Polyoxy Patents (Class 562/587)
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Publication number: 20090312555Abstract: There is provides a process for the preparation of a compound of formula (7): wherein R is an optionally substituted hydrocarbyl group or an optionally substituted heterocyclic group; provides that R is not a compound of Formula (a): wherein Ra represents an alkyl group, such as a C1-16 alkyl group, and preferably an isopropyl group; Rb represents an aryl group, preferably a 4-fluorophenyl group; Rc represents hydrogen, a protecting group or an alkyl group, such as a C1-16 alkyl group, and preferably a methyl group; and Rd represents hydrogen, a protecting group or a SO2Re group where Re is an alkyl group, such as a C1-16 alkyl group, and preferably a methyl group.Type: ApplicationFiled: November 28, 2005Publication date: December 17, 2009Applicant: NPIL PHARMACEUTICAL (UK) LIMITEDInventors: David John Moody, Jonathan William Wiffen
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Publication number: 20090281335Abstract: The present invention provides compound(s) selected from the group of compounds represented by structural Formula (I): wherein X, Y and R1 are as described herein, use of such compounds as anaerobic cure accelerators, and compostions including such compounds.Type: ApplicationFiled: May 7, 2008Publication date: November 12, 2009Applicant: HENKEL CORPORATIONInventors: Andrew Messana, Anthony F. Jacobine, Steven Thomas Nakos, David M. Glaser
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Publication number: 20090233880Abstract: A composition which can significantly accelerate equol production is provided. When formulated in a pharmaceutical preparation or a food or drink, this composition exerts effects of preventing a vascular disease by the cholesterol lowering function, preventing breast cancer or prostatic cancer, and preventing and/or treating osteoporosis. Also, when formulated in a feed or a pet food, the bone density is enhanced, so that it exerts effects to prevent weak legs of a pig, to strengthen egg shell of a laying hen, to prevent osteoporosis in a dog etc., and the like. It is a composition which comprises lactobionic acid, a salt of lactobionic acid or lactobionolactone as an active ingredient and a food or drink, a feed, a pet food or a pharmaceutical preparation, which contains the composition, and have effects to prevent and treat osteoporosis, an function to increase bone density, an effect to prevent breast cancer or prostatic cancer, and a cholesterol lowering function.Type: ApplicationFiled: June 15, 2007Publication date: September 17, 2009Inventors: Kenichi Oe, Takashi Kimura
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Publication number: 20090156673Abstract: (Neuro)protectin D1 (1OR,17S-dihydroxy-docosa-4Z,7Z,11E,13E,15Z,19Z-hexaenoic acid) and 15,16-dehydro-PD1 and their derivatives are useful in the treatment of airway inflammation, especially asthma.Type: ApplicationFiled: October 3, 2006Publication date: June 18, 2009Applicant: The Brigham and Women's Hospital, Inc. Corporate Sponsored Research & LicensingInventors: Charles N. Serhan, Nicos A. Petasis, Bruce D. Levy
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Patent number: 7504532Abstract: Synthesis methods for the preparation of intermediates which are suitable for the preparation of statin derivatives, and especially to synthesis methods for the intermediate of formula (VI) wherein Ra? and Rc? are each independently of the other hydrogen or hydroxy-protecting group, or together are a bridging hydroxy-protecting group; and Rb is a carboxy-protecting group.Type: GrantFiled: November 16, 2007Date of Patent: March 17, 2009Assignee: Teva Pharmaceutical Industries Ltd.Inventors: Reinhold Öhrlein, Gabriele Baisch, Hans Jörg Kirner, Stephan Burkhardt, Martin Studer, Frank Bienewald
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Publication number: 20080319218Abstract: Provided are compounds and a process for preparing benzyl pentahydroxyhexylcarbamoylundecanoate (I) and uses thereof.Type: ApplicationFiled: June 22, 2007Publication date: December 25, 2008Inventors: Andreas Haubrich, Bernd Junker, Javier Manero, Theo Wollmann
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Publication number: 20080214387Abstract: Process for modifying catalysts via the deposition of carbon containing residues in the presence of one or more solvents, where the gas phase over the catalyst treatment solution during the treatment is air or an inert gas, and/or the liquid phase contains a templating agent and/or base. The modified catalyst can be used for stereo-, chemo- and regioselective transformations of organic compounds.Type: ApplicationFiled: November 12, 2004Publication date: September 4, 2008Inventors: Daniel Ostgard, Virginie Duprez, Roberta Olindo, Stefan Roder, Monika Berweiler
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Publication number: 20080188651Abstract: Dictyostatin and its analogs show great promise as new anticancer agents. The present invention provides dictyostatin analogs, synthetic intermediates for the synthesis of dictyostatin analogs, and synthetic methods for the synthesis of such analogs and intermediates.Type: ApplicationFiled: January 2, 2008Publication date: August 7, 2008Inventors: Dennis P. Curran, Youseung Shin, Jean-Hugues Fournier, John Mancuso, Billy W. Day, Arndt Bruckner, Yoshikazu Fukui
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Patent number: 7393812Abstract: Methylidene mevalonic acid, a material isolated from a fungal extract, and its primary alcohol and carboxylic acid derivatives, are potent herbicides demonstrating a broad spectrum of weed control. These materials are useful for weed control and for the cultivation of organically grown crops.Type: GrantFiled: November 18, 2005Date of Patent: July 1, 2008Assignee: Dow AgroSciences LLCInventors: Ben Clifford Gerwick, III, Paul Richard Graupner, Stephen Craig Fields, Paul Richard Schmitzer, William Kirkland Brewster
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Publication number: 20080153889Abstract: Derivative compounds of 11-nonyloxy-undec-8(Z)-eonic acid that mimic epoxide metabolites are provided. Also provided are compositions comprising a therapeutically effective amount of the derivative compounds.Type: ApplicationFiled: February 29, 2008Publication date: June 26, 2008Inventors: John D. Imig, John R. Falck
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Publication number: 20080091047Abstract: The present invention relates to a high yield process to prepare high purity crystalline glycolic acid using a multi-loop crystallization process characterized by high liquid and/or solid recycle, said process suitable for large scale purification and producing high purity glycolic acid with low diglycolic acid content.Type: ApplicationFiled: October 11, 2007Publication date: April 17, 2008Inventors: F. Glenn Gallagher, Rod K. Hackman, Daniel Albert Green
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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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Publication number: 20080004469Abstract: The object is to provide a method and apparatus for producing a polyhydroxy carboxylic acid according to which an annular diner can be efficiently obtained in the production of polyhydroxy carboxylic acid which is small in distribution breadth of molecular weight in depolymerization and opening ring polymerization steps. There are provided a depolymerization device 11 which depolymerizes hydroxy carboxylic acid or a polycondensate thereof into an annular dimer, a upper distillation column 13 which condenses the annular dimer vaporized in the depolymerization device 11, and lower distillation column 12 which refluxes the annular dimer and is provided between the depolymerization device 11 and the upper distillation column 13, said depolymerization device 11 having a polycondensate feed opening 54 and an annular dimer discharge opening 55 which are provided at a casing 50, a liquid film being formed inside the casing 50 and heated by a heating part.Type: ApplicationFiled: June 28, 2007Publication date: January 3, 2008Inventors: Masayuki KAMIKAWA, Toshiaki Matsuo, Kenichiro Oka, Naruyasu Okamoto, Ryuji Kaziya
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Process for the solvent-free preparation of ethercarboxylic acids having a low residual salt content
Patent number: 7208118Abstract: The invention provides a process for preparing compounds of the formula (1) where A is C2- to C4-alkylene, B is C1- to C4-alkylene, n is a number from 1 to 100, and R is C1- to C30-alkyl, C2- to C30-alkenyl, or C6— to C30-aryl, by a) alkylating a basic mixture of oxoalkylated alcohols of the formula R—O-(-A-O—)n—H and alkoxides thereof with a C2- to C5-chlorocarboxylic acid in the absence of a solvent, b) converting the thus obtained ethercarboxylic acid salt to the free ethercarboxylic acid by adding an acid, the pH being adjusted to 3 or less, c) freeing the thus obtained ethercarboxylic acid, without washing, of water present down to a residual water content of <0.30% by distillation under reduced pressure, and d) removing the precipitated metal salts by filtration, so that the resulting product has a residual salt content of <0.2%.Type: GrantFiled: March 4, 2005Date of Patent: April 24, 2007Assignee: Clariant Produkte (Deutschland) GmbHInventors: Dirk Leinweber, Uwe Dahlmann, Rainer Kupfer -
Patent number: 7186856Abstract: Processes for preparing carboxylic acids and derivatives thereof in which an ammonium salt of the carboxylic acid is heated in the presence of an organic reagent to split the salt and form the acid or, where the organic reagent is an esterifying agent, the corresponding ester. Both the acid and the ester may be dehydrated to form unsaturated counterparts.Type: GrantFiled: May 7, 2002Date of Patent: March 6, 2007Assignee: Cargill, IncorporatedInventors: Xiangsheng Meng, Paraskevas Tsobanakis, Jeffrey Malsam, Timothy W. Abraham
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Patent number: 7179939Abstract: A process is provided for preparing a sodium ferric gluconate complex, substantially free of excipients, for providing a sodium ferric gluconate complex co-precipitated with sucrose, and for providing sodium ferric gluconate complexes in aqueous solution.Type: GrantFiled: July 12, 2004Date of Patent: February 20, 2007Assignee: Navinta LLCInventors: Jagadeesh Babu Rangisetty, Christopher Benny Newton
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Patent number: 7153999Abstract: In the method of the present invention, a dimethylolcarboxylic acid is produced by reacting a trimethylolalkane and formaldehyde to prepare a cyclic formal having a formal protecting group, followed by the oxidation of the cyclic formal by using nitric acid as an oxidizing agent to prepare a cyclic carboxylic acid which is then subjected to cleavage to remove the formal protecting group. The formal protecting group protects two of the methylol groups against the oxidation to enable the production of the dimethylolcarboxylic acid with a high selectivity.Type: GrantFiled: January 22, 2002Date of Patent: December 26, 2006Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Toshio Watanabe, Atsushi Iwamoto, Soemu Miyashita, Masafumi Watanabe
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Patent number: 7141537Abstract: The present invention provides the use of a fluorinated polyether composition as a surfactant, said fluorinated polyether composition comprising a mixture of fluorinated polyethers of the formula: (Rf)n—Xw—Z ??(I) wherein n is 1 or 2, w is 0 or 1, X is a divalent or trivalent organic linking group, Z is a polar group selected from the group consisting of an acid group or a salt thereof, an ammonium group, an amine-oxide group and an amphoteric group, and Rf represents a perfluorinated polyether group of the formula: CF3CF2CF2—O—[CF(CF3)CF2O]k—CF(CF3)— wherein k is at least 1; said mixture of fluorinated polyethers having a weight average molecular weight between 750 g/mol and 5000 g/mol and the amount of perfluorinated polyether groups in said mixture where k is 2 or less, is not more than 10% by weight of the total amount of perfluorinated polyether groups in said mixture.Type: GrantFiled: October 30, 2003Date of Patent: November 28, 2006Assignee: 3M Innovative Properties CompanyInventors: Frans A. Audenaert, Rudolf J. Dams, Lian S. Tan
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Patent number: 7008636Abstract: This invention provides compounds of Formula I having the structure or a pharmaceutically acceptable salt thereof, which are useful in treating metabolic disorders related to insulin resistance or hyperglycemia.Type: GrantFiled: May 11, 2004Date of Patent: March 7, 2006Assignee: WyethInventors: John A. Butera, Craig E. Caufield, Russell F. Graceffa, Alexander Greenfield, Eric G. Gundersen, Lisa Marie Havran, Alan H. Katz, Joseph R. Lennox, Scott C. Mayer, Robert E. McDevitt
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Patent number: 6965029Abstract: The invention relates to a process for the preparation of compounds of the general formula I in which R1 represents a C1-C20-alkyl group, a C3-C12-cycloalkyl group, a C7-C12-aralkyl group or a mono- or bi-nuclear aryl group, in which a ketone of formula II wherein R1 is as defined above, is subjected to asymmetric hydrogenation.Type: GrantFiled: July 17, 2001Date of Patent: November 15, 2005Assignee: Viatris GmbH & Co. KGInventor: Rainer Gewald
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Patent number: 6951956Abstract: Crystalline polyglycolic acid wherein a difference between the melting point Tm and the crystallization temperature Tc2 is not lower than 35° C., and a difference between the crystallization temperature Tc1 and the glass transition temperature Tg is not lower than 40° C. A production process of polyglycolic acid modified in crystallinity, comprising applying heat history to crystalline polyglycolic acid at a temperature of not lower than (the melting point Tm of the crystalline polyglycolic acid+38° C.). A polyglycolic acid composition comprising crystalline polyglycolic acid and a heat stabilizer, wherein a difference (T2?T1) between the temperature T2 at 3%-weight loss on heating of the polyglycolic acid composition and the temperature T1 at 3%-weight loss on heating of the crystalline polyglycolic acid is not lower than 5° C.Type: GrantFiled: April 25, 2002Date of Patent: October 4, 2005Inventors: Kazuyuki Yamane, Hiromitsu Miura, Toshihiko Ono, Junji Nakajima, Daisuki Itoh
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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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Patent number: 6844467Abstract: Glyceric acid compounds of the formula (I) R1R2C(OH)—CR3(OH)—COOX??(I) where R1, R2 and R3 are independently hydrogen, C1-12-alkyl, C6-12-aryl, C7-13-alkaryl or C7-13-aralkyl and X is hydrogen, an alkali metal, an alkaline earth metal/2 or NH4, are prepared by saponification of glycidic acid compounds of the formula (II) where Y is NH2 or OR4 in which R4 is C1-12-alkyl or C7-13-aralkyl, with ring-opening addition of water onto the epoxide ring. Preferably, Y is NH2 and the glycidamide of the formula (II) which is used is prepared by reacting acrylonitriles of the formula (III) R1R2C?CR3CN??(III) with hydrogen peroxide.Type: GrantFiled: March 5, 2002Date of Patent: January 18, 2005Assignee: BASF AktiengesellschaftInventors: Georg Heinrich Grosch, Werner Bochnitschek, Peter Neumann, Arend Jouke Kingma
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Publication number: 20040259946Abstract: In one aspect, the invention provides a process for the preparation of compounds of Formula I 1Type: ApplicationFiled: August 12, 2004Publication date: December 23, 2004Inventors: Tom Thomas Puthiaparampil, Acharya Poornaprajna, Chandrashekar Aswathanarayanappa, Madhavan Sridharan, Sambasivam Ganesh
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Patent number: 6723836Abstract: To provide low odor polyoxyalkylene polyol, a process for producing the same, and a low odor urethane prepolymer and a low odor urethane composition using the same as a raw material. The low odor polyoxyalkylene polyol comprising polyoxyalkylene polyol with amine added thereto, the amine having at least one amino group represented by the following formula (1): is provided, wherein R1, R2 and R3 independently represent hydrogen atom or an organic group which may contain a hetero atom in which an atom bonded to nitrogen atom is carbon atom.Type: GrantFiled: April 20, 2000Date of Patent: April 20, 2004Assignee: The Yokohama Rubber Co., Ltd.Inventors: Kiminori Araki, Kazunori Ishikawa
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Patent number: 6713452Abstract: A mixture of conjugates in which each conjugate in the mixture comprises a calcitonin drug coupled to an oligomer that includes a polyalkylene glycol moiety is disclosed. The mixture may lower serum calcium levels in a subject by 10, 15 or even 20 percent or more. Moreover, the mixture may be more effective at surviving an in vitro model of intestinal digestion than non-conjugated calcitonin. Furthermore, the mixture may exhibit a higher bioavailability than non-conjugated calcitonin.Type: GrantFiled: June 4, 2001Date of Patent: March 30, 2004Assignee: Nobex CorporationInventors: Nnochiri N. Ekwuribe, Christopher H. Price, Aslam M. Ansari, Amy L. Odenbaugh
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Patent number: 6605741Abstract: The present invention provides an efficient synthetic method of &agr;-ketol unsaturated fatty acid having a double bond at a &bgr;-position to the ketone group thereof. It comprises the steps of: preparing compound (4) by reacting monosubstituted acetylene (2) with epoxide (3); and preparing &agr;-ketol unsaturated fatty acid (1) from said compound (4) as shown in Reaction Formula 1: wherein R1 represents an alkyl group of 1-18 carbon atoms or an aliphatic hydrocarbon group of 2-18 carbon atoms having 1-5 double or triple bonds at given positions; R2 represents a protecting group for a hydroxyl group; R3 represents a protecting group for a carboxyl group; R is identical to R1 or, when R1 has one or more triple bonds, represents an aliphatic hydrocarbon group in which each triple bond of R1 is converted to a double bond; and A represents an alkylene group of 1-18 carbon atoms.Type: GrantFiled: April 10, 2002Date of Patent: August 12, 2003Assignee: Shiseido Co., Ltd.Inventors: Yoshihiro Yokokawa, Koji Kobayashi, Shosuke Yamamura
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Patent number: 6534073Abstract: Cosmetic skin care methods and compositions containing carboxymethylates of branched alcohols and/or ethoxylates thereof. The inventive compositions provide control of sebum secretion from sebocytes, improved oil control and improved skin feel, prevent shine and stickiness, while also providing anti-aging benefits which results in reduced appearance of wrinkles and aged skin, improved skin color, treatment of photoaged skin, improvement in skin's radiance and clarity and finish, and an overall healthy and youthful appearance of the skin.Type: GrantFiled: June 1, 2001Date of Patent: March 18, 2003Assignee: Unilever Home & Personal Care USA division of Conopco, Inc.Inventors: Bijan Steven Harichian, Laurence Boen, John Steven Bajor
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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: 6509496Abstract: A process for forming a mineral, food or pharmaceutical grade salt product is described. The process comprises completing all the process steps in a single reactor vessel resulting in high yield and purity in shortened processing times on the order of {fraction (1/10)} to ⅓ of the processing times required in prior processes.Type: GrantFiled: October 19, 2000Date of Patent: January 21, 2003Assignee: Nutrapure, Inc.Inventors: Dennis M. Hager, William E. Stern, Kim R. Nielsen
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Patent number: 6459003Abstract: The present invention relates to novel ether compounds, compositions comprising ether compounds, and methods useful for treating and preventing cardiovascular diseases, dyslipidemias, dysproteinemias, and glucose metabolism disorders comprising administering a composition comprising an ether compound. The compounds, compositions, and methods of the invention are also useful for treating and preventing Alzheimer's Disease, Syndrome X, peroxisome proliferator activated receptor-related disorders, septicemia, thrombotic disorders, obesity, pancreatitis, hypertension, renal disease, cancer, inflammation, and impotence. In certain embodiments, the compounds, compositions, and methods of the invention are useful in combination therapy with other therapeutics, such as hypocholesterolemic and hypoglycemic agents.Type: GrantFiled: March 31, 2000Date of Patent: October 1, 2002Assignee: Esperion Therapeutics, Inc.Inventors: Jean-Louis Henri Dasseux, Carmen Daniela Oniciu
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Publication number: 20020119538Abstract: An enzymatic system comprised of glucose oxidase and a catalase of the same or different sources to result in the complete conversion of glucose to gluconic acid at a glucose concentration greater than 25% (w/w) ds. The resultant gluconic acid, which is essentially free from impurities normally associated with the fermentation process, is then spray granulated to produce a low-dust dry product.Type: ApplicationFiled: April 12, 2001Publication date: August 29, 2002Inventors: Oreste J. Lantero, Jayarama K. Shetty
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Patent number: 6423869Abstract: A compound of the formula (I): wherein R1 represents an amino group which may be substituted; R2 represents a carboxy group which may be esterified or amidated; R3, R4, R5 and R6 each represent a hydroxy group which may be protected; Q represents an aryl group which may be substituted; or a salt thereof is disclosed. The compound (I) possesses ant-Helicobacter pylori activity, and is useful in the prevention or treatment of various diseases associated with Helicobacter bacteria, such as duodenal ulcer, gastric ulcer, chronic gastritis and cancer of the stomach.Type: GrantFiled: November 1, 1999Date of Patent: July 23, 2002Assignee: Takeda Chemical Industries, Inc.Inventors: Ken-ichiro Miyagawa, Shigetoshi Tsubotani, Masafumi Nakao, Yoshitaka Nakano, Keiji Kamiyama, Motoo Izawa, Yohko Akiyama, Yuji Nishikimi
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Publication number: 20020091288Abstract: The present invention provides discrete-length polyethylene glycol and polyethylene glycol containing compounds and methods for their preparation.Type: ApplicationFiled: September 24, 2001Publication date: July 11, 2002Applicant: The University of WashingtonInventors: D. Scott Wilbur, Pradip M. Pathare
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Patent number: 6384241Abstract: A purified salt of &bgr;-hydroxyethoxy acetic acid of formula (1) having a fusion peak-top temperature detected by differential scanning calorimetry (DSC) and a purified 2-p-dioxanone of formula (2) derived from the purified salt of &bgr;-hydroxyethoxy acetic acid of formula (1). (wherein in formula (1), n=1-2, and if n=1, M is Na and/or K, and, if n=2, M is Ca and/or Mg.Type: GrantFiled: March 30, 2001Date of Patent: May 7, 2002Assignee: Mitsui Chemicals, Inc.Inventors: Satoru Nakatani, Takuji Matsumoto, Yoshinori Nakahara, Hideyuki Akieda, Takeshi Ishitoku
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Publication number: 20010056192Abstract: A purified salt of &bgr;-hydroxyethoxy acetic acid of formula (1) having a fusion peak-top temperature detected by differential scanning calorimetry (DSC) and a purified 2-p-dioxanone of formula (2) derived from the purified salt of &bgr;-hydroxyethoxy acetic acid of formula (1).Type: ApplicationFiled: March 30, 2001Publication date: December 27, 2001Inventors: Satoru Nakatani, Takuji Matsumoto, Yoshinori Nakahara, Hideyuki Akieda, Takeshi Ishitoku
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Patent number: 6288244Abstract: A process for the preparation of 3,4-dihydroxybutanoic acid (I) and 3-hydroxy-&ggr;-butyrolactone (V) thereof from a 3-leaving group substituted pentose source is described. In particular, the process relates to the synthesis of (R)-3,4-dihydroxybutanoic acid and (R)-3-hydroxy-&ggr;-butyrolactone from a 3-leaving group substituted L-pentose sugars. The process uses a base and a peroxide to convert the pentose source to the chiral 3,4-dihydroxybutanoic acid compound. The chiral 3,4-dihydroxybutanoic acid can be further converted to 3-hydroxy-&ggr;-butyrolactone by acidification. The chiral compound is useful as a chemical intermediate to the synthesis of various drugs and other products.Type: GrantFiled: September 21, 2000Date of Patent: September 11, 2001Assignee: Board of Trustees operating Michigan State UniversityInventor: Rawle I. Hollingsworth
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Patent number: 6245940Abstract: The invention relates to a method of manufacturing an acid derivative of ose containing n carbon atoms on the carbonic chain, characterised by the fact that an acid derivative of ose with n+1 carbon atoms containing at least one &agr; ketone function, and/or one of its salts, is brought into contact with hydrogen peroxide in a reaction medium without pH regulation.Type: GrantFiled: March 14, 2000Date of Patent: June 12, 2001Assignee: Roquette FreresInventor: Rodolphe Tamion
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Patent number: 6235930Abstract: A process for the preparation of 3,4-dihydroxybutanoic acid (I) and 3-hydroxy-&ggr;-butyrolactone (V) thereof from a 3-leaving group substituted pentose source is described. In particular, the process relates to the synthesis of (R)-3,4-dihydroxybutanoic acid and (R)-3-hydroxy-&ggr;-butyrolactone from a 3-leaving group substituted L-pentose sugars. The process uses a base and a peroxide to convert the pentose source to the chiral 3,4-dihydroxybutanoic acid compound. The chiral 3,4-dihydroxybutanoic acid can be further converted to 3-hydroxy-&ggr;-butyrolactone by acidification. The chiral compound is useful as a chemical intermediate to the synthesis of various drugs and other products.Type: GrantFiled: March 31, 1999Date of Patent: May 22, 2001Assignee: Board of Trustees operating Michigan State UniversityInventor: Rawle I. Hollingsworth
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Patent number: 6191314Abstract: A process for obtaining (per) fluoropolyethers substituted at one or at both end groups with a halogen atom selected from bromine or iodine, having the formula: A—CF2—O—(CF2CF2O)p—(CF2O)q—CF2—B (III) wherein A=B=halogen; or A=halogen and B=COOH or F, and the halogen is I or Br; p and q are integers such as to give a number average molecular weight (MW) in the range 350-5000 and the ratio p/q=0.5-2.0. The process includes treating di- or poly-acylperoxides having an average equivalent weight in the range 350-5000, of formula: T—CF2—O—[(CF2CF2O)p—(CF2O)q—CF2—CO—O—O——CO—CF2—(OCF2)q—(OCF2CF2)p]y—OCF2—COOH (II) with a halogen selected from iodine or bromine, in a polyhalogenated organic solvent, at temperatures between 20° and 80° C.Type: GrantFiled: June 9, 1999Date of Patent: February 20, 2001Assignee: Ausimont S.p.A.Inventors: Ivan Wlassics, Vito Tortelli
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Patent number: 6072082Abstract: A process for producing 2,2'-bis(hydroxymethyl)alkanoic acid of the present invention, comprises:a 2,2'-bis(hydroxymethyl)alkanal production step (A1) of reacting aliphatic aldehyde having two hydrogen atoms bonded to .alpha.Type: GrantFiled: February 9, 1999Date of Patent: June 6, 2000Assignee: Nippon Kasei Chemical CompanyInventors: Hideshi Saito, Mikio Suzuki, Shoji Sakamoto, Toshiharu Yokoyama, Kouji Maeda
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Patent number: 6066763Abstract: A process for preparing .alpha.-hydroxy acids by heating ammonium salts of .alpha.-hydroxy acids of general formula (I), removing the formed ammonia and water, adding water to the residue, and heating the obtained mixture, wherein R is hydrogen, C.sub.1 -C.sub.6 alkyl, alkyl(C.sub.1 -C.sub.6)thioalkyl (C.sub.1 -C.sub.6), phenyl or the like. This process is freed from the problem of disposal of by-products such as ammonium bisulfate and makes it possible to prepare a free .alpha.-hydroxy acid from an ammonium salt thereof economically and in a high yield.Type: GrantFiled: August 25, 1998Date of Patent: May 23, 2000Assignee: Nippon Soda Co., Ltd.Inventor: Koichi Hayakawa
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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: 5852211Abstract: A process for the conversion of the sodium salt of 2-keto-L-gulonic acid, which is present in an aqueous fermentation solution, into an alcoholic solution of the free acid and, if desired, into an alkyl ester of the acid comprises a) recovering the sodium 2-keto-L-gulonate monohydrate from an aqueous fermentation solution by crystallization involving evaporation, cooling or displacement and, if desired, pulverizing the thus-obtained crystallizate by grinding, b1) suspending the optionally ground sodium 2-keto-L-gulonate monohydrate obtained in step a) in a lower alcohol, leaving the crystals to swell and thereafter adding an acid of low water content, whereby the measured pH value should lie above 1.5, or b2) adding the optionally ground sodium 2-keto-L-gulonate monohydrate obtained in step a) together with an about stoichiometric amount of an acid of low water content to a lower alcohol using a wet grinding system, whereby the measured pH value should lie above 1.Type: GrantFiled: April 17, 1997Date of Patent: December 22, 1998Assignee: Roche Vitamins Inc.Inventors: Ralf Dumpelmann, Tomislav Keglevic
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Patent number: 5834576Abstract: A novel acrylic ester which is represented by general formula (2) ##STR1## wherein R.sub.1 and R.sub.2 independently represent a hydrogen atom or an organic residue, R.sub.3 represents an organic residue, n is a positive number among 1 to 3, and m is a positive number among 1 to 100 and which is applicable to various uses, is obtained by reacting an acrylic ester of general formula (3) ##STR2## wherein R.sub.1 represents a hydrogen atom or an organic residue, and R.sub.3 represents an organic residue, with a cyclic ether compound of general formula (4) ##STR3## wherein R.sub.2 represents a hydrogen atom or an organic residue, and n is a positive number among 1 to 3. Moreover, a novel acrylic acid derivative whose use is even wider is obtained by hydrolyzing the acrylic acid derivative.Type: GrantFiled: February 27, 1996Date of Patent: November 10, 1998Assignee: Nippon Shokubai Co., Ltd.Inventors: Hideaki Nagano, Koichi Nakagawa, Keiji Yurugi, Mitsuaki Makino, Tsuyoshi Hirata, Koichiro Nagare, Yuichi Kita
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Patent number: 5801277Abstract: The present invention provides: a solid catalyst which enables a person to simply and efficiently carry out an etherification reaction; and a process by which an ether compound is simply and efficiently produced using the solid catalyst. The solid catalyst is a first solid catalyst comprising at least one rare earth element, or is a second solid catalyst comprising a metallic compound which includes a metal atom and a nonmetal atom bonded to the metal atom, wherein the metallic compound has molecular orbitals including: at least one orbital (L) having an energy of E.sub.L (eV) which satisfies E.sub.LUMO .ltoreq.E.sub.L .ltoreq.(E.sub.LUMO +0.05) wherein E.sub.LUMO is an energy (eV) of the lowest unoccupied molecular orbital around the metal atom; and at least one orbital (H) having an energy of E.sub.H (eV) which satisfies (E.sub.HOMO -0.02).ltoreq.E.sub.H .ltoreq.E.sub.HOMO wherein E.sub.Type: GrantFiled: May 19, 1997Date of Patent: September 1, 1998Assignee: Nippon Shokubai Co., Ltd.Inventors: Yasutaka Sumida, Miaki Asakawa, Yuichi Kita, Mitsuhiro Kitajima, Yoshiyuki Takahashi, Kazuo Sagi
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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: 5789186Abstract: A sample is treated with a phosphoglyceric acid mutase (PGAM) inhibitor (polythionic acid (salt) such as potassium tetrathionate) to inactivate the M-type isozyme activity and the B-type PGAM is quantified by determining PGAM isozymes by a rate assay. The B-type PGAM is a novel marker for cerebral apoplexy, and the diagnosis of cerebral apoplexy is enabled by assaying it.Type: GrantFiled: June 3, 1996Date of Patent: August 4, 1998Assignee: Oriental Yeast Co., Ltd.Inventors: Hitoshi Takeshita, Hiroshi Morita, Akira Fujiwara, Yasutaka Kaneda, Tohru Watanabe, Taizou Hayashi, Kohji Uchida, Yushi Matsuo, Takekazu Horio
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Patent number: 5777142Abstract: Compositions comprising unsaturated hydroxycarboxylic compounds, a process for reacting olefinic compounds with carboxylic reagents and products prepared by the process. The compositions containing the hydroxycarboxylic compounds and the products of the process are useful as intermediates for preparing additives for lubricants and fuels.Type: GrantFiled: August 22, 1995Date of Patent: July 7, 1998Assignee: The Lubrizol CorporationInventors: Paul E. Adams, Mark R. Baker, Jeffry G. Dietz
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Patent number: 5734031Abstract: A new cation exchange resin is formed by mixing phytic acid with a material selected from the group consisting of polyhydroxy polymer, .beta.-cyclodextrin and gluconic acid, and heating the mixture for about 130.degree.-180.degree. C. for about 15 minutes to 3 hours. A large number of different materials may be removed from solution by the resin including inorganic cations, organic pesticides and nitrogen bases.Type: GrantFiled: September 25, 1995Date of Patent: March 31, 1998Assignee: The United States of America as represented by the Secretary of AgricultureInventor: Jacob Lehrfeld