US 12,275,729 B2
Substituted tetrahydroquinolin compounds as indoleamine 2,3-dioxygenase (IDO) inhibitors
Yongqi Deng, Newton, MA (US); Abdelghani Achab, Melrose, MA (US); David Jonathan Bennett, Winchester, MA (US); Indu Bharathan, Somerville, MA (US); Xavier Fradera, Boston, MA (US); Craig Gibeau, Northborough, MA (US); Yongxin Han, Needham, MA (US); Derun Li, West Roxbury, MA (US); Kun Liu, Needham, MA (US); Qinglin Pu, Needham, MA (US); Sulagna Sanyal, Belmont, MA (US); David Sloman, Newton, MA (US); Wensheng Yu, Edison, NJ (US); and Hongjun Zhang, Boston, MA (US)
Assigned to Merck Sharp & Dohme LLC, Rahway, NJ (US)
Appl. No. 16/758,717
Filed by Merck Sharp & Dohme LLC, Rahway, NJ (US)
PCT Filed Oct. 29, 2018, PCT No. PCT/US2018/057916
§ 371(c)(1), (2) Date Apr. 23, 2020,
PCT Pub. No. WO2019/089412, PCT Pub. Date May 9, 2019.
Claims priority of provisional application 62/580,273, filed on Nov. 1, 2017.
Prior Publication US 2021/0179607 A1, Jun. 17, 2021
Int. Cl. C07D 471/04 (2006.01); A61K 45/06 (2006.01); C07D 215/14 (2006.01)
CPC C07D 471/04 (2013.01) [A61K 45/06 (2013.01); C07D 215/14 (2013.01)] 5 Claims
 
1. A compound of formula (Ia), formula (If), or formula (Ig), or a pharmaceutically acceptable salt thereof:

OG Complex Work Unit Chemistry
wherein:
A is phenyl, optionally substituted with 1-3 halogens;
X is selected from (1)-NHC(O)— and (2)—C(O)NH—;
each of R1 and R2 is independently selected from:
(1) H, and
(2) C1-4 alkyl, optionally substituted with 1-3 halogens;
or alternatively, R1 and R2 together with the carbon to which they are attached form a 3-5 membered ring selected from:
(1) cyclopropyl, optionally substituted with 1-3 halogens,
(2) cyclobutyl, optionally substituted with 1-3 halogens,
(3) oxiranyl, and
(4) oxetanyl;
R3 is selected from:
(1) phenyl, optionally substituted with 1-3 halogens, and
(2) a 4-6 membered monocyclic aromatic heterocyclyl selected from oxadiazolyl, oxazolyl, pyrazolyl, pyrazinyl, pyridinyl, pyrimidinyl, thiazolyl, and triazolyl, each of which is optionally substituted with 1-3 substituents independently selected from:
(a) halogen,
(b)—CH3, optionally substituted with 1-3 halogens,
(c)—O—CH3, and
(d) cyclopropyl; and
each of R4 and R5 is H.