CH221517A - Process for the preparation of a salt of a derivative of p-aminobenzenesulfonamide. - Google Patents

Process for the preparation of a salt of a derivative of p-aminobenzenesulfonamide.

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Publication number
CH221517A
CH221517A CH221517DA CH221517A CH 221517 A CH221517 A CH 221517A CH 221517D A CH221517D A CH 221517DA CH 221517 A CH221517 A CH 221517A
Authority
CH
Switzerland
Prior art keywords
salt
methylpyridine
preparation
derivative
soluble
Prior art date
Application number
Other languages
German (de)
Inventor
Chemisches Industrielles Cilag
Original Assignee
Cilag Chemisches Ind Lab A G
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
Priority claimed from CH221517T external-priority
Application filed by Cilag Chemisches Ind Lab A G filed Critical Cilag Chemisches Ind Lab A G
Publication of CH221517A publication Critical patent/CH221517A/en

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic 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
    • C07D213/02Heterocyclic 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
    • C07D213/04Heterocyclic 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
    • C07D213/60Heterocyclic 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
    • C07D213/72Nitrogen atoms
    • C07D213/76Nitrogen atoms to which a second hetero atom is attached

Description

  

  Verfahren zur Darstellung eines Salzes eines Abkömmlings des       p-Aminobenzolsulfonamids.       Das in neuester Zeit bekannt :gewordene  2 - (p -     Aeetylaminobenzo@isul.f        onylamino-)    6     -          m-ethylpyridin    hat     sieh        @al's    geeignet     erwiesen     zur Bekämpfung infektiöser, insbesondere  durch Kokken hervorgerufener Krankheiten.  



  Es wurde nun gefunden,     d'ass    das, durch  Ersatz des     Wasserstoffatoms        seiner        Sulfon-          amidgruppe        d'ureh    Kalzium erhältliche     Kal-          ziumsalz    des     2-(p-Acetylaminobenzoltsulfonyl-          amina-)6-methylpyridinsi    gegenüber .der ent  sprechenden     Wasserstoffverbindung        .die,

      oben  erwähnten     therapeutischen        EigensichaTten    in       verstärktem    Masse     aufweist    und ausserdem  eine bessere Verträglichkeit besitzt. Die neue  Verbindung     soll    daher zur Bekämpfung       infektiöser    Erkrankungen, .speziell der durch       Strepto-,        Gono-    und.     Pneumokokken    verur  sachten, verwendet werden.  



  Das,     erfindungsgemässe    Verfahren zur  Darstellung der neuen Verbindung ist da  durch .gekennzeichnet, dass man     2-(p-Acetgl-          aminobenzoleulf        o@nylamino-)    6 -     methylpyridin       und eine zum     Austausch        desi    Wasserstoffes  der     Sulfonamid'gruppe    gegen     Kalzium    be  fähigte     Verhindlung,    z.

   B.     galziumhydrogyd.,     lösliches-     Kalziumslalz,    wie     galziumehlo@rid,     aufeinander einwirken lässt, wobei sieh       d@ae    neutrale     Kal'ziumsalz    des,     2-(p-Acetyl-          a.minobenzolsulfonyilamina-)6-methylpyridins.     bildet.  



  <I>Ausführungsbeispiel:</I>  10 g     2-#(p-Acetylaminobenzo#lsulfonyl-          amino-)6-methylpyridin        werden    in stark kon  zentriertem, wässerigem Ammoniak .gelöst.  Zu dieser Lösung     fügt    man tropfenweise eine       konzentrierte,    heisse,     wässemige        Lösung    von  zirka 60 g     Kalziumehforid.    Man     lässt        über     Nacht stehen,

       nutscht        das        auskristallisierte     2 - (p -     Acetylaminobenzolsulf        onylamino-)    6     -          methylpyridin-Kallzium    ab und wäscht es  mit wenig kaltem     Wasser.    Die     Ausbeute    be  trägt 8 .g.  



  Die neue Verbindung zersetzt     sieh:    ober  halb 250' C ohne zu schmelzen, ist ziemlich      löslich in warmem und kaltem Wasser und       Pyridin,    weniger gut     löslich    in Alkohol,       schwerlöslich    in Azeton, Äther und Benzol.



  Process for the preparation of a salt of a derivative of p-aminobenzenesulfonamide. The recently known 2 - (p - aeetylaminobenzo@isul.f onylamino-) 6 - m-ethylpyridine has proven to be suitable for combating infectious diseases, especially those caused by cocci.



  It has now been found that the calcium salt of 2- (p-acetylaminobenzenesulfonylamine) 6-methylpyridine, obtainable by replacing the hydrogen atom of its sulfonamide group with calcium, is compared to the corresponding hydrogen compound.

      Has the above-mentioned therapeutic properties to a greater extent and also has better tolerability. The new compound should therefore be used to combat infectious diseases, especially those caused by strepto-, gono- and. Pneumococci can be used.



  The process according to the invention for the preparation of the new compound is characterized by the fact that 2- (p-Acetgl- aminobenzoleulf o @ nylamino-) 6 - methylpyridine and an exchange desi hydrogen of the sulfonamid'gruppe against calcium be able prevention, z .

   B. Galziumhydrogyd., Soluble calcium salt, such as Galziumehlo @rid, lets act on each other, where see the neutral calcium salt of 2- (p-acetyl-a.minobenzolsulfonyilamina-) 6-methylpyridine. forms.



  <I> Exemplary embodiment: </I> 10 g of 2 - # (p-acetylaminobenzo #isulfonylamino) 6-methylpyridine are dissolved in highly concentrated aqueous ammonia. A concentrated, hot, aqueous solution of about 60 g of calcium hydroxide is added dropwise to this solution. One lets stand overnight

       The crystallized 2 - (p - Acetylaminobenzolsulfonylamino-) 6 - methylpyridin-Kalzium sucks off and washes it with a little cold water. The yield be 8 g.



  The new compound decomposes: above 250 ° C without melting, it is fairly soluble in warm and cold water and pyridine, less soluble in alcohol, sparingly soluble in acetone, ether and benzene.

 

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines Salzes eines Abkömmlings des p- Aminobenzol@sul- fonamida-, dadurch gekennzeichnet, dass man 2 - (p-. Aoetylaminobenzolsulfony lamino -) 6- methylpyridin und eine zum Austausch des Wasserstoffes der Su@lfonamidgruppe gegen Kalzium befähigte Verbindung aufeinander einwirken lässt, PATENT CLAIM: Process for the preparation of a salt of a derivative of p-aminobenzene @ sulfonamida-, characterized in that 2 - (p-. Aoetylaminobenzolsulfony lamino-) 6-methylpyridine and one to exchange the hydrogen of the sulfonamide group for calcium Allows connection to interact, wobei sich das neutrale Kal- ziumsa.lz des 2-(p-Aaetylaminobenzolsulfonyi- amino-)6-methylpyridins@ bildet. Das Verfahrensprodukt zersetzt sich ober halb 250 C ohne zu schmelzen, ist ziemlich löslich in warmem und kaltem Wasser und Pyridin, weniger gut löslich in Alkohol, schwerlöslich in Azeton, Äther und Benzol. the neutral calcium salt of 2- (p-acetylaminobenzene sulfonyi-amino) 6-methylpyridine @ is formed. The process product decomposes above 250 C without melting, is fairly soluble in warm and cold water and pyridine, less soluble in alcohol, sparingly soluble in acetone, ether and benzene. Es soll zur Bekämpfung infektiöser Erkran kungen, speziell der durch Strepto-, Gono- und Pneumokokken verure-achten, verwendet werden. It should be used to combat infectious diseases, especially those caused by streptococci, gonococci and pneumococci.
CH221517D 1939-11-21 1939-11-21 Process for the preparation of a salt of a derivative of p-aminobenzenesulfonamide. CH221517A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH221517T 1939-11-21
CH213815T 1943-03-13

Publications (1)

Publication Number Publication Date
CH221517A true CH221517A (en) 1942-05-31

Family

ID=25725497

Family Applications (1)

Application Number Title Priority Date Filing Date
CH221517D CH221517A (en) 1939-11-21 1939-11-21 Process for the preparation of a salt of a derivative of p-aminobenzenesulfonamide.

Country Status (1)

Country Link
CH (1) CH221517A (en)

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