]pyrimidin-4-amine; and
provided that A ring is not 5-membered unsaturated heterocycle having 2 nitrogen atoms.