GB893141A - Improvements in or relating to steroids and the manufacture thereof - Google Patents

Improvements in or relating to steroids and the manufacture thereof

Info

Publication number
GB893141A
GB893141A GB16653/58A GB1665358A GB893141A GB 893141 A GB893141 A GB 893141A GB 16653/58 A GB16653/58 A GB 16653/58A GB 1665358 A GB1665358 A GB 1665358A GB 893141 A GB893141 A GB 893141A
Authority
GB
United Kingdom
Prior art keywords
hydroxy
methyl
androstene
compound
dione
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
GB16653/58A
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.)
Pharmacia and Upjohn Co
Original Assignee
Upjohn 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 Upjohn Co filed Critical Upjohn Co
Publication of GB893141A publication Critical patent/GB893141A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J1/00Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
    • C07J1/0003Androstane derivatives
    • C07J1/0011Androstane derivatives substituted in position 17 by a keto group

Abstract

The invention comprises compounds of the general formulae <FORM:0893141/IV (b)/1> and <FORM:0893141/IV (b)/2> wherein X represents a keto or b -hydroxy group, Y represents hydrogen, fluorine, chlorine or bromine, Z represents a keto or b -hydroxy group or an acyloxy group derived from an organic carboxylic or sulphonic acid, and A represents a tertiary amino group of the general formula <FORM:0893141/IV (b)/3> wherein n and n1 represent 1 or 2, a process for the preparation of a compound of the second general formula above by reducing the corresponding 3-(N-cyclic tertiary amino)-6-methyl-11b -hydroxy-3,5-androstadiene-17-one with an alkali metal hydride such as lithium aluminium hydride, sodium hydride or sodium or potassium borohydride, a process for the preparation of 6a - methyl - 11b , 17a - dihydroxy - 4 - androsten - 3-one by hydrolysing a compound of the second general formula above in an aqueous medium with the optional further step of acylating the 17-hydroxy group with an organic carboxylic or sulphonic acid anhydride or halide (other acylating agents, such as isopropenyl acylate or ketene may be used) to form a 6a -methyl-11b ,17b -dihydroxy-4-androsten-3-one 17-acylate and with the optional further step of oxidizing the resulting 17-acylate with chromic acid (other oxidising agents, such as N-haloacid-amides and N-haloacidimides may be used) to form the corresponding 6a -methyl-17b -hydroxy - 4 - androstene - 3, 11 - dione 17 - acylate and, if desired, hydrolysing the 17-acylate to form 6a -methyl-17b -hydroxy-4-androstene-3, 11 - dione, a process for the preparation of 6a -methyl-11b -hydroxy-4-androstene-3,17-dione by hydrolysing in an aqueous medium a compound of the general formula <FORM:0893141/IV (b)/4> wherein A has the above significance, a process for the preparation of 6a -methyl-andrenosterone by oxidising 6a -methyl-11b -hydroxy-4-androstene - 3, 17 - dione, 6a - methyl - 17b - hydroxy - 4 - androstene - 3, 11 - dione or 6a - methyl - 11b , 17b - dihydroxy - 4 - androstene - 3 - one with chromic acid, a process for the preparation of a compound of the general formula <FORM:0893141/IV (b)/5> wherein Z represents a hydroxy or keto group, by treating the corresponding 11b -hydroxy compound with N-bromoacetamide and then with sulphur dioxide, a process for the preparation of a compound of the general formula <FORM:0893141/IV (b)/6> wherein Z represents a hydroxy or keto group and Y1 represents bromine or chlorine, by reacting the corresponding 9(11)-unsaturated compound free from a substituent at the 11-position with N-bromo- and N-chloro-acetamide in the presence of perchloric acid, with the optional further step of treating the product with potassium acetate to form a 9b ,11b -oxido compound of the general formula <FORM:0893141/IV (b)/7> wherein Z represents a hydroxy or keto group, and with the optional further step of treating the 9b ,11b -oxido compound with hydrogen fluoride to form a compound of the general formula <FORM:0893141/IV (b)/8> wherein Z has the same significance, a process for the preparation of 6a -methyl-9a -fluoro-17b -hydroxy-4-androstene-3, 11-dione or a 17-acylate thereof by acylating 6a -methyl-9a -fluoro-11b ,17b -dihydroxy-4-androstene-3-one, and then oxidising the 17b -acylate with chromic anhydride in acetic acid to form 6a -methyl-9a -fluoro-17b -hydroxy - 4 - androstene - 3, 11 - dione 17b - acylate and, when required, hydrolysing to form the corresponding free 17b -hydroxy compound, and a process for the preparation of 6a -methyl-9a -fluoroadrenosterone by oxidizing 6a -methyl-9a - fluoro - 17b - hydroxy - 4 - androstene - 3,11-dione with potassium dichromate or by oxidising 6a - methyl - 9a - fluoro - 11b - hydroxy - 4-androstene-3,17-dione with chromic anhydride in acetic acid. Detailed examples are given. Specification 893,142 is referred to.ALSO:A pharmaceutical composition suitable for administration orally or by injection, especially as a suspension in an oil, contains as the active ingredient a steroid of the general formula <FORM:0893141/VI/1> wherein X represents a keto or b -hydroxy group, Y represents hydrogen, fluorine, chlorine or bromine, and Z represents a keto or b -hydroxy group or a b -acyloxy group derived from an organic carboxylic or sulphonic acid. 6a -Methyl - 11b - hydroxy - testosterone or 6a -methyl - 11 - keto - testosterone may be incorporated into tablets together with hexyl barbital sodium. Specification 893,142 is referred to.
GB16653/58A 1957-05-27 1958-05-23 Improvements in or relating to steroids and the manufacture thereof Expired GB893141A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US893141XA 1957-05-27 1957-05-27

Publications (1)

Publication Number Publication Date
GB893141A true GB893141A (en) 1962-04-04

Family

ID=22216946

Family Applications (1)

Application Number Title Priority Date Filing Date
GB16653/58A Expired GB893141A (en) 1957-05-27 1958-05-23 Improvements in or relating to steroids and the manufacture thereof

Country Status (1)

Country Link
GB (1) GB893141A (en)

Similar Documents

Publication Publication Date Title
GB893141A (en) Improvements in or relating to steroids and the manufacture thereof
GB820780A (en) Cyclopentanophenanthrene derivatives
GB936391A (en) Process for the fluorination of steroids
AU523501B2 (en) 21 hydroxy 20 oxo 17 alpha pregnanes
GB959793A (en) Improvements in or relating to steroids
GB1152180A (en) delta&lt;8(14)&gt;-Steroids
GB893142A (en) Improvements in or relating to steroids and the manufacture thereof
GB969300A (en) New steroids of the androstane series and process for their production
GB1185381A (en) 05,16beta-Methylene Steroids of the 19-Nor-Androstane Series and Process for their Manufacture
ES252321A1 (en) 6alpha, 16alpha-dialkyl steroid intermediates and proceses
GB909614A (en) New cyclopentanophenanthrene derivatives and processes for the production thereof
GB745636A (en) Cyclopentanophenanthrene derivatives and process for their manufacture
GB944716A (en) 10ยช -fluoro steroids and their preparation
GB1022042A (en) Improvements in or relating to steroids and the manufacture thereof
GB923944A (en) Improvements in or relating to steroids and the manufacture thereof
ES262796A1 (en) New steroid compounds and their production
GB936224A (en) Novel steroids and their preparation
GB904123A (en) New cyclopentanophenanthrene compounds and process for the production thereof
GB854408A (en) New cyclopentanophenanthrene derivatives and process for the production thereof
GB803655A (en) Dehydrocortical hormones
GB991475A (en) Novel steroid compounds and processes for their production
GB852647A (en) Steroid compounds and preparation thereof
GB921533A (en) Cyclopentanophenanthrene derivatives and process for the production thereof
GB907190A (en) 21-trihalo steroids and a process for the manufacture thereof
GB750941A (en) Steroids