US 12,110,299 B2
Thiazole derivatives and pharmaceutically acceptable salts thereof
Kwang Ok Lee, Gyeonggi-Do (KR); Jakyung Yoo, Gyeonggi-Do (KR); Jun Hee Lee, Gwangjin-gu (KR); Mijung Lee, Hwaseong-Si (KR); Kangwoo Lee, Osan-Si (KR); and Jieun Min, Suwon-Si (KR)
Assigned to YUNGJIN PHARM. CO., LTD., Seoul (KR)
Appl. No. 17/277,033
Filed by YUNGJIN PHARM. CO., LTD., Songpa-gu (KR)
PCT Filed Sep. 11, 2019, PCT No. PCT/KR2019/011887
§ 371(c)(1), (2) Date Mar. 17, 2021,
PCT Pub. No. WO2020/060112, PCT Pub. Date Mar. 26, 2020.
Claims priority of application No. 10-2018-0111001 (KR), filed on Sep. 17, 2018.
Prior Publication US 2021/0284658 A1, Sep. 16, 2021
Int. Cl. C07D 498/18 (2006.01); C07D 277/46 (2006.01); C07D 417/12 (2006.01); C07D 417/14 (2006.01); C07D 471/04 (2006.01); C07D 487/18 (2006.01)
CPC C07D 498/18 (2013.01) [C07D 277/46 (2013.01); C07D 417/12 (2013.01); C07D 417/14 (2013.01); C07D 471/04 (2013.01); C07D 487/18 (2013.01)] 17 Claims
 
1. A compound represented by Formula (I), or a pharmaceutically acceptable salt thereof

OG Complex Work Unit Chemistry
wherein:
ring A is phenyl, pyridinyl, pyrazinyl, pyrazolyl, thiophenyl, thiazolyl, or piperidinyl;
ring B is phenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, pyrazolyl, imidazolyl, thiazolyl, tetrahydropyridinyl, piperidinyl, or piperazinyl;
R1 is halo, C1-C6 alkyl, C3-C7 cycloalkyl, C1-C6 haloalkyl, cyano, —SRc, —C(O)Rc, —C(O)OR, —N(Rc)(Rd), —ORc, or —C(Rg)—ORc;
Rc and Rd are each independently H or C1-C6 alkyl;
Rg is H or C1-C6 alkyl;
R2V and R2w are each independently H, halo, or C1-C6 alkyl or
R2v and R2w, taken together with the atom to which they are attached, form a C3-C7 cycloalkyl;
L1 is absent, —N(Re)—, or —*CH2N(Rc)—, * is the site in which L1 is attached to ring B;
where Re is H or C1-C6 alkyl; or Re is bound to an atom on ring B, thereby forming ring B-fused pyrrole or pyrrolidine which is unsubstituted or substituted with C1-C6 alkyl;

OG Complex Work Unit Chemistry
wherein Rf1 is H, halo, C1-C6 alkyl, or cyano;
Rf2 and Rf3 are each independently H, C1-C6 alkyl, C3-C7 cycloalkyl, —N(Rc′ (Rd′), or —CH2N(Rc′)(Rd′);
Rc′ and Rd′ are each independently C1-C6 alkyl; or
Rc′ and Rd′, taken together with the atom to which they are attached, form azetidinyl; piperidinyl; morpholinyl; piperazinyl which is unsubstituted or substituted with C1-C6 alkyl; 2,5-diazabicyclo[2.2.1heptanyl which is unsubstituted or substituted with C1-C6 alkyl; 2-oxa-5-azabicyclo[2.2.11heptanyl: or pyrrolidinyl which is unsubstituted or substituted with halo, hydroxy or C1-C6 alkoxy-C1-C6 alkyl;
Ra is H, halo, or C1-C6 alkyl;
Rb is H, halo, C1-C6 alkyl, C3-C7 cycloalkyl, C1-C6 alkoxy, cyano, C1-C6 haloalkyl, —N(CH3)—CH2CH—N(CH3), or piperazinyl which is unsubstituted or substituted with C1-C6 alkyl;
m and n are each integer 1.