Polyoxy Acid Moiety Patents (Class 560/186)
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Patent number: 7321059Abstract: Compounds of formula (I): or salts or solvate thereof, wherein: n and N independently represent an integer 2 to 12; m1 and m2 independently represent an integer 1 to 15; and R1 and R2 independently represent —(CO)xC1-9 alkyl or —(CO)xC1-9 fluoroalkyl, which fluoroalkyl moiety contains at least 1 fluorine atom and not more than 3 consecutive perfluorocarbon atoms wherein x represents 0 or 1, as well as pharmaceutical formulations containing such compounds and processes for the manufacture of such compounds are disclosed. Intermediates of such compounds and processes for the manufacture of such intermediates are also disclosed.Type: GrantFiled: October 17, 2002Date of Patent: January 22, 2008Assignee: Glaxo Group LimitedInventors: Brian Edgar Looker, Christopher James Lunniss, Alison Judith Redgrave
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Patent number: 7169950Abstract: The invention relates to a method for producing monocarbonyl compounds or biscarbonyl compounds or hydroxyl compounds by ozonizing, unsaturated organic carbon compounds that, per molecule, have one or more olefinic or aromatic double bonds, which can be cleaved by ozone, and by subsequently processing the ozonization products.Type: GrantFiled: February 13, 2002Date of Patent: January 30, 2007Assignee: DSM Fine Chemicals Austria NFG GmbH & Co KGInventors: Alexander Sajtos, Engelbert Kloimstein, Curt Zimmermann
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Patent number: 7157255Abstract: A process is provided for the preparation of a compound of formula (1) wherein R and R? represent optionally substituted hydrocarbyl groups and X represents a hydrocarbyl linking group. The process comprises either the stereoselective reduction of the keto group in a dihydroxy keto precursor followed by selective esterification of a primary hydroxy, or selective esterification of a primary hydroxy of a dihydroxy keto precursor followed by stereoselective reduction of the keto group.Type: GrantFiled: May 1, 2001Date of Patent: January 2, 2007Assignee: AstraZeneca UK LimitedInventors: Andrew John Blacker, Christopher David Reeve, Robert Antony Holt
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Patent number: 7091375Abstract: The invention relates to a method for producing 2-keto-L-gulonic acid-C4–C10 alkyl ester by esterifying 2-keto-L-gulonic acid (KGS) with an unsaturated, branched or unbranched C4–C10 alcohol. The inventive method is characterized by the fact that an aqueous KGS solution is reacted with a C4–C10 alcohol up to an esterification degree of 20 to 70 percent in a pre-esterification process carried out under acidic catalysis conditions; and the obtained product is dehydrogenated with an unsaturated, branched or unbranched C4–C10 alcohol in a continuous rectification device, whereby the esterification reaction continues, n-butanol preferably being used as the alkyl alcohol. In a preferred embodiment, the aqueous KGS solution is concentrated up to or beyond the limit of solubility prior to the esterification process, preferably by catalyzing a homogeneous or heterogeneous catalyst, especially sulfonic acid, at temperatures of 50 to 120° C.Type: GrantFiled: November 7, 2003Date of Patent: August 15, 2006Assignee: BASF AktiengesellschaftInventors: Thomas Domschke, Martin Merger, Georg Grossmann, Tillmann Faust
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Patent number: 6956018Abstract: A polymerizable polyoxyalkylene monoalkyl ether derivative prepared by using a polyoxyalklene monoalkyl ether which gives, in gel permeation chromatography, a chromatogram which satisfies a relation expressed by an equation: S1/S0?0.Type: GrantFiled: July 13, 2004Date of Patent: October 18, 2005Assignee: Nof CorporationInventors: Akinori Itoh, Susumu Honda, Tatsuya Matsui, Yoshihiro Hayashi
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Patent number: 6867321Abstract: The present invention provides a method for producing compound (XIV) useful as an intermediate for pharmaceutical agents efficiently and economically on an industrial scale without using ozone oxidation and highly toxic reagent, and an intermediate used for this method. Particularly, the present invention provides a method for producing a compound having an absolute configuration represented by the formula (XV) and an enantiomer thereof without using a technique such as optical resolution and the like, and an intermediate used for this method. (1) Compound (XIII) as a starting material is led to compound (I), and after introducing a protecting group, subjected to reduction and cyclization to give compound (XIV). Particularly, compound (XIII) as a material is led to compound (I) via compound (XX) to produce compound (XIV).Type: GrantFiled: December 23, 2003Date of Patent: March 15, 2005Assignee: Sumitomo Chemical Company, LimitedInventors: Tetsuya Ikemoto, Dongguo Piao
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Publication number: 20040254392Abstract: A method for producing an optically active 3,5-dihydroxyhexanoic acid derivative by stereoselectively reducing an optically active 3-oxo-5-hydroxyhexanoic acid derivative is provided. The method, which requires neither an ultralow-temperature reactor, an incubator, nor protection of the 5-position hydroxy group, is simple and economical.Type: ApplicationFiled: April 13, 2004Publication date: December 16, 2004Inventors: Masanobu Sugawara, Kenji Inoue
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Patent number: 6825377Abstract: This invention relates to process for dihydroxylation of olefins using transition metal catalysts to obtain monofunctional, bifunctional, and/or polyfunctional 1,2-diols of the formula (I) R1R2C(OH)—C(OH)R3R4 (I) where R1 to R4 are defined herein, by reacting an olefin of the formula (II) R1R2C═CR3R4 (II) where R1 to R4 are defined as for formula (I), with molecular oxygen in the presence of an osmium, ruthenium, or manganese compound in water or a water-containing solvent mixture at a pH of from 7.5 to 13.Type: GrantFiled: October 19, 2001Date of Patent: November 30, 2004Assignee: Bayer AktiengesellschaftInventors: Matthias Beller, Christian Döbler, Gerald Mehltretter, Uta Sundermeier
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Patent number: 6812368Abstract: The invention relates to a novel process of diastereoselective hydrogenation of 1,3-hydroxyketones of formula (I) wherein R, R′ and R″ are as defined in claim 1 which is carried out in a solvent in the presence of a magnesium salt, a heterogeneous platinum catalyst and optionally an oxidant.Type: GrantFiled: July 2, 2003Date of Patent: November 2, 2004Assignee: Solvias AGInventors: Martin Studer, Stephan Burkhardt, Ulrike Nettekoven
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Publication number: 20040192770Abstract: The present invention relates to the preparation and biological activity of 3-deoxy-Dmyo-inositol ether lipid analogs as inhibitors of phosphatidylinositol-3-kinase signaling and cancer cell growth. The compounds of the present invention are useful as anti-tumor 5 agents which effectively inhibit the growth of mammalian cells.Type: ApplicationFiled: December 11, 2003Publication date: September 30, 2004Inventors: Alan P. Kozikowski, Lixin Qiao, Garth Powis
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Patent number: 6667340Abstract: The present invention relates to the preparation and biological activity of 3-deoxy-Dmyo-inositol ether lipid analogs as inhibitors of phosphatidylinositol-3-kinase signaling and cancer cell growth. The compounds of the present invention are useful as anti-tumor 5 agents which effectively inhibit the growth of mammalian cells.Type: GrantFiled: June 12, 2001Date of Patent: December 23, 2003Assignees: Arizona Board of Regents on behalf of the University of Arizona, Georgetown University School of MedicineInventors: Alan P. Kozikowski, Lixin Qiao, Garth Powis
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Patent number: 6649786Abstract: This invention provides a process to produce a hydroxyl group-containing ester-forming addition reaction product having an acid value of 20 mgKOH/g or less, which process is characterized in that 2,2-dimethylolalkanoic acid having 6 to 8 carbon atoms is melted, and is then mixed with alkanoic acid monoglycidylester having 8 to 24 carbon atoms so that an ester-forming addition reaction may occur. Thus obtained reaction product contains almost no undesirable high-molecular components, is quite excellent in reactivity and compatibility with a curing agent, and is useful for the manufacture of high-solids paint etc.Type: GrantFiled: August 21, 2002Date of Patent: November 18, 2003Assignee: Kansai Paint Co., Ltd.Inventor: Hisashi Isaka
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Patent number: 6620964Abstract: A description is given of a process for preparing dihydroxycarboxylic esters and of an overall process for preparing R-(+)-&agr;-lipoic acid.Type: GrantFiled: December 2, 2002Date of Patent: September 16, 2003Assignee: BASF AktiengesellschaftInventors: Martin Jochen Klatt, Markus Niebel, Melanie Erhardt
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Patent number: 6610892Abstract: The invention relates to a process for preparing 2,7-dimethyl-2,4,6-octatrienal monoacetals of the general formula I which comprises a) condensing an ester phosphonium salt of the general formula II or an ester phosphonate of the general formula III with an aldehyde of the formula IV in a Wittig or Wittig-Horner reaction to give an acetal ester of the general formula V b) reducing the ester of the formula V to give an acetal alcohol of the general formula VI and c) oxidizing the alcohol to 2,7-dimethyl-2,4,6-octatrienal monoacetals of the general formula I, where the substituents have the meaning defined in the description.Type: GrantFiled: March 12, 2002Date of Patent: August 26, 2003Assignee: BASF AktiengesellschaftInventors: Hansgeorg Ernst, Klaus Henrich
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Publication number: 20030158412Abstract: The invention relates to new protected 3,5-dihydroxy-2,2-dimethyl-valeroamides for the synthesis of epothilones and derivatives and process for the production and the use of the new compounds for the production of epothilones or epothilone derivatives.Type: ApplicationFiled: August 5, 2002Publication date: August 21, 2003Applicant: Schering AktiengesellschaftInventors: Jurgen Westermann, Johannes Platzek, Orlin Petrov
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Patent number: 6608230Abstract: A single-stage method for producing &agr;-hydroxy ethers by oxidizing olefinic substrates with organic hydroperoxides and opening the resultant oxirane ring by means of monovalent or polyvalent alcohols wherein a molybdenum compound in combination with a compound selected from the group consisting of boron trifluoride, aluminum oxides, 1,8-diazabicyclo-[5.4.0]-undec-7-ene or 1,4-diazabicyclo-[2.2.2]-octane, and mixtures thereof is used as a catalyst system.Type: GrantFiled: November 8, 2001Date of Patent: August 19, 2003Assignee: WE-DEA Aktiengesellschaft für Mineraloel und ChemieInventors: Mark Rüsch gen. Klaas, Siegfried Warwel, Hans-Martin Zillmann, Klaus Kwetkat
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Publication number: 20030134900Abstract: A process is provided for the preparation of a compound of formula (1) 1Type: ApplicationFiled: November 1, 2002Publication date: July 17, 2003Inventors: Andrew John Blacker, Christopher David Reeve, Robert Antony Holt
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Publication number: 20030109720Abstract: A description is given of a process for preparing dihydroxycarboxylic esters and of an overall process for preparing R-(+)-&agr;-lipoic acid.Type: ApplicationFiled: December 2, 2002Publication date: June 12, 2003Inventors: Martin Jochen Klatt, Markus Niebel, Melanie Erhardt
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Patent number: 6573400Abstract: C1-C10-alkyl 2-keto-L-gulonates are prepared by esterifying 2-keto-L-gulonic acid or diacetone-2-keto-L-gulonic acid with a C1-C10-alcohol in the presence of an acidic catalyst by a process in which the esterification is carried out in a liquid film on a hot surface with simultaneous removal of water.Type: GrantFiled: August 14, 2000Date of Patent: June 3, 2003Assignee: BASF AktiengesellschaftInventors: Andreas Böttcher, Wolfram Burst
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Publication number: 20030065208Abstract: Provided are a novel triphenyl phosphine derivative synthesized from a triphenylphosphine and a hydroxy-containing lactone; a palladium and a nickel complexes comprising the derivative as a ligand; and a process for preparing a biaryl derivative using the complex as a catalyst. A product can be easily separated from a catalyst or a phosphorus compound, and biaryl derivative can be synthesized in a higher yield, by using the complex of the present invention as a catalyst.Type: ApplicationFiled: September 13, 2002Publication date: April 3, 2003Inventor: Norio Miyaura
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Publication number: 20020161267Abstract: A polyoxyalkylene monoalkyl ether which gives, in gel permeation chromatography, a chromatogram which satisfies a relation expressed by an equation: S1/S0≦0.Type: ApplicationFiled: June 15, 1999Publication date: October 31, 2002Applicant: NOF CORPORATION, Tokyo, JapanInventors: AKINORI ITOH, SUSUMU HONDA, TATSUYA MATSUI, YOSHIHIRO HAYASHI
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Patent number: 6462206Abstract: Ketones and aldehydes are hydrogenated to the corresponding alcohol or alkyl group, using H2 gas as the stoichiometric reductant, and organometallic ruthenium complexes as the catalysts.Type: GrantFiled: June 20, 2001Date of Patent: October 8, 2002Assignees: E. I. du Pont de Nemours and Company, Brookhaven Science AssociatesInventors: R. Morris Bullock, Marcel Schlaf, Elisabeth M. Hauptman
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Patent number: 6452042Abstract: Substituted propenoates are prepared by eliminating an alcohol from a substituted malondialdehyde acetal, optionally in the presence of a homogeneous or heterogeneous catalyst.Type: GrantFiled: January 28, 2000Date of Patent: September 17, 2002Assignee: Creanova, Inc.Inventors: Frank Bauer, Chitoor Subramaniam
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Patent number: 6407265Abstract: Tin polyaalkanecarboxylates having the formula [(R1pR2qSn)rOs]t wherein R1 represents C1-C6 alkyl, branched or straight, substituted or not by one or more hydroxyl groups or halogen atoms, or a phenyl group, substituted or not by one or more hydroxyl groups or halogen atoms, R2 is carboxylic residue selected from (I), (II), (III) or (IV); and p, q, r, s and t have the following meanings: P=3, q=1, r=1, s=) and t=1, p=2, q=2, r=1, s=0, and t=1, p=2, q=1, r=2, s=1 and t=2, have anti-tumor activity.Type: GrantFiled: January 29, 2001Date of Patent: June 18, 2002Assignee: Pharmachemie B.V.Inventors: Marcel Gielen, Rudolph Willem, Monique Biesemans, Martine Kemmer, Dick de Vos
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Patent number: 6395920Abstract: A process directed to the preparation of 2-substituted and 2,2-disubstituted acetals of malondialdehyde from ortho formates and substituted vinyl ethers in the presence of an acidic catalyst.Type: GrantFiled: January 28, 2000Date of Patent: May 28, 2002Assignee: Creanova, Inc.Inventors: Frank Bauer, Chitoor Subramaniam
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Patent number: 6380439Abstract: A single-stage method for producing &agr;-hydroxy ethers by oxidizing olefinic substrates with organic hydroperoxides and opening the resultant oxirane ring by means of monovalent or polyvalent alcohols wherein a molybdenum compound in combination with a compound selected from the group consisting of boron trifluoride, aluminum oxides, 1,8-diazabicyclo-[5.4.0]-undec-7-ene or 1,4-diazabicyclo-[2.2.2]-octane, and mixtures thereof is used as a catalyst system.Type: GrantFiled: January 25, 2000Date of Patent: April 30, 2002Assignee: RWE-DEA Aktiengesellschaft fur Mineraloel und ChemieInventors: Mark Rüsch gen. Klaas, Siegfried Warwel, Hans-Martin Zillmann, Klaus Kwetkat
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Patent number: 6359168Abstract: Compounds of formula (I) in which R=H or CH3 and n is a whole number from 1 to 4. These compounds are useful as refreshing agents in various compositions, articles or products from flavor manufacture or perfumery.Type: GrantFiled: May 24, 2000Date of Patent: March 19, 2002Assignee: Firmenich SAInventors: Eric Frerot, Nicole Van Beem
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Patent number: 6329542Abstract: The glycinamide of the formula is reacted with the dioxolane of the formula wherein L is a leaving group such as iodo, bromo, alkylsulfonyloxy, or arylsulfonyloxy to give the dioxolane of the formula Treating the dioxolane of formula III under aqueous refluxing conditions followed by exchanging the dioxolane acetal with a dimethoxy acetal and introduction of the methyl ester gives (S)-2-amino-6,6-dimethoxyhexanoic acid, methyl ester which is an intermediate in the preparation of the dual inhibitor [4S-[4&agr;(R*),7&agr;,10a&bgr;]]-octahydro-4-[(2-mercapto-1-oxo-3-phenylpropyl)-amino]-5-oxo-7H-pyrido[2,1-b][1,3]thiazepine-7-carboxylic acid. Also disclosed are storage stable salts of (S)-2-amino-6, 6-dimethoxyhexanoic acid, methyl ester.Type: GrantFiled: October 12, 2000Date of Patent: December 11, 2001Assignee: Bristol-Myers Squibb Co.Inventors: Jollie D. Godfrey, Jr., David R. Kronenthal, Mark D. Schwinden, Sushil K. Srivastava, Keith Ramig, John J. Venit, Paul A. Jass, Saibaba Racha, John L. Dillon, Jr., Nachimuthu Soundararajan, Gerald L. Powers, Atul S. Kotnis
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Patent number: 6297396Abstract: A method for synthesizing alkyl gallates. Gallic acid and an alkyl alcohol of the order of the desired gallate are heated in a reaction vessel in the presence of a catalyst such as sulfuric acid or para-toluene sulfonic acid. Water is generated, forming an azeotrope with the alkyl alcohol. Distillation or Soxhlet extraction using a drying agent removes the formed water. Upon completion of the reaction, the reaction mixture is added while stirring to an alkane solvent and cooled to produce crystals of the desired alkyl gallate. The crystals may be further recrystallized and washed to improve their purity.Type: GrantFiled: December 30, 1999Date of Patent: October 2, 2001Inventors: Benedikt Sas, Bruno Coppens, Johan Van hemel
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Patent number: 6288272Abstract: The present invention relates to a continuous process for preparing optically pure (S)-3,4-dihydroxybutyric acid derivatives expressed by the following Formula 1 and more particularly, to the continuous process which enables preparing optically pure (S)-3,4-dihydroxybutyric acid derivatives economically in large quantities, by: (a) Preparing &agr;-(1,4) linked oligosaccharide having adequate sugar distribution by reacting amylopectin which is easily available from natural product with enzyme under a specific condition; and (b) Performing oxidatioin by running basic anion exchange resin with an oxidant to give (S)-3,4-dihydroxybutyric acid-anion exchange resin complex, dissociating the (S)-3,4-dihydroxybutyric acid from anion exchange resin complex and esterification sequentially under a specific condition. wherein Represents linear or branched alkyl group with 1˜5 carbon atoms.Type: GrantFiled: July 23, 1999Date of Patent: September 11, 2001Assignee: Samsung Fine Chemicals Co., Ltd.Inventors: Kyoung Rok Roh, Jongpil Chun, Yik-haeng Cho, Young Mi Park, Hosung Yu, Dae Il Hwang
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Patent number: 6184376Abstract: Methods and novel intermediates of the formula: wherein R6 and R7 are lower alkyl or benzyl or R6 and R7 taken together are —CH2CH2—, —CH2CH2CH2— or —CH2CH2CH2CH2CH2—, R8 is C1-C21 alkyl or a C2-C21 monounsaturated alkenyl, which may optionally be substituted with substitution substituents independently selected from the group consisting of hydroxy, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkoxy C1-C6 alkyl, C1-C6 alkanoyl, amino, halo, cyano, azido, oxo, mercapto and nitro, and R9 is an alcohol protecting group. The intermediates are useful for the preparation of acyclic nucleoside derivatives of the formula: where one of R1 and R2 is an amino acid acyl group and the other of R1 and R2 is a —C(O)C3-C21 saturated or monounsaturated, optionally substituted alkyl and R3 is OH or H; or a pharmaceutically acceptable salt thereof.Type: GrantFiled: August 6, 1998Date of Patent: February 6, 2001Assignee: Mediver ABInventors: M. Robert Leanna, Steven M. Hannick, Michael Rasmussen, Jien-Heh J. Tien, Lakshmi Bhagavatula, Pulla Reddy Singam, Bradley D. Gates, Lawrence Kolaczkowski, Ramesh R. Patel, Greg Wayne, Greg Lannoye, Weijiang Zhang, Zhenping Tian, Kirill A. Lukin, Bikshandarkoil A. Narayanan, David A. Riley, Howard Morton, Sou-Jen Chang, Cynthia B. Curty, Daniel Plata, John Bellettini, Bhadra Shelat, Tiffany Spitz, Cheng-Xi Yang
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Patent number: 6043389Abstract: This invention relates to compositions for and methods of treating, preventing or ameliorating cancer and other proliferative diseases as well as methods of inducing wound healing, treating cutaneous ulcers, treating gastrointestinal disorders, treating blood disorders such as anemias, immunomodulation, enhancing recombinant gene expression, treating insulin-dedendent patients, treating cystic fibrosis patients, inhibiting telomerase activity, treating virus-associated tumors, especially EBV-associated tumors, augmenting expression of tumor suppressor genes, inducing tolerance to antigens, or treating, preventing or ameliorating protozoan infection or inhibiting histone deacetylase in cells. The compositions of the invention are to and the methods of the invention use hydroxy and ether-containing oxyalkylene esters.Type: GrantFiled: March 11, 1997Date of Patent: March 28, 2000Assignees: Mor Research Applications, Ltd., Beacon Laboratories, Inc., Bar-Ilan UniversityInventors: Abraham Nudelman, Ada Rephaeli
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Patent number: 6037489Abstract: A method for purifying glyoxylates includes (1) a coarse distillation process in which a crude glyoxylate in which water coexists is, in a film form, continuously subjected to coarse distillation, and (2) an azeotropic dehydration process in which the crude glyoxylate purified through the coarse distillation process is subjected to azeotropic dehydration in the presence of an azeotropic agent such as propyl acetate. By this method, high-purity glyoxylates can be efficiently and easily obtained at lower costs.Type: GrantFiled: April 10, 1998Date of Patent: March 14, 2000Assignee: Nippon Shokubai Co., Ltd.Inventors: Hideyuki Baba, Satoru Miura, Masanori Nonoguchi, Noboru Saito
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Patent number: 5997610Abstract: The invention concerns amphiphilic compounds of general formula (I) ##STR1## with at least two hydrophilic and at least two hydrophobic groups based on diacarboxylic acid diamides. The amphiphilic compounds according to the invention are mostly surface-active and are suitable for use as emulsifiers, demulsifiers, detergents, dispergents and hydrotropic agents in industry and households, for example, in the treatment of metals, ore processing, surface finishing, washing, cleaning, cosmetics, medicine and food processing and preparation.Type: GrantFiled: August 18, 1997Date of Patent: December 7, 1999Assignee: Huels AktiengesellschaftInventors: Klaus Kwetkat, Wulf Ruback
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Patent number: 5965119Abstract: The present invention is directed to double prodrugs containing polymeric-based transport forms. These polymeric prodrugs are preferably of the formula: ##STR1## wherein: B is a leaving group or a residue of an amine-containing target moiety;G is ##STR2## or CH.sub.2 ; Y.sub.1-2 are independently O or S;M is X or Q; where X is an electron withdrawing group and Q is a moiety containing a free electron pair positioned three to six atoms from C(.dbd.Y.sub.2);R.sub.1, R.sub.4, R.sub.7, R.sub.8, R.sub.9, R.sub.10 and R.sub.13 are independently selected from the group consisting of hydrogen, C.sub.1-6 alkyls, C.sub.3-12 branched alkyls, C.sub.3-8 cycloalkyls, C.sub.1-6 substituted alkyls, C.sub.3-8 substituted cycloalkyls, aryls, substituted aryls, aralkyls, C.sub.1-6 heteroalkyls, substituted C.sub.1-6 heteroalkyls;R.sub.2, R.sub.3, R.sub.5 and R.sub.6 are independently selected from the group consisting of hydrogen, C.sub.1-6 alkyls, C.sub.1-6 alkoxy, phenoxy, C.sub.1-8 heteroalkyls, C.sub.Type: GrantFiled: December 30, 1997Date of Patent: October 12, 1999Assignee: Enzon, Inc.Inventors: Richard B. Greenwald, Yun H. Choe
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Patent number: 5939580Abstract: Process for preparing glyoxylic esters or their hydrates in which a water-soluble salt of a maleic or fumaric monoester or a mixture thereof is reacted with ozone in aqueous solution at temperatures of from 0 to 50.degree. C., and the corresponding glyoxylic ester or its hydrate is isolated from the resulting reaction mixture.Type: GrantFiled: November 21, 1997Date of Patent: August 17, 1999Assignee: DSM Fine Chemicals Austria GmbHInventors: Engelbert Kloimstein, Wolfram Hendel, Klaus Reiter, Christian Burger, Antonia Praus, Karl Heinz Giselbrecht, Eduard Perndorfer
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Patent number: 5928393Abstract: A fuel additive which comprises a compound selected from a novel amine, oxygen-containing and nitrogen-containing compounds having selected structures. The inventive additive when blended with a gasoline serves to suppress sludge or deposits in fuel intake systems or combustion chambers for example of an automobile engine.Type: GrantFiled: July 17, 1997Date of Patent: July 27, 1999Assignee: Nippon Oil Co., Ltd.Inventors: Noboru Ishida, Katsuhiko Haji, Masaki Nagao, Toru Yoshii
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Patent number: 5902895Abstract: A method for the continuous production of esters of thermally unstable acids by the esterification, with or without a catalyst, of the acids with alcohols is provided. The method involves esterification at temperatures of approximately 80.degree. C. to approximately 130.degree. C., essentially in a single reaction zone, to which the acid and an excess of alcohol are continuously supplied and from which a vapor stream containing alcohol and water produced by the esterification reaction are removed, while at the same time removing an ester-rich liquid reaction mixture from the single reaction zone, from which the ester is obtained.Type: GrantFiled: May 5, 1997Date of Patent: May 11, 1999Assignee: Huels AktiengesellschaftInventor: Manfred Kaufhold
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Patent number: 5877334Abstract: A solid phase synthesis method and intermediates useful in the process are disclosed for the preparation of diamino diol and diamino alcohol inhibitors of HIV protease.Type: GrantFiled: July 23, 1996Date of Patent: March 2, 1999Assignee: Abbott LaboratoriesInventor: Gary T. Wang
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Patent number: 5866606Abstract: A nutritional formulation containing an amount of diacetyltartaric acid esters of mono- and diglycerides effective to inhibit the infectious activity of pathogenic microorganisms is provided. A process of inhibiting the infectious activity of pathogenic microorganisms including the step of feeding the nutritional composition to a subject is also provided.Type: GrantFiled: July 2, 1997Date of Patent: February 2, 1999Assignee: Abbott LaboratoriesInventors: Joseph Schaller, Steven N. Anderson, Terry Bruce Mazer, Milo Duane Hilty, Melinda Guzman-Harty, Theresa Siu-Ling Wai Lee, Tammy Marie Bowman, Jill M. Lamm, Jin-Zhou Liu
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Patent number: 5808107Abstract: Preparation of 4-hydroxy substituted butyrolactones is described. A process for the preparation of 3-hydroxybutyrolactone, 1,2,4-trihydroxybutane and 3,4-dihydroxy acid methyl ester from malic acid is particularly described. The preparation of 4-hydroxymethyl-4-hydroxybutyric acid -1-methyl ester and 4-hydroxymethyl butyrolactone is particularly described. The compounds are intermediates to various pharmaceutical and agricultural products.Type: GrantFiled: October 31, 1997Date of Patent: September 15, 1998Assignee: Board of Trustees operating Michigan State UniversityInventor: Rawle I. Hollingsworth
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Patent number: 5792876Abstract: A process is described for producing acetals comprising reacting an aldehyde or a ketone with an alcohol in the presence of a titanium compound having an acetylacetone as a ligand, or in the presence of a compound selected from the group consisting of stannous chloride dihydrate, cerium chloride hexahydrate and bismuth chloride. The process can be used in the synthesis of unstable acetals or when water exists in the reaction mixture, and therefore the process can be used for a wide variety of applications.Type: GrantFiled: November 6, 1996Date of Patent: August 11, 1998Assignee: Kuraray Co., Ltd.Inventors: Hideharu Iwasaki, Masahiko Kitayama, Takashi Onishi
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Patent number: 5777150Abstract: A compound of the formula (I) or its pharmaceutically acceptable salt or ester: ##STR1## wherein each of ##STR2## which are the same or different, is an aryl group or a heteroaromatic ring group; A is a C.sub.3-8 linear saturated or unsaturated aliphatic hydrocarbon group which may have substituent(s) selected from the group consisting of a lower alkyl group, a hydroxyl group, a lower alkoxy group, a carboxyl group, an aryl group and an aralkyl group; Q is a single bond or a group of the formula --CO--O--, --O--CO--, --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, --OCH.sub.2 --, --SCH.sub.2 --, --CH.sub.2 O-- or --CH.sub.2 S--; each of R.sup.1, R.sup.2, R.sup.3 and R.sup.4 which are the same or different, is a hydrogen atom, a halogen atom, a lower alkyl group, a hydroxyl group, a lower alkoxy group, or an aryl or heteroaromatic ring group which may have substituent(s) selected from the group consisting of a halogen atom, a lower alkyl group and a lower alkoxy group; each of R.sup.5, R.sup.6 and R.sup.Type: GrantFiled: August 13, 1996Date of Patent: July 7, 1998Assignee: Banyu Pharmaceutical Co., Ltd.Inventors: Takashi Nomoto, Masahiro Hayashi, Jun Shibata, Yoshikazu Iwasawa, Morihiro Mitsuya, Yoshiaki Iida, Katsumasa Nonoshita, Yasufumi Nagata
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Patent number: 5767277Abstract: An optically active .beta.-aminoalkoxyborane complex of the formula (I): ##STR1## wherein R.sup.1 is C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.7 -C.sub.11 aralkyl or C.sub.6 -C.sub.10 aryl, R.sup.2 is hydrogen, C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.7 cycloalkyl or C.sub.7 -C.sub.11 aralkyl, or R.sup.1 and R.sup.2 together form (CH.sub.2).sub.n wherein n is 3 or 4, and Ar is naphthyl, anthryl or phenanthryl, which may be substituted by from 1 to 3 substituents selected from the group consisting of halogen, nitro, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 alkynyl, C.sub.7 -C.sub.11 aralkyl, C.sub.6 -C.sub.10 aryl, C.sub.1 -C.sub.6 alkoxy and styrene polymer substituents.Type: GrantFiled: January 7, 1997Date of Patent: June 16, 1998Assignee: Nissan Chemical Industries Ltd.Inventors: Hiroshi Kashihara, Mikio Suzuki, Yoshio Ohara
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Patent number: 5744634Abstract: A process for the manufacture of methyl or ethyl 2-keto-L-gulonate by esterifying 2-keto-L-gulonic acid with methanol or ethanol continuously in the presence of an acidic ion exchanger in the temperature range between room temperature and about 80.degree. C. and with average residence times between about 10 and about 120 minutes and with superficial velocities of about 0.5 m/h to about 7.5 m/h. The esterification is advantageously carried out under slight over-pressure. The thus-manufactured esters are important intermediates for the synthesis of vitamin C and the respective esterification product can be converted directly into vitamin C by lactonization.Type: GrantFiled: May 19, 1997Date of Patent: April 28, 1998Assignee: Roche Vitamins Inc.Inventor: Joachim Veits
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Patent number: 5693251Abstract: An optically active phenol useful in the preparation of liquid crystalline compounds which is represented by the formula (V): ##STR1## wherein R.sub.2 represents an alkyl or alkoxyalkyl group having 1 to 20 carbon atoms optionally substituted by halogen atoms; Z' represents ##STR2## wherein q represents a number of 1 to 5 and * indicates asymmetric carbon atom; l represents a number of 2; t represents a number of 1 to 5; s represents a number of 0 or 1.Type: GrantFiled: November 23, 1994Date of Patent: December 2, 1997Assignee: Sumitomo Chemical Company, LimitedInventors: Takayuki Higashii, Isao Kurimoto, Shoji Toda, Masayoshi Minai, Takeshi Tani, Chizu Kawakami, Koichi Fujisawa
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Patent number: 5677432Abstract: A compound useful for forming immunoconjugates used in the detection of organophosphate pesticides is provided. The compound has the formula ##STR1## wherein X is selected from the group consisting of R--O--, R--S-- and R--NH--, where R is an optionally substituted aromatic or heterocyclic group, or an optionally substituted alkyl or alkenyl group;Y is O or S;R.sup.1 is H or alkyl; andR.sup.2 is a group of the formula --(CH.sub.2).sub.n -- wherein n is an integer of from 1 to 10, or branched chain alkylene, or a group of the formula R.sup.3 --O--R.sup.4 wherein R.sup.3 and R.sup.4 are both or straight or branched chain alkylene;or a salt or ester thereof.Type: GrantFiled: August 19, 1994Date of Patent: October 14, 1997Assignee: The Horticulture and Food Research Institute of New Zealand LimitedInventors: William Thomas Jones, Hans Wynberg, Wolter Ten Hoeve
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Patent number: 5663348Abstract: An optically active .beta.-aminoalkoxyborane complex of the formula (I): ##STR1## wherein R.sup.1 is C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.7 -C.sub.11 aralkyl or C.sub.6 -C.sub.10 aryl, R.sup.2 is hydrogen, C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.7 cycloalkyl or C.sub.7 -C.sub.11 aralkyl, or R.sup.1 and R.sup.2 together form (CH.sub.2).sub.n wherein n is 3 or 4, and Ar is naphthyl, anthryl or phenanthryl, which may be substituted by from 1 to 3 substituents selected from the group consisting of halogen, nitro, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 alkynyl, C.sub.7 -C.sub.11 aralkyl, C.sub.6 -C.sub.10 aryl, C.sub.1 -C.sub.6 alkoxy and styrene polymer substituents.Type: GrantFiled: July 19, 1995Date of Patent: September 2, 1997Assignee: Nissan Chemical Industries Ltd.Inventors: Hiroshi Kashihara, Mikio Suzuki, Yoshio Ohara
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Patent number: 5523479Abstract: A process for the preparation of carboxylic acids which contain ether groups by the catalytically accelerated addition of alcoholic hydroxyl groups from mono- or polyhydric alcohols to tertiary-alkyl esters of .alpha.,.beta.-unsaturated carboxylic acids, and followed with acid hydrolysis of the tertiary-alkyl .beta.-ethercarboxylate obtained as intermediates in this way.Type: GrantFiled: April 20, 1994Date of Patent: June 4, 1996Assignee: Bayer AktiengesellschaftInventors: Josef Sanders, Klaus Konig
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Patent number: RE38324Abstract: Preparation of 4-hydroxy substituted butyrolactones is described. A process for the preparation of 3-hydroxybutyrolactone, 1.2.4-trihydroxybutane and 3,4-dihydroxy acid methyl ester from malic acid is particularly described. The preparation of 4-hydroxymethyl-4-hydroxybutyric acid -1-methyl ester and 4-hydroxymethyl butyrolactone is particularly described. The compounds are intermediates to various pharmaceutical and agricultural products.Type: GrantFiled: March 28, 2002Date of Patent: November 18, 2003Assignee: Board of Trustees of Michigan State UniversityInventor: Rawle I. Hollingworth