CH259711A - Process for the preparation of a biguanide derivative. - Google Patents

Process for the preparation of a biguanide derivative.

Info

Publication number
CH259711A
CH259711A CH259711DA CH259711A CH 259711 A CH259711 A CH 259711A CH 259711D A CH259711D A CH 259711DA CH 259711 A CH259711 A CH 259711A
Authority
CH
Switzerland
Prior art keywords
preparation
bromo
acid
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 CH259711A publication Critical patent/CH259711A/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)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

      Verfahren    zur Herstellung eines     Biguanidderivates.       Die vorliegende Erfindung betrifft ein  Verfahren mir     Herstellung    von     N1-3-Brom--1-          jodphenyl-N -isopropyIbigtianid,    welches ein  wertvolles     eliemotherapeutisehes        -Mittel    ist.  oder als     Zwisehenproduktfür    die Herstellung  von     ehemotherapeutisehen    Mitteln     verwendet     werden kann. Es ist     insbesondere    ein wert  volles     Antimalariamitt.el.     



  Erfindungsgemäss wird die besagte neue       Verbindung,    nämlich     Nl-3-Broin-4-jodphenyl-          N'-isopropylbiguanid,    dadurch erhalten, dass       i)iati        N"-Isopropyldieyancliamid    mit     3-Brom-          -1-jodanilin    umsetzt.  



  Die     Umsetzung    erfolgt zweckmässig durch       l@rhitzen    eines Salzes des Amins mit dem sub  stituierten     Dicyandianiid    in Gegenwart eines       Lösungsmittels,    wie z. B. Wasser oder       Äthoxyäthanol.     



  Das     N'-3-Brom-4.-joclplienyl-N'-isopropy1-          biguanid    stellt. eine starke Base dar, welche  mit. organischen und anorganischen Säuren  beständige Salze     ergibt,    die in manchen Fäl  len in     Wasser    leicht     löslieli    sind. Die Salze  lassen sich dadurch herstellen, dass die Base in       Wässrigen    Lösungen der Säure gelöst und  Hierauf das Wasser verdampft wird,     doc!i     können sie in trockener Form bequemer durch  Vermischen der Komponenten in einem     orga-          n        ischen    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,     llilehsä.ure,        lethansulfon-          säure,        Methylendisalicylsäure,        Methylen-bis        ss-          cxynaplithoesänre    und Salzsäure     bequem    her  stellen.  



  Das folgende Beispiel diene zur Erläute  rung der Erfindung.    <I>Beispiel:</I>    Ein Gemisch von 12,6 Teilen     N'-Isopropyl-          diey        andiamid    und 23,4 Teilen     3-Brom-4-jod-          anilin-ehlorlivdrat    in 100 Teilen. Wasser wird       wäliren.d    3 Stunden     -unter        Rüekfluss    zum Sie  den erhitzt. Hierauf lässt man das Gemisch  abkühlen, worauf     abfiltriert    wird. Der feste  Rückstand wird mit kaltem. Wasser gewaschen  und aus     Wasser    umkristallisiert..

   Auf diese  Weise erhält. man N     1-3-Br        om-l-jodpheny        1-N'-          isopropyIbiguanid    in Form seines     llonohydro-          clilorids,welches    bei 236  C schmilzt.



      Process for the preparation of a biguanide derivative. The present invention relates to a process for the preparation of N1-3-bromo-1-iodophenyl-N -isopropylbigtianide, which is a valuable eliemotherapeutic agent. or it can be used as an intermediate for the manufacture of post-therapeutic agents. In particular, it is a valuable antimalarial agent.



  According to the invention, the said new compound, namely Nl-3-broin-4-iodophenyl-N'-isopropylbiguanide, is obtained by i) reacting iati N'-isopropyldieyancliamide with 3-bromo-1-iodaniline.



  The reaction is conveniently carried out by l @ rhitzen a salt of the amine with the sub-substituted dicyandianiid in the presence of a solvent, such as. B. water or ethoxyethanol.



  The N'-3-bromo-4.-joclplienyl-N'-isopropy1-biguanid provides. a strong base, which with. organic and inorganic acids result 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. 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 sparse Lich soluble. In this way, for example, the salts with acetic acid, lilehic acid, lethanesulphonic acid, methylenedisalicylic acid, methylene bis-s-cxynaplithoic acid and hydrochloric acid can be conveniently prepared.



  The following example serves to explain the invention. <I> Example: </I> A mixture of 12.6 parts of N'-isopropyl-dieyandiamide and 23.4 parts of 3-bromo-4-iodo-aniline-ehlorlivdrat in 100 parts. Water is heated for 3 hours under reflux to you. The mixture is then allowed to cool and it is filtered off. The solid residue is with cold. Water washed and recrystallized from water ..

   That way it gets. one N 1-3-Brom-1-iodopheny 1-N'-isopropyIbiguanid in the form of its llonohydro- clilorids, which melts at 236C.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von N1-3- Brom-4-jodphenyl-N'-isopropylbiguanid, da durch gekennzeichnet, dass man N3-Isopropyl- dieyandiamid mit 3-Brom-4-jodanilin umsetzt. Das Nl-3-Brom-4-joclphenyl-N'-isopropyl- biguanid ist. eine starke Base, deren Mono- hy droehlorid bei 236 C schmilzt. Die neue Base besitzt kräftige Antimalariaeigensehaften. PATENT CLAIM: A process for the preparation of N1-3-bromo-4-iodophenyl-N'-isopropylbiguanide, characterized in that N3-isopropyldiyandiamide is reacted with 3-bromo-4-iodaniline. The Nl-3-bromo-4-joclphenyl-N'-isopropyl biguanide is. a strong base whose monohydrochloride melts at 236C. The new base has strong anti-malarial properties.
CH259711D 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative. CH259711A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB259711X 1945-10-08
GB170946X 1946-09-17
CH254800T 1946-10-08

Publications (1)

Publication Number Publication Date
CH259711A true CH259711A (en) 1949-01-31

Family

ID=27178067

Family Applications (1)

Application Number Title Priority Date Filing Date
CH259711D CH259711A (en) 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative.

Country Status (1)

Country Link
CH (1) CH259711A (en)

Similar Documents

Publication Publication Date Title
CH259711A (en) Process for the preparation of a biguanide derivative.
CH259713A (en) Process for the preparation of a biguanide derivative.
CH259681A (en) Process for the preparation of a biguanide derivative.
CH259698A (en) Process for the preparation of a biguanide derivative.
CH259703A (en) Process for the preparation of a biguanide derivative.
CH259693A (en) Process for the preparation of a biguanide derivative.
CH259714A (en) Process for the preparation of a biguanide derivative.
CH259704A (en) Process for the preparation of a biguanide derivative.
CH259661A (en) Process for the preparation of a biguanide derivative.
CH259683A (en) Process for the preparation of a biguanide derivative.
CH259699A (en) Process for the preparation of a biguanide derivative.
CH259682A (en) Process for the preparation of a biguanide derivative.
CH259656A (en) Process for the preparation of a biguanide derivative.
CH259663A (en) Process for the preparation of a biguanide derivative.
CH259677A (en) Process for the preparation of a biguanide derivative.
CH259679A (en) Process for the preparation of a biguanide derivative.
CH259690A (en) Process for the preparation of a biguanide derivative.
CH259700A (en) Process for the preparation of a biguanide derivative.
CH259660A (en) Process for the preparation of a biguanide derivative.
CH259678A (en) Process for the preparation of a biguanide derivative.
CH259669A (en) Process for the preparation of a biguanide derivative.
CH259689A (en) Process for the preparation of a biguanide derivative.
CH259666A (en) Process for the preparation of a biguanide derivative.
CH259674A (en) Process for the preparation of a biguanide derivative.
CH259688A (en) Process for the preparation of a biguanide derivative.