Societe Cortial, S.a.

Laboratoires Sarget

Francoise Guichard

Claude Feniou

Gisele Prat

Henri Pontagnier

Marie-Helene Creuzet

Jacqueline Mosser

Marie-H/e/ L/e/ Creuzet

Gis/e/ Le Prat

Compounds of the formula (I): ##STR1## wherein n is 0 or 1, R.sub.1 is H or a lower alkyl of 1 to 6 carbon atoms, R.sub.2 is an unsubstituted phenyl group or a phenyl group substituted by one or more of the same or different substituents selected from the group consisting of hydroxy, lower alkyl of 1 to 6 carbon atoms, lower alkoxy of 1 to 6 carbon atoms, chloro, fluoro, trifluoromethyl or a 2-, 3- or 4- pyridyl ring, in the form of a free base or a pharmaceutically acceptable acid addition salt thereof. The compounds of the present invention are useful in cardiovascular, antiallergy, psychotropic and hypolipidemic therapy.

Derivatives of 4-(arylpiperazinyl-ethylaminoethoxy) phenol useful for

A compound of the formula ##STR1## wherein R.sub.1 is C.sub.3 -C.sub.6 branched alkyl group, e.g., an isopropyl group or a tert-butyl group, R.sub.2 is a C.sub.1 -C.sub.6 alkoxy group, e.g., a methoxy, an ethoxy or a propoxy group, and X is a CHOH group or a (CH.sub.2).sub.n --group where n=0, 1 or 2 and a process for making this compound are disclosed. This compound is useful in human and veterinary therapeutics.

(Alkoxy-2)phenylpiperazines having alpha-1 and beta blocking properties

This invention relates to 2-(4-phenylpiperazinylethyl)anilines, to methods for preparing them and to their uses in medical therapy. These compounds have the following general formula ##STR1## wherein R.sub.1 represents one or more substituents selected from the group consisting of H, CH.sub.3, CF.sub.3, F, Cl, and OCH.sub.3 ; R.sub.2 and R.sub.3, which may be the same or different, and are selected from the group consisting of H and (C.sub.1 -C.sub.4) alkoxy, or R.sub.2 and R.sub.3 taken together can form a chain selected from the group consisting of --O-- (CH.sub.2).sub.n --O--, wherein n=1 or 2 and --O--CH.sub.2 --O--CH.sub.2 with the proviso that R.sub.1 is not meta CF.sub.3 when R.sub.2 =R.sub.3 =H, and pharmaceutically non-toxic salts thereof. The compounds of this invention are useful in the treatment of allergic and anaphylatic conditions and motion sickness.

2-(4-Phenylpiperazinylethyl) anilines

This invention relates to new products of the general formula ##STR1## where R.sub.1 =H, OH, OCOCH.sub.3, OSO.sub.2 CH.sub.3, branched or unbranched alkyl containing 1 to 5 carbon atoms. R.sub.2 =NHCOR.sub.3, NHCOCH.sub.2 X, NHSO.sub.2 CH.sub.3, N(SO.sub.2 CH.sub.3).sub.2, SO.sub.2 N(CH.sub.3).sub.2, SO.sub.2 NHCH.sub.3, SO.sub.2 NCH.sub.3 CH.sub.2 CH.sub.2 OH, SO.sub.2 NH.sub.2 wherein R.sub.3 is a lower alkyl containing 1 to 4 carbon atoms; and X is NR.sub.4 R.sub.5 or ##STR2## wherein R.sub.4 and R.sub.5 are both independently lower alkyls containing 1 to 4 carbon atoms and ##STR3## is piperidine, pyrrolidine or morpholine. These products can be in the form of pharmaceutically acceptable derivatives such as esters, amides, salts. When R.sub.2 contains an amino function, the product can be in the form of an acid salt. These products are prepared from their methyl esters either by reaction between ##STR4## and paramethoxycarbonylbenzoic acid chloride or by means of derivative I such as R.sub.2 is NH.sub.2. The products of this invention are used in therapy in the prevention and treatment of complications from diabetes or as diuretics.

4'-flavonecarboxylic acids and pharmaceutically acceptable derivatives

This invention relates to quercetin or fisetin derivatives substituted on the oxygen in the 3 position by groups such as lower alkyl, cycloalkyl, methanesulfonyl or paratoluenesulfonyl. The derivatives substituted by methanesulfonyl or paratoluenesulfonyl are obtained from a 3-O-glycoside whose phenol OH groups are blocked in the form of benzoate, and from which the OH in the 3 position is released by the action of concentrated HCl; this OH is esterified by mesityl chloride or paratoluenesulfonic acid chloride, and the benzoate groups are eliminated by soda treatment. The O derivatives substituted by alkyl or cycloakyl are prepared from a suitably substituted acetonitrile or metadiphenol; the resulting derivative reacts with 3,4-dibenzyloxybenzoic acid and the resulting flavone is debenzylated by hydrogenolysis. The derivatives, object of this invention, are useful in preventive or curative therapy of ocular and nervous complications from diabetes and are also useful as hypolipidemic or hypoglycemic agents.

3-hydroxyflavones: their preparation and therapeutic application

This invention relates to 3-(2-(4-phenylpiperazinylethyl)anilino)-isobenzofuranones, their method of preparation and their use in the treatment of conditions such as hypertension, and allergies. These compounds are characterized by the formula: ##STR1## in which R.sub.1 may be one or more substituents located at the ortho, meta, or para positions selected from the group of H, CH.sub.3, CF.sub.3, F, Cl and OCH.sub.3 ; R.sub.2 and R.sub.3 are the same or different and are H or OCH.sub.3. These compounds are in the form of free bases or their pharmaceutically safe salts. They can be obtained by a reaction between a 2-(phenylpiperazinylethyl) aniline and an aromatic aldehyde having an acid function at the ortho position of the carboxaldehyde function. These derivatives are useful for the treatment of hypertension and allergic conditions.

3-(2-(4-phenylpiperazinylethyl)anilino)-isobenzofuranones, their method

Compounds, exhibiting central nervous system activity, of the formula ##STR1## wherein R.sub.1 is phenyl which is unsubstituted or substituted by at least one member selected from the group consisting of halogen, CF.sub.3, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy and COOH, or

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Bordeaux, France

Francoise Guichard