Acyclic Nitrogen Bonded Directly To A -c(=x)- Group, Wherein X Is Chalcogen Patents (Class 546/224)
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Patent number: 4716187Abstract: both R.sub.1 's and CH.sub.3 or together form --CH.sub.2).sub.5 ;both R.sub.2 's are CH.sub.3 or together form --CH.sub.2).sub.5 ;R.sub.3 has a significance of R, independently of R, except for oxygen;X is --O--, --NH-- or ##STR2## m is an integer from 1 to 4 inclusive; R.sub.4 is a saturated or unsaturated aliphatic group unsubstituted or substituted by one or two groups selected from --OH and C.sub.1-4 alkoxy and which can be interrupted by an oxygen or sulphur atom; or an aromatic group unsubstituted or substituted by one or two groups selected from --OH, C.sub.1-4 alkyl and C.sub.1-4 alkoxy are useful as U.V. light stabilizers in polymeric organic compounds.Type: GrantFiled: March 15, 1985Date of Patent: December 29, 1987Assignee: Sandoz Ltd.Inventor: Lajos Avar
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Patent number: 4647560Abstract: The present invention relates to novel benzodiazepines, acid addition salts thereof, processes for their preparation and their use in combating diseases, in particular for the treatment of cerebral disorders caused by old age and for the treatment of disorders in learning and memory and amnesia.Type: GrantFiled: August 8, 1985Date of Patent: March 3, 1987Assignee: Troponwerke GMBH & Co. KGInventors: Karl-Heinz Boltze, Eugen Etschenberg, Jorg Traber, Herbert Busgen
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Patent number: 4642384Abstract: Processes and intermediates for the preparation of the antiarrhythmic agent 2,5-bis(2,2,2-trifluoroethoxy)-N-(2-piperidylmethyl)benzamide.Type: GrantFiled: September 4, 1985Date of Patent: February 10, 1987Assignee: Riker Laboratories, Inc.Inventor: Charles M. Leir
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Patent number: 4617396Abstract: Processes for the preparation of the antiarrhythmic agent 2,5-bis(2,2,2-trifluoroethoxy)-N-(2-piperidylmethyl)benzamide.Type: GrantFiled: September 4, 1985Date of Patent: October 14, 1986Assignee: Riker Laboratories, Inc.Inventor: Charles M. Leir
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Patent number: 4603138Abstract: Compounds of the formula (I): ##STR1## and pharmaceutically acceptable acid addition salts thereof, wherein,Ar is optionally substituted phenyl or naphthyl, or pyridyl;E is O, S or a bond;R.sub.5 is hydrogen, andJ is C.sub.3-5 polymethylene, optionally substituted by one or two groups selected from methyl or optionally derivatized hydroxy; orAr and R.sub.5 together form a group ##STR2## where Ar.sup.1 is optionally substituted 1,2-phenylene;Z is O or CH.sub.2, andm is 0 or 1, when E is O or S, or 1 when E is bond;R.sub.1 is hydrogen, C.sub.1-4 alkyl optionally substituted phenyl; C.sub.3-8 alkanoyl, or phenyl C.sub.2-8 alkanoyl, any phenyl moiety being optionally substituted; a group COR.sub.2 where R.sub.2 is C.sub.2-3 alkoxy, phenyl C.sub.1-4 alkoxy, the phenyl moiety being optionally substituted, or C.sub.1-4 alkoxy C.sub.3-4 alkoxy; or a group CXNHR.sub.3 where X is O or S and R.sub.3 is C.sub.2-4 alkyl, C.sub.2-4 alkenyl, phenyl or phenyl C.sub.Type: GrantFiled: June 9, 1983Date of Patent: July 29, 1986Assignee: Beecham Wuelfing GmbH & Co. KGInventor: Harald Maschler
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Patent number: 4584303Abstract: Compounds are disclosed of the formula ##STR1## optically active isomeric forms thereof, and/or pharmaceutically acceptable acid addition salts thereof, in which formula: R is defined in the disclosure.Type: GrantFiled: April 17, 1985Date of Patent: April 22, 1986Assignee: The BOC Group, Inc.Inventors: Bao-Shan Huang, Ross C. Terrell, Kirsten H. Deutsche, Linas V. Kudzma, Nhora L. Lalinde
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Patent number: 4560684Abstract: 1,4-Benzodiazepine derivatives of the formula: ##STR1## (in which R.sup.1 is pyrrolidinyl or piperidinyl each optionally substituted by C.sub.1-3 alkyl, phenyl-C.sub.1-3 alkyl, C.sub.1-5 alkanoyl, or C.sub.2-5 alkoxycarbonyl,R.sup.2 is hydrogen, hydroxy, or acetoxy,R.sup.3 is C.sub.1-3 alkyl, phenyl-C.sub.1-3 alkyl, or phenyl optionally substituted by one or two halogens,X is hydrogen, halogen, C.sub.1-3 alkyl, C.sub.1-3 alkoxy, nitro, trifluoromethyl, or di-C.sub.1-3 alkyl-amino, andn is 1 or 2)or pharmaceutically acceptable acid addition salts thereof, which are useful as a psychotropic agent such as anti-depressant or anxiolytic agent can be prepared from several routes.Type: GrantFiled: December 13, 1983Date of Patent: December 24, 1985Assignee: Shionogi & Co., Ltd.Inventors: Tsutomu Sugasawa, Makoto Adachi, Kazuyuki Sasakura, Akira Matsushita, Masami Eigyo
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Patent number: 4558131Abstract: Compounds which contain in their molecule both a hydroquinone monoether or resorcinol monoether radical and a polyalkylpiperidine radical are effective stabilizers for photographic dyes and their intermediates. In particular, they act as stabilizers against damage by light.Type: GrantFiled: December 15, 1983Date of Patent: December 10, 1985Assignee: Ciba-Geigy AGInventors: David G. Leppard, Jean Rody
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Patent number: 4539323Abstract: Compounds of the formula ##STR1## wherein R.sub.1 and R.sub.2, which may be identical to or different from each other, are each independently hydrogen, straight or branched alkyl of 1 to 8 carbon atoms or arylmethyl; orR.sub.1 and R.sub.2, together with each other, are --(CH.sub.2).sub.4 or --(CH.sub.2).sub.5 --; andR.sub.3 and R.sub.4, which may be identical to or different from each other, are each independently hydrogen, straight or branched alkyl of 1 to 4 carbon atoms or arylmethyl; orR.sub.3 and R.sub.4, together with each other, are --CH.sub.3 -- or --CH.sub.2 --CH.sub.2 --;and non-toxic, pharmacologically acceptable acid addition salts thereof. The compounds as well as their salts are useful for the treatment of cardiovascular diseases, especially hypertension.Type: GrantFiled: September 14, 1983Date of Patent: September 3, 1985Assignee: Boehringer Ingelheim KGInventors: Anton Mentrup, Ernst-Otto Renth, Kurt Schromm, Wolfgang Hoefke, Wolfram Gaida
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Patent number: 4533739Abstract: This invention relates to the novel use of certain aromatic substituted amidines as antidiarrheals.Type: GrantFiled: October 12, 1982Date of Patent: August 6, 1985Assignee: G. D. Searle & Co.Inventors: Barnett S. Pitzele, Stella S. T. Yu, Robert W. Hamilton, Alan E. Moormann
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Patent number: 4481315Abstract: Compounds which contain, in their molecule, at least one 2-(2'-hydroxyphenyl)-benztriazole group or one 2-hydroxybenzophenone group and at least one polyalkylpiperidine group are effective light stabilizers for organic materials, in particular for polymers. The use of the compounds as light stabilizers for lacquers is of particular importance.Type: GrantFiled: February 28, 1983Date of Patent: November 6, 1984Assignee: Ciba-Geigy CorporationInventors: Jean Rody, Mario Slongo
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Patent number: 4468403Abstract: Pharmaceutical compounds of the general formula (1) have been prepared ##STR1## and non-toxic pharmaceutically acceptable salts thereof, wherein R.sub.1 is a lower alkyl, phenyl lower alkyl, amino substituted phenyl lower alkyl, nitro substituted phenyl lower alkyl, cycloalkyl lower alkyl or a lower alkenyl substituent, R.sub.2 is a member selected from the group consisting of a cyano, pyridylsulfonyl, lower alkyl substituted sulfonyl, phenylsulfonyl, lower alkyl substituted phenylsulfonyl, lower alkoxy substituted phenylsulfonyl, halogen substituted phenylsulfonyl, nitro substituted phenylsulfonyl, amino substituted phenylsulfonyl and lower alkyl amido substituted phenylsulfonyl; R.sub.3 is a hydrogen or halogen atom; and R.sub.4 is a hydrogen, lower alkyl or lower alkoxy substituent, lower denoting a straight or branched chain having from 1-4 carbon atoms. These compounds exhibit analgesic agonist activity or analgesic agonist-antagonist activities.Type: GrantFiled: July 20, 1982Date of Patent: August 28, 1984Assignee: Canadian Patents & Development LimitedInventors: Edward E. Knaus, Brent K. Warren, Theodore A. Ondrus
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Patent number: 4444928Abstract: Polymers or oligometic compounds of the general formula ##STR1## in which X, X.sup.a and X.sup.b are an ester, amide or cyano group, Y, Y.sup.a and Y.sup.b are --O-- or --NR.sup.10 --, R.sup.1, R.sup.1a and R.sup.1b are a group which contains a polyalkylpiperidine radical, and R.sup.1a can also be alkyl, and R.sup.3, R.sup.3a and R.sup.3b are alkylene, alkenylene, arylene-dialkylene, cycloalkylene-dialkylene or monooxa-alkylene or polyoxa-alkylene, can be prepared by the polycondensation of malonic acid esters or amides or cyanoacetic acid esters or amides with difunctional compounds, preferably dihalogen compounds, in the presence of bases. The products obtained have a molecular weight of 800 to 20,000 and are outstanding light stabilizers for organic polymers.Type: GrantFiled: August 4, 1982Date of Patent: April 24, 1984Assignee: Ciba-Geigy CorporationInventor: Friedrich Karrer
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Patent number: 4435398Abstract: Compounds of the formula ##STR1## and their pharmaceutically acceptable acid addition salts are disclosed. The compounds are useful as anthelmintics.Type: GrantFiled: February 8, 1982Date of Patent: March 6, 1984Assignee: Schering CorporationInventor: M. Mehdi Nafissi-Varchei
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Patent number: 4426387Abstract: The invention concerns compounds of formula ##STR1## and acid addition and quaternary ammonium salts thereof, wherein the dotted line represents an optional bond, Ar represents a ring system of formula ##STR2## in which Q is O,S,--CR.sup.7 .dbd.CR.sup.8 --, --N.dbd.CR.sup.8 -- and --N.dbd.N--; R.sup.4, R.sup.5 and R.sup.6, and R.sup.7 and R.sup.8 when present, each represent hydrogen or defined substituents and additionally either R.sup.4 and R.sup.5 when adjacent or R.sup.6 and R.sup.8 when adjacent, together with the carbon atoms to which they are attached also represent a fused five or six membered carbocyclic or heterocyclic ring optionally carrying one or more defined substituents; R is an optionally substituted aryl or heteroaryl radical or a cycloalkyl radical containing 5 to 7 carbon atoms; R.sup.1, R.sup.2, R.sup.3 and R.sup.9 are each hydrogen or a lower alkyl group; n is 0 or 1; X is .dbd.O, .dbd.S or .dbd.NH; Y is --O-- or a direct bond and Z is --CO-- or --CH.sub.Type: GrantFiled: April 7, 1982Date of Patent: January 17, 1984Assignee: John Wyeth & Brother Ltd.Inventors: John L. Archibald, Terrence J. Ward
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Patent number: 4367232Abstract: This invention relates to new therapeutically useful piperidine derivatives and salts thereof. The invention also relates to processes for their preparation and pharmaceutical compositions containing them.Type: GrantFiled: October 27, 1977Date of Patent: January 4, 1983Assignee: Fordonal, S.A.Inventors: Jose Boix-Igleasias, Jose P. Soto, Armando Vega-Noverola, Robert G. W. Spickett, Jacinto M. Mauri
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Patent number: 4348524Abstract: Compounds of the formula I ##STR1## in which m is 0 or 1 and n is 1 or 2 and R, R.sup.1, R.sup.2, Z and X are as defined in claim 1, and also salts of these compounds, are valuable light stabilizers for organic materials, especially for polymers. The compounds of the formula I can be prepared from the corresponding 4-sec.-aminopiperidines by reaction with cyclic dicarboxylic acid anhydrides and appropriate further reactions.Type: GrantFiled: March 17, 1981Date of Patent: September 7, 1982Assignee: Ciba-Geigy CorporationInventors: Friedrich Karrer, Paul Moser
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Patent number: 4348401Abstract: An N-phenoxyalkylpiperidine derivative of the formula ##STR1## wherein R.sub.1 is a hydrogen atom, an acyl radical or an optionally substituted aryl radical, R.sub.2 is a hydroxymethyl radical, a cyano group, an amidino group, an amidino group substituted by hydroxyl, a 1H tetrazol-5-yl radical or a --CO--R.sub.3 radical, R.sub.3 is a hydroxyl group, a lower alkoxy radical, an amino group, or an amino group substituted by a 1H-tetrazol-5-yl radical, X is an imino group or an oxymethyl radical, A is an alkylene radical containing 2 to 4 carbon atoms, and B is a valency bond or a 4-hydroxypyrimidin-2,5-diyl radical; or a pharmacologically acceptable salt thereof. The compounds exhibit anti-histaminic, anti-oedematous and anti-phlogistic activity.Type: GrantFiled: September 10, 1980Date of Patent: September 7, 1982Assignee: Boehringer Mannheim GmbHInventors: Walter-Gunar Friebe, Wolfgang Kampe, Max Thiel, Wolfgang Schaumann, Otto-Henning Wilhelms
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Patent number: 4348406Abstract: Compounds of the formula: ##STR1## and their pharmaceutically acceptable acid addition salts, useful as anthelmintics are disclosed.Type: GrantFiled: October 20, 1980Date of Patent: September 7, 1982Assignee: Schering CorporationInventor: M. Mehdi Nafissi-Varchei
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Patent number: 4339576Abstract: 1-[(3- or 4-Benzoylphenyl)-lower-alkyl]-[(CH.sub.2).sub.n --N.dbd.B]-substituted-piperidines, useful as anti-asthmatic, anti-allergic, anti-cholinergic, bronchodilator and anti-inflammatory agents, are prepared by alkylation of an appropriate substituted piperidine with a (3- or 4-benzoylphenyl)-lower-alkyl halide or tosylate; by reaction of a 1-[2-(3- or 4-lithiophenyl)-lower-alkyl]-[(CH.sub.2).sub.n --N.dbd.B]-substituted-piperidine with benzonitrile and hydrolysis of the resulting benzimidoyl compound; or by reduction of a 1-[.alpha.-(3- or 4-benzoylphenyl)-lower-alkanoyl]-[(CH.sub.2).sub.n --N.dbd.B]-substituted-piperidine. The analogous carbinols are prepared by reduction, with an alkali metal borohydride, of the ketone.Type: GrantFiled: August 24, 1981Date of Patent: July 13, 1982Assignee: Sterling Drug Inc.Inventor: Bernard L. Zenitz
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Patent number: 4329344Abstract: This invention provides compounds, having major tranquilizing activity, of the formula (II): ##STR1## wherein R.sub.1 is a phenyl group optionally substituted by a fluorine, chlorine or bromine atom or an alkyl or alkoxyl group of up to 3 carbon atoms; R.sub.2 is a hydrogen atom or an alkyl group of up to 4 carbon atoms; R.sub.3 is a hydrogen atom or an amino group, a nitro group or a group of the formula NHCOR.sub.4 or NHCO.sub.2 R.sub.4 where R.sub.4 is an alkyl group of up to 4 carbon atoms optionally substituted by one, two or three chlorine atoms or by three fluorine atoms attached to the same carbon atom; n is 0, 1 or 2; and X is a group of the sub-formula (a), (b), (c) or (d): ##STR2## wherein R.sub.5 is an alkyl group of up to 4 carbon atoms; or a N-oxide thereof of the nitrogen atom to which the CHR.sub.2 --(CH.sub.2).sub.n --R.sub.1 moiety is attached; and salts thereof; pharmaceutical compositions containing them; processes for their preparation; and intermediates useful in said process.Type: GrantFiled: May 12, 1980Date of Patent: May 11, 1982Assignee: Beecham Group LimitedInventor: Michael S. Hadley
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Patent number: 4304937Abstract: A process of preparing a carboxylic acid amide which comprises reacting (a) an aldehyde with (b) at least one compound selected from the group consisting of ammonia, a primary amine and a secondary amine in the presence of a molecular oxygen-containing gas and palladium metal or platinum metal as the catalyst.Type: GrantFiled: November 13, 1979Date of Patent: December 8, 1981Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Nishikido Joji, Tamura Nobuhiro, Fukuoka Yohei
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Patent number: 4304911Abstract: 1-[(3- or 4-Benzoylphenyl)-lower-alkyl]-[(CH.sub.2).sub.n -N.dbd.B]-substituted-piperidines, useful as anti-asthmatic, anti-allergic, anti-cholinergic, bronchodilator and anti-inflammatory agents, are prepared by alkylation of an appropriate substituted piperidine with a (3- or 4-benzoylphenyl)-lower-alkyl halide or tosylate; by reaction of a 1-[2-(3- or 4-lithiophenyl)-lower-alkyl]-.differential.(CH.sub.2).sub.n --N.dbd.]-substituted-piperidine with benzonitrile and hydrolysis of the resulting benzimidoyl compound; or by reduction of a 1-[.alpha.-(3- or 4-benzoylphenyl)-lower-alkanoyl]-[(CH.sub.2).sub.n --N.dbd.B]-substituted-piperidine.Type: GrantFiled: November 19, 1980Date of Patent: December 8, 1981Assignee: Sterling Drug Inc.Inventor: Bernard L. Zenitz
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Patent number: 4296125Abstract: Derivatives of benzoylphenoxyalkanoic acids corresponding to the formula: ##STR1## wherein: X represents for example a halogen, R.sup.1 and R.sup.2 represent for example alkyl groups, R represents for example an aminoacid; and the salts thereof are new products showing antilipaemic and anticholesterolemic pharmacological activity.Type: GrantFiled: February 21, 1980Date of Patent: October 20, 1981Assignee: Alpha Farmaceutici S.p.A.Inventors: Valerio Borzatta, Manlio Cristofori, Mauro Morotti, Giuseppe Mascellani
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Patent number: 4289686Abstract: Compounds which contain, in their molecule, at least one 2-(2'-hydroxyphenyl)-benztriazole group or one 2-hydroxybenzophenone group and at least one polyalkylpiperidine group are effective light stabilizers for organic materials, in particular for polymers. The use of the compounds as light stabilizers for lacquers is of particular importance.Type: GrantFiled: September 17, 1979Date of Patent: September 15, 1981Assignee: Ciba-Geigy CorporationInventors: Jean Rody, Mario Slongo
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Patent number: 4281132Abstract: Compounds of formula ##STR1## in which X represents oxygen or sulphur;Y represents --CHOH-- or ##STR2## Z represent ##STR3## or a direct bond; R represents cycloalkyl group having 5 to 7 carbon atoms or an optionally substituted aryl or heteroaryl radical, or when --Z-- is a direct bond R also represents hydrogen;R.sup.1 represents hydrogen or lower alkyl;R.sup.2 represents hydrogen, halogen, lower alkyl or lower alkoxy; andR.sup.3 represents hydrogen or lower alkyl, and a pharmaceutically acceptable acid addition or quarternary ammonium salts thereof, are disclosed which possess hypotensive activity.Type: GrantFiled: October 24, 1978Date of Patent: July 28, 1981Assignee: John Wyeth & Brother LimitedInventor: Terence J. Ward
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Patent number: 4281006Abstract: Compounds having the formula ##STR1## wherein A is a bond or C.sub.1-4 alkylene; R.sup.1, R.sup.2 and R.sup.3 are independently a halogen atom, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 alkylthio, CF.sub.3, SCF.sub.3 or OCF.sub.3 ; R.sup.4 is a hydrogen atom or C.sub.1-4 alkyl; and n, m and q are independently an integer from 0 to 3; and pharmaceutically acceptable acid addition salts thereof, are useful for the treatment of gastrointestinal hypersecretion.Type: GrantFiled: May 2, 1980Date of Patent: July 28, 1981Assignee: Richardson-Merrell Inc.Inventors: J. Martin Grisar, Norbert L. Wiech
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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: 4260410Abstract: Novel N-haloacetylphenylamino carbonyl oximes represented by the formula ##STR1## wherein Ar is phenyl or substituted phenyl; R.sup.1 is halomethyl; R.sup.2 and R.sup.3 are each independently hydrogen, alkyl, phenyl, benzyl, substituted phenyl or benzyl, haloalkyl, cyanoalkyl, alkoxyalkyl, alkylthioalkyl or thiocyanoalkyl; R.sup.4 is hydrogen or alkyl; n is 0 or 1; m is 0 or 1; R is hydrogen, alkyl, alkenyl, alkynyl, alkylthioalkyl, haloalkyl, alkoxyalkyl, cyanoalkyl, phenyl, benzyl, substituted phenyl or benzyl, or R is acyl of the formula ##STR2## wherein R.sup.5 is hydrogen, alkyl, haloalkyl, alkoxyalkyl, alkylthioalkyl, alkoxy, alkylthio, acetonyl, or the group -NR'R" wherein R' and R" are independently hydrogen, alkyl or phenyl; with the proviso that R.sup.2 and R.sup.3 may be joined together to form a carbocyclic ring or a heterocyclic ring; or R and R.sup.2 may be joined together to form a heterocyclic ring; or R and R.sup.3 may be joined together to form a heterocyclic ring.Type: GrantFiled: February 23, 1979Date of Patent: April 7, 1981Assignee: Chevron Research CompanyInventors: William L. Schinski, David C. K. Chan, Irene C. Huang
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Patent number: 4247694Abstract: The invention relates to metal salts of hydroxybenzoic acids which are complexed with a 4-amino-polyalkylpiperidine derivative or to mixed metal salts of a hydroxybenzoic acid and a polyalkylpiperidine carboxylic acid which may be complexed or not with an 4-amino-polyalkylpiperidine. The metal cation may be that of a di- or trivalent metal such as Ni, Co, Al, Zn or Ca. From hydroxybenzoic acids the 3,5-di-tert.butylbenzoic acid is preferred.These salts are valuable light stabilizers for plastics, especially for polyolefins, styrene polymers and polyamides or polyurethanes respectively. The salts show a strong tendency to retain water. For high compatibility with plastics a low water content is of importance.Type: GrantFiled: October 10, 1978Date of Patent: January 27, 1981Assignee: Ciba-Geigy CorporationInventor: Michael Rasberger
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Patent number: 4246267Abstract: This invention relates to 4-aminopiperidines and more precisely to 4-aminopiperidines the nitrogen atom of the piperidine ring is substituted with an aryl lower alkyl side-chain.This invention also relates to processes for producing the same.This invention further extends to pharmaceutical compositions and to the method of using the same.Type: GrantFiled: October 4, 1978Date of Patent: January 20, 1981Assignee: Science Union et CieInventors: Michel Vincent, Georges Remond, Michel Laubie
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Patent number: 4242347Abstract: 1-(Indolyl-3-alkyl)-3 or 4-(ureido or guanidino)-piperidines, e.g. those of the formula ##STR1## R=H; alkyl; free, etherified or esterified OH or SH; CF.sub.3, NO.sub.2 or NH.sub.2m=1-4;n=2 or 3;X=O, S or NHacyl derivatives and salts thereof are antihypertensive agents.Type: GrantFiled: June 18, 1979Date of Patent: December 30, 1980Assignee: Ciba-Geigy CorporationInventor: Charles F. Huebner
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Patent number: 4235915Abstract: Compounds of formula ##STR1## in which X represents oxygen or sulphur;Y represents --CHOH-- or ##STR2## Z represents ##STR3## or a direct bond; R represents cycloalkyl group having 5 to 7 carbon atoms or an optionally substituted aryl or heteroaryl radical, or when --Z-- is a direct bond R also represents hydrogen;R.sup.1 represents hydrogen or lower alkyl.andR.sup.2 represents hydrogen, halogen, lower alkyl or lower alkoxy;ora pharmaceutically acceptable acid addition or quaternary ammonium salt thereof, are disclosed which reduce heart rate or have hyperglycaemic activity.Type: GrantFiled: December 5, 1977Date of Patent: November 25, 1980Assignee: John Wyeth & Brother LimitedInventors: John L. Archibald, Terence J. Ward
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Patent number: 4226999Abstract: A compound of the formula I ##STR1## in which R.sub.2 is an optionally substituted 4-piperidinyl bonded via oxy or imino, or an optionally substituted 2-(piperidino)-ethoxy, n is 1 or 2, R.sub.7 and R.sub.8 are hydrocarbon radicals, R.sub.9 is hydrogen or methyl, R.sub.14 is cyano, --CH.sub.2 OH, a hydroxymethyl which is C-substituted by an optionally substituted 4-piperidinyl bonded via oxy or imino, or by an optionally substituted 2-(piperidino)-ethoxy, or R.sub.14 is also acyl or nitro, and, when n=1, R.sub.15 is hydrogen, a substituted hydroxybenzyl, an optionally substituted hydrocarbon radical, an optionally substituted 4-piperidinyl, or alkylene which is optionally linked to R.sub.14 and optionally substituted, or, when n=2, R.sub.15 is a direct bond or an optionally interrupted hydrocarbon radical, and its salts as stabilizers for organic material.Type: GrantFiled: January 5, 1979Date of Patent: October 7, 1980Assignee: Ciba-Geigy CorporationInventors: Roger Malherbe, Michael Rasberger
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Patent number: 4223034Abstract: This invention provides compounds, having major tranquilizing activity, of the formula (II): ##STR1## wherein R.sub.1 is a phenyl group optionally substituted by a fluorine, chlorine or bromine atom or an alkyl or alkoxyl group of up to 3 carbon atoms; R.sub.2 is a hydrogen atom or an alkyl group of up to 4 carbon atoms; R.sub.3 is a hydrogen atom or an amino group, a nitro group or a group of the formula NHCOR.sub.4 or NHCO.sub.2 R.sub.4 where R.sub.4 is an alkyl group of up to 4 carbon atoms optionally substituted by one, two or three chlorine atoms or by three fluorine atoms attached to the same carbon atom; n is 0, 1 or 2; and X is a group of the sub-formula (a), (b), (c) or (d):--CH.sub.2 --CH.sub.2 --NR.sub.5 -- (a) ##STR2## wherein R.sub.5 is an alkyl group of up to 4 carbon atoms; or a N-oxide thereof of the nitrogen atom to which the CHR.sub.2 --(CH.sub.2).sub.n --R.sub.Type: GrantFiled: April 10, 1978Date of Patent: September 16, 1980Assignee: Beecham Group LimitedInventor: Michael S. Hadley
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Patent number: 4223147Abstract: The invention relates to new methylol derivatives of 2,2,6,6-tetraalkylpiperidines, to their production and to their use as chemically attached stabilizers for polymers containing reactive OH- and NH-groups.Type: GrantFiled: September 19, 1977Date of Patent: September 16, 1980Assignee: Bayer AktiengesellschaftInventors: Harald Oertel, Paul Uhrhan, Reinhard Lantzsch, Ernst Roos, Hans Schroer, Dieter Arlt
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Patent number: 4209521Abstract: The invention concerns a compound of formula II ##STR1## or a pharmaceutically acceptable acid addition or quaternary ammonium salt thereof wherein R.sup.5 represents hydrogen, hydroxy, lower alkoxy or lower alkyl, R.sup.6 represents hydrogen or lower alkyl, and R.sup.7 represents phenyl, lower alkoxy phenyl, halophenyl, or thenyl and X represents oxygen or sulphur. These indole derivatives exhibit psychotropic activity. The invention includes a method of alleviating depression in a warm blooded animal afflicted with depression which method comprises administering to said animal an effective amount of a compound of formula II or a pharmaceutically acceptable acid addition salt thereof.Type: GrantFiled: November 8, 1978Date of Patent: June 24, 1980Assignee: John Wyeth & Brother LimitedInventors: John L. Archibald, Terence J. Ward
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Patent number: 4208418Abstract: Novel N-aryl-N-(1-L-4-piperidinyl)arylacetamides useful as anti-arrhythmic agents, a method of treating arrhythmia which comprises the systemic administration of such compounds to warm-blooded animals and pharmaceutical compositions to be used therefor.Type: GrantFiled: July 13, 1978Date of Patent: June 17, 1980Assignee: Janssen Pharmaceutica N.V.Inventors: Stefan Sanczuk, Hubert K. Fr. Hermans
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Patent number: 4197236Abstract: Compounds of the general formula I ##STR1## or their acid addition salts in which one of R.sub.1 and R.sub.3 is --OH and the other is hydrogen and R.sub.2 denotes C.sub.1 -C.sub.12 -alkyl, C.sub.5 -C.sub.7 -cycloalkyl, C.sub.6 -C.sub.10 -aryl or C.sub.7 -C.sub.9 -aralkyl and R.sub.4 and R.sub.5 are hydrogen, C.sub.1 -C.sub.12 -alkyl, C.sub.5 -C.sub.7 -cycloalkyl, C.sub.6 -C.sub.10 -aryl or C.sub.7 -C.sub.9 -aralkyl and R.sub.6 denotes hydrogen, C.sub.1 -C.sub.12 -alkyl, C.sub.5 -C.sub.7 -cycloalkyl, phenyl or benzyl and R.sub.7 is hydrogen or C.sub.1 -C.sub.8 -alkyl and R.sub.8 is hydrogen, oxyl, C.sub.1 -C.sub.12 -alkyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.4 -alkinyl, C.sub.2 -C.sub.21 -alkoxyalkyl, C.sub.7 -C.sub.8 -aralkyl, 2,3-epoxypropyl, an aliphatic acyl group with 1-4 C atoms or one of the groups --CH.sub.2 COOR.sub.9, --CH.sub.2 --CH(R.sub.10)--OR.sub.11, --COOR.sub.12 or -- CONHR.sub.12, in which R.sub.9 is C.sub.1 -C.sub.12 -alkyl, C.sub.3 -C.sub.6 -alkenyl, phenyl, C.sub.7 -C.sub.Type: GrantFiled: August 7, 1978Date of Patent: April 8, 1980Assignee: Ciba-Geigy CorporationInventors: Siegfried Rosenberger, Samuel Evans
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Patent number: 4197303Abstract: Novel N-aryl-N-(1-L-4-piperidinyl)arylacetamides useful as anti-arrhythmic agents, a method of treating arrhythmia which comprises the systemic administration of such compounds to warm-blooded animals and pharmaceutical compositions to be used therefor.Type: GrantFiled: July 13, 1978Date of Patent: April 8, 1980Assignee: Janssen Pharmaceutica N.V.Inventors: Stefan Sanczuk, Hubert K. F. Hermans
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Patent number: 4191683Abstract: Derivatives of sterically hindered 4-aminopiperidines are effective as light-stabilizers for organic polymers, especially for polyolefins. The piperidine ring is substituted with at least five alkyl groups, preferably methyl and ethyl groups. The 4-amino group is substituted with mono- or divalent acyl groups. The nitrogen in 1-position may also be substituted with a monovalent organic substituent. The compounds can be synthesized starting from higher homologs of acetone in sequence of several reaction steps.Type: GrantFiled: November 21, 1977Date of Patent: March 4, 1980Assignees: Ciba-Geigy Corporation, Sankyo Company LimitedInventors: Heimo Brunetti, Jean Rody, Nobuo Soma, Tomoyuki Kurumada
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Patent number: 4177279Abstract: The invention provides compounds of general formula I ##STR1## and pharmaceutically acceptable acid addition and quaternary ammonium salts thereof, wherein R represents hydrogen or lower alkyl, R.sup.1 represents hydrogen or lower alkyl, R.sup.2 represents hydrogen or lower alkyl, R.sup.3 represents hydrogen, halogen, lower alkoxy, hydroxy, or lower alkyl, R.sup.4 represents hydrogen, lower alkyl, cycloalkyl of 5 to 7 carbon atoms, thienyl, furyl, phenyl; phenyl mono- or disubstituted by halogen, lower alkyl, lower alkoxy, hydroxy or trifluoromethyl; or benzoyl, halobenzoyl, lower alkanoyl, cycloalkanoyl of 6 to 8 carbon atoms, or thienoyl, A represents an alkylene, mono- or diketo- or hydroxy-alkylene radical having from 1 to 5 carbon atoms and X is oxygen or sulphur.The compounds exhibit action on the cardiovascular system particularly hypotensive and/or anti-hypertensive activity.Type: GrantFiled: July 21, 1975Date of Patent: December 4, 1979Assignee: John Wyeth & Brother Ltd.Inventors: John L. Archibald, John L. Jackson
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Patent number: 4174210Abstract: Novel N-haloacetylphenylamino carbonyl oximes represented by the formula ##STR1## wherein Ar is aryl, R.sup.1 is halomethyl, R.sup.2 is hydrogen, alkyl or aryl, R.sup.3 is hydrogen, alkyl or aryl, n is 0 or 1 and R is hydrogen, aryl, alkyl, alkenyl or alkynyl, with the proviso that R.sup.2 and R.sup.3 may be joined together to form a carbocyclic ring of 5 to 6 carbon atoms or a heterocyclic ring of one N, O or S hetero atom and 4 to 5 carbon atoms. The oxime compounds are useful as herbicides and plant growth regulators.Type: GrantFiled: March 31, 1978Date of Patent: November 13, 1979Assignee: Chevron Research CompanyInventors: William L. Schinski, Irene C. Huang, David C. K. Chan
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Patent number: 4167574Abstract: Novel compounds of the series of N-phenyl-N-(4-piperidinyl)amides having a (4,5-dihydro-4-R-5-oxo-1H-tetrazol-1-yl)alkyl or (4,5-dihydro-4-R-5-thioxo-1H-tetrazol-1-yl)alkyl substituent group in the 1-position of the piperidine nucleus, said compounds being useful as analgesic agents.Type: GrantFiled: October 25, 1978Date of Patent: September 11, 1979Assignee: Janssen Pharmaceutica, N.V.Inventor: Frans Janssens
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Patent number: 4166813Abstract: New polyalkylated 4-aminopiperidine derivatives contain in their molecule two or three piperidine rings, each having two alkyl substituents at both the 2- and the 6- positions, optionally having substituents at the 1- and 3- positions and having an amino substituent at the 4- position. The piperidine rings are joined together by attachment of the 4-amino substituents through, where there are two piperidine rings, a polyalkylene, polyether or polyester chain, or through, where there are three piperidine rings, an isocyanurate or glycerol system. These compounds and their acid addition salts are useful as stabilizers for synthetic polymers.Type: GrantFiled: May 8, 1978Date of Patent: September 4, 1979Assignee: Sankyo Company Ltd.Inventors: Nobuo Soma, Syoji Morimura, Takao Yoshioka, Tomoyuki Kurumada
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Patent number: 4166117Abstract: This invention relates to novel quinazolinones, the nitrogen of which is bound to 4-amino piperidinyl-1 structures.This invention also relates to processes for producing these compounds.They have interesting pharmacological properties which make them useful in human or veterinary medicine for treating hypertension.Type: GrantFiled: July 11, 1977Date of Patent: August 28, 1979Assignee: Science Union et CieInventors: Michel Vincent, Georges Remond, Michel Laubie
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Patent number: 4163789Abstract: This invention relates to piperidine derivatives. More particularly, the invention relates to substituted benzoic acid amides of N-substituted piperidine and to pharmaceutical compositions thereof, which are useful in antagonizing the effects of dopamine or dopaminergic agents of endogenous or exogenous origin and in treating nausea and vomiting resulting from gastrointestinal disorders, congestive heart failure, post operative conditions, etc., other gastrointestinal disorders such as dyspepsia, flatulence, bile regurgitations, hiatus hernia, peptic ulcer, reflux aerophagitis, gastritis, duodenitis, and cholethiasis, and a variety of conditions affecting the central nervous system such as acute and chronic psychoses, maniacal psychosis, schizophrenias, serious disturbances of behavior and non-melancholic depressive state and migraine. The invention also relates to methods of preparing piperidine derivatives.Type: GrantFiled: February 17, 1977Date of Patent: August 7, 1979Assignee: Anphar, S.A.Inventors: Jacinto M. Mauri, Armando Vega-Noverola, Robert G. W. Spickett
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Patent number: 4157393Abstract: Novel N-aryl-N-(1-L-4-piperidinyl)arylacetamides useful as antiarrhythmic agents, a method of treating arrhythmia which comprises the systemic administration of such compounds to warm-blooded animals and pharmaceutical compositions to be used therefor.Type: GrantFiled: July 13, 1978Date of Patent: June 5, 1979Assignee: Janssen Pharmaceutica N.V.Inventors: Stefan Sanczuk, Hubert K. Fr. Hermans
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Patent number: 4151286Abstract: Novel N-aryl-N-(1-L-4-piperidinyl)-arylacetamides useful as antiarrhythmic agents, a method of treating arrhythmia which comprises the systemic administration of such compounds to warm-blooded animals and pharmaceutical compositions to be used therefor.Type: GrantFiled: July 13, 1978Date of Patent: April 24, 1979Assignee: Janssen Pharmaceutica N.V.Inventors: Stefan Sanczuk, Hubert K. Fr. Hermans
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Patent number: 4148784Abstract: A compound of the formula I ##STR1## in which R.sub.2 is an optionally substituted 4-piperidinyl bonded via oxy or imino, or an optionally substituted 2-(piperidino)-ethoxy, n is 1 or 2, R.sub.7 and R.sub.8 are hydrocarbon radicals, R.sub.9 is hydrogen or methyl, R.sub.14 is cyano, --CH.sub.2 OH, a hydroxymethyl which is C-substituted by an optionally substituted 4-piperidinyl bonded via oxy or imino, or by an optionally substituted 2-(piperidino)-ethoxy, or R.sub.14 is also acyl or nitro, and, when n=1, R.sub.15 is hydrogen, a substituted hydroxybenzyl, an optionally substituted hydrocarbon radical, an optionally substituted 4-piperidinyl, or alkylene which is optionally linked to R.sub.14 and optionally substituted, or, when n=2, R.sub.15 is a direct bond or an optionally interrupted hydrocarbon radical, and its salts as stabilizers for organic material.Type: GrantFiled: December 16, 1976Date of Patent: April 10, 1979Assignee: Ciba-Geigy CorporationInventors: Roger Malherbe, Michael Rasberger