CH237572A - Process for the preparation of 2-acetylamino-thiazole-5-sulfonamide. - Google Patents

Process for the preparation of 2-acetylamino-thiazole-5-sulfonamide.

Info

Publication number
CH237572A
CH237572A CH237572DA CH237572A CH 237572 A CH237572 A CH 237572A CH 237572D A CH237572D A CH 237572DA CH 237572 A CH237572 A CH 237572A
Authority
CH
Switzerland
Prior art keywords
sulfonamide
thiazole
acetylamino
preparation
aminothiazole
Prior art date
Application number
Other languages
German (de)
Inventor
Georg Henning Chem Pharm Gmbh
Original Assignee
Georg Henning Chem Pharm Werk
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 Georg Henning Chem Pharm Werk filed Critical Georg Henning Chem Pharm Werk
Publication of CH237572A publication Critical patent/CH237572A/en

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Description

  

  Verfahren zum Herstellen von     2-Acetylamino-thiazol-5-sulfonamid.       Die bakteriziden Wirkungen von     p-Amino-          benzolsulfonamid    sind seit längerer Zeit be  kannt, und es ist auch versucht worden, diese  zur Bekämpfung bakterieller Infektionen  nutzbar zu machen.

   Durch Änderungen die  ses Körpers durch Substitution,     insbesondere     in der     Sulfonamidgruppe,    sind Verbesserun  gen hinsichtlich der Wirksamkeit und Ver  träglichkeit erzielt worden, wobei sich insbe  sondere gezeigt hat, dass die Einführung des       Pyridin-        bezw.    des     Thiazolringes        (2-Sulfani-          lylaminopyridin        bezw.        2-Sulfanilylaminothi-          azol)    günstig wirkt.

   Es sind auch     2-Amino-          pyridin-        bezw.        -pyrimidin-5-sulfonamide    her  gestellt worden, die ebenfalls bakterizide Ei  genschaften zeigen. In all diesen Verbindun  gen liegt als Grundkörper ein Sechsring vor,  in welchem sich die     Amino-    und die     Sulfon-          amidgruppe    in     Parastellung    befinden.  



  Nach dem vorliegenden Verfahren wird  eine neue Verbindung hergestellt, die als  Grundkörper nicht einen Sechs-, sondern    einen Fünfring, nämlich den     Thiazolring    ent  hält, in welchem sich die     Amino-    und die       Sulfonamidgruppe    in 2-,     5-Stellung    gegen  überstehen. Trotz der von den vorstehend er  wähnten bekannten Verbindungen abwei  chenden Struktur weist der neue Stoff stark  bakterizide Wirkungen auf; ausserdem sind  in ihm die für eine chemotherapeutische Ver  wendung erforderlichen Eigenschaften in  günstiger Weise vereinigt. Die Verbindung  zeichnet sich auch durch besonders gute Re  sorptionsfähigkeit aus.  



  Erfindungsgemäss wird die neue Verbin  dung, das 2 -     Acetylamino    -     thiazol    - 5 -     sulfon-          amid,    hergestellt durch Umsetzen von     acety-          liertem        2-Aminothiazol-5-sulfochlorid    mit       Ammoniumverbindungen,    aus denen die       Aminogruppe    in das Endprodukt übergeht.       Geeignet    hierfür sind     Ammoniumhydrogyd     und     Ammoncarbonat.    Das     2-Acetyl-amino-          thiazol-5-sulfonamid    hat den Zersetzungs  punkt 262 .

   Es ist schwer löslich in Wasser      und Alkohol, leicht löslich in Aceton, unlös  lich in Benzol und     rlther.     



  Das     2-Aminothiazol    kann     iiacli    Treu  mann ("Annalen der Chemie", Band 249,  Seite 36) aus     Dichloräthyläther    und     Thio-          harnstoff    hergestellt  -erden. Es kann in  Form seiner     Acetylverbindung    durch     vorsich-          ti(re    Behandlung mit     Chlorsulfonsäure    zum       Sulfochlorid    umgesetzt      -erden,    das als Aus  gangsmaterial des vorliegenden Verfahrens  dient.  



       Beispiel:     1 g     2-Acetylamino-tliiazol-5-sulfoelilorid     wird in wenig Aceton gelöst und mit einem  kleinen     Lfiberschuss    an     25i;igem    Ammoniak  versetzt. Aceton und     "Wasser    werden ver  dampft und das aus dem Rückstand mit Al  kohol extrahierte     2-Acetylamino-thiazol-5-          sulfonamid    aus Wasser mit Tierkohle um-    kristallisiert. Farblose Kristalle, die sich un  ter     Diuikelfärben    bei<B>262'</B> zersetzen.  



  Die     erfindungsgemäss    hergestellte Verbin  dung soll als Heilmittel verwendet werden.



  Process for the preparation of 2-acetylamino-thiazole-5-sulfonamide. The bactericidal effects of p-aminobenzenesulfonamide have been known for a long time, and attempts have also been made to make them useful for combating bacterial infections.

   By changes this body through substitution, especially in the sulfonamide group, improvements have been made in terms of effectiveness and tolerability, and it has been shown in particular that the introduction of the pyridine and respectively. of the thiazole ring (2-sulfanilylaminopyridine or 2-sulfanilylaminothiazole) has a favorable effect.

   There are also 2-aminopyridine respectively. -pyrimidine-5-sulfonamides have been made, which also show bactericidal properties. In all of these compounds there is a six-membered ring in which the amino and sulfonamide groups are in the para position.



  According to the present process, a new compound is produced which, as a basic body, does not have a six-membered ring but a five-membered ring, namely the thiazole ring, in which the amino and sulfonamide groups face each other in the 2-, 5-position. Despite the structure deviating from the known compounds mentioned above, the new substance has strong bactericidal effects; In addition, the properties required for chemotherapeutic use are advantageously combined in it. The connection is also characterized by particularly good absorption capacity.



  According to the invention, the new compound, 2-acetylamino-thiazole-5-sulfonamide, is produced by reacting acetylated 2-aminothiazole-5-sulfochloride with ammonium compounds from which the amino group is converted into the end product. Ammonium hydrogen and ammonium carbonate are suitable for this. The 2-acetyl-aminothiazole-5-sulfonamide has the decomposition point 262.

   It is sparingly soluble in water and alcohol, slightly soluble in acetone, and insoluble in benzene and ether.



  The 2-aminothiazole can iiacli Treu mann ("Annalen der Chemie", Volume 249, page 36) produced -erden from dichloroethyl ether and thiourea. In the form of its acetyl compound, careful treatment with chlorosulfonic acid can convert it to sulfochloride, which is used as the starting material for the present process.



       Example: 1 g of 2-acetylamino-thiiazole-5-sulfoeliloride is dissolved in a little acetone and mixed with a small excess of 25% ammonia. Acetone and water are evaporated and the 2-acetylamino-thiazole-5-sulfonamide extracted from the residue with alcohol is recrystallized from water with animal charcoal. Colorless crystals, which turn under a yellow color at <B> 262 '</ B > decompose.



  The compound produced according to the invention is intended to be used as a remedy.

 

Claims (1)

PATENTANSPRUCH: Verfahren zum Herstellen von 2-Acetyl- ainino-thiazol-)-sulfonamid, dadurch gekenn zeichnet, dass man acetyliertes 2-Aminothi- azol-5-sulforlilorid mit einer Ammoniumver- bindung umsetzt, aus der die Aminogruppe in das Endprodukt übergeht. Das Produkt hat den Zersetzungspunkt 26 ? . Es ist schwer löslich in NVasser und Alkohol, leicht löslich in Aceton, unlöslieli in Benzol und Äther. PATENT CLAIM: Process for producing 2-acetyl-ainino-thiazole -) - sulfonamide, characterized in that acetylated 2-aminothiazole-5-sulfonamide is reacted with an ammonium compound from which the amino group is converted into the end product. The product has a decomposition point of 26? . It is sparingly soluble in water and alcohol, easily soluble in acetone, and insoluble in benzene and ether.
CH237572D 1941-04-09 1942-03-27 Process for the preparation of 2-acetylamino-thiazole-5-sulfonamide. CH237572A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE237572X 1941-04-09
CH231794T 1942-03-27

Publications (1)

Publication Number Publication Date
CH237572A true CH237572A (en) 1945-04-30

Family

ID=25727632

Family Applications (1)

Application Number Title Priority Date Filing Date
CH237572D CH237572A (en) 1941-04-09 1942-03-27 Process for the preparation of 2-acetylamino-thiazole-5-sulfonamide.

Country Status (1)

Country Link
CH (1) CH237572A (en)

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