Back to results
US 2023/0364277 A1Published application
E-selectin targeting agents
AssigneeGlycoMimetics, Inc.
InventorsJohn L. MAGNANI, John M. PETERSON, William E. FOGLER, Myung-Gi BAEK
Life of this patent
Estimating the term…
Abstract
E-selectin ligands which are useful for the synthesis of E-selectin ligand-bearing carriers, wherein said E-selectin ligand-bearing carriers are directly or indirectly linked to or associated with at least one therapeutic agent, diagnostic agent, imaging agent, or radiopharmaceutical are described herein.
Claims66
At least one entity chosen from compounds of Formula (I):
- and pharmaceutically acceptable salts thereof, wherein
- R1 is chosen from H, C1-12 alkyl, C2-12 alkenyl, C2-12 alkynyl, C1-12 haloalkyl, C2-12 haloalkenyl, C2-12 haloalkynyl,
- groups, wherein n is chosen from integers ranging from 0 to 2, R6 is chosen from H, C1-12 alkyl, C2-12 alkenyl, C2-12 alkynyl, C4-16 cycloalkylalkyl, and —C(═O)R7 groups, and each R7 is independently chosen from H, C1-12 alkyl, C2-12 alkenyl, C2-12 alkynyl, C4-16 cycloalkylalkyl, C6-18 aryl, and C1-13 heteroaryl groups;
- R2 is chosen from —OH, —OY1, halo, —NH2, —NHY1, —NY1Y2, —OC(═O)Y1, —NHC(═O)Y1, —NHC(═O)NHY1, and —NHC(═O)NY1Y2 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, C1-12 haloalkyl, C2-12 haloalkenyl, C2-12 haloalkynyl, C4-16 cycloalkylalkyl, C2-12 heterocyclyl, C6-15 aryl, and C1-13 heteroaryl groups, or Y1 and Y2 may join together along with the heteroatom to which they are attached to form an optionally substituted, saturated or unsaturated ring;
- R3 is chosen from —CN, —CH2CN, —C(═O)Y3, —C(═O)OH, —C(═O)OY3, —C(═O)NH2, —C(═O)NHOH, —C(═O)NHOCH3, —NHCN, —C(═O)NHY3, —C(═O)NY3Y4, —S(═O)2Y3, —S(═O)20Y3, —S(═O)2NH2, —S(═O)2NHY3, and —S(═O)2NY3Y4 groups, wherein Y3 and Y4, which may be identical or different, are independently chosen from C1-12 alkyl, C2-12 alkenyl, C2-12 alkynyl, C1-12 haloalkyl, C2-12 haloalkenyl, C2-12 haloalkynyl, C1-13 heterocyclyl, and C7-12 arylalkyl groups, or Y3 and Y4 join together along with the heteroatom to which they are attached to form an optionally substituted, saturated or unsaturated ring;
- R4 is chosen from H, C1-12 alkyl, C2-12 alkenyl, C2-12 alkynyl, C1-12 haloalkyl, C2-12 haloalkenyl, C2-12 haloalkynyl, C1-12 alkoxy, C4-16 cycloalkylalkyl, C6-18 aryl, and C2-13 heteroaryl groups;
- R5 is chosen from —CN, C1-12 alkyl, and C1-12 haloalkyl groups;
- L1 is chosen from
- L2 is chosen from —CH2(OCH2CH2)mV—, —CH2CH2(OCH2CH2)mV—, and —(CH2) mV— groups, wherein V is chosen from a bond, —O—, —OCH2—, —NHC(═O)CH2CH2—, and —C(═O)NHCH2CH2—, and wherein m is chosen from integers ranging from 1 to 46;
- and
- Z is chosen from lipids, nucleophiles, electrophiles, and groups capable of undergoing a cycloaddition reaction.
8 more elements
At least one entity chosen from compounds of Formula (II):
- and pharmaceutically acceptable salts thereof, wherein
- R1 is chosen from H, C1-12 alkyl, C2-12 alkenyl, C2-12 alkynyl, C1-12 haloalkyl, C2-12 haloalkenyl, C2-12 haloalkynyl,
- groups, wherein n is chosen from integers ranging from 0 to 2, R6 is chosen from H, C1-12 alkyl, C2-12 alkenyl, C2-12 alkynyl, C4-16 cycloalkylalkyl, and —C(═O)R7 groups, and each R7 is independently chosen from H, C1-12 alkyl, C2-12 alkenyl, C2-12 alkynyl, C4-16 cycloalkylalkyl, C6-18 aryl, and C1-13 heteroaryl groups;
- R2 is chosen from —OH, —OY1, halo, —NH2, —NHY1, —NY1Y2, —OC(═O)Y1, —NHC(═O)Y1, —NHC(═O)NHY1, and —NHC(═O)NY1Y2 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, C1-12 haloalkyl, C2-12 haloalkenyl, C2-12 haloalkynyl, C4-16 cycloalkylalkyl, C2-12 heterocyclyl, C6-18 aryl, and C1-13 heteroaryl groups, or Y1 and Y2 may join together along with the heteroatom to which they are attached to form an optionally substituted, saturated or unsaturated ring;
- R3 is chosen from —CN, —CH2CN, —C(═O)Y3, —C(═O)OH, —C(═O)OY3, —C(═O)NH2, —C(═O)NHOH, —C(═O)NHOCH3, —NHCN, —C(═O)NHY3, —C(═O)NY3Y4, —S(═O)2Y3, —S(═O)20Y3, —S(═O)2NH2, —S(═O)2NHY3, and —S(═O)2NY3Y4 groups, wherein Y3 and Y4, which may be identical or different, are independently chosen from C1-12 alkyl, C2-12 alkenyl, C2-12 alkynyl, C1-12 haloalkyl, C2-12 haloalkenyl, C2-12 haloalkynyl, C1-13 heterocyclyl, and C7-12 arylalkyl groups, or Y3 and Y4 join together along with the heteroatom to which they are attached to form an optionally substituted, saturated or unsaturated ring;
- R4 is chosen from H, C1-12 alkyl, C2-12 alkenyl, C2-12 alkynyl, C1-12 haloalkyl, C2-12 haloalkenyl, C2-12 haloalkynyl, C1-12 alkoxy, C4-16 cycloalkylalkyl, C6-15 aryl, and C2-13 heteroaryl groups;
- R5 is chosen from —CN, C1-12 alkyl, and C1-12 haloalkyl groups;
- L1 is chosen from
- L2 is chosen from —CH2(OCH2CH2)mV—, —CH2CH2(OCH2CH2)mV—, and —(CH2) mV— groups, wherein V is chosen from a bond, —O—, —OCH2—, —NHC(═O)CH2CH2—, and —C(═O)NHCH2CH2—, and wherein m is chosen from integers ranging from 1 to 46;
- L3 is chosen from a bond and linker groups;
- and
- Z′ is chosen from a lipid-lipid non-covalent association, —C(═O)HN—, —CH2NH—, —CH2S—,
9 more elements
Dependencies are inferred from the claim text.