GB883310A - Improvements in or relating to hormonal agents - Google Patents

Improvements in or relating to hormonal agents

Info

Publication number
GB883310A
GB883310A GB25754/59A GB2575459A GB883310A GB 883310 A GB883310 A GB 883310A GB 25754/59 A GB25754/59 A GB 25754/59A GB 2575459 A GB2575459 A GB 2575459A GB 883310 A GB883310 A GB 883310A
Authority
GB
United Kingdom
Prior art keywords
compound
methyl
treated
dione
fluoro
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
GB25754/59A
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.)
GD Searle LLC
Original Assignee
GD Searle LLC
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 GD Searle LLC filed Critical GD Searle LLC
Publication of GB883310A publication Critical patent/GB883310A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J75/00—Processes for the preparation of steroids in general

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Steroid Compounds (AREA)

Abstract

The invention comprises compounds of the general formula <FORM:0883310/IV (b)/1> wherein X represents an alkyl group containing less than 7 carbon atoms. The compounds may be prepared by a halogen interchange with the corresponding 17a -hydroxy-21-iodo compounds followed by esterification of the 17-hydroxy. In examples: (1) 3,20-bisethylenedioxy-17a ,21-dihydroxy-5-pregnene is converted to the corresponding 21-acetate, the 21-acetate is converted to 3,20 - bisethylenedioxy - 5a ,6a - epoxy - 17a - hydroxy - 21 - acetoxypregnane by reaction with peroxyacetic acid in the presence of chloroform and methylethyldioxolane, the 5a ,6a -epoxy compound is reacted with methyl magnesium bromide to form 3,20 - bisethylenedioxy - 6b - methyl - 5a ,17a ,21 - tri - hydroxypregnane, this compound is hydrolysed to form 6b -methyl-5a ,17a ,21 - trihydroxypregnane - 3,20 - dione, this compound is treated with benzenesulphonyl chloride to form 6b -methyl-21-chloro-5a ,17a -dihydroxy-pregnane-3,20-dione, the 21-chloro compound is treated with sodium iodide to form the corresponding 21-iodo compound and then with silver fluoride to form the corresponding 21-fluoro compound, the 21-fluoro compound is esterified and dehydrated with a mixture of acetic acid and acetic anhydride or with a mixture of caproic acid and caproic anhydride to form the enol acetates 6-methyl-21-fluoro-3,17a -diacetoxy (and dihexanoyloxy)-3,5-pregnadien-20-one which are hydrolysed with methanolic hydrogen chloride to form 6a -methyl-17a -acetoxy (and hexanoyloxy)-21-fluoroprogester-one; (2) 6b -methyl-5a ,17a , 21-trihydroxypregnane- 3,20-dione is treated with aqueous sodium hydroxide to form 6a - methyl - 17a ,21 - dihydroxy - 4 - pregnene - 3,20 - dione, this compound is treated with benzenesulphonyl chloride to form 6a - methyl - 17a - hydroxy - 21 - chloro - 4 - pregnene - 3,20 - dione, this compound is treated with sodium iodide to form the corresponding 21-iodo-compound and then with silver fluoride to form the corresponding 21-fluoro compound, this compound is esterified with acetic acid and acetic anhydride to form 3,17a -diacetoxy - 6 p - methyl - 21 - fluoro - 3,5 - pregnadien-20-one which is then treated as in (1).
GB25754/59A 1958-07-28 1959-07-27 Improvements in or relating to hormonal agents Expired GB883310A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US883310XA 1958-07-28 1958-07-28

Publications (1)

Publication Number Publication Date
GB883310A true GB883310A (en) 1961-11-29

Family

ID=22210746

Family Applications (1)

Application Number Title Priority Date Filing Date
GB25754/59A Expired GB883310A (en) 1958-07-28 1959-07-27 Improvements in or relating to hormonal agents

Country Status (1)

Country Link
GB (1) GB883310A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3183228A (en) * 1962-06-25 1965-05-11 American Home Prod 21-fluoro-17alpha-methylpregnane derivatives

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3183228A (en) * 1962-06-25 1965-05-11 American Home Prod 21-fluoro-17alpha-methylpregnane derivatives

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