US 12,281,108 B2
Pyrrolidinone derivatives as formyl peptide 2 receptor agonists
Nicholas R. Wurtz, Pennington, NJ (US); James A. Johnson, Pennington, NJ (US); Zulan Pi, Pennington, NJ (US); and Andrew Quoc Viet, Schwenksville, PA (US)
Assigned to Bristol-Myers Squibb Company, Princeton, NJ (US)
Appl. No. 17/295,092
Filed by BRISTOL-MYERS SQUIBB COMPANY, Princeton, NJ (US)
PCT Filed Nov. 25, 2019, PCT No. PCT/US2019/062905
§ 371(c)(1), (2) Date May 19, 2021,
PCT Pub. No. WO2020/112583, PCT Pub. Date Jun. 4, 2020.
Claims priority of provisional application 62/819,832, filed on Mar. 18, 2019.
Claims priority of provisional application 62/771,196, filed on Nov. 26, 2018.
Prior Publication US 2022/0002281 A1, Jan. 6, 2022
Int. Cl. C07D 413/14 (2006.01); C07D 413/12 (2006.01); C07D 417/12 (2006.01); C07D 417/14 (2006.01); C07D 498/04 (2006.01); A61K 31/423 (2006.01); A61K 31/4245 (2006.01); A61K 31/433 (2006.01); A61P 9/04 (2006.01); A61P 9/10 (2006.01); A61P 11/00 (2006.01)
CPC C07D 413/14 (2013.01) [C07D 413/12 (2013.01); C07D 417/12 (2013.01); C07D 417/14 (2013.01); C07D 498/04 (2013.01)] 7 Claims
 
1. A compound of formula I

OG Complex Work Unit Chemistry
where:
R1 is absent, Ar3, cycloalkyl substituted with 0-2 halo and 0-1 Ar4 substituents, or ((Ar5)alkyl)(H)NCO;
R2 is hydrogen, alkyl, or CH2CO2H;
Ar1 is isoxazolyl, oxadiazolyl, thiadiazolyl, benzoisoxazolyl, isoxazolopyridinyl, or benzooxazolyl, and is substituted with 0-2 halo, alkyl, alkoxy, fluoroalkyl, or fluoroalkoxy substituents;
Ar2 is phenyl, pyridinyl, or pyridazinyl, and is substituted with 1 alkoxy, halo, haloalkyl or haloalkoxy substituent in the 4-position and 0-2 additional halo substituents;
Ar3 is phenyl, pyridinyl, pyridazinyl, pyrimidinyl, or pyrazinyl, and is substituted with 0-3 substituents selected from cyano, halo, alkyl, haloalkyl, cycloalkyl, alkoxy, (cycloalkyl)alkoxy, haloalkoxy, OAr6, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, and pyrazolyl;
Ar4 is phenyl or pyridinyl substituted with 0-3 substituents selected from cyano, halo, alkyl, haloalkyl, alkoxy, and haloalkoxy;
Ar5 is phenyl or pyridinyl substituted with 0-3 substituents selected from cyano, halo, alkyl, haloalkyl, alkoxy, and haloalkoxy; and
Ar6 is phenyl, pyridinyl, pyridazinyl, pyrimidinyl, or pyrazinyl, and is substituted with 0-3 substituents selected from cyano, halo, alkyl, haloalkyl, alkoxy, and haloalkoxy;
Provided when Ar1 is oxadiazolyl or thiadiazolyl, Ar1 is substituted with 0-1 halo, alkyl, alkoxy, fluoroalkyl, or fluoroalkoxy substituent;
or a pharmaceutically acceptable salt thereof.