Roussel Uclaf

David A Rowlands

John Bodenham Taylor

Alan C Barnes

Robert Westwood

Saroop Singh Matharu

Stephen Clements-Jewery

Julian M Golec

Wilfred R Tully

David P Kay

Peter D Kennewell

Peter Wilfred Hairsine

Colin R Gardner

Ian R Ager

Roger J Gillespie

Frederick L Parker

Novel pyrimido[2,1-b]benzothiazoles of the formula ##STR1## wherein R and R.sub.3 are individually selected from the group consisting of hydrogen and alkyl of 1 to 6 carbon atoms or taken together with the carbon to which they are attached form a cycloalkyl of 3 to 6 carbon atoms, R.sub.1 is selected from the group consisting of hydroxy, alkoxy of 1 to 12 carbon atoms, cycloalkyl of 7 to 12 carbon atoms, and ##STR2## R.sub.5 and R.sub.6 are individually selected from the group consisting of hydrogen and alkyl of 1 to 6 carbon atoms or taken together with the nitrogen form piperidino or morpholino, R.sub.2 is selected from the group consisting of hydrogen, alkyl of 1 to 6 carbon atoms, alkoxycarbonyl of 2 to 7 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, heteroaryl, aralkyl and optionally substituted aryl with at least one substituent selected from the group consisting of halogen, nitro, and alkyl and alkoxy of 1 to 6 carbon atoms and their salts with non-toxic, pharmaceutically acceptable acids and bases having antiallergic activity.

Pyrimido[2,1-b]benzothiazoles having antiallergic activity

Novel compounds of the formula ##STR1## wherein A is selected from the group consisting of nitrogen and .dbd.CH--, G is ##STR2## Z is selected from the group consisting of hydrogen and alkyl of 1 to 5 carbon atoms or taken with Y forms a carbon-carbon bond, Z' is selected from the group consisting of hydrogen and halogen, Y is hydrogen, or taken with Z is a carbon-carbon bond or taken with X is .dbd.O and X is hydrogen or taken with Y is .dbd.O, R is selected from the group consisting of hydroxymethyl, formyl, tetrazol-5-yl, N-(tetrazol-5-yl) carbamoyl, aminomethyl and carbamoyl, R.sub.1 is selected from the group consisting of hydrogen, halogen and alkoxy of 1 to 5 carbon atoms and its non-toxic, pharmaceutically acceptable acid addition salts having antiallergic activity and their preparation.

Imidazo[2,1-C]quinolines, useful as antiallergic agents

Novel benzothiopyranopyridinones of the formula ##STR1## wherein A,B,C and D are individually selected from the group consisting of hydrogen, alkyl and alkoxy of 1 to 6 carbon atoms, nitro, halogen, amino and acylamino of 2 to 7 carbon atoms or A and B or C and D taken with the carbon atoms to which they are attached form a benzene ring, R is selected from the group consisting of hydrogen and R', R' is selected from the group consisting of alkyl of 1 to 9 carbon atoms, alkenyl of 2 to 9 carbon atoms optionally substituted with an --OH, cycloalkyl of 3 to 9 carbon atoms, phenyl, aralkyl of 7 to 9 carbon atoms and --(CH.sub.2).sub.n --Z, n is an integer from 1 to 4, Z is selected from the group consisting of cycloalkyl and cycloalkenyl of 3 to 9 carbon atoms, dioxanyl, 2-oxobenzimidazolyl, benzoyl, halo substituted benzoyl, cyano, alkoxy carbonyl of 2 to 7 carbon atoms and carbamoyl and their non-toxic, pharmaceutically acceptable acid addition salts having antipsychotic and antidepressant and antidopaminergic activity.

Benzothiopyranopyridinones

Novel compounds of the formula ##STR1## wherein A is selected from the group consisting of nitrogen and .dbd.CH--, G is selected from the group consisting of --0--, ##STR2## Z is selected from the group consisting of hydrogen and alkyl of 1 to 5 carbon atoms or taken with Y forms a carbon-nitrogen or carbon-carbon bond, Z' is selected from the group consisting of hydrogen and halogen, Y is hydrogen, or taken with Z is a carbon-nitrogen or carbon-carbon bond or taken with X is .dbd.0 and X is hydrogen or taken with Y is .dbd.0, R is selected from the group consisting of hydroxymethyl, formyl, tetrazol-5-yl, N-(tetrazol-5-yl) carbamoyl, aminomethyl and carbamoyl, R.sub.1 is selected from the group consisting of hydrogen, halogen and alkoxy of 1 to 5 carbon atoms and its non-toxic, pharmaceutically acceptable acid addition salts having anti-allergic activity and their preparation.

Substituted imidazo 1,2-a-quinoxaline-4-(5H)ones, their compositions and

Novel triazoloquinazolones of the formula ##STR1## wherein R and R' are individually selected from the group consisting of hydrogen, halogen, nitro and alkyl and alkoxy of 1 to 3 carbon atoms, Y is selected from the group consisting of alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 4 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, aryl of 6 to 8 carbon atoms and aralkyl of 7 to 8 carbon atoms, B is an alkylene of 1 to 3 carbon atoms, X is selected from the group consisting of ##STR2## R.sub.1 and R.sub.2 are individually selected from the group consisting of hydrogen, alkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, aryl of 6 to 8 carbon atoms, aralkyl of 7 to 8 carbon atoms, aminoalkyl of 2 to 4 carbon atoms, mono- and dialkylaminoalkyl with each alkyl having 2 to 4 carbon atoms, piperidinoalkyl of 1 to 4 alkyl carbon atoms, morpholinoalkyl of 1 to 4 alkyl carbon atoms and piperazinylalkyl of 1 to 4 alkyl carbon atoms or R.sub.1 and R.sub.2 taken together with the nitrogen to which they are attached form a saturated mono- or bicyclic heterocyclic ring with 4 to 8 carbon atoms optionally substituted with 1 to 2 methyls and optionally containing in the ring a heteroatom selected from --O--, --S-- and ##STR3## and R.sub.3 is selected from the group consisting of hydrogen, alkyl of 1 to 3 carbon atoms, hydroxyalkyl of 1 to 3 carbon atoms, alkoxycarbonyl of 2 to 5 carbon atoms, aryl of 6 to 8 carbon atoms and aralkyl of 7 to 8 carbon atoms and their non-toxic, pharmaceutically acceptable acid addition salts having antihistaminic and bronchospasmolytic activity and their preparation and intermediates.

Triazoloquinazolones having antihistaminic and bronchospasmolytic

Novel imidazoquinoxalines of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of hydroxy, alkoxy of 1 to 5 carbon atoms and cyclohexylcarbonyloxymethoxy, R.sub.2 is selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms, alkoxycarbonylvinyl of 4 to 7 carbon atoms, --COR, --CONH(CH.sub.2).sub.n --X and --A--(CH.sub.2).sub.m --Y, R is selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms, cycloalkyl of 3 to 10 carbon atoms, alkenyl of 2 to 4 carbon atoms, alkoxy of 1 to 5 carbon atoms, alkoxycarbonyl of 2 to 5 carbon atoms, amino, --CF.sub.3, --CHCl.sub.2 --, phenyl, aralkyl of 7 to 10 carbon atoms, aralkoxy of 7 to 10 carbon atoms, n is 0 and X is phenyl or n is an integer from 1 to 5 and X is selected from the group consisting of ##STR2## R.sub.3 and R.sub.4 are individually selected from the group consisting of hydrogen, alkyl of 1 to 5 carbon atoms, cycloalkyl of 3 to 7 carbon atoms, aryl of 6 carbon atoms and aralkyl of 7 to 8 carbon atoms or R.sub.3 and R.sub.4 taken together with the nitrogen atom to which they are attached form a saturated heterocycle with 4 to 8 ring carbon atoms optionally containing at least one oxygen atom or sulfur atom or nitrogen atom optionally substituted with alkyl of 1 to 3 carbon atoms or alkoxycarbonyl of 2 to 5 carbon atoms, Hal is chlorine or bromine, A is selected from the group consisting of ##STR3## m is a integer from 1 to 3, Y is ##STR4## their non-toxic, pharmaceutically acceptable acid addition salts when R.sub.1 is other than --OH and their salts with pharmaceutically acceptable metals or nitrogen bases when R.sub.1 is --OH, having antiallergic properties.

4,5-Dihydroimidazo-[1,2-a]quinoxaline-2-carboxylic acids and their

Novel compounds of the formula ##STR1## wherein A is selected from the group consisting of nitrogen and .dbd.CH--, G is selected from the group consisting of ##STR2## Z is selected from the group consisting of hydrogen and alkyl of 1 to 5 carbon atoms or taken with Y forms a carbon-nitrogen or carbon-carbon bond, Z' is selected from the group consisting of hydrogen and halogen, Y is hydrogen, or taken with Z is a carbon-nitrogen or carbon-carbon bond or taken with X is .dbd.O and X is hydrogen or taken with Y is .dbd.O, R is selected from the group consisting of hydroxymethyl, formyl, tetrazol-5-yl, N-(tetrazol-5-yl) carbamoyl, aminomethyl and carbamoyl, R.sub.1 is selected from the group consisting of hydrogen, halogen and alkoxy of 1 to 5 carbon atoms and its non-toxic, pharmaceutically acceptable acid addition salts having antiallergic activity and their preparation.

Imidazoquinoxalines and pyrroloquinoxalines

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 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.

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.

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Cirencester, United Kingdom

David A Rowlands