Side-chain unsaturated 1-hydroxyvitamin D compounds

• US 4,719,205 A
• Filed: 11/04/1985
• Issued: 01/12/1988
• Est. Priority Date: 01/30/1984
• 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: Tanaka, Yoko, DeLuca, Hector F., Sicinski, Rafal R., Schnoes, Heinrich K.
• Primary Examiner(s): Schenkman, Leonard
• Assistant Examiner(s): Lipovsky, Joseph A.
• Application Number:
  US06/794,325
• Time in Patent Office: 799 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 71/0042 Nitrogen only
• 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

Abstract

Novel 1-hydroxylated vitamin D compounds containing a 22, 23-cis double bond in the side chain are provided. The compounds are characterized by an unexpectedly high binding affinity for the protein receptor forecasting their ready applicability as substitutes for vitamin D or various of its metabolites in their various known applications and in the treatment of various metabolic bone diseases.

Claims

1. Compounds having the formula ##STR4## wherein X₁ and X₂ is hydrogen or acyl and where the substituent at carbon 1 may have the α

or β

stereochemical orientation.

2. Compounds according to claim 1 where X₁ and X₂ are hydrogen.

3. Compounds according to claim 1 wherein at least one of X₁ and X₂ are acetyl.

4. Compound having the formula ##STR5## wherein X₁ and X₂ are hydrogen or acyl.

5. The compound according to claim 4 wherein X₁ and X₂ are hydrogen.

6. The compound of claim 5 in crystalline form.

7. A pharmaceutical composition comprising the compound of claim 5 together with a pharmaceutically acceptable excipient.

8. A pharmaceutical composition comprising at least one of the compounds of claim 4 together with a pharmaceutically acceptable excipient.

9. Compounds having the formula ##STR6## wherein X₁ and X₂ are hydrogen or acyl.

10. A pharmaceutical composition comprising at least one of the compounds of claim 9, together with a pharmaceutically acceptable excipient.

11. The compound according to claim 9 wherein X₁ and X₂ are hydrogen.

12. A pharmaceutical composition comprising the compound of claim 11 together with a pharmaceutically acceptable excipient.

13. A pharmaceutical composition comprising in admixture the compounds of claim 5 and claim 11 and a pharmaceutically acceptable excipient.