Roussel Uclaf

Derek Ralph Harrison

John Bodenham Taylor

Novel 1,2-dihydro-6-phenyl-1H,4H-imidazo[1,2-a][1,4]-benzodiazepin-1-ones of the formula ##STR1## wherein R is selected from the group consisting of hydrogen, halogen, nitro and trifluoromethyl, R.sub.1 is selected from the group consisting of hydrogen and halogen, R.sub.2 is selected from the group consisting of hydrogen and methyl and R.sub.3 and R.sub.4 are individually selected from the group consisting of hydrogen, alkyl of 1 to 5 carbon atoms, hydroxyalkyl of 1 to 5 carbon atoms, aminoalkyl of 1 to 5 carbon atoms, mono-and di-alkylaminoalkyl with each alkyl having 1 to 5 carbon atoms, cycloalkyl of 3 to 8 carbon atoms and mono and di-nuclear aryl or R.sub.3 and R.sub.4 taken together with the nitrogen atom to which they are attached form a saturated heterocycle which may contain a second heteroatom optionally substituted with at least one member of the group consisting of alkyl of 1 to 5 carbon atoms, hydroxyalkyl of 1 to 5 carbon atoms, dialkylphosphinylalkyl with 1 to 5 carbon atoms in the alkyl groups, cycloalkylalkyl with 3 to 6 carbon atoms in the ring and 1 to 5 alkyl carbon atoms, alkenyl of 2 to 5 carbon atoms, phenyl and nitrogen heterocycles and their non-toxic, pharmaceutically acceptable acid addition salts having sedative, hypnotic, anxiolytic, tranquilizing, anticonvulsive and myorelaxant properties and their preparation.

1,2-Dihydro-6-phenyl-1H,4H-imidazobenzodiazepin-1-ones

Novel 1,2-dihydro-6-phenyl-1H,4H-imidazo[1,2-a] [1,4]-benzodiazepin-1-ones of the formula ##STR1## wherein R is selected from the group consisting of hydrogen, halogen, nitro and trifluoromethyl, R.sub.1 is selected from the group consisting of hydrogen and halogen, R.sub.2 is selected from the group consisting of hydrogen and methyl and R.sup.3 and R.sup.4 are individually selected from the group consisting of hydrogen, alkyl of 1 to 5 carbon atoms, hydroxyalkyl of 1 to 5 carbon atoms, aminoalkyl of 1 to 5 carbon atoms, mono-and di-alkyl-aminoalkyl with each alkyl having 1 to 5 carbon atoms, cycloalkyl of 3 to 8 carbon atoms and mono and di-nuclear aryl or R.sub.3 and R.sub.4 taken together with the nitrogen atom to which they are attached form a saturated heterocycle which may contain a second heteroatom optionally substituted with at least one member of the group consisting of alkyl of 1 to 5 carbon atoms, hydroxyalkyl of 1 to 5 carbon atoms, dialkylphosphinylalkyl with 1 to 5 carbon atoms in the alkyl groups, cycloalkylalkyl with 3 to 6 carbon atoms in the ring and 1 to 5 alkyl carbon atoms, alkenyl of 2 to 5 carbon atoms, phenyl and nitrogen heterocycles and their non-toxic, pharmaceutically acceptable acid addition salts having sedative, hypnotic, anxiolytic, tranquilizing, anticonvulsive and myorelaxant properties and their preparation.

Novel 1,2-dihydro-6-phenyl-1H,4H-imidazo[1,2-a][1,4]-benzodiazepin-1-ones of the formula ##STR1## wherein R is selected from the group consisting of hydrogen, halogen, nitro and trifluoromethyl, R.sub.1 is selected from the group consisting of hydrogen and halogen, R.sub.2 is selected from the group consisting of hydrogen and methyl and R.sub.3 and R.sub.4 are individually selected from the group consisting of hydrogen, alkyl of 1 to 5 carbon atoms, hydroxyalkyl of 1 to 5 carbon atoms, aminoalkyl of 1 to 5 carbon atoms, mono- and di-alkylaminoalkyl with each alkyl having 1 to 5 carbon atoms, cycloalkyl of 3 to 8 carbon atoms and mono and di-nuclear aryl or R.sub.3 and R.sub.4 taken together with the nitrogen atom to which they are attached form a saturated heterocycle which may contain a second heteroatom optionally substituted with at least one member of the group consisting of alkyl of 1 to 5 carbon atoms, hydroxyalkyl of 1 to 5 carbon atoms, dialkylphosphinylalkyl with 1 to 5 carbon atoms in the alkyl groups, cycloalkylalkyl with 3 to 6 carbon atoms in the ring and 1 to 5 alkyl carbon atoms, alkenyl of 2 to 5 carbon atoms, phenyl and nitrogen heterocycles and their non-toxic, pharmaceutically acceptable acid addition salts having sedative, hypnotic, anxiolytic, tranquilizing, anticonvulsive and myorelaxant properties and their preparation.

A derivative of 4(3H)-quinazolone, its method of preparation, and pharmaceutical compositions are described. In particular, 2-methyl-3-(o-cyanophenyl)-4(3H)-quinazolone and its acid addition salts are described. This compound may be prepared by the reaction of N-acetylanthranilic acid with anthranilonitrile in the presence of a dehydrating agent. The quinazolone and its salts possess pharmacological activity.

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Swindon, United Kingdom

Derek Ralph Harrison