CH230441A - Process for the preparation of a new ester of the oxy-stilbene series. - Google Patents

Process for the preparation of a new ester of the oxy-stilbene series.

Info

Publication number
CH230441A
CH230441A CH230441DA CH230441A CH 230441 A CH230441 A CH 230441A CH 230441D A CH230441D A CH 230441DA CH 230441 A CH230441 A CH 230441A
Authority
CH
Switzerland
Prior art keywords
preparation
oxy
agent
new ester
diethyl
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 CH230441A publication Critical patent/CH230441A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • C07C69/78—Benzoic acid esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/205—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing only six-membered aromatic rings as cyclic parts with unsaturation outside the rings
    • C07C39/21—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing only six-membered aromatic rings as cyclic parts with unsaturation outside the rings with at least one hydroxy group on a non-condensed ring
    • C07C39/215—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing only six-membered aromatic rings as cyclic parts with unsaturation outside the rings with at least one hydroxy group on a non-condensed ring containing, e.g. diethylstilbestrol
    • 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/96—Esters of carbonic or haloformic acids

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

  

  Verfahren zur Darstellung eines neuen Esters der     Oxy-stilbenreihe.       Es wurde gefunden, dass man zu einem  neuen Ester gelangen kann, wenn man     a,a'-          Diäthyl-4,4'-dioxystilben    mit einem     n-valery-          lierenden    Mittel behandelt.  



  Geeignete     n-valerylierende    Mittel sind  zum Beispiel die     n-Valeriansäure    selbst, ihre       Halogenide    oder Ester mit niederen Alkoho  len (Umeiterung), ihr     Anhydrid    sowie auch  das von ihr abgeleitete     Keten.     



  Die neue Verbindung, das     a,ä        -Diäthyl-          4,4'-dioxystilben-di-n-valerianat,    schmilzt bei  76,5 bis 77,5 . Sie zeigt gegenüber den be  kannten hormonal wirksamen Verbindungen  ohne Steroidcharakter eine     protrahiertere     Wirkung im     Oestrus-    und     Uteruswachstums-          test    und soll deshalb therapeutische     Verwen-          dung    finden.  



  <I>Beispiel:</I>  Ein Gemisch von 1 Teil     a,a'-Diäthyl-4,4'-          dioxystilben,    15 Teilen     Pyridin    und 5     Teilen          n-Valeriansäureanhydrid    wird einige Zeit auf       120     erhitzt. Hierauf     lässt    man     erkalten    und    versetzt das Gemisch mit Wasser, wobei sich  ein     0'1    ausscheidet. Dieses wird     in    Äther auf  genommen und nacheinander mit     n-Schwefel-          säure,    Wasser und     n/10    Natronlauge gewa  schen.

   Nach     Abdunsten    des Äthers bleibt ein  01 zurück, das bald erstarrt. Der     Valerian-          säurediester    wird aus wässerigem Äthanol  umgelöst. F. 76,5 bis 77,5 .     01  



  Process for the preparation of a new ester of the oxy-stilbene series. It has been found that a new ester can be obtained if a, a'-diethyl-4,4'-dioxystilbene is treated with an n-valerating agent.



  Suitable n-valerylating agents are, for example, n-valeric acid itself, its halides or esters with lower alcohols (diversion), its anhydride and also the ketene derived from it.



  The new compound, the a, ä -diethyl 4,4'-dioxystilbene-di-n-valerianate, melts at 76.5 to 77.5. Compared to the known hormonally active compounds without steroid character, it shows a more protracted effect in the oestrus and uterus growth test and is therefore intended to be used therapeutically.



  <I> Example: </I> A mixture of 1 part of a, a'-diethyl-4,4'-dioxystilbene, 15 parts of pyridine and 5 parts of n-valeric anhydride is heated to 120 for some time. It is then allowed to cool and water is added to the mixture, a 0'1 being precipitated. This is absorbed in ether and washed successively with n-sulfuric acid, water and n / 10 sodium hydroxide solution.

   After the ether has evaporated, an 01 remains, which soon solidifies. The valeric acid diester is redissolved from aqueous ethanol. F. 76.5 to 77.5. 01

Claims (1)

PATENTANSPRUCH Verfahren zur Darstellung eines neuen Esters, dadurch gekennzeichnet, dass man a,a'-Diäthyl-4,4'-dioxystilben mit einem n- valerylierenden Mittel behandelt. Die neue Verbindung, das a,a'-Diäthyl- 4,4'-.dioxystilben-@di-n-valerianat, schmilzt bei 76,5 bis 77,5 . PATENT CLAIM Process for the preparation of a new ester, characterized in that a, a'-diethyl-4,4'-dioxystilbene is treated with an n-valerylating agent. The new compound, the a, a'-diethyl 4,4 '-. Dioxystilben- @ di-n-valerianate, melts at 76.5 to 77.5. Sie zeigt gegenüber den be kannten hormonal wirksamen Verbindungen ohne Steroidcharakter eine protrahiertere Wirkung im Oestrus- und 1-Tteruswachstums- test und soll deshalb therapeutische Verwen dung finden,, UNTERAN SPRüCHE 1. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass als n-valerylieren- des Mittel n-Valeriansäureanhydrid verwen det wird. 2. Compared to the known hormonally active compounds without steroid character, it shows a more protracted effect in the oestrus and 1-tterus growth test and is therefore intended to be used therapeutically. of the agent n-valeric anhydride is used. 2. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass als n-valerylieren- des Mittel ein n-Valeriansäurehalogenid ver wendet wird. Process according to patent claim, characterized in that an n-valeric acid halide is used as the n-valerylating agent.
CH230441D 1938-07-02 1938-07-02 Process for the preparation of a new ester of the oxy-stilbene series. CH230441A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH230441T 1938-07-02
CH225257T 1938-07-02

Publications (1)

Publication Number Publication Date
CH230441A true CH230441A (en) 1943-12-31

Family

ID=25726834

Family Applications (1)

Application Number Title Priority Date Filing Date
CH230441D CH230441A (en) 1938-07-02 1938-07-02 Process for the preparation of a new ester of the oxy-stilbene series.

Country Status (1)

Country Link
CH (1) CH230441A (en)

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