CH259672A - Process for the preparation of a biguanide derivative. - Google Patents
Process for the preparation of a biguanide derivative.Info
- Publication number
- CH259672A CH259672A CH259672DA CH259672A CH 259672 A CH259672 A CH 259672A CH 259672D A CH259672D A CH 259672DA CH 259672 A CH259672 A CH 259672A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- bromophenyl
- biguanide derivative
- water
- acid
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims 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
- -1 N'-p-bromophenyl-N "-isopropylbiguanide Chemical compound 0.000 claims description 3
- 239000000155 melt Substances 0.000 claims description 2
- WDFQBORIUYODSI-UHFFFAOYSA-N 4-bromoaniline Chemical compound NC1=CC=C(Br)C=C1 WDFQBORIUYODSI-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
- 229940123208 Biguanide Drugs 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000002246 antineoplastic agent Substances 0.000 description 2
- 229940127089 cytotoxic agent Drugs 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
- LWHDQPLUIFIFFT-UHFFFAOYSA-N 2,3,5,6-tetrabromocyclohexa-2,5-diene-1,4-dione Chemical compound BrC1=C(Br)C(=O)C(Br)=C(Br)C1=O LWHDQPLUIFIFFT-UHFFFAOYSA-N 0.000 description 1
- 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
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 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
- 150000001875 compounds Chemical class 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 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
- 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'-p-Brom- phenyl-N'-isopropylbiguanid, welches 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, nämlich N'-p-Bromphenyl-N'- isopropylbiguanid, dadurch erhalten, dass man N3-Isopropyldicyandiamid mit p-Brom- anil'in umsetzt.
Die Umsetzung erfolgt. zweckmässig durch Erhitzen eines Salzes des Amins mit dem substituierten Dieyandiamid in Gegenwart eines Lösungsmittels, wie z. B. Wasser oder ss-Äthoxyäthanol.
Das N'-p-Bromphenyl-N''-isopropylbigua- nid 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 las sen 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 orga nischen Lösungsmittel, wie z. B. Aceton, gder in einem Alkohol, in welchem die Salze spärlich löslich sind, hergestellt werden.
Auf diese Weise kann man beispielsweise die Salze mit Essigsäure, Milchsäure, Methan- sulfonsäure, Methylendisal'icylsäure, Methy- len-bis-fl-oxynaphthoesäure und Salzsäure be quem herstellen.
Das folgernde Beispiel diene zur Erläute rung der Erfindung.
<I>Beispiel:</I> Ein Gemisch von 12,6 Teilen N3-Isopro- pyldicyand,iamid und 27,9 Teilen p-Bromani- lin-chlorhydrat in 350 Teilen Wasser wird während 3 Stunden unter Rückfluss zum Sie den erhitzt. Hierauf lässt man das Gemisch abkühlen, worauf abfiltriert wird.
Der feste Rückstand wird mit kaltem Wasser gewa- achen und aus Wasser umkristallisiert. Auf diese Weise erhält man N'-p-B.romphenyl-N'\- isopropylbiguanid in Form seines Mono- hydrochlorids, welches bei 246 C schmilzt.
Process for the preparation of a biguanide derivative. The present invention relates to a process for the preparation of N'-p-bromophenyl-N'-isopropyl biguanide, 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, said new compound, namely N'-p-bromophenyl-N'-isopropylbiguanide, is obtained by reacting N3-isopropyldicyandiamide with p-bromoanil'ine.
The implementation takes place. Conveniently by heating a salt of the amine with the substituted Dieyandiamid in the presence of a solvent, such as. B. water or ss-ethoxyethanol.
The N'-p-bromophenyl-N "- isopropylbiguanide is a strong base, which with. organic and inorganic acids result in permanent salts, which in some cases are easily 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 mixed in dry form. the components in an orga African solvent, such as. B. acetone, or in an alcohol in which the salts are sparingly soluble, can be prepared.
In this way, for example, the salts with acetic acid, lactic acid, methanesulfonic acid, methylenedisalicylic acid, methylene-bis-f-oxynaphthoic acid and hydrochloric acid can be easily prepared.
The following example serves to explain the invention.
<I> Example: </I> A mixture of 12.6 parts of N3-isopropyldicyand, iamide and 27.9 parts of p-bromaniline chlorohydrate in 350 parts of water is refluxed for 3 hours. 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, N'-p-B.romphenyl-N '\ - isopropyl biguanide is obtained in the form of its monohydrochloride, which melts at 246 ° C.
Claims (1)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB259672X | 1945-10-08 | ||
| GB170946X | 1946-09-17 | ||
| CH254800T | 1946-10-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH259672A true CH259672A (en) | 1949-01-31 |
Family
ID=27178028
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH259672D CH259672A (en) | 1945-10-08 | 1946-10-08 | Process for the preparation of a biguanide derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH259672A (en) |
-
1946
- 1946-10-08 CH CH259672D patent/CH259672A/en unknown
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