CH259688A - Process for the preparation of a biguanide derivative. - Google Patents

Process for the preparation of a biguanide derivative.

Info

Publication number
CH259688A
CH259688A CH259688DA CH259688A CH 259688 A CH259688 A CH 259688A CH 259688D A CH259688D A CH 259688DA CH 259688 A CH259688 A CH 259688A
Authority
CH
Switzerland
Prior art keywords
preparation
chloro
biguanide derivative
bromophenyl
biguanide
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 CH259688A publication Critical patent/CH259688A/en

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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 zur Herstellung von     Nl-4-Chlor-3-          hromphenyl-NS-isopropylbiguanid,    welches ein  wertvolles     ehemotherapeutisehes    Mittel ist oder  als Zwischenprodukt für die Herstellung von  chemotherapeutischen Mitteln     verwendet    wer  den kann. Es ist insbesondere ein wertvolles       Antimalariamittel.     



  Erfindungsgemäss wird die besagte neue  Verbindung,     nämlich        Nl-4-Chlor-3-brom-          phenyl-NS-isopropylbiguanid,    dadurch erhal  ten, dass man     N3-Isopropyldiey        andiauuuid    mit       4-Chlor-3-bromanilin    umsetzt.  



  Die Umsetzung erfolgt zweckmässig durch  Erhitzen eines Salzes des Amins mit dem  substituierten     Dieyandiamid    in Gegenwart  eines Lösungsmittels, wie z. B. Wasser oder       /1-Äthoxyäthanol.     



  Das     N'-4-Clulor-3-bromphenyl-N'-isopropi-1-          biguanid    stellt eine starke Base dar, welche  mit organischen und anorganischen Säuren  beständige Salze ergibt, die in manchen Fällen  in Wasser leicht löslich sind. Die Salze lassen  sich dadurch herstellen, dass die Base in     wäss-          rigen    Lösungen der Säure gelöst und hierauf  das Wasser verdampft wird, doch können sie  in trockener Form bequemer durch Ver  mischen der Komponenten in einem organi  schen Lösungsmittel, wie z. B. Aceton, oder in  einem Alkohol, in welchem die Salze spärlich  löslich sind, hergestellt werden.

   Auf diese  Weise kann man beispielsweise die Salze mit    Essigsäure, Milchsäure,     -#Iethansulfonsäure,          llethylendisalieylsänre,        Met.hylen-bis-ss'-ox5--          naphthoesäure    und Salzsäure bequem her  stellen.  



  Das folgende Beispiel diene zur Erläute  rung der Erfindung.    <I>Beispiel:</I>  Ein Gemisch von 13,9 Teilen     N?-Isopro-          pyldicy        andiamid    und ?4,3 Teilen     4-Chlor-3-          bromanilin-ehlorhydrat    in 80 Teilen     ss-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     -'#thvl-          aeetat    gewaschen und aus Wasser umkristalli  siert.

   Auf diese Weise erhält man N     1-4-Chlor-          3-brompheiiyl-N -isopropylbiguanid    in Form  seines     illonoluydrochlorids,    welches bei     239'C     schmilzt.



  Process for the preparation of a biguanide derivative. The present invention relates to a process for the preparation of Nl-4-chloro-3-hromphenyl-NS-isopropylbiguanide, which is a valuable former therapeutic 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 Nl-4-chloro-3-bromophenyl-NS-isopropylbiguanide, is obtained by reacting N3-isopropyldieyandiauuuid with 4-chloro-3-bromoaniline.



  The reaction is conveniently carried out by heating a salt of the amine with the substituted dieyandiamide in the presence of a solvent, such as. B. water or / 1-ethoxyethanol.



  The N'-4-chloro-3-bromophenyl-N'-isopropi-1-biguanide is a strong base, which gives stable salts with organic and inorganic acids, 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 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, - # ethanesulfonic acid, llethylendisalieylsänre, methylene-bis-ss'-ox5-- naphthoic acid and hydrochloric acid can be conveniently prepared.



  The following example serves to explain the invention. <I> Example: </I> A mixture of 13.9 parts of N? -Isopropyldicyandiamide and? 4.3 parts of 4-chloro-3-bromaniline ehlorhydrat in 80 parts of β-ethoxyethanol is used for 3 hours heated to boiling under reflux. The mixture is then allowed to cool and it is filtered off. The solid residue is washed with cold - '# thvl- aeetat and recrystallized from water.

   In this way, N 1-4-chloro-3-bromopheiiyl-N -isopropylbiguanide is obtained in the form of its illonoluydrochloride, which melts at 239.degree.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von N@-4- C:hlor-3-bromphenyl-N"-isopropylbiguanid, da durch gekennzeichnet, dass man N3-Isopropy 1- clicyandiamid mit 4-Chlor-3-bromanilin um setzt. Das NI-4-Chlor-3-bromphenyl-N"-isopropy 1 biguanid ist. eine starke Base, deren 3tono- hydroehlorid bei '?39 C schmilzt. Die neue Base besitzt kräftige Antimalariaeigenschaften. PATENT CLAIM: Process for the preparation of N @ -4- C: chloro-3-bromophenyl-N "-isopropylbiguanide, characterized in that N3-isopropy 1-clicyandiamide is reacted with 4-chloro-3-bromaniline. 4-chloro-3-bromophenyl-N "-isopropy 1 is biguanide. a strong base whose 3tonohydrochloride melts at 15 ° C. The new base has powerful anti-malarial properties.
CH259688D 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative. CH259688A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB259688X 1945-10-08
GB170946X 1946-09-17
CH254800T 1946-10-08

Publications (1)

Publication Number Publication Date
CH259688A true CH259688A (en) 1949-01-31

Family

ID=27178044

Family Applications (1)

Application Number Title Priority Date Filing Date
CH259688D CH259688A (en) 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative.

Country Status (1)

Country Link
CH (1) CH259688A (en)

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