US 12,275,721 B2
Indazole carboxamides as kinase inhibitors
Jie Chen, Cambridge, MA (US); Carolyn Diane Dzierba, Medford, MA (US); Junqing Guo, Princeton, NJ (US); Amy C. Hart, Littleton, CO (US); William J. Pitts, Newtown, PA (US); and Sing-Yuen Sit, Meriden, CT (US)
Assigned to Bristol-Myers Squibb Company, Princeton, NJ (US)
Appl. No. 17/762,771
Filed by BRISTOL-MYERS SQUIBB COMPANY, Princeton, NJ (US)
PCT Filed Oct. 2, 2020, PCT No. PCT/US2020/053882
§ 371(c)(1), (2) Date Mar. 23, 2022,
PCT Pub. No. WO2021/067654, PCT Pub. Date Apr. 8, 2021.
Claims priority of provisional application 62/909,920, filed on Oct. 3, 2019.
Prior Publication US 2022/0380355 A1, Dec. 1, 2022
Int. Cl. C07D 409/04 (2006.01); C07D 403/04 (2006.01); C07D 417/04 (2006.01)
CPC C07D 409/04 (2013.01) [C07D 403/04 (2013.01); C07D 417/04 (2013.01)] 12 Claims
 
1. A compound having formula (I), or salt thereof, wherein

OG Complex Work Unit Chemistry
Ring B is a 5-membered heterocycle having 1-2 heteroatoms selected from N, S, and O, and substituted with 0-2 C1-2 alkyl groups;
R1 is C1-6 alkyl, C1-6 haloalkyl, or C1-6 deuteroalkyl;
R2 is C1-6 alkyl, C1-6 haloalkyl, C0-6 alkyl-C6-10 aryl, C0-6 alkyl-C3-6 cycloalkyl, or a C0-6 alkyl-3 to 6 membered heterocycle having 1-4 heteroatoms selected from N, S and O, wherein any of the aryl, cycloalkyl, or heterocycle groups are substituted with 0-3 R2a, and wherein any of the alkyl groups are substituted with 0-1 OH;
R2a is halo, CN, ═O, C1-6 alkyl, C1-6 alkoxy, hydroxy-C1-6 alkoxy, C1-6 deuteroalkyl, C1-6 deuteroalkoxy, C1-6 haloalkyl, C1-6 haloalkoxy, C0-3 alkyl-C3-6 cycloalkyl-C0-3 alkyl-, C3-6 halocycloalkyl, C3-6 cycloalkoxy, C3-6 cycloalkyl-C1-6 alkoxy-, C3-6 cycloalkyl-C1-3 deuteroalkoxy-, C3-6 cycloalkyl-C1-3 haloalkoxy-, C1-6 alkoxy-C1-3 alkyl-, C3-6 cycloalkoxy-C1-3 alkyl-, C6-10 aryl, phenyl-C1-3 alkoxy-, C6-10 aryl-O—, phenyl C1-4 alkyl-SO2—, C1-4 alkyl-SO2—, C3-6 cycloalkyl-SO2—, NR3R3CO—, NR3R3—(CH2)n—, R4—C(O)—, R4—OC(O)—, R4—C(O)O—, R3—NH—C(O)O—, R5—OC(O)NH—, R3—NH—C(O)NR3—, R5—SO2—, R4—SO2NH—, R4—NHSO2—, or heterocycle, wherein the heterocycle is independently a 4-6 membered ring having 1-2 heteroatoms selected from N and O, and wherein each alkyl, cycloalkyl, aryl, phenyl, or heterocycle are substituted with 0-2 R2b;
R2b, at each occurrence, is independently OH, C1-3 alkyl, C1-3 alkoxy, hydroxy C1-3 alkyl, hydroxy C1-3 alkoxy, halo, C═O, C1-3 haloalkyl, or C1-3 haloalkoxy;
R3 is, independently at each occurrence, H, C1-6 alkyl, C0-3 alkyl-C3-6 cycloalkyl, or C0-3 alkyl-phenyl;
R4 is, independently at each occurrence, H, C1-6 alkyl, C0-3 alkyl-C3-6 cycloalkyl, C0-3 alkyl-phenyl or C1-6 haloalkyl;
R5 is, independently at each occurrence, C1-6 alkyl, C0-3 alkyl-C3-6 cycloalkyl, or C0-3 alkyl-phenyl; and
n is 0, 1 or 2.