Processes Patents (Class 536/55.3)
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Patent number: 8410076Abstract: A cationized hyaluronic acid and/or a salt thereof includes a quaternary ammonium group-containing group, and has a degree of cationization of 0.15 to 0.6.Type: GrantFiled: April 23, 2008Date of Patent: April 2, 2013Assignee: Q.P. CorporationInventors: Kazunori Asaoka, Shunichi Fujikawa, Tomoyuki Kanemitsu, Wakako Sakamoto
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Process for preparing glycopeptides having asparagine-linked oligosaccharides, and the glycopeptides
Patent number: 8399656Abstract: Glycopeptide having at least one asparagine-linked oligosaccharide at a desired position of the peptide chain obtained by: (1) esterifying hydroxyl of a resin and carboxyl of an amino acid having amino group nitrogen protected with a fat-soluble protective group (AGFPG), (2) removing the protective group to form a free amino group, (3) amidating the free amino group and carboxyl of an amino acid having AGFPG, (4) removing the protective group, (5) repeating the steps (3) and (4), (6) amidating the free amino group and carboxyl of the asparagine portion of an asparagine-linked oligosaccharide having AGFPG, (7) removing the protective group, (8) amidating the free amino group and carboxyl of an amino acid having AGFPG, (9) repeating steps (7) and (8), (10) removing the protective group, and (11) cutting off the resin with an acid; glycopeptide obtained by transferring sialic acid or a derivative thereof to the above glycopeptide.Type: GrantFiled: October 14, 2011Date of Patent: March 19, 2013Assignees: Otsuka Chemical Co., Ltd.Inventor: Yasuhiro Kajihara -
Patent number: 8389713Abstract: A photocrosslinked polysaccharide pseudo-sponge exhibiting a low swelling property and a high degradation ability in vivo while retaining a suitable strength. The polysaccharide pseudo-sponge is produced by a crosslinking reaction of a photoreactive polysaccharide obtained by introducing a photoreactive group into a polysaccharide, and exhibits a low swelling property and a blue dextran-low dyeaffinity.Type: GrantFiled: October 26, 2011Date of Patent: March 5, 2013Assignee: Seikagaku CorporationInventor: Tomoya Sato
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Patent number: 8383808Abstract: A method to prepare D-glucosamine hydrochloride, obtaining product from raw material of citric acid residue from citric acid production by means of fermentation, and through processes of hydrolysis, suction filtering, concentration etc. Due to recovery of the citric acid residue, the present invention alleviates the environment pollution caused by the residue; Moreover, the D-glucosamine hydrochloride product produced from the raw material of citric acid residue is vegetarian D-glucosamine hydrochloride, without fishy odor and heavy metal pollution, safe and environment-friendly, with product purity up to 98-102%, and in line with the U.S.Type: GrantFiled: October 14, 2010Date of Patent: February 26, 2013Inventors: Jianguo Bai, Degui Wang, Jian Wang
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Publication number: 20130035481Abstract: The present invention relates to a method for preparation of the trisaccharide 6?-0-sialyllactose (formula (I)) or salts thereof as well as intermediates in the synthesis and for the use of 6?-0-sialyllactose salts in pharmaceutical or nutritional compositions.Type: ApplicationFiled: February 21, 2011Publication date: February 7, 2013Applicant: GLYCOM A/SInventors: Ignacio Pérez Figueroa, Ferenc Horváth, Gyula Dekany, Károly Ágoston, Ágnes Ágoston, István Bajza, Julien Boutet, Markus Hederos, Piroska Kovács-Pénzes, Lars Kröger, Christoph Röhrig, Andreas Schroven, Ioannis Vrasidas, Christian Risinger
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Patent number: 8357794Abstract: An isolated polysaccharide has the structure [-?(1,3)-D-GalpNAc-?(1,4)-D-Glcp-]n The polysaccharide may be from a Bifidobacterium strain NCIMB41003. The polysaccharide exhibits immunomodulatory activity.Type: GrantFiled: May 2, 2008Date of Patent: January 22, 2013Assignee: The Procter & Gamble Company and Alimentary Health LimitedInventors: Raymond Alan Grant, Liam O'Mahony, Barbara Sheil
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Publication number: 20130005954Abstract: Processes are disclosed for the synthesis of the Factor Xa anticoagulant fondaparinux and related compounds. Protected pentasaccharide intermediates and 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 are provided.Type: ApplicationFiled: June 28, 2011Publication date: January 3, 2013Inventors: Ravishanker KOVI, Ashish Naik, Brijesh Patel, Muralikrishna Madala
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Patent number: 8338388Abstract: A process for the crosslinking of at least one polymer selected from polysaccharides and derivatives thereof, which is carried out in an aqueous solvent by the action of an effective and non-excessive amount of at least one crosslinking agent, characterized in that it is carried out on a mixture containing at least one low-molecular weight polymer and at least one high-molecular weight polymer. A process for the preparation of an injectable monophase hydrogel of at least one crosslinked polymer selected from polysaccharides and derivatives thereof. Crosslinked polymers and injectable monophase hydrogels respectively obtainable by each of said processes.Type: GrantFiled: May 18, 2010Date of Patent: December 25, 2012Assignee: Allergan, Inc.Inventor: Pierre Lebreton
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Publication number: 20120309854Abstract: Compositions comprising compounds having an aldohexose moiety, a highly fluorinated moiety, and a nitrogen-containing functional group linking the moieties together are disclosed. The aldohexose-based fluoroadditives are effective in reducing the surface tension of water and are useful in various surfactant applications. Also disclosed are processes for making aldohexose-based fluoroadditives.Type: ApplicationFiled: May 14, 2012Publication date: December 6, 2012Applicant: E I DU PONT DE NEMOURS AND COMPANYInventors: ANILKUMAR RAGHAVANPILLAI, Stefan Reinartz
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Patent number: 8324356Abstract: Disclosed are polysaccharides containing residues of glucosamine or galactosamine in the repetitive unit, characterized by the presence of esters on the hydroxyls or amides on the amine functions, with lipoic acid or with mixtures of lipoic acid and formic acid.Type: GrantFiled: December 11, 2008Date of Patent: December 4, 2012Assignee: Sigea S.R.L.Inventors: Fabrizio Picotti, Marco Bosco, Luca Stucchi, Matteo Fabbian
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Patent number: 8314219Abstract: C-glycoside keto-amide derivatives, including C-glycoside keto-hydrazones and C-glycoside keto-oximes, may be prepared from plant or animal lipids and saccharides. These C-glycoside keto-amide derivatives are of the formula: wherein: R is a saccharide; Y is independently selected from H or a halogen; m is an integer greater than or equal to 1; X is NH (as in C-glycoside keto-hydrazones) or O (as in C-glycoside keto-oximes); and R2 is an acyl moiety derived from any lipid fatty acid of the formula —C(O)—R3, wherein R3 is a C5 to C22 straight or branched chain hydrocarbon which may be saturated or unsaturated. These C-glycoside keto-amide derivatives have potential applications as surfactants, detergents, liposomes, and bilayers.Type: GrantFiled: May 11, 2010Date of Patent: November 20, 2012Assignee: The United States of America as represented by the Secretary of AgricultureInventor: Neil P Price
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Patent number: 8293889Abstract: A method of manufacturing water-treatment particles comprises respectively preparing a particle-fabricating solution that comprises chitinous composition and a forming solution first. Next, a complex solution is prepared by adding calcium sulfite into the particle-fabricating solution. Finally, the complex solution is pumped into the forming solution to form water-treatment particles. In addition, water-treatment particles manufactured by the method above are also disclosed in the specification.Type: GrantFiled: March 7, 2012Date of Patent: October 23, 2012Assignee: Taiwan Textile Research InstituteInventors: Su-Chen Chen, Jui-Sheng Lee
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Publication number: 20120264702Abstract: The present invention relates to methods and compositions for the synthesis, production, and use of pro-drug propofol analogs. This invention relates to a method for the production of a broad group of glycosylated propofol carbohydrate derivatives.Type: ApplicationFiled: April 9, 2012Publication date: October 18, 2012Inventors: Brian Shull, John Baldwin, Ramesh Gopalaswamy, Zishan Haroon
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Publication number: 20120264927Abstract: Methods for labeling glycans that include a step of freeze-drying a labeled glycan preparation. The labeled glycan preparation is maintained in a substantially frozen state for the duration of the freeze-drying process.Type: ApplicationFiled: April 15, 2008Publication date: October 18, 2012Inventors: Ian Christopher Parsons, Lakshmanan Thiruneelakantapillai, Carlos J. Bosques, Brian Edward Collins
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Publication number: 20120259067Abstract: Provided is a method for producing a 2-cyanoethyl group-containing organic compound having a high ratio of replacement by cyanoethyl groups and a high dielectric constant. More specifically, provided is a method for producing a 2-cyanoethyl group-containing organic compound comprising a step of reacting acrylonitrile with a hydroxyl group-containing organic compound in the presence of a quaternary ammonium salt as a catalyst through a Michael addition.Type: ApplicationFiled: March 27, 2012Publication date: October 11, 2012Inventors: Ikuo Fukui, Kazuhisa Hayakawa, Soji Tanioka, Masahiro Ohgata, Masaaki Kajitani
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Publication number: 20120244625Abstract: The invention provides the use of 2-picoline borane (2-PB) for the reductive amination of carbohydrates, especially glycans from book plasma, wherein the concentration of 2-PB is less than the concentration of NaBH(OAc)3 or NaBH3CN required to obtain comparable conversion of the carbohydrate. It also describes a process for labelling a carbohydrate, the process comprising contacting the carbohydrate with a labelling agent, e.g. 2-aminobenzoic acid, 2-aminobenzamide, APTS, etc. in the presence of 2-picoline borane as reducing agent. Labelling the carbohydrate in this way facilitates detection using HPLC techniques, e.g. HILIC-HPLC-FL, HILIC-ESI-IT-MS, or capillary electrophoresis.Type: ApplicationFiled: September 27, 2010Publication date: September 27, 2012Applicant: LEIDEN UNIVERSITY MEDICAL CENTERInventors: Lucia Renee Ruhaak, Manfred Wuhrer
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Patent number: 8247546Abstract: Acid polysaccharides characterized by the concomitant presence of partial esters with non-polysaccharide carboxylic acids and esters between the acid groups of the initial polysaccharide and the alcohol groups of the repetitive units, with the formation of crosslinking among the polysaccharide chains.Type: GrantFiled: December 18, 2007Date of Patent: August 21, 2012Assignee: Siega S.R.L.Inventors: Luca Stucchi, Marco Bosco, Rita Gianni, Fabrizio Picotti
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Patent number: 8236935Abstract: The invention relates to a gem-difluoride glycoconjugated compound with formula (I): where R represents II or a benzyl, acetyl, benzoyl alkyl group, R1 and R2 may be identical or different and represent H or an alkyl, benzyl, benzoyl, acetyl, pivaloyl, trialkylsilyl, tertiobutyldiphenylsilyl protective group or an acetal group of the CR?R? type, where R? and R? may be identical or different and represent H or an alkyl, aryl, benzyl or thiophene group, R3 represents H or an alkyl, benzyl, benzoyl, acetyl, pivaloyl, trialkylsilyl or tertiobutyldiphenylsilyl protective group, R4 represents OR?, NGR?GR?, N3, or a phthalimide, where R? represents H or an alkyl, benzyl, benzoyl, acetyl, pivaloyl, trialkylsilyl or tertiobutyldiphenylsilyl protective group, GR? and GR? may be identical or different and represent II or an alkyl, benzyl, benzoyl, acetyl, alkyloxycarbonyl, allyloxycarbonyl or benzyloxycarbonyl group, R5 represents a free or protected hydroxyl group or a halogen, R6 represents H or an alkyl, acetyl, benzType: GrantFiled: April 24, 2007Date of Patent: August 7, 2012Assignee: Institut National des Sciences Appliquees de Rouen (INSA)Inventors: Jean-Charles Quirion, Geraldine Castle Deliencourt-Godefroy, Christophe Audouard
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Publication number: 20120190631Abstract: Techniques to glycosylation are described, and more particularly to the production of glycosylation structures that are resistant to enzymatic degradation, thereby modulating one or more of their biological properties or those of therapeutic moieties incorporating them, and in particular to reacting activated carbohydrate substrates containing fluorine, such as 3-fluoro sialic acid compounds, with sugar acceptors to produce covalent conjugates of the sugar acceptor and one or more of the sialic acid compounds.Type: ApplicationFiled: June 16, 2010Publication date: July 26, 2012Inventors: Andrew Graham Watts, Amanda Barbara MacKenzie, Terrence Kantner
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Patent number: 8211680Abstract: A method is presented for the production of cellulosic ethanol, acetic acid and derivatives from the extract containing fibers and hemicelluloses after steam cooking of biomass in a host plant. The process is integrated with the host plant process to minimize the effect of loss of heat value from the extracted hemicelluloses and eliminate the need for the waste water treatment plant.Type: GrantFiled: May 28, 2009Date of Patent: July 3, 2012Assignee: API Intellectual Property Holdings, LLCInventors: Theodora Retsina, Vesa Pylkkanen, Kimberley Nelson
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Publication number: 20120157672Abstract: A porous structure includes a polysaccharide and having a multitude of pores wherein an average pore size of the pores is not smaller than 40 ?m and a ratio of the number of pores having a pore size not smaller than 50 ?m to the total number of the pores is not less than 30%. The porous structure improves the solubility of a polysaccharide in water.Type: ApplicationFiled: February 27, 2012Publication date: June 21, 2012Applicant: Terumo Kabushiki KaishaInventors: Naotaka CHINO, Miho Kai
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Publication number: 20120157671Abstract: Enantiomerically enriched (1S,4R)-2-oxa-3-azabicyclo[2.2.1]hept-5-ene of formula wherein PG1 is an amino-protective group, are prepared from cyclopentadiene via hetero-Diels-Alder cycloaddition with protected 1-C-nitroso-?-D-ribofuranosyl halides of formula wherein X is a halogen atom selected from fluorine, chlorine, bromine and iodine, PG2 is a hydroxyl-protective group and PG3 is a 1,2-diol-protective group.Type: ApplicationFiled: August 25, 2010Publication date: June 21, 2012Inventors: Manuela Franzen, Christian Noti
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Patent number: 8202971Abstract: A process for preparing compounds of chitosan saccharified with aminosugar, adopts chitosan derivatives, aminosugar derivatives and anhydride derivatives as raw materials to synthesize target products. The process comprises: covalently bonding an anhydride derivative as a bonding arm to an aminosugar derivative, so as to form a monosaccharide derivative having an end group of carboxyl; and then covalently bonding the monosaccharide derivative having an end group of carboxyl to a primary amino group of a chitosan derivative via the carboxyl, so as to form a compound of chitosan saccharified with aminosugar.Type: GrantFiled: July 8, 2009Date of Patent: June 19, 2012Assignee: Ocean University of ChinaInventors: Xiguang Chen, Jing Li, Xiaojie Cheng, Tao Jiang
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Patent number: 8202986Abstract: A branched hyaluronic acid, wherein the linear backbone comprises hyaluronic acid in which one or more N-Acetyl-Glucosamine has been deacetylated to Glucosamine, with branching sidechain(s) covalently linked to the primary amine(s) of said deacetylated Glucosamine thus forming a secondary amine(s); a precursor for producing said branched hyaluronic acid; and a method for producing said branching hyaluronic acid.Type: GrantFiled: July 13, 2007Date of Patent: June 19, 2012Assignee: Novozymes Biopolymer AISInventors: Kristoffer Toemmeraas, Khadija Schwach-Abdellaoui
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Patent number: 8193340Abstract: Provided is a preparation method of a porous hyaluronic acid sponge comprising the steps of: dissolving hyaluronic acid in an aqueous sodium hydroxide solution; adding an epoxy-based crosslinking agent to the resultant aqueous sodium hydroxide solution in which hyaluronic acid is dissolved and homogenizing the hyaluronic acid solution; hydrogelating the homogenized hyaluronic acid solution; washing the hydrogelated hyaluronic acid hydrogel with ultrapure water; swelling the washed hyaluronic acid hydrogel to attain porosity; and freeze-drying the hyaluronic acid hydrogel to obtain a porous hyaluronic acid sponge.Type: GrantFiled: May 2, 2007Date of Patent: June 5, 2012Assignees: Seoul National University Industry Foundation, Prostemics Co., Ltd.Inventors: Dae-Duk Kim, Jeong-Yeon Kang, Chung-Wook Chung, In-Soo Yoon, Sun-Young Kim, Byung-Soon Park, Jong-Hyuk Sung
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Publication number: 20120116066Abstract: The present invention relates to a process for the synthesis of the Factor Xa anticoagulent Fondaparinux and related compounds. The invention relates, in addition, to efficient and scalable processes for the synthesis of various intermediates useful in the synthesis of Fondaparinux and related compounds.Type: ApplicationFiled: October 29, 2010Publication date: May 10, 2012Applicant: Reliable Biopharmaceutical CorporationInventors: Payal P. Patel, Chun Ma, Kevin K. Ohrr, Sourena Nadji
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Patent number: 8168598Abstract: The invention provides a tobramycin formulation for delivery by aerosolization in the form of additive-free, isotonic solution whose pH has been optimised to ensure adequate shelf-life at room temperature. Said formulation can be advantageously used for the treatment and prophylaxis of acute and chronic endobronchial infections, in particular those caused by the bacterium Pseudomonas aeruginosa associated to lung diseases such as cystic fibrosis.Type: GrantFiled: May 6, 2011Date of Patent: May 1, 2012Assignee: Chiesi Farmaceutici S.p.A.Inventors: Chiara Malvolti, Raffaella Garzia
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Publication number: 20120095205Abstract: This invention relates to a novel method of preparation of hyaluronic acid derivatives by means of a reaction of the hyaluronic acid with the complex (O-acyl-O?-alkyl carbonate-substituted pyridine) of the general formula R—CO—O—CO—O—R1 and R25C5N. The reaction takes place in DMSO in the presence of an external base, forming O-acylated products. The method leads to higher substitution degrees and shorter reaction times compared to the known analogues, hi case the agent comprises two or more functional groups R(CO—O—CO—O—R1)n, crosslinked hyaluronic acid derivatives are formed.Type: ApplicationFiled: March 13, 2010Publication date: April 19, 2012Applicant: CONTIPRO CInventors: Radovan Buffa, Vladimir Velebny, Lucie Pospisilova, Eva Prikopova, Martin Pravda, Pavel Nikodym, Lukas Palek
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Patent number: 8158763Abstract: An asparagine-linked ?2,3-oligosaccharide having undeca- to hepta-saccharides, an asparagine-linked ?2,6-oligosaccharide having undeca- to hepta-saccharides and containing fluorine and an asparagine-linked oligosaccharide derivative containing at least one fucose in N-acetylglucosamine on the nonreducing terminal side of an asparagine-linked oligosaccharide wherein the asparagine has amino group protected with a lipophilic protective group, and a process for producing these compounds.Type: GrantFiled: October 25, 2007Date of Patent: April 17, 2012Assignees: Otsuka Chemical Co. Ltd.Inventors: Yasuhiro Kajihara, Kazuaki Kakehi, Kazuhiro Fukae
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Patent number: 8153440Abstract: Various methods for altering surface characteristics of a microsphere are provided. One method includes coupling an enolic acid to the microsphere to modify the surface characteristics of the microsphere. The surface characteristics may include charge density and/or pKa. A reagent can be coupled to the microsphere via the enolic acid. The reagent may include a biomolecule. The modified surface characteristics may increase a stability of the reagent when the reagent is coupled to the microsphere. The modified surface characteristics may also improve performance of an assay carried out with the microsphere. Another embodiment relates to a microsphere that includes an enolic acid coupled to a polymer core of the microsphere such that the enolic acid modifies surface characteristics of the microsphere. A reagent can be coupled to the microsphere via the enolic acid.Type: GrantFiled: December 16, 2010Date of Patent: April 10, 2012Assignee: Luminex CorporationInventors: Ananda G. Lugade, Kurt D. Hoffacker
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Publication number: 20120035340Abstract: The present invention relates to a method for reductive amination of a water soluble carbohydrate. An aminated water soluble carbohydrate is a prerequisite in processes for further modification of cellulose. The synthesis of this molecule comprises, providing a water soluble carbohydrate, an amine and a reducing agent, which are reacted under acidic conditions, isolated to give an aminated water soluble carbohydrate with a yield larger than 60%. The invention also relates to an aminated hemicellulose molecule with a molecular weight of at least 1 kDa, especially xyloglucan.Type: ApplicationFiled: February 5, 2010Publication date: February 9, 2012Applicant: SWETREE TECHNOLOGIES ABInventors: Rikard Slättegård, Marcus Ruda, Harry Brumer
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Patent number: 8110677Abstract: This invention relates to a method of extracting crude polysaccharide by microwave-assisted from Artemisia sphaerocephala seed de-oiling dregs. In particular, the invention comprising: microwave-assisted extraction, enzymatic hydrolysis, dialysis et. al. It provides a technique whereby the polysaccharide can be extracted effectively, in a relatively short period of time (20-30 min) with respect to conventional extraction methods and allows for an enhanced extraction yield (more than 30%). Furthermore, the invention also allows for the extraction of material with less solvent consumption, good reproducibility, excellent solubility, energy conservation, environmental protection, and showed great potential for efficient sample preparation and large-scale industrial application in the near future. With great resource advantage of Artemisia sphaerocephala in China, the invention has bright perspectives in promoting local economic development.Type: GrantFiled: February 24, 2009Date of Patent: February 7, 2012Assignee: Northwest Normal UniversityInventors: Ji Zhang, Junlong Wang, Yiqian Wu, Jian Yao, Yunpu Wang, Junyu Liang, Yanan Zhang, Xiaodong Wang, Xiaoqing Xu
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Patent number: 8106184Abstract: The invention relates to compositions of nicotinoyl ribosides and nicotinamide riboside derivatives and their methods of use. In some embodiments, the invention relates to methods of making nicotinoyl ribosides. In some embodiments, the invention relates to pharmaceutical compositions and nutritional supplements containing a nicotinoyl riboside. In further embodiments, the invention relates to methods of using nicotinoyl ribosides and nicotinamide riboside derivatives that promote the increase of intracellular levels of nicotinamide adenine dinucleotide (NAD+) in cells and tissues for improving cell and tissue survival.Type: GrantFiled: November 17, 2006Date of Patent: January 31, 2012Assignee: Cornell UniversityInventors: Anthony Andrew Sauve, Tianle Yang
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Patent number: 8101393Abstract: The invention provides polypeptides having any cellulolytic activity, e.g., a cellulase activity, a endoglucanase, a cellobiohydrolase, a beta-glucosidase, a xylanase, a mannanse, a ?-xylosidase, an arabinofuranosidase, and/or an oligomerase activity, polynucleotides encoding these polypeptides, and methods of making and using these polynucleotides and polypeptides. In one aspect, the invention is directed to polypeptides having any cellulolytic activity, e.g., a cellulase activity, e.g., endoglucanase, cellobiohydrolase, beta-glucosidase, xylanase, mannanse, ?-xylosidase, arabinofuranosidase, and/or oligomerase activity, including thermostable and thermotolerant activity, and polynucleotides encoding these enzymes, and making and using these polynucleotides and polypeptides. In one aspect, the invention provides polypeptides having an oligomerase activity, e.g., enzymes that convert recalcitrant soluble oligomers to fermentable sugars in the saccharification of biomass.Type: GrantFiled: December 8, 2006Date of Patent: January 24, 2012Assignee: BP Corporation North America Inc.Inventors: Kevin A. Gray, Lishan Zhao, Michelle H. Cayouette
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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: 8071756Abstract: A photocrosslinked polysaccharide pseudo-sponge exhibiting a low swelling property and a high degradation ability in vivo while retaining a suitable strength. The polysaccharide pseudo-sponge is produced by a crosslinking reaction of a photoreactive polysaccharide obtained by introducing a photoroactive group into a polysaccharide, and exhibits a low swelling property and a blue dextran-low dyaffinity.Type: GrantFiled: September 10, 2004Date of Patent: December 6, 2011Assignee: Seikagaku CorporationInventor: Tomoya Sato
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Process for preparing glycopeptides having asparagine-linked oligosaccharides, and the glycopeptides
Patent number: 8063202Abstract: Glycopeptide having at least one asparagine-linked oligosaccharide at a desired position of the peptide chain obtained by: (1) esterifying hydroxyl of a resin and carboxyl of ah amino acid having amino group nitrogen protected with a fat-soluble protective group (AGFPG), (2) removing the protective group to form a free amino group, (3) amidating the free amino group and carboxyl of an amino acid having AGFPG, (4) removing the protective group, (5) repeating the steps (3) and (4), (6) amidating the free amino group and carboxyl of the asparagine portion of an asparagine-linked oligosaccharide having AGFPG, (7) removing the protective group, (8) amidating the free amino group and carboxyl of an amino acid having AGFPG, (9) repeating steps (7) and (8), (10) removing the protective group, and (11) cutting off the resin with an acid; glycopeptide obtained by transferring sialic acid or a derivative thereof to the above glycopeptide.Type: GrantFiled: April 16, 2009Date of Patent: November 22, 2011Assignees: Otsuka Chemical Co., Ltd., Yasuhiro KajiharaInventor: Yasuhiro Kajihara -
Patent number: 8058424Abstract: The present invention provides a method for the preparation of 5-azacytidine, wherein 5-azacytidine is represented by the structure: The method involves the silylation of 5-azacytosine, followed by the coupling of silylated 5-azacytosine to a protected ?-D-ribofuranose derivative. The coupling reaction is catalyzed by trimethylsilyl trifluoromethanesulfonate (TMS-Triflate).Type: GrantFiled: December 20, 2010Date of Patent: November 15, 2011Assignee: Pharmion LLCInventors: Dumitru Ionescu, Peter Blumbergs
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Patent number: 8049002Abstract: Processes for the synthesis of lipochitooligosaccharides were developed. A fully acylated oligoglucosamine precursor is prepared and reacted with a glucosamine monomer that has an amine protecting phthaloyl group. With removal of the phthaloyl group, a fatty acid may be added on the terminal glucosamine unit, forming a lipochitooligosaccharide. The processes can be adapted for use on a commercial scale.Type: GrantFiled: May 7, 2009Date of Patent: November 1, 2011Assignee: E.I. du Pont de Nemours and CompanyInventor: Subramaniam Sabesan
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Patent number: 8034925Abstract: Glucosamine suitable for human or animal consumption is disclosed. The glucosamine is derived from fungal biomass containing chitin. Various methods of producing glucosamine by acid hydrolysis of fermented fungal biomass are also disclosed.Type: GrantFiled: March 18, 2010Date of Patent: October 11, 2011Assignee: Cargill, IncorporatedInventors: Lawrence E. Fosdick, John A. Bohlmann, James R. Trinkle, Brenda L. Ray
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Patent number: 8034767Abstract: A method is provided for producing a purine nucleoside, such as inosine and guanosine, and a method for producing a 5?-purine nucleotide such as 5?-inosinic acid or 5?-guanylic acid, using a bacterium belonging to the either genus Escherichia or genus Bacillus, wherein purine nucleoside productivity of said bacterium is enhanced by enhancing an activity of a protein encoded by the yeaS (leuE) gene.Type: GrantFiled: June 2, 2009Date of Patent: October 11, 2011Assignee: Ajinomoto Co., Inc.Inventors: Ekaterina Aleksandrovna Kutukova, Natalia Pavlovna Zakataeva, Vitaly Arkadievich Livshits
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Patent number: 8026356Abstract: The present invention provides a method for preparing pure Stavudine having purity more than 99.5% comprises: i) Converting 3?,5?-anhydrothymidine to crude Stavudine, ii) Converting crude Stavudine to stable solvates of Stavudine, iii) Desolvation of the solvates to give pure Stavudine. The present invention also disclosed novel solvates of Stavudine and conversion of novel Stavudine solvates to Stavudine.Type: GrantFiled: November 17, 2006Date of Patent: September 27, 2011Assignee: Matrix Laboratories, Ltd.Inventors: Purna Chandra Ray, Jagan Mohana Chary Tummanapalli, Seeta Ramanjaneyulu Gorantla
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Publication number: 20110224424Abstract: A solution phase synthesis method for preparing an oligonucleotide, wherein at least some of the reagents are solid supported. The method suitable for large- scale synthesis comprises coupling a protected compound with a nucleotide derivative having a protection group in the presence of a solid supported activator to give an elongated oligonucleotide with a P(III)-internucleotide bond; optionally processing the elongated oligonucleotide by capping by reaction with a solid supported capping agent and/or by oxidizing or sulfurizing by reaction of the oligonucleotide with a solid supported oxidizing or sulfurization reagent; and removing the protection group. The coupling may include reacting a 3?-protected compound of formula: with a nucleotide derivative having a 5?-protection group, or reacting a 5?-protected compound of formula with a nucleotide derivative having a 3?-protection group.Type: ApplicationFiled: May 25, 2011Publication date: September 15, 2011Applicants: GIRINDUS AG, CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE, UNIVERSITY OF MONTPELLIER IIInventors: Ilaria ADAMO, Cécile DUEYMES, Andreas SCHÖNBERGER, Jean-Louis IMBACH, Albert MEYER, Francois MORVAN, Francoise DEBART, Jean-Jacques VASSEUR, Meinolf LANGE, Fritz LINK
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Patent number: 8012942Abstract: Provided are thieno[3,4-d]pyrimidin-7-yl and furo[3,4-d]pyrimidin-7-yl ribosides, riboside phosphates and prodrugs thereof as well as intermediates and methods of preparation. The compounds, compositions, and methods provided are useful for the treatment of Flaviviridae virus infections.Type: GrantFiled: February 9, 2010Date of Patent: September 6, 2011Assignee: Gilead Sciences, Inc.Inventors: Thomas Butler, Aesop Cho, Choung U. Kim, Jie Xu
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Publication number: 20110213137Abstract: The present disclosure provides methods of making isotopically-labeled glycans or a mixture of glycans (e.g., a glycan preparation) via reductive amination. Such methods are useful, for example, in the determination of the relative amounts of a glycan species present in two or more glycoprotein preparations using mass spectroscopy. In one aspect, the present disclosure provides a method of making an isotopically-labeled glycan by a glycan with an amine and an isotopically-labeled reducing agent to provide an isotopically-labeled aminated glycan. In certain embodiments, the amine is an isotopically-labeled amine.Type: ApplicationFiled: April 15, 2008Publication date: September 1, 2011Applicant: MOMENTA PHARMACEUTICALS, INC.Inventors: Carlos J. Bosques, Ian Christopher Parsons, Lakshmanan Thiruneelakantapillai, Brian Edward Collins, Hetal Sarvaiya
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Patent number: 7993678Abstract: The present invention relates to the modification of hyaluronic acid (HA) with aryl/alkyl succinic anhydrides (ASA) to produce aryl/alkyl succinic anhydride HA derivatives, to the derivatives as such, and to their applications and uses, particularly in the cosmetic and biomedical industries. The ASA-HA derivatives are expected to have interesting properties that can be used for advanced formulation (bind stronger to the skin compared to non-modified HA), possibly also in delivery systems for actives or drugs by encapsulation (nano/micro capsules) or formation of nano/micro spheres. Further, the low MW ASA-HA derivatives are expected to penetrate the skin more efficiently than non-modified HA of the same MW.Type: GrantFiled: August 26, 2006Date of Patent: August 9, 2011Assignee: Novozymes Biopolymer A/SInventors: Kristoffer Tømmeraas, Corinne Eenschooten
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Publication number: 20110178267Abstract: Methods for obtaining Tamaritt and Tamaritt-Intermediate based materials are implemented through a secondary chemical reactor providing a second chemical reaction conducted with at least two reactants. The first reactant is Tamaritt and the second is an inorganic, or organic, or bio-molecular reagent, or their combination. Tamaritt is produced in a primary chemical reactor, modulating chemical reactions, preferably using a plasma device, and producing certain byproducts. A solid organic dye is dissolved in water producing a solution placed into the primary reactor, wherein the temperature and pressure are predeterminedly adjusted. The byproducts are injected into the solution, thereby commencing a first chemical reaction conducted until it finally results in obtaining Tamaritt. Tamaritt-Intermediate byproducts, being bond-altering catalyst-reagents, are obtained at a certain stage of the process.Type: ApplicationFiled: January 15, 2010Publication date: July 21, 2011Inventor: Vladimir Tarnovsky
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Patent number: 7973157Abstract: Novel processes for the purification of an imino or amino sugar, such as D-1-deoxygalactonojirimycin (DGJ). Particularly, there are described processes for the purification of multi-kilogram scale sugars using hydrochloric acid.Type: GrantFiled: June 8, 2006Date of Patent: July 5, 2011Assignee: Amicus Therapeutics, Inc.Inventors: Michael Major, Robert Peterson, Szymon Kosinski
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Patent number: 7960523Abstract: This invention relates to processes for production of alkylamino glucosaminide phosphate compounds, and of disaccharide compounds, including various novel intermediates and intermediate processes. In one aspect, glycosyl halides are produced by reaction of an O-silyl glycoside with a dihalomethyl alkyl ether.Type: GrantFiled: October 4, 2007Date of Patent: June 14, 2011Assignee: Corixa CorporationInventor: David A. Johnson
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Publication number: 20110130560Abstract: A cartridge in which sonication is applied to biological matter to disrupt and release nucleic acids from the matter is formed from a cartridge body containing a series of wells connected by fluid passages engineered to prevent backflow, with at least one well containing a sonication window covered by a thin lamina to transmit sonic vibrations from a sonication horn contacting the exterior surface of the window. Fluid transport among the wells is achieved by pressure differentials through the fluid passages, and a succession of functions is performed in the various wells, including disruption, mixing, binding of the released nucleic acids to binding materials, washing, elution, and collection.Type: ApplicationFiled: May 27, 2010Publication date: June 2, 2011Applicant: BIO-RAD LABORATORIES, INC.Inventors: Amir M. Sadri, Nenad Kircanski, Manja Kircanski, Neven Nikolic, Milija Timotijevic