CH214045A - Method for the preparation of p-aminobenzenesulfon-a-aminopyridine-methylensulfonic acid sodium. - Google Patents

Method for the preparation of p-aminobenzenesulfon-a-aminopyridine-methylensulfonic acid sodium.

Info

Publication number
CH214045A
CH214045A CH214045DA CH214045A CH 214045 A CH214045 A CH 214045A CH 214045D A CH214045D A CH 214045DA CH 214045 A CH214045 A CH 214045A
Authority
CH
Switzerland
Prior art keywords
aminopyridine
aminobenzenesulfon
acid sodium
methylensulfonic
preparation
Prior art date
Application number
Other languages
German (de)
Inventor
Dr A Wander A G
Original Assignee
Wander Ag Dr A
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 Wander Ag Dr A filed Critical Wander Ag Dr A
Publication of CH214045A publication Critical patent/CH214045A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyridine Compounds (AREA)

Description

  

  Verfahren zur Darstellung von     p-aminobenzolsulfon-a-aminopyridin-          methylensulfonsaurem    Natrium.    Die     bakteriziden    Eigenschaften des     p-          A.minobenzols.ulfon-a-aminopyriclins        sind    be  kannt.

   Diese     Verbindung    besitzt jedoch     ,den     grossen Nachteil, in Wasser     äusserst    schwer  löslich zu     ,sein.    Ihre Salze, speziell das bereits  beschriebene     Chlorhydrat,    kommen infolge  ihrer stark sauren     Reaktion    für die     parente-          rale        Anwendung    nicht in     Betracht.     



  Es wurde nun gefunden, dass das Reak  tionsprodukt des     Formald-ehydnatriumbi6ul-          fits    und     des        p-Aminobenzolsulfon-a-amino-          pyridine        nicht    nur sehr leicht     wass        @erlöslieh     ist, sondern in Lösung auch eine Wasserstoff  ionenkonzentration aufweist, die nahe bei 7  liegt, also     praktisch    neutral     ist.     



  Das     vorliegende    Patent hat zum     Gegen-          ,stand        ein    Verfahren zur Herstellung von p       a.minobe@nzolsulfon-a-aminopyri,din-methylen-          sulfonsaurem    Natrium, welches     @dadumh    ge  kennzeichnet     äst,        dass    man     p-Aminobenzol-          sulfon-a-aminopyridin    und     Formaldehyd-          natriumbisulfit        aufeinander    einwirken     lässt,       und zwar     zweckmässä,

  g    unter Erwärmen in  Gegenwart eines Lösungsmittels.  



  Das erhaltene Produkt     ist        farblos,        kristal-          länisch        und        in    Wasser sehr leicht löslich.       Seine    Lösung ist     neutral.    Die     Verbindung     soll     therapeutische    Anwendung finden.  



  <I>Beispiel:</I>  Man erhitzt 0,1     Mol        4-Aminobenzolsulfon-          a-aminopyridin    mit 0,15     Mol        F'ormaldehyd-          natrium:

  bisulfit        .in    Gegenwart von<B>300</B> cm'  Wasser     während    einer     Stunde.    Die     entstan-          dene    Lösung bleibt auch nach dem Erkalten  klar.

       Durch        vorsichtiges    Eindampfen, gege  benenfalls im Vakuum, erhält man     das    kri  stallinische     Reaktionsprodukt,    das aus     einem          geeigneten        Lösungsmittel,        beispielsweise    aus       verdünntem    Alkohol,     umkristallisiert    werden  kann.



  Process for the preparation of p-aminobenzenesulfon-a-aminopyridine-methylensulfonsaurem sodium. The bactericidal properties of p-A.minobenzols.ulfon-a-aminopyriclins are known.

   However, this compound has the great disadvantage of being extremely sparingly soluble in water. Their salts, especially the hydrochloride already described, are not suitable for parenteral use because of their strongly acidic reaction.



  It has now been found that the reaction product of the formaldehyde-sodium sulphate and p-aminobenzene-sulfone-a-aminopyridine is not only very easily soluble in water, but also has a hydrogen ion concentration in solution that is close to 7, is practically neutral.



  The subject matter of the present patent is a process for the preparation of p a.minobe @ nzenesulfone-a-aminopyri, din-methylene-sulfonic acid sodium, which @dadumh indicates that p-aminobenzenesulfone-a-aminopyridine is used and formaldehyde sodium bisulfite to act on each other, specifically

  g with heating in the presence of a solvent.



  The product obtained is colorless, crystalline and very easily soluble in water. His solution is neutral. The compound is intended to find therapeutic use.



  <I> Example: </I> 0.1 mol of 4-aminobenzenesulfon-a-aminopyridine is heated with 0.15 mol of sodium formaldehyde:

  bisulfite in the presence of <B> 300 </B> cm 'of water for one hour. The resulting solution remains clear even after cooling.

       Careful evaporation, if necessary in vacuo, gives the crystalline reaction product, which can be recrystallized from a suitable solvent, for example from dilute alcohol.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von p-amino benzolsulfon-a-aminopyridin-methylensulrfon- saurem Natrium, dadureh ,gekennzeichnet, dass man p-Aminobenzolsulfon-a-aminopyri- din und Formaldehyd@natriumbieulfit aufein ander einwirken lässt. Das entstandene p- aminobenzolsulfon-a-amänopyridin -methylen- sulfonsaure Natrium ist ein farbloser PATENT CLAIM: Process for the production of p-amino benzenesulfon-a-aminopyridine-methylensulfonic acid sodium, characterized in that p-aminobenzenesulfon-a-aminopyridine and formaldehyde @ sodium bendulfite are allowed to act on each other. The resulting p-aminobenzenesulfon-a-amenopyridine-methylene sulfonic acid sodium is colorless kristal- linischer Körper, der in Wasser leicht lös lich ist. Die Lösung ist neutral. ÜNTERANSPRt?CIIE 1. Verfahren nach Patentanspruch, da- duTOh ,gekennzeichnet, dass in Gegenwart eines Lösungsmittels gearbeitet wird. 2. crystalline body that is easily soluble in water. The solution is neutral. ÜNTERANSPRt? CIIE 1. Process according to claim, da- duTOh, characterized in that it is carried out in the presence of a solvent. 2. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man die Reaktion In der Wärme vollzieht. Method according to claim, characterized in that the reaction is carried out in the heat.
CH214045D 1939-12-04 1939-12-04 Method for the preparation of p-aminobenzenesulfon-a-aminopyridine-methylensulfonic acid sodium. CH214045A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH214045T 1939-12-04

Publications (1)

Publication Number Publication Date
CH214045A true CH214045A (en) 1941-03-31

Family

ID=4448518

Family Applications (1)

Application Number Title Priority Date Filing Date
CH214045D CH214045A (en) 1939-12-04 1939-12-04 Method for the preparation of p-aminobenzenesulfon-a-aminopyridine-methylensulfonic acid sodium.

Country Status (1)

Country Link
CH (1) CH214045A (en)

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