CH201536A - Process for the preparation of a new ester. - Google Patents

Process for the preparation of a new ester.

Info

Publication number
CH201536A
CH201536A CH201536DA CH201536A CH 201536 A CH201536 A CH 201536A CH 201536D A CH201536D A CH 201536DA CH 201536 A CH201536 A CH 201536A
Authority
CH
Switzerland
Prior art keywords
preparation
water
androstenol
new
ester
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 CH201536A publication Critical patent/CH201536A/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)

Description

  

  Verfahren zur Darstellung eines neuen Esters.    Gegenstand des vorliegenden Patentes       bildet    ein Verfahren zur Darstellung eines  neuen     Esters,    welches dadurch gekennzeich  net ist, dass man     44,5-Androstenol-(17)-on-(3)     mit einem     Mol        Phosphorogyhalogenid    umsetzt  und auf das     Reaktionsprodukt    Wasser ein  wirken lässt.  



  Der so gewonnene     44,5        Androstenol-(17)-          on-(3)-monophosphorsäureester    der Formel  
EMI0001.0010     
    hat den F.<B>150'.</B> Seine     Alkalisalze,    sowie  auch sein Ammonium- und     Triäthanolamin-          salz    sind     in    Wasser leicht löslich.  



  Die neue     Verbindung    soll therapeutische  Verwendung finden.    <I>Beispiel:</I>    1,0 g Testosteron werden in 10,0 cm' abso  lutem     Pyridin    gelöst und 0,54 g     frisch        destil-          liertes        Phosphorogychlorid    hinzugegeben, wo  bei     Erwärmung        eintritt.    Nach     etwa        22stün-          digem    Stehen bei     Zimmertemperatur    wird das  Reaktionsgemisch in Wasser gegossen.

   Beim       Ansäuern    der Lösung     mit    verdünnter Salz  säure scheidet sich der     Testosteron-mono-          phosphorsäureester    vom F.<B>150'</B> aus. Er wird       abfiltriert,    mit Wasser gewaschen und im  Vakuum getrocknet.  



  An Stelle von     Phosphorogychlorid    kann  man zum Beispiel auch     Phosphorogybromid          verwenden.  



  Process for the preparation of a new ester. The subject of the present patent is a process for the preparation of a new ester, which is characterized in that 44,5-androstenol- (17) -one- (3) is reacted with one mole of phosphorogyhalide and water is allowed to act on the reaction product.



  The 44.5 androstenol- (17) -on- (3) -monophosphoric acid ester of the formula obtained in this way
EMI0001.0010
    has the F. <B> 150 '. </B> Its alkali salts, as well as its ammonium and triethanolamine salts, are easily soluble in water.



  The new compound should find therapeutic use. <I> Example: </I> 1.0 g of testosterone are dissolved in 10.0 cm of absolute pyridine and 0.54 g of freshly distilled phosphorogychloride are added, which occurs when heated. After standing for about 22 hours at room temperature, the reaction mixture is poured into water.

   When the solution is acidified with dilute hydrochloric acid, the testosterone monophosphoric acid ester is separated from the F. <B> 150 '</B>. It is filtered off, washed with water and dried in vacuo.



  For example, phosphorogybromide can also be used instead of phosphorogychloride.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines neuen Esters, dadurch gekennzeichnet, dass man d4,5-Androstenol-(17)-on-(3) mit einem Mol Phosphoroxyhalogenid umsetzt und auf das Reaktionsprodukt Wasser einwirken lässt. Claim: Process for the preparation of a new ester, characterized in that d4,5-androstenol- (17) -one- (3) is reacted with one mole of phosphorus oxyhalide and water is allowed to act on the reaction product. Der so gewonnene 445- Androstenol-(17)- on@(3)-monophosphorsäureester der Formel EMI0002.0004 hat den F.<B>150'.</B> Seine Alkalisalze, sowie auch sein Ammonium- und Triäthanolamin- salz sind in Wasser leicht löslich. Die neue Verbindung soll therapeutische Verwendung finden. UNTERANSPRUCH: Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man in Gegenwart ter tiärer Basen arbeitet. The 445-androstenol- (17) -on @ (3) -monophosphoric acid ester of the formula obtained in this way EMI0002.0004 has the F. <B> 150 '. </B> Its alkali salts, as well as its ammonium and triethanolamine salts, are easily soluble in water. The new compound should find therapeutic use. SUBCLAIM: Process according to claim, characterized in that one works in the presence of tertiary bases.
CH201536D 1935-08-02 1935-08-02 Process for the preparation of a new ester. CH201536A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH201536T 1935-08-02
CH195775T 1935-08-02

Publications (1)

Publication Number Publication Date
CH201536A true CH201536A (en) 1938-11-30

Family

ID=25722795

Family Applications (1)

Application Number Title Priority Date Filing Date
CH201536D CH201536A (en) 1935-08-02 1935-08-02 Process for the preparation of a new ester.

Country Status (1)

Country Link
CH (1) CH201536A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2928849A (en) * 1953-11-20 1960-03-15 Leo Ab High-molecular weight derivatives of steroids containing hydroxyl groups and method of producing the same

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2928849A (en) * 1953-11-20 1960-03-15 Leo Ab High-molecular weight derivatives of steroids containing hydroxyl groups and method of producing the same

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