CH215549A - 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
CH215549A
CH215549A CH215549DA CH215549A CH 215549 A CH215549 A CH 215549A CH 215549D A CH215549D A CH 215549DA CH 215549 A CH215549 A CH 215549A
Authority
CH
Switzerland
Prior art keywords
preparation
acid
derivative containing
enol derivative
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 CH215549A publication Critical patent/CH215549A/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     Enolderivates.       Gegenstand der vorliegenden Erfindung  bildet ein Verfahren zur Darstellung eines  neuen, den     Sterinkern    enthaltenden     Enol-          derivates,    welches dadurch gekennzeichnet  ist,     da.ss    man auf 4     4,5    -Testosteron -17     -          acetat    ein     propionylierendes    Mittel einwirken  lässt.  



  Das so gewonnene     Enolpropionat    des       Testosteronacetates    bildet Kristalle vom  F. 139,5-141  . Mit     Tetranitromethan    färbt  es sich intensiv braun.  



  Das neue     Enolderivat    soll therapeutische  Verwendung finden oder als Zwischenpro  dukt zur Gewinnung     therapeutisch        wirksamer     Verbindungen dienen.  



       Beispiel:     0,5 Teile     Testosteronacetat    werden mit  0,5     Teilen    wasserfreiem     Natriumpropionat    in  20     Teilen        Propionsäureanhydrid    während  6 Stunden zum Sieden erhitzt. Nach Ab  destillieren des     Propionsäureanhydrides    im  Vakuum bringt man das Reaktionsprodukt    durch Aufnehmen in heissem,     wässrigem    Al  kohol und Abkühlen zum     Kristallisieren.    Es  wird hierauf ans Methanol umgelöst     und     schmilzt bei 139,5-141  .

   Mit     Tetranitro-          metha.n    gemischt tritt starke     Braunfärbung     auf.  



  Man kann an Stelle von     Natriumapropio-          nat    auch     ein        anderes    Salz der     Propionsäure     verwendet oder ohne Zusatz eines solchen ar  beiten.  



  Denselben     Endstoff    erhält man auch  durch Kochen von     Testosteronacetat,    zum  Beispiel mit     Propionylchlorid,    in einem orga  nischen     Lösungsmittel,    wie Benzin, bis zur       vollendeten        Reaktion.    Ferner kann man 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 nucleus, which is characterized in that a propionylating agent is allowed to act on 4 4,5-testosterone-17-acetate.



  The enol propionate of testosterone acetate obtained in this way forms crystals of F. 139.5-141. With tetranitromethane it turns an intense brown.



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



       Example: 0.5 part of testosterone acetate is heated to boiling with 0.5 part of anhydrous sodium propionate in 20 parts of propionic anhydride for 6 hours. After the propionic anhydride has been distilled off in vacuo, the reaction product is crystallized by being taken up in hot, aqueous alcohol and cooled. It is then redissolved in methanol and melts at 139.5-141.

   When mixed with tetranitomethane, a strong brown color appears.



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



  The same end product is also obtained by boiling testosterone acetate, for example with propionyl chloride, in an organic solvent such as gasoline until the reaction is complete. Furthermore, 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- flVestosteron-1?-a,etat ein propionylierendes Mittel einwirken lässt. Das so gewonnene Enolpropionat des Testosteronacetates bildet Kristalle vom F. 139,5-141 . Mit Tetranitromethan färbt. 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 d4.5-flVestosterone-1? -A, etat. The enol propionate of testosterone acetate obtained in this way forms crystals of F. 139.5-141. Stains with tetranitromethane. es sich intensiv braun. Das neue Enolderivat soll therapeutische Verwendung finden oder als Zwischenpro dukt =Gewinnung therapeutisch wirksamer Verbindung dienen. UNTERANSPRüCHE 1. Verfahren nach Patentanspruah, da durch gekennzeichnet, dass man als pro- pionylierendes Mittel Propionsäureanhydri.d verwendet. 2. it turns intense brown. The new enol derivative is intended to be used therapeutically or as an intermediate product = to obtain a therapeutically effective compound. SUBClaims 1. Process according to patent claim, characterized in that propionic anhydride is used as the propionylating agent. 2. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man als pro- pionylierendes Mittel ein Halogenid der Pro- pionsäure verwendet. . Verfahren nach Patentanspruch und Unteranspruch ?, dadurch gekennzeichnet, dass man in Anwesenheit eines säurebinden den Mittels arbeitet. 4. 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 gekennzeichnet, dass man als säurebindendes Mittel Pyridin verwendet. Process according to patent claim, characterized in that a halide of propionic acid is used as the propionylating agent. . Method according to patent claim and dependent claim?, Characterized in that one works in the presence of an acid-binding agent. 4. The method according to 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 subclaims 2, 3 and 4, characterized in that the acid-binding agent used is pyridine.
CH215549D 1936-05-18 1936-05-18 Process for the preparation of a new enol derivative containing the sterol core. CH215549A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH215549T 1936-05-18
CH211649T 1936-05-18

Publications (1)

Publication Number Publication Date
CH215549A true CH215549A (en) 1941-06-30

Family

ID=25725033

Family Applications (1)

Application Number Title Priority Date Filing Date
CH215549D CH215549A (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) CH215549A (en)

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