Viscosity Or Degree Of Polymerization Changed (e.g., Degrading, Cross Linking, Etc.) Patents (Class 536/41)
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Patent number: 5672482Abstract: An exo-enzyme having an ability to cut .beta.-(2.fwdarw.1) fructoside bond or a microorganism which produces the enzyme is allowed to act on a saccharide solution containing cyclic inulooligosaccharide in which fructose molecules are bonded through .beta.-(2.fwdarw.1) bond in a cyclic configuration, and other saccharides such as monosaccharide, disaccharide, linear oligosaccharide and inulin, and then the cyclic inulooligosaccharide is collected from an obtained saccharide solution. Thus cyclic inulooligosaccharide can be purified inexpensively at a high yield without using any solvent.Type: GrantFiled: April 7, 1995Date of Patent: September 30, 1997Assignees: Mitsubishi Chemical Corporation, Mitsubishi Kasei Engineering CompanyInventors: Sachiko Kushibe, Masao Tamura
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Patent number: 5670486Abstract: New A83543 components, including fermentation products A83543K, A83543O, A83543P, A83543U, A83543V, A83543W and A83543Y and N-demethyl derivatives, and salts thereof, are useful for the control of insects and mites. The pseudoaglycones of the new A83543 components are useful for the preparation of A83543 components. Methods are provided for making the new A83543 components by culturing of Saccharopolyspora spinosa NRRL 18395, NRRL 18537, NRRL 18538, or NRRL 18539, or NRRL 18743 or NRRL 18719 or NRRL 18823 in suitable culture medium. Insecticidal and ectoparasiticidal compositions containing new A83543 components are also provided.Type: GrantFiled: June 7, 1995Date of Patent: September 23, 1997Assignee: DowElancoInventors: Jon S. Mynderse, James A. Mabe, Jan R. Turner, Mary L. B. Huber, Mary C. Broughton, Walter M. Nakatsukasa, Lawrence Creemer, Herbert A. Kirst, James W. Martin
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Patent number: 5670364Abstract: New A83543 components, including fermentation products A83543K, A835430, A83543P, A83543U, A83543V, A83543W and A83543Y and N-demethyl derivatives, and salts thereof, are useful for the control of insects and mites. The pseudoaglycones of the new A83543 components are useful for the preparation of A83543 components. Methods are provided for making the new A83543 components by culturing of Saccharopolyspora spinosa NRRL 18395, NRRL 18537, NRRL 18538, or NRRL 18539, or NRRL 18743 or NRRL 18719 or NRRL 18823 in suitable culture medium. Insecticidal and ectoparasiticidal compositions containing new A83543 components are also provided.Type: GrantFiled: June 7, 1995Date of Patent: September 23, 1997Assignee: DowElancoInventors: Jon S. Mynderse, James A. Mabe, Jan R. Turner, Mary L. B. Huber, Mary C. Broughton, Walter M. Nakatsukasa, Lawrence Creemer, Herbert A. Kirst, James W. Martin
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Patent number: 5665561Abstract: The present invention relates to compositions and methods for preventing pneumococcal infection. In particular, this invention relates to the identification of the minimum receptor targets of pneumococcal adherence to pulmonary and vascular endothelium, and to compositions and methods for preventing such adherence. In particular, the invention relates to the ability of one or more carbohydrate entities having the following motif or motifs: a disaccharide N-acetyl-D-galactosamine .beta.1-3Gal motif, a disaccharide N-acetyl-D-galactosamine .beta.1-4Gal motif, and an N-acetyl-D-glucosamine motif, effective to induce elution of adherent S. pneumoniae from host cells. In particular, a composition containing all three motifs can elute about 100% of pneumococcal bacteria from lung epithelial cells, and from venous endothelial cells. In a particular embodiment, a pharmaceutical composition of the invention can be used to treat pneumococcal infections in which the host cells are lung epithelial cells.Type: GrantFiled: June 6, 1994Date of Patent: September 9, 1997Assignee: The Rockefeller UniversityInventors: Elaine I. Tuomanen, Diana R. Cundell
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Patent number: 5663320Abstract: The present invention relates to highly diastereoselective processes for production of cis-nucleosides and nucleoside analogues and derivatives in high optical purity and intermediates useful in those processes.Type: GrantFiled: June 5, 1995Date of Patent: September 2, 1997Assignee: BioChem Pharma, Inc.Inventors: Tarek Mansour, Haolun Jin, Allan H.L. Tse, M. Arshad Siddiqui
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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: 5659015Abstract: This invention relates to a method of producing peracetyloxazolines from peracetyl saccharides. The method involves reacting the starting material, a peracetyl saccharide, with a reagent combination, to directly produce the peracetyl oxazoline. This method may be used for the activation of oligosaccharides, wherein an oligosaccharide containing a reducing GlcNAc terminus is activated by the formation of an oxazolide at the terminal GlcNAc, and then coupled with a bifunctional spacer to provide an oligosaccharide-spacer conjugate. The activated oligosaccharide-spacer conjugate is then coupled to a protein, such as granulocyte colony stimulating factor or .gamma.-interferon, providing a neoglycoprotein conjugate. The invention provides a method for forming neoglycoprotein conjugates which may improve biological and physiochemical properties of the protein. For example, serum lifetime or efficiency of drug delivery of the peptide to a target organ or cell may be improved.Type: GrantFiled: October 13, 1992Date of Patent: August 19, 1997Inventors: Marcelo Colon, Jeffrey T. Davis, James R. Rasmussen, Marianne Borowski, Barbara Y. Wan, Shirish Hirani
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Patent number: 5658886Abstract: The claims cover a bioactive compound N-methyl-N-.alpha.-D-glucopyranosil-ammonium-2-acridone-9-on-10-yl-acetate designated CYCLOFERONE which was obtained by chemical synthesis and is a heterocyclic compound. Specifically CYCLOFERONE is an acridanone derivative of formula ##STR1## CYCLOFERONE exhibits interferonogenic, anti-vital (including anti-HIV), anti-parasitic, anti-promotive, and radioprotective effects.Type: GrantFiled: December 7, 1994Date of Patent: August 19, 1997Assignee: Limited Liability Partnership "POLYSAN"Inventors: Novomir Pavlovich Chizhov, Roald Antonovich Kupchinsky, Ljudmila Evgenievna Alekseeva, Aleksei Leonidovich Kovalenko, Margarita Alekseevna Borisova
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Patent number: 5659027Abstract: A novel class of pharmaceutically active boronated compounds are provided. The boronated compounds include boronated purine and pyrimidine bases and boronated nucleosides, as well as phosphate esters and oligomers thereof. The compounds are boronated at the ring nitrogen of the purine or pyrimidine base, or at a 2', 3' or 5' amino substituent of the nucleoside sugar.Type: GrantFiled: November 4, 1994Date of Patent: August 19, 1997Assignees: University of North Carolina, Boron Biologicals, Inc., Duke UniversityInventors: Bernard F. Spielvogel, Anup Sood, Iris H. Hall, Barbara Ramsay Shaw, Jeno Tomasz
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Patent number: 5659021Abstract: Enantiomerically pure glycerol derivatives, e.g. S-1,2-O-isopropylidene, S-1,2-O-benzylidene, and R-1,2-O-dibenzyl glycerol, have been prepared from 1,2R-O-protected erythritols in high yields. The latter compounds are easily obtained from erythorbic acid and are useful building blocks in the synthesis of a host of optically active compounds having biological activity.Type: GrantFiled: July 25, 1994Date of Patent: August 19, 1997Assignee: The Board of Governors for Higher Education, State of Rhode Island and Providence PlantationsInventor: Elie Abushanab
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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: 5656460Abstract: Disclosed is a novel .alpha.-glycosyl derivative of a catecholamine or its salt, said .alpha.-glycosyl derivative being prepared by allowing a saccharide-transferring enzyme together with or without glucoamylase to act on a solution containing an .alpha.-glucosyl saccharide and one of catecholamines in order to form an .alpha.-glycosyl derivative of said catecholamines, and recovering the resultant .alpha.-glycosyl derivative. The .alpha.-glycosyl derivative overcomes conventional drawbacks of catecholamines, and does not substantially exhibit or have a reducing activity and undesirable toxicity, but has a relatively-high stability and exerts the inherent physiological activities of catecholamines in vivo. Thus, the .alpha.-glycosyl derivative is advantageously used as a variety of pharmaceuticals in the form of an injection, tablet, etc.Type: GrantFiled: August 26, 1994Date of Patent: August 12, 1997Assignee: Kabushiki Kaisha Hayashibara Seibutsu Kagaku KenkyujoInventors: Tetsuya Nakada, Michio Kubota
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Patent number: 5654282Abstract: Glyco-amino acids and glycopeptides having three-dimensionally stable configurations are described. These glyco-amino acids and glycopeptides have glycoside functional groups, such as fucose and analogues and derivatives thereof, covalently bound to an amino acid or peptide having a free carboxylic group or sulfate group in an orientation that facilitates the binding between these groups and selectin receptors. The present glyco-amino acids and glycopeptides may be used in the treatment of selectin-mediated disorders, such as inflammation, autoimmune disease and cancer.Type: GrantFiled: June 6, 1995Date of Patent: August 5, 1997Assignee: Glycomed IncorporatedInventors: Peng Cho Tang, Daniel Emil Levy, Kevin Ross Holme, Saeed Abdalla Abbas
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Patent number: 5654163Abstract: The invention concerns new indophenyl-substituted maltose derivatives, their use for the determination of the enzymatic activity of .alpha.-amylase and reagents for the determination of .alpha.-amylase which contain the new indophenyl-substituted maltose derivatives as the enzyme substrate.Type: GrantFiled: July 24, 1995Date of Patent: August 5, 1997Assignee: Boehringer Mannheim GmbHInventors: Martina Junius-Comer, Axel Schmidt, Elli Rauscher
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Patent number: 5652345Abstract: 4-(3-beta-D-galactopyranosylphenyl)-4-methoxyspiro[1,2-dioxetane-3,2'-adama ntane] which is useful in various chemiluminescent assays.Type: GrantFiled: January 25, 1994Date of Patent: July 29, 1997Assignee: Tropix, Inc.Inventors: Arthur Paul Schaap, Hashem Akhavan-Tafti
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Patent number: 5652346Abstract: What is disclosed is a dicarboxylic acid oxidation product of a immunologically reactive mono- or a polysaccharide having vicinal diols.Type: GrantFiled: March 6, 1996Date of Patent: July 29, 1997Assignee: Johnson & Johnson Clinical Diagnostics, Inc.Inventors: Michael Ray Detty, Susan Jean Danielson
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Patent number: 5650393Abstract: Amphiphilic derivatives of amino acids or peptides are provided, comprising a polyhydroxylated hydrophilic part derived from a sugar, from a polyol, from an aminopolyol or from an oligosaccharide, and at least one hydrophobic part derived from a hydrocarbon, fluorocarbon, or a mixed fluorocarbon/hydrocarbon, saturated or unsaturated, having from 5 to 20 carbon atoms, the hydrophobic part(s) being linked to the hydrophilic part by a junction bearing an amino acid or a peptide.Type: GrantFiled: June 7, 1995Date of Patent: July 22, 1997Assignee: Alliance Pharmaceutical Corp.Inventors: Andre A. Pavia, Bernard Pucci, Jean G. Riess, Leila Zarif, Camille Guedj
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Patent number: 5648473Abstract: A stereoselective glycosylation process for preparing beta-anomer enriched 2'-deoxy-2',2'-difluoropyrimidine nucleosides and 2'-deoxy-2'-fluoropyrimidine nucleosides which involves reacting an alpha-anomer enriched 2-deoxy-2,2-difluorocarbohydrate or 2-deoxy-2-fluorocarbohydrate with at least a molar equivalent of a pyrimidine nucleobase derivative in a low freezing inert solvent.Type: GrantFiled: May 30, 1995Date of Patent: July 15, 1997Assignee: Eli Lilly and CompanyInventor: Ta-Sen Chou
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Patent number: 5648474Abstract: The present invention provides temperature stable crystalline etoposide 4'-phosphate diethanol solvate, and a process for its preparation.Type: GrantFiled: October 8, 1991Date of Patent: July 15, 1997Assignee: Bristol-Myers SquibbInventor: Denis Favreau
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Patent number: 5644041Abstract: The present invention generally relates to an alkyl glycoside of the formula (I): RCH.sub.2 O(G).sub.x H, wherein R is an alkyl group having a total of 8-12 carbon atoms and containing 2-4 groups of the formula --CH(CH.sub.3)-- in its carbon chain; G is a monosaccharide residue; and x is 1-4. The invention also relates to the use of the alkyl glycoside as a surfactant in the cleaning of hard surfaces. A composition containing an alkyl glycoside of formula (I), a complexing agent and a solubilizer is also disclosed.Type: GrantFiled: October 18, 1995Date of Patent: July 1, 1997Assignee: Akzo Nobel nvInventor: Ingegard Johansson
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Patent number: 5643884Abstract: This invention relates generally to the field of medicinal chemistry, and more specifically to derivatives of a subclass of triterpenoid acids that have multi-medicament properties, that is derivatives of the lupane, betulinic acid, formulations containing such, and their use to prevent or treat certain diseases, and preferably to derivatives or analogues of betulinic acid, that have the following structural formula (1): ##STR1## wherein: Y is OR.sup.1, NR.sup.1.sub.2, O.sup.- M.sup.1 ;R.sup.1 is H, LOWER ALKYL,M.sup.1 is Na.sup.+, K.sup.+, Mg.sup.++, Ca.sup.++ ions;each R.sup.2 is independently CH.sub.2 OR.sub.1 or CH.sub.3 ;each R.sup.3 is independently H, CH.sub.3, lower alkyl, COY, CH.sub.2 OH, CH.sub.2 OCH.sub.2 CH=CH.sub.2, CH.sub.2 OSO.sub.3.sup.- M.sup.1 ;each Z is independently NHR.sup.1.sub.2, NR.sup.1 Ac, NR.sup.1 Bz, H, OCH.sub.3, lower alkyl, OH, OSO.sub.3.sup.- M.sup.1, OCH.sub.2 CH=CH.sub.2, OCH.sub.2 CO.sub.2 H or O-glucoside;each X is independently O, S, NR.sup.1 or NR.sub.2.sup.Type: GrantFiled: August 9, 1993Date of Patent: July 1, 1997Assignee: Glycomed IncorporatedInventors: Mark Brian Anderson, John Henry Musser
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Patent number: 5644042Abstract: A process for the preparation of aldobionamides directly from an aldobionic acid starting material, in which an aldobionic acid is reacted by removing water by azeotropic distillation to obtain an aldobionolactone. The aldobionolactone can then be reacted with amines without further purification or isolation steps to obtain the aldobionamide.Type: GrantFiled: December 21, 1995Date of Patent: July 1, 1997Assignee: Solvay Pharma Deutschland GmbHInventors: Klaus Guenther Gerling, Claudia Schreer, Petra Schwarz, Kornelia Wendler
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Patent number: 5644044Abstract: Sugar alcohols can be prepared from the corresponding sugars by catalytic hydrogenation in aqueous solution with hydrogen, the hydrogenation being carried out continuously at a hydrogen pressure of 100 to 400 bar and a reaction temperature of 40.degree. to 80.degree. C. on support-free shaped bodies which are arranged in a fixed bed and are composed of pressed powders of alloys of the elements of the iron sub group of sub group VIII of the Periodic Table of the Elements containing elements of sub group VI. The shaped bodies have a compressive strength of 20 to 250 N and an internal surface area of 10 to 80 m.sup.2 /g.Type: GrantFiled: April 28, 1995Date of Patent: July 1, 1997Assignee: Bayer AktiengesellschaftInventor: Gerhard Darsow
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Patent number: 5644043Abstract: This invention provides 2',3'-dideoxy-2',2'-difluoronucleosides of the structure ##STR1## wherein R.sup.1 -R.sup.4 are defined in the specification. These compounds have been shown to be useful for treating a variety of vital infections in experimental animals as well as having antineoplastic activity against various mouse tumors.Type: GrantFiled: December 27, 1993Date of Patent: July 1, 1997Assignee: Eli Lilly and CompanyInventors: Larry W. Hertel, Julian S. Kroin
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Patent number: 5641872Abstract: The sugar alcohols mentioned as title compounds can be prepared from the corresponding sugars by catalytic hydrogenation in aqueous solution with hydrogen, the hydrogenation being carded out continuously at a hydrogen pressure of 100 to 400 bar and a reaction temperature of 40.degree. to 80.degree. C. on support-free shaped bodies which are arranged in a fixed bed and are composed of pressed powders of alloys of the elements of the iron sub group of sub group VIII of the Periodic Table of the Elements containing elements of sub group VI. The shaped bodies have a compressive strength of 20 to 250 N and an internal surface area of 10 to 80 m.sup.2 /g.Type: GrantFiled: May 1, 1995Date of Patent: June 24, 1997Assignee: Bayer AktiengesellschaftInventor: Gerhard Darsow
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Patent number: 5639866Abstract: The invention relates to methods that permit the rapid construction of oligosaccharides and other glycoconjugates. Methods for forming multiple glycosidic linkages in solution in a single step are disclosed. The invention takes advantage of the discovery that the relative reactivity of glycoside residues containing anomeric sulfoxides and nucleophilic functional groups can be controlled. In another aspect of the invention, the reactivity of activated anomeric sugar sulfoxides is utilized in a solid phase method for the formation of glycosidic linkages. The methods disclosed may be applied to the preparation of specific oligosaccharides and other glycoconjugates, as well as to the preparation of glycosidic libraries comprising mixtures of various oligosaccharides, including glycoconjugates, which can be screened for biological activity.Type: GrantFiled: February 23, 1993Date of Patent: June 17, 1997Assignee: Princeton UniversityInventor: Daniel Evan Kahne
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Patent number: 5639733Abstract: Alkyl glycoside aqueous solutions, which satisfy the following conditions (a) and/or (b):(a) the solution is maintained at a pH value exceeding 7, and(b) the solution contains a water-soluble alcohol, are highly stable with respect to microbial activities, such as putrefaction and fungal growth, and are useful as surface active agents.Type: GrantFiled: November 14, 1994Date of Patent: June 17, 1997Assignee: Kao CorporationInventors: Toyomi Koike, Hiroshi Nagumo, Akira Yamamuro, Yukinaga Yokota
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Patent number: 5639737Abstract: Growth or metastasization of malignant tumors can be inhibited by administering to a patient in need thereof sufficient lactose to block crucial lectins on the affected organ so that the tumor cells cannot anchor to other locations in the body. Lactose can be administered alone, or in combination with conjugates of cytotoxic drugs. Preferably, lactose is conjugated to a cytotoxic substance so that the primary tumor is treated concurrently with prevention of metastasis. Additionally, by conjugating a cytotoxic drug to lactose, the cytotoxic drug is maintained in close proximity to the tumor because of the receptors on the tumor which bind the lactose (and therefore the cytotoxic agent bound thereto) to the tumor cells. By using a conjugate of lactose with a cytotoxic agent, one dose is generally sufficient to destroy the receptor sites on the tumor and prevent metastasis of the tumor while treating the tumor.Type: GrantFiled: December 21, 1994Date of Patent: June 17, 1997Assignee: Co Enzyme Technology Ltd.Inventor: David Rubin
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Patent number: 5639735Abstract: Hayumicin compounds, obtainable by cultivation of a strain of Actinomadura sp. designated ATCC 55432, and analogs of these compounds. The novel compounds have antitumor as well as antibiotic, particularly antibacterial, activity.Type: GrantFiled: September 19, 1994Date of Patent: June 17, 1997Assignee: Bristol-Myers Squibb CompanyInventors: Rolf Menzel, Scott T. Taylor, Mitsuaki Tsunakawa, Keiichi Numata, Tamotsu Furumai
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Patent number: 5639734Abstract: The present invention provides a composition of matter comprising a biosynthetic anti-inflammatory oligosaccharide, comprising the structure of: sugar - sugar - X - R; wherein said sugar is selected from the group consisting of N-acetylneuraminic acid, galactose, N-acetylglucosamine, N-acetylgalactosamine, fucose and mannose; wherein X is a bridging atom selected from the group consisting of oxygen, sulfur, nitrogen and carbon; and wherein R is an aglycone selected from the group consisting of naphthol, naphthalenemethane, indenol, a heterocyclic derivative of indenol, a heterocyclic derivative of naphthol and a heterocyclic derivative of naphthalenemethanol. Also provided is a method of treating an inflammatory disease in an individual comprising the step of administering to said individual a therapeutically effective dose of the novel composition of the present invention.Type: GrantFiled: December 20, 1994Date of Patent: June 17, 1997Inventors: Jeffrey D. Esko, Arun K. Sarkar
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Patent number: 5637570Abstract: Novel dlsubstituted and trisubstituted derivatives of 2,3:4,6-di-O-isopropylidene-.alpha.-L-xylo-2-hexulofuranosonic acid containing at least one alkyl group at position 1, position 4 being occupied by OH, O-alkylamino or O-alkylaminoheterocyclic moiety, and the OH group at position 6 being replaced by a saturated heterocyclic moiety or aminoalkyl heterocyclic group. These compounds exhibit anti-cancer, anti-inflammatory and/or anti-proliferative activities. Methods of preparation, pharmaceutical compositions containing the compounds and methods of treating cancer, inflammatory and/or autoimmune disorders employing the compounds are described.Type: GrantFiled: May 9, 1995Date of Patent: June 10, 1997Assignee: Chemora PharmochemInventors: Sudershan K. Arora, Manoj K. Gupta, Pushappam Lukos, Ravinder Kumar, Shanti N. Sawhney
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Patent number: 5637680Abstract: An etoposide phosphate represented by the formula ##STR1## is prepared by blocking the hydroxyl groups of the saccharide moiety of etoposide with halogenoacetyl groups, thereafter phosphorylating the 4'-position, and removing the halogenoacetyl groups from the obtained phosphate in the presence of an amine. This process can give the objective etoposide phosphate in a higher yield than that of the prior art to enable the industrial mass-production thereof.Type: GrantFiled: June 7, 1995Date of Patent: June 10, 1997Assignee: Nippon Kayaku Kabushiki KaishaInventors: Yoshinobu Miyazawa, Hitoshi Sato, Hiroshi Yoshikawa, Kouichi Ohkawa, Noriko Tomiyoshi
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Patent number: 5637569Abstract: Ganglioside lactam analogue derivatives of general formula (I) in which A is a sialic acid residue of formula (II) which is bound via the dashed line in the 2-position; and in which Z.sup.1 is --OH or a group --NHX.sup.1, and Y.sup.30 is --CH.sub.3 or --CH.sub.2 OH; X.sup.1 and Y.sup.1 together form a bond and Y.sup.2 is --OH or a group OR.sup.20, or X.sup.1 and Y.sup.2 together form a bond and Y.sup.1 is --OH or --NHAc; Y.sup.3 is --OH or a group --OR.sup.20 ; R.sup.1 is H or a sialic acid residue of formula (III) which is bound via the dashed line in the 2-position; and in which Z.sup.2 is --OH or a group --NHX.sup.2, and Y.sup.30 is as defined above; X.sup.2 and Y.sup.10 together form a bond and Y.sup.20 is --OH, or X.sup.2 and Y.sup.20 together form a bond and Y.sup.10 is --OH; with the provisos that when R.sup.1 is H, then Z.sup.1 is --NHX.sup.1, and that when R.sup.1 is a sialic acid residue of formula (III), then at least one of Z.sup.1 and Z.sup.2 is different from --OH; R.sup.Type: GrantFiled: September 12, 1994Date of Patent: June 10, 1997Assignee: Symbicom AktiebolagInventors: Hans G. Magnusson, Asim K. Ray
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Patent number: 5635611Abstract: A process for producing a saccharide carboxylic acid or a salt thereof characterized in that a microorganism belonging to the genus Pseudogluconobacter and capable of oxidizing a hydroxymethyl group and/or hemiacetal hydroxyl-associated carbon atom to a carboxyl group, or an artifact derived from the microorganism, is permitted to act on a hydroxymethyl and/or hemiacetal hydroxyl-containing saccharide or saccharide derivative to produce and accumulate the corresponding carboxylic acid and the carboxylic acid so accumulated is harvested and novel saccharide carboxylic acids produced by the above production method, and by the process, from a broad range of saccharides, saccharic acids having carboxyl groups derived from hydroxymethyl and/or hemiacetal OH groups can be produced with high selectivity and in good yield, the resultant saccharide acids are resistant to enzymatic degradation and have improved water solubility, among other characteristics.Type: GrantFiled: April 10, 1995Date of Patent: June 3, 1997Assignee: Takeda Chemical Industries, Ltd.Inventors: Toshihiro Ishiguro, Masahide Oka, Takamasa Yamaguchi, Ikuo Nogami
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Patent number: 5635612Abstract: The invention relates to methods that permit the rapid construction of oligosaccharides and other glycoconjugates. Methods for forming multiple glycosidic linkages in solution in a single step are disclosed. The invention takes advantage of the discovery that the relative reactivity of glycoside residues containing anomeric sulfoxides and nucleophilic functional groups can be controlled. In another aspect of the invention, the reactivity of activated anomeric sugar sulfoxides is utilized in a solid phase method for the formation of glycosidic linkages. The methods disclosed may be applied to the preparation of specific oligosaccharides and other glycoconjugates, as well as to the preparation of glycosidic libraries comprising mixtures of various oligosaccharides, including glycoconjugates, which can be screened for biological activity.Type: GrantFiled: February 18, 1994Date of Patent: June 3, 1997Assignee: The Trustees of Princeton UniversityInventor: Daniel E. Kahne
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Patent number: 5635610Abstract: A process for producing a saccharide carboxylic acid or a salt thereof characterized in that a microorganism belonging to the genus Pseudogluconobacter and capable of oxidizing a hydroxymethyl group and/or hemiacetal hydroxyl-associated carbon atom to a carboxyl group, or an artifact derived from the microorganism, is permitted to act on a hydroxymethyl and/or hemiacetal hydroxyl-containing saccharide or saccharide derivative to produce and accumulate the corresponding carboxylic acid and the carboxylic acid so accumulated is harvested and novel saccharide carboxylic acids produced by the above production method, and by the process, from a broad range of saccharides, saccharic acids having carboxyl groups derived from hydroxymethyl and/or hemiacetal OH groups can be produced with high selectivity and in good yield, the resultant saccharide acids are resistant to enzymatic degradation and have improved water solubility, among other characteristics.Type: GrantFiled: April 10, 1995Date of Patent: June 3, 1997Assignee: Takeda Chemical Industries, Ltd.Inventors: Toshihiro Ishiguro, Masahide Oka, Takamasa Yamaguchi, Ikuo Nogami
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Patent number: 5633357Abstract: A method of producing a carboxylic acid glucuronide by reacting a carboxylic acid precursor with a blocked sugar epoxide precursor is disclosed. Also disclosed are: deuterated 11-nor-.DELTA..sup.8 - or .DELTA..sup.9 -THC carboxylic acid glucuronide having a deuterated hydrocarbon chain; 5'-deuterated 11-nor-.DELTA..sup.8 - or .DELTA..sup.9 -THC-carboxylic acid or 5'-deuterated .DELTA..sup.8 - or .DELTA..sup.9 -THC glucuronide. The compositions are useful as GC-MS standards; in methods for preparing antibodies reactive with a THC glucuronide; and, in GC-MS diagnostic methods for THC metabolites.Type: GrantFiled: March 4, 1994Date of Patent: May 27, 1997Assignee: Synthetic Technology CorporationInventors: Marcus A. Tius, Mark R. Hagadone
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Patent number: 5631357Abstract: A process for making nonionic emulsifiers involving the steps of: (a) performing an acid-catalyzed acetalization reaction on a mixture of (i) sugars or water-containing starch degradation products and (ii) primary alcohols in a molar ratio of (i):(ii) of from 1:2 to 1:8; (b) terminating the reaction at a conversion ranging from 60% to 90% of the theoretical to form a reaction product; (c) neutralizing the reaction product to form a neutralized reaction product; and (d) purifying the neutralized reaction product by back-mixing the product through at least one coarse filter until the product becomes clear.Type: GrantFiled: January 26, 1996Date of Patent: May 20, 1997Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Manfred Weuthen, Petra Riegels, Irmgard Hartel
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Patent number: 5631353Abstract: Alkene adamantane compounds useful as intermediates for producing the corresponding 1,2-dioxetanes which are useful in chemiluminescent assays.Type: GrantFiled: July 27, 1995Date of Patent: May 20, 1997Assignee: Board of Governors of Wayne State UniversityInventors: Arthur P. Schaap, Hashem Akhavan-Tafti
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Patent number: 5629411Abstract: A process for producing a saccharide carboxylic acid or a salt thereof characterized in that a microorganism belonging to the genus Pseudogluconobacter and capable of oxidizing a hydroxymethyl group and/or hemiacetal hydroxyl-associated carbon atom to a carboxyl group, or an artifact derived from the microorganism, is permitted to act on a hydroxymethyl and/or hemiacetal hydroxyl-containing saccharide or saccharide derivative to produce and accumulate the corresponding carboxylic acid and the carboxylic acid so accumulated is harvested and novel saccharide carboxylic acids produced by the above production method, and by the process, from a broad range of saccharides, saccharic acids having carboxyl groups derived from hydroxymethyl and/or hemiacetal OH groups can be produced with high selectivity and in good yield, the resultant saccharide acids are resistant to enzymatic degradation and have improved water solubility, among other characteristics.Type: GrantFiled: April 10, 1995Date of Patent: May 13, 1997Assignee: Takeda Chemical Industries, Ltd.Inventors: Toshihiro Ishiguro, Masahide Oka, Takamasa Yamaguchi, Ikuo Nogami
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Patent number: 5624908Abstract: Anti-cancer compositions containing chiral monosaccharides and methods of their use are disclosed herein. The compositions, exhibiting cytostatic and cytotoxic properties with regard to neoplastic cells are formulated using the L-isomeric form of monosaccharides. A preferred embodiment of the invention employs the L-isomeric form of glucose with a pharmaceutically acceptable carrier. The compositions may be used alone or as an adjunct to other forms of cancer therapy. They are useful in combination with all major forms of cancer therapy including surgery, biological and chemical therapies, radiation therapy, and hyperthermia. In addition to increasing the mortality rate of neoplastic cells, these compositions can reduce the metastatic potential of the tumor, and slow the growth of the malignancy.Type: GrantFiled: June 7, 1995Date of Patent: April 29, 1997Assignee: Valley Cancer InstituteInventor: Haim I. Bicher
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Patent number: 5624906Abstract: The present invention is related to new oral hygiene compositions that have improved foam, viscosity, clarity and good taste due to the inclusion of a new type of alkyl aldonamide compound, specifically heteroatom containing alkyl aldonamide compounds.Type: GrantFiled: December 8, 1994Date of Patent: April 29, 1997Assignee: Lever Brothers Company, Division of Conopco, Inc.Inventor: Robert Vermeer
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Patent number: 5622937Abstract: This invention relates to compounds that inhibit the binding of E-selectin or P-selectin to sialyl-Lewis.sup.x or sialyl-Lewis.sup.a presented on a cell surface having the general structure: ##STR1## This invention also relates to methods of inhibiting the binding of E-selectin or P-selectin to sialyl-Lewis.sup.x or sialyl-Lewis.sup.a presented on a cell surface using said compounds and to pharmaceutically active compositions comprising compounds that inhibit the binding of E-selectin to sialyl-Lewis.sup.x and to methods of treatment of septic shock, ARDS, Crohn's disease, chronic inflammatory diseases, such as psoriasis and rheumatoid arthritis, and reperfusion injuries that occurs following heart attacks, strokes and organ transplants and to the treatment of cancer.Type: GrantFiled: May 1, 1996Date of Patent: April 22, 1997Assignee: Texas Biotechnology CorporationInventors: Timothy P. Kogan, Brian Dupre, Huong Dao, Pamela J. Beck
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Patent number: 5620690Abstract: The invention relates to immunogenic complexes such as two-dimensional lamellae having a honeycomb structure and in particular three-dimensional iscoms, which immunogenic complexes are composed of at least one sterol, one saponin and, in the case of iscoms, also a phospholipid and also, optionally, at least one antigen generating an immune reaction. The saponin used is at least one of the fractions which are derived from Quil A by means of hydrophobic interaction chromatography and have the designations QA 1 to QA 23, as is shown in the figure by the numerals 1 to 23. Preferably, the saponin used is one or more of the fractions derived from Quil A having the designations QA 3, QA 17 and QA 23.Type: GrantFiled: April 19, 1993Date of Patent: April 15, 1997Assignee: De Stat Der Nederlanden Vertegenwoordigd Door De Minister Van Welzijn Volksgezondheid En CultuurInventors: Gideon F. A. Kersten, Arjan Spiekstra, Gerrit Van Der Werken, Eduard C. Beuvery
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Patent number: 5620961Abstract: A specialized derivative of fructose in which the compound is a fructose ester complexed with .beta.-cyclodextrin. Preferably, the fructose derivative is fructosehexanoate .beta.-cyclodextrin complex, and more preferably the fructose derivative is fructose-1-O-hexanoate .beta.-cyclodextrin complex. Fructose pentanoate and fructose heptanoate .beta.-cyclodextrin complexes are also included within the scope of the invention, and the fructose ester and the .beta.-cyclodextrin must be combined in approximately molar equivalent amounts. The present invention also includes a method for treating animals and humans with the instant fructose derivatives, to protect against tissue damage caused by doxorubicin cytotoxicity (particularly doxorubicin-induced cardiomyopathy or mucositis), ischemia, radiation damage and other sources of free oxygen radical cellular damage to the tissue of living animals and humans.Type: GrantFiled: October 24, 1994Date of Patent: April 15, 1997Inventors: Nenad S. Markovic, Olivera T. Markovic
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Patent number: 5620864Abstract: A biologically active oligosaccharide compound comprising at least two L hexose rings connected together by an ether oxygen atom. The ether oxygen atom is connected to a first of the rings at the first carbon atom to the right of the hexose ring oxygen atom. The compound contains at least one sulfate or phosphate group connected to the first ring at the third carbon atom to the right of the ring oxygen or to a methyl group at the fifth carbon atom to the right of the ring oxygen atom.The invention further includes the method for using the above oligosaccharide compound to detect .alpha. 1,3-L-fucosyltransferases or to block the activity of such .alpha. 1,3-L-fucosyltransferases or structures which mimic the structure of such fucosyltransferases to the extent that such structures bind to compounds of the present invention, e.g., as in the case of HIV virus.Type: GrantFiled: June 29, 1992Date of Patent: April 15, 1997Assignee: Health Research, Inc.Inventors: Khushi L. Matta, E. V. Chandrasekaran, Rakesh K. Jain
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Patent number: 5621094Abstract: A method of preserving delicate biological substances or organic compounds (a) in a dry state and/or (b) at elevated temperatures and/or (c) under irradiation comprises incorporating in a system containing the said substances or compounds, a sugar or a sugar derivative selected from (i) a non-reducing glycoside of a polyhydroxy compound selected from sugar alcohols and other straight chain polyalcohols, or (ii) a non-reducing oligosaccharide selected from raffinose, stachyose and melezitose. In particular, methods for preserving dehydrated agarose gels comprising adding lactitol or glucopyranosyl-mannitol or glucopyranosyl-sorbitol to the gel during formation and prior to dehydration are disclosed.Type: GrantFiled: June 8, 1994Date of Patent: April 15, 1997Assignee: Quadrant Holdings Cambridge LimitedInventors: Bruce J. Roser, Camilo Colaco
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Patent number: 5621084Abstract: This invention relates to a process for the removal of an allyl or allyloxycarbonyl group from an allyl or allyloxycarbonyl group protected compound (such as an allylic ester, carbonate, carbamate, O-allyl derivatives or N-allyl derivatives), which comprises contacting the allyl or allyloxycarbonyl group protected compound with a sulfinic acid compound, in the presence of a palladium catalyst in a reaction-inert solvent. Preferably, the sulfinic acid compound is represented by the formula:X--SO.sub.2 M (I)wherein X is C.sub.1-20 alkyl, substituted C.sub.1-20 alkyl (wherein the substituent(s) are independently halo, nitro, sulfo, oxo, amino, cyano, carboxy, hydroxy or moieties derived therefrom), phenyl, substituted phenyl (wherein the substituent(s) are independently C.sub.1-3 alkyl, halo nitro, sulfo, oxo, amino, cyano, carboxy, hydroxy, acetamido or moieties derived therefrom), furyl or thienyl; and M is hydrogen, an alkali metal or ammonium salt residue.Type: GrantFiled: April 3, 1995Date of Patent: April 15, 1997Assignee: Pfizer Inc.Inventors: Msanori Honda, Hiromasa Morita, Isao Nagakura
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Patent number: 5618705Abstract: Anti-inflammatory compounds are useful, for example, in treating arthritis and heart attack patients. Novel oligosaccharides useful in the rapid synthesis of certain anti-inflammatory compounds are disclosed, as is a rapid method of synthesizing the oligosaccharides. Low pH can loosen the acceptor specificity of galactosyltransferase (lactose synthase: EC 2.4.1.22), allowing the rapid synthesis of novel oligosaccharides. The disaccharides cellobiose (.beta.1.fwdarw.4), laminaribiose (.beta.1.fwdarw.3), gentiobiose (.beta.1.fwdarw.6) and maltose (.alpha.1.fwdarw.4) acted as acceptors for lactose synthase under low pH conditions. From these four acceptors, the following four novel trisaccharides were synthesized: Gal.sub.p (.beta.1.fwdarw.4)Glc.sub.p (.beta.1.fwdarw.3)-Glc, Gal.sub.p (.beta.1.fwdarw.4)Glc.sub.p (.beta.1.fwdarw.4)-Glc, Gal.sub.p (.beta.1.fwdarw.4)Glc.sub.p (.beta.1.fwdarw.6)-Glc and Gal.sub.p (.beta.1.fwdarw.4)Glc.sub.p (.alpha.1.fwdarw.4) Glc.Type: GrantFiled: May 31, 1995Date of Patent: April 8, 1997Assignee: Board of Supervisors of Louisiana State University Mechanical CollegeInventors: Roger A. Laine, Eunsun Yoon
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Patent number: RE35524Abstract: Phosphate derivatives of 4'-demethylepipodophyllotoxin glucosides are novel antitumor agents and the salts thereof offer the pharmaceutical advantage of high water solubility.Type: GrantFiled: April 19, 1994Date of Patent: June 3, 1997Assignee: Bristol-Myers Squibb CompanyInventors: Mark G. Saulnier, Peter D. Senter, John F. Kadow