GB893145A - 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
GB893145A
GB893145A GB669/59A GB66959A GB893145A GB 893145 A GB893145 A GB 893145A GB 669/59 A GB669/59 A GB 669/59A GB 66959 A GB66959 A GB 66959A GB 893145 A GB893145 A GB 893145A
Authority
GB
United Kingdom
Prior art keywords
fluoro
androstane
hydroxy
keto
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
GB669/59A
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 GB893145A publication Critical patent/GB893145A/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

Abstract

The invention comprises a 6-fluoro compound of the formula <FORM:0893145/IV (b)/1> wherein R is methyl or hydrogen, R1 is hydroxyl, O acyl or keto, the term acyl representing the acyl radical of an organic carboxylic acid, X is a carbonyl radical or a hydroxymethylene radical, and Z is hydroxyl or keto, and the preparation thereof by a process which comprises treating compounds of the formula <FORM:0893145/IV (b)/2> p wherein R, R1 and Z are as defined above, with hydrogen in the presence of a noble metal catalyst to obtain compounds of the formula <FORM:0893145/IV (b)/3> wherein R, R1 and Z are as defined above, treating the compounds thus obtained with sodium or potassium borohydride thereby producing a 3-hydroxy compound and, if desired, acylating the hydroxy group in 17-position if present. Illustrative products of the invention are 6a -fluoro - 17b - hydroxy - 5a - androstane - 3, 11 - dione, 6a - fluoro - 11b , 17b - dihydroxy - 5a - androstane - 3 - one, 6a - fluoro - 5a - androstane - 3 17 - dione, 6a - fluoro - 5a - androstane - 3, 11, 17 - trione, 6a - fluoro - 11b - hydroxy - 5a - androstane - 3, 17 - dione, 6a - fluoro - 3b , 17b - dihydroxy - 5a - androstan - 11 - one, 6a - fluoro - 3b , 11b , 17b - trihydroxy - 5a - androstane, 6a - fluoro - 3b - hydroxy - 5a - androstan - 11, 17 - dione, and 6a - fluoro - 3b , 11b - dihydroxy - 5a - androstan - 17 - one. Specification 893,147 is referred to.ALSO:Pharmaceutical compositions comprise a compound having the formula <FORM:0893145/VI/1> wherein R is methyl or hydrogen, R1 is hydroxyl, O-acyl or keto, X is a carbonyl radical or a hydroxymethylene radical, and Z is hydroxyl or keto and a pharmaceutical diluent. They are employed orally as pills, tablets, capsules, syrups or elixirs or in liquid forms for injectable products. Specification 893,147 is referred to.
GB669/59A 1958-02-19 1959-01-07 Improvements in or relating to steroids and the manufacture thereof Expired GB893145A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US893145XA 1958-02-19 1958-02-19

Publications (1)

Publication Number Publication Date
GB893145A true GB893145A (en) 1962-04-04

Family

ID=22216951

Family Applications (1)

Application Number Title Priority Date Filing Date
GB669/59A Expired GB893145A (en) 1958-02-19 1959-01-07 Improvements in or relating to steroids and the manufacture thereof

Country Status (1)

Country Link
GB (1) GB893145A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5656621A (en) * 1983-08-02 1997-08-12 Research Corporation Tech., Inc. Steroids useful as anti-cancer and anti-obesity agents
US5714481A (en) * 1983-08-02 1998-02-03 Research Corporation Technologies, Inc. Derivatives of 5-androsten-17 ones and 5-androstan-17-ones
US5804576A (en) * 1983-08-02 1998-09-08 Research Corporation Technologies, Inc. Derivatives of 5-androsten-17-ones and 5-androstan-17-ones

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5656621A (en) * 1983-08-02 1997-08-12 Research Corporation Tech., Inc. Steroids useful as anti-cancer and anti-obesity agents
US5696106A (en) * 1983-08-02 1997-12-09 Research Corporation Technologies, Inc. Steroids useful as anti-cancer and anti-obesity agents
US5700793A (en) * 1983-08-02 1997-12-23 Research Corporation Technologies, Inc. Steroids useful as anti-cancer and anti-obesity agents
US5714481A (en) * 1983-08-02 1998-02-03 Research Corporation Technologies, Inc. Derivatives of 5-androsten-17 ones and 5-androstan-17-ones
US5744462A (en) * 1983-08-02 1998-04-28 Research Corporation Technologies, Inc. Steroids useful as anti-cancer and anti-obesity agents
US5804576A (en) * 1983-08-02 1998-09-08 Research Corporation Technologies, Inc. Derivatives of 5-androsten-17-ones and 5-androstan-17-ones

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