Rhone-poulenc Sante

Rhone-poulenc Rorer S.a.

Phone-poulenc Sante

Gerard Taurand

Claude Guyon

Claude Cotrel

Gerard Roussel

Bernard Plau

Claude Garret

Daniel Farge

Jean-Dominique Bourzat

Jean-Marc Paris

New phenothiazine derivatives of general formula (I) in which

Phenothiazine derivatives, their preparation and pharmaceutical

Phenothiazine derivatives of general formula (I), in which R is a linear or branched (1 to 6 C) alkyl radical and R.sub.1 and R.sub.2, which may be identical or different, are linear or branched (1 to 4 C) alkyl radicals or form, with the nitrogen atom to which they are attached, a 4- to 7-membered heterocycle, their isomeric forms and mixtures thereof as well as their addition salts with acids, possess analgesic and diuretic activity. ##STR1##

Analgesic phenothiazine derivatives

Phenothiazine derivatives of formula: ##STR1## in which Y is hydrogen or halogen, R.sub.1 and R.sub.2, which may be identical or different, denote alkyl, cycloalkyl-alkyl, hydroxyalkyl or acetyloxyalkyl radicals or form, together with the nitrogen atom to which they are attached, an optionally substituted, saturated or partially unsaturated 4- to 7-membered heterocycle; and either X is oxygen, sulphur or: N-R.sub.4, R is cycloalkyl, phenyl or --CH.sub.2 R.sub.3, R.sub.3 is H, alkyl (1 to 5 C), alkenyl or alkynyl (2 to 4 C), cycloalkyl (3 to 6 C), phenyl, substituted phenyl or a heterocyclic radical, R.sub.4 is H or --CN, except that X is not oxygen if, simultaneously, R.sub.3 is H or alkyl, R.sub.1 and R.sub.2 are alkyl or NR.sub.1 R.sub.2 forms an unsubstituted heterocycle, and Y is H; or X is: N-R.sub.4 and R.sub.4 forms, with R and the neighbouring atoms, an optionally substituted imidazolyl or imidazolinyl radical or a hexahydrobenzimidazolyl radical, in their isomeric forms and mixtures thereof and their acid addition salts are useful as analgesics and diuretics.

Phenothiazine derivatives of formula ##STR1## in which R represents --NR.sub.1 R.sub.2 in which R.sub.1 and R.sub.2, which may be identical or different, are alkyl, hydroxyalkyl or acetyloxyalkyl radicals, or form, together with the nitrogen atom to which they are attached, a heterocycle containing 4 to 7 members which may be substituted by 1 or 2 alkyl, hydroxyalkyl or acetyloxyalkyl radicals, or R represents --N.sup.+ R.sub.1 R.sub.2 R.sub.3 in which R.sub.1 and R.sub.2 are as defined above and R.sub.3 is alkyl or phenylalkyl, their isomeric forms and their mixtures, and their salts, are useful in the field of antidiarrhetics.

Derivatives of phenothiazine and the compositions which contain them

The invention provides new substituted amides of formula

Amides based on certain 1,8-naphtyridine-2-amines useful as anxiolytics

The invention provides new substituted amides of formula:

Anxiolytic amides derived from certain 1,8-naphthyridine-2-amines

Amides of formula ##STR1## in which either R is 2-quinolyl, substituted phenyl (substituted by Br, 3-Cl, CF.sub.3, alkyloxycarbonyl, 4-dialkylamino), dichlorophenyl, trialkyloxyphenyl, benzyl, styryl, benzoyl or anilino and R' is halogen, phenyl or anilino or R' is phenoxy or 4-chlorophenoxy when R is 2-quinolyl, substituted phenyl, trialkyloxyphenyl, benzyl or styryl or R' is 4-fluoro(or alkyloxy)phenyl when R is 4-trifluoromethyl (or dialkylamino)phenyl, or R' is 3-bromophenyl when R is anilino, or R is phenyl or alkyloxyphenyl and R' is phenyl, 4-chlorophenoxy, anilino or 1-pyrrolidinyl or R' is 2-(or 4-)chlorophenyl, 3-(or 4-)bromophenyl, 4-alkyloxyphenyl or 3,4-dichloro(or dibromo)phenyl when R is phenyl or R is 3-halophenyl and R' is 3-(or 4-)fluorophenyl, 3-(or 4-)bromophenyl, 4-chlorophenyl, 2-(or 3-)-alkyloxyphenyl, 3-alkylphenyl or 3,4-difluoro(dichloro or dibromo)phenyl, the straight-chain or branched alkyl radical containing 1 to 4 carbon atoms each, are useful as immunostimulant agents. The invention also provides processes for their preparation and pharmaceutical compositions containing them.

N-1,8-naphthyridin-2-yl amides useful as immunostimulants

The invention provides novel substituted amides of formula:

N-(1,8-naphthyridin-2-yl) amides and their pharmaceutical use

New derivatives of the general formula (I) in which:

Anti-rheumatic 5-(substituted amino)-1,2-dithiol-3-one compounds and

New compounds of the formula: ##STR1## wherein X.sup..crclbar. is an anion, R is (C.sub.1-7) alkyl [unsubstituted or substituted by hydroxy, carboxy, alkoxycarbonyl, cyano, dialkylamino, alkylcarbonyl, or benzoyl which is unsubstituted or substituted by one or more halogen atoms or radicals selected from alkyl (optionally substituted by one or more halogens), alkoxy, hydroxy, amino, alkylamino, dialkylamino, cyano and nitro, or by a thenoyl radical (which is unsubstituted or substituted by one or more halogens or radicals selected from alkyl, cyano and nitro), or a pyridinecarbonyl, carbamoyl or dialkylcarbamoyl radical (the alkyl radicals of which can form a 5-membered or 6-membered heterocyclic ring) or a pyridyl radical], dialkylcarbamoyl (the alkyl radicals of which can form a 5-membered or 6-membered heterocyclic ring), (C.sub.2-4) alkenyl, (C.sub.2-4) alkynyl, alkoxycarbonyl or a 2-oxotetrahydrofuran-3-yl or 2-oxotetrahydropyran-3-yl ring, and either R.sub.1 and R.sub.2 are phenyl, cycloalkyl, alkyl or phenylalkyl or together form a 5-membered to 7-membered heterocyclic ring, or R.sub.1 is phenyl optionally substituted by one or more halogen atoms or radicals selected from alkyl optionally substituted by one or more halogens, alkoxy, hydroxy, amino, alkylamino, dialkylamino, cyano and nitro, or alternatively is cycloalkyl, alkyl or phenylalkyl, and R.sub.2 is a hydrogen atom, are useful as cytoprotective anti-ulcer agents.

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Creteil, France

Gerard Taurand