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:
Oct. 10, 1978
Filed:
Mar. 29, 1977
Peter Wieland, Oberwil, CH;
Ciba-Geigy Corporation, Ardsley, NY (US);
Abstract
The invention provides a novel general process for the manufacture of 6.beta.,7-methylene-3-oxo-4-ene-steroids by successively (a) reacting a 3.xi.,5.beta.-dihydroxy-6-ene-steroid which is optionally etherified or esterified in the 3-position with a zinc/copper-methylene iodide reagent to introduce the 6.beta.,7-methylene bridge, (b) liberating an etherified or esterified 3-hydroxyl group if such a group is present, (c) treating the resultant 6.beta.,7-methylene-3.xi.,5.beta.-dihydroxy-steroid with an oxidizing agent to dehydrogenate the 3-hydroxyl group to the oxo group, and (d) dehydrating the 6.beta.,7-methylene-5.beta.-hydroxy-3-oxo-steroid to form the 4,5-double bond. The starting materials, which form a novel class of compounds, can be obtained by a novel process by converting a 5.beta.,6-oxido-3.xi.-hydroxy-steroid with a selenol, for example phenylselenol, to a 6.alpha.-alkyl- or arylseleno-3.xi.,5.beta.-dihydroxy-steroid, oxidizing this compound with a peroxidic reagent, for example hydrogen peroxide, in a weakly acid medium to give the corresponding 6-selenonyl compound, and converting this compound, preferably by treatment with a base, preferably with 1,5-diazabicyclo[4,3,0]non-5-ene, to give the 3.xi.,5.beta.-dihydroxy-6-ene-steroid. During the course of these reactions, the 3-hydroxyl group is preferably temporarily protected by esterification or etherification.