US 11,873,317 B2
Galectin-3 inhibiting c-glycosides
John L. Magnani, Gaithersburg, MD (US); John M. Peterson, Slate Hill, NY (US); Arun K. Sarkar, North Potomac, MD (US); Yusufbhai U. Vohra, Germantown, MD (US); Indranath Ghosh, Olney, MD (US); and Jason Nogueira, Germantown, MD (US)
Assigned to GLYCOMIMETICS, INC., Rockville, MD (US)
Appl. No. 17/418,590
Filed by GLYCOMIMETICS, INC., Rockville, MD (US)
PCT Filed Dec. 26, 2019, PCT No. PCT/US2019/068597
§ 371(c)(1), (2) Date Jun. 25, 2021,
PCT Pub. No. WO2020/139960, PCT Pub. Date Jul. 2, 2020.
Claims priority of provisional application 62/927,192, filed on Oct. 29, 2019.
Claims priority of provisional application 62/785,588, filed on Dec. 27, 2018.
Prior Publication US 2022/0073555 A1, Mar. 10, 2022
Int. Cl. C07H 19/056 (2006.01); C07H 19/06 (2006.01); C07H 19/24 (2006.01); A61K 31/7056 (2006.01)
CPC C07H 19/056 (2013.01) [A61K 31/7056 (2013.01); C07H 19/06 (2013.01); C07H 19/24 (2013.01)] 61 Claims
 
1. At least one compound chosen from compounds of Formula (I):

OG Complex Work Unit Chemistry
and pharmaceutically acceptable salts thereof,
wherein
R1 is chosen from —CN, —CH2CN, and —C(═O)Q groups, wherein Q is chosen from —OZ1, —NHOH, —NHOCH3, —NHCN, and —NZ1Z2 groups, wherein Z1 and Z2, which may be identical or different, are independently chosen from H, C1-8 alkyl, C2-12 heterocyclyl, C6-18 aryl, and C1-13 heteroaryl groups, wherein the C2-12 heterocyclyl, C6-18 aryl and C1-13 heteroaryl groups are optionally substituted with one or more groups independently chosen from halo, C1-8 alkyl, C1-8 hydroxyalkyl, C1-8 haloalkyl, C6-18 aryl, —OT1, —C(═O)OT1, —C(═O)NT1T2, —CN, —ST1, S(O)T1, and —SO2T1 groups, wherein T1 and T2, which may be identical or different, are independently chosen from H, C1-8 alkyl, and C1-8 haloalkyl groups, or T1 and T2 join together along with the nitrogen atom to which they are attached to form a ring, or Z1 and Z2 join together along with the nitrogen atom to which they are attached to form a ring;
R2 is chosen from H, C1-8 alkyl, C2-8 alkenyl, C2-8 alkynyl, C1-8 haloalkyl, C2-8 haloalkenyl, C2-8 haloalkynyl, C4-16 cycloalkylalkyl, C6-18 aryl, C1-13 heteroaryl, C7-19 arylalkyl, and C2-14 heteroarylalkyl groups, wherein the C1-8 alkyl, C2-8 alkenyl, C2-8 alkynyl, C1-8 haloalkyl, C2-8 haloalkenyl, C2-8 haloalkynyl, C4-16 cycloalkylalkyl, C6-18 aryl, C1-13 heteroaryl, C7-19 arylalkyl, and C2-14 heteroarylalkyl groups are optionally substituted with one or more groups independently chosen from halo, C1-8 alkyl, C1-8 hydroxyalkyl, C1-8 haloalkyl, C6-18 aryl, —OZ3, —C(═O)OZ3, —C(═O)NZ3Z4, and —SO2Z3 groups, wherein Z3 and Z4, which may be identical or different, are independently chosen from H, C1-8 alkyl, and C1-8 haloalkyl groups, or Z3 and Z4 join together along with the nitrogen atom to which they are attached to form a ring;
R3 is chosen from C6-18 aryl and C1-13 heteroaryl groups, wherein the C6-18 aryl and C1-13 heteroaryl groups are optionally substituted with one or more groups independently chosen from R4, C1-8 alkyl, C1-8 haloalkyl, —C(═O)OZ5, and —C(═O)NZ5Z6 groups, wherein R4 is independently chosen from C6-18 aryl groups optionally substituted with one or more groups independently chosen from halo, C1-8 alkyl, —OZ7, —C(═O)OZ7, and —C(═O)NZ7Z8 groups, wherein Z5, Z6, Z7 and Z8, which may be identical or different, are independently chosen from H and C1-8 alkyl groups, or Z5 and Z6 join together along with the nitrogen atom to which they are attached to form a ring and/or Z7 and Z8 join together along with the nitrogen atom to which they are attached to form a ring;
X is chosen from —O—, —S—, —CH2—, and —N(R5)—, wherein R5 is chosen from H, C1-8 alkyl, C2-8 alkenyl, C2-8 alkynyl, C1-8 haloalkyl, C2-8 haloalkenyl, and C2-8 haloalkynyl groups;
Y is chosen from H, halo, and —OZ9 groups, wherein Z9 is chosen from H and C1-8 alkyl groups; and
wherein each of Z1, Z2, Z3, Z4, Z5, Z6, Z7, Z8, and Z9 is optionally substituted with one or more groups independently chosen from halo and —OR6 groups, wherein R6 is independently chosen from H and C1-8 alkyl groups.