Halogen Containing Reactant Patents (Class 568/316)
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Patent number: 7067702Abstract: A process for preparing vinyl substituted beta-diketones includes reacting a halogen-containing beta-diketone with an olefin in a reaction zone under Heck coupling reaction conditions in the presence of a catalyst, a base, and an organic phosphine to provide a vinyl substituted beta-diketone product.Type: GrantFiled: May 12, 2005Date of Patent: June 27, 2006Assignee: The Johns Hopkins UniversityInventors: Glen E. Southard, George M. Murray
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Patent number: 7060859Abstract: The invention concerns the use of a solid basic catalyst comprising a hydrotalcite structure wherein part at least of the compensating anions are fluoride anions F? for producing Knoevenagel of Michael condensation reactions. The invention also concerns novel solid basic catalysts comprising a hydrotalcite structure characterized by a Mg/Al molar ratio ranging between 2.5 and 3.8 wherein at least part of the compensating anions are fluoride anions F?, and methods for preparing said novel catalysts.Type: GrantFiled: June 6, 2005Date of Patent: June 13, 2006Assignee: Council of Scientific and Industrial ResearchInventors: Francois Figueras, Boyapati Manoranjan Choudary, Mannepalli Lakshmi Kantam, Vattipally Neeraja, Kottapalli Koteswara Rao
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Patent number: 7005453Abstract: The present invention provides methods, products, and compositions for selectively inhibiting the growth of Staphylococcus aureus without preventing the growth of Lactobacillus species. Specifically, the present invention discloses the use of tetrahydroiso alpha acid or hexahydro beta acid at a concentration effective to inhibit the growth of S. aureus without preventing the growth of Lactobacillus. The inhibition of S. aureus in accordance with the present invention thus provides useful methods, compositions and products such as feminine hygiene products for treating the diseases associated with S. aureus infections and infestations, i.e., toxic shock syndrome, without disrupting the normal bacterial flora in the area of its application.Type: GrantFiled: September 18, 2000Date of Patent: February 28, 2006Assignee: Miller Brewing CompanyInventors: Michael C. Barney, Alfonso L. Navarro, David S. Ryder
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Patent number: 6984735Abstract: A process for making an aromatic aldehyde in which a sulfoxide is reacted with a dihalogenated aromatic compound in the absence of an effective amount of an activating reagent. The aldehyde may then be used to make other compounds, such as a compound that acts as a cPLA inhibitor.Type: GrantFiled: November 26, 2003Date of Patent: January 10, 2006Assignee: WyethInventors: John C. McKew, Steven Y. Tam, Katherine L. Lee, Lihren Chen, Paresh Thakker, Fuk-Wah Sum, Mark Behnke, Baihua Hu, James D. Clark, Wei Li
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Patent number: 6930207Abstract: Novel and known trifluoroacetyl-substituted phenyl, phenol and benzoyl compounds for the treatment and/or inhibition of obesity and of concomitant and/or secondary diseases involved therewith, in particular metabolic syndrome and cardiovascular diseases. Novel trifluoroacetyl-substituted phenyl, phenol and benzoyl compounds, pharmaceutical preparations containing them and processes for the preparation of these compounds. Also compounds acting as inhibitors of lipase, in particular pancreatic lipase.Type: GrantFiled: January 16, 2004Date of Patent: August 16, 2005Assignee: Solvay Pharmaceutical GmbHInventors: Jochen Antel, Harald Waldeck, Andreas Potthoff, Sabine Irmer, Peter-Colin Gregory
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Patent number: 6924397Abstract: The present invention relates to a process for the preparation of ?-chloroketones from readily available alkyl esters by the reaction of a sulfoxonium ylide on said alkyl esters to generate a keto sulfoxonium ylide that is in turn treated with anhydrous HCl.Type: GrantFiled: October 22, 2003Date of Patent: August 2, 2005Assignee: Bristol-Myers Squibb CompanyInventors: William Aloysius Nugent, Dengjin Wang
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Patent number: 6919485Abstract: The invention relates to benzophenones of formula (I), in which the substituents have the following meanings: X represents halogen; R1 represents hydrogen, halogen, C1-C6 alkyl, halo-C1-C2 alkyl, C1-C4 alkoxy, oxyhalomethyl or nitro, and; R2 represents hydrogen, C1-C6 alkyl, benzyl, cyclohexylmethyl or C3-C6 alkenyl.Type: GrantFiled: March 9, 2002Date of Patent: July 19, 2005Assignee: BASF AktiengesellschaftInventors: Thomas Grote, Andreas Gypser, Joachim Rheinheimer, Ingo Rose, Peter Schäfer, Frank Schieweck, Norbert Götz, Karl Eicken, Eberhard Ammermann, Siegfried Strathmann, Gisela Lorenz, Reinhard Stierl
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Patent number: 6881865Abstract: Disclosed is a synthesis method of cyclohexyl phenyl ketone with a high selectivity and a high yield from 1,3-butadiene and acrylic acid in the presence or absence of benzene or a non-aromatic organic solvent in the same reaction without a step of separating or purifying intermediates, the synthesis method including sequentially carrying out a [2+4] Diels-Alder reaction, a hydrogenation reaction, a chlorination reaction and a Friedel-Crafts reaction in the presence/absence of benzene or a non-aromatic organic solvent without separation of intermediates.Type: GrantFiled: July 28, 2003Date of Patent: April 19, 2005Assignee: Korea Kumho Petrochemical Co., Ltd.Inventors: Young J. Joo, Jin Eok Kim, Jeong Im Won, Tae Yi Kang
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Patent number: 6867323Abstract: Improved methods for generating a —C—C— bond by cross-coupling of a transferable group with an acceptor group. The transferable group is a substituent of an organosilicon nucleophile and the acceptor group is provided as an organic electrophile. The reaction is catalyzed by a Group 10 transition metal complex (e.g., Ni, Pt or Pd), particularly by a palladium complex. Certain methods of this invention use improved organosilicon nucleophiles which are readily prepared, can give high product yields and exhibit high stereoselectivity. Methods of this invention employ activating ions such as halides, hydroxide, hydride and silyloxides. In specific embodiments, organosilicon nucleophilic reagents of this invention include siloxanes, particularly cyclic siloxanes. The combination of the cross-coupling reactions of this invention with ring-closing metathesis, hydrosilylation and intramolecular hydrosilylation reactions provide useful synthetic strategies that have wide application.Type: GrantFiled: June 6, 2001Date of Patent: March 15, 2005Assignee: The Board of Trustees of the University of IllinoisInventors: Scott E. Denmark, Jun Young Choi, Daniel Wehrli, Zhicai Wu, Luc Neuville, Weitao Pan, Ramzi F. Sweis, Zhigang Wang, Shyh-Ming Yang
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Patent number: 6867310Abstract: The present invention provides transition-metal-catalyst-based methods for the arylation and vinylation of activated methyl, methylene, and methine carbons with aryl halides, vinyl halides, and the like. The methods of the invention provide several improvements over existing methods, including the ability to synthesize efficiently and under mild conditions ?-aryl and ?-vinyl products from a wide range of starting materials, including ketones, esters, hydrazones, and imines. Furthermore, the methods of the invention may be used in an asymmetric sense, i.e. to produce enantiomerically-enriched chiral ?-aryl and ?-vinyl products.Type: GrantFiled: January 27, 1999Date of Patent: March 15, 2005Assignee: Massachusetts Institute of TechnologyInventors: Stephen L. Buchwald, John P. Wolfe, Jens Ahman, Malisa Troutman, Michael Palucki, Ken Kamikawa, Andre Chieffi
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Publication number: 20040082785Abstract: A process for making an aromatic aldehyde in which a sulfoxide is reacted with a dihalogenated aromatic compound in the absence of an effective amount of an activating reagent. The aldehyde may then be used to make other compounds, such as a compound that acts as a cPLA inhibitor.Type: ApplicationFiled: November 26, 2003Publication date: April 29, 2004Applicant: WyethInventors: John C. McKew, Steven Y. Tam, Katherine L. Lee, Lihren Chen, Paresh Thakker, Fuk-Wah Sum, Mark Behnke, Baihua Hu, James D. Clark, Wei Li
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Patent number: 6696611Abstract: The present invention provides a method for enantioselectively reducing a prochiral carbon centered radical having one or more electron donator groups attached directly to the central prochiral carbon atom of the radical, and/or attached to a carbon atom within 1 to 4 atoms of the central prochiral carbon atom, comprising treating said radical with a chiral non-racemic organotin hydride in the presence of a Lewis acid.Type: GrantFiled: July 27, 2001Date of Patent: February 24, 2004Assignee: Chirogen Pty. LimitedInventors: Dainis Dakternieks, Carl H. Schiesser, Tamara Perchyonok
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Patent number: 6683220Abstract: A process for producing substantially optically pure sertraline utilizes chromatographic separation on a solid stationary chiral phase of spherical clay particles having an interlayer containing an optically pure metal-organic complex, and a liquid mobile phase preferably containing at least methyl acetate. The liquid mobile phase is preferably free of acetonitrile. The process is operable at temperatures above 40° C.Type: GrantFiled: September 18, 2002Date of Patent: January 27, 2004Assignee: Pfizer, Inc.Inventors: Laurent Berger, Raphael Duval, Philippe Taillasson, Ingo Weber, Alexander Wick
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Patent number: 6593499Abstract: The present invention relates to a process for the preparation of phenyl ketones of formula-I, Wherein R represents —COCH3, —COC2H5 or —COC6H5, which comprises acylating the biphenyl with an acylating agent in an organic solvent in the presence of a solid crystalline microporous calalyst composite material.Type: GrantFiled: August 29, 2001Date of Patent: July 15, 2003Assignee: Council of Scientific & Industrial ResearchInventors: Mandan Chidambaram, Chithravel Venkatesan, Anand Pal Singh, Arumugamangalam Venkataraman Ramaswamy
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Patent number: 6586599Abstract: A process for conducting coupling reactions of aryl halides with unsaturated silanes is described. The processes use N-heterocyclic carbenes as ancillary ligands in these coupling reactions. A coupling of an aryl halide with an unsaturated silane can be carried out by mixing, in a liquid medium, at least one strong base; at least one aryl halide or aryl pseudohalide in which all substituents are other than silyl groups, wherein the aryl halide has, directly bonded to the aromatic ring(s), at least one chlorine atom, bromine atom, or iodine atom; at least one silane wherein the silicon atom is quaternary, wherein one group bound to the silicon atom is unsaturated at the alpha or beta position, and wherein each of the remaining groups bound to the silicon atom is a saturated hydrocarbyl or a saturated hydrocarbyloxy group; at least one nickel, palladium, or platinum compound, wherein the formal oxidation state of the metal is zero or two; and at least one N-heterocyclic carbene.Type: GrantFiled: April 20, 2000Date of Patent: July 1, 2003Assignee: University of New Orleans Research and Technology FoundationInventors: Steven P. Nolan, Hon Man Lee
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Patent number: 6583307Abstract: A Pd(OAc)2/diazabutadiene system has been developed for the catalytic cross-coupling of aryl halides with arylboronic acids. A combination of the diazabutadiene DAB-Cy (1, N,N′-Dicyclohexyl-1,4-dizabutadiene) and Pd(OAc)2 was found to form an excellent catalyst for the Suzuki-Miyaura cross-coupling of various aryl bromides and activated aryl chlorides with arylboronic acids.Type: GrantFiled: March 7, 2002Date of Patent: June 24, 2003Assignee: University of New Orleans Research and Technology Foundation, Inc.Inventors: Steven P. Nolan, Gabriela Grasa
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Publication number: 20030065226Abstract: A method for preparing bromofluorenes includes a step of dispersing a compound selected from the group consisting of fluorene, fluorenone, and derivatives of fluorene and fluorenone in water to prepare a disperse system. Bromination is initiated by adding bromine Br2 into the disperse system. Thus, bromofluorenes can be efficiently and economically prepared without using any environmentally harmful organic solvent requiring a high cost to dispose of.Type: ApplicationFiled: September 17, 2002Publication date: April 3, 2003Applicant: ADCHEMCO CorporationInventors: Tetsuo Hachiya, Naoyuki Kitamura, Hiroaki Mori, Toshiyuki Yasuda
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Publication number: 20030060664Abstract: A method for producing a fluoropolymer, which comprises polymerizing a monomer containing a fluoromonomer having a polymerizable double bond, using an initiator, in a medium containing fluoroform and water, under a condition such that fluoroform is in a supercritical state.Type: ApplicationFiled: September 26, 2002Publication date: March 27, 2003Applicant: Asahi Glass Company, LimitedInventors: Yoshio Okahata, Toshiaki Mori, Yuri Tsuchiya
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Patent number: 6444854Abstract: A process for the production of enantiomerically pure or optically enriched sertraline-tetralone from a mixture containing two enantiomers using continuous chuomatography. The chromatography comprises a liquid mobile phase comprising at least one polar solvent and a solid chiral stationary phase comprising a derivatized polysaccharide that is selected from amylosic, cellulosic, chitosan, xylan, curdlan, and inulan class of polysaccharide.Type: GrantFiled: May 1, 2001Date of Patent: September 3, 2002Assignee: Chiral Technologies EuropeInventors: Oliver Dapremont, Fiona Geiser, Tong Zhang, Subramanian S. Guhan, Robert M. Guinn, George J. Quallich
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Publication number: 20020120169Abstract: The present invention relates to a process facilitating the regeneration of a catalyst based on a zeolite, employed in an acylation reaction.Type: ApplicationFiled: February 21, 2002Publication date: August 29, 2002Inventors: Michel Spagnol, Laurent Gilbert, Anne-Marie Le Govic
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Patent number: 6417357Abstract: This invention relates to a novel, inventive process for the preparation of biphenyls or aromatic olefins by coupling reactions of the Suzuki coupling and Heck coupling type, using allylpalladium catalysts of the &mgr;-halo(triisopropylphosphine)(&eegr;3-allyl)palladium(II) type.Type: GrantFiled: September 14, 2000Date of Patent: July 9, 2002Assignee: Ciba Specialty Chemicals CorporationInventors: Michael Tinkl, Andreas Hafner
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Publication number: 20020077507Abstract: The present invention relates to a process for preparing 1-indanones of formula I: 1Type: ApplicationFiled: October 31, 2001Publication date: June 20, 2002Inventor: Richard Herman Woudenberg
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Patent number: 6392111Abstract: Olefins containing aromatic substituents are synthesized without the addition of phosphonium salts or phosphanes with the aid of a PdII compound as a catalyst in the presence of nitrogen-containing additives such as N,N-dimethylglycine and a base.Type: GrantFiled: March 21, 2001Date of Patent: May 21, 2002Assignee: Studiengesellschaft Kohle mbHInventors: Manfred T. Reetz, Gunther Lohmer, Renate Lohmer, Elke Westermann
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Patent number: 6271421Abstract: A process for selectively debrominating polybromoalkyl aryl ketones and polybromoalkyl heteroaryl ketones is disclosed. The process comprises contacting an alpha-polybrominated ketone with an alkali metal sulfite in the presence of a C2-C6 alkylcarboxylic acid to obtain a selectively mono-debrominated product.Type: GrantFiled: November 12, 1999Date of Patent: August 7, 2001Assignee: Merck & Co., Inc.Inventor: Anthony O. King
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Patent number: 6245944Abstract: A process for preparing a compound of the formula I where R1 and R2 are hydrogen or C1-C4-alkyl and R3 is C1-C10-alkyl, phenyl or C1-C4-alkyl-substituted phenyl, comprises reacting a compound II with a compound of the formula III where X is chlorine, bromine or iodine, in the presence of a Friedel-Crafts catalyst in one step to give a compound I.Type: GrantFiled: December 9, 1998Date of Patent: June 12, 2001Assignee: BASF AktiengesellschaftInventors: Carsten Süling, Heike Gregorius, Walter Dobler, Roland Hingmann, Bernhard Rieger, Ulf Dietrich, Jürgen Matthäus Wagner, Hans-Joachim Müller
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Patent number: 6159988Abstract: Compounds of formula I, ##STR1## and the physiologically tolerable salts thereof, wherein the substituents R.sub.1 -R.sub.4 have the meanings given in the specifications and show an activity against inflammatory conditions.Type: GrantFiled: June 29, 1998Date of Patent: December 12, 2000Assignee: Hoeschst AktiengesellschaftInventors: Ramachandra Ganapati Naik, Vilas Narayan Mumbaikar, Ravishankar Vasumathy, Aftab Dawoodbhai Lakdawala, Mandakini Bipin Alreja, Bansi Lal, Jurgen Blumbach, Klaus Ulrich Weithmann, Robert Ryder Bartlett, Kalpana Sanjay Joshi, Swati Bal-Tembe, Sadagopan Raghavan
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Patent number: 6096929Abstract: The preparation of aromatic ketones substituted with a thioether group at the ortho position is accomplished by the initial reaction of an aromatic nucleus substituted with a halide and an ortho nitro group with a nitroalkane in the presence of a hydroxide base. The resulting ortho-nitroalkyl nitroarene compound is converted to the corresponding ortho-nitroaryl ketone by an oxidative Nef reaction. The aromatic nitro group of the ortho-nitroaryl ketone is replaced with a thioether group by reaction with a thiolate anion, most preferably under phase-transfer conditions. Aromatic ketones may be used to prepare various pharmaceutical and herbicidal compounds.Type: GrantFiled: August 6, 1999Date of Patent: August 1, 2000Assignee: Eastman Kodak CompanyInventor: Neil W. Boaz
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Patent number: 6020502Abstract: A method for the fluorination of 1,3-diketones and 1,3-ketoesters is disclosed.Type: GrantFiled: February 21, 1997Date of Patent: February 1, 2000Assignee: BNFL Fluorochemicals Ltd.Inventors: Richard D. Chambers, John Hutchinson, Martin P. Greenhall, John S. Moilliet, Julie Thomson
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Patent number: 5981803Abstract: An effective and efficient process for the preparation of chloro-benzoylchlorides of formula I, ##STR1## (n is defined in the specification). In this process a a chloro-trichloromethylbenzene of formula II ##STR2## is treated with water acid in the presence of a Lewis at temperatures below 80.degree. C. The compounds obtained according to this process can be used to prepare certain chloro-substituted benzophenones.Type: GrantFiled: January 15, 1999Date of Patent: November 9, 1999Assignee: American Cyanamid CompanyInventors: Laurens Wilhelm van den Akker, Monika Brink
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Patent number: 5922898Abstract: The present invention provides a process for preparing biaryl compounds comprising reacting an arylmetal reagent selected from arylmagnesium reagents and aryllithium reagents with an arylhalide in the presence of a catalyst system comprising a catalyst selected from nickel catalysts and palladium catalysts and a cocatalyst selected from zinc cocatalysts and cadmium cocatalysts. The present invention specifically provides a process for the preparation of 2-(4'-methylphenyl)benzonitrile comprising reacting a 4-methylphenylmagnesium reagent with a 2-halobenzonitrile in the presence of a catalyst system comprising a catalyst selected from nickel catalysts and palladium catalysts and a zinc cocatalyst.Type: GrantFiled: November 7, 1997Date of Patent: July 13, 1999Assignee: Catalytica Pharmaceuticals, Inc.Inventors: Joseph Arthur Miller, Robert Patrick Farrell
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Patent number: 5910596Abstract: Processes for preparing substituted 3-aryl-5-haloalkyl-pyrazoles and, specifically, for preparing C.sub.1-5 alkyl esters of 5- ?1-(C.sub.1-5 alkyl) -4-halo-5-(C.sub.1-3 haloalkyl) -1H-pyrazole-3-yl!-2,4-dihalo-benzoic acids such as isopropyl 5-?4-bromo-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl!-2-chloro-4-fluor obenzoate, are presented. The described processes include novel approaches for forming phenyl-diketones, forming and alkylating pyrazoles, brominating heterocyclic compounds, oxidizing alkyl-substituted benzene compounds, and esterifying carboxylic acids. These processes may be combined to prepare 3-aryl-5-haloalkyl pyrazoles, or alternatively, used in subcombinations or individually to prepare intermediates or other useful compounds.Type: GrantFiled: October 3, 1997Date of Patent: June 8, 1999Assignee: Monsanto CompanyInventor: Michael K. Mao
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Patent number: 5883263Abstract: Processes for preparing substituted 3-aryl-5-haloalkyl-pyrazoles and, specifically, for preparing C.sub.1-5 alkyl esters of 5-?1-(C.sub.1-5 alkyl)-4-halo-5-(C.sub.1-3 haloalkyl)-1H-pyrazole-3-yl!-2,4-dihalo-benzoic acids such as isopropyl 5-?4-bromo-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl!-2-chloro-4-fluor obenzoate, are presented. The described processes include novel approaches for forming phenyldiketones, forming and alkylating pyrazoles, brominating heterocyclic compounds, oxidizing alkyl-substituted benzene compounds, and esterifying carboxylic acids. These processes may be combined to prepare 3-aryl-5-haloalkyl pyrazoles, or alternatively, used in subcombinations or individually to prepare intermediates or other useful compounds.Type: GrantFiled: October 3, 1997Date of Patent: March 16, 1999Assignee: Monsanto CompanyInventors: Bruce C. Hamper, Michael K. Mao, Wendell Gary Phillips
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Patent number: 5811585Abstract: A process for preparing 5-chloro-2,3-dihydro-1H-inden-1-one comprising contacting 3-chloro-1-(chlorphenyl)-1-propanone with a catalyst selected from sulfuric acid and solid acid catalysts.Type: GrantFiled: June 24, 1997Date of Patent: September 22, 1998Assignee: E. I. du Pont de Nemours and CompanyInventors: Donald Joseph Dumas, Sourav Kumar Sengupta, David Richard Corbin
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Patent number: 5786515Abstract: A simple, high yielding synthesis of a-chloro ketones is described, involving acylation of Grignard and organolithium reagents with N-methoxy-N-methylchloroacetamide. The efficiency of the process is further enhanced by recycling N,O-dimethylhydroxylamine.Type: GrantFiled: August 30, 1996Date of Patent: July 28, 1998Assignee: Merck & Co., Inc.Inventors: Ulf H. Dolling, Lisa F. Frey, Richard D. Tillyer, David M. Tschaen
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Patent number: 5736274Abstract: A polymer containing a recurring unit of a conjugated N-fluoropyridinium salt and an active material for a positive electrode, an electrolyte, a battery material for the positive electrode and a battery which use such a polymer. That polymer provides a battery material and a primary battery or a secondary battery which have high electromotive force, high energy density, high environmental acceptability, a low internal resistance in charging and discharging and strong recoverability of the electromotive force, and can be useful as a fluorinating agent.Type: GrantFiled: April 18, 1997Date of Patent: April 7, 1998Assignee: Daikin Industries, Ltd.Inventors: Teruo Umemoto, Kenji Adachi, Ginjiro Tomizawa, Sumi Ishihara, Masayuki Nagayoshi
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Patent number: 5710341Abstract: A process for preparing .alpha.-chloroalkyl aryl ketones of the formula I ##STR1## where n is 1 to 5,R.sub.1 independently of one another are H, alkyl, alkoxy, aryl, aryloxy, acyloxy, acylamino, halogen or nitro,R.sub.2,3 independently of one another are H, alkyl or aryl,by chlorination of alkyl aryl ketones of the formula II ##STR2## with sulfuryl chloride is described, the chlorination being carried out in the presence of an aliphatic alcohol.Type: GrantFiled: March 22, 1996Date of Patent: January 20, 1998Assignee: BASF AktiengesellschaftInventors: Wolfgang Siegel, Walter Dobler, Michael John
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Patent number: 5703269Abstract: The preparation of aromatic olefins from haloaromatics and olefins (Heck reaction) is carried out in the presence of palladium complexes as catalysts, which complexes contain heterocyclic carbenes as ligands.Type: GrantFiled: December 29, 1995Date of Patent: December 30, 1997Assignee: Hoechst AktiengesellschaftInventors: Wolfgang A. Herrmann, Jakob Fischer, Martina Elison, Christian Kocher
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Patent number: 5684205Abstract: The invention relates to the use of substituted cyclopentane-diones and cyclopentane-triones for the preparation of medicaments which as chloride channel blockers are suitable for controlling airway diseases, secretory diarrhea and inflammatory diseases.Type: GrantFiled: September 8, 1995Date of Patent: November 4, 1997Assignee: Bayer AktiengesellschaftInventors: Peter Norman, Roderick L. Hall, Graham A. Place, Graham Holmwood, Gabriele Braunlich
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Patent number: 5663447Abstract: A particularly advantageous process for the preparation of 2,2-dialkyl-arylidene-cycloalkanones is characterized in that 2-alkyl-arylidene-cycloalkanones are reacted with alkyl halides in the presence of metal hydroxides and tertiary alcohols.Type: GrantFiled: June 20, 1996Date of Patent: September 2, 1997Assignee: Bayer AktiengesellschaftInventors: Nikolaus Muller, Thomas Essert
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Patent number: 5639917Abstract: There is described a continuous process for preparing 1-(4-chlorophenyl)-4,4-dimethyl-pentan-3-one from 1-(4-chlorophenyl)-4,4-dimethyl-pent-1-en-3-one, wherein the 1-(4-chlorophenyl)-4,4-dimethyl-pent-1-en-3-one is hydrogenated in the liquid phase in alcoholic solution with hydrogen at a pressure of from 50 to 400 bar and a reaction temperature of from 80.degree. to 160.degree. C. over support-free shaped bodies of pressed powders of the elements of the iron subgroup of transition group VIII of the Periodic Table or their alloys or mixtures with one another or their alloys or mixtures with elements of transition group VI, which shaped bodies are arranged in a fixed bed, to give 1-(4-chlorophenyl)-4,4-dimethyl-pentan-3-one. The shaped bodies have a compressive strength of from 20 to 250N and an internal surface area of from 10 to 80 m.sup.2 /g.Type: GrantFiled: February 15, 1996Date of Patent: June 17, 1997Assignee: Bayer AktiengesellschaftInventor: Gerhard Darsow
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Patent number: 5600009Abstract: The palladium-catalyzed coupling of aryl and vinyl halides with vinylic compounds is disclosed. A preferred embodiment relating to the palladium catalyzed coupling of 4-substituted and 6-substituted-2-methoxynaphthalene to form nabumetone is also disclosed. The beauty of this novel reaction is that methylvinylketone, normally employed by the art directly as-is for the preparation of nabumetone, is formed in situ. We have discovered a mechanism to take advantage of the in situ formation of methylvinylketone, thus avoiding the use of expensive, toxic, and unstable methyl vinyl ketone feed. This reaction may be employed for a variety of pharmaceutically active and non-pharmaceutical compounds.Type: GrantFiled: April 9, 1996Date of Patent: February 4, 1997Assignee: Hoechst Celanese CorporationInventors: John F. Fritch, Mohammad Aslam, Dora E. Rios, Joel C. Smith
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Patent number: 5569778Abstract: A process for preparing a fluorine-containing dicarbonyl compound of the formula: R.sup.1 COCFR.sup.2 COR.sup.3 in which R.sup.1 is a hydrogen atom, or a substituted or unsubstituted alkyl or aryl group; R.sup.2 is a hydrogen atom, a halogen atom, or a substituted or unsubstituted alkyl or aryl group; and R.sup.3 is a hydrogen atom, or a substituted or unsubstituted alkyl, aryl, alkoxy or aryloxy group, provided that at least two of R.sup.1, R.sup.2 and R.sup.3 may together form a part of a cyclic structure with or without a hetero atom, by reacting a dicarbonyl compound of the formula: R.sup.1 COCHR.sup.2 COR.sup.3 in which R.sup.1, R.sup.2 and R.sup.3 are the same as defined above with fluorine (F.sub.2) in at least one solvent selected from the group consisting of halogenated hydrocarbons having 1 to 5 carbon atoms and nitrile compounds, or in a solvent in the presence of a salt, or an acid having pKa of 6 or less.Type: GrantFiled: April 28, 1995Date of Patent: October 29, 1996Assignee: Daikin Industries Ltd.Inventors: Teruo Umemoto, Ginjiro Tomizawa
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Patent number: 5481043Abstract: Certain new phenone derivatives of the formula (I) ##STR1## in which R.sup.1 =CH.sub.3,R.sup.2 =H, Cl, Br, I, methyl, hydroxy, methoxy, propoxy, propoxy or ethoxy;R.sup.3 =H or .beta.-D-glykosyl;R.sup.4 =H, Cl, Br, I, methyl, hydroxy, methoxy, propoxy, iso-propoxy or ethoxy;R.sup.5 =H or hydroxy,and the pharmaceutically acceptable salts, ethers and esters thereof, with the exception of the compounds 4-hydroxyacetophenone, 4-hydroxy-3-methoxy-acetophenone, 4-glucopyranosyloxy-acetophenone, 4-glucopyranosyloxy-3-methoxyacetophenone, 4-galactopyranosyloxy-3-methoxy-acetophenone, 4-glucopyranosyloxy-3,5-dimethoxy-acetophenone and galactopyranosyloxy-3,5-dimethoxy-acetophenone and a method for manufacturing them and pharmaceutical preparations containing them. The invention also concerns pharmaceutical preparations containing at least one compound of the formula (II) ##STR2## in which R.sup.1 denotes H, OH, alkoxy or C.sub.1-8 alkyl;R.sup.2 denotes H or C.sub.1-4 alkoxy;R.sup.3 denotes OH or a .beta.Type: GrantFiled: February 18, 1992Date of Patent: January 2, 1996Assignee: Plantamed Arzneimittel GmbHInventors: Hildebert Wagner, Walter Dorsch, Hermann Stuppner, Sandor Antus
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Patent number: 5463135Abstract: Fluorinated benzils and a process for their preparation A process for the preparation of fluorinated benzils of the formula (1) ##STR1## in which X.sub.1 -X.sub.6, R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are hydrogen, fluorine, chlorine or bromine atoms, or alkyl(C.sub.1 -C.sub.10), phenyl or naphthyl groups which may be substituted, or are groups reducing the electron density, at least one of the substituents X.sub.1 -X.sub.6 being a fluorine atom, by reacting 1 mol of a benzil of the formula (1), in which X.sub.1 -X.sub.6 and R.sub.1 and R.sub.2 have the abovementioned meanings, with the proviso that at least one of the substituents X.sub.1 -X.sub.6 is a chlorine atom, with about 0.8 to about 2.5 mol of potassium fluoride, rubidium fluoride, cesium fluoride or tetraalkyl (C.sub.1 -C.sub.18)-ammonium fluoride per chlorine atom to be exchanged, at temperatures of from about 100.degree. C. to about 280.degree. C.Type: GrantFiled: November 4, 1993Date of Patent: October 31, 1995Assignee: Hoechst AktiengesellschaftInventors: Andreas Kanschik-Conradsen, Theodor Papenfuhs
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Patent number: 5442124Abstract: A process for the preparation of novel compounds with a tetraline-type structure, which are useful as perfuming ingredients, is described.Type: GrantFiled: February 14, 1994Date of Patent: August 15, 1995Assignee: Firmenich SAInventors: Charles Fehr, Jose Galindo
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Patent number: 5430172Abstract: A process for preparing 4-alkanoylaryl benzyl ethers of the general formula I ##STR1## where R is hydrogen, halogen, cyano; alkyl, alkoxy;X is CH.sub.2, CH--CH.sub.3, CH--CH.sub.2 --CH.sub.3, CH--OCH.sub.3 or N--OCH.sub.3 ;Y is oxygen, sulfur, direct linkage or nitrogen;m is 0, 1, 2 or 3;R.sup.1 is hydrogen; alkyl, alkenyl, alkynyl or alkoxy;R.sup.2 is cyano, halogen, alkyl, alkoxy or haloalkyl;R.sup.3 is alkyl; haloalkyl; cycloalkyl; or an unsubstituted or substituted mono- to trinuclear aromatic system,comprises reacting an aryl benzyl ether of the general formula II ##STR2## where X, Y, R, R.sup.1, R.sup.2 and m have the abovementioned meanings, with a carbonyl halide or with a carboxylic anhydride or with a carboxylic sulfonic anhydride in the presence of an acid and in the presence or absence of a diluent.Type: GrantFiled: April 15, 1994Date of Patent: July 4, 1995Assignee: BASF AktiengesellschaftInventors: Wassilios Grammenos, Wolfgang Siegel, Klaus Oberdorf, Bernd Mueller, Hubert Sauter, Reinhard Doetzer
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Patent number: 5426233Abstract: A process for preparing an hydroxyketone of the formula (X): ##STR1## wherein Ar represents substituted phenyl, aromatic heterocyclic, or substituted aromatic heterocyclic; R.sup.1 and R.sup.2 independently represents hydrogen, C-1 to C-16 alkyl, aromatic, substituted aromatic, aromatic heterocyclic, substituted aromatic heterocyclic or C-1 to C-5 alkyl covalently bonded to Ar, with the provision that R.sup.1 and R.sup.2 are different. The process comprises contacting a compound of the formula (V): ##STR2## with a solvent, a base and a chiral hydroxylating agent at a temperature of about -85.degree. C. or less.Compounds of the formulae ##STR3## also are disclosed.Type: GrantFiled: September 23, 1993Date of Patent: June 20, 1995Assignee: Schering CorporationInventor: Dinesh Gala
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Patent number: 5395975Abstract: Polyacylated aromatic compounds of formula I ##STR1## where R.sup.1 is phenyl which is unsubstituted or has inert substituents or is .alpha.-halo-C.sub.1 -C.sub.6 -alkyl, it being possible for these radicals to be identical or different;R.sup.2 is C.sub.1 -C.sub.4 -alkyl;m is 2 or 3;n is 0 to 4, it being possible for the R.sup.2 substituents to be different when n>1,with the proviso that m+n.ltoreq.6, are prepared by reacting an acylaromatic compound of the formula II ##STR2## where p is 1 or 2, with a carbonyl halide of the formula III ##STR3## where X is halogen, in an amount appropriate for the desired degree of acylation, in the presence of Fe(II), Fe(III), Zn(II), Mo(VI), W(VI) or Sn(IV) compounds.Type: GrantFiled: December 1, 1993Date of Patent: March 7, 1995Assignee: BASF AktiengesellschaftInventors: Wolfgang Siegel, Jochen Schroeder
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Patent number: 5391811Abstract: .alpha.-fluoro-.beta.-dicarbonyl compounds are prepared by reacting a halogenated dicarbonyl compound at temperatures of 20.degree. to 100.degree. C. with an addition product of hydrogen fluoride and a trialkylamine. This process is easy to carry out in technical terms and can also be carried out on a large scale.Type: GrantFiled: November 3, 1993Date of Patent: February 21, 1995Assignee: Bayer AktiengesellschaftInventors: Stefan Bohm, Albrecht Marhold
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Patent number: 5360935Abstract: A novel process for the preparation of 3-pheny-2-propenones of the formula ##STR1## which process comprises reacting phenylmethanesulphonyl fluorides of the formula ##STR2## with ketones of the formula ##STR3## in which A, R, Z and M have the meanings given in the specification,in the presence of a phase transfer catalyst and in the presence of acid binders and inert solvents.The products are known intermediates for the preparation of pesticides and pharmaceuticals.Type: GrantFiled: September 14, 1992Date of Patent: November 1, 1994Assignee: Nihon Bayer Agrochem K.K.Inventors: Shinzo Kagabu, Katsuaki Wada