http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-886619-A

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classificationCPCInventive http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07J75-00
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filingDate 1959-08-28-04:00^^<http://www.w3.org/2001/XMLSchema#date>
inventor http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_5ea1b1f894bcaccf97bf2b47e592a945
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publicationDate 1962-01-10-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber GB-886619-A
titleOfInvention 6-methyl-16-methylene steroids
abstract The invention comprises (a) 17a -acyloxy-6-methyl - 16 - methylenepregna - 4 : 6 - diene - 3 : 20-diones (wherein the acyl group contains at most 6 carbon atoms) and their preparation by oxidising with an alkaline peroxidizing agent 3b -hydroxy- or a 3b -acyloxy-6 : 16-dimethylpregna- 5 : 16-dien-20-one to the corresponding 3b -hydroxy-16a : 17a -epoxide, acylating the 3b -hydroxy group, treating the 3b -acyloxy-16a : 17a -epoxide with a source of hydrogen ions to give a steroid of the formula <FORM:0886619/IV (b)/1> (wherein R1 is an acyl group containing at most 6 carbon atoms), acylating this to give a 3b : 17a -diacylate, preferentially hydrolysing this to give the corresponding 3b -hydroxy-17a -acyloxy compound and subjecting this to an Oppenauer oxidation in the presence of a benzoquinone; and (b) a steroid of the above formula wherein R1 is an acetyl group, and the corresponding 3b : 17a -diacetate and 3b -hydroxy-17-acetate. In the above process the preferred reagents for each reaction stage are hydrogen peroxide in alkaline alcohol as peroxidizing agent, sulphuric acid or hydrogen bromide in a non-polar solvent as source of hydrogen ions, acetic acid in presence of toluene p-sulphonic acid monohydrate as 17-acetylating agent, hot ethanolic or methanolic hydrochloric acid as preferential hydrolysing agent, and p-benzoquinone or chloranil, an aluminium alkoxide, e.g. the t-butoxide, and a solvent such as benzene as reagents for the Oppenauer oxidation. Examples are given. Specifications 850,423, 870,286 and 886,620 are referred to.ALSO:17a - Acetoxy - 6 - methyl - 16 - methylene-pregna-4 : 6-diene-3 : 20-dione is made up into tablets, elixirs, suppositories or injections, and is stated to have progestational activity. Specifications 850,423, 870,286 and 886,620 are referred to.
priorityDate 1959-08-28-04:00^^<http://www.w3.org/2001/XMLSchema#date>
type http://data.epo.org/linked-data/def/patent/Publication

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