CH220592A - Process for the preparation of B- (4-oxy-3,6-diiodophenyl) -a-phenyl-propionic acid. - Google Patents

Process for the preparation of B- (4-oxy-3,6-diiodophenyl) -a-phenyl-propionic acid.

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Publication number
CH220592A
CH220592A CH220592DA CH220592A CH 220592 A CH220592 A CH 220592A CH 220592D A CH220592D A CH 220592DA CH 220592 A CH220592 A CH 220592A
Authority
CH
Switzerland
Prior art keywords
phenyl
propionic acid
oxy
preparation
diiodophenyl
Prior art date
Application number
Other languages
German (de)
Inventor
Schering A G
Original Assignee
Schering Ag
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 Schering Ag filed Critical Schering Ag
Publication of CH220592A publication Critical patent/CH220592A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
    • C07C59/56—Unsaturated compounds containing hydroxy or O-metal groups containing halogen

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

  Verfahren zur Herstellung von     ss-(4-Ogy-3,6-dijodphenyl)-a-phenyl-propionsäure.       Ausser dem bekannten     Tetrajodphenol-          plitalein,    das zur     röntgenologischen        Sichtbar-          machung    der Gallenblase benutzt wird, sind  auch jodierte Abkömmlinge der     2-Phenyl-          cinchoninsäure    für diese Verwendung heran  gezogen worden. Alle diese Substanzen geben  zwar einen guten Schatten, sie haben sich  jedoch in der zur     Applikation    nötigen Menge  physiologisch nicht als so indifferent erwiesen,  wie es für diagnostische Mittel gefordert wer  den muss.  



  Es wurden nun in den     polyjodierten     Abkömmlingen der     Oxydiphenylcarbonsäuren          lipoidlösliche    Verbindungen gefunden, die im       Gegensatz    zu den bisher bekannten Gallen  kontrastmitteln mit guter Kontrastwirkung  auch     eine    vorzügliche Verträglichkeit     aufweis    en.  Ihre Herstellung erfolgt durch     Jodierung    von  o- oder     p-Oxydiphenylcarbonsäureri    nach an  sich üblichen Methoden.  



  Gegenstand des vorliegenden Patentes ist  ein     Verfahren    zur Herstellung der     ss'-(4-Oxy-          3,6    -     dijodphenyl)    - a -     pheny        1-propionsäure,    das    dadurch gekennzeichnet ist, dass man     P-(4-          Oxyphenyl)-a-phenyl-propionsäure    mit einem  jodierenden Mittel behandelt.  



  Die neue Verbindung soll insbesondere als  Gallenkontrastmittel Verwendung finden.    <I>Beispiel:</I>  Eine Lösung von 24,2 g     ss-(4-Oxyphenyl)-a-          phenyl-propionsäure    in 800 n/2 Natronlauge  wird unter Rühren langsam bei gewöhnlicher  Temperatur mit einer     Lösungvon    50,8 g Jod und  50,8 g     Jodkalium    in 250 cm' Wasser versetzt.  Aus der annähernd neutralen, schwach gefärb  ten Lösung wird das     Jodierungsprodukt    durch  Zusatz von schwefliger Säure und Salzsäure  ausgefällt. Es wird noch eine Zeitlang gerührt,  das fast farblose Produkt dann abgesaugt und  mit Wasser ausgewaschen.

   Nachdem Trocknen  wird aus Benzol unter Zusatz von Tierkohle       umkristallisiert.    Farblose Prismen vom     Smp.     <B>159'.</B> Die Ausbeute beträgt 42 g = 85  /o  der Theorie. Die     @3-(4-Oxy-3,5-dijodpheiiyl)-a-          phenyl-propionsäure    ist leicht löslich in Äther,      Alkohol und Aceton, schwerer in Benzol,     Toluol     und     Chloroform,    unlöslich in Wasser und       Ligroin.  



  Process for the preparation of ss- (4-Ogy-3,6-diiodophenyl) -a-phenyl-propionic acid. In addition to the well-known tetraiodophenol plitalein, which is used for radiological visualization of the gall bladder, iodinated derivatives of 2-phenyl-cinchonic acid have also been used for this purpose. Although all these substances give a good shade, they have not proven to be physiologically as indifferent in the amount necessary for application as must be required for diagnostic agents.



  In the polyiodinated derivatives of the oxydiphenylcarboxylic acids, lipoid-soluble compounds have now been found which, in contrast to the previously known bile contrast media with a good contrast effect, also have excellent compatibility. They are produced by iodination of o- or p-Oxydiphenylcarbonsäureri according to conventional methods.



  The present patent relates to a process for the preparation of ss' - (4-oxy-3,6 - diiodophenyl) - a - pheny 1-propionic acid, which is characterized in that P- (4-oxyphenyl) -a-phenyl -propionic acid treated with an iodine agent.



  The new compound is intended to be used in particular as a biliary contrast medium. <I> Example: </I> A solution of 24.2 g of ss- (4-oxyphenyl) -aphenyl-propionic acid in 800 n / 2 sodium hydroxide solution is slowly mixed with a solution of 50.8 g of iodine at normal temperature while stirring and 50.8 g of potassium iodide are added to 250 cm of water. The iodination product is precipitated from the approximately neutral, weakly colored solution by adding sulfurous acid and hydrochloric acid. The mixture is stirred for a while, then the almost colorless product is filtered off with suction and washed out with water.

   After drying, it is recrystallized from benzene with the addition of animal charcoal. Colorless prisms with a melting point <B> 159 '. </B> The yield is 42 g = 85 / o of theory. The @ 3- (4-oxy-3,5-dijodpheiiyl) -aphenylpropionic acid is easily soluble in ether, alcohol and acetone, more difficult in benzene, toluene and chloroform, insoluble in water and ligroin.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von 13-(4-Oxy- 3, .5 - dij odphenyl) - a - phenyl-propionsäure, da durch gekennzeichnet, dar man ,3-(4-Oxy- phenyl)-a-phenyl-propioiisäure mit einem jodie- renden Mittel behandelt. Die neue Verbindung bildet farblose Prismen vom Smp. 159 . Sie ist leicht löslich in Äther. PATENT CLAIM: A process for the preparation of 13- (4-oxy- 3, .5 - dijodophenyl) - a - phenylpropionic acid, characterized in that it is 3- (4-oxyphenyl) -a-phenyl-propionic acid treated with an iodizing agent. The new compound forms colorless prisms of m.p. 159. It is easily soluble in ether. Alkohol und Aceton, schwerer in Benzol, Toluol und Chloroform, unlöslich in Wasser und Ligroin. Alcohol and acetone, heavier in benzene, toluene and chloroform, insoluble in water and ligroin.
CH220592D 1939-12-18 1940-05-18 Process for the preparation of B- (4-oxy-3,6-diiodophenyl) -a-phenyl-propionic acid. CH220592A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE220592X 1939-12-18

Publications (1)

Publication Number Publication Date
CH220592A true CH220592A (en) 1942-04-15

Family

ID=5835395

Family Applications (1)

Application Number Title Priority Date Filing Date
CH220592D CH220592A (en) 1939-12-18 1940-05-18 Process for the preparation of B- (4-oxy-3,6-diiodophenyl) -a-phenyl-propionic acid.

Country Status (1)

Country Link
CH (1) CH220592A (en)

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