Rhone-poulenc Industries

Rhone-poulenc S.a.

Claude Jeanmart

Claude Cotrel

Mayer Naoum Messer

Michel Barreau

Andre Leger

Cornel Crisan

Francois Debarre

Pierre Edouard Simon

Heterocyclic compounds of the formula: ##STR1## wherein the pyrroline ring and the symbols R.sub.1 and R.sub.2 together form an isoindoline, 6,7-dihydro-5H-pyrrolo-[3,4-b]pyrazine, 2,3,6,7-tetrahydro-5H-1,4-oxathiino-[2,3-c]pyrrole or 2,3,6,7-tetrahydro-5H-1,4-dithiino-[2,3-c]pyrrole nucleus, Het represents an optionally substituted pyrid-2-yl, quinol-2-yl or 1,8-naphthyridin-2-yl radical, Z represents oxygen or sulphur and R represents hydrogen, alkyl or halo-substituted alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, optionally substituted phenyl, phenylalkyl, the phenyl ring of which may optionally be substituted, phenylalkenyl, the phenyl ring of which may optionally be substituted, or R represents a 5- or 6-membered heterocyclic radical containing one or two hetero-atoms selected from nitrogen, oxygen and sulphur, and, when the pyrroline ring and the symbols R.sub.1 and R.sub.2 together form an isoindoline nucleus, the residue of the isoindoline nucleus represented by R.sub.1 and R.sub.2 may optionally be substituted, possess pharmacological properties, and are especially useful as tranquillizers, anti-convulsant agents, decontracturants and agents to produce hypnosis.

Heterocyclic compounds

1,2-Dithiole derivatives of the formula: ##STR1## wherein Het represents a pyridazin-3-yl radical, or a pyrimidin-2-yl, -4-yl or -5-yl radical, each such radical being optionally substituted by a halogen atom or by an alkyl radical of 1 through 4 carbon atoms, an alkoxy radical of 1 through 4 carbon atoms, the mercapto radical, an alkylthio radical of 1 through 4 carbon atoms or a dialkylamino group having 1 through 4 carbon atoms in each alkyl radical, are new compounds useful in the treatment of bilharziasis and amoebiasis.

Pyrimidinyl-1,2-dithiole compounds and anti-bilharzia compositions

1,2-Dithiole derivatives of the formula: ##STR1## wherein Het represents an aromatic heterocyclic radical with six atoms in the ring two of which are nitrogen atoms, the heterocyclic radical optionally carrying a single substituent selected from halogen, alkyl, alkoxy, mercapto, alkylthio, dialkylamino, pyrrolidin-1-yl, piperidino, morpholino and 4-alkylpiperazin-1-yl, and R represents halogen, alkyl (optionally substituted by alkoxycarbonyl), carboxy, alkoxycarbonyl, carbamoyl, N-alkylcarbamoyl or a group R.sub.1 --CH(OH)-- in which R.sub.1 represents hydrogen or alkyl, the said alkyl, alkoxy and alkylthio radicals or alkyl or alkoxy moieties containing 1 to 4 carbon atoms except in the case of R.sub.1 which contains 1 to 3 carbon atoms when an alkyl radical, are new compounds useful in the treatment of bilharziasis.

1,2-Dithiole pyrimidines

1,2-Dithiole derivatives

Heterocyclic compounds of the formula: ##STR1## wherein the pyrroline ring and the symbols X.sub.1 and X.sub.2 together form an unsubstituted or substituted isoindoline nucleus, or a 6,7-dihydro-5H-pyrrolo[3,4-b]pyrazine, 6,7-dihydro-5H-pyrrolo[3,4-b]pyridine or 2,3,6,7-tetrahydro-5H-1,4-oxathiino[2,3-c]pyrrole nucleus, the 1,8-naphthyridin-2-yl nucleus is unsubstituted or substituted, and the grouping --NR.sub.1 R.sub.2 is an amino or substituted amino group, are new compounds which are active as tranquillizers, hypnotics, anti-convulsant agents and anti-spasmodics.

Naphtyridine derivatives

Compounds of the formula: ##STR1## wherein A represents a phenyl, pyrid-2-yl, quinol-2-yl or 1,8-naphthyridin-2-yl radical, each such radical being optionally substituted by a halogen atom, an alkyl radical of 1 through 4 carbon atoms, an alkoxy radical of 1 through 4 carbon atoms, the cyano or nitro radical, and R represents hydrogen or an alkyl radical of 1 through 4 carbon atoms, an alkenyl radical of 2 through 4 carbon atoms or an alkanoyl radical of 1 through 4 carbon atoms, possess pharmacological properties and are particularly active as tranquillizers, anti-convulsant agents, decontracturants and agents to produce hypnosis.

Derivatives of dithiepino[1,4][2,3-C]pyrrole

1,2-Dithiole derivatives of the formula: ##STR1## WHEREIN Het represents an aromatic heterocyclic radical with six atoms in the ring two of which are nitrogen atoms, the heterocyclic radical optionally carrying a single substituent selected from halogen, alkyl, alkoxy, mercapto, alkylthio, dialkylamino, pyrrolidin-1-yl, piperidino, morpholino and 4-alkylpiperazin-1-yl and R represents halogen, alkyl (optionally substituted by alkoxycarbonyl), carboxy, alkoxycarbonyl, carbamoyl, N-alkylcarbamoyl or a group R.sub.1 --C(OH)-- in which R.sub.1 represents hydrogen or alkyl, the said alkyl, alkoxy and alkylthio radicals or alkyl or alkoxy moieties containing 1 to 4 carbon atoms except in the case of R.sub.1 which contains 1 to 3 carbon atoms when an alkyl radical, are new compounds useful in the treatment of bilharziasis.

1,2-Dithiole derivatives of the formula: ##STR1## wherein Het represents a pyridazin-3-yl radical, or a pyrimidin-2-yl, -4-yl or -5-yl radical, each such radical being optionally substituted by a halogen atom or by an alkyl radical of 1 through 4 carbon atoms, an alkoxy radical of 1 through 4 carbon atoms, the mercapto radical, an alkylthio radical of 1 through 4 carbon atoms or a dialkylamino group having 1 through 4 carbon atoms in each alkyl radical, are new compounds useful in the treatment of bilharziasis and amoebiases.

Derivatives of 1,2-dithiole and anti-bilharzia compositions thereof

Naphthyridine derivatives

1,2-Dithiole derivatives of the formula: ##STR1## wherein X.sub.1, X.sub.2 and X.sub.3 represent hydrogen, alkyl of 1 through 4 carbon atoms or alkoxy of 1 through 4 carbon atoms, at least one of X.sub.1, X.sub.2 and X.sub.3 representing hydrogen, and Y represents sulphur or oxygen or the hydroxyimino radical, are new compounds useful in the treatment of bilharziasis and amoebiasis.

Isoindolin-1-one derivatives substituted on the nitrogen atom in the 2-position by an unsubstituted or substituted phenyl radical or a heterocyclic radical having aromatic characteristics, substituted in the 3-position by a 3-amino(or substituted amino)-2-hydroxy-propoxy group, and optionally substituted in the 5- and/or 6-positions by one or two alkoxy radicals or optionally substituted in the 5- and 6-positions by a methylenedioxy radical, possess pharmacodynamic properties, and are especially useful as antiarrhythmic agents.

Isoindolin-1-one derivatives

Compounds of the formula: ##STR1## wherein one of the symbols =X- represents =N- and the other three each represent a group ##STR2## in which Y represents hydrogen, halogen, alkyl, alkoxy, cyano or nitro, =A- and =A.sub.1 - represent a group =CH- or =N-, =A.sub.1 - representing a group =CH- or =N- when =A- represents =CH- and =A.sub.1 - representing =N- when A represents =N-, Z represents hydrogen, halogen, alkyl, alkoxy or nitro, m represents zero or an integer from 1 to 4, and (i) n represents zero and R represents hydrogen, alkyl, alkenyl, alkynyl, hydroxyalkyl or phenyl, or (ii) n represents 1 and R represents alkyl, hydroxyalkyl or phenyl, are new compounds possessing pharmacological properties; they are particularly active as tranquilizers and anticonvulsant agents.

6-(1,8-Naphthyridin-2-yl)-5-piperazino

1,4-Oxathiino[2,3-c]pyrrole derivatives of the formula: ##STR1## wherein A represents a phenyl, 2-pyridyl, 3-pyridazinyl, 2-quinolyl or naphthyridinyl radical, or a said radical substituted by one or two atoms or radicals selected from halogen, alkyl of 1 through 4 carbon atoms, alkoxy of 1 through 4 carbon atoms and nitro, and R represents alkyl of 1 through 4 carbon atoms, cycloalkyl of 3 through 6 carbon atoms, alkenyl of 2 through 4 carbon atoms or alkynyl of 2 through 4 carbon atoms, possess pharmacological properties, and are especially useful as tranquillizers, anti-convulsant agents, decontracturants, and agents to produce hypnosis.

1,4-Oxathiino[2,3-c]pyrrole derivatives

Compounds of the formula: ##STR1## wherein one of the symbols =X-- represents =N-- and the other three each represent a group ##STR2## in which Y represents hydrogen, halogen, alkyl, alkoxy, cyano or nitro, at least two of the symbols representing hydrogen, Z represents hydrogen, halogen, alkyl, alkoxy, trifluoromethyl or nitro, and (i) n represents zero and R represents hydrogen, alkyl, alkenyl, alkynyl, hydroxyalkyl or phenyl, or (ii) n represents 1 and R represents alkyl, hydroxyalkyl or phenyl, are new compounds possessing pharmacological properties; they are particularly active as tranquilizers and anti-convulsant agents.

Imidazo[2,1-b]thiazoles carrying in the 2-position a phenyl radical unsubstituted or substituted by one or two atoms or radicals selected from halogen atoms and alkyl, alkoxy, alkylthio, dialkylamino, dialkylsulphamoyl, nitro, cyano and trifluoromethyl radicals or carrying in the 2-position a 2-, 3- or 4-pyridyl radical unsubstituted or substituted by an alkyl or alkoxy radical, are new compounds possessing pharmacological properties and useful, in particular, as anti-depressants and psycho-energisers.

Growing community of inventors

Brunoy, France

Claude Jeanmart