CH259694A - Process for the preparation of a biguanide derivative. - Google Patents

Process for the preparation of a biguanide derivative.

Info

Publication number
CH259694A
CH259694A CH259694DA CH259694A CH 259694 A CH259694 A CH 259694A CH 259694D A CH259694D A CH 259694DA CH 259694 A CH259694 A CH 259694A
Authority
CH
Switzerland
Prior art keywords
preparation
biguanide derivative
acid
dibromophenyl
salts
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 CH259694A publication Critical patent/CH259694A/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     Ni-3,4-Di-          broinlihenyl-N5-n-propylbiguanid,    welches  ein wertvolles chemotherapeutisches Mittel  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     N'-3,4-DiIironipIienvl-          N5-n-propylbigtianid,    dadurch erhalten, dass  man     N'-n-Propyldicyandiamid    mit     3,4-Di-          bronianilin    umsetzt.  



  Die     Unisetzung    erfolgt     zweckmässig    durch  Erhitzen eines Salzes des Amins mit. dem       substituierten        Dicyandiamid    in Gegenwart  eines Lösungsmittels, wie z. B.     Wasser    oder       ss-Ät        holyäthanol    .  



  Das     Ni-3,4-Dibromplienyl-N5-n-pi-opyl-          biguanid    stellt eine starke Base dar, welche       finit    organischen     und    anorganischen Säuren  beständige Salze ergibt, die in manchen Fäl  len in Wasser leicht löslich sind. Die Salze       lassen    sich 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 sind, hergestellt werden.

   Auf  diese Weise kann man beispielsweise die Salze    mit Essigsäure, Milchsäure,     Methansulfon-          säure,        Methylendisalieylsäure,        Methylen-bis-          ss-oxy        naphthoesäure    und Salzsäure bequem  herstellen.  



  Das folgende Beispiel diene zur Erläute  rung der Erfindung.  



  <I>Beispiel:</I>  Ein Gemisch von 12,6 Teilen     N3-n-Propyl-          dicy        andiamid    und 28,8 Teilen     3,4-Dibrom-          aiiilin-chlorhydrat    in 80 Teilen     f3-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     Äthyl-          acetat    gewaschen und aus Wasser umkristalli  siert.

   Auf diese Weise erhält man     N1-3,4-Di-          bromphenyl.-N'-n-propylbiguanid    in Form  seines     Monohydrochlorids,    welches bei 217 bis  218  C schmilzt.



  Process for the preparation of a biguanide derivative. The present invention relates to a process for the preparation of Ni-3,4-dibroinlihenyl-N5-n-propylbiguanide, which is a valuable chemotherapeutic agent or can be used as an intermediate for the manufacture of chemotherapeutic agents. It is a particularly valuable antimalarial drug.



  According to the invention, said new compound, namely N'-3,4-diironipIienvl-N5-n-propylbigtianide, is obtained by reacting N'-n-propyldicyandiamide with 3,4-di-bronianiline.



  The dissolution is expediently carried out by heating a salt of the amine. the substituted dicyandiamide in the presence of a solvent, such as. B. water or ss-Ät holyäthanol.



  The Ni-3,4-dibromoplienyl-N5-n-pi-opyl-biguanid is a strong base, which gives finite organic and inorganic acids stable salts, 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 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 sparingly soluble.

   In this way, for example, the salts with acetic acid, lactic acid, methanesulfonic acid, methylenedisalic acid, methylene-bis-s-oxy naphthoic 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 N3-n-propyl dicyandiamide and 28.8 parts of 3,4-dibromo-aiiilin chlorohydrate in 80 parts of f3-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 ethyl acetate and recrystallized from water.

   In this way, N1-3,4-dibromophenyl.-N'-n-propylbiguanide is obtained in the form of its monohydrochloride, which melts at 217 to 218.degree.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von N1-3,4-Di- bromphenyl-N'-n-propylbiguanid, dadurch ge kennzeichnet, dass man N3-n-Propyldicy an diamid mit 3,4-Dibromanilin umsetzt. Das N'-3,4-Dibromphenyl-N'-n-propyl- biguanid ist eine starke Base, deren Mono- hydrochlorid bei 217 bis 218 C schmilzt. Die neue Base besitzt kräftige Antimalariaeigen- sehaften. PATENT CLAIM: Process for the preparation of N1-3,4-dibromophenyl-N'-n-propylbiguanide, characterized in that N3-n-propyldicyclic is reacted on diamide with 3,4-dibromaniline. N'-3,4-dibromophenyl-N'-n-propyl biguanide is a strong base whose monohydrochloride melts at 217 to 218 ° C. The new base has strong antimalarial properties.
CH259694D 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative. CH259694A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB259694X 1945-10-08
GB170946X 1946-09-17
CH254800T 1946-10-08

Publications (1)

Publication Number Publication Date
CH259694A true CH259694A (en) 1949-01-31

Family

ID=27178050

Family Applications (1)

Application Number Title Priority Date Filing Date
CH259694D CH259694A (en) 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative.

Country Status (1)

Country Link
CH (1) CH259694A (en)

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