2-methylene-19-nor-(23S)-25-dehydro-1α-hydroxyvitamin D3-26,23-lactone and 2-methylene-19-nor-(23R)-25-dehydro-1α-hydroxyvitamin D3-26,23-lactone

• US 7,235,680 B2
• Filed: 03/28/2006
• Issued: 06/26/2007
• Est. Priority Date: 03/29/2005
• 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, Chiellini, Grazia
• Primary Examiner(s): QAZI, SABIHA NAIM
• Application Number:
  US11/390,999
• Publication Number:
  US 20060223782A1
• Time in Patent Office: 455 Days
• Field of Search: 514/167, 552/653
• US Class Current: 552/653
• CPC Class Codes: A61P 11/06 Antiasthmatics
• CPC Class Codes: A61P 17/00 Drugs for dermatological disorders
• CPC Class Codes: A61P 25/30 for treating abuse or dependence
• 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 39/00 General protective or antinoxious agents
• 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: C07F 7/1804 Compounds having Si-O-C linkages Si-O-acyl linkages C07F7/1896
• CPC Class Codes: Y02P 20/55 Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Abstract

Compounds of formula 1A and 1B are provided where X¹ and X² are independently selected from H or hydroxy protecting groups. Such compounds may be used in preparing pharmaceutical compositions and are useful in treating a variety of biological disorders

Claims

1. A compound having the formula 1A, 1B, or a mixture thereof,

2. The compound of claim 1, wherein X¹ and X² are both hydroxy protecting groups.

3. The compound of claim 2, wherein X¹ and X² are both t-butyldimethylsilyl groups.

4. The compound of claim 1, wherein X¹ and X² are both H and the compound has the formula 1A1 or 1B1:

5. A pharmaceutical composition, comprising an effective amount of the compound of claim 4 and a pharmaceutically acceptable carrier.

6. The pharmaceutical composition of claim 5 wherein the effective amount comprises from about 0.01 μ

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

7. The pharmaceutical composition of claim 5 wherein the effective amount comprises from about 0.1 μ

g to about 500 μ

g of the compound per gram of the composition.

8. The compound of claim 1, wherein X¹ and X² are both H and the compound has formula 1A2 or 1B2:

9. The compound of claim 1, wherein the mixture thereof comprises the compound of formula 1A and the compound of formula 1B, and the ratio of the compound of formula 1A to the compound of formula 1B ranges from 50:

50 to 99.9;

01.

10. The compound of claim 9, wherein the ratio of the compound of formula 1A to the compound of formula 1B ranges from 70:

30 to 99.9;

0.1.

11. The compound of claim 1, wherein the mixture thereof comprises the compound of formula 1A and the compound of formula 1B, and the ratio of the compound of formula 1B to the compound of formula 1A ranges from 50:

50 to 99.9;

0.1.

12. The compound of claim 11, wherein the ratio of the compound of formula 1B to the compound of formula 1A ranges from 70:

30 to 99.9;

0.1.