US 11,878,026 B2
Galactopyranosyl-cyclohexyl derivatives as e-selectin antagonists
John L. Magnani, Gaithersburg, MD (US); John M. Peterson, Slate Hill, NY (US); Arun K. Sarkar, North Potomac, MD (US); Yusuf U. Vohra, Germantown, MD (US); and Myung-Gi Baek, Boyds, MD (US)
Assigned to GLYCOMIMETICS, INC., Rockville, MD (US)
Filed by GLYCOMIMETICS, INC., Rockville, MD (US)
Filed on Nov. 9, 2021, as Appl. No. 17/522,378.
Application 17/522,378 is a continuation of application No. 16/493,448, granted, now 11,197,877, previously published as PCT/US2018/021977, filed on Mar. 12, 2018.
Claims priority of provisional application 62/471,860, filed on Mar. 15, 2017.
Prior Publication US 2022/0175808 A1, Jun. 9, 2022
This patent is subject to a terminal disclaimer.
Int. Cl. A61K 31/7036 (2006.01); A61K 45/06 (2006.01)
CPC A61K 31/7036 (2013.01) [A61K 45/06 (2013.01)] 29 Claims
 
1. At least one compound chosen from glycomimetic E-selectin antagonists having the following Formulae:

OG Complex Work Unit Chemistry
and pharmaceutically acceptable salts of any of the foregoing, wherein
R1 is chosen from H, C1-12 alkyl, C2-12 alkenyl, C2-12 alkynyl, C1-8 haloalkyl, C2-8 haloalkenyl, C2-8 haloalkynyl,

OG Complex Work Unit Chemistry
groups, wherein n is chosen from integers ranging from 0 to 2, R7 is chosen from H, C1-8 alkyl, C2-8 alkenyl, C2-8 alkynyl, C4-16 cycloalkylalkyl, and —C(═O) R8 groups, and each R8 is independently chosen from H, C1-8 alkyl, C2-8 alkenyl, C2-8 alkynyl, C4-16 cycloalkylalkyl, C6-18 aryl, and C1-13 heteroaryl groups;
R3 is chosen from —OH, −OY1, halo, —NH2, —NHY1, —NY1Y2, —OC(═O)Y1, —NHC(═O)Y1, and —NHC(═O)NHY1 groups, wherein Y1 and Y2, which may be the same or different, are independently chosen from C1-12 alkyl, C2-12 alkenyl, C2-12 alkynyl, C4-16 cycloalkylalkyl, C2-12 heterocyclyl, C6-18 aryl, and C1-13 heteroaryl groups, wherein Y1 and Y2 may join together along with the nitrogen atom to which they are attached to form a ring; and
M is chosen from linker groups.