US 12,441,746 B2
HCK inhibitors for the treatment of fibrosis and cancer
Barbara Murphy, New York, NY (US); Bhaskar Das, West Nyack, NY (US); Chengguo Wei, New York, NY (US); and Li Li, New York, NY (US)
Assigned to Icahn School of Medicine At Mount Sinai, New York, NY (US)
Appl. No. 18/001,114
Filed by Icahn School of Medicine at Mount Sinai, New York, NY (US)
PCT Filed Jun. 9, 2021, PCT No. PCT/US2021/036644
§ 371(c)(1), (2) Date Dec. 8, 2022,
PCT Pub. No. WO2021/252650, PCT Pub. Date Dec. 16, 2021.
Claims priority of provisional application 63/037,174, filed on Jun. 10, 2020.
Prior Publication US 2023/0212197 A1, Jul. 6, 2023
Int. Cl. C07F 5/02 (2006.01); A61P 13/12 (2006.01)
CPC C07F 5/027 (2013.01) [A61P 13/12 (2018.01)] 20 Claims
 
1. A compound of formula I:

OG Complex Work Unit Chemistry
wherein
X is selected from O, NR3, and S;
R1 is selected from O and phenyl optionally substituted with one or more substituents selected from C1-C6 alkyl, C1-C6 alkoxy, C1-C6 fluoroalkyl, and halogen;
R2 is selected from halogen, hydrogen, C1-C6 alkyl, C1-C3 alkoxy, C1-C3 fluoroalkyl, and phenyl;
R3 is selected from hydrogen and C1-C6 alkyl;
Ar is selected from phenyl, a 5-membered heteroaryl, and a 6-membered heteroaryl, wherein said phenyl, 5-membered heteroaryl, or 6-membered heteroaryl is optionally substituted with amino, cyano, halogen, hydroxy, —C(O)NH2, —C(═O)OR4, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, or C1-C6 haloalkoxy;
R4 is selected from hydrogen and C1-C6 alkyl; and
custom character indicates a single bond or a double bond.