CH237324A - Process for the preparation of a salt of a derivative of p-amino-benzenesulfonamide. - Google Patents

Process for the preparation of a salt of a derivative of p-amino-benzenesulfonamide.

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Publication number
CH237324A
CH237324A CH237324DA CH237324A CH 237324 A CH237324 A CH 237324A CH 237324D A CH237324D A CH 237324DA CH 237324 A CH237324 A CH 237324A
Authority
CH
Switzerland
Prior art keywords
sep
benzene
amino
salt
pyrimidine
Prior art date
Application number
Other languages
German (de)
Inventor
Ag Cilag Chemisch Laboratorium
Original Assignee
Cilag Chemisches Ind Lab 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
Priority claimed from CH237324T external-priority
Application filed by Cilag Chemisches Ind Lab Ag filed Critical Cilag Chemisches Ind Lab Ag
Publication of CH237324A publication Critical patent/CH237324A/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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/69Benzenesulfonamido-pyrimidines

Description

  

  Verfahren zur Darstellung eines Salzes eines     Abkömmlings    des     p-Amino-          benzolsulfonamids.       Das in neuester Zeit bekannt gewordene  2-     (p-Acetylamino-benzol-sulfonylamino-)py-          rimidin    hat sich als geeignet erwiesen zur  Bekämpfung infektiöser, insbesondere durch       Kokken    hervorgerufener Krankheiten.  



  Es wurde nun gefunden, dass das durch  Ersatz des Wasserstoffatoms seiner     Sulfon-          amidgruppe    durch Kalzium erhältliche     Kal-          ziumsalz    des     2-(p-Acetylamino-benzol-sulfo-          nylamino-)pyrimidins    gegenüber der entspre  chenden Wasserstoffverbindung die oben er  wähnten therapeutischen Eigenschaften in  verstärktem Masse aufweist und ausserdem  eine bessere Verträglichkeit besitzt. Die neue  Verbindung soll daher zur Bekämpfung in  fektiöser Erkrankungen, speziell der durch       Strepto-,        Gono-    und     Pneumokokken    verursach  ten, verwendet werden.  



  Das erfindungsgemässe     Verhhren    zur  Darstellung der neuen Verbindung ist da  durch gekennzeichnet, dass man     2-(p-Acetyl-          amino-benzol-sulfonylamino-)pyrimidin    und  eine zum Austausch des Wasserstoffes der       Sulfonamidgruppe    gegen     Kalziiun    befähigte    Verbindung, z.

   B.     Kalziumhydrogyd,    lös  liches     galziumsalz,    wie     Kalziumchlorid,    auf  einander einwirken lässt, wobei sich das     Di-          [2    - (p -     Acetylamino-benzol    -     sulfonylamino)-          pyrimidin]-ealcium    bildet.  



  <I>Ausführungsbeispiel:</I>  20 g     2-(p-Acetylamino-benzol-sulfonyl-          amino-)pyrimidin    werden in stark konzen  triertem, wässerigem Ammoniak gelöst. Zu  der warmen     Lösung    fügt man tropfenweise  eine konzentrierte, heisse, wässerige Lösung  von zirka 100 g     Kalziumchlorid.    Man lässt  über Nacht stehen,     nutscht    das auskristalli  sierte     Di-        [2-(p-Acetylamino-benzol-sulfonyl-          amino-)pyrimidin]-calcium    ab und wäscht es  mit wenig kaltem Wasser. Die Ausbeute be  trägt 16 g.  



  Die neue, farblose, kristalline Verbin  dung zersetzt sich oberhalb 250  C ohne zu  schmelzen, ist sowohl in warmem als auch in  kaltem Wasser ziemlich löslich, ebenfalls in       Pyridin,    wenig löslich in Alkohol, schwer  löslich in Azeton, Äther und Benzol.



  Process for the preparation of a salt of a derivative of p-Amino-benzenesulfonamide. The recently known 2- (p-acetylamino-benzene-sulfonylamino) pyrimidine has proven to be suitable for combating infectious diseases, in particular those caused by cocci.



  It has now been found that the calcium salt of 2- (p-acetylamino-benzene-sulfonylamino-) pyrimidine, which can be obtained by replacing the hydrogen atom of its sulfonamide group with calcium, enhances the above-mentioned therapeutic properties compared with the corresponding hydrogen compound Has mass and also has better compatibility. The new compound should therefore be used to combat fectious diseases, especially those caused by streptococci, gonococci and pneumococci.



  The process according to the invention for the preparation of the new compound is characterized in that 2- (p-acetylamino-benzene-sulfonylamino) pyrimidine and a compound capable of exchanging the hydrogen of the sulfonamide group for calcium, eg.

   B. calcium hydrogen, soluble galcium salt, such as calcium chloride, can act on each other, forming the di- [2 - (p - acetylamino-benzene - sulfonylamino) - pyrimidine] -ealcium.



  <I> Exemplary embodiment: </I> 20 g of 2- (p-acetylamino-benzene-sulfonyl-amino) pyrimidine are dissolved in highly concentrated, aqueous ammonia. A concentrated, hot, aqueous solution of about 100 g of calcium chloride is added dropwise to the warm solution. It is left to stand overnight, the di- [2- (p-acetylamino-benzene-sulfonyl-amino) pyrimidine] calcium which has crystallized out is suction filtered and washed with a little cold water. The yield be 16 g.



  The new, colorless, crystalline compound decomposes above 250 C without melting, is fairly soluble in both warm and cold water, also in pyridine, slightly soluble in alcohol, sparingly soluble in acetone, ether and benzene.

 

Claims (1)

PATENTAN SPRUCH Verfahren zur Darstellung eines Salzes eines Abkömmlings des p-Amino-benzolsul- fonamids, dadurch gekennzeichnet. dass man - (p - Acety lamino-benzol-sulfonylamino-)py- rimidin und eine zum Austausch des Was serstoffes der Sulfonamidgruppe gegen Kal zium befähigte Verbindung aufeinander ein wirken lässt, wobei sieh das Di-[?-(p- Acetyl amino-benzol-sulfonylamino-) PATENT ANNOUNCEMENT Process for the preparation of a salt of a derivative of p-amino-benzenesulfonamide, characterized. that - (p - acetylamino-benzene-sulfonylamino-) pyrimidine and a compound capable of exchanging the hydrogen of the sulfonamide group for calcium are allowed to act on one another, see the di - [? - (p- acetyl amino- benzene sulfonylamino) pyrimidin]-cal- cium bildet. EMI0002.0016 Das <SEP> farblose, <SEP> kristalline <SEP> Verfahrenspro dukt <SEP> zersetzt <SEP> sich <SEP> oberhalb <SEP> ?<I>"3</I>0" <SEP> C <SEP> ohne <SEP> zu <tb> scliinelzeri, <SEP> ist <SEP> so\volil <SEP> in <SEP> warmem <SEP> als <SEP> auch <SEP> in <tb> kaltem <SEP> Wasser <SEP> ziemlich <SEP> löslich. <SEP> ebenfalls <SEP> in <tb> Pyridin, <SEP> wenig <SEP> löslich <SEP> in <SEP> Alkohol, <SEP> schwer löslieh <SEP> in <SEP> Azeton. <SEP> Xtlier <SEP> und <SEP> Benzol. <SEP> Es <SEP> soll <tb> zur <SEP> I3elzänipfung <SEP> infektiöser <SEP> Erkrankungen. <tb> speziell <SEP> der <SEP> durch <SEP> Strepto-, <SEP> Gono- <SEP> und <tb> Pneumokokken <SEP> verursachten. <SEP> verwendet <SEP> wer den. pyrimidine] calcium. EMI0002.0016 The <SEP> colorless, <SEP> crystalline <SEP> process product <SEP> decomposes <SEP> <SEP> above <SEP>? <I> "3 </I> 0" <SEP> C <SEP> without <SEP> to <tb> scliinelzeri, <SEP> is <SEP> so \ volil <SEP> in <SEP> warm <SEP> as <SEP> also <SEP> in <tb> cold <SEP> water <SEP> fairly <SEP> soluble. <SEP> also <SEP> in <tb> Pyridine, <SEP> slightly soluble <SEP> <SEP> in <SEP> alcohol, <SEP> poorly soluble <SEP> in <SEP> acetone. <SEP> Xtlier <SEP> and <SEP> benzene. <SEP> It should <SEP> <tb> for <SEP> I3elzänipfung <SEP> infectious <SEP> diseases. <tb> especially <SEP> the <SEP> through <SEP> Strepto-, <SEP> Gono- <SEP> and <tb> Pneumococci <SEP> caused. <SEP> is used <SEP>.
CH237324D 1941-10-28 1941-10-28 Process for the preparation of a salt of a derivative of p-amino-benzenesulfonamide. CH237324A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH237324T 1941-10-28
CH213815T 1943-03-13

Publications (1)

Publication Number Publication Date
CH237324A true CH237324A (en) 1945-04-15

Family

ID=25725499

Family Applications (1)

Application Number Title Priority Date Filing Date
CH237324D CH237324A (en) 1941-10-28 1941-10-28 Process for the preparation of a salt of a derivative of p-amino-benzenesulfonamide.

Country Status (1)

Country Link
CH (1) CH237324A (en)

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