US 11,919,868 B2
Heterocyclic compounds and related methods
Michael James Genin, Draper, UT (US); Joseph Carpenter, Bountiful, UT (US); and Carl Brooks, Salt Lake City, UT (US)
Assigned to RECURSION PHARMACEUTICALS, INC., Salt Lake City, UT (US)
Filed by Recursion Pharmaceuticals, Inc., Salt Lake City, UT (US)
Filed on Mar. 1, 2022, as Appl. No. 17/684,352.
Claims priority of provisional application 63/155,651, filed on Mar. 2, 2021.
Prior Publication US 2022/0380323 A1, Dec. 1, 2022
Int. Cl. C07D 471/04 (2006.01); A61K 31/5513 (2006.01); A61P 31/04 (2006.01); C07D 243/30 (2006.01); C07D 487/04 (2006.01); C07D 491/04 (2006.01); C07D 495/04 (2006.01); C07D 498/04 (2006.01); C07D 513/04 (2006.01)
CPC C07D 243/30 (2013.01) 24 Claims
 
1. A compound of Formula (I):

OG Complex Work Unit Chemistry
or a stereoisomer, a tautomer, or a pharmaceutically acceptable salt thereof;
wherein
X1, X2, and X3 are each independently CR2, N, NR5, O, or S;
X4 and X5 are each independently C(H) or N;
m is an integer of 0, 1, or 2;
Z is a 6- to 10-membered aryl or, 5- to 10-membered heteroaryl containing 1 to 3 heteroatoms independently selected from N, O, and S;
R1 and R2 are each independently hydrogen, halo, cyano, hydroxyl, amino, C1-6 alkyl, alkylamino, haloalkyl, hydroxyalkyl, aminoalkyl, alkoxyalkyl, haloalkoxyalkyl, alkoxy, or haloalkoxy;
R3 and R4 are each independently hydrogen, C1-6 alkyl, alkylamino, haloalkyl, alkoxy, haloalkoxy, 6- to 10-membered aryl, 5- to 10-membered heteroaryl containing 1 to 3 heteroatoms independently selected from N, O, and S, 3- to 10-membered carbocyclyl, or 4- to 10-membered heterocyclyl containing 1 to 3 heteroatoms independently selected from N, O, and S, wherein the aryl, heteroaryl, carbocyclyl, and heterocyclyl are independently substituted with 0 to 5 R5;
R5 is hydrogen, halo, cyano, hydroxyl, amino, C1-6 alkyl, alkylamino, haloalkyl, hydroxyalkyl, hydroxycycloalkyl, aminoalkyl, alkoxyalkyl, haloalkoxyalkyl, alkoxy, haloalkoxy or —C(O)OR6; and
R6 is hydrogen or C1-6 alkyl.