CH215550A - 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
CH215550A
CH215550A CH215550DA CH215550A CH 215550 A CH215550 A CH 215550A CH 215550D A CH215550D A CH 215550DA CH 215550 A CH215550 A CH 215550A
Authority
CH
Switzerland
Prior art keywords
preparation
propionate
acid
derivative containing
agent
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 CH215550A publication Critical patent/CH215550A/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)
  • Steroid Compounds (AREA)

Description

  

  Verfahren zur Darstellung eines neuen, den     Sterinkern    ' enthaltenden     Enolderioates.       Gegenstand der vorliegenden Erfindung  bildet ein Verfahren zur Darstellung eines  neuen, den     Sterinkern    enthaltenden     Enol-          derivates,    welches dadurch gekennzeichnet  ist, dass man auf d     4,5    - Testosteron -17     -          propionat    ein     propionylierend-es    Mittel ein  wirken lässt.  



       Da.s    so gewonnene     Enolpropionat    des       Testosteron-propionates    bildet     Kristalle    vom  F. 125-127  . Mit     Tetranitromethan    färbt es  sich intensiv braun.  



  Das neue     Enolderivat    soll therapeutische       Verwendung    finden oder als Zwischenpro  dukt zur Gewinnung     therapeutisch        wirLamer     Verbindungen dienen.    <I>Beispiel:</I>    0,1 Teile     Testosteronpropionat    werden mit  4 Teilen     Propionsäureanhydrid    und 0,2 Tei  len wasserfreiem     Natriumpropionat    während  5 Stunden am     Rückfluss    gekocht.

   Das nach  dem     Abdestillieren        d.es        Propionsäureanhydri-          des    im Vakuum erhaltene     Reaktionsprodukt       wird aus verdünntem Alkohol beim Abkühlen       kristallin    gewonnen. Nach     Umlösen    aus Me  thanol     schmilzt    es bei     125-I27      und gibt  mit     Tetranitromethan    eine Braunfärbung.  



       Man    kann an Stelle von     Natriumpropionat     auch ein anderes Salz der     Propionsäure    ver  wenden oder ohne Zusatz eines solchen ar  beiten.  



       Denselben        Endstoff    erhält man auch  durch Kochen von     Testosteronpropionat,    zum  Beispiel mit     Propionylchlorid,    in einem orga  nischen     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 dioate containing the sterol core. The subject matter of the present invention is a method for the preparation of a new enol derivative containing the sterol core, which is characterized in that a propionylating agent is allowed to act on d 4,5 - testosterone -17 - propionate.



       The enol propionate of testosterone propionate thus obtained forms crystals of F. 125-127. With tetranitromethane it turns an intense brown.



  The new enol derivative is intended to be used therapeutically or as an intermediate product to obtain therapeutically effective compounds. <I> Example: </I> 0.1 parts of testosterone propionate are refluxed with 4 parts of propionic anhydride and 0.2 parts of anhydrous sodium propionate for 5 hours.

   The reaction product obtained after the propionic anhydride has been distilled off in vacuo is obtained in crystalline form from dilute alcohol on cooling. After dissolving from methanol, it melts at 125-127 and turns brown with tetranitromethane.



       Instead of sodium propionate, another salt of propionic acid can also be used or work without the addition of such a salt.



       The same end product is obtained by boiling testosterone propionate, for example with propionyl chloride, in an organic solvent such as gasoline until the reaction is complete. Furthermore, you can bind the hydrochloric acid formed to. Example a tertiary base such as pyridine and. like that, admit.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines neuen, den Sterinkern enthaltenden Enolderivates, dadurch gekennzeichnet, dass man auf 44,5- Testosteron-17-propionat ein propionylieren- des Mittel einwirken lässt. Das so gewonnene Enolpropionat des Testosteron-propionates bildet Kristalle vom F. 125-127 . PATENT CLAIM: Process for the preparation of a new enol derivative containing the sterol core, characterized in that a propionylating agent is allowed to act on 44,5-testosterone-17-propionate. The enol propionate of testosterone propionate obtained in this way forms crystals of F. 125-127. Mit Tetranitromethan färbt es sich intensiv braun. Das neue Enolderivat soll therapeutische Verwendung finden oder als Zwischenpro dukt zur Gewinnung therapeutisch wirksamer Verbindung dienen. UNTERANSPRÜCHE: 1. With tetranitromethane it turns an intense brown. The new enol derivative is intended to be used therapeutically or as an intermediate product to obtain therapeutically effective compounds. SUBCLAIMS: 1. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man als pro- pionylierendes Mittel Propionsäureanhydrid verwendet. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man als pro- pionylierendes Mittel ein Halobenid der Pro- pionsä.ure verwendet. Process according to patent claim, characterized in that propionic anhydride is used as the propionylating agent. Process according to patent claim, characterized in that a halobide of propionic acid is used as the propionylating agent. Verfahren nach Patentanspruch und Unteranspruch \?. dadurch gekennzeichnet, dass man in Anwesenheit eines säurebinden den :Mittels arbeitet. 4. Verfahren nach Patentanspruch und den Unteransprüchen ? und 3, dadurch ge kennzeichnet, dass man als säurebindendes Mittel eine tertiäre Base verwendet. 5. Method according to patent claim and subclaim \ ?. characterized in that one works in the presence of an acid-binding agent. 4. Method according to claim and the subclaims? and 3, characterized in that a tertiary base is used as the acid-binding agent. 5. Verfahren nach Patentanspruch und den Unteransprüchen \?, 3 und 4, dadurch gekennzeichnet, da,ss man als säurebindendes Mittel Pyridin verwendet. Process according to patent claim and the dependent claims 3 and 4, characterized in that the acid-binding agent used is pyridine.
CH215550D 1936-05-18 1936-05-18 Process for the preparation of a new enol derivative containing the sterol core. CH215550A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH211649T 1936-05-18
CH215550T 1936-05-18

Publications (1)

Publication Number Publication Date
CH215550A true CH215550A (en) 1941-06-30

Family

ID=25725034

Family Applications (1)

Application Number Title Priority Date Filing Date
CH215550D CH215550A (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) CH215550A (en)

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