Double Bond Between Ring Members Of The Lactone Ring Or Chalcogen Double Bonded Directly At The 3- Or 4-position Of The Lactone Ring (e.g., Ascorbic Acid, Etc.) Patents (Class 549/315)
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Patent number: 6344567Abstract: A process for producing an ascorbic acid-2-phosphoric ester salt, where an ascorbic acid-2-phosphoric ester salt solution reduced in the content of excess phosphoric acid or a salt thereof mingled in the solution can be obtained from a solution containing an ascorbic acid-2-phosphoric ester or a salt thereof and a phosphoric acid or a salt thereof, with industrially high efficiency. A process for producing an alkaline earth metal salt of an ascorbic acid-2-phosphoric ester, comprising adding an alkaline earth metal compound to a stock solution containing an ascorbic acid-2-phosphoric ester or a salt thereof and a phosphoric acid or a salt thereof, at a liquid temperature of 0 to 30° C. to adjust the pH to 8.5 to 10.5.Type: GrantFiled: July 31, 2000Date of Patent: February 5, 2002Assignee: Showa Denko Kabushiki KaishaInventors: Yoshio Fujiwara, Yuji Kobayashi, Makoto Saito
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Publication number: 20020010210Abstract: A pharmaceutical preparation comprising at least one L-ascorbic acid derivative and at least one antimalignant tumor agent, wherein said L-ascorbic acid derivative provides, on culturing zooblast for 20 hours in a culture medium containing the L-ascorbic acid derivative in a concentration of 5 &mgr;M, an L-ascorbic acid intracellular cumulative amount equal to or greater than that obtained by culturing the zooblast in a culture medium containing magnesium L-ascorbic acid-2-phosphate in a concentration of 50 &mgr;M. Also disclosed is a method of inhibiting cancer metastasis which comprises administering to a person in need of such treatment a dosage effective amount of the L-ascorbic acid derivative. Also disclosed is a method of treating cancer which comprises administering to a person in need of such treatment a dosage effective amount of the pharmaceutical preparation.Type: ApplicationFiled: April 6, 1998Publication date: January 24, 2002Inventors: NOBUHIKO MIWA, MASAHIRO SUZUKI, TOSHI TSUZUKI, TOSHIYUKI TSUCHIYA, SHINOBU ITO, EIJI OGATA
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Patent number: 6340746Abstract: Disclosed are prodrugs as follows: (I) a prodrug of the formula where A is a sulfur or a selenium, and R is a mono- di- or oligo-saccharide; (II) a prodrug of the formula where A is sulfur or selenium, R′ is a sugar, or ═O, and the R″ groups are hydrogen, alkyl, alkoxy, carboxy; (III) a conjugate of an antioxidant vitamin and a thiolamine or selenolamine; (IV) a prodrug of the formula where A is sulfur or selenium, and R′ is a sugar, or an alkyl or aryl group, or ═O, and R‡ is an alkoxy, or an amine group; (V) a prodrug of the formula R is COOH or H, and R′ is a sugar or ═O.Type: GrantFiled: July 20, 2000Date of Patent: January 22, 2002Assignee: University of UtahInventors: Jeannette C. Roberts, Britta H. Wilmore, Pamela B. Cassidy, Pamela K. Dominick, Megan D. Short
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Patent number: 6320061Abstract: A process for recovering an organic acid or a metal salt thereof includes contacting an alcoholic phase containing one or more organic acid(s) or metal salt(s) thereof with water under conditions effective to provide an aqueous phase containing a portion of the organic acid(s) or metal salt(s) thereof. The aqueous phase does not contain substantial amounts of the alcohol(s). This process can also include recovery of the organic acid(s) or metal salt(s) thereof from the aqueous phase.Type: GrantFiled: June 5, 2000Date of Patent: November 20, 2001Assignee: Eastman Chemical CompanyInventors: Nick Allen Collins, Steven Thomas Perri
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Patent number: 6294678Abstract: A treatment for cancer and compounds for use therewith are provided. The compounds treat cancer by correcting a TATA box lesion in DNA that leads to the cancer's uncontrolled cell proliferation. The preferred compounds each contain strontium; iodine; ascorbic acid; and a diamagnetic ion, either bismuth, zinc, or potassium. These components orient the compound, transport it to the lesion, dissociate the aberrational bonds of the lesion, hydrogenate the dissociated TATA nucleotides at the lesion, and reconvert the lesion's chemical structure to that of normal DNA.Type: GrantFiled: January 12, 1998Date of Patent: September 25, 2001Inventor: George P. Sakalosky
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Patent number: 6274744Abstract: A process for preparing alkali metal salts of L-ascorbic acid comprising the following steps: a) esterifying 2-keto-L-gulonic acid or diacetone-2-keto-L-gulonic acid with a C1-C10-alkohol in the presence of an acid catalyst, b) rearranging the resultant 2-keto-L-gulonic acid C1-C10-alkyl ester in the presence of an alkali metal C1-C10-alkoxide, comprises carrying out each of the process steps a) and b) continuously.Type: GrantFiled: October 17, 2000Date of Patent: August 14, 2001Assignee: BASF AktiengesellschaftInventors: Wolfram Burst, Gerd Kaibel, Andreas Böttcher, Veronique Kessler, Thomas Kuntze
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Patent number: 6265436Abstract: The present invention broadly relates to racemic or optically active 5-substituted 3,4-dihydroxy-2(5H)-furanone compounds and their pharmaceutically acceptable salts, useful for treating a pathology in which reactive oxygen species and inflammatory mediators are contributing deleterious factors, such as acute or chronic inflammatory disorders, for example, asthma, rheumatoid arthritis, inflammatory bowel disease, and acute respiratory distress syndrome; neurodegenerative disorders, such as Alzheimer disease, Parkinson disease, amyotrophic lateral sclerosis, traumatic brain injury and multiple sclerosis; cardiovascular diseases, such as atherosclerosis; viral diseases, such as AIDS; skin diseases, such as psoriasis, sunburn and premature aging; and eye diseases, such as glaucoma, cataract, senile macular degeneration, inflammatory eye conditions, trauma, post-traumatic eye disorders, diabetic retinopathy, and eye infections.Type: GrantFiled: September 27, 1999Date of Patent: July 24, 2001Assignee: Oxis Therapeutics Inc.Inventors: Georges Appéré, Irene Erdelmeier, Claire Banissi, Marc Moutet, Allen Hopper
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Publication number: 20010007649Abstract: Ascorbic acid and/or ascorbic acid salt is made to act together with oxygen on an organic compound. Alternatively, light radiation is applied during chemical action with oxygen so as to improve a composition efficiency of an organic compound and obtain a preferable decomposition amount. This reduces the load caused by an organic compound decomposition on the environment.Type: ApplicationFiled: January 11, 2001Publication date: July 12, 2001Applicant: Sony CorporationInventor: Yasuhito Inagaki
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Patent number: 6255291Abstract: A composition containing alph-alanine, adenosine compound and a glucan. Methods for treating cancer and immunological disorders with said composition.Type: GrantFiled: February 27, 1998Date of Patent: July 3, 2001Assignee: Peregrine Pharmaceuticals, Inc.Inventor: Yveta Germano
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Patent number: 6248905Abstract: Acyl derivatives of glycosyl-L-ascorbic acids which have a higher oil-solubility than L-ascorbic acid, glycosyl-L-ascorbic acids, and inorganic esters of L-ascorbic acid such as phosphates and sulfates of L-ascorbic acid. When administered to living bodies, the acyl derivatives easily permeate into living tissues to release L-ascorbic acid, resulting in an exertion of the physiological action inherent to L-ascorbic acid. Thus, the derivatives can be arbitrarily used in food products, cosmetics, and pharmaceuticals.Type: GrantFiled: March 3, 1999Date of Patent: June 19, 2001Assignees: Kabushiki Kaisha Hayashibara Seibutsu Kagaku KenkyujoInventors: Yoshihito Fujinami, Shino Okazaki, Akihiro Tai, Kenji Sasaki, Itaru Yamamoto
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Publication number: 20010000028Abstract: Nonalcoholic steatohepatitis (NASH) is a disease of the liver characterized by inflammation and damage to the liver cells. Typically, steatohepatitis involves inflammation of the liver related to fat accumulation, and mimics alcoholic hepatitis but is observed in patients who seldom or never consume alcohol. Nonalcoholic steatohepatitis can lead to serious liver damage, and ultimately cirrhosis. The present invention provides methods and compositions useful for the treatment or alleviation of nonalcoholic steatohepatitis and the pharmaceutical formulations for their administration to a human. Specifically, compositions comprised of lecithin, antioxidants and vitamin B complex are administered parenterally, most preferably by oral administration. Specific therapeutic formulations include admixtures of these compounds and specific dosage formulations include daily oral administrations of these compounds in tablet or powder forms.Type: ApplicationFiled: November 29, 2000Publication date: March 15, 2001Inventors: Houn Simon Hsia, David Fan
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Patent number: 6197977Abstract: The invention relates to a process for the preparation of L-ascorbic acid, which comprises lactonizing a melt of alkyl 2-keto-L-gulonate under acidic conditions.Type: GrantFiled: April 20, 2000Date of Patent: March 6, 2001Assignee: BASF AktiengesellschaftInventors: Andreas Böttcher, Hans Gurski, Thomas Kuntze, Karsten Kjaergaard
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Patent number: 6177470Abstract: Optimum conditions for prostaglandin synthesis are provided by internally administering an ascorbic-6-acid ester of gamma-linolenic acid or an ascorbic-6-acid ester of dihomo-gamma-linolenic acid.Type: GrantFiled: March 2, 1998Date of Patent: January 23, 2001Assignee: Scotia Holdings PLCInventors: David F Horrobin, Philip Knowles, Mehar S Manku
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Patent number: 6177598Abstract: A process for the hydrogenation of a sugar or a mixture of two or more thereof comprises the following step: Bringing the sugar or the mixture of two or more thereof into contact with hydrogen in the presence of specific catalysts to give a sugar alcohol or a mixture of two or more thereof, wherein the catalyst comprises at least one metal of transition group VIII of the Periodic Table, either alone or together with at least one metal of transition group I or VII of the Periodic Table.Type: GrantFiled: April 1, 1999Date of Patent: January 23, 2001Assignee: BASF AktiengesellschaftInventors: Melanie Brunner, Boris Breitscheidel, Jochem Henkelmann, Arnd Böttcher
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Patent number: 6172242Abstract: The invention provides a process for the recovery of erythorbic acid from an aqueous feed solution containing values of erythorbic acid at a concentration of less than 0.7 mol/kg, comprising extracting said erythorbic acid with a water-immiscible organic extractant composition comprising at least one secondary or tertiary alkyl amine in which the aggregate number of carbon atoms is at least 20, as a primary extractant, and a polar extraction enhancer compound; wherein said extractant composition comprises at least 2 moles of said polar extraction enhancer compound per one mole of primary extractant; separating said erythorbic acid-containing organic extractant composition from residual aqueous solution, and subjecting said erythorbic acid-containing organic extractant composition to a stripping operation with aqueous solution at a temperature of at least 20° C.Type: GrantFiled: April 22, 1999Date of Patent: January 9, 2001Assignee: Yissum Research Development Company of the Hebrew University of JerusalemInventors: Aharon Meir Eyal, Asher Vitner, Tal Reuveni, Betty Hazan
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Patent number: 6169187Abstract: The invention provides a process for the recovery of ascorbic acid from a feed containing at least one precursor of ascorbic acid comprising converting the precursor into at least one product, the at least one product being ascorbic acid in an organic extractant composition, the organic extractant composition comprising at least one secondary or tertiary alkyl amine in which the aggregate number of carbon atoms is at least 20, as a primary extractant, and a polar extraction enhancer compound; wherein the extractant composition comprises at least 2 moles of the polar extraction enhancer compound per one mole of primary extractant; and subjecting the ascorbic acid-containing organic extractant composition to a stripping operation with aqueous solution at a temperature of at least 20° C. higher than the temperature at which the conversion is carried out; whereby there is obtained an aqueous solution of ascorbic acid in which the concentration of ascorbic acid is higher than 5%.Type: GrantFiled: August 9, 1999Date of Patent: January 2, 2001Assignee: Yissum Research Development Company of the Hebrew University of JerusalemInventor: Aharon Meir Eyal
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Patent number: 6150543Abstract: The invention relates to a process for the enzymatic preparation of regioselective fatty acid esters of ascorbic acid and selected fatty acid alkyl esters.Ascorbic acid and fatty acid alkyl esters are reacted in a solvent or suspending agent at reduced pressure in relation to the atmosphere and temperatures above the boiling point of the resulting alcohol of reaction.Type: GrantFiled: December 14, 1998Date of Patent: November 21, 2000Assignee: Th. Goldschmidt AgInventors: Burghard Gruning, Geoffrey Hills
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Patent number: 6143906Abstract: Ascorbyl sorbates of the formula I, ##STR1## where the variables independently of one another have the following meanings:R.sup.1 and R.sup.2are hydrogen, C.sub.1 -C.sub.12 -alkyl, C.sub.1 -C.sub.20 -acyl;where R.sup.1 and R.sup.2, together with the oxygen atoms to which they are bonded and the carbon atoms bonded to the oxygen atoms, can form an unsubstituted or substituted heterocycle;R.sup.3 is hydrogen or a cation selected from the group consisting of alkali metals and alkaline earth metals.Type: GrantFiled: October 26, 1998Date of Patent: November 7, 2000Assignee: BASF AktiengesellschaftInventors: Harald Streicher, Linda von dem Bussche-Hunnefeld, Horst Westenfelder, Hans-Ulrich Wekel
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Patent number: 6136832Abstract: The present invention relates to synthetic methods for the production of both optically active and racemic 5,5-disubstituted-3,4-dihydroxy-2(5H)-furanones; 5-[(4-aryl)-3-butynyl]-3,4-dihydroxy-2(5H)-furanones; 5-(2-arylthio)ethyl-3,4-dihydroxy-2(5H)-furanones; and 5-(2-aryloxy)ethyl-3,4-dihydroxy-2(5H)-furanones. This invention further relates to the use of the above mentioned compounds as anti-inflammatory agents through their action as mixed inhibitors of lipid peroxidation, 5-lipoxygenase, cyclooxygenase-1 and cyclooxygenase-2. The invention further relates to the use of such compounds in the treatment of chronic inflammatory disorders such as asthma, rheumatoid arthritis, inflammatory bowel disease, atherosclerosis, acute respiratory distress syndrome, and central nervous system disorders such as Alzheimer's and Parkinson's disease wherein reactive oxygen species and inflammatory mediators are contributing deleterious factors.Type: GrantFiled: May 19, 1999Date of Patent: October 24, 2000Assignee: Oxis International Inc.Inventors: Allen T. Hopper, John A. Ziemniak, Robert E. Johnson
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Patent number: 6084110Abstract: This invention relates to a stable vitamin C preparation and a method for stabilizing vitamin C preparation. According to the invention, the vitamin C preparation stable for a long period of time can be obtain, since the preparation contains magnesium ions which have the effect of stabilizing vitamin C.Type: GrantFiled: October 28, 1998Date of Patent: July 4, 2000Assignee: Welfide CorporationInventors: Takae Kido, Hideto Kodaira, Koji Munechika, Shunichi Abe, Yasuo Ueda
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Patent number: 6060046Abstract: An antifouling composition that comprises an effective amount of a furanone of the structure shown and a suitable carrier therefor. In the figure, substituents R.sub.1, R.sub.2 and R.sub.3 are each a hydrogen atom, a hydroxyl group, an alkyl group containing from 1 to 10 carbon atoms, an ether group containing from 1 to 10 carbon atoms, an ester group containing from 1 to 10 carbon atoms or a halogenated alkene containing from 1 to 10 carbon atoms or R.sub.2 and R.sub.3 together may comprise an unsubstituted or a halogenated alkene containing from 1 to 10 carbon atoms and R.sub.4 is a hydrogen or halogen atom, and a suitable carrier therefor.Type: GrantFiled: February 18, 1997Date of Patent: May 9, 2000Assignee: Unisearch LimitedInventors: Peter D. Steinberg, Peter C. De Nys
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Patent number: 6037480Abstract: The invention provides an extraction process for the recovery of ascorbic id from an aqueous feed solution containing the acid at a concentration of less than 0.7 mol/kg.Type: GrantFiled: February 23, 1998Date of Patent: March 14, 2000Assignee: Yissum Research Development Company of The Hebrew University of JerusalemInventors: Aharon M. Eyal, Betty Hazan
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Patent number: 6037481Abstract: The present invention refers to a process for stabilizing LAA in an aqueous medium, which includes the step of contacting the LAA with at least one compound capable of forming hydrogen bridges with the LAA. In another aspect, the invention relates to a stable aqueous LAA composition which includes, in addition to said ascorbic acid, at least one compound which is linked to the LAA by hydrogen bridges, and to a process for preparing it. The present invention further relates to an emulsion including, in its aqueous phase, at least one compound linked to levogyre ascorbic acid (LAA) by hydrogen bridges. Further according to the present invention a vitamin product is provided, in which a stable LAA composition as described above is contained in organic envelopes which enable a gradual and prolonged release of the LAA into the organism. The vitamin product may further include a compound capable of stimulating the metabolism of the fibroblasts.Type: GrantFiled: October 22, 1997Date of Patent: March 14, 2000Assignee: Industria E Comercio De Cosmeticos Natura LtdaInventors: Roberto Alcantara Martins Zucchetti, Simoni Chitarra Souza, Philippe Joseph Pommez, Karla De Souza Araujo
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Patent number: 6020367Abstract: A method of preparing a supersaturated and stable solution of ascorbic acid, supersaturated ascorbic acid solutions and compositions containing such supersaturated solutions. A polyol vehicle is heated to an elevated temperature, and the ascorbic acid is dissolved therein to form an ascorbic acid/polyol solution. The method provides a solution containing a significant concentration of ascorbic acid that is stable over time, temperature changes and other environmental factors.Type: GrantFiled: December 2, 1997Date of Patent: February 1, 2000Assignee: Avon Products, Inc.Inventors: John A. Duffy, Dmitri Ptchelintsev
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Patent number: 6005000Abstract: The present invention relates to synthetic methods for the production of both optically active and racemic 5,5-disubstituted-3,4-dihydroxy-2(5H)-furanones; 5-[(4-aryl)-3-butynyl]-3,4-dihydroxy-2(5H)-furanones; 5-(2-arylthio)ethyl-3,4-dihydroxy-2(5H)-furanones; and 5-(2-aryloxy)ethyl-3,4-dihydroxy-2(5H)-furanones. This invention further relates to the use of the above mentioned compounds as anti-inflammatory agents through their action as mixed inhibitors of lipid peroxidation, 5-lipoxygenase, cyclooxygenase-1 and cyclooxygenase-2. The invention further relates to the use of such compounds in the treatment of chronic inflammatory disorders such as asthma, rheumatoid arthritis, inflammatory bowel disease, atherosclerosis, acute respiratory distress syndrome, and central nervous system disorders such as Alzheimer's and Parkinson's disease wherein reactive oxygen species and inflammatory mediators are contributing deleterious factors.Type: GrantFiled: August 20, 1997Date of Patent: December 21, 1999Assignee: Oxis International, Inc.Inventors: Allen T. Hopper, John A. Ziemniak, Robert E. Johnson
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Patent number: 5998634Abstract: A method is provided for producing L-ascorbic acid (Vitamin-C) in a single process step. Starting material, particularly a mixture of compounds from the group consisting of glucose, sorbitol, sorbose, and 2-keto-L-gulonic acid, is catalytically oxidized in aqueous solution by hypochlorous acid. L-ascorbic acid then can be separated from the aqueous solution, and the unconverted reactants recycled for greater conversion. The reaction occurs in the aqueous state at ambient temperature near a pH of 5.5 when an optimum amount of hydrous cobalt-oxide is present in the solution.Type: GrantFiled: March 15, 1999Date of Patent: December 7, 1999Assignee: The United States of America as represented by the Secretary of the InteriorInventors: Andrew P. Murphy, Lisa Renee Henthorne
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Patent number: 5977073Abstract: A composition and method for its use in treatment of an immune disorder in a mammal. The composition includes, in relative amounts, between 50 and 3000 mg of a purified compound selected from oxidized and unoxidized gamma-L-glutamyl-L-cysteinylglycine, gamma-L-glutamyl-L-cysteine, N-acetyl-L-cysteine, N-acetyl-L-cysteine-glycine, and any other pharmaceutically active compound which directly enhances the level of gamma-L-glutamyl-L-cysteinylglycine in a mammal, and any salt or ester of said compound, between 50 and 3000 mg purified L-glutamine, between 50 and 10,000 mg purified vitamin C, between 50 and 500 mg purified vitamin E, between 10 and 100 mg purified Beta-carotene, and between 1 and 25 mg purified vitamin B.sub.6.Type: GrantFiled: June 6, 1991Date of Patent: November 2, 1999Assignee: Life Sciences' Technologies, Inc.Inventor: F. Mahnaz Khaled
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Patent number: 5962701Abstract: Chromanylascorbic acid derivatives of the general formula I ##STR1## where R.sup.1 is an organic radical having 1 to 12 C atoms, in particular a methyl group,R.sup.2 is an organic radical having 8 to 30 C atoms, which is unsubstituted or substituted by functional groups, in particular the phytyl 30 radical, andR.sup.3 is the --PO.sub.3 H.sub.2 -- radical or a glycosidyl radical,R.sup.3, R.sup.4 and R.sup.5 are hydrogen, or an alkyl or acyl group having 1 to 20 C atoms, in particular hydrogen, andR.sup.Type: GrantFiled: August 18, 1997Date of Patent: October 5, 1999Assignee: BASF AktiengesellschaftInventors: Thomas Rosenau, Wolf-Dieter Habicher, Harald Streicher
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Patent number: 5922382Abstract: This invention relates to a novel method of preserving fresh cut fruit for a prolonged period of time. More particularly, this invention is directed to a novel method of preparing and preserving fresh, vitaminized flavored or unflavored cut apple pieces to be stored in containers for extended periods of time of up to 6 weeks at refrigerated temperatures with the retention of acceptable naturally-occurring and adjunctive flavors, crisp texture and original whiteness or yellowness, being free of enzymatic browning.Type: GrantFiled: November 8, 1996Date of Patent: July 13, 1999Assignee: The University of British ColumbiaInventors: William Duncan Powrie, Chiu Hui Wu
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Patent number: 5916915Abstract: Disclosed herein are a L-ascorbic acid derivative having an improved water-in-stability, represented by a following general formula (I): ##STR1## and a method for preparation thereof, and to a skin-whitening cosmetic composition containing the same as an active ingredient.Type: GrantFiled: June 4, 1998Date of Patent: June 29, 1999Assignee: Pacific CorporationInventors: Jong Eon Hong, Ki Hwa Lee, Jun Chul Cho, Jang Sob Lee, Jung No Lee, Ji Min Chun, Dong Il Jang, Ok Sob Lee, Sang Rhin Lee
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Patent number: 5902885Abstract: L-ascorbic acid is produced by allowing an acid to act on 2-keto-L-gulonic acid in a mixture solvent of an inert organic solvent and an aliphatic ketone in the presence of water and a surfactant.The method produces L-ascorbic acid in a high yield 90% or more and is an industrially advantageous method.Type: GrantFiled: January 8, 1993Date of Patent: May 11, 1999Assignee: Takeda Chemical Industries, Ltd.Inventors: Kunio Takanohashi, Mitsutaka Tanaka, Toru Yamano
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Patent number: 5859262Abstract: The invention provides a process for the recovery of erythorbic acid from an aqueous feed solution containing values of erythorbic acid at a concentration of less than 0.7 mol/kg, comprising adsorbing a major portion of said erythorbic acid with a solid phase adsorbent resin selected from resins carrying a pyridine function and resins of similar or weaker basicity; separating said erythorbic acid-containing resin from residual aqueous solution, and subjecting said erythorbic acid-containing resin to a desorbing operation with a neutral solvent at a temperature of at least 20.degree. C. higher than the temperature at which said adsorption is carried out, whereby there is obtained a solution of erythorbic acid in solvent in which the concentration of erythorbic acid is at least equal to its concentration in said aqueous feed solution.Type: GrantFiled: November 26, 1997Date of Patent: January 12, 1999Assignee: Yissum Research Development CompanyInventors: Aharon Meir Eyal, Asher Vitner, Tal Reuveni, Betty Hazan
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Patent number: 5780504Abstract: This disclosure relates to a method for topical use of a derivative of L-ascorbic acid which is stable, easily incorporated into cosmetically acceptable vehicles and enzymatically bioreversible in the skin to free ascorbic acid and a safe alkanol component. An exemplary embodiment uses the alkyl-2-O-L-ascorbyl-phosphate which is shown in Formula I.Type: GrantFiled: February 28, 1997Date of Patent: July 14, 1998Assignee: Avon Products, Inc.Inventor: Dmitri Ptchelintsev
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Patent number: 5767149Abstract: .alpha.-Glycosyl-L-ascorbic acid exhibiting no direct reducing activity is formed in a solution containing L-ascorbic acid and an .alpha.-glucosyl saccharide when subjected to the action of a saccharide-transferring enzyme. .alpha.-Glycosyl-L-ascorbic acid is superiorly stable, and readily hydrolyzable in vivo to exhibit the activities inherent to L-ascorbic acid. Thus, .alpha.-glycosyl-L-ascorbic acid is favorably useful as a stabilizer, quality-improving agent, antioxidant, physiologically active agent and uv-absorbent in food pharmaceutical and cosmetic industries.Type: GrantFiled: January 14, 1997Date of Patent: June 16, 1998Assignee: Kabushiki Kaisha Hayashibara Seibutsu Kagaku KenkyujoInventors: Itaru Yamamoto, Norio Muto, Toshio Miyake
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Patent number: 5744618Abstract: A process for the preparation of L-ascorbic acid by reacting 2-keto-L-gulonic acid with aqueous mineral acid in a solvent mixture containing an inert organic solvent, an aliphatic ketone and also an acid chloride.Type: GrantFiled: December 13, 1996Date of Patent: April 28, 1998Assignee: Merck Patent Gesellschaft Mit Beschrankter HaftungInventors: Ulrich Fechtel, Karlheinz Wembacher
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Patent number: 5656662Abstract: The present invention relates to a method for synthesis of optically pure 4-alkenyl or 4-alkanyl-2-hydroxytetronic acids from an optically pure aldehyde. The invention further relates to the use of such optically pure compounds as potent inhibitors of platelet aggregation by working at the level of cyclooxygenase, thus making them useful in the treatment of coronary artery diseases, especially atherosclerosis, and additionally, as inhibitors of various inflammatory cytokines, making them useful in the treatment of both acute and chronic inflammation, as well in the treatment of cachexia, rheumatoid arthritis, multiple sclerosis, Crohn's disease and ulcerative colitis. The invention further relates to pharmaceutical compositions of the instant compounds.Type: GrantFiled: June 7, 1995Date of Patent: August 12, 1997Assignee: The Ohio State University Research FoundationInventors: Padmaja Mantri, Donald T. Witiak
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Patent number: 5637734Abstract: A process for producing L-ascorbic acid, which comprises reacting 2-keto-L-gulonic acid with an acid in an ether or an inert organic solvent containing an ether in the presence of water and a surfactant.Type: GrantFiled: November 3, 1995Date of Patent: June 10, 1997Assignee: Takeda Chemical Industries, Ltd.Inventors: Haruomi Honda, Toru Yamano, Masayuki Yamashita
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Patent number: 5616611Abstract: .alpha.-Glycosyl-L-ascorbic acid exhibiting no direct reducing activity is formed in a solution containing L-ascorbic acid and an .alpha.-glucosyl saccharide when subjected to the action of a saccharide-transferring enzyme. .alpha.-Glycosyl-L-ascorbic acid is superiorly stable, and readily hydrolyzable in vivo to exhibit the activities inherent to L-ascorbic acid. Thus, .alpha.-glycosyl-L-ascorbic acid is favorably useful as a stabilizer, quality-improving agent, antioxidant, physiologically active agent and uv-absorbent in food pharmaceutical and cosmetic industries.Type: GrantFiled: December 11, 1991Date of Patent: April 1, 1997Assignee: Kabushiki Kaisha Hayashibara Seibutsu Kagaku KenkyujoInventors: Itaru Yamamoto, Norio Muto, Toshio Miyake
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Patent number: 5610122Abstract: The present invention relates to a new 3-aryl-4-hydroxy-.DELTA..sup.3 -dihydrofuranone derivatives of the general formula (I) ##STR1## in which the radicals A, B, G, X, Y, Z and n have the meaning given in the description, to a plurality of processes for their preparation, and to their use as pesticides.Type: GrantFiled: September 9, 1994Date of Patent: March 11, 1997Assignee: Bayer AktiengesellschaftInventors: Reiner Fischer, Thomas Bretschneider, Bernd-Wieland Kr uger, Hans-Joachim Santel, Markus Dollinger, Ulrike Wachendorff-Neumann, Christoph Erdelen
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Patent number: 5607968Abstract: This disclosure relates to a method for topical use of a derivative of L-ascorbic acid which is stable, easily incorporated into cosmetically acceptable vehicles and enzymatically bioreversible in the skin to free ascorbic acid and a safe alkanol component. An exemplary embodiment uses the alkyl-2-O-L-ascorbyl-phosphate which is shown in Formula I.Type: GrantFiled: June 7, 1995Date of Patent: March 4, 1997Assignee: Avon Products, Inc.Inventor: Dmitri Ptchelintsev
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Patent number: 5559251Abstract: The invention relates to the process for the preparation of new derivatives of amino-ascorbic acid, their acid and alkali salts, processes for preparation and action.According to this invention derivatives of amino-ascorbic acid are prepared by three types of reactions: 1. reductive alkylation of amino-ascorbic acid; 2. alkylation of primary and secondary amines with halogen-ascorbic acid and 3. acylation of amino-ascorbic acid.Type: GrantFiled: February 3, 1994Date of Patent: September 24, 1996Assignee: Pliva, farmaceutskaInventors: Bozidar Suskovic, Vanja Vela, Mira Buncic
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Patent number: 5550241Abstract: The present invention relates to novel adducts of cyclic carbonyl monomers with substituted olefins, which also are useful as solution viscosifiers.Type: GrantFiled: March 18, 1993Date of Patent: August 27, 1996Assignee: Exxon Research and Engineering CompanyInventor: Stanley J. Brois
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Patent number: 5536500Abstract: The present invention provides vitamin C derivatives and cosmetic, pharmaceutical and nutritional compositions containing same which impart protective properties against oxidation of lipidic constituents of the skin.Type: GrantFiled: January 20, 1995Date of Patent: July 16, 1996Assignee: L'OrealInventors: Jean-Baptiste Galey, Eric Terranova
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Patent number: 5534531Abstract: New compounds having the general formula I ##STR1## wherein L may be H or D; Y may be CN or ##STR2## wherein A may be H, D, alkyl with 1-4 carbon atoms, OR wherein R is H or alkyl with 1-4 carbon atoms, or CR.sub.1 R.sub.2 R.sub.3 wherein R.sub.1, R.sub.2 and R.sub.3 are the same or different and are H or alkyl with 1-4 carbon atoms; Z is H, D, Y or alkyl with 1-4 C-atoms, halogen, nitro, amino, monoalkyl amino or dialkyl amino wherein the alkyl groups have 1-4 C atoms, or OR wherein R may be H or alkyl with 1-4 C-atoms, or CR.sub.4 R.sub.5 R.sub.6 wherein R.sub.4, R.sub.5 and R.sub.6 may be the same or different and may be H or F; X.sub.1 and X.sub.2 may be the same or different and may be OR, NR.sub.1 R.sub.2 or SR, wherein R, R.sub.1 and R.sub.2 may be the same or different and may be alkyl having 1-22 carbon atoms which may be branched or straight chained and/or may be further substituted; or X.sub.1 and X.sub.Type: GrantFiled: January 19, 1993Date of Patent: July 9, 1996Assignee: Norsk Hydro A.S.Inventors: Erik O. Pettersen, Rold O. Larsen, John M. Dornish, Bernt Boorretzen, Reidar Oftebro, Thomas Ramdahl
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Patent number: 5508275Abstract: Lipid-selective antioxidants of the formula I(A).sub.a (L)(X).sub.a, (I),in whichA=an antioxidative component,L=a bridging member,X=a lipophilic componenta and a'=independently of one another the numbers 1 or 2.The compounds are used for the protection of lipid-containing substances against oxidation and in pharmaceuticals for the prophylaxis and treatment of diseases in which bioradicals are involved, in particular of coronary, circulatory and vascular diseases.Type: GrantFiled: March 15, 1994Date of Patent: April 16, 1996Assignee: Hoechst AktiengesellschaftInventors: Klaus-Ulrich Weithmann, Gunther Wess, Dirk Seiffge
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Patent number: 5508391Abstract: 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: December 19, 1994Date of Patent: April 16, 1996Assignee: Kabushiki Kaisha HayashibaraInventors: Shuzo Sakai, Masaru Yoneyama, Toshio Miyake
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Patent number: 5504107Abstract: The present invention relates to a method for synthesis of optically pure 4-alkenyl or 4-alkanyl-2-hydroxytetronic acids from an optically pure aldehyde. The invention further relates to the use of such optically pure compounds as potent inhibitors of platelet aggregation by working at the level of cyclooxygenase. The invention further relates to the pharmaceutical use of such compounds in the treatment of coronary artery diseases, especially in the treatment and/or prevention of atherosclerosis.Type: GrantFiled: May 19, 1994Date of Patent: April 2, 1996Assignee: The Ohio State University Research FoundationInventors: Padmaja Mantri, Donald T. Witiak
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Patent number: 5504108Abstract: The present invention relates to a method for synthesis of optically pure stereogenically labile 4-aryl-2-hydroxytetronic acids from an optically pure aidehyde. The invention further relates to the use of such optically pure compounds as potent inhibitors of platelet aggregation by working at the level of cyclooxygenase, and additionally as inhibitors of cyclooxygenase and 5-lipoxygenase. The invention further relates to the pharmaceutical use of such.compounds in the treatment of coronary artery diseases, especially in the treatment and/or prevention of atherosclerosis, and in the treatment of various inflammatory pathologies, especially arthritis.Type: GrantFiled: December 5, 1994Date of Patent: April 2, 1996Assignee: The Ohio State University Research FoundationInventors: Donald T. Witiak, Allen T. Hopper
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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: 5466830Abstract: This invention relates to 4-phenoxy (and 4-substituted phenoxy)5-hydroxy-2(5H)-furanones of the formula: ##STR1## where Z is ##STR2## where R is H, halogen, C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.8 cycloalkyl, trifluoromethyl, or ##STR3## and X is H, C.sub.1 -C.sub.8 alkyl, --O--C.sub.1 -C.sub.8 alkyl, or halogen;a process for their preparation, their use in the treatment of osteoporosis, and pharmaceutical compositions thereof.Type: GrantFiled: May 18, 1994Date of Patent: November 14, 1995Assignee: American Home Products CorporationInventor: Joseph P. Sabatucci