Nitrogen Attached Directly To The Six-membered Hetero Ring By Nonionic Bonding Patents (Class 546/297)
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3-(2-pyridylaminoalkylamino)cyclobutenediones and pyridones useful as histamine H.sub.1 -antagonists
Patent number: 4659725Abstract: Pyridine derivatives are disclosed which are useful as histamine H.sub.1 -antagonists.Type: GrantFiled: June 19, 1986Date of Patent: April 21, 1987Assignee: Smith Kline & French Laboratories LimitedInventor: Robert J. Ife -
Patent number: 4657908Abstract: The invention relates to carbonyl derivatives which are histamine H-2 antagonists and which inhibit gastric acid secretion. According to the invention where is provided a guanidine derivative of the formula I: ##STR1## in which R.sup.1 and R.sup.2, same or different, are hydrogen or 1-10C alkyl, 3-8C cycloalkyl or 4-14C cycloalkylalkyl, each alkyl, cycloalkyl or cycloalkylalkyl optionally carrying one or more F, Cl or Br atoms, provided that one of R.sup.1 and R.sup.2 is halogen substituted, or R.sup.2 is hydrogen and R.sup.1 is R.sup.5 -E-W in which W is 2-6C alkylene optionally substituted by 1 or 2 1-4C alkyls, E is O, S, SO, SO.sub.2 or NR.sup.6 in which R.sup.6 is H or 1-6C alkyl, R.sup.5 is H or 1-6C alkyl optionally substituted by 1 or 2 1-4C alkyls, or R.sup.5 and R.sup.6 are joined to form a pyrrolidine, piperidine, morpholine, piperazine or N-methylpiperazine ring, or R.sup.2 is H and R.sup.Type: GrantFiled: February 12, 1985Date of Patent: April 14, 1987Assignees: ICI Americas, Inc., Imperial Chemical Industries PLCInventors: Tobias O. Yellin, David J. Gilman, Philip N. Edwards, Michael S. Large, Derrick F. Jones, Keith Oldham
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Patent number: 4652650Abstract: Pyridine derivatives are disclosed which are useful as histamine H.sub.1 -antagonists.Type: GrantFiled: August 5, 1985Date of Patent: March 24, 1987Assignee: Smith Kline & French Laboratories LimitedInventor: Robert J. Ife
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Patent number: 4652572Abstract: This invention relates to 2-amino-3-hydroxy, and 3-carboxy pyridine derivatives, in which the amino group is substituted by a methylthioethyl, butyl or oxypropyl group bearing a terminal heterocyclic group. The compounds have histamine H.sub.2 -antagonist activity. A specific compound of this invention is 2-[2-(2-guanidino-4-thiazolylmethylthio)ethyl]amino pyridine 3-carboxylic acid.Type: GrantFiled: July 12, 1985Date of Patent: March 24, 1987Assignee: Smith Kline & French Laboratories LimitedInventors: Martin Jones, Rodney C. Young
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Patent number: 4647569Abstract: Pyridylaminoethene derivatives of the formula: ##STR1## wherein R.sup.1 is pyridyl, unsubstituted or substituted by one or more substituents R.sup.4 selected from halogen, amino, carboxy, cyano nitro, hydroxy, formyl, trifluoromethyl, aryl, aryloxy, arylthio, benzyloxycarbonylamino, sulphamoyl, tetrazol-5-yl, carbamoyl, thiocarbamoyl, arylcarbamoyl, aroyl, alkyl, alkoxy, alkylthio, alkylsulphonyl, alkylamino, alkylsulphamoyl, arylalkyl, alkanoyl, alkoxycarbonyl, alkoxycarbonylamino, alkylcarbamoyl, alkanoylamino, N-benzyloxycarbonyl-N-alkylamino, or dialkylsulphamoyl, dialkylamino or dialkylcarbamoyl, wherein the alkyl groups may together form a ring, and R.sup.2 and R.sup.3 each represents phenyl, unsubstituted or substituted by one or more substituents R.sup.4 as hereinbefore defined, possess antiarthritic properties.Type: GrantFiled: September 19, 1985Date of Patent: March 3, 1987Assignee: May & Baker LimitedInventors: Raymond F. Collins, Philip Knowles, Libert C. Saunders, Francis J. Tierney, Peter J. Warne
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Patent number: 4643995Abstract: There are disclosed pyridine-2-ethers and pyridine-2-thioethers having a nitrogen-containing cycloaliphatic ring corresponding to the formula ##STR1## the pyridine-N-oxides and/or amine oxides thereof and the pharmaceutically acceptable salts thereof. The compounds show analgesic activity.Type: GrantFiled: December 17, 1984Date of Patent: February 17, 1987Assignee: Degussa AktiengesellschaftInventors: Jurgen Engel, Vladimir Jakovlev, Bernd Nickel, Klaus Thiemer, Gerhard Scheffler
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Patent number: 4643849Abstract: This invention relates to amine derivatives and salts thereof. These compounds have an anti-ulcer activity which is effective to human beings and animals. This disclosure relates to such compounds, a process for the preparation thereof and an anti-ulcer agent containing the same.Type: GrantFiled: November 14, 1983Date of Patent: February 17, 1987Assignee: Toyama Chemical Co., Ltd.Inventors: Shiro Hirai, Hiroshi Hirano, Hirotoshi Arai, Yasuo Kiba, Hisanari Shibata, Yoshikazu Kusayanagi, Minako Yotsuji, Kazuhiko Hashiba, Kikuko Tanada
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Patent number: 4638068Abstract: There are provided novel 2-(2-imidazolin-2-yl)pyridine and quinoline compounds, a process and intermediate compounds for the preparation thereof, and a method for controlling a wide variety of annual and perennial plant species therewith.Type: GrantFiled: May 25, 1982Date of Patent: January 20, 1987Assignee: American Cyanamid CompanyInventor: Marinus Los
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Patent number: 4634764Abstract: Compounds of the formula ##STR1## wherein each R is independently --N(R.sub.1).sub.2, --N.sup..sym. (R.sub.2).sub.3 A.sup..crclbar. or hydroxy, whereineach R.sub.1 is independently hydrogen, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl or aryl orboth R.sub.1 's taken together and with the nitrogen atom to which they are attached form a 5- or 6-membered saturated heterocyclic ring,each R.sub.2 is independently alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl or aryl ortwo R.sub.2 's taken together and with the nitrogen atom to which they are attached form a 5- or 6-membered saturated heterocyclic ring orall three R.sub.2 's taken together and with the nitrogen atom to which they are attached form a 5- or 6-membered unsaturated heterocyclic ring, andA.sup..crclbar. is a non-chromophoric anion,each T is independently a bridging radical, andZ is hydrogen or --N.dbd.Type: GrantFiled: November 10, 1983Date of Patent: January 6, 1987Assignee: Sandoz Ltd.Inventor: Manfred Greve
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Patent number: 4634771Abstract: There is disclosed a method for the conversion of a carboxylic acid group on the ring of an aromatic or N-heteroaromatic compound to a trichloromethyl group which comprises contacting the aromatic or N-heteroaromatic compound with a phenylphosphonous dichloride, phosphorus trichloride and chlorine.Type: GrantFiled: July 25, 1985Date of Patent: January 6, 1987Assignee: Stauffer Chemical CompanyInventors: Kyung S. Shim, Arthur D. F. Toy, James B. Heather
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Patent number: 4631081Abstract: The invention concerns novel compounds of the formula I ##STR1## wherein: Z is selected from oxygen and the group --YAn wherein Y is selected from C.sub.1 to C.sub.6 alkyl and benzyl and An is an anion;k is zero or the integer 1;n is an integer selected from 3 and 4;X is selected from halogen, nitro, cyano, alkyl, substituted alkyl, hydroxy, alkoxy, substituted alkoxy, alkenyl, alkenyloxy, alkynyl, alkynyloxy, acyloxy, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, sulfamoyl, substituted sulfamoyl, alkanoyloxy, benzyloxy, substituted benzyloxy, amino, substituted amino and the groups formyl and alkanoyl and the oxime, imine and Schiff base derivatives thereof;R.sup.1 is selected from hydrogen, alkyl, alkenyl, alkynyl, substituted alkyl, alkylsulfonyl, arylsulfonyl, acyl and an inorganic or organic cation;R.sup.2 is selected from alkyl, substituted alkyl, alkenyl, haloalkenyl, alkynyl and haloalkynyl;R.sup.3 is selected from alkyl, fluoroalkyl, alkenyl, alkynyl, and phenyl; andR.sup.Type: GrantFiled: September 27, 1983Date of Patent: December 23, 1986Assignee: ICI Australia LimitedInventors: Keith G. Watson, Graham J. Bird, Graeme J. Farquharson, Richard J. Conway, Peter G. Tucker
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Patent number: 4628100Abstract: Intermediates for preparing pyrido [1,4] benzodiazepines having antidepressant activity are disclosed of the formula ##STR1## wherein, R is hydrogen, loweralkyl, --alk.sup.1 --NR.sup.1 R.sup.2, --alk.sup.1 --N.dbd.CH--OC.sub.2 H.sub.5 or ##STR2## R.sup.1 and R.sup.2 are loweralkyl, --C(O)--O--loweralkyl or R.sup.1 and R.sup.2 taken together with the adjacent nitrogen atom may form a 1-piperidinyl, 1-phthalimido, 1-pyrrolidinyl, 4-morpholino, 1-piperazinyl or 4-substituted-1-piperazinyl;Ar is 2, 3 or 4-pyridinyl, 2 or 3-thienyl, phenyl or phenyl substituted by 1 to 3 radicals selected from halo, loweralkyl, loweralkoxy, trifluoromethyl or nitro and may be the same or different;alk.sup.1 is a straight or branched hydrocarbon chain containing 1-8 carbon atoms;Z is hydrogen, halogen, loweralkyl, loweralkoxy, hydroxy or nitro;Y is hydrogen or 1-2 radicals selected from loweralkyl, loweralkoxy or hydroxy and may be the same or different,and the acid addition salts thereof.Type: GrantFiled: June 26, 1985Date of Patent: December 9, 1986Assignee: A. H. Robins Company, IncorporatedInventor: Young S. Lo
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Patent number: 4626272Abstract: Compounds of the formula ##STR1## wherein Z is phenyl optionally mono- or di-substituted by halogen, nitro, cyano, trifluoromethyl, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkyl; naphthyl; or furyl;R is cyano, C.sub.1 -C.sub.4 alkoxy, di(C.sub.1 -C.sub.6 -alkyl)-amino, halogen or C.sub.1 -C.sub.4 alkyl;n is 0, 1 or 2;Y is oxygen or sulfur;Q is straight-chain or branched-chain C.sub.2 -C.sub.6 -alkylene;each of R.sub.1 and R.sub.2 is C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkynyl or C.sub.3 -C.sub.8 -cycloalkyl; orR.sub.1 and R.sub.2 together with the nitrogen atom to which they are attached form a C.sub.5 or C.sub.6 heterocyclic group with a maximum of two hetero atoms, which group is optionally substituted by C.sub.1 -C.sub.3 alkyl are useful selective herbicides for post-emergence application in crops of cereals, rice and maize.Type: GrantFiled: December 14, 1984Date of Patent: December 2, 1986Assignee: Ciba-Geigy CorporationInventors: Hans-Georg Brunner, Rolf Schurter, Henry Szczepanski
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Patent number: 4617397Abstract: 2-Alkylaminopyridine derivatives represented by the general formula ##STR1## wherein R denotes a lower alkyl group and Y denotes a halogen atom, and a process for producing the same. These compounds are useful as intermediates in medicines and agricultural chemicals. The final products prepared from the intermediates of the invention are especially useful as herbicides for use in paddy fields and farmlands.Type: GrantFiled: June 21, 1985Date of Patent: October 14, 1986Assignee: Toyo Soda Manufacturing Co., Ltd.Inventors: Kenji Tsuzuki, Hideo Morinaka
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Patent number: 4610819Abstract: A process for the preparation of 1,4-oxazepinones and thiones having the formula: ##STR1## wherein A is an aromatic ring selected from benzene, naphthalene, quinoline or pyridine; n is 1 to 3; Z is an amino radical; R is hydrogen, loweralkyl, cycloalkyl or phenylloweralkyl; and R.sup.4 and R.sup.5 are hydrogen and loweralkyl starting from chloroaromatic carboxylates and alkanolamines is disclosed.Type: GrantFiled: September 19, 1984Date of Patent: September 9, 1986Assignee: A. H. Robins Company, Inc.Inventors: Young S. Lo, Albert D. Cale, Jr.
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Patent number: 4609732Abstract: 2-(Alpha-perhaloalkylbenzyloxy)pyridyl compounds of the following structural formula are intermediates to N-[(alpha-perhaloalkylbenzyloxy)pyridyl]-N'-benzoylurea insecticides: ##STR1## in which R.sub..alpha. is a perhaloalkyl substituent;R.sub.3 is selected from the group consisting of -hydrogen, -halogen and -phenylthio;R.sub.4 is selected from the group consisting of -hydrogen, -halogen, -lower alkyl, -lower alkoxy, -lower alkoxyalkyl, -lower haloalkoxy, -lower alkylthio, -lower alkylsulfonyl, and -diallylamino; orR.sub.3 and R.sub.4 at adjacent ring positions constitute a --OCH.sub.2 O--, --CH.sub.2 C(CH.sub.3).sub.2 O--, or --CF.sub.2 CF.sub.2 O-- bridge;R.sub.5 is -hydrogen or -lower alkyl; andZ is -amino or -nitro.Type: GrantFiled: January 3, 1986Date of Patent: September 2, 1986Assignee: FMC CorporationInventor: Ernest L. Plummer
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Patent number: 4604465Abstract: Compounds useful for inhibiting gastric acid secretion and for the treatment of peptic ulcers caused or exacerbated by gastric acidity having the following formula (I): ##STR1## in which R.sup.1 and R.sup.2, are H, C.sub.1-10 alkyl, C.sub.3-8 cycloalkyl or cycloalkylalkyl in which the alkyl part is C.sub.1-6 and the cycloalkyl part is C.sub.3-8, each of the alkyl, cycloalkyl and cycloalkylalkyls being optionally substituted by one or more halogens selected from F, Cl and Br, provided that at least one of R.sup.1 and R.sup.2 is a halogen substituted alkyl, cycloalkyl or cycloalkylalkyl and provided that there is no halogen substituent on the carbon directly attached to the nitrogen; and X, m, Y, n and R.sup.3 are as described in the specification; and the pharmaceutically-acceptable acid-addition salts thereof.Type: GrantFiled: September 21, 1982Date of Patent: August 5, 1986Assignees: ICI Americas, Inc., Imperial Chemical Industries, LimitedInventors: Tobias O. Yellin, Philip N. Edwards, Michael S. Large
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Patent number: 4602013Abstract: Substituted 2-amino-4(1H)pyridones are provided which are renal vasodilators and bronchodilators.Type: GrantFiled: February 8, 1984Date of Patent: July 22, 1986Assignee: Ortho Pharmaceutical CorporationInventor: Jack B. Jiang
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Patent number: 4596599Abstract: New dextrorotatory enantiomers of phenoxy propionic acid derivatives of the formula ##STR1## in which R.sup.1 represents a radical of the formula ##STR2## wherein X.sup.1 represents hydrogen or halogen,X.sup.2 represents halogen or trifluoromethyl,X.sup.3 represents halogen or trifluoromethyl,X.sup.4 represents hydrogen or halogen andX.sup.5 represents hydrogen or halogen,Y represents oxygen or the radical SO.sub.m,whereinm represents 0, 1 or 2,R.sup.2 represents hydrogen or methyl,n represents 1 or 2 andR.sup.3 and R.sup.4 independently of one another represent hydrogen, halogen, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, nitro, cyano or alkoxycarbonyl with 1 to 4 carbon atoms in the alkoxy group, and their use as herbicides.Type: GrantFiled: December 12, 1983Date of Patent: June 24, 1986Assignee: Bayer AktiengesellschaftInventors: Koichi Moriya, Uwe Priesnitz, Hans-Jochem Riebel, Ludwig Eue, Robert R. Schmidt
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Patent number: 4596869Abstract: A novel compound, useful as an intermediate in the production of compounds of high antimicrobial activity, of the formula: ##STR1## wherein R.sub.a.sup.1 is hydrogen, amino or a protected amino group,R.sub.b.sup.1 and R.sub.c.sup.1 are each hydrogen, halogen, lower alkoxy or arylthio,R.sup.14 is carboxy or a protected carboxy group,X is lower alkylene or a group of the formula: ##STR2## in which R.sup.6 is hydrogen or an organic residue which may have suitable substituent(s), andZ is N or CH,or a salt thereof.Type: GrantFiled: September 19, 1985Date of Patent: June 24, 1986Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Takashi Kamiya, Tsutomu Teraji, Yoshiharu Nakai, Kazuo Sakane, Jiro Goto
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Patent number: 4595763Abstract: Aromatic hydroxyl- or thiol-containing compounds are methylated by contacting with methyl trichloroacetate at elevated temperatures in the presence of an initiator.Type: GrantFiled: June 27, 1983Date of Patent: June 17, 1986Assignee: The Dow Chemical CompanyInventors: James M. Renga, Pen-Chung Wang
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Patent number: 4588816Abstract: The invention is a process for the preparation of (2-(6-substituted)pyridinyloxy)alkanols comprising contacting a 2-(6-substituted)pyridinol with an organic carbonate at a temperature of between about 0.degree. C. and 250.degree. C.Type: GrantFiled: May 8, 1984Date of Patent: May 13, 1986Assignee: The Dow Chemical CompanyInventor: Abel Mendoza
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Patent number: 4568751Abstract: Novel 5-acyl-2-(1H)pyridinones and their use as cardiotonic agents. Typical of the compounds is 5-acetyl-1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile which is prepared by condensing anionic cyano acetamide with 3-[(dimethylamino)methylenyl]-2,4-pentanedione in an inert organic solvent.Type: GrantFiled: April 29, 1983Date of Patent: February 4, 1986Assignee: Merrell Dow Pharmaceuticals Inc.Inventors: Winton D. Jones, Richard C. Dage, Richard A. Schnettler
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Patent number: 4567272Abstract: New 2-aminonitropyridine derivatives are disclosed of the formula: ##STR1## wherein the nitro group is in the 3- or 5-position and X represents hydrogen, an alkoxy group with 1 to 3 C atoms or an unsubstituted or alkyl- or hydroxyalkyl substituted amino group, the alkyl portion of which has 1 to 3 C atomsR.sub.1 and R.sub.2 may be the same or different and represent hydrogen, divalent alkyl- with 1 to 3 C atoms, divalent cyclopropyl- or divalent alkenyl with 1 to 3 C atoms, phenylene- or divalent pyrrol andY and Z may be the same or different and represent hydrogen, hydroxyl- or amino group of the formula II: ##STR2## wherein R.sub.3 and R.sub.4 may be the same or different and represent hydrogen, an unsubstituted alkyl or alkyl with 1 to 3 C atoms, substituted at any position by hydroxy or amino with 1 to 3 C atoms, with the proviso that whenever X represents hydrogen, then R.sub.1 and R.sub.2 cannot both be hydrogen, and R.sub.1 is not hydrogen, R.sub.Type: GrantFiled: September 11, 1984Date of Patent: January 28, 1986Assignee: Rutgerswerke AktiengesellschaftInventors: Winfried Orth, Werner Fickert
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Patent number: 4567188Abstract: Compounds of the formula ##STR1## in which R.sup.1 is an optionally substituted aryl or heteroaryl radical,R.sup.2 is an alkyl or alkenyl radical which is optionally substituted by alkoxy or cycloalkyl, or an optionally substituted aryl or heteroaryl radical, and X is an optionally aklyl-substituted methylene radical or a direct bond, but if X is a direct bond R.sup.2 is not aryl,or physiologically acceptable acid addition salts thereof, exhibit activity on the circulation system particularly as hypotensive agents.Type: GrantFiled: August 10, 1983Date of Patent: January 28, 1986Assignee: Bayer AktiengesellschaftInventors: Ekkehard Niemers, Andreas Knorr, Bernward Garthoff
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Patent number: 4563528Abstract: 5-Pyridinyl-6-R.sub.2 -3-R.sub.1 -2(1H)-pyridinones (I), where R.sub.2 is hydrogen or lower alkyl and R.sub.1 is a cyano, a carbamoyl or an amino group are prepared: by reaction of 1-R.sub.2 -1-oxo-2-pyridinyl-3-dialkylaminopropane (II) with malonamide under solid-liquid or liquid-liquid phase transfer catalysis conditions to obtain 1,2-dihydro-2-oxo-6-R.sub.2 -5-pyridinylnicotinamide (IV), or by reaction of II with cyanoacetamide under solid-liquid or liquid-liquid phase transfer catalysis conditions to obtain 1,2-dihydro-2-oxo-6-R.sub.2 -5-pyridinylnicotinonitrile (III) and partially hydrolizing III to yield IV; finally the carbamoyl group of IV is converted to amino and 1,2-dihydro-2-oxo-6-R.sub.2 -5-pyridinyl-3-aminopyridin-2-one are obtained.Type: GrantFiled: April 19, 1984Date of Patent: January 7, 1986Assignee: Fabrica De Productos Quimicos Y Farmaceuticos Abello, S.A.Inventors: Vicente Gomez Parra, Pedro Gonzalez Hernandez, Felix Sanchez Alonso, Tomas Torres Cebada
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Patent number: 4560762Abstract: 2-Alkylaminopyridine derivatives represented by a general formula of ##STR1## wherein R denotes a lower alkyl group and Y denotes a methoxy group or a halogen atom, and method for producing the same.Type: GrantFiled: May 23, 1983Date of Patent: December 24, 1985Assignee: Toyo Soda Manufacturing Co. Ltd.Inventors: Kenji Tsuzuki, Hideo Morinaka
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Patent number: 4557871Abstract: Novel styrene derivatives of the general formula ##STR1## wherein X is hydrogen or halogen, X.sup.1 is halogen, R is hydrogen or methyl, Y is hydroxymethyl, carboxyl, --COOR.sup.1 or --COR.sup.2 wherein R.sup.1 is prenyl, geranyl, farnesyl, cyclohexyl, phthalidyl, straight or branched chain alkyl having 1 to 6 carbon atoms, or said alkyl substituted with hydroxy, methoxy, pyridyl or alkanoyloxy having 2 to 16 carbon atoms, and R.sup.2 is amino, hydroxyamino mono-(or di-)alkylamino in which the alkyl moiety contains 1 or 2 carbon atoms, ethoxycarbonylmethylamino, carboxymethylamino, thiazolylamino, cyclohexylamino, pyridylamino, morpholino, N-methylpiperazino, phenylamino, phenylamino substituted with one or two of halogen, hydroxy, methyl, methoxy, trifluoromethyl or carboxyl at the phenyl ring, and the pharmaceutically acceptable salts thereof when Y is carboxyl are disclosed. These compounds exhibit high and long-lasting anti-inflammatory, analgesic and anti-pyretic activity.Type: GrantFiled: May 14, 1984Date of Patent: December 10, 1985Assignee: Taisho Pharmaceutical Co., Ltd.Inventors: Katsuo Hatayama, Kensei Yoshikawa, Tatsuhiko Sano, Yutaka Ohuchi, Tomomi Ota, Kazuto Sekiuchi, Kaoru Sota
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Patent number: 4556668Abstract: Described herein are compounds of the formula ##STR1## wherein R.sub.1 is alkyl of from 1 to about 5 carbon atoms, alkenyl of from 2 to about 5 carbon atoms, alkynyl of from 3 to about 5 carbon atoms, cycloalkyl of from 3 to about 7 carbon atoms, alkylcarboxymethyl wherein the alkyl portion is from 1 to about 5 carbon atoms, arylcarboxymethyl wherein the aryl portion is from 6 to about 10 carbon atoms, aryl of from 6 to about 10 carbon atoms, or aralkyl wherein the alkyl portion is from 1 to about 5 carbon atoms and the aryl portion is from about 6 to about 10 carbon atoms; R.sub.2 and R.sub.Type: GrantFiled: July 15, 1983Date of Patent: December 3, 1985Assignee: American Hospital Supply CorporationInventors: Paul W. Erhardt, Chi Woo
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Patent number: 4555517Abstract: Described are compounds of the formula ##STR1## wherein R is hydrogen, lower alkyl, halo, cyano, hydroxy, amino, lower alkylamino, --CH.sub.2 NH.sub.2, CH.sub.2 OH or COOR"; R' is hydrogen, lower cycloalkyl or lower alkyl; R" is lower alkyl or --CH.sub.2 Ar wherein Ar is phenyl, substituted phenyl, furan or thiophene; R'" is COOR", ##STR2## and x is oxygen or nitrogen; or a pharmaceutically acceptable salt thereof and their use in the treatment of impaired ventricular myocardial contractility.The compounds exhibit cardiotonic activity.Type: GrantFiled: August 3, 1984Date of Patent: November 26, 1985Assignee: American Hospital Supply CorporationInventors: David M. Stout, Diane M. Yamamoto, Cynthia Barcelon-Yang
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Patent number: 4551169Abstract: Carbamate derivatives having the formula: ##STR1## wherein X represents an oxygen atom or a sulfur atom and Y represents a --CH-- group or a nitrogen atom; and herbicides utilizing the same.Type: GrantFiled: March 17, 1983Date of Patent: November 5, 1985Assignee: Toyo Soda Manufacturing Company, LimitedInventors: Tetsuo Takematsu, Makoto Konnai, Hideo Morinaka, Yunji Nonaka, Akira Nakanishi
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Patent number: 4550205Abstract: The invention relates to new diphenyl ethers of the general formula ##STR1## wherein X is a hydrogen atom, a halogen atom, a nitro group, an optionally halogenated alkyl, alkoxy or alkylthio group having 1-6 carbon atoms, or an alkanoyl group having 1-4 carbon atoms;Y is a nitrogen atom or a group of the formula CH or CCl;Z is a hydrogen atom, a halogen atom, a nitro group, an optionally halogenated alkyl group having 1-4 carbon atoms, or an alkanoyl group having 1-4 carbon atoms; n is 0-2;R.sub.1 is a hydrogen atom, or an alkyl or alkanoyl group having 1-4 carbon atoms;R.sub.2 and R.sub.3 are equal or different and represent hydrogen atoms or alkyl groups having 1-4 carbon atoms; andA is a group of the general formula ##STR2## wherein R.sub.4 is a hydrogen atom, an alkyl group having 1-6 carbon atoms, or a cation of an alkali metal, alkaline earth metal or an alkylated or non-alkylated ammonium group, andR.sub.5 and R.sub.Type: GrantFiled: November 4, 1982Date of Patent: October 29, 1985Assignee: Duphar International Research B.V.Inventors: Gerard B. Paerels, Cornelis W. Raven
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Patent number: 4547218Abstract: Novel compounds having a pyridinyl radical positioned adjacent to the propanoic acid portion, e.g., ethyl 2-((6-(2-chloro-4-(trifluoromethyl)-phenoxy)-3-nitro-2-pyridinyl)oxy)propi onate, which are selective herbicides useful for controlling weeds in valuable crops.Type: GrantFiled: October 7, 1983Date of Patent: October 15, 1985Assignee: The Dow Chemical CompanyInventors: Sudarshan K. Malhotra, B. Clifford Gerwick, III
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Patent number: 4542221Abstract: A process for preparing a fluoropyridine compound by reacting a chlorinated pyridine compound with a molar excess of an alkali metal fluoride, especially potassium fluoride, in the presence of a catalytic amount of a catalyst selected from halides of organometals and halides of metals of the iron, nickel and copper groups, and which is preferably FeCl.sub.3, whereby at least one chlorine atom of the chlorinated pyridine compound is replaced by a fluorine atom. Of special interest is the preparation of 3,5-dichloro-2,4,6-trichloropyridine from pentachloropyridine.The compounds prepared by such a process are useful for the preparation of agriculturally-useful fluoropyridines.Type: GrantFiled: June 3, 1983Date of Patent: September 17, 1985Assignee: The Dow Chemical CompanyInventor: Edward M. Jones
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Patent number: 4540578Abstract: Novel phenoxyphenyl and phenoxypyridyl benzoyl ureas and a process for their preparation are provided. The novel ureas are useful as the active toxicant in pesticidal compositions.Type: GrantFiled: December 30, 1982Date of Patent: September 10, 1985Assignee: Union Carbide CorporationInventors: David T. Chou, John A. Durden, Themistocles D. J. D'Silva
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Patent number: 4530842Abstract: The compounds of formula I ##STR1## wherein R, R.sub.1 and R.sub.2 have various significances, are useful as agents against heart insufficiency.Type: GrantFiled: May 12, 1983Date of Patent: July 23, 1985Assignee: Sandoz Ltd.Inventor: Gerhard Bormann
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Patent number: 4529800Abstract: A novel simple process for the preparation of 2-halo-3-nitro-6-alkoxy-pyridines having 1 to 6 alkoxy carbon atoms of high purity comprising adding 2-halo-6-alkoxy-pyridine in portions at 0.degree. to 40.degree. C. to a mixture of concentrated sulfuric acid and concentrated nitric acid to obtain impure 2-halo-3-nitro-6-alkoxy-pyridine, treating the latter with a solution of an alkaline reacting compound in a protic solvent and recovering the said pyridine in substantially pure form which are important intermediates for analgesics.Type: GrantFiled: July 11, 1983Date of Patent: July 16, 1985Assignee: Rutgerswerke AktiengesellschaftInventors: Winfried Orth, Werner Fickert
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Patent number: 4528296Abstract: Derivatives of aminopyridinecarboxylic acids which inhibit the dipeptidyl carboxy peptidase (DPCP), methods for their preparation and pharmaceutical compositions containing them.The compounds have formula: ##STR1## where Z is hydrogen, alkyl having from 1 to 3 carbon atoms, halogen or alkoxy having from 1 to 3 carbon atoms;R1 is hydrogen, alkyl having from 1 to 6 carbon atoms, arylalkyl having from 7 to 12 carbon atoms, aryl having from 6 to 15 carbon atoms;m and n are an integer of from 0 to 4 each provided, however, the m+n is lower than 5;R2 is hydrogen, alkyl having from 1 to 6 carbon atoms or arylalkyl having from 7 to 12 carbon atoms;R3 is hydrogen or acyl having from 1 to 8 carbon atoms;R4 is hydrogen or alkyl having from 1 to 3 carbon atoms;and their pharmaceutically acceptable salts with organic or inorganic acids.Type: GrantFiled: December 2, 1983Date of Patent: July 9, 1985Assignee: Simes, Societa Italiana Medicinalle SinteticiInventors: Vittorio Vecchietti, Giorgio Ferrari, Cesare Casagrande
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Patent number: 4526608Abstract: Substituted phenoxyphenylhydroxyamines and pyridyloxyphenylhydroxyamines, and the use thereof for the control of weeds.Type: GrantFiled: March 31, 1983Date of Patent: July 2, 1985Assignee: Zoecon CorporationInventor: Shy-Fuh Lee
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Patent number: 4526974Abstract: The invention provides a process for preparing 2-pyridylalkylamines by reacting an alkali metal derivative of a 2-methylpyridine with a haloalkylamine. The compounds are useful as intermediates in the preparation of compounds having histamine H.sub.1 - and H.sub.2 -antagonist activity.Type: GrantFiled: March 22, 1983Date of Patent: July 2, 1985Assignee: Smith Kline & French Laboratories LimitedInventors: Brian M. Adger, Antonietta R. Mastrocola
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Patent number: 4522647Abstract: Substituted phenoxyalkanediones and intermediates therefor, and the use of said compounds for the control of weeds.Type: GrantFiled: June 29, 1983Date of Patent: June 11, 1985Assignee: Zoecon CorporationInventors: Richard J. Anderson, Shy-Fuh Lee
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Patent number: 4521426Abstract: Novel bicyclooxyheterocyclyl aroyl ureas and a process for their preparation are provided. The novel ureas are useful as the active toxicant in pesticidal compositions.Type: GrantFiled: September 30, 1982Date of Patent: June 4, 1985Assignee: Union Carbide CorporationInventor: Paul A. Cain
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Patent number: 4520199Abstract: 3-Alkoxy-4-substituted phenoxy alkanoic acid esters, derivatives thereof, and the use thereof for the control of weeds.Type: GrantFiled: August 13, 1982Date of Patent: May 28, 1985Assignee: Zoecon CorporationInventors: Gustave K. Kohn, Joe T. Bamberg
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Patent number: 4517193Abstract: A benzoylurea compound of formula: ##STR1## in which each of P and Q independently represents a halogen atom or an alkyl group; m represents 0, 1 or 2; R represents an optionally-substituted alkyl, alkenyl, alkynyl, cycloalkyl or phenyl group, a hydrogen atom, one equivalent of an alkali metal or alkaline earth metal, or an ammonium or substituted ammonium group; each X independently represents a halogen atom, a cyano, nitro or carboxy group, or an optionally-substituted alkyl, alkoxy, alkylthio, cycloalkyl, cycloalkyloxy, cycloalkylthio, alkenyl, alkenylthio, alkylcarbonyl, alkoxycarbonyl, alkylsulphonyl, alkynyl, phenyl, phenoxy, phenylthio or amino group; q=0, 1, 2, 3 or 4; T represents a halogen atom, an alkyl, haloalkyl, alkoxy, haloalkoxy, alkenyloxy or haloalkenyloxy group, or a phenoxy or pyridyloxy group optionally substituted by one or more substituents selected from halogen atoms and nitro, alkyl, haloalkyl and cyano groups; each Y independently represents a halogen atom or a nitro, cyano, alkyl orType: GrantFiled: September 7, 1983Date of Patent: May 14, 1985Assignee: Shell Oil CompanyInventor: Martin Anderson
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Patent number: 4508906Abstract: 3-Amino-4-substituted phenoxy alkanoic (alkenoic) acid esters, derivatives thereof, and the use thereof for the control of weeds.Type: GrantFiled: February 21, 1984Date of Patent: April 2, 1985Assignee: Zoecon CorporationInventors: Joe T. Bamberg, Gustave K. Kohn
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Patent number: 4503061Abstract: Certain 2(1H)-pyridinones are cardiotonic agents. Methods for their preparation and use are disclosed.Type: GrantFiled: July 22, 1983Date of Patent: March 5, 1985Assignee: Warner-Lambert CompanyInventors: James A. Bristol, Ila Sircar
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Patent number: 4493730Abstract: A phenoxypyridine compound represented by the formula: ##STR1## wherein X represents a hydrogen atom, an alkyl group, an alkoxy group, an amino group, a cyano group, a hydroxy group, a halogen atom, or a 2-chloro-4-trifluoromethylphenoxy group, which compound is useful as a herbicide or an intermediate for agricultural chemicals, is disclosed.Type: GrantFiled: September 10, 1982Date of Patent: January 15, 1985Assignee: Ishihara Sangyo Kaisha, Ltd.Inventors: Fumio Kimura, Takahiro Haga
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Patent number: 4482562Abstract: A compound represented by the following formula ##STR1## wherein A represents a direct bond or the bond --O--CH.sub.2 --,B represents a C.sub.1 -C.sub.11 alkylene group bonded to a carbon atom of the aromatic ring D either directly or through --O--, --S--, --SO-- or --NH--,W represents a carbon or nitrogen atom,R.sub.1 represents a C.sub.3 -C.sub.7 alkyl group, a hydroxy-C.sub.1 -C.sub.6 alkyl group, or a phenyl- or diphenyl-alkyl group with the alkyl group having 1 to 4 carbon atoms,R.sub.2 represents a member selected from the group consisting of hydrogen, halogen, OH, C.sub.1 -C.sub.4 alkyl, NO.sub.2, C.sub.1 -C.sub.4 alkoxy, acetyl, allyloxy, carbamoyl and sulfamoyl, and when two or more R.sub.2 groups exist, they may be identical or different, andn represents 1, 2 or 3 and m represents 1 or 2, provided that n+m.gtoreq.4;and an acid addition salt thereof; a process for producing the same; and a pharmaceutical composition comprising aforesaid compound.Type: GrantFiled: September 3, 1982Date of Patent: November 13, 1984Assignee: Kowa Company, Ltd.Inventors: Masami Shiratsuchi, Noboru Shimizu, Hiromichi Shigyo, Yoshinori Kyotani, Hisashi Kunieda, Kiyoshi Kawamura, Seiichi Sato, Toshihiro Akashi, Masahiko Nagakura, Naotoshi Sawada, Yasumi Uchida
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Patent number: 4480100Abstract: [2-[(Nitropyridinyl)amino]phenyl]arylmethanones as chemical intermediates and/or having antidepressant activity having the formula: ##STR1## wherein: B is carbonyl, thioxomethyl, ketal or thioketal,R is hydrogen or -alk.sup.1 -Q,Q is hydrogen, --NR.sup.1 R.sup.2 or halogenare disclosed in a process for preparing pyrido[1,4]benzodiazepines.Type: GrantFiled: September 30, 1982Date of Patent: October 30, 1984Assignee: A. H. Robins Company, Inc.Inventors: Young S. Lo, Chandler R. Taylor, Jr.
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Patent number: 4477672Abstract: 3-Alkylsulfonyloxy-4-substituted phenoxy alkanoic acid esters and the use thereof as intermediates for and as herbicides.Type: GrantFiled: August 6, 1982Date of Patent: October 16, 1984Assignee: Zoecon CorporationInventors: Gustave K. Kohn, Joe T. Bamberg