CH265666A - Process for the preparation of a new condensation product of 6-sulfanilamido-3-methyl-pyridazine. - Google Patents

Process for the preparation of a new condensation product of 6-sulfanilamido-3-methyl-pyridazine.

Info

Publication number
CH265666A
CH265666A CH265666DA CH265666A CH 265666 A CH265666 A CH 265666A CH 265666D A CH265666D A CH 265666DA CH 265666 A CH265666 A CH 265666A
Authority
CH
Switzerland
Prior art keywords
pyridazine
sulfanilamido
methyl
condensation product
preparation
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellschaft Ciba
Original Assignee
Ciba Geigy
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 Ciba Geigy filed Critical Ciba Geigy
Publication of CH265666A publication Critical patent/CH265666A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
    • C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members 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
    • C07D237/20—Nitrogen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

  

  <B>Verfahren zur Herstellung eines neuen Kondensationsproduktes des</B>     6-Sulfanilamido-          3-methyl-pyridazins.       Die vorliegende Erfindung betrifft ein  Verfahren zur Herstellung     eines    -Kondensa  tionsproduktes des Formaldehyds     mit        6-Sulf-          anilamido-3-methyl-pyridazin.    Die neue Ver  bindung zeigt gegenüber dem     6-Sulfanilamido-          3-methyl-pyridazin        wertvollere    therapeutische  Eigenschaften.  



  Das neue Kondensationsprodukt des       6-Sulfanilamido-3-methyl-pyridazins    wird er  findungsgemäss dadurch erhalten, dass man       6-Sulfanilamido-3-methyl-pyridazin    mit Form  aldehyd umsetzt. Statt Formaldehyd selbst  können auch Formaldehyd abgebende Mittel,  wie     Paraformaldeliyd    oder     Hexamethylen-          tetramin,        verwendet    werden.

   Die Umsetzung  wird vorteilhaft in Gegenwart von     Verdün-          nungsmitteln,    wie Wasser,     verdünnten    Säu  ren oder     organischen        Lösungsmitteln,    bei  spielsweise Alkohol, durchgeführt.  



  Die     Herstellbarkeit    des neuen     Kondensa-          tionsproduktes    sowie besonders die     llög@ich-          keit    seiner Isolierung in einer für die thera  peutische Verwendung geeigneten Form war  durchaus nicht selbstverständlich.     Gewisse          Sulfanilamide    der     lieterocyclischen    Reihe  geben mit Formaldehyd nur schmierige Reak  tionsprodukte.  



  Die verfahrensgemäss erhaltene Verbin  dung bildet ein gelbliches Pulver, das in  Säuren unlöslich ist. Sie soll als Heilmittel  Verwendung finden.  



  <I>Beispiel:</I>  26,4     Gewichtsteile    6 -     Sulfanilamido    - 3     -          methyl-pyridazin    werden in 250     Volumteilen       Nasser aufgeschwemmt und durch Zusatz  von 25 V     olumteilen    konzentrierter     Salzsäure     in Lösung gebracht. Hierauf tropft man  unter gutem Rühren 15     Volumteile    40%ige       Formaldehydlösung    allmählich ein. Das Reak  tionsprodukt beginnt bald sieh in feiner Form  abzuscheiden.

   Nachdem alle     Formaldehycl-          lösung    zugesetzt     ist,    lässt man 1 Stunde  stehen, saugt ab,     wäscht    gründlich mit  Wasser, schwemmt in Wasser auf, neu  tralisiert die letzten Spuren Säure mit       Sodalösung,    saugt ab, trocknet bei 50  C  und siebt durch ein feines Sieb. Man erhält  so 26 Gewichtsteile eines     gelblichen    Pulvers,       das    in Säuren unlöslich ist. In Berührung  mit     Ätzalkalien    verändert sich das     Produkt     in kurzer Zeit, und es tritt Auflösung ein.



  <B> Process for the preparation of a new condensation product of </B> 6-sulfanilamido-3-methyl-pyridazine. The present invention relates to a process for the preparation of a condensation product of formaldehyde with 6-sulfanilamido-3-methyl-pyridazine. Compared to 6-sulfanilamido-3-methyl-pyridazine, the new compound shows more valuable therapeutic properties.



  The new condensation product of 6-sulfanilamido-3-methyl-pyridazine is obtained according to the invention by reacting 6-sulfanilamido-3-methyl-pyridazine with formaldehyde. Instead of formaldehyde itself, formaldehyde-releasing agents, such as paraformaldelyde or hexamethylene tetramine, can also be used.

   The reaction is advantageously carried out in the presence of diluents, such as water, dilute acids or organic solvents, for example alcohol.



  The producibility of the new condensation product and especially the ability to isolate it in a form suitable for therapeutic use was by no means a given. Certain sulfanilamides of the lieterocyclic series give only greasy reaction products with formaldehyde.



  The compound obtained according to the process forms a yellowish powder which is insoluble in acids. It is said to be used as a remedy.



  <I> Example: </I> 26.4 parts by weight of 6 - sulfanilamido - 3 - methyl-pyridazine are suspended in 250 parts by volume of water and dissolved by adding 25 parts by volume of concentrated hydrochloric acid. 15 parts by volume of 40% formaldehyde solution are then gradually added dropwise with thorough stirring. The reaction product soon begins to separate out in fine form.

   After all the formaldehyde solution has been added, the mixture is left to stand for 1 hour, suctioned off, washed thoroughly with water, washed up in water, the last traces of acid are neutralized with soda solution, suctioned off, dried at 50 C and sieved through a fine sieve. This gives 26 parts by weight of a yellowish powder which is insoluble in acids. In contact with caustic alkalis, the product changes in a short time and dissolution occurs.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines neuen Kondensationsproduktes des 6-Sulfanilamido- 3-methy 1-pyridazins, dadurch gekennzeichnet, dass man 6-Sulfanilamiclo-3-methyl-pyridazin mit Formaldehyd umsetzt. Das erhaltene Kondensationsprodukt bildet ein gelbliches Pulver, das in Säuren unlöslich ist. Es soll als Heilmittel Verwendung finden. UNTERANSPRUCH: Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man die Umsetzung in Gegenwart von verdünnten Säuren durch führt. PATENT CLAIM: Process for the preparation of a new condensation product of 6-sulfanilamido-3-methy 1-pyridazine, characterized in that 6-sulfanilamiclo-3-methyl-pyridazine is reacted with formaldehyde. The condensation product obtained forms a yellowish powder which is insoluble in acids. It is said to be used as a remedy. SUBSTANTIAL CLAIM: Process according to patent claim, characterized in that the reaction is carried out in the presence of dilute acids.
CH265666D 1947-10-09 1947-10-09 Process for the preparation of a new condensation product of 6-sulfanilamido-3-methyl-pyridazine. CH265666A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH265666T 1947-10-09

Publications (1)

Publication Number Publication Date
CH265666A true CH265666A (en) 1949-12-15

Family

ID=4475813

Family Applications (1)

Application Number Title Priority Date Filing Date
CH265666D CH265666A (en) 1947-10-09 1947-10-09 Process for the preparation of a new condensation product of 6-sulfanilamido-3-methyl-pyridazine.

Country Status (1)

Country Link
CH (1) CH265666A (en)

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