US 12,281,119 B2
Imidazo[2,1-f][1,2,4]triazin-4-amine derivatives as TLR7 agonist
Guoliang Zhang, Beijing (CN); Jianzhuang Miao, Beijing (CN); Changyou Zhou, Beijing (CN); Gang Chen, Beijing (CN); and Jing Li, Beijing (CN)
Assigned to BEIGENE, LTD., Grand Cayman (KY)
Appl. No. 17/428,856
Filed by BEIGENE, LTD., Grand Cayman (KY)
PCT Filed Feb. 6, 2020, PCT No. PCT/CN2020/074437
§ 371(c)(1), (2) Date Aug. 5, 2021,
PCT Pub. No. WO2020/160711, PCT Pub. Date Aug. 13, 2020.
Claims priority of application No. PCT/CN2019/074732 (WO), filed on Feb. 7, 2019; application No. PCT/CN2019/098757 (WO), filed on Jul. 31, 2019; and application No. PCT/CN2020/073673 (WO), filed on Jan. 22, 2020.
Prior Publication US 2022/0119394 A1, Apr. 21, 2022
Int. Cl. C07D 487/04 (2006.01); A61P 35/00 (2006.01); C07D 519/00 (2006.01)
CPC C07D 487/04 (2013.01) [A61P 35/00 (2018.01); C07D 519/00 (2013.01); C07B 2200/05 (2013.01)] 9 Claims
 
1. A compound of Formula (I),

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt thereof, or a stereoisomer thereof, wherein
X is N;
L1 is —CH2—,
R1 is —OR1a, wherein R1a is a branched —C4-8 alkyl, wherein the branched —C4-8 alkyl is at the alpha position with respect to the oxygen atom;
R2 and R3, at each occurrence, are independently hydrogen;
R4 is hydrogen;
Ring A is phenyl or pyridyl;
R5 is halogen, alkyl, or haloalkyl;
p is a number of 0, 1, 2 or 3;
L2 is —O—;
R6 is alkyl, said alkyl is optionally substituted with one or two or three substituents R6c;
R6c is independently hydrogen, halogen, —OR6d, —SR6d, —NR6dR6e, —COR6d, —SO2R6d, —C(═O)NR6dR6e, or alkyl, said alkyl, is optionally substituted with one or two or three substituents R68;
R6d and R6e are independently hydrogen, alkyl, alkenyl, heterocyclyl, or aryl, each of said alkyl, alkenyl, heterocyclyl, or aryl, is optionally substituted with one or two or three substituents R6g;
R6g, at each occurrence, is independently hydrogen, halogen, —OR6h, —SR6h, —NR6hR6i, —N(R6h)C(═O)OR6i, alkyl, heterocyclyl, aryl, or heteroaryl,
R6h and R6i are independently hydrogen or alkyl.