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).

  • Patent number: 4104384
    Abstract: 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: Grant
    Filed: November 28, 1977
    Date of Patent: August 1, 1978
    Assignee: Delalande S.A.
    Inventors: Claude P. Fauran, Michel J. Turin, Thierry F. Imbert, Guy M. Raynaud, Nicole A. M. Dorme
  • Patent number: 4072682
    Abstract: 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: Grant
    Filed: December 22, 1975
    Date of Patent: February 7, 1978
    Assignee: Delalande S.A.
    Inventors: Claude P. Fauran, Michel J. Turin, Thierry F. Imbert, Guy M. Raynaud, Nicole A. M. Dorme
  • Patent number: 4049658
    Abstract: 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: Grant
    Filed: December 6, 1976
    Date of Patent: September 20, 1977
    Assignee: Delalande S.A.
    Inventors: Claude P. Fauran, Guy M. Raynaud, Michel J. Turin, Janine M. Thomas
  • Patent number: 4049660
    Abstract: 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: Grant
    Filed: December 6, 1976
    Date of Patent: September 20, 1977
    Assignee: Delalande S.A.
    Inventors: Claude P. Fauran, Guy M. Raynaud, Michel J. Turin, Janine M. Thomas
  • Patent number: 4048164
    Abstract: 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: Grant
    Filed: January 16, 1975
    Date of Patent: September 13, 1977
    Assignee: Delalande S.A.
    Inventors: Claude P. Fauran, Guy M. Raynaud, Michel J. Turin, Janine M. Thomas
  • Patent number: 4041030
    Abstract: 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: Grant
    Filed: August 16, 1976
    Date of Patent: August 9, 1977
    Assignee: Delalande S.A.
    Inventors: Claude P. Fauran, Guy R. Bourgery, Guy M. Raynaud, Claude J. Gouret
  • Patent number: 4031089
    Abstract: 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: Grant
    Filed: August 18, 1976
    Date of Patent: June 21, 1977
    Assignee: Delalande S.A.
    Inventors: Claude P. Fauran, Guy R. Bourgery, Guy M. Raynaud, Nicole A. M. Dorme
  • Patent number: 4029789
    Abstract: 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: Grant
    Filed: November 20, 1975
    Date of Patent: June 14, 1977
    Assignee: Delalande S.A.
    Inventors: Claude P. Fauran, Nicole Dorme, Guy M. Raynaud, Jeannine Eberle
  • Patent number: 4029650
    Abstract: 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: Grant
    Filed: November 20, 1975
    Date of Patent: June 14, 1977
    Assignee: Delalande S. A.
    Inventors: Guy M. Raynaud, Bernard M. Pourrias, Claude P. Fauran, Michel J. Turin
  • Patent number: 4025514
    Abstract: 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: Grant
    Filed: August 16, 1976
    Date of Patent: May 24, 1977
    Assignee: Delalande S.A.
    Inventors: Claude P. Fauran, Guy R. Bourgery, Guy M. Raynaud, Claude J. Gouret
  • Patent number: 4016154
    Abstract: 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: Grant
    Filed: July 15, 1975
    Date of Patent: April 5, 1977
    Assignee: Delalande S.A.
    Inventors: Michel J. Turin, Guy M. Raynaud, Bernard M. Pourrias, Patrick G. Guerret
  • Patent number: 4013768
    Abstract: 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: Grant
    Filed: March 3, 1975
    Date of Patent: March 22, 1977
    Assignee: Delalande S.A.
    Inventors: Claude P. Fauran, Jeannine A. Eberle, Guy R. Bourgery, Guy M. Raynaud, Claude J. Gouret
  • Patent number: 4007187
    Abstract: 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: Grant
    Filed: September 17, 1974
    Date of Patent: February 8, 1977
    Assignee: Delalande S.A.
    Inventors: Claude P. Fauran, Guy R. Bourgery, Guy M. Raynaud, Nicole A. M. Dorme
  • Patent number: 3978055
    Abstract: 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: Grant
    Filed: September 3, 1974
    Date of Patent: August 31, 1976
    Assignee: Delalande S.A.
    Inventors: Claude P. Fauran, Guy R. Bourgery, Guy M Raynaud, Claude J. Gouret
  • Patent number: 3971793
    Abstract: 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: Grant
    Filed: February 1, 1974
    Date of Patent: July 27, 1976
    Assignee: Delalande S.A.
    Inventors: Claude P. Fauran, Jeannine A. Eberle, Guy R. Bourgery, Guy M. Raynaud, Bernard M. Pourrias
  • Patent number: 3962256
    Abstract: 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: Grant
    Filed: June 20, 1974
    Date of Patent: June 8, 1976
    Assignee: Delalande S.A.
    Inventors: Claude P. Fauran, Jeannine A. Eberle, Guy M. Raynaud, Nicole A. M. Dorme
  • Patent number: 3959270
    Abstract: 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: Grant
    Filed: March 21, 1974
    Date of Patent: May 25, 1976
    Assignee: Delalande S.A.
    Inventors: Claude P. Fauran, Guy M. Raynaud, Michel J. Turin, Claude J. Gouret
  • Patent number: 3951968
    Abstract: 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: Grant
    Filed: September 17, 1974
    Date of Patent: April 20, 1976
    Assignee: Delalande S.A.
    Inventors: Claude P. Fauran, Jeannine A. Eberle, Michel J. Turin, Guy M. Raynaud, Claude J. Gouret
  • Patent number: RE29607
    Abstract: 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: Grant
    Filed: June 4, 1976
    Date of Patent: April 11, 1978
    Assignee: Delalande S. A.
    Inventors: Claude P. Fauran, Guy M. Raynaud, Rene A. Oliver, Colette A. Douzon
  • Patent number: RE29934
    Abstract: 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: Grant
    Filed: March 3, 1976
    Date of Patent: March 13, 1979
    Assignee: Delalande S. A.
    Inventors: Claude P. Fauran, Guy M. Raynaud, Rene A. Oliver, Colette A. Douzon