CH259711A - Process for the preparation of a biguanide derivative. - Google Patents
Process for the preparation of a biguanide derivative.Info
- Publication number
- CH259711A CH259711A CH259711DA CH259711A CH 259711 A CH259711 A CH 259711A CH 259711D A CH259711D A CH 259711DA CH 259711 A CH259711 A CH 259711A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- bromo
- acid
- biguanide derivative
- water
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation 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 3
- 239000000155 melt Substances 0.000 claims description 2
- HBCBLDVYTZWYLL-UHFFFAOYSA-N 3-bromo-4-iodoaniline Chemical compound NC1=CC=C(I)C(Br)=C1 HBCBLDVYTZWYLL-UHFFFAOYSA-N 0.000 claims 1
- 229940123208 Biguanide Drugs 0.000 claims 1
- 230000000078 anti-malarial effect Effects 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
- 239000002253 acid Substances 0.000 description 4
- 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
- 239000000203 mixture 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
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- -1 3-bromo-1-iodaniline Chemical compound 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
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000003814 drug Substances 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
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229940124597 therapeutic agent Drugs 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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines Biguanidderivates. Die vorliegende Erfindung betrifft ein Verfahren mir Herstellung von N1-3-Brom--1- jodphenyl-N -isopropyIbigtianid, welches ein wertvolles eliemotherapeutisehes -Mittel ist. oder als Zwisehenproduktfür die Herstellung von ehemotherapeutisehen Mitteln verwendet werden kann. Es ist insbesondere ein wert volles Antimalariamitt.el.
Erfindungsgemäss wird die besagte neue Verbindung, nämlich Nl-3-Broin-4-jodphenyl- N'-isopropylbiguanid, dadurch erhalten, dass i)iati N"-Isopropyldieyancliamid mit 3-Brom- -1-jodanilin umsetzt.
Die Umsetzung erfolgt zweckmässig durch l@rhitzen eines Salzes des Amins mit dem sub stituierten Dicyandianiid in Gegenwart eines Lösungsmittels, wie z. B. Wasser oder Äthoxyäthanol.
Das N'-3-Brom-4.-joclplienyl-N'-isopropy1- biguanid stellt. eine starke Base dar, welche mit. organischen und anorganischen Säuren beständige Salze ergibt, die in manchen Fäl len in Wasser leicht löslieli sind. Die Salze lassen sich dadurch herstellen, dass die Base in Wässrigen Lösungen der Säure gelöst und Hierauf das Wasser verdampft wird, doc!i können sie in trockener Form bequemer durch Vermischen der Komponenten in einem orga- n ischen 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, llilehsä.ure, lethansulfon- säure, Methylendisalicylsäure, Methylen-bis ss- cxynaplithoesänre und Salzsäure bequem her stellen.
Das folgende Beispiel diene zur Erläute rung der Erfindung. <I>Beispiel:</I> Ein Gemisch von 12,6 Teilen N'-Isopropyl- diey andiamid und 23,4 Teilen 3-Brom-4-jod- anilin-ehlorlivdrat in 100 Teilen. Wasser wird wäliren.d 3 Stunden -unter Rüekfluss zum Sie den 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 N 1-3-Br om-l-jodpheny 1-N'- isopropyIbiguanid in Form seines llonohydro- clilorids,welches bei 236 C schmilzt.
Process for the preparation of a biguanide derivative. The present invention relates to a process for the preparation of N1-3-bromo-1-iodophenyl-N -isopropylbigtianide, which is a valuable eliemotherapeutic agent. or it can be used as an intermediate for the manufacture of post-therapeutic agents. In particular, it is a valuable antimalarial agent.
According to the invention, the said new compound, namely Nl-3-broin-4-iodophenyl-N'-isopropylbiguanide, is obtained by i) reacting iati N'-isopropyldieyancliamide with 3-bromo-1-iodaniline.
The reaction is conveniently carried out by l @ rhitzen a salt of the amine with the sub-substituted dicyandianiid in the presence of a solvent, such as. B. water or ethoxyethanol.
The N'-3-bromo-4.-joclplienyl-N'-isopropy1-biguanid provides. a strong base, which with. organic and inorganic acids result in stable 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. 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 sparse Lich soluble. In this way, for example, the salts with acetic acid, lilehic acid, lethanesulphonic acid, methylenedisalicylic acid, methylene bis-s-cxynaplithoic 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'-isopropyl-dieyandiamide and 23.4 parts of 3-bromo-4-iodo-aniline-ehlorlivdrat in 100 parts. Water is heated for 3 hours under reflux to you. The mixture is then allowed to cool and it is filtered off. The solid residue is with cold. Water washed and recrystallized from water ..
That way it gets. one N 1-3-Brom-1-iodopheny 1-N'-isopropyIbiguanid in the form of its llonohydro- clilorids, which melts at 236C.
Claims (1)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB259711X | 1945-10-08 | ||
| GB170946X | 1946-09-17 | ||
| CH254800T | 1946-10-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH259711A true CH259711A (en) | 1949-01-31 |
Family
ID=27178067
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH259711D CH259711A (en) | 1945-10-08 | 1946-10-08 | Process for the preparation of a biguanide derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH259711A (en) |
-
1946
- 1946-10-08 CH CH259711D patent/CH259711A/en unknown
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