Additional Chalcogen Attached Indirectly To The Hetero Ring By Nonionic Bonding Patents (Class 549/488)
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Patent number: 7803800Abstract: New inhibitors of histone deacetylases having antitumor activity, and the process of preparation thereof are herein described. These compounds belong to the structural formula (I) where R1 is a linear or branched chain containing at least two conjugated double bonds, A is an optionally substituted phenyl or pyridyl ring, Ar is an aryl or heteroaryl group, and R3 is hydrogen or alkoxyalkyl. The application also describes the use of said compounds in the treatment of diseases associated to the deregulation of histone deacetylases activity, such as tumors, as well as the relevant pharmaceutical compositions for administration to patients requiring said treatment.Type: GrantFiled: September 30, 2005Date of Patent: September 28, 2010Assignee: DAC S.R.L.Inventors: Saverio Minucci, Pier Giuseppe Pelicci, Antonello Mai, Marco Ballarini, Gaetano Gargiulo, Silvio Massa
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Publication number: 20100240629Abstract: The present invention provides crystalline forms of Fluticasone furoate, characterized by the data disclosed in the specification; pharmaceutical compositions comprising any one or combination of the crystalline forms of Fluticasone furoate and at least one pharmaceutically acceptable excipient; and the use of the crystalline forms of Fluticasone furoate in the preparation of pharmaceutical formulations.Type: ApplicationFiled: March 19, 2010Publication date: September 23, 2010Inventors: Adrienne KOVACSNE-MEZEI, Roman Gabriel, Alexandr Jegorov
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Publication number: 20100191004Abstract: The present invention relates to systems and methods for producing fuels and fuel precursors from carbohydrates. In an embodiment the invention includes a method of producing 5-hydroxymethylfurfural (HMF), including contacting a saccharide with a metal oxide catalyst at a temperature of greater than about 100 degrees Celsius. In an embodiment the invention includes a method of producing a biofuel including contacting a saccharide with a metal oxide catalyst at a temperature of greater than about 100 degrees Celsius. Other embodiments are also described herein.Type: ApplicationFiled: December 22, 2009Publication date: July 29, 2010Applicant: SARTEC CORPORATIONInventors: Clayton V. McNeff, Daniel T. Nowlan
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Publication number: 20100152470Abstract: A method of oxidizing hydroxymethylfurfural (HMF) includes providing a starting material which includes HMF in a solvent comprising water into a reactor. At least one of air and O2 is provided into the reactor. The starting material is contacted with the catalyst comprising Pt on a support material where the contacting is conducted at a reactor temperature of from about 50° C. to about 200° C. A method of producing an oxidation catalyst where ZrO2 is provided and is calcined. The ZrO2 is mixed with platinum (II) acetylacetonate to form a mixture. The mixture is subjected to rotary evaporation to form a product. The product is calcined and reduced under hydrogen to form an activated product. The activated product is passivated under a flow of 2% O2.Type: ApplicationFiled: February 24, 2010Publication date: June 17, 2010Applicant: BATTELLE MEMORIAL INSTITUTEInventors: Michael A. Lilga, Richard T. Hallen, Jianli Hu, James F. White, Michel J. Gray
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Patent number: 7700788Abstract: A method of oxidizing hydroxymethylfurfural (HMF) includes providing a starting material which includes HMF in a solvent comprising water into a reactor. At least one of air and O2 is provided into the reactor. The starting material is contacted with the catalyst comprising Pt on a support material where the contacting is conducted at a reactor temperature of from about 50° C. to about 200° C. A method of producing an oxidation catalyst where ZrO2 is provided and is calcined. The ZrO2 is mixed with platinum (II) acetylacetonate to form a mixture. The mixture is subjected to rotary evaporation to form a product. The product is calcined and reduced under hydrogen to form an activated product. The activated product is passivated under a flow of 2% O2.Type: GrantFiled: October 31, 2007Date of Patent: April 20, 2010Assignee: Battelle Memorial InstituteInventors: Michael A. Lilga, Richard T. Hallen, Jianli Hu, James F. White, Michel J. Gray
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Publication number: 20100058650Abstract: Accordingly, the current invention provides a method for the manufacture of a mixture of 5-hydroxymethylfurfural ethers by reacting a hexose-containing starting material or HMF with mixed alcohols in the presence of an acid catalyst.Type: ApplicationFiled: September 5, 2008Publication date: March 11, 2010Applicant: FURANIX TECHNOLOGIES B.V.Inventors: Gerardus Johannes Maria Gruter, Leo Ernest Manzer
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Patent number: 7670991Abstract: The invention relates to novel substituted benzoylcyclohexenones of the formula (I) in which Q, R1, R2, R3, R4, R5, Y and Z have one of the meanings given in the disclosure, to processes for their preparation, and to their use.Type: GrantFiled: May 3, 2002Date of Patent: March 2, 2010Assignee: Bayer CropScience AGInventors: Hans-Georg Schwarz, Klaus-Helmut Muller, Stefan Herrmann, Dorothee Hoischen, Kristian Kather, Stefan Lehr, Otto Schallner, Mark Wilhelm Drewes, Peter Dahmen, Dieter Feucht, Rolf Pontzen, Shinichi Narabu, Akihiko Yanagi, Shinichi Shirakura, Toshio Goto, Yoshihiro Yamaguchi
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Publication number: 20100029745Abstract: The present invention relates to compounds derived from substituted 3-phenyl-1-(thien-2-yl)propan-1-ones, pharmaceutical compositions comprising them as well as their therapeutic applications, notably in the field of human and animal health.Type: ApplicationFiled: December 28, 2007Publication date: February 4, 2010Inventor: Jean-Francois Delhomel
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Publication number: 20090313889Abstract: The invention provides a process for making hydroxymethylfurfural. A reaction mixture comprising a saccharide and a metal complex of an N-heterocyclic carbene is initially provided. The saccharide is then allowed to react at about 70° C. or below to form hydroxymethylfurfural. The saccharide may be a hexose or a mixture of hexoses, or a dimer, oligomer or polymer or copolymer of a hexose or a mixture thereof.Type: ApplicationFiled: April 8, 2009Publication date: December 24, 2009Applicant: Agency for Science, Technology and ResearchInventors: Yugen ZHANG, Jin Y.G. Chan
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Publication number: 20090281338Abstract: A method for utilizing an industrially convenient fructose source for a dehydration reaction converting a carbohydrate to a furan derivative is provided. Recovery methods also are provided. Embodiments of the methods improve upon the known methods of producing furan derivatives.Type: ApplicationFiled: July 13, 2009Publication date: November 12, 2009Inventor: Alexandra J. Sanborn
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Patent number: 7592467Abstract: The present invention relates to novel inhibitors of prolyl endopeptidase of formula (1) wherein I, A, X, Y and Z are specified in the description. The compounds are useful for the treatment of diseases such as mild cognitive impairment (MCI), Alzheimer's disease, Down Syndrome, Parkinson disease and Chorea Huntington.Type: GrantFiled: April 7, 2006Date of Patent: September 22, 2009Assignee: Probiodrug AGInventors: Andre Johannes Niestroj, Ulrich Heiser, Hans-Ulrich Demuth, Susanne Aust
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Patent number: 7579489Abstract: A method for utilizing an industrially convenient fructose source for a dehydration reaction converting a carbohydrate to a furan derivative is provided. Recovery methods also are provided. Embodiments of the methods improve upon the known methods of producing furan derivatives.Type: GrantFiled: September 28, 2007Date of Patent: August 25, 2009Assignee: Archer-Daniels-Midland CompanyInventor: Alexandra J. Sanborn
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Patent number: 7572925Abstract: Described is a catalytic process for converting sugars to furan derivatives (e.g. 5-hydroxymethylfurfural, furfural, dimethylfuran, etc.) using a biphasic reactor containing a reactive aqueous phase and an organic extracting phase. The process provides a cost-effective route for producing di-substituted furan derivatives. The furan derivatives are useful as value-added intermediates to produce polymers, as precursors to diesel fuel, and as fuel additives.Type: GrantFiled: June 4, 2007Date of Patent: August 11, 2009Assignee: Wisconsin Alumni Research FoundationInventors: James A. Dumesic, Yuriy Rom{acute over (α)}n-Leshkov, Juben N. Chheda
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Publication number: 20090156841Abstract: A method of producing substantially pure HMF, HMF esters and other derivatives from a carbohydrate source by contacting the carbohydrate source with a solid phase catalyst. A carbohydrate starting material is heated in a solvent in a column and continuously flowed through a solid phase catalyst in the presence of an organic acid, or heated with the organic acid and a solid catalyst in solution to form a HMF ester. Heating without organic acid forms HMF. The resulting product is purified by filtration to remove the unreacted starting materials and catalyst. The HMF ester or a mixture of HMF and HMF ester may then be oxidized to 2,5-furandicarboxylic acid (FDCA) by combining the HMF ester with an organic acid, cobalt acetate, manganese acetate and sodium bromide under pressure. Alternatively, the HMF ester may be reduced to form a furan or tetrahydrofuran diol.Type: ApplicationFiled: December 12, 2008Publication date: June 18, 2009Inventors: Alexandra J. SANBORN, Stephen J. Howard
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Publication number: 20090143602Abstract: Disclosed are compositions and methods for the production of mono-esters and di-esters from the reaction of HMF and a reactant selected from a diacid or a diacid derivative; typical reactants are PAN, phthaloyl dichloride, dimethyl phthalate, maleic acid, and maleic anhydride or mono-esters that can be prepared from HMF and MAN.Type: ApplicationFiled: February 7, 2007Publication date: June 4, 2009Inventors: Herman P. Benecke, Jerry L. King, II, Alex Walter Kawczak, Donald W. Zehnder, II, Erica E. Hirschl
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Patent number: 7528157Abstract: Compounds of formula (I): wherein: R2 is H or an optionally substituted C1-4 alkyl group; Y is either —(CH2)n—X—, where n is 1 or 2 and X is O, S, S(?O), S(?O)2, or NRN1, where RN1 is selected from H or optionally substituted C1-4 alkyl, or Y is —C(?O)NRN2—, where RN2 is selected from H, and optionally substituted C1-7 alkyl or C5-20 aryl; R3 is an optionally substituted C6 aryl group linked to a further optionally substituted C6 aryl group, wherein if both C6 aryl groups are benzene rings, there may be an oxygen bridge between the two rings, bound adjacent the link on both rings; A is a single bond or a C1-3 alkylene group; and R5 is either: (i) carboxy; (ii) a group of formula (II): (iii) a group of formula (III): wherein R is optionally substituted C1-7 alkyl, C5-20 aryl or NRN3RN4, where RN3 and RN4 are independently selected from optionally substituted C1-4 alkyl; (iv) tetrazol-5-yl.Type: GrantFiled: December 22, 2006Date of Patent: May 5, 2009Assignee: Asterand UK LimitedInventors: Alexander W. Oxford, Richard J. Davis, Robert A. Coleman, Kenneth L. Clark, David E. Clark, Neil V. Harris, Garry Fenton, George Hynd, Keith A. J. Stuttle, Jonathan M. Sutton, Christopher G. Newton
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Publication number: 20090075819Abstract: The present invention relates to Indanyl- and Tetrahydronaphtyl-amino-thiourea compounds of formula I wherein the variables R1 to R4 are as in the description. The invention relates also to methods of combating or controlling insects, arachnids or nematodes, to methods for protecting growing plants from attack or infestation by insects, arachnids or nematodes, to methods for the protection of seeds from soil insects and of the seedlings' roots and shoots from soil and foliar insects and to methods for treating, controlling, preventing or protecting animals against infestation or infection.Type: ApplicationFiled: November 15, 2006Publication date: March 19, 2009Applicant: BASF SEInventors: Markus Kordes, Christopher Koradin, Deborah L. Culbertson
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Publication number: 20090053780Abstract: A method of converting hydroxymethylfurfural and is derivative species into hydroxymethylfurfural oxidation products is disclosed. The method includes contacting the hydroxymethylfurfural species in a mixture with an enzyme that oxidizes the hydroxymethylfurfural species while controlling hydrogen peroxide in the mixture. In one exemplary embodiment the enzyme is chloroperoxidase and the hydrogen peroxide is metered into the mixture to predominantly and selectively make at least one of formylfuran carboxylic acid or furan dicarboxylic acid. In another embodiment the enzyme is aryl alcohol oxidase and catalase is included in the mixture to remove unwanted hydrogen peroxide by product and the reaction predominantly makes at least one of dimethylfuran or formylfuran carboxylic acid. When the predominant product is a carboxylic acid or furan dicarboxylic acid, it can be recovered in substantially pure form by acid precipitation.Type: ApplicationFiled: August 11, 2008Publication date: February 26, 2009Inventor: Paul D. Hanke
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Publication number: 20090030215Abstract: A method of producing HMF by mixing or agitating an aqueous solution of fructose and inorganic acid catalyst with a water immiscible organic solvent to form an emulsion of the aqueous and organic phases. The mixture is heated in a flow-through reactor at elevated pressures and then separated into aqueous and organic phases to obtain HMF. The aqueous phase and the organic phase are mixed with an in-line mixer prior to, preferably, immediately before addition of the biphasic reaction mixture into the reactor. After separation, HMF is recovered from the aqueous and organic phases to obtain high yields of HMF without the presence of insoluble solid impurities.Type: ApplicationFiled: July 18, 2008Publication date: January 29, 2009Inventors: Christine DIGNAN, Alexandra J. SANBORN
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Publication number: 20090018352Abstract: Disclosed are methods of at least partially purifying HMF from an aqueous mixture containing reactants and products of HMF synthesis from fructose that relies on use of non-functional polymeric resins. A first type of non-functional polymeric resin preferentially adsorbs HMF relative to fructose and is used to remove a majority of fructose from the reaction mixture. HMF is desorbed from the first non-functional polymeric resin with an organic solvent such as acetone. A second type of non-functional polymeric resin preferential adsorbs furfural from an aqueous reaction mixture allowing HMF to pass through. In one embodiment, these non-functional polymeric resins may be used alone in combination with each other to obtain HMF of high purity. In other embodiments, one or more of the foregoing non-functional polymeric resin resins is used in combination with cation exchange chromatography to still further purify the HMF.Type: ApplicationFiled: June 18, 2008Publication date: January 15, 2009Inventors: Douglas F. Geier, John Glenn Soper
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Publication number: 20080200698Abstract: 5-hydroxymethylfurfural of the formula II is prepared via a 5-acyloxymethylfurfural as an intermediate.Type: ApplicationFiled: February 15, 2008Publication date: August 21, 2008Applicant: EVONIK DEGUSSA GmbHInventors: Dietmar Reichert, Martin Sarich, Friedhelm Merz
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Patent number: 7411078Abstract: A method for producing furan-2,5-dicarboxylic acid (FDCA) is provided which can efficiently and quantitatively producing FDCA under mild conditions, without employing an expensive catalyst and with a reduced energy consumption. A furan ring compound having two functional groups selected from a hydroxymethyl group, a formyl group and a carboxyl group in the 2- and 5-positions of the furan ring, is oxidized with a metal permanganate in an alkaline environment to produce furan-2,5-dicarboxylic acid. Advantageously, the alkaline environment contains at least one of alkali metal hydroxides and alkali earth metal hydroxides, and the oxidation is performed at a temperature of from 1 to 50° C. by adding the permanganate metal salt to the alkaline aqueous solution containing the furan ring compound.Type: GrantFiled: March 7, 2007Date of Patent: August 12, 2008Assignee: Canon Kabushiki KaishaInventors: Toshinari Miura, Hirokazu Kakinuma, Takenobu Kawano, Hirohide Matsuhisa
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Patent number: 7101878Abstract: Non-peptide GnRH agents capable of inhibiting the effect of gonadotropin-releasing hormone are described. Such compounds and their pharmaceutically acceptable salts, multimers, prodrugs, and active metabolites are suitable for treating mammalian reproductive disorders and steroid hormone-dependent tumors as well as for regulating fertility, where suppression of gonadotropin release is indicated. Methods for synthesizing the compounds and intermediates useful in their preparation are also described.Type: GrantFiled: August 20, 1999Date of Patent: September 5, 2006Assignee: Agouron Pharmaceuticals, Inc.Inventors: Mark Brian Anderson, Haresh N. Vazir, David Robert Luthin, Genevieve DeGuzman Paderes, Ved P. Pathak, Lance Christopher Christie, Yufeng Hong, Eileen Valenzuela Tompkins, Haitao Li, James Faust
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Patent number: 7019024Abstract: The invention provides a pharmaceutical for treatment of neurological and neuropsychiatric disorders comprising a compound of the formula: or a pharmaceutically acceptable salt thereof.Type: GrantFiled: January 9, 2001Date of Patent: March 28, 2006Assignee: Allelix Neuroscience Inc.Inventors: Vassil Iliya Ognyanov, Laurence A. Borden, Stanley Charles Bell, Jing Zhang
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Patent number: 6963010Abstract: The disclosed invention provides new polyamine analogs and derivatives containing a hydrophobic region and a polyamine region as well as methods and compositions for their use.Type: GrantFiled: January 8, 2002Date of Patent: November 8, 2005Assignee: MediQuest Therapeutics, Inc.Inventors: Mark R. Burns, Gerard F. Graminski
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Patent number: 6603026Abstract: Sugars derived from acidic hydrolysis of biomass consist of glucose and xyloses which are subjected to dehydration, within the hydrolysis environment, to form heterocyclic compounds, furfural and hydroxymethylfurfural. By providing a vessel for hydrolysis of biomass, a hydrolysate containing acid and heterocyclic compounds is formed. Upon withdrawing the hydrolysate from the vessel, and employment of separating means for removing heterocyclic compounds from the hydrolysate, a hydrolysate substantially devoid of heterocyclic compounds is provided for recycle to the vessel and will provide heterocyclic compounds. By withdrawing solids, containing lignins remaining from hydrolysis of biomass, from the vessel, and filtering the solids, to result in a filtrate for recycle to the vessel and provide filtered solids for subsequent processing.Type: GrantFiled: August 7, 2001Date of Patent: August 5, 2003Inventor: Gene E. Lightner
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Patent number: 6589970Abstract: This invention provides novel compounds, pharmaceutical compositions and methods of treating thrombotic disorders in mammals, the compounds having the formula: Wherein: Ar is phenyl, naphthyl, furanyl, benzofuranyl, indolyl, pyrazolyl, oxazolyl, fluorenyl, phenylcycloalkane where the cycloalkane can be cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl and Ar can be optionally substituted by 1 to 3 groups selected from C1-C6 alkyl, C1-C6 alkoxy, hydroxy, phenyl-(CH2)0-6—, phenyl-(CH2)0-6O—, C3-C6 cycloalkyl, —(CH2)—C3-C6 cycloalkyl, halogen, C1-C3 perflouroalkyl and C1-C3 perfluoroalkoxy where phenyl can be substituted with from 1 to 3 groups selected from C1-C6 alkyl, C1-C6 alkoxy, phenyl, halogen, trifluoromethyl or trifluoromethoxy; R1 is hydrogen, C1-C6 alkyl or phenyl-(CH2)1-6— where phenyl can be substituted with C1-C6 alkyl, C1-C6 alkoxy, halo, trifluoromethyl or trifluoromethoxy; R2 and R3 are H, C1-C6 alkyl, phenyl-(CH2)0-3—, halo and C1-C3 perfluType: GrantFiled: June 13, 2002Date of Patent: July 8, 2003Assignee: WyethInventors: Thomas Joseph Commons, Susan Christman Croce, Richard Page Woodworth, Eugene John Trybulski, Hassan Mahmoud Elokdah, David LeRoy Crandall
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Patent number: 6420392Abstract: 2,5-Diaryl tetrahydrofurans, 2,5-diaryl tetrahydrothiophenes, 1,3-diaryl cyclopentanes are disclosed that reduce the chemotaxis and respiratory burst leading to the formation of damaging oxygen radicals of polymorphonuclear leukocytes during an inflammatory or immune response. The compounds exhibit this biological activity by acting as PAF receptor antagonists, by inhibiting the enzyme 5-lipoxygenase, or by exhibiting dual activity, i.e., by acting as both a PAF receptor antagonist and inhibitor of 5-lipoxygenase. Also disclosed is a method to treat disorders mediated by PAF and/or leukotrienes that includes administering an effective amount of one or more of the above-identified compounds or a pharmaceutically acceptable salt thereof, optionally in a pharmaceutically acceptable carrier, to a patient in need of such therapy.Type: GrantFiled: October 9, 1996Date of Patent: July 16, 2002Assignee: Millennium Pharmaceuticals, Inc.Inventors: Tesfaye Biftu, Xiong Cai, Sajjat Hussoin, Gurmit Grewal, T Y Shen
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Patent number: 6369225Abstract: Compounds having Formula 8 wherein the symbols have the meaning defined in the specification are inhibitors of the cytochrome P450RAI (retinoic acid inducible) enzyme, and are used for treating diseases responsive to treatment by retinoids.Type: GrantFiled: August 29, 2000Date of Patent: April 9, 2002Assignee: Allergan Sales, Inc.Inventors: Jayasree Vasudevan, Alan T. Johnson, Dehua Huang, Roshantha A. Chandraratna
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Patent number: 6362166Abstract: Picornaviral 3C protease inhibitors, obtainable by chemical synthesis, inhibit or block the biological activity of picornaviral 3C proteases. These compounds, as well as pharmaceutical compositions that contain these compounds, are suitable for treating patients or hosts infected with one or more picornaviruses. Several novel methods and intermediates can be used to prepare the novel picornaviral 3C protease inhibitors of the present invention.Type: GrantFiled: October 13, 2000Date of Patent: March 26, 2002Assignee: Agouron Pharmaceuticals, Inc.Inventors: Stephen E. Webber, Peter S. Dragovich, Thomas J. Prins, Siegfried H. Reich, Thomas L. Little, Jr., Ethel S. Littlefield, Joseph T. Marakovits, Robert E. Babine, Ted M. Bleckman
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Patent number: 6353119Abstract: The present invention relates to a process for the preparation of 3-substituted-4-arylquinolin-2-one derivatives from a substituted coumarin and using a photochemical cyclization method on a dihydrofuran intermediate.Type: GrantFiled: November 28, 2000Date of Patent: March 5, 2002Assignee: Bristol-Myers Squibb CompanyInventors: Gerard A. Crispino, Shaopeng Wang, Jun Li
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Patent number: 6255340Abstract: A pesticidal composition comprising prallethrin and a neonicotinoid compound given in the following formula (1), (2) or (3), as an active ingredient wherein, A represents a 6-chloro-3-pyridyl, 2-chloro-5-thiazolyl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, 5-methyltetrahydrofuran-3-yl, 3-pyridyl, 6-bromo-3-pyridyl, 3-cyanophenyl, 2-methyl-5-thiazolyl, 2-phenyl-5-thiazolyl or 2-bromo-5-thiazolyl group; R1 represents a hydrogen atom, methyl, ethyl, formyl or acetyl group; R2 represents a methyl, amino, methylamino, N,N-dimethylamino, ethylamino, N,N-diethylamino, N-methyl-N-ethylamino, 1-pyrrolidinyl, (6-chloro-3-pyridyl) methylamino or N-methyl-N-(6-chloro-3-pyridyl)methylamino group; R3 represents a methyl, ethyl, propyl, propenyl or propynyl group; X represents a nitrogen atom or CH group; Y represents a cyano, nitro or trifluoroacetyl group; Z represents a NH group or sulfur atom; D represents an oxygen atom or —N(CH3)— group; m represents 0 or 1; and n represents 2 or 3, hasType: GrantFiled: April 7, 1999Date of Patent: July 3, 2001Assignee: Sumitomo Chemical Company, LimitedInventor: Izumi Fujimoto
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Patent number: 6150397Abstract: The present invention relates to certain 5-aroylnaphthalene derivatives of formula (I): ##STR1## that are inhibitors of prostaglandin G/H synthase, pharmaceutical compositions containing them, methods for their use, and methods for preparing these compounds.Type: GrantFiled: June 21, 1999Date of Patent: November 21, 2000Assignee: Syntex (U.S.A.) Inc.Inventors: David Mark Rotstein, Eric Brian Sjogren
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Patent number: 6127576Abstract: The present invention provides o-aminophenyl ketone derivatives which are intermediates useful in the manufacture of herbicidal sulfamoyl urea compounds, including the crop selective herbicide 1-{[o-(cyclopropylcarbonyl)phenyl]-sulfamoyl}-3-(4,6-dimethoxy-2-pyrimidin yl)urea. Also provided is a method for the preparation of said intermediates.Type: GrantFiled: November 5, 1997Date of Patent: October 3, 2000Assignee: American Cyanamid CompanyInventors: David A. Cortes, Kenneth A. M. Kremer
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Patent number: 6124502Abstract: This invention relates to matrix metalloproteinase (MMP) inhibiting compounds of the formula: ##STR1## where R.sup.1 is C.sub.1 -C.sub.12 alkyl, straight or branched and optionally substituted by halogen, hydroxy, C.sub.1 -C.sub.6 alkoxy, amino, carboxyl, C.sub.1 -C.sub.6 alkoxycarbonyl, carboxamido, nitrile, mono- or di-(C.sub.1 -C.sub.6)alkylamino, thio, C.sub.1 -C.sub.6 alkylthio, aryl, --Oaryl or --OCH.sub.2 aryl where aryl is optionally substituted with C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, carboxy, halogen, cyano, nitro, carboxamido, or hydroxy; and C.sub.1 -C.sub.6 alkanesulfonyloxy. R.sup.2 is .alpha.-OH or .beta.-OH and R.sup.6 is H or R.sup.2 and R.sup.6 together are carbonyl; the chemical intermediates; and processes for the preparation of these compounds and the intermediates thereto.Matrix metalloproteinases (MMP) are a family of zinc-containing calcium dependent proteinases, including stromelysins, collagenases, and gelatinases.Type: GrantFiled: October 9, 1998Date of Patent: September 26, 2000Assignee: American Cyanamid CompanyInventor: Jeremy Ian Levin
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Patent number: 6103708Abstract: This invention provides compounds of Formula I having the structure: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, W, X, Y, and Z are as defined in the specification, or a pharmaceutically acceptable salt thereof, which are useful in treating metabolic disorders related to insulin resistance or hyperglycemia.Type: GrantFiled: May 10, 1999Date of Patent: August 15, 2000Assignee: American Home Products CorporationInventors: Paul J. Dollings, Robert E. McDevitt, Folake O. Adebayo
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Patent number: 6100253Abstract: The present invention relates to novel N-substituted azaheterocyclic compounds of the general formula ##STR1## wherein X, Y, Z, R.sup.1, R.sup.2 and r are as defined in the detailed part of the present description, or salts thereof, to methods for their preparation, to compositions containing them, and to their use for the clinical treatment of painful, hyperalgesic and/or inflammatory conditions in which C-fibers play a pathophysiological role by eliciting neurogenic pain or inflammation as well as their use for treatment of indications caused by or related to the secretion and circulation of insulin antagonising peptides, e.g. non-insulin-dependent diabetes mellitus (NIDDM) and ageing-associated obesity.Type: GrantFiled: August 17, 1999Date of Patent: August 8, 2000Assignee: Novo Nordisk A/SInventors: Knud Erik Andersen, Tine Krogh J.o slashed.rgensen, Rolf Hohlweg, Erik Fischer, Uffe Bang Olsen, Zdenek Polivka, Karel Sindelar, Vladimir Valenta
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Patent number: 6054611Abstract: A method of producing dehydration products from one more 5-carbon or 6-carbon sugars includes reacting said one or more sugars at 40-240.degree. C. for 1 to 96 hours in the presence of 5-90% sulfuric acid, separating the reaction products, and recovering levulinic acid. The sugars are can be generated from strong acid hydrolysis of biomass, such as rice straw, paper, cotton and other cellulosic materials.Type: GrantFiled: May 13, 1998Date of Patent: April 25, 2000Assignee: Arkenol, Inc.Inventors: William A. Farone, John E. Cuzens
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Patent number: 6037367Abstract: Compounds of formula (I) wherein: R.sub.1 is --(CR.sub.4 R.sub.5).sub.n C(O)O(CR.sub.4 R.sub.5).sub.m R.sub.6, --(CR.sub.4 R.sub.5).sub.n C(O)NR.sub.4 (CR.sub.4 R.sub.5).sub.m R.sub.6, (CR.sub.4 R.sub.5).sub.n O(CR.sub.4 R.sub.5).sub.m R.sub.6, or --(CR.sub.4 R.sub.5).sub.r R.sub.6 : W is alkynyl or 2 carbon atoms; R.sub.3 is H or R.sub.7 ; Z is C(O)R.sub.13, (CH.sub.2).sub.0-1 C(O)OR.sub.13, (CH.sub.2).sub.0-1 C(O)NR.sub.10 R.sub.13, (CH.sub.2).sub.0-1 C(R.sub.8 R.sub.8)OR.sub.8, --NHC(O)R.sub.7, (CH.sub.2).sub.0-1 NR.sub.10 R.sub.13, NH[C(O)C(O)OR.sub.8 ], CH.sub.2 NH[C(O)CNR.sub.10 R.sub.13 ], CH.sub.2 S(O).sub.q R.sub.7, CH[S(O).sub.q R.sub.7 ].sub.2, dithiolane, (tetrazol-5-yl), thiazol-2-yl, [1,2,4]thiadiazol-5-yl, [1,3,4]oxadiazol-2-yl, imidazol-2-yl, oxazol-2-yl, or (3- or 5-oxadiazolyl[1,2,4]; R.sub.7 is --(CR.sub.4 R.sub.5).sub.q R.sub.11 or C.sub.1-6 alkyl wherein the R.sub.11 or C.sub.Type: GrantFiled: September 14, 1998Date of Patent: March 14, 2000Assignee: SmithKline Beecham CorporationInventors: Siegfried B. Christensen, IV, Joseph M. Karpinski, James S. Frazee
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Patent number: 5905166Abstract: A new type of yellow dyes with general formula Q-CO--CO--X is disclosed. They can be used in photographic materials as antihalation dyes, acutance dyes or filter dyes. Preferably they are incorporated in UV sensitive contact materials for pre-press applications.Type: GrantFiled: August 12, 1997Date of Patent: May 18, 1999Assignee: Agfa-Gevaert, N.V.Inventor: Eric Kiekens
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Patent number: 5856530Abstract: Picornaviral 3C protease inhibitors, obtainable by chemical synthesis, inhibit or block the biological activity of picornaviral 3C proteases. These compounds, as well as pharmaceutical compositions that contain these compounds, are suitable for treating patients or hosts infected with one or more picornaviruses. Several novel methods and intermediates can be used to prepare the novel picornaviral 3C protease inhibitors of the present invention.Type: GrantFiled: May 2, 1997Date of Patent: January 5, 1999Assignee: Agouron Pharmaceuticals, Inc.Inventors: Stephen E. Webber, Peter S. Dragovich, Thomas J. Prins, Siegfried H. Reich, Thomas L. Little, Jr., Ethel S. Littlefield, Joseph T. Marakovits, Robert E. Babine, Ted M. Bleckman
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Patent number: 5856323Abstract: 2,5-Diaryl tetrahydrofurans, 2,5-diaryl tetrahydrothiophenes, 2,4-diaryl tetrahydrofurans, 2,4-diaryl tetrahydrothiophenes, 1,3-diaryl cyclopentanes, 2,4-diaryl pyrrolidines, and 2,5-diaryl pyrrolidines are disclosed that reduce the chemotaxis and respiratory burst leading to the formation of damaging oxygen radicals of polymorphonuclear leukocytes during an inflammatory or immune response. The compounds exhibit this biological activity by acting as PAF receptor antagonists, by inhibiting the enzyme 5-lipoxygenase, or by exhibiting dual activity, i. e., by acting as both a PAF receptor antagonist and inhibitor of 5-lipoxygenase.A method to treat disorders mediated by PAF or leukotrienes is also disclosed, that includes administering an effective amount of one or more of the above-identified compounds or a pharmaceutically acceptable salt thereof, optionally in a pharmaceutically acceptable carrier.Type: GrantFiled: June 7, 1995Date of Patent: January 5, 1999Assignee: CytoMed, Inc.Inventors: Xiong Cai, Sajjat Hussoin, San-Bao Hwang, David Killian, T. Y. Shen
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Patent number: 5852213Abstract: This invention relates to matrix metalloproteinase (MMP) inhibiting compounds of the formula: ##STR1## where R.sup.1 is C.sub.1 -C.sub.12 alkyl, straight or branched and optionally substituted by halogen, hydroxy, C.sub.1 -C.sub.6 alkoxy, amino, carboxyl, C.sub.1 -C.sub.6 alkoxycarbonyl, carboxamido, nitrile, mono- or di-(C.sub.1 -C.sub.6)alkylamino, thio, C.sub.1 -C.sub.6 alkylthio, aryl, --Oaryl or --OCH.sub.2 aryl where aryl is optionally substituted with C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, carboxy, halogen, cyano, nitro, carboxamido, or hydroxy; and C.sub.1 -C.sub.6 alkanesulfonyloxy. R.sup.2 is .alpha.-OH or .beta.-OH and R.sup.6 is H or R.sup.2 and R.sup.6 together are carbonyl; the chemical intermediates; and processes for the preparation of these compounds and the intermediates thereto.Matrix metalloproteinases (MMP) are a family of zinc-containing calcium dependent proteinases, including stromelysins, collagenases, and gelatinases.Type: GrantFiled: July 2, 1997Date of Patent: December 22, 1998Assignee: American Cyanamid CompanyInventor: Jeremy Ian Levin
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Patent number: 5716624Abstract: Novel pharmaceutically/cosmetically-active polyaromatic propynyl compounds have the structural formula (1): ##STR1## in which X is one of the radicals: ##STR2## and are useful for the treatment of a wide variety of disease states, whether human or veterinary, for example dermatological, rheumatic, respiratory, cardiovascular and ophthalmological disorders, as well as for the treatment of mammalian skin and hair conditions/disorders.Type: GrantFiled: December 15, 1994Date of Patent: February 10, 1998Assignee: C.I.R.D. GaldermaInventor: Jean-Michel Bernardon
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Patent number: 5663199Abstract: Compounds of the formula ##STR1## wherein Q is ##STR2## R.sup.1 is hydrogen or halogen R.sup.2 is hydrogen or halogen;R.sup.3 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.4 is C.sub.3 -C.sub.6 alkenyl or C.sub.3 -C.sub.6 alkynyl;R.sup.5 is hydrogen or halo; andR.sup.6 is ##STR3## Z.sup.2 is S; and R.sup.A is an unsubstituted or methyl- substituted furanyl.These compounds are useful for treating HIV infection.Type: GrantFiled: November 30, 1994Date of Patent: September 2, 1997Assignee: Uniroyal Chemical Ltd./LteeInventor: Walter Gerhard Brouwer
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Patent number: 5648486Abstract: 2,5-Diaryl tetrahydrofurans, 2,5-diaryl tetrahydrothiophenes, 2,4-diaryl tetrahydrofurans, 2,4-diaryl tetrahydrothiophenes, 1,3-diaryl cyclopentanes, 2,4-diaryl pyrrolidines, and 2,5-diaryl pyrrolidines are disclosed that reduce the chemotaxis and respiratory burst leading to the formation of damaging oxygen radicals of polymorphonuclear leukocytes during an inflammatory or immune response. The compounds exhibit this biological activity by acting as PAF receptor antagonists, by inhibiting the enzyme 5-lipoxygenase, or by exhibiting dual activity, i.e., by acting as both a PAF receptor antagonist and inhibitor of 5-lipoxygenase.A method to treat disorders mediated by PAF or leukotrienes is also disclosed, that includes administering an effective amount of one or more of the above-identified compounds or a pharmaceutically acceptable salt thereof, optionally in a pharmaceutically acceptable carrier.Type: GrantFiled: May 12, 1993Date of Patent: July 15, 1997Assignee: CytoMed, Inc.Inventors: Xiong Cai, Sajjat Hussoin, San-Bao Hwang, David Killian, T. Y. Shen
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Patent number: 5610320Abstract: Sulfonamide compounds of the formula or pharmacologically acceptable salts thereof: ##STR1## wherein: R.sup.1 is a hydrogen atom, halogen atom, lower alkyl group, lower alkoxy group, hydroxyl group, nitro group, phenoxy group, cyano group, acetyl group, amino group or a protected amino group; R.sup.2 and R.sup.3 may be the same or different from each other and each is a hydrogen atom, halogen atom, lower alkyl group or lower alkoxy group; R.sup.4 and R.sup.7 may be the same or different from each other and each is a hydrogen atom or a lower alkyl group; R.sup.5 and R.sup.6 may be the same or different from each other and each is a hydrogen atom, halogen atom, lower alkoxy group, amino group or amino group substituted with a lower alkyl or a phenyl group; A is .dbd.CH--; B is .dbd.CH--; and E is selected from the group consisting of ##STR2## in which Q is an oxygen atom or a sulfur atom; and R.sup.Type: GrantFiled: May 26, 1995Date of Patent: March 11, 1997Assignee: Eisai Co., Ltd.Inventors: Hiroshi Yoshino, Norihiro Ueda, Hirovuki Sugumi, Jun Niijima, Yoshihiko Kotake, Toshimi Okada, Nozomu Koyanagi, Tatsuo Watanabe, Makoto Asada, Kentaro Yoshimatsu, Atsumi Iijima, Takeshi Nagasu, Kappei Tsukahara, Kyosuke Kitoh
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Patent number: 5610319Abstract: The invention generally relates to compounds of the formula I, which are in equilibrium with their 4-hydroxy tautomers, and their pharmaceutically acceptable salts: ##STR1## where n is 0 to 2; A is S, CH.sub.2, O, NH or Se, and when n is 0, A is not CH.sub.2, and when n is 1, A is not CH.sub.2 or NH; X is a substituted or unsubstituted C.sub.1 -C.sub.3 alkyl, C.sub.2 -C.sub.3 alkenyl, C.sub.2 -C.sub.3 alkynyl or amino, or sulfur or oxygen; Ar is a substituted or unsubstituted monocyclic carbocycle or heterocycle, or fused or nonfused polycyclic carbocycle or heterocycle; and R.sub.1 and R.sub.2 are hydrogen or a moiety that forms together with the attached CO.sub.2 a readily hydrolyzable ester group. These compounds and their salts are useful as inhibitors of GARFT or as antiproliferative agents. The invention also pertains to pharmaceutical compositions and methods employing such Compounds as GARFT inhibitors or antiproliferative agents.Type: GrantFiled: June 7, 1995Date of Patent: March 11, 1997Assignee: Agouron Pharmaceuticals, Inc.Inventors: Michael D. Varney, William H. Romines, Cynthia L. Palmer
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Patent number: 5594152Abstract: This invention comprises a process for production of a compound of the formula: ##STR1## in which R.sup.1 is selected from the group consisting of H, lower alkyl(C.sub.1 -C.sub.3), alkoxy(C.sub.1 -C.sub.3), bromo, chloro, fluoro, iodo, --COlower alkyl(C.sub.1 -C.sub.3), and --CF.sub.3 ;R.sup.2 is selected from the group consisting of H, lower alkyl(C.sub.1 -C.sub.3), alkoxy(C.sub.1 -C.sub.3), amino, bromo, chloro, fluoro, iodo, and --COlower alkyl(C.sub.1 -C.sub.3);or R.sup.1 and R.sup.2 taken together are methylenedioxy or ethylenedioxy;R.sup.3 is an aldehyde or carboxcylic acid moiety;the moiety ##STR2## wherein Z represents substituted or unsubstituted phenyl ring or an optionally substituted 5 or 6-membered aromatic heterocyclic ring.Type: GrantFiled: March 10, 1995Date of Patent: January 14, 1997Assignee: American Cyanamid CompanyInventors: Aranapakam M. Venkatesan, Jay D. Albright
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Patent number: 5591756Abstract: This invention relates to a compound of the formula: ##STR1## or a pharmaceutically acceptable salt thereof wherein X is oxygen, sulfur, --CH.dbd.CH--, or --CH.dbd.N--;wherein R.sup.1 is --CO.sub.2 R.sup.2 or tetrazole;wherein R.sup.2 is hydrogen, alkyl of 1 to 6 carbons or a pharmaceutically acceptable cation;wherein R is an alkyl of from 1 to 20 carbons, --(CH.sub.2).sub.p CF.sub.3 or --(CH.sub.2).sub.q R.sup.3 wherein R.sup.3 is alkoxy, phenoxy or alkoxy substituted phenoxy wherein the alkoxy group has from 1 to 8 carbons;wherein p and q are integers from 0 to 20;wherein n is 0 or 1; andwherein m is 0, 1, 2, or 3.Type: GrantFiled: May 19, 1995Date of Patent: January 7, 1997Assignee: G. D. Searle & Co.Inventors: Stevan W. Djuric, Richard A. Haack, Julie M. Miyashiro