Vitamin D3 analogs

• US 6,329,538 B1
• Filed: 08/25/2000
• Issued: 12/11/2001
• Est. Priority Date: 05/23/1996
• Status: Expired due to Fees

• Current Assignee: Hoffmann-La Roche Incorporated (Roche Holding AG)
• Original Assignee: Hoffmann-La Roche Incorporated (Roche Holding AG)
• Inventors: Uskokovic, Milan Radoje, Iacobelli, Jerome Anthony, Hennessy, Bernard Michael, Batcho, Andrew David
• Primary Examiner(s): QAZI, SABIHA NAIM
• Application Number:
  US09/648,817
• Time in Patent Office: 473 Days
• Field of Search: 552/653, 514/167, 514/168
• US Class Current: 552/653
• CPC Class Codes: A61K 31/59 Compounds containing 9, 10- seco- cyclopenta[a]hydrophenanthrene ring systems
• 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

A compound of the formula

wherein R is hydrogen or hydroxy, each R² is independently H or halogen, X is ═CH₂, or when R is hydroxy, X is hydrogen or ═CH₂, and A is —C≡C—,

or —CH₂—CH₂—, provided that when A is —CH₂—CH₂—, R₂ is H.

Claims

1. A compound of the formula

wherein R is hydrogen or hydroxy, each R² is independently H or halogen, X is ═

CH₂, or when R is hydroxy, X is hydrogen or ═

CH₂, and A is —

C≡

C—

,

or —

CH₂—

CH₂—

, provided that when A is —

CH₂—

CH₂—

, R₂ is H.

2. A compound of claim 1, wherein R is hydroxy.

3. A compound of claim 2, wherein A is —

C≡

C—

.

4. A compound of claim 2, wherein A is —

CH₂—

CH₂.

5. A compound of claim 2, wherein

6. A compound of claim 3, wherein each R₂ is F.

7. A compound of claim 4, wherein each R₂ is F.

8. A compound of claim 5, wherein each R₂ is F.

9. A compound of claim 3, wherein each R₂ is H.

10. A compound of claim 4, wherein each R₂ is H.

11. A compound of claim 5, wherein each R₂ is H.

12. A compound of claim 2, wherein X is hydrogen.

13. A compound of claim 1, wherein R is hydrogen.

14. The compound of claim 1, which is 25-dihydroxy-16-ene-23-yne-20-epi-cholecalciferol.

15. The compound of claim 1, which is 1,25-dihydroxy-16-ene-23-yne-26,27-hexafluoro-20-epi-cholecalciferol.

16. The compound of claim 1, which is 1,25-dihydroxy-16,23E-diene-26,27-hexafluoro-20-epi-cholecalciferol.

17. The compound of claim 1, which is 1,25-dihydroxy-16,23Z-diene-26,27-hexafluoro-20-epi-cholecalciferol.

18. The compound of claim 1, which is 1,25-dihydroxy-16,23Z-diene-26,27-hexafluoro-20-epi-19-nor-cholecalficerol.