CH259675A - Process for the preparation of a biguanide derivative. - Google Patents

Process for the preparation of a biguanide derivative.

Info

Publication number
CH259675A
CH259675A CH259675DA CH259675A CH 259675 A CH259675 A CH 259675A CH 259675D A CH259675D A CH 259675DA CH 259675 A CH259675 A CH 259675A
Authority
CH
Switzerland
Prior art keywords
methyl
preparation
bromophenyl
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 CH259675A publication Critical patent/CH259675A/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     Nl-p-Brom-          phenyl-N'-metliyl-N'-isopropylbiguanid,    wel  ches ein wertvolles chemotherapeutisches  Mittel ist oder     als        Zwischenprodukt.    für die  Herstellung von chemotherapeutischen Mit  teln verwendet werden kann. Es ist insbeson  dere ein wertvolles     Antimalaxiamittel.     



  Erfindungsgemäss wird die     besagte    neue  Verbindung, nämlich     Nl-p-Bromphenyl-N'-          methyl-N'-isopropylbiguanid,    dadurch erhal  ten,     da.ss        rnan        N3-Methyl-N's-isopropyldicya,n-          diamid        mit        p-Bromanilin    umsetzt.  



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



  Das     N'-p-Bromphenyl-N'-metliy        l-N'        -iso-          propyll>iguanid    stellt eine starke Base dar,  welche mit     orga.nisehen    und     a.norga.nischen     Säuren     beständige    Salze ergibt, die in man  chen     Fällen    in Wasser leicht löslich sind.

   Die       Salze    lassen sich dadurch     herstellen,    dass die  Base in     wässr.igen        Lösungen    der Säure gelöst       lind    hierauf das Wasser     verdampft    wird, doch  können sie in trockener Form bequemer durch       Verrnischen    der Komponenten in einem orga  nischen 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, Milchsäure, Methan-         sulfonsäure,        Methylendisalicylsäure,        Methy-          len-bis-ss-oxynaphthoesäure    und Salzsäure be  quem     herstellen.     



  Das folgende     Beispiel    diene zur Erläu  terung der Erfindung.         Bleispiel:            Ein    Gemisch von 14 Teilen     N"-Methyl-          N'-isopropyldicyandiamäd    und. 23 Teilen     p-          Bromanilin-chlorhydrat    in 250 Teilen Was  ser wird während 3 Stunden unter     Rückfluss     zum Sieden 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     NI-p-Brom-          pllenyl-N'-met-Iiyl-N'-isopropylbigaanid    in  Form     seines        Monohydroehlorids,    welches bei  251  C schmilzt.



  Process for the preparation of a biguanide derivative. The present invention relates to a process for the preparation of Nl-p-bromophenyl-N'-methyl-N'-isopropylbiguanide, which is a valuable chemotherapeutic agent or as an intermediate. can be used for the manufacture of chemotherapeutic agents. It is especially a valuable antimalaxic agent.



  According to the invention, the said new compound, namely Nl-p-bromophenyl-N'-methyl-N'-isopropylbiguanide, is obtained by reacting N3-methyl-N's-isopropyldicyanide with p-bromoaniline.



  The reaction 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-ethoxyethanol.



  The N'-p-bromophenyl-N'-methyl lN'-isopropyl iguanide is a strong base which, with organic and a.norganic acids, gives stable salts, which in some cases are easy in water are soluble.

   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 sparse Lich soluble, are produced.

   In this way, for example, the salts with acetic acid, lactic acid, methanesulfonic acid, methylenedisalicylic acid, methylene-bis-β-oxynaphthoic acid and hydrochloric acid can be easily prepared.



  The following example serves to explain the invention. Lead example: A mixture of 14 parts of N "-methyl-N'-isopropyldicyandiamad and 23 parts of p-bromoaniline chlorohydrate in 250 parts of water is heated to boiling under reflux for 3 hours. The mixture is then allowed to cool and then filtered off The solid residue is washed with cold water and recrystallized from water.

    In this way, NI-p-bromopllenyl-N'-met-IIyl-N'-isopropylbigaanide is obtained in the form of its monohydrochloride, which melts at 251.degree.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von NI-p-Brom- phenyl-N'-methyl-N'-isopropyl'biguanid, da durch gekennzeichnet, da.ss man N'-Methy l- N'-isopropyl.dicyandiamid mit p-Bromanilin umsetzt. Das NI-p-Bromphenyl-N'-methyl-N'-iso- propylbigua.nid ist eine starke Base, deren Monohydrochlorid bei 251 C schmilzt. Die neue Base besitzt kräftige Antimala.riaeigen- schaften. PATENT CLAIM: Process for the production of NI-p-bromophenyl-N'-methyl-N'-isopropyl'biguanide, characterized by the fact that N'-methyl-N'-isopropyl.dicyandiamide is used with p-bromoaniline implements. NI-p-bromophenyl-N'-methyl-N'-isopropylbigua.nid is a strong base whose monohydrochloride melts at 251 ° C. The new base has strong antimalarial properties.
CH259675D 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative. CH259675A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB259675X 1945-10-08
GB170946X 1946-09-17
CH254800T 1946-10-08

Publications (1)

Publication Number Publication Date
CH259675A true CH259675A (en) 1949-01-31

Family

ID=27178031

Family Applications (1)

Application Number Title Priority Date Filing Date
CH259675D CH259675A (en) 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative.

Country Status (1)

Country Link
CH (1) CH259675A (en)

Similar Documents

Publication Publication Date Title
CH259675A (en) Process for the preparation of a biguanide derivative.
CH259698A (en) Process for the preparation of a biguanide derivative.
CH259676A (en) Process for the preparation of a biguanide derivative.
CH259657A (en) Process for the preparation of a biguanide derivative.
CH259707A (en) Process for the preparation of a biguanide derivative.
CH259670A (en) Process for the preparation of a biguanide derivative.
CH259671A (en) Process for the preparation of a biguanide derivative.
CH259706A (en) Process for the preparation of a biguanide derivative.
CH259693A (en) Process for the preparation of a biguanide derivative.
CH259677A (en) Process for the preparation of a biguanide derivative.
CH259663A (en) Process for the preparation of a biguanide derivative.
CH259673A (en) Process for the preparation of a biguanide derivative.
CH259681A (en) Process for the preparation of a biguanide derivative.
CH259674A (en) Process for the preparation of a biguanide derivative.
CH259683A (en) Process for the preparation of a biguanide derivative.
CH259713A (en) Process for the preparation of a biguanide derivative.
CH259694A (en) Process for the preparation of a biguanide derivative.
CH259656A (en) Process for the preparation of a biguanide derivative.
CH259668A (en) Process for the preparation of a biguanide derivative.
CH259661A (en) Process for the preparation of a biguanide derivative.
CH259708A (en) Process for the preparation of a biguanide derivative.
CH254800A (en) Process for the preparation of a biguanide derivative.
CH259704A (en) Process for the preparation of a biguanide derivative.
CH259662A (en) Process for the preparation of a biguanide derivative.
CH259702A (en) Process for the preparation of a biguanide derivative.