CH232489A - Process for the production of an estrogenic substance. - Google Patents

Process for the production of an estrogenic substance.

Info

Publication number
CH232489A
CH232489A CH232489DA CH232489A CH 232489 A CH232489 A CH 232489A CH 232489D A CH232489D A CH 232489DA CH 232489 A CH232489 A CH 232489A
Authority
CH
Switzerland
Prior art keywords
production
ethane
phenyl
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 CH232489A publication Critical patent/CH232489A/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
    • 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
    • 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. ä     -Di-(p-propogy-phenyl)-          a   <I>. a</I>     =di-äthyl-äthans,    das dadurch gekenn  zeichnet ist, dass man auf a .     a,'-Di-(p-ogy-          phenyl)-a    .

   ä     -di-äthyl-äthan    ein     propionylie-          iendes        Mittel        einwirken    lässt.  



  Als     propionylierende    Mittel können     Pro-          pionsäure,    ihr     Anhydrid    oder     Propionsäure-          halogenide        Verwendung        finden.            Beispiel:     Eine Lösung von 5 g<I>a. ä</I>     -Di-(p-ogy-phe-          nyl)-a    . ä     -di-äthyl-äthan    in 50     cm@    trockenem       Pyridin    wird mit 7 g     Propionsäureanhydrid     vermischt und während 2 Tagen bei Zimmer  temperatur stehen gelassen.

   Das     Pyridin        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 zu  rückbleibende     Dipropionat    liefert nach Um  kristallisieren aus Methylalkohol 7,4 g farb  lose, kleine Stäbchen vom     Smp.    125  C. Die       oestrogene        Wirkung    an der kastrierten weib  lichen Ratte beträgt etwa<I>2 y.</I>



  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 for the production of medicaments a. - Di (p-propogy-phenyl) - a <I>. a </I> = di-ethyl-ethane, which is characterized by the fact that one clicks on a. a, '- di- (p-ogy-phenyl) -a.

   ä -di-ethyl-ethane allows a propionylating agent to act.



  Propionic acid, its anhydride or propionic acid halides can be used as propionylating agents. Example: A solution of 5 g <I> a. ä </I> -Di- (p-ogy-phenyl) -a. ä -di-ethyl-ethane in 50 cm @ dry pyridine is mixed with 7 g of propionic 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, then with water, dried and evaporated. After recrystallization from methyl alcohol, the remaining dipropionate provides 7.4 g of colorless, small rods with a melting point of 125 C. The estrogenic effect on the castrated female rat is about <I> 2 y. </I>

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von a . ä -Di- (p-propogy-phenyl)-a . a'-di-äthyl-äthan, da durch gekennzeichnet, dass man auf<I>a . ä</I> -Di- (p-ogy-phenyl)-a . a'-di-äthyl-äthan ein pro- pionylierendes Mitteleinwirken lässt. PATENT CLAIM: Process for the production of a. ä -Di- (p-propogy-phenyl) -a. a'-di-ethyl-ethane, as characterized by the fact that one clicks on <I> a. ä </I> -Di- (p-ogy-phenyl) -a. a'-di-ethyl-ethane allows a propionylating agent to act. Die neue Verbindung besitzt nach dem Umkristallisieren aus Methylalkohol die Form farbloser kleiner Stäbchen vom Smp. 125 C. UNTERANSPRUCH: Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man als propionylieren- des Mittel Propionsäureanhydrid verwendet. After recrystallization from methyl alcohol, the new compound has the form of colorless small rods with a melting point of 125 C. SUBSTANTIAL CLAIM: Process according to patent claim, characterized in that propionic anhydride is used as the propionylating agent.
CH232489D 1938-08-29 1939-08-28 Process for the production of an estrogenic substance. CH232489A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE232489X 1938-08-29
CH223951T 1939-08-28

Publications (1)

Publication Number Publication Date
CH232489A true CH232489A (en) 1944-05-31

Family

ID=25726759

Family Applications (1)

Application Number Title Priority Date Filing Date
CH232489D CH232489A (en) 1938-08-29 1939-08-28 Process for the production of an estrogenic substance.

Country Status (1)

Country Link
CH (1) CH232489A (en)

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