(20S)-1α-hydroxy-2-methylene-19-nor-bishomopregnacalciferol and its uses

• US 6,887,860 B2
• Filed: 06/16/2003
• Issued: 05/03/2005
• Est. Priority Date: 02/18/2002
• Status: Expired

• Current Assignee: Wisconsin Alumni Research Foundation (University of Wisconsin System)
• Original Assignee: Wisconsin Alumni Research Foundation (University of Wisconsin System)
• Inventors: Plum, Lori A., DeLuca, Hector F., Clagett-Dame, Margaret
• Primary Examiner(s): HUI, SAN MING R
• Application Number:
  US10/462,272
• Publication Number:
  US 20040033998A1
• Time in Patent Office: 687 Days
• Field of Search: 514/167
• US Class Current: 514/167
• CPC Class Codes: A61K 31/59 Compounds containing 9, 10- seco- cyclopenta[a]hydrophenanthrene ring systems
• CPC Class Codes: A61P 19/00 Drugs for skeletal disorders
• CPC Class Codes: 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

Abstract

This invention discloses (20S)-1α-hydroxy-2-methylene-19-nor-bishomopregnacalciferol and pharmaceutical uses therefor. This compound exhibits 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 has little, if any, calcemic activity and therefore may be used to treat immune disorders in humans as well as renal osteodystrophy.

Claims

1. A method of treating psoriasis comprising administering to a patient with psoriasis an effective amount of (20S)-1α

-hydroxy-2-methylene -19-nor-bishomopregnacalciferol having the formula;

2. The method of claim 1 wherein (20S)-1α

-hydroxy-2-methylene-19-nor-bishomopregnacalciferol is administered orally.

3. The method of claim 1 wherein (20S)-1α

-hydroxy-2-methylene-19-nor-bishomopregnacalciferol is administered parenterally.

4. The method of claim 1 wherein (20S)-1α

-hydroxy-2-methylene-19-nor-bishomopregnacalciferol is administered transdermally.

5. The method of claim 1 wherein (20S)-1α

-hydroxy-2-methylene-19-nor-bishomopregnacalciferol is administered topically.

6. The method of claim 1 wherein (20S)-1α

-hydroxy-2-methylene-19-nor-bishomopregnacalciferol is administered in a dosage of from about 0.01 μ

g/day to about 100 μ

g/day.