DE837694C - Process for the preparation of a new condensation product of 2- (4-aminobenzene-1'-sulfonamido) -thiazole - Google Patents

Process for the preparation of a new condensation product of 2- (4-aminobenzene-1'-sulfonamido) -thiazole

Info

Publication number
DE837694C
DE837694C DEP27044D DEP0027044D DE837694C DE 837694 C DE837694 C DE 837694C DE P27044 D DEP27044 D DE P27044D DE P0027044 D DEP0027044 D DE P0027044D DE 837694 C DE837694 C DE 837694C
Authority
DE
Germany
Prior art keywords
thiazole
sulfonamido
aminobenzene
condensation product
preparation
Prior art date
Legal status (The legal status 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 status listed.)
Expired
Application number
DEP27044D
Other languages
German (de)
Inventor
Dr Otto Allemann
Dr Jean Druey
Dr Max Hartmann
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Novartis AG
BASF Schweiz AG
Original Assignee
Ciba Geigy AG
Ciba 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 Ciba Geigy AG, Ciba AG filed Critical Ciba Geigy AG
Application granted granted Critical
Publication of DE837694C publication Critical patent/DE837694C/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/38—Nitrogen atoms
    • C07D277/50—Nitrogen atoms bound to hetero atoms
    • C07D277/52—Nitrogen atoms bound to hetero atoms to sulfur atoms, e.g. sulfonamides

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Thiazole And Isothizaole Compounds (AREA)

Description

Verfahren zur Herstellung eines neuen Kondensationsproduktes des 2-(4'-Aminobenzol-1'-sulfonamido)-thiazols Die vorliegende Erfindung betrifft die Her- stellung eines Kondensationsproduktes von 2-(4 - .\ininolx@tizol-i'-sulfonamido)-thiazol mit Form- al deliyd. Die neue «\-erhindung ist bei Koickeninfektionen im Gegensatz zu 2-(4 -Aminohenzol-i'-sulfon- amido)-thiazol bei subkutaner und intraperitonaler .11>plikation sehr gut wirksam. Besonders bemer- kenswert ist, (laß sie eine langanhaltende Wirkung zeigt. So haben Versuche mit Mäusen, die mit Streptokokken infiziert waren, ergeben, daß bei einmaliger, sul)kutaner oder intraperitonaler Ver- al)reicliting von 0,5 g/kg der neuen Verbindung alle 'fiere am Leben blieben. Demgegenüber waren mit der entsprechenden Menge 2-(4 -Aminobenzol-i'- sulfonaniido)-thiazol unter den gleichen Bedingun- gen drei Viertel der Tiere nach io Tagen einge- gangen. Das neue Kondensationsprodukt des 2-(4 -=#minol>enzol-i'-sulfonamido)-thiazols wird erhalten, wenn man 2-(4 -Aminobenzol-i'-sulfonamido)-thiazol mit Formaldehyd umsetzt. Statt Formaldehyd selbst können auch Formaldehyd abgebende Mittel, wie Paraformaldehyd oder Hexamethylentetramin, verwendet werden. Die Umsetzung wird vorteilhaft in Gegenwart von Verdünnungsmitteln, wie Wasser, verdünnten Säuren oder organischen Lösungsmitteln, beispielsweise Alkohol, durchgeführt.Process for the preparation of a new condensation product of 2- (4'-aminobenzene-1'-sulfonamido) -thiazole The present invention relates to the manufacture formation of a condensation product of 2- (4 - . \ ininolx @ tizol-i'-sulfonamido) -thiazole with form- al deliyd. The new "\ -invention is with Koicken infections in contrast to 2- (4-aminohenzene-i'-sulfone- amido) -thiazole for subcutaneous and intraperitoneal .11> application very effective. Particularly noteworthy is worth it, (let it have a long-lasting effect shows. So have experiments with mice that with Streptococci were infected, show that one-time, sul) cutaneous or intraperitoneal treatment al) reicliting from 0.5 g / kg of the new compound all 'fiere stayed alive. In contrast, were with the corresponding amount of 2- (4-aminobenzene-i'- sulfonaniido) thiazole under the same conditions three quarters of the animals arrived after 10 days. went. The new condensation product of 2- (4 - = #minol>enzol-i'-sulfonamido) -thiazole is obtained when 2- (4-aminobenzene-i'-sulfonamido) -thiazole is reacted with formaldehyde. Instead of formaldehyde itself, formaldehyde-releasing agents, such as paraformaldehyde or hexamethylenetetramine, can also be used. The reaction is advantageously carried out in the presence of diluents, such as water, dilute acids or organic solvents, for example alcohol.

Die verfahrensgemäß erhaltene Verbindung soll als Heilmittel Verwendung finden. Beispiel i 2j g 2-(4 -Aminobenzol-i'-sulfonamido)-thiazol, suspendiert in 25o cm3 95°/oigem Alkohol, werden unter Rühren bei 75° mit einem auf 75° vorgewärmten Gemisch von i-5 cm3 4oo/oigem Formaldehycl und ioo cm3 95o/oigem Alkohol versetzt. Es tritt dabei für kurze Zeit eine klare Lösunein, aus welcher sich sehr bald das Kondensationsprodukt abzuscheiden beginnt. Man läßt 2.4 Stunden stehen, 'sammelt den entstandenen Niederschlag auf einer N utsche, wäscht mit Alkohol, trocknet und pulverisiert. Die Ausbeute beträgt 27 bis 28 g. Die neue Verbindung schmilzt bei 266° unter Zersetzung. Beispiel e 5o g 2-(4 -Aminobenzol-i'-sulfonamiclo)-thiazol werden in 5oo cm3 etwa normaler Salzsäure gelöst. Unter energischem Rühren werden 24 cm3 qoo/oige wässerige Formaldehydlösung eingetropft. Das Reaktionsprodukt scheidet sich dabei sofort in sehr feiner Form ab. Es wird abgetrennt, zweckmäßig beispielsweise durch Zentrifugieren, mit Wasser gründlich gewaschen und bei ioo° getrocknet. Man erhält so 56 g einer neuen Substanz vom Schmelzpunkt 266° (Zersetzung).The compound obtained according to the method is intended to be used as a medicinal product Find. Example i 2j g 2- (4-aminobenzene-i'-sulfonamido) -thiazole, suspended in 250 cm3 of 95% alcohol are preheated to 75 ° with stirring at 75 ° mixture of i-5 cm3 400% formaldehyde and 100 cm3 95% alcohol. It kicks for a short time a clear solution, from which the condensation product very soon emerges begins to deposit. The mixture is left to stand for 2.4 hours and the precipitate formed is collected on a slide, washes with alcohol, dries and powdered. The yield is 27 to 28 g. The new compound melts at 266 ° with decomposition. example e 50 g of 2- (4-aminobenzene-i'-sulfonamiclo) -thiazole are about more normal in 5oo cm3 Dissolved hydrochloric acid. With vigorous stirring, 24 cm3 qoo / o aqueous formaldehyde solution are added dripped in. The reaction product separates out immediately in a very fine form away. It is separated off, expediently, for example by centrifugation, with water washed thoroughly and dried at 100 °. 56 g of a new substance are obtained in this way melting point 266 ° (decomposition).

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines neuen Kondensationsproduktes des 2-(4 -Aminobenzol-i'-sulfonamido)-thiazolS, dadurch gekennzeichnet, daß man 2-(4 -Amiiiol)enzol-i'-sulfonamido)-thiazol mit Formaldehyd oder Formaldehyd abgebenden Mitteln, zweckmäßig in Gegenwart von Lösungs- oder Verdünnungsmitteln, umsetzt.PATENT CLAIM: Process for the production of a new condensation product des 2- (4-aminobenzene-i'-sulfonamido) -thiazolS, characterized in that one 2- (4-Amiiiol) enzol-i'-sulfonamido) -thiazole with formaldehyde or formaldehyde donating Agents, expediently in the presence of solvents or diluents, reacted.
DEP27044D 1945-11-29 1948-12-25 Process for the preparation of a new condensation product of 2- (4-aminobenzene-1'-sulfonamido) -thiazole Expired DE837694C (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH837694X 1945-11-29

Publications (1)

Publication Number Publication Date
DE837694C true DE837694C (en) 1952-05-02

Family

ID=4540883

Family Applications (1)

Application Number Title Priority Date Filing Date
DEP27044D Expired DE837694C (en) 1945-11-29 1948-12-25 Process for the preparation of a new condensation product of 2- (4-aminobenzene-1'-sulfonamido) -thiazole

Country Status (1)

Country Link
DE (1) DE837694C (en)

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