Vitamin D derivative with substituent at the 2.beta.-position

• US 5,877,168 A
• Filed: 09/03/1996
• Issued: 03/02/1999
• Est. Priority Date: 02/10/1995
• Status: Expired due to Fees

• Current Assignee: Chugai Seiyaku Kabushiki Kaisha (Roche Holding AG)
• Original Assignee: Chugai Seiyaku Kabushiki Kaisha (Roche Holding AG)
• Inventors: Kubodera, Noboru, Miyamoto, Katsuhito
• Primary Examiner(s): Dees, Jose G.
• Assistant Examiner(s): BADIO, BARBARA P
• Application Number:
  US08/706,969
• Time in Patent Office: 910 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

Abstract

A 1α-hydroxy-vitamin D derivative represented by formula (I): ##STR1## wherein R₁ represents a hydrogen atom or a hydroxyl group; and R₂ represents a straight-chain or branched lower alkyl, lower alkenyl or lower alkynyl group, which is substituted with a hydroxyl group, a halogen atom, a cyano group, a lower alkoxy group, an amino group or an acylamino group,

is disclosed. The compound exhibits calcium metabolism regulating activity and differentiation stimulating activity on tumor cells, etc. and is useful as a treating agent for diseases caused by abnormal calcium metabolism, such as osteoporosis and osteomalacia, or as an antitumor agent.

Claims

1. A compound represented by formula (I):

##STR6## wherein R₁ represents a hydrogen atom or a hydroxyl group; and

R₂ represents a straight-chain or branched C₁ -C₇ alkyl, C₂ -C₇ alkenyl or C₂ -C₇ alkynyl group, which is substituted with a hydroxyl group, a halogen atom, a cyano group, a lower alkoxy group, an amino group or an acylamino group.

2. The compound of claim 1 which is 2β

-(4-hydroxybutyl)-1α

,3-dihydroxy-9,10-secocholesta-5,7,10(19)-triene.

3. The compound of claim 1 which is 1α

,3β

-dihydroxy-2β

-(6-hydroxyhexyl)-9,10-secocholesta-5,7,10(19)-triene.

4. The compound of claim 1 which is 2β

-(6-hydroxyhexyl)-1α

,3β

,25-trihydroxy-9,10-secocholesta-5,7,10(19)-triene.

5. The compound of claim 1 which is 2β

-(4-hydroxybutyl-1α

,3β

,25-trihydroxy-9,10-secocholesta-5,7,10(19)-triene.

6. The compound of claim 1 which is 2β

-(3-hydroxy-propyl)-1α

,3β

,25-trihydroxy-9,10-secocholesta-5,7,10(19)-triene.

7. The compound of claim 1 which is 2β

-(5-hydroxy-pentyl)-1α

,3β

,25-trihydroxy-9,10-secocholesta-5,7,10(19)-triene.

8. The compound of claim 1 which is 1α

,3β

-dihydroxy-2β

-(5-hydroxypentyl)-9,10-secocholesta-5,7,10(19)-triene.

12. A method for treating osteoporosis comprising administering to a patient in need thereof an effective amount of a compound according to claim 1.

9. Pharmaceutical composition comprising a pharmacologically effective amount of a compound represented by formula (I):

##STR7## wherein R₁ represents a hydrogen atom or a hydroxyl group; and

R₂ represents a straight-chain or branched C_1-C7 alkyl, C₂ -C₇ alkenyl or C_2-C7 alkynyl group, which is substituted with a hydroxyl group, a halogen atom, a cyano group, a lower alkoxy group, an amino group or an acylamino group, and a pharmaceutically acceptable carrier.

10. A pharmaceutical composition according to claim 9 wherein said pharmaceutically acceptable carrier comprises an edible oil.

11. A pharmaceutical composition according to claim 9 wherein said compound is 2β

-(5-hydroxypentyl)-1α

,3β

,25-trihydroxy-9,10-secocholestra-5,7,10(19)-triene and said pharmaceutically acceptable carrier comprises an edible food product.

13. A method for treating osteoporosis comprising administering to a patient in need thereof an effective amount of a composition according to claim 9.