CH259677A - Process for the preparation of a biguanide derivative. - Google Patents

Process for the preparation of a biguanide derivative.

Info

Publication number
CH259677A
CH259677A CH259677DA CH259677A CH 259677 A CH259677 A CH 259677A CH 259677D A CH259677D A CH 259677DA CH 259677 A CH259677 A CH 259677A
Authority
CH
Switzerland
Prior art keywords
preparation
iodophenyl
biguanide derivative
acid
biguanide
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 CH259677A publication Critical patent/CH259677A/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)

Description

  

  Verfahren zur Herstellung eines     Biguanidderivates.       Die vorliegende Erfindung     betrifft    ein  Verfahren zur Herstellung von     N'-p-Jod-          phenyl-N'-isopropylbigua.nid,    welches ein       wertvolles    chemotherapeutisches Mittel ist  oder als Zwischenprodukt für die Herstel  lung von     chemotherapeutisehen    Mitteln ver  wendet werden kann. Es ist insbesondere ein  wertvolles     Antimalariamittel.     



  Erfindungsgemäss wird die besagte neue  Verbindung, nämlich     Nl-p-Jodphenyl-N'-iso-          propylbiguanid,    dadurch erhalten, dass man       N3-Isopropyldieyandiami.d    mit.     p-Jodanilin     umsetzt.  



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



  Das     NI-p-Jodphenyl-N'-isopropylbiguanid     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 lassen sich  dadurch herstellen,     da.ss    die Base in     wässrigen          Lösungen    der Säure gelöst und hierauf das       Wasser    verdampft wird, doch können sie in  trockener Form bequemer durch Vermischen  der     K;omponen.ten    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-    säure, Milchsäure,     Methansulfonsäure,        Me-          thylendisalicylsä-ure,        Methylen-bi,s    -     ss    -     oxy-          naphthoesäure    und Salzsäure bequem her  stellen.  



  Das<B>,</B> folgende Beispiel diene zur Erläute  rung der Erfindung.  



       Beispiel:     Ein Gemisch von 12,6 Teilen.     N3-Isopro-          pyldicyandiamid    und 26 Teilen     p-Jodanilin-          chlorhydTat    in 100 Teilen     p-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     Athyl-          acetat    gewaschen und aus Wasser     umkristal-          lisiert.    Auf diese Weise erhält man     N'-p-Jod-          phenyl-N'-isopropylbigua.nid    in Form seines       Monohydrochlorids,    welches bei     239     C  schmilzt.



  Process for the preparation of a biguanide derivative. The present invention relates to a process for the preparation of N'-p-iodophenyl-N'-isopropylbigua.nid, 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 Nl-p-iodophenyl-N'-isopropyl biguanide, is obtained by using N3-isopropyldieyandiami.d with. p-iodaniline converts.



  The reaction is conveniently carried out by heating a salt of the amine with the substituted dicya, ndiamide in the presence of a solvent, such as B. water or ss-ethoxyethanol.



  The NI-p-iodophenyl-N'-isopropylbiguanid 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 by dissolving the base in aqueous solutions of the acid and then evaporating the water, but they can be more conveniently prepared in dry form by mixing the components in an organic solvent, e.g. B. acetone, or in an alcohol in which the salts are sparselös Lich are prepared.

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



  The following example serves to explain the invention.



       Example: A mixture of 12.6 parts. N3-isopropyldicyandiamide and 26 parts of p-iodoaniline chlorohydrate in 100 parts of p-ethoxyethanol are heated to boiling under reflux 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, N'-p-iodophenyl-N'-isopropylbigua.nide is obtained in the form of its monohydrochloride, which melts at 239.degree.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von Nl-p-Jod- phenyl-N'-isopropylbiguanid, dadurch ge kennzeichnet, dass man N3-Isopropyldicyan- diamid mit p-Jodanilin umsetzt. Das N'-p-Jodphenyl-N'-isopropylbigua- nid ist eine starke Base, deren Monohydro- chlorid bei 239 C schmilzt. Die neue Base besitzt kräftige Antimalariaeigenschaften. PATENT CLAIM: Process for the production of Nl-p-iodophenyl-N'-isopropyl biguanide, characterized in that N3-isopropyl dicyanodiamide is reacted with p-iodoaniline. The N'-p-iodophenyl-N'-isopropylbiguanide is a strong base whose monohydrochloride melts at 239 ° C. The new base has powerful antimalarial properties.
CH259677D 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative. CH259677A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB259677X 1945-10-08
GB170946X 1946-09-17
CH254800T 1946-10-08

Publications (1)

Publication Number Publication Date
CH259677A true CH259677A (en) 1949-01-31

Family

ID=27178033

Family Applications (1)

Application Number Title Priority Date Filing Date
CH259677D CH259677A (en) 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative.

Country Status (1)

Country Link
CH (1) CH259677A (en)

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