CH259663A - Process for the preparation of a biguanide derivative. - Google Patents

Process for the preparation of a biguanide derivative.

Info

Publication number
CH259663A
CH259663A CH259663DA CH259663A CH 259663 A CH259663 A CH 259663A CH 259663D A CH259663D A CH 259663DA CH 259663 A CH259663 A CH 259663A
Authority
CH
Switzerland
Prior art keywords
methyl
preparation
biguanide derivative
diiodophenyl
acid
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 CH259663A publication Critical patent/CH259663A/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     N1-3,4-Dijod-          phenyl-N'-metliyl-N"-n-propylbi,-uanid,    wel  ches ein wertvolles chemotherapeutisches Mit  tel ist oder als Zwischenprodukt für die Her  stellung von chemotherapeutischen Mitteln  verwendet werden kann. Es ist insbesondere  ein wertvolles     Antimalariamittel.     



       Erfindungsgemäss    wird die besagte neue  Verbindung, nämlich     N1-3,4-Dijodphenyl-N'-          methyl-N        "-n-propylbibiianid,    dadurch erhal  ten, dass man     N3-Methyl-N'-n-propy        ldicyandi-          amid    mit     3,4-Dijodanilin    umsetzt.  



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



  Das     N1-3,4-Dijodphenyl-N"-methyl-N"-n-          propylbiguanid    stellt eine starke Base dar,  welche mit organischen und anorganischen  Säuren beständige Salze ergibt, die in man  chen Fällen in Wasser leicht löslich sind. Die  Salze lassen sich dadurch herstellen, dass die  Base in     wässriben    Lösungen der Säure gelöst  und hierauf das Wasser verdampft wird,  doch können sie in trockener Form bequemer  durch Vermischen der Komponenten in einem  organischen Lösungsmittel, wie z. B. Aceton,  oder in einem Alkohol, in welchem die Salze  spärlich löslich sind, herbestellt werden.

   Auf  diese Weise kann man beispielsweise die Salze  mit Essigsäure, Milchsäure, Methansulfon-    säure,     Methylendisalicylsäure,        Methylen-bis-ss-          oxy        naphthoesäure    und Salzsäure bequem her  stellen.  



  Das folgende Beispiel diene zur Erläute  rung der Erfindung.    <I>Beispiel:</I>    Ein Gemisch von 14 Teilen     N@-1@-Ietliy        1-N3-          ri-propyldieyandiamid        und    38,2 Teilen     3,4-          Dijodanilin-chlorhydrat    in 125 Teilen     ss-Äth-          oxy        äthanol    wird während 3 Stünden unter       Rückfluss    zum Sieden erhitzt. Hierauf lässt  man das Gemisch abkühlen, worauf     abfil-          triert    wird. Der feste Rückstand wird mit  kaltem Äthylalkohol gewaschen und aus  Wasser umkristallisiert.

   Auf diese Weise er  hält man     N1-3,4-Dijodphenyl-N'-methyl-N"-n-          propylbiguanid    in Form seines     Monohydro-          chlorids,    welches bei 235  C     schmilzt.  



  Process for the preparation of a biguanide derivative. The present invention relates to a process for the preparation of N1-3,4-diiodophenyl-N'-methyl-N "-n-propylbi, -uanide, wel Ches is a valuable chemotherapeutic agent or as an intermediate for the manufacture of chemotherapeutic agents, it is particularly a valuable antimalarial agent.



       According to the invention, said new compound, namely N1-3,4-diiodophenyl-N'-methyl-N "-n-propylbibiianid, obtained by adding N3-methyl-N'-n-propy ldicyandiamide with 3, 4-Diiodaniline converts.



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



  The N1-3,4-diiodophenyl-N "-methyl-N" -n-propylbiguanide 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 conveniently in dry form by mixing the components in an organic solvent, such as. B. acetone, or in an alcohol in which the salts are sparingly soluble, can be produced.

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



  The following example serves to explain the invention. <I> Example: </I> A mixture of 14 parts of N @ -1 @ -ietliy 1-N3-ri-propyldieyandiamide and 38.2 parts of 3,4-diiodaniline chlorohydrate in 125 parts of ß-ethoxyethanol is used heated to boiling for 3 hours under reflux. The mixture is then allowed to cool, whereupon it is filtered off. The solid residue is washed with cold ethyl alcohol and recrystallized from water.

   In this way, N1-3,4-diiodophenyl-N'-methyl-N "-n-propylbiguanide is obtained in the form of its monohydrochloride, which melts at 235.degree.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von N1-3,4-Di- joclphenyl-NI-methyl-N'-n-propylbi,uanid, da durch gekennzeichnet, dass man N3-Methyl- NI-n-propyldicyaridiamid mit 3,4-Dijodanilin umsetzt. Das N1-3,4-Dijodphenyl-N"-methyl-N"-n- propylbiguanid ist eine starke Base, deren 3blonohy drochlorid bei 235 C schmilzt. Die neue Base besitzt kräftige Antimalariaeigen- schaften. PATENT CLAIM: Process for the production of N1-3,4-di-joclphenyl-NI-methyl-N'-n-propylbi, uanid, characterized in that N3-methyl-NI-n-propyldicyaridiamide with 3,4-diiodaniline implements. The N1-3,4-diiodophenyl-N "-methyl-N" -n-propylbiguanid is a strong base whose 3blonohy hydrochloride melts at 235.degree. The new base has powerful antimalarial properties.
CH259663D 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative. CH259663A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB259663X 1945-10-08
GB170946X 1946-09-17
CH254800T 1946-10-08

Publications (1)

Publication Number Publication Date
CH259663A true CH259663A (en) 1949-01-31

Family

ID=27178019

Family Applications (1)

Application Number Title Priority Date Filing Date
CH259663D CH259663A (en) 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative.

Country Status (1)

Country Link
CH (1) CH259663A (en)

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