CH259680A - Process for the preparation of a biguanide derivative. - Google Patents

Process for the preparation of a biguanide derivative.

Info

Publication number
CH259680A
CH259680A CH259680DA CH259680A CH 259680 A CH259680 A CH 259680A CH 259680D A CH259680D A CH 259680DA CH 259680 A CH259680 A CH 259680A
Authority
CH
Switzerland
Prior art keywords
sep
preparation
biguanide derivative
methyl
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 CH259680A publication Critical patent/CH259680A/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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

  Verfahren zur Herstellung eines     Biguanidderivates.       Die vorliegende Erfindung betrifft ein  \'erfahren zur Herstellung von     Ni-p-Jod-          pheiiyl-N'-nietliyl-I@T'-isopropylbiguanid,    wel  ches ein     wertvolles        ehemothera.peutisches    Mit  tel ist oder als Zwischenprodukt für die Her  stellung von     chemotherapeutischen    Mitteln       verwendet:    werden kann. Es ist     insbesondere     ein wertvolles     Antimalariamittel.     



  Erfindungsgemäss wird die besagte neue  Verbindung, nämlich     N1-p-Jodplienyl-N'-me-          thyl-N'-isopropylbiguanid,    dadurch erhalten,       class    man     N''-btethy        l-N''-isopropy        ldieyandi-          amid    mit     p-Jodaniliri    umsetzt.  



  Die     Unisetzung    erfolgt     zweckmässig    durch  Erhitzen eines Salzes des Amins mit dem       substituierten        Dicyandiamid    in Gegenwart  eines Lösungsmittels, wie z. B. Wasser oder       f-Äthoxy        ätha.nol.     



  Das     N'-p-Jodphenyl-N'-methyl-N'-isopro-          pylbiguanid    stellt eine     -starke        Base    dar, wel  che mit organischen und     ariorga.nischen    Säu  ren beständige Salze ergibt, die in manchen  Fällen in     Wa,ser    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  spärlich     löslich    Kind, hergestellt werden.

   Auf  diese Weise kann man beispielsweise die  Salze mit Essigsäure, Milchsäure, Methan-         sulfonsäure,        Methylendisalicylsäure,        Methy-          len-bis-%3-oxyna.phtlioesä        ure    und Salzsäure  bequem herstellen.  



  Das folgende Beispiel diene zur Erläute  rung der Erfindung.  



       Beispiel:     Ein Gemisch von 12,6 Teilen     N"'-31:ethyl-          N3-isopropyldicyandiamid    und 28 Teilen     p-          Jodanilin-chlorhy        drat    in 200     Teilenfl-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       /3-Athoxyäth.anol        gewaschen    und aus Wasser  umkristallisiert.

   Auf diese Weise erhält man       NI    - p -     Jodphenyl        -N'-        methyl-N'-hsopropylbi-          hua.nid    in Form seines     1Vlonohydrochlorids,          welches    bei 236 bis     237     C schmilzt..



  Process for the preparation of a biguanide derivative. The present invention relates to an \ 'experience for the production of Ni-p-iodine-pheiiyl-N'-nietliyl-I @ T'-isopropylbiguanid, which is a valuable former therapeutic agent or as an intermediate for the manufacture of chemotherapeutic agents Means used: can be. It is a particularly valuable antimalarial drug.



  According to the invention, the said new compound, namely N1-p-iodoplienyl-N'-methyl-N'-isopropylbiguanide, is obtained by classifying N "-btethy l-N" -isopropy ldieyandiamide with p-iodaniliri implements.



  It is conveniently carried out by heating a salt of the amine with the substituted dicyandiamide in the presence of a solvent, such as. B. water or f-ethoxy ätha.nol.



  The N'-p-iodophenyl-N'-methyl-N'-isopropyl biguanide is a strong base which, with organic and aromatic acids, results in stable salts which, in some cases, are easily soluble in water are.

   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 prepared in dry form by mixing the components in an organic solvent, such as e.g. B. Acetone, or in an alcohol in which the salts are sparingly soluble in kind.

   In this way, for example, the salts with acetic acid, lactic acid, methanesulfonic acid, methylenedisalicylic acid, methylene bis% 3-oxyna.phtlioic acid and hydrochloric acid can be conveniently prepared.



  The following example serves to explain the invention.



       Example: A mixture of 12.6 parts of N "'- 31: ethyl-N3-isopropyldicyandiamide and 28 parts of p-iodaniline chlorohydrate in 200 parts of fl-ethoxyethanol is refluxed for 3 hours the mixture is cooled, whereupon it is filtered off, the solid residue is washed with cold / 3-ethoxyethanol and recrystallized from water.

   In this way one receives NI - p - iodophenyl -N'-methyl-N'-hsopropylbi- hua.nid in the form of its 1Vlonohydrochlorids, which melts at 236 to 237 C ..

Claims (1)

EMI0001.0065 PATENTANSPRUCH: <tb> -'erfahren <SEP> zur <SEP> Herstellung <SEP> von <SEP> N'-p-Jod phenyl--N''-methyl-N'-isopropylbiguanid, <SEP> da durch <SEP> gekennzeichnet, <SEP> dass <SEP> man <SEP> N3-ATethyl N'-isopropyldicyandiamid <SEP> mit <SEP> p-Jodanilin <tb> umsetzt, <tb> Das <SEP> N'-p-Jodphenyl-N'-rnethyl-N'-isopro pylbiguanid <SEP> ist <SEP> eine <SEP> starke <SEP> Base, <SEP> deren <SEP> Mono hydrochlorid <SEP> bei <SEP> 236 <SEP> bis <SEP> 2370 <SEP> C <SEP> schmilzt. <tb> Die <SEP> neue <SEP> Base <SEP> besitzt <SEP> kräftige <SEP> Antimalaria eigenschaften. EMI0001.0065 PATENT CLAIM: <tb> -'erfahren <SEP> for <SEP> production <SEP> of <SEP> N'-p-iodine phenyl - N '' - methyl-N'-isopropylbiguanide, <SEP> as marked by <SEP> , <SEP> that <SEP> one <SEP> N3-ATethyl N'-isopropyldicyandiamide <SEP> with <SEP> p-iodoaniline <tb> implements, <tb> <SEP> N'-p-iodophenyl-N'-methyl-N'-isopropylbiguanide <SEP> is <SEP> a <SEP> strong <SEP> base, <SEP> its <SEP> monohydrochloride <SEP> at <SEP> 236 <SEP> to <SEP> 2370 <SEP> C <SEP> melts. <tb> The <SEP> new <SEP> Base <SEP> has <SEP> powerful <SEP> antimalarial properties.
CH259680D 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative. CH259680A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB259680X 1945-10-08
GB170946X 1946-09-17
CH254800T 1946-10-08

Publications (1)

Publication Number Publication Date
CH259680A true CH259680A (en) 1949-01-31

Family

ID=27178036

Family Applications (1)

Application Number Title Priority Date Filing Date
CH259680D CH259680A (en) 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative.

Country Status (1)

Country Link
CH (1) CH259680A (en)

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