CH86314A - Process for the preparation of a readily soluble compound of CC-phenylethylbarbituric acid. - Google Patents
Process for the preparation of a readily soluble compound of CC-phenylethylbarbituric acid.Info
- Publication number
- CH86314A CH86314A CH86314DA CH86314A CH 86314 A CH86314 A CH 86314A CH 86314D A CH86314D A CH 86314DA CH 86314 A CH86314 A CH 86314A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- preparation
- phenylethylbarbituric
- compound
- readily soluble
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 4
- -1 amine salt Chemical class 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 238000002347 injection Methods 0.000 claims description 3
- 239000007924 injection Substances 0.000 claims description 3
- 150000003388 sodium compounds Chemical class 0.000 claims description 3
- 239000000243 solution Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 235000011187 glycerol Nutrition 0.000 claims description 2
- 230000000147 hypnotic effect Effects 0.000 claims description 2
- 150000002894 organic compounds Chemical class 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 150000007513 acids Chemical class 0.000 description 2
- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/60—Three or more oxygen or sulfur atoms
- C07D239/62—Barbituric acids
- C07D239/64—Salts of organic bases; Organic double compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Saccharide Compounds (AREA)
Description
Verfahren zur Darstellung einer leicht löslichen Verbindung der CC-phenyläthylbarbitursäure. Die CC-dialkyl- und CC-arylalkylbarbitur- säuren besitzen in kaltem Wasser nur eine geringe Löslichkeit. Ihre wässerigen Lösun gen sind daher für Injektionszwecke und der gleichen nicht geeignet. Um den Anforde rungen in dieser Richtung zu genügen, hat man die Säuren in ihre Natriumsalze über geführt.
Diese Verbindungen haben den Nachteil, dass ihre wässerige Lösung stark alkalisch reagiert und die Barbitursäure durch das hydrolytisch abgespaltene Alkali eine Zersetzung erleidet, welche mit einer erheblichen Einbusse der Wirksamkeit ver bunden ist.
Gegenstand der vorliegenden Erfindung ist ein Verfahren zur Darstellung einer leicht löslichen Verbindung der CC-phenyl- äthylbarbitursäure, welches darauf beruht, dass man auf CC-phenyläthylbarbitursäi.ire Dimethylamin einwirken lässt.
Die ,Verbindung der CC-phenyläthyl- barbitursäure mit Dimethylamin ist ein kri stallisierter Körper, welcher sich in Wasser, sowie, im Gegensatze zu der Natriumverbin- dung der. entsprechenden Säure, in Alkohol leicht löst und sich gegenüber dem Aus gangsmaterial durch eine verstärkte hypno tische Wirkung auszeichnet. Die wässerigen Lösungen des Aminsalzes sind besonders bei Gegenwart von Alkohol oder andern hy.droxylhaltigen organischen Verbindungen, wie Glyzerin und dergleichen, haltbar.
Es ist daher möglich, die Lösungen des Salzesi auch auf dem Wege der Injektion zur \Vir- kung zu bringen.
Das neue Aminsalz soll in der Therapie Verwendung finden.
<I>Beispiel:</I> 1 Teil Phenyläthylbarbitursäure wird mit etwas mehr als der berechneten Menge einer 30 %igen wässerigen Lösung von Di- metbylamin versetzt. Unter Erwärmung ent steht eine sirupöse Lösung, aus welcher die Verbindung der Phenyläthylbarbitursäure mit Dimethylamin, nach dem Einengen im Vakuum, auskristallisiert.
Process for the preparation of a readily soluble compound of CC-phenylethylbarbituric acid. The CC-dialkyl- and CC-arylalkylbarbituric acids have only a low solubility in cold water. Your aqueous solutions are therefore not suitable for injections and the like. In order to meet the requirements in this direction, the acids have been converted into their sodium salts.
These compounds have the disadvantage that their aqueous solution reacts strongly alkaline and the barbituric acid undergoes decomposition as a result of the hydrolytically split off alkali, which is associated with a considerable loss of effectiveness.
The present invention relates to a process for the preparation of a readily soluble compound of CC-phenyl-ethylbarbituric acid, which is based on the fact that dimethylamine is allowed to act on CC-phenyläthylbarbituric acid.
The compound of CC-phenylethylbarbituric acid with dimethylamine is a crystallized body, which is in water and, in contrast to the sodium compound, the. corresponding acid, easily dissolves in alcohol and is characterized by an increased hypnotic effect compared to the starting material. The aqueous solutions of the amine salt are particularly stable in the presence of alcohol or other hydroxyl-containing organic compounds such as glycerine and the like.
It is therefore possible to make the saline solutions active by injection.
The new amine salt will be used in therapy.
<I> Example: </I> 1 part of phenylethylbarbituric acid is mixed with a little more than the calculated amount of a 30% aqueous solution of dimethylamine. When heated, a syrupy solution is created from which the compound of phenylethylbarbituric acid with dimethylamine crystallizes out after concentration in vacuo.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH84997T | 1917-08-04 | ||
| CH86314T | 1917-08-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH86314A true CH86314A (en) | 1920-08-16 |
Family
ID=25703411
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH86314D CH86314A (en) | 1917-08-04 | 1917-08-04 | Process for the preparation of a readily soluble compound of CC-phenylethylbarbituric acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH86314A (en) |
-
1917
- 1917-08-04 CH CH86314D patent/CH86314A/en unknown
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