CH214329A - Process for the preparation of a new enol derivative containing the sterol core. - Google Patents

Process for the preparation of a new enol derivative containing the sterol core.

Info

Publication number
CH214329A
CH214329A CH214329DA CH214329A CH 214329 A CH214329 A CH 214329A CH 214329D A CH214329D A CH 214329DA CH 214329 A CH214329 A CH 214329A
Authority
CH
Switzerland
Prior art keywords
preparation
benzoate
derivative containing
new
enol derivative
Prior art date
Application number
Other languages
German (de)
Inventor
Gesellschaft Fuer Chemis Basel
Original Assignee
Chem Ind Basel
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 Chem Ind Basel filed Critical Chem Ind Basel
Publication of CH214329A publication Critical patent/CH214329A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
    • 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
    • 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
    • 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
    • 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)

Description

  

  Verfahren zur Darstellung eines neuen den     Sterinkern    enthaltenden     Enolderivates.       Gegenstand der vorliegenden Erfindung  bildet ein Verfahren zur     Darstellung    eines  neuen den     Sterinkern    enthaltenden     Enol-          derivates,    welches dadurch gekennzeichnet  ist, dass man auf     d4>5-Testoteron-benzoat    ein       benzoylierendes    Mittel einwirken lässt.  



  Das so gewonnene     Enolbenzoat    des     Testo-          steron-benzoates    bildet Kristalle vom F. 183  bis 184'. Mit     Tetranitromethan    färbt es sich  intensiv gelbbraun.  



  Das neue     Enolderivat    soll therapeutische  Verwendung finden oder als Zwischenprodukt  zur Gewinnung therapeutisch wirksamer Ver  bindungen dienen.    <I>Beispiel:</I>    0,256 Teile     Testosteronbenzoat    werden in  12,5 Teilen Benzin und 2,3 Teilen     Benzoyl-          chlorid    während etwa 44 Stunden zum Sieden  erhitzt. Nach Absaugen des Benzins und       Benzoylehlorids    kristallisiert das     Enolbenzoat     des     Testosteron-17-benzoats    aus und kann    durch Verreiben     mit    Aceton rein erhalten  werden (F. l83-184   unter Zersetzung).  



  Man kann an Stelle von     Benzoylchlorid     ein anderes     Benzoylhalogenid    oder auch       Benzoesäureanhydrid    verwenden und zur  Bindung der     entstehenden    Salzsäure zum Bei  spiel eine     tertiäre    Base wie     Pyridin    und der  gleichen zugeben.



  Process for the preparation of a new enol derivative containing the sterol core. The subject matter of the present invention is a process for the preparation of a new enol derivative containing the sterol core, which is characterized in that a benzoylating agent is allowed to act on d4> 5-testoterone benzoate.



  The enol benzoate of testosterone benzoate obtained in this way forms crystals with a mp of 183 to 184 '. With tetranitromethane, it turns an intense yellow-brown.



  The new enol derivative is intended to be used therapeutically or to serve as an intermediate product for obtaining therapeutically effective compounds. <I> Example: </I> 0.256 parts testosterone benzoate are heated to the boil in 12.5 parts gasoline and 2.3 parts benzoyl chloride for about 44 hours. After suctioning off the gasoline and benzoylechloride, the enol benzoate of testosterone 17-benzoate crystallizes out and can be obtained in pure form by trituration with acetone (F. 183-184 with decomposition).



  Instead of benzoyl chloride, another benzoyl halide or benzoic anhydride can be used and, for example, a tertiary base such as pyridine and the like can be added to bind the hydrochloric acid formed.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines neuen den Sterinkern enthaltenden Enolderivates, dadurch gekennzeichnet, dass man auf d4,5- Testosteron-benzoat ein benzoylierendes Mit tel einwirken lässt. Das so gewonnene Enolbenzoat des Testo- steron-benzoates bildet Kristalle vom F. 183 bis 184'. Mit Tetranitromethan färbt es sieh intensiv gelbbraun. PATENT CLAIM: Process for the preparation of a new enol derivative containing the sterol core, characterized in that a benzoylating agent is allowed to act on d4,5-testosterone benzoate. The enol benzoate of testosterone benzoate obtained in this way forms crystals with a mp of 183 to 184 '. With tetranitromethane, it turns an intense yellow-brown. Das neue Enolderivat soll therapeutische Verwendung finden oder als Zwischenprodukt zur Gewinnung therapeutisch wirksamer Ver bindungen dienen. UNTERANSPRWHE 1. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man als benzoylie- rendes Mittel ein Benzoylhalogenid verwen det. 2. Verfahren nach Patentanspruch und Unteranspruch 1, dadurch gekennzeichnet, dass man in Anwesenheit eines säurebinden den Mittels arbeitet. 3. The new enol derivative is intended to be used therapeutically or as an intermediate product to obtain therapeutically effective compounds. SUB-CLAIM 1. The method according to claim, characterized in that a benzoyl halide is used as the benzoylating agent. 2. The method according to claim and dependent claim 1, characterized in that one works in the presence of an acid-binding agent. 3. Verfahren nach Patentanspruch und Unteransprüchen 1 und 2, dadurch gehenn- zeichnet, da.ss man als säurebindendes Mittel eine tertiäre Base verwendet. 4. Verfahren nach Patentanspruch und Unteransprüchen 1 bis 3, dadurch gekenn zeichnet, dass man als säurebindendes Mittel Pyridin verwendet. 5. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man als ben- zoylierendes Mittel Benzoesäureanhydrid ver wendet. Process according to patent claim and dependent claims 1 and 2, characterized in that a tertiary base is used as the acid-binding agent. 4. The method according to claim and dependent claims 1 to 3, characterized in that the acid-binding agent used is pyridine. 5. The method according to claim, characterized in that the benzoylating agent used is benzoic anhydride.
CH214329D 1936-05-18 1936-05-18 Process for the preparation of a new enol derivative containing the sterol core. CH214329A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH211649T 1936-05-18
CH214329T 1936-05-18

Publications (1)

Publication Number Publication Date
CH214329A true CH214329A (en) 1941-04-15

Family

ID=25725028

Family Applications (1)

Application Number Title Priority Date Filing Date
CH214329D CH214329A (en) 1936-05-18 1936-05-18 Process for the preparation of a new enol derivative containing the sterol core.

Country Status (1)

Country Link
CH (1) CH214329A (en)

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