Patents by Inventor Michel Laubie
Michel Laubie has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).
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Patent number: 5162324Abstract: Compounds of formula I: ##STR1## in which: n=1-4,R represents hydrogen, halogen, alkyl, hydroxyl or alkoxy, R.sub.1 represents a radical --NHCOR2 (A.sub.1); (in which R.sub.2 represents alkyl, cycloalkyl, phenyl optionally substituted-, -O-alkyl, 3-pyridyl, 2-pyrrolyl, quinolyl, 1-isoquinolyl, 2-thienyl or 3-indolyl); a radical of --NHSO2R3 (A.sub.2) (in which R.sub.3 represents alkyl, cycloalkyl or phenyl optionally substituted); a radical --NHCONHR4 (A.sub.3) (in which R.sub.4 represents alkyl or phenyl-optionally substituted); a phthalimido radical (A.sub.4); an o-sulfobenzoic imido radical (A.sub.5); a di(benzoyl)amino radical (A.sub.6) optionally substituted; a radical of formula A.sub.7 : ##STR2## (in which R.sub.5 represents carbamoyl, cyano, carboxy or alkoxycarbonyl); or a radical of formula A.sub.8 : ##STR3## their stereoisomers and their addition salts with a pharmaceutically-acceptable inorganic or organic acid, are disclosed to be useful as 5-HT.sub.Type: GrantFiled: August 29, 1991Date of Patent: November 10, 1992Assignee: Adir et CompagnieInventors: Gilbert Lavielle, Michel Laubie, Francis Colpaert
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Patent number: 5162321Abstract: Compounds of formula I: ##STR1## in which: n=1-4;R represents hydrogen, halogen, alkyl, hydroxyl or alkoxy, R.sub.1 represents a radical --NHCOR2 (A.sub.1); (in which R.sub.2 represents alkyl, cycloalkyl, phenyl optionally substituted-, --O-alkyl, 3-pyridyl, 2-pyrrolyl, quinolyl, 1-isoquinolyl, 2-thienyl or 3-indolyl); a radical of --NHSO2R3 (A.sub.2) (in which R.sub.3 represents alkyl, cycloalkyl or phenyl optionally substituted); a radical --NHCONHR4 (A.sub.3) (in which R.sub.4 represents alkyl or phenyl-optionally substituted); a phthalimido radical (A.sub.4); an o-sulfobenzoic imido radical (A.sub.5); a di(benzoyl)amino radical (A.sub.6) optionally substituted; a radical of formula A.sub.7 : ##STR2## (in which R.sub.5 represents carbamoyl, cyano, carboxy or alkoxycarbonyl); or a radical of formula A.sub.8 : ##STR3## their stereoisomers and their addition salts with a pharamaceutically-acceptable inorganic or organic acid, are disclosed to be useful as 5-HT.sub.Type: GrantFiled: August 29, 1991Date of Patent: November 10, 1992Assignee: Adir et CompagnieInventors: Gilbert Lavielle, Michel Laubie, Francis Colpaert
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Patent number: 5143916Abstract: Compounds of the formula I: ##STR1## in which: n=1-4,R represents hydrogen, halogen, alkyl, hydroxyl or alkoxy, R.sub.1 represents a radical --NHCOR2 (A.sub.1); (in which R.sub.2 represents alkyl, cycloalkyl, phenyl optionally substituted-, --O-alkyl, 3-pyridyl, 2-pyrrolyl, quinolyl, 1-isoquinolyl, 2-thienyl or 3-indolyl); a radical of --NHS02R3 (A.sub.2) (in which R.sub.3 represents alkyl, cycloalkyl or phenyl optionally substituted); a radical --NHCONHR4 (A.sub.3) (in which R.sub.4 represents alkyl or phenyl-optionally substituted); a phthalimido radical (A.sub.4); an o-sulfobenzoic imido radical (A.sub.5); a di(benzoyl)amino radical (A.sub.6) optionally substituted; a radical of formula A.sub.7 : ##STR2## (in which R.sub.5 represents carbamoyl, cyano, carboxy or alkoxycarbonyl); or a radical of formula A.sub.8 : ##STR3## their stereoisomers and their addition salts with a pharmaceutically-acceptable inorganic or organic acid, are disclosed to be useful as 5-HT.sub.Type: GrantFiled: December 19, 1990Date of Patent: September 1, 1992Assignee: Adir et CompagnieInventors: Gilbert Lavielle, Michel Laubie, Francis Colpaert
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Patent number: 5079249Abstract: The invention relates to compounds of formula I: ##STR1## in which m=2-4,n and p, which may be identical or different, are an integer equal to 1, 2 or 3, with the proviso that the sum of n and pq=0 or 1,R is a 1,2,3,4-tetrahydro-2,4-dioxo-3-quinazolinyl radical, optionally substituted, a 1,3,4,6,11,11a-hexahydro-1,3-dioxo-2H-pyrazino[1,2-b]isoquinol-2-yl radical, a 1,2-dihydro-1-oxo-2-phthalazinyl radical, optionally substituted, a 2,6-dioxo-1-piperazinyl radical of formula W: ##STR2## (R.sub.3 is a 2-pyridyl radical or an optionally substituted phenyl radical),a radical of formula Z: ##STR3## (R.sub.4 is a carbamoyl radical, a cyano radical, a hydroxycarbonyl radical or an alkoxycarbonyl radical having 1 to 6 carbon atoms),or a radical of formula Y: ##STR4## (R.sub.5 is a 2-pyrimidinyl radical, a 1-isoquinolyl radical, a 2-quinolyl radical, a 2-pyridyl radical, a benzyl radical, optionally substituted, a 2-thiazolyl radical, optionally substituted, or a 2-benzothiazolyl radical) andeither R.sub.1 and R.sub.Type: GrantFiled: August 24, 1990Date of Patent: January 7, 1992Assignee: Adir et CompagnieInventors: Gilbert Lavielle, Francis Colpaert, Michel Laubie
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Patent number: 5077288Abstract: The invention relates to the compounds of general formula I: ##STR1## in which: m represents an integer from 2 to 4,n and p, which may be identical or different, each represent an integer from 1 to 3,q represents 0 or 1, andR represents:either a group of formula (A): ##STR2## or a radical of formula (B): ##STR3## or a 2,4-dioxo-1,2,3,4-tetrahydroquinazolinyl radical, on condition, however, that, in this case, n and p do not simultaneously represent the number 2,or a benzhydryloxy group,or a 1-oxophthalazinyl radical,or a 5-oxothiazolo[3,2-A]pyrimidinyl radical,or a group of formula C: ##STR4## their possible stereoisomers and their addition salts with a pharmaceutically acceptable inorganic or organic acid.The compounds of formula I are medicinal products with useful 5-HT.sub.2 - and .alpha..sub.1 -antagonistic activities.Type: GrantFiled: March 20, 1990Date of Patent: December 31, 1991Assignee: Adir et CompagnieInventors: Gilbert Lavielle, Francis Colpaert, Michel Laubie
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Patent number: 5071847Abstract: The invention relates to compounds of formula I: ##STR1## in which m=2-4,n and p, which may be identical or different, are an integer equal to 1, 2 or 3, with the proviso that the sum of n and p is 5,q=0 or 1,R is a 1,2,3,4-tetrahydro-3-quinazolinyl radical, optionally substituted, a 1,3,4,6,11,11a-hexahydro-1,3-dioxo-2H-pyrazino[1,2-b]isoquinol-2-yl radical, a 1,2-dihydro-1-oxo-2-phthalazinyl radical, optionally substituted, a 2,6-dioxo-1-piperazinyl radical of formula W: ##STR2## (R.sub.3 is a 2-pyridyl radical or an optionally substituted phenyl radical),a radical of formula Z: ##STR3## (R.sub.4 is a carbamoyl radical, a cyano radical, a hydroxycarbonyl radical or an alkoxycarbonyl radical having 1 to 6 carbon atoms),or a radical of formula Y: ##STR4## (R.sub.5 is a 2-pyrimidinyl radical, a 1-isoquinolyl radical, a 2-quinolyl radical, a 2-pyridyl radical, a benzyl radical, optionally substituted, a 2-thiazolyl radical, optionally substituted, or a 2-benzothiazolyl radical) andeither R.sub.1 and R.sub.Type: GrantFiled: August 24, 1990Date of Patent: December 10, 1991Assignee: Adir et CompagnieInventors: Gilbert Lavielle, Francis Colpaert, Michel Laubie
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Patent number: 5030646Abstract: The invention relates to compounds of general formula: ##STR1## in which A, B, G, D which may be identical or different, each denote a hydrogen atom or a halogen atom, a lower alkoxy group or alternatively a lower alkyl group optionally substituted with one or more halogen atoms,X denotes a hydrogen atom, a linear or branched lower alkyl group or a group SO.sub.2 E in which E denotes a linear or branched lower alkyl group or an aryl group optionally substituted with a linear or branched lower alkyl group,T denotes a hydrogen atom or a lower alkyl group,R.sub.3 denotes a hydrogen atom or a linear or branched lower alkyl group or an aryl group optionally substituted with one or more linear or branched lower alkyl groups,n and m, which may be identical or different, each denote 0 or 1,R.sub.1 and R.sub.2, which may be identical or different, each denote a hydrogen atom or a linear or branched lower alkyl group,or alternatively,R.sup.1 and R.sup.Type: GrantFiled: December 5, 1989Date of Patent: July 9, 1991Assignee: Adir et CompagnieInventors: Charles Malen, Jean-Michel Lacoste, Michel Laubie
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Patent number: 4959372Abstract: Compounds of formula (I): ##STR1## in which E denotes a lower alkyl group, or preferably a hydrogen atom, and their addition salts with a pharmaceutically acceptable acid or base, the preparation thereof and pharmaceutical compositions containing them.Type: GrantFiled: August 26, 1988Date of Patent: September 25, 1990Assignee: Adir et lieInventors: Michel Vincent, Georges Remond, Michel Laubie
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Patent number: 4644008Abstract: Compounds of the general formula: ##STR1## wherein: the ring A is saturated and n=0 or 1, orthe ring A is a benzene ring and n=1,R.sub.1 represents a lower alkyl group which can carry an amino group,R.sub.2 represents a hydrogen atom or a lower alkyl group,R.sub.3 represents a straight or branched alkyl group, a mono- or di-cycloalkylalkyl or phenylalkyl group having no more than a total of 9 carbon atoms, or a substituted alkyl group, and also the salts thereof.These compounds are useful as therapeutic drugs.Type: GrantFiled: October 10, 1984Date of Patent: February 17, 1987Assignee: AdirInventors: Michel Vincent, Georges Remond, Michel Laubie
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Patent number: 4616030Abstract: Compounds of the general formula: ##STR1## wherein: the ring A is saturated and n=0 or 1, orthe ring A is a benzene ring and n=1,R.sub.1 represents a lower alkyl group which can carry an amino group,R.sub.2 represents a hydrogen atom or a lower alkyl group,R.sub.3 represents a straight or branched alkyl group, a mono- or di-cycloalkylalkyl or phenylalkyl group having no more than a total of 9 carbon atoms, or a substituted alkyl group, and also the salts thereof.These compounds are useful as therapeutic drugs.Type: GrantFiled: December 6, 1984Date of Patent: October 7, 1986Assignee: ADIRInventors: Michel Vincent, Georges Remond, Michel Laubie
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Patent number: 4616031Abstract: Compounds of the general formula: ##STR1## wherein: the ring A is saturated and n=0 or 1, orthe ring A is a benzene ring and n=1,R.sub.1 represents a lower alkyl group which can carry an amino group,R.sub.2 represents a hydrogen atom or a lower alkyl group,R.sub.3 represents a straight or branched alkyl group, a mono- or di-cycloalkylalkyl or phenylalkyl group having no more than a total of 9 carbon atoms, or a substituted alkyl group, and also the salts thereof.These compounds are useful as thereapeutic drugs.Type: GrantFiled: October 10, 1984Date of Patent: October 7, 1986Assignee: ADIRInventors: Michel Vincent, Georges Remond, Michel Laubie
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Patent number: 4616029Abstract: Compounds of the general formula: ##STR1## wherein: the ring A is saturated and n=0 or 1, orthe ring A is a benzene ring and n=1,R.sub.1 represents a lower alkyl group which can carry an amino group,R.sub.2 represents a hydrogen atom or a lower alkyl group,R.sub.3 represents a straight or branched alkyl group, a mono- or di-cycloalkylalkyl or phenylalkyl group having no more than a total of 9 carbon atoms, or a substituted alkyl group, and also the salts thereof.These compounds are useful as therapeutic drugs.Type: GrantFiled: October 10, 1984Date of Patent: October 7, 1986Assignee: ADIRInventors: Michel Vincent, Georges Remond, Michel Laubie
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Anti-hypoxic disubstituted polymethylene imine derivatives, compositions, and method of use therefor
Patent number: 4593026Abstract: Disubstituted polymethylene imines of the formula: ##STR1## in which: A is a straight or branched chain (C.sub.3 -C.sub.5) hydrocarbon containing radical optionally containing one or two double bond and optionally substituted by one or more hydroxy;n is zero, one or two;Z is oxygen or NH; andR is:either COR', in which R' is:(a) a straight or branched chain (C.sub.1 -C.sub.6), hydrocarbon containing radical, optionally containing one oxygen or sulfen or a double bond and optionally substituted by phenyl or substituted phenyl; or(b) phenyl, halophenyl, lower alkoxyphenyl, (di-or-tri-methylene) dioxyphenyl or;(c) furyl, thienyl, benzofuryl, benzothienyl or benzodioxannyl; or(d) ##STR2## in which R.sub.1 and R.sub.2 are hydrogen or lower alkyl or ##STR3## is a five or six membered heterocyclic radical which may contain an oxygen;or--SO.sub.2 R" in which R" is (C.sub.1 -C.sub.3) alkyl or phenyl.Type: GrantFiled: April 6, 1984Date of Patent: June 3, 1986Assignee: Adir, S.A.R.L.Inventors: Gilbert Regnier, Alain Dhainaut, Michel Laubie, Jacques Duhault, Francois Roman -
Patent number: 4567181Abstract: Compounds of the formula: ##STR1## in which: R.sub.1 and R.sub.2 each represent, independently of one another, hydrogen, halogen, alkyl or alkoxy having from 1 to 4 carbon atoms, sulphonamide possibly substituted by an alkyl radical having from 1 to 4 carbon atoms; or together methylenedioxy, n is 0 or 1,in racemic form or in the form of optical isomers, and also their salts of addition with pharmaceutically acceptable acids. Useful in the treatment of ailments and/or conditions which are adrenoreceptor-related, such relationship being well known in the art.Type: GrantFiled: April 5, 1984Date of Patent: January 28, 1986Assignee: ADIR, s.a.r.l.Inventors: Charles Malen, Jean-Louis Peglion, Michel Laubie, Jean-Claude Poignant
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Patent number: 4565819Abstract: Compounds of the general formula: ##STR1## wherein: the ring A is saturated and n=0 or 1, orthe ring A is a benzene ring and n=1,R.sub.1 represents a lower alkyl group which can carry an amino group,R.sub.2 represents a hydrogen atom or a lower alkyl group,R.sub.3 represents a straight or branched alkyl group, a mono- or di-cycloalkylalkyl or phenylalkyl group having no more than a total of 9 carbon atoms, or a substituted alkyl group, and also the salts thereof.These compounds are useful as therapeutic drugs.Type: GrantFiled: September 20, 1982Date of Patent: January 21, 1986Assignee: ADIRInventors: Michel Vincent, Georges Remond, Michel Laubie
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Patent number: 4529729Abstract: Piperazine and homopiperazine compounds of the formula: ##STR1## in which: A is a hydrocarbon radical from C.sub.3 to C.sub.5, in a straight or branched chain, which may contain one or two double bonds, and optionally substituted by one or more OH;B is CH or a nitrogen atom;m is 2 or 3;X--Y-- represents --CH.dbd.CH--(CR'R").sub.n - in which n is zero or 1, and R' and R" are hydrogen or methyl;Z is oxygen or sulfur,R is hydrogen, alkyl from C.sub.1 to C.sub.5, cycloalkyl from C.sub.3 to C.sub.7, or phenyl optionally substituted by fluorine, chlorine or alkyl from C.sub.1 to C.sub.5, andT is hydrogen, fluorine, chlorine or alkyl from C.sub.1 to C.sub.5.These compounds and physiologically tolerable acid addition salts thereof may be used as medicines especially in the treatment of all kinds of tissular hypoxia.Type: GrantFiled: June 20, 1984Date of Patent: July 16, 1985Assignee: AdirInventors: Gilbert Regnier, Michel Laubie, Jacques Duhault
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Patent number: 4514398Abstract: Polymethylene-imines of the formula: ##STR1## in which: A is a hydrocarbon radical from C.sub.3 to C.sub.5 in a straight or branched chain possibly containing one or two double bonds and possibly substituted by one or more hydroxy radicals;X is CH or nitrogen;n is zero, one or two;Y is oxygen or N--R.sub.1 in which R.sub.1 is hydrogen, alkyl from C.sub.1 to C.sub.5, alkenyl from C.sub.2 to C.sub.5, cycloalkyl or cycloalkenyl from C.sub.3 to C.sub.7, or acetyl;R is hydrogen, alkyl from C.sub.1 to C.sub.5, cycloalkyl from C.sub.5 to C.sub.7 or phenyl optionally substituted by one or more fluorine or chlorine; andB is hydrogen, alkyl from C.sub.1 to C.sub.5, alkenyl from C.sub.2 to C.sub.5, or phenyl, naphthyl, benzofuranyl, benzothienyl, benzodioxolyl, benzodioxanyl, benzodioxinyl, .DELTA.3-chromanyl, thiochromenyl or chromanyl, each optionally substituted by fluorine, chlorine, alkyl or alkoxy from C.sub.1 to C.sub.5 ; ora radical of the formula: ##STR2## in which: R.sub.2, R.sub.3 and R.sub.Type: GrantFiled: March 25, 1983Date of Patent: April 30, 1985Assignee: ADIRInventors: Gilbert Regnier, Alain Dhainaut, Michel Laubie, Jacques Duhault
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Patent number: 4514399Abstract: N,N'-substituted polymethylene diamines of the formula: ##STR1## in which: A is a hydrocarbon radical from C.sub.3 to C.sub.5 in a straight or branched chain optionally containing one and two double bonds and possibly substituted by one or more hydroxy radicals;X is CH or nitrogen;n is an integer from 2 to 6;R.sub.1 is hydrogen, or alkyl from C.sub.1 to C.sub.5 ;R.sub.2 is hydrogen, alkyl from C.sub.1 to C.sub.5, cycloalkyl from C.sub.5 to C.sub.7, or phenyl optionally substituted by one or more fluorine or chlorine, andB is:phenyl, naphthyl, benzofuranyl, benzothionyl, benzodioxolyl, benzodioxanyl, benzodioxinyl, .DELTA.3-chromenyl, thiochromenyl or chromanyl, each of them optionally substituted by fluorine, chlorine, alkyl or alkoxy from C.sub.1 to C.sub.5, or methylene-dioxy, ora radical of the formula: ##STR2## in which R.sub.3, R.sub.4 and R.sub.5 which may be the same or different, each represent hydrogen or phenyl optionally substituted by fluorine or chlorine.Type: GrantFiled: April 18, 1983Date of Patent: April 30, 1985Assignee: AdirInventors: Gilbert Regnier, Alain Dhainaut, Michel Laubie, Jacques Duhault
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Patent number: 4508729Abstract: Compounds of the general formula: ##STR1## wherein: the ring A is saturated and n=0 or 1, orthe ring A is a benzene ring and n=1,R.sub.1 represents a lower alkyl group which can carry an amino group,R.sub.2 represents a hydrogen atom or a lower alkyl group,R.sub.3 represents a straight or branched alkyl group, a mono- or di-cycloalkylalkyl or phenylalkyl group having no more than a total of 9 carbon atoms, or a substituted alkyl group, and also the salts thereof.These compounds are useful as therapeutic drugs.Type: GrantFiled: October 2, 1981Date of Patent: April 2, 1985Assignee: AdirInventors: Michel Vincent, Georges Remond, Michel Laubie
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Patent number: 4492696Abstract: Piperazine and homopiperazine compounds of the formula: ##STR1## in which: A is a hydrocarbon radical from C.sub.3 to C.sub.5, in a straight or branched chain, which may contain one or two double bonds, and optionally substituted by one or more OH;B is CH or a nitrogen atom;m is 2 or 3;X--Y-- represents --CH.dbd.CH-- (CR'R").sub.n -- in which n is zero or 1, and R' and R" are hydrogen or methyl;Z is oxygen or sulfur,R is hydrogen, alkyl from C.sub.1 to C.sub.5, cycloalkyl from C.sub.3 to C.sub.7, or phenyl optionally substituted by fluorine, chlorine or alkyl from C.sub.1 to C.sub.5, andT is hydrogen, fluorine, chlorine or alkyl from C.sub.1 to C.sub.5.These compounds and physiologically tolerable acid addition salts thereof may be used as medicines especially in the treatment of all kinds of tissular hypoxy.Type: GrantFiled: February 15, 1983Date of Patent: January 8, 1985Assignee: ADIRInventors: Gilbert Reginier, Michel Laubie, Jacques Duhault