US 12,269,819 B2
Small molecule inhibitors of Galectin-3
Chunjian Liu, Pennington, NJ (US); Jianxin Feng, Bensalem, PA (US); Pratik Devasthale, Plainsboro, NJ (US); Natesan Murugesan, Princeton Junction, NJ (US); Bruce A. Ellsworth, Princeton, NJ (US); Alicia Regueiro-Ren, New Hope, PA (US); Susheel Jethanand Nara, Mumbai (IN); Prasada Rao Jalagam, Bangalore (IN); and Manoranjan Panda, Bangalore (IN)
Assigned to Bristol-Myers Squibb Company, Princeton, NJ (US)
Appl. No. 17/601,942
Filed by BRISTOL-MYERS SQUIBB COMPANY, Princeton, NJ (US)
PCT Filed Apr. 8, 2020, PCT No. PCT/US2020/027203
§ 371(c)(1), (2) Date Oct. 7, 2021,
PCT Pub. No. WO2020/210308, PCT Pub. Date Oct. 15, 2020.
Claims priority of provisional application 62/831,753, filed on Apr. 10, 2019.
Prior Publication US 2022/0144818 A1, May 12, 2022
Int. Cl. C07H 17/02 (2006.01); C07D 405/04 (2006.01); C07D 405/14 (2006.01); C07D 409/14 (2006.01); C07D 417/14 (2006.01)
CPC C07D 417/14 (2013.01) [C07D 405/04 (2013.01); C07D 405/14 (2013.01); C07D 409/14 (2013.01); C07H 17/02 (2013.01)] 13 Claims
 
1. A compound of Formula (I) or (II):

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt thereof, wherein:
X is independently selected from —C(O)—, —CH2—, and —CH2C(O)—;
Ar1 is independently phenyl or naphthyl; and wherein each ring moiety is substituted with 1 to 5 substituents selected from cyano, halogen, C1-4 alkyl, C1-4 alkoxy, C1-4 haloalkyl, and C1-4 haloalkoxy;
R1 is independently selected from H, C1-4 alkyl, and C1-4 haloalkyl;
R2 is independently H or C1-4 alkyl;
R3 is independently selected from Ar2, —(CH2)1-2Ar2, and —CH2CH2NR4Ar2;
Ar2 is independently selected from a heteroaryl including from 9 to 10 ring atoms, wherein from 1 to 4 ring atoms are each independently selected from N, N(R5), O, and S; and wherein each ring moiety is substituted with 0 to 4 substituents selected from OH, cyano, halogen, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy, C1-4 haloalkoxy, N(C1-4 alkyl)2, —SO2(C1-4 alkyl), —OPh, —OBn, C3-6 cycloalkyl, and phenyl substituted with 0 to 1 substituent selected from cyano, halogen, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy, C1-4 haloalkoxy, —NH2, —NH(C1-4 alkyl), and —N(C1-4 alkyl)2;
R4 is independently H or C1-4 alkyl; and
R5 is independently H or C1-4 alkyl.