CH97751A - Process for the preparation of a compound of isopropylallylbarbituric acid. - Google Patents
Process for the preparation of a compound of isopropylallylbarbituric acid.Info
- Publication number
- CH97751A CH97751A CH97751DA CH97751A CH 97751 A CH97751 A CH 97751A CH 97751D A CH97751D A CH 97751DA CH 97751 A CH97751 A CH 97751A
- Authority
- CH
- Switzerland
- Prior art keywords
- compound
- acid
- solvents
- yellow
- double
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 21
- UORJNBVJVRLXMQ-UHFFFAOYSA-N aprobarbital Chemical compound C=CCC1(C(C)C)C(=O)NC(=O)NC1=O UORJNBVJVRLXMQ-UHFFFAOYSA-N 0.000 title claims description 12
- 229960003153 aprobarbital Drugs 0.000 title claims description 12
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 2
- 239000002904 solvent Substances 0.000 claims description 6
- 239000000155 melt Substances 0.000 claims description 5
- 230000000202 analgesic effect Effects 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229940127240 opiate Drugs 0.000 claims description 2
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- RMMXTBMQSGEXHJ-UHFFFAOYSA-N Aminophenazone Chemical compound O=C1C(N(C)C)=C(C)N(C)N1C1=CC=CC=C1 RMMXTBMQSGEXHJ-UHFFFAOYSA-N 0.000 description 2
- 239000011872 intimate mixture Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- QNMHBBMZKIRNNI-UHFFFAOYSA-N 4-(dimethylamino)-1,4-dihydropyrazol-5-one Chemical compound CN(C1C=NNC1=O)C QNMHBBMZKIRNNI-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms
- C07D231/46—Oxygen atom in position 3 or 5 and nitrogen atom in position 4
- C07D231/48—Oxygen atom in position 3 or 5 and nitrogen atom in position 4 with hydrocarbon radicals attached to said nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung einer Verbindung der Isopropylallylbar bitursäure. Gegenstand der vorliegenden Erfindung ist ein Verfahren zur Herstellung einer Ver bindung der Isopropylallylbarbitursäure, wel ches darin besteht, dass man Isopropylally l barbitursäure mit i-Phenyl-2,3-dirnethyl-4-di- methylamino-5-pyrazolorr zusammerrschmilzt.
Aus den beiden farblosen Ausgangsstoffen entsteht dabei ein gelbgefärbtes Produkt, wel che, wenn zur Schmelze molekulare Mengen der Komponenten verwendet wurden, scharf zwischen 92 und 93 schmilzt. Gegenüber Lösungsmitteln verhält sich die neue Verbin dung verschieden. Kohlenwasserstoffe zerlegen sie nur geringfügig; die Lösung ist stark gelb gefärbt. Hydrogylhaltige Lösungsmittel, ins besondere Wasser, ergeben nur schwach gelbe Lösungen, was darauf hindeutet, dass die Doppelverbindung in derartigen Lösungsmit teln weitgehend zerlegt ist. Dementsprechend gelingt es auch, aus solchen Lösungen eine der beiden Komponenten ohne Beimengung der andern auskristallisieren zu lassen.
Die Doppelverbindung der Isopropylallylbarbitur- säure mit 1-Phenyl- 2,3-dimethyl-4-dimethyl- amino-5-pyrazolon ist deshalb von Bedeutung, da es sich gezeigt hat, dass zur Auslösung von Schlaf davon kleinere Mengennotwendig sind, als ihrem Gehalt an Isopropylallylbar- bitursäure entspricht.
Besonders wertvoll aber ist, dass die analgetische Wirkung der neuen Verbindung gegenüber dem reinen Pyrazolon- derivat stark erhöht ist, so dass es mit Hilfe dieser neuen Verbindung gelingt, meistens auch dann noch Schlaf zu erzeugen, wenn derselbe durch körperliche Schmerzen behin dert wird. Diese Doppelverbindung vermag also die Opiate teilweise zu ersetzen.
Die Herstellung der Doppelverbindung er folgt am zweckmässigsten durch Zusammen schmelzen der Komponenten in molekularem Verhältnis. Doch erhält man auch bei nicht zu weit davon abliegendem Verhältnis Pro dukte, die gleich aussehen, sich höchstens nur durch einen unscharfen Schmelzpunkt als nicht einheitlich erweisen.
Wenn auch solche Mi schungen der neuen Verbindung mit dem Über schuss der einen Komponente nicht einheit lich aus der neuen Verbindung bestehen, so teilen diese durch Zusammenschmelzen ge wonnenen Mischungen mit der einheitlichen Doppelverbindung den Vorteil gegenüber ein fachen innigen Mischungen von Isopropylallyl- barbitursäure mit 1-Phenyl-2,3-dimetliyl-4-di- methylamino-5-pyrazolon, dass sie vollkommen unverändert haltbar sind.
Einfache innige Mi schungen der Komponenten, insbesondere dar aus hergestellte Tabletten, verfärben sieh all mählich durch Bildung der Doppelverbindung an den sich engberührenden Stellen.
Beispiel <I>1:</I> 10 Gewichtsteile Isopropylallylbarbitur- säure und 11 Gewichtsteile 1-Phenyl-2,3-di- inethyl-4-diniethylamirio-5-pyi@azolori werden gemischt und auf 100-120 erwärmt. Es ent steht ein klarer gelber Schmelzfluss, den man unter Rühren erhalten lässt. Die festgewor dene Verbindung wird darauf gepulvert, das Pulver ist deutlich gelb gefärbt, sein Schmelz punkt liegt scharf zwischen 92 und 93 und ist in dieser Form unverändert haltbar.
<I>Beispiel</I> ?: 6 Gewichtsteile Isopropylally lbarbitursäure und 10 Gewichtsteile 1-Phenyl-2,3-dimethy 1 4-dimethylamino-5-pyrazolon werden bei 110 zusammengeschmolzen, der Schmelzfluss unter Rühren langsam erhalten gelassen und als dann zerkleinert. Das so erhaltene gelbliche Pulver ist wie das nach Beispiel 1 erhaltene unverändert haltbar.
Process for the preparation of a compound of isopropylallylbar bituric acid. The present invention relates to a process for the production of a compound of isopropylallylbarbituric acid, which consists in melting isopropylallylbarbituric acid with i-phenyl-2,3-dimethyl-4-dimethylamino-5-pyrazolorrm.
The two colorless starting materials result in a yellow-colored product which, if molecular quantities of the components are used for the melt, melts sharply between 92 and 93. The new compound behaves differently towards solvents. They break down hydrocarbons only slightly; the solution is strongly yellow in color. Hydrogen-containing solvents, in particular water, only give pale yellow solutions, which indicates that the double compound is largely broken down in such solvents. Accordingly, one of the two components can also be allowed to crystallize from such solutions without admixing the other.
The double compound of isopropylallylbarbituric acid with 1-phenyl-2,3-dimethyl-4-dimethylamino-5-pyrazolone is important because it has been shown that smaller amounts are necessary to induce sleep than its content of isopropylallylbarbituric acid.
It is particularly valuable, however, that the analgesic effect of the new compound is greatly increased compared to the pure pyrazolone derivative, so that with the help of this new compound it is possible to generate sleep in most cases even when it is hindered by physical pain. This double compound can therefore partially replace the opiates.
The most convenient way to produce the double compound is to melt the components together in a molecular ratio. However, even if the ratio is not too far from this, products are obtained that look the same, at most only prove to be non-uniform due to a fuzzy melting point.
Even if such mixtures of the new compound with the excess of one component do not consist uniformly of the new compound, these mixtures with the single double compound obtained by melting together share the advantage over simple intimate mixtures of isopropylallyl barbituric acid with 1- Phenyl-2,3-dimethyl-4-dimethylamino-5-pyrazolon that they can be kept completely unchanged.
Simple intimate mixtures of the components, in particular tablets made from, gradually discolor due to the formation of the double compound at the closely contacting points.
Example <I> 1: </I> 10 parts by weight isopropylallylbarbituric acid and 11 parts by weight 1-phenyl-2,3-dimethyl-4-diniethylamirio-5-pyi @ azolori are mixed and heated to 100-120. A clear, yellow melt flow results, which can be maintained with stirring. The solidified compound is powdered onto it, the powder is clearly yellow in color, its melting point is between 92 and 93 and can be kept unchanged in this form.
<I> Example </I>?: 6 parts by weight of isopropylally lbarbituric acid and 10 parts by weight of 1-phenyl-2,3-dimethy 1 4-dimethylamino-5-pyrazolone are melted together at 110, the melt flow is allowed to slowly maintain with stirring and then comminuted . The yellowish powder obtained in this way can be kept unchanged like that obtained in Example 1.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH97751T | 1921-09-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH97751A true CH97751A (en) | 1923-02-16 |
Family
ID=4355527
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH97751D CH97751A (en) | 1921-09-05 | 1921-09-05 | Process for the preparation of a compound of isopropylallylbarbituric acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH97751A (en) |
-
1921
- 1921-09-05 CH CH97751D patent/CH97751A/en unknown
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