2-methylene-19-nor-1α-hydroxy-17-ene-homopregnacalciferol and its uses

• US 7,704,982 B2
• Filed: 07/09/2007
• Issued: 04/27/2010
• Est. Priority Date: 11/22/2004
• Status: Expired due to Fees

• 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, Tadi, Bulli Padmaja
• Primary Examiner(s): QAZI, SABIHA NAIM
• Application Number:
  US11/775,117
• Publication Number:
  US 20070249569A1
• Time in Patent Office: 1,023 Days
• Field of Search: 552/653, 514/167
• US Class Current: 514/167
• CPC Class Codes: A61P 1/00 Drugs for disorders of the alimentary tract or the digestive system
• 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 11/00 Drugs for disorders of the respiratory system
• CPC Class Codes: A61P 11/06 Antiasthmatics
• CPC Class Codes: A61P 17/00 Drugs for dermatological disorders
• CPC Class Codes: A61P 17/06 Antipsoriatics
• CPC Class Codes: A61P 19/00 Drugs for skeletal disorders
• 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 3/00 Drugs for disorders of the metabolism of the blood or the extracellular fluid A61P7/00
• CPC Class Codes: A61P 3/02 Nutrients, e.g. vitamins, minerals
• CPC Class Codes: A61P 3/04 Anorexiants; Antiobesity agents
• CPC Class Codes: A61P 3/06 Antihyperlipidemics
• 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 37/00 Drugs for immunological or allergic disorders
• CPC Class Codes: A61P 37/02 : Immunomodulators
• CPC Class Codes: A61P 37/06 : Immunosuppressants, e.g. drugs for graft rejection
• CPC Class Codes: A61P 37/08 : Antiallergic agents antiasthmatic agents A61P11/06; ophthalmic antiallergics A61P27/14
• CPC Class Codes: A61P 43/00 : Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• 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
• CPC Class Codes: Y02P 20/55 : Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Abstract

This invention discloses 2-methylene-19-nor-17-ene vitamin D analogs, and specifically 2-methylene-19-nor-1α-hydroxy-17-ene-homopregnacalciferol 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 autoimmune disorders and inflammatory diseases in humans as well as renal osteodystrophy. This compound may also be used for the treatment or prevention of obesity.

Claims

1. 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 a compound having the formula

2. The method of claim 1 wherein the compound is administered orally.

3. The method of claim 1 wherein the compound is administered parenterally.

4. The method of claim 1 wherein the compound is administered transdermally.

5. The method of claim 1 wherein the compound is administered rectally.

6. The method of claim 1 wherein the compound is administered nasally.

7. The method of claim 1 wherein the compound is administered sublingually.

8. The method of claim 1 wherein the compound is administered in a dosage of from about 0.01 μ

g/day to about 1000 μ

g/day.

9. The method of claim 1 wherein the compound is 2-methylene-19-nor-1α

-hydroxy-17-ene-homopregnacalciferol having the formula

10. The method of claim 1 wherein the animal is a human.

11. The method of claim 1 wherein the animal is a domestic animal.

12. The method of claim 1 wherein the animal is an agricultural animal.

13. A method of treating acne in an animal, the method comprising administering to an animal in need thereof an effective amount of a compound having the formula

14. The method of claim 13 wherein the compound is administered orally.

15. The method of claim 13 wherein the compound is administered parenterally.

16. The method of claim 13 wherein the compound is administered transdermally.

17. The method of claim 13 wherein the compound is administered rectally.

18. The method of claim 13 wherein the compound is administered nasally.

19. The method of claim 13 wherein the compound is administered sublingually.

20. The method of claim 13 wherein the compound is administered in a dosage of from about 0.01 μ

g/day to about 1000 μ

g/day.

21. The method of claim 13 wherein the compound is 2-methylene-19-nor-1α

-hydroxy-17-ene-homopregnacalciferol having the formula;

22. A method of treating hypertension in an animal, the method comprising administering to an animal in need thereof an effective amount of a compound having the formula

23. The method of claim 22 wherein the compound is administered orally.

24. The method of claim 22 wherein the compound is administered parenterally.

25. The method of claim 22 wherein the compound is administered transdermally.

26. The method of claim 22 wherein the compound is administered rectally.

27. The method of claim 22 wherein the compound is administered nasally.

28. The method of claim 22 wherein the compound is administered sublingually.

29. The method of claim 22 wherein the compound is administered in a dosage of from about 0.01 μ

g/day to about 1000 μ

g/day.

30. The method of claim 22 wherein the compound is 2-methylene-19-nor-1α

-hydroxy-17-ene-homopregnacalciferol having the formula;