Roussel Uclaf

John Bodenham Taylor

David A Rowlands

Derek Ralph Harrison

Alan C Barnes

Peter Wilfred Hairsine

Peter John Ramm

Robert Westwood

Saroop Singh Matharu

Novel imidazobenzoxazines of the formula ##STR1## wherein X is selected from the group consisting of hydrogen, halogen and alkyl of 1 to 5 carbon atoms, R is selected from the group consisting of hydrogen, alkyl of 1 to 5 carbon atoms, and an equivalent of alkali metal, alkaline earth metal, magnesium, aluminum and nitrogen bases, Y is selected from the group consisting of hydrogen and alkyl of 1 to 5 carbon atoms, Z is selected from the group consisting of hydrogen and alkoxy of 1 to 5 carbon atoms with the proviso that at least one but not more than 2 of X, Y and Z are hydrogen, and their non-toxic, pharmaceutically acceptable acid addition salts having antiallergic and bronchodilatory activity and their preparation.

Novel imidazobenzoxazines

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 pyrroloquinoxalines of the formula ##STR1## wherein X and Y are individually selected from the group consisting of hydrogen, halogen, alkyl and alkoxy of 1 to 5 carbon atoms and --NO.sub.2, Z is selected from the group consisting of alkyl of 1 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, alkenyl of 2 to 6 carbon atoms and phenyl and R is selected from the group consisting of hydrogen, alkyl of 1 to 5 carbon atoms, ##STR2## and non-toxic, pharmaceutically acceptable cations, n is an integer from 1 to 6 and R.sub.1 and R.sub.2 are individually alkyl of 1 to 5 carbon atoms and the non-toxic, pharmaceutically acceptable acid addition salts thereof having antiallergic activity and to a novel process for their preparation.

Pyrroloquinoxalines

Novel imidazobenzoxazines of the formula ##STR1## wherein X is selected from the group consisting of hydrogen, nitro, NH.sub.2 and a protected amino Z is selected from the group consisting of --COOR, and ##STR2## R is selected from the group consisting of hydrogen, alkyl of 1 to 5 carbon atoms, ##STR3## alkali metal, alkaline earth metal, magnesium, aluminum and nitrogen bases, n is 1,2 or 3, R.sub.1 and R.sub.2 individually are selected from the group consisting of hydrogen and alkyl of 1 to 5 carbon atoms and taken together with the nitrogen atom to which they are attached form a saturated heterocyclic ring of 4 to 6 carbon atoms optionally interrupted by another heteroatom which may optionally be substituted with alkyl of 1 to 5 carbon atoms and their non-toxic, pharmaceutically acceptable acid addition salts having antiallergic and bronchodilatory activity 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.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 xanthone-2-carboxylic acid compounds of the formula ##STR1## wherein A is selected from the group consisting of --COOR', a 1H-tetrazol-5-yl and a 1H-tetrazolylcarbamoyl, R' is selected from the group consisting of hydrogen, alkyl of 1 to 5 carbon atoms and cation of a non-toxic, pharmaceutically acceptable organic or inorganic base, R is selected from the group consisting of hydrogen, alkyl of 1 to 9 carbon atoms, alkoxy of 1 to 9 carbon atoms and alkoxy alkoxy of 2 to 9 carbon atoms and X is selected from the group consisting of ##STR2## AND ##STR3## WHEREIN R.sub.1 is alkyl of 1 to 5 carbon atoms, R.sub.2 is selected from the group consisting of hydrogen, acyl of an aliphatic acid of 1 to 5 carbon atoms, aroyl of 7 to 8 carbon atoms, araliphatic acyl with 1 to 5 carbon atoms in the aliphatic portion and 6 or 7 carbon atoms in the aryl portion, aralkyl of 7 to 8 carbon atoms, arylsulfonyl, a carbamoyl, a carboxyalkyl of 1 to 5 carbon atoms, --CO--(CH.sub.2).sub.n -- Het where n is 1,2 or 3 and Het is a N-attached nitrogen heterocyclic which may contain an additional heteroatom and ##STR4## AND Alk is alkyl of 1 to 5 carbon atoms and R.sub.3 is arylsulfonyl which possess anti-allergic properties and their preparation.

Novel xanthone-2-carboxylic acid compounds

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.

Novel xanthone-2-carboxylic acid compounds of the formula ##STR1## wherein A is selected from the group consisting of --COOR', a 1H-tetrazol-5-yl and a 1H-tetrazolylcarbamoyl, R' is selected from the group consisting of hydrogen, alkyl of 1 to 5 carbon atoms and cation of a non-toxic, pharmaceutically acceptable organic or inorganic base, R is selected from the group consisting of hydrogen, alkyl of 1 to 9 carbon atoms, alkoxy of 1 to 9 carbon atoms and alkoxy alkoxy of 2 to 9 carbon atoms and X is selected from the group consisting of ##STR2## AND ##STR3## WHEREIN R.sub.1 is alkyl of 1 to 5 carbon atoms, R.sub.2 is selected from the group consisting of hydrogen, acyl of an aliphatic acid of 1 to 5 carbon atoms, aroyl of 7 to 8 carbon atoms, araliphatic acyl with 1 to 5 carbon atoms in the aliphatic portion and 6 or 7 carbon atoms in the aryl portion, aralkyl of 7 to 8 carbon atoms, arylsulfonyl, a carbamoyl, a carboxyalkyl of 1 to 5 carbon atoms, --CO--(CH.sub.2).sub.n -- Het where n is 1, 2 or 3 and Het is a N-attached nitrogen heterocyclic which may contain an additional heteroatom and ##STR4## AND Alk is alkyl of 1 to 5 carbon atoms and R.sub.3 is arylsulfonyl which possess anti-allergic properties and their preparation.

Xanthone-2-carboxylic acid compounds

The present invention relates to derivatives of hexahydrodibenzofuran-3-one and their salts possessing interesting antitussive activity, their process of preparation, intermediates, and pharmaceutical compositions.

Derivatives of hexahydrodibenzofuran-3-one, their preparation and use in

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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Down Ampney, near Cirencester, undefined

John Bodenham Taylor