CH259712A - Process for the preparation of a biguanide derivative. - Google Patents
Process for the preparation of a biguanide derivative.Info
- Publication number
- CH259712A CH259712A CH259712DA CH259712A CH 259712 A CH259712 A CH 259712A CH 259712D A CH259712D A CH 259712DA CH 259712 A CH259712 A CH 259712A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- preparation
- bromo
- biguanide derivative
- water
- Prior art date
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)
- 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-3-Brom-4- jodphenyl-N'-n-prop@-l.biguanid, welehes ein wertvolles chemotherapeutisches Mittel ist oder als Zwischenprodukt für die Herstellung von chemotherapeutischen Mitteln verwendet werden kann. Es ist insbesondere ein wert volles Antimalariamittel..
Erfindungsgemäss wird die besagte neue Verbindung, nämlieh Nl-3-Broin-4-jodphenyl- N'-n-liropylbiguanid, dadurch erhalten, dass man N"-n-Propyldicy andianiid mit 3-Broni-4- jodanilin umsetzt.
Die Unisetzung erfolgt zweckmässig dureh Erhitzen eines Salzes des Amins mit dem substituierten 1)ieyandiainid in Gegenwart eines Lösungsmittels, wie z. B. Wasser oder ss-Äthoyyätlianol.
Das N'-3-Brom-4-jodphenyl-N'-n-propyl- bin2tanid stellt eine starke Base dar, welehe mit orgaiiisclieii und anorganisehen Säuren beständige Salze ergibt, die in manehen Fäl len in Wasser leieht löslieh sind.
Die Salze lassen sieh dadurch herstellen, dass die Base in wälirigen Lösungen der Säure gelöst und hierauf das Wasser verdampft wird, doch können sie in trockener Form bequemer durch Verinisehen der Komponenten in einem orga nischen Lösungsmittel, wie z. B. Aceton, oder in einem Alkohol, in welchem die Salze spär lich löslieli sind, hergestellt werden.
Auf diese Weise kann man beispielsweise die Salze mit
EMI0001.0040
Essigsäure, <SEP> Milehsäure, <SEP> 1Iethansulfonsäure.
<tb> 1Iethylendisalicylsäure, <SEP> Methylen-bis-ss-o:cy naphtlioesätire <SEP> und <SEP> Salzsäure <SEP> bequem <SEP> her stellen.
<tb> Das <SEP> folgende <SEP> Beispiel <SEP> diene <SEP> zur <SEP> Erläute rung <SEP> der <SEP> Erfindung. <I>Beispiel:</I> Ein Gemiseh von 12,6 Teilen N3-n-Propyl- dicyandia.mid und 23,4 Teilen 3-Brom-4-jod- anilin-chlorhvdrat in 60 Teilen Wasser wird \#,ährend 3 Stunden unter Rüekfluss zum Sie den erhitzt.
Hierauf lässt man das Cremiseli abkühlen, worauf abfiltriert wird. Der feste li,ückstand wird finit kaltem Wasser gewasehen und aus Wasser umkristallisiert. Auf diese Weise erhält man Nl-3-Brom-4-jodplietiyl-N'- n-propylbigtianid in Form seines l onohydro- chlorids, welehes bei 227 bis 228 C sehmilzt.
Process for the preparation of a biguanide derivative. The present invention relates to a process for the preparation of Nl-3-bromo-4-iodophenyl-N'-n-prop@-l.biguanide, which is a valuable chemotherapeutic agent or can be used as an intermediate for the preparation of chemotherapeutic agents. In particular, it is a valuable antimalarial agent.
According to the invention, the said new compound, namely Nl-3-broin-4-iodophenyl-N'-n-liropylbiguanide, is obtained by reacting N "-n-propyldicyandianiide with 3-broni-4-iodaniline.
The unisetzung takes place expediently by heating a salt of the amine with the substituted 1) ieyandiainid in the presence of a solvent, such as. B. water or ss-Ethoyyätlianol.
The N'-3-bromo-4-iodophenyl-N'-n-propylbin2tanide is a strong base which, with organic and inorganic acids, gives stable salts which in some cases are slightly soluble in water.
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 in dry form by verinisehen the components in an orga African solvent such. B. acetone, or in an alcohol in which the salts are sparse Lichlöslieli are prepared.
In this way you can, for example, the salts with
EMI0001.0040
Acetic acid, <SEP> lactic acid, <SEP> 1ethanesulfonic acid.
<tb> Ethylenedisalicylic acid, <SEP> methylene-bis-ss-o: cy naphtlioesätire <SEP> and <SEP> hydrochloric acid <SEP> conveniently <SEP>.
<tb> The <SEP> following <SEP> example <SEP> serves <SEP> for <SEP> explanation <SEP> of the <SEP> invention. <I> Example: </I> A mixture of 12.6 parts of N3-n-propyl-dicyandia.mid and 23.4 parts of 3-bromo-4-iodo-aniline-chlorohydrate in 60 parts of water is used 3 hours under reflux to the heated.
The Cremiseli is then left to cool, after which it is filtered off. The solid liquid residue is finitely washed with cold water and recrystallized from water. In this way, Nl-3-bromo-4-iodoplietiyl-N'-n-propylbigtianide is obtained in the form of its ionohydrochloride, which melts at 227 to 228C.
Claims (1)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB259712X | 1945-10-08 | ||
GB170946X | 1946-09-17 | ||
CH254800T | 1946-10-08 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH259712A true CH259712A (en) | 1949-01-31 |
Family
ID=27178068
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH259712D CH259712A (en) | 1945-10-08 | 1946-10-08 | Process for the preparation of a biguanide derivative. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH259712A (en) |
-
1946
- 1946-10-08 CH CH259712D patent/CH259712A/en unknown
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