CH259679A - Process for the preparation of a biguanide derivative. - Google Patents

Process for the preparation of a biguanide derivative.

Info

Publication number
CH259679A
CH259679A CH259679DA CH259679A CH 259679 A CH259679 A CH 259679A CH 259679D A CH259679D A CH 259679DA CH 259679 A CH259679 A CH 259679A
Authority
CH
Switzerland
Prior art keywords
preparation
biguanide derivative
iodophenyl
acid
ethyl
Prior art date
Application number
Other languages
German (de)
Inventor
Limited Imperial Ch Industries
Original Assignee
Ici Ltd
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 Ici Ltd filed Critical Ici Ltd
Publication of CH259679A publication Critical patent/CH259679A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C279/20—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylguanidines
    • C07C279/24—Y being a hetero atom
    • C07C279/26—X and Y being nitrogen atoms, i.e. biguanides

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Description

  

  Verfahren zur Herstellung eines     Biguanidderivates.       Die vorliegende Erfindung betrifft ein  Verfahren zur Herstellung von     XL'-p-Jod-          phenyl-N'-äthylbiguanid,    welches ein wert  volles chemotherapeutisches Mittel ist oder  als Zwischenprodukt für die     Herstellung    von  chemotherapeutischen Mitteln verwendet wer  den kann.     Es    ist insbesondere ein wertvolles       Antimalariamittel.     



  Erfindungsgemäss wird die besagte neue  Verbindung, nämlich     N'-p-Jodphenyl-N'-          äthylbiguanid,    dadurch erhalten, dass man       N3-Äthyldieyandia.mid    mit     p-Jodanilin    um  setzt.  



  Die Umsetzung erfolgt zweckmässig durch  Erhitzen eines .Salzes des Amins mit dem  substituierten     Dicyandiamid    in Gegenwart  eines     Lösungsmittels,    wie z. B. Wasser oder       ss-Ätlioxyäthanol.     



  Das N' -     p    -     Jodphenyl-N'    -     äthylbiguanid     stellt     eine    starke     Base    dar, welche mit orga  nischen und anorganischen Säuren beständige  Salze ergibt, die in manchen Fällen in Was  ser leicht     löslich    sind.

   Die Salze lasen sich  dadurch     herstellen,    dass die Base in     wässrigen          Gösizngen    der Säure gelöst und hierauf das       Wasser    verdampft wird, doch können sie in  trockener Form bequemer durch     Vermischen     der Komponenten in     einem    organischen Lö  sungsmittel,     wie    z. B. Aceton, oder in einem  Alkohol, in welchem die Salze spärlich lös  lich sind, hergestellt. werden.

   Auf diese Weise  kann     man        beispielsweise    die Salze mit     Essig-          k#       säure, Milchsäure,     Methansulfonsäure,        Me-          thylendisalicylsäure,        llethylen,-bis-ss-oxy-          naphthoesä.ure    und Salzsäure bequem     her-          .stellen.     



  Das folgende Beispiel diene zur Erläute  rung der Erfindung.    <I>Beispiel:</I>  Ein Gemisch von 15 Teilen     N3-Äthyl-          dicyandiamid    und 31 Teilen     p-Jodanilin-          chlorhydrat    in 75 Teilen     ss-Äthoxyäthanol     wird während 3 Stunden     unter        Rückfluss     zum .Sieden erhitzt. Hierauf lässt man das  Gemisch abkühlen, worauf     abfiltriert    wird.  Der feste     Rückstand    wird mit kaltem     Äthyl-          acetat    gewaschen und aus Wasser umkristal  lisiert.

   Auf     diese    Weise erhält man     Nl-p-Jod-          phenyl-N'-äthylbigua.nid    in Form eines       Monohydrochlorids,    welches bei. 239 bis  2400 C schmilzt.



  Process for the preparation of a biguanide derivative. The present invention relates to a process for the preparation of XL'-p-iodophenyl-N'-ethylbiguanide, which is a valuable chemotherapeutic agent or can be used as an intermediate for the preparation of chemotherapeutic agents. It is a particularly valuable antimalarial drug.



  According to the invention, the said new compound, namely N'-p-iodophenyl-N'-ethylbiguanide, is obtained by reacting N3-Äthyldieyandia.mid with p-iodoaniline.



  The reaction is conveniently carried out by heating a .Salzes of the amine with the substituted dicyandiamide in the presence of a solvent, such as. B. water or ß-Ätlioxyäthanol.



  The N '- p - iodophenyl-N' - äthylbiguanid is a strong base which, with organic and inorganic acids, results in stable salts, which in some cases are easily soluble in water.

   The salts can be prepared in that the base is dissolved in aqueous Gösizngen of the acid and then the water is evaporated, but they can be more convenient in dry form by mixing the components in an organic solvent such as. B. acetone, or in an alcohol in which the salts are sparsely soluble Lich made. will.

   In this way, for example, the salts with acetic acid, lactic acid, methanesulfonic acid, methylenedisalicylic acid, ethylene, bis-ss-oxynaphthoic acid and hydrochloric acid can be conveniently prepared.



  The following example serves to explain the invention. <I> Example: </I> A mixture of 15 parts of N3-ethyl dicyandiamide and 31 parts of p-iodoaniline chlorohydrate in 75 parts of ß-ethoxyethanol is refluxed to boiling for 3 hours. The mixture is then allowed to cool and it is filtered off. The solid residue is washed with cold ethyl acetate and recrystallized from water.

   In this way, Nl-p-iodophenyl-N'-äthylbigua.nid is obtained in the form of a monohydrochloride, which in. Melts from 239 to 2400 C.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von Nl-p-Jod- phenyl-N '-iithylbigua.nid. dadurch gekenn zeichnet, dass ma.n N''-Äthyldicyandiamid mit p-Jodanilin umsetzt. Das N'-p-Jodphenyl-N'-äthylbiguanid ist. eine starke Base, deren Monohydrochlorid bei. 239 bis 240 C schmilzt. Die neue Base besitzt kräftige Antimalariaeigenschaften. PATENT CLAIM: Process for the production of Nl-p-iodo- phenyl-N '-iithylbigua.nid. characterized in that ma.n reacts N '' - ethyl dicyandiamide with p-iodoaniline. The N'-p -iodophenyl-N'-ethyl biguanide is. a strong base whose monohydrochloride is at. Melts from 239 to 240 C. The new base has powerful anti-malarial properties.
CH259679D 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative. CH259679A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB259679X 1945-10-08
GB170946X 1946-09-17
CH254800T 1946-10-08

Publications (1)

Publication Number Publication Date
CH259679A true CH259679A (en) 1949-01-31

Family

ID=27178035

Family Applications (1)

Application Number Title Priority Date Filing Date
CH259679D CH259679A (en) 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative.

Country Status (1)

Country Link
CH (1) CH259679A (en)

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