PROCESS FOR PRODUCING VITAMIN D DERIVATIVE USING PHOTOREACTION

• US 20100261917A1
• Filed: 11/30/2006
• Published: 10/14/2010
• Est. Priority Date: 11/30/2005
• Status: Active Grant

• Current Assignee: Chugai Seiyaku Kabushiki Kaisha (Roche Holding AG)
• Original Assignee: Chugai Seiyaku Kabushiki Kaisha (Roche Holding AG)
• Inventors: Kawase, Akira, Ikeda, Takuma, Kato, Yasuharu, Kitoh, Yasushi, Kobayashi, Mio, Maruyama, Noriaki, Kinoshita, Kazutomo, Haneishi, Tsuyoshi
• Granted Patent: US 8,212,059 B2
• Time in Patent Office: Days
• US Class Current: 552/610
• CPC Class Codes: A61P 17/00 Drugs for dermatological disorders
• CPC Class Codes: A61P 17/06 Antipsoriatics
• 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 41/00 Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
• CPC Class Codes: C07J 71/00 Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring spiro-condensed heterocyclic rings C07J21/00, C07J33/00, C07J43/00

Abstract

There are provided a novel process for producing [{(5Z,7E)-(1S,3R,20S)-1,3-dihydroxy-9,10-secopregna-5,7,10(19),16-tetraen-20-yl}oxy]-N-(2,2,3,3,3-pentafluoropropyl)acetamide, which process is characterized by irradiating a compound represented by the formula:

with UV to ring-open the compound, and then isomerizing the resulting compound; an intermediate useful for carrying out the process; and a process for producing the intermediate.

Claims

1. A process for producing a compound represented by Formula (1):

2. The process according to claim 1, wherein said compound represented by Formula (2) is obtained by a process comprising the steps of:

subjecting a compound represented by Formula (3);

3. The process according to claim 1, wherein said compound represented by Formula (2) is obtained by a process comprising the steps of:

reacting a compound represented by Formula (4);

4. The process according to claim 2, wherein both of R¹ and R² are tert-butyldimethylsilyl groups.

5. A compound represented by Formula (3):

6. The compound according to claim 5, wherein both of R¹ and R² are tert-butyldimethylsilyl groups.

7. A compound represented by Formula (2):