Homologated vitamin D.sub.2 compounds and the corresponding 1.alpha.-hydroxylated derivatives

• US 5,260,290 A
• Filed: 02/13/1991
• Issued: 11/09/1993
• Est. Priority Date: 02/14/1990
• 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: DeLuca, Hector F., Schnoes, Heinrich K., Perlman, Kato L.
• Primary Examiner(s): Mars, Howard T.
• Assistant Examiner(s): PRIOR, KIMBERLY
• Application Number:
  US07/654,746
• Time in Patent Office: 1,000 Days
• Field of Search: 552/653, 514/167
• US Class Current: 514/167
• 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: C07J 71/0042 Nitrogen only

Abstract

The invention provides new 24, 26, and/or 27 homologated vitamin D₂ compounds, such as 26,27-dihomo-1α-hydroxyvitamin D₂, 26,27-dihomo-1α-hydroxy-24-epi-vitamin D₂, 26,27-dihomo-1α,25-dihydroxy-24-epi-vitamin D₂ and certain hydroxy-protected derivatives thereof. The new epi compounds in particular exhibit a distinctive activity pattern comprising high potency in stimulating intestinal calcium transport and little or no activity in inducing bone calcium mobilization or the differentiation of undifferentiated cells in culture, thereby evincing utility in the treatment of diseases characterized by loss of bone mass. In contrast, the natural form exhibits no activity in either mobilizing calcium from bone or stimulating intestinal calcium transport. A process for preparing such compounds is also disclosed.

Claims

1. 26,27-dihomo-1α

,25-dihydroxy-24-epi-vitamin D₂.

2. A pharmaceutical composition comprising 26,27-dihomo-1α

,25-dihydroxy-24-epi-vitamin D₂ together with a pharmaceutically acceptable excipient.