CH259704A - Process for the preparation of a biguanide derivative. - Google Patents

Process for the preparation of a biguanide derivative.

Info

Publication number
CH259704A
CH259704A CH259704DA CH259704A CH 259704 A CH259704 A CH 259704A CH 259704D A CH259704D A CH 259704DA CH 259704 A CH259704 A CH 259704A
Authority
CH
Switzerland
Prior art keywords
preparation
bromo
iodophenyl
biguanide derivative
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 CH259704A publication Critical patent/CH259704A/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     Nl-4-Brom-3-          jodphenyl-NS-n-propylbiguanid,    welches ein.  wertvolles chemotherapeutisches Mittel ist  oder als Zwischenprodukt für die Herstellung  von chemotherapeutischen Mitteln verwendet  werden kann. Es ist insbesondere ein wert  volles     Antimalariamittel.     



       Erfindungsgemäss    wird die besagte neue  Verbindung, nämlich     NI-4-Brom-3-jodphenyl-          NS-n-propylbiguanid,    dadurch erhalten, dass  man     N3-n-Propyldicyandiamid    mit     4-Brom-3-          jodanilin    umsetzt.  



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



  Das     Ni-4-Brom-3-jodphenyl-N'-n-propyl-          biguanid    stellt eine starke Base dar, welche  mit organischen und anorganischen Säuren  beständige Salze ergibt, die in manchen Fäl  len in Wasser leicht 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 Form bequemer durch  Vermischen der Komponenten in einem orga  nischen Lösungsmittel, wie z. B. Aceton, oder  in einem Alkohol, in welchem die Salze spär  lich löslich sind, hergestellt werden.

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



  Das folgende Beispiel diene zur Erläute  rung der Erfindung.  



       Beispiel:     Ein     CTemisch    von 12,6 Teilen     N3-n-Propyl-          dicyandiamid    und 34 Teilen     4-Brom-3-jod-          anilin-chlorhydrat    in 150 Teilen     fl-Äthoxy-          äthanol    wird während 3 Stunden unter Rück  fluss zum Sieden erhitzt. Hierauf lässt man  das Gemisch abkühlen, worauf     abfiltriert    wird.  Der feste Rückstand wird mit kaltem     Äthyl-          acetat    gewaschen und aus Wasser umkristalli  siert.

   Auf diese Weise erhält man     Nl-4-Brom-          3-jodphenyl-N'-n-propylbiguanid    in Form  seines     Monohydrochlorids,    welches bei 232 bis  233  C schmilzt.



  Process for the preparation of a biguanide derivative. The present invention relates to a process for the preparation of Nl-4-bromo-3-iodophenyl-NS-n-propylbiguanide, which is a. is a valuable chemotherapeutic agent or can be used as an intermediate in the manufacture of chemotherapeutic agents. It is a particularly valuable antimalarial drug.



       According to the invention, said new compound, namely NI-4-bromo-3-iodophenyl-NS-n-propylbiguanide, is obtained by reacting N3-n-propyldicyandiamide with 4-bromo-3-iodoaniline.



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



  Ni-4-bromo-3-iodophenyl-N'-n-propyl-biguanide 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 Lich soluble, are produced.

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



  The following example serves to explain the invention.



       Example: A mixture of 12.6 parts of N3-n-propyl dicyandiamide and 34 parts of 4-bromo-3-iodoaniline chlorohydrate in 150 parts of fl-ethoxyethanol is 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, Nl-4-bromo-3-iodophenyl-N'-n-propylbiguanide is obtained in the form of its monohydrochloride, which melts at 232-233.degree.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von N1-4-Broin- 3-jodphenyl-Nj-n-propylbiguanid, dadurch ge kennzeichnet, dass man N3-n-Propyldicyan- diamid mit 4-Brom-3-jodanilin umsetzt. Das Nl-4-Brom-3-jodphenyl-N6-n-propyl- biguanid ist eine starke Base, deren Mono- hydrochlorid bei 232 bis 233 C schmilzt. Dia neue Base besitzt kräftige Antimalariaeigen- schaften. PATENT CLAIM: Process for the preparation of N1-4-broin-3-iodophenyl-Nj-n-propylbiguanide, characterized in that N3-n-propyldicyanodiamide is reacted with 4-bromo-3-iodaniline. The Nl-4-bromo-3-iodophenyl-N6-n-propyl-biguanide is a strong base, the monohydrochloride of which melts at 232-233C. The new base has powerful antimalarial properties.
CH259704D 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative. CH259704A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB259704X 1945-10-08
GB170946X 1946-09-17
CH254800T 1946-10-08

Publications (1)

Publication Number Publication Date
CH259704A true CH259704A (en) 1949-01-31

Family

ID=27178060

Family Applications (1)

Application Number Title Priority Date Filing Date
CH259704D CH259704A (en) 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative.

Country Status (1)

Country Link
CH (1) CH259704A (en)

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