CH259712A - Process for the preparation of a biguanide derivative. - Google Patents

Process for the preparation of a biguanide derivative.

Info

Publication number
CH259712A
CH259712A CH259712DA CH259712A CH 259712 A CH259712 A CH 259712A CH 259712D A CH259712D A CH 259712DA CH 259712 A CH259712 A CH 259712A
Authority
CH
Switzerland
Prior art keywords
sep
preparation
bromo
biguanide derivative
water
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 CH259712A publication Critical patent/CH259712A/en

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C279/00Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C279/20Derivatives 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
    • C07C279/24Y being a hetero atom
    • C07C279/26X and Y being nitrogen atoms, i.e. biguanides

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (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     Nl-3-Brom-4-          jodphenyl-N'-n-prop@-l.biguanid,        welehes    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,     nämlieh        Nl-3-Broin-4-jodphenyl-          N'-n-liropylbiguanid,    dadurch erhalten, dass  man     N"-n-Propyldicy        andianiid    mit     3-Broni-4-          jodanilin    umsetzt.  



  Die     Unisetzung    erfolgt zweckmässig     dureh          Erhitzen    eines Salzes des Amins mit dem       substituierten        1)ieyandiainid    in Gegenwart       eines        Lösungsmittels,    wie z. B. Wasser oder       ss-Äthoyyätlianol.     



  Das     N'-3-Brom-4-jodphenyl-N'-n-propyl-          bin2tanid    stellt eine     starke    Base dar,     welehe     mit     orgaiiisclieii    und     anorganisehen    Säuren  beständige Salze ergibt, die in     manehen    Fäl  len in Wasser     leieht        löslieh    sind.

   Die Salze  lassen sieh dadurch herstellen,     dass    die Base  in     wälirigen        Lösungen    der Säure gelöst und  hierauf das     Wasser    verdampft wird, doch  können sie in trockener Form bequemer durch       Verinisehen    der     Komponenten    in einem orga  nischen Lösungsmittel, wie z. B. Aceton, oder  in einem Alkohol, in welchem die Salze spär  lich     löslieli    sind, hergestellt werden.

   Auf diese       Weise    kann man beispielsweise die Salze mit  
EMI0001.0040     
  
    Essigsäure, <SEP> Milehsäure, <SEP> 1Iethansulfonsäure.
<tb>  1Iethylendisalicylsäure, <SEP> Methylen-bis-ss-o:cy  naphtlioesätire <SEP> und <SEP> Salzsäure <SEP> bequem <SEP> her  stellen.
<tb>  Das <SEP> folgende <SEP> Beispiel <SEP> diene <SEP> zur <SEP> Erläute  rung <SEP> der <SEP> Erfindung.       <I>Beispiel:</I>  Ein     Gemiseh    von 12,6 Teilen     N3-n-Propyl-          dicyandia.mid    und 23,4 Teilen     3-Brom-4-jod-          anilin-chlorhvdrat    in 60 Teilen Wasser wird       \#,ährend    3 Stunden unter     Rüekfluss    zum Sie  den erhitzt.

   Hierauf lässt man das     Cremiseli     abkühlen, worauf     abfiltriert    wird. Der feste       li,ückstand    wird     finit    kaltem Wasser     gewasehen     und aus Wasser umkristallisiert. Auf diese  Weise erhält man     Nl-3-Brom-4-jodplietiyl-N'-          n-propylbigtianid    in Form seines     l        onohydro-          chlorids,        welehes    bei 227 bis 228 C     sehmilzt.  



  Process for the preparation of a biguanide derivative. The present invention relates to a process for the preparation of Nl-3-bromo-4-iodophenyl-N'-n-prop@-l.biguanide, which is a valuable chemotherapeutic agent or can be used as an intermediate for the preparation of chemotherapeutic agents. In particular, it is a valuable antimalarial agent.



       According to the invention, the said new compound, namely Nl-3-broin-4-iodophenyl-N'-n-liropylbiguanide, is obtained by reacting N "-n-propyldicyandianiide with 3-broni-4-iodaniline.



  The unisetzung takes place expediently by heating a salt of the amine with the substituted 1) ieyandiainid in the presence of a solvent, such as. B. water or ss-Ethoyyätlianol.



  The N'-3-bromo-4-iodophenyl-N'-n-propylbin2tanide is a strong base which, with organic and inorganic acids, gives stable salts which in some cases are slightly 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 verinisehen the components in an orga African solvent such. B. acetone, or in an alcohol in which the salts are sparse Lichlöslieli are prepared.

   In this way you can, for example, the salts with
EMI0001.0040
  
    Acetic acid, <SEP> lactic acid, <SEP> 1ethanesulfonic acid.
<tb> Ethylenedisalicylic acid, <SEP> methylene-bis-ss-o: cy naphtlioesätire <SEP> and <SEP> hydrochloric acid <SEP> conveniently <SEP>.
<tb> The <SEP> following <SEP> example <SEP> serves <SEP> for <SEP> explanation <SEP> of the <SEP> invention. <I> Example: </I> A mixture of 12.6 parts of N3-n-propyl-dicyandia.mid and 23.4 parts of 3-bromo-4-iodo-aniline-chlorohydrate in 60 parts of water is used 3 hours under reflux to the heated.

   The Cremiseli is then left to cool, after which it is filtered off. The solid liquid residue is finitely washed with cold water and recrystallized from water. In this way, Nl-3-bromo-4-iodoplietiyl-N'-n-propylbigtianide is obtained in the form of its ionohydrochloride, which melts at 227 to 228C.

 

Claims (1)

EMI0001.0060 PATENTANSPRUCH: <tb> Verfahren <SEP> zur <SEP> I-Ierstellung <SEP> von <SEP> Nl-3-Broiii 4-jodphenyl-N'-n-prop#-lbi=,nanid, <SEP> dadurch <SEP> ge kennzeichnet, <SEP> dass <SEP> inan <SEP> #N'-n-PropyIdicyan diamid. <SEP> mit <SEP> 3-Brom-4-joclanilin <SEP> umsetzt. <tb> Das <SEP> Ni-3-Brom-4-jodplienyl-N'-n-propyl biguanid <SEP> ist <SEP> eine <SEP> starke <SEP> Base, <SEP> deren <SEP> Mono hvdroehlorid <SEP> bei <SEP> 227 <SEP> bis <SEP> 2,'38 <SEP> C <SEP> schmilzt. <SEP> Die <tb> neue <SEP> Base <SEP> besitzt. <SEP> kräftige <SEP> Ant.iinalariaeigen schaften. EMI0001.0060 PATENT CLAIM: <tb> Method <SEP> for the <SEP> I-I-I creation <SEP> of <SEP> Nl-3-Broiii 4-iodphenyl-N'-n-prop # -lbi =, nanid, <SEP> thereby <SEP> marked, <SEP> that <SEP> inan <SEP> # N'-n-PropyIdicyan diamid. <SEP> with <SEP> 3-bromo-4-joclanilin <SEP> converts. <tb> The <SEP> Ni-3-bromo-4-iodplienyl-N'-n-propyl biguanid <SEP> is <SEP> a <SEP> strong <SEP> base, <SEP> its <SEP> monohydrochloride <SEP> at <SEP> 227 <SEP> to <SEP> 2, '38 <SEP> C <SEP> melts. <SEP> The <tb> has new <SEP> Base <SEP>. <SEP> strong <SEP> antialarial properties.
CH259712D 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative. CH259712A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB259712X 1945-10-08
GB170946X 1946-09-17
CH254800T 1946-10-08

Publications (1)

Publication Number Publication Date
CH259712A true CH259712A (en) 1949-01-31

Family

ID=27178068

Family Applications (1)

Application Number Title Priority Date Filing Date
CH259712D CH259712A (en) 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative.

Country Status (1)

Country Link
CH (1) CH259712A (en)

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