US 12,226,425 B2
Inhibitors of ARG1 and/or ARG2
Joel Beatty, San Mateo, CA (US); Eric Thomas Newcomb, Menlo Park, CA (US); Jay Patrick Powers, Pacifica, CA (US); Brandon Reid Rosen, San Mateo, CA (US); Yongli Su, Foster City, CA (US); Anh Thu Tran, Union City, CA (US); Corinne Nicole Foley, San Carlos, CA (US); Rebecca Louise Grange, Union City, CA (US); Tezcan Guney, Hayward, CA (US); Steven Donald Jacob, Oakland, CA (US); Jaroslaw Kalisiak, Mountain View, CA (US); Manmohan Reddy Leleti, Dublin, CA (US); Erick Allen Lindsey, Fremont, CA (US); and Debashis Mandal, Fremont, CA (US)
Assigned to Arcus Biosciences, Inc., Hayward, CA (US)
Appl. No. 17/294,353
Filed by Arcus Biosciences, Inc., Hayward, CA (US)
PCT Filed Nov. 15, 2019, PCT No. PCT/US2019/061657
§ 371(c)(1), (2) Date May 14, 2021,
PCT Pub. No. WO2020/102646, PCT Pub. Date May 22, 2020.
Claims priority of provisional application 62/768,284, filed on Nov. 16, 2018.
Prior Publication US 2022/0016143 A1, Jan. 20, 2022
Int. Cl. A61K 31/69 (2006.01); A61K 31/282 (2006.01); A61K 31/704 (2006.01); A61K 33/243 (2019.01); A61K 39/395 (2006.01); C07F 5/02 (2006.01)
CPC A61K 31/69 (2013.01) [A61K 31/282 (2013.01); A61K 31/704 (2013.01); A61K 33/243 (2019.01); A61K 39/3955 (2013.01); C07F 5/025 (2013.01)] 11 Claims
 
1. A compound having the Formula (I) or a pharmaceutically acceptable salt, hydrate, or solvate thereof, wherein,

OG Complex Work Unit Chemistry
X is N or CR4a,
each R1 is independently H or C1-8 alkyl,
R2 is H or CH3;
each R3 is independently H or C1-8 alkyl; or two R3 groups are joined together to form a 5 or 6-membered ring which is unsubstituted or substituted with from 1 to 4 Ra;
each R4a, R4b, R4c, and R4d is independently selected from the group consisting of H, halogen, CN, C1-8 alkyl, C1-8 alkoxy, C1-8 hydroxyalkyl, C1-8 haloalkyl, C1-8 haloalkoxy, -X1-Y,-X1—SO2R5a, and -X1—NR5bR5c, each R5a, R5b, and R5c is independently selected from the group consisting of H, C1-8 alkyl, C1-8 haloalkyl, C1-8 alkylC (O)-, C3-7 cycloalkyl, 3- to 7-membered heterocycloalkyl, aryl, heteroaryl, and an amino acid, or R5b and R5c are joined together to form a 4- to 6-membered ring; and wherein each of the 4- to 6-membered ring, C3-7 cycloalkyl, or 3- to 7-membered heterocycloalkyl, aryl, and heteroaryl, are unsubstituted or substituted with from 1 to 4 Rb;
each X1 is a bond, —O—, C1-6 alkylene, or —O—C1-6 alkylene, wherein the alkylene portions are unsubstituted or substituted with 1 to 4 Rc and 0 or 1 oxo;
each Ra, Rb, and Rc is independently halogen, CN, OH, NH2, CO2H, C1-4 alkyl, C1-4 haloalkyl, C3-6 cycloalkyl, or phenyl, or two Re are combined to form a C3-6 cycloalkyl which is unsubstituted or substituted with 1 to 3 Rd;
each Y is independently phenyl, a 5- or 6-membered heteroaryl, 3- to 7-membered heterocycloalkyl, or C3-6 cycloalkyl, each of which is unsubstituted or substituted with from 1 to 3 Rd, and
each Rd is independently halogen, C1-4 alkyl, amino, aminoC1-4 alkyl, C1-4 haloalkyl, OH, or C1-4
hydroxyalkyl.