Societe Cortial, S.a.

Laboratoires Sarget

Societe Cortial

Henri Pontagnier

Claude Feniou

Gisele Prat

Marie-Helene Creuzet

Francoise Guichard

Jacqueline Mosser

Guillaume Le Baut

Louis Sparfel

Christian Jarry

Henri Combier

Chantal Boyer

Michel Laguerre

Christian Courtiol

Marie-H/e/ L/e/ Creuzet

Gis/e/ Le Prat

Bernadette Rezzonico

Brigitte Lacourt

Jean C Colleter

Micheline Grignon

A compound with alpha 1-blocking activity having the formula: ##STR1## wherein R.sub.1 is --H, --CH.sub.3 or --COCH.sub.3 ; R.sub.2 is --H or CH.sub.3 ; and R.sub.3 is ##STR2## wherein .SIGMA. is --H or one or more substituents selected from the group consisting of halogen, --OH and --OCH.sub.3 ; or a pharmaceutically acceptable salt thereof.

Derivatives of 4-aminoethoxy-5-isopropyl-2-methylbenzenes: methods of

The present invention relates to a novel method of preparing D-ribose. In this method, a 1,5-di-O-alkyl derivative of D-xylofuranose is prepared; the hydroxyl groups in positions 2 and 3 are each substituted by a group which is preferably mesyl (CH.sub.3 SO.sub.2) or methyldithiocarbonyl, CH.sub.3 SC(=S); the 2,3-unsaturated derivative is prepared; and D-ribose is finally obtained by cis-hydoxylation of the carbon-carbon double bond, followed by acid hydrolysis of the resulting 1,5-O-dialkyl derivative.

Method of preparing D-ribose

The present invention to pharmaceutical composition comprising an effective amount of products having the structural formula ##STR1## where R.sub.1 is a hydrogen atom or a lower alkyl group such as methyl or ethyl,

N-substituted 2-aminomethylene-1,3-indanediones for treating arterial

Therapeutic application of N-substituted

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

A compound having the formula: ##STR1## wherein n is an integer between 6 and 11, inclusive; or the pharmaceutically-acceptable salts thereof. The compounds of the present invention and compositions containing the same are useful as antimicrobial agents in the disinfection of healthy or injured skin or mucous or serous membranes.

1-cycloalkylamino-3-t-butylamino-2-propanols, a method of preparing the

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

This invention relates to new N-(5-aminomethyl-2-oxazoline-2-yl)-N'-phenylureas, the method for producing them and their application in therapy, particularly in treating convulsions, rhythm troubles, ulcerous disorders or inflammatory or edematous conditions. The products of this invention have the general formula: ##STR1## wherein R.sub.1 and R.sub.2 independently represent an alkyl radical of C.sub.1 to C.sub.4, or a carbocyclic alkyl radical having 3 or less rings, or a carbocyclic radical having 3 or less rings; R.sub.1 and R.sub.2 can form, with the nitrogen atom to which they are attached, a 4 to 7 member heterocycle containing 1 or 2 nitrogen atoms and 1 or 0 oxygen atoms, said heterocycle can be substituted by R with R being an alkyl radical of C.sub.1 to C.sub.4, allyl, benzyl, pyridyl, phenyl substituted or not by one or more substituents such as halogen, trihalomethyl, alkyl of C.sub.1 to C.sub.4, hydroxy, or alkoxy having a C.sub.1 to C.sub.4 alkyl radical.

N-(5-aminomethyl-2-oxazolin-2-yl)-N'-phenylureas, compositions and use

This invention relates to new 2-amino-5-aminomethyl-2-oxazolines, the method of preparing them, and their pharmacological properties making possible their application in cardiovascular, psychotropic, antiinflammatory antiallergic, antihistamine, antiH.sub.2 therapy. These new products have the general formula: ##STR1## wherein R.sub.1 and R.sub.2 independently represent an alkyl radical of C.sub.1 to C.sub.4, or a carbocyclic alkyl radical having less than 4 rings, or a carbocyclic radical having less than 4 rings; R.sub.1 and R.sub.2 can form, with the nitrogen atom to which they are attached, a 4 to 7 member heterocycle containing 1 or 2 nitrogen atoms, and either 1 or 0 oxygen atoms. This heterocycle can be substituted by R with R being a lower alkyl, allyl, benzyl, pyridyl, phenyl substituted or not by one or more substituents such as halogen, trifluoromethyl, methyl, methoxy, hydroxy.

2-Amino-5-aminomethyl-2-oxazolines, compositions and use

The present invention concerns a new triterpenic saponin derived from caulophyllogenin, the process for extracting it from varieties of Chrysanthellum, and its therapeutic use. This saponin is characterized as being the ester of O-.beta.-D-glucosyl-3.beta.-caulophyllogenin and an oligosaccharide comprising two units of L-rhamnose and two units of D-xylose. It is extracted from vegetable matter and purified using pressurized liquid preparative chromatographic techniques. This saponin is useful in human and veterinary therapeutics in phlebology, rheumatology, and traumatology.

Triterpenic saponin having pharmacological potency

New compounds of the general formula: ##STR1## wherein R.sub.1 is an unsaturated heterocyclic radical selected from the group consisting of: ##STR2## wherein R.sub.2 is H or one substituent selected from the group consisting of CH.sub.3, halogen, and nitro, are useful as anti-inflammatories and in the oral treatment of diabetes.

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Pessac, France

Henri Pontagnier