CH232491A - Process for the production of an estrogenic substance. - Google Patents

Process for the production of an estrogenic substance.

Info

Publication number
CH232491A
CH232491A CH232491DA CH232491A CH 232491 A CH232491 A CH 232491A CH 232491D A CH232491D A CH 232491DA CH 232491 A CH232491 A CH 232491A
Authority
CH
Switzerland
Prior art keywords
production
butyrylating
ethane
ethyl
estrogenic substance
Prior art date
Application number
Other languages
German (de)
Inventor
Ag Schering
Original Assignee
Ag Schering
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 Ag Schering filed Critical Ag Schering
Publication of CH232491A publication Critical patent/CH232491A/en

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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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
    • C07C69/22—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety
    • C07C69/28—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety esterified with dihydroxylic compounds
    • 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)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Description

  

  Verfahren zur Herstellung eines     oestrogenen        Stoffes.       Gegenstand des vorliegenden Patentes ist  ein Verfahren zur Herstellung des     oestrogen     wirksamen, als Arzneimittel und Zwischen  produkt zur Herstellung von Arzneimitteln  verwendbaren a.     a'-Di-(p-n-butyroxy-phenyl)-          a   <I>. ä</I>     -di-äthyl-äthans,    das     dadurch    gekenn  zeichnet ist, dass man auf<I>a . ä</I>     -Di-(p-oxy-          phenyl)-a    .

       a'-di-äthyl-äthan    ein     n-butyrylie-          rendes    Mittel     einwirken    lässt.  



  Als     n-butyrylierende    Mittel     eignen    sich       n-Buttersäure,    ihr     Anhydrid    oder     n-Butter-          säurehalogenide.     



       Beispiel:     Eine Lösung von 5 g a . a'-     Di    - (p -     oxy-          phenyl)-a    .     a'-di-äthyl-äthan    in 50     cm@        trok-          kenem        Pyridin    wird mit 7 g     n-Buttersäure-          anhydrid    vermischt und während 2 Tagen bei       Zimmertemperatur    stehen gelassen. Das     Py-          ridin    wird dann im Vakuum     entfernt    und der  feste Rückstand in Äther aufgenommen.

   Die  ätherische Lösung wird zunächst mit 5 %     iger     Natronlauge, dann mit Wasser ausgeschüt  telt, getrocknet und eingedampft. Das zurück-    bleibende     Di-n-butyrat    liefert nach     Umkri-          stallisieren    aus Methylalkohol farblose Kri  stalle vom     Smp.    105 bis 108 . Die     oestrogene          Wirkung    an der kastrierten weiblichen Ratte  beträgt etwa 1,8 y.



  Process for the production of an estrogenic substance. The subject of the present patent is a process for the production of the estrogenic, usable as a medicament and intermediate product for the production of medicaments a. a'-di- (p-n-butyroxy-phenyl) - a <I>. ä </I> -di-äthyl-äthans, which is characterized by the fact that one clicks on <I> a. ä </I> -Di- (p-oxyphenyl) -a.

       a'-di-ethyl-ethane allows an n-butyrylating agent to act.



  Suitable n-butyrylating agents are n-butyric acid, its anhydride or n-butyric acid halides.



       Example: A solution of 5 g a. a'- di - (p - oxyphenyl) -a. a'-Di-ethyl-ethane in 50 cm @ dry pyridine is mixed with 7 g of n-butyric anhydride and left to stand for 2 days at room temperature. The pyridine is then removed in vacuo and the solid residue is taken up in ether.

   The ethereal solution is first extracted with 5% sodium hydroxide solution and then with water, dried and evaporated. The remaining di-n-butyrate, after recrystallization from methyl alcohol, gives colorless crystals with a melting point of 105 to 108. The estrogenic effect on the castrated female rat is about 1.8 y.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von<I>a . ä</I> -Di- (p-n-butyroxy-phenyl)-a. ä -,di-äthyl-äthan, dadurch gekennzeichnet, däss man auf<I>a. ä</I> - Di-(p-oxy-phenyl)-a ..ä -di-äthyl-äthan ein n- butyrylierendes Mittel einwirken lässt. Die neue Verbindung besitzt nach dem Umkristallisieren aus Methylalkohol die Form farbloser Kristalle vom Smp. 105 bis 108 . PATENT CLAIM: Process for the production of <I> a. ä </I> -Di- (p-n-butyroxy-phenyl) -a. ä -, di-ethyl-ethane, characterized in that on <I> a. ä </I> - Di- (p-oxy-phenyl) -a ..ä -di-ethyl-ethane allows an n-butyrylating agent to act. After recrystallization from methyl alcohol, the new compound has the form of colorless crystals with a melting point of 105 to 108. UNTERANSPRUCH: Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man als n-butyrylieren- des Mittel n-Buttersäureanhydrid verwendet. SUBSTANTIAL CLAIM: Process according to patent claim, characterized in that n-butyric anhydride is used as the n-butyrylating agent.
CH232491D 1938-08-29 1939-08-28 Process for the production of an estrogenic substance. CH232491A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE232491X 1938-08-29
CH223951T 1939-08-28

Publications (1)

Publication Number Publication Date
CH232491A true CH232491A (en) 1944-05-31

Family

ID=25726761

Family Applications (1)

Application Number Title Priority Date Filing Date
CH232491D CH232491A (en) 1938-08-29 1939-08-28 Process for the production of an estrogenic substance.

Country Status (1)

Country Link
CH (1) CH232491A (en)

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