Chalcogen Bonded Directly To The Bicyclo-carbocyclic Ring System Patents (Class 546/206)
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Patent number: 4508724Abstract: Novel aryloxymethylpyrrolidinols and piperidinols are provided of the formula: ##STR1## wherein R.sup.1 is hydrogen, loweralkyl and phenylloweralkyl; R.sup.2 is hydrogen, loweralkyl and acyl; R.sup.3 is phenyl, naphthyl, 4-indanyl and 5-indanyl; m is 2 or 3 and n is 1 or 2; and the pharmaceutically acceptable salts thereof, having antiarrhythmic, antidepressant and antihypertensive activity.Type: GrantFiled: February 3, 1984Date of Patent: April 2, 1985Assignee: A. H. Robins Company, Inc.Inventors: Chandler R. Taylor, Jr., Harold F. Stauffer, Jr.
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Patent number: 4507292Abstract: Aryl N-oxalyl-N-methyl-carbamates of the general formula ##STR1## in which X represents an alkoxy, alkenoxy, alkinoxy, aryloxy, alkylthio, alkenylthio, alkinylthio or arylthio radical, each of which may be optionally substituted, or represents a radical of the general formula --N R.sup.3 R.sup.4, wherein R.sup.3 and R.sup.4 are identical or different and represent a hydrogen atom or an alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkenyl or aryl radical, each of which may be optionally substituted,or the radicals R.sup.3 and R.sup.4, together with the N atom to which they are bonded, form an optionally substituted heterocyclic ring, andR.sup.1 represents an aryl radical which is optionally substituted,are novel and find use as pesticides, especially for combating insects, acarids and nematodes.Type: GrantFiled: January 27, 1983Date of Patent: March 26, 1985Assignee: Bayer AktiengesellschaftInventors: Gerhard Heywang, Engelbert Kuhle, Wolfgang Behrenz, Ingeborg Hammann, Bernhard Homeyer
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Patent number: 4500529Abstract: N-(Aryloxyalkyl)-N'-(aminoalkyl)ureas and thioureas having the formula: ##STR1## wherein R.sup.1 and R.sup.2 are hydrogen, loweralkyl, cycloalkyl, phenyl or phenyllower alkyl, and R.sup.3 and R.sup.4 are hydrogen, loweralkyl, phenyl and phenylalkyl or R.sup.3 and R.sup.4 taken together with the adjacent nitrogen form a heterocyclic residue are disclosed in a method of suppressing cardiac arrhythmias.Type: GrantFiled: May 9, 1983Date of Patent: February 19, 1985Assignee: A. H. Robins Company, IncorporatedInventors: James R. Shanklin, Jr., Christopher P. Johnson, III
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Patent number: 4499089Abstract: 2-Alkylthio-1-aminoalkyl-2-pyrroline-3-carbonitriles and pharmaceutically acceptable acid addition salts, processes for their preparation and formulation into pharmaceutical compositions as well as their activity as thrombocyte aggregation-inhibitors are described. The compounds are thus useful for the prophylaxis and therapy of thrombotic states.Type: GrantFiled: May 10, 1984Date of Patent: February 12, 1985Assignee: Warner-Lambert CompanyInventors: Hubert Barth, Johannes Hartenstein, Gerhard Satzinger, Edgar Fritschi, Volker Ganser, Horst-Dietmar Tauschel, Gunter Wolf
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Patent number: 4486349Abstract: Process for preparing a para-quinone or ortho-quinone derivative, possibly alkoxylated or aryloxylated, which consists in oxidizing respectively the corresponding hydroquinone or pyrocatechic derivative, by means of the complex prepared, in situ or separately, by combining a cuprous salt, a hydrocarbon substituted by a cyano group and molecular oxygen, the oxidation being possibly carried out in the presence of an alkoxylating or aryloxylating agent of the hydroxylated derivative type.Type: GrantFiled: November 12, 1982Date of Patent: December 4, 1984Assignee: Delalande, S.A.Inventors: Michel Maumy, Patrice J. G. Capdevielle, Philippe L. Dostert, Michel Langlois
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Patent number: 4485109Abstract: 4-Aryl-4-piperidinecarbinols, for example, ##STR1## useful as antidepressants and, in some cases, as anorectic agents.Type: GrantFiled: February 25, 1983Date of Patent: November 27, 1984Assignee: E. I. Du Pont de Nemours and CompanyInventor: Engelbert Ciganek
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Patent number: 4485108Abstract: Compounds of the formula (I) and salts thereof: ##STR1## wherein: A is a bond, --CH.sub.2 -- or --CH.dbd.CH--;R.sup.2 is hydrogen and R.sup.1 is selected from C.sub.1-4 alkyl, hydroxyl, C.sub.1-4 alkoxy, C.sub.1-4 alkanoyloxy, hydrogen, halogen, nitro, cyano, and amino optionally substituted by one or two C.sub.1-4 alkyl groups or by C.sub.1-4 alkanoyl;R.sup.4 is C.sub.1-4 alkyl, hydroxy, C.sub.1-4 alkoxy, C.sub.1-4 alkanoyloxy or nitrato;R.sub.2 N is 1-piperidyl, morpholino or 4-methyl-1-piperazyl, optionally substituted by one or two methyl groups in the 2-, 4- or 6- positions as apt, or 1-pyrrolidyl substituted by one or two methyl groups.m is 0 or 1; andn is 0 to 3a process for their preparation and compositions containing them.Type: GrantFiled: September 24, 1982Date of Patent: November 27, 1984Assignee: Beecham Wuelfing GmbH & Co., KGInventor: Ljerka Jozic
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Patent number: 4447428Abstract: Prostanoid compounds are described having the formula: ##STR1## where A is a cyclopentane ring, which is substituted by oxo and/or hydroxy or etherified hydroxy and may be saturated or unsaturated; X is --CH.dbd.CH--or --(CH.sub.2).sub.2 --; R is alkyl having a terminal --COOH or ester group; and Y is amino or substituted amino, particularly heterocyclic amino.The compounds have bronchodilator activity and/or inhibit blood platelet aggregation.The preparation and pharmaceutical formulation of the compounds is also described.Type: GrantFiled: July 15, 1983Date of Patent: May 8, 1984Assignee: Glaxo Group LimitedInventors: Eric W. Collington, Harry Finch, Roger F. Newton
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Patent number: 4447368Abstract: Aromatic aminosulphonic acids which have a reduced content of discoloring by-products are obtained when aromatic amines are reacted with a sulphonating agent in a reaction medium at least some of which consists of tetramethylene sulphone.Type: GrantFiled: March 31, 1982Date of Patent: May 8, 1984Assignee: Siemens-Allis, Inc.Inventors: Herbert Emde, Heinz U. Blank, Peter Schnegg
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Patent number: 4443462Abstract: Novel compounds of the formula ##STR1## wherein n is an integer of from 2 to 5, R is hydrogen, alkyl, alkoxy, halogen or trifluoromethyl, R.sub.1 is hydrogen, alkyl, alkoxy or halogen, and Z is carbonyl or hydroxymethylene and their pharmaceutically acceptable acid addition salts are useful as antipsychotic agents having a low potential for extrapyramidal side effects. The novel compounds are prepared from novel intermediates of formula ##STR2## or their salts wherein R has the meanings defined above and R.sub.2 is hydrogen, lower alkyl or phenyl(lower alkyl).Type: GrantFiled: September 24, 1982Date of Patent: April 17, 1984Assignee: Merrell Dow Pharmaceuticals Inc.Inventors: Albert A. Carr, Robert A. Farr
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Patent number: 4436908Abstract: Compounds of the formula (I):R.sub.2 N--(CH.sub.2).sub.n --NH--SO.sub.2 R.sup.1 (I)and salts thereof wherein NR.sub.2 represents a piperidyl, pyrrolidyl, or N-methylpiperazyl group any of which may be substituted by one or two methyl groups; R.sup.1 is a 1-naphthyl group substituted by one or two moieties selected from fluorine, chlorine, bromine, methoxyl, ethoxyl, hydroxyl, acetoxyl, nitro, cyano, amino optionally substituted by one or two C.sub.1-6 alkyl groups, methyl, ethyl, carboxyl, methoxycarbonyl, ethoxycarbonyl, acetamido or carboxamido; and n is 2 or 3, pharmaceutical compositions containing them and a process for their preparation.Type: GrantFiled: March 12, 1982Date of Patent: March 13, 1984Assignee: Johann A. WuelfingInventor: Ljerka Jozic
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Patent number: 4435334Abstract: Compounds which contain ammonium groups and sulphonic acid groups and which, in the betaine form, correspond to the formula ##STR1## wherein X denotes --CO-- or --SO.sub.2 --,R.sub.1 denotes hydrogen or alkyl,R.sub.2, R.sub.3 and R.sub.4, independently of one another denote alkyl, alkenyl or aralkyl, orR.sub.4 denotes ##STR2## Y denotes alkylene or xylylene, m denotes 1 or 2,n denotes 0 or 1, andR.sub.5 and R.sub.6, independently of one another, denote hydrogen, alkyl, alkoxy or halogen,and in addition, if n=1,R.sub.2 or R.sub.4 denotes amino, alkylamino, dialkylamino, aryl or cycloalkyl,R.sub.2 and R.sub.3, together with the nitrogen atom which is bonded to them, denote a 5-membered or 6-membered ring,R.sub.2, R.sub.3 and R.sub.4, together with the nitrogen atom which is bonded to them, denote a pyridinium ring, a group of the formula ##STR3## or hydrogen, Y denotes arylene, benzylene or a radical of the formula ##STR4## Z denotes a direct bond, --(CH.sub.2).sub.p --, --O--, --O--(CH.sub.2).sub.Type: GrantFiled: December 28, 1981Date of Patent: March 6, 1984Assignee: Bayer AktiengesellschaftInventors: Frank-Michael Stohr, Peter Wild, Horst Nickel
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Patent number: 4435336Abstract: Aminoarylsulphonic acids which have a relatively high purity and a relatively low content of aminoaryldisulphonic acids can be obtained, if they are prepared, from the corresponding arylammonium hydrogen sulphates, by an improved version of the so-called baking process, wherein the reaction is carried out under pressure at a temperature of at least 140.degree. C. and, at least partially, in the presence of water.Type: GrantFiled: March 31, 1982Date of Patent: March 6, 1984Assignee: Bayer AktiengesellschaftInventors: Herbert Emde, Heinz U. Blank, Peter Schnegg
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Patent number: 4433152Abstract: A compound of the formula, ##STR1## wherein R represents a hydrogen atom, a naphthyl, indanyl, tetrahydronaphthyl or pyridyl group, or a phenyl group which may have 1 to 3 substituents selected from the group consisting of a halogen atom, and an alkyl, alkenyl, alkoxy, alkanoyl, cyano, formyl, trifluoromethyl, phenyl, phenylalkyl, alkanoyl-amino, aminosulfonyl, carboxyl, alkoxycarbonyl, benzyloxycarbonyl, benzoylvinyl, phenylvinylcarbonyl, carboxyvinyl, and diphenyl-methyloxycarobnylvinyl group, A represents an oxygen or sulfur atom, and n represents an integer of 0 to 3, with the proviso that when n is an integer of 0, R must not be a hydrogen atom, or a pharmaceutically acceptable salt thereof is effectively useful for inhibiting a complement reaction, inflammation caused by an allergic reaction, and platelet aggregation.Type: GrantFiled: May 19, 1982Date of Patent: February 21, 1984Assignee: Nippon Chemiphar Co., Ltd.Inventors: Mutsumi Muramatsu, Toshio Satoh, Hiroyasu Sekine, Atsushi Tendo, Yoshio Kikawa, Kaname Kondo
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Patent number: 4431834Abstract: This invention relates to certain bicyclic derivatives which are indane and tetralin compounds and which have herbicidal properties, to processes for their preparation, to herbicidal compositions containing them and to a method of using them as herbicides.Type: GrantFiled: March 29, 1982Date of Patent: February 14, 1984Assignee: Imperial Chemical Industries PLCInventor: David Cartwright
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Patent number: 4429162Abstract: The instant invention relates to compounds of the formula ##STR1## wherein each R.sub.f is independently straight or branched chain perfluoroalkyl of 2 to 18 carbon atoms or perfluoroalkoxy-perfluoroalkyl of 4 to 18 carbon atoms;each R.sub.1 is independently straight or branched chain alkylene of 1 to 12 carbon atoms, alkylenethioalkylene of 2 to 12 carbon atoms, alkyleneoxyalkylene of 2 to 12 carbon atoms, or alkyleneiminoalkylene of 2 to 12 carbon atoms where the imino nitrogen atom contains as a third substituent, hydrogen or alkyl of 1 to 6 carbon atoms;R.sub.2, R.sub.3 and R.sub.4 are independently hydrogen, chloro, bromo, alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, hydroxyalkyl of 1 to 6 carbon atoms or alkoxy of 1 to 6 carbon atoms, and R.sub.2 and R.sub.3 additionally may, together with the carbon atoms to which they are attached, form a fused benzo ring;R.sub.Type: GrantFiled: February 1, 1982Date of Patent: January 31, 1984Assignee: Ciba-Geigy CorporationInventors: Thomas W. Cooke, Robert A. Falk
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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: 4414211Abstract: 5-Membered, 6-membered and 7-membered heterocyclic derivatives of guanidine having hypoglycemic activity.Type: GrantFiled: March 14, 1980Date of Patent: November 8, 1983Assignee: McNeilab, Inc.Inventor: Chris R. Rasmussen
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Patent number: 4390537Abstract: 1-(Substituted-aminoalkoxyphenyl)-2-methylene-1-alkanones, a class of compounds possessing anti-allergic properties for use in the treatment of allergic conditions, such as asthma prepared by etherifying an alkanoylphenol with an aminoalkyl halide, converting the ether formed to a salt of Mannich base by reacting it with a salt of a secondary amine in the presence of formaldehyde or paraformaldehyde and treating the Mannich salt with a weak base to deaminate the same and form the final product.Type: GrantFiled: May 19, 1982Date of Patent: June 28, 1983Assignee: Merck & Co., Inc.Inventor: Edward J. Cragoe, Jr.
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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: 4376123Abstract: Basic ethers of the formula ##STR1## wherein Z is CH.sub.3 --NR.sup.2 --CH.sub.2 CH.sub.2 --CHR.sup.1 --, (1-R.sup.2 -3-piperidyl)-CHR.sup.3 --, (1-R.sup.2 -2-piperidyl)-CH.sub.2 --CHR.sup.3 - or 1-R.sup.2 -3-R.sup.4 -hexahydroazepinyl; R.sup.1 is cyclopropyl or Ar; R.sup.2 is H, alkyl of 1-4 C atoms, alkenyl of 2-4 C atoms, cycloalkylalkyl of 4-8 C atoms or benzyl; R.sup.3 is H or Ar; R.sup.4 is H or alkyl of 1-4 C atoms, Y is --O--CHQ.sup.1 --CHQ.sup.2 --CH.sub.2 --, --O--CHQ.sup.1 --CHQ.sup.2 --CO--, --O--CQ.sup.1 .dbd.CQ.sup.2 --CO-- or --CH.sub.2 --CHQ.sup.1 --CHQ.sup.2 --CO--; Q.sup.1 and Q.sup.2 are independently each H, alkyl of 1-4 C atoms, cycloalkyl or alkylcycloalkyl each of 3-6 total C atoms or Ar; and Ar is phenyl or phenyl substituted by F, Cl, alkoxy or alkylthio, each of 1-4 C atoms, methylenedioxy or CF.sub.3 ; with the proviso that when Z is (CH.sub.3 ).sub.2 N--CH.sub.2 CH.sub.2 --CHR.sup.1 in 7-position and Y is --O--C(C.sub.6 H.sub.5).dbd.CH--CO-- or --O--C(C.sub.6 H.sub.5).dbd.C(CH.sub.Type: GrantFiled: December 15, 1980Date of Patent: March 8, 1983Assignee: Merck Patent Gesellschaft mit Beschrankter HaftungInventors: Hans-Heinrich Hausberg, Helmut Prucher, Jurgen Uhl, Christoph Seyfried, Klaus Minck
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Patent number: 4372955Abstract: Compounds of the formula (I):R.sub.2 N--(CH.sub.2).sub.n --NH--SO.sub.2 R.sup.1 (I)and salts thereof wherein NR.sub.2 represents a piperidyl, pyrrolidyl, or N-methylpiperazyl group any of which may be substituted by one or two methyl groups; R.sup.1 is a 1-naphthyl group substituted by one or two moieties selected from fluorine, chlorine, bromine, methoxyl, ethoxyl, hydroxyl, acetoxyl, nitro, cyano, amino optionally substituted by one or two C.sub.1-6 aklkyl groups, methyl, ethyl, carboxyl, methoxycarbonyl, ethoxycarbonyl, acetamido or carboxamido; and n is 2 or 3, pharmaceutical compositions containing them and a process for their preparation.Type: GrantFiled: March 12, 1982Date of Patent: February 8, 1983Assignee: Johann A. WuelfingInventor: Ljerka Jozic
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Patent number: 4357337Abstract: Compounds, which can be used as medicaments, of the formula: ##STR1## in which n is 1, 2 ore 3, X is fixed in position 4, 5, 6 or 7 on the cycle ##STR2## and represents a hydrogen atom or a halogen atom or an alkyl, alkoxy or alkylthio group having 1 to 4 carbon atoms, the ##STR3## is fixed in position 2 or 3 on the cycle ##STR4## and the broken line represents a second possible bond, are disclosed for the treatment of states of depression, as analgesics and anti-migraine substances.Type: GrantFiled: June 8, 1981Date of Patent: November 2, 1982Assignee: PharmindustrieInventors: Marie-Christine Dubroeucq, Claude G. A. Gueremy, Christian L. A. Renault, Gerard R. Le Fur
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Patent number: 4344893Abstract: Novel compounds are described which are substituted benzophenone hydrazones. They have pesticidal activity, especially against insects and acarids, and pesticidal compositions and methods are described. Methods of making the compounds, and novel intermediates, are also described.Type: GrantFiled: February 25, 1980Date of Patent: August 17, 1982Assignee: The Boots Company LimitedInventors: Leonard G. Copping, John C. Kerry, Thomas I. Watkins, Robert J. Willis, Bryan H. Palmer
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Patent number: 4341906Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is hydrogen, benzyl, benzoyl, alkanoyl of 1 to 5 carbon atoms or --CO--(CH.sub.2).sub.p --NR'R" wherein p is 0 or an integer from 1 to 4; each of R' and R" when taken individually is hydrogen or alkyl of 1 to 4 carbon atoms; R' and R" when taken together with the nitrogen to which they are attached form a 5- or 6-membered heterocyclic ring selected from piperidino, pyrollo, pyrrolidino, morpholino and N-alkylpiperazino having from 1 to 4 carbon atoms in the alkyl group;R.sub.2 is selected from hydrogen, alkanoyl of 1 to 6 carbon atoms and benzoyl;R.sub.3 is selected from hydrogen, methyl and ethyl;R.sub.4 is selected from hydrogen, alkyl of 1 to 6 carbon atoms and benzyl;Z is selected from:(a) alkylene having from one to nine carbon atoms;(b) -(alk.sub.1).sub.m -X-(alk.sub.2).sub.n - wherein each of (alk.sub.1) and (alk.sub.2) is alkylene having from 1 to 9 carbon atoms, with the proviso that the summation of carbon atoms in (alk.sub.1) plus (alk.sub.Type: GrantFiled: December 22, 1980Date of Patent: July 27, 1982Assignee: Pfizer Inc.Inventors: Thomas H. Althuis, Charles A. Harbert, Michael R. Johnson, Lawrence S. Melvin, Jr.
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Patent number: 4334004Abstract: This invention relates to 2-hydroxy-3-naphthoic acid amides of the general formula: ##STR1## wherein R.sub.1 is hydrogen, a substituted or unsubstituted alkyl, cycloalkyl, aralkyl, or aryl group, and R.sub.2 and R.sub.3 are identical or different and are hydrogen, a substituted or unsubstituted alkyl, cycloalkyl, aralkyl, or aryl group, or, together with the nitrogen atom to which they are attached, a substituted or unsubstituted heterocyclic group.Type: GrantFiled: March 16, 1979Date of Patent: June 8, 1982Assignee: Hoechst AktiengesellschaftInventor: Siegfried Scheler
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Patent number: 4329345Abstract: Compounds of the formula ##STR1## wherein R is hydrogen, alkyl, alkoxy, halo, amino, alkylamino, dialkylamino, hydroxy, nitro, trifluoromethyl, mercapto, or alkylmercapto, and may be the same or different,n is an integer from 2 to 4, andR.sub.1 and R.sub.2 are hydrogen or alkyl and may be the same or different, or R.sub.1 and R.sub.2 taken together with the nitrogen to which they are attached may be pyrrolidino, piperidino or morpholinoand their pharmaceutically acceptable, non-toxic acid addition salts have anti-arrhythmic activity.Type: GrantFiled: April 28, 1980Date of Patent: May 11, 1982Assignee: USV Pharmaceutical CorporationInventors: James R. Shroff, Rohit Desai
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Patent number: 4328233Abstract: The invention relates to 2-hydroxymethyl-3,4,5-trihydroxy-6-substituted-piperidines and methods for their preparation. The invention also includes compositions containing said 2-hydroxymethyl-3,4,5-trihydroxy-6-substituted-piperidines and the use of said compounds and compositions for influencing carbohydrate metabolism and fat metabolism and for use in animal nutrition as feed additives.Type: GrantFiled: October 29, 1979Date of Patent: May 4, 1982Assignee: Bayer AktiengesellschaftInventors: Horst Boshagen, Rudiger Sitt, Ernst Truscheit
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Patent number: 4327022Abstract: Aminoalkylnaphthols and esters thereof, useful as cardiotonic or antibacterial agents, are prepared from the corresponding RO-naphthalenealkylamines, certain of which are also useful as cardiotonic agents.Type: GrantFiled: August 1, 1979Date of Patent: April 27, 1982Assignee: Sterling Drug Inc.Inventor: Denis M. Bailey
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Patent number: 4321373Abstract: This invention relates to 2-hydroxy-3-naphthoic acid amides of the general formula: ##STR1## wherein R.sub.1 is hydrogen, a substituted or unsubstituted alkyl, cycloalkyl, aralkyl, or aryl group, and R.sub.2 and R.sub.3 are identical or different and are hydrogen, a substituted or unsubstituted alkyl, cycloalkyl, aralkyl, or aryl group, or, together with the nitrogen atom to which they are attached, a substituted or unsubstituted heterocyclic group. The compounds are useful as coupling components for diazo printing.Type: GrantFiled: August 29, 1980Date of Patent: March 23, 1982Assignee: Hoechst AktiengesellschaftInventor: Siegfried Scheler
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Patent number: 4310669Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is hydrogen, benzyl, benzoyl, alkanoyl of 1 to 5 carbon atoms or --CO--(CH.sub.2).sub.p --NR'R" wherein p is 0 or an integer from 1 to 4; each of R' and R" when taken individually is hydrogen or alkyl of 1 to 4 carbon atoms; R' and R" when taken together with the nitrogen to which they are attached form a 5- or 6-membered heterocyclic ring selected from piperidino, pyrrolo, pyrrolidino, morpholino and N-alkylpiperazino having from 1 to 4 carbon atoms in the alkyl group;R.sub.2 is selected from hydrogen, alkanoyl of 1 to 6 carbon atoms and benzoyl;R.sub.3 is selected from hydrogen, methyl and ethyl;R.sub.4 is selected from hydrogen, alkyl of 1 to 6 carbon atoms and benzyl;Z is selected from:(a) alkylene having from one to nine carbon atoms;(b) -(alk.sub.1).sub.m -X-(alk.sub.2).sub.n - wherein each of (alk.sub.1) and (alk.sub.2) is alkylene having from 1 to 9 carbon atoms, with the proviso that the summation of carbon atoms in (alk.sub.1) plus (alk.sub.Type: GrantFiled: December 22, 1980Date of Patent: January 12, 1982Assignee: Pfizer Inc.Inventors: Thomas H. Althuis, Charles A. Harbert, Michael R. Johnson, Lawrence S. Melvin, Jr.
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Patent number: 4277474Abstract: New propanone derivatives, useful for treating allergic diseases, the pharmacologically allowable salts thereof, their manufacturing process and pharmaceutical composition containing at least one of them as the active ingredient.Type: GrantFiled: September 27, 1979Date of Patent: July 7, 1981Assignee: Nippon Zoki Pharmaceutical Co., Ltd.Inventors: Akihide Kohda, Teikichi Kurosaki
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Patent number: 4267334Abstract: The invention concerns 6-methoxy-2-acetylnaphthalene oxime derivatives of the general formula ##STR1## in which R.sub.1 and R.sub.2 each represent a lower alkyl radical, or form, in association with the nitrogen atom to which they are linked, a saturated heterocyclic group, and the acid addition salts thereof with physiologically acceptable acids. These derivatives have analgesic, antipyretic and anti-inflammatory activity and can be made up into pharmaceutical compositions in tablet, capsule, suppository and the like forms. The derivatives of the invention may be prepared by reacting the corresponding 2-acetyl-6-methoxynaphthalene oximes with an appropriate substituted halogeno-ethylamine.Type: GrantFiled: July 20, 1979Date of Patent: May 12, 1981Assignee: Productos Esteve Internacional S.A.Inventor: Antonio Esteve Subirana
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Patent number: 4249021Abstract: Substituted 1-oxo-2,2-disubstituted-5-indanacetic acids and their salts, esters and amides are disclosed. The products display a dual pharmaceutical utility in that they exhibit diuretic, saluretic and uricosuric activity.Type: GrantFiled: February 26, 1979Date of Patent: February 3, 1981Assignee: Merck & Co., Inc.Inventors: Edward J. Cragoe, Jr., Haydn W. R. Williams, Otto W. Woltersdorf, Jr.
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Patent number: 4247715Abstract: Indanyloxy compounds having 2-alkynyl substituents which exhibit diuretic, saluretic, and uricosuric activity are described. The compounds are obtained according to a process involving selective etherification of a 5-hydroxyindanone followed by alkynylation with a silylated alkynyl bromide to provide novel silylated intermediates which are hydrolyzed to indanyloxy compounds such as (6,7-dichloro-1-oxo-2-phenyl-2-propargyl-5-indanyloxy)acetic acid.Type: GrantFiled: April 9, 1979Date of Patent: January 27, 1981Assignee: Mead Johnson & CompanyInventors: Porter C. Johnson, William L. Matier
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Patent number: 4246269Abstract: The present invention provides new derivatives of perhydro-aza-heterocycles of the formula ##STR1## in which X is the oxo radical or hydrogen and the radical OR.sub.1, in which R.sub.1 is hydrogen or a substituted or unsubstituted aliphatic hydrocarbon radical, a substituted or unsubstituted araliphatic hydrocarbon radical or a substituted or unsubstituted aromatic hydrocarbon radical or an acyl radical, R.sub.2 is hydrogen or a substituted or unsubstituted aliphatic hydrocarbon radical, Y is oxygen or sulphur, n.sub.1 and n.sub.2 each are values of 1 to 3, n.sub.1 +n.sub.2 being at most four, and Ar is a substituted or unsubstituted aromatic hydrocarbon radical, and the acid addition salts, in particular the pharmaceutically acceptable acid addition salts thereof. These new substances possess valuable pharmacological properties, in particular antidepressant activity, and can be used for the treatment of mental depressions.Type: GrantFiled: April 5, 1979Date of Patent: January 20, 1981Assignee: Ciba-Geigy CorporationInventor: Romeo Paioni
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Patent number: 4246268Abstract: Novel compounds of the formula ##STR1## wherein n is an integer of from 2 to 5, R is hydrogen, alkyl, alkoxy, halogen or trifluoromethyl, R.sub.1 is hydrogen, alkyl, alkoxy or halogen, X is carbonyl, hydroxymethylene or methylene, and Z is carbonyl or hydroxymethylene and their pharmaceutically acceptable acid addition salts are useful as antipsychotic agents having a low potential for extrapyramidal side effects. The novel compounds are prepared from novel intermediates of formula ##STR2## or their salts wherein R and X have the meanings defined above.Type: GrantFiled: February 9, 1979Date of Patent: January 20, 1981Assignee: Richardson-Merrell Inc.Inventor: Albert A. Carr
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Patent number: 4239886Abstract: Salts of N-acylaminohydroxynaphthalenesulphonic acids which, in the form of the free acid, correspond to the formula ##STR1## wherein R denotes hydrogen or alkyl,X denotes the radical of a monovalent or divalent acyl group,m denotes 1 or 2 andn denotes 1 or 2,and wherein at least one of the sulphonic acid groups contains, as a cation, a cation of the formula ##STR2## wherein R.sub.1 and R.sub.2 independently of one another denote C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.4 -alkyl or R.sub.3, orR.sub.1 and R.sub.2, together with the nitrogen atom, denote piperidinyl, morpholinyl or pyrrolinyl,R.sub.3 denotes the group ##STR3## R.sub.4 denotes hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.4 -alkyl or the group ##STR4## R.sub.5 and R.sub.6 denote hydrogen, methyl or ethyl and p represents an integer between 1 and 10,a process for their preparation and their use as coupling components for the preparation of azo dyestuffs or concentrated solutions thereof.Type: GrantFiled: February 16, 1979Date of Patent: December 16, 1980Assignee: Bayer AktiengesellschaftInventors: Peter Wild, Horst Nickel
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Patent number: 4238612Abstract: A process for the conversion of compounds of the formula: ##STR1## in which R is a hydrogen atom or a substituent and for which the carbon carrying the vinyl group has the rectus configuration, into the corresponding compounds of formula (I) for which the carbon carrying the vinyl group has the sinister configuration, and vice versa, which comprises subjecting a compound of formula (I) for which the carbon carrying the vinyl group has the rectus or sinister configuration, partially or entirely salified, to a heating at a temperature above 50.degree. C. in a protic solvent or a mixture of protic solvents in the presence or absence of formaldehyde, and isolating the compound of formula (I) for which the carbon carrying the vinyl group has the sinister or rectus configuration thus formed.Type: GrantFiled: March 21, 1979Date of Patent: December 9, 1980Assignee: PharmindustrieInventors: Jean-Jacques Barieux, Marie-Christine Dubroeucq, Francois Rocquet
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Patent number: 4225708Abstract: 2-Sulfamoyl-5-sulfamido-1-naphthols represented by the formula: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 can be the same or different and each represent a hydrogen atom, a straight-chain alkyl group, a branched alkyl group or a cycloalkyl group; or R.sup.1 and R.sup.Type: GrantFiled: August 22, 1979Date of Patent: September 30, 1980Assignee: Konishiroku Photo Industry Co., Ltd.Inventors: Masaru Kanbe, Kazumasa Watanabe, Morito Uemura, Jiro Takahashi, Ryuichiro Kobayashi, Tatsuhiko Kobayashi
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Patent number: 4173640Abstract: Compounds are provided having the structure ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 or R.sub.4 is hydrogen or acyl and R.sub.5 is hydrogen or acyl, X is a straight or branched bivalent alkylene radical and Y is ##STR2## These compounds are useful in the treatment of hypertension.Type: GrantFiled: August 4, 1977Date of Patent: November 6, 1979Assignee: E. R. Squibb & Sons, Inc.Inventors: Frederic P. Hauck, Michael E. Condon, Joyce Reid
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Patent number: 4172945Abstract: Compounds are provided having the structure ##STR1## wherein n is 1, 2 or 3, m is 0, 1 or 2, R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 may be the same or different and can be hydrogen, lower alkyl, halo-lower alkyl, acyl, lower alkoxy-carbonyl ##STR2## amido ##STR3## or lower alkoxyalkylene, X is a straight or branched bivalent aliphatic radical and Y is ##STR4## These compounds are useful in the treatment of hypertension.Type: GrantFiled: July 27, 1978Date of Patent: October 30, 1979Assignee: E. R. Squibb & Sons, Inc.Inventors: Frederic P. Hauck, Joseph E. Sundeen, Joyce Reid
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Patent number: 4172093Abstract: The present invention relates to new pharmacodynamically active compounds of the general structure ##STR1## as well as the corresponding amine oxides, quarternary ammonium compounds and salts with physiologically acceptable acids. In formula I R.sup.1 signifies hydrogen, halogen or alkoxy radicals having 1-3 carbon atoms, R.sup.2 and R.sup.3 signify alkyl radicals having 1-3 carbon atoms, which togetner with the carbon atom, to which they are connected, may form a ring, A either signifies a possibly lower alkyl substituted ethylene, trimethylene or tetramethylene group, in which case D is a group ##STR2## wherein R.sup.4 and R.sup.Type: GrantFiled: March 20, 1973Date of Patent: October 23, 1979Assignee: AB KabiInventors: Barbro K. Goransson-Dahlander, Nils A. Jonsson, Ferenc Merenyi
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Patent number: 4170653Abstract: Disclosed herein are compounds of the formula ##STR1## in which Ar is phenyl or 1-naphthyl; R.sup.1 is hydrogen or lower alkyl; and R.sup.2 and R.sup.3 together with the nitrogen atom to which they are joined form a heterocyclic amine radical selected from the group consisting of 1-pyrrolidinyl, piperidino, morpholino and 4-(lower alkyl)-1-piperazinyl. The compounds are antidepressant agents and methods for their preparation and use also are disclosed.Type: GrantFiled: September 1, 1977Date of Patent: October 9, 1979Assignee: Ayerst McKenna and Harrison LimitedInventors: Jean-Marie Ferland, Real Laliberte, Wilbur Lippmann, Thomas A. Pugsley
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Patent number: 4169108Abstract: Aminoalkylnaphthols and esters thereof, useful as cardiotonic agents, prepared from the corresponding RO-naphthalenealkylamines, certain of which are also useful as cardiotonic agents, are disclosed.Type: GrantFiled: August 16, 1973Date of Patent: September 25, 1979Assignee: Sterling Drug Inc.Inventor: Denis M. Bailey
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Patent number: 4160837Abstract: The present invention provides new derivatives of perhydro-aza-heterocycles of the formula ##STR1## in which X is the oxo radical or hydrogen and the radical OR.sub.1, in which R.sub.1 is hydrogen or a substituted or unsubstituted aliphatic hydrocarbon radical, a substituted or unsubstituted araliphatic hydrocarbon radical or a substituted or unsubstituted aromatic hydrocarbon radical or an acyl radical, R.sub.2 is hydrogen or a substituted or unsubstituted aliphatic hydrocarbon radical, Y is oxygen or sulphur, n.sub.1 and n.sub.2 each are values of 1 to 3, n.sub.1 +n.sub.2 being at most four, and Ar is a substituted or unsubstituted aromatic hydrocarbon radical, and the acid addition salts, in particular the pharmaceutically acceptable acid addition salts thereof. These new substances possess valuable pharmacological properties, in particular antidepressant activity, and can be used for the treatment of mental depressions.Type: GrantFiled: August 24, 1977Date of Patent: July 10, 1979Assignee: Ciba-Geigy CorporationInventor: Romeo Paioni
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Patent number: 4156723Abstract: Compounds are provided having the structure ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 or R.sub.4 is hydrogen or acyl, and R.sub.5 is hydrogen or acyl, X is a straight or branched bivalent alkylene radical and Y is ##STR2## These compounds are useful in the treatment of hypertension.Type: GrantFiled: August 4, 1977Date of Patent: May 29, 1979Assignee: E. R. Squibb & Sons, Inc.Inventors: Frederic P. Hauck, Michael E. Condon, Joyce Reid
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Patent number: 4156730Abstract: A compound of formula (I): ##STR1## wherein: M IS 0 OR 1;N is 4 to 8;A is hydrogen, and when m is 0 and R.sub.5 is methyl it may also be methyl or a group CO.sub.2 B wherein B is hydrogen or CO.sub.2 B represents an ester group in which the B moiety contains from 1 to 12 carbon atoms;X is CO, protected CO, CROH in which R is hydrogen or C.sub.1-4 alkyl and in which 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 1 to 12 carbon atoms;R.sub.4 is 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;D is a group --CH.sub.2 --CH(R.sub.6)--CH(R.sub.7)--C(R.sub.2)(R.sub.3)--, a group--CH.sub.2 --CH(R.sub.6)--CH(R.sub.7)--CH(R.sub.8)--C(R.sub.2)(R.sub.3)--, a group--CH.sub.Type: GrantFiled: May 13, 1977Date of Patent: May 29, 1979Assignee: Beecham Group LimitedInventors: Richard W. Moore, Frederick Cassidy, Gordon Wootton
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Patent number: 4154852Abstract: Novel 7-aminobenzocycloheptenes of the formula ##STR1## wherein X is selected from the group consisting of --NO.sub.2, --NH.sub.2, CH.sub.3 O-- and --OH, R.sub.1 is selected from the group consisting of hydrogen and alkyl of 1 to 5 carbon atoms, R.sub.2 is alkyl of 1 to 5 carbon atoms and R.sub.1 and R.sub.2 together with the nitrogen atom to which they are attached form a saturated heterocycle of 4 to 6 ring carbon atoms optionally containing a second heteroatom in the ring and optionally substituted with an alkyl of 1 to 5 carbon atoms and their non-toxic, pharmaceutically acceptable acid addition salts in optically active or racemic mixture form having antidepressant activity and a process for their preparation.Type: GrantFiled: September 20, 1977Date of Patent: May 15, 1979Assignee: Roussel UclafInventors: Lucien Nedelec, Daniel Frechet, Claude Dumont
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Patent number: 4145427Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is alkyl of 1 to 6 carbon atoms, phenyl, substituted phenyl or heteroaryl;R.sub.2 is hydrogen or alkyl; andR.sub.3 is hydrogen, methyl, methoxy or halogen;And non-toxic, pharmacologically acceptable acid addition salts thereof. The compounds are useful as neuroleptics.Type: GrantFiled: April 14, 1978Date of Patent: March 20, 1979Assignee: Boehringer Ingelheim GmbHInventors: Adolf Langbein, Karl-Heinz Weber, Karin Boke