GB935334A - New anabolic steroids and the preparation thereof - Google Patents

New anabolic steroids and the preparation thereof

Info

Publication number
GB935334A
GB935334A GB25315/61A GB2531561A GB935334A GB 935334 A GB935334 A GB 935334A GB 25315/61 A GB25315/61 A GB 25315/61A GB 2531561 A GB2531561 A GB 2531561A GB 935334 A GB935334 A GB 935334A
Authority
GB
United Kingdom
Prior art keywords
methylene
methyl
compound
androsten
testosterone
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
GB25315/61A
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.)
Merck KGaA
Original Assignee
E Merck AG
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 E Merck AG filed Critical E Merck AG
Publication of GB935334A publication Critical patent/GB935334A/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
    • C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J75/00—Processes for the preparation of steroids in general
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Steroid Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention comprises 16-methylene-17a -methyl-5-androstene-3b ,17b -diol, 16-methylene-17a -methyl-testosterone and the corresponding 1-dehydro compound, and 16-methylene-17a -methyl-testosterone-3-oxime and the corresponding 1-dehydro compound, and a process that comprises treating 16-methylene-5-androsten-3b -ol-20-one with an alkali metal methyl or a methyl magnesium halide to form 16-methylene-17a -methyl-5-androstene-3b ,17b -diol, if desired, mildly oxidising this compound to form 16-methylene-17a -methyltestosterone and, if desired, dehydrogenating this compound microbiologically or chemically in the 1,2-position and/or converting the 3-keto-group into a 3-oxime group. The oxidation may be carried out using the Oppenauer method or by the action of a culture of the microorganism Flavobacterium dehydrogenans. If a culture of the microorganism Corynebacterium simplex is used for the oxidation, dehydrogenation in the 1,2-position also takes place to form 16-methylene-1-dehydro- 17a -methyl-testosterone in one step. The dehydrogenation step may be carried out with selenium dioxide or 2,3-dichloro-5,6-dicyano-benzoquinone, or by means of a culture of any of the microorganisms Bacillus sphaericus, Fusarium solani, Corynebacterium simplex, Alternaria sp., Mycobacterium smegmatis, Calonectria decora, Mycobacterium lacticola, Ophiobolus sp., Alcaligenes sp., Didymella lycopersici, Protaminobacter sp., Septomyxa affinis, Nocardia sp., Cylindrocarpon radicicola, Streptomyes lavendulae, and Bacillus cyclooxydans. In the above process it is possible to convert the 3b -ol-5-ene system into a 3-keto-4-ene system, and to introduce the 1,2-double bond before the reaction with the alkali metal methyl or methyl magnesium halide. Therapeutic compositions having anabolic activity contain as the active ingredient a 16-methylene-steroid compound detailed above. The composition may be in the form of a pill, tablet, dragee, suppository, emulsion or injectable solution. 16-Methylene-5-androsten-3b -ol-20-one is prepared by a Mannich condensation with 5-androsten-3b -ol-20-one to form 16-dimethylaminomethyl- 5-androsten-3b -ol-20-one which is then decomposed by steam distillation.
GB25315/61A 1960-07-23 1961-07-12 New anabolic steroids and the preparation thereof Expired GB935334A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEM46033A DE1159942B (en) 1960-07-23 1960-07-23 Process for the production of new anabolically effective 16-methylene steroids

Publications (1)

Publication Number Publication Date
GB935334A true GB935334A (en) 1963-08-28

Family

ID=7305476

Family Applications (1)

Application Number Title Priority Date Filing Date
GB25315/61A Expired GB935334A (en) 1960-07-23 1961-07-12 New anabolic steroids and the preparation thereof

Country Status (4)

Country Link
CH (1) CH401959A (en)
DE (1) DE1159942B (en)
FR (1) FR1309M (en)
GB (1) GB935334A (en)

Also Published As

Publication number Publication date
FR1309M (en) 1962-05-14
CH401959A (en) 1965-11-15
DE1159942B (en) 1963-12-27

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