DE716089C - Process for the preparation of new derivatives of p-aminobenzenesulfonamide - Google Patents

Process for the preparation of new derivatives of p-aminobenzenesulfonamide

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Publication number
DE716089C
DE716089C DEC55266D DEC0055266D DE716089C DE 716089 C DE716089 C DE 716089C DE C55266 D DEC55266 D DE C55266D DE C0055266 D DEC0055266 D DE C0055266D DE 716089 C DE716089 C DE 716089C
Authority
DE
Germany
Prior art keywords
der
derivatives
preparation
aminobenzenesulfonamide
absolute alcohol
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
DEC55266D
Other languages
German (de)
Inventor
Dr Zoltan Foeldi
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.)
Chinoin Private Co Ltd
Original Assignee
Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Zrt
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 Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Zrt filed Critical Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Zrt
Application granted granted Critical
Publication of DE716089C publication Critical patent/DE716089C/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/37—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring

Description

Verfahren zur Herstellung neuer Derivate des p-Aminobenzolsulfonarnids Die therapeutische Verwendung von ver- bindungen. von der Type des p-Aminob,enzol- sulfonamids, insbesondere bei Stneptokokken- infektionen, ist bekannt. Das p-Aminob,enzol- sulfonamid ist aber in Wasser nur im ge- i-inn,,,-xn Maße löslich und daher zur Herst.el- lung von genügend konzentrierten, für Injek- tionen geeigneteiz Lösungen. nicht brauchbar. Die wäßrigen Löstmgen der mit Säuren ge- bildeten Salze haben stark sauren Charakter und sind demzufolge zur Herstellung injizier- barer Lösungen ebenfalls urigeeignet. Gemäß vorliegender Erfindung kann man in Wasser leicht und finit zu Injektionen. geeigneter Reak- tion lösliche p-Aminob,enzolsulfonamidderivate herstellen, wenn man p Aminobenzolsulfamid oder seine im Kam oder in Elen Stickstoff- atomen. substituierten Abkömmlinge der Ein- wirkung von Formaldehydsulfoxylat unter- wirft, wobei die Menge des Formaldehydsulf- axylatS zweckmäßig z Mol ist, berechnet auf i Mol der p-Aminioben7olsulfonamidverhin- dung. Die Umsetzung von p Aminnbenzolsulfan- amiden mit z Mol Sulfoxyl.at ist eine sehr langsame. Es entstehen dahei p =-minobenzolsulfon- ani:dabk#ömmlinge, die zwei Sulfoxylatreste je Mol Sulfonamid gebunden enthalten. Ein geeigneter Ansatz enthält z. B. 5o g p-Amino.- benzolsulfonamid, 75 ; la-istallwasserfreies Formaldehydsulfoxylatnatrium und. ioo cm3 Wasser. Das Erhitzen hat in diesem Falle auf dem Wasserhad bei 7o bis 9o° während ungefähr 2o Stunden. zu erfolgen. Das er- haltene Produkt löst sich spielend leicht in Wasser; beim Ansäuern mit Mineralsäuren fällt aber die freie Säure nicht aus. Das Ab- trennen des Produktes aus dem Re.akti@onsgemisch erfolgt daher. zweckmäßig durch Eingießen in die 6- bis iofache Menge absoluten Alkohols, wobei das Produkt zunächst als klebrige Masse ausfällt. Nach einiger Zeit wird die Flüssigkeit .abgegossen und die klehrige Masse mit frischem absolutem A11>ohol übergossen, wobei sie in eine weiße pulverförmige Masse übergeht. Nach dem Trocknen erhält man ein in Wasser sehr leicht lösliches Produkt, das laut Analyse auf je 2 Stickstoffatome praktisch 3 Schwefelatome enthält; im Produkt entfallen also: zwei Sulfoxylatgruppen auf i Mo1 Aminobenzolsulfonamid.Process for the preparation of new derivatives of p-aminobenzene sulfonamide The therapeutic use of ver ties. of the type of p-aminob, enzol- sulfonamids, especially with stneptococcal infections, is known. The p-aminob, enzol- However, sulfonamide is only present in water i-inn ,,, - xn measure soluble and therefore for the production- sufficient concentration for injection options suitableiz solutions. not usable. The aqueous solutions of those treated with acids The salts formed have a strongly acidic character and are therefore injectable for manufacture also suitable for rustic solutions. According to The present invention can be used in water easy and finite to injections. suitable react tion soluble p-aminob, enzenesulfonamide derivatives produce when you p aminobenzenesulfamide or his in the Kam or in Elen nitrogen atoms. substituted descendants of the effect of formaldehyde sulfoxylate throws, whereby the amount of formaldehyde sulf axylatS is expediently z mol, calculated on i mole of the p-aminioben7olsulfonamidver- manure. The implementation of p Aminnbenzenesulfan- amides with z moles Sulfoxyl.at is a very slow. The result is p = -minobenzenesulfone- ani: dabk # ömmlinge, the two sulfoxylate residues contain bound per mole of sulfonamide. A suitable approach includes z. B. 50 g p-amino. benzenesulfonamide, 75; la-istall anhydrous Formaldehyde sulfoxylate sodium and. ioo cm3 Water. The heating in this case has on the Wasserhad at 7o to 9o ° during about twenty hours. to be done. The The product that is held dissolves in Water; when acidifying with mineral acids but the free acid does not precipitate. The Ab- separation of the product from the Re.akti@onsverbindungen takes place. expediently by pouring into 6 to 10 times the amount of absolute alcohol, the product initially precipitating as a sticky mass. After a while, the liquid is poured off and fresh, absolute alcohol is poured over the sticky mass, turning it into a white powdery mass. After drying, a product is obtained which is very easily soluble in water and which, according to analysis, contains practically 3 sulfur atoms for every 2 nitrogen atoms; In the product there are therefore: two sulfoxylate groups per 1 mol of aminobenzenesulfonamide.

Die Sulfoxylatgruppen sind mittels Titrierens auf Indigok.armin leicht nachweisbar.The sulphoxylate groups are easy by means of titration on Indigok.armine verifiable.

Das die zwei Sulfoxylatgruppenenthaltend c, Erzeugnis weist in wäßriger Lösung eine wesentlich größere Luftbeständigkeit auf als die nur eine Sulfoxyl.atgruppe enthaltende Verbindung. Die wä ßrigen Lösungen reagieren gegen Lakmus.alkalisch, gegen Phenolplithalein hingegen praktisch neutral. Sie befinden sich also innerhalb der für Injektionslösungen g^-eigneten Reaktionsgrenzen. In gleicher Weis: wie das p Aminobenzoisulfonamid kann man auch seine im Kern substituierten Abkömmlinge verwenden. Auch p-Aminobenzolsulfonamide, deren Stickstoffatome teilweise durch Alkyle ersetzt sind, kommen in Betracht.The product containing the two sulfoxylate groups has an aqueous Solution has a much greater air resistance than the only one sulfoxyl.atgruppe containing compound. The aqueous solutions react against lakmus. Alkaline, on the other hand practically neutral to phenolplithalein. So you are within the reaction limits suitable for injection solutions. In the same way: like that p Aminobenzoisulfonamid one can also use its core-substituted derivatives. Also p-aminobenzenesulfonamides, whose nitrogen atoms are partially replaced by alkyls are eligible.

Die antikoldh#ozide Wirksamkeit der Ausgangsstoffe ist in den neuen Verbindungen in praktisch hinreichendem 1-Ial;@c (--rlialten blieben.The antikoldh # ozide effectiveness of the raw materials is in the new Compounds in practically sufficient 1-Ial; @c (-rlialten remained.

Es war schon bekannt (vgl. Comptes rendu= de la Soc. de Blol, Band 121, S. i o,3q: . Lösungen von p AminobenzolsulfOna.niidforma!deliydbisulfitnatrium zu Injektionszwecken zu verwenden. Derartige Injektionsflüssig sind jedoch starr> empfindlich. so daß sie sich schon in einigen Tagen Sehr merklich rötlich färben. Sie sind für längere Zeit wenig lagerfähig. Die neuen. Verfahrensproduhte «-eisen diese Nachteile nicht auf.It was already known (cf. Comptes rendu = de la Soc. De Blol, volume 121, pp. I o, 3q:. Solutions of p AminobenzolsulfOna.niidforma! Deliydbisulfitnatrium to be used for injections. However, such injection liquids are rigid> sensitive. so that they turn very noticeably reddish in a few days. They cannot be stored for a long time. The new. Process products «iron do not have these disadvantages.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung neuer Derivate des p-Aninob,enz,olsulfonamids oder seiner im Ring oder in den Sticl>stoffatomeii substituierten Derivate, dadurch gehen!-- zeichnet, daß man p-Aminobenzolsttifor:- amic' oder seine im Kern -der in den Stickstoffatomen substituierten Derivate der Ehii"-"irlzun- von YorinaldehydsLilf- oxylat in großem überschuß, zweckmäßig von etwa 2 Mol Sulfoxylat auf i _'1Io@ der p Aminot.enzolsulfonamidc-erbii:duit"-, unter Erhitzen auf etwa So' während 2o Stunden unterwirft und danach das Reaktionsge- misch zweckmäßig in, die 5- bis iof:@clic@ Menge absoluten Alkohols gießt, den aus- geschiedenen Niederschlag mit absolutem Alkohol verreibt und schließlich trocknet.
PATENT CLAIM: Process for the preparation of new derivatives of p-aninobium, enz, olsulfonamide or its in the ring or in the stitch substituted derivatives, go through it! - draws that p-aminobenzolsttifor: - amic 'or its in the core -der in the Derivatives substituted by nitrogen atoms der Ehii "-" irlzun- from YorinaldehydsLilf- oxylate in large excess, appropriate of about 2 moles of sulfoxylate to i _'1Io @ der p Aminot.enzolsulfonamidc-erbii: duit "-, under Heat to about 20 hours subject and then the reaction mixed functional in, the 5- to iof: @ clic @ Amount of absolute alcohol pours out divorced precipitate with absolute Alcohol rubs in and finally dries.
DEC55266D 1937-02-13 1938-02-01 Process for the preparation of new derivatives of p-aminobenzenesulfonamide Expired DE716089C (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
HU716089X 1937-02-13

Publications (1)

Publication Number Publication Date
DE716089C true DE716089C (en) 1942-01-13

Family

ID=10980094

Family Applications (1)

Application Number Title Priority Date Filing Date
DEC55266D Expired DE716089C (en) 1937-02-13 1938-02-01 Process for the preparation of new derivatives of p-aminobenzenesulfonamide

Country Status (1)

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DE (1) DE716089C (en)

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