Aldehyde Or Ketone Patents (Class 562/577)
  • Patent number: 6528668
    Abstract: 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: Grant
    Filed: January 14, 2002
    Date of Patent: March 4, 2003
    Assignee: Toray Industries, Inc.
    Inventors: Hideaki Takaoka, Sigeru Wada, Nobuhiko Ito, Akio Hasebe, Shinzo Imamura, Hideo Muraoka
  • Patent number: 6518454
    Abstract: 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: Grant
    Filed: October 12, 2001
    Date of Patent: February 11, 2003
    Assignee: Eastman Chemical Company
    Inventors: Bhaskar Krishna Arumugam, Larry Wayne Blair, Brendan William Boyd, Nick Allen Collins, David Anthony Larkin, Steven Thomas Perri, Chester Wayne Sink
  • Patent number: 6492550
    Abstract: 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: Grant
    Filed: February 8, 2001
    Date of Patent: December 10, 2002
    Assignee: Bristol-Myers Squibb Company
    Inventors: Jacques Banville, Serge Plamondon, Yonghua Gai, Neelakantan Balasubramanian
  • Patent number: 6436994
    Abstract: Heteroatom-interrupted HETE derivatives and methods of their use for treating dry eye are disclosed.
    Type: Grant
    Filed: June 25, 2001
    Date of Patent: August 20, 2002
    Assignee: Alcon Universal Ltd.
    Inventors: Raymond E. Conrow, Peter G. Klimko
  • Patent number: 6417389
    Abstract: 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: Grant
    Filed: September 25, 2000
    Date of Patent: July 9, 2002
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Martin Studer, Peter Herold, Adriano Indolese, Stefan Burckhardt
  • Patent number: 6342631
    Abstract: 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: Grant
    Filed: August 30, 2000
    Date of Patent: January 29, 2002
    Assignee: SKW Trostberg Aktiengesellschaft
    Inventors: Ivo Pischel, Stefan Weiss, Gunter Ortenburger, Harro Konig
  • Patent number: 6331566
    Abstract: Heteroatom-interrupted HETE derivatives and methods of their use for treating dry eye are disclosed.
    Type: Grant
    Filed: October 23, 2000
    Date of Patent: December 18, 2001
    Assignee: Alcon Universal Ltd.
    Inventors: Raymond E. Conrow, Peter G. Klimko
  • Patent number: 6274766
    Abstract: 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: Grant
    Filed: May 19, 1999
    Date of Patent: August 14, 2001
    Assignee: Bayer Corporation
    Inventors: Dennis E. Jackman, Cathy L. Howerton
  • Patent number: 6268530
    Abstract: 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: Grant
    Filed: January 5, 1998
    Date of Patent: July 31, 2001
    Assignees: DSM N.V., E. I. DuPont de Nemours and Company
    Inventors: Imre Toth, Onko Gelling, Rudolf P. M. Guit, Antonius J. F. Simons, Simon Hans H. Niemann
  • Patent number: 6252105
    Abstract: 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: Grant
    Filed: July 6, 1999
    Date of Patent: June 26, 2001
    Assignee: Solvay Fluor und Derivate GmbH
    Inventors: Max Braun, Johannes Eicher, Francine Janssens, Kerstin Eichholz, Stefan Palsherm
  • Patent number: 6245884
    Abstract: 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: Grant
    Filed: October 16, 1998
    Date of Patent: June 12, 2001
    Inventor: Vivian Y. H. Hook
  • Patent number: 6232497
    Abstract: 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: Grant
    Filed: December 20, 1999
    Date of Patent: May 15, 2001
    Assignee: SKW Trostberg Aktiengesellschaft
    Inventor: Ivo Pischel
  • Patent number: 6153791
    Abstract: 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: Grant
    Filed: August 2, 1999
    Date of Patent: November 28, 2000
    Assignee: Archer-Daniels-Midland Company
    Inventor: Kevin M. Moore
  • Patent number: 6127498
    Abstract: 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: Grant
    Filed: April 6, 1998
    Date of Patent: October 3, 2000
    Assignee: Ausimont S.p.A.
    Inventors: Claudio Tonelli, Giovanni Simeone, Tania Trombetta
  • Patent number: 6087138
    Abstract: 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: Grant
    Filed: February 3, 1999
    Date of Patent: July 11, 2000
    Assignee: Unilever Patent Holdings BV
    Inventors: Amir Maximiliaan Batenburg, Johannes Jan Wesdorp
  • Patent number: 5968727
    Abstract: 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: Grant
    Filed: March 1, 1999
    Date of Patent: October 19, 1999
    Assignee: Case Western Reserve University
    Inventors: Henri Brunengraber, Catherine Bomont, France David, Peter T. Hallowell
  • Patent number: 5965558
    Abstract: 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: Grant
    Filed: October 29, 1997
    Date of Patent: October 12, 1999
    Assignee: Ontogen Corporation
    Inventors: Adnan Mjalli, Sepehr Sarshar, Xiaodong Cao, Farid Bakir
  • Patent number: 5962734
    Abstract: 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: Grant
    Filed: October 21, 1997
    Date of Patent: October 5, 1999
    Assignee: SKW Trostberg Aktiengesellschaft
    Inventors: Ivo Pischel, Stefan Weiss, Gunter Ortenburger, Harro Konig
  • Patent number: 5919978
    Abstract: 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: Grant
    Filed: April 15, 1997
    Date of Patent: July 6, 1999
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Diane Lee Packett, Thomas Carl Eisenschmid, Michael Allen Brammer, John Michael Maher
  • Patent number: 5907047
    Abstract: 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: Grant
    Filed: July 23, 1998
    Date of Patent: May 25, 1999
    Assignee: Boehringer Mannheim GmbH
    Inventors: Fritz Hansske, Olov Sterner, Marc Satadler, Heidrun Anke, Liesel Dorge, Rudong Shan
  • Patent number: 5750769
    Abstract: 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: Grant
    Filed: November 8, 1995
    Date of Patent: May 12, 1998
    Assignee: Zeneca Limited
    Inventor: Martin Charles Bowden
  • Patent number: 5723661
    Abstract: 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: Grant
    Filed: March 11, 1997
    Date of Patent: March 3, 1998
    Assignee: DSM Chemie Linz GmbH
    Inventors: Curt Zimmermann, Kurt Weissenbock
  • Patent number: 5705522
    Abstract: 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: Grant
    Filed: February 13, 1996
    Date of Patent: January 6, 1998
    Assignee: Compagnie de Developpement Aguettant S.A.
    Inventors: Farid Hamedi-Sangsari, Fabienne Nugier, Thierry Vallet, Jacques Grange, Jorge Vila
  • Patent number: 5693828
    Abstract: 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: Grant
    Filed: May 9, 1996
    Date of Patent: December 2, 1997
    Assignee: International Flavors & Fragrances Inc.
    Inventor: Robert P. Belko
  • Patent number: 5677423
    Abstract: 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: Grant
    Filed: December 10, 1996
    Date of Patent: October 14, 1997
    Assignee: Eli Lilly and Company
    Inventor: Michael J. Rodriguez
  • Patent number: 5648387
    Abstract: 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: Grant
    Filed: March 24, 1995
    Date of Patent: July 15, 1997
    Assignee: Warner-Lambert Company
    Inventors: Charles Larry Bisgaier, Paul Leroy Creger, Alan Robert Saltiel, Sherrie Rae Tafuri
  • Patent number: 5627288
    Abstract: 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: Grant
    Filed: March 11, 1996
    Date of Patent: May 6, 1997
    Assignee: Toyotama Perfumery Co., Ltd.
    Inventors: Hidemichi Fukawa, Masamichi Nishitani, Mitsuo Chiba, Ruriko Murakami
  • Patent number: 5610314
    Abstract: 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: Grant
    Filed: April 3, 1995
    Date of Patent: March 11, 1997
    Assignee: Bristol-Myers Squibb Company
    Inventors: Peter T. W. Cheng, Chong-Oing Sun, Michael A. Poss
  • Patent number: 5602280
    Abstract: 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: Grant
    Filed: June 27, 1994
    Date of Patent: February 11, 1997
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koichi Nagai, Yoshisaburou Nomura, Yoshihiko Nagaoka
  • Patent number: 5554790
    Abstract: 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: Grant
    Filed: March 22, 1995
    Date of Patent: September 10, 1996
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Yoshiyuki Harano, Yoshiaki Morimoto
  • Patent number: 5449823
    Abstract: 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: Grant
    Filed: April 28, 1994
    Date of Patent: September 12, 1995
    Assignee: Givaudan-Roure Corporation
    Inventor: Konrad Lerch
  • Patent number: 5449821
    Abstract: 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: Grant
    Filed: June 30, 1994
    Date of Patent: September 12, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans-Peter Neumann, Hans Martan, Hermann Petersen, Walter Doerflinger
  • Patent number: 5395965
    Abstract: 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: Grant
    Filed: May 20, 1994
    Date of Patent: March 7, 1995
    Assignee: Degussa Aktiengesellschaft
    Inventors: Roland Burmeister, Klaus Deller, Bertrand Despeyroux, Hatte Christine
  • Patent number: 5393924
    Abstract: 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: Grant
    Filed: April 29, 1994
    Date of Patent: February 28, 1995
    Assignee: Hoechst Celanese Corporation
    Inventors: Ahmed M. Tafesh, Olan S. Fruchey, Charles B. Hilton
  • Patent number: 5286893
    Abstract: 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: Grant
    Filed: January 28, 1992
    Date of Patent: February 15, 1994
    Assignee: Board of Governors of Wayne State University
    Inventor: Shahriar Mobashery
  • Patent number: 5276180
    Abstract: 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: Grant
    Filed: September 6, 1989
    Date of Patent: January 4, 1994
    Assignee: Cetus Oncology Corporation
    Inventor: Corey H. Levenson
  • Patent number: 5202461
    Abstract: 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: Grant
    Filed: October 5, 1990
    Date of Patent: April 13, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Merger, Juergen Frank
  • Patent number: 5202467
    Abstract: 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: Grant
    Filed: February 7, 1991
    Date of Patent: April 13, 1993
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Takaharu Ikeda, Seiichi Kai, Masayoshi Minai
  • Patent number: 5202476
    Abstract: 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: Grant
    Filed: April 29, 1991
    Date of Patent: April 13, 1993
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Masahiko Tsuda, Kimio Iwai
  • Patent number: 5189215
    Abstract: 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: Grant
    Filed: October 28, 1991
    Date of Patent: February 23, 1993
    Assignee: Chemie Linz Gesellschaft m.b.H.
    Inventors: Lorenz Farnleitner, Hubert Stuckler, Herbert Kaiser, Engelbert Kloimstein
  • Patent number: 5175358
    Abstract: 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: Grant
    Filed: December 11, 1989
    Date of Patent: December 29, 1992
    Assignee: Societe Francaise d'Organo-Synthese
    Inventors: Bernard Capai, Guy Lartigau
  • Patent number: 5169862
    Abstract: This invention is directed to the analogs of viscosin, pharmaceutical compositions thereof and to their use as antibacterial, antiviral and antitrypanosomal therapeutic compounds.
    Type: Grant
    Filed: November 18, 1991
    Date of Patent: December 8, 1992
    Assignee: Peptide Technologies Corporation
    Inventors: Terrence Burke, Jr., Bhaskar Chandrasekhar, Martha Knight
  • Patent number: 5162552
    Abstract: 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: Grant
    Filed: April 30, 1987
    Date of Patent: November 10, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Merger, Rolf Fischer, Hans Horler, Juergen Frank
  • Patent number: 5138096
    Abstract: 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: Grant
    Filed: November 16, 1990
    Date of Patent: August 11, 1992
    Assignee: Societe Francaise Hoechst
    Inventors: Alain Schouteeten, Jean-Michel Alarcon
  • Patent number: 5091566
    Abstract: 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: Grant
    Filed: July 3, 1989
    Date of Patent: February 25, 1992
    Assignee: Societe Francaise Hoechst
    Inventors: Alain Schouteeten, Yani Christidis
  • Patent number: 5091568
    Abstract: 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: Grant
    Filed: May 23, 1986
    Date of Patent: February 25, 1992
    Assignee: Mobay Corporation
    Inventor: Dennis E. Jackman
  • Patent number: 5068417
    Abstract: 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: Grant
    Filed: May 25, 1990
    Date of Patent: November 26, 1991
    Assignee: Chemie Linz Gesellschaft m.b.H.
    Inventors: Alexander Sajtos, Engelbert Kloimstein, Karl Hollinger, Lorenz Farnlettner
  • Patent number: 5053527
    Abstract: 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: Grant
    Filed: May 18, 1990
    Date of Patent: October 1, 1991
    Assignee: Societe Francaise Hoechst
    Inventors: Yani Christidis, Jean-Claude Vallejos
  • Patent number: 4973747
    Abstract: 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: Grant
    Filed: August 15, 1989
    Date of Patent: November 27, 1990
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Janak Singh, Richard H. Mueller
  • Patent number: 4950429
    Abstract: 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: Grant
    Filed: March 23, 1989
    Date of Patent: August 21, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Uwe Vagt, Rolf Fischer, Franz Merger, Hans-Martin Hutmacher