Roussel Uclaf

Claude Dumont

Lucien Nedelec

Jacques Guillaume

Daniel Frechet

Andre Pierdet

Marie-Helene Kannengiesser

Pierre Henri Derible

Vesperto Torelli

Robert Fournex

Claude Oberlander

Peter F Hunt

Neil L Brown

Jacques Laurent

Guy Plassard

Lucien Ledelec

Novel piperidin-3-yl-indoles of the formula ##STR1## wherein R is selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms and aralkyl of 7 to 12 carbon atoms, X is selected from the group consisting of hydrogen, halogen and alkyl of 1 to 8 carbon atoms or with c is .dbd.0, Y is alkyl of 1 to 8 carbon atoms, c and d form a carbon-carbon bond or c with X is .dbd.0 and d is hydrogen, Z is selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms, hydroxyalkyl of 2 to 8 carbon atoms, cycloalkylalkyl of 4 to 12 carbon atoms, alkenyl and alkynyl of 3 to 8 carbon atoms, aryloxyalkyl of 7 to 12 carbon atoms and aralkyl of 7 to 12 carbon atoms optionally substituted with at least one member of the group consisting of halogen, alkoxy and alkyl of 1 to 4 carbon atoms, --OH, --CF.sub.3, --OCF.sub.3. --NO.sub.2 and --NH.sub.2 and their non-toxic, pharmaceutically acceptable acid addition salts possessing remarkable dopaminergic stimulating properties and antianoxic properties and their preparation.

Dopaminergic stimulating piperidin-3-yl-indoles

Novel 2H-indole-2-ones of the formula ##STR1## wherein R is selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms and aralkyl of 7 to 12 carbon atoms, a and b are both hydrogen or together form a carbon-carbon bond, Z is selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms, hydroxyalkyl of 2 to 8 carbon atoms, aryloxyalkyl of 7 to 12 carbon atoms, cycloalkylalkyl of 4 to 12 carbon atoms, alkenyl and alkynyl of 3 to 8 carbon atoms and aralkyl of 7 to 12 carbon atoms optionally substituted with at least one member of the group consisting of halogen, alkoxy of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms, --OH, --CF.sub.3, --OCF.sub.3, --NO.sub.2 and --NH.sub.2 and their nontoxic, pharmaceutically acceptable acid addition salts having remarkable dopaminergic stimulating and antianoxic properties and their preparation.

Dopaminergic stimulating and antianoxic 4-substituted 2H-indole-2-ones

Novel 3-(1,2,5,6-tetrahydropyridin-3-yl)-phenols of the formula ##STR1## wherein X is selected from the group consisting of hydrogen and an acyl of an organic carboxylic acid of 2 to 7 carbon atoms, Y is selected from the group consisting of hydrogen and --OX, R is selected from the group consisting of hydrogen, alkyl of 1 to 5 carbon atoms optionally substituted with --OH, cycloalkylalkyl of 4 to 7 carbon atoms, alkenyl and alkynyl of 3 to 5 carbon atoms and aralkyl of 7 to 12 carbon atoms optionally substituted on the alkyl with --OH with the proviso that when R is hydrogen, X is hydrogen and their non-toxic, pharmaceutically acceptable acid addition salts having dopaminergic agonist and/or antagonist properties and their preparation.

3-(1,2,5,6-Tetrahydropyridin-3-yl)-phenols and their use in

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 tetrahydro-pyridinyl-indoles of the formula ##STR1## wherein R is selected from the group consisting of amino, trifluoromethyl and methylthio, R.sub.1 and R.sub.2 are individually selected from the group consisting of hydrogen and alkyl of 1 to 3 carbon atoms and their non-toxic, pharmaceutically acceptable acid addition salts having antidepressive, antiparkinson and antiemetic activity and their preparation.

Tetrahydropyridinyl-indoles

Novel indoles of the formula ##STR1## wherein R is selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms and aralkyl of 7 to 12 carbon atoms, X is selected from the group consisting of hydrogen and alkyl of 1 to 18 carbon atoms, Y is selected from the group consisting of hydrogen and halogen, Z is selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms, hydroxy alkyl of 1 to 8 carbon atoms, aryloxyalkyl of 7 to 12 carbon atoms, arylalkyl of 7 to 12 carbon atoms optionally substituted with at least one member of the group consisting of halogen, alkoxy of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms, --OH, --CF.sub.3, --OCF.sub.3, --NO.sub.2 and NH.sub.2, cycloalkylalkyl of 4 to 12 carbon atoms, alkenyl of 3 to 8 carbon atoms and alkynyl of 3 to 8 carbon atoms, and a and b may each be hydrogen or form a double bond or a is hydrogen and b is selected from the group consisting of --OH and alkoxy of 1 to 8 carbon atoms and their non-toxic, pharmaceutically acceptable acid addition salts having dopaminergic stimulating properties optionally accompanied with adrenergic and serotoninergic activity and their preparation and novel intermediates.

Dopaminergically stimulating 4-substituted indoles

Novel tetranydro-pyridinyl-indoles of the formula ##STR1## wherein X is selected from the group consisting of alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 5 carbon atoms, alkynyl of 3 to 5 carbon atoms, cycloalkyl of 5 to 6 carbon atoms, cycloalkylalkyl of 4 to 7 carbon atoms, aralkyl of 7 to 12 carbon atoms, hydroxyalkyl of 2 to 5 carbon atoms and phenoxyalkyl of 1 to 5 alkyl carbon atoms, R is selected from the group consisting of hydrogen, halogen, alkoxy of 1 to 3 carbon atoms, nitro, amino, trifluoromethyl and methylthio, R.sub.1 and R.sub.2 are individually selected from the group consisting of hydrogen and alkyl of 1 to 3 carbon atoms with the proviso that if R is hydrogen, halogen or alkoxy of 1 to 3 carbon atoms, X must be hydroxyalkyl or phenoxyalkyl and their non-toxic, pharmaceutically acceptable acid addition salts having neuroleptic, antipsychotic and antiemetic activity and their preparation.

Antipsychotic tetrahydropyridinyl-indoles, compositions and method of use

Novel indolobenzoxazines 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, R.sub.2 ' is selected from the group consisting of hydrogen, optionally substituted 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 the dotted line between 5 and 5a indicates the optional presence of a double bond and their non-toxic, pharmaceutically acceptable acid addition salts having hypotensive, antihypertensive and dopaminergic agonist properties and a process for their preparation.

Indolobenzoxazines

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 tetrahydropyridinyl indoles of the formula ##STR1## wherein R' is selected from the group consisting of hydrogen, halogen and alkoxy of 1 to 3 carbon atoms, R.sub.1 and R.sub.2 are individually selected from the group consisting of hydrogen and alkyl of 1 to 3 carbon atoms and X' is selected from the group consisting of alkyl of 1 to 6 carbon atoms, cycloalkyl of 4 to 7 carbon atoms, alkenyl and alkynyl of 2 to 5 carbon atoms and aralkyl of 7 to 12 carbon atoms with the proviso that when X' is methyl, at least one of R', R.sub.1 and R.sub.2 contain more than one carbon atom and when X' is benzyl, at least one of R', R.sub.1 and R.sub.2 must not be hydrogen and their non-toxic, pharmaceutically acceptable acid addition salts having antidepressive and neuroleptic properties as well as antiemetic properties.

Tetrahydropyridinyl indoles

Novel m-trifluoromethylphenyl-piperidines of the formula ##STR1## wherein R is selected from the group consisting of hydrogen, branched or straight chain alkyl of 1 to 5 carbon atoms, alkenyl of 3 to 5 carbon atoms, alkynyl of 3 to 5 carbon atoms and phenyl alkyl of 1 to 3 alkyl carbon atoms and their non-toxic, pharmaceutically acceptable acid addition salts having antidepressive, anorexigenic and antiparkinsonian activity and their preparation and novel intermediates formed therein.

Method for using m-trifluoromethylphenyl-piperidines

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

A novel process for the preparation of piperidylindoles of the formula ##STR1## wherein R is selected from the group consisting of hydrogen and alkyl of 1 to 3 carbon atoms and X is selected from the group consisting of hydrogen, nitro, fluorine, bromine, chlorine and alkoxy of 1 to 3 carbon atoms and their non-toxic, pharmaceutically acceptable acid addition salts thereof by reacting an indole of the formula ##STR2## with 4-piperidone hydrochloride in an alkaline medium to obtain the compound of formula I which is optionally salified and the novel product, 5-nitro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole and its non-toxic, pharmaceutically acceptable acid addition salts.

Process for preparation of piperidyl-indoles

Novel 4H-thieno-[3,2-b][1]-benzazepines of the formula ##STR1## wherein R, R.sub.1 and R.sub.2 are individually selected from the group consisting of hydrogen and halogen, X and Y are hydrogen or together form a carbon-carbon double bond, p is 2 or 3 and A is selected from the group consisting of alkyl of 1 to 5 carbon atoms and hydroxyalkyl of 2 to 5 carbon atoms and their non-toxic, pharmaceutically acceptable acid addition salts having neuro sedative and antihistaminic properties and their preparation and intermediates therefor.

Growing community of inventors

Nogent-Sur-Marne, France

Claude Dumont