US 12,071,435 B2
TLR8 agonist
Fei Sun, Shanghai (CN); Zhe Cai, Shanghai (CN); Charles Z. Ding, Shanghai (CN); and Shuhui Chen, Shanghai (CN)
Assigned to CHIA TAI TIANQING PHARMACEUTICAL GROUP CO., LTD., Jiangsu (CN)
Appl. No. 17/286,316
Filed by CHIA TAI TIANQING PHARMACEUTICAL GROUP CO., LTD., Jiangsu (CN)
PCT Filed Oct. 18, 2019, PCT No. PCT/CN2019/111897
§ 371(c)(1), (2) Date Apr. 16, 2021,
PCT Pub. No. WO2020/078455, PCT Pub. Date Apr. 23, 2020.
Claims priority of application No. 201811221301.1 (CN), filed on Oct. 19, 2018; and application No. 201910161144.8 (CN), filed on Mar. 4, 2019.
Prior Publication US 2021/0340141 A1, Nov. 4, 2021
Int. Cl. C07D 471/04 (2006.01); C07D 403/12 (2006.01)
CPC C07D 471/04 (2013.01) [C07D 403/12 (2013.01)] 14 Claims
 
1. A compound of formula (I), or a stereoisomer thereof, or a pharmaceutically acceptable salt thereof,

OG Complex Work Unit Chemistry
wherein,
the carbon atom with “*” is a chiral carbon atom;
the carbon atom with “#” is a chiral carbon atom present in a form of a single (S) enantiomer or in a form enriched with (S) enantiomer;
X is selected from the group consisting of CH and N;
Y is selected from the group consisting of CR2 and N;
n is selected from the group consisting of 0, 1, 2 and 3;
L is selected from the group consisting of —O— and —CR3R4—;
R1 is selected from the group consisting of C1-6 alkyl, wherein the C1-6 alkyl is optionally substituted with 1, 2 or 3 Ra;
R2 is selected from the group consisting of H, CN, NH2, halogen, C1-6 alkyl, C1-6 alkyl-O—, NHRb, N(Rc)2, C3-6 cycloalkyl, —C(═O)Ra, —C(═O)—O—Re, —O—C(═O)—Re, —S(═O)2Rf and —S(═O)Rg;
R3 and R4 are each independently selected from the group consisting of H, halogen and C1-3 alkyl, wherein the C1-3 alkyl is optionally substituted with 1, 2 or 3 Rh;
alternatively, R3 and R4 are linked to form a 3-6 membered saturated ring, wherein the 3-6 membered saturated ring is optionally substituted with 1, 2 or 3 Ri;
Ra, Rb, Rc, Ra, Re, Rf, Rg, Rh and Ri are each independently selected from the group consisting of F, Cl, Br, I, OH, CN, NH2, C1-6 alkyl, C1-6 heteroalkyl, C3-6 cycloalkyl, 3-6 membered heterocycloalkyl, phenyl and 5-6 membered heteroaryl, wherein the C1-6 alkyl, C1-6 heteroalkyl, C3-6 cycloalkyl, 3-6 membered heterocycloalkyl, phenyl and 5-6 membered heteroaryl are optionally substituted with 1, 2 or 3 R;
R is each independently selected from the group consisting of F, Cl, Br, I, OH, CN, NH2, CH3,

OG Complex Work Unit Chemistry
and the C1-6 heteroalkyl, 3-6 membered heterocycloalkyl and 5-6 membered heteroaryl each contain 1, 2, 3 or 4 heteroatoms or heteroatom groups independently selected from the group consisting of —NH—, —O—, —S— and N.