Vitamin D derivatives

• US 7,985,744 B2
• Filed: 06/14/2001
• Issued: 07/26/2011
• Est. Priority Date: 06/15/2000
• 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, Emura, Takashi, Ohmori, Masayuki, Morikawa, Kazumi, Shimizu, Kazuki
• Primary Examiner(s): Qazi; Sabiha
• Application Number:
  US10/311,538
• Publication Number:
  US 20040019023A1
• Time in Patent Office: 3,694 Days
• Field of Search: 514/167, 552/653, 552/553
• US Class Current: 514/167
• CPC Class Codes: A61K 31/592 9,10-Secoergostane derivatives, e.g. ergocalciferol, i.e. vitamin D2
• CPC Class Codes: A61K 31/593 9,10-Secocholestane derivatives, e.g. cholecalciferol, i.e. vitamin D3
• CPC Class Codes: A61P 17/00 Drugs for dermatological disorders
• CPC Class Codes: A61P 17/06 Antipsoriatics
• CPC Class Codes: A61P 3/02 Nutrients, e.g. vitamins, minerals
• CPC Class Codes: C07C 235/06 having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
• CPC Class Codes: C07C 2601/14 The ring being saturated
• CPC Class Codes: C07C 2602/24 the ring system containing nine carbon atoms, e.g. perhydroindane
• 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: C07D 295/185 from aliphatic carboxylic acids
• CPC Class Codes: C07F 7/1804 Compounds having Si-O-C linkages Si-O-acyl linkages C07F7/1896
• CPC Class Codes: C07J 7/00 Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms C07J5/00 takes precedence
• 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
• CPC Class Codes: Y02P 20/55 Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Abstract

The object of the present invention is to provide vitamin D derivatives that have excellent physiological activities as medicines, particularly as therapeutic agents for skin diseases such as psoriasis, and that have a reduced hypercalcemic effect.

The present invention provides a vitamin D derivative of Formula (1):

• • wherein
    • X represents an oxygen atom or a sulfur atom;
    • m represents a number of 1 to 3;
    • R₁ and R₂ each represent a hydrogen atom or an alkyl group;
    • R₄ and R₅ each represent a hydrogen atom or a hydroxyl group, etc.;
    • R₃ represents —YR₈, etc.;
    • R₆ represents a hydrogen atom, etc.;
    • R₇ represents a hydrogen atom, etc.

Claims

1. A compound of Formula (1):

3. A pharmaceutical composition comprising a compound according to claim 1.

4. A method of treating psoriasis, which comprises the step of administering to a patient in need of such treatment a therapeutically effective amount of the compound according to claim 1.

5. The pharmaceutical composition according to claim 3 wherein said composition is used for treating psoriasis.

6. A method for inhibiting the growth of human keratinocytes comprising administering to a patient in need thereof an effective amount of a pharmaceutical composition according to claim 3 to inhibit the growth of human keratinocytes.

2. {(1α

,3β

-Dihydroxy-9,10-secopregna-5,7,10(19),16-tetraen-20(S)-yl)oxy}-N-(2,2,3,3,3-pentafluoropropyl)acetamide.