US 12,331,018 B2
Pyrrolidine orexin receptor agonists
Stephane L. Bogen, Somerset, NJ (US); Michael J. Breslin, Drexel Hill, PA (US); Dane James Clausen, Rahway, NJ (US); Anthony Ginnetti, Perkasie, PA (US); Michael T. Rudd, Collegeville, PA (US); Shawn J. Stachel, Perkasie, PA (US); Craig A. Stump, Pottstown, PA (US); and Dexi Yang, Livingston, NJ (US)
Assigned to Merck Sharp & Dohme LLC, Rahway, NJ (US)
Appl. No. 17/430,409
Filed by Merck Sharp & Dohme LLC, Rahway, NJ (US)
PCT Filed Feb. 11, 2020, PCT No. PCT/US2020/017573
§ 371(c)(1), (2) Date Aug. 12, 2021,
PCT Pub. No. WO2020/167701, PCT Pub. Date Aug. 20, 2020.
Claims priority of provisional application 62/804,995, filed on Feb. 13, 2019.
Prior Publication US 2022/0144771 A1, May 12, 2022
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 207/14 (2006.01)
CPC C07D 207/14 (2013.01) 6 Claims
 
1. A compound of the formula I:

OG Complex Work Unit Chemistry
wherein:
X is —O— or —NH—, or X may be a direct bond to R1;
Y is N or CH;
R1 is selected from:
(1) -C1-6alkyl, where the alkyl is unsubstituted or substituted with one to six substituents independently selected from R4, and
(2) -C3-6cycloalkyl, where the cycloalkyl is unsubstituted or substituted with one to six substituents independently selected from R4;
R2 is selected from:
(1) hydrogen,
(2) -C1-6alkyl, where the alkyl is unsubstituted or substituted with one to six substituents independently selected from R4,
(3) -C3-6cycloalkyl, where the cycloalkyl is unsubstituted or substituted with one to six substituents independently selected from R4,
(4) -phenyl, where the phenyl is unsubstituted or substituted with one to three substituents independently selected from R4, and
(5) -heteroaryl, where the heteroaryl is selected from: pyridyl, pyrimidinyl, and pyrazinyl, and the heteroaryl is unsubstituted or substituted with one to three substituents independently selected from R4;
R2a and R2b are independently selected from:
(1) hydrogen,
(2) hydroxyl,
(3) halogen, and
(4) -C1-6alkyl, where the alkyl is unsubstituted or substituted with one to six substituents independently selected from halogen;
R3 is phenyl, where the phenyl is unsubstituted or substituted with one to three substituents independently selected from R4,
R4 is selected from:
(1) hydroxyl,
(2) halogen,
(3) C1-6alkyl, which is unsubstituted or substituted with one to six fluoro,
(4) -C3-6cycloalkyl,
(5) —O-C1-6alkyl,
(6) —O (C═O)-C1-6 alkyl,
(7) —NH2,
(8) —NH-C1-6alkyl,
(9) —NO2,
(10) phenyl,
(11) —CO2H, and
(12) —CN;
or a pharmaceutically acceptable salt thereof.