US 12,091,405 B2
Substituted pyrazole compounds as indoleamine 2,3-dioxygenase inhibitors
Dane Clausen, Rahway, NJ (US); Xavier Fradera, Boston, MA (US); Liangqin Guo, Monroe Township, NJ (US); Yongxin Han, Needham, MA (US); Shuwen He, Fanwood, NJ (US); Joseph Kozlowski, Princeton, NJ (US); Guoqing Li, Belle Mead, NJ (US); Theodore A. Martinot, Southborough, MA (US); Alexander Pasternak, Jamaica Plain, MA (US); David Sloman, Newton, MA (US); Li Xiao, Cranbury, NJ (US); Wensheng Yu, Edison, NJ (US); and Rui Zhang, Plainsboro, NJ (US)
Assigned to Merck Sharp & Dohme LLC, Rahway, NJ (US)
Appl. No. 17/287,256
Filed by Merck Sharp & Dohme LLC, Rahway, NJ (US)
PCT Filed Oct. 28, 2019, PCT No. PCT/US2019/058246
§ 371(c)(1), (2) Date Apr. 21, 2021,
PCT Pub. No. WO2020/092183, PCT Pub. Date May 7, 2020.
Claims priority of provisional application 62/753,988, filed on Nov. 1, 2018.
Prior Publication US 2021/0395240 A1, Dec. 23, 2021
Int. Cl. C07D 413/14 (2006.01); C07D 401/14 (2006.01)
CPC C07D 413/14 (2013.01) [C07D 401/14 (2013.01)] 13 Claims
 
1. A compound of formula (I), or a pharmaceutically acceptable salt thereof:

OG Complex Work Unit Chemistry
wherein:
each of the dashed lines “ . . . ” is an optional bond;
m is 1; n is 1;
Ra is selected from: (1) hydrogen and (2) C1-6 alkyl;
Rb is hydrogen;
Rc is selected from: (1) hydrogen, (2) halogen, and (3) C1-6 alkyl;
R1 and R2 together with the nitrogen to which they are attached form a 4-6 membered heterocyclyl containing the one nitrogen to which they are attached and zero to two additional hetero atoms independently selected from N, S and O; wherein the heterocyclyl is optionally substituted with one to four substituents independently selected from:
(a) halogen,
(b) —OH,
(c) C1-6 alkyl, optionally substituted with one to four substituents independently selected from (i) —OH, (ii) halogen and (iii) —C(O)—NHRe, wherein Re is selected from (i) hydrogen and (ii) C1-6 alkyl,
(d) —O—C1-6 alkyl, optionally substituted with one to four substituents independently selected from (i) —OH and (ii) halogen,
(e) —NHRf, wherein Rf is selected from (i) hydrogen, (ii) C1-6 alkyl and (iii) —C(O)—C1-6 alkyl, and
(f) —C(O)—C1-6 alkyl, optionally substituted with one to four substituents independently selected from (a) —OH and (b) halogen; and
R3 is selected from (1) C6-10 carbocyclyl and (2) heterocyclyl, wherein each of the carbocyclyl and heterocyclyl is optionally substituted with one to four substituents independently selected from:
(a) halogen,
(b) C1-6 alkyl, optionally substituted with one to four halogens,
(c) —O—C1-6 alkyl, optionally substituted with one to four halogens,
(d) —CN, and
(e) C3-6 cycloalkyl, optionally substituted with C1-6 alkyl.