US 11,780,873 B2
Highly potent multimeric e-selectin antagonists
John L. Magnani, Gaithersburg, MD (US); John M. Peterson, Slate Hill, NY (US); and Myung-Gi Baek, Boyds, MD (US)
Assigned to GlycoMimetics, Inc., Rockville, MD (US)
Filed by GLYCOMIMETICS, INC., Rockville, MD (US)
Filed on Jun. 15, 2021, as Appl. No. 17/347,744.
Application 17/347,744 is a division of application No. 16/339,646, granted, now 11,072,625, previously published as PCT/US2017/055648, filed on Oct. 6, 2017.
Claims priority of provisional application 62/451,415, filed on Jan. 27, 2017.
Claims priority of provisional application 62/405,792, filed on Oct. 7, 2016.
Prior Publication US 2021/0323990 A1, Oct. 21, 2021
Int. Cl. C07H 15/207 (2006.01); A61K 31/7034 (2006.01); A61P 35/04 (2006.01); A61P 1/04 (2006.01); C07H 7/06 (2006.01); C07H 15/26 (2006.01); A61K 47/60 (2017.01); C07H 7/04 (2006.01)
CPC C07H 7/06 (2013.01) [A61K 31/7034 (2013.01); A61K 47/60 (2017.08); A61P 1/04 (2018.01); A61P 35/04 (2018.01); C07H 7/04 (2013.01); C07H 15/207 (2013.01); C07H 15/26 (2013.01)] 42 Claims
OG exemplary drawing
 
1. A method for treatment of at least one disease, disorder, and/or condition where inhibition of E-selectin mediated functions is useful, the method comprising administering to a subject in need thereof an effective amount of at least one compound chosen from glycomimetic E-selectin antagonists of Formula (I):

OG Complex Work Unit Chemistry
and pharmaceutically acceptable salts thereof,
wherein
each R1, which may be identical or different, is independently chosen from H, C1-12 alkyl, C2-12 alkenyl, C2-12 alkynyl, and —NHC(═O)R5 groups, wherein each R5, which may be identical or different, is independently chosen from C1-12 alkyl, C2-12 alkenyl, C2-12 alkynyl, C6-18 aryl, and C1-13 heteroaryl groups;
each R2, which may be identical or different, is independently chosen from halo, —OY1, —NY1Y2, —OC(═O)Y1, —NHC(═O)Y1, and —NHC(═O)NY1Y2 groups, wherein each Y1 and each Y2, which may be identical or different, are independently chosen from H, C1-12 alkyl, C2-12 alkenyl, C2-12 alkynyl, C1-12 haloalkyl, C2-12 haloalkenyl, C2-12 haloalkynyl, 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;
each R3, which may be identical or different, is independently chosen from

OG Complex Work Unit Chemistry
wherein each R6, which may be identical or different, is independently chosen from H, C1-12 alkyl, and C1-12 haloalkyl groups, and wherein each R7, which may be identical or different, is independently chosen from C1-8 alkyl, C2-8 alkenyl, C2-8 alkynyl, —OY3, —NHOH, —NHOCH3, —NHCN, and —NY3Y4 groups, wherein each Y3 and each Y4, which may be identical or different, are independently chosen from H, C1-8 alkyl, C2-8 alkenyl, C2-8 alkynyl, C1-8 haloalkyl, C2-8 haloalkenyl, and C2-8 haloalkynyl groups, wherein Y3 and Y4 may join together along with the nitrogen atom to which they are attached to form a ring;
each R4, which may be identical or different, is independently chosen from —CN, C1-4 alkyl, and C1-4 haloalkyl groups;
m is 2; and
L is chosen from

OG Complex Work Unit Chemistry
wherein Q is chosen from

OG Complex Work Unit Chemistry
wherein R8 is chosen from H and benzyl, and wherein p is chosen from integers ranging from 0 to 30.