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CH210771A - Process for the preparation of an oxyketone ester of the androstane series. - Google Patents

Process for the preparation of an oxyketone ester of the androstane series.

Info

Publication number
CH210771A
CH210771A CH210771DA CH210771A CH 210771 A CH210771 A CH 210771A CH 210771D A CH210771D A CH 210771DA CH 210771 A CH210771 A CH 210771A
Authority
CH
Switzerland
Prior art keywords
oxidizing agent
ester
oxyketone
preparation
butyrate
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 CH210771A publication Critical patent/CH210771A/en

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
    • 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)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

  

      Verfahren    zur Darstellung eines     Ogyketonesters    der     Androstanreihe.       Es wurde gefunden, dass man zu einem       Oxyketonester    der     Androstanreihe    gelangen  kann, wenn man auf ein     Androstan.diol-          (3,17)-17-n-butyrat    der Formel  
EMI0001.0008     
    ein Oxydationsmittel einwirken lässt.

      Das so gewonnene     Androstanol-(17)-on-          (3)-n-butyrat    der Formel  
EMI0001.0011     
         kristallisiert    in     dimorphen    Formen der  Schmelzpunkte<B>90,5-91'</B>     resp.        100-101'.       Wie     Versuche    ergaben, gelingt     es    leicht,  den     Oxyketonester    entweder. durch direkte  Kristallisation oder durch Bereitung schwer  löslicher     Derivate    in reiner     Form    abzuschei  den.

   Solche schwer lösliche Derivate erhält  man zum Beispiel durch Umsetzung des     Oxy-          ketonesters    mit :den     üblichen        Ketonreagen-          zien    wie     Semicarbazid,        Thiosemicarbazid,          Hydroxylamin,        Aminoguanidin,        Phenylhydra-          zinen,

      neutralen oder     basischen        Acylhydra.zi-          den.    Durch     Einwirkung    hydrolytisch wirken  der     Mittel    werden die zwecks     Reinigung    des       Oxyketonesters    hergestellten Verbindungen  wieder in ihre Komponenten gespalten.  



  Geeignete     Oxydationsmittel    sind zum  Beispiel 6wertige Chromverbindungen wie  Chromsäure in Eisessig, ferner Kupferoxyd,       Permanganate    und dergleichen.  



  Die erhaltene Verbindung zeichnet sich  durch hohe Wirksamkeit am     Kapaunenkamm     und an der Samenblase aus. Sie soll thera  peutische Verwendung finden.           'Beispiel:     Zu einer Lösung von 3,8g     Androstan-3-          trans-17-trans-diol-17-n-butyrat    in 50 cm'       Eisessig    gibt man in der Kälte eine solche  von 1,0 g     Chromtrioxyd    in 30 cm' 901357<I>irr</I>e<B>r</B>  Essigsäure und lässt das Ganze     24    Stunden  bei     Zimmertemperatur    stehen.

   Dann wird mit  1 Liter Wasser verdünnt, das ausgefallene  Produkt abgesaugt, mit Wasser nach  gewaschen und     getrocknet.    Man erhält so das  nach     Umkristallisation    aus verdünntem Me  thanol in     dimorphen    Formen schmelzende       Androstanol-(17)-on-(3)-n-butyrat,    das sich  zum     Beispiel    auch über das ,schwer lösliche       Semicarbazon    isolieren und reinigen lässt.  



  Statt von der     3-trans-Verbindung    kann  man     ebensogut    von der     3-eis-Verbindung    aus  gehen.  



  An Stelle von Chromsäure kann zur Oxy  dation zum Beispiel auch Kupferoxyd Ver  wendung finden.



      Process for the preparation of an ogyketone ester of the androstane series. It has been found that an oxyketonic ester of the androstane series can be obtained if one uses an androstane diol (3,17) -17-n-butyrate of the formula
EMI0001.0008
    allows an oxidizing agent to act.

      The androstanol- (17) -one- (3) -n-butyrate of the formula obtained in this way
EMI0001.0011
         crystallizes in dimorphic forms with melting points <B> 90.5-91 '</B> resp. 100-101 '. As experiments have shown, it is easy to either use the oxyketone ester. by direct crystallization or by preparing poorly soluble derivatives in pure form.

   Such poorly soluble derivatives are obtained, for example, by reacting the oxy ketone ester with: the usual ketone reagents such as semicarbazide, thiosemicarbazide, hydroxylamine, aminoguanidine, phenylhydrazines,

      neutral or basic acylhydrazides. When the agents act hydrolytically, the compounds produced for the purpose of cleaning the oxyketone ester are split back into their components.



  Suitable oxidizing agents are, for example, hexavalent chromium compounds such as chromic acid in glacial acetic acid, as well as copper oxide, permanganates and the like.



  The compound obtained is characterized by its high effectiveness on the capon comb and on the seminal vesicle. It should find therapeutic use. Example: To a solution of 3.8 g of androstane-3-trans-17-trans-diol-17-n-butyrate in 50 cm 'of glacial acetic acid, a solution of 1.0 g of chromium trioxide in 30 cm' 901357 is added in the cold <I> irr </I> e <B> r </B> acetic acid and leave the whole thing to stand for 24 hours at room temperature.

   It is then diluted with 1 liter of water, and the precipitated product is filtered off with suction, washed with water and dried. This gives androstanol- (17) -one- (3) -n-butyrate, which melts in dimorphic forms after recrystallization from dilute methanol and which can also be isolated and purified, for example, via the sparingly soluble semicarbazone.



  Instead of the 3-trans connection, one can just as well start from the 3-cis connection.



  Instead of chromic acid, for example, copper oxide can also be used for oxidation.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines neuen Oxyketonesters der Androstanreihe, dadurch gekennzeichnet, dass man auf ein Androstan- diol-(3,17)-17-n-butyrat der Formel EMI0002.0022 ein Oxydationsmittel einwirken lässt. PATENT CLAIM: Process for the preparation of a new oxyketone ester of the androstane series, characterized in that an androstanediol (3,17) -17-n-butyrate of the formula EMI0002.0022 allows an oxidizing agent to act. Das so gewonnene Androstanol-(17)-on- (3)-n-butyrat der Formel EMI0002.0026 kristallisiert in dimorphen Formen der Schmelzpunkte 90,15-91' reep. 100-101'. Die erhaltene Verbindung zeichnet sich durch hohe Wirksamkeit am Kapaunenkamm und an der Samenblase aus. Sie soll thera peutische Verwendung finden. UNTERANSPRÜCHE: 1. The androstanol- (17) -one- (3) -n-butyrate of the formula obtained in this way EMI0002.0026 crystallizes in dimorphic forms with melting points 90.15-91 'reep. 100-101 '. The compound obtained is characterized by its high effectiveness on the capon comb and on the seminal vesicle. It should find therapeutic use. SUBCLAIMS: 1. Verfahren nach Patentansprueh, dadurch gekennzeichnet, dass man als Oxydations mittel Chromsäure verwendet. \?. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man als Oxydations mittel ein Permanganat verwendet. B. Verfahren nach Patentansprucb, dadurch gekennzeichnet, dass man als Oxydations mittel Kupferoxyd verwendet. 4. Verfahren nach Patentanispruc .h, dadurch gekennzeichnet, dass man den Endstoff durch direkte Kristallisation reinigt. 5. Process according to patent claim, characterized in that chromic acid is used as the oxidizing agent. \ ?. Method according to claim, characterized in that a permanganate is used as the oxidizing agent. B. The method according to patent claims, characterized in that copper oxide is used as the oxidizing agent. 4. The method according to patent anispruc .h, characterized in that the end product is purified by direct crystallization. 5. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man den Endstoff durch Umsetzung mit Ketonreagenzien und anschliessende hydrolytische .Spaltung des Reaktionsproduktes reinigt. Process according to claim, characterized in that the end product is purified by reaction with ketone reagents and subsequent hydrolytic cleavage of the reaction product.
CH210771D 1935-06-18 1935-06-18 Process for the preparation of an oxyketone ester of the androstane series. CH210771A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH208082T 1935-06-18
CH210771T 1935-06-18

Publications (1)

Publication Number Publication Date
CH210771A true CH210771A (en) 1940-07-31

Family

ID=25724489

Family Applications (1)

Application Number Title Priority Date Filing Date
CH210771D CH210771A (en) 1935-06-18 1935-06-18 Process for the preparation of an oxyketone ester of the androstane series.

Country Status (1)

Country Link
CH (1) CH210771A (en)

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