CH291376A - Process for the preparation of o- (N-2- (B-oxy-ethoxy) -3-oxymerkuri-propyl-carbamido) -phenoxyacetic acid. - Google Patents
Process for the preparation of o- (N-2- (B-oxy-ethoxy) -3-oxymerkuri-propyl-carbamido) -phenoxyacetic acid.Info
- Publication number
- CH291376A CH291376A CH291376DA CH291376A CH 291376 A CH291376 A CH 291376A CH 291376D A CH291376D A CH 291376DA CH 291376 A CH291376 A CH 291376A
- Authority
- CH
- Switzerland
- Prior art keywords
- phenoxyacetic acid
- carbamido
- oxymerkuri
- propyl
- oxy
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 229940100892 mercury compound Drugs 0.000 claims description 2
- 150000002731 mercury compounds Chemical class 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000002934 diuretic Substances 0.000 description 2
- 230000001882 diuretic effect Effects 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229960000278 theophylline Drugs 0.000 description 2
- 208000004880 Polyuria Diseases 0.000 description 1
- OFIHJYLASXZYAR-UHFFFAOYSA-N [Hg](=O)=O Chemical compound [Hg](=O)=O OFIHJYLASXZYAR-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- WRYNUJYAXVDTCB-UHFFFAOYSA-M acetyloxymercury Chemical compound CC(=O)O[Hg] WRYNUJYAXVDTCB-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 229940030606 diuretics Drugs 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(II) oxide Inorganic materials [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/10—Mercury compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von o-[N-2-(ss-Oxy-äthoxy)-3-oxymerkuri-propyl-carbamido]- phenoxyessigsäure. Die vorliegende Erfindung bezieht sich auf ein Verfahren zur Herstellung von o-[N- 2- (f-Oxy - äthoxy) - 3-oxy-merkuri-pr opy 1-carb- aniiclo]-phenoxyessigsäure, einer weissen, kri stallinen Substanz, die in Wasser unlöslich und in den meisten organischen Lösungsmit teln mir wenig löslich ist.
Das erfindungsgemässe Verfahren ist da durch gekennzeichnet, dass man o-Allylcarb- amiclo-phenoxyessigsäure in Äthylenglykol löst. und eine den Rest HOHg- bildende Mer- kuriverbindung, wie z. B. Merkuriaeetat oder Merkurioxyd, zur Einwirkung bringt. Beim Stehenlassen fällt die merkurierte Verbindung in Forni von Kristallen aus dem Reaktions gemisch aus. Die Kristalle werden beispiels weise durch Filtrieren oder sonstwie abge trennt.
<I>Beispiel 1:</I> Man vermischt 235 g (1 Mol) o-(N-Allyl- earbaniido) -phenoxyessigsäure mit 1 Liter Äthylenglykol, versetzt das Gemisch mit 318 g (1 Mo1) Merkuriacetat und rührt, bis die festere Substanzen in Lösung gegangen sind. Die erhaltene Lösung wird bei Raumtempera tur während etwa 3 Tagen stehengelassen.
Während dieser Zeit scheidet sich ein aus o- [N-2- (ss- Oxy- äthoxy) -3-oxymerkuri-propyl- earbamido] - phenoxyessigsäure bestehender kristalliner Niederschlag ab. Der Niederschlag wird abfiltriert, mit Äthylalkohol gründlich gewaschen und dann getrocknet. Auf diese Weise werden 433 g o-[N-2-(fl'-Oxy-äthoxy)-3- oxymerkuri-propyl- carbamido ] -phenoxyessig- säure erhalten.
Eine Probe dieser Substanz zersetzt sieh beim Erhitzen bei etwa 200 bis 202 C.
Die Analyse dieser Verbindung ergibt einen Quecksilbergehalt von 38,62%, während der berechnete Wert 39,10% beträgt.
<I>Beispiel 2:</I> 235 g (1 Mol) o-(N-Allyl-carbamido)-phen- oxyessigsäure werden in 1 Liter frisch destil liertes Äthylenglykol eingetragen. Das Ge misch wird unter Rühren mit 216,6 g (1 Mol) rotem Merkurioxyd versetzt. Dann versetzt.
man mit 19,8 g (0,33 Mol) Eisessig und er wärmt das Gemisch unter Rühren auf 40 bis 50 C. -Man unterbricht das Erhitzen und rührt das Reaktionsgemisch während 2 Stun den, während welcher Zeit sich ein aus o-[N- 2- (fl-Oxy- äthoxy) - 3 - oxymerkuri-propyl-carb- amido] -phenoxyessigsäure bestehender, kri stalliner, weisser Niederschlag abscheidet. Der Niederschlag wird abfiltriert, mit warmem destilliertem Wasser und Äthanol gewaschen und getrocknet.
Die auf diese Weise erhaltene o-[N-2-(ss- Oxyäthoxy) -3-oxymerkuri-propyl-carbamido] - phenoxyessigsäure zersetzt sich beim Erhitzen bei etwa 200 bis 202 C.
Die o-[N 2-(ss-Oxy-äthoxy)-3-oxymerkuri- propyl-earbamido]-phenoxyessigsäure ist ein wirksames Diuretikum. Für die therapeu tische Verwendung werden vorzugsweise die Salze der Säure verwendet, da sie in Wasser leicht. löslich sind. Die Salze werden zweek- mässig in wässeriger Lösung (5 bis 20 Ge wichtsteile Salz auf 100 Volumteile Lösung) verwendet.
Den wässerigen Lösungen wird ausserdem vorzugsweise Theophyllin oder ein Salz des letzteren in einer Menge von etwa 5 bis 10 Gewichtsteilen auf 100 Volumteile der wässerigen Lösung zugesetzt. Das zuge- setzte Theophyllin erhöht die diuret.ische Wir kung und lindert die Schmerzen und die Rei zung, die gewöhnlich bei der Einspritzeng von quecksilberhaltigen Diuretika auftreten, und ermöglicht sogar die subkutane Verabreiehung der neuen Verbindungen.
Process for the preparation of o- [N-2- (ss-oxy-ethoxy) -3-oxymerkuri-propyl-carbamido] -phenoxyacetic acid. The present invention relates to a process for the preparation of o- [N- 2- (f-oxy - ethoxy) - 3-oxy-merkuri-pr opy 1-carbaniiclo] -phenoxyacetic acid, a white, crystalline substance, which is insoluble in water and not very soluble in most organic solvents.
The process according to the invention is characterized in that o-allylcarbamiclo-phenoxyacetic acid is dissolved in ethylene glycol. and a mercury compound forming the remainder HOHg, such as e.g. B. Merkuriaeetat or Merkurioxyd brings to action. When left to stand, the mercurized compound precipitates in the form of crystals from the reaction mixture. The crystals are, for example, separated by filtration or otherwise.
<I> Example 1: </I> 235 g (1 mol) of o- (N-allyl-earbaniido) -phenoxyacetic acid are mixed with 1 liter of ethylene glycol, 318 g (1 mol) of mercury acetate are added to the mixture and the mixture is stirred until the solid substances have gone into solution. The solution obtained is left to stand at room temperature for about 3 days.
During this time, a crystalline precipitate consisting of o- [N-2- (ss-oxyethoxy) -3-oxymerkuri-propyl-earbamido] -phenoxyacetic acid separates out. The precipitate is filtered off, washed thoroughly with ethyl alcohol and then dried. In this way 433 g of o- [N-2- (fl'-oxy-ethoxy) -3-oxymerkuri-propyl-carbamido] -phenoxyacetic acid are obtained.
A sample of this substance decomposes when heated at around 200 to 202 C.
The analysis of this compound shows a mercury content of 38.62%, while the calculated value is 39.10%.
Example 2: 235 g (1 mol) of o- (N-allyl-carbamido) -phenoxyacetic acid are introduced into 1 liter of freshly distilled ethylene glycol. The mixture is mixed with 216.6 g (1 mol) of red mercury dioxide while stirring. Then moved.
one with 19.8 g (0.33 mol) of glacial acetic acid and he warms the mixture with stirring to 40 to 50 ° C. -Man interrupts the heating and stirs the reaction mixture for 2 hours, during which time an o- [N - 2- (fl-oxyethoxy) - 3 - oxymerkuri-propyl-carbamido] -phenoxyacetic acid existing, crystalline, white precipitate separates out. The precipitate is filtered off, washed with warm distilled water and ethanol and dried.
The o- [N-2- (ss- oxyethoxy) -3-oxymerkuri-propyl-carbamido] -phenoxyacetic acid obtained in this way decomposes when heated at about 200 to 202 ° C.
The o- [N 2- (ss-oxy-ethoxy) -3-oxymerkuripropyl-earbamido] -phenoxyacetic acid is an effective diuretic. The salts of the acid are preferably used for therapeutic use, since they are easily absorbed in water. are soluble. The salts are used in an aqueous solution (5 to 20 parts by weight of salt per 100 parts by volume of solution).
In addition, theophylline or a salt of the latter is preferably added to the aqueous solutions in an amount of about 5 to 10 parts by weight per 100 parts by volume of the aqueous solution. The theophylline added increases the diuretic effect and alleviates the pain and irritation that usually occurs with the injection of diuretics containing mercury, and even allows the new compounds to be administered subcutaneously.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US291376XA | 1950-02-13 | 1950-02-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH291376A true CH291376A (en) | 1953-06-15 |
Family
ID=21847438
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH291376D CH291376A (en) | 1950-02-13 | 1950-12-14 | Process for the preparation of o- (N-2- (B-oxy-ethoxy) -3-oxymerkuri-propyl-carbamido) -phenoxyacetic acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH291376A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1468201B1 (en) * | 1961-01-19 | 1971-11-11 | Merck & Co Inc | phenoxy-acetic acid compounds and processes for their preparation |
-
1950
- 1950-12-14 CH CH291376D patent/CH291376A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1468201B1 (en) * | 1961-01-19 | 1971-11-11 | Merck & Co Inc | phenoxy-acetic acid compounds and processes for their preparation |
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