GB737773A - Improvements relating to 11-a-hydroxy-testosterone and esters thereof - Google Patents

Improvements relating to 11-a-hydroxy-testosterone and esters thereof

Info

Publication number
GB737773A
GB737773A GB26710/53A GB2671053A GB737773A GB 737773 A GB737773 A GB 737773A GB 26710/53 A GB26710/53 A GB 26710/53A GB 2671053 A GB2671053 A GB 2671053A GB 737773 A GB737773 A GB 737773A
Authority
GB
United Kingdom
Prior art keywords
hydroxy
testosterone
acid
aqueous
androstadiene
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB26710/53A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Wyeth Holdings LLC
Original Assignee
American Cyanamid Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by American Cyanamid Co filed Critical American Cyanamid Co
Publication of GB737773A publication Critical patent/GB737773A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J75/00—Processes for the preparation of steroids in general
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Abstract

The invention comprises 11-b -hydroxy-testosterone and esters thereof of the general formula <FORM:0737773/IV (b)/1> wherein R represents hydrogen or -OR represents the acyloxy residue of a fatty acid containing up to 6 carbon atoms or benzoic acid, and the preparation thereof by heating a D 3,5-androstadiene-11b , 17b -diol-3-ether in aqueous acid solution, e.g. with aqueous acetic acid or dilute hydrochloric or sulphuric acid, to produce 11b -hydroxy-testosterone, and if desired reacting this compound with anhydrides or acid chlorides of fatty acids containing up to 6 carbon atoms or benzoic acid. The heating with the aqueous acid solution may be effected at a temperature of 60 DEG to 120 DEG C. The 11b -hydroxy-testosterone is preferably recovered from the aqueous acid solution by treatment with an aqueous alkaline solution to neutralize the acid and then extraction with an organic solvent. An alternative method for the preparation of the above compounds is to protect the 3-keto group of D 4-androstene-3,11,17-trione by the formation of an ether radical, e.g. by treatment with benzyl or ethyl alcohol, the protected compound is then treated with lithium aluminium hydride to reduce the keto groups in the 11- and 17-positions to hydroxy radicals and the protective group in the 3-position is removed to form 11b -hydroxy testosterone. In the examples, 11b -hydroxy-testosterone is prepared by etherifying D 4-androstene-3,11,17-trione with benzyl alcohol to form 3-benzyloxy-D 3,5-androstadiene-11,17-dione, reduction with lithium aluminium hydrides gives 3-benzyloxy-D 3,5-androstadiene-11b , 17b -diol which is then hydrolysed with acetic acid, and 11b -hydroxy-testosterone acetate is prepared from the free hydroxy compound. The propionate, butyrate and benzoate esters are also referred to.
GB26710/53A 1952-10-08 1953-09-29 Improvements relating to 11-a-hydroxy-testosterone and esters thereof Expired GB737773A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US737773XA 1952-10-08 1952-10-08

Publications (1)

Publication Number Publication Date
GB737773A true GB737773A (en) 1955-09-28

Family

ID=22115741

Family Applications (1)

Application Number Title Priority Date Filing Date
GB26710/53A Expired GB737773A (en) 1952-10-08 1953-09-29 Improvements relating to 11-a-hydroxy-testosterone and esters thereof

Country Status (1)

Country Link
GB (1) GB737773A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3017419A (en) * 1957-07-20 1962-01-16 Syntex Sa 11alpha-methyl-androstane derivatives
US3076822A (en) * 1958-11-19 1963-02-05 British Drug Houses Ltd 4-methyl-3-oxo-delta steroids and methods for preparing same

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3017419A (en) * 1957-07-20 1962-01-16 Syntex Sa 11alpha-methyl-androstane derivatives
US3076822A (en) * 1958-11-19 1963-02-05 British Drug Houses Ltd 4-methyl-3-oxo-delta steroids and methods for preparing same

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