CH230445A - 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.

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Publication number
CH230445A
CH230445A CH230445DA CH230445A CH 230445 A CH230445 A CH 230445A CH 230445D A CH230445D A CH 230445DA CH 230445 A CH230445 A CH 230445A
Authority
CH
Switzerland
Prior art keywords
preparation
oxy
agent
new ester
diogystilbene
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 CH230445A publication Critical patent/CH230445A/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     Oxy-stilbenr        eihe.       Es wurde gefunden, dass man zu einem  neuen Ester gelangen kann, wenn man     a,ä        -          Diätliyl-4,4'-diogystilben    mit einem     palmity-          lierenden        Mittel    behandelt.  



  Geeignete     palmitylierendeMittel    sind zum  Beispiel die     Palmitinsäure    selbst, ihre Halo  genide oder Ester mit niederen Alkoholen       (Umesterung),    ihr     Anhydrid        sowie    auch das  von ihr abgeleitete     Keten.     



  Die neue     Verbindung,    das     a,ä        -Diäthyl-          4,4'-diogystilben-di-palmitat,    schmilzt bei 82  bis 84 . Sie zeigt gegenüber den bekannten  hormonal wirksamen Verbindungen ohne     Ste-          roidcharakter    eine     protrahiertere    Wirkung  im     Oestrus-    und     Uteruswachstumstest    und  soll     dQshalb    therapeutische Verwendung fin  den.  



  <I>Beispiel:</I>  3 Teile     a,a        =Diäthyl-4,4'-diogystilben    wer  den in 50 Teilen     Chinolin    mit 5 Teilen     Pal-          mitinsäurechlorid    versetzt und 14 Stunden  bei 80  stehen gelassen. Dann wird vorsich  tig mit Eiswasser     verdünnt        tmd    das aUsfal-         lende    Produkt in Äther aufgenommen. Die  Ätherlösung wird dann mit verdünnter  Schwefelsäure, Wasser und     n/10    Natronlauge  gewaschen.

   Aus der über Natriumsulfat ge  trockneten Lösung gewinnt man den     Palmi-          tinsäureester.    Er schmilzt nach     Umlösen    aus  verdünntem Methanol bei 82     bis    84 .  



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



  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 - dietliyl-4,4'-diogystilbene is treated with a palmitylating agent.



  Suitable palmitylating agents are, for example, palmitic acid itself, its halides or esters with lower alcohols (transesterification), its anhydride and also the ketene derived from it.



  The new compound, the a, ä -diethyl-4,4'-diogystilbene-di-palmitate, melts at 82 to 84. Compared to the known hormonally active compounds without steroid character, it shows a more protracted effect in the oestrus and uterine growth test and is therefore intended to find therapeutic use.



  <I> Example: </I> 3 parts of a, a = diethyl-4,4'-diogystilbene who added 5 parts of palmitic acid chloride in 50 parts of quinoline and left to stand at 80 for 14 hours. Then it is carefully diluted with ice water and the precipitating product is taken up in ether. The ether solution is then washed with dilute sulfuric acid, water and n / 10 sodium hydroxide solution.

   The palmitic acid ester is obtained from the solution dried over sodium sulfate. After dissolving in dilute methanol, it melts at 82 to 84.



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

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines neuen Esters, dadurch gekennzeichnet, dass man a,a'-Diäthyl-4,4'-diogystilben mit einem pal- mitylierenden Mittel behandelt. Die neue Verbindung, das a,ä -Diäthyl- 4,4'-diogystilben-di-palmitat, schmilzt bei 82 bis 84 . Claim: Process for the preparation of a new ester, characterized in that a, a'-diethyl-4,4'-diogystilbene is treated with a palmitylating agent. The new compound, the a, ä -diethyl-4,4'-diogystilbene-di-palmitate, melts at 82 to 84. Sie zeigt gegenüber den bekannten hormonal wirksamen Verbindungen ohne Ste- roidcharakter eine protrahiertere Wirkung im Oestrus- und Uteruswachstumstest und soll deshalb therapeutische Verwen_dang finden. U-XTERA',\L-SPRüCHE 1. Compared to the known hormonally active compounds without steroid character, it shows a more protracted effect in the oestrus and uterus growth test and should therefore find therapeutic use. U-XTERA ', \ L-SPRüCHE 1. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass als palmity lieren- des Mittel Palmitinsäureanhydrid verwendet 5 wird. 2. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass als pa,lmitylieren.- des Mittel ein Palmitinsäurehalogenid ver wendet wird. Method according to claim, characterized in that palmitic anhydride is used as the palmity-lating agent. 2. The method according to claim, characterized in that a palmitic acid halide is used as the pa, imitylating agent.
CH230445D 1938-07-02 1938-07-02 Process for the preparation of a new ester of the oxy-stilbene series. CH230445A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH225257T 1938-07-02
CH230445T 1938-07-02

Publications (1)

Publication Number Publication Date
CH230445A true CH230445A (en) 1943-12-31

Family

ID=25726838

Family Applications (1)

Application Number Title Priority Date Filing Date
CH230445D CH230445A (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) CH230445A (en)

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