US 12,304,899 B2
Factor XI activation inhibitors
Jacqueline D. Hicks, Watchung, NJ (US); John S. Debenham, Scotch Plains, NJ (US); Amjad Ali, Freehold, NJ (US); Lan Wei, Berkeley Heights, NJ (US); Tianying Jian, Westfield, NJ (US); Dexi Yang, Livingston, NJ (US); Anthony K. Ogawa, San Mateo, CA (US); Wenlang Fu, Madison, NJ (US); Matthew Lombardo, Flemington, NJ (US); Rongze Kuang, Green Brook, NJ (US); Meng Yang, Westfield, NJ (US); Sung-Sau So, Verona, NJ (US); Kenneth Ellsworth, Cranbury, NJ (US); Peter Nizner, Fanwood, NJ (US); Daniel A. Tatosian, Berkeley Heights, NJ (US); Robert R. Wilkening, Maplewood, NJ (US); and Jun Wang, Avon, CT (US)
Assigned to Merck Sharp & Dohme LLC, Rahway, NJ (US)
Appl. No. 17/613,988
Filed by Merck Sharp & Dohme LLC, Rahway, NJ (US)
PCT Filed May 26, 2020, PCT No. PCT/US2020/034468
§ 371(c)(1), (2) Date Nov. 24, 2021,
PCT Pub. No. WO2020/243049, PCT Pub. Date Dec. 3, 2020.
Claims priority of provisional application 62/854,749, filed on May 30, 2019.
Prior Publication US 2022/0235033 A1, Jul. 28, 2022
Int. Cl. C07D 401/14 (2006.01); C07D 405/14 (2006.01); C07D 413/14 (2006.01); C07D 417/14 (2006.01); C07D 471/04 (2006.01); C07D 471/14 (2006.01)
CPC C07D 401/14 (2013.01) [C07D 405/14 (2013.01); C07D 413/14 (2013.01); C07D 417/14 (2013.01); C07D 471/04 (2013.01)] 13 Claims
 
1. A compound of the formula:

OG Complex Work Unit Chemistry
wherein
R1 is phenyl or heteroaryl, which may be monocyclic or bicyclic, wherein said phenyl and heteroaryl groups are optionally substituted with one to three substituents independently selected from the group consisting of halo, oxo, cyano, R4, OR4, R6 and NO2;
R2 is piperidinyl, NR4R5 or NR4R6, wherein said piperidinyl group is optionally substituted with one to three halo;
R3 is heterocyclyl, which may be monocyclic or bicyclic, or NHC(CH3)2R6, wherein said heterocyclyl is optionally substituted with one to three substituents independently selected from the group consisting of halo, cyano, R4, OR4, R6, CONR4R5, NR4COR5, (C1-3 alkyl) R6 and SO2R4,
R4 is hydrogen or C1-6 alkyl, which is optionally substituted with one to three halo;
R5 is hydrogen or C1-6 alkyl, which is optionally substituted with one to three halo;
R6 is phenyl, C3-6 cycloalkyl, heterocyclyl or heteroaryl, wherein said heteroaryl is optionally substituted with one to three substituents independently selected from the group consisting of C1-6 alkyl and halo;
Rx is hydrogen, halo or C1-6 alkyl;
n is an integer from one to three;
or a pharmaceutically acceptable salt thereof.