Carboxylic Patents (Class 536/119)
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Patent number: 6291671Abstract: A method for preparing a drug complex in which a polysaccharide derivative having carboxyl groups and a residue of a drug compound are bound to each other by means of a spacer comprising an amino acid or a spacer comprising peptide-bonded 2 to 8 amino acids, or a drug complex in which a polysaccharide derivative having carboxyl groups and a residue of a drug compound are bound to each other without the spacer, characterized in that an organic amine salt of the polysaccharide derivative having carboxyl groups is reacted with the drug compound or the spacer bound to the drug compound in a non-aqueous system. The reaction between the polysaccharide derivative having carboxyl groups and the drug compound bound with the spacer or the like can be carried out in high yields, and when a drug compound having a lactone ring is subjected to the reaction, side reactions can be reduced.Type: GrantFiled: March 22, 1999Date of Patent: September 18, 2001Assignee: Daiichi Pharmaceutical Co., Ltd.Inventors: Kazuhiro Inoue, Hiroshi Susaki, Masahiro Ikeda
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Patent number: 6274356Abstract: A carbohydrate complex, which is a mixture of low molecular-weight polysaccharides of an arabinomannan structure extracted from Mycobacterium tuberculosis, is highly effective in treating various cancer patients without incurring any adverse side effects.Type: GrantFiled: December 9, 1999Date of Patent: August 14, 2001Inventors: Tai-Ho Chung, Chong-Chan Chung
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Patent number: 6268493Abstract: Cellobiuronic acid may be prepared by hydrolysis of gellan. The method provides embodiments expressed in terms of amounts of cellobiuronic acid produced, amounts of gellan gum hydrolyzed and amounts of cellobiuronic acid present in fractions of a hydrolysate The method may further include isolation of a separated fraction of the hydrolysate where the separated fraction comprises cellobiuronic acid. A preferred embodiment of the method includes hydrolyzing gellan gum with a protic acid under reaction conditions that convert at least 95 wt. % of the gellan gum to a hydrolysate comprised of cellobiuronic acid and monosaccharides and isolating a separated fraction of the hydrolysate where cellobiuronic acid comprises at least a 95 wt. % of saccharides in the separated fraction.Type: GrantFiled: August 7, 1998Date of Patent: July 31, 2001Assignee: Center for the Application of Molecular Biology to International AgricultureInventor: Richard A. Jefferson
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Patent number: 6258799Abstract: An aqueous coating composition comprising hydroxypropyl methyl cellulose trimellitate typically having a mean particle size of up to 10 &mgr;m and a plasticizer is applied to a solid pharmaceutical preparation to form a coating film having acid resistance and solubility at about pH 4. The coated preparation has an improved bioavailability.Type: GrantFiled: September 24, 1999Date of Patent: July 10, 2001Assignee: Shin-Etsu Chemical Co. Ltd.Inventors: Hiroyasu Kokubo, Yuichi Nishiyama
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Patent number: 6245902Abstract: The invention provides versatile sialic acid C-glycoside precursors that are useful for preparing C-glycoside analogs of Gangliosides, peptides, and proteins, as well as synthetic intermediates useful for the preparation of the precursors, and synthetic methods useful for preparing the precursors and the intermediates. The invention also provides gangliosides, peptides, and proteins that comprise sialic acid C-glycoside components, as well as synthetic methods useful for the preparation of such compounds.Type: GrantFiled: August 9, 1999Date of Patent: June 12, 2001Assignee: University of Iowa Research FoundationInventors: Robert J. Linhardt, Helene G. Bazin, Yuguo Du, Tulay Polat
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Patent number: 6229009Abstract: A cross-linked copolymer based on at least one non-crosslinked polycarboxylic polysaccharide and at least one second non-crosslinked polycarboxylic polymer which is not a polycarboxylic polysaccharide and a cross-linking agent having at least two amine functions.Type: GrantFiled: February 18, 1999Date of Patent: May 8, 2001Assignee: Societe de Conseils de Recherches et d'Applications Scientifiques (S.C.R.A.S.)Inventors: Nada Lambert, Denis Labarre, Hatem Fessi
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Patent number: 6222031Abstract: Disclosed is a process for preparing a water-soluble tricarboxypolysaccharide which includes the step of oxidizing an &agr;-bonding type polysaccharide with a ruthenium compound and an oxidizing agent. The water-soluble tricarboxypolysaccharide, having a high carboxyl group content, can easily and inexpensively be prepared in a high yield without any problem of a post-treatment after the reaction, and thus the present invention is desirable as an industrial preparation process of the water-soluble tricarboxpolysaccharide.Type: GrantFiled: January 27, 1998Date of Patent: April 24, 2001Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Hidechika Wakabayashi, Toru Takahashi, Masaru Sakamoto, Rieko Sano
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Patent number: 6204256Abstract: A cyclodextrin derivative, wherein at least 60 percent of the free hydroxy groups of said cyclodextrin are acylated with acyl groups where at least one of said acyl groups comprise a free carboxylic group.Type: GrantFiled: April 8, 1999Date of Patent: March 20, 2001Assignee: PolymedInventors: Shalaby W. Shalaby, Joel Thomas Corbett
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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: 6140313Abstract: The present application describes total or partial butyric esters of polysaccharides as novel compounds; the number of hydroxyl groups esterified with butyric residues per each glycosidic monomer is preferably higher than 0.001; the application also describes the process of preparation of said esters, their use in therapy as antiproliferative agents, and pharmaceutical compositions containing them.Type: GrantFiled: May 25, 1999Date of Patent: October 31, 2000Inventors: Alberto Perbellini, Danila Coradini
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Patent number: 6130329Abstract: An anionic surface active agent such as the monoglyceride of succinic acid is incorporated into an aqueous solution of a fatty ester of sucrose to prepare an aqueous solution of a fatty ester of sucrose having a reduced viscosity. A process for reducing the viscosity of an aqueous solution of a fatty ester of sucrose is disclosed, which comprises incorporating an anionic surface active agent in an aqueous solution containing from 8 to 50% by weight of a fatty ester of sucrose having an HLB of from 5 to 20 in an amount of from 1 to 50 parts by weight based on 100 parts by weight of the fatty ester of sucrose. A novel process is also provided, which comprises the use of an aqueous solution of a fatty ester of sucrose having a viscosity thus reduced as an emulsifying agent for dispersing a sparingly water- soluble particulate inorganic compound or cosmetic material therein.Type: GrantFiled: September 30, 1997Date of Patent: October 10, 2000Assignee: Mitsubishi Chemical CorporationInventors: Akihiro Ogawa, Naoya Otomo, Toru Tagawa
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Patent number: 6121440Abstract: A process for preparing esterified polyol fatty acid polyesters is provided, where the polyol has n hydroxyl groups. The process provides for independent control of the level of fully esterified polyols, on the one hand, and the level of n-3 and lower esters, on the other hand. The process is especially suited for preparing sucrose polyester, wherein the process provides for independent control of the level of octaesters, on the one hand, and penta and lower level esters, on the other hand. The process can be used to reduce the level of undesirable reaction byproducts, such as difatty ketone and beta ketoester.Type: GrantFiled: February 12, 1998Date of Patent: September 19, 2000Assignee: The Procter & Gamble CompanyInventors: Corey James Kenneally, Gary Allen Busch, Patrick Joseph Corrigan, Eric Paul Granberg, John Keeney Howie, Richard Gerard Schafermeyer, James Earl Trout
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Patent number: 6113918Abstract: Aminoalkyl glucosamine phosphate compounds that are adjuvants and immunoeffectors are described and claimed. The compounds have a 2-deoxy-2-amino glucose in glycosidic linkage with an aminoalkyl (aglycon) group. Compounds are phosphorylated at the 4 or 6 carbon on the glucosamine ring and comprise three 3-alkanoyloxyalkanoyl residues. The compounds augment antibody production in immunized animals as well as stimulate cytokine production and activate macrophages. Methods for using the compounds as adjuvants and immunoeffectors are also disclosed.Type: GrantFiled: May 8, 1997Date of Patent: September 5, 2000Assignee: Ribi ImmunoChem Research, Inc.Inventors: David A. Johnson, C. Gregory Sowell
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Patent number: 6103885Abstract: The Invention pertains to a process for the amidation of a material having at least one carboxyl-containing polysaccharide. The provided process involves a first step in which the carboxyl groups are reacted with an ammonium donor of the general formula >NH to form the corresponding polysaccharide carboxyl ammonium salt, and a second step in which the polysaccharide carboxyl ammonium salt is heated so as to convert the ammonium groups into the corresponding amido groups. The invention also pertains to fatty amide modified carboxyl-containing polysaccharides, and particularly to fatty amide modified carboxymethyl cellulose. The products in accordance with the invention can be widely employed, e.g. in the field of biodegradable plastics, as anti-redeposition agents for synthetic fibers, as polymeric emulsifiers, as pigment dispersing agents, in cosmetic applications, as thickeners, as oil drilling fluids, as superabsorbers, and in mineral processing.Type: GrantFiled: November 14, 1995Date of Patent: August 15, 2000Assignee: Akzo Nobel NVInventors: Jan Gerardus Batelaan, Peter Marten Van Der Horst
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Patent number: 6086789Abstract: A pyruvate compound suitable for cosmetically or dermatologically administering to the skin and for use in treating diabetic ketosis or other medical treatments. The compound includes a pyruvate selected from the group of pyruvate thioester, dihydroxyacetonepyruvate, and an ester of pyruvate and a sugar or a polyol.Type: GrantFiled: May 12, 1998Date of Patent: July 11, 2000Assignee: Case Western Reserve UniversityInventors: Henri Brunengraber, Catherine Bomont, France David, Peter T. Hallowell, Kevin D. Cooper, Takhar Kasoumov
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Patent number: 6087339Abstract: Disclosed are novel saccharide derivatives which inhibit binding of toxins, such as heat-labile enterotoxin or cholera toxin, to their receptors either in vitro or in vivo. Additionally, disclosed are compounds which inhibit binding of enterovirulent organisms (e.g., bacteria, virus, fungi, and the like), such as Vibrio cholerae and enterotoxigenic strains of Escherichia coli, to their cell surface receptors.Type: GrantFiled: November 14, 1997Date of Patent: July 11, 2000Assignee: Synsorb Biotech, Inc.Inventor: Ole Hindsgaul
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Patent number: 6080853Abstract: Polyol polyesters useful as nondigestible fat substitutes are prepared by improved heterogeneous interesterification processes between fatty acid esters of easily removable alcohol and polyol wherein the particle size of the polyol is reduced to less than 100 microns, and when the degree esterification of the polyol is between about 15% and no more than 75% substantially all of the unreacted polyol is removed. In the initial or early stages of the reaction, reaction conditions are adjusted to maintain a sufficient level of lower partial fatty acids to act as an emulsifier. The initial catalyst level is from about 0.001 to about 0.5 catalyst per mole of catalyst.Type: GrantFiled: November 21, 1997Date of Patent: June 27, 2000Assignee: The Procter & Gamble CompanyInventors: Patrick Joseph Corrigan, Roger Stephen Berger
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Patent number: 6077556Abstract: Fatty acid esters of sucrose wherein the fatty acid groups consist essentially of short chain fatty acid radicals containing from 2 to 10 carbon atoms and long chain fatty acid radicals containing from 20 to 24 carbon atoms in a molar ratio of short chain:long chain radicals of 3:5 to 5:3, the said esters having a degree of esterification of about 7 to 8. The compounds are useful as nondigestible substitutes for solid fats in foods.Type: GrantFiled: September 8, 1992Date of Patent: June 20, 2000Assignee: The Procter & Gamble CompanyInventors: James Carey Letton, Robert David Feeney
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Patent number: 6075139Abstract: Sucrose ester and ether products, useful as food or beverage bulking agents, reduced calorie sweeteners, fat replacement agents, stabilizing agents, thickening agents and emulsifying agents; adhesives; biodegradable plastics and films; sizing agents for paper and textiles; ethical pharmaceuticals and new fibers are prepared by using a two-phase reaction system in which sucrose is dissolved in an alkaline, aqueous solution and an acidic reagent such as a bifunctional acid dichloride or epoxide is added to the sucrose in a water-immiscible organic solvent. Several types of products are produced: water-insoluble sucrose ester (ether) copolymers; water-soluble sucrose ester (ether) copolymers; sucrose ester (ether) dimers; and intramolecular, cyclic sucrose esters (ethers). These products can be further varied by using different kinds of acid dichlorides or epoxides that contain different kinds of functional groups.Type: GrantFiled: July 24, 1996Date of Patent: June 13, 2000Assignee: Iowa State University Research Foundation, Inc.Inventors: John F. Robyt, Rupendra Mukerjea
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Patent number: 6063916Abstract: 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, .alpha.-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). Electron spectroscopy chemical analysis (ESCA) of the first 100 .ANG.Type: GrantFiled: November 27, 1996Date of Patent: May 16, 2000Assignee: 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: 6054577Abstract: A novel endo-fucoidan-lyase and a novel microorganism useful in the production of sugar compounds. Sugar compounds represented by the following general formula (1), wherein at least one of alcoholic hydroxyl group has been sulfated, or salts thereof: ##STR1## wherein Y represents hydrogen or a group represented by the following formula (2).Type: GrantFiled: September 26, 1997Date of Patent: April 25, 2000Assignees: Takara Shuzo Co., Ltd., Research Institute For GlycotechnologyInventors: Takeshi Sakai, Hitomi Kimura, Kaoru Kojima, Katsushige Ikai, Sumiko Akiyoshi, Yoshikuni Nakanishi, Ikunoshin Kato
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Patent number: 6051701Abstract: Hyaluronic acid, hyaluronate esters and salts thereof are sulfated such that the number of sulfate groups per monomeric unit is in the range of from 0.5 to 3.5. The sulfated derivatives exhibit anticoagulant and cell adhesion reduction properties, and may be used to prepare biomaterials.Type: GrantFiled: July 30, 1998Date of Patent: April 18, 2000Assignee: Fidia Advanced Biopolymers SRLInventors: Gloria Cialdi, deceased, Agnese Magnani
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Patent number: 6046313Type: GrantFiled: July 31, 1996Date of Patent: April 4, 2000Assignee: Salford Ultrafine Chemicals and Research LimitedInventors: Feodor Scheinmann, Keith William Lumbard, Richard Talbot Brown, Stephen Patrick Mayalarp, Neil Edward Carter
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Patent number: 6008345Abstract: There is described a polycarboxylic acid or a salt thereof obtained by oxidation of a polysaccharide containing an anhydrous glucose as a constituent unit, wherein the carboxyl group content thereof is high and the weight average molecular weight thereof is not less than 2000. This polycarboxylic acid is suitable for use as a builder for detergent because the amount of an alkali required to perform neutralization titration of the polycarboxylic acid is not less than 435 mg in terms of sodium hydroxide and because the chelate force thereof to a polyvalent cation is high.The polycarboxylic acid is produced by oxidizing a polysaccharide with an oxidizing agent in the presence of a transition metal catalyst.Type: GrantFiled: December 16, 1997Date of Patent: December 28, 1999Assignee: Lion CorporationInventors: Yukihiro Dannoue, Kiyoshi Morohara, Kiyoshi Nakayama
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Patent number: 5981743Abstract: An oligomer composed of a carbohydrate head group and an oligomer chain is disclosed. Methods for increasing the oligomerization rates of lactones and cyclic carbonates are also disclosed.Type: GrantFiled: March 28, 1997Date of Patent: November 9, 1999Assignee: University of MassachusettsInventors: Richard A. Gross, Kirpal Bisht, David Kaplan, Graham Swift, Fang Deng
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Patent number: 5977349Abstract: A process for separating, in the liquid phase, a reaction mixture which comprises a first chlorinated sucrose and at least one additional component selected from the group consisting of at least one other chlorinated sucrose different from said first chlorinated sucrose, salt and solvent, by injecting said reaction mixture onto a fixed bed of solid adsorbent and treating with a desorbent such that:(a) the first chlorinated sucrose passes through the adsorbent into a first recoverable product stream rich in said first chlorinated sucrose at a rate, which is different than the rate at which,(b) at least one of said additional components passes through the adsorbent into at least a second recoverable stream rich in said additional component.Type: GrantFiled: February 11, 1998Date of Patent: November 2, 1999Assignee: McNeil-PPC, Inc.Inventors: Steven J. Catani, Duane A. Leinhos, Thomas O'Connor
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Patent number: 5977326Type: GrantFiled: April 14, 1997Date of Patent: November 2, 1999Assignee: Salford Ultrafine Chemicals and Research LimitedInventors: Feodor Scheinmann, Simon Joel, Andrew V. Stachulski
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Patent number: 5972907Abstract: Compounds which bind to selectin receptors and thus may modulate the course of inflammation, cancer and related processes by intervening with cell-cell adhesion events. Further, such compounds can be used for identification and analysis of such receptors. In this regard the invention is directed to compounds of formula (I). ##STR1## wherein R.sup.1 is independently H, alkyl, aryl, an aryl alkyl, alkenyl or one or more additional saccharide residues; R.sup.2 =H or OH provided that when R.sup.2 is H, R.sup.3 is OH; R.sup.3 =H or OH provided that when R.sup.3 is H, R.sup.2 is OH; X=H, SO.sub.3.sup.- or PO.sub.4.sup.- ; Y is independently H, OH, OR.sup.4 or NHCOR.sup.4, wherein R.sup.4 is alkyl, and Z is an organic acid residue. .alpha.-L-Fucose residue can be modified or replaced with suitable bioisosters or a different saccharide residue such as D-mannose. Modification of L-fucose may include replacement of each or all of the hydroxyl groups with H or OR' wherein R' can be methyl, ethyl or allyl groups.Type: GrantFiled: October 31, 1997Date of Patent: October 26, 1999Assignee: Health Research, Inc.Inventors: Khushi L. Matta, Rakesh K. Jain
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Patent number: 5945529Abstract: Processes for the synthesis of polyol fatty acid polyester by transesterification of a polyol comprise reacting polyol with a first portion of fatty acid lower alkyl ester to provide a first step reaction product in which substantially all of the polyol is reacted with at least one fatty acid lower alkyl ester. The processes then employ a multistage column providing substantial plug flow of liquid therein for further transesterification of the first step reaction product. Partially esterified polyol, a second portion of fatty acid lower alkyl ester and catalyst are fed to the column to form a mixture and cause further transesterification of the partially esterified polyol and fatty acid lower alkyl ester, with lower alkyl alcohol being formed as a by product. The resulting liquid mixture of reactants and product is passed in a first direction between adjacent stages through the column for further reaction of partially esterified polyol with fatty acid lower alkyl ester.Type: GrantFiled: July 19, 1996Date of Patent: August 31, 1999Assignee: The Procter & Gamble CompanyInventors: Patrick Joseph Corrigan, Corey James Kenneally, Eric Paul Granberg
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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: 5929230Abstract: The invention relates to acylated sucrosemonocarboxylic acids, the preparation and use thereof as surface-active substance.Type: GrantFiled: November 13, 1996Date of Patent: July 27, 1999Assignee: Sudzucker AktiengesellschaftInventors: Sonja Ehrhardt, Markwart Kunz, Mohammad Munir
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Patent number: 5922682Abstract: This invention provides a polyester of a polyol, said polyol containing at least 3 hydroxyl groups and having a molecular weight of up to 20,000 at least 1 hydroxyl group in said polyol being in the form of an ester, with a poly- or co-poly-lactic acid residue, each having a molecular weight of at least 5,000. These are useful for parenteral depot formulations.Type: GrantFiled: February 11, 1992Date of Patent: July 13, 1999Assignee: Novartis AGInventors: Zdenek Brich, Thomas Kissel
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Patent number: 5922338Abstract: This invention provides a polyester of a polyol, said polyol containing at least 3 hydroxyl groups and having a molecular weight of up to 20,000 at least 1 hydroxyl group in said polyol being in the form of an ester, with a poly- or co-poly-lactic acid residue, each having a molecular weight of at least from 5,000. These are useful for parenteral depot formulations.Type: GrantFiled: June 6, 1995Date of Patent: July 13, 1999Assignee: Novartis AGInventors: Zdenek Brich, Thomas Kissel
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Patent number: 5916883Abstract: A cyclodextrin derivative, wherein at least 60 percent of the free hydroxy groups of said cyclodextrin are acylated with acyl groups where at least one of said acyl groups comprise a free carboxylic group.Type: GrantFiled: November 1, 1996Date of Patent: June 29, 1999Assignee: Poly-Med, Inc.Inventors: Shalaby W. Shalaby, Joel Thomas Corbett
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Patent number: 5914320Abstract: A process for making a mixture of polyol and at least one additional reaction component for the manufacture of polyol fatty acid polyesters comprises co-milling the polyol and the additional reaction component. The co-milling reduces the particulate size of the polyol and the additional reaction component while creating particles which include an admixture of polyol and the additional reaction component. The co-milled mixture of polyol and additional reaction component can be used, for example, as a feed stream for the transesterfication reaction of the polyol to produce a polyol fatty acid polyester.Type: GrantFiled: July 19, 1996Date of Patent: June 22, 1999Assignee: The Procter & Gamble CompanyInventor: Steven Robert Alexander
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Patent number: 5906924Abstract: High quality trehalose derivatives are readily prepared in a considerably high yield by reacting anhydrous trehalose with reactive reagents under anhydrous conditions. The trehalose derivatives can be used in a variety of fields in the production, the chemical synthesis, and the enzymatic synthesis of foods, cosmetics, pharmaceuticals, detergents and chemicals as surfactants, humectants, skin-beautifying agents, antitumor agents, and intermediates for chemical and enzymatic syntheses.Type: GrantFiled: November 28, 1995Date of Patent: May 25, 1999Assignee: Kabushiki Kaisha Hayashibara Seibutsu Kaguku KenkyujoInventors: Takahiko Mandai, Takashi Shibuya, Toshiyuki Sugimoto
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Patent number: 5877144Abstract: The invention relates to aliphatic carboxylate esters of long-chain inulin, to methods for synthesizing them and to their use as surface-active substances.Type: GrantFiled: February 28, 1997Date of Patent: March 2, 1999Assignee: Sudzucker Aktiengesellschaft Mannheim/OchsenfurtInventors: Sonja Ehrhardt, Alireza Haji Begli, Markwart Kunz, Linda Scheiwe
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Patent number: 5872245Abstract: This present invention pertains to a process for the synthesis of sucrose fatty acid esters by reacting sucrose and a purified specific fatty acid ester under substantially solvent free conditions in the presence of a transesterification stationary catalyst and mechanical emulsification. The process is continuous, yielding selected individual products of separated simple sucrose fatty acid esters of mono-, di-, tri- and polyesters while recycling the unwanted ester fractions, the unreacted sucrose and fatty acid ester.Type: GrantFiled: September 30, 1992Date of Patent: February 16, 1999Assignee: Optima Technologies GroupInventor: Donald C. Wilson
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Patent number: 5858365Abstract: This invention is directed to methods of administering physiologically stable and safe compositions of butyric acid salts and derivatives to a patient for the purpose of wound healing.Type: GrantFiled: June 7, 1995Date of Patent: January 12, 1999Assignee: Trustees of Boston UniversityInventor: Douglas V Faller
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Patent number: 5856299Abstract: Provided are active esters of carboxy polysaccharides and semisynthetic derivatives of carboxy polysaccharides, wherein all or part of the carboxy groups thereof are esterified with an aromatic alcohol, a substituted aromatic alcohol, an aromatic heterocyclic alcohol, a substituted aromatic heterocyclic alcohol, an N-hydroxylamine, or a combination thereof. Also provided is a process for producing such active esters. These active esters can be used for the preparation of modified carboxy polysaccharides or modified semisynthetic derivatives of such carboxy polysaccharides, in the form of esters, thioesters, or amides. Such active esters, modified polysaccharides, and modified semisynthetic derivatives of carboxy polysaccharides can be used in the biomedical and pharmaceutical fields to prepare, for example, cosmetic articles, health care articles, surgical articles, and diagnostic kits.Type: GrantFiled: November 26, 1996Date of Patent: January 5, 1999Assignee: Fidia Advanced Biopolymers S.r.l.Inventors: Zefferino Righetto, Davide Bellini
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Patent number: 5854368Abstract: A polyester represented by the following general formula (I) and a copolymer which comprises two structural units represented by the following general formulae (I') and (II). ##STR1## and a coating material for use in large intestine-selective drug release pharmaceutical preparations, which contains the above polyester and/or copolymer. The polyester and copolymer of the present invention contain a saccharide residue which is hydrolyzed and/or assimilated specifically in the large intestine, drugs contained in solid oral pharmaceutical administration pharmaceutical preparations coated with the coating material of the present invention are not decomposed or absorbed by digestive organs other than the large intestine, but instead are released selectively and therefore in a high concentration in the large intestine.Type: GrantFiled: December 30, 1996Date of Patent: December 29, 1998Assignee: Kanegafuchi Kagaku Kogyo Kabushiki KaishaInventors: Koji Iritani, Tetsuya Kawasaki, Nobutaka Tani, Shigeki Masuda, Yoshiaki Yano
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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: 5837300Abstract: Mixtures of liquid sucrose fatty acid esters comprise an improved class of physiologically compatible fat replacements for foods. The compositions melt cleanly at 95.degree. F. or below and comprise at least 35 percent of a mixture of tetra-, penta- and hexa- esters.Type: GrantFiled: December 19, 1990Date of Patent: November 17, 1998Assignee: Nabisco Technology CompanyInventors: Lawrence P. Klemann, John W. Finley
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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: 5827937Abstract: The present invention provides a process for preparing a cross-linked biocompatible polysaccharide gel composition, which comprises:forming an aqueous solution of a water soluble, cross-linkable polysaccharide;initiating a cross-linking of said polysaccharide in the presence of a polyfunctional cross-linking agent therefor;sterically hindering the cross-linking reaction from being terminated before gelation occurs, an activated poly-saccharide being obtained; andreintroducing sterically unhindered conditions for said activated polysaccharide so as to continue the cross-linking thereof to a viscoelastic gel. The invention also provides a gel composition obtainable by such a process as well as gel compositions for different medical uses.Type: GrantFiled: July 17, 1995Date of Patent: October 27, 1998Assignee: Q Med ABInventor: Bengt .ANG.gerup
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Patent number: 5827831Abstract: The oral delivery of many classes of drugs is facilitated by converting drugs having suitable functional groups to 1-O-alkyl-, 1-O-acyl-, 1-S-acyl, and 1-S-alkyl-sn- glycero-3-phosphate derivatives. The method confers the ability to be absorbed through the digestive tract to drugs that are not orally bioavailable in the non-derivatized state, and enhances the effectiveness of drugs that are poorly absorbed or rapidly eliminated. The method provides orally bioavailable lipid prodrugs of pharmaceutical compounds having diverse physiological activities, including anticancer and antiviral agents, anti-inflammatory agents, antihypertensives and antibiotics. Potency of the lipid prodrugs is comparable to that of the corresponding non-derivatized drugs.Type: GrantFiled: June 7, 1995Date of Patent: October 27, 1998Assignee: NeXstar Pharmaceuticals, Inc.Inventors: Karl Y. Hostetler, Raj Kumar, Nagarajan C. Sridhar
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Patent number: 5821360Abstract: A process for producing polycarboxylic acids or their salts from polysaccharides is provided. Solid particulate polysaccharides having at least one primary alcohol group in the polysaccharides are oxidized with nitrogen dioxide in a fluid bed. The fluidizing gas contains nitrogen dioxide and the process is operated at a pressure of from 0.5 to 12 bars and a temperature between the boiling point of nitrogen dioxide and 160.degree. C. At least two moles of nitrogen dioxide for the equivalent of the primary alcohol groups reacted over the entire reaction are provided.Type: GrantFiled: July 31, 1996Date of Patent: October 13, 1998Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Konrad Engelskirchen, Herbert Fischer, Werner Juettner, Hans-Wilhelm Verholt, Thomas Moeller
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Patent number: 5808049Abstract: There is disclosed an ester compound that is resistant to decomposition in blood, but is quickly hydrolyzed in cancer cells, and functions as an anticancer agent. The ester compound has a structure represented by formula (I) or formula (II): ##STR1## wherein R.sub.1 represents a methyl group, a methoxy group, or a trifluoroacetamido group; R.sub.2 represents a phenyl group or a phenylmethyl group; and the absolute configuration of the asymmetric center marked with an asterisk is R.Type: GrantFiled: June 28, 1996Date of Patent: September 15, 1998Assignee: Director-General of Agency of Industrial Science and TechnologyInventors: Yoshimitsu Yamazaki, Yoshikatsu Ogawa, Hiroaki Okuno
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Patent number: 5801238Abstract: A method for producing a water absorbent resin comprising the step of radically polymerizing a water-soluble radically polymerizable monomer having an acid group or a group of the salt thereof and optionally a polysaccharide in the presence of water using a crosslinking agent (C), wherein 0.0001 to 1 weight % of a thiol compound (D) having a radically polymerizable double bond, based on the above mentioned water-soluble radically polymerizable monomer (A), is used as the copolymerizing component to provide a water absorbent resin having a high absorbency and a good gel stability after absorbing body fluid, and a water absorbent comprising the water absorbent resin produced thereby.Type: GrantFiled: September 10, 1996Date of Patent: September 1, 1998Assignee: Sanyo Chemical Industries, Ltd.Inventors: Keiji Tanaka, Masashi Date, Kenjiro Tsubota, Tsuyoshi Yuki, Satoshi Tamabuchi