Viscosity Or Degree Of Polymerization Changed (e.g., Degrading, Cross Linking, Etc.) Patents (Class 536/41)
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Patent number: 5380834Abstract: An immuno-suppressive agent containing, as an effective component, an, enopyranose derivative of the following formula (I) or its salt: ##STR1## wherein R.sup.1 is a hydrogen atom, alkyl which may be substituted, alkenyl, alkynyl, --OSO.sub.2 R.sup.7, a halogen atom, --OCOR.sup.7, --NHCOR.sup.8, alkoxy, phenyl which may be substituted or a saccharose residue, R.sup.2 is a hydrogen atom or alkyl, R.sup.3 is a hydrogen atom or a halogen atom, R.sup.4 is a hydrogen atom, --COR.sup.9, silyl which may be substituted or alkyl which may be substituted, one of R.sup.5 and R.sup.6 is hydroxyl, alkoxy which may be substituted, a saccharose residue, cycloalkyloxy which may be substituted or --OCOR.sup.10 and the other is a hydrogen atom or alkyl which may be substituted, or R.sup.4 and R.sup.5 together form a single bond, while R.sup.6 is a hydrogen atom or alkyl which may be substituted, each of R.sup.7, R.sup.9 and R.sup.10 is alkyl or phenyl which may be substituted, R.sup.Type: GrantFiled: January 27, 1993Date of Patent: January 10, 1995Assignee: Ishihara Sangyo Kaisha Ltd.Inventors: Sadanori Mizukoshi, Fuminori Kato, Masamitsu Tsukamoto, Kenji Kon
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Patent number: 5380714Abstract: Compounds of the formula I: ##STR1## wherein: X is O, S or NH;n is O or an integer of from 1 to 3;R.sup.1 is hydrogen, (1-6C)alkyl, or (1-4C)alkanoyl;R.sup.2 is CH.sub.2 R.sup.3, NHR.sup.4, SO.sub.2 NR.sup.5 YNR.sup.6 R.sup.7 or R.sup.8, in which R.sup.3 is hydroxy, (1-4C)alkoxy or (1-4C)alkylsulphonyl; R.sup.4 is (1-4C)alkylsulphonyl, (1-4C)haloalkylsulphonyl, formyl, carbamoyl or 2,6-dichloro-4-(2-(1,1-dimethylethyl)amino-1-hydroxyethyl)phenyl; R.sup.5 is hydrogen or (1-4C)alkyl; Y is CO or (1-6C)alkylene; R.sup.6 and R.sup.7 are independently (1-4C)alkyl, or R.sup.6 is hydrogen and R.sup.7 is (1-4C)alkyl, (1-4C)haloalkyl, phenyl(1-4C)alkyl or, when Y is (1-6C)alkylene, is (1-4C)alkylaminocarbonyl or (5-6C)cycloalkylaminocarbonyl; and R.sup.8 is a sugar residue of formula II in which R.sup.Type: GrantFiled: November 20, 1992Date of Patent: January 10, 1995Assignee: Imperial Chemical Industries PLCInventors: Geraint Jones, Roger James, Rodney B. Hargreaves
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Patent number: 5378831Abstract: Galactosyl maltooligosaccharide derivatives represented by formula (1): ##STR1## wherein at least one of X.sub.1 and X.sub.2 represents a galactosyl group and the other represents a hydrogen atom, R represents a hydrogen atom or a substituted or unsubstituted phenyl group, and n is an integer of from 2 to 5. The derivatives are prepared by reacting a sugar with a galactosyl group with a maltooligosaccharide represented by formula (2): ##STR2## R represents a hydrogen atom or a substituted or unsubstituted phenyl group, and n is an integer of from 2 to 5; in the presence of .alpha.-galactosidase or .beta.-galactosidase. The derivatives are used for measurement of .alpha.-amylase activity.Type: GrantFiled: September 4, 1992Date of Patent: January 3, 1995Assignees: Nihon Shokuhin Kako Co., Ltd., Yaizu Suisan Kagaku Kogyou Co., Ltd.Inventors: Taichi Usui, Osamu Uejima, Koichi Ogawa
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Patent number: 5374711Abstract: This invention relates to novel elsamicin A derivatives wherein the 2"-amino group is selectively modified by acylation or alkylation, a process for producing said elsamicin A derivatives, an antitumor composition containing the same as the active ingredient, and a method for therapy using said compositions.Type: GrantFiled: September 15, 1993Date of Patent: December 20, 1994Assignee: Bristol-Myers Squibb CompanyInventors: Soichiro Toda, Haruhiro Yamashita, Takayuki Naito, Yuji Nishiyama
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Patent number: 5372937Abstract: A method of producing an oligosaccharide compound which either consists of or is a fragment or analog of the carbohydrate part in a glycoconjugate is disclosed which involves reacting(a) at least one oligosaccharide, disaccharide, monosaccharide, or glycoside as donor substance,(b) at least one acceptor substance containing a monosaccharide, disaccharide, oligosaccharide, glycoside, or saccharide analog, and(c) at least one enzyme composition produced from a mollusc and containing E.C. group 3.2 glycosidase, or the glycosidase is at least one glycosidase which has been cloned with recombinant technique and which has at least 70% homology in its amino acid sequence with the corresponding mollusc enzyme, to form the oligosaccharide compound;wherein the oligosaccharide compound contains(i) GlcNAc.beta.1-3Gal.beta. and the glycosidase is N-acetyl-.beta.-D-glucosaminidase,(ii) GlcNAc.beta.1-6Man.alpha. and the glycosidase is N-acetyl-.beta.-D-glucosaminidase,(iii) GlcNAc.beta.1-6Gal.alpha.Type: GrantFiled: February 18, 1992Date of Patent: December 13, 1994Assignee: Procur AktiebolagInventor: Kurt G. I. Nilsson
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Patent number: 5372949Abstract: The present invention is directed to a fluorescence polarization immunoassay for determining the 3-methoxy-4-hydroxyphenylglycol content in body fluids, to the various components needed for preparing and carrying out such an assay, and to methods of making these components. Specifically, tracers, immunogens and antibodies are disclosed, as well as methods for preparing them. The assay is conducted by measuring the degree of polarization of plane polarized light that has been passed through a sample containing antiserum and tracer.Type: GrantFiled: September 3, 1992Date of Patent: December 13, 1994Assignee: Abbott LaboratoriesInventors: Christine H. Zeitvogel, Maciej B. Adamczyk, David A. Betebenner, Kenward S. Vaughan
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Patent number: 5371202Abstract: An improved process for the preparation of O-glycosyl compounds of sialic acid, which are useful as intermediates in the synthesis of sialoconjugated glycosides. This process comprises effecting condensation reaction between thioglycosides of sialic acid and sugar derivatives in the presence of N-iodosuccinimide and trifluoromethanesulfonic acid. O-glycosyl compounds of sialic acid are prepared in high resio- and stereo-selectivity and in high yields.Type: GrantFiled: February 12, 1992Date of Patent: December 6, 1994Assignee: The Nisshin Oil Mills, Ltd.Inventor: Akira Hasegawa
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Patent number: 5366963Abstract: A method for suppressing immune responses in animals by administering a mixture of gangliosides to the animal where the gangliosides have heterogeneous ceramide structures containing fatty acid portions with carbon chain lengths of 21-30 or less than 18 carbon atoms. Ganglioside mixtures which are homogeneous with respect to the fatty acid portion are also effective immunosuppressive agents when the carbon chain length of the fatty acid portion is less than 18. Compositions containing the above specified ganglioside mixtures are also disclosed.Type: GrantFiled: February 23, 1993Date of Patent: November 22, 1994Assignee: The Regents of the University of CaliforniaInventor: Stephan Ladisch
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Patent number: 5367062Abstract: Derivatives of disubstituted and deoxydisubstituted .alpha.-D-lyxofuranosides and intermediates for preparing these derivatives are described. These compounds exhibit significant antiinflammatory and anti-proliferative activity and are useful for treating inflammatory and/or autoimmune disorders such as psoriasis, asthma, atopic dermatitis, rheumatoid arthritis, osteoarthritis, scleroderma, systemic lupus erythematosus, and cancer (particularly melanoma and colon cancer).Type: GrantFiled: August 21, 1992Date of Patent: November 22, 1994Assignee: Medicarb Inc.Inventors: Sudershan K. Arora, Peter J. Schied
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Patent number: 5364794Abstract: A simplified process is provided for producing saccharides of definite chain length, such as glucose, maltose and maltooligosaccharides, each in an isolated state and with a high purity.The process comprises transferring a saccharide chain, using a saccharide chain transferase, from a saccharide chain source to a substance substantially separable from the saccharides mentioned above and treating the thus-obtained oligosaccharide with an enzyme capable of excising the saccharide chain of definite chain length in an exo manner.Type: GrantFiled: February 4, 1993Date of Patent: November 15, 1994Assignee: Nippon Shinyaku Company LimitedInventors: Yohji Ezure, Shigeaki Maruo, Katsunori Miyazaki, Naoyoshi Yamada
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Patent number: 5364767Abstract: The present invention relates to chromogenic compounds which are represented by the general Formula (I): ##STR1## wherein R.sub.1 is a sugar group, ester group, hydrocarbyl group, phosphate group, sulfate group or a salt thereof, with the proviso that R.sub.1 is other than .beta.-D-glucuronic acid or .beta.-D-galactopyranoside, R.sub.2 is H or hydrocarbyl group containing 1 to about 5 carbon atoms, X is Cl or H, and Y is Cl or H. The present invention further relates to a method for quantitatively identifying and differentiating a first biological material having enzyme specificity for a first chromogenic compound as represented by Formula (I) above, and a second biological material having enzyme specificity for a second chromogenic compound.Type: GrantFiled: February 11, 1993Date of Patent: November 15, 1994Assignee: Research Organics, In.Inventors: Daniel G. Flowers, Marvin Sternfeld
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Patent number: 5362628Abstract: The subject invention provides a method for analyzing the metabolic activity in cells by improving the retention of a detectable reporter molecule only in intact cells where a particular enzyme is present. In particular, improved retention results from a two part process involving conjugation of haloalkyl-substituted derivatives of a reporter molecule with intracellular cysteine-containing peptides while unblocking the reporter molecule. The method for analyzing metabolic activity of cells involves the use of a substrate having the formXR-REPORTER-BLOCKwherein -BLOCK is a group selected to be removable by action of a specific analyte, to give REPORTER spectral properties different from those of the substrate,-REPORTER- is a molecule that, when no longer bound to BLOCK by a BLOCK-REPORTER bond, has spectral properities different from those of the substrate, andXR-- is a haloalkyl moiety that can covalently react with an intracellular thiol (Z--S--H) to form a thioether conjugate (Z--S--R--).Type: GrantFiled: March 5, 1993Date of Patent: November 8, 1994Assignee: Molecular Probes, Inc.Inventors: Richard P. Haugland, Yu-Zhong Zhang, Ram Sabnis, Nels A. Olson, John J. Naleway, Rosaria P. Haugland
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Patent number: 5362861Abstract: A continuous method of bleaching an alkylpolyglycoside, substantially free of alcohol, with peroxy compounds, preferably hydrogen peroxide, which is highly efficient to provide an unexpected high degree of color reduction from a dark brown to a light, white product, from an extinction coefficient color respectively of about 10 to about 15 to about 0.025 to about 0.15. The bleaching is carried out at controlled pH and temperature, under pressure preferably in the presence of Mg or MgO.Type: GrantFiled: July 15, 1992Date of Patent: November 8, 1994Assignee: Henkel CorporationInventors: Patrick M. McCurry, Jr., Robert L. Klein, Jr., Michael W. Gibson, James D. Beaulieu, Janet R. Varvil
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Patent number: 5362860Abstract: A solid composition for stabilizing the dosage of cognition activator CI-979 HCl by formation of a complex with cyclic polydextrose. In particular, compositions with HP.beta.CD have been found to stabilize CI-979 HCl even in the presence of other excipients such as sodium carbonate. Pharmaceutical formulations for the treatment of cognitive disorders in humans are based on the stabilizing composition of CI-979 HCl and cyclic polydextrose, including appropriate amounts of other excipients or components as known in the formulation art.Type: GrantFiled: February 1, 1993Date of Patent: November 8, 1994Assignee: Warner-Lambert CompanyInventors: Hua-Pin Huang, Scott C. Wootton, Thomas N. Julian, Galen W. Radebaugh, Mahdi B. Fawzi
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Patent number: 5360792Abstract: The compounds of this invention are 5- or 6-deoxy hexose monosaccharides having a saturated nitrogen-containing heterocycle at the 5- or 6-position bound through the nitrogen atom. The saturated nitrogen-containing heterocycle substituent is shown by the following formula: ##STR1## where X is CH.sub.2, NH or O; and n ranges from 3-6. These hexose monosaccharides may also be ethereally substituted at least one other position. The compounds exhibit anti-proliferative and anti-inflammatory activity. Methods of preparation, pharmaceutical compositions containing the compounds and methods of treating inflammatory and/or autoimmune disorders employing the compounds are disclosed.Type: GrantFiled: June 29, 1992Date of Patent: November 1, 1994Assignee: Greenwich Pharmaceuticals IncorporatedInventors: Sudershan K. Arora, David S. Thomson, M. Nayeem Akhtar
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Patent number: 5360899Abstract: Hydrophilic, water-dilatable cyclodextrin polymerizates have a high cyclodextrin content and possess good mechanical properties. The cyclodextrin pearl polymerizates are produced by reacting hydroxyalkyl cyclodextrin derivatives with bifunctional crosslinking agents such as epichlorohydrin or diepoxides, followed by hydroxyalkylation of the primary product so obtained. The cyclodextrin polymerizates produced in this manner have mechanical properties appreciably superior to those of known, comparable cyclodextrin polymers.Type: GrantFiled: September 25, 1992Date of Patent: November 1, 1994Assignee: Consortium fur Elektrochemische Industries GmbHInventors: Peter Nussstein, Guenther Staudinger, Wolfram Steinert, Franz-Heinrich Kreuzer, Wolfgang Schmitt-Sody
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Patent number: 5360794Abstract: The compounds of the present invention are deoxy disubstituted or dideoxy disubstituted derivatives of .alpha.-D-mannofuranoside and .beta.-L-gulofuranoside hexoses which exhibit anti-inflammatory and anti-proliferative activity. Pharmaceutical compositions containing the compounds and methods of treating inflammatory and/or autoimmune disorders employing the compounds are disclosed.Type: GrantFiled: August 3, 1992Date of Patent: November 1, 1994Assignee: Medicarb Inc.Inventor: Sudershan K. Arora
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Patent number: 5358936Abstract: A glucofuranose derivative substituted at the 3,5,6- or 3,6-positions with a radical that provides an anionic charge at physiological pH values is disclosed, as are pharmaceutical compositions, and methods of making and using the same. The compounds are useful in treating inflammation, and particularly conditions that involve neutrophil influx; they are also useful in inhibiting gastric ulcer formation.Type: GrantFiled: July 31, 1991Date of Patent: October 25, 1994Assignee: Paul GordonInventors: Paul Gordon, Edward P. Gamson
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Patent number: 5358854Abstract: A chromogenic .beta.-galactosidase substrate producing an insoluble precipitate of a first color when reacted upon by .beta.-galactosidase and a chromogenic .beta.-glucuronidase substrate producing an insoluble precipitate of a second, contrasting color when reacted upon by .beta.-glucuronidase are combined in test medium for quantitatively identifying and differentiating general coliforms and E. coli. The .beta.-galactosidase substrate 5-bromo-4-chloro-3-indolyl-.beta.-D-galactopyranoside which produces an indigo blue precipitate when reacted upon by .beta.-galactosidase may be used with one of the novel compounds 6-chloroindolyl-.beta.-D-glucuronide, 4,6-dichloroindolyl-.beta.-D-glucuronide, 6,7-dichloroindolyl-.beta.-D-glucuronide, and 4,6,7-trichloroindolyl-.beta.-D-glucuronide, which produce mauve or magenta precipitates when reacted upon by .beta.-glucuronidase. The .beta.-glucuronidase substrate 5-bromo-4-chloro-3-indolyl-.beta.Type: GrantFiled: June 3, 1993Date of Patent: October 25, 1994Assignee: Research Organics, Inc.Inventor: Wilfred J. Ferguson
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Patent number: 5358656Abstract: The present invention relates to liquid detergent compositions wherein the detergent active mixture of the compositions comprises 65 to 99% of a glyceroglycolipid compound having an amine linkage and 1 to 35% of a nonionic surfactant. Unexpectedly, applicants have discovered a synergy in the mixture of these surfactants which leads to enhanced detergency.Type: GrantFiled: November 25, 1992Date of Patent: October 25, 1994Assignee: Lever Brothers Company, Division of Conopco, Inc.Inventors: Robert W. Humphreys, Anthony Hung, Shang-Ren Wu, Abid N. Khan-Lodhi
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Patent number: 5356882Abstract: Pyrimidine 4'-thionucleosides of the formula I ##STR1## wherein Y is hydroxy or amino, and X is chloro, bromo, iodo, trifluoromethyl, C.sub.2-6 alkyl, C.sub.2-6 alkenyl, C.sub.2-6 haloalkenyl or C.sub.2-6 alkynyl and physiologically functional derivatives thereof. These compounds have utility as anti-vital agents.Type: GrantFiled: June 30, 1993Date of Patent: October 18, 1994Assignee: University of BirminghamInventors: Richard Walker, Paul L. Coe
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Patent number: 5356790Abstract: Myo-inositol in a specimen is assayed by reacting a specimen containing myo-inositol with:a) myo-inositol dehydrogenase using a thio-NADP group or thio-NAD group and an NADP group or NAD group as coenzymes, and which catalyzes a reversible reaction forming myo-inosose from myo-inositol,b ) A.sub.1 andc) B.sub.1to effect a cycling reaction ##STR1## wherein A.sub.1 is a thio-NADP group, thio-NAD group, NADP group or NAD group, A.sub.2 is a reduced form of A.sub.1, when A.sub.1 is a thio-NADP group or thio-NAD group, B.sub.1 is a reduced NADP group or reduced NAD group and when A.sub.1 is an NADP group or NAD group, B.sub.1 is a reduced thio-NADP group or reduced thio-NAD group, and wherein B.sub.2 is an oxidized form of B.sub.1. The change in the amount of A.sub.2 generated or B.sub.1 consumed by the cycling reaction is measured to perform the assay. A composition for performing the assay comprises the above myo-inositol dehydrogenase, as well as the above components A.sub.1 and B.sub.1.Type: GrantFiled: August 16, 1993Date of Patent: October 18, 1994Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Shigeru Ueda, Mamoru Takahashi, Hideo Misaki, Shigeyuki Imamura, Kazuo Matsuura
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Patent number: 5356883Abstract: This invention describes a method for preparing water-insoluble biocompatible gels, films and sponges by reacting hyaluronic acid, or a salt thereof, with a carbodiimide in the absence of a nucleophile or a polyanionic polysaccharide. The water-insoluble gels, films and sponges of this invention may be used as surgical aids to prevent adhesions of body tissues and as drug delivery vehicles.Type: GrantFiled: July 28, 1992Date of Patent: October 18, 1994Assignees: Research Foundation of State University of N.Y., Anika Research, Inc.Inventors: Jing-Wen Kuo, David A. Swann, Glenn D. Prestwich
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Patent number: 5354853Abstract: Novel phospholipid-saccharide conjugates are produced by the reaction of a phospholipid derivative and an activated saccharide. The resulting conjugates can be used to make liposomes which are target-specific or resistant to degradation in vivo.Type: GrantFiled: March 12, 1993Date of Patent: October 11, 1994Assignee: Genzyme CorporationInventors: Mark M. Staveski, Barbara Y. F. Wan, Alan E. Walts
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Patent number: 5346997Abstract: An agent for complexing sodium in aqueous solution comprises a glucuronic acid, specifically, beta-d-glucopyranosiduronic acid. The agent of the present invention furthermore includes the salts and esters of beta-d-glucopyranosiduronic acid. The salt of this acid is the triethanolamine salt of benzyl beta-d-glucopyranosiduronic acid. The ester of this acid is the benzyl ester. The agent of the present invention complexes sodium in aqueous solution in the pH range of living systems. Accordingly, it has use against such maladies as hypertension when taken internally and baldness when applied topically using a carrier in oil form.Type: GrantFiled: August 26, 1992Date of Patent: September 13, 1994Inventor: James G. Murphy
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Patent number: 5342929Abstract: The invention relates to a process for the preparation of glycosides by reacting protected sugars carrying an anomeric hydroxyl group with an aglycon selected from the group consisting of alcohol, thiol and a protected sugar carrying a non-anomeric hydroxyl group, in an inert solvent, in the preferred temperature range from -20.degree. to +250.degree. C., in the presence of catalytic amounts of metal complex salts. The glycosides are obtained in high yield. Often an excess of the .alpha.- or .beta.-form is obtained and even the pure .alpha.- oder .beta.-forms are obtainable.Type: GrantFiled: August 31, 1992Date of Patent: August 30, 1994Assignee: Ciba-Geigy CorporationInventors: Beat Ernst, Michael Heneghan, Andreas Hafner
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Patent number: 5340803Abstract: Tumor cells which have .beta.-glucuronidase and tyrosinase activity are selectively treated by administration of a conjugate of a cytotoxic compound which is a substrate for tyrosinase and glucuronic acid or a pharmaceutically acceptable salt or ester thereof particularly the methyl-triacetylated form of glucuronic acid. Among the cytotoxic phenolic compounds which are substrates for tyrosinase which can be used are 4-hydroxyanisole, butylated hydroxyanisole, L-3,4-dihydroxy-phenylalanine, dopamine (3,4-dihydroxyphenethylamine), terbutylcatechol, hydroquinone, resorcinol, 6-hydroxydopa (3,4,6-trihydeoxyphenylalanine) and methyl gallate.The efficacy of the treatment is enhanced by also administering a compound that inhibits the action of glutathione reductase.Type: GrantFiled: May 5, 1993Date of Patent: August 23, 1994Assignee: Co Enzyme Technology Ltd.Inventor: David Rubin
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Patent number: 5338838Abstract: An antioxidant substance which is a green leaf component in a green plant, comprising a component which is substantially insoluble in n-hexane but soluble in an aqueous ethanol solution having a water content of 0 to 80% by volume. The substance has an antioxidant activity as potent as or more potent than .alpha.-tocopherol, and is useful as an antioxidant for use in the field of foods, and medicines. Particularly, the antioxidant substance can be used for maintaining the freshness and quality of foods or storage thereof. The substance can be blended with cosmetics for skin and hair and are useful for the prevention of spots, freckles, chapping and sunburning.Type: GrantFiled: June 3, 1992Date of Patent: August 16, 1994Assignee: Yoshihide HagiwaraInventors: Yoshihide Hagiwara, Hideaki Hagiwara
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Patent number: 5336764Abstract: A compound has the formula ##STR1## wherein R is selected from the group consisting of (C.sub.7 -C.sub.20)aroyl, (C.sub.6 -C.sub.20)aryl, aralkyl and alkylaryl, and (C.sub.1 -C.sub.10)alkyl-di(C.sub.6 -C.sub.20)aryl Si, R' is selected from the group consisting of (C.sub.1 -C.sub.10)alkyl, (C.sub.7 -C.sub.20)aroyl and (C.sub.2 -C.sub.12)acyl, all of which may be further substituted with O, S, N or alkyl, and R'" is selected from the group consisting of halogen, (C.sub.1 -C.sub.10)alkoxy, (C.sub.1 -C.sub.10)acyloxy, O-methane-sulfonyl and O-p-toluenesulfonyl. A composition of matter comprises 0.001 to 99.999 wt % of the above compound.Type: GrantFiled: October 29, 1992Date of Patent: August 9, 1994Assignee: The United States of America as represented by the Department of Health and Human ServicesInventors: Victor E. Marquez, John S. Driscoll, Ronald J. Wysocki, Jr., Maqbool A. Siddiqui
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Patent number: 5332662Abstract: Methods and compositions are disclosed for determining a peroxidatively active substance (PAS). The methods comprise the step of detecting a fluorescent signal produced upon cleavage of a compound of the formula F-L-Q, wherein F is a fluorester capable of producing the signal, Q is a quencher capable of quenching the signal when linked to F, and L is a bond, or a linking group having a bond, wherein the bond is capable of being cleaved by a reaction of the PAS with a substrate of the PAS and a hydrogen donor wherein the cleavage of the bond substantially reduces the quenching. The methods have application in a wide variety of systems including assays and improved assays for analytes. Also disclosed are kits for conducting the methods and improvements in accordance with the present invention.Type: GrantFiled: July 31, 1992Date of Patent: July 26, 1994Assignee: Syntex (U.S.A.) Inc.Inventor: Edwin F. Ullman
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Patent number: 5326752Abstract: The compounds are of the formula ##STR1## wherein each R.sup.1 is independently H or lower alkyl (1-4C); R.sup.2 is H, lower alkyl (1-4C), alkylaryl or one or more additional saccharide residues; R.sup.3 and R.sup.4 are independently H, alkyl (1-6C), aryl or R.sup.3 and R.sup.4, taken together, form a five or six-membered ring optionally containing a hetroatom selected from the group consisting of O, S, and NR.sup.1 ; wherein said five- or six-membered ring may further be substituted by one or more substituents selected from the group consisting of (CHOR.sup.1).sup.m H wherein m is 1-4, OR.sup.1, OOCR.sub.1, NR.sup.1, NCOR.sup.1 and SR.sup.1 ; Y is H, OR.sup.1, OOCR.sup.1, NR.sup.1.sub.2, NCOR.sub.1 or SR.sub.1 ; and X is --CHR.sup.5 (CHOR.sup.1).sub.2 CHR.sup.6 OR.sup.1 wherein R.sup.5 and R.sup.6 are independently H, lower alkyl (1-4C) optionally substituted with one or more R, or result in a five- or six-membered ring optionally containing a heteroatom selected from the group consisting of O, S and NR.sup.Type: GrantFiled: November 27, 1991Date of Patent: July 5, 1994Assignee: Glycomed IncorporatedInventors: Mina Nashed, Falguni Asgupta, Saeed Abbas, John Musser, Darwin Asa
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Patent number: 5326864Abstract: The invention provides a method for the preparation of a calcium-complexing polycarboxy compound by oxidising inulin in the presence of a low concentration of hypohalite, resulting in the production of a polycarboxyinulin containing about 1.2-2.6 carboxyl groups per monosaccharide unit. The hypohalite is preferably hypobromite, which can be produced in situ by chemical or electrochemical oxidation of a catalytic amount of bromide. The polycarboxyinulin can be used as a phosphate substitute in calcium-binding agents and detergents.Type: GrantFiled: December 7, 1992Date of Patent: July 5, 1994Assignee: Nederlandse Organisatie Voor Toegepast-Natuurwetenschappelijk Onderzoek TnoInventors: Arie C. Besemer, Herman Van Bekkum
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Patent number: 5322693Abstract: Lactoneotrehalose, a novel saccharide shown by the formula O-.beta.-D-galactopyranosyl-(1.fwdarw.4)-O-.beta.-D-glucopyranosyl .alpha.-D-glucopyranoside, is prepared by allowing a saccharide-transferring enzyme to act on an aqueous solution containing lactose and amylaceous substance. Lactoneotrehalose is a non-reducing oligosaccharide, extremely stable, readily soluble in water, and substantially free of hygroscopicity, as well as having a satisfiable quality and moderate sweetness. These render lactoneotrehalose very useful in the preparations of orally-administrable products, cosmetics and pharmaceuticals.Type: GrantFiled: April 5, 1993Date of Patent: June 21, 1994Assignee: Kabushiki Kaisha Hayashibara Seibutsu Kagaku KenkyujoInventors: Takashi Shibuya, Hiroto Chaen, Shuzo Sakai
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Patent number: 5321013Abstract: Pharmaceutical compositions in the form of stable sucralfate suspensions free of suspending agents, wherein the sucralfate is present in the form of a gel having self-suspending properties and is suspended in an aqueous carbohydrate solution in a quantity of between 1 and 40% of sucralfate by weight.Said gel has a surface area exceeding 200 m.sup.2 /g and is prepared by dissolving powdered sucralfate in an HCl solution and then precipitating it with an NaOH solution added to a pH of between 4 and 4.5.Type: GrantFiled: January 8, 1990Date of Patent: June 14, 1994Assignee: Lisapharma SpAInventors: Giorgio G. Z. Zagnoli, Ubaldo Conte, Paolo Colombo, Carla Caramella
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Patent number: 5321129Abstract: Novel compounds having the general formulaS--Ar--Xin whichS denotes a saccharide residueAr denotes an aryl residue andX denotes a straight-chained or branched alkyl residue with 2 to 20 carbon atoms,provided that the aryl residue may not be a 4-ethylphenyl, 4-isopropylphenyl, 4-sec.-butyl or 4-dodecylphenyl residue if the saccharide is a galactopyranoside residue, are interesting surface-active agents and are particularly suitable in diagnostic tests in order to clear serum.Type: GrantFiled: May 14, 1992Date of Patent: June 14, 1994Assignee: Boehringer Mannheim GmbHInventors: Peter Sluka, Hans-Georg Batz, Bernd Vogt
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Patent number: 5320954Abstract: An aromatic substituted glycoside is disclosed of the formula ##STR1## wherein the configuration of the substituted --OR on the anomeric carbon is alpha, n is an integer of 0 or 1, and R is a substituted aromatic radical selected from the group ##STR2## where R.sub.1 through R.sub.6 are independently halogen, NO.sub.2, SO.sub.3 H, COR.sub.7, ##STR3## where R.sub.7 is lower alkyl; and includes its stereoisomers, optical isomers and geometric isomers and mixtures of the foregoing isomers. These substrates are useful as direct substrates for alpha-amylases. A process for the preparation of the substrates and related substances is also described.Type: GrantFiled: September 3, 1992Date of Patent: June 14, 1994Assignee: Hoechst Celanese CorporationInventors: Rodrigo G. Chavez, Harold David, Ernest K. Metzner, Gerald F. Sigler, Emily S. Winn-Deen
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Patent number: 5319076Abstract: An oligosaccharide derivative of the formula: ##STR1## wherein R is --SR.sup.2, ##STR2## R.sup.1 is an optically detectable group, etc.; R.sup.2 is alkyl or substituted alkyl; and n is zero or 1-5, is effective as a substrate for measuring .alpha.-amylase activity and can be synthesized easily in high yield.Type: GrantFiled: February 10, 1993Date of Patent: June 7, 1994Assignee: Wako Pure Chemical Industries, Inc.Inventors: Akira Hasegawa, Makoto Kiso, Shinji Satomura
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Patent number: 5318794Abstract: A method for producing caramel having a high content of fructose oligosaccharides and caramel product produced thereby is disclosed which comprises mixing sucrose and an organic acid in a ball mill for approximately 0.5 to 4 hours, heating to a temperature of 130.degree.-160.degree. C. for 0.5 to 15 minutes and cooling quickly to produce a caramel product. The ball milling reduces crystallinity and intimately mixes the sucrose and organic acid, lowering the thermolization temperature. The product contains a high proportion of fructose oligosaccharides (D.P. .about.3-10).Type: GrantFiled: December 2, 1992Date of Patent: June 7, 1994Assignee: The University of MontanaInventor: Geoffrey N. Richards
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Patent number: 5312907Abstract: Glycosiduronic acids, such as alkyl glycosiduronic acids or alkenyl glycosiduronic acids, which may be used in the preparation of surfactant compositions, such as detergents and cleansers, are prepared by reacting an oxidized mono-, oligo-, or polysaccharide with up to 10 monomer units with one or more fatty alcohols having 8-22 carbon atoms in the presence of a catalyst, preferably in bulk, and after acetalization removing the excess alcohol. Preferably the oxidized mono-saccharide used is glucuronic acid and/or glucuronic acid-3,6-lactone.Type: GrantFiled: October 5, 1992Date of Patent: May 17, 1994Assignee: Akzo N.V.Inventors: Manfred Schattschneider, Burkhard Weuste, Hans J. Weissen
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Patent number: 5312908Abstract: A chitin oligosaccharide which is a chitin oligomer having a 2,5-anhydromannose group or a chitosan oligosaccharide which is a chitosan oligomer having a 2,5-anhydromannose group having a structure of the formula shown below at a terminal end: ##STR1## wherein it can be prepared by allowing chitin or chitosan to react with nitrous acid at a temperature of 10.degree. C.Type: GrantFiled: July 13, 1992Date of Patent: May 17, 1994Assignee: Tamatsukuri CorporationInventor: Etsuko Nakao
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Patent number: 5310889Abstract: Carbohydrate substituted dibenzo[d,f][1,3,2]dioxaphosphepin compounds of formula I ##STR1## where A is a carbohydrate residue are effective stabilizers for polymers processed at elevated temperatures and subject to thermal or oxidative degradation.Type: GrantFiled: July 22, 1992Date of Patent: May 10, 1994Assignee: Ciba-Geigy CorporationInventors: Stephen D. Pastor, Joseph E. Babiarz
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Patent number: 5310890Abstract: Carbohydrate substituted dibenzo[d,g][1,3,2]dioxaphosphocin compounds of formula I ##STR1## where A is a carbohydrate residue are effective stabilizers for polymers processed at elevated temperatures and subject to thermal or oxidative degradation.Type: GrantFiled: July 22, 1992Date of Patent: May 10, 1994Assignee: Ciba-Geigy CorporationInventors: Stephen D. Pastor, Joseph E. Babiarz
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3,9-carbohydrate substituted 2,4,8,10-tetraoxa-3,9-diphosphaspiro(5.5)undecane phosphite stabilizers
Patent number: 5310891Abstract: Carbohydrate substituted phosphites of Formula I ##STR1## where A is a carbohydrate residue are effective stabilizers for polymers processed at elevated temperatures and subject to thermal or oxidative degradation.Type: GrantFiled: July 22, 1992Date of Patent: May 10, 1994Assignee: Ciba-Geigy CorporationInventors: Joseph E. Babiarz, Stephen D. Pastor -
Patent number: 5304380Abstract: Disclosed are a glucosamine derivative represented by the following formula [I] or a pharmacologically acceptable salt thereof, and a liposome containing the glucosamine derivative as a membrane constituting component: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, and m represent the following R.sup.1 and R.sup.2 ;a hydrogen atom or a --CO(CH.sub.2).sub.n CH.sub.3 group, n representing an integer from 10 to 22 and R.sup.1 and R.sup.2 being not simultaneously hydrogen atomsR.sup.3 ;a hydrogen atom or a lower alkyl group, andm;an integer from 0 to 3.Type: GrantFiled: June 8, 1992Date of Patent: April 19, 1994Assignee: Japan Tobacco Inc.Inventors: Koichiro Miyajima, Kaoru Fuji
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Patent number: 5302514Abstract: The present invention provides a maltooligoside derivative represented by the formula: ##STR1## wherein n denotes an integer 3-5, R represents an aromatic chromophoric group, X represents a group >CHCH.sub.2 N.sub.3 or >C.dbd.CH.sub.2, and Y represents a hydrogen atom, a substituted or unsubstituted hydrocarbon group or an alkyl- or arylsulfonyl group, a reagent for determining .alpha.-amylase activity which comprises said maltooligoside derivative as an effective ingredient, and a process for determining .alpha.-amylase activity, characterized in that said maltooligoside derivative and coupled enzymes are added to an .alpha.-amylase containing sample to conduct an enzymatic reaction and a liberated aromatic chromophoric compound is quantitatively determined. The compound of the present invention is very useful as a substrate for determining .alpha.-amylase activity, and .alpha.Type: GrantFiled: June 5, 1992Date of Patent: April 12, 1994Assignees: Kikkoman Corporation, Daiichi Pure Chemicals Co. Ltd., Seishin Pharmaceutical Co., Ltd.Inventors: Shoichi Tokutake, Tadashi Tomikura, Kazuo Kotani, Kazunori Saito, Kohichiro Tobe
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Patent number: 5300634Abstract: A maltooligosaccharide derivative very useful, for example, as a precursor of a modified oligosaccharide derivative having one or more modifying groups at the 6-position or the 4- and 6-positions of the non-reducing end glucose residue which can be effectively used as a substrate for determining .alpha.-amylase activity or an intermediate thereof, can be produced by reacting a compound of the formula: ##STR1## with a compound of the formula: ##STR2## to convert at least the hydroxyl groups at the 4- and 6-positions of non-reducing end glucose residue of the compound of the formula (1) into a cyclic boric acid ester, acylating the reaction product, and then treating the acylated product.Type: GrantFiled: May 4, 1992Date of Patent: April 5, 1994Assignee: Wako Pure Chemical Industries, Ltd.Inventors: Atsunori Sano, Naoki Teno
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Patent number: 5298611Abstract: A process for producing substantially pure sucralose pentaester from a mixture of 6-O-acyl-4,1' ,6' -trichloro-4,1',6'-trideoxygalactosucrose in a reaction medium comprising a tertiary amide, wherein said process comprises the steps of:(a) recovering the 6-O-acyl-4,1' ,6' -trichloro-4,1' ,6' -trideoxygalactosucrose from said mixture;(b) peracylating the 6-O-acyl-4,1' ,6' -trichloro-4,1' ,6' -trideoxygalactosucrose product of step (a) to produce thereby 4,1',6' -trichloro-4,1' ,6' -trideoxygalactosucrose pentaester; and(c) crystallizing the 4,1',6' -trichloro-4,1' ,6' -trideoxygalactosucrose pentaester product of step (b) to produce substantially pure 4,1',6' -trichloro-4,1' ,6' -trideoxygalactosucrose pentaester.Type: GrantFiled: March 12, 1993Date of Patent: March 29, 1994Assignee: McNeil-PPC, Inc.Inventors: Juan L. Navia, Robert E. Walkup, Nicholas M. Vernon, Robert E. Wingard, Jr.
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Patent number: 5298494Abstract: Derivatives of simple monosaccharides which exhibit anti-proliferative and/or anti-inflammatory activity and are useful for treating mammals having inflammatory disorders and/or autoimmune disorders. This invention also encompasses pharmaceutical compositions containing these compounds and methods of treating inflammatory and/or autoimmune disorders.Type: GrantFiled: June 30, 1993Date of Patent: March 29, 1994Assignee: Greenwich Pharmaceuticals IncorporatedInventors: Sudershan K. Arora, Roy L. Whistler, Albert V. Thomas
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Patent number: 5296588Abstract: A process of preparing aldonamides and N-substituted aldonamides which includes the steps of recovering a by-product of the process (an ammonium salt of an aldonic acid) and converting it into at least one starting material. Aldonolactone is reacted with a primary or secondary amine and the resulting solution containing the by-product of the reaction is treated with a solid base to obtain a solid aldonate salt and a second solution containing the starting amine and some aldonamide. The second solution may be recycled as part of the starting material mixture. Alternatively, the amine and the aldonamide may be recovered from the second solution, and the amine alone may be recycled. The solid salt of aldonic acid may be converted into aldonic acid, which in turn may be converted into aldonolactone. The obtained aldono-1,5-lactone may also be utilized as a starting ingredient in the synthesis according to the present invention.Type: GrantFiled: October 8, 1992Date of Patent: March 22, 1994Assignee: Lever Brothers Company, Division of Conopco, Inc.Inventors: Van Au, Bijan Harirchian
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Patent number: 5290576Abstract: The present invention relates to the novel tert-butyloxycarbonyl-L-tyrosylpeptidoglycan monomer ##STR1## and to its .sup.125 I-labelled Boc-Tyr-PGM derivative; to the preparation and use thereof as pharmaceuticals of immunostimulating and antitumor activity.Type: GrantFiled: December 20, 1991Date of Patent: March 1, 1994Assignees: Pliva Farmaceutska, Kemijska PrehrambenaInventors: Djurdjica Ljevakovic, Branka Vranesic, Jelka Tomasic, Ivo Hrsak, Branko Ladesic