US 11,053,225 B2
Pyrimidine derivative compound, optical isomer thereof, or pharmaceutically acceptable salt thereof, and composition for preventing or treating Tyro 3 related disease comprising same as active ingredient
Sung Yun Cho, Daejeon (KR); Chang Hoon Lee, Daejeon (KR); Yong Ki Min, Daejeon (KR); and Jong Yeon Hwang, Jeollabuk-do (KR)
Assigned to KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY, Daejeon (KR)
Appl. No. 16/610,327
Filed by KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY, Daejeon (KR)
PCT Filed May 2, 2018, PCT No. PCT/KR2018/005162
§ 371(c)(1), (2) Date Nov. 1, 2019,
PCT Pub. No. WO2018/203691, PCT Pub. Date Nov. 8, 2018.
Claims priority of application No. 10-2017-0056002 (KR), filed on May 2, 2017; application No. 10-2017-0114317 (KR), filed on Sep. 7, 2017; and application No. 10-2017-0114322 (KR), filed on Sep. 7, 2017.
Prior Publication US 2020/0087286 A1, Mar. 19, 2020
Int. Cl. C07D 401/14 (2006.01); C07D 403/04 (2006.01); A61K 31/506 (2006.01); C07D 403/14 (2006.01); C07D 239/48 (2006.01); C07D 405/04 (2006.01); C07D 405/14 (2006.01); C07D 409/14 (2006.01); C07D 413/14 (2006.01); C07D 417/14 (2006.01)
CPC C07D 403/14 (2013.01) [C07D 239/48 (2013.01); C07D 403/04 (2013.01); C07D 405/04 (2013.01); C07D 405/14 (2013.01); C07D 409/14 (2013.01); C07D 413/14 (2013.01); C07D 417/14 (2013.01)] 10 Claims
 
1. A pyrimidine derivative compound represented by Chemical Formula 1 below, an optical isomer thereof, or a pharmaceutically acceptable salt thereof:

OG Complex Work Unit Chemistry
wherein:
R1 is substituted pyrazole-4-yl,
wherein the substituted pyrazole-4-yl is substituted with hydroxy C1-C4 alkyl or substituted or unsubstituted piperidinyl, and
wherein the substituted piperidinyl is substituted with at least one substituent selected from the group consisting of halogen, C1-C10 haloalkyl, oxo (═O), hydroxy, cyano, nitro, amino, acetamino, trihalogen acetamino, trihalogen acetyl, C1-C10 alkyl, C1-C10 alkoxy, C4-C10 cycloalkyl, C4-C10 heterocycloalkyl, C4-C10 aryl, or C4-C10 heteroaryl;
R2 is substituted or unsubstituted C4-C10 cycloalkyl, substituted or unsubstituted C4-C8 heterocycloalkyl, substituted or unsubstituted C4-C10 aryl, substituted or unsubstituted C4-C10 heteroaryl, or a substituted or unsubstituted fused ring in which C4-C10 aryl is fused with C4-C8 heterocycloalkyl,
wherein the substituted cycloalkyl, substituted heterocycloalkyl, substituted aryl, substituted heteroaryl, or fused ring is substituted with at least one substituent selected from the group consisting of halogen, C1-C10 haloalkyl, oxo (═O), hydroxy, cyano, nitro, acetamino, trihalogen acetamino, trihalogen acetyl, C4-C10 cycloalkyl, C4-C8 heterocycloalkyl, C4-C10 aryl, C4-C10 heteroaryl;
R3 is substituted or unsubstituted C4-C10 cycloalkyl, substituted or unsubstituted C4-C8 heterocycloalkyl, substituted or unsubstituted C4-C10 aryl, substituted or unsubstituted C4-C10 heteroaryl, substituted or unsubstituted C4-10 aryl C1-10 alkyl, substituted or unsubstituted C4-C10 heteroaryl C1-10 alkyl, or a substituted or unsubstituted fused ring in which C4-C10 aryl is fused with C4-C10 cycloalkyl or C4-C8 heterocycloalkyl,
wherein the substituted cycloalkyl, substituted heterocycloalkyl, substituted aryl, substituted heteroaryl, substituted arylalkyl, substituted heteroarylalkyl, or substituted fused ring is substituted with at least one substituent selected from the group consisting of halogen, C1-C10 haloalkyl, hydroxy, cyano, nitro, amino, acetamino, trihalogen acetamino, trihalogen acetyl, oxo (═O), C4-C10 cycloalkyl, C4-C8 heterocycloalkyl, C4-C10 heteroaryl, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C1-C10 alkoxy, or substituted or unsubstituted C4-C10 aryl,
wherein the substituted alkyl, substituted alkoxy, or substituted aryl is substituted with at least one substituent selected from the group consisting of halogen, oxo (═O), or substituted or unsubstituted C1-C10 alkyl, and
wherein the substituted alkyl is substituted with at least one substituent selected from halogen or oxo (═O); and
R4 is hydrogen.