Reacting A Carbohydrate With An Organic -o- Containing Compound (e.g., Reacting Glucose With Methanol, Etc.) Patents (Class 536/18.6)
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Patent number: 11466298Abstract: The present invention relates to a method for preparing phosphorylated keto polyols by biocatalysis and uses thereof.Type: GrantFiled: May 22, 2018Date of Patent: October 11, 2022Assignees: COMMISSARIAT A L'ENERGIE ATOMIQUE ET AUX ENERGIES ALTERNATIVES, CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE, UNIVERSITE CLERMONT AUVERGNE, UNIVERSITE D'EVRY VAL D'ESSONNEInventors: Véronique De Berardinis, Marcel Salanoubat, Marielle Lemaire, Christine Guerard-Helaine
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Patent number: 11325937Abstract: The present invention discloses a glycoside compound represented by Formula III, and a preparation method, a composition, use and an intermediate thereof. The glycoside compound provided in the present invention has simple preparation method, can significantly increase the expression of VEGF-A mRNA, and is effective in promoting the angiogenesis. This provides a reliable guarantee for the development of drugs with pro-angiogenic activity for treating cerebral infarction cerebral stroke, myocardial infarction, and ischemic microcirculatory disturbance of lower limbs.Type: GrantFiled: May 7, 2019Date of Patent: May 10, 2022Assignee: SHANGHAI HUTCHISON PHARMACEUTICALS LIMITEDInventors: Guoqiang Lin, Jiange Zhang, Ping Tian, Chenguo Feng, Changsen Zhan, Junjie Zhou
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Patent number: 11312928Abstract: This invention provides a cleaning agent composition that exhibits good storage stability, especially storage stability at low temperature, and a cleaning agent composition that can be favorably dispensed from a dispenser. The cleaning agent composition of the present invention comprises (a) a fatty acid salt and (b) a sophorose lipid, wherein the proportion of the component (a) is 4 to 18 mass % based on the cleaning agent composition taken as 100 mass %; the proportion of a fatty acid salt having 12 or fewer carbon atoms is 15 parts by mass or more, and the proportion of a fatty acid salt having 16 or more carbon atoms is 60 parts by mass or less, based on 100 parts by mass of the total amount of the component (a); the proportion of an acidic sophorose lipid is 80 mass % or more based on the total amount of the component (b) taken as 100 mass %; and the proportion of the component (b) is 5 to 80 parts by mass per 100 parts by mass of the total amount of the component (a).Type: GrantFiled: March 7, 2018Date of Patent: April 26, 2022Assignee: SARAYA CO., LTD.Inventors: Emi Okada, Reiko Matsumura, Masashi Yamamoto
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Patent number: 10106862Abstract: The present invention relates to a process for generating glucose and glucose derivatives from the direct contacting of cellulose, hemicelluloses and/or polysaccharides with a mixed super critical fluid system of alcohol and water whereby the partial pressure of the system provides for both alcoholysis and hydrolysis of the material to generate primarily glucose, and glucose derivatives.Type: GrantFiled: March 27, 2017Date of Patent: October 23, 2018Assignee: INVENTURE RENEWABLES, INC.Inventors: William W. Berry, William Rusty Sutterlin, Mark G. Tegen
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Patent number: 9605325Abstract: The present invention relates to a process for generating glucose and glucose derivatives from the direct contacting of cellulose, hemicelluloses and/or polysaccharides with a mixed super critical fluid system of alcohol and water whereby the partial pressure of the system provides for both alcoholysis and hydrolysis of the material to generate primarily glucose, and glucose derivatives.Type: GrantFiled: May 24, 2016Date of Patent: March 28, 2017Assignee: Inventure Renewables, Inc.Inventors: William W. Berry, William Rusty Sutterlin, Mark G. Tegen
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Patent number: 9527928Abstract: Anhydrous methods of fractionating corn grain that do not require the use of water but rather depends on use of organic solvents are described. The methods include contacting whole grain corn flour with a at least one organic solvent selected from the group consisting of a C1-C6 alcohol, ketone, ester or furan to form an admixture having no more than 15% w/w water. The admixture is separated into i) a solids fraction enriched with corn fiber and protein and 2) a liquid organic slurry comprising suspended starch, dissolved corn oil and the organic solvent. The starch is separated from the first organic slurry to obtain a solvent extracted solid starch fraction and a clarified organic solution. The clarified organic solution which contains dissolved oils is retained and may be evaporated to obtain corn oil that can be further refined.Type: GrantFiled: May 8, 2013Date of Patent: December 27, 2016Assignee: Archer-Daniels-Midland-CompanyInventor: Thomas P. Binder
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Patent number: 9266918Abstract: An alkenyl glycoside is prepared by reacting a metathesis-derived unsaturated fatty alcohol containing 10 to 30 carbon atoms with either (1) a reducible monosaccharide or composition hydrolyzable to a reducible monosaccharide, or (2) a hydrocarbyl glycoside produced by reacting an alcohol containing up to 6 carbon atoms with a reducible monosaccharide or composition hydrolyzable to a reducible monosaccharide. Each of these reactions is performed in the presence of an acid catalyst and under conditions sufficient to form the alkenyl glycoside or hydrocarbyl glycoside. The preferred alkenyl glycosides are 9-decen-1-yl glycoside; 9-dodecen-1-yl glycoside; 9-tridecen-1-yl glycoside; 9-pentadecen-1-yl glycoside; 9-octadecen-yl glycoside; or 9-octadecen-1,18-diyl glycoside.Type: GrantFiled: March 10, 2014Date of Patent: February 23, 2016Assignee: Elevance Renewable Sciences, Inc.Inventors: Ryan A. Littich, Jonathan Brekan, Timothy Montavon
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Patent number: 9035032Abstract: A method of preparing the anthracyclin carminomycin using a starting material comprising daunorubicin. The method comprises reacting daunorubicin or N-protected daunorubicin with soft Lewis acids for the demethylation of the 4-methoxy group, resulting in a reaction mass. The reaction mass is treated with an aqueous solution of a strong organic acid or a mineral acid. After decomposition of the resulting carminomycin and Lewis acids reactive complex, the reaction mass is extracted using a water insoluble organic solvent. As a result, carminomycin is extracted as a base.Type: GrantFiled: December 13, 2006Date of Patent: May 19, 2015Assignee: SOLUX CORPORATIONInventors: Alexander F. Zabudkin, Victor Matvienko, Alexey Matveev, Aleksandr M. Itkin
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Patent number: 8987437Abstract: The invention provides synthetic processes and synthetic intermediates that can be used to prepare compounds having useful anti-HIV properties.Type: GrantFiled: May 18, 2012Date of Patent: March 24, 2015Assignee: Gilead Sciences, Inc.Inventors: Richard Hung Chiu Yu, Brandon Heath Brown, Richard P. Polniaszek, Benjamin R. Graetz, Keiko Sujino, Duong Duc-Phi Tran, Alan Scott Triman, Kenneth M. Kent, Steven Pfeiffer
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Publication number: 20150038689Abstract: Provided are methods for the efficient stereoselective formation of glycosidic bonds, without recourse to prosthetic or directing groups.Type: ApplicationFiled: July 29, 2014Publication date: February 5, 2015Inventors: Clay S. Bennett, John P. Issa, Dina Lloyd
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Patent number: 8927698Abstract: The present invention relates to an improved synthesis of a trisaccharide of the formula, novel intermediates used in the synthesis and the preparation of the intermediates.Type: GrantFiled: April 7, 2010Date of Patent: January 6, 2015Assignee: Glycom A/SInventors: Gyula Dékany, Istvan Bajza, Julien Boutet, Ignacio Pérez Figueroa, Markus Hederos, Ferenc Horvath, Piroska Kovács-Pénzes, Lars Kröger, Johan Olsson, Christoph Röhrig, Andreas Schroven, Ioannis Vrasidas
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Publication number: 20140275506Abstract: An alkenyl glycoside is prepared by reacting a metathesis-derived unsaturated fatty alcohol containing 10 to 30 carbon atoms with either (1) a reducible monosaccharide or composition hydrolyzable to a reducible monosaccharide, or (2) a hydrocarbyl glycoside produced by reacting an alcohol containing up to 6 carbon atoms with a reducible monosaccharide or composition hydrolyzable to a reducible monosaccharide. Each of these reactions is performed in the presence of an acid catalyst and under conditions sufficient to form the alkenyl glycoside or hydrocarbyl glycoside. The preferred alkenyl glycosides are 9-decen-1-yl glycoside; 9-dodecen-1-yl glycoside; 9-tridecen-1-yl glycoside; 9-pentadecen-1-yl glycoside; 9-octadecen-yl glycoside; or 9-octadecen-1,18-diyl glycoside.Type: ApplicationFiled: March 10, 2014Publication date: September 18, 2014Applicant: ELEVANCE RENEWABLE SCIENCES, INC.Inventors: Ryan A. Littich, Jonathan Brekan, Timothy Montavon
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Publication number: 20140221633Abstract: The present invention provides a one-pot method of preparing an unprotected ?-O-glycolipid. The first step involves contacting a protected ?-iodo sugar with a catalyst and a lipid comprising a hydroxy group, under conditions sufficient to prepare a protected ?-O-glycolipid. The second step involves deprotecting the protected ?-O-glycolipid under conditions sufficient to prepare the unprotected ?-O-glycolipid, wherein the contacting and deprotecting steps are performed in a single vessel. The present invention also provides a one-pot method of preparing an unprotected ?-O-glycolipid following the steps for the preparation of the unprotected ?-O-glycolipid.Type: ApplicationFiled: January 6, 2014Publication date: August 7, 2014Inventors: Jacquelyn Gervay-Hague, Wenjun Du, Suvarn S. Kulkarni, Matthew Schombs
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Patent number: 8765936Abstract: An amine or hydrazide derivative of a sialic acid unit, e.g. in a polysaccharide, is reacted with a bifunctional reagent at least one of the functionalities of which is an ester of N-hydroxy succinimide, to form an amide or hydrazide product. The product has a useful functionality, which allows it to be conjugated, for instance to proteins, drugs, drug delivery systems or the like. The process is of particular utility for derivatising amine groups introduced in sialic acid terminal groups of polysialic acids.Type: GrantFiled: October 8, 2012Date of Patent: July 1, 2014Assignee: Lipoxen Technologies LimitedInventors: Sanjay Jain, Ioannis Papaioannou, Smita Thobhani
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Patent number: 8710210Abstract: A method for synthesizing an oligonucleotide which comprises using a sulfurizing agent of general formula (I) for sulfurizing at least one phosphorus internucleotide linkage of a precursor of the oligonucleotide, wherein R is an aryl group or a heteroaryl group, which is bonded to the S-atom through an annular carbon atom; and R1 and R2 are independently organic residues, preferably a C1-C20 hydrocarbon residue. The method may further comprise purifying the oligonucleotide. Also included is a process for the synthesis of the sulfurizing agent.Type: GrantFiled: June 30, 2011Date of Patent: April 29, 2014Assignee: Girindus America, Inc.Inventors: Yigang He, Victor Sorokin, Wieslaw Adam Mazur
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Patent number: 8703923Abstract: Processes for the synthesis of the Factor Xa anticoagulent Fondaparinux, and related compounds are described. Also described are protected pentasaccharide intermediates as well as efficient and scalable processes for the industrial scale production of Fondaparinux sodium by conversion of the protected pentasaccharide intermediates via a sequence of deprotection and sulfonation reactions.Type: GrantFiled: September 14, 2012Date of Patent: April 22, 2014Assignee: Reliable Biopharmaceutical CorporationInventors: Sourena Nadji, James T. Smoot, Joseph A. Vanartsdalen
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Patent number: 8653049Abstract: The invention provides a compound (which can act as an adjuvant) of Formula I or Formula (II), wherein R1 R4 R5 R6 and R7 are each independently selected from hydrogen, acetyl, hydrocarbyl, a lipid moiety and a lipid acyl moiety; R2 is a hydroxyl, a hydrocarbyl, a lipid moiety, a lipid acyl moiety; or an amino hydrocarbyl group optionally substituted with a hydrocarbyl, a lipid moiety or a lipid acyl moiety; R3 and R8 are each independently selected from acetyl, a hydrocarbyl, a lipid moiety and a lipid acyl moiety; X is a peptide chain; The above normuramylglycopeptide compounds can be located in liposomes and micelles and can function as immunomodulators, along with a desired antigen (or DNA encloding the antigen), in (e.g. DNA) vaccines.Type: GrantFiled: March 17, 2009Date of Patent: February 18, 2014Assignees: Imuthes Limited, Institute of Organic Chemistry and Biochemistry AV CR, V.V.I., Vyzkumny USTAV Veterinarniho Lekarstvi, V.V.I.Inventors: Karsten Hipler, Andrew Miller, Jaroslav Turanek, Miroslav Ledvina
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Patent number: 8637649Abstract: A method of preparing a ribofuranose derivative essentially free of pyranose compounds includes a step of contacting a solution of MDR containing MDRP as an impurity in a solvent including methanol and/or tetrahydrofuran with at least one alkali metal periodate under conditions sufficient to oxidize at least a portion of the MDRP. MDR containing at most 5 wt % of MDRP based on the total weight of MDR and MDRP may be produced.Type: GrantFiled: November 23, 2011Date of Patent: January 28, 2014Assignee: Johnson Matthey Public Limited Co.Inventors: Xing Fu, Albrecht Zumbrunn
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Publication number: 20130331556Abstract: A catalytic glycosylation method comprising: installing thioether to an anomeric carbon of a carbohydrate; and catalytically activating the thioether with a non-oxophilic Lewis acid. The thioether may comprise an anomerically stable thioether leaving group. The catalytic glycosylation method may further comprise: utilizing an acid-sensitive ester protecting group as permanent protecting group or using a reactivity-based one-pot glycosylation that employs a single-component catalyst to accelerate an oligosaccharide assembly process. A protecting group to mask hydroxyl functionalities in the production of oligosaccharides, natural products or any molecule having a hydroxyl group comprising an acid-labile ester protecting group.Type: ApplicationFiled: June 6, 2013Publication date: December 12, 2013Inventor: Xinyu Liu
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Publication number: 20130324708Abstract: A carbohydrate-containing feedstock is converted in a process by contacting the feedstock in a first step with an alcohol in the presence of a first acid catalyst at a temperature below 100° C. to yield an intermediate product, and contacting at least part of the intermediate product in a second step with an alcohol in the presence of a second acid catalyst at a temperature of at least 100° C. Products of such conversion may include hydroxymethylfurfural, hydroxymethylfurfural ethers, levulinic acid, esters thereof and furfural.Type: ApplicationFiled: December 28, 2011Publication date: December 5, 2013Applicant: FURANIX TECHNOLOGIES B.V.Inventors: Ana Sofia Vagueiro de Sousa Dias, Gerardus Johannes Maria Gruter, Robert-Jan van Putten
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Publication number: 20130303742Abstract: The present invention relates to a process for generating glucose and glucose derivatives from the direct contacting of cellulose, hemicelluloses and/or polysaccharides with a mixed super critical fluid system of alcohol and water whereby the partial pressure of the system provides for both alcoholysis and hydrolysis of the material to generate primarily glucose, and glucose derivatives.Type: ApplicationFiled: November 1, 2011Publication date: November 14, 2013Inventors: William Rusty Sutterlin, Mark G. Tegen, William Berry
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Patent number: 8513395Abstract: The present invention relates to methods of preparing anthocyanins, and methods of preparing precursors of anthocyanins. The methods utilize a coupling reaction between a sugar and a suitable electrophilic precursor to form Eastern half intermediates that are then reacted with Western half intermediates to form the target anthocyanins. Some Eastern half intermediates and electrophilic precursors also form part of the invention.Type: GrantFiled: June 15, 2006Date of Patent: August 20, 2013Assignee: Biosynth ASInventor: Einar Bakstad
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Patent number: 8470984Abstract: The present invention provides a process for the preparation of a morpholinyl anthracycline derivative in good yields and purity, including 3?-deamino-3?-4?-anhydro-[2?(S)-methoxy-3?(R)-hydroxy-4?-morpholinyl]doxorubicin (1).Type: GrantFiled: December 1, 2011Date of Patent: June 25, 2013Assignee: Nerviano Medical Sciences S.R.L.Inventors: Michele Caruso, Vittoria Lupi, Matteo Salsa
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Publication number: 20130158242Abstract: The present invention provides an ?-selective glycosylation method. The ?-selective glycosylation method includes performing a reaction of a donor having a saccharide structure and a formamide-containing compound to form a glycosyl imidate compound; and in one pot environment, performing an addition reaction of the glycosyl imidate compound and an acceptor having a hydroxyl group to form an ?-glycoside with high ?-selectivity. The ?-selective glycosylation method is applicable to the large scale production and easy to recover the formamide-containing compound.Type: ApplicationFiled: June 18, 2012Publication date: June 20, 2013Applicant: National Chiao Tung UniversityInventors: Kwok-Kong Tony Mong, Chin-Sheng Chao, Shao-Ru Lu, Chih-Yueh Liu
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Publication number: 20130066057Abstract: The invention relates to a method for obtaining surfactants from cellulose and hemicellulose, which comprises one reaction in a single reactor (one pot) and which includes at least the following steps: a) a first hydrolysis step, in which the cellulose is mixed with at least one ionic liquid, water and a catalyst; and b) a second glycosylation step, in which at least one alcohol is added when the hydrolysis level of the cellulose is between 10 and 80%. The resulting products are preferably alkyl-?,?-glycosides.Type: ApplicationFiled: March 10, 2011Publication date: March 14, 2013Applicants: UNIVERSIDAD POLITECNICA DE VALENCIA, CONSEJO SUPERIOR DE INVESTIGACIONES CIENTIFICAS (CSIC)Inventors: Avelino Corma Canos, Nicolás David Villandier
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Patent number: 8394755Abstract: Provided are compositions comprising one or more compounds having a structure comprising a node structure with from four to twelve carbon atoms, one or more (poly)glyceryl groups, and one or more hydrophobic moieties, wherein each of the one or more (poly)glyceryl groups is linked to the node structure by a first primary linking group, the one or more hydrophobic moieties are each independently linked either to the node structure by a primary linking group or to one of the (poly)glyceryl groups by a secondary linking group, and wherein the polyglyceryl thickener has an average degree of glyceryl polymerization of from greater than 3 to less than about 11 and an average number of hydrophobic groups per primary linking group of about 0.35 or greater. Also provided are polyglyceryl compounds, compositions comprising water, a surfactant, and a polyglyceryl thickener, as well as, methods of making polyglyceryl compounds and compositions of the present invention.Type: GrantFiled: March 30, 2011Date of Patent: March 12, 2013Assignee: Johnson & Johnson Consumer Companies, Inc.Inventors: Sasa Andjelic, Modesto Erneta, Michael J. Fevola, Frank C. Sun
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Patent number: 8394935Abstract: An object of the present invention is to provide a industrially appropriate method for producing the ?-anomers of ribofuranose derivatives in a highly selective manner at a high yield. The present invention provides a method for producing ribofuranose derivatives wherein ?-anomers is precipitated from among the generated furanose derivatives by controlling the amount of a reaction reagent used and/or using a poor solvent in the acetolysis reactions of 2,3,5-tri-O-acyl-1-O-alkyl-ribofuranose and 2,3-di-O-acyl-1-O-alkyl-5-deoxy-ribofuranose.Type: GrantFiled: December 7, 2007Date of Patent: March 12, 2013Assignee: API CorporationInventors: Manabu Katsurada, Tomoko Sasaki, Yasuko Nakajima, Nobuo Kyoumura
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Publication number: 20130060015Abstract: The present invention relates to methods for producing glucosides directly from glucose or a polysaccharide comprising glucose as a structural unit. The present invention provides a method comprising reacting glucose or a polysaccharide comprising glucose as a structural unit with a compound represented by R—OH in the presence of a supercritical or subcritical carbon dioxide to produce glucosides and a method comprising dissolving or suspending glucose or a polysaccharide comprising glucose as a structural unit in an organic solvent containing a compound represent by R—OH and reacting the glucose or polysaccharide with the compound represented by R—OH in the presence of a supercritical or subcritical carbon dioxide to produce glucosides.Type: ApplicationFiled: May 13, 2011Publication date: March 7, 2013Applicants: JX NIPPON OIL & ENERGY CORPORATION, NAGASAKI UNIVERSITYInventors: Suguru Motokucho, Toshio Inoue
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Patent number: 8389698Abstract: A method of generating synthetic metabolites of tanaproget derivatives thereof is provided. These compounds and methods of using these derivatives for detecting tanaproget metabolites in samples are provided.Type: GrantFiled: June 26, 2009Date of Patent: March 5, 2013Assignee: Wyeth LLCInventors: Li Shen, Kelly Keating, Oliver McConnell, William DeMaio, Appavu Chandrasekaran
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Patent number: 8298436Abstract: Fire extinguishing compositions and methods of extinguishing a fire comprising compounds of formula (I) where Rf is a fluorocarbon group. The compounds and compositions described herein are useful as intermediates in the preparation of or as additives to AFFF (aqueous film forming foam) formulations used for the extinguishment of fuel and solvent fires.Type: GrantFiled: October 14, 2008Date of Patent: October 30, 2012Assignee: Ansul, IncorporatedInventor: Jeffrey D. Michael
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Patent number: 8293878Abstract: Methods of synthesizing sodium glucose co-transporter 2 inhibitors, as well as compounds useful therein, are disclosed. Particular inhibitors are compounds of formula I.Type: GrantFiled: August 11, 2011Date of Patent: October 23, 2012Assignee: Lexicon Pharmaceuticals, Inc.Inventors: Nicole Cathleen Goodwin, Bryce Alden Harrison, Shinya Iimura, Ross Mabon, Qiuling Song, Wenxue Wu, Jie Yan, Haiming Zhang, Matthew Mangzhu Zhao
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Patent number: 8252752Abstract: Hydrophilic transportable N-linked glycosyl dopaminergic prodrug compounds according to FORMULA V and methods of their use, wherein, Ring 1 comprises an aryl or heteroaryl ring having 4 to 8 carbon atoms, among which atoms are counted “X” and “Y”; each of X and Y is optional; X, when present is either —C(R1)2— or —C(R)2—; Y, when present, is either —CH2— or —CH2—CH2—; z, R5 and R5? are optional, and when present z, R5 and R5? together form a lower alkyl or a substituted lower alkyl moiety; N is part of either an amine or an amide linkage; E is a saccharide which forms a linkage with N through a single bond from a carbon or oxygen atom thereof; R1 and R4 are selected form the group consisting of hydrogen, hydroxyl, halogen, halo-lower alkyl, alkoxyl, alkoxyl-lower alkyl, halo-alkoxy, thioamido, amidosulfonyl, alkoxylcarbonyl, carboxamide, aminocarbonyl, and alkylamino-carbonyl; R2 and R3 are hydroxyl; R5 and R6, when present, are selected from the group consisting of hydrogen, hydroxyl, alkoxyl, carbonylType: GrantFiled: December 27, 2007Date of Patent: August 28, 2012Assignee: Glycon LLCInventor: Samuel T. Christian
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Patent number: 8212013Abstract: In preparing a glycoside compound from (a) a furanose compound or pyranose compound, and (b) an alcohol compound, a process for preparing a glycoside compound in which glycosidic bond locates selectively trans form relative to C-2 hydroxyl group, the process comprising using a furanose compound wherein the hydroxyl at the 2-position may have a substituent protected with a group A, or a pyranose compound which may have a substituent wherein R2 and R3 are the same or different and are each alkyl having 1 to 4 carbon atoms or aryl having or not having a substituent, or R2 and R3 are combined to form alkylene having 2 to 4 carbon atoms (the alkylene may be substituted with alkyl having 1 to 4 carbon atoms, or may have intervening phenylene), and m and n are each an integer of 0 or 1.Type: GrantFiled: February 20, 2006Date of Patent: July 3, 2012Assignee: Otsuka Chemical Co., Ltd.Inventor: Shigeru Yamago
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Patent number: 8211850Abstract: Provided are compositions comprising one or more compounds having a structure comprising a node structure with from four to twelve carbon atoms, one or more (poly)glyceryl groups, and one or more hydrophobic moieties, wherein each of the one or more (poly)glyceryl groups is linked to the node structure by a first primary linking group, the one or more hydrophobic moieties are each independently linked either to the node structure by a primary linking group or to one of the (poly)glyceryl groups by a secondary linking group, and wherein the polyglyceryl thickener has an average degree of glyceryl polymerization of from greater than 3 to less than about 11 and an average number of hydrophobic groups per primary linking group of about 0.35 or greater. Also provided are polyglyceryl compounds, compositions comprising water, a surfactant, and a polyglyceryl thickener, as well as, methods of making polyglyceryl compounds and compositions of the present invention.Type: GrantFiled: March 30, 2011Date of Patent: July 3, 2012Assignee: Johnson & Johnson Consumer Companies, Inc.Inventors: Sasa Andjelic, Modesto Erneta, Michael J. Fevola, Frank C. Sun
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Publication number: 20120116065Abstract: The present invention relates to an improved synthesis of a trisaccharide of the formula, novel intermediates used in the synthesis and the preparation of the intermediates.Type: ApplicationFiled: April 7, 2010Publication date: May 10, 2012Applicant: Glycom A/SInventors: Gyula Dékany, Istvan Bajza, Julien Boutet, Ignacio Pérez Figueroa, Markus Hederos, Piroska Kovács-Pénzes, Lars Króger, Johan Olsson, Christoph Róhrig, Andreas Schroven, Ioannis Vrasidas
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Patent number: 8163891Abstract: A process for the preparation of a poly(alkoxylated) oligonucleotide is provided. The process comprises reacting an oligonucleotide which has been purified by ultrafiltration with a poly(alkoxide) thereby to form a poly(alkoxylated) oligonucleotide. The poly(alkoxyalted) oligonucleotide may be separated from non-poly(alkoxyalted) oligonucleotide by ultrafiltration under denaturing conditions, such as the presence of organic solvents, for example, ethanol; the presence of urea; the addition of chaotropic salts, for example perchlorate and guanidinium salts; the presence of formamide; and the application of heat, for example a temperature of up to about 70° C.Type: GrantFiled: November 20, 2006Date of Patent: April 24, 2012Assignee: Avecia Biotechnology IncInventors: Nanda Dulal Sinha, Saied Shaikh, Satya Kuchimanchi
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Publication number: 20120095199Abstract: A method of forming a sucrose-6-ester includes in sequence the steps of: a) contacting sucrose with a organotinbased acylation promoter in a solvent in the presence of a base selected from amines and basic alkali metal salts; b) removing water to form a tin-sucrose adduct; and c) contacting the tin-sucrose adduct with an acylating agent to form the sucrose- 6-ester. The sucrose-6-ester may then be converted to sucralose.Type: ApplicationFiled: March 10, 2010Publication date: April 19, 2012Applicant: Tate & Lyle Technology Ltd.Inventors: Thomas Kennedy Hutton, Peter Jay Seaberg, Christopher C. Kerwood
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Patent number: 8119781Abstract: The present invention provides luminescent metal ion complexes for use in a wide range of biological and chemical studies. The luminescent metal ion complexes of the invention comprise a metal ion chelating component covalently bound to a carrier molecule. Also provided are methods of making and using the luminescent metal ion complexes.Type: GrantFiled: December 21, 2009Date of Patent: February 21, 2012Assignee: Biosearch Technologies, Inc.Inventors: Ronald M. Cook, Matt Lyttle, Mary Katherine Johannson
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Patent number: 8114987Abstract: A method of preparing 2-deoxy-L-ribose represented by the following formula I is disclosed. The preparation method includes the steps of: treating L-arabinose with an alcohol solvent in the presence of an acid to prepare 1-alkoxy-L-arabinopyranose; allowing the prepared 1-alkoxy-L-arabinopyranose to react with acyl chloride so as to prepare 1-alkoxy-2,3,4-triacyl-L-arabinopyranose; brominating the alkoxy group of the prepared 1-alkoxy-2,3,4-triacyl-L-arabinopyranose to prepare a 1-bromo-2,3,4-triacyl compound; allowing the prepared compound to react with zinc in the presence of ethyl acetate and an organic base so as to prepare glycal; treating the glycal with an alcohol solvent in the presence of an acid to prepare 1-alkoxy-2-deoxy-3,4-diacyl-L-ribopyranose; treating the prepared 1-alkoxy-2-deoxy-3,4-diacyl-L-ribopyranose with a base to prepare 1-alkoxy-2-deoxy-L-ribopyranose; and hydrolyzing the prepared 1-alkoxy-2-deoxy-L-ribopyranose in the presence of an acid catalyst.Type: GrantFiled: October 24, 2007Date of Patent: February 14, 2012Assignee: Samchully Pharm. Co. Ltd.Inventors: Kyung-Il Kim, Seung-Bum Ha, Jae-Hoon Jeon, Soon-Jeong Kwon, Yong-Tae Kim, Ji-Suk Yun
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Patent number: 8110667Abstract: Methods are described for conversion of carbohydrate polymers in ionic liquids, including cellulose, that yield value-added chemicals including, e.g., glucose and 5-hydroxylmethylfurfural (HMF) at temperatures below 120° C. Catalyst compositions that include various mixed metal halides are described that are selective for specified products with yields, e.g., of up to about 56% in a single step process.Type: GrantFiled: April 28, 2008Date of Patent: February 7, 2012Assignee: Battelle Memorial InstituteInventors: Zongchao C. Zhang, Heather M. Brown, Yu Su
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Patent number: 8080641Abstract: The present invention relates to a process for the production of cross-linked hyaluronic acid (HA) derivatives, in particular multiple, e.g. double cross-linked hyaluronic acid derivatives. The invention also provides novel cross-linked HA derivatives, products containing them and their uses in medical and pharmaceutical and cosmetic applications.Type: GrantFiled: March 23, 2009Date of Patent: December 20, 2011Assignee: Mentor Worldwide LLCInventor: Xiaobin Zhao
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Patent number: 8026347Abstract: Methods of synthesizing sodium glucose co-transporter 2 inhibitors, as well as compounds useful therein, are disclosed.Type: GrantFiled: July 17, 2008Date of Patent: September 27, 2011Assignee: Lexicon Pharmaceuticals, Inc.Inventors: Nicole Cathleen Goodwin, Bryce Alden Harrison, Shinya Iimura, Ross Mabon, Qiuling Song, Wenxue Wu, Jie Yan, Haiming Zhang, Matthew Mangzhu Zhao
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Publication number: 20110196139Abstract: Provided is a method for preparing a cellulose phosphite compound, more particularly a method for preparing a cellulose phosphite compound whereby cellulose is phosphorylated using an ionic liquid comprising an amine-based cation and a phosphite-based anion. Thus prepared cellulose phosphite compound has a good solubility in water and is highly valuable as concentration control agent, medicine, biomembrane, or the like.Type: ApplicationFiled: October 21, 2010Publication date: August 11, 2011Applicant: Korea Institute of Science and TechnologyInventors: Hyun Joo Lee, Bang Sook Lee, Young-Woong Suh, Byoung Koun Min, Byoung Sung Ahn, Hoon Sik Kim
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Publication number: 20110059022Abstract: Disclosed herein are compounds useful as two-photon tracers. Also, methods are provided for visualizing intracellular glucose uptake, screening anticancer agents, and diagnosing cancer using the compounds. They exhibit preferential uptake by cancer cells, penetrability sufficient to allow bright section images, high water solubility, high pH resistance and low toxicity in addition to applicability to living cells in deep tissues over a long period of time.Type: ApplicationFiled: September 7, 2010Publication date: March 10, 2011Applicant: SNU R&DB FOUNDATIONInventors: Seung Bum PARK, Bong Rae CHO, Hyang Yeon LEE, Jong Min PARK
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Patent number: 7875708Abstract: An amine or hydrazide derivative of a sialic acid unit, e.g. in a polysaccharide, is reacted with a bifunctional reagent at least one of the functionalities of which is an ester of N-hydroxy succinimide, to form an amide or hydrazide product. The product has a useful functionality, which allows it to be conjugated, for instance to proteins, drugs, drug delivery systems or the like. The process is of particular utility for derivatising amine groups introduced in sialic acid terminal groups of polysialic acids.Type: GrantFiled: August 12, 2005Date of Patent: January 25, 2011Assignee: Lipoxen Technologies LimitedInventors: Sanjay Jain, Ioannis Papaioannou, Smita Thobhani
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Publication number: 20100286376Abstract: The invention relates to a process for separating bioactive compounds obtained from vegetable materials. The invention also relates to a process for extracting bioactive compounds from vegetable material.Type: ApplicationFiled: October 9, 2008Publication date: November 11, 2010Applicant: Lang Technologies Pty., LimitedInventors: Tim Lang, Wayne Simpkins
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Patent number: 7820810Abstract: The present invention provides an improved process for the synthesis of 2?-O-substituted purine nucleosides. The process includes anhydro or thioanhydro ring opening of a selected 8,2?-cyclopurine nucleoside with a weak nucleophile in the presence of a Lewis acid ester, followed by reduction to afford the desired 2?-O-substituted purine nucleoside.Type: GrantFiled: March 19, 2008Date of Patent: October 26, 2010Assignee: Isis Pharmaceuticals, Inc.Inventor: Vasulinga Ravikumar
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Patent number: 7795423Abstract: The present invention provides a new labeling reagent for preparing modified oligonucleotides and processes for their production wherein these oligonucleotides contain at least once the structure P?N—SO2-benzole-L-M-X, characterized in that L is either —(CH2)n- or polyethylene glycol, M is selected from a group consisting of —NH—, —O—, —S—, and —COO—, and X is either a protecting group or a detectable unit. L is preferably either —(CH2)n- or polyethylene glycol.Type: GrantFiled: May 20, 2008Date of Patent: September 14, 2010Assignee: Roche Diagnostics Operations, Inc.Inventor: Dieter Heindl
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Patent number: 7772381Abstract: A method to synthesize benzyl group protected alpha-pentagalloylglucose (?-PGG) and related compounds. The method comprises the steps of: suspending a highly reactive acylation agent and an acylating catalyst in a donor solvent; adding ?-D-glucose or an analogue thereof to the mixture; reacting the mixture at room temperature for a time sufficient for reaction to occur; evaporating the solvent; taking up the residue in an appropriate solvent; filtering the residue and solvent mixture; and evaporating off the solvent.Type: GrantFiled: January 24, 2005Date of Patent: August 10, 2010Assignee: Ohio UniversityInventors: Klaus B. Himmeldirk, Xiaozhou Chen
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Patent number: 7732583Abstract: Novel glycolipid derivatives, where the substituent of the sphingosine base part is a short carbon chain alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted aryl group or substituted or unsubstituted aralkyl group and efficient synthetic methods for practical mass production of the same and intermediates useful for the synthesis of these compounds. Glycolipids having the formula (I): where R3 indicates a substituted or unsubstituted C1 to C7 linear alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted aryl group, or substituted or unsubstituted aralkyl group and R8 indicates a substituted or unsubstituted C1 to C35 alkyl group, substituted or unsubstituted aryl group or substituted or unsubstituted aralkyl group are chemically synthesized.Type: GrantFiled: February 13, 2004Date of Patent: June 8, 2010Assignee: Japan as represented by President of National Center of Neurology and PsychiatryInventors: Hirokazu Annoura, Kenji Murata, Takashi Yamamura