Halogen Bonded Directly To The Benzene Ring Patents (Class 568/656)
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Publication number: 20150011749Abstract: Metal-accumulating plants for preparing compositions including a metal catalyst derived from the plants. The composition is substantially devoid of organic matter. Also, carrying out chemical reactions with the compositions prepared from metal-accumulating plants.Type: ApplicationFiled: March 5, 2013Publication date: January 8, 2015Applicants: UNIVERSITE MONTPELLIER 2 SCIENCES ET TECHNIQUES, CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUEInventors: Claude Grison, Vincent Escande
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Publication number: 20140303380Abstract: An efficient process is disclosed for producing the compound of formula I, which is the CETP inhibitor anacetrapib, which raises HDL-cholesterol and reduces LDL-cholesterol in human patients and may be effective for treating or reducing the risk of developing atherosclerosis:Type: ApplicationFiled: October 26, 2012Publication date: October 9, 2014Inventors: Cheol K. Chung, Guy R. Humphey, Peter E. Maligres, Timothy J. Wright
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Publication number: 20140135368Abstract: The present invention relates to the field of organic chemistry, more specifically to the synthesis of intermediate compounds which can be used in the synthesis of pharmaceutically active agents such as anacetrapib or derivatives thereof.Type: ApplicationFiled: December 21, 2011Publication date: May 15, 2014Applicant: LEK PHARMACEUTICALS D.D.Inventors: Jan Humljan, Nenad Maras
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Patent number: 8642576Abstract: Compounds of formula Ia and Ib wherein A, B, C and R1 are described herein.Type: GrantFiled: August 29, 2012Date of Patent: February 4, 2014Assignee: Bristol-Myers Squibb CompanyInventors: Mark E. Salvati, Heather Finlay, Bang-Chi Chen, Lalgudi S. Harikrishnan, Ji Jiang, James A. Johnson, Muthoni G. Kamau, R. Michael Lawrence, Jianqing Li, John Lloyd, Michael M. Miller, Zulan Pi, Jennifer X. Qiao, Richard A. Rampulla, Jacques Y. Roberge, Tammy C. Wang, Yufeng Wang, Wu Yang
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Patent number: 8586803Abstract: A liquid crystal compound and a liquid crystal medium are described. The liquid crystal compound is stable to heat and light and has a large dielectric anisotropy and a large optical anisotropy. The liquid crystal medium has a wide temperature range of liquid crystal phase, a large optical anisotropy and a large dielectric anisotropy, and exhibits an optically isotropic liquid crystal phase. The liquid crystal compound has 4 or 5 benzene rings, one of which is a chlorofluorobenzene ring. The liquid crystal medium is characterized in containing the liquid crystal compound and a chiral dopant and exhibiting an optically isotropic liquid crystal phase.Type: GrantFiled: November 30, 2012Date of Patent: November 19, 2013Assignees: JNC Corporation, JNC Petrochemical CorporationInventor: Yasuhiro Haseba
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Patent number: 8575285Abstract: Provided is a catalyst used for a living radical polymerization method, which contains a central element consisting of carbon and at least one halogen atom binding to the central element. Further, a hydrocarbon compound can be used as a catalyst precursor. A monomer having a radical-reactive unsaturated bond is subjected to a radical polymerization reaction in the presence of the catalyst, consequently a polymer having narrow molecular weight distribution can be obtained, and thus the cost of the living radical polymerization can be remarkably reduced. The present invention is significantly more environmentally friendly and economically excellent than conventional living radical polymerization methods, due to advantages such as low toxicity of the catalyst, low amount of the catalyst used, high solubility of the catalyst, mild reaction conditions, and no coloration/no odor (no need of any post-treatments for a molded article), and the like.Type: GrantFiled: September 8, 2009Date of Patent: November 5, 2013Assignee: Kyoto UniversityInventors: Atsushi Goto, Yoshinobu Tsujii, Takeshi Fukuda
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Publication number: 20130211096Abstract: There is disclosed compounds of formula 1, their preparation, intermediates for the preparation and the use of the compounds of the formula 1 as catalysts in various metathesis reactions. The novel metathesis catalysts, which are obtained from readily available precursors, have a high activity and can be used for any type of metathesis reaction.Type: ApplicationFiled: September 10, 2012Publication date: August 15, 2013Inventors: Dieter Arlt, Michal Bieniek, Ralf Karch
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Publication number: 20130178655Abstract: The invention relates to a method for synthesizing 3,5-dichloroanisole from 1,3,5-trichlorobenzene, which comprises: a) the reaction between 1,3,5-trichlorobenzene and a methanolate of an alkaline or alkaline-earth metal in a first solvent chosen from among dimethylsulfoxide and 1,1,3,3-tetramethylurea; b) the precipitation of the product resulting from step a) in a second solvent which is not included among substances considered carcinogenic, mutagenic and/or toxic for reproduction by Regulation (EC) n° 1272/2008 of the European Parliament and of the Council of 16 Dec. 2008; then c) the recovery of the precipitate thus obtained. Application: synthesis of 1,3,5-triamino-2,4,6-trinitrobenzene of which 3,5-dichloroanisole is an intermediate product.Type: ApplicationFiled: January 12, 2011Publication date: July 11, 2013Applicant: Commissariat a l'energie atomique et aux energies alternativesInventors: Eric Pasquinet, Anne Wuillaume, Didier Poullain, François Kosciusko-Morizet, Bénédicte Geneviève Jeanne Marie Treuille, Caroline Marie Catherine Kosciusko-Morizet, Nathalie Geneviève Marie Kosciusko-Morizet, Pierre Thaddée Jacques Hubert Kosciusko-Morizet
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Publication number: 20130165658Abstract: This invention is directed to a process for the preparation of high yield alkyl or aryl iodide from its corresponding carboxylic acid using N-iodo amides.Type: ApplicationFiled: June 9, 2011Publication date: June 27, 2013Inventors: Gennady Nisnevich, Mark Gandelman, Kseniya Kulbitski
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Patent number: 8465850Abstract: The invention provides methods for the application of active materials onto active surfaces useful in organic electronic devices. The methods of the invention include selecting a liquid composition including an active material and a suitable liquid medium whereby when the liquid composition is deposited on the desired active surface it has no greater than about a 40° contact angle; treating the active surface to raise its surface tension before the deposition of a liquid composition containing the desired active material is deposited thereon; and combination thereof. The invention also provides organic electronic devices having at least two active layers, wherein at least one active layer comprises an active material that was deposited using at least one practice of the method of the invention.Type: GrantFiled: April 5, 2011Date of Patent: June 18, 2013Assignee: E I du Pont de Nemours and CompanyInventors: Viacheslav A. Petrov, Daniel David Lecloux
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Publication number: 20130144071Abstract: A method of the present invention, for producing an iodizing agent, includes the step of electrolyzing iodine molecules in a solution by using an acid as a supporting electrolyte. This realizes (i) a method of producing an iodine cation suitable for use as an iodizing agent that does not require a sophisticated separation operation after iodizing reaction is completed, and (ii) an electrolyte used in the method. Further, a method of the present invention, for producing an aromatic iodine compound, includes the step of causing an iodizing agent, and an aromatic compound whose nucleus has one or more substituent groups and two or more hydrogen atoms, to react with each other under the presence of a certain ether compound. This realizes such a method of producing an aromatic iodine compound that position selectivity in iodizing reaction of an aromatic compound is improved.Type: ApplicationFiled: January 30, 2013Publication date: June 6, 2013Applicants: NIPPOH CHEMICALS CO., LTD., JAPAN SCIENCE AND TECHNOLOGY AGENCYInventors: Japan Science and Technology Agency, Nippoh Chemicals Co., Ltd.
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Patent number: 8409673Abstract: A liquid crystal compound having a large refractive index anisotropy, a large dielectric anisotropy, and a low melting point, and a liquid crystal medium having a liquid crystal phase over a wide temperature range, a large refractive index anisotropy, a large dielectric anisotropy, and having an optically isotropic liquid crystal phase, are provided. The present invention is a liquid crystal compound having a chlorobenzene ring, and a liquid crystal medium characterized by containing the liquid crystal compound and a chiral reagent, and exhibiting an optically isotropic liquid crystal phase.Type: GrantFiled: May 7, 2010Date of Patent: April 2, 2013Assignees: JNC Corporation, JNC Petrochemical CorporationInventors: Yasuhiro Haseba, Takafumi Kuninobu
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Patent number: 8357738Abstract: A flame retardant blend comprises at least first and second halogenated non-polymeric phenyl ethers having the general formula (I): wherein each X is independently Cl or Br, each m is independently an integer of 1 to 5, each p is independently an integer of 1 to 4, n is an integer of 1 to 5 and wherein the values of n for the first and second ethers are different.Type: GrantFiled: November 24, 2009Date of Patent: January 22, 2013Assignee: Chemtura CorporationInventors: Larry D. Timberlake, James D. Siebecker
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Publication number: 20120322761Abstract: Compounds of formula Ia and Ib wherein A, B, C and R1 are described herein.Type: ApplicationFiled: August 29, 2012Publication date: December 20, 2012Inventors: Mark E. Salvati, Heather Finlay, Bang-Chi Chen, Lalgudi S. Harikrishnan, Ji Jiang, James A. Johnson, Muthoni G. Kamau, R. Michael Lawrence, Jianqing Li, John Lloyd, Michael M. Miller, Zulan Pi, Jennifer X. Qiao, Richard A. Rampulla, Jacques Y. Roberge, Tammy C. Wang, Yufeng Wang, Wu Yang
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Publication number: 20120316341Abstract: Methods for fluorinating organic compounds are described herein.Type: ApplicationFiled: April 11, 2012Publication date: December 13, 2012Inventors: Tobias Ritter, Pingping Tang
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Patent number: 8287766Abstract: The invention provides methods for the application of active materials onto active surfaces useful in organic electronic devices. The methods of the invention include selecting a liquid composition including an active material and a suitable liquid medium whereby when the liquid composition is deposited on the desired active surface it has no greater than about a 40° contact angle; treating the active surface to raise its surface tension before the deposition of a liquid composition containing the desired active material is deposited thereon; and combination thereof. The invention also provides organic electronic devices having at least two active layers, wherein at least one active layer comprises an active material that was deposited using at least one practice of the method of the invention.Type: GrantFiled: June 16, 2005Date of Patent: October 16, 2012Assignee: E I du Pont de Nemours and CompanyInventors: Viacheslav A. Petrov, Daniel David Lecloux
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Patent number: 8273420Abstract: Disclosed is a liquid crystal composition suitable for producing a liquid crystal electrooptical element which can be driven at a low voltage in a wide temperature range and has high display quality. Also disclosed is a liquid crystal electrooptical element produced by using the liquid crystal composition. Further disclosed is a liquid crystal compound represented by the formula [R1-(A1)a-Z1-(A2)b-Z2-(A7)e-Z5-A3-CF?CFCF2O-A4-Z3-(A5)c-Z4-(A6)d-R2].Type: GrantFiled: May 2, 2011Date of Patent: September 25, 2012Assignee: AGC Seimi Chemical Co., Ltd.Inventors: Atsushi Kawamata, Tomoyuki Asai, Hidemasa Koh
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Publication number: 20120172615Abstract: A substituted alkenylbenzene compound of formula (4): wherein X1 is a halogen atom, —SF5, C1-C6haloalkyl, hydroxy C1-C6haloalkyl, C1-C6alkoxy C1-C6haloalkyl, C3-C8halocycloalkyl, C1-C6haloalkoxy, C1-C3haloalkoxy C1-C3haloalkoxy, C1-C6haloalkylthio, C1-C6haloalkylsulfinyl or C1-C6haloalkylsulfonyl; X3 is a hydrogen, halogen, cyano, nitro, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy or C1-C6alkylthio; X4 is a hydrogen, halogen, cyano, C1-C4alkyl, C1-C4alkoxy or C1-C4haloalkoxy; R3 is —C(R3a)(R3b)R3c, where R3a and R3b are a halogen, or R3a and R3b together form a 3- to 6-membered ring together with the carbon bonding them by forming a C2-C5haloalkylene chain, and R3c is a hydrogen, halogen, C1-C5alkyl, C1-C5haloalkyl, C1-C4haloalkoxy or C1-C4haloalkylthio, with a proviso that where X1 is a fluorine, chlorine or trifluoromethyl, and X2 and X3 are hydrogen, where X1 and X2 are fluorine and X3 is a hydrogen, or where X1 and X2 are trifluoromethyl and X3 is a hydrogen, R3c is a hydrogen, chlorine, bromine, iodine,Type: ApplicationFiled: January 13, 2012Publication date: July 5, 2012Applicant: NISSAN CHEMICAL INDUSTRIES, LTD.Inventors: Takeshi MITA, Takamasa KIKUCHI, Takashi MIZUKOSHI, Manabu YAOSAKA, Mitsuaki KOMODA
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Publication number: 20120171111Abstract: The present invention provides a process for producing an oxidation reaction product of an aromatic compound, having excellent environmental load reduction performance, cost reduction performance, etc. Provided is a process for producing an oxidation reaction product of a raw material aromatic compound by reacting the raw material aromatic compound with an oxidizing agent. The process further uses an electron donor-acceptor linked molecule. The process includes the step of: reacting the electron donor-acceptor linked molecule in an electron-transfer state, the oxidizing agent, and the raw material aromatic compound, thereby generating an oxidation reaction product resulting from oxidation of the raw material aromatic compound.Type: ApplicationFiled: September 15, 2010Publication date: July 5, 2012Applicant: OSAKA UNIVERSITYInventors: Kei Ohkubo, Shunichi Fukuzumi, Kentaro Mizushima
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Publication number: 20120123120Abstract: Phenyliodonium ylide derivatives substituted with electron donating as well as electron withdrawing groups on the aromatic ring are shown for use as precursors in aromatic nucleophilic substitution reactions. The iodonium ylide group is substituted by nucleophiles such as halide ions to provide the corresponding haloaryl derivatives. No-carrier-added [F-18]fluoride ion exclusively substitutes the iodonium ylide moiety in these derivatives and provides high specific activity F-18 labeled fluoro derivatives. Protected L-dopa-6-iodonium ylide derivative have been synthesized as a precursors for the preparation of no-carrier-added 6-[F-18]fluoro-L-dopa. The iodonium ylide group in this L-dopa.derivative is nucleophilically substituted by no-carrier-added [F-18]fluoride ion to provide a [F-18]fluoro intermediates which upon acid hydrolysis yielded 6-[F-18]fluoro-L-dopa.Type: ApplicationFiled: April 1, 2010Publication date: May 17, 2012Applicant: The Regents of the University of CaliforniaInventors: Nagichettiar Satyamurthy, Jorge R. Barrio
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Publication number: 20110275775Abstract: Provided is a catalyst used for a living radical polymerization method, which contains a central element consisting of carbon and at least one halogen atom binding to the central element. Further, a hydrocarbon compound can be used as a catalyst precursor. A monomer having a radical-reactive unsaturated bond is subjected to a radical polymerization reaction in the presence of the catalyst, consequently a polymer having narrow molecular weight distribution can be obtained, and thus the cost of the living radical polymerization can be remarkably reduced. The present invention is significantly more environmentally friendly and economically excellent than conventional living radical polymerization methods, due to advantages such as low toxicity of the catalyst, low amount of the catalyst used, high solubility of the catalyst, mild reaction conditions, and no coloration/no odor (no need of any post-treatments for a molded article), and the like.Type: ApplicationFiled: September 8, 2009Publication date: November 10, 2011Applicant: Kyoto UniversityInventors: Atsushi Goto, Yoshinobu Tsujii, Takeshi Fukuda
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Patent number: 7981486Abstract: A compound represented by the following formula (1), a liquid crystal composition containing the compound and a liquid crystal display device containing the composition: all the symbols in the formula (1) are defined in the specification.Type: GrantFiled: March 18, 2009Date of Patent: July 19, 2011Assignees: JNC Corporation, Chisso Petrochemical CorporationInventor: Yasuyuki Sasada
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Patent number: 7951433Abstract: The invention provides a five-ring liquid crystal compound having a CF2O bonding group as a new compound having a general physical properties necessary for compounds, stability to heat, light and so forth, a wide temperature range of liquid crystal phases, a high clearing point, a good compatibility with other compounds, a large dielectric anisotropy and refractive index anisotropy, and an especially high clearing point and an especially large refractive index anisotropy, and provides a liquid crystal composition and a liquid crystal display device.Type: GrantFiled: February 20, 2008Date of Patent: May 31, 2011Assignees: Chisso Corporation, Chisso Petrochemical CorporationInventor: Hiroyuki Tanaka
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Publication number: 20110124923Abstract: A tetrafluorotoluene compound represented by the formula (1): wherein R represents a C1-C6 alkyl group, and a method for producing a tetrafluorotoluene compound represented by the formula (1) which comprises hydrogenating a tetrafluorobenzyl alcohol compound represented by the formula (2): Wherein R represents a C1-C6 alkyl group.Type: ApplicationFiled: December 19, 2006Publication date: May 26, 2011Applicant: SUMITOMO CHEMICAL COMPANY, LIMITEDInventor: Koji Hagiya
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Publication number: 20110054175Abstract: Described herein are fluorinated organic compounds and methods of making fluorinated organic compounds, for example, using palladium complexes. Also described herein are compositions and kits containing compounds and palladium complexes described herein.Type: ApplicationFiled: February 2, 2009Publication date: March 3, 2011Inventors: Tobias Ritter, Takeru Furuya, Hanns M. Kaiser
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Patent number: 7846513Abstract: A compound represented by the following formula (1), a liquid crystal composition containing the compound and a liquid crystal display device containing the composition: all the symbols in the formula (1) are defined in the specification.Type: GrantFiled: November 9, 2005Date of Patent: December 7, 2010Assignees: Chisso Corporation, Chisso Petrochemical CorporationInventor: Yasuyuki Sasada
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Patent number: 7786330Abstract: The present invention relates to a process for producing a 2-fluoro-6-halophenol as an intermediate; a process for producing a 2-alkoxy-3-fluorophenol and further a 1,2-dialkoxy-3-fluorobenzene from the 2-fluoro-6-halophenol; a second process for producing a 1,2-dialkoxy-3-fluorobenzene from the 2-fluoro-6-halophenol; and a 2-alkoxy-3-fluorophenol. The 2-fluoro-6-halophenol can be obtained using a 2-fluorophenol as a starting material and through a sulfonation reaction, a halogenation reaction, and a deprotection reaction. The 2-fluoro-6-halophenol is alkyl-etherified, and subsequently the halogen atom is converted into a hydroxyl group to obtain the 2-alkoxy-3-fluorophenol, which is further alkyl-etherified to thereby obtain the 1,2-dialkoxy-3-fluorobenzene. Alternatively, a 1,2-dialkoxy-3-fluorobenzene is also obtained by converting the halogen atom of the 2-fluoro-6-halophenol into a hydroxyl group to thereby form 3-fluorocatechol and subsequently alkyl-etherifying two hydroxyl groups thereof.Type: GrantFiled: February 24, 2009Date of Patent: August 31, 2010Assignees: Asahi Glass Company, Limited, Charna Chemicals, Ltd.Inventors: Mingjian Qiu, Wei Zhang, Zhaohui Chen, Chunshan Zhang, Yali Zhang
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Patent number: 7758931Abstract: Such a liquid crystal compound is provided that has stability to heat, light and so forth, has a nematic phase in a wide temperature range, has a small viscosity, a suitable optical anisotropy, and suitable elastic constants K33 and K11 (K33: bend elastic constant, K11: splay elastic constant), and has suitable negative dielectric anisotropy and excellent compatibility with other liquid crystal compounds. A liquid crystal composition containing the liquid crystal compound, and a liquid crystal display device containing the liquid crystal composition are also provided.Type: GrantFiled: June 29, 2009Date of Patent: July 20, 2010Assignees: Chisso Corporation, Chisso Petrochemical CorporationInventors: Yasuyuki Goto, Teru Shimada, Teruyo Sugiura
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Patent number: 7686978Abstract: The invention provides methods for the application of active materials onto active surfaces useful in organic electronic devices. The methods of the invention include selecting a liquid composition including an active material and a suitable liquid medium whereby when the liquid composition is deposited on the desired active surface it has no greater than about a 40° contact angle; treating the active surface to raise its surface tension before the deposition of a liquid composition containing the desired active material is deposited thereon; and combination thereof. The invention also provides organic electronic devices having at least two active layers, wherein at least one active layer comprises an active material that was deposited using at least one practice of the method of the invention.Type: GrantFiled: September 24, 2003Date of Patent: March 30, 2010Assignee: E. I. du Pont de Nemours and CompanyInventors: Viacheslav A. Petrov, Daniel David Lecloux
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Publication number: 20090326280Abstract: A process for the preparation of alkyl aryl ethers from alcohols and aryl halides, usually as intermediates in organic synthesis. In a method, the mixing aryl halide and an alcohol is mixed with dimethyl sulfoxide, water, and a metal hydroxide to form a mixture and the mixture is heated to reflux. Additional steps may then be performed to provide for purification.Type: ApplicationFiled: June 26, 2009Publication date: December 31, 2009Inventor: Todd Coleman
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Publication number: 20090264683Abstract: Such a liquid crystal compound is provided that has stability to heat, light and so forth, has a nematic phase in a wide temperature range, has a small viscosity, a suitable optical anisotropy, and suitable elastic constants K33 and K11 (K33: bend elastic constant, K11: splay elastic constant), and has suitable negative dielectric anisotropy and excellent compatibility with other liquid crystal compounds. A liquid crystal composition containing the liquid crystal compound, and a liquid crystal display device containing the liquid crystal composition are also provided.Type: ApplicationFiled: June 29, 2009Publication date: October 22, 2009Applicants: CHISSO CORPORATION, CHISSO PETROCHEMICAL CORPORATIONInventors: YASUYUKI GOTO, Teru Shimada, Teruyo Sugiura
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Patent number: 7531700Abstract: The invention provides new fluorinated solvents that have many uses. One such use is as a solvent useful in the deposition of organic active materials in the manufacture of organic electronic devices. The new fluorinated solvents are fluorinated arylethers and can be readily prepared from corresponding phenols and fluorinated olefins.Type: GrantFiled: September 24, 2003Date of Patent: May 12, 2009Assignee: E.I. du Pont de Nemours and CompanyInventor: Viacheslav A. Petrov
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Patent number: 7498468Abstract: 4-Aminopicolinic acids having tri- and tetra-substituted aryl substituents in the 6-position, and their amine and acid derivatives, are potent herbicides demonstrating a broad spectrum of weed control.Type: GrantFiled: October 4, 2007Date of Patent: March 3, 2009Assignee: Dow AgroSciences LLCInventors: Terry W. Balko, John F. Daeuble, Thomas L. Siddall
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Publication number: 20090054422Abstract: There is provided compounds of formula I, wherein R1, R2, R3, R41 to R46, X, Y and Z have meanings given in the description, which compounds are useful in the prophylaxis and in the treatment of arrhythmias, in particular atrial and ventricular arrhythmias.Type: ApplicationFiled: June 12, 2006Publication date: February 26, 2009Applicant: ASTRAZENECA ABInventors: Annika Bjore, David Cladingboel, Gareth Ensor, Adam Herring, Johan Kajanus, Robert Lundqvist, Christina Olsson, Carl-Gustav Sigfridsson, Gert Strandlund
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Publication number: 20090054667Abstract: Methods for introducing a 1-halo-1-haloalkene compound onto an aromatic or heteroaromatic ring are provided, including processes for the production of certain 1-halovinyl aryl or heteroaryl derivatives in which the 1-halovinyl group is either 1-fluoro or 1-chlorovinyl and the aromatic species phenyl or thiophene, the processes including coupling an arylmagnesium species with a dihalo olefin in the presence of a nickel or iron catalyst.Type: ApplicationFiled: August 9, 2006Publication date: February 26, 2009Applicant: Replidyne, Inc.Inventors: Joseph W. Guiles, Jian Qiu, Theodore M. Tarasow
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Patent number: 7256316Abstract: A fluorine-containing vinyl ether represented by formula 1, wherein R represents an organic group containing at least one fluorine atom and a cyclic structure is provided. A fluorine-containing copolymer containing (a) a first unit derived from a first monomer that is a fluorine-containing vinyl ether represented by formula 8: where R1 is —H or a C1-C8 alkyl group that optionally contains an oxygen atom; and (b) a second unit derived from a second monomer that is at least one selected from acrylic esters and methacrylic esters is also provided.Type: GrantFiled: October 30, 2003Date of Patent: August 14, 2007Assignee: Central Glass Company, LimitedInventors: Satoru Kobayashi, Kazuhiko Maeda, Tooru Tsujishita
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Patent number: 7115784Abstract: The present invention relates to copper-catalyzed carbon-heteroatom and carbon-carbon bond-forming methods. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of an amide or amine moiety and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In additional embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between a nitrogen atom of an acyl hydrazine and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In other embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of a nitrogen-containing heteroaromatic, e.g., indole, pyrazole, and indazole, and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate.Type: GrantFiled: January 4, 2005Date of Patent: October 3, 2006Assignee: Massachusetts Institute of TechnologyInventors: Stephen L. Buchwald, Artis Klapars, Jon C. Antilla, Gabriel E. Job, Martina Wolter, Fuk Y. Kwong, Gero Nordmann, Edward J. Hennessy
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Patent number: 7091270Abstract: The present invention provides novel pentabromobenzyl alkyl ethers serving as highly effective flame retardants in polymers. The invention further provides a fire retarded polymer composition comprising said pentabromobenzyl alkyl ethers.Type: GrantFiled: January 23, 2000Date of Patent: August 15, 2006Assignee: Bromine Compounds Ltd.Inventors: Joseph Zilberman, Alon Tavor, Dorit Canfi, David Ioffe, Grigory Titelman, Samuel Bron, Olga Weinberg
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Patent number: 6881868Abstract: Compounds of formula (I), wherein R1 and R2 are, independently of one another, H,C1-C6alkyl, C1-C6halogenalkyl, C1-C6alkoxyl, C1-C6alkoxy-C1-C6alkyl, or C1-C6alkoxy-C1-C6alkyloxy, and R3 is C1-C6alkyl, are obtainable in high yiedls by stereoselective addition of R3-substituted propionic acid esters to R1- and R2-substituted benzaldehydes of formula R—CHO to form corresponding 3-R-3-hydroxy-2-R3-propionic acid esters, conversion of the OH group to a leaving group, subsequent regioselective elimination to form 3-R-2-R3-propenic acid esters, and reduction to corresponding 3-R-2-R3-allyl alcohols and their enantioselective hydrogenation, wherein R is (a).Type: GrantFiled: June 26, 2001Date of Patent: April 19, 2005Assignee: Speedel Pharma AGInventors: Stefan Stutz, Peter Herold, Felix Spindler, Walter Weissensteiner, Thomas Sturm
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Patent number: 6770788Abstract: A two-step process for the preparation of fluoroolefin compounds of formula I wherein R is hydrogen or alkyl, and R1 is alkyl or cyclopropyl, or R and R1 are taken together with the carbon atom to which they are attached to form a cyclopropyl group; Ar is phenyl or naphthyl both of which are optionally substituted; Ar1 is phenoxyphenyl, biphenyl, phenyl, benzylphenyl, or benzoylphenyl, all of which may be optionally substituted, comprising reacting fluorobromoolefin compounds of formula II with organozinc compounds of formula III or IV BrZnCH2Ar1 III Zn[CH2Ar1]2 IV in the presence of a palladium catalyst and a solvent, which compounds of formula II are obtained by reacting aldehyde compounds of formula V with (a) fluorotribromomethane, (b) a tri(substituted)phosphine or a hexaalkylphosphoramide or a mixture thereof, and (c) zinc, in the presence of a solvent, compounds of formula II.Type: GrantFiled: October 21, 2002Date of Patent: August 3, 2004Assignee: BASF AktiengesellschaftInventor: William Wakefield Wood
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Patent number: 6706929Abstract: An accelerated process for preparing an O-methyl phenol comprising reacting a phenol with dimethyl carbonate in the presence of a catalyst selected from 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-diazabicyclo[2.2.2]octane; and dimethylaminopyridine. According to another aspect, the invention provides an accelerated process for preparing an N-methyl heteroaromatic compound comprising reacting an NH-containing heteroaromatic compound with dimethyl carbonate in the presence of a catalyst selected from 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-diazabicyclo[2.2.2]octane; and dimethylaminopyridine. According to an additional aspect, the invention provides an accelerated process for preparing a methylated aminophenol comprising reacting an aminophenol having at least one N—H with dimethyl carbonate in the presence of a catalyst selected from 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-diazabicyclo[2.2.2]octane; and dimethylaminopyridine.Type: GrantFiled: June 12, 2003Date of Patent: March 16, 2004Assignee: Novartis AGInventors: Wen-Chung Shieh, Steven Dell
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Patent number: 6677002Abstract: Novel phenylcyclohexanes of the formula I: in which n is 0 to 7, Q1 and Q2 are H, or one of these radicals is alternatively CH3, r is 0, 1, 2, 3, 4 or 5, A is trans-1,4-cyclohexylene, 1,4-phenylene, 3-fluoro-1,4-phenylene or a single bond, X is F, Cl, —CF3, —CN, —OCF3 or —OCHF2, and Y and Z are each, independently of one another, H or F, with the proviso that, in the case where A is a single bond, Q1═Q2═H and simultaneously X═CN, Y and/or Z are F.Type: GrantFiled: February 8, 2001Date of Patent: January 13, 2004Assignee: Merck Patent Gesellschaft mit Beschrankter HaftungInventors: Andreas Wächtler, Reinhard Hittich, Eike Poetsch, Herbert Plach, David Coates, Bernhard Rieger, Joachim Krause
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Patent number: 6399837Abstract: A method of polymerizing at least one olefin comprising contacting the olefin with a catalyst composition comprising: 1) a procatalyst composition comprising a magnesium and titanium-containing component and an electron donor compound of the structure: wherein R1 is ethoxy, and R2 is an alkoxy group having from one to ten carbon atoms, and R3-R6 are each individually, hydrogen, hydrocarbyl, hydrocarboxy, nitro, a silyl group or a halogen, 2) a cocatalyst and optionally 3) a selectivity control agent.Type: GrantFiled: June 5, 2000Date of Patent: June 4, 2002Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Stanley Edward Wilson, Robert Converse Brady, III
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Patent number: 6399835Abstract: Processes for the electrophilic substitution of aromatic compounds, such as alkylation, with a desired substituent are disclosed. The processes include contacting the aromatic compound, a precursor of the desired substituent and an aqueous reagent containing zinc halide at elevated temperatures such as above 50° C.Type: GrantFiled: April 6, 2000Date of Patent: June 4, 2002Assignee: Bromine Compounds Ltd.Inventors: Ariel Ewenson, David Itzhak, Miriam Freiberg Bergstein, Asher Shushan, Bertha Croitoru, David Beneish, Naim Faza
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Patent number: 6380440Abstract: Process for the preparation of 3-bromoanisole comprising methoxydenitrating 3-bromonitrobenzene in the presence of a phase-transfer catalyst (PTC), and the preparation of 3-bromonirtobenzene by the bromination of nitrobenzene with bromine in oleum. The methoxydenitration reagent in an alkali metal methoxide, which is selected from sodium methoxide and potassium methoxide. The amount of methoxide used is 1-1.5 mol per mol of 3-bromonitrobenzene. The alkali methoxide can be a pre-prepared solid or it can be prepared in situ, by the reaction of the corresponding alkali hydroxide and methanol. In the case when pre-prepared solid methoxide is used, the effective amount of alkali hydroxide is between 1.2-1.7 mol per mol of 3-bromonitrobenzebe. The reaction temperatures are between about 40 to 80° C., with preference to reaction temperatures of 50 to 55° C. In the case in which methoxide is prepared in situ, the effective amount of alkali hydroxide is between 2.2-2.4 mol per mol of 3-bromonitrobenzene.Type: GrantFiled: October 5, 2000Date of Patent: April 30, 2002Assignee: Bromine Compounds Ltd.Inventors: Mark Gelmont, Joseph Zilberman
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Patent number: 6369279Abstract: Styrene derivatives of formula (1) are novel wherein R1 is hydrogen, C1-20 alkyl, fluoro-substituted C1-20 alkyl, chloro, or trichloromethyl, R2 is a phenol protecting group, p, q and r are integers in the range of 0≦p<5, 0≦q<5, 0<r<5, and 0<p+q<5. Polymers obtained by polymerizing the styrene derivatives are useful as the base polymer of resist compositions.Type: GrantFiled: September 7, 2000Date of Patent: April 9, 2002Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Mutsuo Nakashima, Jun Hatakeyama, Jun Watanabe, Yuji Harada
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Patent number: 6355813Abstract: Invented is an improved process for preparing aromatic ring-fused cyclopentane derivatives. Preferred compounds prepared by this invention are indane carboxylates and cyclopentanopyridine derivatives. The most preferred compounds prepared by this invention are (+)(1S, 2R, 3S)-3-[2-(2-hydroxyeth-1-yloxy)-4-methoxyphenyl]-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane-2-carboxylic acid and pharmaceutically acceptable salts thereof and (+)(1S, 2R, 3S)-3-(2-carboxymethoxy-4-methoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane-2-carboxylic acid and pharmaceutically acceptable salts thereof. Also invented are novel intermediates useful in preparing these compounds.Type: GrantFiled: June 29, 2000Date of Patent: March 12, 2002Assignee: SmithKline Beecham CorporationInventors: William Morrow Clark, Ivan Lantos, Robert John Mills, Lendon Norwood Pridgen, Ann Marie Tickner
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Patent number: 6333436Abstract: Styrene derivatives of formula (1) are novel wherein R1 is H, F, C1-20 alkyl or fluorinated C1-20 alkyl, R2 in cis or trans conformation is F, C1-20 alkyl or fluorinated C1-20 alkyl, R3 is a phenol protecting group, p, q and r are integers in the range of 0≦p<5, 0≦q<5, 0<r<5, and 0≦p+q<5. Polymers obtained by polymerizing the styrene derivatives are useful as the base polymer of resist compositions.Type: GrantFiled: October 12, 2000Date of Patent: December 25, 2001Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Matsuo Nakashima, Jun Hatakeyama, Jun Watanabe, Yuji Harada
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Patent number: 6288242Abstract: The invention relates to processes for preparing a compound of the formula and the enantiomer of said compound, wherein the benzoic acid moiety is attached at position 6 or 7 of the chroman ring, and R1, R2, and R3 are as defined herein. The invention further relates to intermediates that are useful in the preparation of the compound of formula X above.Type: GrantFiled: February 23, 2000Date of Patent: September 11, 2001Assignee: Pfizer Inc.Inventors: Anthony Piscopio, Joel M. Hawkins, Stephanie Caron, Sarah E. Kelly, Jeffrey W. Raggon, Michael J. Castaldi, Robert W. Dugger, Sally G. Ruggeri
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Patent number: 6239317Abstract: There is described a four step process for the production of halogeno-o-hydroxydiphenyl compounds having the formula in which X is —O—or —CH2—; m is 1 to 3; and n is 1 or 2; wherein in the first step, a diphenyl compound is chlorinated; in a second step the chlorinated compound is acylated in a Friedel-Crafts reaction and optionally again chlorinated after the acylation; in a third step the acyl compound is oxidised; and in a fourth step the oxidized compound is hydrolyzed. The compounds of formula (1) are useful for the protection of organic materials against microorganisms.Type: GrantFiled: February 5, 1998Date of Patent: May 29, 2001Assignee: Ciba Specialty Chemicals CorporationInventors: Surendra Umesh Kulkarni, Vadiraj Subbanna Ekkundi, Pradeep Jeevaji Nadkarni, Chandrasekhar Dayal Mudaliar, Kishore Ramachandra Nivalkar