CH230443A - 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
CH230443A
CH230443A CH230443DA CH230443A CH 230443 A CH230443 A CH 230443A CH 230443D A CH230443D A CH 230443DA CH 230443 A CH230443 A CH 230443A
Authority
CH
Switzerland
Prior art keywords
preparation
stearylating
oxy
new ester
agent
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 CH230443A publication Critical patent/CH230443A/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)

Description

  

      Verfahren    zur Darstellung eines neuen Esters der     Ogy-stilbenreihe.       Es wurde gefunden, dass man zu einem  neuen Ester gelangen kann, wenn man     a,ä        -          Diäthyl-4,4'-dioxystilben    mit einem     steary-          lierenden    Mittel behandelt.    Geeignete     stearylierende    Mittel sind zum  Beispiel die     Stearinsäure    selbst, ihre Halo  genide oder Ester mit niederen Alkoholen       (Umesterung),    ihr     Anhydrid        sowie    auch das  von ihr abgeleitete Beten.

      Die reue Verbindung, das     a,a'-Diäthyl-          4,4'-dioxystilben-di-stearat,    schmilzt bei 84  bis 86 . Sie zeigt gegenüber den bekannten  hormonal wirksamen Verbindungen ohne     Ste-          roidcharakter    eine     protrahiertere    Wirkung  im     Oestrus-    und     Uteruswachstumstest    und  soll deshalb therapeutische Verwendung fin  den.  



  <I>Beispiel:</I>  3 Teile     a,ä        -Diäthyl-4,4'-dioxystilben    wer  den in 50 Teilen     Pyridin    mit 4 Teilen     Stea-          rinsäurechlorid    versetzt und 12 Stunden bei  Raumtemperatur stehen gelassen.     Dann,        wird       Wasser zugegeben, das ausfallende 01 in  Äther aufgenommen und     nacheinander    mit       n-Schwefelsäure,    Wasser und     n/10    Natron  lauge gewaschen.

   Aus der Ätherlösung ge  winnt man durch     Abdunsten    den     Di-stearin-          säureester,    der nach     Umlösen    aus verdünntem  Methanol bei 84 bis 86      schmilzt.     



  Die gleiche Verbindung erhält man durch  Erhitzen des     Stilbenderivates    mit Stearin  säureanhydrid.



      Process for the preparation of a new ester of the Ogy stilbene series. It has been found that a new ester can be obtained if a, a - diethyl-4,4'-dioxystilbene is treated with a stearylating agent. Suitable stearylating agents are, for example, the stearic acid itself, its halides or esters with lower alcohols (transesterification), its anhydride and also the praying derived from it.

      The remorseful compound, the a, a'-diethyl 4,4'-dioxystilbene di-stearate, melts at 84 to 86. 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 find therapeutic use.



  <I> Example: </I> 3 parts of a, a-diethyl-4,4'-dioxystilbene are added to 50 parts of pyridine with 4 parts of stearic acid chloride and left to stand for 12 hours at room temperature. Then, water is added, the precipitating oil is taken up in ether and washed successively with n-sulfuric acid, water and n / 10 sodium hydroxide solution.

   The di-stearic acid ester is obtained from the ether solution by evaporation; it melts at 84 to 86 after being dissolved in dilute methanol.



  The same compound is obtained by heating the stilbene derivative with stearic anhydride.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines neuen Esters, dadurch gekennzeichnet, dass man a,a'-Diäthyl-4,4'-dioxystilben mit einem stea- rylierenden Mittel behandelt. Die neue Verbindung, das a,a'-Diäthyl- 4,4'-dioxystilben-@di-,stearat,.schmilzt bei 84 bis. 86 . Sie zeigt gegenüber den bekannten hor monal wirksamen Verbindungen ohne Steroid charakter eine protrahiertere Wirkung im Oestrus- und Uteruswachstumstest und soll deshalb therapeutische Verwendung finden. Claim: Process for the preparation of a new ester, characterized in that a, a'-diethyl-4,4'-dioxystilbene is treated with a stearylating agent. The new compound, the a, a'-diethyl 4,4'-dioxystilbene @ di-, stearate, melts at 84 to. 86. Compared to the known hormonal active compounds without steroid character, it shows a more protracted effect in the oestrus and uterus growth test and should therefore be used therapeutically. UNTERANSPRüCHE 1. Verfahren nach Patentanspruch. da durch gekennzeichnet, dass als stearylierendes Mittel Stearinsäureanhydrid verwendet wird. 2. Verfahren nach Patentanspx-ttch, da durch gekennzeichnet, dass als stearylierendes 111ittel ein Stea,rinsäurehalogenid verwendet wird. SUBClaims 1. Method according to patent claim. characterized in that stearic anhydride is used as the stearylating agent. 2. The method according to patent claim, characterized in that a stearic acid halide is used as the stearylating agent.
CH230443D 1938-07-02 1938-07-02 Process for the preparation of a new ester of the oxy-stilbene series. CH230443A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH225257T 1938-07-02
CH230443T 1938-07-02

Publications (1)

Publication Number Publication Date
CH230443A true CH230443A (en) 1943-12-31

Family

ID=25726836

Family Applications (1)

Application Number Title Priority Date Filing Date
CH230443D CH230443A (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) CH230443A (en)

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