Ether-esters Patents (Class 536/116)
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Publication number: 20020034774Abstract: Novel methods for the treatment and/or prophylaxis of diseases caused by tissue-adhering bacteria are disclosed. By interacting with periplasmic molecular chaperones it is achieved that the assembly of pili is prevented or inhibited and thereby the infectivity of the bacteria is diminished. Also disclosed are methods for screening for drugs as well as methods for the de novo design of such drugs, methods which rely on novel computer drug modelling methods involving an approximative calculation of binding free energy between macromolecules. Finally, novel pyranosides which are believed to be capable of interacting with periplasmic molecular chaperones are also disclosed.Type: ApplicationFiled: March 7, 2001Publication date: March 21, 2002Inventors: Scott Hultgren, Meta Kuehn, Zheng Xu, Derek Ogg, Mark Harris, Matti Lepisto, Charles Hal Jones, Jan Kihlberg
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Publication number: 20020022597Abstract: Novel sulforhamnosylacylglycerol derivatives represented by General Formula (1): 1Type: ApplicationFiled: August 24, 2001Publication date: February 21, 2002Applicant: TOYO SUISAN KAISHA, LTD.Inventors: Takayuki Yamazaki, Fumio Sugawara, Keisuke Ohta, Kazuyoshi Masaki, Kotaro Nakayama, Kengo Sakaguchi, Noriyuki Sato, Hiroeki Sahara, Tatsuya Fujita
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Publication number: 20020002274Abstract: The invention relates to a process for the production of perbenzylated 1-O-glycosides of general formula I or salts thereof 1Type: ApplicationFiled: March 8, 2001Publication date: January 3, 2002Applicant: SCHERING AKTIENGESELLSCHAFTInventors: Johannes Platzek, Ulrich Niedballa, Peter Mareski
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Publication number: 20010053846Abstract: The invention is related to a preparation method of arbutin intermediate (chemical formula I). It is characterized by the glycosylation of hydroquinone or mono-protectected hydroquinone (chemical formula II) with pentaacetyl-&bgr;-D-glucose (chemical formula III) in the presence of Lewis acid and base as catalysts.Type: ApplicationFiled: April 20, 2001Publication date: December 20, 2001Applicant: Bioland Co., Ltd.Inventors: Yeon Soo Lee, Bum Tae Kim, Yong Ki Min, No Kyum Park, Ki Ho Kim, Jae Seob Lee, See Wha Jeoung, Ki Soo Kim
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Patent number: 6303777Abstract: An improved, solvent-free, two-stage transesterification process for preparing, from a polyol and fatty acid esters of an easily removable alcohol highly esterified polyol fatty acid polyesters having reduced levels of difatty ketones and &bgr;-ketoesters is disclosed. These reduced levels of difatty ketones/&bgr;-ketoesters are achieved by controlling the level of generated alcohol in the liquid phase of the reaction mixture and heating the reaction mixture to certain temperatures during the second stage of this improved process. Other optional reaction conditions, such as keeping the molar ratio of fatty acid esters to polyol within a specified range and reducing the level of basic catalyst, can also be used during the second stage reaction to further reduce the level of difatty ketones and/or &bgr;-ketoesters.Type: GrantFiled: July 6, 1994Date of Patent: October 16, 2001Assignee: The Procter & Gamble Co.Inventors: Ju-Nan Kao, John Keeney Howie, Patrick Joseph Corrigan, Richard Gerard Schafermeyer, Katherine Eleanor Flynn, Nelson James Holzschuh, David Joseph Bruno, Jr.
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Patent number: 6228997Abstract: Bacillus subtilis protease catalyzes the acylation of organic solvent-insoluble polysaccharides in isooctane solution containing vinyl esters of fatty acids as acyl donor. The reaction occurs only when the enzyme is solubilized via ion-pairing with the anionic surfactant dioctyl sulfosuccinate, sodium salt (AOT). Enzyme based acylation was demonstrated with amylose, cyclodextrins, cellulose, cellulose derivatives, and other polysaccharides such as chitosan, pullulan, and maltodextrose. These polysaccharides are reactive either as a cryogenically milled powder suspended in the organic solvent or as a thin film deposited onto ZnSe slides. For chitosan, &agr;-cyclodextrin, and hydroxyethyl cellulose (HEC), the enzymatic crosslinking reaction occurs using adipic acid divinyl ester (C6DVE). HEC forms a compound that gels in solvents such as ethyl alcohol and dimethyl sulfone oxide (DMSO).Type: GrantFiled: July 10, 1998Date of Patent: May 8, 2001Assignee: The United States of America as represented by the Secretary of the ArmyInventors: Joseph A. Akkara, David L. Kaplan, Ferdinando F. Bruno, Jonathan S. Dordick
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Patent number: 6214978Abstract: The invention concerns a new lipoteichoic acid which can be isolated from the new Streptococcus sp DSM 8747. The new LTA is called LTA-T. It has a lipid anchor, which is a galacto-furanosyl-beta-1-3-glycerol with different rests of fatty acids esterified in the two adjacent hydroxy groups in the glycerol moiety and a non-glycosylated, linear, unbranched GroP chain with an unusual short hydrophilic GroP chain. The hydrophilic backbone consists of only 10 glycerophosphate units esterified with D-alanine in an extent of 30%. The invention further concerns a pharmaceutical composition with the new LTA-T, optionally together with a monokine and/or hyaluronidase, a method of treating cancer comprising administration of an antitumor effective amount thereof, a method of producing the new compound and the new pharmaceutical composition, two degradation products of the new LTA-T and their use, and the new Streptococcus strain from which the new compound can be isolated.Type: GrantFiled: January 15, 1999Date of Patent: April 10, 2001Assignee: Lunamed AGInventors: Peter Truog, Peter Rothlisberger
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Patent number: 6207649Abstract: The invention relates to pharmaceutical compositions of nucleoside dimers containing an L-sugar in at least one of the nucleosides.Type: GrantFiled: December 23, 1998Date of Patent: March 27, 2001Assignee: Lipitek International, Inc.Inventors: Alexander L Weis, Kirupathevy Pulenthiran
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Patent number: 6201070Abstract: Methods are disclosed for enhancing the toughness, e.g., resistance to cracking upon flexation, of coatings made from cycloaliphatic epoxide derivatives wherein the cycloaliphatic epoxide derivative is a cycloaliphatic epoxide ester of a hydroxy-functional compound containing at least one branched, 1,2-alkylene oxide unit. Processes for making the cycloaliphatic epoxide derivatives and coating formulations comprising the cycloaliphatic epoxide derivatives are also disclosed.Type: GrantFiled: November 20, 1996Date of Patent: March 13, 2001Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Naofumi Kumabe, Thomas Andrew Upshaw, Robert Francis Eaton, Bharat Kanaiyalal Patel, John Kellis Braddock
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Patent number: 6063752Abstract: Acylated carbohydrates with at least one carboxyalkyl group etherified with the carbohydrate of the following general formulaKH(--O--CHR.sub.1 --(CH.sub.2).sub.p --(COOH or COO.sup.-)).sub.n (--O--CO--R.sub.2).sub.m,wherein KH (carbohydrate) is a monosaccharide, disaccharide, trisaccharide or polysaccharide, and whereinif KH is a monosaccharide, then n=1 to 4 and m=1 to 4 with n+m=2 to 5;if KH is a disaccharide, then n=1 to 7 and m=1 to 7 with n+m=2 to 8;if KH is a trisaccharide, then n=1 to 10 and m=1 to 10 with n+m=2 to 11; andif KH is a polysaccharide, then n=0.2 to 2.8 and m=0.2 to 2.8 with n+m=0.4 to 3 (with polysaccharide referred to the monosaccharide unit of the KH), and whereinR1 is=H or a moiety with 1-9 carbon atoms, in particular an alkyl or acyl moiety, andR2 is a moiety with 1-9 carbon atoms, in particular an alkyl or acyl moiety, and wherein p=0 to 9.Type: GrantFiled: June 18, 1997Date of Patent: May 16, 2000Assignee: Sudzucker Aktiengesellschaft Mannheim/OchsenfurtInventors: Sonja Ehrhardt, Alireza Haji Begli, Markwart Kunz
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Patent number: 6025335Abstract: The invention relates to nucleoside dimers containing an L-sugar in at least one of the nucleosides and their pharmaceutical compositions.Type: GrantFiled: September 21, 1995Date of Patent: February 15, 2000Assignee: Lipitek International, Inc.Inventors: Alexander L. Weis, Charles T. Goodhue, Kirupathevy Pulenthiran
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Patent number: 5945519Abstract: The invention relates to a process for the solvent-free preparation of sucrose fatty acid esters, their mixtures with nonsugar polyol fatty acid esters, and in particular of sucrose glycerides. In a first process step, sucrose is reacted with fatty acid alkyl esters in the presence of basic catalyst at reduce pressure and elevated temperature. In a further reaction step, the reaction mixture obtained above is reacted at reduced pressure and elevated temperature with 0.1 to 0.5 mol of polyol per mole of fatty acid alkyl ester employed and then filtered. The products of the process according to the invention have very high sucrose ester contents. They are free of undesired, unreacted alkyl ester.Type: GrantFiled: June 2, 1998Date of Patent: August 31, 1999Assignee: Th Goldschmidt AGInventors: Natvarlal Desai, Burghard Gruning
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Patent number: 5905071Abstract: The present invention relates to (2-aminoacylamino-2-deoxy-glycosyl)-amides, which are substituted on the nitrogen atom of the amino acid, of the general formula (I) ##STR1## in which the substituents have the meaning given in the description, to processes for their preparation and to their use in medicaments.Type: GrantFiled: June 25, 1996Date of Patent: May 18, 1999Assignee: Bayer AktiengesellschaftInventors: Oswald Lockhoff, Burkhard Mielke, Helmut Brunner, Klaus Schaller
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Patent number: 5861506Abstract: Thermoplastic and compostable cellulose ether esters with 2-hydroxycarboxylic acids as acid components and mixed esters which, in addition to 2-hydroxycarboxylic acid groups, have further mono-, dicarboxylic acid or carbamate groups.Type: GrantFiled: May 7, 1997Date of Patent: January 19, 1999Assignee: Wolff Walsrode AGInventors: Joachim Simon, Hanns Peter Muller, Rainhard Koch, Dirk Jacques Dijkstra, Jurgen Engelhardt, Volkhard Muller
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Patent number: 5854030Abstract: Sugar-containing poly(acrylate)-based hydrogels and methods of preparing these hydrogels are disclosed. Poly(sugar acrylate)s are chemeoenzymatically prepared and crosslinked to form hydrogels, which are water absorbant.Type: GrantFiled: December 11, 1995Date of Patent: December 29, 1998Assignee: University of Iowa Research FoundationInventors: Jonathan S. Dordick, David G. Rethwisch, Damodar R. Patil, Brett D. Martin, Robert J. Linhardt
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Patent number: 5840703Abstract: A reaction mixture for manufacturing polyol fatty acid polyesters comprises a polyol, a fatty acid lower alkyl ester, a base initiator and a phase transfer catalyst. The phase transfer catalyst can be a quaternary ammonium compound, a crown ether, a polyethylene glycol, a polyethylene glycol ether, a polyethylene glycol ester or mixtures thereof. The process of making polyol fatty acid polyesters is carried out at low temperatures and essentially in the absence of a solvent or emulsifier. The polyol fatty acid polyester product stream produced by the foregoing process and reaction mixture has a lower concentration of reaction by-products such as di-fatty ketones and beta-ketoesters and of caramelized by-product which results from the breakdown of the polyol reactant.Type: GrantFiled: November 15, 1996Date of Patent: November 24, 1998Inventors: Patrick J. Corrigan, John K. Howie
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Patent number: 5830872Abstract: Esters associating phenylacetic, 3-phenylpropionic, 4-phenylbutyric and n-butyric acids with Su(OH).sub.n monosaccharides or sugar alcohols, of general formula (I), in which the Su(OH).sub.n precursor is a monosaccharide or sugar alcohol, selected so that its structure or that of its derivatives ensures that internal interesterification does not take place either because the ester based on the general formula does not have a free hydroxyl grouping, or because with regard to the ester grouping, the free hydroxyl groupings are remotely located and/or badly aligned and/or bonded to a secondary carbon atom, and in which the Su(OH).sub.n monosaccharide or sugar alcohol is preferably D-mannose carrying the ester grouping on the anomeric carbon atom or else is a pentitol, for example, xylitol carrying the ester grouping on the C-1 primary carbon atom. These novel esters are useful as drugs, in particular in the treatment of haemoglobin diseases and premalignant or malignant tumours.Type: GrantFiled: March 11, 1997Date of Patent: November 3, 1998Assignee: L'Associazione di volontariato "Pro La Fondazione Futuro Senza Thalassemia"Inventors: Pierre Jean Baldwin, Olivier Claude Eric Douillet, Philippe Rene Michel Pouillart, Gino Lino Ronco, Pierre Joseph Villa
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Patent number: 5681948Abstract: A two-stage method for the preparation of polyol fatty acid polyesters is provided. The resulting polyol fatty acid polyesters are very lightly colored (i.e., colorless to slightly yellow) and have a high degree of substitution with fatty acid groups. The first stage of this two-stage method is a solvent-based esterification reaction; the second stage is an essentially solvent-free esterification reaction. In the first stage, a polyol in a solvent (e.g., sucrose in dimethylsulfoxide)) is reacted with fatty acid lower alkyl esters at relatively low temperatures using an alkaline salt catalyst. After the desired degree of esterification is obtained, the resulting partially-esterified polyol fatty acid polyesters and the solvent-containing phase are separated.Type: GrantFiled: March 6, 1995Date of Patent: October 28, 1997Assignee: Kraft Foods, Inc.Inventors: Mark Stuart Miller, Leslie George West, Robert Charles Dinwoodie, Richard S. Silver
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Patent number: 5679657Abstract: Low molecular weight acetylhyaluronate has the following characteristics:intrinsic viscosity: 50 to 200 cm.sup.3 /gsubstitution degree of acetyl group: 2.6 to 3.6 (excluding N-acetyl group)A skin-softening composition is mainly composed of this low molecular weight acetylhyaluronate. It can exhibit excellent skin-softening effect and moisturizing effect, while appropriately suppressing the thread-forming ability inherent in hyaluronic acid. A method of manufacturing acetylhyaluronate comprises the steps of suspending hyaluronic acid powder in an acetic anhydride solvent and then adding concentrated sulfuric acid thereto to effect acetylation. A method of purifying acetylhyaluronate comprises the steps of adding raw acetylhyaluronate to an aqueous acetone solution, adding and dissolving sodium lactate therein, and then adding highly concentrated acetone thereto to precipitate highly pure acetylhyaluronate. Acetylhyaluronate having highly purity can be obtained inexpensively.Type: GrantFiled: August 2, 1996Date of Patent: October 21, 1997Assignee: Shiseido Co., Ltd.Inventors: Takashi Oka, Toshio Yanaki, Michihiro Yamaguchi
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Patent number: 5661130Abstract: The present invention relates to a method of increasing the absorption of a compound via the ocular, nasal, nasolacrimal or inhalation route into the circulatory system of a patient. In particular, a method comprising administering with the compound an absorption enhancer comprising a nontoxic, nonionic alkyl glycoside is provided. Additionally provided are methods of raising or lowering the blood glucose level by administering glucagon or insulin, respectively, with such absorption enhancers. Finally, compositions for raising or lowering the blood glucose level are provided.Type: GrantFiled: June 24, 1993Date of Patent: August 26, 1997Assignee: The UAB Research FoundationInventors: Elias Meezan, Dennis J. Pillion
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Patent number: 5658880Abstract: Compounds that exhibit selectin binding activity are described and have the following structural formula: ##STR1## where W is selected from a group including structures a-d below ##STR2## wherein p is an integer of from 0-2, q is an integer of from 0-3, and r is an integer of from 0-5;A is selected from the group consisting of .alpha. and .beta. forms of sialic acid, Kemp's acid, quinic acid, R and S forms of mandelic acid, R and S forms of glyceric acid, R and S forms of lactic acid, propionic and acetic acid, and esters and amides thereof, --SO.sub.3, sulfonate, --PO.sub.3, phosphonate, trifluoromethyl, diazine and triazine;B is selected from a group consisting of .alpha. and .beta. forms of fucose, arabinose and esters and substituted forms thereof wherein one or more of the OH groups is independently substituted with F, N.sub.3, NHAc, NHCOCF.sub.3. The remaining variable are described in the specification.Type: GrantFiled: August 12, 1994Date of Patent: August 19, 1997Assignee: Glycomed IncorporatedInventors: Falguni Dasgupta, John H. Musser, Daniel E. Levy, Peng Cho Tang
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Patent number: 5618933Abstract: Chemoenzymatic methods of making sugar-based polymers are disclosed as well as novel sugar-based polymers. In one embodiment, acylated sugars are copolymerized with coreactants to yield novel sugar-based polymers. In another embodiment, non-reducing sugars acylated with a compound having a terminal double bond are polymerized to yield novel sugar-based polymers.Type: GrantFiled: May 31, 1994Date of Patent: April 8, 1997Assignee: University of Iowa Research FoundationInventors: Jonathan S. Dordick, David G. Rethwisch, Damodar R. Patil
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Patent number: 5597906Abstract: Carbon linked glycosyl compounds are disclosed and synthesized. The synthesis employs a blocked carbohydrate donor and a blocked glycosyl acceptor. The blocked carbohydrate donor includes an acid labile phosphite leaving group attached to the anomeric carbon. The blocked glycosyl acceptor includes an unprotected carbon susceptible to electrophilic attack. The reaction is initiated by the addition of a Lewis acid so as to activate the acid labile phosphite leaving group on the carbohydrate donor. The substitution reaction may be conducted at -78.degree. C. in a solvent which favors the formation of carbon linked glycosylation products.Type: GrantFiled: March 18, 1993Date of Patent: January 28, 1997Assignee: The Scripps Research InstituteInventors: Chi-Huey Wong, Hirosato Kondo
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Patent number: 5565129Abstract: The polycarbonates of the present invention include those of sucrose series having a specific cyclic structure, those of oligosaccharide and monosaccharide series other than the sucrose series, those derived from specific saccharides having no cyclic structure, those having a skeletal structure of pentaerythritol, neopentyl glycol or trimethylolmethane, and specific dicarbonates.The lubricating oil and electrical insulating oil of the invention contain the above-mentioned polycarbonates.The polycarbonates of the invention are excellent in compatibility with Freon R-134a (HFC) as well as in lubricating properties, detergency and electrical insulating properties, and are capable of providing lubricating oil for refrigerator, automotive engine oil, automotive gear oil, lubricating oil for rolling and lubricating oil for fiber, especially lubricating oil for which electrical insulating properties are required, and electrical insulating oil.Type: GrantFiled: June 1, 1995Date of Patent: October 15, 1996Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Masahide Tanaka, Tadaaki Fujimoto, Tetsuo Hayashi, Takashi Hayashi, Kazunori Takahata
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Patent number: 5559226Abstract: Polyol fatty acid polyesters having improved oxidative stability are prepared using the addition of an alkaline material to the synthesized crude polyol fatty acid polyesters before conducting the finishing of the crude. The alkaline material is added in an amount such that the finished product has a pH of from about 6.0 to about 8.5.Type: GrantFiled: March 21, 1994Date of Patent: September 24, 1996Assignee: The Procter & Gamble CompanyInventor: Robert J. Sarama
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Patent number: 5550155Abstract: Monofucosylated and monosialyated derivatives of the compound .beta.Gal(1-4).beta.GlcNAc(1-3).beta.Gal(1-4).beta.GlcNAc-OR, where R is hydrogen, a saccharide, an oligosaccharide or an aglycon moiety have been found to be useful in modulating a cell-mediated immune inflammatory response in mammals.Type: GrantFiled: October 14, 1994Date of Patent: August 27, 1996Assignee: Alberta Research CouncilInventors: Mohammed A. Kashem, Andre P. Venot, Richard Smith
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Patent number: 5550225Abstract: A process for preparing monoesters predominantly in the 6' position of D-maltose involves, in a first step forming in an organic solvent a mixed anhydride of formula (I): ##STR1## wherein R represents a linear or branched alkyl or alkenyl radical having 7-21 carbon atoms or R represents a defined mixture of the alkyl or alkenyl radicals, and R' represents a linear or branched alkyl having 2-10 carbon atoms, by reacting in the presence of a base, an R--COOH acid wherein R has the meaning given above with a ClCOOR' alkyl chloroformate wherein R' has the meaning given above, and in a second step reacting the mixed anhydride of formula (I) in solution in an organic solvent with D-maltose. The monoesters are employed in cosmetic, buccal-dental, pharmaceutical or food compositions.Type: GrantFiled: March 26, 1993Date of Patent: August 27, 1996Assignee: L'OrealInventor: Michel Philippe
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Patent number: 5545731Abstract: Alkyl and/or alkenyl oligoglycoside carbonates are obtainable by condensation of alkyl and/or alkenyl oligoglycosides corresponding to formula (I)R.sup.1 O--(R.sup.2 O).sub.x --[G].sub.p (I)in whichR.sup.1 is a C.sub.1-22 alkyl and/or alkenyl radical,R.sup.2 is a C.sub.2-4 alkylene radical,x is 0 or a number of 1 to 30,[G] is a sugar unit containing 5 or 6 carbon atoms andp is a number of 1 to 10,with dialkyl carbonates corresponding to formula (II)R.sup.3 O--CO--OR.sup.4 (II)in whichR.sup.3 and R.sup.4 independently of one another represent C.sub.1-10 alkyl radicals,in the presence of basic catalysts.Type: GrantFiled: October 3, 1994Date of Patent: August 13, 1996Assignee: Henkel Kommanditgesellschaft auf AktienInventor: Manfred Weuthen
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Patent number: 5543512Abstract: The invention concerns a process for preparing saccharide monomers comprising at least one polymerizable acrylate or methacrylate group whereby the saccharide used in the process is selected from mono-, di- and tri-saccharides, in particular from non-reducing mono-, di- and tri-saccharides. The process comprises reacting the saccharide in an aqueous medium with an esterifying reagent containing the polymerizable acrylate or methacrylate group in the presence of a base while maintaining the pH of the reaction medium to a value within the range of 7 to 11 during the entire reaction time. The invention furthermore concerns saccharide monomers comprising at least one polymerizable acrylate or methacrylate group with a controlled degree of substitution.Type: GrantFiled: January 26, 1995Date of Patent: August 6, 1996Assignee: Beghin-SayInventors: Julio Mentech, Isabelle Betremieux, Bruno Legger
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Patent number: 5508394Abstract: Esters of citric acid or acetylcitric anhydride with compounds of at least 3 OH groups selected from the group consisting of polyglycerol, sugarcarboxylic acids, alkyl glucosides, derivatives of oligosaccharides, aminosorbitol, aminodisorbitol, glucosamine, triethanolamine and trishydroxyethylmelamine, each OH group of the alcohol component of the esters being esterified on average with from 0.15 to 1 molecule of citric acid or acetylcitric anhydride, are useful as additives in low-phosphate or phosphate-free detergents.Type: GrantFiled: September 16, 1993Date of Patent: April 16, 1996Assignee: BASF AktiengesellschaftInventors: Elisabeth Kappes, Alfred Oftring, Richard Baur, Alexander Kud, Dieter Boeckh, Heinrich Hartmann, Volker Schwendemann
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Patent number: 5504202Abstract: A process for preparing a sucrose fatty acid polyester comprising mixing a sucrose ether having an average degree of etherification of from about 4 to about 8 with a basic catalyst and an excess of a fatty acid lower alkyl ester, heating the resultant mixture to a temperature of from about 120.degree. C. to about 180.degree. C. at a pressure of up to about 10 mm of mercury while removing the alcohol formed during the formation of the sucrose fatty acid polyester, and then separating the sucrose fatty acid polyester from the reaction mixture. The sucrose fatty acid polyester is a synthetic low calorie fat substitute and is useful in preparing edible non-digestible food products.Type: GrantFiled: April 5, 1994Date of Patent: April 2, 1996Assignee: Henkel CorporationInventor: Robert B. Hutchison
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Patent number: 5502175Abstract: Fatty acid esters of methylglucoside derivatives of formula I ##STR1## wherein A, B, C, D=21 to 75, R.sub.1, R.sub.2, R.sub.3, R.sub.4 =H or ##STR2## with R.sub.1 -R.sub.4 not simultaneously being H, and M=C.sub.11 -C.sub.18 alkenyl or alkyl.Type: GrantFiled: April 21, 1994Date of Patent: March 26, 1996Assignee: Th. Goldschmidt AGInventors: Natvarlei Desai, Klaus Wisotzki
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Patent number: 5498708Abstract: A new process is disclosed for the preparation of esters of polyhydroxy compounds having three or more hydroxy compounds. The process is based on the reaction with an alkyl chloroformate to form a mixed anhydride which is contacted with a polyol.Type: GrantFiled: July 18, 1989Date of Patent: March 12, 1996Assignee: Montefiore Medical CenterInventor: Iraj Lalezari
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Patent number: 5498602Abstract: Oligosaccharide aromatic glycoside sulfates and physiologically acceptable salts thereof, are disclosed. Further, antiviral agents having these sulfate compounds as the active components, and particularly an antiviral agent, wherein the virus is one which causes AIDS (Acquired Immune Deficiency Syndrome), are disclosed. The active components or the glycoside sulfates, and the salts thereof, are characterized by an oligosaccharide aromatic glycoside sulfate in which the hydrogen of the position-1 hydroxyl group of the terminal sugar of an oligosaccharide is substituted with a specified formula having an alkyl group consisting of 1 to 18 carbons, an oxygen or no oxygen, and an allylene group. The number of constituent monosaccharides in the oligosaccharide portion is preferably within a range of 2 to 20. Further, 10% or more of the remaining hydroxyl groups of the sugar subunits are subjected to sulfated esterification.Type: GrantFiled: September 11, 1992Date of Patent: March 12, 1996Assignee: Dainippon Ink and Chemicals, Inc.Inventors: Tadao Shoji, Nahoko Takahashi, Naoya Ikushima, Toshiyuki Uryu, Takashi Yoshida, Naoki Yamamoto, Hideki Nakashima, Kaname Katsuraya, Koichiro Adachi, Fusayo Kataoka
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Patent number: 5491226Abstract: A process for preparing polyol fatty acid polyesters having levels of triglyceride below 0.5% is described. Methyl esters having a level of monoglycerides below 500 ppm, a nondetectable level of di- and triglyceride and a glycerine level of less than about 200 ppm are prepared and then used in a two-stage, solvent-free transesterification reaction to prepare the polyol fatty acid polyesters.Type: GrantFiled: April 6, 1994Date of Patent: February 13, 1996Assignee: Procter & Gamble CompanyInventor: Corey J. Kenneally
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Patent number: 5489675Abstract: Novel NeuAc-Gal dissacharide sialidase substrates and inhibitors which are locked into rigid conformation by the attachment of an alkyl group at the C-6 arm of the galactose core are provided. Also provided is a method for the inhibition of sialidase activity.Type: GrantFiled: November 3, 1993Date of Patent: February 6, 1996Assignee: E. I. Du Pont de Nemours and CompanyInventor: Subramaniam Sabesan
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Patent number: 5488102Abstract: Compounds of formulae I and IaR--Y--CO--R.sub.3 --CO--O--A (I),R--Y--CO--R.sub.3 --CO--O--CH.sub.2 --A.sub.1 (Ia),whereinR is a radically polymerisable hydrocarbon group,R.sub.3 is a direct bond, linear or branched C.sub.1 -C.sub.22 alkylene, C.sub.3 -C.sub.8 cycloalkylene or C.sub.6 -C.sub.14 arylene,A is the radical, reduced by a hydroxy group in a 2- or 3position, of a cyclic-oligomeric carbohydrate or of a derivative of such a carbohydrate,A.sub.1 is the radical, reduced by a hydroxymethyl group, of a monomeric or linear oligomeric carbohydrate or of a derivative of such a carbohydrate, andY is --O--, --NH-- or --N(C.sub.1 -C.sub.6 alkyl)-.Homo- and co-polymers having those monomers have, depending upon their composition, hydrophilic, amphiphilic or hydrophobic properties and are able to form hydrogels. The polymers can be used, for example, as surfactants, thickeners, carriers for biologically active ingredients or in the manufacture of contact lenses.Type: GrantFiled: July 26, 1994Date of Patent: January 30, 1996Assignee: Ciba Geigy CorporationInventor: Dirk Vetter
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Patent number: 5474915Abstract: A poly(sugar acrylate) is prepared by reacting vinyl acrylate with a sugar in the presence of hydrolytic enzymes to prepare an acryloyl ester of the sugar. The acryloyl ester of the sugar is then polymerized to form the poly(sugar acrylate). Useful hydrolytic enzymes include alkaline protease, aminoacylase, fungal amylase, bacterial protease, lipase from Pseudomonas cepacia and subtilisin. Useful sugars include .alpha.- or .beta.-alkyl- or .alpha.- or .beta.-halo-glycosides, sucrose, fructose, mannose, trehalose, raffinose, lactose and maltose. A free radical initiator can be used in the polymerization. A copolymer can be formed by mixing the sugar ester with a monomer such as 2-hydroxyethyl methacrylate before polymerizing. During formation of the copolymer, a cross-linking agent such as ethylene glycol dimethacrylate may be present. The poly(sugar acrylates) form hydrogels which are useful in absorbent materials such as diaper liners, packaging materials and drug delivery polymers.Type: GrantFiled: February 7, 1994Date of Patent: December 12, 1995Assignee: University of Iowa Research FoundationInventors: Jonathan S. Dordick, Brett D. Martin, Robert J. Linhardt
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Patent number: 5470969Abstract: Sucrose is mono-acylated in the 6-position by reacting sucrose with a carboxylic acid anhydride such as acetic or benzoic anhydride in a reaction mixture containing a polar aprotic solvent and a catalytic quantity of a 1,3-diacyloxy-1,1,3,3-tetra(hydrocarbyl)distannoxane, for a period of time and at a temperature sufficient to produce a sucrose-6-ester.Type: GrantFiled: May 2, 1994Date of Patent: November 28, 1995Assignee: McNeil-PPC, Inc.Inventors: George H. Sankey, Nicholas M. Vernon, Robert E. Wingard, Jr.
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Patent number: 5459257Abstract: A sulfated oligoglycoside acylate comprising monosaccharides of a single or two kinds as the constituents, wherein the hydrogen in the hydroxyl group at the 1-position of a reducing end sugar of the oligosaccharide formed via the glycoside bond of these monosaccharides has been substituted with an aglycon selected from a group consisting of alkyl groups, aromatic alkyl groups, aromatic alkoxy groups and tocopheryl groups; from 12 to 80% of the residual hydroxyl groups have been acylated with an acyl group selected from a group consisting of aliphatic acyl groups and aromatic acyl groups; and 88 to 20% thereof have been sulfated; or a physiologically acceptable salt thereof provided that compounds wherein the aglycon is an alkyl group and the acyl group is an aliphatic acyl group are excluded is disclosed. Further, an antiviral agent, which exerts a long-lasting antiviral action particularly on HIV, containing said compound as an active ingredient is disclosed.Type: GrantFiled: January 7, 1994Date of Patent: October 17, 1995Assignee: Dainippon Ink and Chemicals, Inc.Inventors: Tadao Shoji, Akira Kasai, Osamu Misumi, Naoya Ikushima, Naoki Yamamoto, Hideki Nakashima, Kazuhiko Inazawa, Nahoko Takahashi
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Patent number: 5449772Abstract: A method is provided for the preparation of a sucrose 6-ester by: (i) reacting a solution of sucrose in an inert organic solvent with a reagent selected from the group consisting of a trialkyl orthoester and a ketene acetal, in the presence of an acid catalyst to provide a sucrose alkyl 4,6-orthoester, (ii) treating the sucrose alkyl 4,6-orthoester under mild aqueous acidic conditions to provide a mixture of sucrose 4- and 6-monoesters, (iii) treating the mixture of esters with a base to convert the sucrose 4-ester into sucrose 6-ester, and (iv) neutralizing the solution and isolating the sucrose 6-ester, in which stage (i) is effected in a continuous manner by passing the solution of sucrose and reagent through a strong acid macroreticular ion exchange resin at ambient temperature. Sucralose is prepared by chlorinating the sucrose 6-esters obtained.Type: GrantFiled: May 20, 1993Date of Patent: September 12, 1995Assignee: Tate & Lyle Public Ltd. Co.Inventor: George H. Sankey
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Patent number: 5440026Abstract: A method for the preparation of a sucrose 6-ester comprises:(i) reacting sucrose with a ketene acetal in the presence of an acid catalyst in an inert organic solvent to form a sucrose alkyl 4, 6-orthoester;(ii) subjecting the sucrose alkyl 4, 6-orthoester to mild acidic hydrolysis to provide a mixture of 4- and 6-monoesters of sucrose; and(iii) treating the mixture of sucrose monoesters with a base to convert the sucrose 4-ester into sucrose 6-ester. Sucralose may be prepared by chlorination of sucrose 6-esters prepared according to the invention.Type: GrantFiled: May 21, 1992Date of Patent: August 8, 1995Assignee: Tate & Lyle Public Limited Co.Inventors: Riaz A. Khan, Keith Smith, Andrew Pelter, Jin Zhao
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Patent number: 5440027Abstract: An improved method for the preparation of saccharide fatty acid polyesters via a two-step process is provided. In the first step, a saccharide is partially esterified so as to contain, on average, between about 1.5 to 3.5 lower acyl ester groups. In the second step, the partially esterified saccharide is reacted with a fatty acid-containing reagent (for example, fatty acids, fatty acid esters, salts of fatty acids, or fatty acid anhydrides) whereby the lower acyl ester groups and the hydroxyl groups on the partially esterified saccharide are replaced with fatty acid ester groups in a transesterification reaction to form a saccharide fatty acid polyesters. The use of a partially esterified saccharide as a reactant in the transesterification reaction allows for a more homogeneous reaction system, less caramelization or other decomposition reactions, and less low molecular weight ester by-product formation.Type: GrantFiled: October 5, 1993Date of Patent: August 8, 1995Assignee: Kraft General Foods, Inc.Inventor: Gerry Hasenhuettl
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Patent number: 5432267Abstract: A compound represented by formula (I): ##STR1## wherein R.sup.1 represents --CO--Z.sup.1 --N(Z.sup.11)--CO--Z.sup.2 --H or --CO--Z.sup.3 --H, wherein Z.sup.1, Z.sup.2, and Z.sup.3 each represent an alkylene group having from 1 to 20 carbon atoms, a phenylene group, or a combination thereof, and Z.sup.11 represents a hydrogen atom, an alkyl group having from 1 to 20 carbon atoms which may be substituted with a phenyl group, a phenyl group which may be substituted with an alkyl group having from 1 to 20 carbon atoms, or an alkylene group having from 1 to 20 carbon atoms which may contain therein a phenylene group; R.sup.2 represents --CO--Z.sup.4 --N(Z.sup.12)--CO--Z.sup.5 --H, --CO--Z.sup.6 --H or a hydrogen atom, wherein Z.sup.4, Z.sup.5, and Z.sup.6 each have the same meaning as Z.sup.1, and Z.sup.12 has the same meaning as Z.sup.11 ; Q.sup.1 and Q.sup.2 each represent a carboxyl group or a phosphonoxy group; Q.sup.Type: GrantFiled: March 31, 1993Date of Patent: July 11, 1995Assignee: Daiichi Pharmaceutical Co., Ltd.Inventors: Tsuneo Kusama, Tsunehiko Soga, Akiko Tohgo
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Patent number: 5424420Abstract: An improved method for the preparation of saccharide fatty acid polyesters via an intermolecular transesterification reaction is provided. A saccharide lower acyl ester (for example, sucrose octaacetate) is reacted with a fatty acid lower alkyl ester (for example, methyl stearate) in the presence of an alkali metal alkoxide catalyst to produce a saccharide fatty acid polyester. The reaction is carried out at relatively low temperatures in the absence of solvent. The relatively low molecular weight by-produce ester is removed from the reaction mixture during the course of the reaction in order to drive the equilibrium transesterification reaction to completion. The saccharide fatty acid polyesters are useful as fat substitutes or low-calorie fats in food compositions.Type: GrantFiled: October 5, 1993Date of Patent: June 13, 1995Assignee: Kraft Foods, Inc.Inventors: Gerry Hasenhuettl, Laura Labeots
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Patent number: 5386019Abstract: The total synthesis of a group of compounds with inhibitory effects on calmodulin-mediated enzyme activities has been accomplished. Among these synthesized compounds are KS-501 and KS-502. Other compounds that have been synthesized by the described scheme are ent-KS-501 and ent-KS-502 which are enantiomers of KS-501 and KS-502 and which also have inhibitory effects on calmodulin-mediated enzyme activities.Type: GrantFiled: January 15, 1992Date of Patent: January 31, 1995Assignee: Yale UniversityInventors: Samuel J. Danishefsky, Russell Dushin, William N. Hait
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Process for purifying products containing esters of a non-reducing sugar and one or more fatty acids
Patent number: 5378834Abstract: The invention relates to a process for purifying crude products containing esters of a non-reducing sugar like sucrose, and one or more fatty acids such as palmitic acid, stearic acid etc. by subjecting the crude esterification products to an extraction treatment with supercritical carbon dioxide. After carrying out this extraction treatment a residue comprising the fatty acid esters of non-reducing sugars, the unreacted sugar and the salts as well as an extract comprising the fatty acids, fatty acid alkyl esters and also any solvents, if present, are obtained. The unreacted sugar and the salts, present in the obtained residue, can be removed from the residue by, for example, a washing operation resulting in a final product of pure esters of the non-reducing sugar and one or more fatty acids. This last removal step concerning the unreacted sugar and salts may also be carried out before the application of the above indicated extraction treatment with supercritical carbon dioxide.Type: GrantFiled: July 14, 1993Date of Patent: January 3, 1995Assignee: Cooperatieve Vereniging Suiker Unie U.A.Inventors: Kees Koerts, Age Bakker, Gerardus M. Vianen -
Patent number: 5374655Abstract: Disclosed are methods for the preparation of monofucosylated and sialylated derivatives of the compound .beta.Gal(1-4).beta.GlcNAc(1-3).beta.Gal(1-4).beta.GlcNAc-OR. In particular, the methods of this invention provide for a multi-step synthesis wherein selective monofucosylation is accomplished on the 3-hydroxy group on only one of the GlcNAc units found in the .beta.Gal(1-4) .beta.GlcNAc (1-3) .beta.Gal (1-4) .beta.GlcNAc-OR compound. In this step, monofucosylation is achieved by use of the .alpha.(1-3)fucosyltransferase.Type: GrantFiled: July 14, 1992Date of Patent: December 20, 1994Assignee: Alberta Research CouncilInventors: Mohammed Kashem, Andre P. Venot, Richard Smith
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Patent number: 5278303Abstract: This invention relates to the preparation of oligosaccharides, using polymer supported methodology. By this method, which offers anomeric control, oligosaccharides are produced very rapidly in comparison with known methodologies. Thus, there is disclosed a process for the preparation of oligosaccharides which comprisesa) forming a synthon of a saccharide and a monomethylether of polyethylene glycol or a derivative thereof, the synthon having a linkage between the oligosaccharide and the monomethylether of polyethylene glycol or a derivative thereof, which linkage can be severed under conditions that do not damage glycosidic or other bonds in a desired end product;b) subjecting the synthon to repeated additions of a suitable glycosylating agent to form a desired oligosaccharide-polyethylene glycol linked product;c) isolating the linked product as a solid;d) purifying this solid; ande) releasing the oligosaccharide from the polyethylene glycol.Type: GrantFiled: June 12, 1992Date of Patent: January 11, 1994Assignee: University of Toronto Innovations FoundationInventors: Jiri J. Krepinsky, Stephen P. Douglas, Dennis M. Whitfield
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Patent number: 5270461Abstract: Benzoic acid esters of an ethoxylated methyl glucosides and of a propoxylated methyl glucosides exhibit enhanced characteristics that make these esters ideally suited for skin and hair care compositions. These esters demonstrate enhanced capabilities as foam boosters, emollients, conditioners, clarifiers, solubilizers, and carriers (diluents). In addition, oxybenzone, benzocaine, ibuprofin and dihydroxyacetone (DHA) can be solubilized by these esters. These esters have the ability to solubilize both hydrophilic and hydrophobic materials such as DHA. The benzoate esters have lower surface tensions than the glucam polyol molecules from which they were derived.Type: GrantFiled: November 19, 1991Date of Patent: December 14, 1993Assignee: Finetex, Inc.Inventors: Ismail I. Walele, Nicolas J. Scarangella, Anthony Ansaldi, Ann M. Andrews