Hydroxylated 24-homo-vitamin D derivatives and methods for preparing same

• US 4,857,518 A
• Filed: 02/28/1986
• Issued: 08/15/1989
• Est. Priority Date: 10/04/1984
• 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., Tanaka, Yoko, Ikekawa, Nobuo
• Primary Examiner(s): NOT, DEFINED
• Assistant Examiner(s): Lipovsky, Joseph A.
• Application Number:
  US06/835,065
• Time in Patent Office: 1,264 Days
• Field of Search: 260/397.2, 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 17/00 Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton cardanolide, bufanolide C07J19/00
• CPC Class Codes: C07J 71/001 Oxiranes
• CPC Class Codes: C07J 9/00 Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
• CPC Class Codes: C07J 9/005 containing a carboxylic function directly attached or attached by a chain containing only carbon atoms to the cyclopenta[a]hydrophenanthrene skeleton

Abstract

This invention is directed to new 24-homo-vitamin D compounds, to methods for preparing the same and novel intermediate compounds.

The compounds are characterized by vitamin D-like activity of the order of 1α,25-dihydroxyvitamin D₃, the recognized circulating hormonal form of vitamin D, or various of its derivatives and by greater antineoplastic activity than such compounds but without their attendant calcemic activity. The compounds are useful in the treatment of disease states characterized by calcium-phosphorous imbalances and where antineoplastic activity is indicated.

Claims

1. Compounds having the formula ##STR3## where R₁, R₂ and R₃ are each selected from the group consisting of hydrogen, an acyl group having from 1 to about 4 carbon atoms and benzoyl and R₄ and R₅ each represent hydrogen atoms or taken together form a carbon to carbon double bond.

2. A compound according to claim 1 wherein R₁, R₂ and R₃ are hydrogen and R₄ and R₅ are hydrogen atoms.

3. The compound of claim 2 in crystalline form.

4. A composition comprising the compound of claim 2 and a pharmaceutically acceptable excipient.

5. A compound according to claim 2 wherein the Δ

22 bond is in the E configuration.

6. A compound according to claim 2 wherein the Δ

22 bond is in the Z configuration.

7. A compound according to claim 1 wherein R₁, R₂ and R₃ are hydrogen and R₄ and R₅ together represent a carbon to carbon double bond.

8. The compound of claim 7 in crystalline form.

9. Compounds having the formula ##STR4## where R is selected from the group consisting of hydrogen, an acyl group having from 1 to about 4 carbon atoms, benzoyl and methoxymethyl.

10. Compounds having the formula ##STR5## where R is selected from the group consisting of an acyl group having from about 1 to about 4 carbon atoms and benzoyl and R₄ and R₅ represent hydrogen atoms or taken together form a carbon to carbon double bond.