16-ENE-vitamin D derivatives

• US 6,326,503 B1
• Filed: 08/18/2000
• Issued: 12/04/2001
• Est. Priority Date: 12/20/1996
• Status: Expired due to Fees

• Current Assignee: Chugai Seiyaku Kabushiki Kaisha (Roche Holding AG)
• Original Assignee: Chugai Seiyaku Kabushiki Kaisha (Roche Holding AG)
• Inventors: Kawase, Akira
• Primary Examiner(s): QAZI, SABIHA NAIM
• Application Number:
  US09/640,800
• Time in Patent Office: 473 Days
• Field of Search: 552/523, 552/623, 552/632
• US Class Current: 552/623
• 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 31/006 not covered by C07J31/003
• CPC Class Codes: C07J 7/007 not substituted in position 17 alfa
• CPC Class Codes: Y02P 20/55 Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Abstract

A compound having the formula (4): wherein

X is oxygen or sulfur, R₉ and R₁₀ are each a hydrogen or a protecting group, and R₁₁ is an aliphatic hydrocarbon, a —COR₁₂ group where R₁₂ is alkyl, aryl or alkoxy, or a group of formula

wherein R₅ and R₆ are each hydrogen or hydroxyl, m is 1 to 4, and n is 0-2.

Claims

1. A compound of general formula (4):

wherein

X represents an oxygen or sulfur atom,

R₁₁ represents

(i) a saturated C1-C15 aliphatic hydrocarbon group or unsaturated C2-C15 aliphatic hydrocarbon group which may be substituted by a hydroxyl group or a protected hydroxyl group,

(ii) a —

COR₁₂ group where R₁₂ represents an alkyl, aryl or alkoxy group, or

 

wherein R₅ and R₆ each represent a hydrogen atom or a hydroxyl group, m represents an integer of 1 to 4, and n represents an integer of 0 to 2,

R₂ represents —

OR₉ or a hydrogen atom, and

R₉ and R₁₀ may by the same or different and each represents a hydrogen atom or a protecting group.

2. The compound of claim 1, wherein R₁₁ is a saturated C1-C15 aliphatic hydrocarbon group which may be substituted by a hydroxyl group.

3. The compound of claim 1, wherein R₁₁ is an unsaturated C2-C15 aliphatic hydrocarbon group which may be substituted by a hydroxyl group.

4. The compound of claim 1, wherein R₁₁ is a group (2):

wherein R₃ and R₄ may be the same or different and each represent a hydrogen atom or a hydroxyl group, or are combined to represent=0, provided that R₃ and R₄ cannot be a hydroxyl group simultaneously, R₅ and R₆ each represent a hydrogen atom or a hydroxyl group, but R₆ cannot be a hydroxyl group simultaneously with R₃ or R₄, m represents an integer of 1 to 4, and n represents an integer of 0 to 2;

or a group (3);

wherein R₅ and R₆ may be the same or different and each represent a hydrogen atom or a hydroxyl group, R₇ and R₈ each represent a hydrogen atom or are combined to represent a covalent bond, p represents an integer of 1 to 3, and q represents an integer of 0 to 2.

5. The compound of claim 1, wherein R₁₁ is a 3-hydroxy-3-methylbutyl group.