Roussel Uclaf

Neil L Brown

Francois Clemence

Lucien Nedelec

Daniel Frechet

Guy Plassard

Jacques Guillaume

Claude Dumont

Novel ethenylphenol indoles of the formula ##STR1## wherein R and R.sub.1 are individually selected from the group consisting of hydrogen, alkyl of 1 to 5 carbon atoms, cycloalkyl of 3 to 7 carbon atoms, cycloalkylalkyl of 4 to 7 carbon atoms and aralkyl of 7 to 12 carbon atoms optionally substituted with 1 to 3 members of the group consisting of halogen, methyl, ethyl, methoxy, ethoxy, methylthio, --CF.sub.3, --NH.sub.2 and --NO.sub.2 or R and R.sub.1 together with the nitrogen atom form an optionally unsaturated heterocycle optionally containing a second heteroatom selected from the group consisting of --O--, --S-- and ##STR2## R' is hydrogen or alkyl of 1 to 5 carbon atoms, a together with X is .dbd.0 and b is hydrogen or a together with b is a carbon-carbon bond and X is hydrogen, the dotted line indicates the possibility of a double bond with the compounds having the trans configuration if a double bond, A is selected from the group consisting of ##STR3## and --(CH.sub.2).sub.n --, n is 2,3,4 or 5, R.sub.2 is selected from the group consisting of hydrogen and alkyl of 1 to 5 carbon atoms with the proviso that R and R.sub.1 are not both hydrogen when A is ##STR4## and their non-toxic, pharmaceutically acceptable acid addition salts having anti-arrhythmic and anti hypertensive properties and the property of blocking slow calcium-sodium channels and novel intermediates.

Ethenylphenol-indoles having antiarythmic utility

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 4-(1H-indol-3-yl)-.alpha.-methyl-piperidine-1-ethanol derivatives of the formula ##STR1## wherein R is selected from the group consisting of hydrogen, halogen, alkyl and alkoxy of 1 to 5 carbon atoms, --NO.sub.2, --NH.sub.2, CF.sub.3 -- and CH.sub.3 S--, R.sub.1 is selected from the group consisting of hydrogen and alkyl of 1 to 5 carbon atoms, R.sub.2 is selected from the group consisting of hydrogen, alkyl of 1 to 5 carbon atoms and --OH, Ar is selected from the group consisting of optionally substituted aryl and heteroaryl, the dotted line indicates the optional presence of a double bond and their non-toxic, pharmaceutically acceptable acid addition salts having remarkable antagonistic properties toward calcium ion and antihypertensive activity and certain compounds possess .alpha. and/or .beta.-blocking properties.

4-(1H-indol-3-yl)-.alpha.-methyl-piperidine-1-ethanol derivatives

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.

Growing community of inventors

Paris, France

Neil L Brown