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CH210770A - 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
CH210770A
CH210770A CH210770DA CH210770A CH 210770 A CH210770 A CH 210770A CH 210770D A CH210770D A CH 210770DA CH 210770 A CH210770 A CH 210770A
Authority
CH
Switzerland
Prior art keywords
oxidizing agent
ester
preparation
process according
oxyketone
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 CH210770A publication Critical patent/CH210770A/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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Steroid Compounds (AREA)

Description

  

  Verfahren zur Darstellung eines     Oxyhetonesters    der     Androstanreihe.       Es wurde gefunden, dass man zu einem       Ogyketonester    der     Androstanreihe    gelangen  kann, wenn man auf ein     Androstandiol-          (3,17)-17-monopropionat    der Formel  
EMI0001.0007     
    ein     Oxydationsmittel    einwirken lässt.  



  Das so gewonnene     Androstanol-(17)-on-          (3)-propionat    der Formel  
EMI0001.0011     
    bildet farblose Kristalle vom F.     121-121,5'.       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        Acylhydrazi-          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,       Permanganat    und dergleichen.  



       Die        erhaltene    Verbindung zeichnet sich  durch hohe Wirksamkeit am     Kapaunenkamm     und an der Samenblase aus. Sie     ,soll        thera-          peutieche    Verwendung     finden.              Beispiel:

       Zu einer Lösung von<B>3,6</B> g     Androstan-3-          trans    - 17 -     trane    -     diol    -17 -     monopropionat    in  50 cm' Eisessig gibt man in der Kälte eine  solche von 1,0 g     Chromtrioxyd    in 30 cm'  90 ö     iger    Essigsäure und lässt das Ganze  24 Stunden     bei        Zimmertemperatur        stehen.     Dann wird mit 1 Liter     Waseer    verdünnt,  das ausgefallene Produkt abgesaugt, mit  Wasser nachgewaschen und getrocknet.     :

  Ulan     erhält so das nach     Umkristallisation    aus       Hexan    bei     121-1291,5'    schmelzende     Andro-          stanol-(17)-on-(3)-propionat,    das sich zum       Beispiel    auch über das schwer lösliche     Semi-          carbazon    isolieren und reinigen lässt.  



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



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



  Process for the preparation of an oxyhetonester of the androstane series. It has been found that an ogyketone ester of the androstane series can be obtained if one uses an androstanediol (3,17) -17-monopropionate of the formula
EMI0001.0007
    allows an oxidizing agent to act.



  The androstanol- (17) -one- (3) -propionate of the formula obtained in this way
EMI0001.0011
    forms colorless crystals of F. 121-121.5 '. Experiments have shown that it is easy to separate the oxyketone ester in pure form either by direct crystallization or by preparing poorly soluble derivatives.

   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, and also copper oxide, permanganate and the like.



       The compound obtained is characterized by its high effectiveness on the capon comb and on the seminal vesicle. It should be used therapeutically. Example:

       To a solution of <B> 3.6 </B> g androstane-3-trans-17-trane-diol -17-monopropionate in 50 cm 'glacial acetic acid, a solution of 1.0 g chromium trioxide in 30 is added in the cold cm '90 ° acetic acid and leave the whole thing 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. :

  Ulan thus receives the androstanol- (17) -one- (3) -propionate, which melts at 121-1291.5 'after recrystallization from hexane 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)

<B>PATENTANSPRUCH:</B> Verfahren zur Darstellung eines neuen Oxyli:etonesters der Androstanreihe, dadurch gekennzeichnet, dass man auf ein Androstan- diol-(3,17)-17-monopropionat der Formel EMI0002.0030 ein Oxydationsmittel einwirken lässt. Das so gewonnene Androstanol-(17)-on- (3)-propionat der Formel EMI0002.0033 bildet farblose Kristalle vom F.121-1\21,5\'. Die erhaltene Verbindung zeichnet sich durch hohe Wirksamkeit am Kapaunenkamm und an der Samenblase aus. Sie soll thera peutische Verwendung finden. <B> PATENT CLAIM: </B> Process for the preparation of a new Oxyli: etonic ester of the androstane series, characterized in that an androstanediol- (3,17) -17-monopropionate of the formula EMI0002.0030 allows an oxidizing agent to act. The androstanol- (17) -one- (3) -propionate of the formula obtained in this way EMI0002.0033 forms colorless crystals of F.121-1 \ 21.5 \ '. The compound obtained is characterized by its high effectiveness on the capon comb and on the seminal vesicle. It should find therapeutic use. U \ TERAN SPRü CHE 1. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man als Oxydations mittel Chromsäure verwendet. 2. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man als Oxydations mittel ein Permanganat verwendet. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man als Oxydations mittel Kupferoxyd verwendet. 4. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man den Endstoff durch direkte Kristallisation reinigt. 5. U \ TERAN SPRü CHE 1. Process according to claim, characterized in that chromic acid is used as the oxidizing agent. 2. The method according to claim, characterized in that a permanganate is used as the oxidizing agent. Process according to claim, characterized in that copper oxide is used as the oxidizing agent. 4. The method according to claim, 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 patent claim, characterized in that the end product is purified by reaction with ketone reagents and subsequent hydrolytic cleavage of the reaction product.
CH210770D 1935-06-18 1935-06-18 Process for the preparation of an oxyketone ester of the androstane series. CH210770A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH208082T 1935-06-18
CH210770T 1935-06-18

Publications (1)

Publication Number Publication Date
CH210770A true CH210770A (en) 1940-07-31

Family

ID=25724488

Family Applications (1)

Application Number Title Priority Date Filing Date
CH210770D CH210770A (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) CH210770A (en)

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