DE2142317A1 - Hypnotic uracil derivs - which do not have narcotic props - Google Patents

Hypnotic uracil derivs - which do not have narcotic props

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Publication number
DE2142317A1
DE2142317A1 DE19712142317 DE2142317A DE2142317A1 DE 2142317 A1 DE2142317 A1 DE 2142317A1 DE 19712142317 DE19712142317 DE 19712142317 DE 2142317 A DE2142317 A DE 2142317A DE 2142317 A1 DE2142317 A1 DE 2142317A1
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Germany
Prior art keywords
phenyluracil
uracil
phenyl
methyl
chlorophenyl
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DE19712142317
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German (de)
Inventor
Gerd Dr Aichinger
Hermann Dr Hagemann
Friedrich Dr Hoffmeister
Kurt Prof Dr Ley
Ekkehard Dr Niemers
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Bayer AG
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Bayer AG
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Priority to DE19712142317 priority Critical patent/DE2142317A1/en
Publication of DE2142317A1 publication Critical patent/DE2142317A1/en
Pending legal-status Critical Current

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    • 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
    • C07D239/52—Two oxygen atoms
    • C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals

Abstract

Hypnotic agents contain >=1 uracil deriv. of formula (I): (where R1 is alkyl, alkenyl, cycloalkyl, aralkyl, aryl, alkoxyalkyl, alkoxy, aralkoxy, dialkylaminoalkoxy, dialkylamino, 5- to 8-membered N-heterocyclyl, dialkenylamino or morpholino; R2 is H, alkyl, alkenyl, dialkylaminoalkyl or aralkyl; R3 is H, alkyl, aryl or halogen; and R4 is alkyl, alkenyl, cycloalkyl, aralkyl, aralkenyl, aryl or heterocyclyl).

Description

Hypnotisches Mittel Die vorliegende Erfindung betrifft die Verwendung von weitgehend bekannten Uracil-Derivaten als Hypnotika. Hypnotic Agent The present invention relates to use of widely known uracil derivatives as hypnotics.

Die meisten der gegenwärtig als Arzneimittel eingeführten, hypnotisch wirksamen Pharmaka haben in Dosen, die nicht wesentlich über den hypnotisch wirksamen liegen, allgemein zentral-dämpSende Wirkungen, die bis zur Narkose, im Extremfall bis zum Narkosetod gehen können (vgl. H. Koch, J. Kothan, H. Braun, Monatshefte für Chemie 98, 702 - 712 (1967)).Most of the currently druged, hypnotic Effective drugs have been given in doses that are not significantly above the hypnotically effective ones generally central dampening effects that go as far as anesthesia, in extreme cases can go up to death by anesthesia (cf. H. Koch, J. Kothan, H. Braun ,monthshefte for Chemistry 98, 702-712 (1967)).

Es ist deshalb wünschenswert - um eine größere Sicherheit bei der Therapie von Schlafstörungen zu erreichen -, Pharmaka zu entwickeln, die hypnotisch wirken und narkotische Eigenschaften nicht oder zumindest in weniger ausgeprägtem Maße besitzen.It is therefore desirable - to provide greater security in the To achieve therapy of sleep disorders - to develop drugs that are hypnotic have no effect and narcotic properties, or at least to a lesser extent Own dimensions.

Es wurde gefunden, daß die weitgehend bekannten Uracil-Derivate der Formel in welcher R1 für Alkyl, Alkenyl, Cycloalkyl, Aralkyl, Aryl, Alkoxyalkyl, Alkoxy, Aralkoxy, Dialkylaminoalkoxy, Dialkylamino der Formel wobei R' und R" zusammen mit dem Stickstoff gegebenenfalls einen 5- bis 8-gliedrigen Ring bilden, Dialkenylamino oder Morpholino steht, und R2 für Wasserstoff, Alkyl, Alkenyl, Dialkylaminoalkyl oder Aralkyl steht, und R3 für Wasserstoff, Alkyl, Aryl oder Halogen steht, und R4 für Alkyl, Alkenyl, Cycloalkyl, Aralkyl, Aralkenyl, Aryl oder einen heterocyclischen Rest steht, starke hypnotische Eigenschaften aufweisen.It has been found that the widely known uracil derivatives of the formula in which R1 represents alkyl, alkenyl, cycloalkyl, aralkyl, aryl, alkoxyalkyl, alkoxy, aralkoxy, dialkylaminoalkoxy, dialkylamino of the formula where R 'and R "together with the nitrogen optionally form a 5- to 8-membered ring, is dialkenylamino or morpholino, and R2 is hydrogen, alkyl, alkenyl, dialkylaminoalkyl or aralkyl, and R3 is hydrogen, alkyl, aryl or halogen and R4 is alkyl, alkenyl, cycloalkyl, aralkyl, aralkenyl, aryl or a heterocyclic radical, have strong hypnotic properties.

Überraschenderweise zeigen die Uracil-Derivate erhebliche hypnotische Wirkungen, die nicht wie bei den meisten im Handel befindlichen Schlafmitteln mit narkotischen Eigenschaften verbunden sind. Die erfindungsgemäßen Wirkstoffe stellen somit eine Bereicherung der Pharmazie dar.Surprisingly, the uracil derivatives show considerable hypnotic properties Effects that are not found with most sleeping pills on the market narcotic properties are linked. The active ingredients according to the invention provide thus an enrichment of pharmacy.

Die erfindungsgemäß zu verwendenden Uracil-Derivate sind durch die Formel (I) genau definiert und sind bereits weitgehend bekannt (vgl. D.O.S. 1 959 705.8/I).The uracil derivatives to be used according to the invention are by the Formula (I) precisely defined and are already largely known (cf. D.O.S. 1 959 705.8 / I).

Die genannten Alkyl-, Alkenyl- und Alkoxyreste R1 bis R4 haben im allgemeinen 1 bis 12 Kohlenstoffatome, sie sind geradkettig oder verzweigt. R3 und R4 sind gegebenenfalls auch über Kohlenstoff-Kohlenstoff-Bindungen miteinander verknüpft. Die Arylreste sind gegebenenfalls durch Alkyl-, Alkoxy-, Halogen-, Cyan-, Nitro-, Amino-, Dialkylamino-, alkoxy-, Alkoxycarbonyl- oder Acylamino-Reste ein- oder mehrfach substituiert.The alkyl, alkenyl and alkoxy radicals R1 to R4 mentioned have im generally 1 to 12 carbon atoms, they are straight-chain or branched. R3 and R4 are optionally also linked to one another via carbon-carbon bonds. The aryl radicals are optionally substituted by alkyl, alkoxy, halogen, cyano, nitro, Amino, dialkylamino, alkoxy, alkoxycarbonyl or acylamino radicals substituted one or more times.

Als Beispiele für die erfindungr;gemäßen Wirkstoffe seien genannt: 1-(4-Chlorphenyl)-6-phenyluracil 1,6-Diphenyluracil 1 -Phenyl-6- (2-chlorphenyl)-uracil 1-Phenyl-6-(4-chlorphenyl-uracil 1-Phenyl-6-(3-fluorphenyl)-uracil 1-Phenyl-6-(4-fluorphenyl)-uracil 1-Phenyl-6-(3,5-dichlorphenyl)-uracil l-Phenyl-6-(2-nitrophenyl)-uracil 1 -Phenyl-6- (3-nitrophenyl) -urac il 1-Phenyl-6-(4-nitrophenyl)-uracil 1-Phenyl-6-(4-tolyl)-uracil 1-Phenyl-6-(3,4-dimethylphenyl)-uracil 1-Phenyl-6-(4-isopropylphenyl)-uracil 1-Phenyl-6-(2-methoxyphenyl)-uracil 1-Phenyl-6-(3-methoxyphenyl-uracil 1-Phenyl-6-(4-methoxyphenyl)-uracil 1-Phenyl-6-(2-äthoxyphenyl)-uracil 1 -Phenyl-6- (4-äthoxyphenyl)-uracil 1-Phenyl-6-(3-methyl-4-methoxyphenyl)-uracil 1-Phenyl-6-(4-methyl-2-äthoxyphenyl)-uracil 1-Phenyl-6-(2,4-diäthoxyphenyl)-uracil 1-Phenyl-6-(4-cyanophenyl)-uracil 1-Phenyl-6-(4-diäthylaminoäthoxyphenyl)-uracil 1-Phenyl-6-isobutykyuracil 1-Phenyl-6-tert.-butyluracil 1 -Phenyl-6-cyclohexyluracil 1-Phenyl-6-(1-phenyläthyl)-uracil 1-Phenyl-6-(2,2-dimethylvinyl)-uracil 1-Phenyl-6-styryluracil 1,6-Diphenyl-5-methyluracil 1,6-Diphenyl-5-isopropyl-uracil 1,6-Diphenyl-5-chloruracil 1-Phenyl-6-(3-pyridyl)-uracil 1-Phenyl-6-(4-pyridyl)-uracil 1-Phenyl-6-(2-furyl)-uracil 1-Phenyl-6-(2-thienyl)-uracil 1-(2-Chlorphenyl)-6-phenyluracil 1-(3-Chlorphenyl)-6-phenyluracil 1-(3,4-Dichlorphenyl)-6-phenyluracil 1-(3-Methylphenyl)-6-phenyluracil 1-(4-Methylphenyl)-6-phenyluracil 1-(4-Äthylphenyl)-6-phenyluracil 1-(3,4-Dimethylphenyl)-6-phenyluracil 1-(4-Methoxyphenyl)-6-phenyluracil 1-(4-Methoxycarbonylphenyl)-6-phenyluracil 1-Methyl-6-phenyluracil 1-Propyl-6-phenyluracil 1-n-Butyl-6-phenyluracil 1-Isobutyl-6-phenyluracil 1-Dodecyl-6-phenyluracil 1-Cyclohexyl-6-phenyluracil 1-Cyclohexyl-5-methyl-6-phenyluracil 1-Allyl-6-phenyluracil 1-(3-Äthoxypropyl)-6-phenyluracil 1-(4-Chlorphenyl)-6-(2-chlorphenyl)-uracil 1-(3,4-Dichlorphenyl)-6-(2-chlorphenyl)-uracil 1-n-Butyl-6-(2-chlorphenyl)-uracil 1-(3-Äthoxypropyl)-6-(4-chlorphenyl)-uracil 1-Methoxy-6-phenyluacil 1-Methoxy-6-(2-chlorphenyl)-uracil 1-Äthoxy-6-phenyloxuracil 1-(2-Dimethylamino-äthoxy)-6-phenyluracil 1-Benzyloxy-6-phenyluracil 1-(4-Methyl-benzyloxy)-6-phenyluracil 1-(3-n-Propoxy-benzyloxy)-6-phenyluracil 1-(2-Chlor-benzyloxy)-6-phenyluracil 1-(3-Nitro-benzyloxy)-6-phenyluracil 1-(2-Phenäthoxy)-6-phenyluracil 1-(Dimethylcarbamoyloxy)-6-phenyluracil 1 -Perhydroazepino-6-phenyluracil 1-(Dimethylamino)-6-phenyluracil 1-(4-Chlorphenyl)-3-methyl-6-phenyluracil 1,6-Diphenyl-3-methyluracil 1-Phenyl-3-methyl-6-(2-chlorphenyl)-uracil 1-Phenyl-3-methyl-6-(4-chlorphenyl)-uracil 1-Phenyl-3-methyl-6-(3-nitrophenyl)-uracil 1-Phenyl-3-methyl-6-(4-äthoxyphenyl)-uracil 1-Phenyl-3-methyl-6-(2,4-diäthoxyphenyl)-uracil 1-(4-Chlorphenyl)-3-methyl-6-(2-chlorphenyl)-uracil 1-(3,4-Dichlorphenyl)-3-methyl-6-(2-chlorphenyl)-uracil 1,3-Dimethyl-6-phenyluracil 1-n-Propyl-3-methyl-6-phenyluracil 1-n-Buthyl-3-methyl-6-phenyluracil 1-Allyl-3-methyl-6-phenyluracil 1-(4-Chlorphenyl)-3-äthyl-6-phenyluracil 1-Methyl-3-äthyl-6-phenyluracil 1-(4-Chlorphenyl)-3-n-propyl-6-phenyluracil 1-(4-Chlorphenyl)-3-isopropyl-6-phenyluracil 1-(4-Chlorphenyl)-3-allyl-6-phenyluracil 1-(4-Chlorphenyl)-3-benzyl-6-phenyluracil 1-Methyl-3-benzyl-6-phenyluracil 1,6-Diphenyl-3-diäthylaminoäthyl-uracil 1-(4-Chlorphenyl)-3-diäthylaminoäthyl-6-phenyluracil 1-(4-Chlorphenyl)-3-dimethylaminopropyl-6-phenyluracil 1-Methoxy-3-methyl-6-phenyluracil 1-Benzyloxy-3-methyl-6-phenyluracil 1-Methoxy-3-(2-diäthylamino-äthyl)-6-phenyluracil 1-(Dimethylamino)-3-methyl-6-phenyluracil 1-(Dimethylamino)-3-(dimethylaminopropyl)-6-phenyluracil 1-Dimethylamino)-3-allyl-6-phenyluracil 1-Phenyl-6-(3-aminophenyl)-uracil 1-Phenyl-3-methyl-6-(3-aminophenyl)-uracil 1-Phenyl-3-methyl-6-(4-aminophenyl)-uracil 1-Phenyl-3-methyl-6-(3-acetamidophenyl)-uracil 1-Phenyl-6-(3-acetamidophenyl)-uracil 1-Phenyl-3-methyl-6-(4-acetamidophenyl)-uracil 1-Piperidino-6-phenyluracil 1-Morpholino-6-phenyluracil 1-(Diallylamino)-6-phenyluracil 1-(Dimethylamino)-6-methyluracil 1-(Dimethylamino)-5-methyl-6-phenyluracil 1-(Dimethylamino)-2,4-dioxo-12,3,4,5,7,8-octahydroxhinazolin Einzelne der erfindungsgemäßen Wirkstoffe sind neu, sie können jedoch nacn bekannten Verfahren in ein-facher Weise hergestellt werden. Man erhält sie z.B., wenn man Verbindungen der Formel in welcher R1, R3 und R4 die oben angegebene Bedeutung haben, mit N-Chlorcarbonylisocyanat in Gegenwart von Verdünnungsmitteln wie Chlorbenzol, Chloroform oder Methylenchlorid, und gegebenenfalls von Säurebindern wie T'riäthylamin oder Dimethylanilin bei Temperaturen zwischen Oo und 1300C um setzt und anschließend gegebenenfalls in 3-Stellung nach Literatur-bekannten Methoden alkyliert (Chien-Pen Lo, Elwood Y. Shropshire, J. Org. Chem. 22, 99 - 1000 (1957)).Examples of the active ingredients according to the invention are: 1- (4-chlorophenyl) -6-phenyluracil 1,6-diphenyluracil 1-phenyl-6- (2-chlorophenyl) uracil 1-phenyl-6- (4-chlorophenyl -uracil 1-phenyl-6- (3-fluorophenyl) -uracil 1-phenyl-6- (4-fluorophenyl) -uracil 1-phenyl-6- (3,5-dichlorophenyl) -uracil l-phenyl-6- ( 2-nitrophenyl) uracil 1-phenyl-6- (3-nitrophenyl) -uracil 1-phenyl-6- (4-nitrophenyl) uracil 1-phenyl-6- (4-tolyl) -uracil 1-phenyl- 6- (3,4-dimethylphenyl) uracil 1-phenyl-6- (4-isopropylphenyl) uracil 1-phenyl-6- (2-methoxyphenyl) uracil 1-phenyl-6- (3-methoxyphenyl uracil 1 -Phenyl-6- (4-methoxyphenyl) -uracil 1-phenyl-6- (2-ethoxyphenyl) -uracil 1 -phenyl-6- (4-ethoxyphenyl) -uracil 1-phenyl-6- (3-methyl-4 -methoxyphenyl) -uracil 1-phenyl-6- (4-methyl-2-ethoxyphenyl) -uracil 1-phenyl-6- (2,4-diethoxyphenyl) -uracil 1-phenyl-6- (4-cyanophenyl) -uracil 1-phenyl-6- (4-diethylaminoethoxyphenyl) -uracil 1-phenyl-6-isobutykyuracil 1-phenyl-6-tert.-butyluracil 1-phenyl-6-cyclohexyluracil 1-phenyl-6- (1-phenylät hyl) -uracil 1-phenyl-6- (2,2-dimethylvinyl) -uracil 1-phenyl-6-styryluracil 1,6-diphenyl-5-methyluracil 1,6-diphenyl-5-isopropyl-uracil 1,6- Diphenyl-5-chloruracil 1-phenyl-6- (3-pyridyl) -uracil 1-phenyl-6- (4-pyridyl) -uracil 1-phenyl-6- (2-furyl) -uracil 1-phenyl-6- (2-thienyl) uracil 1- (2-chlorophenyl) -6-phenyluracil 1- (3-chlorophenyl) -6-phenyluracil 1- (3,4-dichlorophenyl) -6-phenyluracil 1- (3-methylphenyl) - 6-phenyluracil 1- (4-methylphenyl) -6-phenyluracil 1- (4-ethylphenyl) -6-phenyluracil 1- (3,4-dimethylphenyl) -6-phenyluracil 1- (4-methoxyphenyl) -6-phenyluracil 1 - (4-Methoxycarbonylphenyl) -6-phenyluracil 1-methyl-6-phenyluracil 1-propyl-6-phenyluracil 1-n-butyl-6-phenyluracil 1-isobutyl-6-phenyluracil 1-dodecyl-6-phenyluracil 1-cyclohexyl -6-phenyluracil 1-cyclohexyl-5-methyl-6-phenyluracil 1-allyl-6-phenyluracil 1- (3-ethoxypropyl) -6-phenyluracil 1- (4-chlorophenyl) -6- (2-chlorophenyl) -uracil 1- (3,4-dichlorophenyl) -6- (2-chlorophenyl) uracil 1-n-butyl-6- (2-chlorophenyl) uracil 1- (3-ethoxypropyl) -6- (4-chlorop henyl) uracil 1-methoxy-6-phenyluacil 1-methoxy-6- (2-chlorophenyl) -uracil 1-ethoxy-6-phenyloxuracil 1- (2-dimethylamino-ethoxy) -6-phenyluracil 1-benzyloxy-6-phenyluracil 1- ( 4-methyl-benzyloxy) -6-phenyluracil 1- (3-n-propoxy-benzyloxy) -6-phenyluracil 1- (2-chloro-benzyloxy) -6-phenyluracil 1- (3-nitro-benzyloxy) -6- phenyluracil 1- (2-phenethoxy) -6-phenyluracil 1- (dimethylcarbamoyloxy) -6-phenyluracil 1 -perhydroazepino-6-phenyluracil 1- (dimethylamino) -6-phenyluracil 1- (4-chlorophenyl) -3-methyl-6-phenyluracil 1,6-diphenyl-3-methyluracil 1-phenyl-3-methyl-6- (2-chlorophenyl) uracil 1-phenyl-3-methyl-6- (4-chlorophenyl) uracil 1-phenyl-3-methyl-6- (3-nitrophenyl) uracil 1-phenyl-3-methyl-6 - (4-ethoxyphenyl) uracil 1-phenyl-3-methyl-6- (2,4-diethoxyphenyl) uracil 1- (4-chlorophenyl) -3-methyl-6- (2-chlorophenyl) uracil 1- (3,4-dichlorophenyl) -3-methyl-6- (2-chlorophenyl) uracil 1,3-dimethyl-6-phenyluracil 1-n-propyl-3-methyl-6-phenyluracil 1-n-butyl-3 -methyl-6-phenyluracil 1-allyl-3-methyl-6-phenyluracil 1- (4-chlorophenyl) -3-ethyl-6-phenyluracil 1-methyl-3-ethyl-6-phenyluracil 1- (4-chlorophenyl) -3-n-propyl-6-phenyluracil 1- (4-chlorophenyl) -3-isopropyl-6-phenyluracil 1- (4-chlorophenyl) -3-allyl-6-phenyluracil 1- (4-chlorophenyl) -3- benzyl-6-phenyluracil 1-methyl-3-benzyl-6-phenyluracil 1,6-diphenyl-3-diethylaminoethyl uracil 1- (4-chlorophenyl) -3-diethylaminoethyl-6-phenyluracil 1- (4-chlorophenyl) - 3-dimethylamino propyl-6-phenyluracil 1-methoxy-3-methyl-6-phenyluracil 1-benzyloxy-3-methyl-6-phenyluracil 1-methoxy-3- (2-diethylamino-ethyl) -6-phenyluracil 1- (dimethylamino) - 3-methyl-6-phenyluracil 1- (dimethylamino) -3- (dimethylaminopropyl) -6-phenyluracil 1-dimethylamino) -3-allyl-6-phenyluracil 1-phenyl-6- (3-aminophenyl) uracil 1-phenyl -3-methyl-6- (3-aminophenyl) -uracil 1-phenyl-3-methyl-6- (4-aminophenyl) -uracil 1-phenyl-3-methyl-6- (3-acetamidophenyl) -uracil 1- Phenyl-6- (3-acetamidophenyl) -uracil 1-phenyl-3-methyl-6- (4-acetamidophenyl) -uracil 1-piperidino-6-phenyluracil 1-morpholino-6-phenyluracil 1- (diallylamino) -6- phenyluracil 1- (dimethylamino) -6-methyluracil 1- (dimethylamino) -5-methyl-6-phenyluracil 1- (dimethylamino) -2,4-dioxo-12,3,4,5,7,8-octahydroxhinazoline some of the Active ingredients according to the invention are new, but they can be prepared in a simple manner by known processes. They are obtained, for example, when using compounds of the formula in which R1, R3 and R4 have the meaning given above, reacts with N-chlorocarbonyl isocyanate in the presence of diluents such as chlorobenzene, chloroform or methylene chloride, and optionally acid binders such as triethylamine or dimethylaniline at temperatures between Oo and 1300C and then optionally in 3-position alkylated by methods known from the literature (Chien-Pen Lo, Elwood Y. Shropshire, J. Org. Chem. 22, 99-1000 (1957)).

Die 6-(Aminophenyl)-uracile erhält man aus den entsprechenden 6-(Nitrophenyl)-uracilen durch Hydrierung mit Raney-Nickel. Durch Umsetzung dieser Aminoverbindungen mit Acetanhydrid erhält man die entsprechenden Acetamido-Derivate.The 6- (aminophenyl) uracils are obtained from the corresponding 6- (nitrophenyl) uracils by hydrogenation with Raney nickel. By reacting these amino compounds with Acetic anhydride gives the corresponding acetamido derivatives.

Die als Ausgangsstoffe verwendeten Verbindungen der Formel (II) sind teilweise literaturbekannt (J. S. Walia, L. Heindl, H. Lader, P. 5. Walia, Chem. Ind. 1968, 155 - 156), teilweise wurden sie aus den entsprechenden Ketonen oder Aminen nach literaturbekannten Verfahren erhalten (J. S. Walia, L. Heindl, H. Lader, P. S. Walia, Chem. Ind. 1968, 155 - 156).The compounds of formula (II) used as starting materials are partly known from the literature (J. S. Walia, L. Heindl, H. Lader, P. 5. Walia, Chem. Ind. 1968, 155 - 156), some of them were derived from the corresponding ketones or Amines obtained by processes known from the literature (J. S. Walia, L. Heindl, H. Lader, P. S. Walia, Chem. Ind. 1968, 155-156).

Die erfindungsgemäßen Wirkstoffe haben stark ausgeprägte hypnotische, d.h. Schlaf produzierende Eigenschaften, ohne narkotisch zu wirken. Sie können demzufolge bei der Therapie von Schlafstörungen jeglicher Genese des Menschen mit Vorteil eingesetzt werden. Wegen ihrer auch bei Tieren stark ausgeprägten Schlaf induzierenden Wirkung sind sie weiterhin anwendbar in allen Situationen, in denen es wünschenswert erscheint, ein Tier ohne sonstige Beeinträchtigung in Schlaf zu versetzen. Dies ist z.B. unter TransportbedingungenSnach Operationen usw. der Fall.The active ingredients according to the invention have strongly pronounced hypnotic, i.e. sleep-producing properties without being narcotic. You can therefore used with advantage in the therapy of sleep disorders of any origin in humans will. Because of its strong sleep-inducing effect, also in animals are they still applicable in all situations in which it appears desirable to put an animal to sleep without any other impairment. This is e.g. under The case after operations etc.

Die erfindungsgemäßen Wirkstoffe können in bekannter Weise in die üblichen Formulierungen übergeführt werden, wie Tabletten, Kapseln, Dragees, Pillen, Granulate, Suppositorien, lösliche Pulver, Lösungen, Sirupe, Emulsionen und Suspensionen. Als Hilfsstoffe für die Herstellung dieser Zubereitungen eignen sich inerte, nicht toxische, pharmazeutisch geeignete feste, halbfeste und flüssige Trägerstoffe, Emulgiermittel, Dispergiermittel.The active compounds according to the invention can in a known manner in the common formulations, such as tablets, capsules, coated tablets, pills, Granules, suppositories, soluble powders, solutions, syrups, emulsions and suspensions. Inert ones are not suitable as auxiliaries for the production of these preparations toxic, pharmaceutically suitable solid, semi-solid and liquid carriers, emulsifiers, Dispersants.

Die Konzentration der Wirkstoffe in den Formulierungen liegt zwischen 1 und 80 , vorzugsweise (in Tabletten, Pillen, Kapseln, Dragees) zwischen 20 und 80 %.The concentration of the active ingredients in the formulations is between 1 and 80, preferably (in tablets, pills, capsules, coated tablets) between 20 and 80%.

Die erfindungsgemäßen Wirkstoffe können in üblicher Weise angewendet werden, insbesondere oral, rectal, parenteral, wie z.B. intramuskulär, intravenös, intraperitoneal.The active compounds according to the invention can be used in the customary manner especially oral, rectal, parenteral, such as intramuscular, intravenous, intraperitoneally.

Der Dosierungsbereich liegt bei oraler Zufuhr zwischen 0,2 und 30 mg/kg für je 24 Stunden.The dosage range for oral administration is between 0.2 and 30 mg / kg for every 24 hours.

Die erfindungsgemäßen Verbindungen haben im Tierexperiment starke hypnotische Wirkungen bei fehlenden oder wenig ausgeprägten narkotischen Eigenschaften. Die Wirkungen der erfindungsgemäßen.Verbindungen im Tierexperiment sind in der beiliegenden Tabelle dargestellt, wobei ihre Wirkungen mit denen der handelsüblichen Hypnotika Methyprylon und Cyclobarbital verglichen wurden.The compounds according to the invention are strong in animal experiments Hypnotic effects in the absence of or poorly developed narcotic properties. The effects of the compounds according to the invention in animal experiments are shown in FIG enclosed Table shown, showing their effects with those of commercially available hypnotics Methyprylon and cyclobarbital were compared.

Im einzelnen wurde untersucht: die Toxizität (DL50 bei oraler Zufuhr an der Maus), die Hemmung der Orientierungsmobilität (DE50 ;mittlere wirksame Dosis bei oraler Zufuhr), die IlarSotische Wirkung an der Maus (Hemmung des Righting-Reflexes DE50 Maus bei oraler Zufuhr), die hypnotische Wirkung beim Kaninchen (Bestimmung der SD50 = Dosis, die den elektroencephalografisch meßbaren Schlaf des Kaninchens um 50 % erhöht) und die narkotische Wirkung beim Kaninchen (die geringste Dosis, die Narkosestadium III nach Magnus Girnd hervorruft).The following were examined in detail: the toxicity (DL50 with oral intake on the mouse), the inhibition of orientation mobility (DE50; mean effective dose in the case of oral intake), the IlarSotic effect in the mouse (inhibition of the righting reflex DE50 mouse after oral intake), the hypnotic effect in rabbits (determination the SD50 = dose, the electroencephalographically measurable sleep of the rabbit increased by 50%) and the narcotic effect in rabbits (the lowest dose, which causes stage III anesthesia according to Magnus Girnd).

Aus der Toxizität einerseits und der hemmenden Wirkung auf die Orientierungsmotilität der Maus wurde der therapeutische Index (DL50 : DE errechnet. Aus der narkotischen 50 Wirkung an der Maus (Hemmung des Righting-Reflexes) und dem Einfluß auf die Motilität wurde der Narkoseindex bestimmt. Für das Kaninchen wurde ein Narkoseindex errechnet, in dem die geringste Dosis, die Narkosestadium III hervorruft, zu der im elektroencephalografischen Versuch bestimmten SD50 in Beziehung eingesetzt wurde.From the toxicity on the one hand and the inhibiting effect on orientation motility the therapeutic index (DL50: DE) was calculated for the mouse. From the narcotic 50 Effect on the mouse (inhibition of the righting reflex) and the influence on motility the anesthetic index was determined. An anesthetic index was calculated for the rabbit, in which the lowest dose that produces stage III anesthesia is compared to that in the electroencephalographic Attempt specific SD50 was used in relation.

Wie aus der Tabelle hervorgeht, haben die Mehrzahl der erfindungsgemänen Substanzen an der Maus stärkere motilitätshemmende, d.h. hypnotische Wirkung als die Vergleichsprodukte. Der therapeutische Index bei der Maus ist bei allen dukte. Der therapeutische Index bei der Maus, der Narkose-Index bei der Maus und derNarkose-Index beim Kaninchen ist bei den erfindungstemäßen Produkten (soweit untersucht) größer als bei den Vergleichsprodukten. Dies bedeutet, daß der Abstand zwischen den Schlaf induzierenden (hypnotisch wirksamen) Dosen una den toxischen Dosen sowie der Abstand zwischen den hypnotisch wirksamen Dosen und den narkotisch wirksamen Dosen bei den erfindungsgemäßen Verbindungen größer ist, als bei den Vergleichsprodukten. Die erfindungsgemäßen Verbindungen sind demzufolge den Vergleichsverbindungen Uberlegen. Toxizi- Hemmung Thera- Hemmung Narkose- Hyp- Narko- Narkose- tät der peuti- des Index noti- se-Ka- Index Maus Orien- scher Righting- Maus sche nin- Kanin- Substanz DL50 tierungs- Index Reflexes Righting- Wir- chen chen mg/kg Motili- Toxizi- Maus Reflex kung Ge- Dosis p.o. tät tät DL50 DE50 DE50 beim ring- Stadium Maus Motili- Motili- Kanin- ste III ** DE50 tät DE50 p.o. tät DE50 chen Dosis SD50 mg/kg EEg- mg/kg p.o. Ver- p.o. such) Sta- SD50* dium III Methyprylon 1143 47,0 24 596 13 61 200 3,3 (948- (560- 1422) 642) Cyclobarbital 773 92,9 8,3 206 2,2 83 250 3,4 (464- (193- 1072) 218) 1,6-Diphenyl- 2175 31,0 70 5000 161 25 2000 80 uracil (1568- (25- 3309) 39) 1-Phenyl-6-(2- 1000 14,7 68 1000 68 40 500 13 chlorphenyl)- uracil Toxizi- Hemmung Thera- Hemmung Narkose- Hyp- Narko- Narkose- tät der peuti- des Index noti- se-Ka- Index Maus Orien- scher Righting- Maus sche nin- Kanin- Substanz DL50 tierungs- Index Reflexes Righting- Wir- chen chen mg/kg Motili- Toxizi- Maus Reflex kung Ge- Dosis p.o. tät tät DL50 DE50 DE50 beim ring- Stadium Maus Motili- mg/kg Motili- Kanin- ste III** DE50 tät DE50 p.o. tät DE50 chen Dosis SD50 mg/kg EEg- mg/kg Ver- p.o. p.o. such) Sta- SD50* dium III 1-(4-Chlorphenyl)- 616 16,5 37 445 27 4 500 125 6-phenyluracil (525- (332- 692) 560) 1-p-Tolyl-6- 2500 113 22 - - 50 500 10 phenyluracil (76- 149) 1-(4-Chlorphenyl)- 1000 40 25 - - 6 - - 6-(2-chlorphenyl)- (31- uracil 49) 1-(4-Chlorphenyl)- 1000 23 43 - - 20 500 25 3-methyl-6-phenyl- (15- uracil 39) Toxizi- Hemmung Thera- Hemmung Narkose- Hyp- Narko- Narkose- tät der peuti- des Index noti- se-Ka- Index Maus Orien- scher Righting- Maus sche nin- Kanin- Substanz DL50 tierungs- Index Reflexes Righting- Wir- chen chen mg/kg Motili- Toxizi- Maus Reflex kung Ge- Dosis p.o. tät tät DL50 DE50 DE50 beim ring- Stadium Maus Motili- mg/kg Motili- Kanin- ste III** DE50 tät DE50 p.o. tät DE50 chen Dosis SD50 mg/kg EEg- mg/kg p.o. Ver- p.o. such) Sta- SD50* dium III 1-Phenyl-3- - 16 - - - 45 500 11 methyl-6-(2- (14- chlorphenyl)- 19) uracil 1-Methoxy-6- 2000 80 25 1000 13 66 500 7,6 phenyluracil (65- 99) * SD50 = Dosis, die den elektroencephalografischen Schlaf um 50 % vermehrt ** = Dosis Stadium III, geringste Dosis, die Narkose Stadium III nach Magnus Girnd hervorruft Beispiel 1: Zu einer Lösung von 86,6 g (0,825 Mol) N-Chlorcarbonylisocyanat in 600 ml Chlorbenzol werden bei 30 bis 35 0C innerhalb einer Stunde 188,5 g (0,825 Mol) des Ketimins aus Acetophenon und p-Chloranilin gegeben, die in 500 ml Chlorbenzol gelöst sind. Das Gemisch wird 15 Minuten nachgerührt und anschließend innerhalb drei Stunden auf 1300C erhitzt.As can be seen from the table, the majority of the substances according to the invention have a stronger motility-inhibiting, ie hypnotic, effect on the mouse than the comparison products. The therapeutic index in the mouse is the same for all products. The therapeutic index in the mouse, the anesthesia index in the mouse and the anesthesia index in the rabbit is greater for the products according to the invention (as far as investigated) than for the comparison products. This means that the distance between the sleep-inducing (hypnotically active) doses and the toxic doses and the distance between the hypnotically active doses and the narcotically active doses is greater for the compounds according to the invention than for the comparison products. The compounds according to the invention are accordingly superior to the comparison compounds. Toxic- inhibition Thera- inhibition anesthesia hyp anesthesia anesthesia ity of the peutic index note-ka- index Mouse orien- righting- mouse nin- rabbit- Substance DL50 ting index reflexes righting action mg / kg Motili- Toxici- Mouse Reflex kung Ge dose po ity DL50 DE50 DE50 at the ring stage Mouse Motili- Motili- Rabbit III ** DE50 ity DE50 po ity DE50 chen dose SD50 mg / kg EEg- mg / kg po ver po such) Sta- SD50 * dium III Methyprylon 1143 47.0 24 596 13 61 200 3.3 (948- (560- 1422) 642) Cyclobarbital 773 92.9 8.3 206 2.2 83 250 3.4 (464- (193- 1072) 218) 1,6-diphenyl-2175 31.0 70 5000 161 25 2000 80 uracil (1568- (25- 3309) 39) 1-phenyl-6- (2- 1000 14.7 68 1000 68 40 500 13 chlorophenyl) - uracil Toxic- inhibition Thera- inhibition anesthesia hyp anesthesia anesthesia ity of the peutic index note-ka- index Mouse orien- righting- mouse nin- rabbit- Substance DL50 ting index reflexes righting action mg / kg Motili- Toxici- Mouse Reflex kung Ge dose po ity DL50 DE50 DE50 at the ring stage Mouse Motili- mg / kg Motili- rabbit III ** DE50 ity DE50 po ity DE50 chen dose SD50 mg / kg EEg- mg / kg Ver po po such) Sta- SD50 * dium III 1- (4-chlorophenyl) - 616 16.5 37 445 27 4,500 125 6-phenyluracil (525- (332- 692) 560) 1-p-Tolyl-6- 2500 113 22 - - 50 500 10 phenyluracil (76- 149) 1- (4-chlorophenyl) - 1000 40 25 - - 6 - - 6- (2-chlorophenyl) - (31- uracil 49) 1- (4-chlorophenyl) - 1000 23 43 - - 20 500 25 3-methyl-6-phenyl- (15- uracil 39) Toxic- inhibition Thera- inhibition anesthesia hyp anesthesia anesthesia ity of the peutic index note-ka- index Mouse orien- righting- mouse nin- rabbit- Substance DL50 ting index reflexes righting action mg / kg Motili- Toxici- Mouse Reflex kung Ge dose po ity DL50 DE50 DE50 at the ring stage Mouse Motili- mg / kg Motili- rabbit III ** DE50 ity DE50 po ity DE50 chen dose SD50 mg / kg EEg- mg / kg po ver po such) Sta- SD50 * dium III 1-phenyl-3- - 16 - - - 45 500 11 methyl-6- (2- (14- chlorphenyl) - 19) uracil 1-methoxy-6- 2000 80 25 1000 13 66 500 7.6 phenyluracil (65- 99) * SD50 = dose that increases electroencephalographic sleep by 50% ** = dose stage III, lowest dose that causes stage III anesthesia according to Magnus Girnd Example 1: 188.5 g (0.825 mol) of the ketimine from acetophenone and p-chloroaniline are added to a solution of 86.6 g (0.825 mol) of N-chlorocarbonyl isocyanate in 600 ml of chlorobenzene at 30 to 35 ° C., which in 500 ml Chlorobenzene are dissolved. The mixture is stirred for a further 15 minutes and then heated to 130.degree. C. over the course of three hours.

(Bei ca. 800C beginnt eine sehr lebhafte HCl-Entwicklung.) Nach dem Erkalten wird das ausgefallene Produkt abgesaugt und aus Äthanol und Dimethylformamid umkristallisiert.(At approx. 800C a very lively evolution of HCl begins.) After the The product which has precipitated out is filtered off with suction and made from ethanol and dimethylformamide recrystallized.

Man erhält 240.3 g (0,804 Mol = 97,4% der Theorie) 1-(4-chlorphenyl)-6-phenyluracil vom Schmelzpunkt 271-273°C.240.3 g (0.804 mol = 97.4% of theory) of 1- (4-chlorophenyl) -6-phenyluracil are obtained from melting point 271-273 ° C.

Analog lassen sich herstellen: Ausbeute: 1,6-Diphenyluracil Fp.: 2620C 85 % 1-Phenyl-6-(2-chlorphenyl)-uracil Fp.: 271 - 2730C 90 % 1-Phenyl-6-(4-chlorphenyl)-uracil Fp.: 234 - 235°C 85 % 1-Phenyl-6-(3-fluorphenyl)-uracil Fp.: ?57 - 2589C 70 % 1-Phenyl-6-(4-fluorphenyl)-uracil Fp.: 252 - 2530C 75 5' ?-Phenyl-6-(3,4-dichloPphenyl)-uracil Fp.: 251 - 2540C 80 % Ausbeute: 1-Phenyl-6-(2-nitrophenyl)-uracil Fp.: 2160C 50 % -1 -Phenyl-6- (3-nitrophenyl) -uracil Fp.: 240 - 2420C 70 % 1-Phenyl-6-(4-nitrophenyl)-uracil Fp.: 261 - 2630C 70 % 1-Phenyl-6-(4-tolyl)-uracil Fp.: 240 - 242°C 70 % 1-Phenyl-6-(3,4-dimethylphenyl)-uracil Fp.: 227 - 2290C 75 % 1 -Phenyl-6- (4-isopropylphenyl) -uracil Fp.: 205 - 2060C 75 % 1-Phenyl-6-(2-methoxyphenyl)-uracil Fp.: 247 - 2490C 55 % 1-Phenyl-6-(3-methoxyphenyl)-uracil Fp.: 191 - 193°C 85% 1-Phenyl-6-(4-methoxyphenyl)-uracil Fp.: 242 - 2440C 85 % 1-Phenyl-6-(2-äthoxyphenyl)-uracil Fp.: 250 - 2520C 85 % 1-Phenyl-6-(4-äthoxyphenyl)-uracil Fp. 200 - 2020C 80 % 1-Phenyl-6-(3-methyl-4-methoxyphenyl)-uracil F 228 - 2300C 85 % 1-Phenyl-6-(4-methyl-2-äthoxyphenyl)-uracil Fp.: 273 - 275°C 85% 1-Phenyl-6-(2,4-diäthoxyphenyl)-uracil Fp.: 233 - 2350C 60 % 1-Phenyl-6-(4-cyanophenyl)-uracil Fp.: 252 - 2540C 20 % 1-Phenyl-6-(4-diäthylaminoäthoxyphenyl)-uracil Fp.: Hydrochlorid 234 - 2360C 10 % 1-Phenyl-6-isobutyluracil Fp. 2210C 80 % Ausbeute: 1-Phenyl-6-tert.-butyluracil Fp.: 270 - 272°C 80 % 1-Phenyl-6-cyclohexyluracil Fp.: 234 - 2350C 87 % 1-Phenyl-6-(1-phenyläthyl)-uracil Fp.: 167 - 1690C 65 % 1-Phenyl-6-(2,2-dimethylvinyl)-uracil Fp.: 239 - 2410C 57 % 1-Phenyl-6-styryluracil Fp.: 247 - 2480C 85 % 1,6-Diphenyl-5-methyluracil Fp.: 3190C 79 5' 1,6-Diphenyl-5-isopropyluracil Fp.: 268 - 2700C 65 % 1-Phenyl-6-(3-pyridyl)-uracil Fp.: 236 - 238°C 15 % 1-Phenyl-6-(4-pyridyl)-uracil Fp.: Hydrochlorid 1880C 21 % 1-Phenyl-6-(2-furyl)-uracil Fp.: 278 - 2800C 16 % 1-Phenyl-6-(2-thienyl)-uraci1 Fp.: 272 - 2740C 80 % 1-(2-Chlorphenyl)-6-phenyluracil Fp.: 288 - 2900C 72 % 1-(3-Chlorphenyl)-6-phenyluracil Fp.: 236 - 2380C 93 % 1-(3,4-Dichlorphenyl)-6-phenyluracil Fp.: 250 - 254°C 80 % 1-(3-Methylphenyl)-6-Phenyluracil Fp.: 235 - 2360C 93 % -(4-Methylphenyl)-6-phenyluracil Fp.: 258 - 2590C 95 5' 1-(4-Äthylphenyl)-6-phenyluracil Fp.: 250°C 63% Ausbeute: 1-(3,4-Dimethylphenyl)-6-phenyluracil Fp.: ?78 - 2800C 85 % 1-(4-Methoxyphenyl)-6-phenyluracil Fp.: 224 - 2260C 26 % 1-(4-Methoxycarbonylphenyl)-6-phenyluracil Fp.: 229 - 231°C 83 % 1-Methyl-6-phenyluracil Fp.: 199 - 201°C 50 % 1-Propyl-6-phenyluracil Fp.: i29 - 131°C 80 5' 1 -n-Butyl-6-phenyluracil Fp.: 123 - 125°C 85 % 1-Isobutyl-6-phenyluracil Fp.: 164 - 1650C 85 % 1-Dodecyl-6-phenyluracil Fp.: 64 - 680C 75 5' 1-Cyclohexyl-6-phenyluracil Fp.: 2200C 80 % 1 -Cyclohexyl-5-methyl-6-phenylurac il Fp.: 221°C 80 % 1-Allyl-6-phenyluracil Fp.: 138 - 1400C 80 % 1-(3-Äthoxypropyl)-6-phenyluracil Fp.: 113 - 116°C 80 % 1-(4-Chlorphenyl)-6-(2-chlorphenyl)-uracil Fp.: 247 - 2490C 85 % 1-(3,4-Dichlorphenyl)-6-(2-chlorphenyl)-uracil Fp.: 236 - 2380C 85 % 1-n-Butyl-6-(2-chlorphenyl)-uracil Fp.: 130 - 1320C 80 % 1-(3-Äthoxypropyl)-6-(4-chlorphenyl)-uracil Fp.: 130 - 1320C 80 % Fp.: 254°C Ausbeute: 76% Fp.: Ausbeute: 30 % Beispiel 2: Zu einer Lösung von 5,3 g (0,05 Mol) N-Chlorcarbonylisocyana-t in 100 ml Chlorbenzol -tropSt man bei 30 bis 350C innerhalb einer halben Stunde die Lösung von 7,5 g (0,05 Mol) Acetophenon-0-methyl-oxirn in 25 ml Chlorbenzol, rührt das Reaktionsgemisch 15 Minuten nach und erhitzt es dan innerhalb 3 Stunden auf 1300C, wobei HCl-Entwicklung festzustellen ist. Der Ansatz wird anschließend gekühlt, der ausgefallene Niederschlag abgesaugt, mit etwas Chlorbenzol und Äther gewaschen, ge-trocknet und aus Methanol umkristallisiert. Man erhält 6,9 g (63 % der Theorie) 1-Methoxy-6-phenyluracil vom Fp. 200 - 201 0C.The following can be prepared in the same way: Yield: 1,6-Diphenyluracil M.p .: 2620C 85% 1-Phenyl-6- (2-chlorophenyl) uracil M.p .: 271-2730C 90% 1-Phenyl-6- (4-chlorophenyl) -uracil m.p .: 234-235 ° C 85% 1-phenyl-6- (3-fluorophenyl) -uracil m.p .: 57-2589C 70% 1-phenyl-6- (4-fluorophenyl) -uracil m.p .: 252-2530C 75 5'-phenyl-6- (3,4-dichloPphenyl) uracil m.p .: 251-2540C 80% yield: 1-phenyl-6- (2-nitrophenyl) uracil m.p .: 2160C 50% -1-phenyl-6- (3-nitrophenyl) -uracil m.p .: 240-2420C 70% 1-phenyl-6- (4-nitrophenyl) -uracil m.p .: 261-2630C 70% 1-phenyl-6- ( 4-tolyl) uracil m.p .: 240-242 ° C 70% 1-phenyl-6- (3,4-dimethylphenyl) uracil m.p .: 227-2290C 75% 1-phenyl-6- (4-isopropylphenyl) -uracil m.p .: 205-2060C 75% 1-phenyl-6- (2-methoxyphenyl) -uracil m.p .: 247-2490C 55% 1-phenyl-6- (3-methoxyphenyl) -uracil m.p .: 191-193 ° C 85% 1-phenyl-6- (4-methoxyphenyl) -uracil m.p .: 242 - 2440C 85% 1-phenyl-6- (2-ethoxyphenyl) -uracil m.p .: 250 - 2520C 85% 1-phenyl- 6- (4-ethoxyphenyl) uracil m.p. 200-2020C 80% 1-P henyl-6- (3-methyl-4-methoxyphenyl) -uracil F 228-2300C 85% 1-phenyl-6- (4-methyl-2-ethoxyphenyl) -uracil m.p .: 273-275 ° C 85% 1- Phenyl-6- (2,4-diethoxyphenyl) uracil m.p .: 233-2350C 60% 1-phenyl-6- (4-cyanophenyl) uracil m.p .: 252-2540C 20% 1-phenyl-6- (4th diethylaminoethoxyphenyl) uracil m.p .: hydrochloride 234-2360C 10% 1-phenyl-6-isobutyluracil m.p. 2210C 80% yield: 1-phenyl-6-tert.-butyluracil m.p .: 270-272 ° C 80% 1- Phenyl-6-cyclohexyluracil m.p .: 234-2350C 87% 1-phenyl-6- (1-phenylethyl) uracil m.p .: 167-1690C 65% 1-phenyl-6- (2,2-dimethylvinyl) uracil m.p .: .: 239-2410C 57% 1-phenyl-6-styryluracil m.p .: 247-2480C 85% 1,6-diphenyl-5-methyluracil m.p .: 3190C 79 5 '1,6-diphenyl-5-isopropyluracil m.p .: 268-2700C 65% 1-phenyl-6- (3-pyridyl) uracil m.p .: 236-238 ° C 15% 1-phenyl-6- (4-pyridyl) uracil m.p .: hydrochloride 1880C 21% 1- Phenyl-6- (2-furyl) -uracil m.p .: 278-2800C 16% 1-phenyl-6- (2-thienyl) -uraci1 m.p .: 272-2740C 80% 1- (2-chlorophenyl) -6- phenyluracil m.p .: 288-2900C 72% 1- (3-chlorophenyl) -6-phenyluracil m.p .: 236-2380C 93% 1- (3,4-dichlorophenyl) -6-phenyluracil m.p .: 250-254 ° C 80% 1- (3-methylphenyl ) -6-Phenyluracil m.p .: 235-2360C 93% - (4-methylphenyl) -6-phenyluracil m.p .: 258-2590C 95 5 '1- (4-ethylphenyl) -6-phenyluracil m.p .: 250 ° C 63 % Yield: 1- (3,4-Dimethylphenyl) -6-phenyluracil M.p .:? 78-2800C 85% 1- (4-methoxyphenyl) -6-phenyluracil M.p .: 224-2260C 26% 1- (4-methoxycarbonylphenyl ) -6-phenyluracil m.p .: 229-231 ° C 83% 1-methyl-6-phenyluracil m.p .: 199-201 ° C 50% 1-propyl-6-phenyluracil m.p .: i29-131 ° C 80 5 ' 1-n-Butyl-6-phenyluracil m.p .: 123-125 ° C 85% 1-isobutyl-6-phenyluracil m.p .: 164-1650C 85% 1-dodecyl-6-phenyluracil m.p .: 64-680C 75 5 ' 1-Cyclohexyl-6-phenyluracil M.p .: 2200C 80% 1-Cyclohexyl-5-methyl-6-phenyluracil M.p .: 221 ° C 80% 1-Allyl-6-phenyluracil M.p .: 138-1400C 80% 1- (3-Ethoxypropyl) -6-phenyluracil m.p .: 113-116 ° C 80% 1- (4-chlorophenyl) -6- (2-chlorophenyl) uracil m.p .: 247-2490C 85% 1- (3.4 -Dichlorophenyl) -6- (2-ch lorphenyl) uracil m.p .: 236-2380C 85% 1-n-butyl-6- (2-chlorophenyl) uracil m.p .: 130-1320C 80% 1- (3-ethoxypropyl) -6- (4-chlorophenyl) -uracil m.p .: 130-1320C 80% M.p .: 254 ° C Yield: 76% Fp .: Yield: 30% Example 2: To a solution of 5.3 g (0.05 mol) of N-chlorocarbonylisocyana-t in 100 ml of chlorobenzene -tropSt at 30 to 350 ° C., the solution of 7.5 g (0.05 mol) of acetophenone-0 is added within half an hour methyl oxime in 25 ml of chlorobenzene, the reaction mixture is stirred for 15 minutes and then heated to 130 ° C. within 3 hours, evolution of HCl being observed. The batch is then cooled, the precipitate which has separated out is filtered off with suction, washed with a little chlorobenzene and ether, dried and recrystallized from methanol. 6.9 g (63% of theory) of 1-methoxy-6-phenyluracil with a melting point of 200-20 ° C. are obtained.

C11H10N203 (218,2) ber.: C 60,54 H 4,62 N 12,84 gef.: C 60,87 H 4,87 N 13,16 Analog lassen sich herstellen: Ausbeute: 1-Methoxy-6-(2-chlorphenyl)-uracil Fp.: 184°C 50 % 1-Methoxy-5-methyl-6-phenyl-uracil Fp.: 195 - 1970C 40 % 1 -Äthoxy-6-phenyl-uracil Fp.: 1470C 58,5 % 1-(2-Dimethylamino-äthoxy)-6-phenyl-uracil Fp.: Hydrochlorid 204 - 2050C 19 5' 1-Benzyloxy-6-phenyluracil Fp.: 181°C 48 % 1- (4-Methyl-benzyloxy) -6-phenyluracil Fp.: 191 0C 47 % 1-(3-n-Propoxy-benzyloxy)-6-phenyluracil Fp.: 121 0C 49,5 % 1-(2-Chlor-benzyloxy)-6-phenyluracil Fp.: 186 - 1870C 30,5 % 1-(4-Chlor-benzyloxy)-6-phenyluracil Fp.: 1990C 44,5 % 1-(3-Nitro-benzyloxy)-6-phenyluracil Fp.: 229 - 2300C 26,5 5' 1-(2-Phenäthoxy)-6-phenyluracil Fp.: 134°C 29 % 1-(Dimethylcarbamoyloxy)-6-phenyluracil Fp.: 192 - 1930C 15 5' Fp.: 198°C 56 5' Fp.: Hydrochlorid 156 - 1570C Ausbeute: 34,5 % Beispiel 3: Zu einer Lösung von 26,7 g (0,254 Mol) N-Chlorcarbonylisocyanat in 300 ml Chlorbenzol werden bei 30 bis 35 0C 55 g (0,254 Mol) des Hydrazons aus Acetophenon und N-Aminoperhydroazepin zugetropft, die in 300 ml Chlorbenzol gelöst sind. Das Gemisch wird 15 Minuten nachgerührt und anschließend innerhalb 3 Stunden auf 95 0C erhitzt. Nach dem Erkalten wird das Lösungsmittel im Vakuum abgezogen und der Rückstand aus Äthanol umkristallisiert. Man erhält 34,9 g (0,1225 Mol = 48,2 % der Theorie) 1-Perhydroazepino-6-phenyluracil vom Schmelzpunkt 230 - 2320C.C11H10N203 (218.2) calc .: C 60.54 H 4.62 N 12.84 found: C 60.87 H 4.87 N 13.16 The following can be prepared in the same way: Yield: 1-methoxy-6- ( 2-chlorophenyl) uracil m.p .: 184 ° C 50% 1-methoxy-5-methyl-6-phenyl-uracil m.p .: 195-1970C 40% 1-ethoxy-6-phenyl-uracil m.p .: 1470C 58, 5% 1- (2-dimethylamino-ethoxy) -6-phenyl-uracil m.p .: hydrochloride 204-2050C 19 5 '1-benzyloxy-6-phenyluracil m.p .: 181 ° C 48% 1- (4-methyl-benzyloxy ) -6-phenyluracil m.p .: 191 ° C. 47% 1- (3-n-propoxy-benzyloxy) -6-phenyluracil m.p .: 121 ° C. 49.5% 1- (2-chloro-benzyloxy) -6-phenyluracil .: 186-1870C 30.5% 1- (4-chloro-benzyloxy) -6-phenyluracil M.p .: 1990C 44.5% 1- (3-nitro-benzyloxy) -6-phenyluracil M.p .: 229-2300C 26 , 5 5 '1- (2-phenethoxy) -6-phenyluracil m.p .: 134 ° C 29% 1- (dimethylcarbamoyloxy) -6-phenyluracil m.p .: 192-1930C 15 5' M.p .: 198 ° C 56 5 ' Mp .: Hydrochloride 156-1570C Yield: 34.5% Example 3: To a solution of 26.7 g (0.254 mol) of N-chlorocarbonyl isocyanate in 300 ml of chlorobenzene, 55 g (0.254 mol) of the hydrazone of acetophenone and N-aminoperhydroazepine, which are dissolved in 300 ml of chlorobenzene, are added dropwise at 30 to 35 ° C. The mixture is stirred for a further 15 minutes and then heated to 95 ° C. over the course of 3 hours. After cooling, the solvent is stripped off in vacuo and the residue is recrystallized from ethanol. 34.9 g (0.1225 mol = 48.2% of theory) of 1-perhydroazepino-6-phenyluracil with a melting point of 230-2320 ° C. are obtained.

Analog lassen sich herstellen: Ausbeute 1 -Piperidino-6-phenyluracil Fp.: 228 - 2290C 60 % 1-Morpholino-6-phenyluracil Fp.: 238 - 2390C 50 % 1- (Dimethylamino) -6-phenyluracil Fp.: 258 - 2600C 30 5' Ausbeute: 1-(Diallylamino)-6-phenyluracil Fp.: 169 - 171°C 35 5' 1-(Dimethylamino)-6-methyluracil Fp.: 208-210°C 30% 1-(Dimethylamino)-5-methyl-6-phenyluracil Fp.: 241 - 2430C 25 % 1-(Dimethylamino)-2,4-dioxo-1,2,3,4,5,6,7,8-octahydro-chinazolin Fp.: 189 - 1900C 25 O/o Beispiel 4: Zu einem Gemisch aus 29,8 g (0,1 Mol) 1-(4-Chlorphenyl)-6-phenyluracil, 30 g gesiebter, wasserfreier Pottasche und 300 ml Dimethylformamid werden unter intensivem Rühren bei 30 bis 350C 18,5 g (0,13 Mol) Methyljodid gegeben.The following can be prepared in the same way: Yield 1-piperidino-6-phenyluracil m.p .: 228-2290C 60% 1-morpholino-6-phenyluracil m.p .: 238-2390C 50% 1- (dimethylamino) -6-phenyluracil m.p .: 258 - 2600C 30 5 'Yield: 1- (diallylamino) -6-phenyluracil m.p .: 169-171 ° C 35 5' 1- (dimethylamino) -6-methyluracil m.p .: 208-210 ° C 30% 1- (dimethylamino) -5-methyl-6-phenyluracil m.p .: 241-2430C 25% 1- (dimethylamino) -2,4-dioxo-1,2,3,4,5,6,7,8-octahydro-quinazoline m.p .: 189 - 1900C 25 O / o Example 4: To a mixture of 29.8 g (0.1 mol) 1- (4-chlorophenyl) -6-phenyluracil, 30 g of sieved, anhydrous potash and 300 ml of dimethylformamide, 18.5 g (0 , 13 mol) methyl iodide.

Das Reaktionsgemisch wird anschließend noch 5 Stunden bei 400C gerührt. Danach wird der unlösliche Teil abgetrennt, die Lösung im Vakuum zur Trockne eingeengt und der Rückstand aus Äthanol umkristallisiert. Es werden 26,9 g (0,86 Mol =A 86 % der Theorie) 1-(4-Chlorphenyl)-3-methyl-6-phenyluracil vom Schmelzpunkt 211 - 213 0C erhalten.The reaction mixture is then stirred at 40 ° C. for a further 5 hours. The insoluble part is then separated off and the solution is concentrated to dryness in vacuo and the residue is recrystallized from ethanol. There are 26.9 g (0.86 mol = A 86 % of theory) 1- (4-chlorophenyl) -3-methyl-6-phenyluracil with a melting point of 211 - 213 0C received.

Analog lassen sich (unter Verwendung von Methyljodid, Äthylbromid, n-Propylbromid, Isopropyljodid, n-Butylbromid, Allylbromid, Benzylchlorid, 2-Diäthylaminoäthylchlorid, 3-Dimethylamino-propylchlorid als Alkylierungsmittol) herstelle 1 6-Diphenyl-3-methyluracil Fp.; 235 - 2360C; Ausbeute 80% 1-Phenyl-3-methyl-6-(2-chlorphenyl)-uracil Fp.: 148 - 1500C; Ausbeute 80 % 1-Phenyl-3-methyl-6-(4-chlorphenyl)-uracil Fp.: 167 - 1680C; Ausbeute 80 % 1-Phenyl-3-methyl-6-(3-nitrophenyl)-uracil Fp.: 174 - 1760C; Ausbeute 70 % 1-Phenyl-3-methyl-6-(4-äthoxypyhenyl)-uracil Fp.: 134 - 1360C; Ausbeute 80 % 1-Phenyl-3-methyl-6-(2,4-diäthoxyphenyl)-uracil Fp.: 120 - 1220C; Ausbeute 70 % 1-(4-Chlorphenyl)-3-methyl-6-(2-chlorphenyl)-uracil Fp.: 165 - 1670C; Ausbeute 80 % 1-(3,4-Dichlorphenyl)-3-methyl-6-(2-chlorphenyl)-uracil Fp.: 201 - 2030C; Ausbeute 70% 1,3-Dimethyl-6-phenyluracil Fp.: 124 - 1260C; Ausbeute 70 % 1-n-Propyl-3-methyl-6-phenyluracil Fp.: 75 - 770C; Ausbeute 85 % 1-n-Butyl-3-methyl-6-phenyluracil Fp.: 65 - 670C; Ausbeute 85 % 1-Allyl-3-methyl-6-phenyluracil Fp.: 88 90°C; Ausbeute 70% 1-(4-Chlorphenyl)-3-äthyl-6-phenyluracil Fp.: 164 - 166°C; Ausbeute 70 % 1-Methyl-3-äthyl-6-phenylurcil Fp.: 123 - 124°C; Ausbeute 70 % 1-(4-Chlorphenyl)-3-n-propyl-6-phenyluracil Fp.: 167 - 1680C; Ausbeute 80 % 1-(4-Chlorphenyl)-3-isopropyl-6-phenyluracil Fp.: 169 171°C; Ausbeute 75 % 1- (4-Chlorphenyl) -3-allyl-6-phenyluracil Fp.: 123 - 125°C; Ausbeute 70 5' 1-(4-Chlorphenyl)-3-benzyl-6-phenyluracil Fp.: 138 - 1400C; Ausbeute 85% 1-Methyl-3-benzyl-6-phenyluracil Fp.: 134 - 136°C; Ausbeute 85 % 1,6-Diphenyl-3-diäthylaminoäthyl-uracil Fp.: 91 - 93°C; Ausbeute 70 % 1-(4-Chlorphenyl)-3-diäthylaminoäthyl-6-phenyluracil Fp.: 102 - 103°C; Ausbeute 70 % 1-(4-Chlorphenyl)-3-dimethylaminopropyl-6-phenyluracil Fp.: 135°C; Ausbeute 70 % 1 -Methoxy-3-methyl-6-phenyluracil Fp.: 870C; Ausbeute 60% 1-Benzyloxy-3-methyl-6-phenyluracil Fp.: 1360C; Ausbeute 82 % 1-Methoxy-3-(2-diäthylamino-äthyl)-6-phenyluracil Fp.: Hydrochlorid 166 - 1670C; Ausbeute 58% 1- (Dimethylamino) -3-methyl-6-phenyluracil Fp.: 162 - 1640C; Ausbeute 70 % 1-(Dimethylamino)-3-(dimethylaminopropyl)-6-phenyluracil Fp.: 75 - 770C; Ausbeute 65 % 1-(Dimethylamino)-3-allyl-6-phenyluracil Fp.: 100 - 102°C; Ausbeute 75 % Beispiel 5: 1-(4-Chlorphenyl)-3-allyl-6-phenyluracil Fp.: 123 - 1250C; Ausbeute 70 5' 1-(4-Chlorphenyl)-3-benzyl-6-phenyluracil Fp.: 138 - 1400C; Ausbeute 85 % 1-Methyl-3-benzyl-6-phenyluracil Fp.: 134 - 136°C; Ausbeute 85 % 1,6-Diphenyl-3-diathylaminoäthyl-uracil Fp.: 91 - 930C; Ausbeute 70 % 1-(4-Chlorphenyl)-3-diäthylaminoäthyl-6-phenyluracil Fp.: 102 - 1030C; Ausbeute 70 % 1- (4-Chlorphenyl ) -3-dimethylaminopropyl-6-phenyluracil Fp.: 1350C; Ausbeute 70 % 1-Methoxy-3-methyl-6-phenyluracil Fp.: 870C; Ausbeute 60 % 1-Benzyloxy-3-methyl-6-phenyluracil Fp.: 1360C; Ausbeute 82 % 1-Methoxy-3-(2-diäthylamino-äthyl)-6-phenyluracil Fp.: Hydrochlorid 166 - 1670C; Ausbeute 58 % 1-(Dimethylamino)-3-methyl-6-phenyluracil Fp.: 162 - 1640C; Ausbeute 70 % 1-(Dimethylamino)-3-(dimethylaminopropyl)»6-phenyluracil Fp.: 75 - 77°C; Ausbeute 65 % 1-(Dimethylamino)-3-allyl-6-phenyluracil Fp.: 100 - 102°C; Ausbeute 75 % Beispiel 5: 10 g (0,032 Mol) 1-Phenyl-6-(3-nitrophenyl)-uracil werden in 150 ml Dimethylformamid gelöst und mit 5 g Raney-Nickel bei Raumtemperatur und Normaldruck hydriert. Anschließend wird der Katalysator entfernt, das Lösungsmittel im Vakuum abgezogen und der Rückstand aus Äthanol umkristallisiert.1 6-Diphenyl-3-methyluracil Fp .; 235-2360C; Yield 80% 1-phenyl-3-methyl-6- (2-chlorophenyl) uracil m.p .: 148-1500C; Yield 80% 1-phenyl-3-methyl-6- (4-chlorophenyl) uracil m.p .: 167-1680C; Yield 80% 1-phenyl-3-methyl-6- (3-nitrophenyl) uracil m.p .: 174-1760C; Yield 70% of 1-phenyl-3-methyl-6- (4-ethoxypyhenyl) uracil m.p .: 134-1360C; Yield 80% of 1-phenyl-3-methyl-6- (2,4-diethoxyphenyl) uracil m.p .: 120-1220C; Yield 70% 1- (4-chlorophenyl) -3-methyl-6- (2-chlorophenyl) uracil m.p .: 165-1670C; Yield 80% 1- (3,4-dichlorophenyl) -3-methyl-6- (2-chlorophenyl) uracil m.p .: 201-2030C; Yield 70% 1,3-dimethyl-6-phenyluracil m.p .: 124-1260C; Yield 70% of 1-n-propyl-3-methyl-6-phenyluracil m.p .: 75-770C; Yield 85% of 1-n-butyl-3-methyl-6-phenyluracil m.p .: 65-670C; Yield 85% of 1-allyl-3-methyl-6-phenyluracil M.p .: 88-90 ° C; Yield 70% of 1- (4-chlorophenyl) -3-ethyl-6-phenyluracil; Mp .: 164-166 ° C; Yield 70% of 1-methyl-3-ethyl-6-phenylurcil. Mp .: 123-124 ° C; Yield 70% 1- (4-chlorophenyl) -3-n-propyl-6-phenyluracil m.p .: 167-1680C; Yield 80% 1- (4-chlorophenyl) -3-isopropyl-6-phenyluracil m.p .: 169 171 ° C; Yield 75% 1- (4-chlorophenyl) -3-allyl-6-phenyluracil M.p .: 123-125 ° C; Yield 70 5 '1- (4-chlorophenyl) -3-benzyl-6-phenyluracil m.p .: 138-1400C; Yield 85% of 1-methyl-3-benzyl-6-phenyluracil M.p .: 134-136 ° C; Yield 85% 1,6-diphenyl-3-diethylaminoethyl-uracil mp: 91-93 ° C; Yield 70% of 1- (4-chlorophenyl) -3-diethylaminoethyl-6-phenyluracil; Mp .: 102-103 ° C; Yield 70% of 1- (4-chlorophenyl) -3-dimethylaminopropyl-6-phenyluracil M.p .: 135 ° C; Yield 70% of 1-methoxy-3-methyl-6-phenyluracil m.p .: 870C; Yield 60% 1-benzyloxy-3-methyl-6-phenyluracil m.p .: 1360C; Yield 82% of 1-methoxy-3- (2-diethylamino-ethyl) -6-phenyluracil M.p .: hydrochloride 166-1670C; Yield 58% 1- (dimethylamino) -3-methyl-6-phenyluracil m.p .: 162-1640C; Yield 70% 1- (dimethylamino) -3- (dimethylaminopropyl) -6-phenyluracil m.p .: 75-770C; Yield 65% 1- (dimethylamino) -3-allyl-6-phenyluracil M.p .: 100-102 ° C; Yield 75% Example 5: 1- (4-chlorophenyl) -3-allyl-6-phenyluracil m.p .: 123-1250C; Yield 70 5 '1- (4-chlorophenyl) -3-benzyl-6-phenyluracil m.p .: 138-1400C; Yield 85% of 1-methyl-3-benzyl-6-phenyluracil M.p .: 134-136 ° C; Yield 85% 1,6-diphenyl-3-diethylaminoethyl-uracil M.p .: 91-930C; Yield 70% of 1- (4-chlorophenyl) -3-diethylaminoethyl-6-phenyluracil; Mp .: 102-1030C; Yield 70% 1- (4-chlorophenyl) -3-dimethylaminopropyl-6-phenyluracil m.p .: 1350C; Yield 70% of 1-methoxy-3-methyl-6-phenyluracil m.p .: 870C; Yield 60% 1-benzyloxy-3-methyl-6-phenyluracil m.p .: 1360C; Yield 82% of 1-methoxy-3- (2-diethylamino-ethyl) -6-phenyluracil M.p .: hydrochloride 166-1670C; Yield 58% 1- (dimethylamino) -3-methyl-6-phenyluracil m.p .: 162-1640C; Yield 70% of 1- (dimethylamino) -3- (dimethylaminopropyl) »6-phenyluracil melting point: 75-77 ° C; Yield 65% 1- (dimethylamino) -3-allyl-6-phenyluracil M.p .: 100-102 ° C; Yield 75% Example 5: 10 g (0.032 mol) of 1-phenyl-6- (3-nitrophenyl) uracil are dissolved in 150 ml of dimethylformamide and hydrogenated with 5 g of Raney nickel at room temperature and normal pressure. The catalyst is then removed, the solvent is stripped off in vacuo and the residue is recrystallized from ethanol.

Man erhält 7,2 g (0,026 Mol # 80 % der Theorie) 1-Phenyl-6-(3-aminophenyl)-uracil vom Schmelzpunkt 244 - 2460C.7.2 g (0.026 mol # 80% of theory) of 1-phenyl-6- (3-aminophenyl) uracil are obtained from melting point 244-2460C.

Analog lassen sich herstellen: 1-Phenyl-3-methyl-6-(3-aminophenyl)-uracil Fp.: 244 - 245°C; Ausbeute 70 Xo 1-Phenyl-3-methyl-6-(4-aminophenyl)-uracil Fp.: 243 - 2450C; Ausbeute 70 % Beispiel 6i 14,7 g (0,05 Mol) 1-Phenyl-3-methyl-6-(3-aminophenyl)-uracil und 100 ml Acetanhydrid werden eine Stunde auf 80°C erhitzt. Danach wird im Vakuum zur Trockne eingeengt. Der Rückstand wird zunächst mit Wasser gewaschen, dann aus Äthanol umkristallisiert. Man erhält 13,7 g (0,041 Mol - 82 5 der Theorie) 1-Phenyl-3-methyl-6-(3-acetamidophenyl)-uracil vom Schmelzpunkt 131 - 133 ÖC.The following can be prepared analogously: 1-Phenyl-3-methyl-6- (3-aminophenyl) -uracil; melting point: 244-245 ° C .; Yield 70 Xo 1-phenyl-3-methyl-6- (4-aminophenyl) uracil m.p .: 243-2450C; Yield 70% Example 6i 14.7 g (0.05 mol) of 1-phenyl-3-methyl-6- (3-aminophenyl) uracil and 100 ml of acetic anhydride are heated to 80 ° C. for one hour. It is then concentrated to dryness in vacuo. The residue is first washed with water, then recrystallized from ethanol. 13.7 g (0.041 mol - 82.5 of theory) of 1-phenyl-3-methyl-6- (3-acetamidophenyl) uracil with a melting point of 131-133 ° C. are obtained.

Analog lassen sich herstellen: 1-Phenyl-6-(3-acetamidophenyl)-uracil Fp.: 305 - 3060C; Ausbeute 70 % 1-Phenyl-3-methyl-6-(4-acetamidphenyl)-uracil Fp.: 149 - 1500C; Ausbeute 70 %The following can be prepared analogously: 1-phenyl-6- (3-acetamidophenyl) uracil M.p .: 305-3060C; Yield 70% 1-phenyl-3-methyl-6- (4-acetamidphenyl) uracil. 149-1500C; Yield 70%

Claims (3)

Patentansprüche: 1) Hypnotisches Mittel, gekennzeichnet durch einen Gehalt an mindestens einem Uracil-Derivat der Formel in welcher R1 für Alkyl, Alkenyl, Cycloalkyl, Aralkyl, Aryl, Alkoxyalkyl, Alkoxy, Aralkoxy, Dialkylaminoalkoxy, Dialkylamino der Formel wobei R' und R" zusammen mit dem Stickstoff gegebenenfalls einen 5- bis 8-gliedrigen Ring bilden, Dialkenylamino oder Morpholino steht, und R2 für Wasserstoff, Alkyl, Alkenyl, Dialkylaminoalkyl oder Aralkyl steht, und R3 für Wasserstoff, Alkyl, Aryl oder Halogen steht, und R4 für Alkyl, Alkenyl, Cycloalkyl, Aralkyl, Aralkenyl, Aryl oder einen heterocyclischen Rest steht.Claims: 1) Hypnotic agent, characterized by a content of at least one uracil derivative of the formula in which R1 represents alkyl, alkenyl, cycloalkyl, aralkyl, aryl, alkoxyalkyl, alkoxy, aralkoxy, dialkylaminoalkoxy, dialkylamino of the formula where R 'and R "together with the nitrogen optionally form a 5- to 8-membered ring, dialkenylamino or morpholino , and R2 stands for hydrogen, alkyl, alkenyl, dialkylaminoalkyl or aralkyl, and R3 stands for hydrogen, alkyl, aryl or halogen, and R4 stands for alkyl, alkenyl, cycloalkyl, aralkyl, aralkenyl, aryl or a heterocyclic radical. 2) Verfahren zur Herstellung eines hypnotischen Mittels, dadurch gekennzeichnet, daß man Uracile gemäß Anspruch 1 mit inerten, nichttoxischen, pharmazeutisch geeigneten Trägerstoffen vermischt.2) A method for producing a hypnotic agent, characterized in that that uracils according to claim 1 with inert, non-toxic, pharmaceutically suitable Mixed carriers. 3) Verfahren zur Behandlung von Schlafstörungen, dadurch gekennzeichnet, daß man Uracile gemäß Anspruch 1 Menschen oder Tieren appliziert, die an Schlafstörungen erkrankt sind.3) method for the treatment of sleep disorders, characterized in that that uracile is administered according to claim 1 to humans or animals suffering from sleep disorders are sick.
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US4395550A (en) * 1979-07-05 1983-07-26 Sandoz Ltd. Tetrahydro-2(1H)-quinazolinones and cyclohexene nitriles
US4495349A (en) * 1983-07-11 1985-01-22 The Upjohn Company 6-Aryluracils
US4521599A (en) * 1983-07-11 1985-06-04 The Upjohn Company Process for the preparation of 1,3-oxazine-4-ones
US4578466A (en) * 1983-07-11 1986-03-25 The Upjohn Company Processes for the preparation of 6-aryluracils
US4593030A (en) * 1983-07-11 1986-06-03 The Upjohn Company Use of 6-aryluracils as antiinflammatory and antiarthritic agents
US4625028A (en) * 1983-07-11 1986-11-25 The Upjohn Company 6-aryluracils and selected novel intermediates used in the preparation thereof
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US5461060A (en) * 1989-09-29 1995-10-24 Mitsubishi Kasei Corporation Pyrimidine derivatives and anti-viral agent containing the same as active ingredient thereof
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US6649618B2 (en) 2000-07-18 2003-11-18 Bayer Aktiengesellschaft Substituted amidoalkyl-uracils and their use
US7125995B2 (en) 2000-11-14 2006-10-24 Bayer Aktiengesellschaft Substituted amidoalkyl uracils and their use as inhibitors of the poly(adp-ribose) synthetase (PARS)
WO2003084937A3 (en) * 2002-04-10 2004-06-03 Orchid Chemicals & Pharm Ltd Pyrimidinedione derivatives useful for the treatment of inflammation and immunological diseases
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