CH259660A - Process for the preparation of a biguanide derivative. - Google Patents
Process for the preparation of a biguanide derivative.Info
- Publication number
- CH259660A CH259660A CH259660DA CH259660A CH 259660 A CH259660 A CH 259660A CH 259660D A CH259660D A CH 259660DA CH 259660 A CH259660 A CH 259660A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- propylbiguanide
- biguanide derivative
- water
- diiodophenyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 4
- 150000004283 biguanides Chemical class 0.000 title description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- GHWMYAKHPIIZNH-UHFFFAOYSA-N 3,4-diiodoaniline Chemical compound NC1=CC=C(I)C(I)=C1 GHWMYAKHPIIZNH-UHFFFAOYSA-N 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 1
- 230000000078 anti-malarial effect Effects 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- -1 N'-3 Chemical class 0.000 description 2
- 239000002246 antineoplastic agent Substances 0.000 description 2
- 229940127089 cytotoxic agent Drugs 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- SWHSXWLSBBYLGM-UHFFFAOYSA-N 2-[(2-carboxyphenoxy)methoxy]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1OCOC1=CC=CC=C1C(O)=O SWHSXWLSBBYLGM-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003430 antimalarial agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
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)
Description
Verfahren zur Herstellung eines Biguanidderivates. Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung von N'-3,4-Dijod- plienyl-N--,-n-propylbiguanid, welches ein wert volles chemotherapeutisches 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 N'-3,4-Dijodplienyl-N- ii-propylbiguanid, dadurch erhalten, dass man N'-n-Propyldieyandiamid mit 3,4-Dijodanilin umsetzt.
Die Umsetzung erfolgt zweckmässig durch Erhitzen eines Salzes des Amins mit dein substituierten Dieyandiamid in Gegenwart eines Lösungsmittels, wie z. B. Wasser oder ss-'@tlioxyäthanol.
Das N'-3,4-Dijodphenyl-NS-n-propylbi- guanid stellt eine starke Base dar, welche mit organischen und anorganischen Säuren be ständige Salze ergibt, die in manchen Fällen 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 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 Essigsäure, Milchsäure, Methansulfonsäure, Methylendisalicylsäure, Methylen-bis-ss-oxy- naphthoesäure und Salzsäure bequem her stellen.
Das folgende Beispiel diene zur Erläute rung der Erfindung.
<I>Beispiel:</I> Ein Gemisch von 12,6 Teilen N--n-Propyl- dicyandiamid und 38,2 Teilen 3,4-Dijod- anilin-ehlorhydrat in<B>250</B> Teilen Wasser wird während 3 Stunden unter Rüekfluss 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 N1-3,4-Dijodphenyl-N'-n- propylbiguanid in Form seines Monohydro- ehlorids, welches bei 226-227 C schmilzt.
Process for the preparation of a biguanide derivative. The present invention relates to a process for the preparation of N'-3,4-diiodoplienyl-N -, - n-propylbiguanide, which is a valuable chemotherapeutic 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, the said new compound, namely N'-3,4-diiodoplienyl-N-ii-propylbiguanide, is obtained by reacting N'-n-propyldiyandiamide with 3,4-diiodaniline.
The reaction is conveniently carried out by heating a salt of the amine with your substituted dieyandiamide in the presence of a solvent, such as. B. water or ss - '@ tlioxyäthanol.
The N'-3,4-diiodophenyl-NS-n-propylbiguanide is a strong base which, with organic and inorganic acids, results in 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 convenient in dry form by mixing the components in an orga African solvent, such as. B. acetone, or in an alcohol in which the salts are sparse Lichlöslieli are prepared.
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 conveniently prepared.
The following example serves to explain the invention.
<I> Example: </I> A mixture of 12.6 parts of N-n-propyl dicyandiamide and 38.2 parts of 3,4-diiodoaniline chlorohydrate in 250 parts of water is used heated to boiling for 3 hours under reflux. The mixture is then allowed to cool and it is filtered off. The solid residue is washed with cold water and recrystallized from water. In this way, N1-3,4-diiodophenyl-N'-n-propylbiguanide is obtained in the form of its monohydrochloride, which melts at 226-227 ° C.
Claims (1)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB259660X | 1945-10-08 | ||
| GB170946X | 1946-09-17 | ||
| CH254800T | 1946-10-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH259660A true CH259660A (en) | 1949-01-31 |
Family
ID=27178016
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH259660D CH259660A (en) | 1945-10-08 | 1946-10-08 | Process for the preparation of a biguanide derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH259660A (en) |
-
1946
- 1946-10-08 CH CH259660D patent/CH259660A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH259660A (en) | Process for the preparation of a biguanide derivative. | |
| CH259707A (en) | Process for the preparation of a biguanide derivative. | |
| CH259704A (en) | Process for the preparation of a biguanide derivative. | |
| CH259713A (en) | Process for the preparation of a biguanide derivative. | |
| CH259708A (en) | Process for the preparation of a biguanide derivative. | |
| CH259699A (en) | Process for the preparation of a biguanide derivative. | |
| CH259706A (en) | Process for the preparation of a biguanide derivative. | |
| CH259666A (en) | Process for the preparation of a biguanide derivative. | |
| CH254800A (en) | Process for the preparation of a biguanide derivative. | |
| CH259698A (en) | Process for the preparation of a biguanide derivative. | |
| CH259684A (en) | Process for the preparation of a biguanide derivative. | |
| CH259661A (en) | Process for the preparation of a biguanide derivative. | |
| CH259693A (en) | Process for the preparation of a biguanide derivative. | |
| CH259690A (en) | Process for the preparation of a biguanide derivative. | |
| CH259700A (en) | Process for the preparation of a biguanide derivative. | |
| CH259681A (en) | Process for the preparation of a biguanide derivative. | |
| CH259655A (en) | Process for the preparation of a biguanide derivative. | |
| CH259659A (en) | Process for the preparation of a biguanide derivative. | |
| CH259709A (en) | Process for the preparation of a biguanide derivative. | |
| CH259663A (en) | Process for the preparation of a biguanide derivative. | |
| CH259695A (en) | Process for the preparation of a biguanide derivative. | |
| CH259672A (en) | Process for the preparation of a biguanide derivative. | |
| CH259714A (en) | Process for the preparation of a biguanide derivative. | |
| CH259654A (en) | Process for the preparation of a biguanide derivative. | |
| CH259694A (en) | Process for the preparation of a biguanide derivative. |