CH215558A - 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
CH215558A
CH215558A CH215558DA CH215558A CH 215558 A CH215558 A CH 215558A CH 215558D A CH215558D A CH 215558DA CH 215558 A CH215558 A CH 215558A
Authority
CH
Switzerland
Prior art keywords
acetate
agent
preparation
acid
derivative containing
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 CH215558A publication Critical patent/CH215558A/en

Links

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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (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        Enolderi-          vates,    welches dadurch gekennzeichnet ist,  dass man auf     Desogycorticosteron-21-acetat     ein     acetylierendes        Mittel    einwirken lässt.  



  Das so gewonnene     Enolacetat    des     Desogy-          corticosteronacetatas    bildet Kristalle vom  F. 111 bis 112'. Mit     Tetranitromethan    färbt  es sich intensiv braun.  



  Das neue     Enolderivat    soll therapeutische  Verwendung finden oder als Zwischenprodukt  zur Gewinnung     therapeutisch        wirksamer    Ver  bindungen dienen.  



       Beispiel:     0,1 Teile     Desogycorticosteronacetat    wer  den mit 3,5 Teilen     Acetanhydrid    und 0,2 Tei  len     frischgeschmolzenem        galiumacetat    wäh  rend     etwa.    42     Stunden    zum Sieden erhitzt.  Das Reaktionsprodukt wird in Wasser ge  gossen und in Äther aufgenommen.

   Nach  dem Waschen der ätherischen Lösung mit    verdünnter     Sodalösung    und Wasser wird mit       Natriumsulfat    getrocknet, das     Lösungsmittel     verdampft     und        das    erhaltene     Reaktionspro-          dukt    aus     Hegan    umgelöst. Das so gewonnene       Enolacetat    des     Desogycorticosteronacetates          schmilzt    bei 11 bis 112'. Mit     Tetranitro-          methan        zeigt    es deutliche Braunfärbung.  



  Man kann an Stelle von     galiumacetat     auch ein     anderes    Salz der Essigsäure verwen  den oder ohne Zusatz eines solchen arbeiten.  



  Denselben Endstoff erhält man auch  durch Kochen von     Desogycorticosteronacetat,     zum Beispiel mit     Acetylehlorid    in einem or  ganischen     Lösungsmittel,        wie        Benzin,    bis zur  vollendeten Reaktion.     Ferner    kann man zur  Bindung der     entstehenden    Salzsäure zum  Beispiel eine tertiäre Base, wie     Pyridin    und  dergleichen, 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 nucleus, which is characterized in that an acetylating agent is allowed to act on desogycorticosterone-21-acetate.



  The enol acetate of desogycorticosterone acetate obtained in this way forms crystals with a melting point of 111 to 112 '. With tetranitromethane it turns an intense brown.



  The new enol derivative is intended to be used therapeutically or to serve as an intermediate product for obtaining therapeutically effective compounds.



       Example: 0.1 part of desogycorticosterone acetate with 3.5 parts of acetic anhydride and 0.2 parts of freshly melted galium acetate during about. Heated to the boil for 42 hours. The reaction product is poured into water and taken up in ether.

   After washing the ethereal solution with dilute soda solution and water, it is dried with sodium sulfate, the solvent is evaporated and the Hegan reaction product obtained is redissolved. The enol acetate of desogycorticosterone acetate obtained in this way melts at 11 to 112 '. With tetranitomethane it shows a clear brown color.



  Another salt of acetic acid can be used in place of galium acetate, or it can be used without the addition of one.



  The same end product is also obtained by boiling desogycorticosterone acetate, for example with acetyl chloride in an organic solvent such as gasoline, until the reaction is complete. Furthermore, to bind the hydrochloric acid formed, for example a tertiary base such as pyridine and the like can be added.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines neuen, den Sterinkern enthaltenden Enolderivates, dadurch gekennzeichnet, dass man auf Desogy- corticosteron-21-acetat ein acetylierendes Mit tel einwirken lässt. Das. so gewonnene Enolacetat des Desozy- corticosteronacetates bildet Kristalle vom F. l11 bis 112'. Mit Tetranitromethan färbt es sich intensiv braun. PATENT CLAIM: Process for the preparation of a new enol derivative containing the sterol core, characterized in that an acetylating agent is allowed to act on desogycorticosterone-21-acetate. The. The enol acetate of desocycorticosterone acetate obtained in this way forms crystals from F. 11 to 112 '. With tetranitromethane it turns an intense brown. Das neue Enolderivat soll therapeutische Verwendung finden oder als Zwischenprodukt zur Gewinnung therapeutisch wirksamer Ver bindungen dienen. <B>UNTERANSPRÜCHE:</B> 1. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man als acetylie- rendes Mittel Essigsäureanhydrid verwendet. 2. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man als acetylie- rendes Mittel ein Halogenid der Essigsäure verwendet. Verfahren nach Patentanspruch und Unteranspruch 2, dadurch gekennzeichnet, dass man in Anwesenheit eines säurebinden den Mittels arbeitet. 4. The new enol derivative is intended to be used therapeutically or to serve as an intermediate product for obtaining therapeutically effective compounds. <B> SUBClaims: </B> 1. Method according to patent claim, characterized in that acetic anhydride is used as the acetylating agent. 2. The method according to claim, characterized in that a halide of acetic acid is used as the acetylie- rendes agent. Method according to claim and dependent claim 2, characterized in that the agent is used in the presence of an acid-binding agent. 4th Verfahren nach Patentanspruch und .den Unteransprüchen 2 und 3, dadurch ge kennzeichnet, @dass man als säurebindendes Mittel eine tertiäre Base verwendet. 5. Verfahren nach Patentanspruch und den Unteransprüchen 2, 3 und 4, dadurch ge kennzeichnet, dass man als säurebindendes Mittel Pyridin verwendet. A method according to patent claim and. The dependent claims 2 and 3, characterized in that a tertiary base is used as the acid-binding agent. 5. The method according to claim and the dependent claims 2, 3 and 4, characterized in that the acid-binding agent used is pyridine.
CH215558D 1936-05-18 1936-05-18 Process for the preparation of a new enol derivative containing the sterol core. CH215558A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH215558T 1936-05-18
CH211649T 1936-05-18

Publications (1)

Publication Number Publication Date
CH215558A true CH215558A (en) 1941-06-30

Family

ID=25725042

Family Applications (1)

Application Number Title Priority Date Filing Date
CH215558D CH215558A (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) CH215558A (en)

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