Intermediates for the synthesis of 19-nor vitamin D compounds

• US 5,086,191 A
• Filed: 05/28/1991
• Issued: 02/04/1992
• Est. Priority Date: 05/28/1991
• Status: Expired due to Term

• Current Assignee: Wisconsin Alumni Research Foundation (University of Wisconsin System)
• Original Assignee: Wisconsin Alumni Research Foundation (University of Wisconsin System)
• Inventors: DeLuca, Hector F., Schnoes, Heinrich K., Perlman, Kato L.
• Primary Examiner(s): Mars, Howard T.
• Assistant Examiner(s): PRIOR, KIMBERLY
• Application Number:
  US07/705,932
• Time in Patent Office: 252 Days
• Field of Search: 552/653
• US Class Current: 552/653
• CPC Class Codes: C07C 47/267 containing rings other than six-membered aromatic rings
• CPC Class Codes: C07C 47/277 containing ether groups, groups, groups, or groups
• CPC Class Codes: C07F 7/1804 Compounds having Si-O-C linkages Si-O-acyl linkages C07F7/1896

Abstract

New intermediate compounds that can be used effectively for the synthesis of a broad range of 1α-hydroxy-19-nor-vitamin D compounds. These novel intermediates are characterized by a group selected from hydroxy methyl (--CH₂ OH), carboxaldehyde (--CHO), and carboxy ester (--COOAlkyl) at the carbon 22 position of the side chain of a 19-nor-vitamin D nucleus. Intermediates of this type are useful for the introduction of side chain units and thus represent important synthons for the preparation of many different 19-nor-vitamin D compounds.

Claims

1. A compound of the formula

where X¹ and X², which may be the same or different, represent hydrogen or a hydroxy-protecting group, and where R¹ is selected from the group consisting of hydroxy-methyl, hydroxy-protected hydroxymethyl, carboxaldehyde (--CHO), and carboxyalkyl (--COOAlkyl).