The Chalcogen Is In An -oh Or -om Group (m Is Group Ia Or Group Iia Light Metal) Patents (Class 546/240)
  • Patent number: 4426386
    Abstract: 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: Grant
    Filed: December 5, 1980
    Date of Patent: January 17, 1984
    Assignee: Astra Lakemedel Aktiebolag
    Inventors: 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
  • Patent number: 4407670
    Abstract: 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: Grant
    Filed: February 23, 1981
    Date of Patent: October 4, 1983
    Assignee: National Research Development Corporation
    Inventors: Trevor A. Crabb, Graham C. Jackson, Philip A. Jupp
  • Patent number: 4408043
    Abstract: Fluorinated compounds of the formula ##STR1## are disclosed. The cationic amine compounds are useful as surfactants.
    Type: Grant
    Filed: March 8, 1982
    Date of Patent: October 4, 1983
    Assignee: Nalco Chemical Company
    Inventors: Virgil L. Seale, James R. Stanford, James E. Briscoe, Glenn S. Penny
  • Patent number: 4405737
    Abstract: 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: Grant
    Filed: February 5, 1982
    Date of Patent: September 20, 1983
    Assignee: Adeka Argus Chemical Co., Ltd.
    Inventors: Bunji Hirai, Naohiro Kubota, Kazuo Sugibuchi
  • Patent number: 4404377
    Abstract: Heterocyclic/aromatic fluorinated compounds of the formula ##STR1## are disclosed. The cationic compounds are useful as surfactants.
    Type: Grant
    Filed: March 8, 1982
    Date of Patent: September 13, 1983
    Assignee: Nalco Chemical Company
    Inventors: Virgil L. Seale, James R. Stanford, James E. Briscoe, Glenn S. Penny
  • Patent number: 4377691
    Abstract: 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: Grant
    Filed: December 4, 1980
    Date of Patent: March 22, 1983
    Assignee: Kabushiki Kaisha Cosmos Enterprise
    Inventors: Bompei Yasui, Tomohisa Miyamoto, Katsuyuki Hiraoka, Yoshitaka Sako
  • Patent number: 4342692
    Abstract: 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: Grant
    Filed: October 20, 1980
    Date of Patent: August 3, 1982
    Assignee: USV Pharmaceutical Corporation
    Inventors: John T. Suh, Rack H. Chung, Nai-Yi Wang, Jeffrey N. Barton
  • Patent number: 4332942
    Abstract: 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: Grant
    Filed: October 20, 1980
    Date of Patent: June 1, 1982
    Assignee: Pfizer, Inc.
    Inventors: Thomas H. Althuis, Charles A. Harbert, Michael R. Johnson, Lawrence S. Melvin, Jr.
  • Patent number: 4296029
    Abstract: 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: Grant
    Filed: June 23, 1980
    Date of Patent: October 20, 1981
    Assignee: John Wyeth & Brother Limited
    Inventors: Brian J. Bushell, John F. Cavalla, Robin G. Shepherd, Alan C. White
  • Patent number: 4294841
    Abstract: 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: Grant
    Filed: November 27, 1979
    Date of Patent: October 13, 1981
    Assignee: Pharmindustrie
    Inventors: Alain A. Champseix, Gerard R. Le Fur
  • Patent number: 4285957
    Abstract: 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: Grant
    Filed: October 14, 1980
    Date of Patent: August 25, 1981
    Assignee: Richardson-Merrell Inc.
    Inventors: Albert A. Carr, Joseph E. Dolfini, George J. Wright
  • Patent number: 4285958
    Abstract: 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: Grant
    Filed: October 14, 1980
    Date of Patent: August 25, 1981
    Assignee: Richardson-Merrell Inc.
    Inventors: Albert A. Carr, Joseph E. Dolfini, George J. Wright
  • Patent number: 4284635
    Abstract: 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: Grant
    Filed: November 29, 1978
    Date of Patent: August 18, 1981
    Assignee: Eli Lilly and Company
    Inventor: Dennis M. Zimmerman
  • Patent number: 4266087
    Abstract: 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: Grant
    Filed: November 13, 1978
    Date of Patent: May 5, 1981
    Assignee: Givaudan Corporation
    Inventors: Alan J. Chalk, Steven A. Magennis
  • Patent number: 4263202
    Abstract: Metal phenolates having at least one piperidinyl group sterically hindered on the nitrogen atom are suitable as additives for organic material.
    Type: Grant
    Filed: July 10, 1978
    Date of Patent: April 21, 1981
    Assignee: Ciba-Geigy Corporation
    Inventors: Michael Rasberger, Samuel Evans, Paul Moser
  • Patent number: 4260749
    Abstract: 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: Grant
    Filed: May 9, 1980
    Date of Patent: April 7, 1981
    Assignee: L'Oreal
    Inventors: Andree Bugaut, Monique Laudon
  • Patent number: 4254129
    Abstract: 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: Grant
    Filed: April 10, 1979
    Date of Patent: March 3, 1981
    Assignee: Richardson-Merrell Inc.
    Inventors: Albert A. Carr, Joseph E. Dolfini, George J. Wright
  • Patent number: 4244963
    Abstract: 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: Grant
    Filed: September 27, 1979
    Date of Patent: January 13, 1981
    Assignee: Merck & Co., Inc.
    Inventors: Nathaniel Grier, Richard A. Dybas, Bruce E. Witzel
  • Patent number: 4241071
    Abstract: Novel azacycloalkanes, azacycloalkenes and derivatives thereof and methods of preparing same are described. These compounds are useful as antidepressants, anticonvulsants, tranquilizers and analgetics.
    Type: Grant
    Filed: January 25, 1979
    Date of Patent: December 23, 1980
    Assignee: American Hoechst Corporation
    Inventors: Lawrence L. Martin, Helen H. Ong, Vernon B. Anderson, Charles A. Crichlow
  • Patent number: 4225608
    Abstract: 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: Grant
    Filed: March 16, 1979
    Date of Patent: September 30, 1980
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Jurgen Uhl, Dieter Marx, Hans-Heinrich Hausberg, Wighard Strehlow, Klaus-Otto Minck, Helmut Muller-Calgan, Christoph Seyfried
  • Patent number: 4219560
    Abstract: 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: Grant
    Filed: April 17, 1978
    Date of Patent: August 26, 1980
    Assignee: Sandoz, Inc.
    Inventor: William J. Houlihan
  • Patent number: 4210755
    Abstract: 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: Grant
    Filed: July 10, 1978
    Date of Patent: July 1, 1980
    Assignee: L'Oreal
    Inventors: Guy Vanlerberghe, Georges Rosenbaum
  • Patent number: 4199589
    Abstract: 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: Grant
    Filed: February 6, 1979
    Date of Patent: April 22, 1980
    Inventor: Jacob Szmuszkovicz
  • Patent number: 4197241
    Abstract: 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: Grant
    Filed: November 15, 1978
    Date of Patent: April 8, 1980
    Assignee: John Wyeth & Brother Limited
    Inventors: John F. Cavalla, Alan C. White
  • Patent number: 4197239
    Abstract: 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: Grant
    Filed: November 15, 1978
    Date of Patent: April 8, 1980
    Assignee: John Wyeth & Brother Limited
    Inventors: John F. Cavalla, Alan C. White, Robin G. Shepherd
  • Patent number: 4183927
    Abstract: 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: Grant
    Filed: September 13, 1977
    Date of Patent: January 15, 1980
    Assignee: The Dow Chemical Company
    Inventors: Louis E. Begin, Robert J. Broersma, Jr., George D. Dickerson, Joseph E. Dunbar
  • Patent number: 4180669
    Abstract: 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: Grant
    Filed: March 27, 1978
    Date of Patent: December 25, 1979
    Assignee: Abbott Laboratories
    Inventor: Martin Winn
  • Patent number: 4170653
    Abstract: 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: Grant
    Filed: September 1, 1977
    Date of Patent: October 9, 1979
    Assignee: Ayerst McKenna and Harrison Limited
    Inventors: Jean-Marie Ferland, Real Laliberte, Wilbur Lippmann, Thomas A. Pugsley
  • Patent number: 4157398
    Abstract: 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: Grant
    Filed: February 21, 1978
    Date of Patent: June 5, 1979
    Assignee: The Upjohn Company
    Inventor: Jacob Szmuszkovicz
  • Patent number: 4149001
    Abstract: 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: Grant
    Filed: August 18, 1978
    Date of Patent: April 10, 1979
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Joseph E. Sundeen, Frederic P. Hauck
  • Patent number: 4146630
    Abstract: 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: Grant
    Filed: October 27, 1977
    Date of Patent: March 27, 1979
    Assignee: Boehringer Mannheim GmbH
    Inventors: Wolfgang Kampe, Walter-Gunar Friebe, Fritz Wiedemann, Gisbert Sponer, Wolfgang Bartsch, Karl Dietmann
  • Patent number: 4145435
    Abstract: 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: Grant
    Filed: November 12, 1976
    Date of Patent: March 20, 1979
    Assignee: The Upjohn Company
    Inventor: Jacob Szmuszkovicz
  • Patent number: 4145362
    Abstract: 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: Grant
    Filed: May 10, 1977
    Date of Patent: March 20, 1979
    Assignee: S.A. P R B en Neerlandais PRB N.V.
    Inventors: Joseph R. Brepoels, Jean-Marie Vaneghem