Having -c(=x)-, Wherein X Is Chalogen, Attached Directly Or Indirectly To The Piperidine Ring By Nonionic Bonding Patents (Class 546/221)
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Patent number: 4528294Abstract: The present invention relates to new benzoyl-phenyl-piperidine derivatives selected from the group consisting of:(i) 2-piperidinobenzophenones of the general formula: ##STR1## in which: R.sub.1, R.sub.2 and R.sub.3, which are identical or different, each represent an atom of hydrogen, a hydroxy group, CF.sub.3, a halogen, a lower alkyl group or a lower alkoxy group;R.sub.4 represents an atom of hydrogen, a halogen, an NO.sub.2 group, an NR'R" group [where R' and R", which are identical or different, represent an atom of hydrogen, a lower alkyl group or a CO.sub.2 R group (where R represents a lower alkyl group or a benzyl group)];R.sub.5 and R.sub.6, which are identical or different, each represent an atom of hydrogen, a C.sub.1 -C.sub.4 -alkyl group, an OH group, a phenyl group or a benzyl group; and(ii) acid addition salts thereof.The invention also relates to the method for preparing these new derivatives and to their use in therapeutics, particularly as immunostimulant and immunoadjuvant agents.Type: GrantFiled: June 24, 1982Date of Patent: July 9, 1985Assignee: Societe de Recherches Industrielle S.O.R.I.Inventors: Bernard Majoie, Francois Bellamy, Pierre Dodey, Jacques Robin
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Patent number: 4521537Abstract: Spiro[2H-1,4-benzodioxepin-3(5H)4'-piperidine and -3'-pyrrolidine] compounds of the formula ##STR1## where the substituents are as defined herein, are useful in the treatment of hypertension in mammals. Such compounds, their use as antihypertensive agents, pharmaceutical compositions containing the compounds, intermediates and processes for preparing the compounds are provided.Type: GrantFiled: April 2, 1984Date of Patent: June 4, 1985Assignee: Hoechst-Roussel Pharmaceuticals IncorporatedInventors: Raymond W. Kosley, Jr., Robert J. Cherill
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Patent number: 4518713Abstract: There are described analgesic substituted-1-aminoalkylamino-4-aryloxypiperidines of the formula ##STR1## where X is hydrogen, loweralkyl, CF.sub.3, acetyl or halogen; n is 1 or 2; R.sub.1 is H.sub.2 or oxygen; R.sub.2 is H, loweralkyl or benzyl; and R.sub.3 is oxygen or --OCH.sub.2 CH.sub.2 O--, which are useful as analgesic agents and intermediate compounds therefor.Type: GrantFiled: April 13, 1984Date of Patent: May 21, 1985Assignee: Hoechst-Roussel Pharmaceuticals Inc.Inventors: Raymond W. Kosley, Jr., Richard C. Allen
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Patent number: 4518799Abstract: Novel processes for making arylpropionic acids are described. One process comprises carboxylating particular Grignard compounds which are the products of a catalyzed reaction between corresponding arylmagnesium bromides and ethylene. Furthermore, the reaction making the particular Grignard compounds is itself novel. Also, an improved method is disclosed for making coupled aryl compounds useful as intermediates for making compounds having a pharmaceutical use. For example, particular biaryls may be used to make some of the Grignard compounds herein from which the arylpropionic acids are made. Finally, an improved bromination is disclosed giving high yields of 4-bromo-2-fluoroaniline, which is thereafter coupled with benzene, then used to make the arylmagnesium bromide reacted with ethylene to obtain the particular Grignard compound and subsequent desired arylpropionic acid, i.e. 2-(2-fluoro-4-biphenylyl)propionic acid.Type: GrantFiled: June 8, 1982Date of Patent: May 21, 1985Assignee: The Upjohn CompanyInventor: Thomas A. Hylton
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Patent number: 4497954Abstract: Certain substituted cyclopentanone ethylene ketal compounds, and ketones and amides derived therefrom are useful synthetic intermediates for compounds of pharmaceutical interest. A synthetic process for using the intermediates is also described.Type: GrantFiled: November 15, 1983Date of Patent: February 5, 1985Assignee: Riker Laboratories, Inc.Inventor: Elden H. Banitt
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Patent number: 4496734Abstract: Synthetic 5-hydroxy-N-(6-oxo-2-piperidylmethyl)-2-(2,2,2-trifluoroethoxy) benzamide. The compound 5-hydroxy-N-(6-oxo-2-piperidylmethyl)-2-(2,2,2-trifluoroethoxy) benzamide is a metabolite of the antiarrhythmic agent 2,5-bis(2,2,2-trifluoroethoxy)-N-(2-piperidylmethyl)-benzamide.Type: GrantFiled: November 15, 1983Date of Patent: January 29, 1985Assignee: Riker Laboratories, Inc.Inventors: Roy L. McQuinn, William R. Bronn, Elden H. Banitt
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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: 4476311Abstract: Analgesic and anti-inflammatory compounds are provided. These compounds possess the following general formula: ##STR1## wherein R=--COOR.sub.5, --CH.sub.2 CO.sub.2 H, ##STR2## wherein A and B=hydrogen, lower alkyl, hydroxy alkyl, lower alkyl amine, substituted lower alkyl amine, aminoalkyl, substituted aminoalkyl;R.sub.5 =lower alkyl;R.sub.1 =aryl, substituted aryl, aralkyl, alkyl, hydrogen, substituted aralkyl and heterocycle;R.sub.2 =aryl, substituted aryl, aralkyl, alkyl, substituted aralkyl, heterocycle, substituted heterocycle, biphenyl, substituted biphenyl, naphthyl, and substituted naphthyl;R.sub.3 =aryl, substituted aryl, hydrogen, aralkyl, substituted aralkyl, alkyl, heterocycle and substituted heterocycle;R.sub.2 and R.sub.3 together form a ring;R.sub.4 =hydrogen, phenyl, substituted phenyl, heterocycle; alkyl, substituted alkyl; or, R.sub.1 and R.sub.4 may form a ring;X=>C.dbd.O, --CH.sub.2 --;Y=--S--CHR.sub.4 --, --O--OHR.sub.4 --, --CHR.sub.4 --, --CR.sub.6 R.sub.7 --CHR.sub.Type: GrantFiled: February 19, 1982Date of Patent: October 9, 1984Assignee: The Purdue Frederick CompanyInventors: Bola V. Shetty, Arthur McFadden, Peter Hofer
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Patent number: 4472580Abstract: Spiro[2H-1,4-benzodioxepin-3(5H)4'-piperidine and -3-pyrrolidine] compounds of the formula ##STR1## where the substituents are as defined herein, are useful in the treatment of hypertension in mammals. Such compounds, their use as antihypertensive agents, pharmaceutical compositions containing the compounds, intermediates and processes for preparing the compounds are provided.Type: GrantFiled: July 25, 1983Date of Patent: September 18, 1984Assignee: Hoechst-Roussel Pharmaceuticals IncorporatedInventors: Raymond W. Kosley, Jr., Robert J. Cherill
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Patent number: 4472412Abstract: A fungicidal agent contains a phenylpropylammonium salt of the formula ##STR1## where R.sup.1, R.sup.2 and R.sup.3 are each hydrogen, unsubstituted or substituted alkyl, unsubstituted or substituted aryl or aralkyl, cycloalkyl, alkoxy, acyl or halogen, R.sup.4 is alkyl, alkenyl or alkoxy, R.sup.5 is alkyl, alkenyl, alkynyl or unsubstituted or substituted aralkyl, R.sup.6 and R.sup.7 are each hydrogen, alkyl, CH.sub.2 OH or OH, X is CH.sub.2, O, S, C.dbd.O, (CH.sub.2).sub.2 or CH.sub.2 CH--R.sup.8 where R.sup.8 is alkyl, m is 0, 1 or 2, n is 0 or 1 and Y.crclbar. is the anion of a non-phytotoxic acid, with the proviso that the bond represented by the broken line may be hydrogenated if m is 0 or 1, and is always hydrogenated if m is 2.Type: GrantFiled: August 24, 1982Date of Patent: September 18, 1984Assignee: BASF AktiengesellschaftInventors: Ernst Buschmann, Bernd Zeeh, Ernst-Heinrich Pommer, Eberhard Ammermann
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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: 4464354Abstract: Monofunctional psoralen derivatives having the general formula ##STR1## wherein R represents a hydrogen atom, a lower alkyl group having from 1 to 4 atoms, preferably a methyl radical, or a lower alkoxy radical having from 1 to 4 carbon atoms, preferably a methoxy radical are described. The derivatives are photobiologically active and are useful in photochemical therapy and in cosmetics.Type: GrantFiled: February 24, 1983Date of Patent: August 7, 1984Assignee: Institut National de la Sante et de la Recherche MedicaleInventors: Emile Bisagni, Louis Dubertret, Jacqueline Moron, Dietrich Averbeck, Dora Papadopoulo, Jocelyne Blais, Paul Vigny, Maria N. Schwencke, Ethel Moustacchi, Silvano Nocentini, Francois Zajdela
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Patent number: 4463177Abstract: m-Hydroxyphenyl substituted compounds of formula ##STR1## where R is an organic radical and R.sup.1 is hydroen or an organic radical are prepared by dehydrohalogenating a compound of formula ##STR2## (where X is chlorine or bromine, and R and R.sup.1 have the above meanings). Preferred novel starting materials of formula (II) are of the formula ##STR3## (where R.sup.1 and X are as above, n is 2,3 or 4, R.sup.2 is hydrogen or lower alkyl and R.sup.3 is hydrogen, lower alkyl, lower alkenyl, lower alkynyl, cycloalkyl(lower)alkyl or aryl(lower)alkyl).Type: GrantFiled: November 26, 1982Date of Patent: July 31, 1984Assignee: John Wyeth & Brother LimitedInventor: Robin G. Shepherd
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Patent number: 4446141Abstract: The present invention relates to a novel compound represented by the general formula: ##STR1## wherein Ar represents a naphthyl, phenyl or substituted phenyl group, Q represents ##STR2## wherein R.sub.1 represents a hydrogen atom, or an alkyl, alkanoyl or alkoxycarbonyl group, R represents a hydrogen atom or an alkyl group, and Z represents a substituted benzimidazolinyl group; the broken line in piperidine ring means that 3,4-positions in the piperidine ring are saturated or form a double bond. Said compound and the pharmaceutically acceptable acid addition salts thereof have a hypotensive action and therefore are useful as medicine.Type: GrantFiled: February 2, 1980Date of Patent: May 1, 1984Inventors: Nobuhiro Nakamizo, Hiroyuki Obase, Kazuhiro Kubo, Yutaka Kasuya
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Patent number: 4439364Abstract: Certain antihypertensive 1-substituted cyclic lactam-2-carboxylic acids and their derivatives are prepared by reacting an ester of the formula ##STR1## with a suitable derivative of the formula ##STR2##Type: GrantFiled: September 1, 1982Date of Patent: March 27, 1984Assignee: E. I. Du Pont de Nemours & CompanyInventor: Alexander L. Johnson
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Patent number: 4438112Abstract: Prostanoids are described of the formulae ##STR1## (and the salts thereof) in which: X is cis or trans --CH.dbd.CH-- or CH.sub.2 CH.sub.2 --;R.sup.1 is C.sub.1-7 alkyl terminated by --COOR.sup.10 where R.sup.10 is H, C.sub.1-6 alkyl or aralkyl;Y is a saturated heterocyclic amino group; andR.sup.4 is aralkyl (in which the aryl portion is substituted by alkylthio, alkylsulphinyl, alkylsulphonyl, alkanoylamino, aroylamino, phenalkyl, aminosulphonyl, alkanoylaminosulphonyl, phenylsulphonyl, nitro, tetrazolyl, substituted phenyl or thienyl).These compounds inhibit blood platelet aggregation and have bronchodilatory action, and may be formulated for use as anti-asthmatics and antithrombotic agents.Type: GrantFiled: September 17, 1982Date of Patent: March 20, 1984Assignee: Glaxo Group LimitedInventors: Eric W. Collington, Peter Hallett, Christopher J. Wallis, John Bradshaw
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Patent number: 4424357Abstract: Novel 4-aryloxy- and 4-arylthio-3-phenylpiperidines and related compounds, physiologically acceptable salts thereof and intermediates therefor possessing analgesic, antidepressant properties, and a process for the preparation of such compounds, derivatives and intermediates are described.Type: GrantFiled: December 28, 1979Date of Patent: January 3, 1984Assignee: Hoechst-Roussel Pharmaceuticals, Inc.Inventors: Solomon S. Klioze, Frederick J. Ehrgott
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Patent number: 4405631Abstract: Spiro[2H-1,4-benzodioxepin-3(5H)4'-piperidine and -3-pyrrolidine] compounds of the formula ##STR1## where the substituents are as defined herein, are useful in the treatment of hypertension in mammals. Such compounds, their use as antihypertensive agents, pharmaceutical compositions containing the compounds, intermediates and processes for preparing the compounds are provided.Type: GrantFiled: August 20, 1982Date of Patent: September 20, 1983Assignee: Hoechst-Roussel Pharmaceuticals Inc.Inventors: Raymond W. Kosley, Jr., Robert J. Cherill
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Patent number: 4398938Abstract: This invention relates to compounds of the formula: ##STR1## wherein X is halogen or trifluoromethyl; hydrogen, halogen or cyano; Z is halogen, cyano or nitro; R is alkyl; m is an integer from 0 to 6; and n is an integer from 3 to 5.Type: GrantFiled: May 20, 1982Date of Patent: August 16, 1983Assignee: Velsicol Chemical CorporationInventors: Leonard J. Stach, Frank Wu
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Patent number: 4387229Abstract: 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: February 26, 1982Date of Patent: June 7, 1983Assignee: Pfizer Inc.Inventors: Thomas H. Althuis, Charles A. Harbert, Michael R. Johnson, Lawrence S. Melvin, Jr.
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Patent number: 4383999Abstract: N-Substituted azaheterocyclic carboxylic acids and their esters, useful as inhibitors of GABA uptake, are prepared by reacting an appropriate N-alkylating derivative with an ester of an N-unsubstituted azaheterocyclic carboxylic acid followed by hydrolysis of the ester.Type: GrantFiled: April 28, 1982Date of Patent: May 17, 1983Assignee: Smithkline Beckman CorporationInventors: William E. Bondinell, John J. Lafferty, Charles L. Zirkle
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Patent number: 4379785Abstract: What are disclosed are sulfonyl ureas of the formula ##STR1## in which R.sup.1, X and Y are as defined in the specification, and their physiologically acceptable salts, pharmaceutical formulations on the basis of these compounds, and their use in the treatment of diabetes.Type: GrantFiled: December 17, 1980Date of Patent: April 12, 1983Assignee: Hoechst AktiengesellschaftInventors: Rudi Weyer, Volker Hitzel, Karl Geisen, Gunter Regitz
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Patent number: 4369274Abstract: Compounds of the formula ##STR1## and polymers thereof are useful as ultraviolet radiation stabilizers for polymers.Type: GrantFiled: July 20, 1981Date of Patent: January 18, 1983Assignee: American Cyanamid CompanyInventor: Walter M. Thomas
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Patent number: 4366162Abstract: Aryl ethers of N-alkyl-piperdines having the formula ##STR1## wherein R.sub.1 represents hydrogen, halogen including F, Cl and Br, a lower alkanoyl group (e.g. alkanoyl of up to five carbon atoms), an alkenyl group (having three to five carbon atoms) or phenoxy, R.sub.2 represents hydrogen, halogen including F, Cl and Br, --CN group, a lower alkoxy group (e.g. alkoxy of up to five carbon atoms), a lower alkanoyl group (e.g. alkanoyl of up to five carbon atoms), an alkenyloxy or alkynyloxy group (having three to five carbon atoms) or a lower alkoxycarbonyl group (e.g. alkoxycarbonyl of up to five carbon atoms), R.sub.3 and R.sub.4 independently represent hydrogen, halogen including F, Cl and Br, a --CF.sub.3 group, a lower alkyl group (e.g. alkyl of up to five carbon atoms) or a lower alkoxy group (e.g. alkoxy of up to five carbon atoms), R.sub.5 represents hydrogen or an acyl group with 2-19 carbon atoms and n=3 or 4, and pharmaceutically acceptable acid addition salts.Type: GrantFiled: October 25, 1978Date of Patent: December 28, 1982Assignee: AB FerrosanInventors: Anders K. K. Bjork, Aina L. Abramo, Bengt E. S. Kjellberg
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Patent number: 4349452Abstract: Anisotropic compounds of the formula (1) ##STR1## wherein X and Y are each hydrogen, C.sub.1 -C.sub.12 alkyl, C.sub.1 -C.sub.12 alkoxy, N-monoalkaylamine having 1 to 12 carbon atoms in the alkyl group, halogen, cyano, nitro, or a cyclic radical of the formula ##STR2## wherein R is hydrogen, halogen, cyano, nitro, C.sub.1 -C.sub.12 alkyl, or C.sub.1 -C.sub.12 alkoxy, Z.sup.1 is a --COO-- group or a --OOC-- group and Z.sup.2 may be the same as Z.sup.1 or a single convalent bond, with the proviso that:(a) only one of the groups X and Y is a cyclic radical, and(b) neither of the groups X or Y is hydrogen, bromine, or poperidino when the other is hydrogen, have low .DELTA.n-values without a greay tendency to form smectic phases and are useful in preparing liquid crystal devices.Type: GrantFiled: July 15, 1980Date of Patent: September 14, 1982Assignee: Merck Patent GmbHInventors: Maged A. Osman, Laszlo Revesz
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Patent number: 4346224Abstract: This invention relates to the production of 4a-aryldecahydroisoquinolines where the aryl group is selected as 3-methoxy phenyl and intermediates. These compounds are morphine analogs and show utility similar to the known morphine, codeine, and thebaine.Type: GrantFiled: January 14, 1981Date of Patent: August 24, 1982Assignee: The United States of America as represented by the Department of Health and Human ServicesInventors: Henry Rapoport, Dwight D. Weller, Richard D. Gless
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Patent number: 4341789Abstract: Compounds of formula (I): ##STR1## wherein: m is 1 or 2; n is 4 to 8; X is CO, protected CO, or CROH wherein R is hydrogen or C.sub.1-4 alkyl and wherein the OH moiety may be protected; R.sub.1 is hydrogen or CO.sub.2 R.sub.1 represents an ester group in which the R.sub.1 moiety contains from 1 to 12 carbon atoms; R.sub.3 is hydroxy, or protected hydroxy; R.sub.2 and R.sub.4 are separately hydrogen, C.sub.1-9 alkyl, C.sub.5-8 cycloalkyl, C.sub.5-8 cycloalkyl-C.sub.1-6 alkyl, phenyl, phenyl C.sub.1-6 alkyl, naphthyl, naphthyl C.sub.1-6 alkyl, any of which phenyl or naphthyl moieties may be substituted by one or more halogen, trifluoromethyl, C.sub.1-6 alkyl, C.sub.1-6 alkoxy or nitro groups; or R.sub.2 and R.sub.4 taken with the carbon atom to which they are joined represent a C.sub.5-8 cycloalkyl group; and salts thereof; except that when one of R.sub.2 and R.sub.4 is hydrogen or C.sub.1-4 alkyl then the other of R.sub.2 and R.sub.4 cannot be hydrogen or C.sub.Type: GrantFiled: November 20, 1978Date of Patent: July 27, 1982Assignee: Beecham Group LimitedInventors: Frederick Cassidy, Gordon Wootton
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Patent number: 4333942Abstract: 4-Phenoxypiperidines of the general formula I ##STR1## wherein R.sup.1 denotes a hydrogen atom, an alkyl group with 1 to 5 carbon atoms, an alkenyl group with 3 to 5 carbon atoms, a cycloalkylmethyl group with 3 to 7 carbon atoms in the cycloalkyl part or a phenylalkyl group with 1 to 3 carbon atoms in the alkyl part,R.sup.2 denotes a hydrogen atom, a nitro group, an amino group or an acylamino group andR.sup.3 denotes a phenyl group or a benzyl group,and their N-oxides and their acid-addition salts are new compounds. They have an antiptotic and analgesic action and are suitable for the treatment of depressions and painful conditions. Processes for the preparation of the new compounds are provided.Type: GrantFiled: July 11, 1980Date of Patent: June 8, 1982Assignee: BYK Gulden Lomberg Chemische Fabrik GmbHInventors: Klaus Eistetter, Hans-Peter Kley, Heinz-Gunter Menge, Hartmann Schaefer
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Patent number: 4332804Abstract: Compounds useful in the prevention and/or treatment of hypertension, congestive heart failure, arrhythmia, migraine, vasospastic disorders, and asthma are represented by the formula ##STR1## wherein: R, R.sup.1, R.sup.2, R.sup.3, and R.sup.4 are independently hydrogen or lower alkyl of one to four carbon atoms; andR.sup.5 and R.sup.6 are independently hydrogen, lower alkyl of one to four carbon atoms or lower alkoxy of one to four carbon atoms; andthe pharmaceutically acceptable acid addition salts thereof.Type: GrantFiled: March 23, 1981Date of Patent: June 1, 1982Assignee: Syntex (U.S.A.) Inc.Inventor: Robin D. Clark
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Patent number: 4330548Abstract: This invention is directed to compounds of the formula ##STR1## which are useful in the treatment of hypertension.Type: GrantFiled: June 29, 1981Date of Patent: May 18, 1982Assignee: E. R. Squibb & Sons, Inc.Inventor: Miguel A. Ondetti
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Patent number: 4312876Abstract: Novel 4-aryloxy- and 4-arylthio-3-phenylpiperidines and related compounds, physiologically acceptable salts thereof and intermediates therefor possessing analgesic, antidepressant properties, and a process for the preparation of such compounds, derivatives and intermediates are described.Type: GrantFiled: February 19, 1980Date of Patent: January 26, 1982Assignee: Hoechst-Roussel Pharmaceuticals IncorporatedInventors: Solomon S. Klioze, Frederick J. Ehrgott
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Patent number: 4311820Abstract: Homopolymers and copolymers of vinyl ethers of the formula I ##STR1## in which R is hydrogen or methyl and R.sup.1 is hydrogen, C.sub.1 -C.sub.8 -alkyl, benzyl, allyl or C.sub.1 -C.sub.2 -acyl, are effective stabilizers for plastics, especially to protect them against photochemical degradation. The monomeric vinyl ethers of the formula I are novel compounds, which can be prepared from the corresponding piperidinols by vinylation by means of acetylene or by transvinylation by means of vinyl ethers or vinyl esters.Type: GrantFiled: February 4, 1980Date of Patent: January 19, 1982Assignee: Ciba-Geigy CorporationInventor: Erwin Nikles
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Patent number: 4309425Abstract: Sulfonamides, such as N-[N-(2-chloro-5-(trifluoromethyl)phenyl]-N-[2,4-dinitro-6-(trifluoromethy l)phenyl]aminothio]-N,4-dimethylbenzenesulfonamide, are useful for control of arthropod pests of plants and animals and fungus disease of plants.Type: GrantFiled: April 11, 1980Date of Patent: January 5, 1982Assignee: E. I. Du Pont de Nemours and CompanyInventor: Jiin-Duey Cheng
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Patent number: 4302590Abstract: Novel 4-aryloxy- and 4-arylthio-3-phenylpiperidines and related compounds, physiologically acceptable salts thereof and intermediates therefor possessing analgesic, antidepressant properties, and a process for the preparation of such compounds, derivatives and intermediates are described.Type: GrantFiled: December 28, 1979Date of Patent: November 24, 1981Assignee: Hoechst-Roussel Pharmaceuticals, Inc.Inventors: Solomon S. Klioze, Frederick J. Ehrgott
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Patent number: 4301287Abstract: The compound Ia ##STR1## has been shown to possess GABA-related activity. The invention relates to Ia and derivatives thereof, covered by the formula ##STR2## in which R" is hydrogen, acetyl or a group of the general formula VII ##STR3## in which R.sub.5 is C.sub.1-8 alkyl; phenyl; phenyl substituted in the 4-position with halogen, lower alkoxy, or lower alkyl; or phenylalkyl in which the phenyl group may be substituted in the 4-position with halogen, lower alkoxy, or lower alkyl; and salts thereof.Type: GrantFiled: December 17, 1979Date of Patent: November 17, 1981Assignee: H. Lundbeck & Co. A/SInventor: Povl Krogsgaard-Larsen
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Patent number: 4296113Abstract: This invention is directed to compounds of the formula ##STR1## which are useful in the treatment of hypertension.Type: GrantFiled: January 14, 1980Date of Patent: October 20, 1981Assignee: E. R. Squibb & Sons, Inc.Inventor: Miguel A. Ondetti
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Patent number: 4296110Abstract: 1-Substituted cyclic lactam-2-carboxylic acids and their derivatives are useful as antihypertensive agents.Type: GrantFiled: October 28, 1980Date of Patent: October 20, 1981Assignee: E. I. Du Pont de Nemours and CompanyInventor: Alexander L. Johnson
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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: 4293468Abstract: Malonates of the formula I ##STR1## in which R.sub.1 is hydrogen or C.sub.1 -C.sub.4 -alkyl, R.sub.2 is C.sub.1 -C.sub.12 -alkyl, C.sub.3 -C.sub.4 -alkenyl, benzyl or phenyl which is optionally substituted by C.sub.1 -C.sub.8 -alkyl or C.sub.1 -C.sub.8 -alkoxy, or is cyano, R.sub.3 is C.sub.1 -C.sub.12 -alkyl, C.sub.3 -C.sub.4 -alkenyl or benzyl and X denotes 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.4, --CH.sub.2 --CH(R.sub.5)--OR.sub.6, --COOR.sub.7 or --CONHR.sub.7, in which R.sub.4 is C.sub.1 -C.sub.8 -alkyl, C.sub.3 -C.sub.6 -alkenyl, phenyl, C.sub.7 -C.sub.8 -aralkyl or cyclohexyl and R.sub.5 is hydrogen, methyl or phenyl and R.sub.Type: GrantFiled: February 4, 1980Date of Patent: October 6, 1981Assignee: Ciba-Geigy AGInventor: Jean Rody
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Patent number: 4293557Abstract: Phenoxypropylamine derivatives of the general formula ##STR1## wherein R.sub.1 represents a hydrogen atom or a methyl or ethyl group, R.sub.2 and R.sub.3, independently from each other, represent a lower alkyl group, or together form a linear alkylene group having 4 to 7 carbon atoms which may be optionally substituted by a hydroxyl or hydroxymethyl group, and R.sub.4 represents a hydrogen atom or a group of the formula --R.sub.5 --Z in which R.sub.5 represents a lower alkylene group, and Z represents a hydrogen atom or an amino, mono- or di-(lower alkyl)-amino, hydrdoxy lower alkylamino, lower alkanoylamino, hydroxyl, lower alkoxy, lower alkanoyloxy, phenoxy, halophenoxy, benzoyloxy or halobenzoyloxy group, andthe salts thereof; to a process for production thereof; and to their medicinal use, particularly to antiulcer agents comprising these phenoxypropylamine derivatives or their salts.Type: GrantFiled: June 30, 1980Date of Patent: October 6, 1981Assignee: Teikoku Hormone Mfg. Co., Ltd.Inventors: Kenyu Shibata, Toshihisa Itaya, Nobuaki Yamakoshi, Shigeru Kurata, Naoyuki Koizumi, Masaaki Tarutani, Hideki Sakuma, Kunihiro Konishi
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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: 4284779Abstract: New substituted acyl derivatives of amino acids which have the general formula ##STR1## are useful as angiotensin converting enzyme inhibitors.Type: GrantFiled: October 31, 1977Date of Patent: August 18, 1981Assignee: E. R. Squibb & Sons, Inc.Inventors: Miguel A. Ondetti, Michael E. Condon
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Patent number: 4284780Abstract: New substituted acyl derivatives of amino acids which have the general formula ##STR1## are useful as angiotensin converting enzyme inhibitors.Type: GrantFiled: May 1, 1978Date of Patent: August 18, 1981Assignee: E. R. Squibb & Sons, Inc.Inventors: Miguel A. Ondetti, Michael E. Condon
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Patent number: 4264572Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is C.sub.1-4 alkyl, C.sub.1-4 alkyl substituted by OH or C.sub.1-2 alkoxy; R.sub.2, R.sub.3 and R.sub.4 are independently each hydrogen or C.sub.1-4 alkyl; Z is --A--NHCH.sub.3 or when R.sub.1 is hydroxy or alkoxy substituted alkyl and/or when R.sub.3 is lower alkyl, Z can also be hydroxy-C.sub.2-5 -alkylamino;R.sub.5 is C.sub.1-4 alkyl or C.sub.1-4 alkyl substituted by OH; n is 1, 2 or 3; and A is: ##STR2## wherein R.sub.7 is H or C.sub.1-4 alkyl; R.sub.8 is H, C.sub.1-4 alkyl or C.sub.1-4 alkyl substituted by OH or C.sub.1-2 alkoxy; or together R.sub.7 and R.sub.8 form a propylene or hydroxypropylene ring; and m is 0 or 1;or an ester thereof with a C.sub.1 -C.sub.4 alkanol or a physiologically acceptable salt thereof with a base, are valuable as X-ray contrast media.Type: GrantFiled: November 30, 1979Date of Patent: April 28, 1981Assignee: Schering AktiengesellschaftInventors: Erich Klieger, Wolfgang Mutzel
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Patent number: 4263438Abstract: 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: January 2, 1979Date of Patent: April 21, 1981Assignee: Pfizer Inc.Inventors: Thomas H. Althuis, Charles A. Harbert, Michael R. Johnson, Lawrence S. Melvin, Jr.
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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: 4252804Abstract: Compounds of the formula I ##STR1## wherein m and n are 0, 1 or 2, X represents oxygen, imino, benzylimino, or morpholinoethylimino, Y represents CO, CONH, COO or SO.sub.2, and NR.sub.1 R.sub.2 represents a dimethylamino, diethylamino, dipropylamino, dibutylamino, allylamino, isobutenylamino, cyclopentylamino, cyclohexylamino, cycloheptylamino, cyclooctylamino, N-methyl N-cyclopentylamino, N-methyl N-cyclohexylamino, N-allyl N-cyclohexylamino, adamantylamino, diethoxyethylamino, dimethylaminoethylamino, dimethylaminopropylamino, N-methyl N-dimethylaminopropyl-amino, benzylamino, 3,4,5-trimethoxybenzylamino, phenethylamino, p-chlorophenethylamino, tetrahydrofurfurylamino, tetrahydropyranylmethylamino, pyrrolidino, isoxazolidinyl, piperidino, 4-hydroxypiperidino, 4-m-chlorophenyl-4-hydroxypiperidino, homopiperidino, 1,2,3,6-tetrahydropyridyl, morpholino, 2-methylmorpholino, 2,6-dimethylmorpholino, 2-morpholinoethylamino, thiamorpholino, piperazino, 4-methylpiperazino, 4-(.alpha.Type: GrantFiled: January 13, 1978Date of Patent: February 24, 1981Assignee: Metabio-JoullieInventors: Maurice Joullie, Gabriel Maillard, Lucien Lakah, Christian J. M. Warolin
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Patent number: 4252947Abstract: The novel product, dextrorotary 7-bromo-6-chloro-3-[3-(3-hydroxy-2-piperidyl)-acetonyl]-4(3H)-quinazolinon e and its non-toxic, pharmaceutically acceptable acid addition salts having anticoccidiosis activity and its preparation and use.Type: GrantFiled: January 26, 1977Date of Patent: February 24, 1981Assignee: Roussel UclafInventors: Jean Jolly, Primo Rizzi, Jean A. Grandadam
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Patent number: 4248877Abstract: The present invention concerns novel compounds of formula I, ##STR1## wherein R.sub.1 is phenethyl, phenethyl monosubstituted in the phenyl ring by fluorine, chlorine, bromine, lower alkyl or lower alkoxy, butyrophenone or butyrophenone monosubstituted in the phenyl ring by fluorine, chlorine, bromine, lower alkyl or lower alkoxy,R.sub.2 is an OR.sub.5 group, wherein R.sub.5 is lower alkyl, lower alkenyl, phenyl or phenyl monosubstituted by fluorine, chlorine, bromine, lower alkyl or lower alkoxy, or an ##STR2## 10 group, wherein independently each of R.sub.6 and R.sub.7 is hydrogen, lower alkyl or cycloalkylalkyl, cycloalkyl, phenyl, phenyl monosubstituted by fluorine, chlorine, bromine, lower alkyl or lower alkoxy, lower phenylalkyl or lower phenylalkyl monosubstituted in the phenyl ring by fluorine, chlorine, bromine, lower alkyl or lower alkoxy, or wherein R.sub.6 and R.sub.Type: GrantFiled: February 22, 1979Date of Patent: February 3, 1981Assignee: Sandoz Ltd.Inventors: Erwin Rissi, Anton Ebnother
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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