Roussel Uclaf

Daniel Frechet

Lucien Nedelec

Claude Dumont

Michel Fortin

Francois Clemence

Gilles Hamon

Simone Jouquey

Jean-Paul Vevert

Anne-Marie Moura

Neil L Brown

Guy Plassard

Peter F Hunt

Marie-Helene Kannengiesser

Jean Vacher

Jean-Cyr Gaignault

Imidazoles of the formula ##STR1## and their non-toxic, pharmaceutically acceptable salts with acids and bases having an antagonistic activity against angiotensin II receptors.

Imidazoles and their salts having antagonistic activity to angiotesin II

Imidazole derivatives having angiotensin II receptor antagonistic

Novel imidazoles of the formula ##STR1## and their non-toxic, pharmaceutically acceptable salts with acids and bases having an antagonistic activity against angiotensin II receptors.

Benzimidazole compounds

Novel all possible enantiomeric and diastereoisomeric forms of compounds of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of hydrogen, halogen, alkyl and alkoxy of 1 to 5 carbon atoms, --No.sub.2, --NH.sub.2 and mono and dialkylamino of 1 to 5 alkyl carbon atoms, A and B have the trans configuration, one of A and B being ##STR2## R.sub.2 is hydrogen or alkyl of 1 to 5 carbon atoms, Z is --(CH.sub.2).sub.n2, n.sub.2 being an integer from 0 to 5 or branched alkylene of 2 to 8 carbon atoms or --CH.sub.2 --O--, Y is selected from the group consisting of phenyl, naphthyl, indenyl, heteromonocycle of 5 to 6 ring atoms and heterobicycle, all optionally having at least one substituent and the other of A and B is ##STR3## R.sub.4 and R.sub.5 individually being selected from the group consisting of hydrogen and alkyl of 1 to 5 carbon atoms or taken together with the nitrogen to which they are attached form a 5 to 6 ring heterocycle optionally containing a heteroatom selected from the group consisting of --O--, --S-- and --NH-- and their non-toxic, pharmaceutically acceptable acid addition salts having central analgesic properties and a strong affinity for opiate receptors.

Benzocyclohexanes and benzocycloheptanes useful as analgesics

Novel enantiomeric and diasteroisomeric forms of tetrahydropyridines of the formula ##STR1## wherein n.sub.1 is 0 or 2, A is selected from the group consisting of --(CH.sub.2).sub.n2 -- and alkylene substituted with alkyl having a total of 2 to 8 carbon atoms and n.sub.2 is 0 to 5, Z is selected from the group consisting of phenyl, naphthyl, indenyl, heteromonocycle of 5 to 6 ring members and heterobicycle, each optionally substituted with at least one substituent and their non-toxic, pharmaceutically acceptable acid addition salts and quarternary ammonium salts having central analgesic properties as well as diuretic, anti-arrhythmic, anti-cerebral-ischemia and hypotensive properties.

Compositions and method of treating arrythmia with tetrahydropyridines

Novel all possible enantiomeric and diastereoisomeric forms of compounds of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of hydrogen, halogen, alkyl and alkoxy of 1 to 5 carbon atoms, --NO.sub.2, --NH.sub.2 and mono and dialkylamino of 1 to 5 alkyl carbon atoms, n is 1 or 2, A and B have the trans configuration, one of A and B being ##STR2## R.sub.2 is hydrogen or alkyl of 1 to 5 carbon atoms, Z is --(CH.sub.2)--.sub.n2, n.sub.2 being an integer from 0 to 5 or branched alkylene of 2 to 8 carbon atoms or --CH.sub.2 --O--, Y is selected from the group consisting of phenyl, naphthyl, indenyl, heteromonocycle of 5 to 6 ring atoms and heterobicycle, all optionally having at least one substituent and the other of A and B is ##STR3## R.sub.4 and R.sub.5 individually being selected from the group consisting of hydrogen and alkyl of 1 to 5 carbon atoms or taken together with the nitrogen to which they are attached form a 5 to 6 ring heterocycle optionally containing a heteroatom selected from the group consisting of --O--, --S-- and --NH-- with the proviso 1) A is ##STR4## wherein R.sub.4 l and R.sub.5 have the above definitions and B is ##STR5## wherein R.sub.2, Z and Y have the above definition or 2) Z is --(CH.sub.2).sub.n2 -- and n.sub.2 is 0,2,3,4 or 5 or branched alkylene of 2 to 8 carbon atoms or --CH.sub.2 O-- yr 3) Y is phenyl substituted with at least one member of the group consisting of alkyl of 1 to 5 carbon atoms, alkoxy of 2 to 5 carbon atoms, --NH.sub.2 and mono and dialkylamino or 4) Y is naphthyl, indenyl, heteromonocycle of 5 to 6 ring atoms or heterobicycle, all optionally substituted with at least one substituent, except unsubstituted benzothiophene or 5) R.sub.1 is --NO.sub.2 or 6) R.sub.2 is alkyl of 4 to 5 carbon atoms or 7) R.sub.1 is hydrogen, n.sub.1 is 1, A is ##STR6## Y is selected from the group consisting of 3,4-dimethoxy-phenyl, 4-nitro-phenyl and benzothienyl and B is pyrrolidinyl or 8) R.sub.1 is hydrogen, n.sub.1 is 2, A is ##STR7## Y is selected from the group consisting of 3,4-dimethoxy-phenyl, 3,4-dichloro-phenyl, 4-trifluoromethyl-phenyl, 4-nitro-phenyl and benzothienyl and B is pyrrolidinyl and their non-toxic, pharmaceutically acceptable acid addition salts having central analgesic properties and a strong affinity for opiate receptors.

Benzocyclohexanes and analgesic compositions thereof

A compound selected from the group consisting of all possible isomeric forms, racemic or optically active of a compound of the formula ##STR1## wherein the substituents are defined in the specification, and their non-toxic, pharmaceutically acceptable acid addition salts having antiarhythmic activity.

Benzothiazepines

Novel enantiomeric and diasteroisomeric forms of tetrahydropyridines of the formula ##STR1## wherein n.sub.1 is 0 or 2, A is selected from the group consisting of --(CH.sub.2).sub.n2 -- and alkylene substituted with alkyl having a total of 2 to 8 carbon atoms and n.sub.2 is 0 to 5, Z is selected from the group consisting of phenyl, naphthyl, indenyl, heteromonocycle of 5 to 6 ring members and heterobicycle, each optionally substituted with at least one substituent and their non-toxic, pharmaceutically acceptable acid addition salts and quaternary ammonium salts having central analgesic properties as well as diuretic, anti-arrhythmic, anti-cerebral-ischemia and hypotensive properties.

Novel tetrahydropyridines having analgesic activity

Novel 6-amino-7-hydroxy-4,5,6,7-tetrahydro-imidazo[4,5,l-j-k][1]-benzazepin-2-(1 H)-one derivatives of the formula ##STR1## wherein R is selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms optionally substituted with a hydroxyl, aryl and aryloxy of 6 to 10 carbon atoms, cycloalkyl of 3 to 7 carbon atoms optionally interrupted with a heteroatom optionally substituted with alkyl of 1 to 4 carbon atoms and the wavy lines indicates that the 7-OH and 6-amino have the trans configuration and their non-toxic, pharmaceutically acceptable acid addition salts having remarkable anti-hypertensive and hypotensive activity and vasodilatatory activity and their preparation.

Novel

Novel trans cyclohept[c,d]indolols of the formula ##STR1## wherein R is selected from the group consisting of hydrogen, alkyl of 1 to 5 carbon atoms and optionally substituted aralkyl of 7 to 12 carbon atoms and R.sub.1 is selected from the group consisting of hydrogen, alkyl of 1 to 5 carbon atoms, cycloalkylalkyl of 4 to 7 carbon atoms and optionally substituted aralkyl of 7 to 12 carbon atoms and their non-toxic, pharmaceutically acceptable acid addition salts having hypotensive and antihypertensive activity and a process for their preparation.

5 Amino-3,4,5,6 tetrahydro-1H-[-6-]cyclohept[c,d]indolols and a method

Novel compounds selected from the group consisting of optically active isomers and racemic mixtures of cycloheptindoles of the formula ##STR1## wherein R is selected from the group consisting of hydrogen, alkyl of 1 to 5 carbon atoms and optionally substituted aralkyl of 7 to 12 carbon atoms, R.sub.1 is selected from the group consisting of hydrogen, chlorine and bromine and R.sub.2 is selected from the group consisting of hydrogen, alkyl of 1 to 5 carbon atoms, cycloalkylalkyl of 4 to 7 carbon atoms, alkenyl and alkynyl of 3 to 7 carbon atoms and optionally substituted aralkyl of 7 to 12 carbon atoms and their non-toxic, pharmaceutically acceptable acid addition salts having dopaminergic agonist and antianoxic properties and a process for their preparation and novel intermediates.

Cycloheptindoles, compositions and use

Novel benzene-propanamines of the formula ##STR1## wherein X is selected from the group consisting of hydrogen, chlorine, fluorine and bromine, R.sub.1 is selected from the group consisting of hydrogen and alkyl of 1 to 5 carbon atoms, R.sub.2 is alkyl of 1 to 5 carbon atoms, R.sub.3 is selected from the group consisting of hydrogen, chlorine, bromine, --CF.sub.3, methyl and methoxy when R.sub.4 is nitro and R.sub.3 is selected from the group consisting of amino and acetamido when R.sub.4 is hydrogen and their non-toxic, pharmaceutically acceptable acid addition salts having anorexigenic activity and inhibit serotonine uptake in vivo and in vitro and their preparation.

3-Aryloxy-3-aryl-propaneamines and their method of use

Novel derivatives of 3-(aminoethyl)-phenols of the formula ##STR1## wherein A is a simple bond or alkylene of 1 to 6 carbon atoms and B is selected from the group consisting of aryl, diarylmethyl, cycloalkyl of 3 to 10 carbon atoms and heteroaryl with the proviso that B is not phenyl when A is ethylene and their non-toxic, pharmaceutically acceptable acid addition salts having a dopaminergic activity and their preparation.

Novel 3-(aminoethyl)-phenols

Novel 5H-benzocyclohepten-7-amines of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of hydrogen and methyl, R.sub.2 and R.sub.3 are individually selected from the group consisting of hydrogen, fluorine, chlorine, bromine, nitro, amino, --CF.sub.3 and methoxy, X is selected from the group consisting of hydrogen and halogen, and their non-toxic, pharmaceutically acceptable acid addition salts having remarkable in vivo and in vitro inhibiting properties for the capture of serotonine and their preparation.

Novel 5H-benzocyclohepten-7-amines

N-phenethyl-N-propyl-3,4-dihydroxyphenethylamine and its non-toxic, pharmaceutically acceptable acid addition salts possessing dopaminergic properties.

Growing community of inventors

Paris, France

Daniel Frechet