GB965292A - Halogenated steroid derivatives - Google Patents

Halogenated steroid derivatives

Info

Publication number
GB965292A
GB965292A GB43294/61A GB4329461A GB965292A GB 965292 A GB965292 A GB 965292A GB 43294/61 A GB43294/61 A GB 43294/61A GB 4329461 A GB4329461 A GB 4329461A GB 965292 A GB965292 A GB 965292A
Authority
GB
United Kingdom
Prior art keywords
alkanoate
haloethynyl
hydroxy
compound
norandrost
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
GB43294/61A
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 GB965292A publication Critical patent/GB965292A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
    • 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 steroids of the general formula: <FORM:0965292/C1/1> wherein X represents fluorine or chlorine, R represents hydrogen or methyl, R11 represents hydrogen or lower alkanoyl containing not more than 6 carbon atoms, there is a double bond in the 4(5)- or 5(10)-position, and R1 represents hydrogen or methyl when the double bond is in the 4-position. The 10, 13-dimethyl compounds having a double bond in the 4(5)-position are prepared by treating steroids of the general formula: <FORM:0965292/C1/2> wherein R has the above significance and R111 represents hydrogen or the lower alkanoyl radical, with fluoroacetylene or 1,2-dichloroethylene in the presence of sodium amide to form the corresponding 17b -hydroxy-17a -haloethynyl compound, (if required, esterifying this compound to form the corresponding 17b -alkanoate), hydrolysing the 3-alkanoate group with methanolic hydrogen chloride, if necessary selectively, to form the corresponding 3b , 17b -dihydroxy-17a -haloethynyl compound or a 17b -alkanoate thereof, and oxidising by the Oppenauer method to form the 3-keto group (a free 17b -hydroxy group in the product may then be converted to a 17b -alkanoyloxy group). The 19-nor-compounds of the first general formula above are prepared by treating compounds of the general formula: <FORM:0965292/C1/3> with fluoroacetylene or 1,2-dichloroethylene in the presence of sodium amide to form the corresponding 17b -hydroxy-17a -haloethynyl compound (if required esterifying this compound to form the corresponding 17b -alkanoate), and either heating the previously mentioned 17b -hydroxy compound or corresponding 17-alkanoate in the presence of methanolic acetic acid to form 17a -haloethynyl-17b -hydroxy-19-norandrost-5(10)-en-3-one or the corresponding 17-alkanoate, or warming the said compounds in the presence of mineral acid to form 17a -haloethynyl-17b -hydroxy-19-norandrost-4-en-3-one or the corresponding 17-alkanoate. The 17a -haloethynyl-17b -hydroxy-19-norandrost-4-en-3-one may be acetylated with isopropenyl acetate to form the corresponding 17b -ol-3,5-dienol-3, 17b -diacetate and then partially saponified form 17a -haloethynyl-17b -acetoxy-19-norandrost-4-en-3-one.
GB43294/61A 1960-12-05 1961-12-04 Halogenated steroid derivatives Expired GB965292A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US7348760A 1960-12-05 1960-12-05

Publications (1)

Publication Number Publication Date
GB965292A true GB965292A (en) 1964-07-29

Family

ID=22113980

Family Applications (1)

Application Number Title Priority Date Filing Date
GB43294/61A Expired GB965292A (en) 1960-12-05 1961-12-04 Halogenated steroid derivatives

Country Status (2)

Country Link
FR (1) FR1632M (en)
GB (1) GB965292A (en)

Also Published As

Publication number Publication date
FR1632M (en) 1963-01-02

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