US 12,378,250 B2
Tricyclic compound as IRAK4 inhibitor
Heeyeong Cho, Daejeon (KR); Hee-Jong Lim, Daejeon (KR); Woo Kyu Park, Daejeon (KR); Dae Young Jeong, Daejeon (KR); Hyeon Young Kim, Daejeon (KR); Sae-Bom Yoon, Daejeon (KR); Chong Ock Lee, Daejeon (KR); Heung Kyoung Lee, Daejeon (KR); Victor Sukbong Hong, Daejeon (KR); and Ji Hye Choi, Daejeon (KR)
Assigned to KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY, Daejeon (KR)
Appl. No. 17/294,705
Filed by KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY, Daejeon (KR)
PCT Filed Nov. 20, 2019, PCT No. PCT/KR2019/015948
§ 371(c)(1), (2) Date May 18, 2021,
PCT Pub. No. WO2020/106059, PCT Pub. Date May 28, 2020.
Claims priority of application No. 10-2018-0144188 (KR), filed on Nov. 21, 2018; and application No. 10-2019-0148566 (KR), filed on Nov. 19, 2019.
Prior Publication US 2022/0009933 A1, Jan. 13, 2022
Int. Cl. C07D 487/04 (2006.01); A23L 33/10 (2016.01); C07D 487/14 (2006.01); C07D 519/00 (2006.01)
CPC C07D 487/04 (2013.01) [A23L 33/10 (2016.08); C07D 487/14 (2013.01); C07D 519/00 (2013.01); A23V 2002/00 (2013.01)] 6 Claims
 
1. A compound represented by the following Chemical Formula 1:

OG Complex Work Unit Chemistry
wherein,
A1 is CH,
A2 is N,
A3 is CR1,
R1 is hydrogen, a halogen, —COOR5,
R2 is hydrogen, an amino group, —COOR6,

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry
R3 is hydrogen or a (C6-C12) aryl,
R4 is -L1-L2-R7,
an amino group (—NH2), a (C1-C12) heteroaryl or a (C6-C12) aryl of R2 is optionally substituted with at least one or more groups selected from the group consisting of a (C1-C4) alkyl, a (C1-C4) alkyl substituted with a halogen, a (C1-C4) thioalkyl, an amino group (—NH2), a methylamino group (—NHCH3), a dimethylamino group (—N(CH3)2), —CH2OH, a (C1-C4) alkoxy, a hydroxyl group (—OH), a halogen, a methanesulfonyl group (—SO2CH3), —SO2N(CH3)2, a nitro group (—NO2), a cyano group (—CN),

OG Complex Work Unit Chemistry
a (C6-C12) aryl of R3 is optionally substituted with a nitro group (—NO2),
L1 is —N(R8)— or —O—,
L2 is —(CH2)m—,

OG Complex Work Unit Chemistry
and m is an integer from 2 to 5,
R7 is —N(R9)2, —OR10, —SO2CH3, —SO2N(CH3)2, or a monocyclic 5- to 7-membered saturated heterocycle, wherein the heterocycle comprises 1 to 3 heteroatoms selected from nitrogen, oxygen and sulfur,
R5 is a (C1-C4) alkyl,
R6 is a (C1-C4) alkyl,
R8 is hydrogen or a (C1-C4),
R9 is a (C1-C4) alkyl,
R10 is a (C1-C4) alkyl,
a heterocycloalkyl amino of R7 is optionally substituted with at least one or more groups selected from the group consisting of —SO2CH3 and —COOC(CH3)3 (—Boc).