# US 9,434,670 B2 · Family of aryl, heteroaryl, O-aryl and O-heteroaryl carbasugars > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 9,434,670 B2 - Document ID: US9434670B2 - Status: Granted - Kind: B2 - Application number: 14/119,265 - Filed: 2012-05-29 - Published: 2014-04-17 - Granted: 2016-09-06 - Earliest claimed: 2011-05-26 - Assignees: Tfchem - Applicants: Geraldine Deliencourt-Godefroy; Lenaig Lopes - Inventors: Geraldine Deliencourt-Godefroy; Lenaig Lopes - Web page: https://patentgrep.com/patent/US9434670B2 ## CPC - C07C 43/29: containing halogen - A61K 8/347: {Phenols} - A61K 8/494: {with more than one nitrogen as the only hetero atom} - A61K 8/4946: {Imidazoles or their condensed derivatives, e.g. benzimidazoles} - A61K 8/4986: {with sulfur as the only hetero atom} - A61K 8/69: containing fluorine - A61P 3/00: Drugs for disorders of the metabolism (of the blood or the extracellular fluid A61P7/00) - A61P 3/04: Anorexiants; Antiobesity agents - A61P 3/06: Antihyperlipidemics - A61P 3/10: for hyperglycaemia, e.g. antidiabetics - A61P 7/02: Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors - A61P 9/10: for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis - A61P 13/00: Drugs for disorders of the urinary system - A61P 13/12: of the kidneys - A61P 19/02: for joint disorders, e.g. arthritis, arthrosis - A61P 25/00: Drugs for disorders of the nervous system - A61P 27/02: Ophthalmic agents - A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] - A61P 31/00: Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics - A61P 31/12: Antivirals - A61P 35/00: Antineoplastic agents - A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00 - A61Q 19/02: for chemically bleaching or whitening the skin - C07C 41/09: by dehydration of compounds containing hydroxy groups - C07C 41/22: by introduction of halogens; by substitution of halogen atoms by other halogen atoms - C07C 41/24: by elimination of halogens, e.g. elimination of HCl - C07C 43/225: containing halogen - C07C 43/23: containing hydroxy or O-metal groups - C07C 43/247: containing halogen - C07C 43/253: containing hydroxy or O-metal groups - C07D 231/20: One oxygen atom attached in position 3 or 5 - C07D 333/16: by oxygen atoms - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - 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 - A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) ## Abstract The present invention relates to a compound of the following formula (I): as well as its process of preparation, pharmaceutical and cosmetics composition comprising it and use thereof, notably as an inhibitor of the sodium-dependent glucose co-transporter, such as SGLT1, SGLT2 and SGLT3, in particular in the treatment or prevention of diabetes, and more particularly type-II diabetes, diabetes-related complications, such as arthritis of the lower extremities, cardiac infarction, renal insufficiency, neuropathy or blindness, hyperglycemia, hyperinsulinemia, obesity, hypertriglyceridemia, X syndrome and arteriosclerosis, as well as for its use as an anticancer, anti-infective, anti-viral, anti-thrombotic or anti-inflammatory drug, or for lightening, bleaching, depigmenting the skin, removing blemishes from the skin, particularly age spots and freckles, or preventing pigmentation of the skin. ## Claims ### Claim 1 A compound having the following formula (I): or a pharmaceutically or cosmetically acceptable salt thereof, or a tautomer, or a stereoisomer or a mixture of stereoisomers, wherein: n=1 and m=0, p=0, R is CH2OH, R1, R2 and R3 are OH, R4 is a hydrogen atom, X1 is a hydrogen atom, an halogen atom, OH, (C1-C6)-alkyl, OR24, or OCOR24, U is a phenyl ring, said ring being optionally substituted with one or more substituents selected from the group consisting of an halogen atom, OH, (C1-C6)-alkyl, OR24, and OCOR24, and R24 is a (C1-C6)-alkyl. ### Claim 2 (depends on 1) The compound according to claim 1, having the following formula (I-1), (I-1), (I-1b) or (I-1c): or a pharmaceutically or cosmetically acceptable salt thereof, a tautomer, a stereoisomer or a mixture of stereoisomers, wherein: X1, X2, X3, X4 and X5 are, independently from one another, a hydrogen atom, an halogen atom, OH, (C1-C6)-alkyl, OR24, or OCOR24. ### Claim 3 (depends on 1) The compound according to claim 1, wherein U is a phenyl ring, said ring being optionally substituted with one or more substituents selected from the group consisting of an halogen atom, OH, (C1-C6)-alkyl, and OR24, and X1 is selected from the group consisting of a hydrogen atom, a halogen atom, OH, (C1-C6)-alkyl, and OR24. ### Claim 4 (depends on 1) The compound according to claim 1, selected from: ### Claim 5 (depends on 2) The compound according to claim 2, wherein X1, X2, X3, X4 and X5 are, independently from one another, a hydrogen atom, an halogen atom, OH, (C1-C6)-alkyl or OR24. ### Claim 6 (depends on 2) The compound according to claim 2, wherein X1, X2, X3, X4 and X5 are, independently from one another, a hydrogen atom, an halogen atom, OH, or OR24. ### Claim 7 (depends on 3) The compound according to claim 3, wherein U is a phenyl ring, said ring being optionally substituted with one or more substituents selected from the group consisting of an halogen atom, OH, and OR24, and X1 is selected from the group consisting of a hydrogen atom, a halogen atom, OH, and OR24. ### Claim 8 (depends on 1) A method for lightening, bleaching, depigmenting the skin, or removing blemishes from the skin, comprising the topical application of at least one compound according to claim 1. ### Claim 9 (depends on 8) The method according to claim 8, wherein the blemishes of the skin are age spots or freckles. ### Claim 10 (depends on 1) A pharmaceutical or cosmetic composition including at least one compound according to claim 1 and at least one pharmaceutically or cosmetically acceptable vehicle. ### Claim 11 A compound of following formula: or a pharmaceutically or cosmetically acceptable salt thereof. ### Claim 12 (depends on 11) A method for inhibiting a sodium-dependent glucose co-transporter comprising the administration to a person in need thereof of an effective amount of a compound according to claim 11. ### Claim 13 (depends on 12) The method according to claim 12, wherein the sodium-dependent glucose co-transporter is SGLT1, SGLT2 or SGLT3. ### Claim 14 (depends on 11) A method for treating diabetes; diabetes-related complications selected from the group consisting of arteritis of the lower extremities, cardiac infarction, renal insufficiency, neuropathy and blindness; hyperglycemia; hyperinsulinemia; obesity; hypertriglyceridemia; X syndrome; or arteriosclerosis, or for an anti-cancer, anti-infective, anti-viral, anti-thrombotic or anti-inflammatory treatment, including the administration of an effective amount of at least one compound according to claim 11 to a patient in need thereof. ### Claim 15 (depends on 14) The method according to claim 14, wherein the method is for treating type-II diabetes, arteritis of the lower extremities, cardiac infarction, renal insufficiency, neuropathy or blindness. ### Claim 16 (depends on 11) A pharmaceutical or cosmetic composition including at least one compound according to claim 11 and at least one pharmaceutically or cosmetically acceptable vehicle.