CH280319A - Process for the preparation of a new barbituric acid compound. - Google Patents
Process for the preparation of a new barbituric acid compound.Info
- Publication number
- CH280319A CH280319A CH280319DA CH280319A CH 280319 A CH280319 A CH 280319A CH 280319D A CH280319D A CH 280319DA CH 280319 A CH280319 A CH 280319A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- preparation
- barbituric acid
- acid compound
- new
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- -1 barbituric acid compound Chemical class 0.000 title description 4
- 238000002360 preparation method Methods 0.000 title description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- RVBUGGBMJDPOST-UHFFFAOYSA-N 2-thiobarbituric acid Chemical compound O=C1CC(=O)NC(=S)N1 RVBUGGBMJDPOST-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 239000007864 aqueous solution 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
- 239000012259 ether extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000002695 general anesthesia Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000002557 soporific effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000816 toxic dose Toxicity 0.000 description 1
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Description
Verfahren zur Herstellung einer neuen Barbitursäureverbindung. Geo-enstand der vorliegenden Erfindung ist ein Verfahren zur Herstellung einer neuen Barbitursäureverbindung, nämlich der Spiro- 2,3,5-triniethyley elopentan-(1),5'-thiobarbitur- säure.
Die neue Thiobarbitursäure besitzt berulii- Oende, einschläfernde und anästhetiselie Eigen schaften von bemerkenswerter kurzer Dauer. Sie ist in kleinen Dosen wirksam und zeigst. einen weiten Sieherheitsbereieh zwischen therapeutischer und toxischer Dosis. Sie ist besonders geeignet, um durch intravenöse Ver- abreiehung eine allgemeine Anästhesie von kurzer Dauer zu erzeugen.
Die neue Verbindung kann durch die fol- gc@n(le Formel wiedergegeben -erden:
EMI0001.0022
Das erfindungsgemässe Verfahren ist da- dureli gelzennzeielinet, dass man 3.,1-Diea@b- iillioxz='?,3,5-trimetlivieyelopentan mit Thio- liarnstoff kondensiert.
Die neue Barbitursäure lässt sich in Salze überführen, beispielsweise mittels Natrium- alkoholat in wasserfreier Alkohollösung oder mit. Natriumhydroxyd in wässeriger Alkohol lösung, in (las Natriumsalz. Für pharmazeu- tiselie Zwecke wird gewöhnlich das Natrium salz zur Verwendung belangen. Die neue Ver- bindung ist im allgemeinen in Wasser wenig löslich und lässt sich oral verabreichen.
Für die subkutane Verabreichung wird die neue Verbindung vorzugsweise in Form ihrer was serlöslichen Salze und insbesondere des @a- triumsalzes verwendet.
Beispiel: Es wird ein 38 g in 495 ema absolutem Me thanol gelöstes Natrium und 62 g Thioharn- stoff enthaltendes Gemisch hergestellt, welches mit 141 g 1,1-Diearbäthoxy-2,3,5-trimethyley- elopenta.n versetzt wird. Das erhaltene Gemisch wird während sechs Stunden unter Rückfluss erhitzt und anschliessend zur Entfernung des Methanols destilliert.
Der Rückstand wird ge kühlt und mit Wasser versetzt, worauf das wässerige Gemisch zur Entfernung von in Al kali unlöslichem Öl wiederholt mit Äther ex trahiert wird. Der Ätherextrakt wird verwor fen. Die wässerige Lösung wird gekühlt und unter Rühren mit verdünnter Salzsäure be handelt, bis das Gemisch neutral reagiert. Da bei bildet sich ein Niederschlag der gewünseh- ten Spiro-2,3,5-trimethyleyclopentan-(1),5'- thiobarbitursäure in roher Form.
Der Niederschlag wird durch Filtrieren isoliert, mit Wasser gewaschen und mehrmals aus verdünntem Alkohol umkristallisiert. Die gereinigte, kristalline Säure schmilzt bei 175 bis 177 C (unkorr.) und ist in -Wasser nur wenig löslich, in Alkohol dagegen gut löslich.
Analyse: Gefunden N---11,541/o; Berech- net: N=71,67%.
Process for the preparation of a new barbituric acid compound. The subject matter of the present invention is a process for the production of a new barbituric acid compound, namely spiro-2,3,5-triniethyley elopentanoic (1), 5'-thiobarbituric acid.
The new thiobarbituric acid has berulant, soporific and anesthetic properties of remarkably short duration. It is effective in small doses and shows. a wide range of confidence between therapeutic and toxic dose. It is particularly suitable for creating general anesthesia of short duration by intravenous administration.
The new compound can be represented by the following formula:
EMI0001.0022
The process according to the invention is characterized in that 3., 1-Diea @ b-iillioxz = '?, 3,5-trimethyl-yelopentane is condensed with thiolarea.
The new barbituric acid can be converted into salts, for example using sodium alcoholate in anhydrous alcohol solution or with. Sodium hydroxide in aqueous alcohol solution, in (as the sodium salt. The sodium salt is usually used for pharmaceutical purposes. The new compound is generally sparingly soluble in water and can be administered orally.
For subcutaneous administration, the new compound is preferably used in the form of its water-soluble salts and in particular the @ a- trium salt.
Example: A mixture containing 38 g of sodium dissolved in 495 ema absolute methanol and 62 g of thiourea is produced, to which 141 g of 1,1-diearbethoxy-2,3,5-trimethyleyelopenta.n are added. The resulting mixture is refluxed for six hours and then distilled to remove the methanol.
The residue is cooled and water is added, whereupon the aqueous mixture is repeatedly extracted with ether to remove oil which is insoluble in alkali. The ether extract is discarded. The aqueous solution is cooled and treated with dilute hydrochloric acid while stirring until the mixture reacts neutrally. A precipitate of the desired spiro-2,3,5-trimethyleyclopentane (1), 5'-thiobarbituric acid forms in crude form.
The precipitate is isolated by filtration, washed with water and recrystallized several times from dilute alcohol. The purified, crystalline acid melts at 175 to 177 C (uncorrupted) and is only sparingly soluble in water, but readily soluble in alcohol.
Analysis: Found N --- 11.541 / o; Calculated: N = 71.67%.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US280319XA | 1948-05-28 | 1948-05-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH280319A true CH280319A (en) | 1952-01-15 |
Family
ID=21841174
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH280319D CH280319A (en) | 1948-05-28 | 1949-05-28 | Process for the preparation of a new barbituric acid compound. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH280319A (en) |
-
1949
- 1949-05-28 CH CH280319D patent/CH280319A/en unknown
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