The Chalcogen Is In An -oh Or -om Group (m Is Group Ia Or Group Iia Light Metal) Patents (Class 546/240)
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Patent number: 4426386Abstract: Compounds of the formula ##STR1## wherein n is 1 or 2, Y is OH, R.sup.1 COO--, R.sup.2 R.sup.3 NCOO-- or R.sup.4 O whereby R.sup.1 is an alkyl group, or a possibly substituted phenyl group, R.sup.2 is an alkyl, phenethyl, benzyl or phenyl group, R.sup.3 is H or an alkyl group and R.sup.4 is an allyl or benzyl group, and R is an alkyl, hydroxyalkyl, dimethylaminoalkyl or methylthioalkyl group or alkenyl group, processes for their preparation and pharmaceutical preparations and methods of treatment employing such compounds. The compounds are useful for therapeutic purposes, especially for treatment of disorders in the central nervous system.Type: GrantFiled: December 5, 1980Date of Patent: January 17, 1984Assignee: Astra Lakemedel AktiebolagInventors: Folke L. Arvidsson, Per A. E. Carlsson, Uli A. Hacksell, John S. M. Hjorth, Per. L. Lindberg, John L. G. Nilsson, Domingo Sanchez, Nils U. E. Svensson, Hakan V. Wikstrom
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Patent number: 4407670Abstract: Biocidal compositions and methods of inhibiting biological growth employ, as the active agent, certain monocyclic and bicyclic heterocyclic compounds, some novel perse, of general formula I ##STR1## in which X is 0,1 or 2, R.sup.1, R.sup.2, R.sup.5 and R.sup.6 are a hydrogen atom, an alkyl radical containing up to 20 carbon atoms or an aryl radical; R.sup.3 is a hydrogen atom or a lower alkyl radical containing up to 6 carbon atoms; and R.sup.7 and R.sup.8, when taken separately, are hydrogen atoms or, when taken together, are ##STR2## in which R.sup.4 is a hydrogen atom, an alkyl radical containing up to 16 carbon atoms or an aryl radical.The preferred active agents generally have low solubility in sea water, are toxic to algal, barnacle or fungal growth, and are colorless. They may be used to form anti-fouling paints free from undesirable heavy metals or as anti-fungal additives in hydrocarbon fuels.Type: GrantFiled: February 23, 1981Date of Patent: October 4, 1983Assignee: National Research Development CorporationInventors: Trevor A. Crabb, Graham C. Jackson, Philip A. Jupp
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Patent number: 4408043Abstract: Fluorinated compounds of the formula ##STR1## are disclosed. The cationic amine compounds are useful as surfactants.Type: GrantFiled: March 8, 1982Date of Patent: October 4, 1983Assignee: Nalco Chemical CompanyInventors: Virgil L. Seale, James R. Stanford, James E. Briscoe, Glenn S. Penny
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Patent number: 4405737Abstract: N-2-Hydroxypropyl piperidines are provided, as well as a process for preparing these compounds, having the formula: ##STR1## wherein X is selected from the group consisting of , ##STR2## wherein R.sub.1 is selected from the group consisting of hydrogen; alkyl; alkenyl; cycloalkyl; alkaryl; hydroxyalkyl; oxyalkyl; acyl and aroyl having from one to about eighteen carbon atoms;R.sub.2 and R.sub.3 are each selected from the group consisting of alkyl, alkenyl, cycloalkyl, alkaryl, hydroxyalkyl, oxyalkyl and haloalkyl having from one to about eighteen carbon atoms;R.sub.4, R.sub.5 and R.sub.6 each are selected from the group consisting of hydrogen, alkyl, alkenyl, cycloalkyl, alkaryl, hydroxyalkyl, oxyalkyl and haloalkyl having from one to about eighteen carbon atoms; and --CH.sub.2 --O--R.sub.1 ;n is 1 or 2; andY, when n is 1, is hydroxy or ##STR3## and when n is 2, is oxyoxygen.Type: GrantFiled: February 5, 1982Date of Patent: September 20, 1983Assignee: Adeka Argus Chemical Co., Ltd.Inventors: Bunji Hirai, Naohiro Kubota, Kazuo Sugibuchi
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Patent number: 4404377Abstract: Heterocyclic/aromatic fluorinated compounds of the formula ##STR1## are disclosed. The cationic compounds are useful as surfactants.Type: GrantFiled: March 8, 1982Date of Patent: September 13, 1983Assignee: Nalco Chemical CompanyInventors: Virgil L. Seale, James R. Stanford, James E. Briscoe, Glenn S. Penny
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Patent number: 4377691Abstract: A process for the preparation of 1-(4-hydroxyphenyl)-2-(4-benzylpiperidino)-1-propanol (i.e. ifenprodil) and acid-addition salts thereof, characterized by brominating 4'-hydroxypropiophenone in a single or mixed solvent selected from the group consisting of methanol, ethanol and a saturated aliphatic ether, removing hydrogen bromide formed in the course of the bromination, adding 4-benzylpyridine to the reaction mixture, heating the reaction mixture under reflux in a single or mixed solvent selected from the group consisting of methanol and ethanol, and then subjecting the resultant reaction mixture to catalytic reduction to form 1-(4-hydroxyphenyl)-2-(4-benzylpiperidino)-1-propanol hydrobromide in the reaction mixture. The end product (i.e.Type: GrantFiled: December 4, 1980Date of Patent: March 22, 1983Assignee: Kabushiki Kaisha Cosmos EnterpriseInventors: Bompei Yasui, Tomohisa Miyamoto, Katsuyuki Hiraoka, Yoshitaka Sako
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Patent number: 4342692Abstract: Compounds of the formulae: ##STR1## wherein, Z and Y are each alkylene containing one to about five carbon atoms in the principal chain or said alkylene substituted with OH, alkanoyloxy, alkoxy, mercapto or alkylmercapto;each of R.sub.1, R.sub.2 and R.sub.3 is independently H, alkyl, aryl, halo, alkoxy, alkenyloxy, alkylsulfinyl, alkylsulfonyl, alkylmercapto, cyano, carboxy, carbalkoxy, carboxamido, sulfamoyl, trifluoromethyl, hydroxy, hydroxyalkyl, acyloxy, alkylamino, sulfonylamino, or acylamino; and R.sub.1 and R.sub.2, when taken together, form a methylenedioxy or --O--CO--O--;Ar is heteroaryl, cycloalkyl or ##STR2## wherein, R.sub.1, R.sub.2 and R.sub.3 are as hereindescribed; andR is H, alkyl, cycloalkyl, aryl, aralkyl, alkenyl, alkynyl, carboalkoxy, or CONR.sub.4 R.sub.5 wherein each of R.sub.4 and R.sub.5 is H or alkyl; wherein the total number of carbon atoms in each hydrocarbyl group is up to 10;and ##STR3## wherein, each of R.sub.1 and R.sub.Type: GrantFiled: October 20, 1980Date of Patent: August 3, 1982Assignee: USV Pharmaceutical CorporationInventors: John T. Suh, Rack H. Chung, Nai-Yi Wang, Jeffrey N. Barton
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Patent number: 4332942Abstract: Azacycloalkanes, and derivatives thereof, including unsaturated analogs, each of which has at the 3-position a 2-hydroxy-4-substituted phenyl group wherein the 4-position substituent is alkyl which can have an oxygen atom as part of the chain, or aralkyl which can have an oxygen atom as part of the alkyl chain, their use for pharmacological and medicinal purposes, intermediates therefor and processes for their preparation.Type: GrantFiled: October 20, 1980Date of Patent: June 1, 1982Assignee: Pfizer, Inc.Inventors: Thomas H. Althuis, Charles A. Harbert, Michael R. Johnson, Lawrence S. Melvin, Jr.
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Patent number: 4296029Abstract: 2-Oxo-hexahydroazepine, -piperidine or pyrrolidines of formula ##STR1## wherein n is 2,3 or 4, R is hydrogen, lower alkyl, aryl(lower)alkyl, loweralkenylmethyl or cycloalkylmethyl, R.sup.1 is hydrogen or lower alkyl and R.sup.2 is hydrogen, lower alkyl or aryl(lower)alkyl are prepared by a novel process involving reaction of an anion of a lactam of formula ##STR2## where R.sup.3 is lower alkyl, aryl(lower)alkyl, trialkyl-, triaryl- or triarylalkyl-silyl with a benzyne of formula ##STR3## where R.sup.4 is lower alkyl, aryl(lower)alkyl or trialkyl-, triaryl- or triarylalkyl-silyl. The products are useful as intermediates for preparing pharmacologically active 2-unsubstituted -hexahydroazepine, -piperidine and pyrrolidine derivatives.Type: GrantFiled: June 23, 1980Date of Patent: October 20, 1981Assignee: John Wyeth & Brother LimitedInventors: Brian J. Bushell, John F. Cavalla, Robin G. Shepherd, Alan C. White
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Patent number: 4294841Abstract: A drug useful as antiarhythmic, antidepressant and anxiolytic containing as an active agent a compound of the formula ##STR1## wherein X and Y are the same or different and represent hydrogen or halogen atoms, or 1-4C alkyl groups, 1-4C alkoxy groups, 1-4C alkylthio groups, CF.sub.3, OH, NH.sub.2, 1-4C monoalkylamino or amino groups substituted by a 1-4C alkylsulfonyl group, a 1-5C alkylcarbonyl group or an aroyl group and A is a CO, CHOH or CH.sub.2 group, or a salt of said compound with a pharmaceutically acceptable acid, is disclosed together with methods for the preparation thereof and its use in human therapy.Type: GrantFiled: November 27, 1979Date of Patent: October 13, 1981Assignee: PharmindustrieInventors: Alain A. Champseix, Gerard R. Le Fur
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Patent number: 4285957Abstract: Novel compounds of the following formula: ##STR1## wherein R.sub.1 is hydrogen or hydroxy; R.sub.2 is hydrogen; or R.sub.1 and R.sub.2 taken together form a second bond between the carbon atoms bearing R.sub.1 and R.sub.2 ; n is an integer of from 1 to 5; R.sub.3 is --CH.sub.3, --CH.sub.2 OH, --COOH or --COOalkyl wherein the alkyl moiety has from 1 to 6 carbon atoms and is straight or branched; and each of A and B is hydrogen or hydroxy; with the provisos that at least one of A or B is hydrogen and one of A or B is other than hydrogen when R.sub.3 is --CH.sub.3 ; and pharmaceutically acceptable salts thereof.Type: GrantFiled: October 14, 1980Date of Patent: August 25, 1981Assignee: Richardson-Merrell Inc.Inventors: Albert A. Carr, Joseph E. Dolfini, George J. Wright
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Patent number: 4285958Abstract: Pharmaceutically useful compounds of the following formula: ##STR1## wherein R.sub.1 represents hydrogen or hydroxy; R.sub.2 represents hydrogen; or R.sub.1 and R.sub.2 taken together form a second bond between the carbon atoms bearing R.sub.1 and R.sub.2 ; n is a positive whole integer of from 1 to 5; R.sub.3 is --CH.sub.3, --CH.sub.2 OH, --COOH or --COOalkyl wherein the alkyl moiety has from 1 to 6 carbon atoms and is straight or branched; and A and B are individually hydrogen or hydroxy; with the provisos that at least one of A or B is hydrogen and one of A or B is other than hydrogen when R.sub.3 is --CH.sub.3 ; and pharmaceutically acceptable acid addition salts thereof.Type: GrantFiled: October 14, 1980Date of Patent: August 25, 1981Assignee: Richardson-Merrell Inc.Inventors: Albert A. Carr, Joseph E. Dolfini, George J. Wright
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Patent number: 4284635Abstract: 4-Phenylpiperidines bearing substituents at the 1,2,4 and 5-positions are potent analgesics. Pharmaceutical formulations containing such compounds and a method for effecting analgesia are provided.Type: GrantFiled: November 29, 1978Date of Patent: August 18, 1981Assignee: Eli Lilly and CompanyInventor: Dennis M. Zimmerman
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Patent number: 4266087Abstract: The instant invention provides a new and improved method of preparing the Diels Alder mixture of 3 and 4-(4-methyl-4-hydroxyamyl).DELTA..sup.3 -cyclohexenecarboxaldehyde from the readily available myrcene. The novel sequence includes a synthesis of a novel myrcenol, ocimenol intermediate which is substantially free of trans-ocimenol.Type: GrantFiled: November 13, 1978Date of Patent: May 5, 1981Assignee: Givaudan CorporationInventors: Alan J. Chalk, Steven A. Magennis
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Patent number: 4263202Abstract: Metal phenolates having at least one piperidinyl group sterically hindered on the nitrogen atom are suitable as additives for organic material.Type: GrantFiled: July 10, 1978Date of Patent: April 21, 1981Assignee: Ciba-Geigy CorporationInventors: Michael Rasberger, Samuel Evans, Paul Moser
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Patent number: 4260749Abstract: 2,5-diamino-1,4-benzoquinones are used in the production of hair dye compositions and can be prepared by condensing a corresponding 3-amino-4-methoxy phenol derivative on one of a corresponding hydroxy aniline or phenylenediamine derivative, a corresponding benzoquinone imine derivative or a corresponding nitroso derivative.Type: GrantFiled: May 9, 1980Date of Patent: April 7, 1981Assignee: L'OrealInventors: Andree Bugaut, Monique Laudon
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Patent number: 4254129Abstract: Novel compounds of the following formula: ##STR1## wherein R.sub.1 is hydrogen or hydroxy; R.sub.2 is hydrogen; or R.sub.1 and R.sub.2 taken together form a second bond between the carbon atoms bearing R.sub.1 and R.sub.2 ; n is an integer of from 1 to 5; R.sub.3 is --CH.sub.3, --CH.sub.2 OH, --COOH or --COOalkyl wherein the alkyl moiety has from 1 to 6 carbon atoms and is straight or branched; and each of A and B is hydrogen or hydroxy; with the provisos that at least one of A or B is hydrogen and one of A or B is other than hydrogen when R.sub.3 is --CH.sub.3 ; and pharmaceutically acceptable salts thereof.Type: GrantFiled: April 10, 1979Date of Patent: March 3, 1981Assignee: Richardson-Merrell Inc.Inventors: Albert A. Carr, Joseph E. Dolfini, George J. Wright
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Patent number: 4244963Abstract: 1-[2-(Alkyl and arylsulfonyl)-2-propenyl and propyl] substituted piperidines of the formula: ##STR1## where A is ##STR2## and R.sub.1 -R.sub.5 are various substituents, are useful as antimicrobial and anti-inflammatory agents.Type: GrantFiled: September 27, 1979Date of Patent: January 13, 1981Assignee: Merck & Co., Inc.Inventors: Nathaniel Grier, Richard A. Dybas, Bruce E. Witzel
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Patent number: 4241071Abstract: Novel azacycloalkanes, azacycloalkenes and derivatives thereof and methods of preparing same are described. These compounds are useful as antidepressants, anticonvulsants, tranquilizers and analgetics.Type: GrantFiled: January 25, 1979Date of Patent: December 23, 1980Assignee: American Hoechst CorporationInventors: Lawrence L. Martin, Helen H. Ong, Vernon B. Anderson, Charles A. Crichlow
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Patent number: 4225608Abstract: Phenoxyalkylamines of the formulaAr--O--Rwherein Ar is phenyl or phenyl which is monosubstituted or disubstituted by F, Cl, Br, alkyl or alkoxy each of 1-4 carbon atoms, cycloalkoxy of 3-6 carbon atoms, CF.sub.3, CN, alkylthio of 1-4 carbon atoms, SCF.sub.3, OH and/or alkanoyloxy with 1-10 carbon atoms; R is (1-R.sup.1 -2-pyrrolidyl)--CH.sub.2 --CHR.sup.2 --, (1-R.sup.1 -2-piperidyl)-CH.sub.2 --CHR.sup.2 -- or 1-R.sup.1 -3-Z-4-hexahydroazepinyl; R.sup.1 is H, alkyl or alkenyl each of up to 4 carbon atoms, cyclopropylmethyl or benzyl; R.sup.2 is H, alkyl of 1-4 carbon atoms or phenyl; and Z is alkyl of 1-4 carbon atoms with the proviso that Ar is p-fluorophenyl only if R is not 2-(1-methyl-2-piperidyl)-ethyl; and the physiologically acceptable acid addition salts thereof, possess valuable pharmacological properties, e.g., are antidepressants.Type: GrantFiled: March 16, 1979Date of Patent: September 30, 1980Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Jurgen Uhl, Dieter Marx, Hans-Heinrich Hausberg, Wighard Strehlow, Klaus-Otto Minck, Helmut Muller-Calgan, Christoph Seyfried
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Patent number: 4219560Abstract: This disclosure describes novel compounds of the formula: ##STR1## where A is --CH.sub.2 OH or ##STR2## wherein R.sub.4 and R.sub.5 each independently represent hydrogen or lower alkyl having 1 to 2 carbon atoms or together with N represent ##STR3## and, R.sub.1 is hydrogen or lower alkyl having 1 to 2 carbon atoms, andR.sub.2 and R.sub.3 each independently represent hydrogen, chloro, fluoro, methyl, methoxy or together, represent methylenedioxy, andn is 1 or 2, provided that one of R.sub.2 and R.sub.3 is other than hydrogen which are useful as hypolipidemic agents.Type: GrantFiled: April 17, 1978Date of Patent: August 26, 1980Assignee: Sandoz, Inc.Inventor: William J. Houlihan
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Patent number: 4210755Abstract: Aminated .gamma.-dialdehyde and the quaternary ammonium salts thereof are prepared by acid hydrolysis of their respective corresponding 2,5-dialkoxy 3-amino 4-hydroxy tetrahydrofurans or by acid hydrolysis of their respective corresponding tetraalkyl acetals. The aminated .gamma.-dialdehydes and the quaternary ammonium salts thereof are usefully employed in cosmetic compositions to tan the skin or to strengthen or restructure the hair.Type: GrantFiled: July 10, 1978Date of Patent: July 1, 1980Assignee: L'OrealInventors: Guy Vanlerberghe, Georges Rosenbaum
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Patent number: 4199589Abstract: N-(2-aminocycloheptyl)-N-alkanoylanilides and their 2-N-oxides of the formula ##STR1## e.g., trans-3,4-dichloro-N-[2-(dimethylamino)cycloheptyl]acrylanilide, and their pharmacologically acceptable salts, have been found to possess potent Central Nervous System anti-depressant properties. Many of them are new.These compounds are promising anti-depressant drugs which are characterized by lower toxicity than imipramine, and long acting activity which may allow longer durations between administrations, e.g., once a day. Pharmaceutical compositions containing these compounds and a process for treating conditions of depression with these compositions are disclosed.Type: GrantFiled: February 6, 1979Date of Patent: April 22, 1980Inventor: Jacob Szmuszkovicz
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Patent number: 4197241Abstract: The invention concerns novel 2-oxo-hexahydroazepine, -piperidine and -pyrrolidine derivatives of formula (I) and their aromatized derivatives of formula (II) ##STR1## where n is 2, 3 or 4, R is hydrogen, lower alkyl or aryl(lower)alkyl, R.sup.2 is hydrogen, lower alkyl or aryl(lower)alkyl and R.sup.3 is hydrogen, lower alkyl, aryl(lower)alkyl, lower alkenyl or lower alkynyl. The compounds are useful as intermediates for preparing 3,3-disubstituted -hexahydroazepine, -piperidine and -pyrrolidine compounds having pharmacological activity, particularly analgesic activity.Type: GrantFiled: November 15, 1978Date of Patent: April 8, 1980Assignee: John Wyeth & Brother LimitedInventors: John F. Cavalla, Alan C. White
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Patent number: 4197239Abstract: The invention concerns novel 2-oxo-hexahydroazepine, -piperidine and -pyrrolidine of formula I ##STR1## where n is 2,3 or 4, R is hydrogen, lower alkyl or aryl(lower)alkyl and R.sup.1 is lower alkyl. The compounds may be aromatized and the aromatized compounds converted to 3,3-disubstituted-hexahydroazepine, -piperidine and -pyrrolidine compounds having pharmacological activity, particularly analgesic activity.Type: GrantFiled: November 15, 1978Date of Patent: April 8, 1980Assignee: John Wyeth & Brother LimitedInventors: John F. Cavalla, Alan C. White, Robin G. Shepherd
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Patent number: 4183927Abstract: Novel substituted phenylthioalkylamines, salts and pharmaceutical compositions thereof wherein the sulfur may appear as a sulfide, sulfinyl or sulfonyl are disclosed as antithrombotic agents.Type: GrantFiled: September 13, 1977Date of Patent: January 15, 1980Assignee: The Dow Chemical CompanyInventors: Louis E. Begin, Robert J. Broersma, Jr., George D. Dickerson, Joseph E. Dunbar
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Patent number: 4180669Abstract: This invention provides 2-(N-substituted piperidino)-5-alkyl resorcinols of the structure ##STR1## wherein R.sub.1 is H, loweralkyl, loweralkynyl or aralkyl; R.sub.2 and R.sub.3 are each H or when taken together R.sub.2 R.sub.3 =CH.sub.2 CH.sub.2 ; R.sub.4 is a C.sub.1 -C.sub.10 alkyl and R.sub.5 is H or loweralkyl, and the pharmaceutically acceptable salts thereof.These compounds are useful as antisecretory agents.Type: GrantFiled: March 27, 1978Date of Patent: December 25, 1979Assignee: Abbott LaboratoriesInventor: Martin Winn
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Patent number: 4170653Abstract: Disclosed herein are compounds of the formula ##STR1## in which Ar is phenyl or 1-naphthyl; R.sup.1 is hydrogen or lower alkyl; and R.sup.2 and R.sup.3 together with the nitrogen atom to which they are joined form a heterocyclic amine radical selected from the group consisting of 1-pyrrolidinyl, piperidino, morpholino and 4-(lower alkyl)-1-piperazinyl. The compounds are antidepressant agents and methods for their preparation and use also are disclosed.Type: GrantFiled: September 1, 1977Date of Patent: October 9, 1979Assignee: Ayerst McKenna and Harrison LimitedInventors: Jean-Marie Ferland, Real Laliberte, Wilbur Lippmann, Thomas A. Pugsley
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Patent number: 4157398Abstract: N-(2-Aminocyclopentyl)N-alkanoylanilides and their 2-N-oxides of the formula ##STR1## e.g., trans-3,4-dichloro-N-[2-(dimethylamino)cyclopentyl]propionanilide, and their pharmacologically acceptable salts, have been found to possess potent Central Nervous System anti-depressant properties. Many of them are new.These compounds are promising anti-depressant drugs which are characterized by a better therapeutic ratio than imipramine, and long acting activity which may allow longer durations between administrations, e.g., once a day. Pharmaceutical compositions containing these compounds and a process for treating conditions of depression with these compositions are disclosed.Type: GrantFiled: February 21, 1978Date of Patent: June 5, 1979Assignee: The Upjohn CompanyInventor: Jacob Szmuszkovicz
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Patent number: 4149001Abstract: Compounds of the formula ##STR1## wherein R is hydrogen, ##STR2## lower alkyl, ##STR3## R.sub.1 and R.sub.2 are independently selected from hydrogen, lower alkyl, and cycloalkyl or R.sub.1 and R.sub.2 taken together with the nitrogen atom to which they are attached from a ring of the formula ##STR4## N IS 0 OR AN INTEGER FROM 1 TO 3; M IS AN INTEGER FROM 1 TO 3; R.sub.3 and R.sub.4 are independently selected from hydrogen and lower alkyl; X is hydrogen, halogen, lower alkyl, lower alkoxy, or nitro; and their salts; are disclosed. These compounds possess useful antiinflammatory properties.Type: GrantFiled: August 18, 1978Date of Patent: April 10, 1979Assignee: E. R. Squibb & Sons, Inc.Inventors: Joseph E. Sundeen, Frederic P. Hauck
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Patent number: 4146630Abstract: A 3-(4-phenoxymethylpiperidino)-propyl-phenyl-ether of the formula ##STR1## wherein R.sub.1 and R.sub.2 each independently is hydrogen, lower alkyl, hydroxyalkyl, lower alkanoyloxyalkyl or --CO--Z,Z is hydroxy, lower alkyloxy or ##STR2## R.sub.6 and R.sub.7 each independently is hydrogen, lower alkyl or hydroxyalkyl,R.sub.3 is hydrogen or --O--R.sub.8,R.sub.8 is hydrogen, lower alkanoyl or aroyl optionally substituted by halogen, lower alkyl, lower alkoxy, alkoxycarbonyl, hydroxyl, alkylthio, nitrile, nitro or trifluoromethyl,R.sub.4 and R.sub.5 each independently is hydrogen, halogen, hydroxy, benzyloxy, lower alkyl, lower alkoxy, lower alkylthio, carboxy, benzyloxycarbonyl or lower alkoxycarbonyl,X and Y each independently is nitrogen or ##STR3## R.sub.9 is hydrogen, lower allkyl optionally substituted by --O--R.sub.8, or --CO--Z,or a pharmacologically acceptable salt thereof. The compounds lower blood pressure and inhibit adrenergic .beta.-receptors.Type: GrantFiled: October 27, 1977Date of Patent: March 27, 1979Assignee: Boehringer Mannheim GmbHInventors: Wolfgang Kampe, Walter-Gunar Friebe, Fritz Wiedemann, Gisbert Sponer, Wolfgang Bartsch, Karl Dietmann
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Patent number: 4145435Abstract: Cis- and trans-N-(2-aminocycloaliphatic)-2-arylacetamide derivative compounds of the formula ##STR1## e.g., N-?2-(N', N'-dimethylamino)cyclohexyl!-N-methyl-2-(4-bromophenyl)acetamide and trans-N-methyl-N-?2-(1-pyrrolidinyl)cyclohexyl!acetamide, 2-(3,4-dichlorophenyl) and their pharmaceutically acceptable salts, have been found to have potent analgesic activity, and the preferred compounds have in addition only low to moderate apparent physical dependence liability, compared to morphine and methadone. As analgesics they would be useful also as antitussives. Processes for preparation of these compounds are also disclosed. This invention also includes compositions containing these compounds useful in pharmaceutical dosage unit form for alleviating pain in humans and animals, as well as methods for alleviating pain in animals and humans with these compositions.Type: GrantFiled: November 12, 1976Date of Patent: March 20, 1979Assignee: The Upjohn CompanyInventor: Jacob Szmuszkovicz
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Patent number: 4145362Abstract: A process for arylating an olefinic compound by addition of an aryl group to a double bond of said olefinic compound consisting in diazotizing an arylamine in an aqueous acidic solution comprising a lower alkanoic acid to form a solution of an aryldiazonium salt and reacting said aryldiazonium salt solution with an olefinic compound in an organic solvent in the presence of a catalytically effective amount of a copper halide.The amount of alkanoic acid is about 15 to 37% by volume of the total solvents used. The alkanoic acid is preferably acetic acid and the copper halide cuprous chloride.Type: GrantFiled: May 10, 1977Date of Patent: March 20, 1979Assignee: S.A. P R B en Neerlandais PRB N.V.Inventors: Joseph R. Brepoels, Jean-Marie Vaneghem