# US 10,479,764 B2 · 2-methylene-(22E)-25-hexanoyl-24-oxo-26,27-cyclo-22-dehydro-19-nor-vitamin D analogs > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,479,764 B2 - Document ID: US10479764B2 - Status: Granted - Kind: B2 - Application number: 13/533,018 - Filed: 2012-06-26 - Published: 2013-01-03 - Granted: 2019-11-19 - Earliest claimed: 2011-06-28 - Assignees: Wisconsin Alumni Research Foundation - Applicants: Hector F. DeLuca; Margaret Clagett-Dame; Lori A. Plum; Rafal Barycki - Inventors: Hector F. DeLuca; Margaret Clagett-Dame; Lori A. Plum; Rafal Barycki - Web page: https://patentgrep.com/patent/US10479764B2 ## CPC - C07C 401/00: Irradiation products of cholesterol or its derivatives; Vitamin D derivatives, 9,10-seco cyclopenta[a]phenanthrene or analogues obtained by chemical preparation without irradiation - A61P 1/00: Drugs for disorders of the alimentary tract or the digestive system - A61P 3/04: Anorexiants; Antiobesity agents - A61P 3/10: for hyperglycaemia, e.g. antidiabetics - A61P 5/20: for decreasing, blocking or antagonising the activity of PTH - A61P 11/06: Antiasthmatics - A61P 13/12: of the kidneys - A61P 17/00: Drugs for dermatological disorders - A61P 17/06: Antipsoriatics - A61P 19/04: for non-specific disorders of the connective tissue - A61P 25/00: Drugs for disorders of the nervous system - 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 35/02: specific for leukemia - A61P 37/06: Immunosuppressants, e.g. drugs for graft rejection - A61K 31/593: 9,10-Secocholestane derivatives, e.g. cholecalciferol, i.e. vitamin D3 - C07C 2601/02: with a three-membered ring - C07C 2601/14: The ring being saturated - C07C 2602/24: the ring system containing nine carbon atoms, e.g. perhydroindane - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS - 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) ## Abstract This invention discloses 2-methylene-(22E)-25-hexanoyl-24-oxo-26,27-cyclo-22-dehydro-19-nor-vitamin D analogs, and specifically 2-methylene-(22E)-25-hexanoyl-24-oxo-26,27-cyclo-22-dehydro-19-nor-1α-hydroxyvitamin D3, and pharmaceutical uses therefor. This compound exhibits relatively high transcription activity as well as pronounced activity in arresting the proliferation of undifferentiated cells and inducing their differentiation to the monocyte thus evidencing use as an anti-cancer agent and for the treatment of skin diseases such as psoriasis as well as skin conditions such as wrinkles, slack skin, dry skin and insufficient sebum secretion. This compound also shows low activity in vivo on bone calcium mobilization, and therefore may be used to treat autoimmune disorders or inflammatory diseases in humans as well as renal osteodystrophy. This compound may also be used for the treatment or prevention of obesity. ## Claims ### Claim 1 A method of treating psoriasis comprising administering to a subject with psoriasis an effective amount of 2-methylene-(22E)-25-hexanoyl-24-oxo-26,27-cyclo-22-dehydro-19-nor-1α-hydroxyvitamin D3. ### Claim 2 (depends on 1) The method of claim 1 wherein the compound is administered orally. ### Claim 3 (depends on 1) The method of claim 1 wherein the compound is administered parenterally. ### Claim 4 (depends on 1) The method of claim 1 wherein the compound is administered transdermally. ### Claim 5 (depends on 1) The method of claim 1 wherein the compound is administered topically. ### Claim 6 (depends on 1) The method of claim 1 wherein the compound is administered rectally. ### Claim 7 (depends on 1) The method of claim 1 wherein the compound is administered nasally. ### Claim 8 (depends on 1) The method of claim 1 wherein the compound is administered sublingually. ### Claim 9 (depends on 1) The method of claim 1 wherein the compound is administered in a dosage of from about 0.01 μg/day to about 1000 μg/day. ### Claim 10 A method of treating a disease selected from the group consisting of leukemia, colon cancer, breast cancer, skin cancer or prostate cancer comprising administering to a subject with said disease an effective amount of 2-methylene-(22E)-25-hexanoyl-24-oxo-26,27-cyclo-22-dehydro-19-nor-1α-hydroxyvitamin D3. ### Claim 11 (depends on 10) The method of claim 10 wherein the compound is administered orally. ### Claim 12 (depends on 10) The method of claim 10 wherein the compound is administered parenterally. ### Claim 13 (depends on 10) The method of claim 10 wherein the compound is administered transdermally. ### Claim 14 (depends on 10) The method of claim 10 wherein the compound is administered rectally. ### Claim 15 (depends on 10) The method of claim 10 wherein the compound is administered nasally. ### Claim 16 (depends on 10) The method of claim 10 wherein the compound is administered sublingually. ### Claim 17 (depends on 10) The method of claim 10 wherein the compound is administered in a dosage of from about 0.01 μg/day to about 1000 μg/day. ### Claim 18 A method of treating an autoimmune disease selected from the group consisting of multiple sclerosis, lupus, diabetes mellitus, host versus graft rejection, and rejection of organ transplants, comprising administering to a subject with said disease an effective amount of 2-methylene-(22E)-25-hexanoyl-24-oxo-26,27-cyclo-22-dehydro-19-nor-1α-hydroxyvitamin D3. ### Claim 19 (depends on 18) The method of claim 18 wherein the compound is administered orally. ### Claim 20 (depends on 18) The method of claim 18 wherein the compound is administered parenterally. ### Claim 21 (depends on 18) The method of claim 18 wherein the compound is administered transdermally. ### Claim 22 (depends on 18) The method of claim 18 wherein the compound is administered rectally. ### Claim 23 (depends on 18) The method of claim 18 wherein the compound is administered nasally. ### Claim 24 (depends on 18) The method of claim 18 wherein the compound is administered sublingually. ### Claim 25 (depends on 18) The method of claim 18 wherein the compound is administered in a dosage of from about 0.01 μg/day to about 1000 μg/day. ### Claim 26 A method of treating a skin condition selected from the group consisting of wrinkles, lack of adequate skin firmness, lack of adequate dermal hydration and insufficient sebum secretion which comprises administering to a subject with said skin condition an effective amount of a 2-methylene-(22E)-25-hexanoyl-24-oxo-26,27-cyclo-22-dehydro-19-nor-1α-hydroxyvitamin D3. ### Claim 27 (depends on 26) The method of claim 26 wherein the compound is administered orally. ### Claim 28 (depends on 26) The method of claim 26 wherein the compound is administered parenterally. ### Claim 29 (depends on 26) The method of claim 26 wherein the compound is administered transdermally. ### Claim 30 (depends on 26) The method of claim 26 wherein the compound is administered topically. ### Claim 31 (depends on 26) The method of claim 26 wherein the compound is administered rectally. ### Claim 32 (depends on 26) The method of claim 26 wherein the compound is administered nasally. ### Claim 33 (depends on 26) The method of claim 26 wherein the compound is administered sublingually. ### Claim 34 (depends on 26) The method of claim 26 wherein the compound is administered in a dosage of from about 0.01 μg/day to about 1000 μg/day. ### Claim 35 A method of treating renal osteodystrophy comprising administering to a subject with renal osteodystrophy an effective amount of 2-methylene-(22E)-25-hexanoyl-24-oxo-26,27-cyclo-22-dehydro-19-nor-1α-hydroxyvitamin D3. ### Claim 36 (depends on 35) The method of claim 35 wherein the compound is administered orally. ### Claim 37 (depends on 35) The method of claim 35 wherein the compound is administered parenterally. ### Claim 38 (depends on 35) The method of claim 35 wherein the compound is administered transdermally. ### Claim 39 (depends on 35) The method of claim 35 wherein the compound is administered rectally. ### Claim 40 (depends on 35) The method of claim 35 wherein the compound is administered nasally. ### Claim 41 (depends on 35) The method of claim 35 wherein the compound is administered sublingually. ### Claim 42 (depends on 35) The method of claim 35 wherein the compound is administered in a dosage of from about 0.01 μg/day to about 1000 μg/day. ### Claim 43 A method of treating obesity of an animal, inhibiting adipocyte differentiation, inhibiting SCD-1 gene transcription, and/or reducing body fat in an animal comprising administering to an animal in need thereof an effective amount of 2-methylene-(22E)-25-hexanoyl-24-oxo-26,27-cyclo-22-dehydro-19-nor-1α-hydroxyvitamin D3. ### Claim 44 (depends on 43) The method of claim 43 wherein the compound is administered orally. ### Claim 45 (depends on 43) The method of claim 43 wherein the compound is administered parenterally. ### Claim 46 (depends on 43) The method of claim 43 wherein the compound is administered transdermally. ### Claim 47 (depends on 43) The method of claim 43 wherein the compound is administered rectally. ### Claim 48 (depends on 43) The method of claim 43 wherein the compound is administered nasally. ### Claim 49 (depends on 43) The method of claim 43 wherein the compound is administered sublingually. ### Claim 50 (depends on 43) The method of claim 43 wherein the compound is administered in a dosage of from about 0.01 μg/day to about 1000 μg/day. ### Claim 51 (depends on 43) The method of claim 43 wherein the animal is a human. ### Claim 52 (depends on 43) The method of claim 43 wherein the animal is a domestic animal. ### Claim 53 (depends on 43) The method of claim 43 wherein the animal is an agricultural animal.