The patent badge is an abbreviated version of the USPTO patent document. The patent badge does contain a link to the full patent document.
The patent badge is an abbreviated version of the USPTO patent document. The patent badge covers the following: Patent number, Date patent was issued, Date patent was filed, Title of the patent, Applicant, Inventor, Assignee, Attorney firm, Primary examiner, Assistant examiner, CPCs, and Abstract. The patent badge does contain a link to the full patent document (in Adobe Acrobat format, aka pdf). To download or print any patent click here.
Patent No.:
Date of Patent:
Jul. 30, 1985
Filed:
Nov. 02, 1983
William L White, Holliston, MA (US);
Peter B Anzeveno, Zionsville, IN (US);
The Dow Chemical Company, Midland, MI (US);
Abstract
Improved procedures and intermediates for synthesizing 11-deoxyprostaglandins wherein trans-2,3-dicarbomethoxycyclopentanone is subjected to a novel alcoholysis with .beta.,.beta.,.beta.-trichloroethanol to substitute a .beta.,.beta.,62 -trichlorocarboethoxy group at the 2-position followed by alkylation to allow for a wide range of upper side chains to be introduced at the 2-position of the cyclopentanone ring. The unwanted .beta.,.beta.,.beta.-trichlorocarboethoxy group at the 2-position can then be removed easily by a zinc induced elimination-decarboxylation sequence. Base catalyzed epimerization of the 2-position side chain to the desired trans-configuration, relative to the carbomethoxy group in the 3-position, is followed by partial reduction of the 2-hexynyl moiety of the side chain to the desired cis-olefinic group of the E.sub.2 -type 11-dioxyprostaglandins, or through total reduction to the alkane upper side chain of E.sub.1 -type-prostaglandin analogs. Modification thereafter of the carbonyl group at the 3-position of the cyclopentanone ring by a variety of reagents allows introduction of the lower side chain present in the prostaglandins themselves or a variety of other side chains derived from the 3-carboxy-, 3-hydroxymethyl- or 3-aldehyde-substituted cyclopentanone ring. From the latter, 11-deoxyprostaglandins can be prepared by known procedures.