US 9,808,473 B2
Preparation and use of 3-pyridyl substituted-6,6-difluoro bicyclic himbacine derivatives as par-1 receptor antagonists
James Francis Dropinski, Freehold, NJ (US); Milana Maletic, Summit, NJ (US); Jae-Hun Kim, Scotch Plains, NJ (US); and Deyou Sha, Yardley, PA (US)
Assigned to Merck Sharp & Dohme Corp., Rahway, NJ (US)
Appl. No. 14/912,315
Filed by Merck Sharp & Dohme Corp., Rahway, NJ (US)
PCT Filed Aug. 18, 2014, PCT No. PCT/US2014/051404
§ 371(c)(1), (2) Date Feb. 16, 2016,
PCT Pub. No. WO2015/026686, PCT Pub. Date Feb. 26, 2015.
Claims priority of provisional application 61/868,618, filed on Aug. 22, 2013.
Prior Publication US 2016/0200713 A1, Jul. 14, 2016
Int. Cl. A61K 31/34 (2006.01); A61K 31/60 (2006.01); A61K 45/06 (2006.01); A61K 31/4365 (2006.01); A61K 31/444 (2006.01); C07D 405/14 (2006.01); C07D 409/14 (2006.01); C07D 409/04 (2006.01); A61K 31/343 (2006.01)
CPC A61K 31/60 (2013.01) [A61K 31/4365 (2013.01); A61K 31/444 (2013.01); A61K 45/06 (2013.01); C07D 405/14 (2013.01); C07D 409/14 (2013.01); A61K 31/343 (2013.01); C07D 409/04 (2013.01)] 13 Claims
 
1. A compound of the formula

OG Complex Work Unit Drawing
or a pharmaceutically acceptable salt thereof
wherein:
R1 is halo; —CN; alkyl; cycloalkyl; alkoxy; phenyl, which is optionally substituted one or twice independently by alkyl, halo, or —CN; or a thiophene ring, which is optionally substituted once or twice independently by alkyl.