CH201951A - Process for the production of ethynyl androstenediol. - Google Patents

Process for the production of ethynyl androstenediol.

Info

Publication number
CH201951A
CH201951A CH201951DA CH201951A CH 201951 A CH201951 A CH 201951A CH 201951D A CH201951D A CH 201951DA CH 201951 A CH201951 A CH 201951A
Authority
CH
Switzerland
Prior art keywords
sep
acetylene
androstenediol
ethynyl
production
Prior art date
Application number
Other languages
German (de)
Inventor
Schering-Kahlbaum A G
Original Assignee
Schering Kahlbaum Ag
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 Schering Kahlbaum Ag filed Critical Schering Kahlbaum Ag
Publication of CH201951A publication Critical patent/CH201951A/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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

  Verfahren zur Herstellung von     Äthinyl-andr        ostendiol.       Vorliegende Erfindung betrifft ein Ver  fahren zur Herstellung von     Äthinyl-andro-          stendiol.    Dieses ist dadurch gekennzeichnet,  dass man auf     Dehydroandrosteron    Acetylen  einwirken lässt.  



  Die Behandlung mit dem Acetylen wird  mit Vorteil in Anwesenheit von     Alkalimetal-          len    wie Natrium oder     Lithium    usw. oder von       Alkaliverbindungen,    wie     Alkaliamiden,        Alko-          holaten    und     dergl.    durchgeführt.  



  Die neue Verbindung soll als Arzneimit  tel, sowie als Zwischenprodukt bei der Her  stellung von Arzneimitteln Verwendung fin  den.  



       Beispiel:     3,5 g Natrium werden     in        etwa    200 cm'  flüssigem     Ammoniak    unter     Kühlung    mit       Kohlensäureschnee    und Aceton gelöst. In die  tiefblaue Lösung wird Acetylen eingeleitet,  bis die blaue Farbe verschwunden ist. Nun  entfernt man die Kältemischung und gibt un  ter Rühren     eine        Lösung    von 5     g    Dehydro-         androsteron    in 40 ein' Benzol und 150     ein'     Äther hinzu. Man rührt noch 15 Stunden  weiter, wobei das Ammoniak verdampft.

    Nach dieser Zeit wird auf Eis gegossen,     aus-          geäthert    und der Äther mit verdünnter  Schwefelsäure und Wasser gewaschen. Den  Ätherrückstand nimmt man in Methanol auf  und gibt 3 g     Semicarbazidacetat    in Methanol       hinzu.    Es wird 1 Stunde zum schwachen Sie  den erwärmt und dann das ausgeschiedene       Semicarbazon        abfiltriert.    Die     Semicarbazon-          Mutterlauge        wird    in Wasser gegossen und       ausgeäthert,    der Äther mit Soda und Wasser  gewaschen und nach dem     Trocknen    ver  dampft.

   Den Rückstand kristallisiert man aus  Methanol um. Das erhaltene     Äthinylandro-          stendiol        schmilzt    bei 239  .



  Process for the production of ethynyl andr ostendiol. The present invention relates to a method for the production of ethynyl androstenediol. This is characterized by the fact that acetylene is allowed to act on dehydroandrosterone.



  The treatment with the acetylene is advantageously carried out in the presence of alkali metals such as sodium or lithium etc. or of alkali compounds such as alkali amides, alcoholates and the like.



  The new compound is intended to be used as a drug and as an intermediate in the manufacture of drugs.



       Example: 3.5 g of sodium are dissolved in about 200 cm 'of liquid ammonia while cooling with carbon dioxide snow and acetone. Acetylene is introduced into the deep blue solution until the blue color has disappeared. The freezing mixture is now removed and a solution of 5 g of dehydroandrosterone in 40% of benzene and 150% of ether is added with stirring. The mixture is stirred for a further 15 hours, the ammonia evaporating.

    After this time it is poured onto ice, extracted with ether and the ether washed with dilute sulfuric acid and water. The ether residue is taken up in methanol and 3 g of semicarbazide acetate in methanol are added. It is heated to the weak for 1 hour and then the semicarbazone which has separated out is filtered off. The semicarbazone mother liquor is poured into water and extracted with ether, the ether washed with soda and water and evaporated after drying.

   The residue is recrystallized from methanol. The ethinyland rustediol obtained melts at 239.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von Äthinyl- androstendiol, dadurch gekennzeichnet, dass man auf Dehydroandrosteron Acetylen ein- wirken lässt, EMI0002.0001 <U>Das</U> <SEP> so <SEP> erhaltene <SEP> Äthinvl-androstendiol <tb> bildet <SEP> bei <SEP> 239 <SEP> <SEP> schmelzende <SEP> @liristalle. <tb> Ii <SEP> 1 <SEP> TERAV <SEP> SPRüCHE <tb> ?. <SEP> Verfahren <SEP> nach <SEP> Pa.tentansprueh, <SEP> dadm-eh <tb> gekennzeichnet, <SEP> da.ss <SEP> die <SEP> Einwirkung <SEP> des <tb> Acetylens <SEP> in <SEP> Gegenwart <SEP> eines <SEP> Alkalimetal les <SEP> erfolgt. <tb> ?. PATENT CLAIM: Process for the production of ethynyl androstenediol, characterized in that acetylene is allowed to act on dehydroandrosterone, EMI0002.0001 <U> The </U> <SEP> <SEP> obtained in this way <SEP> Ethinvl-androstenediol <tb> forms <SEP> with <SEP> 239 <SEP> <SEP> melting <SEP> @liristalle. <tb> Ii <SEP> 1 <SEP> TERAV <SEP> SPARDS <tb>?. <SEP> procedure <SEP> according to <SEP> Pa.tentansprueh, <SEP> dadm-eh <tb> marked, <SEP> da.ss <SEP> the <SEP> action <SEP> des <tb> Acetylene <SEP> in the <SEP> presence <SEP> of an <SEP> alkali metal <SEP> takes place. <tb>?. <SEP> Verfahren <SEP> nach <SEP> Patentanspruch, <SEP> dadurch <tb> ,gekennzeichnet, <SEP> dass <SEP> die <SEP> Einwirkung <SEP> des <tb> Acetylens <SEP> in <SEP> Gegenwart <SEP> einer <SEP> Alkaliver Bindung <SEP> erfolgt. 3. Verfahren nach Patentanspruch und Un teranspruch 2, dadurch gekennzeichnet, dass die Einwirkung des Acetylens in Ge- genwart eines -1lkaliamides erfolgt. @. Verfahren nach Patentanspruch und Un teranspruch ?, dadurch gekennzeichnet, dass die Ein -,t-irkung des Acetylens in Ge genwart eines Alkalialkoholats erfolgt. <SEP> method <SEP> according to <SEP> patent claim, <SEP> thereby <tb>, marked, <SEP> that <SEP> is the <SEP> action <SEP> of the <tb> Acetylene <SEP> in the <SEP> presence <SEP> of an <SEP> alkaline bond <SEP> takes place. 3. The method according to patent claim and un teran claim 2, characterized in that the action of the acetylene takes place in the presence of a -1lkaliamides. @. Method according to claim and sub-claim?, Characterized in that the action of the acetylene takes place in the presence of an alkali metal alcoholate.
CH201951D 1935-11-22 1936-11-23 Process for the production of ethynyl androstenediol. CH201951A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR201951X 1935-11-22

Publications (1)

Publication Number Publication Date
CH201951A true CH201951A (en) 1938-12-31

Family

ID=8880062

Family Applications (1)

Application Number Title Priority Date Filing Date
CH201951D CH201951A (en) 1935-11-22 1936-11-23 Process for the production of ethynyl androstenediol.

Country Status (1)

Country Link
CH (1) CH201951A (en)

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