Patents Assigned to Rhone-Poulenc Sante
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Patent number: 4711890Abstract: Compounds of the formula: ##STR1## in which R.sub.1 is C.sub.1-6 alkyl, phenyl, C.sub.3-6 cycloalkyl, phenylalkyl, cycloalkyl-alkyl or ##STR2## R.sub.3 and R.sub.4 being H or alkyl, R.sub.5 being alkenyl or alkynyl, and the sum of the carbon atoms in R.sub.3, R.sub.4 and R.sub.5 being 2 to 5, R.sub.2 is as defined for R.sub.1 and may also represent ##STR3## in which n is 0, 1, 2 or 3, it also being possible for R.sub.1 and R.sub.2 to form, with the nitrogen atom to which they are attached, a 5-, 6- or 7-membered heterocyclic radical which can contain another hetero-atom chosen from O and N and which can carry 1 or 2 substituents, Z is phenyl, pyridinyl, thienyl, thiazol-2-yl or substituted phenyl, X and R.sub.0 are H, halogen, C.sub.1-3 alkyl, C.sub.1-3 alkoxy, nitro or CF.sub.3, A represents N or CH and E represents N or CH, some of which are known compounds, are therapeutically useful compounds useful in the treatment of anxiety states or of pulmonary, renal, circulatory or cardiovascular disorders.Type: GrantFiled: December 22, 1983Date of Patent: December 8, 1987Assignee: Rhone-Poulenc SanteInventors: Marie-Christine Dubroeucq, Gerard R. Le Fur, Christian L. A. Renault
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Patent number: 4705650Abstract: Compounds halogenated in the .alpha.-position to an electron-attracting group of formula ##STR1## in which X denotes a halogen atom, R denotes a hydrogen atom or a hydrocarbon radical or a radical --(CH.sub.2).sub.3 --COOR.sub.1 and Z denotes a radical --CHO, --COR.sub.2, --COOR.sub.3, --CONR.sub.4 R.sub.5, --CN, --SO.sub.2 R.sub.6, --NO.sub.2, --CO--(CH.sub.2)p--COO.sub.1 or --COO(CH.sub.2)p--COOR.sub.1 are made by a halogenating deacylation of a compound of formula ##STR2## in which R' denotes a hydrogen atom or a hydrocarbon radical, R" denotes a methyl radical and Z' denotes a radical --CHO, --COR.sub.2, --COOR.sub.3, --CONR.sub.4 R.sub.5, --CN, --SO.sub.2 R.sub.6 or --NO.sub.2 or R' and R" may form a radical --(CH.sub.2)-- or R' and R" may form a radical --CO--(CH.sub.2)p-- or --COO(CH.sub.2)p--, using an alkali metal alcoholate or an alkali or alkaline-earth metal carbonate and a halogenating agent.Type: GrantFiled: July 10, 1985Date of Patent: November 10, 1987Assignee: Rhone-Poulenc SanteInventors: Gerard Mignani, Didier Morel
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Patent number: 4693849Abstract: Unsaturated compounds of the formula: ##STR1## in which: Q denotes alkyloxycarbonyl, cyano or formyl, R.sub.1 denotes a saturated or unsaturated aliphatic radical, R.sub.2 denotes a hydrogen atom or an alkyl radical, R.sub.3 denotes a hydrogen atom or an aliphatic radical and R.sub.4 denotes a hydrogen atom or a saturated or unsaturated aliphatic radical which may be substituted, are useful as intermediates in the synthesis of vitamin E.Type: GrantFiled: September 13, 1985Date of Patent: September 15, 1987Assignee: Rhone-Poulenc SanteInventors: Gerard Mignani, Didier Morel
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Patent number: 4686309Abstract: The invention provides compounds of formula: ##STR1## in which R=H, halogen, alkyl, alkyloxy, alkythio, NH.sub.2, alkylamino, dialkylamino or CF.sub.3, R.sub.3 =H or alkyl, either R.sub.4 and R.sub.5 =H and R.sub.1 and R.sub.2 =H or alkyl, optionally substituted by alkenyl (2 to 4 C) or alternatively R.sub.1 and R.sub.2 form together a saturated heterocyclic ring containing 4 to 7 ring members and optionally containing another heteroatom such as O, S or N optionally substituted by alkyl, or R.sub.4 =H, R.sub.1 =H or alkyl and R.sub.2 and R.sub.5 together form an alkylene (3 to 4 C) radical and (i) either A=alkyl or phenyl which is unsubstituted or substituted by one or two substituents chosen from halogen, alkyl, alkyloxy, alkylthio, NH.sub.2, alkylamino, dialkylamino, NO.sub.2 or CF.sub.3 or alternatively A=pyridyl, benzyl or cycloalkyl (3 to 6C), Y=S, SO or SO.sub.2 or a radical: ##STR2## in which R.sub.6 =H or alkyl and R.sub.Type: GrantFiled: February 15, 1985Date of Patent: August 11, 1987Assignee: Rhone-Poulenc SanteInventors: Jean-Claude Barriere, Jean-Pierre Corbet, Claude Cotrel, Daniel Farge, Jean-Marc Paris
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Patent number: 4684613Abstract: A device for automatically carrying out the withdrawal and deposition of core samples of semi-solid media in which one or more hollow punches are mounted for movement in three mutually perpendicular directions, so that the punch can be brought above and lowered into the media, a vacuum applied to suck the media into a chamber in the punch, the punch then being raised and moved to a position above a second media, the vacuum then being removed and compressed air applied after the punch has been lowered over the other media, thereby to push the sample removed from the first media from the punch. The operations can all be controlled automatically.Type: GrantFiled: April 19, 1985Date of Patent: August 4, 1987Assignee: Rhone-Poulenc SanteInventors: Genevieve C. Barrere, Marie-Helene Beydon, Lionel Drugeault, Jean-Pierre Vasseur
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Patent number: 4684658Abstract: The invention provides novel pyrrole derivatives of formula: ##STR1## in which R'=H, alkyl or phenyl optionally substituted by halogen, alkyl, alkyloxy or alkylthio, Z=0 or S, p=0 or 1, andeither A is a heterocyclic ring such that it forms, with pyrrole, a 1H,3H-pyrrolo[1,2-c]thiazole, 2,3-dihydro-1H-pyrrolizine optionally substituted by OH, 5,6,7,8-tetrahydroindolizine, 1,2-dihydro-4H-pyrrolo[1,2-c]-1,3-thiazine, 2,3-dihydropyrrolo[2,1-b]thiazole, 1H,3H-pyrrolo[1,2-c]oxazole, 1,2-dihydro-4H-pyrrolo]1,2-c]-1,3-oxazine or 2,3-dihydropyrrolo[2,1-b]oxazole ring system, n=0 or 1, Het=3-pyridyl or 5-thiazolyl, and(1) either R=H, halogen, alkyl or phenyl optionally substituted by halogen, alkyloxy or alkylthio and Y=alkyl or phenyl optionally substituted by halogen, alkyl, alkyloxy or alkylthio, or Y=--NR.sub.1 R.sub.2 with:either R.sub.1 =H and R.sub.2 =unsubstituted alkyl, cycloalkyl (C.sub.3 -C.sub.6), alkenyl (C.sub.2 -C.sub.4), alkynyl (C.sub.3 -C.sub.Type: GrantFiled: December 20, 1984Date of Patent: August 4, 1987Assignee: Rhone-Poulenc SanteInventors: Jean-Louis Fabre, Daniel Farge, Claude James, Daniel Lave
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Patent number: 4684652Abstract: Compounds of the formula: ##STR1## in which R.sub.1 is C.sub.1-6 alkyl, phenyl, C.sub.3-6 cycloalkyl, phenylalkyl, cycloalkyl-alkyl or ##STR2## R.sub.3 and R.sub.4 being H or alkyl, R.sub.5 being alkenyl or alkynyl, and the sum of the carbon atoms in R.sub.3, R.sub.4 and R.sub.5 being 2 to 5, R.sub.2 is as defined for R.sub.1 and may also represent ##STR3## in which n is 0, 1, 2 or 3, it also being possible for R.sub.1 and R.sub.2 to form, with the nitrogen atom to which they are attached, a 5-, 6- or 7-membered heterocyclic radical which can contain another hetero-atom chosen from O and N and which can carry 1 or 2 substituents, Z is phenyl, pyridinyl, thienyl, thiazol-2-yl or substituted phenyl, X and R.sub.0 are H, halogen, C.sub.1-3 alkyl, C.sub.1-3 alkoxy, nitro or CF.sub.3, A represents N or CH and E represents N or CH, some of which are known compounds, are therapeutically useful compounds useful in the treatment of anxiety states or of pulmonary, renal, circulatory or cardiovascular disorders.Type: GrantFiled: August 8, 1985Date of Patent: August 4, 1987Assignee: Rhone-Poulenc SanteInventors: Marie-Christine Dubroeucq, Gerard R. Le Fur, Christian L. A. Renault
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Patent number: 4680303Abstract: Thioformamide derivatives of formula: ##STR1## in which R is hydrogen or alkyl (1 to 4 C), R.sub.1 is alkyl (1 to 4 C), and X denotes sulphur or oxygen and Y is sulphur, oxygen, methylene radical, or, when X is oxygen, a valency bond, are inhibitors of gastric secretion and therefore useful in the treatment of gastric ulcers. They may be made by reaction of an amine R--NH.sub.Type: GrantFiled: November 18, 1985Date of Patent: July 14, 1987Assignee: Rhone-Poulenc SanteInventors: Jean C. Aloup, Jean Bouchaudon, Daniel Farge, Claude James
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Patent number: 4670446Abstract: The invention provides the compounds of formula ##STR1## in which n equals 1 or 2,R denotes hydrogen, alkyl of 1 to 4 carbon atoms or phenyl,R.sub.1 denotes hydrogen, alkyl of 1 to 4 carbon atoms or alkenyl of 2 to 4 carbon atoms, X and Y, which may be identical or different, are each attached to the quinoline ring system in position 5, 6, 7 or 8, and each denote hydrogen or alkoxy of 1 to 3 carbon atoms. These compounds are useful in the treatment of cardiac arrhythmias.Type: GrantFiled: March 6, 1985Date of Patent: June 2, 1987Assignee: Rhone-Poulenc SanteInventors: Michel Mestre, Christian Renault
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Patent number: 4668669Abstract: Pristinamycin II.sub.B derivatives of formula: ##STR1## in which R denotes a nitrogen-containing 4 to 7-membered heterocyclic ring optionally substituted by alkyl; or alkyl (2 to 4 C) substituted by 1 or 2 phenyl, cycloalkylamino or N-alkyl-N-cycloalkylamino (3 to 6 ring atoms), alkylamino, dialkylamino or dialkylcarbamoyloxy radicals (the dialkylamino moieties of these 2 latter radicals being capable of forming a 4 to 7-membered cyclic ring optionally substituted by alkyl) or substituted by 1 or 2 nitrogen-containing 4 to 7 membered heterocyclic rings, optionally substituted by alkyl, at least one of the above substituents being a nitrogen-containing substituent capable of forming salts and n is 1 or 2, all the alkyls being linear or branched and containing (unless stated otherwise) 1 to 10 carbon atoms, their isomers, their salts and their preparation. These compounds, optionally in combination with known synergistins or synergistins of formula: ##STR2## are useful as antimicrobial agents.Type: GrantFiled: January 10, 1986Date of Patent: May 26, 1987Assignee: Rhone-Poulenc SanteInventors: Jean-Claude Barriere, Claude Cotrel, Jean-Marc Paris
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Chlorinated derivatives of hexadecene, their preparation and their use in the synthesis of vitamin E
Patent number: 4665244Abstract: Hexadecene derivatives of the formulae: ##STR1## and ##STR2## in which X and X.sub.1, which may be identical or different, each represent hydrogen or chlorine, and their mixtures, are useful in the preparation of tocopherol and tocopherol acetate.Type: GrantFiled: September 19, 1985Date of Patent: May 12, 1987Assignee: Rhone-Poulenc SanteInventors: Pierre Chabardes, Michel Mulhauser -
Patent number: 4665076Abstract: The piperidine derivatives of formula: ##STR1## in which X denotes --CO--, --CHOH-- or --CH(NH.sub.2)-- and Ar denotes ##STR2## in which R denotes hydrogen or alkyl of 1 to 4 carbon atoms, and Y and Z, which may be identical or different, each denote a hydrogen atom or alkoxy of 1 to 3 carbon atoms, and their addition salts with pharmaceutically acceptable inorganic or organic acids are useful for treating and/or preventing disturbances of cardiac rhythm. These compounds are new except when X is --CO-- and Ar is 1-naphthyl or 1-isoquinolyl.Type: GrantFiled: March 6, 1985Date of Patent: May 12, 1987Assignee: Rhone-Poulenc SanteInventors: Michel Mestre, Christian Renault
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Patent number: 4654176Abstract: The invention provides novel sulphonated chiral phosphines of the formula: ##STR1## in which R represents an alkyl radical, a cycloalkyl radical optionally substituted with an alkyl radical, a cycloalkylalkyl radical optionally substituted with an alkyl radical, a phenyl, phenylalkyl, binaphthyl or binaphthylalkyl radical, in which the alkyl, cycloalkyl, phenyl and binaphthyl radicals, and the alkyl portions of the other radicals, can be substituted by a radical of general formula: ##STR2## R.sub.1 represents an alkyl, cycloalkyl, phenyl, or phenylalkyl radical, Ar represents a phenyl or naphthyl radical, m.sup.+ represents a proton or alkali metal ion or alkaline earth metal ion, m=1 or 2, n=0, 1 or 2, p=1 or 2, (p+m) .ltoreq.3, and R and R.sub.1 can be chiral or achiral. These chiral phosphines form water-soluble metal complexes useful as catalysts in asymmetric organic synthesis.Type: GrantFiled: July 27, 1984Date of Patent: March 31, 1987Assignee: Rhone-Poulenc SanteInventors: Tuan-Phat Dang, Jean Jenck, Didier Morel
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Patent number: 4647554Abstract: New immunostimulant substances are obtained by hydrolyzing reduced and alkylated bovine fibrinogen with a proteolytic enzyme and fractionating the product.Type: GrantFiled: June 14, 1985Date of Patent: March 3, 1987Assignee: Rhone-Poulenc SanteInventors: Pierre Jolles, Daniele Migliore-Samour, Fabienne Parker
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Patent number: 4642308Abstract: The invention provides novel substituted amides of formula:R--CONH--Hetin which R is cycloalkyl, cyclohexadienyl, phenyl optionally substituted with one or 2 fluorine atoms or with a hydroxy radical, or substituted at position 3- or 4- with an alkyl or alkyloxy radical, or with a methylenedioxy radical at positions 3- and 4-, or at position 2- or 3- with a dialkylamino radical, or is 3-pyridyl, alkyloxy-3-pyridyl, thienyl, alkylthienyl, furyl, tetrahydropyridyl, pyridazinyl and alkylpyridazinyl, and Het is 2-quinolyl or 1,8-naphthyridin-2-yl, both optionally substituted at position 7- with a halogen atom or a hydroxymethyl, alkyl, alkyloxy, alkyloxyalkyloxy, alkenyloxy or alkynyloxy radical (of 3 or 4 carbon atoms), an alkylthio or benzylthio radical, a phenoxy radical which is optionally substituted (with fluorine, with chlorine or bromine at position 2-, or with an alkyloxy radical or 1 or 2 alkyl radicals) or with pyridyloxy or alkylpiperidyloxy, provided that, when Het is 2-quinolyl, R is other than phenyType: GrantFiled: July 17, 1985Date of Patent: February 10, 1987Assignee: Rhone-Poulenc SanteInventors: Claude Cotrel, Claude Guyon, Gerard Roussel, Gerard Taurand
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Patent number: 4636570Abstract: Tocopherol derivatives of the formula: ##STR1## in which X and X.sub.1, which may be identical or different, each represent hydrogen or chlorine and their acetates are useful in the synthesis of vitamin E.Type: GrantFiled: September 19, 1985Date of Patent: January 13, 1987Assignee: Rhone-Poulenc SanteInventors: Pierre Chabardes, Michel Mulhauser
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Patent number: 4634778Abstract: Process for preparing chlorinated ethylenic derivatives of the formula ##STR1## in which R.sub.1 represents acetyl, formyl optionally in the form of an acetal, hydroxy optionally as an ether or ester, alkyloxycarbonyl, alkyl of 1 to 12 carbon atoms substituted by one or more acetyl, formyl optionally in the form of an acetal, hydroxy optionally in the form of an ether or ester, or alkyloxycarbonyl, alkenyl of 2 to 12 carbon atoms containing one or more double bonds optionally substituted by one or more of acetyl, formyl optionally in the form of an acetal, hydroxy optionally in the form of an ether or ester, or alkyloxycarbonyl, or R.sub.1 represents 3-sulpholenyl or a radical of formula ##STR2## in which R.sub.2 denotes a hydrogen or acetyl, by reacting chlorine in a nonpolar aprotic solvent with a compound of general formula ##STR3## in which R.sub.1 is defined as above. The products of formula I, some of which are new, are useful as intermediates in the synthesis of terpene products such as vitamin E.Type: GrantFiled: November 16, 1984Date of Patent: January 6, 1987Assignee: Rhone-Poulenc SanteInventors: Gerard Mignani, Didier Morel, Pierre Chabardes
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Patent number: 4621165Abstract: A process for removing from a mixture of isoprene trimers compounds of the formula ##STR1## by reacting a mixture of cyclic and linear trimers with a compound having an activated carbon atom, of the formula:X--CH.sub.2 --Yin which one of X or Y is an electron-withdrawing group and the other is an electron-withdrawing or electron-donating group, in the presence of a catalyst consisting of a water-soluble phosphine and a rhodium compound, the reaction being carried out in water or in a water-alcohol medium, and separating the cyclic trimers and linear trimers containing the chain ##STR2## from the mixture of products of the formulae: ##STR3## which can be used, in particular, in the synthesis of vitamin E.Type: GrantFiled: February 23, 1984Date of Patent: November 4, 1986Assignee: Rhone-Poulenc SanteInventor: Didier Morel
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Patent number: 4618599Abstract: The invention provides new synergistine derivatives of the formula: ##STR1## in which Y=H or N(CH.sub.3).sub.2 and (a) R.sub.1 and R.sub.2 =H and R=pyrrolidin-3-ylthio or piperidin-3-ylthio or piperidin-4-ylthio (optionally substituted by alkyl), or altenatively R=alkylthio substituted by 1 or 2 SO.sub.3 H radicals or alkylamino or dialkylamino radicals (optionally substituted) or by 1 or 2 piperazino rings (optionally substituted) or morpholino, thiomorpholino, piperidino, pyrrolidin-1-yl, piperidin-2-yl, piperidin-3-yl or piperidin-4-yl or pyrrolidin-2-yl or pyrrolidin-3-yl rings (these last 5 rings being optionally substituted by alkyl), or(b) R.sub.1 and R.sub.2 form a bond and R=pyrrolidin-3-ylamino, piperidin-3-ylamino or piperidin-4-ylamino, pyrrolidin-3-yloxy, piperidin-3-yloxy or piperidin-4-yloxy, pyrrolidin-3-ylthio, piperidin-3-ylthio or piperidin-4-ylthio (optionally substituted by alkyl), or alternatively R=alkylamino, alkoxy or alkylthio substituted by 1 or 2 SO.sub.Type: GrantFiled: July 12, 1984Date of Patent: October 21, 1986Assignee: Rhone-Poulenc SanteInventors: Jean-Pierre Corbet, Claude Cotrel, Daniel Farge, Jean-Marc Paris
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Patent number: 4617377Abstract: The invention provides new synergistine derivatives of the formula: ##STR1## in which Y=H or N(CH.sub.3).sub.2 and R represents: (a) H or OH,(b) a radical of the formula NR.sub.1 R.sub.2, in which R.sub.1 and R.sub.2 =H, phenyl or pyridyl (optionally substituted by dialkylamino (1 to 4 C), alkyl (1 to 10 C) [optionally substituted by OH, SH, COOH, anilino, or alkylamino or dialkylamino of which at least one of the alkyl parts is substituted by OH, SH, COOH or anilino 9 , alkenyl (3 or 4 C) or alkynyl (3 or 4 C), or alternatively R.sub.1 and R.sub.2 together form a heterocycle optionally containing another heteroatom such as O, S or N (optionally substituted by alkyl), or(c) a halogen atom, a trimethylsilyloxy or dialkylphosphoryloxy radical or a radical --OSO.sub.2 R.sub.3 or --OCOR.sub.4, R.sub.3 being alkyl, trifluoromethyl, trichloromethyl or optionally substituted phenyl and R.sub.4 being defined in the same way as R.sub.Type: GrantFiled: July 12, 1984Date of Patent: October 14, 1986Assignee: Rhone-Poulenc SanteInventors: Jean-Pierre Corbet, Claude Cotrel, Daniel Farge, Jean-Marc Paris