(20S)-1α-hydroxy-2α-methyl and 2β-methyl-19-nor-vitamin D3and their uses

• US 7,094,916 B2
• Filed: 01/18/2005
• Issued: 08/22/2006
• Est. Priority Date: 04/22/2002
• Status: Expired due to Term

• Current Assignee: Wisconsin Alumni Research Foundation (University of Wisconsin System)
• Original Assignee: Wisconsin Alumni Research Foundation (University of Wisconsin System)
• Inventors: DeLuca, Hector F., Sicinski, Rafal R., Grzywacz, Pawel K.
• Primary Examiner(s): QAZI, SABIHA NAIM
• Application Number:
  US11/037,876
• Publication Number:
  US 20050159397A1
• Time in Patent Office: 581 Days
• Field of Search: 552/653, 514/167
• US Class Current: 552/653
• CPC Class Codes: A61K 31/593 9,10-Secocholestane derivatives, e.g. cholecalciferol, i.e. vitamin D3
• CPC Class Codes: A61P 1/04 for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
• CPC Class Codes: A61P 11/06 Antiasthmatics
• CPC Class Codes: A61P 17/06 Antipsoriatics
• CPC Class Codes: A61P 17/16 Emollients or protectives, e.g. against radiation
• CPC Class Codes: A61P 19/02 for joint disorders, e.g. arthritis, arthrosis
• CPC Class Codes: A61P 19/08 for bone diseases, e.g. rachitism, Paget's disease
• CPC Class Codes: A61P 19/10 for osteoporosis
• CPC Class Codes: A61P 25/00 Drugs for disorders of the nervous system
• CPC Class Codes: A61P 29/00 Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
• CPC Class Codes: A61P 3/10 for hyperglycaemia, e.g. antidiabetics
• CPC Class Codes: A61P 35/00 Antineoplastic agents
• CPC Class Codes: A61P 35/02 specific for leukemia
• CPC Class Codes: A61P 37/06 Immunosuppressants, e.g. drugs for graft rejection
• CPC Class Codes: C07C 49/433 the condensed ring system containing seven carbon atoms
• CPC Class Codes: C07C 49/443 the condensed ring system containing eight or nine carbon atoms

Abstract

This invention discloses (20S)-1α-hydroxy-2α-methyl-19-nor-vitamin D₃ and (20S)-1α-hydroxy-2β-methyl-19-nor-vitamin D₃ and pharmaceutical uses therefor. These compounds exhibit 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. These compounds also have very significant calcemic activity and therefore may be used to treat immune disorders in humans as well as metabolic bone diseases such as osteoporosis.

Claims

1. (20S)-1α

-hydroxy-2β

-methyl-19-nor-vitamin D₃ having the formula;