CH84997A - Process for preparing an easily soluble compound of CC-diethylbarbituric acid. - Google Patents
Process for preparing an easily soluble compound of CC-diethylbarbituric acid.Info
- Publication number
- CH84997A CH84997A CH84997DA CH84997A CH 84997 A CH84997 A CH 84997A CH 84997D A CH84997D A CH 84997DA CH 84997 A CH84997 A CH 84997A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- compound
- alcohol
- preparing
- easily soluble
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 9
- 229960002319 barbital Drugs 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000002253 acid Substances 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 239000000243 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 238000002347 injection Methods 0.000 claims description 3
- 239000007924 injection Substances 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 150000003388 sodium compounds Chemical class 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
- 150000003839 salts 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
- 230000002378 acidificating effect Effects 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- FTOAOBMCPZCFFF-UHFFFAOYSA-N 5,5-diethylbarbituric acid Chemical compound CCC1(CC)C(=O)NC(=O)NC1=O FTOAOBMCPZCFFF-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 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
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Description
Verfabren zur Dai-stellung einer leicbt lüsliclien Verbindung der CC-diâtliylbarbitur siiur e. Process for the preparation of an easily soluble compound of the CC-diâtliylbarbitur acid e.
Die CC-dialkyl- und CC-arylalkylbarbitur sâuren besitzen in kaltem Wasser nur eine geringe LSslichkeit. Ihre wâsserigen L6sungen sind daher für Injektionszwecke und der gleichen niclit geeignet. Um den Anforderungen in dieser Richtung zu genügen, hat man die Süuren in ihre Natriumsalze übergeführt. Diese Verbindungen haben den Nachteil, dah ihre wâsserige Lbsung stark alkalisch reagiert und die Barbitursàure durch das hydrolytisch abgespaltene Alkali eine Zersetzung erleidet, welche mit einer erheblichen Einbuee der Wirksamkeit verbunden ist. The CC dialkyl and CC arylalkyl barbituric acids have only a low solubility in cold water. Their aqueous solutions are therefore not suitable for injection purposes and the same. 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 has a strongly alkaline reaction and the barbituric acid undergoes decomposition as a result of the hydrolytically split off alkali, which is associated with a considerable loss of effectiveness.
Gegenstand der vorliegenden Erfindung ist ein Verfahren zur Darstellung einer leiclit 16slichen Verbindung der CC-diâthylbarbitur sâure, welches darauf beruht, daG man auf CC-diâ.thylbarbitursâtire Diâthylamin einwir ken lâBt. The subject of the present invention is a process for the preparation of a soluble compound of CC-diâ.thylbarbituric acid, which is based on allowing diethylamine to act on CC-diâ.thylbarbitursâtire.
Die Verbindung der CC-diâthylbarbitur süure mit Diüthylamin ist ein kristallisierter gSrper, welcher sich in Wasser, sowie, im Gegensatze zu der Natriumverbindung der entsprechenden Sâure, in Alkohol sehr leiclit lbst und sich gegenüber dem Ausgangsmaterial The compound of CC-diethylbarbituric acid with diethylamine is a crystallized body which dissolves very easily in water and, in contrast to the sodium compound of the corresponding acid, in alcohol and differs from the starting material
durcli eine verstiirkte hypnotische Wirkung auszeichnet. Die wüsserigen Lüsungen des Aminsalzes sind besonders bei Gegenwart von Alkoliol oder andern hydroxyllialtigen or ganisclien Verbindungen, wie Glyzerin und dergleichen, haltbar. Es ist daller m;3glich, die Lüsungen des Salzes auch auf dem Wege der Injektion zur Wirkung zu bringen. characterized by an increased hypnotic effect. The aqueous solutions of the amine salt are particularly stable in the presence of alcohol or other hydroxylated organic compounds such as glycerine and the like. It is then possible to bring the solutions of the salt into action by way of injection.
Das noue Aininsalz roll in der Therapie Verwendung finden. The noue Aininsalz roll can be used in therapy.
<I>Beispiel 1:</I> 1 Teil Diüthylbarbitursii,ure wird in 1,7 Teilen absolutem Alkohol unter Zugabe von wenig mehr als der theoretisch notwendigen Menge inüglichst hocliprozentigem Diâthylamin bel 50-60 gelüst. Die warme Lüsung wird filtriert und noch warni mit 2,2 Teilen ab solutem ther versetzt. Aus der zuniichst klarbleibenden Lüsung kristallisiert allmühlich die Hauptinenge der neuen Verbindung aus. <I>Beispiel 2</I> 1 Teil inügliehst fein pulverisierte Diâthyl barbitursâure wird mit dem anderthalbfaehen der theoretisch notwendigen Menge Diâthyl- <I>Example 1:</I> 1 part of diethylbarbituric acid is dissolved in 1.7 parts of absolute alcohol with the addition of a little more than the theoretically necessary amount of diethylamine with the highest possible concentration at 50-60. The warm solution is filtered, and 2.2 parts of absolute ether are still added. The bulk of the new compound gradually crystallizes out of the initially clear solution. <I>Example 2</I> 1 part of the most finely powdered diethyl barbituric acid is mixed with one and a half times the theoretically required amount of diethyl
amie innig verrieben. Unter Erwârmung ver flüssigt sich das Reaktionsgemisch zu einem klaren Sirup, der bald erstarrt. Die entstan dene Verbindung der Diâthylbarbitursâure mit Diâthylamin wird durch kurzes Liegen an der Luft voie überschüssigen Diâthylamin getrennt. Sie ist in Wasser sûr leicht, in den üblichen organischen Lüsungsmitteln leiclit lôslich. amie deeply rubbed. When heated, the reaction mixture liquefies to form a clear syrup, which soon solidifies. The resulting compound of diethylbarbituric acid with diethylamine is separated from excess diethylamine by briefly lying in air. It is very easily soluble in water and slightly soluble in the usual organic solvents.
<I>Beispiel 3</I> 1 Teil Diâtliylbarbitursâui-e wird in 6 Teilo einer wasserigen Lüsung, welche 0,4 Telle Diütlivlamin enthült, eingetragen. Die Diâthyl barhI'tui'Sâ,nrB 1iist sich glatt, und die ent standene Lbsung ist, gegeberienfalls nach vorheriger Filtration, <B>zur</B> Verwendung für theraheutische Zwecke gebrauchsfertig. <I>Example 3</I> 1 part of diethylbarbituric acid is added to 6 parts of an aqueous solution containing 0.4 part of diylivlamin. The Diâthyl barhI'tui'Sâ,nrB 1i is smooth and the resulting solution is ready for use, after prior filtration if necessary, <B>for</B> use for therapeutic purposes.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH84997T | 1917-08-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH84997A true CH84997A (en) | 1920-05-01 |
Family
ID=4341230
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH84997D CH84997A (en) | 1917-08-04 | 1917-08-04 | Process for preparing an easily soluble compound of CC-diethylbarbituric acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH84997A (en) |
-
1917
- 1917-08-04 CH CH84997D patent/CH84997A/en unknown
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