CH213815A - 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
CH213815A
CH213815A CH213815DA CH213815A CH 213815 A CH213815 A CH 213815A CH 213815D A CH213815D A CH 213815DA CH 213815 A CH213815 A CH 213815A
Authority
CH
Switzerland
Prior art keywords
pyridine
calcium
salt
sulfonylamino
derivative
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
Application filed by Cilag Chemisches Ind Lab A G filed Critical Cilag Chemisches Ind Lab A G
Publication of CH213815A publication Critical patent/CH213815A/en
Priority to CH213815T priority Critical

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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

  

      Perfabr    en zur Darstellung eines Salzes eines Abkömmlings des     p-Aminobenzolsulfonamids.       Das in neuester Zeit bekannt gewordene       2-(p-Aminobenzol-sulfonylamino-)        pyridin    hat  sich als geeignet erwiesen zur Bekämpfung  infektiöser, insbesondere durch Kokken her  vorgerufener Krankheiten.  



  Es wurde nun gefunden,- dass das durch Er  satz des     Wasserstoffatoms    seiner Sulfonamid  gruppe durch     Kalzium        erhältliche        Kalzium-          salz    des     2-(p-Aminobenzol-sulfonylamino-)py-          ridins    gegenüber der entsprechenden Wasser  stoffverbindung die oben erwähnten therapeu  tischen Eigenschaften in verstärktem Masse  aufweist, ausserdem eine bessere Verträglich  keit besitzt, und, wie aus den klinischen Un  tersuchungen     hervorgeht,    wahrscheinlich auch  einen günstigen Einfluss auf die Tuberkulose  auszuüben vermag.

   Die neue Verbindung soll  daher zur Bekämpfung infektiöser Erkran  kungen, speziell der durch     Strepto-,        Gono-          und        Pneumokokken    verursachten, verwendet  werden.  



  Das erfindungsgemässe Verfahren zur Dar  stellung der neuen Verbindung ist dadurch  gekennzeichnet, dass man 2-(p-Aminobenzol-         sulfonylamino-)pyridin    und eine zum Aus  tausch des     Wasserstoffes    der     Sulfonamidgruppe     gegen     Kalzium    befähigte Verbindung, z. B.       Kalziumhydroxyd,        lösliches        Kalziumsalz,    wie       Kalziumchlorid,    aufeinander     einwirken    lässt,  wobei sich     Di-[2-(p-Aminobenzöl-sulfonyl-          amino-)pyridin-]        calcium    bildet.  



  <I>1. Ausführungsbeispiel:</I>  25 g     2-(p-Aminobenzol-sulfonylamino-)py-          ridin    und<B>3,7</B> g     Kalziumhydroxyd    werden in  700     cm3    heissem Wasser gelöst. Die     Lösung          wird    so lange gekocht, bis die     anfänglich     vorhandene Trübung     beinahe    verschwunden  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>     Ausführungsbeispiel:     Eine Lösung von     2-(p-Aminobenzol-sulfonyl-          amino-)pyridin    in wenig     verdünnter        Salzsäure     wird bis zum Aufhören der Kohlendioxydent-           wicklung    mit     Kalziumkarbonat    versetzt. Das  hierbei ausgefällte     Kalziumsalz    des     2-(p-Amino-          benzol    -     sulfonylamino    -     )pyridins    wird     abge-          nutscht    und aus heissem Wasser umkristalli  siert.  



  <I>3. Ausführungsbeispiel:</I>  10 g     2-(p-Aminobenzol-sulfoiiylamirio-)-py-          ridin    werden in 100 cm'     20-prozentigem     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       Kalziumsatz    des 2 - (p     -Aminobenzol-        sulfonyl-          amino-)pyridiiis    aus und wird nach dem Er  kalten durch Absaugen von der Mutterlauge  getrennt. Die Ausbeute beträgt 10 g ; sie  kann durch Einengen der Mutterlauge erhöht  werden.  



  Die neue Verbindung bildet sechsseitige  Prismen. Sie zersetzt sich beim Erhitzen ohne  zu schmelzen, ist leicht löslich in heissem       Pyridin,    ziemlich gut löslich in kaltem     Pyri-          din    und heissem Wasser, wenig löslich in kal  tem Wasser, in     Alkohol    und     Azeton.  



      Perfabr en for the preparation of a salt of a derivative of the p-aminobenzenesulfonamide. The recently known 2- (p-aminobenzene-sulfonylamino-) pyridine 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-aminobenzene-sulfonylamino) pyridine obtained by replacing the hydrogen atom of its sulfonamide group with calcium increases the above-mentioned therapeutic properties to a greater extent than the corresponding hydrogen compound also has better tolerability and, as the clinical investigations show, is probably also able to exert a beneficial influence on tuberculosis.

   The new compound should therefore be used to combat infectious diseases, especially those caused by streptococci, gonococci and pneumococci.



  The inventive method for the presentation of the new compound is characterized in that 2- (p-aminobenzene sulfonylamino) pyridine and a compound capable of exchanging the hydrogen of the sulfonamide group for calcium, eg. B. calcium hydroxide, soluble calcium salt, such as calcium chloride, can act on each other, with di- [2- (p-aminobenzol-sulfonyl- amino-) pyridine-] calcium being formed.



  <I> 1. Exemplary embodiment: 25 g of 2- (p-aminobenzene-sulfonylamino) pyridine and 3.7 g of calcium hydroxide are dissolved in 700 cm3 of hot water. The solution is boiled until the initial 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> 2nd </I> embodiment example: A solution of 2- (p-aminobenzene-sulfonyl-amino-) pyridine in a little dilute hydrochloric acid is mixed with calcium carbonate until the evolution of carbon dioxide ceases. The calcium salt of 2- (p-aminobenzene - sulfonylamino -) pyridine precipitated in the process is filtered off with suction and recrystallized from hot water.



  <I> 3. Exemplary embodiment: 10 g of 2- (p-aminobenzene-sulfoiiylamirio-) - pyridine are dissolved in 100 cm 'of 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 residue of the 2- (p -aminobenzenesulfonylamino) pyridium 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 connection forms six-sided prisms. It decomposes when heated without melting, is easily soluble in hot pyridine, fairly soluble in cold pyridine and hot water, slightly soluble in cold water, in alcohol and acetone.

 

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines Salzes eines Abkömmlings des p-Aminosulfonamids, dadurch gekennzeichnet, dass man 2-(p-Aniino- benzol-sulfonylamino-)pyridin und eine zum Austausch des Wasserstoffes der Sulfonamid gruppe gegen Kalzium befähigte Verbindung aufeinander einwirken lässt, wobei sich Di- (2 - (p-Aminobenzol - sulfonylamino - ) Claim: method for the preparation of a salt of a derivative of p-aminosulfonamide, characterized in that 2- (p-aniinobenzene-sulfonylamino-) pyridine and a compound capable of exchanging the hydrogen of the sulfonamide group for calcium are allowed to act on one another, wherein di- (2 - (p-aminobenzene - sulfonylamino -) pyridin - calcium bildet. Das Verfahrensprodukt bildet sechsseitige Prismen. Es zersetzt sich beim Erhitzen ohne zu schmelzen, ist leicht löslich in heissem Pyridin, ziemlich gut löslich in kaltem Py- ridin und heissem Wasser, wenig löslich in kaltem Wasser, in Alkohol und Azeton. pyridine - calcium forms. The product of the process forms six-sided prisms. It decomposes on heating without melting, is easily soluble in hot pyridine, fairly soluble in cold pyridine and hot water, sparingly soluble in cold water, in alcohol and acetone. Es soll zur Bekämpfung infektiöser Erkrankungen, speziell der durch Strepto-, Gono- und Pneumo- kokken verursachten, verwendet werden. It is intended to be used to combat infectious diseases, especially those caused by streptococci, gonococci and pneumococci.
CH213815D 1943-03-13 1939-11-03 Process for the preparation of a salt of a derivative of p-aminobenzenesulfonamide. CH213815A (en)

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Application Number Priority Date Filing Date Title
CH213815T 1943-03-13

Publications (1)

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CH213815A true CH213815A (en) 1941-03-15

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CH213815D CH213815A (en) 1943-03-13 1939-11-03 Process for the preparation of a salt of a derivative of p-aminobenzenesulfonamide.

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2613170A (en) * 1944-03-02 1952-10-07 Physiological Chemicals Compan Calcium sulfanilamide preparations

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2613170A (en) * 1944-03-02 1952-10-07 Physiological Chemicals Compan Calcium sulfanilamide preparations

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