CH213816A - 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.

Info

Publication number
CH213816A
CH213816A CH213816DA CH213816A CH 213816 A CH213816 A CH 213816A CH 213816D A CH213816D A CH 213816DA CH 213816 A CH213816 A CH 213816A
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
Priority claimed from CH213816T external-priority
Application filed by Cilag Chemisches Ind Lab A G filed Critical Cilag Chemisches Ind Lab A G
Publication of CH213816A publication Critical patent/CH213816A/en

Links

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-Aminobenzol-sulfonylamino-)pyridin    hat  sich als geeignet erwiesen zur Bekämpfung  infektiöser, insbesondere durch Kokken her  vorgerufener     Krankheiten.     



  Es wurde     nun    gefunden, dass das durch  Ersatz des Wasserstoffatoms seiner     Sulfon-          amidgruppe    durch     Kalzium        erhältliche        Kal-          ziumsalz    des     2-(p.Aminobenzol-sulfonylamino-)-          pyridins    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     Tln-          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        -Acylamino-          benzol-        sulfonylamino        -)pyridin    mit einer Lö  sung von     Kalziumhydroxyd    behandelt, wobei  durch     Verseifung    der     Acylgruppe    und Ersatz  des am     Amidostickstoff    sitzenden Wasserstoff  atoms     durchKalzium    das     Di-[2-(p-Aminobenzol-          sulfonylamino-)

  pyridin-]        calcium    entsteht.    <I>1.</I>     Ausführungsbeispiel,:       5 g     2-(p-Acetylaminobenzol-sulfonylamino-)-          pyridin    werden mit     einer    Lösung von 5 g       Kalziumhydroxyd        üi    250     cm3    Wasser 35 Stun  den verkocht.

   Das beim Abkühlen auskristal  lisierende     Di    - [2 - (p -     Aminobenzol-        sulfonyl-          amino-)pyridin-]calcium    wird     gesammelt;    die  Ausbeute beträgt 5 g und     kann    durch Ein  engen der Mutterlauge erhöht werden. Die       Reinigung    erfolgt     durch        Umkristallisieren    aus  heissem Wasser.

      <I>2.</I>     Ausführungsbeispiel:     5 g     2-(p-Acetylaminobenzol-sulfonylamino-)-          pyridin    werden mit     einer    Lösung von 5 g           Katziumhydroxyd    in 250 cm' Wasser 10 Stun  den auf 130   C erhitzt. Die Hydrolyse des       Acetylrestes    erfolgt bei dieser Temperatur be  deutend schneller. Aufarbeitung des Verfah  rensproduktes wie     im    Beispiel 1 geschildert.  



  Die neue Verbindung bildet     sechsseitige     Prismen. Sie zersetzt sich beim Erhitzen ohne  zu schmelzen, ist leicht löslich in heissem     Py-          ridin,    ziemlich gut löslich in     kapern        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-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, which can be obtained by replacing the hydrogen atom of its sulfonamide group with calcium, has the above-mentioned therapeutic properties to a greater extent than the corresponding hydrogen compound. also has a better tolerability and, as can be seen from the clinical examinations,

       likely to have 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 -acylamino-benzenesulfonylamino-) pyridine is treated with a solution of calcium hydroxide, saponification of the acyl group and replacement of the hydrogen atom on the amido nitrogen with calcium the di- [2- (p-aminobenzenesulfonylamino-)

  pyridine] calcium is formed. <I> 1st </I> embodiment example: 5 g 2- (p-acetylaminobenzene-sulfonylamino-) - pyridine are boiled for 35 hours with a solution of 5 g calcium hydroxide in 250 cm3 water.

   The di - [2 - (p - aminobenzenesulfonylamino) pyridine] calcium, which crystallizes out on cooling, is collected; the yield is 5 g and can be increased by narrowing the mother liquor. The cleaning is done by recrystallization from hot water.

      <I> 2nd </I> exemplary embodiment: 5 g of 2- (p-acetylaminobenzene-sulfonylamino-) - pyridine are heated to 130 C for 10 hours with a solution of 5 g of potassium hydroxide in 250 cm of water. The hydrolysis of the acetyl radical takes place significantly faster at this temperature. Work-up of the process product as described in Example 1.



  The new connection forms six-sided prisms. It decomposes on heating without melting, is easily soluble in hot pyridine, fairly soluble in large 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-Aminobenzolsulfori- amids, dadurch gekennzeichnet, dass man 2- (p- Acylaminobenzol - sulfonylamino-) pyridin mit einer Lösung von Kalziumhydroxy d be- handelt, PATENT CLAIM Process for the preparation of a salt of a derivative of p-aminobenzenesulforiamide, characterized in that 2- (p-acylaminobenzene - sulfonylamino) pyridine is treated with a solution of calcium hydroxide, wobei durch Verseifung der Acyl- gruppe und Ersatz des am Amidostickstoff sitzenden Wasserstoffatoms durch Kalzium das Di-[2-(p-Aminobenzol.sulfonylamino-)pyridin.]. calcium entsteht. Das Verfahrensprodukt bildet sechsseitige Prismen. Es zersetzt sich beim Erhitzen ohne zu schmelzen, ist leicht löslich in heissem Pyridin, ziemlich gut löslich in kaltem Pyridin und heissem Wasser, wenig löslich in kaltem Wasser, in Alkohol und Azeton. where by saponification of the acyl group and replacement of the hydrogen atom on the amido nitrogen with calcium, the di- [2- (p-aminobenzene.sulfonylamino) pyridine.]. calcium is formed. The product of the process 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. Es soll zur Bekämpfung infektiöser Erkrankungen, speziell der durch Strepto-, Caono- und Pneumokokken verursachten, verwendet werden. It is said to be used to combat infectious diseases, especially those caused by streptococci, caonococci and pneumococci.
CH213816D 1943-06-23 1939-11-21 Process for the preparation of a salt of a derivative of p-aminobenzenesulfonamide. CH213816A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH213816T 1943-06-23

Publications (1)

Publication Number Publication Date
CH213816A true CH213816A (en) 1941-03-15

Family

ID=4448416

Family Applications (1)

Application Number Title Priority Date Filing Date
CH213816D CH213816A (en) 1943-06-23 1939-11-21 Process for the preparation of a salt of a derivative of p-aminobenzenesulfonamide.

Country Status (1)

Country Link
CH (1) CH213816A (en)

Similar Documents

Publication Publication Date Title
CH213816A (en) Process for the preparation of a salt of a derivative of p-aminobenzenesulfonamide.
CH213815A (en) Process for the preparation of a salt of a derivative of p-aminobenzenesulfonamide.
CH237327A (en) Process for the preparation of a salt of a derivative of p-amino-benzenesulfonamide.
CH221518A (en) Process for the preparation of a salt of a derivative of p-aminobenzenesulfonamide.
AT165327B (en) Process for the preparation of pantothenic acid
CH237323A (en) Process for the preparation of a salt of a derivative of p-amino-benzenesulfonamide.
CH212060A (en) Process for the preparation of a derivative of 2-aminopyridine.
CH209822A (en) Process for the preparation of a thiazolium compound.
DE477577C (en) Process for the preparation of salts of papaverine
CH221517A (en) Process for the preparation of a salt of a derivative of p-aminobenzenesulfonamide.
CH214351A (en) Process for the preparation of a derivative of 2-aminopyridine.
DE339101C (en) Process for the preparation of ethers of p-oxyphenylcarbamide
CH221515A (en) Process for the preparation of a salt of a derivative of p-aminobenzenesulfonamide.
CH221516A (en) Process for the preparation of a salt of a derivative of p-aminobenzenesulfonamide.
CH212062A (en) Process for the preparation of a derivative of 2-aminopyridine.
CH209816A (en) Process for the preparation of a thiazolium compound.
DE876999C (en) Process for the production of pellets of 4-aminobenzenesulfonamide
CH237322A (en) Process for the preparation of a salt of a sulfonamide.
CH213150A (en) Process for the preparation of a derivative of 2-amino-6-methylpyridine.
CH209819A (en) Process for the preparation of a thiazolium compound.
CH209823A (en) Process for the preparation of a thiazolium compound.
CH209817A (en) Process for the preparation of a thiazolium compound.
CH234673A (en) Process for the preparation of caffeine from xanthine.
CH237326A (en) Process for the preparation of a salt of a sulfonamide.
CH193539A (en) Process for the preparation of salicylacetyl glycol ester.