Sulfur Containing Patents (Class 536/118)
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Patent number: 6025335Abstract: The invention relates to nucleoside dimers containing an L-sugar in at least one of the nucleosides and their pharmaceutical compositions.Type: GrantFiled: September 21, 1995Date of Patent: February 15, 2000Assignee: Lipitek International, Inc.Inventors: Alexander L. Weis, Charles T. Goodhue, Kirupathevy Pulenthiran
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Patent number: 5986087Abstract: Sulfonated regenerated cellulose fiber obtained by adding a modifier to a viscose dope or alkali cellulose or cellulose solution and spinning fiber therefrom, wherefor the modifier is a starch etherified with C.sub.2 -C.sub.5 -alkylsulfonic acid radicals and having a degree of substitution of 0.1 to 3, a starch admixed with vinylsulfonic acid or a styrenesulfonic acid, or a polymeric styrenesulfonic acid or polymeric vinylsulfonic acid.Type: GrantFiled: November 21, 1997Date of Patent: November 16, 1999Assignee: DyStar Textilfarben GmbH & Co. Deutschland KGInventors: Andreas Schrell, Bernd Huber
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Patent number: 5985582Abstract: Thrombin-based assays are disclosed for determining antithrombin III (ATIII) present in a plasma sample. The assays involve a heparin derivative which, like heparin, effectively enhances the antithrombin activity of ATIII, but which, unlike heparin, does not substantially enhance the antithrombin activity of Heparin cofactor II (HCII). In the present assay, HCII contributes about 15% or less to the determined antithrombin activity. A lyophilized reagent composition, useful in the ATIII assay and comprising thrombin and a heparin derivative, or alternatively comprising thrombin and heparin, is also disclosed. A high-calibrator plasma reference useful in the ATIII assays and in assays for other plasma constituents is also disclosed. Kits employing the several aspects of the invention are disclosed as well.Type: GrantFiled: December 9, 1997Date of Patent: November 16, 1999Assignee: Sigma-Aldrich Co.Inventor: Mark X. Triscott
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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: 5948405Abstract: Fucans with low molecular weight having anticoagulant, antithrombinic and antithrombotic activity.Fucan sulfates having molecular weight between 14000 and 29000 Dalton show a remarkable anticoagulant activity both in the global coagulation mechanism (APTT) and in the last phase of coagulation (antithrombinic activity). These compounds are useful also as antithrombotic drugs.Type: GrantFiled: December 18, 1997Date of Patent: September 7, 1999Assignee: Crinos Industria Farmacobiologica S.p.A.Inventors: Armando Cedro, Roberto Porta, Franco Cattaneo, Fabio Trento, Laura Ferro, Ennio Lanzarotti
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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: 5900478Abstract: Reaction at the interface of an organic solution containing an acidic reactant and an aqueous alkaline solution containing nonreducing carbohydrates such as sucrose, sugar alcohols, cyclodextrins, and polysaccharides imparts a specificity to the reaction for one or more of the primary alcohol groups of the carbohydrate reactant. The resulting activated, nonreducing carbohydrate intermediate can then be converted to a series of substantially pure, low molecular weight reaction products, including a sucrose trimer and dianhydrosucrose, and to a series of substantially pure, higher molecular weight reaction products, including 6-O-sucro cyclodextrins and poly-6-O-sucro amylose.Type: GrantFiled: June 20, 1997Date of Patent: May 4, 1999Assignee: Iowa State University Research Foundation, Inc.Inventors: John F. Robyt, Rupendra Mukerjea
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Patent number: 5869051Abstract: Conjugates of a carrier molecule and an organic molecule producing singlet oxygen after irradiation are useful in diagnostic and therapeutic applications. The organic molecule is a terthienyl or terfuranyl compound derivatized to react with amino, thiol, or saccharide groups of the carrier molecule. Suitable carrier molecules include antibodies, peptides, haptamers, sugars, and other analogous molecules which direct the organic molecule to a biological target.Type: GrantFiled: November 22, 1996Date of Patent: February 9, 1999Assignees: Giovanni Neri, L. Molenti & C. Dei Fratelli Alitti Societa' Di Esercizio Societa' Per AzioniInventors: Gabrio Roncucci, Giovanni Neri
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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: 5801240Abstract: An improved method of producing semi-refined kappa carrageenan is provided having processing steps including: (a) pre-rinsing carrageenan containing seaweed; (b) cooking the seaweed in a cooking tank containing an aqueous solution of KOH to cause desulfation at the 6-position of the galactose units of the carrageenan, to create recurring 3,6 anhydrous galactose polymers by dehydration and reorientation; (c) washing the seaweed in a neutralizing bath; (d) rinsing the seaweed in water; and, (e) drying and chopping the seaweed, the improvement being monitoring the reaction progress of the desulfation, dehydration and reorientation by continuously measuring oxidation-reduction potential of the aqueous KOH solution and, upon the occurrence of substantial reaction equilibrium of the reorientation, as indicated when the oxidation-reduction potential has reached a pre-determined constant value, stopping the reaction by removal of the seaweed from the aqueous KOH solution.Type: GrantFiled: March 7, 1997Date of Patent: September 1, 1998Assignee: Tanvest LimitedInventors: Christopher S. Rideout, Michael G. Bernabe
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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
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Patent number: 5773605Abstract: The invention relates to sulfated glycosaminoglycanoid derivatives of the heparin and heparan sulfate type, of which N-sulfate, N-acetate, and hydroxy groups, are replaced by alkoxy, aryloxy, aralkoxy, or O-sulfate groups. The compounds have antithrombotic and smooth muscle cell proliferation inhibiting activities.Type: GrantFiled: May 23, 1996Date of Patent: June 30, 1998Assignee: Akzo Nobel N.V.Inventors: Maurice Petitou, Constant Adriaan Anton van Boeckel
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Patent number: 5739301Abstract: 1-(2'-hydroxy- and 2'-sulfatoalkyl)glycosides of formula I ##STR1## where X is a hydroxyl or a sulfato group of the formula OSO.sub.3 M, whereM is hydrogen, an alkali metal or an ammonium cation which can be substituted by organic radicals,R is a C.sub.6 - to C.sub.30 -alkyl or alkylene radical andGly is the radical of a monosaccharide acetalized in the 1-position by the group designated above,are described.The glycosides I are suitable as surfactants or emulsifiers in detergents, cleaning compositions or personal hygiene compositions.Type: GrantFiled: August 15, 1996Date of Patent: April 14, 1998Assignee: BASF AktiengesellschaftInventors: Alfred Oftring, Beate Strecker, Gunter Oetter, Richard Schmidt, Wolfgang Klotz, Hendrik Wulff
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Patent number: 5739115Abstract: A novel class of highly sulfated maltooligosaccharide having heparin-like activity is described, as well as methods for using these oligosaccharides to treat certain diseases including cancer, and retinopathies.Type: GrantFiled: September 26, 1994Date of Patent: April 14, 1998Assignee: Glycomed IncorporatedInventors: Peter Fugedi, David J. Tyrrell, Robert J. Tressler, Robert J. Stack, Masayuki Ishihara
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Patent number: 5668274Abstract: The invention relates to sulfated glycosaminoglycanoid derivatives of the dermatan sulfate and chondroitin sulfate type, of which N-sulfate, N-acetate, and hydroxy groups, are replaced by alkoxy, aryloxy, aralkoxy, or O-sulfate groups. The compounds have antithrombotic and smooth muscle cell proliferation inhibiting activities.Type: GrantFiled: May 23, 1996Date of Patent: September 16, 1997Assignee: Akzo Nobel N.V.Inventors: Maurice Petitou, Constant Adriaan Anton van Boeckel
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Patent number: 5661130Abstract: The present invention relates to a method of increasing the absorption of a compound via the ocular, nasal, nasolacrimal or inhalation route into the circulatory system of a patient. In particular, a method comprising administering with the compound an absorption enhancer comprising a nontoxic, nonionic alkyl glycoside is provided. Additionally provided are methods of raising or lowering the blood glucose level by administering glucagon or insulin, respectively, with such absorption enhancers. Finally, compositions for raising or lowering the blood glucose level are provided.Type: GrantFiled: June 24, 1993Date of Patent: August 26, 1997Assignee: The UAB Research FoundationInventors: Elias Meezan, Dennis J. Pillion
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Patent number: 5658880Abstract: Compounds that exhibit selectin binding activity are described and have the following structural formula: ##STR1## where W is selected from a group including structures a-d below ##STR2## wherein p is an integer of from 0-2, q is an integer of from 0-3, and r is an integer of from 0-5;A is selected from the group consisting of .alpha. and .beta. forms of sialic acid, Kemp's acid, quinic acid, R and S forms of mandelic acid, R and S forms of glyceric acid, R and S forms of lactic acid, propionic and acetic acid, and esters and amides thereof, --SO.sub.3, sulfonate, --PO.sub.3, phosphonate, trifluoromethyl, diazine and triazine;B is selected from a group consisting of .alpha. and .beta. forms of fucose, arabinose and esters and substituted forms thereof wherein one or more of the OH groups is independently substituted with F, N.sub.3, NHAc, NHCOCF.sub.3. The remaining variable are described in the specification.Type: GrantFiled: August 12, 1994Date of Patent: August 19, 1997Assignee: Glycomed IncorporatedInventors: Falguni Dasgupta, John H. Musser, Daniel E. Levy, Peng Cho Tang
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Patent number: 5658893Abstract: A method is provided for inhibiting rotavirus infection of human cells by treating the rotavirus with a carrageenan. The most effective agent in inhibiting cellular rotavirus infection is lambda-carrageenan, which may be formulated in a liquid and ingested enterally. A composition containing lambda-carrageenan is an aspect of the invention.Type: GrantFiled: March 29, 1995Date of Patent: August 19, 1997Assignee: Abbott LaboratoriesInventors: Steven Neal Anderson, Joseph Paul Schaller, Terrence Bruce Mazer, Stephen John Kirchner
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Patent number: 5656308Abstract: Disclosed is a novel non-reducing oligosaccharide with neotrehalose structure represented by the general formula as shown by: ##STR1## The oligosaccharide is obtainable by exposing an aqueous solution containing neotrehalose to a saccharide-transferring enzyme, and has a superior stability, reduced sweetness, appropriate viscosity, no susceptibility to crystallization and less fermentability. These features make it very useful in various compositions including foods, beverages, cosmetics and pharmaceuticals.Type: GrantFiled: June 6, 1995Date of Patent: August 12, 1997Assignee: Kabushiki Kaisha Hayashibara Seibutsu Kagaku KenkyujoInventors: Hajime Aga, Takashi Shibuya, Toshiyuki Sugimoto, Toshio Miyake
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Patent number: 5637690Abstract: A sulfate ester of N-acetylneuraminic acid homopolymer represented by the formula (I) or a pharmaceutically acceptable salt thereof: ##STR1## wherein R represents H or SO.sub.3 H, n is 5-1,000, wherein the number of SO.sub.3 H residues per 1 molecule of N-acetylneuraminic acid residues is 0.1 to 3.0, which sulfate ester demonstrates anti-HIV activity.Type: GrantFiled: December 27, 1994Date of Patent: June 10, 1997Assignee: Marukin Shoyu Co., Ltd.Inventors: Jang-ho Lee, Yasuhiro Ota, Yoji Tsukada
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Patent number: 5627273Abstract: The present invention is directed to methods of preparing hydrophobically-terminated polysaccharide polymers. The methods utilized to prepare the hydrophobically-terminated polysaccharide polymers utilize water as the reaction solvent and do not utilize any cosolvent. The invention is also directed to hydrophobically-terminated polysaccharide polymers which are useful as deflocculants in liquid detergent compositions and to the liquid detergent compositions which contain the hydrophobically-terminated polysaccharide polymers.Type: GrantFiled: January 31, 1995Date of Patent: May 6, 1997Assignee: National Starch and Chemical Investment Holding CorporationInventors: John S. Thomaides, James Burkert
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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: 5593887Abstract: Oligosacaharide compounds that are substrates and inhibitors of glycosyltransferase and glycosidase enzymes and compositions containing such compounds are disclosed. A method of glycosylation is also disclosed. An E. coli transformed with phagemid CMPSIL-1, which phagemid comprises a gene for a modified CMP-sialic acid synthetase enzyme, which transformed E. coli has the ATCC accession No. 68531 is also provided.Type: GrantFiled: June 7, 1995Date of Patent: January 14, 1997Assignee: The Scripps Research InstituteInventors: Chi-Huey Wong, Yoshitaka Ichikawa, Gwo-Jenn Shen
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Patent number: 5589588Abstract: A sulfated acid amide having heparin-like properties of the formula:(R.sub.1)--NH--R--NH--(R.sub.1)whereR.sub.1 is a di-, tri- or tetra-saccharide acid selected from cellobiose, cellotriose, cellotetrose, maltose, maltotriose and maltotetrose or mixtures thereof, andR is an alkylene of from 3 to 12 carbons, and is optionally substituted with one or more hydroxyls.Type: GrantFiled: March 30, 1993Date of Patent: December 31, 1996Assignee: Reliable Biopharmaceutical CorporationInventor: Joseph A. Toce
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Patent number: 5589465Abstract: Novel glycolipid derivatives of Formula (I): ##STR1## wherein R is a long chain alkyl, or their salts are disclosed. These compounds act as a ligand for selectin family and exhibit a remarkable inhibitory effect on the binding of selectin family to its native ligand sialyl Lewis.sup.x.Type: GrantFiled: March 1, 1995Date of Patent: December 31, 1996Assignees: Akira Hasegawa, Kanebo Ltd.Inventors: Hideharu Ishida, Makoto Kiso, Akira Hasegawa
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Patent number: 5580858Abstract: Disclosed are novel Lewis.sup.x and Lewis.sup.a analogues, pharmaceutical compositions containing such analogues, methods for their preparation and methods for their use.Type: GrantFiled: November 4, 1994Date of Patent: December 3, 1996Assignee: Alberta Research CouncilInventors: Robert M. Ippolito, Wasimul Haque, Cong Jiang, H. Rizk Hanna, Andre P. Venot, Pandurang V. Nikrad, Mohammed A. Kashem, Richard H. Smith
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Patent number: 5576304Abstract: A pharmaceutical composition comprising dermatan sulphate, together with a low molecular weight heparin, free or fixed combination, is useful as a antithrombolytic agent with a low risk of bleeding complications.Type: GrantFiled: July 9, 1991Date of Patent: November 19, 1996Assignee: Thrombosis Research InstituteInventors: Vijay V. Kakkar, Michael F. Scully
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Patent number: 5563258Abstract: This specification discloses a production process for an sucralfate aqueous suspension stock, the process being characterized by direct dispersement of an sucralfate aqueous stock for sucralfate preparations, which contains sucralfate particles with an average particle size of no more than 50 .mu.m in a concentration of 1-2 g/ml, in water or other aqueous medium without drying the synthesized sucralfate wet powder, followed by milling of the sucralfate particles to an average particle size of no more than 50 .mu.m. When the sucralfate aqueous suspension stock obtained directly from wet powder in accordance with this method is compared to the conventional suspension obtained from dry powder, equivalency of both stocks are obtained in terms of both properties and pharmacological activities. In comparison to the conventional process using dry powder, this wet milling method of production is economically and operationally superior and environmental pollution arising from the conventional process can be prevented.Type: GrantFiled: April 26, 1995Date of Patent: October 8, 1996Assignee: Chugai Seiyaku Kabushiki KaishaInventors: Kiyoshige Ochi, Kazuo Sasahara, Mituo Shiratori, Sakae Takaku
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Patent number: 5552462Abstract: A novel blend composition comprising one or more cationic polygalactomannas and xanthan gum is provided. The blend is capable of producing enhanced viscosities when distributed in a solvent. The blend is suitable for use in foods, explosives, oil field chemicals, textile fibers, agricultural chemicals and cosmetics.Type: GrantFiled: November 22, 1993Date of Patent: September 3, 1996Assignee: Rhone-Poulenc Inc.Inventor: Michael H. Yeh
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Patent number: 5543403Abstract: The invention relates to sulfated glycosaminoglycanoid derivatives of the heparin and heparan sulfate type, of which N-sulfate, N-acetate, and hydroxy groups, are replaced by alkoxy, aryloxy, aralkoxy, or O-sulfate groups. The compounds have antithrombotic and smooth muscle cell proliferation inhibiting activities.Type: GrantFiled: October 19, 1994Date of Patent: August 6, 1996Assignees: AKZO Nobel NV, Sanofi S.A.Inventors: Maurice Petitou, Constant A. A. Van Boeckel
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Patent number: 5529985Abstract: The invention relates to sulfated glycosaminoglycanoid derivatives of the dermatan sulfate and chondroitin sulfate type, of which N-sulfate, N-acetate, and hydroxy groups, are replaced by alkoxy, aryloxy, aralkoxy, or O-sulfate groups. The compounds have antithrombotic and smooth muscle cell proliferation inhibiting activities.Type: GrantFiled: November 2, 1994Date of Patent: June 25, 1996Assignees: Akzo Nobel NV, Sanofi S.A.Inventors: Maurice Petitou, Constant A. A. van Boeckel
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Patent number: 5523099Abstract: Disclosed is a novel non-reducing oligosaccharide with neotrehalose structure represented by the general formula as shown by: ##STR1## The oligosaccharide is obtainable by exposing an aqueous solution containing neotrehalose to a saccharide-transferring enzyme, and has a superior stability, reduced sweetness, appropriate viscosity, no susceptibility to crystallization and less fermentability. These features make it very useful in various compositions including foods, beverages, cosmetics and pharmaceuticals.Type: GrantFiled: December 9, 1994Date of Patent: June 4, 1996Assignee: Kabushiki Kaisha Hayashibara Seibutsu Kagaku KenkyujoInventors: Hajime Aga, Takashi Shibuya, Toshiyuki Sugimoto, Toshio Miyake
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Patent number: 5519010Abstract: The present invention provides a sulfated polysaccharide (D-HG), a pharmaceutically acceptable salt thereof, a process for preparing the same and a medicament containing the same as the effective component for DIC (disseminated intravascular coagulation) and thrombosis, the sulfated polysaccharide (D-HG) being prepared by depolymerization of FGAG (a sulfated polysaccharide extracted from a body wall of a sea cucumber with such activities as those of heparin) or a salt thereof and having the following physicochemical properties:[1] Molecular weight:3,000 to 42,000 (as measured by high performance GPC)[2] Characteristic:white, amorphous, highly hygroscopic powder[3] Solubility:soluble in water but insoluble in ethanol, acetone and like organic solvents[4] Specific rotation:[.alpha.].sub.D.sup.20 =-55 to -73.degree.Type: GrantFiled: May 12, 1994Date of Patent: May 21, 1996Assignees: Taiho Pharmaceutical Co., Ltd., Kotai Kasei Co., Ltd.Inventors: Hui-Zeng Fan, Song Yu, Etsuji Yamanaka, Kazuhiro Numata, Toshinori Oka, Norihiko Suzuki, Yoshiyuki Muranaka
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Patent number: 5514659Abstract: The invention relates to 3-deoxy oligosaccharides of formula I: ##STR1## in which X represents an --OSO.sub.3.sup.- radical, a radical of formula R--O, a radical of formula: ##STR2## or a radical of formula: ##STR3## Y represents a radical of formula: ##STR4## R represents an alkyl radical, R.sub.1, R.sub.3, R.sub.5, R.sub.7, R.sub.8, R.sub.10, R.sub.12 and R.sub.13 represent a hydroxyl radical, an alkoxy radical or an --OSO.sub.3.sup.- radical,R.sub.2, R.sub.4, R.sub.6, R.sub.9 and R.sub.11 represent a hydrogen atom, a hydroxyl radical, an alkoxy radical or an --OSO.sub.3.sup.- radical, with the proviso that at least R.sub.2 or R.sub.4 or R.sub.6 or R.sub.9 or R.sub.11 represents a hydrogen atom,and their pharmaceutically acceptable salts with a base.Type: GrantFiled: April 21, 1994Date of Patent: May 7, 1996Assignees: Elf Sanofi, Akzo Nobel NVInventors: Maurice Petitou, Guy F. B. Jaurand, Constant A. A. Van Boeckel
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Patent number: 5512672Abstract: A beta-1,3-glucan of sulfated curdlan having a sulfur content of 12.4 to 17% and an average molecular weight of 27,000 to 330,000 daltons. Sulfate curdlan exhibits strong HIV inhibitory activity with little anticoagulant activity and little toxicity.Type: GrantFiled: June 14, 1993Date of Patent: April 30, 1996Assignees: Ajinomoto Co., Inc., Fujirebio, Inc.Inventors: Naoki Yamamoto, Hideki Nakashima, Toshiyuki Uryu, Takashi Yoshida, Kei Matsuzaki, Yutaro Kaneko, Toru Mimura
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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: 5489675Abstract: Novel NeuAc-Gal dissacharide sialidase substrates and inhibitors which are locked into rigid conformation by the attachment of an alkyl group at the C-6 arm of the galactose core are provided. Also provided is a method for the inhibition of sialidase activity.Type: GrantFiled: November 3, 1993Date of Patent: February 6, 1996Assignee: E. I. Du Pont de Nemours and CompanyInventor: Subramaniam Sabesan
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Patent number: 5488102Abstract: Compounds of formulae I and IaR--Y--CO--R.sub.3 --CO--O--A (I),R--Y--CO--R.sub.3 --CO--O--CH.sub.2 --A.sub.1 (Ia),whereinR is a radically polymerisable hydrocarbon group,R.sub.3 is a direct bond, linear or branched C.sub.1 -C.sub.22 alkylene, C.sub.3 -C.sub.8 cycloalkylene or C.sub.6 -C.sub.14 arylene,A is the radical, reduced by a hydroxy group in a 2- or 3position, of a cyclic-oligomeric carbohydrate or of a derivative of such a carbohydrate,A.sub.1 is the radical, reduced by a hydroxymethyl group, of a monomeric or linear oligomeric carbohydrate or of a derivative of such a carbohydrate, andY is --O--, --NH-- or --N(C.sub.1 -C.sub.6 alkyl)-.Homo- and co-polymers having those monomers have, depending upon their composition, hydrophilic, amphiphilic or hydrophobic properties and are able to form hydrogels. The polymers can be used, for example, as surfactants, thickeners, carriers for biologically active ingredients or in the manufacture of contact lenses.Type: GrantFiled: July 26, 1994Date of Patent: January 30, 1996Assignee: Ciba Geigy CorporationInventor: Dirk Vetter
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Patent number: 5484777Abstract: This invention encompasses a method and compositions which inhibit pancreatic cholesterol esterase and triglyceride lipase and hence, lower cholesterol and triglycerides in the blood stream.Type: GrantFiled: December 15, 1993Date of Patent: January 16, 1996Inventors: Louis G. Lange, III, Curtis A. Spilburg
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Patent number: 5461143Abstract: Oligosaccharide compounds that are substrates and inhibitors of glycosyltransferase and glycosidase enzymes and compositions containing such compounds are disclosed. A method of glycosylation is also disclosed. An E. coli transformed with phagemid CMPSIL-1, which phagemid comprises a gene for a modified CMP-sialic acid synthetase enzyme, which transformed E. coli has the ATCC accession No. 68531 is also provided.Type: GrantFiled: March 29, 1994Date of Patent: October 24, 1995Assignee: The Scripps Research InstituteInventors: Chi-Huey Wong, Yoshitaka Ichikawa, Gwo-Jenn Shen
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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: 5447919Abstract: The use of compounds of the formula ##STR1## wherein R is hydrogen or a residue --SO.sub.3 M; M is a cation; and R' and R" are hydrogen or an .alpha.-glycosidically linked sulfated mono- or disaccharide residue; and at least one --SO.sub.3 M group is present per monosaccharide unit,as pharmaceutical compositions for the prevention and/or treatment of arteriosclerotic disorders and for the prevention of restenosis after invasive vascular surgery and after organ transplants.Type: GrantFiled: March 17, 1994Date of Patent: September 5, 1995Assignee: Hoffmann-La Roche Inc.Inventors: Markus Hosang, Niggi Iberg, Thomas B. Tschopp, Hans P. Wessel
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Patent number: 5442046Abstract: This invention relates to alkyl and/or alkenyl oligoglycoside isethionates prepared by reacting salts of vinyl sulfonic acid at an elevated temperature and in the presence of basic compounds, with alkyl and/or alkenyl oligoglycosides of the formula (1): R.sup.1 O--(G).sub.p in which R.sup.1 is a straight-chain or branched-chain aliphatic hydrocarbon group with 6 to 22 carbon atoms and 0, 1,2 or 3 double bonds, G is a glycose unit with 5 or 6 carbon atoms, and p is a number between 1 and 10. The products exhibit marked surface-active characteristics and are useful as surfactants.Type: GrantFiled: May 9, 1994Date of Patent: August 15, 1995Assignee: Henkel Kommanditgesellschaft auf AktienInventor: Manfred Weuthen
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Patent number: 5424300Abstract: An agent for treatment of chronic fatigue syndrome, which comprises a polysaccharide having a .beta.-1,3-glucoside bond in the main chain as an effective ingredient.Type: GrantFiled: October 13, 1993Date of Patent: June 13, 1995Assignee: Kaken Pharmaceutical Co.Inventor: Atsushi Uchida
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Patent number: 5424416Abstract: A stereoselective process for preparing a .beta.-anomer enriched 2-deoxy-2,2-difluoro-D-ribofuranosyl-3,5-hydroxy protected-1-alkyl and aryl sulfonate intermediates by contacting an .alpha.-anomer enriched 2-deoxy-2,2-difluoro-D- ribofuranosyl-3,5-hydroxy protected-1-fluoroalkyl and fluoroaryl sulfonate with a conjugate anion of a sulfonic acid containing the desired alkyl or aryl sulfonate.Type: GrantFiled: August 25, 1993Date of Patent: June 13, 1995Assignee: Eli Lilly and CompanyInventor: Charles D. Jones
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Patent number: 5401647Abstract: Disclosed is a method of preparing limulus amoebocyte lysate substantially free from factor G which comprises bringing limulus amoebocyte lysate into contact with an insoluble carrier on which a (1.fwdarw.3)-.beta.-D-glucoside structural portion represented by the following formula [I] produced by depolymerizing and/or fractionating a carbohydrate chain is immobilized: ##STR1## wherein n represents an integer of 2 to 370.Type: GrantFiled: May 27, 1992Date of Patent: March 28, 1995Assignee: Seikagaku Kogyo Kabushiki Kaisha (Seikagaku Corporation)Inventors: Shigenori Tanaka, Jun Aketagawa, Yuko Shibata
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Patent number: 5386019Abstract: The total synthesis of a group of compounds with inhibitory effects on calmodulin-mediated enzyme activities has been accomplished. Among these synthesized compounds are KS-501 and KS-502. Other compounds that have been synthesized by the described scheme are ent-KS-501 and ent-KS-502 which are enantiomers of KS-501 and KS-502 and which also have inhibitory effects on calmodulin-mediated enzyme activities.Type: GrantFiled: January 15, 1992Date of Patent: January 31, 1995Assignee: Yale UniversityInventors: Samuel J. Danishefsky, Russell Dushin, William N. Hait
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Patent number: 5382570Abstract: The invention relates to sulfated glycosaminoglycanoid derivatives of the dermatan sulfate and chondroitin sulfate type, of which N-sulfate, N-acetate, and hydroxy groups, are replaced by alkoxy, aryloxy, aralkoxy, or O-sulfate groups. The compounds have antithrombotic and smooth muscle cell proliferation inhibiting activities.Type: GrantFiled: July 27, 1992Date of Patent: January 17, 1995Assignees: Akzo, N.V., Snofi, S.A.Inventors: Maurice Petitou, Constant A. A. van Boeckel
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Patent number: 5378828Abstract: The present invention provides a process for the preparation of water soluble alkali metal salts of cellulose sulfate having a degree of substitution ranging from 1 to 3 and viscosity of 1 percent aqueous solution in excess of 20 centipoises (cps). The process involves the use of chlorosulfuric acid as a sulfonating agent in the presence of pyridine used as a solvent in reaction. The important steps of the process for preparation of the water soluble salts include presoaking of the cellulose in pyridine followed by washing the pyridine salt with an alcohol such as methanol and reacting saturated alkali metal bicarbonate or carbonate solutions with the sulfonated cellulose.Type: GrantFiled: September 2, 1993Date of Patent: January 3, 1995Assignee: Dextran Products LimitedInventors: Thomas C. Usher, Natu Patel, Chhagan G. Tele
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Patent number: RE36385Abstract: This invention relates to glucopyranose compounds of formula (I) and (IA) ##STR1## and the non-toxic salts thereof wherein the substituents are as defined herein. Such materials possess enhancing activity of cellular immunity (e.g. mitogenic activity) to living tissue and therefore are useful as anti-tumor agents.Type: GrantFiled: May 20, 1993Date of Patent: November 9, 1999Assignee: Ono Pharmaceutical Co., Ltd.Inventors: Masaaki Toda, Yutaro Sasaki, Katsuichi Shimoji