Viscosity Or Degree Of Polymerization Changed (e.g., Degrading, Cross Linking, Etc.) Patents (Class 536/41)
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Patent number: 5473063Abstract: Compounds of formulae ##STR1## wherein X is O;R.sup.1 is OH, phosphate, diphosphate, triphosphate or (CH.sub.2).sub.n --O--CH.sub.2 --O--P(.dbd.O)(OH).sub.2 wherein n is 0-2;R.sup.2 is H and R.sup.3 is CH.sub.3, CH.sub.2 OH, CH.sub.2 --O--CH.sub.3, CH.sub.2 SH, CH.sub.2 F or CH.sub.2 N.sub.3 ; orR3 is H and R.sup.2 is CH.sub.3, CH.sub.2 OH, CH.sub.2 --O--CH.sub.3, CH.sub.2 SH, CH.sub.2 F or CH.sub.2 N.sub.3 ;and Z is Cl, Br, I, acyloxy or alkoxy;are synthesized from acyclic intermediates and are subsequently useful in the preparation of nucleoside analogues with antiviral activity against retroviruses such as HIV and hepatitis B.Type: GrantFiled: May 20, 1993Date of Patent: December 5, 1995Assignee: Medivir ABInventors: Bjorn O. Classon, Bengt B. Samuelsson, Imgemar S. Kvarnstrom, Lars G. Svansson, Stefan C. T. Svensson
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Patent number: 5470715Abstract: A composition for determination of chloride ion, comprising a maltooligosaccharide derivative possessing modified or non-modified non-reducing terminal and modified reducing terminal, a metal chelating agent, .alpha.-amylase and an adjuvant enzyme, provided that the adjuvant enzyme may not be contained when the maltooligosaccharide derivative possesses reducing terminal with a modifying group bound in .alpha.-type, which does not require maintenance and control of special instruments and special treatment of waste liquors, affords good analytic efficiency, determination precision and linearity, and is capable of suppressing rise of reagent blank and giving accurate determination values from test samples showing high values.Type: GrantFiled: January 3, 1994Date of Patent: November 28, 1995Assignee: Toyo Boseki Kabushiki KaishaInventors: Katsuhiko Mizuguchi, Shin'ichi Teshima, Tsuneo Hanyu
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Patent number: 5470843Abstract: Carbohydrate-containing polymers which can have an HLB* of from about 10 to about 20 are disclosed. The compounds comprise a hydrophilic polymer portion, a carbohydrate portion comprising from 1 to about 20 naturally occurring, identical or different, monosaccharide units, at least one bifunctional spacer coupling the carbohydrate portion to the hydrophilic polymer portion, and a potentiator moiety. The potentiator moiety can be is a crosslinking moiety located within the hydrophilic polymer or a hydrophobic, hydrophilic or ionic moiety. Processes for the preparation and use of such polymers are also disclosed.Type: GrantFiled: December 13, 1993Date of Patent: November 28, 1995Assignee: Hoechst AktiengesellschaftInventors: Wilhelm Stahl, Michael Ahlers, Axel Walch, Eckhart Bartnik, Gerhard Kretzschmar, Susanne Grabley, Rudolf Schleyerbach
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Patent number: 5468850Abstract: Disclosed is an industrial-scale preparation of a high 2-O-.alpha.-D-glucopyranosyl-L-ascorbic acid content product with an improved purity, the preparation comprising subjecting a solution containing 2-O-.alpha.-D-glucopyranosyl-L-ascorbic acid and a saccharide derivative of L-ascorbic acid exhibiting a direct reducing activity to an oxidation treatment, subjecting the resultant mixture ti column chromatography using a strongly-acidic cation exchange resin, and recoverying the resultant high 2-O-.alpha.-D-glucopyranosyl-L-ascorbic acid content fraction. Thus, the preparatiobn has a great significance in the industrial field.Type: GrantFiled: October 21, 1992Date of Patent: November 21, 1995Assignees: Kabushiki Kaisha Hayashibara, Seibutsu Kagaku KenkyujoInventors: Takahiko Mandai, Masaru Yoneyama, Shuzo Sakai
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Patent number: 5464942Abstract: This invention relates to compounds prepared by linking glycosaminoglycan to phospholipid or lipid, which are expected to exert a pharmacological effect for inhibiting metastasis because of their excellent function to inhibit adhesion of cancer cells to blood vessel endothelial cells and extracellular matrix. This phospholipid- or lipid-linked glycosaminoglycan can be produced for example by: cleaving and oxidizing reducing terminal group of glycosaminoglycan, and allowing an aldehyde group or a lactone compound of the thus-formed derivative or a carboxyl group in the glycosaminoglycan chain to react with a primary amino group of a phospholipid; or linking a glycosaminoglycan derivative to a phospholipid or a lipid by allowing a primary amino group of the derivative to react with a carboxyl group of the phospholipid or lipid. This phospholipid- or lipid-linked glycosaminoglycan is useful as a metastasis inhibitor because it has no toxicity.Type: GrantFiled: March 24, 1991Date of Patent: November 7, 1995Assignee: Seikagaku Kogyo Kabushiki KaishaInventors: Katsukiyo Sakurai, Nobuo Sugiura, Koji Kimata, Sakaru Suzuki
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Patent number: 5463040Abstract: The present invention relates to a method of increasing the yield of etoposide produced relative to prior art processes. A residue obtained as a result of reacting etoposide triacetate with a first lower alkanol in the presence of a first transesterification catalyst is provided. This residue is then reacted with a second lower alkanol and a second transesterification catalyst.Type: GrantFiled: June 28, 1994Date of Patent: October 31, 1995Assignee: Teva Pharmaceutical Industries, Ltd.Inventor: Calvin Vogel
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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: 5459248Abstract: Etoposide phosphate is prepared by coupling dibenzyl 4'-demethyl-4-epipodophyllotoxin-4'-phosphate with 2,3-di-O-benzyl-4,6-O-ethylidene-.alpha.,.beta.-D-glucopyranose in a solvent and subsequently removing the protecting groups. The tetra-benzyl protected etoposide phosphate is recrystallized from methanol or directly crystallized from acetonitrile by adding methanol to yield substantially the pure C-1"-.beta. form. The benzyl protecting groups are simultaneously removed by hydrogenation to produce etoposide phosphate in high yields. In a further embodiment, etoposide phosphate is treated with a phosphatase enzyme to yield etoposide.Type: GrantFiled: November 4, 1993Date of Patent: October 17, 1995Assignee: Bristol-Myers Squibb CompanyInventors: Lee J. Silverberg, Purushotham Vemishetti, John L. Dillon, Jr., John J. Usher
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Patent number: 5459249Abstract: Alkylglycosides are manufactured by continuous reaction of monosaccharides with fatty alcohols in the presence of an acid catalyst, comprising continuously adding the monosaccharides, fatty alcohols, and catalysts to a continuous stirred-tank reactor (CSTR). The reaction takes place under steady-state conditions with a conversion of 97%.+-.2.5% relative to the monosaccharide used. Water is removed continuously from the CSTR during the reaction, and the reaction mixture is removed from the CSTR in an amount which essentially corresponds to the amount of reactants and catalysts added.Type: GrantFiled: March 18, 1994Date of Patent: October 17, 1995Assignee: Akzo Nobel N.V.Inventors: Manfred J. Bergfeld, Jurgen Seifert
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Patent number: 5457140Abstract: Shaped hydrogel articles such as soft contact lenses are prepared by the steps of:(1) molding or casting a polymerization mixture comprising:(a) a monomer mixture comprising a major proportion of one or more hydrophilic monomers such as 2-hydroxyethyl methacrylate, and one or more cross-linking monomers; and(b) an inert, displaceable diluent selected from the group consisting of:(i) ethoxylated alkyl glucoside;(ii) ethoxylated bisphenol A;(iii) polyethylene glycol;(iv) mixture of propoxylated and ethoxylated alkyl glucoside;(v) single phase mixture of ethoxylated or propoxylated alkyl glucoside and C.sub.2-12 dihydric alcohol;(vi) adduct of .epsilon.-caprolactone and C.sub.2-6 alkanediols and triols;(vii) ethoxylated C.sub.3-6 alkanetriol; and(viii) mixtures of one or more of (i) through (vii),under conditions to polymerize said monomer mixture to produce a shaped gel of a copolymer of said monomers and said diluent; and(2) thereafter replacing said diluent with water.Type: GrantFiled: July 22, 1993Date of Patent: October 10, 1995Assignee: Johnson & Johnson Vision Products, Inc.Inventors: Ivan M. Nunez, Frank F. Molock, Laura D. Elliott, James D. Ford
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Patent number: 5455240Abstract: The present invention relates to compositions and methods for preventing pneumococcal infection. In particular, the invention relates to identification of the major reception for Streptococcus pneumoniae on activated human cells, and diagnostic and therapeutic compositions and methods based thereon. In particular, the invention relates to the discovery that platelet activating factor (PAF) receptor is an adhesive ligand for pneumococcal adherence to activated lung epithelial and venous endothelial (i.e., host) cells. Accordingly, the present invention is directed to a method for preventing or treating an infection with Streptococcus pneumoniae by administering an antagonist of platelet activating factor receptor. The invention further relates to recognition that adherence to activated cells also involves a carbohydrate ligand found on such activated cells.Type: GrantFiled: June 20, 1994Date of Patent: October 3, 1995Assignees: The Rockefeller University, Beth Israel Hospital AssociationInventors: Elaine I. Tuomanen, Diana R. Cundell, Norma P. Gerard
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Patent number: 5455232Abstract: The invention relates to a pharmaceutical preparation comprising as an active ingredient at least one rhamnolipid or a pharmaceutically acceptable salt thereof, and a carrier and/or diluent, preferably comprising a rhamnolipid of the general formula: ##STR1## wherein R.sub.1 =H, alpha-L-rhamnopyranosyl; ##STR2## R.sub.3 =(C.sub.5 -C.sub.20)-saturated, -mono- of poly-unsaturated alkyl; R.sub.4 =(C.sub.5 -C.sub.Type: GrantFiled: April 7, 1994Date of Patent: October 3, 1995Inventors: Goran Piljac, Visnja Piljac
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Patent number: 5451667Abstract: Fumaric acid derivatives of the formula ##STR1## wherein R.sub.1 is a hydrogen atom, a C.sub.1 -C.sub.8 alkyl group or a metallic cation, andR.sub.2 is a saturated or unsaturated aliphatic C.sub.6 -C.sub.24 alkyl group, psoralen-9-yl, retinyl, .alpha.-tocopheryl (vitamin E), calciferyl, corticosteroid-21-yl or monosaccharid-.omega.-yl; a group of fumaric acid derivatives based on glycerol, alkane diol or polyol molecules; and fumaric acid derivatives of the formula ##STR2## wherein n is an integer from to 30 to 260,R.sub.3 is a hydrogen atom or a C.sub.1 -C.sub.3 alkyl group,R.sub.4 is one of the R.sub.3 groups and n is the number of molecule repetitions, processes for their production and compositions containing same are described. These compounds are useful as drugs for the treatment of cryptogenically-caused diseases and have antisporiatic as well as antimicrobial action.Type: GrantFiled: October 8, 1992Date of Patent: September 19, 1995Inventors: Peter P. Speiser, Rajendra K. Joshi
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Patent number: 5451668Abstract: Process for splitting off .DELTA..sup.4 -unsaturated uronic acid from glycosaminoglycan, in which the glycosaminoglycan is treated with an iodine solution or with a bleaching reagent, or with a combination thereof.Type: GrantFiled: January 17, 1990Date of Patent: September 19, 1995Assignee: N.V. AkzoInventors: Constant A. A. Van Boeckel, Gijsbert W. K. Van Dedem
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Patent number: 5449763Abstract: A process for preparing high detergency or surfactant alkyl polyglycoside compositions and a purified alkyl monoglycoside and to compositions employing the polyglycosides for various end use applications. The process involves removal of a substantial portion of the monoglycoside present in a reaction product mixture containing alkyl polyglycosides resulting from the reaction of an alcohol and saccharide at elevated temperatures in the presence of an acid catalyst. Separation of the monoglycoside from the reaction product mixture may be carried out by molecular distillation.Type: GrantFiled: October 6, 1992Date of Patent: September 12, 1995Assignee: Henkel CorporationInventors: Harald P. Wulff, Paul A. Siracusa, Patricia E. Bator, Barry A. Salka, Michael W. Counts, Robert A. Aleksejczyk, Patrick M. McCurry, Jr., Robert S. McDaniel, William G. Kozak, Allen D. Urfer, Gail Howell
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Patent number: 5449663Abstract: 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 11, 1993Date of Patent: September 12, 1995Inventor: Haim I. Bicher
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Patent number: 5445944Abstract: 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 fluorescer 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: April 22, 1994Date of Patent: August 29, 1995Assignee: Syntex (U.S.A.) Inc.Inventor: Edwin F. Ullman
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Patent number: 5444161Abstract: Galactopyranoside derivative compounds for use as substrates for hydrolysis by enzymes with .beta.-galactosidase activity are provided. The concentration of the reaction products can be measured by spectroscopy. The compounds find particular use in diagnostic assays for detection of analyte.Type: GrantFiled: August 16, 1989Date of Patent: August 22, 1995Assignee: Microgenics CorporationInventors: Wayne B. Manning, Pyare Khanna, Glenda Choate
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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: 5438125Abstract: Sialic acid compounds of formula ##STR1## wherein X is hydrogen, a lower alkyl group or benzyl, Y is hydrogen or acetyl, Ac is acetyl, and the wavy line represents that the compound of the formula (I) includes both a .alpha.-anomer and .beta.-anomer, have excellent chemical and enzymatical stability and are useful in the treatment of central or peripheral nervous diseases.Type: GrantFiled: March 4, 1992Date of Patent: August 1, 1995Assignee: Nippon Zoki Pharmaceutical Co., Ltd.Inventors: Kaoru Okamoto, Shinji Morita
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Patent number: 5438124Abstract: A novel, efficient glycosylating reagent, R 3,4-O-isopropylidene-2-O-(4-methoxybenzyl)-1-thio-.beta. -L-fucopyranoside wherein R is a lower alkyl or lower alkenyl of 1 to 8 carbons such as methyl or pentenyl, is described. This novel reagent provides for the facile synthesis of linear and other .alpha.-L-fucosyl oligosaccharides. In addition, a method for the preparation of 2'-O-.alpha.-L-fucopyranosyl-lactose, which comprises reacting the abovementioned glycosylating reagent with solvated 4-O-(6-O-acetyl-3,4-O-isopropylidene-.beta.-D-galactopyranosyl)-2,3,5,6-di -O-isopropylidene-D-glucose, dimethyl acetal, a tetrabutylammonium halide and a catalyst and then de-O-acetylating the resulting reaction product with sodium methoxide methanol, is also disclosed.Type: GrantFiled: July 16, 1991Date of Patent: August 1, 1995Assignee: Health Research, Inc.Inventors: Khushi L. Matta, Rakesh K. Jain, Robert D. Locke
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Patent number: 5436325Abstract: A method is provided for preparing [.sup.18 F]2-fluoro-2-deoxyglucose with an anion exchange resin by effecting an exchange reaction between an aqueous solution of [.sup.18 F]fluoride containing an alkali metal carbonate or bicarbonate, such as sodium bicarbonate, and an anion, such as bicarbonate or carbonate, on the anion exchange resin followed by the displacement reaction with 1,3,4,6-tetra-O-acetyl-2-O-trifluoromethanesulfonyl-.beta.-D-mannopyranose to form the resulting 2-fluoro-2-deoxyglucose tetraacetate. Improved yields of the [.sup.18 F]2-fluoro-2-deoxyglucose are obtained when the alkali bicarbonate or carbonate is used in the target water.Type: GrantFiled: July 18, 1994Date of Patent: July 25, 1995Assignee: General Electric CompanyInventors: Bruce F. Johnson, Maxim Y. Kiselev, Johan Ulin
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Patent number: 5432275Abstract: 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, which 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. The use of a prebleached heel or feed prior to introduction of the unbleached material to be bleached results in a faster approach to equilibrium, steady state, bleaching conditions which results in minimum chemical usage and more rapid production of low color.Type: GrantFiled: February 25, 1994Date of Patent: July 11, 1995Assignee: Henkel CorporationInventors: Patrick M. McCurry, Jr., James D. Beaulieu
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Patent number: 5432269Abstract: A process is disclosed for preparing alkyl glycosides of general formula (I), by reacting an alcohol with a reducing sugar or with an equivalent of the latter, in the presence of a binary catalyst formed by a strong organic acid and a weak, also organic, base, having a K.sub.a within the range of from 10.sup.-8 to 10.sup.-1.Type: GrantFiled: May 7, 1993Date of Patent: July 11, 1995Assignees: Enichem S.p.A., Eniricerche S.p.A.Inventors: Giampietro Borsotti, Claudio Santini, Luigi Nataloni, Tullio Pellizzo
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Patent number: 5432268Abstract: A process is disclosed for producing particular hydroxyalkyl glucosides in the presence of a binary catalyst.Type: GrantFiled: May 7, 1993Date of Patent: July 11, 1995Assignees: Enichem S.p.A., Eniricerche S.p.A.Inventors: Giampietro Borsotti, Massimo Ciali, Tullio Pellizzon, Giovanni Agnes
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Patent number: 5432161Abstract: 2-O-.alpha.-D-Glucopyranosyl-L-ascrobic acid is crystallizable in its supersaturated solution. Crystalline 2-O-.alpha.-D-glucopyranosyl-L-ascorbic acid is substantially nonhygroscopic, free flowing, free of deliquescence, consolidation and direct reducing activity, but is readily soluble in water. Because of these characteristics, crystalline 2-O-.alpha.-D-glucopyranosyl-L-ascorbic acid is handleable with an ease, and superiorly high in stability and physiological activities. Thus, crystalline 2-O-.alpha.-D-glucopyranosyl-L-acorbic acid is favorably useful in vitamin C-enriching agents, foodstuffs, pharmaceuticals and cosmetics.Type: GrantFiled: March 30, 1990Date of Patent: July 11, 1995Assignee: Kabushiki Kaisha Hayashibara Seibutsu Kagaku KenkyujoInventors: Shuzo Sakai, Masaru Yoneyama, Toshio Miyake
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Patent number: 5432163Abstract: Compounds of this invention are derivatives of pentose monosaccharides which exhibit anti-proliferative and anti-inflammatory activity as well as intermediates for the synthesis of these compounds. Methods of preparation, pharmaceutical compositions containing the compounds and methods of treating inflammatory and/or autoimmune disorders employing the compounds are disclosed.Type: GrantFiled: November 13, 1992Date of Patent: July 11, 1995Assignee: Greenwich Pharmaceuticals IncorporatedInventors: M. Nayeem Akhtar, David S. Thomson, Sudershak K. Arora
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Patent number: 5428142Abstract: The present invention relates to a series of silicone containing glycosides prepared by the reaction of a hydroxy containing dimethicone copolyol with a reducing saccharide, or a source of reducing saccharide, in the presence of a suitable catalyst. The invention also relates to the application of these novel compounds in personal care compositions for use on hair and skin.Type: GrantFiled: October 20, 1993Date of Patent: June 27, 1995Assignee: Siltech Inc.Inventor: Anthony J. O'Lenick, Jr.
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Patent number: 5424407Abstract: A stabilized crocetin-containing colorant which has as an effective component a crocetin included by cyclodextrin. This colorant is imparted with resistance against light and various chemicals to crocetin, which is a hydrolysate of crocin, the main component of the carotenoid gardenia yellow pigment. The colorant may be added to various food products for use of crocetin as a stable coloring matter.Type: GrantFiled: November 22, 1993Date of Patent: June 13, 1995Assignee: Ensuiko Sugar Refining Co., Ltd.Inventors: Takemi Tanaka, Hisashi Okemoto, Nobuhiro Kuwahara
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Patent number: 5424294Abstract: N-acyl-N,N'-di-lysogangliosides, N'-acyl-N,N'-di-lysogangliosides and N,N'-diacyl-N,N'-di-lysogangliosides, in which the acyl groups are derived from an organic acid of the aliphatic, aromatic, araliphatic, alicyclic or heterocyclic series and in which at least one of the two acyl groups is not aliphatic, and their preparation are disclosed. Also disclosed is the preparation of the esters, inner esters, amides and hydroxy peracylates of these compounds and salts thereof. These compounds are useful in the treatment of pathologies of the central and peripheral nervous systems.Type: GrantFiled: October 20, 1993Date of Patent: June 13, 1995Assignee: Fidia S.p.A.Inventors: Francesco Della Valle, Aurelio Romeo
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Patent number: 5424406Abstract: A method for treatment of diabetes, which comprises administering to a patient with diabetes an effective amount of a dihydrochalcone derivative of the formula: ##STR1## wherein Ar is an aryl group, R.sup.1 is a hydrogen atom or an acyl group, R.sup.2 is a hydrogen atom, an acyl group or .alpha.-D-glucopyranosyl group, or R.sup.1 and R.sup.2 may combine together to form a substituted methylene group, R.sup.3 and R.sup.4 are each a hydrogen atom or an acyl group, OR.sup.5 is a protected or unprotected hydroxy group or a lower alkoxy group; or a pharmaceutically acceptable salt thereof.Type: GrantFiled: November 10, 1993Date of Patent: June 13, 1995Assignee: Tanabe Seiyaku Co., Ltd.Inventors: Kenji Tsujihara, Mitsuya Hongu, Nobuyuki Funami, Masanori Inamasu, Kenji Arakawa
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Patent number: 5414028Abstract: 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: February 17, 1994Date of Patent: May 9, 1995Assignee: Ciba-Geigy CorporationInventors: Stephen D. Pastor, Joseph E. Babiarz
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Patent number: 5414074Abstract: The invention concerns C-glycosylated derivatives of soft carbon nucleophile compounds, particularly compounds which contain acid-labile structural units. The invention further concerns a mild, cost-effective, non-hazardous and stereoselective method of general application employing a glycal as a glycosyulating agent and iodine as a catalyst for the preparation of C-glycosylated soft carbon nucleophile compounds.Type: GrantFiled: September 25, 1992Date of Patent: May 9, 1995Assignee: University of MichiganInventors: Masato Koreeda, Todd A. Houston
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Patent number: 5412080Abstract: Enterobactin analogs prepared from scyllo-inositol mono-orthoformate and having the following formula: ##STR1## wherein each X.sub.1, X.sub.2 and X.sub.3, independently, is H, C.sub.1-20 alkyl, phenyl, naphthyl, C.sub.7-20 aralkyl, or C.sub.7-20 alkaryl; Y is H, C.sub.1-20 alkyl, phenyl, naphthyl; C.sub.7-20 aralkyl, C.sub.7-20 alkaryl; --(C.sub.p H.sub.2p)--CH.sub.2 OH, --(C.sub.p H.sub.2p)--COOH or its salt, --(C.sub.p H.sub.2p)--NR.sub.1.R.sub.2 or its salt, or --(C.sub.p H.sub.2p)--N.sup.+ R.sub.1.R.sub.2.R.sub.3 ; in which p is 1-20 and each R.sub.1, R.sub.2 and R.sub.3, independently, is H or C.sub.1-5 alkyl; and m, n and o, independently, is 1-6; or the enantiomer thereof.Type: GrantFiled: August 25, 1993Date of Patent: May 2, 1995Assignee: President and Fellow of Harvard CollegeInventors: Yoshito Kishi, Bruno Tse
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Patent number: 5407812Abstract: 2-O-.alpha.-D-Glucopyranosyl-L-ascrobic acid is crystallizable in its supersaturated solution. Crystalline 2-O-.alpha.-D-glucopyranosyl-L-ascorbic acid is substantially nonhygroscopic, free flowing, free of deliquescence, consolidation and direct reducing activity, but is readily soluble in water. Because of these, characteristics crystalline 2-O-.alpha.-D-glucopyranosyl-L-ascorbic acid is handleable with an ease, and superiorly high in stability and physiological activities. Thus, crystalline 2-O-.alpha.-D-glucopyranosyl-L-ascorbic acid is favorably useful in vitamin C-enriching agents, foodstuffs, pharmaceuticals and cosmetics.Type: GrantFiled: November 12, 1993Date of Patent: April 18, 1995Assignee: Kabushiki Kaisha Hayashibara Seibutsu Kagaku KenkyujoInventors: Shuzo Sakai, Masaru Yoneyama, Toshio Miyake
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Patent number: 5405753Abstract: A process for preparing CMP-activated fluorescence indicator-labelled sialic acids is disclosed. According to the process, a 5-acylamido-9-amino-3,5,9-tridesoxy-.beta.-D-glycero-D-galactonoulosonic acid or 5-aminoacylamido-3,5-didesoxy-.beta.-D-glycero-D-galactonoulosonic acid is reacted with cytidine phosphate in the presence of a CMP-sialic acid synthase which is then reacted with a fluorescing compound to give a CMP-activated fluorescing sialic acid. Also disclosed are novel CMP-activated fluorescing sialic acids.Type: GrantFiled: September 28, 1992Date of Patent: April 11, 1995Inventors: Reinhard Brossmer, Hans J. Gross
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Patent number: 5405449Abstract: According to the invention, chain-extended starch is prepared in that starch is polymerized in an aqueous solution at pH 6.0-8.3 by means of glucosyl fluoride in the presence of inorganic phosphate, sucrose phosphorylase and potato phosphorylase.Type: GrantFiled: October 4, 1993Date of Patent: April 11, 1995Assignee: Cooperative Verkoop-en Productievereniging van Aardappelmeel en Derivaten AVEBE B.A.Inventors: Kornelis F. Gotlieb, Peter M. Bruinenberg, Johannes B. Schotting, Doede J. Binnema
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Patent number: 5403922Abstract: The subject of the invention is a surface-active composition, comprising a bolaamphiphile or bolaform chemical compound, containing a linear or branched, hydrophobic carbon chain at the two ends of which are arranged two hydrophilic portions or head group groups, corresponding to the following general formula:R A E A Rin which:E represents the carbon chain, containing at least six carbon atoms, optionally interrupted by at least one aromatic, or heterocyclic, or functional groupA is a bonding functional groupR is a residue of a reducing glucide containing a linear or cyclized chain, or of a derivative of the said glucide, bonded directly or indirectly via one of its aldehyde or ketone functional groups, or derived functional group, to the functional group A.The invention also relates to their applications as components of surface-active agents and vesicular agents, and to a process for their preparation.Type: GrantFiled: June 7, 1994Date of Patent: April 4, 1995Inventors: Rachel Garelli-Calvet, Florence Brisset, Isabelle Rico, Armand Lattes, Lionel Godefroy
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Patent number: 5401839Abstract: A process of preparing N-substituted aldonamides, the process including the steps of mixing and reacting an aldonolactone and an amine in an organic polar solvent, in the presence of an antioxidant and a reducing agent. The aldonamides have improved color; the discoloration or browning of the aldonamides upon storage or elevated temperature processing is eliminated or substantially minimized.Type: GrantFiled: March 23, 1993Date of Patent: March 28, 1995Assignee: Lever Brothers Company, Division of Conopco, Inc.Inventors: Van Au, Bijan Harirchian
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Patent number: 5399710Abstract: Novel labeling reagents are useful for radiolabeling proteins such as antibodies with radionuclide metals such as .sup.99m Tc, .sup.186 Re, and .sup.188 Re. The reagents are of the following formula: ##STR1## wherein: each X is independently chosen from O, S, NH, or NR.sub.2, wherein R.sub.2 is a protecting group or an electron withdrawing group;R.sub.1 represents a protecting group, wherein each R.sub.1 is a separate protecting group or the two R.sub.1 symbols are taken together to represent a single protecting group; andeach T is independently chosen from hydrogen, lower alkyl groups of from 1 to about 6 carbon atoms, electron withdrawing groups, and lower alkyl groups of from 1 to about 6 carbon atoms substituted with electron withdrawing group(s).Type: GrantFiled: December 22, 1992Date of Patent: March 21, 1995Assignee: NeoRx CorporationInventors: Sudhakar Kasina, Ananthachari Srinivasan, James Sanderson, Alan R. Fritzberg
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Patent number: 5399488Abstract: Novel N-acetyl-.beta.-D-glucosamine derivatives and a method for assaying N-acetyl-.beta.-D-glucosaminidase activity using the same as substrate are provided.N-Acetyl-.beta.-D-glucosamine derivatives represented by general formula (I): ##STR1## wherein each of R.sub.1 and R.sub.2 independently represents hydrogen atom or methyl or ethyl group, are mixed with a sample containing N-acetyl-.beta.-D-glucosaminidase (NAG) and then absorbance of the reaction solution is determined to assay NAG activity extremely accurately.Type: GrantFiled: May 23, 1994Date of Patent: March 21, 1995Assignee: Nitto Boseki Co., Ltd.Inventors: Katsumasa Kuroiwa, Katsuhiro Katayama, Toshihide Miura, Takeshi Nagasawa
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Patent number: 5393876Abstract: A polyacyl maltooligosaccharide derivative which is a precursor of a maltooligosaccharide derivative having modified groups at the 6-position or 4- and 6-positions of non-reducing end glucose unit and being effectively used as a substrate for measuring .alpha.-amylase activity, can be produced under mild conditions by crosslinking OH groups in the non-reducing end glucose unit of oligosaccharide with a benzylidene group having an alkoxy group, followed by acylation and treatment with a dilute acid.Type: GrantFiled: April 9, 1993Date of Patent: February 28, 1995Assignee: Wako Pure Chemical Industries, Ltd.Inventors: Atsunori Sano, Satoshi Hashizume, Hiroyuki Tsurumoto
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Patent number: 5391544Abstract: New cyathane derivatives shown by Formula (1) or (2) given below have the effect of stimulating production of nerve growth factors and antimicrobial effects: ##STR1## where R is either CHO or CH.sub.2 OH.Type: GrantFiled: February 10, 1994Date of Patent: February 21, 1995Assignee: Kagome Kabushiki KaishaInventors: Hirokazu Kawagishi, Fumihiro Ojima, Kenji Okamoto, Hideki Sakamoto, Yukio Ishiguro
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Patent number: 5391592Abstract: A process for producing a contact lens and a contact lens comprising a crosslinked lipophilised cyclodextrin derivative, wherein each repeating cyclodextrin unit includes at least one polysiloxane group. The process for producing the contact lens includes the reaction of a cyclodextrin with a polysiloxane.Type: GrantFiled: August 3, 1993Date of Patent: February 21, 1995Assignee: Ciba-Geigy CorporationInventors: Peter Herbrechtsmeier, Horst Schafer, Bernhard Seiferling, Klaus Wenke, Gerhard Wenz
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Patent number: 5385685Abstract: The present invention relates to detergent compositions comprising a glyceroglycolipid having one or two ether linkages for use as a surfactant or cosurfactant in the detergent compositions.Type: GrantFiled: November 25, 1992Date of Patent: January 31, 1995Assignee: 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: 5386016Abstract: The invention relates to 2",3",4'-tris(acetyl)-4",6"-ethylidene-.beta.-D-glucopyranosides, their preparation and their use for the preparation of 4'-demethylepipodophyllotoxin ethylidene-.beta.-D-glucopyranoside. The compounds of the invention are of the formula ##STR1## Their process of preparation comprises the following stages: acylation of a glycosyl derivativeacylation of an aglyconecoupling of the acylated glycosyl derivative and the acylated aglycone, in the presence of a Lewis acid, the acylation being carried out using an acid chloride, which is optionally identical for the two stages of acylation, in which the carbon in .alpha. of the carbonyl function bears at least one heteroatom chosen from among O and S.Type: GrantFiled: November 19, 1993Date of Patent: January 31, 1995Assignee: Pierre Fabre MedicamentInventors: Jean-Pierre Robin, Valerie Lenain
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Patent number: 5386018Abstract: N-substituted aldonamides are synthesized by the reaction of alkylamines and aldonolactone. Commercially available sources of aldonolactones (e.g., lactobiono-1,5-lactone) include aldonic acid (e.g., lactobionic acid). The presence of the acid leads to the formation of an ammonium salt impurity. The ammonium salt formation during the synthesis of N-alkyl aldonamides was minimized by the addition of an external acid. External acids and, optionally, emulsifiers were utilized to substantially reduce or eliminate the formation of an ammonium salt and to obtain N-substituted aldonamides of high purity.Type: GrantFiled: November 4, 1993Date of Patent: January 31, 1995Assignee: Lever Brothers Company, Division of Conopco, Inc.Inventors: Van Au, Bijan Harichian, Michael I. Hill, Mikhail Raykh, Jerry J. Krupa
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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: 5384311Abstract: This invention relates to liquid sucralose concentrate compositions comprising sucralose, a preservative system, a buffering system and a liquid.Type: GrantFiled: August 18, 1992Date of Patent: January 24, 1995Assignee: McNeil-PPC, Inc.Inventors: Robert N. Antenucci, Richard L. Barndt, Kas Mohammed
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Patent number: 5380829Abstract: Disclosed are thioglycoside analogs of gangliosides represented by the formula ##STR1## in which Y represents a radical of the following formula ##STR2## and X represents a radical of the formula ##STR3## wherein m is an integer of 15 to 25, l is an integer of 0 to 3 and n is an integer of 11 to 15. The thioglycoside analogs are expected to exert specific enzyme-inhibitory effects.Type: GrantFiled: February 27, 1992Date of Patent: January 10, 1995Assignees: The Nisshin Oil Mills, Ltd., Akira HasegawaInventors: Akira Hasegawa, Makoto Kiso