19,26,27-trinor-1α,25-dihydroxyvitamin D3 compounds

• US 7,241,909 B2
• Filed: 05/02/2006
• Issued: 07/10/2007
• Est. Priority Date: 05/03/2005
• Status: Active Grant

• 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, Grzywacz, Pawel
• Primary Examiner(s): QAZI, SABIHA NAIM
• Application Number:
  US11/416,401
• Publication Number:
  US 20060264410A1
• Time in Patent Office: 434 Days
• Field of Search: 514/167, 552/653
• US Class Current: 552/653
• CPC Class Codes: A61P 11/06 Antiasthmatics
• CPC Class Codes: A61P 13/12 of the kidneys
• CPC Class Codes: A61P 17/00 Drugs for dermatological disorders
• CPC Class Codes: A61P 17/06 Antipsoriatics
• 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 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 3/14 for calcium homeostasis vitamin D A61P3/02; parathyroid hormones A61P5/18; calcitonin A61P5/22; osteoporosis A61P19/10; bone metastasis A61P35/04
• CPC Class Codes: A61P 35/00 Antineoplastic agents
• CPC Class Codes: A61P 35/02 specific for leukemia
• CPC Class Codes: A61P 43/00 Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• CPC Class Codes: A61P 5/18 of the parathyroid hormones
• 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

Compounds of formula 1 are provided where X¹, X², and X³ are independently selected from H or hydroxy protecting groups, and R¹ and R² have the definitions provided herein. Such compounds may be used in preparing pharmaceutical compositions and are useful in treating a variety of biological conditions

Claims

1. A compound having the formula 1,

2. The compound of claim 1, wherein X³ is H, and the compound of formula 1 has the formula 1A

3. The compound of claim 2, wherein X¹ and X² are both hydroxy protecting groups.

4. The compound of claim 3, wherein X¹ and X² are both t-butyldimethylsilyl groups.

5. The compound of claim 2, wherein X¹ and X² are both H and the compound has the formula 3A

6. The compound of claim 2, wherein X¹ and X² are both H and the compound has the formula 3B

7. The compound of claim 2, wherein X¹ and X² are both H and the compound has the formula 3C

8. A pharmaceutical composition, comprising an effective amount of the compound of claim 1 and a pharmaceutically acceptable carrier.

9. The pharmaceutical composition of claim 8, wherein the effective amount comprises from about 0.01 μ

g to about 1 mg of the compound per gram of the composition.

10. The pharmaceutical composition of claim 9, wherein the effective amount comprises from about 0.1 μ

g to about 500 μ

g of the compound per gram of the composition.

11. The pharmaceutical composition of claim 8, wherein X³ is H.

12. The pharmaceutical composition of claim 11, wherein X¹ and X² are both H.