Aldehyde Or Ketone Patents (Class 562/577)
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Patent number: 6528668Abstract: Methods for making 2-(&ohgr;-alkoxycarbonylalkanoyl)-4-butanolide and derivatives thereof, esters of &ohgr;-hydroxy-(&ohgr;-3)-ketoaliphatic acid and derivatives thereof, which are useful as a variety of synthetic raw materials and intermediates, and are prepared as intermediates in the production step of &ohgr;-hydroxyaliphatic acid being important intermediates of large cyclic lactone-based perfumes in the perfume industry.Type: GrantFiled: January 14, 2002Date of Patent: March 4, 2003Assignee: Toray Industries, Inc.Inventors: Hideaki Takaoka, Sigeru Wada, Nobuhiko Ito, Akio Hasebe, Shinzo Imamura, Hideo Muraoka
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Patent number: 6518454Abstract: Disclosed is a process wherein a solution of a carboxylic acid in a first solvent and an alcohol are fed to a simulated moving bed reactor (SMBR) containing a solid(s) to produce a first stream comprising a solution of an ester of the carboxylic acid and the alcohol and a second stream comprising the first solvent. The solid(s) present in the SMBR facilitates the esterification reaction and the separation of the first solvent from the carboxylic acid. The process is particularly valuable for the preparation of an alkanol solution of an alkyl 2-keto-L-gulonate ester (AKLG) from an aqueous fermentation broth containing dissolved 2-keto-L-gulonic acid (KLG) by feeding the fermentation broth and an alkanol to a simulated moving bed reactor which contains a solid acidic esterification catalyst to produce a stream comprising an alkanol solution of an ALKG. The alkanol solution of an ALKG may be used directly to convert the ALKG to ascorbic acid (Vitamin C).Type: GrantFiled: October 12, 2001Date of Patent: February 11, 2003Assignee: Eastman Chemical CompanyInventors: Bhaskar Krishna Arumugam, Larry Wayne Blair, Brendan William Boyd, Nick Allen Collins, David Anthony Larkin, Steven Thomas Perri, Chester Wayne Sink
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Patent number: 6492550Abstract: Inhibitors of the cytosolic phospholypase A2 enzymes are provided which are of use in controlling a wide variety of inflammatory diseases. The inhibitors of the present invention have the general formula where X, Z, X1, R1, R2, Ra and Rb are as defined in the specification.Type: GrantFiled: February 8, 2001Date of Patent: December 10, 2002Assignee: Bristol-Myers Squibb CompanyInventors: Jacques Banville, Serge Plamondon, Yonghua Gai, Neelakantan Balasubramanian
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Patent number: 6436994Abstract: Heteroatom-interrupted HETE derivatives and methods of their use for treating dry eye are disclosed.Type: GrantFiled: June 25, 2001Date of Patent: August 20, 2002Assignee: Alcon Universal Ltd.Inventors: Raymond E. Conrow, Peter G. Klimko
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Patent number: 6417389Abstract: This invention relates to a novel advantageous process for the stereoselective preparation of 2-hydroxy-4-phenylbutyrates (HPB esters) and of their precursors. This is done by starting from readily accessible &agr;-unsaturated &agr;-hydroxy-&ggr;-keto esters which can be prepared by Claisen condensation.Type: GrantFiled: September 25, 2000Date of Patent: July 9, 2002Assignee: Ciba Specialty Chemicals CorporationInventors: Martin Studer, Peter Herold, Adriano Indolese, Stefan Burckhardt
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Patent number: 6342631Abstract: A method of producing calcium pyruvates is described, in which calcium salts of organic acids or acidic organic keto or hydroxy compounds are reacted with pyruvic acid at a temperature in the range from −20 to +120° C., if necessary in the presence of a solvent or diluent. In this way, high-purity calcium pyruvates are obtained which can be largely free of water and have a very long shelf life.Type: GrantFiled: August 30, 2000Date of Patent: January 29, 2002Assignee: SKW Trostberg AktiengesellschaftInventors: Ivo Pischel, Stefan Weiss, Gunter Ortenburger, Harro Konig
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Patent number: 6331566Abstract: Heteroatom-interrupted HETE derivatives and methods of their use for treating dry eye are disclosed.Type: GrantFiled: October 23, 2000Date of Patent: December 18, 2001Assignee: Alcon Universal Ltd.Inventors: Raymond E. Conrow, Peter G. Klimko
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Patent number: 6274766Abstract: The present invention relates to an improved process for purifying &agr;-keto acids. In particular, the present invention pertains to the isolation of pivalic acid and other organic impurities from &agr;-keto acids. The process of the invention generally includes (i) the partial acidification of an aqueous solution of a sodium salt of the &agr;-keto acid (a“keto salt”), (ii) a first solvent extraction of the keto salt solution to remove organic impurities, (iii) further acidification of the keto salt solution, (iv) a second solvent extraction to remove the &agr;-keto acid, and (v) isolation of the &agr;-keto acid from the solvent. In a preferred embodiment, the present invention relates to the preparation of trimethylpyruvic acid (TMPA) of enhanced purity.Type: GrantFiled: May 19, 1999Date of Patent: August 14, 2001Assignee: Bayer CorporationInventors: Dennis E. Jackman, Cathy L. Howerton
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Patent number: 6268530Abstract: Process to separate linear 5-formylvaleric acid from a mixture of 5- and 3- and 4-formylvaleric acids, wherein the separation is performed by fractional extraction with two immiscible solvents of which one solvent is an aqueous solvent and the other solvent is an organic solvent, in which the organic solvent has a higher or lower affinity for 5-formylvaleric acid than its affinity for the 3-formylvaleric acids and for the 4-formylvaleric acid. Furthermore the invention relates to an improved process to prepare ∈-caprolactam starting from a mixture of branched and linear formylvaleric acids or starting from pentenoic acid.Type: GrantFiled: January 5, 1998Date of Patent: July 31, 2001Assignees: DSM N.V., E. I. DuPont de Nemours and CompanyInventors: Imre Toth, Onko Gelling, Rudolf P. M. Guit, Antonius J. F. Simons, Simon Hans H. Niemann
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Patent number: 6252105Abstract: Organic compounds, e.g. fluorinated organic compounds such as fluorinated carboxylic acids or fluorinated carboxylic acid chlorides, may contain small amounts of carboxylic acid fluorides, hydrogen fluoride or hydrolyzable fluoride, which during the preparation of derivatives of the fluorinated organic compounds, for example by esterification, may yield corrosive fluorides or hydrogen fluoride. The invention is a method for the synthesis and/or purification of preferably fluorinated organic compounds such as carboxylic acids, carboxylic acid chlorides and derivatives such as esters thereof, starting from corresponding carboxylic acid chlorides containing acid fluorides or hydrolyzable fluoride, and alcohols under the catalytic action of “onium” salts of carboxylic acids, to obtain products which have a low fluoride content. Alternatively, an inorganic oxide adsorbent is utilized.Type: GrantFiled: July 6, 1999Date of Patent: June 26, 2001Assignee: Solvay Fluor und Derivate GmbHInventors: Max Braun, Johannes Eicher, Francine Janssens, Kerstin Eichholz, Stefan Palsherm
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Patent number: 6245884Abstract: This invention provides a method of determining the proteolytic activity of the in vivo secretases, particularly the &bgr;-secretase and &ggr;-secretase that produce the A&bgr; peptides found in the plaques of Alzheimer Dementia (AD) patients. The invention also provides methods of isolating such secretases and methods of selecting agents that affect the activity of such secretases for developing drugs to treat or prevent dementia.Type: GrantFiled: October 16, 1998Date of Patent: June 12, 2001Inventor: Vivian Y. H. Hook
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Patent number: 6232497Abstract: A method for producing alkali metal and alkaline earth metal pyruvates is disclosed, in which salts of organic acids or acidic organic keto or hydroxy compounds containing as cation one from the group comprising Li, Na, K, Rb, Cs, Mg, Sr and Ba, or mixtures of these salts, are reacted with pyruvic acid at a temperature ranging from −20 to +120°C., if necessary in the presence of a solvent or diluent. In this way, alkali metal and alkaline earth metal pyruvates of high purity are obtained, which can be largely anhydrous and have a very long shelf life. In addition, novel Rb, Cs, Sr and Ba pyruvates are disclosed. These pyruvates are used, for example, to enhance endurance and strength in the field of sport, as protective substances for body cells and tissues, and as food supplements. They are also used for technical applications.Type: GrantFiled: December 20, 1999Date of Patent: May 15, 2001Assignee: SKW Trostberg AktiengesellschaftInventor: Ivo Pischel
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Patent number: 6153791Abstract: The present invention relates to a process for the purification of 2-keto-L-gulonic acid by continuous liquid chromatography using a weakly basic ion exchange resin.Type: GrantFiled: August 2, 1999Date of Patent: November 28, 2000Assignee: Archer-Daniels-Midland CompanyInventor: Kevin M. Moore
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Patent number: 6127498Abstract: Hydrogenated fluoromodified polymers obtainable by reaction among hydrogenated polymers and the modifier having a polyether structure:RfO(CF.sub.2 CF.sub.2 O).sub.m (CF.sub.2 O).sub.n --CF.sub.2 --A.sub.q --T.sub.p (I)wherein A is a linking bridge bound to the end group --CF.sub.2 -- of the perfluoropolyether chain, T represents one or more reactive functional groups; p and q are integers, p ranges from 1 to 4, q is an integer from 0 to 1; m and n are integers such that m/n is comprised between 0.2 and 5, Rf is a perfluoroalkyl from 1 to 3 carbon atoms.Type: GrantFiled: April 6, 1998Date of Patent: October 3, 2000Assignee: Ausimont S.p.A.Inventors: Claudio Tonelli, Giovanni Simeone, Tania Trombetta
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Patent number: 6087138Abstract: The present invention relates to a process for the preparation of a composition rich in sotolon from a source rich in 4-hydroxy-L-iso-leucine.Type: GrantFiled: February 3, 1999Date of Patent: July 11, 2000Assignee: Unilever Patent Holdings BVInventors: Amir Maximiliaan Batenburg, Johannes Jan Wesdorp
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Patent number: 5968727Abstract: The invention comprises a novel pyruvate compound for the treatment of prevention of reperfusion injury following ischemia, diabetic effects, cholesterol levels, injured organs ethanol intoxication oras s foodstuff. The novel pyruvate compound is particularly a puruvate thiolester, a glucerol-pyruvate ester or a dihydoxyacetone-pyruvate ester.Type: GrantFiled: March 1, 1999Date of Patent: October 19, 1999Assignee: Case Western Reserve UniversityInventors: Henri Brunengraber, Catherine Bomont, France David, Peter T. Hallowell
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Patent number: 5965558Abstract: Y--X--C(R').dbd.C(R")COOR"'(A1)The present invention relates to novel protein tyrosine phosphatase modulating compounds having the general structure shown in Formula (A1), to methods for their preparation, to compositions comprising the compounds, to their use for treatment of human and animal disorders, to their use for purification of proteins or glycoproteins, and to their use in diagnosis. The invention relates to modulation of the activity of molecules with phosphotyrosine recognition units, including protein tyrosine phosphatases (PTPases) and proteins with Src-homology-2 domains, in in vitro systems, microorganisms, eukaryoic cells, whole animals and human beings. R' and R" are independently selected from the group consisting of hydrogen, halo, cyano, nitro, trihalomethyl, alkyl, arylalkyl. R"' is selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, arylalkyl. X is aryl. Y is selected from hydrogen or ##STR1## wherein (*) indicates a potential point of attachment to X.Type: GrantFiled: October 29, 1997Date of Patent: October 12, 1999Assignee: Ontogen CorporationInventors: Adnan Mjalli, Sepehr Sarshar, Xiaodong Cao, Farid Bakir
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Patent number: 5962734Abstract: A method of producing calcium pyruvates is described, in which calcium salts of organic acids or acidic organic keto or hydroxy compounds are reacted with pyruvic acid at a temperature in the range from -20 to +120.degree. C., if necessary in the presence of a solvent or diluent. In this way, high-purity calcium pyruvates are obtained which can be largely free of water and have a very long shelf life.Type: GrantFiled: October 21, 1997Date of Patent: October 5, 1999Assignee: SKW Trostberg AktiengesellschaftInventors: Ivo Pischel, Stefan Weiss, Gunter Ortenburger, Harro Konig
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Patent number: 5919978Abstract: This invention relates in part to processes for producing one or more substituted or unsubstituted aldehyde acids or salts, e.g., 5-formylvaleric acid or salt, which comprises subjecting one or more substituted or unsubstituted alkadienes, e.g., butadiene, to hydroxycarbonylation in the presence of a hydroxycarbonylation catalyst, e.g., a metal-organophosphorus ligand complex catalyst, and optionally neutralization with a base to produce one or more substituted or unsubstituted unsaturated acids or salts, e.g., pentenoic acid or salt, and subjecting said one or more substituted or unsubstituted unsaturated acids or salts to hydroformylation in the presence of a hydroformylation catalyst, e.g., a metal-organophosphorus ligand complex catalyst, to produce said one or more substituted or unsubstituted aldehyde acids or salts and/or one or more substituted or unsubstituted epsilon caprolactam precursors.Type: GrantFiled: April 15, 1997Date of Patent: July 6, 1999Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Diane Lee Packett, Thomas Carl Eisenschmid, Michael Allen Brammer, John Michael Maher
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Patent number: 5907047Abstract: This invention relates to a new biologically active compound as shown in formula (I) and its biologically active derivatives; whereas derivatives are produced by the reaction of formula (I) with nucleophiles.Type: GrantFiled: July 23, 1998Date of Patent: May 25, 1999Assignee: Boehringer Mannheim GmbHInventors: Fritz Hansske, Olov Sterner, Marc Satadler, Heidrun Anke, Liesel Dorge, Rudong Shan
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Patent number: 5750769Abstract: The invention provides novel compounds of formula:CF.sub.3 --CXCl--CH(OH)CH.sub.2 --C(CH.sub.3).sub.2 --CH.sub.2 --CO.sub.2 R(I)where X represents chloro or bromo and R represents hydrogen or alkyl of up to 4 carbon atoms, processes for preparing them and their use as intermediates in the preparation of insecticidal cyclopropane derivatives. Also provided are novel compounds of formula:BrCH.sub.2 --CH.sub.2 --C(CH.sub.3).sub.2 --CH.sub.2 --CO.sub.2 R(IV)wherein R represents alkyl of up to 4 carbon atoms, useful as intermediates in the preparation of the compounds of formula I.Type: GrantFiled: November 8, 1995Date of Patent: May 12, 1998Assignee: Zeneca LimitedInventor: Martin Charles Bowden
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Patent number: 5723661Abstract: A process for preparing high-purity calcium pyruvate or its hydrates by reacting an aqueous solution of pyruvic acid with an inorganic calcium compound with the pH being set to 2 to 7, preferably 2.5 to 4, which comprises reacting an up to 10% strength aqueous solution of pyruvic acid with the calcium compound, in the presence or absence of a stabilizer or complexing agent, and mixing the resulting solution with an organic diluent at temperatures of 0.degree. to 30.degree. C. and isolating the resulting precipitate of calcium pyruvate or its hydrate from the solution.Type: GrantFiled: March 11, 1997Date of Patent: March 3, 1998Assignee: DSM Chemie Linz GmbHInventors: Curt Zimmermann, Kurt Weissenbock
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Patent number: 5705522Abstract: A new family of compounds having anti-inflammatory, anti-viral, and brocho-dilating activity having the following linear and cyclic formulas: ##STR1## and compositions of these, which alone, and in combination with reverse transcriptase inhibitors thereby resulting in an additive or synergistic effect, are useful in inhibiting or suppressing viruses including those exhibiting retroviral replication, or in treating viruses including a retrovirus such as HIV in a human cell population and methods of using these compositions, compounds, and salts thereof.Type: GrantFiled: February 13, 1996Date of Patent: January 6, 1998Assignee: Compagnie de Developpement Aguettant S.A.Inventors: Farid Hamedi-Sangsari, Fabienne Nugier, Thierry Vallet, Jacques Grange, Jorge Vila
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Patent number: 5693828Abstract: Described is a process for preparing cyclopentadecanolide defined according to the structure: ##STR1## using as a starting material the dicarboxylic acid having the structure: ##STR2## according to the reaction sequence: ##STR3## Also described is a process for using the resultant cyclopentadecanolide for augmenting, enhancing or imparting aromas in or to perfume compositions, colognes and perfumed articles including but not limited to solid or liquid anionic, cationic, nonionic or zwitterionic detergents, perfumed polymers, fabric softener compositions, fabric softener articles, cosmetic powders and hair preparations.Type: GrantFiled: May 9, 1996Date of Patent: December 2, 1997Assignee: International Flavors & Fragrances Inc.Inventor: Robert P. Belko
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Patent number: 5677423Abstract: A process for removing .beta.-hydroxy groups from .beta.-hydroxy-containing compounds is disclosed. The process involves the use of a retro-aldol-promoting reagent selected from the group of trimethylamine-N-oxide, triethylamine-N-oxide, trimethylamine-N-oxide-hydrate, and trimethylamine-hydrate and requires dissolution of the substrate in an aprotic solvent and reaction under elevated temperatures. The process is broadly applicable to a variety of substrates including complex cyclic peptides, linear peptides, and non-peptides.Type: GrantFiled: December 10, 1996Date of Patent: October 14, 1997Assignee: Eli Lilly and CompanyInventor: Michael J. Rodriguez
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Patent number: 5648387Abstract: Dialkyl ethers lower Lp(a) and triglycerides, and elevate HDL-cholesterol, and are thereby useful for treating vascular diseases and noninsulin-dependent diabetes mellitus.Type: GrantFiled: March 24, 1995Date of Patent: July 15, 1997Assignee: Warner-Lambert CompanyInventors: Charles Larry Bisgaier, Paul Leroy Creger, Alan Robert Saltiel, Sherrie Rae Tafuri
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Patent number: 5627288Abstract: Disclosed are 3,7-dimethyl-4-oxo-7-octenoic acid and its alkyl esters which are intermediates for producing a fragrance, rosefuran and which are represented by: ##STR1## where R is H or a lower alkyl. The compounds [1] are obtained by reacting 2-methyl-3-alkoxycarbonylpropionic acid halide and 3-methyl-3-butenylmagnesium halide. The octenoic acid [1] is treated with acetic anhydride under heat in the presence of an acidic catalyst to give 3,7-dimethyl-2,6-octadien-4-olide. The olide is reduced in an ordinary manner to give rosefuran.Type: GrantFiled: March 11, 1996Date of Patent: May 6, 1997Assignee: Toyotama Perfumery Co., Ltd.Inventors: Hidemichi Fukawa, Masamichi Nishitani, Mitsuo Chiba, Ruriko Murakami
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Patent number: 5610314Abstract: A process is provided for preparing dioxolenone derivatives of the structure ##STR1## wherein R is alkyl or aryl and R.sub.3 is CO.sub.2 R.sub.2 (where R.sub.2 is alkyl or arylalkyl such as benzyl, diphenylmethyl or para-methoxybenzyl). Intermediates produced in the above process are also provided as well as a method for preparing squalene synthetase inhibitors employing such intermediates.Type: GrantFiled: April 3, 1995Date of Patent: March 11, 1997Assignee: Bristol-Myers Squibb CompanyInventors: Peter T. W. Cheng, Chong-Oing Sun, Michael A. Poss
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Patent number: 5602280Abstract: Disclosed are a process for producing an unsaturated aldehyde and an unsaturated carboxylic acid which comprises subjecting propylene, isobutylene or tertiary butanol to gas phase catalytic oxidation with molecular oxygen in the presence of (i) a catalyst comprising composite oxide of the formula Mo.sub.a Bi.sub.b Fe.sub.c A.sub.d B.sub.e C.sub.f D.sub.g O.sub.x and (ii) a molybdenum oxide which in itself is substantially inert to the gas phase catalytic oxidation; a process for reusing the catalyst deteriorated due to the gas phase catalytic oxidation after mixing it with the molybdenum oxide; and a method of regenerating the deteriorated catalyst by mixing it with the molybdenum oxide.Type: GrantFiled: June 27, 1994Date of Patent: February 11, 1997Assignee: Sumitomo Chemical Company, LimitedInventors: Koichi Nagai, Yoshisaburou Nomura, Yoshihiko Nagaoka
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Patent number: 5554790Abstract: In a process for producing acetic anhydride and acetic acid by reacting methanol and methyl acetate, optionally together with dimethyl ether, with carbon monoxide, acetic anhydride and acetic acid are effectively produced with the use of a sequence of production facilities by carrying out separation of low-boiling point fraction mainly consisting of methyl iodide, methyl acetate and dimethyl ether with the use of at least two distillation zones, separating catalyst drops entrained from the vapor-liquid separation zone in at least one distillation zone and further by controlling the pressurization of the vapor-liquid separation zone and the above distillation zones under 5 bar to a pressure greater than atmospheric pressure.Type: GrantFiled: March 22, 1995Date of Patent: September 10, 1996Assignee: Daicel Chemical Industries, Ltd.Inventors: Yoshiyuki Harano, Yoshiaki Morimoto
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Patent number: 5449823Abstract: Two optically active forms of 4-hydroxy-3-methyl-2-keto-pentanoic acid of the formula ##STR1## wherein carbon atom 4 has the (S)-configuration, and carbon atom 3 can have the (R)-configuration or the (S)-configuration (compound I) are made using a biotransformation process. Compound I may be manufactured by reacting 4-hydroxy-isoleucine (2S, 3R, 4S) of the formula: ##STR2## with microorganisms which have L-amino acid oxidase activity or with an L-amino acid oxidase. Compound I is a flavor precursor and may also be used as an intermediate for the production of the optically active (5S)-3-hydroxy-4,5-dimethyl-2(5H)-furanone: ##STR3## which is useful as a flavorant.Type: GrantFiled: April 28, 1994Date of Patent: September 12, 1995Assignee: Givaudan-Roure CorporationInventor: Konrad Lerch
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Patent number: 5449821Abstract: A process for the gas phase catalytic oxidation of a C.sub.3-6 alkane, alkanol, alkene or alkenal using as a catalyst multimetal oxide compositions of the formula I, [X.sup.1.sub.a X.sup.2.sub.b O.sub.x ].sub.p [X.sup.3.sub.c X.sup.4.sub.d X.sup.5.sub.e X.sup.6.sub.f X.sup.7.sub.g X.sup.2.sub.h O.sub.y ].sub.q, where X.sup.1 is bismuth, tellurium, antimony, tin and/or copper, X.sup.2 is molybdenum and/or tungsten, X.sup.3 is an alkali metal, thallium and/or samarium, X.sup.4 is an alkaline earth metal, nickel, cobalt, copper, manganose, zinc, tin, cadmium and/or mercury, X.sup.6 is iron, chromium, cerium and/or vanadium, X.sup.6 is phosphorus, arsenic, boron and/or antimony, X.sup.7 is a rare-earth metal, titanium, zirconium, niobium, tantalum, rhenium, ruthenium, rhodium, silver, gold, aluminum, gallium, indium, silicon, geranium, lead, thorium and/or uranium, a is from 0.01 to 8, b is from 0.Type: GrantFiled: June 30, 1994Date of Patent: September 12, 1995Assignee: BASF AktiengesellschaftInventors: Hans-Peter Neumann, Hans Martan, Hermann Petersen, Walter Doerflinger
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Patent number: 5395965Abstract: A catalyst containing platinum on carbon as carrier for the catalytic oxidation of glyoxal to glyoxalic acid. Activity and selectivity of the catalyst can be considerably improved by modification with molybdenum and/or cerium.Type: GrantFiled: May 20, 1994Date of Patent: March 7, 1995Assignee: Degussa AktiengesellschaftInventors: Roland Burmeister, Klaus Deller, Bertrand Despeyroux, Hatte Christine
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Patent number: 5393924Abstract: Acylamides or amine acylate salts of arylalkanolamines are prepared by reacting an arylisonitrosoalkanone with hydrogen and a carboxylic acid, carboxylic acid anhydride or carboxylic acid ester or mixture thereof in the presence of a transition metal catalyst; optionally the product is converted to the corresponding arylalkanolamine hydrochloride salt by reaction of the acylamide or amine acylate salt of the arylalkanolamine with hydrogen chloride in a C.sub.1 -C.sub.3 alkyl alcohol.Type: GrantFiled: April 29, 1994Date of Patent: February 28, 1995Assignee: Hoechst Celanese CorporationInventors: Ahmed M. Tafesh, Olan S. Fruchey, Charles B. Hilton
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Patent number: 5286893Abstract: Alkenoic acid compounds are described. The compounds which are dehydropeptidase inactivators contain a ##STR1## moiety which is substituted with a halomethylene or a cyano moiety as R.sub.3. The enzyme deprotonates the alpha --CH.sub.2 group and then the intermediate compound forms a covalent bond with enzymic residue in the active site, resulting in irreversible inactivation of the enzyme. The compounds are particularly inactivators of renal dipeptidases.Type: GrantFiled: January 28, 1992Date of Patent: February 15, 1994Assignee: Board of Governors of Wayne State UniversityInventor: Shahriar Mobashery
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Patent number: 5276180Abstract: The present invention is a simplified process for making succinyl acetone (SA). The most preferred embodiment is a one step process that reacts levulinic acid, ethyl acetate, and a base to form SA. Generally, a levulinic acid group may be reacted with an alkyl ester and a base to form SA. Optionally, the reaction may be acidified after completion to remove byproducts.Type: GrantFiled: September 6, 1989Date of Patent: January 4, 1994Assignee: Cetus Oncology CorporationInventor: Corey H. Levenson
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Patent number: 5202461Abstract: A 3-substituted 2-hydroxy3-formylpropionic ester of the formula I ##STR1## where R.sup.1 is lower alkyl, and R.sup.2 is straight-chain or branched alkyl of 1 to 10 carbon atoms, is obtained by adding an alkanal of the formula II ##STR2## and an alkyl glyoxylate of the formula III ##STR3## simultaneously to a catalyst system composed of a salt or a mixture of a secondary amine and a carboxylic acid in such a way that the temperature does not exceed 90.degree. C., preferably 80.degree. C., or else adding one of the reactants of the formula II or III to a mixture of the catalyst system described above and the other reactant in such a way that the temperature does not exceed 90.degree. C. The 2-hydroxy-3-formylpropionic ester of the formula I can be converted by treatment with dehydrating agents, especially acetic anhydride, into good yields of the corresponding 3-substituted 3-formylacrylic ester.Type: GrantFiled: October 5, 1990Date of Patent: April 13, 1993Assignee: BASF AktiengesellschaftInventors: Franz Merger, Juergen Frank
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Patent number: 5202467Abstract: Process for preparing haloketo acid derivatives [I]: ##STR1## wherein R is H or C.sub.1-6 alkyl, and X is chlorine or bromine, which comprises reacting .beta.-oxo-acid ester [II]: ##STR2## wherein R.sup.1 is C.sub.1-6 alkyl, R.sup.2 is C.sub.1-5 alkyl or OR.sup.3 (R.sup.3 is C.sub.1-6 alkyl), and X is the same as above, with nitrosating agent [IV]:ONOR.sup.4 [IV]wherein R.sup.4 is H, alkyl, halogen or SO.sub.3 H to give 7-halo-2-hydroxyiminoheptanoic acid ester [III]: ##STR3## wherein R.sup.1 and X are the same as above, followed by reacting the product with aldehyde or ketone; and intermediates therefor, and process for preparing said intermediates. Said haloketo acid derivatives are useful as intermediate for synthesis of cilastatin, which is useful as medicament, especially as dehydropeptidase inhibitor.Type: GrantFiled: February 7, 1991Date of Patent: April 13, 1993Assignee: Sumitomo Chemical Company, LimitedInventors: Takaharu Ikeda, Seiichi Kai, Masayoshi Minai
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Patent number: 5202476Abstract: According to the present invention which comprises subjecting an aqueous solution of 2-keto-L-gulonic acid or its water-soluble salt containing an acid impurity, whose acidity is higher than that of 2-keto-L-gulonic acid, to contact with an anion-exchange resin, then allowing the 2-keto-L-gulonic acid or the water-soluble salt thereof to precipitate from the processed solution obtained by allowing the impurity to be adsorbed, 2KGA or its water-soluble salt of a high purity can be separated in a high yield from an aqueous solution of 2KGA or its water-soluble salt containing acid impurities with less number of steps as compared with conventional methods.Type: GrantFiled: April 29, 1991Date of Patent: April 13, 1993Assignee: Takeda Chemical Industries, Ltd.Inventors: Masahiko Tsuda, Kimio Iwai
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Patent number: 5189215Abstract: A process for the preparation of color-stable levulinic acid by saponification of acetylsuccinates with aqueous mineral acids, by continuously treating the starting products with steam in counter-current in a reactor cascade, the reaction being carried out above the boiling point of the alcohol being formed in the reaction or above the boiling point of the aqueous azeotrope being formed.Type: GrantFiled: October 28, 1991Date of Patent: February 23, 1993Assignee: Chemie Linz Gesellschaft m.b.H.Inventors: Lorenz Farnleitner, Hubert Stuckler, Herbert Kaiser, Engelbert Kloimstein
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Patent number: 5175358Abstract: Essentially pure and colorless laevulinic acid is produced by heating and ring-opening furfuryl alcohol in the presence of water and a strong non-oxidizing protonic acid, and which includes establishing a reaction medium containing water, the strong protonic acid and a reaction solvent amount of laevulinic acid, and progressively introducing the furfuryl alcohol into such reaction medium.Type: GrantFiled: December 11, 1989Date of Patent: December 29, 1992Assignee: Societe Francaise d'Organo-SyntheseInventors: Bernard Capai, Guy Lartigau
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Patent number: 5169862Abstract: This invention is directed to the analogs of viscosin, pharmaceutical compositions thereof and to their use as antibacterial, antiviral and antitrypanosomal therapeutic compounds.Type: GrantFiled: November 18, 1991Date of Patent: December 8, 1992Assignee: Peptide Technologies CorporationInventors: Terrence Burke, Jr., Bhaskar Chandrasekhar, Martha Knight
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Patent number: 5162552Abstract: A process for the preparation of 4-acetals of butene-1,4-dial of the formula ##STR1## where R is an alkyl, alkenyl, cycloalkyl or aralkyl radical of 1 to 12 carbon atoms which may contain alkoxy groups, or the two radicals R together form an alkylene or alkenylene radical of 2 to 10 carbon atoms which may contain alkoxy groups, and R.sup.1 is an alkyl, alkenyl or alkynyl radical of 1 to 12 carbon atoms which may be substituted by cycloaliphatic, aromatic or heterocyclic radicals or by hydroxyl, ether, thioether, acyl, alkylamino, carboxyl or carbalkoxy groups, or is an unsubstituted or substituted aryl radical or an alkoxy, alkylthio or acyloxy group, wherein a glyoxal monoacetal of the formula ##STR2## is reacted with an aldehyde of the formulaR.sup.1 --CH.sub.2 --CHO IIIat up to 150.degree. C., and novel acetals of butene-1,4-dial.Type: GrantFiled: April 30, 1987Date of Patent: November 10, 1992Assignee: BASF AktiengesellschaftInventors: Franz Merger, Rolf Fischer, Hans Horler, Juergen Frank
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Patent number: 5138096Abstract: Continuous manufacturing process for an aqueous solution of glyoxylic acid by nitric oxidation of an aqueous solution of glyoxal carried out in the presence of hydrochloric acid in which the oxidation is effected continuously using 0.80.+-.0.2 mole of nitric acid and 0.70.+-.0.05 mole of hydrochloric acid per mole of glyoxal in a reaction medium having a concentration by weight between 5 and 6% of hydrochloric acid and higher than 10% of nitric acid.Type: GrantFiled: November 16, 1990Date of Patent: August 11, 1992Assignee: Societe Francaise HoechstInventors: Alain Schouteeten, Jean-Michel Alarcon
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Patent number: 5091566Abstract: The invention relates to the preparation of glyoxylic acid by oxidizing an aqueous solution of glyoxal having a pH less than 1 with molecular oxygen in the presence of nitrogen monoxide as a catalyst.This process allows the practically total conversion of the starting glyoxal with a good yield of glyoxylic acid.Type: GrantFiled: July 3, 1989Date of Patent: February 25, 1992Assignee: Societe Francaise HoechstInventors: Alain Schouteeten, Yani Christidis
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Patent number: 5091568Abstract: In the oxidation of 2-hydroxy-3,3-dimethyl-butanoic acid in solution in the presence of a ruthenium oxide catalyst to produce 2-oxo-3,3-dimethyl-butanoic acid, the improvement wherein oxidation is effected with oxygen.Type: GrantFiled: May 23, 1986Date of Patent: February 25, 1992Assignee: Mobay CorporationInventor: Dennis E. Jackman
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Patent number: 5068417Abstract: A process for continuous preparation of a concentrated aqueous solution of glyoxylic acid by hydrolysis of glyoxylic acid ester hemiacetals, wherein glyoxylic acid ester hemiacetals are treated with steam in countercurrent in a reactor cascade.Type: GrantFiled: May 25, 1990Date of Patent: November 26, 1991Assignee: Chemie Linz Gesellschaft m.b.H.Inventors: Alexander Sajtos, Engelbert Kloimstein, Karl Hollinger, Lorenz Farnlettner
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Patent number: 5053527Abstract: The invention provides an improved process for the manufacture of alkyl pyruvates having general formula (I):CH.sub.3 --CO--COOR (I)where R represents a C.sub.1 to C.sub.8 alkyl radical, by controlled oxidation of the corresponding alkyl lactate.The process is characterized in that the controlled oxidation is carried out using an aqueous hydrogen peroxide solution in the presence of catalytic quantities of bromium.Type: GrantFiled: May 18, 1990Date of Patent: October 1, 1991Assignee: Societe Francaise HoechstInventors: Yani Christidis, Jean-Claude Vallejos
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Patent number: 4973747Abstract: A process has now been discovered by which an intermediate in preparation of antibiotics ##STR1## may be directly derived from the substrate ##STR2## by treatment with aqueous solutions of MHCO.sub.3 and MOH, wherein: R.sup.1, R.sup.2 and R.sup.3 are each independently alkyl, alkenyl, alkynyl, substituted alkyl, substituted alkenyl, substituted alkynyl, aryl, or substituted aryl;M is alkali metal (such as Na, Li, or K); andX is halogen.Type: GrantFiled: August 15, 1989Date of Patent: November 27, 1990Assignee: E. R. Squibb & Sons, Inc.Inventors: Janak Singh, Richard H. Mueller
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Patent number: 4950429Abstract: 6-Aminocaproic acid is prepared by(a) reacting a 5-formylvaleric acid ester with water in the presence of an acid agent at 30.degree.-200.degree. C. and(b) reacting the 5-formylvaleric acid thus obtained with excess ammonia and hydrogen in the presence of a hydrogenation catalyst and of a solvent which is inert under the reaction conditions at 50.degree.-150.degree. C. under superatmospheric pressure.Type: GrantFiled: March 23, 1989Date of Patent: August 21, 1990Assignee: BASF AktiengesellschaftInventors: Uwe Vagt, Rolf Fischer, Franz Merger, Hans-Martin Hutmacher