Patents by Inventor Guy M. Raynaud
Guy M. Raynaud 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: 4104384Abstract: Compounds of the formula ##STR1## where Ar is phenyl, substituted phenyl, .alpha.-furyl or .alpha.-thienyl, andR is NH.sub.2, NHR.sup.1 wherein R.sup.1 is alkyl or cycloalkyl, or NR.sub.1 R.sub.2 whereinR.sub.1 and R.sub.2 are alkyl or --N.sub.1 R.sub.1 R.sub.2 is piperidino, pyrrolidino, morpholino or hexamethyleneimino. The compounds are prepared by reacting the corresponding Ar-substituted chloromethylated benzimadazole with the corresponding R-substituted piperazine. The compounds possess gastric antisecretory, anti-ulcerous, spasmolytic, anti-cholinergic, anti-bronchoconstrictive, analgesic, anti-inflammatory, anti-hypertensive and diuretic properties.Type: GrantFiled: November 28, 1977Date of Patent: August 1, 1978Assignee: Delalande S.A.Inventors: Claude P. Fauran, Michel J. Turin, Thierry F. Imbert, Guy M. Raynaud, Nicole A. M. Dorme
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Patent number: 4072682Abstract: Compounds of the formula ##STR1## where Ar is phenyl, substituted phenyl, .alpha.-furyl or .alpha.-thienyl, andR is NH.sub.2, NHR.sup.1 wherein R.sup.1 is alkyl or cycloalkyl, or NR.sub.1 R.sub.2wherein R.sub.1 and R.sub.2 are alkyl or --N.sub.1 R.sub.1 R.sub.2 is piperidino, pyrrolidino, morpholino or hexamethyleneimino. The compounds are prepared by reacting the corresponding Ar-substituted chloromethylated benzimidazole with the corresponding R-substituted piperazine. The compounds possess gastric antisecretory, anti-ulcerous, spasmolytic, anti-cholinergic, anti-bronchoconstrictive, analgesic, anti-inflammatory, anti-hypertensive and diuretic properties.Type: GrantFiled: December 22, 1975Date of Patent: February 7, 1978Assignee: Delalande S.A.Inventors: Claude P. Fauran, Michel J. Turin, Thierry F. Imbert, Guy M. Raynaud, Nicole A. M. Dorme
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Patent number: 4049658Abstract: Compounds of the formula ##STR1## wherein Z is --CH.sub.2 CH.sub.2 -- or --CH.dbd.CH--, and R is methyl, ethoxycarbonylmethyl or ##STR2## wherein ##STR3## is methylamino, n-propylamino, isopropylamino, dimethylamino, di(n-propyl)amino, morpholino, pyrrolidino or hexamethyleneimino. The compounds are prepared by reacting piperazine substituted with R, with 4'-bromomethyl-5,2'-spiro-dibenzocycloheptadi(or tri)ene-(1',3') dioxolan. The compounds possess cough-suppressing, spasmolytic, analgesic, respiratory analeptic, hypotensive, vasodilatory, antiarythmic, antiulcerous, antihistamine, sedative, anti-inflammatory, diuretic and antiserotonine properties.Type: GrantFiled: December 6, 1976Date of Patent: September 20, 1977Assignee: Delalande S.A.Inventors: Claude P. Fauran, Guy M. Raynaud, Michel J. Turin, Janine M. Thomas
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Patent number: 4049660Abstract: Compounds of the formula ##STR1## wherein Z is --CH.sub.2 CH.sub.2 -- or --CH.dbd.CH--, and R is methyl, ethoxycarbonylmethyl or ##STR2## wherein ##STR3## is methylamino, n-propylamino, isopropylamino, dimethylamino, di(n-propyl)amino, morpholino, pyrrolidino or hexamethyleneimino. The compounds are prepared by reacting piperazine substituted with R, with 4'-bromomethyl-5,2'-spiro-dibenzocycloheptadi(or tri)ene-(1',3') dioxolan. The compounds possess cough-suppressing, spasmolytic, analgesic, respiratory analeptic, hypotensive, vasodilatory, antiarythmic, antiulcerous, antihistamine, sedative, anti-inflammatory, diuretic and antiserotonine properties.Type: GrantFiled: December 6, 1976Date of Patent: September 20, 1977Assignee: Delalande S.A.Inventors: Claude P. Fauran, Guy M. Raynaud, Michel J. Turin, Janine M. Thomas
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Patent number: 4048164Abstract: Compounds of the formula ##STR1## wherein Z is --CH.sub.2 CH.sub.2 -- or --CH=CH--, and R is methyl, ethoxycarbonylmethyl or ##STR2## wherein ##STR3## is methylamino, n-propylamino, isopropylamino, dimethylamino, di(n-propyl)amino, morpholino, pyrrolidino or hexamethyleneimino. The compounds are prepared by reacting piperazine substituted with R, with 4'-bromomethyl-5,2'-spiro-dibenzocycloheptadi- (or tri)ene-(1',3') dioxolan. The compounds possess cough-suppressing, spasmolytic, analgesic, respiratory analeptic, hypotensive, vasodilatory, antiarythmic, antiulcerous, antihistamine, sedative, anti-inflammatory, diuretic and antiserotonine properties.Type: GrantFiled: January 16, 1975Date of Patent: September 13, 1977Assignee: Delalande S.A.Inventors: Claude P. Fauran, Guy M. Raynaud, Michel J. Turin, Janine M. Thomas
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Patent number: 4041030Abstract: Compounds of the formula ##STR1## WHEREIN Ar is phenyl or phenyl substituted by one or more halogens, a trifluoromethyl, a methylenedioxy, one or more methoxy, an alkyl having one to 4 carbon atoms or a dimethylamino,And R is ##STR2## wherein R.sub.1 and R.sub.2 each are hydrogen or alkyl of 1 to 4 carbon atoms, or ##STR3## PYRROLIDINO, MORPHOLINO, PIPERIDINO OR PIPERAZINO N'-substituted by alkyl of 1 to 4 carbon atoms, or phenyl, or R is para-2-morpholino ethylamino carbonyl, and R.sub.3 is hydrogen or methyl.The compounds are obtained by reacting 2-Ar-2-chloro-6-methyl pyrimidine, with ##STR4## The compounds possess sedative, antiulcerous, antibronchoconstrictive, anticholinergic, diuretic, analgesic myorelaxant and antianoximia properties.Type: GrantFiled: August 16, 1976Date of Patent: August 9, 1977Assignee: Delalande S.A.Inventors: Claude P. Fauran, Guy R. Bourgery, Guy M. Raynaud, Claude J. Gouret
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Patent number: 4031089Abstract: Compounds of the formula ##STR1## wherein R is alkyl of 1-4 carbon atoms, phenyl, or phenyl substituted by one or more halogen or trifluoromethyl, and Z is ##STR2## wherein R.sub.1 is hydrogen, alkyl of 1-4C, 2,2-dimethyldioxolan-4-yl methyl, or 2,3-dihydroxy prop-1-yl, R.sub.2 is ##STR3## wherein ##STR4## is morpholino, pyrrolidino, piperidino or hexamethyleneimino, and n is an integer from 4 to 7.The compounds are prepared by reacting R-substituted 4-chloro-2-methyl furo (2,3d) pyrimidine with HZ. The compounds possess antiulcerous, antibronchoconstrictive and anticholinergic, analgesic, antihistamine, diuretic, cardiovascular analeptic, antiinflammatory and hypertensive properties.Type: GrantFiled: August 18, 1976Date of Patent: June 21, 1977Assignee: Delalande S.A.Inventors: Claude P. Fauran, Guy R. Bourgery, Guy M. Raynaud, Nicole A. M. Dorme
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Patent number: 4029789Abstract: Compounds of the formula ##STR1## in which Ar is .alpha.-furyl or .alpha.-thienyl and pharmacologically acceptable salts thereof are provided as novel therapeutic agents which have inter alia utility in treating asthma, respiratory deficiency, visceral spasms, gastroduodenal ulcers or hyperchlorhydria.Type: GrantFiled: November 20, 1975Date of Patent: June 14, 1977Assignee: Delalande S.A.Inventors: Claude P. Fauran, Nicole Dorme, Guy M. Raynaud, Jeannine Eberle
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Patent number: 4029650Abstract: Compounds having the formula ##STR1## in which R.sub.1 is alkyl having no more than 4 carbon atoms and R.sub.2 is dimethoxyphenylethyl or ##STR2## is piperidino, heptamethyleneimino or 1,2,3,4-tetrahydroisoquinolino. The compounds are prepared by condensing N-(3,4,5-trimethoxy cinnamoyl)N'-(carboxymethyl) piperazine with ##STR3## The compounds possess peripheral, coronary and cerebral vasodilatory properties and an antihypertensive property.Type: GrantFiled: November 20, 1975Date of Patent: June 14, 1977Assignee: Delalande S. A.Inventors: Guy M. Raynaud, Bernard M. Pourrias, Claude P. Fauran, Michel J. Turin
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Patent number: 4025514Abstract: Compounds of the formula ##STR1## wherein Ar is phenyl or phenyl substituted by one or more halogens, a trifluoromethyl, a methylenedioxy, one or more methoxy, an alkyl having one to 4 carbon atoms or a dimethylamino,And R is ##STR2## and R.sub.5 is alkyl of 1 to 4 carbon atoms, 2,3-dihydroxypropyl or 2,2-dimethyl dioxolan-4-yl methyl or hydroxycarbonylmethyl.The compounds are obtained by reacting 2-Ar-4-chloro-6-methyl pyrimidine, with ##STR3## The compounds possess sedative, antiinflammatory, antiulcerous, and anti-anoxemia properties.Type: GrantFiled: August 16, 1976Date of Patent: May 24, 1977Assignee: Delalande S.A.Inventors: Claude P. Fauran, Guy R. Bourgery, Guy M. Raynaud, Claude J. Gouret
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Patent number: 4016154Abstract: A compound having the formula ##STR1## and its pharmacologically acceptable acid addition salts. The compound is prepared by condensing N-(3,4,5-trimethoxy cinnamoyl) piperazine with N-(2-pyrrolidinone) chloroacetamide. The compounds possess peripheral and coronary vasodilatatory properties and hypotensive and antihypertensive properties.Type: GrantFiled: July 15, 1975Date of Patent: April 5, 1977Assignee: Delalande S.A.Inventors: Michel J. Turin, Guy M. Raynaud, Bernard M. Pourrias, Patrick G. Guerret
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Patent number: 4013768Abstract: Compounds of the formula ##STR1## in which R is aminocarbonylphenyl in which amino is --NH.sub.2, pyrrolidino, piperidino or morpholino, and Ar is phenyl substituted with chloro, fluoro, trifluoromethyl, methylenedioxy or one or more methoxy.The compounds are prepared by 2-Ar-4-chloro-pyrimidin-6-yl ethylacetate with ##STR2## and then reacting that reaction product with hydroxylamine hydrochloride. The compounds possess vasodilatatory, anti-ulcerous, respiratory analeptic, hypotensive, diuretic, anti-depressive, analgesic, anti-inflammatory and neurotropic properties.Type: GrantFiled: March 3, 1975Date of Patent: March 22, 1977Assignee: Delalande S.A.Inventors: Claude P. Fauran, Jeannine A. Eberle, Guy R. Bourgery, Guy M. Raynaud, Claude J. Gouret
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Patent number: 4007187Abstract: Compounds of the formula ##STR1## wherein R is alkyl of 1-4 carbon atoms, phenyl, or phenyl substituted by one or more halogen or trifluoromethyl, and Z is ##STR2## wherein R.sub.1 is hydrogen, alkyl of 1-4C, 2,2-dimethyldioxolan-4-yl methyl, or 2,3-dihydroxy prop-1-yl, R.sub.2 is ##STR3## wherein ##STR4## is morpholino, pyrrolidino, piperidino or hexamethyleneimino, and n is an integer from 4 to 7. The compounds are prepared by reacting R-substituted 4-chloro-2-methyl furo (2,3d) pyrimidine with HZ. The compounds possess antiulcerous, antibronchoconstrictive and anticholinergic, analgesic, antihistamine, diuretic, cardiovascular analeptic, antiinflammatory and hypertensive properties.Type: GrantFiled: September 17, 1974Date of Patent: February 8, 1977Assignee: Delalande S.A.Inventors: Claude P. Fauran, Guy R. Bourgery, Guy M. Raynaud, Nicole A. M. Dorme
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Patent number: 3978055Abstract: Compounds of the formula ##SPC1##Wherein Ar is phenyl or phenyl substituted by one or more halogens, by a trifluoromethyl or a methylenedioxy, by one or more methoxy, by an alkyl having one to 4 carbon atoms or by a dimethylamino,And R is ##EQU1## or --O-- ##EQU2## or ##EQU3## wherein R.sub.1 and R.sub.2 each are hydrogen or alkyl of 1 to 4 carbon atoms, or ##EQU4## is pyrrolidino, morpholino, piperidino or piperazino N'-substituted by alkyl of 1 to 4 carbon atoms, or phenyl; R.sub.3 and R.sub.4 each are alkyl of 1 to 3 carbon atoms or ##EQU5## is morpholino, pyrrolidino, piperidino or hexamethyleneimino, n is an integer of 1 to 5; and R.sub.5 is alkyl of 1 to 4 carbon atoms, 2,3-dihydroxypropyl or 2,2-dimethyl dioxolan-4-yl methyl or hydroxycarbonylmethyl.Type: GrantFiled: September 3, 1974Date of Patent: August 31, 1976Assignee: Delalande S.A.Inventors: Claude P. Fauran, Guy R. Bourgery, Guy M Raynaud, Claude J. Gouret
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Patent number: 3971793Abstract: A compound of the formula ##SPC1##In which R is hydrogen, hydroxy, halogen or alkoxy containing up to 3 carbon atoms, and ##EQU1## is dialkylamino in which the alkyls contain up to 3 carbon atoms, or pyrrolidino, piperidino, morpholino or hexamethyleneimino, and n is 2 or 3. The compounds are prepared by reacting R substituted benzaldehyde with a 2,3-dihydrobenzofuran derivative and then reducing that reaction product. The compounds possess antihypertensive, hypotensive, vasodilatatory, spasmolytic, diuretic, sedative, anti-arythmic and anti-inflammatory properties.Type: GrantFiled: February 1, 1974Date of Patent: July 27, 1976Assignee: Delalande S.A.Inventors: Claude P. Fauran, Jeannine A. Eberle, Guy R. Bourgery, Guy M. Raynaud, Bernard M. Pourrias
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Patent number: 3962256Abstract: Compounds having the formula ##EQU1## WHEREIN Ar is phenyl optionally substituted by one or more halogens, alkyl having 1 to 4 carbons or alkoxy containing up to 4 carbons, and R.sub.1 and R.sub.2 each is alkyl having one to 4 carbons or ##EQU2## is piperidino, pyrrolidino, morpholino and hexamethyleneimino. The compounds are prepared by reacting the corresponding 2-chloromethyl benzimidazole with ##EQU3## The compounds possess analgesic, antihypertensive, gastric antisecretory, antiinflammatory, antibronchoconstrictive, anticholinergic, spasmolytic, sedative, antiulcerous, vasodilatatory, central nervous system stimulant, antiarythmic, diuretic and antihistaminic properties.Type: GrantFiled: June 20, 1974Date of Patent: June 8, 1976Assignee: Delalande S.A.Inventors: Claude P. Fauran, Jeannine A. Eberle, Guy M. Raynaud, Nicole A. M. Dorme
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Patent number: 3959270Abstract: A compound of the formula ##SPC1##Wherein R.sub.1 is alkyl having one to 4 carbon atoms, and R.sub.2 is (a) alkyl having one to 4 carbon atoms, or (b) alkyl having one to 4 carbon atoms and substituted by (1) dialkylamino the latter alkyl having from one to 3 carbon atoms, (2) pyrrolidino or (3) morpholino, with the proviso that when R.sub.1 is ethyl, R.sub.2 is not ethyl, propyl, or diethylamino. The compounds are prepared by reacting 2-methyl-3-alkoxycarbonyl-5-hydroxyindole with a primary amine. The compounds possess diuretic, antihypertensive, antiulcerous, antiinflammatory, sedative and analgesic properties.Type: GrantFiled: March 21, 1974Date of Patent: May 25, 1976Assignee: Delalande S.A.Inventors: Claude P. Fauran, Guy M. Raynaud, Michel J. Turin, Claude J. Gouret
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Patent number: 3951968Abstract: Compounds having the formula ##SPC1##Wherein Y is an aliphatic radical having up to 4 carbon atoms, phenyl, or phenyl substituted by one or more halogens, aliphatic radical having up to 4 carbon atoms, methoxy or trifluoromethyl.The compounds are prepared by reacting epichlorohydrin with benzimidazole substituted at the 2 position by ##EQU1## The compounds possess diuretic, sedative, antiulcerous, analgesic, antiinflammatory and cardiac analeptic properties.Type: GrantFiled: September 17, 1974Date of Patent: April 20, 1976Assignee: Delalande S.A.Inventors: Claude P. Fauran, Jeannine A. Eberle, Michel J. Turin, Guy M. Raynaud, Claude J. Gouret
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Patent number: RE29607Abstract: Compounds of the formula ##STR1## in which R is H, .[.Cl, F, CH.sub.3 or CF.sub.3 .]. .Iadd.m-F, p-F, o-F, p-Cl, p-CH.sub.3, m-CH.sub.3 or m-CF.sub.3 .Iaddend.. The compounds are prepared by cyclizing with ethyl carbonate, a compound of the formula ##STR2## The compounds have anti-depressive, myorelaxing, tranquilizing, sedative, analgesic, anti-convulsive, anti-pyretic, anti-inflammatory and uricosuric activities.Type: GrantFiled: June 4, 1976Date of Patent: April 11, 1978Assignee: Delalande S. A.Inventors: Claude P. Fauran, Guy M. Raynaud, Rene A. Oliver, Colette A. Douzon
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Patent number: RE29934Abstract: A compound of the formula ##STR1## .[.in which R is H, halogen, alkyl having 1 to 4 carbon atoms or trifluoromethyl, and R.sub.1 and R.sub.2 each is H or dialkylaminoalkyl or together with N comprise methylpiperazino..]. .Iadd.in which (1) .Iadd. ##STR2## .Iaddend. is -NH.sub.2 and R is H, m-CH.sub.3, o-CF.sub.3, m-Cl, p-Cl, m-Br, m-F, p-F, o-F, p-CH.sub.3 or m-CH.sub.3, or .Iadd. ##STR3## .Iaddend. and R is H, m-CF.sub.3 or m-F, or .Iadd. ##STR4## .Iaddend. and R is H, m-CF.sub.3 or m-F.The compound is prepared by treating the corresponding 5-hydroxymethyl compound with ammonia or an amine in the presence of phosgene.The compounds possess anti-depressive, myorelaxing, tranquilizing, sedative, analgesic, anti-convulsive, anti-pyretic, anti-inflammatory and uricosuric activities.Type: GrantFiled: March 3, 1976Date of Patent: March 13, 1979Assignee: Delalande S. A.Inventors: Claude P. Fauran, Guy M. Raynaud, Rene A. Oliver, Colette A. Douzon