Vitamin D3 derivative and production process thereof

• US 6,177,586 B1
• Filed: 06/08/1999
• Issued: 01/23/2001
• Est. Priority Date: 06/07/1994
• Status: Expired due to Term

• Current Assignee: Teijin Limited
• Original Assignee: Teijin Limited
• Inventors: Tanaka, Hiroko, Manabe, Kenji, Hazato, Atsuo, Tabe, Masayasu, Gao, Qinqzhi
• Primary Examiner(s): Trinh, Ba K.
• Application Number:
  US09/327,489
• Time in Patent Office: 595 Days
• Field of Search: 556/489, 560/119, 560/256, 562/501, 568/374, 568/819
• US Class Current: 556/489
• 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

The starting materials for a production process of a vitamin D₃ derivative are disclosed, e.g., a cyclopentene derivative represented by the formula (1-2):

wherein R₁¹ is a hydrogen atom, tri(C₁ to C₇ hydrocarbon) silyl group, C₂ to C₇ acyl group, group forming an acetal bond together with an oxygen atom of a hydroxyl group, and X₁ is a bromine or iodine atom; and a heptanoic acid derivative represented by the formula (2-4):

wherein X₂ is a bromine atom or iodine atom.

Claims

1. A cyclopentene derivative represented by the following formula (1-2):

wherein, R₁¹ is a hydrogen atom, tri(C₁ to C₇ hydrocarbon)silyl group, C₂ to C₇ acyl group, group forming an acetal bond together with an oxygen atom of a hydroxyl group, and X₁ is a bromine atom or iodine atom.

2. A cyclopentene derivative as claimed in claim 1, wherein the asymmetric center of the C-1 position of the cyclopentene ring of the formula (1-2) is the (R) configuration and the asymmetric center of the C-4 position is the (S) configuration.

3. A cyclopentene derivative as claimed in claim 1, wherein the asymmetric center of the C-1 position of the cyclopentene ring of the formula (1-2) is the (S) configuration and the asymmetric center of the C-4 position is the (S) configuration.

4. A cyclopentene derivative represented by the following formula (1-6):

wherein, R₁¹² is a hydrogen atom, tri(C₁ to C₇ hydrocarbon)silyl group, C₂ to C₇ acyl group, or group forming an acetal bond together with an oxygen atom of a hydroxyl group.

5. A cyclopentene derivative as claimed in claim 4, wherein the asymmetric center of the C-1 position of the cyclopentene ring of the formula (1-6) is the (R) configuration and the asymmetric center of the C-4 position is the (S) configuration.

6. A cyclopentene derivative as claimed in claim 4, wherein the asymmetric center of the C-1 position of the cyclopentene ring represented by the formula (1-6) is the (S) configuration and the asymmetric center of the C-4 position is the (S) configuration.

7. A heptanoic acid derivative represented by the following formula (2-4):

wherein, X₂ is a bromine atom or iodine atom.

8. A heptanoic acid derivative represented by the following formula (3-2):

wherein, R₃¹ is hydrogen or C₁ to C₃ alkyl group and R₃² is hydrogen or R₃¹ and R₃² together are a single substitutable group.

9. A heptanoic acid derivative represented by the following formula (3-3):

wherein, R₃¹ and R₃² are the same as defined above.