Roussel Uclaf

Other

Roussel-ulcaf

Peter D Kennewell

Robert Westwood

David P Kay

Stephen Clements-Jewery

Alan C Barnes

Robert K Smalley

Abdul B Luheshi

Wilfred R Tully

David A Rowlands

Frederick L Parker

Stuart D Jones

A compound selected from the group consisting of a compound of the formula ##STR1## wherein R.sub.1 and R.sub.2 are individually selected from the group consisting of hydrogen, alkyl and hydroxyalkyl of 1 to 5 carbon atoms and amino, n is an integer from 1 to 3, X and X.sub.1 are individually selected from the group consisting of hydrogen and alkyl of 1 to 3 carbon atoms or taken together with the carbon atom to which they are attached are ##STR2## Y is --O-- or --S--, R.sub.3 is alkyl of 1 to 3 carbon atoms or aryl of 6 to 8 carbon atoms, ##STR3## is selected from the group consisting of ##STR4## R.sub.4 and R.sub.5 are individually aryl unsubstituted or substituted with at least one member of the group consisting of halogen, --NO.sub.2 and alkyl and alkoxy of 1 to 3 carbon atoms and non-toxic, pharmaceutically acceptable salts thereof with acids and bases having cyclooxygenase inhibiting and antibiotic acitvity.

Process for the preparation of azabicyclo compounds

A compound selected from the group consisting of a compound of the formula ##STR1## wherein R.sub.1 and R.sub.2 are individually selected from the group consisting of hydrogen, alkyl and hydroxyalkyl of 1 to 5 carbon atoms and amino, n is an integer from 1 to 3, X and X.sub.1 are individually selected from the group consisting of hydrogen and alkyl of 1 to 3 carbon atoms or taken together with the carbon atom to which they are attached are &gt;C.dbd.O Y is --O-- or --S--, R.sub.3 is alkyl of 1 to 3 carbon atoms or aryl of 6 to 8 carbon atoms, ##STR2## is selected from the group consisting of ##STR3## R.sub.4 and R.sub.5 are individually aryl unsubstituted or substituted with at least one member of the group consisting of halogen, --NO.sub.2 and alkyl and alkoxy of 1 to 3 carbon atoms and non-toxic, pharmaceutically acceptable salts thereof with acids and bases having cyclooxygenase inhibiting and antibiotic activity.

Azabicyclo compounds

Novel alkylaminoamides of the formula ##STR1## wherein R is selected from the group consisting of (a) alkyl of 1 to 8 carbon atoms, (b) cycloalkyl of 3 to 7 carbon atoms optionally substituted with phenyl, (c) aryl of 6 to 14 carbon atoms optionally substituted with at least one member of the group consisting of halogen, --CF.sub.3, alkyl of 1 to 6 carbon atoms, --NO.sub.2 and cycloalkyl of 3 to 7 carbon atoms, (d) aralkyl of 7 to 14 carbon atoms and (e) ##STR2## Z is --(CH.sub.2).sub.n -- optionally substituted by an alkyl of 1 to 6 carbon atoms, n is an integer from 1 to 6, Y is --(CH.sub.2).sub.n -- or ##STR3## and their non-toxic, pharmaceutically acceptable acid addition salts having remarkable anti-oedematous and anti-inflammatory activity.

Alkylaminoamide compounds

A compound selected from the group consisting of 8-phenylthio-tetrahydroquinolines of the formula ##STR1## wherein R.sub.1 and R.sub.2 are individually selected from the group consisting of hydrogen, halogen, alkyl of 1 to 6 carbon atoms optionally substituted with hydroxy, alkoxy of 1 to 6 carbon atoms, alkanoyloxy of 1 to 6 carbon atoms, alkoxycarbonyl of 2 to 6 carbon atoms, --OH, --NO.sub.2, --NH.sub.2, --COOH, --CN and aminosulfonyl or when R.sub.1 and R.sub.2 are on adjacent carbon atoms form with the said carbon atoms phenyl and their non-toxic, pharmaceutically acceptable acid addition salts having anti-allergic activity.

8-phenylthio-tetrahydroquinolines and anti-allergic use thereof

A compound selected from the group consisting of a compound of the formula ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are individually selected from the group consisting of hydrogen, halogen and alkyl and alkoxy of 1 to 6 carbon atoms and their non-toxic, pharmaceutically acceptable acid addition salts having anti-allergic and anti-inflammatory properties.

Novel benzimidazolyl-thiomethyl-benzothiazoles

Novel alkylaminoamides of the formula ##STR1## wherein R is selected from the group consisting of (a) alkyl of 1 to 8 carbon atoms, (b) cycloalkyl of 3 to 7 carbon atoms optionally substituted with phenyl, (c) aryl of 6 to 14 carbon atoms optionally substituted with at least one member of the group consisting of halogen, --CF.sub.3, alkyl of 1 to 6 carbon atoms, -- NO.sub.2 and cycloalkyl of 3 to 7 carbon atoms, (d) aralkyl of 7 to 14 carbon atoms and (e) ##STR2## Z is --(CH.sub.2).sub.n -- optionally substituted by an alkyl of 1 to 6 carbon atoms, n is an integer from 1 to 6, Y is --(CH.sub.2).sub.n -- or ##STR3## and their non-toxic, pharmaceutically acceptable acid addition salts having remarkable anti-oedematous and anti-inflammatory activity.

Hexahydrocarbazole containing alkylaminoamide compounds, pharmaceutical

Novel 8-thiotetrahydroquinolines of the formula ##STR1## wherein X is selected from the group consisting of ##STR2## Alk is alkyl of 1 to 6 carbon atoms, R.sub.1 and R.sub.2 are Alk individually selected from the group consisting of hydrogen and aryl or taken together with the carbon atoms to which they are attached form a phenyl optionally substituted with at least one member of the group consisting of alkyl, alkoxy and alkylthio of 1 to 6 carbon atoms, halogen, ##STR3## and Alk' is alkyl of 1 to 6 carbon atoms and their non-toxic, pharmaceutically acceptable acid addition salts having antiallergic activity and their preparation.

8[2-(imidazolyl)thio] and

Novel 1,2,4-thiadiazines of the formula ##STR1## wherein R.sub.3 is selected from the group consisting of hydrogen, --OH, --CF.sub.3, alkyl, alkoxy and alkylthio of 1 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms optionally substituted with alkyl of 1 to 6 carbon atoms and ##STR2## R.sub.1 and R.sub.2 are individually selected from the group consisting of hydrogen and alkyl of 1 to 3 carbon atoms or taken together with the nitrogen to which they are attached form a saturated heterocycle of 4 to 8 carbon atoms optionally containing a heteroatom of the group consisting of --O--, --S-- and ##STR3## and R' is hydrogen or alkyl of 1 to 3 carbon atoms, R.sub.5 is ##STR4## R.sub.4 is selected from the group consisting of hydrogen, halogen and alkyl and alkoxy of 1 to 3 carbon atoms, R.sub.6 is selected from the group consisting of hydrogen, halogen and alkyl of 1 to 3 carbon atoms with the proviso that R.sub.6 may represent halogen only when R.sub.3 is hydrogen, --OH, alkyl and alkoxy of 1 to 6 carbon atoms or cycloalkyl of 3 to 6 carbon atoms optionally substituted with alkyl of 1 to 6 carbon atoms and their non-toxic, pharmaceutically acceptable acid addition salts having a remarkable anxiolytic activity and novel intermediates.

1,2,4-thiadiazines

A compound selected from the group consisting of pyrimido quinoxalines of the formula ##STR1## wherein R.sub.1 represents an alkoxy radical of 1 to 5 carbon atoms and R is selected from the group consisting of hydrogen, alkyl of 1 to 5 carbon atoms, --COR.sub.A, --CHO and ##STR2## R.sub.A is selected from the group consisting of alkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, alkoxy of 1 to 5 carbon atoms and phenyl optionally substituted with at least one member of the group consisting of halogen, --NO.sub.2 and alkoxy of 1 to 3 carbon atoms and their non-toxic, pharmaceutically acceptable acid addition salts having antiallergic properties.

Pyrimido-quinoxalines having antiallergic properties

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

A novel process for the preparation of xanthane-2-carboxylic acids of the formula ##STR1## wherein R is selected from the group consisting of hydrogen and alkyl of 1 to 9 carbon atoms and R.sub.1 is alkyl of 1 to 5 carbon atoms which possess an antiallergic activity and are particularly useful for treating asthma and asthmatic form bronchitisis of allergic origin.

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Swindon, United Kingdom

Peter D Kennewell