# US 10,766,916 B2 · E-selectin antagonist compounds, compositions, and methods of use > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,766,916 B2 - Document ID: US10766916B2 - Status: Granted - Kind: B2 - Application number: 16/689,339 - Filed: 2019-11-20 - Published: 2020-05-21 - Granted: 2020-09-08 - Earliest claimed: 2011-12-22 - Assignees: GlycoMimetics, Inc. - Applicants: GlycoMimetics, Inc. - Inventors: John L. Magnani; Arun K. Sarkar; Myung-Gi Baek; Frank E. Anderson, III; Yanhong Li - Web page: https://patentgrep.com/patent/US10766916B2 ## CPC - C07H 15/207: Cyclohexane rings not substituted by nitrogen atoms, e.g. kasugamycins - A61K 31/7034: attached to a carbocyclic compound, e.g. phloridzin - A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca - A61P 7/02: Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors - A61P 35/00: Antineoplastic agents - A61P 35/02: specific for leukemia - A61P 35/04: specific for metastasis - A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00 - C07H 15/26: Acyclic or carbocyclic radicals, substituted by hetero rings - C09C 1/62: Metallic pigments or fillers {(C09C1/0015 takes precedence)} - C07H: SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS (derivatives of aldonic or saccharic acids C07C, C07D; aldonic acids, saccharic acids C07C59/105, C07C59/285; cyanohydrins C07C255/16; glycals C07D; compounds of unknown constitution C07G; polysaccharides, derivatives thereof C08B; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; sugar industry C13) - A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D) - A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS - C09C: TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES (treatment of materials specially adapted to enhance their filling properties in mortars, concrete or artificial stone C04B14/00, C04B18/00, C04B20/00); PREPARATION OF CARBON BLACK {; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS} ## Abstract Methods and compositions using E-selectin antagonists are provided for the treatment and prevention of diseases and disorders treatable by inhibiting binding of E-selectin to an E-selectin ligand. Described herein are E-selectin antagonists including, for example, glycomimetic compounds, antibodies, aptamers and peptides that are useful in methods for treatment of cancers, and treatment and prevention of metastasis, inhibiting infiltration of the cancer cells into bone marrow, reducing or inhibiting adhesion of the cancer cells to endothelial cells including cells in bone marrow, and inhibiting thrombus formation. ## Claims ### Claim 1 A pharmaceutically acceptable salt of: ### Claim 2 (depends on 1) The pharmaceutically acceptable salt of claim 1, wherein the salt is chosen from the sodium, potassium, lithium, ammonium, calcium, magnesium, iron, zinc, copper, manganese, and aluminum salts. ### Claim 3 (depends on 1) The pharmaceutically acceptable salt of claim 1, wherein the salt is the sodium salt. ### Claim 4 (depends on 1) The pharmaceutically acceptable salt of claim 1, wherein the salt is the potassium salt. ### Claim 5 (depends on 1) The compound of claim 1, wherein the salt is the ammonium salt. ### Claim 6 (depends on 1) The compound of claim 1, wherein the salt is chosen from substituted ammonium salts. ### Claim 7 (depends on 3) A pharmaceutical composition comprising the pharmaceutically acceptable salt of claim 3 and optionally at least one pharmaceutically acceptable excipient. ### Claim 8 (depends on 7) A method for treating, decreasing, inhibiting, or reducing the likelihood of metastasis of cancer cells in a subject, comprising administering to the subject the pharmaceutical composition of claim 7. ### Claim 9 (depends on 7) A method for inhibiting infiltration of cancer cells into bone marrow in a subject, said method comprising administering to the subject the pharmaceutical composition of claim 7. ### Claim 10 (depends on 3) A method for inhibiting adhesion of a tumor cell that expresses a ligand of E-selectin to an endothelial cell expressing E-selectin, said method comprising contacting the endothelial cell with a compound of claim 3 and permitting the compound to interact with E-selectin present on the endothelial cell, thereby inhibiting binding of the tumor cell to the endothelial cell. ### Claim 11 (depends on 3) A method for inhibiting adhesion of a tumor cell that expresses a ligand of E-selectin to an endothelial cell expressing E-selectin, said method comprising administering a pharmaceutical composition comprising a compound of claim 3 and optionally at least one pharmaceutically acceptable excipient and permitting the compound to interact with E-selectin present on the endothelial cell, thereby inhibiting binding of the tumor cell to the endothelial cell. ### Claim 12 (depends on 10, 11) The method of claim 10 or 11, wherein the endothelial cell is present in the bone marrow. ### Claim 13 (depends on 7) A method for treating a cancer in a subject comprising administering to the subject (a) the pharmaceutical composition of claim 7 and (b) at least one of (i) chemotherapy and (ii) radiotherapy. ### Claim 14 (depends on 7) A method for treating, decreasing, inhibiting, or reducing the likelihood of thrombosis in a subject, comprising administering to the subject the pharmaceutical composition of claim 7. ### Claim 15 (depends on 7) A method for enhancing hematopoietic stem cell survival in a subject, comprising administering to the subject the pharmaceutical composition of claim 7. ### Claim 16 (depends on 15) The method of claim 15, wherein the subject has received or will receive chemotherapy or radiotherapy or both chemotherapy and radiotherapy.