CH86317A - Process for the preparation of a readily soluble compound of CC diethylbarbituric acid. - Google Patents
Process for the preparation of a readily soluble compound of CC diethylbarbituric acid.Info
- Publication number
- CH86317A CH86317A CH86317DA CH86317A CH 86317 A CH86317 A CH 86317A CH 86317D A CH86317D A CH 86317DA CH 86317 A CH86317 A CH 86317A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- preparation
- readily soluble
- compound
- diethylbarbituric acid
- Prior art date
Links
- 229960002319 barbital Drugs 0.000 title claims description 8
- 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
- FTOAOBMCPZCFFF-UHFFFAOYSA-N 5,5-diethylbarbituric acid Chemical compound CCC1(CC)C(=O)NC(=O)NC1=O FTOAOBMCPZCFFF-UHFFFAOYSA-N 0.000 title description 6
- 239000002253 acid Substances 0.000 claims description 5
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 claims description 5
- 229960001231 choline Drugs 0.000 claims description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 239000000243 solution Substances 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- -1 amine salt Chemical class 0.000 claims description 3
- 238000002347 injection Methods 0.000 claims description 3
- 239000007924 injection Substances 0.000 claims description 3
- 230000009965 odorless effect Effects 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 2
- 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
- 150000003388 sodium 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
- 150000003839 salts Chemical class 0.000 claims 1
- 150000007513 acids Chemical class 0.000 description 2
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 2
- 239000004381 Choline salt Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 235000019417 choline salt Nutrition 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000000378 dietary effect Effects 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 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)
- Steroid Compounds (AREA)
Description
Verfahren zur Darstellung einer leicht löslichen Verbindung der CC-diäthylbarbitursäure. Die CC-dialkyl- und CC-arylalliylbarbitur- säuren besitzen in kaltem Wasser nur eine geringe Löslichkeit. Ihre wässerigen Lösun gen sind daher für Injektionszwecske 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 finit einer erheblichen Einbusse der Wirksamkeit ver bunden ist.
Gegenstand der vorliegenden Erfindung ist ein Verfahren zur Darstellung einer leicht löslichen Verbindung der CC-di- äthylbarbitursäure, welches darauf beruht, dass man auf CC-diäthylbarbitursäure Cholin einwirken lässt.
Die Verbindung der CC-diäthylbar- bitursäure mit Cholin ist ein geruchloser, kristallisierter Körper, welcher sich in Wasser, sowie, im Gegensatze zu der Natriuniverbin - dung der entsprechenden Säure, in All:
oliol leicht löst und sich gegenüber denn Aus.- gangsinaterial durch eine verstiirkte hypno- tische Wirkung auszeichnet.
Die wässeri-en Lösungen des Aminsalzes sind besonders hei Gegenwart von Alkohol oder andern hydrozyllialtigen organischen Verbi.nditno,eil, wie Glyzerin und dergleichen, lia.ltb@ir. Es ist daher möglich, die Lö sun-en des S@ilz,@s a,ueh auf dein Wege der Injektion zur Wir kung zu bringen.
Das neue Aminsalz soll in der Therapie Verwendung finden.
<I>Beispiel:</I> 184,2 Teile Diäthvlbarbitursäure werden unter Rühren eingetragen in 666-"/" Rauan- teile einer 1J_ normalen Cholinlösung bei.
Zimmertemperatur. Die entstehende Lösung wird filtriert und liefert alsdann beim Ein trocknen unter stank vermindertem Druck eine weisse kristallinische Masse, die das Cholinsalz der Diäthylbarbitursä .ure darstellt. Die Verbindung isty geruchlos und äusserst leicht löslich in Wasser finit alkalischer Reaktion.
Process for the preparation of a readily soluble compound of CC diethylbarbituric acid. The CC-dialkyl and CC-arylalliylbarbituric acids have only a low solubility in cold water. Your aqueous solutions are therefore not suitable for injection purposes 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 finitely linked to a considerable loss of effectiveness.
The present invention relates to a method for the preparation of a readily soluble compound of CC diethylbarbituric acid, which is based on the fact that CC diethylbarbituric acid is allowed to act on choline.
The compound of CC diethylbarbituric acid with choline is an odorless, crystallized body, which is in water, and, in contrast to the sodium compound of the corresponding acid, in space:
oliol dissolves easily and is distinguished from the starting material by an enhanced hypnotic effect.
The aqueous solutions of the amine salt are particularly useful in the presence of alcohol or other hydrocyclic organic compounds, such as glycerine and the like, lia.ltb@ir. It is therefore possible to bring the solutions of S @ ilz, @ s a, ueh to effect by means of injection.
The new amine salt will be used in therapy.
<I> Example: </I> 184.2 parts of dietary barbituric acid are added to 666 - "/" rough parts of a 1J_ normal choline solution with stirring.
Room temperature. The resulting solution is filtered and then, when dried under reduced pressure, gives a white crystalline mass which is the choline salt of diethylbarbituric acid. The compound is odorless and extremely easily soluble in water with a finite alkaline reaction.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH84997T | 1917-08-04 | ||
| CH86317T | 1917-08-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH86317A true CH86317A (en) | 1920-08-16 |
Family
ID=25703414
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH86317D CH86317A (en) | 1917-08-04 | 1917-08-04 | Process for the preparation of a readily soluble compound of CC diethylbarbituric acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH86317A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1134679B (en) * | 1957-01-31 | 1962-08-16 | Leo Werke G M B H | Process for the preparation of a salt of 5-phenyl-5-aethylbarbituric acid |
| DE1147587B (en) * | 1961-08-19 | 1963-04-25 | Leo Werke G M B H | Process for the preparation of choline 5-phenyl-5-ethyl barbiturate |
-
1917
- 1917-08-04 CH CH86317D patent/CH86317A/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1134679B (en) * | 1957-01-31 | 1962-08-16 | Leo Werke G M B H | Process for the preparation of a salt of 5-phenyl-5-aethylbarbituric acid |
| DE1147587B (en) * | 1961-08-19 | 1963-04-25 | Leo Werke G M B H | Process for the preparation of choline 5-phenyl-5-ethyl barbiturate |
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