Esters Patents (Class 536/115)
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Patent number: 5633366Abstract: Nucleoside derivatives such as 2'-deoxy-2'-bromo-5'-O-acetyl-5-methyluridine, etc., are important intermediates which can be converted into nucleoside derivatives, such as 3'-azido-3'-deoxythymidine, etc., which are useful as medicines.Type: GrantFiled: August 4, 1994Date of Patent: May 27, 1997Assignee: Ajinomoto Co., Inc.Inventors: Satoshi Takamatsu, Hiroshi Shiragami, Yumiko Uchida, Kunisuke Izawa
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Patent number: 5629412Abstract: A class of molecules that alter cell adhesion. A cell adhesion affector according to the present invention essentially consists of an amino acid linked to a carbohydrate wherein the amino acid and the carbohydrate are linked to form a compound chosen from the group consisting of Schiff bases, N-glycosides, esters, and Amadori products. The carbohydrate is preferably a monosaccharide or a small oligosaccharide. The carbohydrate and amino acid sub-units may be chemically modified. For example, the amino acid may be modified by covalently bonding other groups to the amino group, carboxyl group, or side chain group of the amino acid. The carbohydrate sub-unit is preferably a pentose such as arabinose, xylose, ribose, ribulose, a hexose such as fructose, deoxyfructose, galactose, glucose, mannose, tagatose, rhamnose, or a disaccharade based on two of the above such as maltose, lactose, maltulose, or lactulose.Type: GrantFiled: July 11, 1994Date of Patent: May 13, 1997Inventor: Guennadi V. Glinskii
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Patent number: 5625044Abstract: The present invention relates to a method for the making pure homologous series of fatty acyl esters of sugars. The production mono- to tetrapalmitates of maltose is particularly examplified. Specific compositions containing di-, tri- and tetrapalmitates of maltose show an antitumoral activity, an immunostimulating and, to some extent, an antiangiogenic effects are also described and claimed. They can be used alone or in the presence of angiostatic steroids for treating angiogenesis-dependent deseases. The characterization of one such new compound, maltose 1, 6, 6' tripalmitate which is the active component of this series is included.Type: GrantFiled: December 16, 1994Date of Patent: April 29, 1997Assignee: Goudreau Gage Dubec & MartineauInventors: Vijai N. Nigam, Prom et eo Madarnas, Gilles Dupuis
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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: 5606036Abstract: The present invention relates to novel ester derivatives of antibiotic A 40926 complex and its N-acylaminoglucuronyl aglycone. The compounds of the invention are prepared according to an esterification process involving reaction of an A 40926 substrate with an excess of the selected alkanol in the presence of concentrated mineral acid and are reactive as antibiotics.Type: GrantFiled: May 22, 1995Date of Patent: February 25, 1997Assignee: Gruppo Lepetit SpAInventors: Rolf H. Hermann, Romeo Ciabatti, Enrico Selva, Maurizio Denaro
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Patent number: 5602103Abstract: Crocetin disaccharide esters represented by the following general formula: ##STR1## wherein R.sub.1 and R.sub.2 are gentiobiose groups or glucose groups and may be the same or different groups from each other, are effective for dose-dependently improving the hippocampal long-term potentiation blocking effect of ethanol and are used as an effective cerebral function-ameliorating agent.Type: GrantFiled: March 3, 1995Date of Patent: February 11, 1997Assignee: Nippon Mektron, LimitedInventors: Minoru Sugiura, Hiroshi Saito, Yukihiro Syoyama
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Patent number: 5599800Abstract: Compositions of gel-like appearance, comprising an oily phase formed of at least 75% of organopolysiloxane, dispersed in an aqueous phase containing at least 25% of water, using an emulsifying agent formed of at least one sucrose ester, are stable in the presence of compounds which are not compatible with conventional gelling agents.Type: GrantFiled: October 4, 1994Date of Patent: February 4, 1997Assignee: L'OrealInventors: Didier Candau, Pascal Simon
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Patent number: 5593853Abstract: Methods are provided for generating highly diverse mixtures of compounds which may be screened for biological activities. Once the activity is found, the component of the mixture which is responsible for the activity can be isolated by fractionation and assay for the biological activity. Polyhydroxylated organic monomers and oligomers are used as starting materials for generating the libraries.Type: GrantFiled: February 9, 1994Date of Patent: January 14, 1997Assignee: Martek CorporationInventors: Hao Chen, Richard Radmer
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Patent number: 5563250Abstract: The present invention provides cleavable conjugates whose linkers contain a labile bond that is cleavable under a variety of mild conditions, including weakly acidic. Since the agent may be bonded directly to the linker, cleavage can result in release of native agent. The invention also provides methods for producing cleavable conjugates. Preferred agents include drugs, toxins, biological response modifiers, radiodiagnostic compounds, radiotherapeutic compounds, and derivatives thereof. The targeting molecule employed in the invention may be an intact molecule, a fragment thereof, or a functional equivalent thereof. In a particularly preferred embodiment, the targeting molecule is a monoclonal antibody directed towards a tumor-associated antigen in man. The invention further provides methods for delivering to the cytoplasm of a target cell an agent free of its targeting molecule carrier.Type: GrantFiled: May 13, 1994Date of Patent: October 8, 1996Assignee: NeoRx CorporationInventors: Mark D. Hylarides, Ananthachari Srinivasan, Jeffrey N. Fitzner, Vivekananda M. Vrudhula
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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: 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: 5536826Abstract: A process for preparing amino-functional cyclodextrin derivatives has an amino function which is linked to the cyclodextrin (CD) via a spacer. Compositions containing CD derivatives are prepared by this process. In this process, .alpha.-cyclodextrin, .beta.-cyclodextrin or .gamma.-cyclodextrin, or their partially substituted derivatives, is reacted individually or in arbitrary mixture with at least one cyclic carbamic ester. The CD derivatives, as regards the listed amino substituents, have an average degree of molar substitution per anhydroglucose unit (MS) of 0.01-0.2 and a proportion of monoamino-substituted CD derivatives which is greater than 70%.Type: GrantFiled: December 13, 1994Date of Patent: July 16, 1996Assignee: Consortium fur elektrochemische Industrie GmbHInventor: Rolf Hirsenkorn
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Patent number: 5536823Abstract: Analogues of RNA and DNA compounds contain a neutral, stereoregular linking group based on replacement of the phosphoryl with a sulfonyl group. Precursors to the analogues are also described, as are methods for preparing the precursors and analogues.Type: GrantFiled: November 3, 1993Date of Patent: July 16, 1996Assignee: Indiana University FoundationInventor: Theodore S. Widlanski
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Patent number: 5532350Abstract: A solid composition of matter comprising one or more polysaccharides which has been cross-linked with either titanium or zirconium cross-linking agents is provided. The composition demonstrates absorbent properties and is useful in absorbent articles of manufacture. Also provided is a method for preparing the compositions.Type: GrantFiled: February 15, 1994Date of Patent: July 2, 1996Assignee: Rhone-Poulenc Inc.Inventors: Ian W. Cottrell, Animesh Goswami, Manjit S. Chowdhary
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Patent number: 5530106Abstract: There is disclosed a process for recovering sucralose-6-ester from a feed mixture of 6-O-acyl-4,1',6'-trichloro-4,1',6'-trideoxygalactosucrose in a reaction medium comprising a tertiary amide (such as N,N-dimethylformamide), wherein said process comprises removing a major proportion of said tertiary amide by steam distillation. In preferred aspects of the invention, the steam distillation is followed by extraction and then purification by crystallization or crystal aging to recover sucralose-6-ester in good yield.Type: GrantFiled: January 4, 1995Date of Patent: June 25, 1996Assignee: McNeil-PPC, Inc.Inventors: Juan L. Navia, Robert E. Walkup, David S. Neiditch
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Patent number: 5527903Abstract: A process for preparing a sucrose fatty acid ester having a low degree of substitution, comprising heat-melting a sucrose fatty acid ester (A) having an average degree of substitution of from 3 to 8 and sucrose or a sucrose fatty acid ester (B) having a lower degree of substitution than that of said sucrose fatty acid ester (A) in the presence of an alkali catalyst and a soap; and a process for preparing a sucrose fatty acid ester having a high degree of substitution comprising a first step of heat-melting a sucrose fatty acid ester (A) having an average degree of substitution of from 3 to 8 and sucrose or a sucrose fatty acid ester (B) having a lower degree of substitution than that of said sucrose fatty acid ester (A) in the presence of an alkali catalyst and a soap and a second step of reacting the resulting molten mixture with a fatty acid lower alkyl ester are disclosed.Type: GrantFiled: June 11, 1992Date of Patent: June 18, 1996Assignee: Mitsubishi Kasei CorporationInventors: Yukio Kasori, Tetsuro Yamazaki
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Patent number: 5523398Abstract: The invention is directed to the formation of cellulose derivatives using homogenous phase reaction conditions. Cellulose is dissolved using DMAc/LiCl and a reagent system is added to promote the acylation of an appropriate acid anhydride or free carboxylic acid. One reagent system includes N,N-dicyclohexylcarbodiimide (DCC) and 4-pyrrolidinopyridine (PP). Another reagent system includes p-toluene sulfonyl chloride (TsCl) and pyridine (Py).Type: GrantFiled: August 31, 1994Date of Patent: June 4, 1996Assignees: The Center for Innovative Technology, Virginia Polytechnic Institute and State University, Virginia Tech Intellectual PropertiesInventors: Wolfgang G. Glasser, Gamini Samaranayake, James E. Sealey, II
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Patent number: 5521304Abstract: Water soluble or water-dispersible cellulose acetoacetate esters are prepared by contacting a cellulose material with diketene, an alkyl acetoacetate, 2,2,6-trimethyl-4H-1,3-dioxin-4-one or a mixture thereof and a carboxylic anhydride in a solvent system comprising lithium chloride plus a carboxamide. Compositions containing the cellulose acetoacetate esters are useful for coatings applications.Type: GrantFiled: February 27, 1995Date of Patent: May 28, 1996Assignee: Eastman Chemical CompanyInventors: Kevin J. Edgar, Jonathan E. Lawniczak
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Patent number: 5514791Abstract: Variant xanthan gums are provided which include a water-soluble polysaccharide polymer comprising repeating pentamer units having a D-glucose:D-mannose:D-glucuronic acid ratio of about 2:2:1, and a water-soluble polysaccharide polymer comprising repeating tetramer units having a D-glucose:D-mannose:D-glucuronic acid ratio of about 2:1:1. The D-glucose moieties are linked in a beta- 1,4! configuration. The inner D-mannose moieties are linked in an alpha- 1,3! configuration, generally to alternate glucose moieties. The D-glucuronic acid moieties are linked in a beta- 1,2! configuration to the inner mannose moieties. The outer mannose moieties are linked to the glucuronic acid moieties in a beta- 1,4! configuration. Processes for preparing the polysaccharide polymers are also provided.Type: GrantFiled: April 25, 1994Date of Patent: May 7, 1996Assignee: Getty Scientific Development CompanyInventors: Daniel H. Doherty, Donna M. Ferber, John D. Marrelli, Rebecca W. Vanderslice, Randal A. Hassler
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Patent number: 5514658Abstract: A method for obtaining oligosaccharides starts with allylation of position (3') of .beta.-lactosides followed by controlled benzylation, which leads to perbenzylated and partially benzylated compounds. The latter are glycosylated at position 3, not benzylated, with a donor of .varies.-fucopyranosyl to yield protected trisaccharides. These and perbenzylated .beta.-Lactosides are deallylated and, later, are glycosylated with 2-azido-2-deoxy-.varies.-D-galactopyranosyl to yield protected tetrasaccharides and trisaccharides, respectively. The debenzylation of said products accompanied by the reduction of the azido group and simultaneous acetylation of the amino group produces intermediary products which, by O-deacetylation, leads respectively to the final tetrasaccharides and trisaccharides.Type: GrantFiled: July 12, 1993Date of Patent: May 7, 1996Assignee: Consejo Superior Investigaciones CientificasInventors: Fernando F. Santos Benito, Manuel Nieto Sampedro, Alfonso Fernandez-Mayoralas, Maanuel Martin Lomas
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Patent number: 5514662Abstract: The invention is directed toward the use of amphotericin B and derivatives thereof as inhibitors of serine-proteases and for applying these inhibitors for the production of medicinal products intended for the treatment of infection by the human immunodeficiency virus (HIV).Type: GrantFiled: November 15, 1993Date of Patent: May 7, 1996Assignee: Laboratoires Mayoly Spindler (S.A.R.L.)Inventor: Michel Seman
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Patent number: 5512671Abstract: Ether lipid nucleoli covalent conjugates and derivatives thereof are disclosed, along with pharmaceutical compositions containing the same and methods of using the same to combat HIV-1 infections. Illustrative are 3'-Azido-3'-deoxythmidine-5'-monophosphate-D,L-3-octadecanamido-2-ethoxypr opane and 3'-Azido-3'-deoxythymidine-5'-butyrate-.gamma.-N,N,N-trimethyl -ammonium-.beta.-(1-phospho-2-ethoxy-3-hexadecyloxypropane).Type: GrantFiled: April 7, 1995Date of Patent: April 30, 1996Assignees: Wake Forest University, University of North Carolina at Chapel HillInventors: Claude Piantadosi, Canio J. Marasco, Jr., Louis S. Kucera
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Patent number: 5508387Abstract: Glyco-amino acids or glycopeptides that have three-dimensionally stable configuration for the presentation of functional groups, fucose, or an analogue or derivative thereof, covalently linked to an amino acid or peptide with a free carboxylic acid group, that facilitate binding between those groups and receptors on selectins, represented by the general structural formula I.Type: GrantFiled: August 4, 1993Date of Patent: April 16, 1996Assignee: Glycomed IncorporatedInventors: Peng C. Tang, Daniel E. Levy, Kevin R. Holme, Saeed A. Abbas
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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: 5496937Abstract: A polysaccharide substance having the following formula is provided: ##STR1## Also provided is a method of producing the polysaccharide substance in which an oligosaccharide having a degree of polymerization from 3 to 10 is chemically bonded to a silane agent at the reducing terminal of the resultant oligosaccharide, the oligosaccharide compound is then polymerized to an average degree of polymerization from 11 to 500 in the presence of an enzyme. Another method for producing the polysaccharide substance is provided in which an aldehyde group at the reducing terminal of an oligosaccharide having a degree of polymerization from 3 to 10 is oxidized with an oxidizing agent, and the saccharide chain of the oxidized product is polymerized to a degree of polymerization from 11 to 500 in the presence of an enzyme, followed by the addition of an acid. The polysaccharide substance has excellent solvent resistance and is useful as a separating agent for chromatography, especially for the separation of chiral compounds.Type: GrantFiled: May 9, 1994Date of Patent: March 5, 1996Assignee: Nakano Vinegar Co., Ltd.Inventors: Yoshio Okamoto, Naoki Enomoto, Sachiko Furukawa, Yasushi Ogasawara, Hirofumi Akano, Yoshiya Kawamura
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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: 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: 5476924Abstract: The present invention relates to a method of protecting the hemiacetal or acetal group at the anomeric carbon of a saccharide molecule comprising forming a 4-alkenyl glycoside or 4-alkenoyl glycosyl ester. The invention also relates to use of 4-alkenyl glycosides and 4-alkenoyl glycosyl esters in carbohydrate chemistry, including in the synthesis of oligosaccharides.Type: GrantFiled: December 21, 1994Date of Patent: December 19, 1995Assignee: Duke UniversityInventors: Bertram O. Fraser-Reid, David R. Mootoo, J. Cristobal Lopez
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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: 5472599Abstract: A separation agent essentially comprises an aliphatic or aromatic ester of a polysaccharide, except for cellulose acetate and an aromatic ester of cellulose. It is useful for separation of various chemical substances, especially optical resolution of optical isomers.Type: GrantFiled: March 9, 1995Date of Patent: December 5, 1995Assignee: Daicel Chemical Industries, Ltd.Inventors: Tohru Shibata, Hajime Namikoshi, Ichiro Okamoto
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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: 5459248Abstract: Etoposide phosphate is prepared by coupling dibenzyl 4'-demethyl-4-epipodophyllotoxin-4'-phosphate with 2,3-di-O-benzyl-4,6-O-ethylidene-.alpha.,.beta.-D-glucopyranose in a solvent and subsequently removing the protecting groups. The tetra-benzyl protected etoposide phosphate is recrystallized from methanol or directly crystallized from acetonitrile by adding methanol to yield substantially the pure C-1"-.beta. form. The benzyl protecting groups are simultaneously removed by hydrogenation to produce etoposide phosphate in high yields. In a further embodiment, etoposide phosphate is treated with a phosphatase enzyme to yield etoposide.Type: GrantFiled: November 4, 1993Date of Patent: October 17, 1995Assignee: Bristol-Myers Squibb CompanyInventors: Lee J. Silverberg, Purushotham Vemishetti, John L. Dillon, Jr., John J. Usher
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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: 5455336Abstract: The invention relates to a process for the preparation of low-calorie polysaccharide derivatives, obtained by feeding a worm shaft reactor, operating at elevated temperature and under elevated pressure, with a mixture of at least a saccharide, a polyol and a food-grade polycarboxylic acid. The products obtained may be added as low-calorie bulking agent to (diet) foodstuffs like puddings, cake etc..Type: GrantFiled: December 3, 1992Date of Patent: October 3, 1995Assignee: Cooperatieve Vereniging Suiker Unie U.A.Inventors: Gerardus M. Vianen, Kees Koerts, Hendrika C. Kuzee
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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: 5430142Abstract: A process for chemically modifying substantially pure xylose-rich oligosaccharides and polysaccharides in homogenous phase solution. The process may be advantageously utilized to produce biodegradable, thermoplastic, melt flowable, low shear resistant and low viscosity xylan derivatives.Type: GrantFiled: August 6, 1993Date of Patent: July 4, 1995Assignee: The Center for Innovative TechnologyInventors: Wolfgang G. Glasser, Rajesh K. Jain, Markku A. Sjostedt
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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: 5415769Abstract: A separation agent essentially comprises an aliphatic or aromatic ester of a polysaccharide, except for cellulose acetate and an aromatic ester of cellulose. It is useful for separation of various chemical substances, especially optical resolution of optical isomers.Type: GrantFiled: April 19, 1994Date of Patent: May 16, 1995Assignee: Daicel Chemical Industries, Ltd.Inventors: Tohru Shibata, Hajime Namikoshi, Ichiro Okamoto
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Patent number: 5416205Abstract: Partial esters of alginic acid and salts thereof possess important bioplastic and pharmaceutical qualities and are useful in various fields including medical, surgical, cosmetics and foods.Type: GrantFiled: November 22, 1993Date of Patent: May 16, 1995Assignee: Fidia, S.p.A.Inventors: Francesco della Valle, Aurelio Romeo
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Patent number: 5386016Abstract: The invention relates to 2",3",4'-tris(acetyl)-4",6"-ethylidene-.beta.-D-glucopyranosides, their preparation and their use for the preparation of 4'-demethylepipodophyllotoxin ethylidene-.beta.-D-glucopyranoside. The compounds of the invention are of the formula ##STR1## Their process of preparation comprises the following stages: acylation of a glycosyl derivativeacylation of an aglyconecoupling of the acylated glycosyl derivative and the acylated aglycone, in the presence of a Lewis acid, the acylation being carried out using an acid chloride, which is optionally identical for the two stages of acylation, in which the carbon in .alpha. of the carbonyl function bears at least one heteroatom chosen from among O and S.Type: GrantFiled: November 19, 1993Date of Patent: January 31, 1995Assignee: Pierre Fabre MedicamentInventors: Jean-Pierre Robin, Valerie Lenain
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Patent number: 5384311Abstract: This invention relates to liquid sucralose concentrate compositions comprising sucralose, a preservative system, a buffering system and a liquid.Type: GrantFiled: August 18, 1992Date of Patent: January 24, 1995Assignee: McNeil-PPC, Inc.Inventors: Robert N. Antenucci, Richard L. Barndt, Kas Mohammed