Vitamin D.sup.3 derivative and production process thereof

• US 5,986,112 A
• Filed: 11/14/1997
• Issued: 11/16/1999
• Est. Priority Date: 06/07/1994
• Status: Expired due to Term

• Current Assignee: Teijin Limited, Teijin Thailand Limited (Teijin Limited)
• Original Assignee: Teijin Limited
• Inventors: Tanaka, Hiroko, Gao, Qingzhi, Manabe, Kenji, Hazato, Atsuo, Tabe, Masayasu
• Primary Examiner(s): OWENS, AMELIA A
• Application Number:
  US08/971,201
• Time in Patent Office: 732 Days
• Field of Search: 549/214, 549/313, 549/323, 549/324
• US Class Current: 549/324
• 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: C07C 69/675 of saturated hydroxy-carboxylic acids
• CPC Class Codes: C07C 69/716 Esters of keto-carboxylic acids or aldehydo-carboxylic acids
• CPC Class Codes: C07C 69/732 of unsaturated hydroxy carboxylic acids
• CPC Class Codes: C07D 307/33 in position 2, the oxygen atom being in its keto or unsubstituted enol form
• CPC Class Codes: C07D 307/58 One oxygen atom, e.g. butenolide
• CPC Class Codes: C07D 317/34 Oxygen atoms
• CPC Class Codes: C07F 7/1804 Compounds having Si-O-C linkages Si-O-acyl linkages C07F7/1896

Abstract

A vitamin D₃ derivative represented by the following formula: wherein, R is, independently, a hydrogen atom, tri(C₁ to C₇ hydrocarbon)silyl group, C₂ to C₈ acyl group, or group forming an acetal bond together with an oxygen atom of a hydroxyl group, A is ##STR1## where, R¹ is a methyl group or methylene group, and when R¹ is a methylene group, the bond between the R¹ and the 3-position of the lactone ring is a double bond, R² is a hydrogen atom or C₁ to C₃ alkyl group, R³ is a hydrogen atom, or R² and R³ together indicate a substitutable single methylene group.

Claims

1. A lactone compound represented by the following (2-2) ##STR94## wherein, R₂¹ is a methyl group or a methylene group, and X₂ is a bromine atom or an iodine atom.

2. A lactone compound represented by the following (2-3):

##STR95## wherein, R₂¹ is a methyl group or a methylene group.

3. An exomethylene derivative represented by the following formula (4-1):

##STR96## wherein, R₄¹ is a hydrogen atom, tri(C₁ to C₇ hydrocarbon)silyl group, A C₂ to C₇ acyl group, or A group forming an acetal bond together with an oxygen atom of a hydroxyl group, and X₄ is a bromine atom or iodine atom.

4. The exomethylene derivative as claimed in claim 3, wherein, in the above formula (4-1), the asymmetric center of the C-3 position of the 2(3H)-furanon ring is A (R) configuration and the asymmetric center of the C-5 position is A (R) configuration.

5. An exomethylene derivative as claimed in claim 3, wherein, in the above formula (4-1), the asymmetric center of the C-3 position of the 2(3H)-furanon ring is the (R) configuration and the asymmetric center of the C-5 position is the (S) configuration.