CH259658A - Process for the preparation of a biguanide derivative. - Google Patents

Process for the preparation of a biguanide derivative.

Info

Publication number
CH259658A
CH259658A CH259658DA CH259658A CH 259658 A CH259658 A CH 259658A CH 259658D A CH259658D A CH 259658DA CH 259658 A CH259658 A CH 259658A
Authority
CH
Switzerland
Prior art keywords
preparation
biguanide derivative
isopropylbiguanide
acid
salts
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 CH259658A publication Critical patent/CH259658A/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     N1-3,5-Di-          cfilorplienyl-N        '-isopropy        lbiguanid,    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     N1-3,5-Diclilorplienyl-          N'-isopropylbiguanid,    dadurch erhalten., dass  man     N3-Isopropyldicyandiamid    mit     3,5-Di-          ehloranilin    umsetzt.  



  Die     Umsetzung        erfolgt        zweckmässig        durch     Erhitzen eines Salzes des Amins mit     dem          substituierten        Dici-ancliamid    in     C7egenwart     eines Lösungsmittels, wie z. B. Wasser oder       f)-Ätliotyätlianol.     



  Das     N1-3,5-Diclilorplienyl-N'-isopropylbi-          guanid    stellt eine starke Base dar, welche mit  organischen     und    anorganischen Säuren be  ständige Salze ergibt, die in manchen Fällen in       Wasser    leicht löslich sind. Die Salze lassen  sieh 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  organischen     Lösungsmittel,    wie z. B.

   Aceton,  oder in einem Alkohol, in welchem die Salze       spärlieh    löslich sind,     hergestellt    werden. Auf  diese     Weise        kann    man beispielsweise die Salze    mit Essigsäure,     Milchsäure,        Methansulfon-          sä.ure,        3lethylendisalicylsäure,        Methylen-bis-ss-          oxynaphthoesäure        und        Salzsäure    bequem her  stellen.  



  Das folgende Beispiel diene zur     Erläute-          rung    der     Erfindung.            Beispiel:       Bin Gemisch von 12,6 Teilen     NI-Isopro-          pyIdicyandiamid    und 22 Teilen     3,5-Dielilor-          anilin-chlorhy        drat    in 100 Teilen     ss-Äthoxy-          äthanol    wird     wärend    3 Stunden unter Rück  fluss zum Sieden erhitzt. Hierauf lässt man  das Gemisch abkühlen, worauf     abfiltriert     wird.

   Der feste Rückstand wird mit kaltem       1ltliy        lacetat    gewaschen und aus Wasser um  kristallisiert. Auf diese Weise erhält man       ,I-3,5-Dichlorphenyl-N'-isopropylbiguanid    in  Form seines     Monohy        clrochlorids,    welches bei       239-2.10"    C schmilzt.



  Process for the preparation of a biguanide derivative. The present invention relates to a process for the preparation of N1-3,5-dicfilorplienyl-N'-isopropylbiguanide, 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, said new compound, namely N1-3,5-diclilorplienyl-N'-isopropylbiguanide, is obtained by reacting N3-isopropyldicyandiamide with 3,5-di-chloroaniline.



  The reaction is conveniently carried out by heating a salt of the amine with the substituted dici-ancliamide in the presence of a solvent, such as. B. water or f) -ätliotyätlianol.



  The N1-3,5-diclilorplienyl-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 by dissolving the base in aqueous solutions of the acid and then evaporating the water, 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. In this way, for example, the salts with acetic acid, lactic acid, methanesulfonic acid, 3-ethylenedisalicylic acid, methylene-bis-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 of NI-IsopropyIdicyandiamid and 22 parts of 3,5-Dieliloroaniline-Chlorhydrat in 100 parts of s-ethoxyethanol is heated to boiling for 3 hours under reflux. The mixture is then allowed to cool and it is filtered off.

   The solid residue is washed with cold 1ltliy lacetat and crystallized from water. In this way, I-3,5-dichlorophenyl-N'-isopropylbiguanide is obtained in the form of its Monohy clrochlorids, which melts at 239-2.10 "C.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von N1-3,5-Di- ehlor phenyl - N' - isopropy lbiguanid, dadurch gekennzeichnet, dass man NI-Isopropy ldicy an- diamid finit 3,5-Diehloranilin umsetzt. PATENT CLAIM: Process for the production of N1-3,5-dichlorophenyl - N '- isopropy lbiguanid, characterized in that NI-isopropyl dicyandiamide finite 3,5-diehloraniline is reacted. Das N1-3,5-Dichlorplienyl-N'-isopropylbi- guanid ist eine starke Base, deren Hono- hydrochlorid bei 239-24011C schmilzt. Die neue Base besitzt kräftige Antiinalariaeigen- schaften. The N1-3,5-dichloroplienyl-N'-isopropylbiguanide is a strong base, the honey hydrochloride of which melts at 239-24011C. The new base has strong anti-alarial properties.
CH259658D 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative. CH259658A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB259658X 1945-10-08
GB170946X 1946-09-17
CH254800T 1946-10-08

Publications (1)

Publication Number Publication Date
CH259658A true CH259658A (en) 1949-01-31

Family

ID=27178014

Family Applications (1)

Application Number Title Priority Date Filing Date
CH259658D CH259658A (en) 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative.

Country Status (1)

Country Link
CH (1) CH259658A (en)

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