US 11,970,511 B2
Tetrahydropyran-based thiodisaccharide mimics as Galectin-3 inhibitors
Richard A. Hartz, Ewing, NJ (US); Li Xu, Hamilton, NJ (US); David S. Yoon, Ambler, PA (US); Alicia Regueiro-Ren, New Hope, PA (US); Prasada Rao Jalagam, Bangalore (IN); Manoranjan Panda, Bangalore (IN); and Satheesh Kesavan Nair, Bangalore (IN)
Assigned to Bristol-Myers Squibb Company, Princeton, NJ (US)
Appl. No. 17/251,964
Filed by BRISTOL-MYERS SQUIBB COMPANY, Princeton, NJ (US)
PCT Filed Jun. 13, 2019, PCT No. PCT/US2019/036877
§ 371(c)(1), (2) Date Dec. 14, 2020,
PCT Pub. No. WO2019/241461, PCT Pub. Date Dec. 19, 2019.
Claims priority of provisional application 62/831,867, filed on Apr. 10, 2019.
Claims priority of provisional application 62/685,395, filed on Jun. 15, 2018.
Prior Publication US 2021/0323991 A1, Oct. 21, 2021
Int. Cl. C07H 17/04 (2006.01); A61P 13/12 (2006.01)
CPC C07H 17/04 (2013.01) [A61P 13/12 (2018.01)] 23 Claims
 
1. A compound of Formula (I)

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt thereof, wherein:
A is O, NH or N(COCH3);
R1 is (R4)CONH— or

OG Complex Work Unit Chemistry
R2 is alkyl, (CO2(R5))alkyl, or (CON(R6)(R7))alkyl;
R3 is cycloalkyl, tetrahydropyranyl, or Ar1, and is substituted with 0-3 substituents selected from cyano, halo, alkyl, haloalkyl, hydroxy, alkoxy, haloalkoxy, CO2R5, and (R6)(R7)N;
R4 is alkyl, cycloalkyl, bicyclo[2.2.1-2]alkyl, or Ar2, and is substituted with 0-5 substituents selected from cyano, halo, alkyl, haloalkyl, hydroxy, alkoxy, haloalkoxy, and CO2R5;
R5 is hydrogen or alkyl;
R6 is hydrogen, alkyl, alkylcarbonyl, or phenyl;
R7 is hydrogen or alkyl;
or (R6)(R7)N taken together is azetidinyl, pyrrolidinyl, piperidinyl, piperazinyl, morpholinyl, or thiomorpholinyl dioxide, and is substituted with 0-3 substituents selected from halo, alkyl, hydroxy, and alkoxy;
Ar1 is phenyl, thiazolyl, pyridinyl, pyridazinyl, pyrimidinyl, or pyrazinyl; and
Ar2 is phenyl, biphenyl, naphthalenyl, thiazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, or quinoxalinyl.