# US 11,583,530 B2 · Compounds for the prevention and treatment of medical disorders and uses thereof > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 11,583,530 B2 - Document ID: US11583530B2 - Status: Granted - Kind: B2 - Application number: 16/629,373 - Filed: 2018-08-03 - Published: 2020-05-14 - Granted: 2023-02-21 - Earliest claimed: 2017-08-03 - Assignees: Galectin Sciences, LLC - Applicants: Galectin Sciences, LLC - Inventors: Raphael Nir; Eliezer Zomer; Peter G. Traber; Joseph M. Johnson; Ryan George; Sharon Shechter - Web page: https://patentgrep.com/patent/US11583530B2 ## CPC - A61K 31/519: ortho- or peri-condensed with heterocyclic rings - A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca - A61P 1/16: for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics - A61P 3/10: for hyperglycaemia, e.g. antidiabetics - A61P 9/00: Drugs for disorders of the cardiovascular system - A61P 11/06: Antiasthmatics - A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] - A61P 35/00: Antineoplastic agents - A61P 37/00: Drugs for immunological or allergic disorders - C07D 401/10: linked by a carbon chain containing aromatic rings - C07D 471/04: Ortho-condensed systems - C07D 471/14: Ortho-condensed systems - C07D 487/04: Ortho-condensed systems - C07D 495/04: Ortho-condensed systems - C07D 495/14: Ortho-condensed systems - 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 - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) ## Abstract Aspects of the invention relate to compounds, pharmaceutical compositions, methods for the manufacturing of compounds and methods for treatment of various disorders mediated at least in part by one or more galectins. ## Claims ### Claim 1 A compound of Formula I or a pharmaceutically acceptable salt or solvate thereof: wherein Y linkage is (—CH═) or (—CH2-) or —CH2-X— wherein X is nitrogen, oxygen, sulfur or selenium; wherein Z is a carbon; wherein R1 is hydrogen, oxygen, amine, carboxyl, C1-C6 alkyl, C1-C4 alkoxy, aryl, halogen, trifluoromethyl, dinitromethyl or a combination of the foregoing; and wherein R2, R3 or R2 and R3 are aryl group with one or more substitutions, wherein the one or more substitution is hydroxyl, amine, C1-C6 alkyl, C1-C4 alkoxy, halogen, benzene or combinations thereof. ### Claim 2 A compound of Formula I or a pharmaceutically acceptable salt or solvate thereof: wherein Y linkage is (—CH═) or (—CH2-) or —CH2-X— wherein X is nitrogen, oxygen, sulfur or selenium; wherein Z is a carbon; wherein R1 is hydrogen, oxygen, amine, carboxyl, C1-C6 alkyl, C1-C4 alkoxy, aryl, halogen, trifluoromethyl, dinitromethyl or a combination of the foregoing; and wherein R2, R3 or R2 and R3 are fluoromethyl. ### Claim 3 A compound selected from the compounds having the formula of Table 1 ### Claim 4 A compound having one of the formula of Table 6 ### Claim 5 (depends on 1) A composition comprising a therapeutically effective amount of the compound of of claim 1, and a pharmaceutically acceptable adjuvant, excipient, formulation carrier or combinations thereof. ### Claim 6 (depends on 1) A composition comprising a therapeutically effective amount of the compound of claim 1, and a therapeutically effective amount of an anti-inflammatory drug, anti-fibrosis drug, pharmaceutical drug, nutraceutical drug, supplement, or combinations thereof. ### Claim 7 (depends on 1) A method of treatment of a disease in a subject in need thereof, comprising administering a therapeutically effective amount of a pharmaceutical composition comprising at least one compound according to claim 1, wherein the disease is a disorder related to pathological disease due to elevated galectin-3. ### Claim 8 (depends on 1) A method of treatment of a disease in a subject in need thereof, comprising administering a therapeutically effective amount of a pharmaceutical composition comprising at least one compound according to claim 1, wherein the disease is alcoholic or viral steatohepatitis a nonalcoholic steatohepatitis, fibrosis, cirrhosis, inflammatory disorder, metabolic disorder, insulin resistance, autoimmune disorder, neoplastic condition, metabolic disorder or cancer. ### Claim 9 (depends on 1) A method of treatment of a disease in a subject in need thereof, comprising administering a therapeutically effective amount of a pharmaceutical composition comprising at least one compound according to claim 1, wherein the disease is heart failure, arrhythmias, uremic cardiomyopathy, chronic kidney, idiopathic lung diseases, skin autoimmune, proliferative and fibrotic skin disorder, optionally psoriasis or atopic dermatitis. ### Claim 10 (depends on 1) A method of treatment of a disease in a subject in need thereof, comprising administering a therapeutically effective amount of a pharmaceutical composition comprising at least one compound according to claim 1, wherein the at least one compound modulates Gal-3 binding to Insulin receptor and Insulin Like Growth Factor 1 Receptor. ### Claim 11 (depends on 1) A method of treatment of a disease in a subject in need thereof, comprising administering a therapeutically effective amount of a pharmaceutical composition comprising at least one compound according to claim 1, wherein the disease is an inflammatory disorder and wherein the inflammatory disorder is inflammatory bowel disease, Crohn's disease, multiple sclerosis, Systemic Lupus Erythematosus, arthritis, rheumatoid arthritis, asthma or ulcerative colitis. ### Claim 12 (depends on 2) A composition comprising a therapeutically effective amount of the compound of claim 2, and a pharmaceutically acceptable adjuvant, excipient, formulation carrier or combinations thereof. ### Claim 13 (depends on 2) A method of treatment of a disease in a subject in need thereof, comprising administering a therapeutically effective amount of a pharmaceutical composition comprising at least one compound according to claim 2, wherein the disease is a disorder related to pathological disease due to elevated galectin-3. ### Claim 14 (depends on 2) A method of treatment of a disease in a subject in need thereof, comprising administering a therapeutically effective amount of a pharmaceutical composition comprising at least one compound according to claim 2, wherein the disease is alcoholic or viral steatohepatitis a nonalcoholic steatohepatitis, fibrosis, cirrhosis, inflammatory disorder, metabolic disorder, insulin resistance, autoimmune disorder, neoplastic condition, metabolic disorder or cancer. ### Claim 15 (depends on 2) A method of treatment of a disease in a subject in need thereof, comprising administering a therapeutically effective amount of a pharmaceutical composition comprising at least one compound according to claim 2, wherein the disease is heart failure, arrhythmias, uremic cardiomyopathy, chronic kidney, idiopathic lung diseases, skin autoimmune, proliferative and fibrotic skin disorder, optionally psoriasis or atopic dermatitis. ### Claim 16 (depends on 2) A method of treatment of a disease in a subject in need thereof, comprising administering a therapeutically effective amount of a pharmaceutical composition comprising at least one compound according to claim 2, wherein the at least one compound modulates Gal-3 binding to Insulin receptor and Insulin Like Growth Factor 1 Receptor. ### Claim 17 (depends on 2) A method of treatment of a disease in a subject in need thereof, comprising administering a therapeutically effective amount of a pharmaceutical composition comprising at least one compound according to claim 2, wherein the disease is an inflammatory disorder and wherein the inflammatory disorder is inflammatory bowel disease, Crohn's disease, multiple sclerosis, Systemic Lupus Erythematosus, arthritis, rheumatoid arthritis, asthma or ulcerative colitis. ### Claim 18 (depends on 3) A composition comprising a therapeutically effective amount of the compound of claim 3, and a pharmaceutically acceptable adjuvant, excipient, formulation carrier or combinations thereof. ### Claim 19 (depends on 3) A method of treatment of a disease in a subject in need thereof, comprising administering a therapeutically effective amount of a pharmaceutical composition comprising at least one compound according to claim 3, wherein the disease is a disorder related to pathological disease due to elevated galectin-3. ### Claim 20 (depends on 3) A method of treatment of a disease in a subject in need thereof, comprising administering a therapeutically effective amount of a pharmaceutical composition comprising at least one compound according to claim 3, wherein the disease is alcoholic or viral steatohepatitis a nonalcoholic steatohepatitis, fibrosis, cirrhosis, inflammatory disorder, metabolic disorder, insulin resistance, autoimmune disorder, neoplastic condition, metabolic disorder or cancer. ### Claim 21 (depends on 3) A method of treatment of a disease in a subject in need thereof, comprising administering a therapeutically effective amount of a pharmaceutical composition comprising at least one compound according to claim 3, wherein the disease is heart failure, arrhythmias, uremic cardiomyopathy, chronic kidney, idiopathic lung diseases, skin autoimmune, proliferative and fibrotic skin disorder, optionally psoriasis or atopic dermatitis. ### Claim 22 (depends on 3) A method of treatment of a disease in a subject in need thereof, comprising administering a therapeutically effective amount of a pharmaceutical composition comprising at least one compound according to claim 3, wherein the at least one compound modulates Gal-3 binding to Insulin receptor and Insulin Like Growth Factor 1 Receptor. ### Claim 23 (depends on 3) A method of treatment of a disease in a subject in need thereof, comprising administering a therapeutically effective amount of a pharmaceutical composition comprising at least one compound according to claim 3, wherein the disease is an inflammatory disorder and wherein the inflammatory disorder is inflammatory bowel disease, Crohn's disease, multiple sclerosis, Systemic Lupus Erythematosus, arthritis, rheumatoid arthritis, asthma or ulcerative colitis. ### Claim 24 (depends on 4) A composition comprising a therapeutically effective amount of the compound of claim 4, and a pharmaceutically acceptable adjuvant, excipient, formulation carrier or combinations thereof. ### Claim 25 (depends on 4) A method of treatment of a disease in a subject in need thereof, comprising administering a therapeutically effective amount of a pharmaceutical composition comprising at least one compound according to claim 4, wherein the disease is a disorder related to pathological disease due to elevated galectin-3. ### Claim 26 (depends on 4) A method of treatment of a disease in a subject in need thereof, comprising administering a therapeutically effective amount of a pharmaceutical composition comprising at least one compound according to claim 4, wherein the disease is alcoholic or viral steatohepatitis a nonalcoholic steatohepatitis, fibrosis, cirrhosis, inflammatory disorder, metabolic disorder, insulin resistance, autoimmune disorder, neoplastic condition, metabolic disorder or cancer. ### Claim 27 (depends on 4) A method of treatment of a disease in a subject in need thereof, comprising administering a therapeutically effective amount of a pharmaceutical composition comprising at least one compound according to claim 4, wherein the disease is heart failure, arrhythmias, uremic cardiomyopathy, chronic kidney, idiopathic lung diseases, skin autoimmune, proliferative and fibrotic skin disorder, optionally psoriasis or atopic dermatitis. ### Claim 28 (depends on 4) A method of treatment of a disease in a subject in need thereof, comprising administering a therapeutically effective amount of a pharmaceutical composition comprising at least one compound according to claim 4, wherein the at least one compound modulates Gal-3 binding to Insulin receptor and Insulin Like Growth Factor 1 Receptor. ### Claim 29 (depends on 4) A method of treatment of a disease in a subject in need thereof, comprising administering a therapeutically effective amount of a pharmaceutical composition comprising at least one compound according to claim 4, wherein the disease is an inflammatory disorder and wherein the inflammatory disorder is inflammatory bowel disease, Crohn's disease, multiple sclerosis, Systemic Lupus Erythematosus, arthritis, rheumatoid arthritis, asthma or ulcerative colitis.