CH259659A - Process for the preparation of a biguanide derivative. - Google Patents

Process for the preparation of a biguanide derivative.

Info

Publication number
CH259659A
CH259659A CH259659DA CH259659A CH 259659 A CH259659 A CH 259659A CH 259659D A CH259659D A CH 259659DA CH 259659 A CH259659 A CH 259659A
Authority
CH
Switzerland
Prior art keywords
preparation
biguanide derivative
acid
diiodophenyl
isopropylbiguanide
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 CH259659A publication Critical patent/CH259659A/en

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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     Nl-3,4-Dijod-          phenyl    -<B>N--'-</B>     isopropylbiguanid,    welches ein  wertvolles     chemotherapeutisches    Mittel ist  oder als     Zwischenprodukt    für die     Herstel-          lun-    von     ehemotherapeatisehen    Mitteln ver  wendet werden kann. Es ist insbesondere ein  wertvolles     Antimalariamittel.     



       Erfindungsgemäss    wird die besagte neue       Verbindung,    nämlich     Nl-3,-I-Dijodphenyl-N--'-          isopi'opylbiguanid,    dadurch erhalten, dass       nian        N'-Isoliropyldieyandiamid    mit     3,1-Dijod-          anilin    umsetzt.  



  Die     L-nisetzun-    erfolgt     zweckmässig        dureli     Erhitzen eines Salzes des Amins mit dem       substituierten        Dieyandiamid    in Gegenwart  eines Lösungsmittels, wie z. B. Wasser oder       f-,'1tlioxyäthaiiol.     



  Das     NI        -3,4-Dijodphenyl-N'-isopropyIbi-          guanid    stellt eine starke Base dar,     welche    mit  organischen und     anorganischen    Säuren be  ständige Salze ergibt, die in manchen Fällen  in Wasser     leielit    löslich sind. Die Salze lassen  sich dadurch herstellen, dass die Base in       wässrigen    Lösungen der Säure gelöst und  hierauf das Wasser verdampft wird, doch  können sie in trockener     Forni    bequemer durch  Vermischen der Komponenten in einem orga  nischen Lösungsmittel, wie z. B.

   Aceton, oder  in einem Alkohol, in     welchem    die Salze spär  lich sind,     hergestellt    werden. Auf diese Weise    kann     nian    beispielsweise die Salze mit     Essi--          säure,    Milchsäure,     Methansulfonsäure,        Me-          tliy        lendisalicy        lsäure,        Methy        len-bis-ss-oxynaph-          t.hoesäure    und Salzsäure bequem herstellen.  



  Das folgende Beispiel diene zur     Erläute-          rung        der        Erfindun-    .  



  <I>Beispiel:</I>  Ein Gemisch von 12,6     Teilen        NI-Isopro-          pyIdieyandiamid    und 38,2 Teilen     3,4-Dijod-          anilin-chlorhy        dr        at    in 100 Teilen     ss-Äthoxy-          äthanol    wird während 3 Stunden unter     Rüek-          fluss    zum Sieden erhitzt. Hierauf lässt man  (las Gemisch abkühlen, worauf     abfiltriert     wird.

   Der feste Rückstand wird mit kaltem  <B><U>,</U></B>     '#thv   <B>,</B>  <B>'</B>     lacetat        gewaschen    und aus Äthylalkohol,       umkristallisiert.    Auf diese Weise erhält man       N'L3,1-Dijodphenyl-N'-isopropylbiguanid    in  Form seines     Monohydrochlorids,    welches bei  237  C schmilzt.



  Process for the preparation of a biguanide derivative. The present invention relates to a process for the production of Nl-3,4-diiodophenyl- <B> N-'- </B> isopropylbiguanide, which is a valuable chemotherapeutic agent or as an intermediate for the production of previous therapies Funds can be used. It is a particularly valuable antimalarial drug.



       According to the invention, said new compound, namely Nl-3, -I-diiodophenyl-N-'- isopi'opylbiguanid, is obtained by reacting N'-isoliropyldieyandiamide with 3,1-diiodoaniline.



  The L-nisetzun- is expediently carried out by heating a salt of the amine with the substituted dieyandiamide in the presence of a solvent, such as. B. water or f -, '1tlioxyäthaiiol.



  The NI -3,4-diiodophenyl-N'-isopropylbiguanide 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 solutions of the acid and then the water is evaporated, but they can be more convenient in dry form by mixing the components in an orga African solvent, such as. B.

   Acetone, or in an alcohol in which the salts are sparse. In this way, Nian can, for example, conveniently prepare the salts with acetic acid, lactic acid, methanesulfonic acid, metal lendisalicic acid, methylene-bis-ss-oxynaphthoic acid and hydrochloric acid.



  The following example serves to explain the invention.



  <I> Example: </I> A mixture of 12.6 parts of NI-isopropyldiyandiamide and 38.2 parts of 3,4-diiodoaniline chlorohydrate in 100 parts of ß-ethoxyethanol is added for 3 hours Reflux heated to the boil. The mixture is then left to cool, whereupon it is filtered off.

   The solid residue is washed with cold <B><U>, </U> </B> '#thv <B>, </B> <B>' </B> lacetate and recrystallized from ethyl alcohol. In this way, N'L3,1-diiodophenyl-N'-isopropyl biguanide is obtained in the form of its monohydrochloride, which melts at 237.degree.

Claims (1)

PATEN TAN SPRUCH Verfahren zur Herstellung von Nl-3,i-Di- joclphen j-1-N5-isopropylbiguanid, dadurch ge kennzeichnet, dass man N3-Isopropyldicyan- diamid mit 3,4-Dijodanilin umsetzt. Das Nl-3,4-Dijodplienj-l-N@-isopropylbi- gnanid ist eine starke Base, deren Mono hydrochlorid bei 237 C schmilzt. Die neue Base besitzt kräftige Antimalariaeigenschaf- ten. PATEN TAN SPRUCH Process for the production of Nl-3, i-dijoclphen j-1-N5-isopropylbiguanide, characterized in that N3-isopropyldicyandiamide is reacted with 3,4-diiodaniline. The Nl-3,4-Dijodplienj-l-N @ -isopropylbi- gnanid is a strong base whose monohydrochloride melts at 237C. The new base has strong antimalarial properties.
CH259659D 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative. CH259659A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB259659X 1945-10-08
GB170946X 1946-09-17
CH254800T 1946-10-08

Publications (1)

Publication Number Publication Date
CH259659A true CH259659A (en) 1949-01-31

Family

ID=27178015

Family Applications (1)

Application Number Title Priority Date Filing Date
CH259659D CH259659A (en) 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative.

Country Status (1)

Country Link
CH (1) CH259659A (en)

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