CH237323A - 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
CH237323A
CH237323A CH237323DA CH237323A CH 237323 A CH237323 A CH 237323A CH 237323D A CH237323D A CH 237323DA CH 237323 A CH237323 A CH 237323A
Authority
CH
Switzerland
Prior art keywords
amino
benzene
salt
pyrimidine
derivative
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
Application filed by Cilag Chemisches Ind Lab Ag filed Critical Cilag Chemisches Ind Lab Ag
Priority to CH237323T priority Critical
Priority to CH213815T priority
Publication of CH237323A publication Critical patent/CH237323A/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 neuerer Zeit bekannt gewordene  2     -(p-Amino-benzol-sulfonylamino-)        pyrimidin     hat sich als geeignet erwiesen zur Bekämp  fung 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 -     Amino    - Benzol -     sulfonyl-          amino-)pyrimidins        gegenüber    der entspre  chenden Wasserstoffverbindung die oben er  wähnten therapeutischen Eigenschaften in  verstärktem Masse aufweist, ausserdem eine  bessere Verträglichkeit besitzt, und, wie aus  den klinischen Untersuchungen hervorgeht,  wahrscheinlich auch einen günstigen Einfluss  auf die Tuberkulose auszuüben vermag.

   Die  neue Verbindung soll daher zur Bekämpfung  infektiöser Erkrankungen, speziell der durch       Strepto-,        Gono-    und     P'neumokokken    verur  sachten, verwendet werden.  



  Das erfindungsgemässe Verfahren zur  Darstellung der neuen Verbindung ist da-    durch gekennzeichnet, dass man     2-(p-Amino-          benzol-sulfonylamino-)pyrimidin    und eine  zum Austausch des Wasserstoffes der     Sul-          fonamidgruppe    gegen Kalzium befähigte  Verbindung, z.

   B.     Kalziumhydrogyd,    lös  liches     Kalziumsalz,    wie     Kalziumchlorid,    auf  einander einwirken lässt, wobei sich das     Di-          [2        --(p,-        Amino-benzol-sulfonylamino-)        pyrimi-          dinl        calcium    bildet.  



  <I>1.</I>     Ausführungsbeispiel:     25 g     2-(p-Amino-benzol-sulfonylamino-)          pyrimidin    und $,7 g     galziumhydrogyd    wer  den in 700 cm' heissem Wasser gelöst. Die  Lösung wird so lange gekocht, bis die an  fänglich vorhandene Trübung beinahe ver  schwunden ist; hierauf wird die noch heisse  Lösung mit Tierkohle versetzt und filtriert.  Beim Erkalten kristallisiert das     Kalziumsalz     grösstenteils aus. Weitere Mengen können  durch Einengen der Mutterlauge gewonnen  werden.

        <I>2.</I>     Aucführ-acngsbeisp;el     Eine Lösung von     2-(p-Amino-benzol-sul-          fony        lamino-)        py        rimidin    in     tvenig    verdünnter  Salzsäure wird bis zum Aufhören der     Koli-          lendioxy        dentwicklung    mit     Kalziumkarbonat     versetzt.

   Das hierbei ausgefällte     Kalziumsalz     des     2-(p-Amino-benzol-sulfonylaniino-)pyri-          midins    wird     abgenutseht    und aus heissem  Wasser umkristallisiert.  



  <I>3.</I>     Aicsfülar?cngsbeispiel:     10 g     \?-(p        Amino-benzol-sulfonylamino-)-          pyrimidin    werden in 100 cm'     20prozentigem     Ammoniak in der Hitze gelöst. Zu dieser Lö  sung wird eine wässerige, konzentrierte Lö  sung von     Kalziumchlorid    im Überschuss zu  gegeben. Nach einiger Zeit kristallisiert das       Kalziumsalz    des     2-(p-Amino-benzol-sulfonyl-          amino-)pyrimidin    aus und     wird    nach dem  Erkalten durch Absaugen von der Mutter  lauge getrennt.

   Die Ausbeute beträgt 10     g-,     sie kann durch Einengen der Mutterlauge er  höht werden.  



  Die neue, farblose, kristalline Verbin  dung zersetzt sich beim Erhitzen ohne zu  schmelzen, ist leicht löslich in heissem Pvri-         din,    ziemlich gut löslich in kaltem     Pyridin     und heissem Wasser, wenig löslich in kaltem  Wasser, in Alkohol und     Azeton.  



  Process for the preparation of a salt of a derivative of p-amino-benzenesulfonamide. The recently known 2- (p-amino-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 - amino - benzene - sulfonylamino) pyrimidine, which can be obtained by replacing the hydrogen atom of its sulfonamide group with calcium, enhances the therapeutic properties mentioned above compared with the corresponding hydrogen compound Has mass, also has a better tolerance, and, as can be seen from the clinical investigations, is probably also able to exert a favorable influence on tuberculosis.

   The new compound should therefore be used to combat infectious diseases, especially those caused by strepto-, gono- and pneumococci.



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

   B. calcium hydrogen, soluble calcium salt, such as calcium chloride, can act on each other, with the di- [2 - (p, - amino-benzene-sulfonylamino-) pyrimidine calcium forms.



  <I> 1. </I> embodiment example: 25 g of 2- (p-amino-benzene-sulfonylamino-) pyrimidine and $, 7 g of calcium hydrogen are dissolved in 700 cm 'of hot water. The solution is boiled until the initially existing cloudiness has almost disappeared; the still hot solution is then mixed with animal charcoal and filtered. Most of the calcium salt crystallizes out on cooling. Further quantities can be obtained by concentrating the mother liquor.

        <I> 2. </I> Aucführ-acngsbeisp; el A solution of 2- (p-amino-benzene-sulphonylamino-) pyrimidine in slightly diluted hydrochloric acid is mixed with calcium carbonate until the development of colil dioxide ceases .

   The calcium salt of 2- (p-amino-benzene-sulfonylaniino-) pyrimidine which has precipitated out in this way is removed by suction and recrystallized from hot water.



  <I> 3. </I> Aicsfülar? Cng example: 10 g \? - (p Amino-benzene-sulfonylamino-) - pyrimidine are dissolved in 100 cm '20 percent ammonia in the heat. An aqueous, concentrated solution of calcium chloride in excess is added to this solution. After some time, the calcium salt of 2- (p-amino-benzene-sulfonyl-amino) pyrimidine crystallizes out and, after cooling, is separated from the mother liquor by suction.

   The yield is 10 g, it can be increased by concentrating the mother liquor.



  The new, colorless, crystalline compound decomposes when heated without melting, is easily soluble in hot pvidin, fairly soluble in cold pyridine and hot water, sparingly soluble in cold water, in alcohol and acetone.

 

Claims (1)

PATENTANSPRUCFI: Verfahren zur Darstellung eines Salzes eines Abkömmlings des p-Amino-benzol-sul- fonamids, dadurch gekennzeichnet, dass man 2 -(p-Aniino-benzol-sulfonylamino-)pyrimidin und eine zum Austausch des Wasserstoffes der Sulfona,midgruppe gegen Kalzium be fähigte Verbindung aufeinander einwirken lässt, wobei sich das Di- [2-(p- Amino-benzol- sulfonylainino-)pyriniidinl-ealcitim bildet. PATENT CLAIM: Process for the preparation of a salt of a derivative of p-amino-benzene-sulphonamide, characterized in that 2 - (p-aniino-benzene-sulphonylamino-) pyrimidine and one to exchange the hydrogen of the sulphonamido group for calcium be able compound can act on each other, whereby the di- [2- (p-amino-benzenesulfonylainino-) pyriniidinl-ealcitim is formed. Das farblose, kristalline Verfahrenspro dukt zersetzt sich beim Erhitzen ohne zu schmelzen, ist leieht löslich in heissem Pyri- din, ziemlich gut löslich in kaltem Pyridin und heissem Wasser, wenig löslich in kaltem Wasser, in Alkohol und Azeton. Es soll zur Bekämpfung infektiöser Erkrankungen, spe ziell der durch Strepto-, Gono- und Pneumo- kokken verursachten, verwendet werden. The colorless, crystalline process product decomposes when heated without melting, is slightly soluble in hot pyridine, fairly soluble in cold pyridine and hot water, slightly soluble in cold water, in alcohol and acetone. It is to be used to combat infectious diseases, especially those caused by streptococci, gonococci and pneumococci.
CH237323D 1941-10-28 1941-10-28 Process for the preparation of a salt of a derivative of p-amino-benzenesulfonamide. CH237323A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
CH237323T 1941-10-28
CH213815T 1943-03-13

Publications (1)

Publication Number Publication Date
CH237323A true CH237323A (en) 1945-04-15

Family

ID=25725498

Family Applications (1)

Application Number Title Priority Date Filing Date
CH237323D CH237323A (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) CH237323A (en)

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