CH213196A - Process for the preparation of a water-soluble, injectable N-benzyl-sulfanilic acid amide compound. - Google Patents

Process for the preparation of a water-soluble, injectable N-benzyl-sulfanilic acid amide compound.

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Publication number
CH213196A
CH213196A CH213196DA CH213196A CH 213196 A CH213196 A CH 213196A CH 213196D A CH213196D A CH 213196DA CH 213196 A CH213196 A CH 213196A
Authority
CH
Switzerland
Prior art keywords
benzyl
acid amide
soluble
sulfanilic acid
injectable
Prior art date
Application number
Other languages
German (de)
Inventor
F Hoffmann- Aktiengesellschaft
Original Assignee
Hoffmann La Roche
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 Hoffmann La Roche filed Critical Hoffmann La Roche
Publication of CH213196A publication Critical patent/CH213196A/en

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Description

  

  Verfahren zur Darstellung einer wasserlöslichen,     injizierbaren          N-Benzyl-salfanilsäureamidverbindung.       Das bei     Streptokokkeninfektionen    sehr  wirksame und viel benützte     Sulfanilsäure-          amid    lässt sich, ebenso wie seine Abkömm  linge, nur per os einnehmen.     Injizierbare     wässerige Lösungen dieser Verbindungen  sind bis jetzt noch nicht bekannt geworden.  



  Es wurde nun gefunden, dass es gelingt,  eine neutrale,     injizierbare,    wässerige Lösun  gen liefernde Verbindung des     N-Benzyl-sulf-          anilsäureamids    zu erhalten, wenn man     N-          Benzyl-sulfanilsäureamid    mit     Phosphoroxy-          halogeniden    erhitzt und das entstandene  Kondensationsprodukt mit wässerigem Am  moniak behandelt.

      Die     N-Benzyl-sulfanilsäureamid-phosph-          amidsäure    ist schwer löslich in kaltem Was  ser und Alkohol; ihre     Alkalisalze        sowie    das       Ammoniumsalz    sind auch in kaltem Wasser  leicht löslich.  



  Die neue Verbindung soll als Arzneimit  tel verwendet werden.         Beispiel:       15 Teile     N-Benzyl-sulfanilsäureamid    wer  den mit 30 Teilen     Phosphoroxychlorid    er  hitzt und die Lösung in eine Mischung von       Benzol-Petroläther    eingetragen. Das ausge  fällte     Phosphorsäuredichlorid    wird unter  Kühlung mit wässeriger     Ammoniaklösung     umgesetzt. Die     ammoniakalische    Lösung  wird im Vakuum     eingeengt    und die     Phosph-          amidsäure    durch     Salzsäurezusatz    gefällt.

   Das  ,<B>-</B>     i        u        sgeschiedene        Rohprodukt        wird        abgesaugt,     in     Sodalösung    gelöst, die Lösung filtriert  und wieder gefällt.



  Process for the preparation of a water-soluble, injectable N-benzyl-salfanilic acid amide compound. The sulfanilic acid amide, which is very effective and widely used in streptococcal infections, can, like its derivatives, only be taken orally. Injectable aqueous solutions of these compounds have not yet become known.



  It has now been found that it is possible to obtain a neutral, injectable, aqueous solution-supplying compound of N-benzyl-sulfanilic acid amide if N-benzyl-sulfanilic acid amide is heated with phosphorus oxyhalides and the condensation product formed is mixed with aqueous ammonia treated.

      N-benzyl-sulfanilic acid amide-phosphamic acid is sparingly soluble in cold water and alcohol; their alkali salts and the ammonium salt are also easily soluble in cold water.



  The new compound is to be used as a drug. Example: 15 parts of N-benzyl sulfanilic acid amide who with 30 parts of phosphorus oxychloride he heated and the solution added to a mixture of benzene petroleum ether. The precipitated phosphoric acid dichloride is reacted with aqueous ammonia solution while cooling. The ammoniacal solution is concentrated in vacuo and the phosphamic acid is precipitated by adding hydrochloric acid.

   The separated crude product is filtered off with suction, dissolved in soda solution, the solution is filtered and precipitated again.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung einer wasser löslichen, injizierbaren N-Benzyl-sulfanil- säureamidverbindung, dadurch gekennzeich net, dass man N-Benzyl-sulfanilsäureamid mit Phosphoroxyhalogeniden erhitzt und auf das erhaltene Kondensationsprodukt wäs seriges Ammoniak einwirken lässt. PATENT CLAIM: Process for the preparation of a water-soluble, injectable N-benzyl-sulfanilic acid amide compound, characterized in that N-benzyl-sulfanilic acid amide is heated with phosphorus oxyhalides and aqueous ammonia is allowed to act on the condensation product obtained. Die N-Benzyl-sulfanilsäureamid-phosph- amidsäure ist schwer löslich in kaltem Was ser und Alkohol; ihre Alkalisalze sowie das Ammoniumsalz sind auch in kaltem Wasser leicht löslich. Die neue Verbindung,soll als Arzneimit tel verwendet werden. N-benzyl-sulfanilic acid amide-phosphamic acid is sparingly soluble in cold water and alcohol; their alkali salts and the ammonium salt are also easily soluble in cold water. The new compound is to be used as a drug.
CH213196D 1938-04-26 1938-04-26 Process for the preparation of a water-soluble, injectable N-benzyl-sulfanilic acid amide compound. CH213196A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH213196T 1938-04-26
CH206549T 1938-04-26

Publications (1)

Publication Number Publication Date
CH213196A true CH213196A (en) 1941-01-15

Family

ID=25724324

Family Applications (1)

Application Number Title Priority Date Filing Date
CH213196D CH213196A (en) 1938-04-26 1938-04-26 Process for the preparation of a water-soluble, injectable N-benzyl-sulfanilic acid amide compound.

Country Status (1)

Country Link
CH (1) CH213196A (en)

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