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: 5464865Abstract: The invention provides novel 5-hydroxy-4-aryl- and 5-hydroxy-4-(arylthio)-2(5H)-furanones of the following structure: ##STR1## wherein R contains from about five to about twenty carbon atoms and is defined herein; X is oxygen, sulfur, SO.sub.2, NH, N(lower alkyl), N(lower acyl), aminocarbonyl, carbonyl, carbonylamino, CH.sub.2 or a carbon-carbon bond; Y is hydrogen, halogen, lower alkyl, nitro, alkylthio, perfluoroalkyl, hydroxy, or lower alkoxy(C.sub.1 -C.sub.8); Z is sulfur or a carbon-carbon bond; and Q is H, an alkyl of from 1-20 carbon atoms, COR', COOR', CONHR', PO(OR')2, PO(OR')R" wherein R' and R" are independently selected from the group consisting of H, an alkyl of from 1-20 carbon atoms, phenyl, and substituted phenyl and prodrugs thereof and pharmaceutically acceptable salts thereof.Type: GrantFiled: December 22, 1993Date of Patent: November 7, 1995Assignee: Ortho Pharmaceutical CorporationInventors: James P. Demers, Richard B. Sulsky
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Patent number: 5457214Abstract: The present invention is directed to a method for the recovery of erythorbates from photographic solutions. In the disclosed method, the photographic solution is first acidified by passing it over an acidic cation exchange resin and the resultant solution is then passed over a weakly basic anion exchange resin.Type: GrantFiled: October 19, 1994Date of Patent: October 10, 1995Assignee: Pfizer Inc.Inventor: Alvin J. O'Donnell
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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: 5399721Abstract: The present invention relates to a method for synthesis of optically pure stereogenically labile 4-aryl-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: February 25, 1994Date of Patent: March 21, 1995Assignee: The Ohio State University Research FoundationInventors: Allen T. Hopper, Donald T. Witiak
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Patent number: 5393741Abstract: New compounds having the general formula I ##STR1## wherein Y may be H or D; and A is H, D, 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 is H or alkyl of 1-4 C-atoms;X.sub.1 and X.sub.2 may together with the carbon atom to which they are bound form a cyclic acetal, thioacetal, dithiane, aminal, oxazolidine or thiazolidine;or pharmaceutically acceptable salts thereof.The compounds are useful as anti-carcinoma agents.Type: GrantFiled: November 27, 1991Date of Patent: February 28, 1995Assignee: Norsk Hydro a.s.Inventors: Erik O. Pettersen, Rolf O. Larsen, Bernt Borretzen, John M. Dornish, Reidar Oftebro
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Patent number: 5391770Abstract: Process for preparing pure ascorbic acid from 2-keto-L-gulonic acid or its sodium salt, by carrying out the following successive steps:esterification of 2-keto-L-gulonic acid or its sodium saltlactonization to sodium ascorbateoptional separation of the sodium ascorbatedisplacement of the ascorbic acid from its saltseparation of the sodium sulphateseparation and purification of the ascorbic acid from its methanolic or aqueous-methanolic solution.Type: GrantFiled: December 23, 1993Date of Patent: February 21, 1995Assignee: Rhone Poulenc Rorer S.A.Inventors: Isidore Le Fur, Jean-Paul Richard, Gerard Wolff
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Patent number: 5380753Abstract: This invention relates to a bath agent containing sodium chloride and a compound represented by the formula ##STR1## (in the formula R.sub.1 and R.sub.2 are the same or different, and are a hydrogen atom or a methyl group) or its salt.This inventive bath agent is to eliminate and prevent skin itching and to prevent skin aging by preventing and removing effectively the free radical produced on the skin surface by ultraviolet rays.Type: GrantFiled: March 30, 1993Date of Patent: January 10, 1995Assignee: Senju Pharmaceutical Co., Ltd.Inventors: Shoji Yoshida, Kazumi Ogata, Osamu Kawahira
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Patent number: 5376374Abstract: There is disclosed a pleasant tasting oral rinse composition and a method of using the same. The composition consists essentially of cayenne pepper, calendula, echinacea, goldenseal, propolis, vinegar, and water in certain proportions.Type: GrantFiled: May 24, 1993Date of Patent: December 27, 1994Inventor: Luz M. Zelaya
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Patent number: 5359139Abstract: A tert-amine which contains an acid-activated color body precursor is treated to prevent it or a derivative thereof, e.g., an amine oxide, betaine, or quaternary ammonium compound, from turning pink when exposed to acidic conditions by contacting it with ascorbic acid.Type: GrantFiled: March 18, 1991Date of Patent: October 25, 1994Assignee: Albemarle CorporationInventors: Kim R. Smith, James E. Borland, Joe D. Sauer
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Patent number: 5336687Abstract: 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: August 4, 1993Date of Patent: August 9, 1994Assignee: American Home Products CorporationInventor: Joseph P. Sabatucci
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Patent number: 5298526Abstract: The present invention relates to a method for synthesis of optically pure stereogenically labile 4-substituted-2-hydroxytetronic acids from an asymmetric .alpha.-hydroxy ester. The chiron approach of the present invention utilizes a non-nucleophilic lithium amide base under kinetically controlled Claisen conditions to produce a 4-substituted-2-pheylmethoxy precursor to the 4-substituted-2-hydroxy tetronic acid. 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: March 6, 1992Date of Patent: March 29, 1994Assignee: The Ohio State University Research FoundationInventors: Donald T. Witiak, Ashok K. Tehim
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Patent number: 5270336Abstract: Derivatives of 3,4-dihydroxy-2,5-dihydrofuran-5-ones, intermediates and processes useful for their preparation are disclosed. These compounds are useful as free-radical scavengers and exhibit cellular protective properties.Type: GrantFiled: August 26, 1992Date of Patent: December 14, 1993Assignee: Merrell Dow Pharmaceuticals Inc.Inventors: Gilbert Marciniak, J. Martin Grisar
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Patent number: 5210220Abstract: The invention is concerned with a process for the manufacture of ascorbyl phosphates, namely of phosphates of the formula ##STR1## wherein M.sup.k.sym. denotes a cation, k.sup..sym. denotes the valency and m denotes the equivalents, with the proviso that the product from k.m=3, by phsophorylating ascorbic acid.k is 1 to 3, especially 1 or 2.The process comprises using pre-formed sodium (or potassium) dichlorophosphate as the phosphorylating reagent, adding ascorbic acid to this pre-formed phosphorylating reagent in aqueous solution, especially at pH values between about 11.0 and about 13.0, in the presence of a water-soluble trialkylamine as the catalyst and at temperatures between about +10.degree. C. and about -8.degree. C., especially at temperatures below 0.degree. C., and, if desired, trans-salting the I which is obtained as the sodium (or potassium) salt and/or, if desired, purifying via an amine salt.Type: GrantFiled: October 25, 1991Date of Patent: May 11, 1993Assignee: Hoffmann-La Roche Inc.Inventors: Horst Pauling, Christof Wehrli
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Patent number: 5202445Abstract: Potassium magnesium L-ascorbate 2-phosphate is prepared from an aqueous solution of potassium L-ascorbate 2-phosphate which is highly contaminated with KCl, as is produced in the phosphorylation of 5,6-isopropylidene-L-ascorbic acid, by adding to the solution about 1 equivalent of magnesium ions per equivalent of L-ascorbate 2-phosphate, and subsequently removing the KCl by electrodialysis. The product of this process is a novel salt of L-ascorbic acid 2-phosphate and has very advantageous handling properties.Type: GrantFiled: August 20, 1991Date of Patent: April 13, 1993Assignee: BASF AktiengesellschaftInventors: Walter Dobler, Hartwig Voss, Friedhelm Balkenhohl, Joachim Paust
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Patent number: 5194445Abstract: The preparation for preventing and curing organ dysfunctions, provided by the present invention, is a medicament having the activity to prevent and cure organ dysfunctions which active oxygen species and active organic radical species would cause, and unconventionally improved in stability in vivo by containing, as an active component, the ascorbic acid derivative of the formula, ##STR1## wherein R.sub.2 is a group selected from the class consisting of an alkylcarbonyl lower alkyl group of which the terminal alkyl group has 7 inclusive to 15 inclusive carbon atoms, an alkyl group having 9 inclusive to 17 inclusive alkyl groups and an alkoxycarbonyl lower alkyl group of which the terminal alkoxy group has 7 inclusive to 20 inclusive carbon atoms; and the ascorbic acid derivative of the above formula in which R.sub.Type: GrantFiled: May 20, 1991Date of Patent: March 16, 1993Assignee: Nippon Hypox Laboratories IncorporatedInventors: Toshio Satoh, Yasunori Niiro, Hisao Kakegawa, Hitoshi Matsumoto
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Patent number: 5189057Abstract: A compound of the formula (I): ##STR1## wherein R.sub.1 and R.sub.2 each is a hydrocarbon residue, R.sub.3 is a sulfo group or phosphono group, --CO--R.sub.4 is an esterified carboxyl group, a thiol-esterified carboxyl group or an amidated carboxyl group; and .about. represents the absolute configuration of R or S, or its salt, which is useful for preventing and treating thrombosis.Type: GrantFiled: July 19, 1991Date of Patent: February 23, 1993Assignee: Takeda Chemical Industries, Ltd.Inventors: Koichi Kato, Hirotomo Masuya, Moriya Norihiko
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Patent number: 5175188Abstract: Derivatives of 3,4-dihydroxy-2,5-dihydrofuran-5-ones, intermediates and processes useful for their preparation are disclosed. These compounds are useful as free-radical scavengers and exhibit cellular protective properties.Type: GrantFiled: January 10, 1992Date of Patent: December 29, 1992Assignee: Merrell Dow Pharmaceuticals Inc.Inventors: Gilbert Marciniak, J. Martin Grisar
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Patent number: 5137723Abstract: .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: March 30, 1990Date of Patent: August 11, 1992Assignee: Kabushiki Kaisha Hayashibara Seibutsu Kagaku KenkyujoInventors: Itaru Yamamoto, Norio Muto, Toshio Miyake
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Patent number: 5128487Abstract: In the process described for the production of sodium or potassium L-ascorbate, 2-keto-L-gulonic acid monhydrate is esterified with methanol. The esterification is only partial, that is, is not carried out until the esterification equilibrium is reached. In an intermediate step, by addition of sodium or potassium bicarbonate in an amount precisely enough for neutralizing the esterified solution, unesterified 2-keto-L-gulonic acid and impurities present are precipitated and separated out. Then by adding more bicarbonate, the lactonizing of the 2-keto-L-gulonic acid methyl ester formed is made possible. In order to reach a high yield, the unesterified 2-keto-L-gulonic acid from the bicarbonate precipitation may be re-esterified by the same process, preferably parallel, and also converted into ascorbate. This process makes possible the production of very pure sodium or potassium ascorbate, suitable for pharmaceutical purposes in a profitable way.Type: GrantFiled: June 22, 1990Date of Patent: July 7, 1992Assignee: Enco Engineering Chur AGInventors: Keglevic Tomislav, Klein Christoph
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Patent number: 5112853Abstract: New furanone compounds have anti-inflammatory, immunosuppresive and anti-proliferative activity and are useful in treating psoriasis and modifying calcium homeostasis. A compound of the invention is 4-[3,6-dihydro-6-hydroxy-5-(3-phenylpropyl)-2H-pyran-2-yl]-5-hydroxy-2-(5H )-furanone.Type: GrantFiled: June 3, 1991Date of Patent: May 12, 1992Assignee: Allergan, Inc.Inventors: Michael E. Garst, Elizabeth T. Syage
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Patent number: 5095126Abstract: The present invention relates to a method for synthesis of optically pure stereogenically labile 4-substituted-2-hydroxytetronic acids from an asymmetric .alpha.-hydroxy ester. The chiron approach of the present invention utilizes a non-nucleophilic lithium amide base under kinetically controlled Clasien conditions to produce a 4-substituted-2-pheylmethoxy precursor to the 4-substituted-2-hydroxy tetronic acid. 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: January 12, 1990Date of Patent: March 10, 1992Assignee: Ohio State University Research FoundationInventors: Donald T. Witiak, Ashok K. Tehim
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Patent number: 5084563Abstract: 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, 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: October 16, 1990Date of Patent: January 28, 1992Assignee: Kabushiki Kaisha Hayashibara Seibutsu Kagaku KenkyujoInventors: Shuzo Sakai, Masaru Yoneyama, Toshio Miyake
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Patent number: 5061812Abstract: This invention relates to a novel ascorbic acid derivative having excellent antioxidant action and a process for preparing the same.Furthermore, this invention also relates to a novel antioxidant comprising the aforementioned ascorbic acid derivative or other known ascorbic acid derivatives.Type: GrantFiled: July 20, 1989Date of Patent: October 29, 1991Assignee: Nippon Hypox Laboratories IncorporatedInventors: Toshio Satoh, Yasunori Niiro, Hisao Kakegawa, Hitoshi Matsumoto
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Patent number: 5043459Abstract: This invention relates to novel saccharoascorbic acid derivatives and their production. The derivatives are represented by the general formula set forth below, for example, an amido, a thioester or carboxylic ester of saccharoascorbic acid, and their salts.The compounds of the present invention are useful for food additives as antioxidants, an intermediate for the production of dichiral compounds and medicines having antithrombotic activity. ##STR1## wherein Z represents ##STR2## --SR.sub.6 or --OR.sub.7, R.sub.4 and R.sub.5 independently represent hydrogen or a hydrocarbon group of 1 to 24 carbon atoms, or R.sub.4 and R.sub.5 may together form --CH.sub.2 --.sub.n in which n is an integer of 4 to 7, R.sub.6 represents a hydrocarbon group of 1 to 24 carbon atoms, R.sub.7 represents hydrogen or a hydrocarbon group of 1 to 24 carbon atoms, R.sub.1, R.sub.2 and R.sub.3 independently represent hydrogen, an acyl group of 1 to 18 carbon atoms or a hydrocarbon group of 1 to 24 carbon atoms, and .about.Type: GrantFiled: January 31, 1990Date of Patent: August 27, 1991Assignee: Takeda Chemical Industries, Ltd.Inventors: Koichi Matsumura, Yoshihiro Sugihara, Yoshiaki Shimizu, Kouichi Iida, Toshiro Yamashita
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Patent number: 5041563Abstract: A process for the manufacture of ascorbic acid from 2-ketogulonic acid esters (KGAE) utilizing amine salts of the latter is disclosed.Type: GrantFiled: May 22, 1990Date of Patent: August 20, 1991Assignee: Hoffman-La Roche Inc.Inventors: Peter Fahrni, Theodor Siegfried
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Patent number: 5034543Abstract: This invention relates to a novel ascorbic acid derivative having excellent antioxidant action, particularly eliminating action on superoxides and a process for preparing the same. Furthermore, this invention also relates to a novel antioxidant comprising the afore-mentioned novel ascorbic acid derivative or other known ascorbic acid derivatives.Type: GrantFiled: July 20, 1989Date of Patent: July 23, 1991Assignee: Nippon Hypox Laboratories IncorporatedInventors: Toshio Satoh, Yasunori Niiro, Hisao Kakegawa, Hitoshi Matsumoto
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Patent number: 5011949Abstract: This invention relates to a novel ascorbic acid derivative having excellent antioxidant action, particularly eliminating action on superoxides and a process for preparing the same.Furthermore, this invention also relates to a novel antioxidant comprising the aforementioned novel ascorbic acid derivative or other known ascorbic acid derivatives.Type: GrantFiled: July 20, 1989Date of Patent: April 30, 1991Assignee: Nippon Hypox Laboratories, Inc.Inventors: Toshio Satoh, Yasunori Niiro, Hisao Kakegawa, Hitoshi Matsumoto
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Patent number: 5008405Abstract: There is disclosed an improved process for substitution of the hydroxy group at 2-position of an ascorbic acid derivative according to the following reaction scheme: ##STR1## wherein R.sup.0 is hydrogen, alkyl having 1 to 6 carbon atoms, phenyl or a group of the formula ##STR2## (wherein X is two hydrogen atoms, or acetal or ketal residue); R.sup.1 is an alkyl or alkenyl group having up to 22 carbon atoms which may be substituted with phenyl or alkoxy having 1 to 22 carbon atoms; Y is halogen or optionally substituted sulfonyloxy; R is hydrogen, or primary, secondary or tertiary alkyl having 1 to 10 carbon atoms; and Z is an alkali metal or an alkali earth metal. There is also disclosed hydrolysis of the following scheme: ##STR3## wherein R.sup.1 is as defined above; and X is acetal or ketal residue.Type: GrantFiled: January 19, 1990Date of Patent: April 16, 1991Assignee: Takeda Chemical Industries, Ltd.Inventors: Chitoshi Hatanaka, Satoru Oi
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Patent number: 4999437Abstract: Ascorbic acid 2-phosphate is prepared by reacting ascorbic acid or an ascorbic acid derivative with POCl.sub.3 in the presence of a tertiary amine in a suitable aqueous solvent at from -10.degree. to 25.degree. C. while maintaining a pH of about 8-13.5 with KOH during the entire phosphorylation reaction and then isolating the ascorbic acid 2-phosphate, by a process in which an aqueous solution of a magnesium compound is added to the reaction mixture obtained in the phosphorylation, without prior treatment with an ion exchanger, until the formation of crystalline KMg PO.sub.4 is complete, the KMgPO.sub.4 which is crystallized out is separated off, the resulting filtrate is evaporated down at a pH of from 6 to 11 and/or from 0.Type: GrantFiled: March 1, 1990Date of Patent: March 12, 1991Assignee: BASF AktiengesellschaftInventors: Walter Dobler, Joachim Paust, Roland Betz
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Patent number: 4997958Abstract: A process for the manufacture of 6-aliphatic C.sub.2-20 -carboxylic acid esters of ascorbic acid by esterifying the ascorbic acid with an aliphatic C.sub.2-20 -carboxylic acid halide in the presence of a N,N-dialkyl-alkanecarboxylic acid amide, of a cyclic amide of the 1-methyl-2-pyrrolidone type, of a tetraalkylcarbamide such as tetramethylurea, of a cyclic carbamide of the 1,3-dimethyl-2-imidazolidinone type or of a phosphoric acid triamide of the hexamethylphosphoric acid triamide type. The 6-ascorbyl linolate which can be manufactured in this manner is novel and is likewise an object of the present invention. The thus-manufacturable 6-aliphatic C.sub.2-20 -carboxylic acid esters of ascorbic acid are important alternative application forms of L-ascorbic acid (vitamin C).Type: GrantFiled: March 10, 1989Date of Patent: March 5, 1991Assignee: Hoffmann-La Roche Inc.Inventors: Horst Pauling, Christof Wehrli
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Patent number: 4959483Abstract: Novel compounds, D-glucosaccharoascorbic acid and a salt thereof, are disclosed. The compounds, which are prepared by treating 2-keto-D-glucaric acid or an 2,3-O-acetal or ketal thereof with an acid, show excellent antioxidant activities. The agent containing the D-glucosaccharoascorbic acid or a salt thereof prevents effectively deterioration of foodstuffs.Type: GrantFiled: June 28, 1989Date of Patent: September 25, 1990Assignee: Takeda Chemical Industries, Ltd.Inventors: Koichi Matsumura, Hiroshi Kimura, Noritoshi Mise, Hiroshi Miki
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Patent number: 4959362Abstract: An ascorbic acid derivative of the formula: ##STR1## wherein R.sup.1 is organic residue having molecular weight of from 15 to 700, R.sup.2 is hydrogen or hydroxyl, R.sup.3 is hydrogen, acyl, optionally substituted phosphono or sulfo, and R.sup.3 and hydroxyl or R.sup.2 may form acetal residue or ketal residue, and a salt thereof are provided.The compound [I] and salts thereof have antioxidant activity and excellent prophylactic and improving actions on disorders of circulatory functions, and they are usefule as antioxidant agent for food and as agents of prophylaxis and improvement of circulatory functional disorders.Type: GrantFiled: September 19, 1988Date of Patent: September 25, 1990Assignee: Takeda Chemical Industries, Inc.Inventors: Shinji Terao, Minoru Hirata
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Patent number: 4939274Abstract: The present invention relates to a compound of the formula: ##STR1## wherein Y is a chemical bond, oxygen atom, phenyleneoxy, or oxyphenyleneoxy; R.sup.1 is hydrogen or hydrocarbon residue; and R.sup.2 is hydrocarbon residue having two or more carbon atoms, production and use thereof.The compound (I) of the present invention has an antioxidation activity and activities of preventing or improving functional disorders due to biologically active oxygen species, thus being useful as a pharmaceutical agent for prophylaxis and therapy of disorders in the circulatory system.Type: GrantFiled: August 7, 1989Date of Patent: July 3, 1990Assignee: Takeda Chemical Industries, Ltd.Inventors: Shinji Terao, Minoru Hirata
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Patent number: 4876273Abstract: New polyether antibiotic A80577, its acyl ester and alkyl ether derivatives, and salts thereof, are useful antibacterial agents and increase feed-utilization efficiency in animals. Methods of making A80577 by culture of Actinomadura verrucosospora, NRRL 18236, and compositions containing an A80577 compound also are provided.Type: GrantFiled: July 18, 1988Date of Patent: October 24, 1989Assignee: Eli Lilly and CompanyInventors: Robert L. Hamill, Raymond C. Yao
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Patent number: 4874780Abstract: Deuterated aromatic aldehydes of the formula: ##STR1## where Ar is substituted phenyl, and derivatives thereof represented by the formula: ##STR2## where Ar is substituted or unsubstituted phenyl, and X.sub.1 and X.sub.2 are substituted hetero atoms or together with the carbon to which they are attached from a heterocycle. These compounds are useful as anticancer agents.Type: GrantFiled: March 11, 1987Date of Patent: October 17, 1989Assignee: Norsk Hydro a.s.Inventors: Bernt Borretzen, Rolf O. Larsen, Erik O. Pettersen, John M. Dornish, Rolf Oftebro
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Patent number: 4870191Abstract: Ascorbic acid and substituted ascorbic acids can be reacted with a tetraorganosilicate such as a tetraalkylorthosilicate to yield a product which contains silicon. The products are generally solid in nature, and typically they are insoluble without hydrolysis. The products are useful as active agents in the prevention, treatment, or delaying of the onset of calcium-related bone disease such as post-menopausal osteoporosis.Type: GrantFiled: July 22, 1988Date of Patent: September 26, 1989Assignee: Ethyl CorporationInventors: Karl E. Wiegand, Patrick C. Hu
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Patent number: 4851390Abstract: Disclosed is a nutritional agent for cerebrospinal nerves comprising ribonucleic acid, ribonucleotide and/or ribonucleoside. It is effective for the alleviation and recovery of conditions of cerebrospinal degenerative diseases such as epilepsy, Parkinson's disease and an attack of convulsion.Type: GrantFiled: August 15, 1986Date of Patent: July 25, 1989Assignee: Nissan Chemical Industries, Ltd.Inventor: Fukumi Morishige
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Patent number: 4845246Abstract: 6-O-(2-keto-L-gulonoyl)-L-ascorbate substantially free from 2-keto-L-gulonic acid is produced by allowing an acid to act on 2-keto-L-gulonic acid in an inert organic solvent and recovering 6-O-(2-keto-L-gulonoyl)-L-ascorbate from the reaction mixture.6-O-(2-keto-L-gulonoyl)-L-ascorbate is more fat-soluble than L-ascorbic acid and is expected of the use as a prodrug for L-ascorbic acid that can be absorbed from the intestinal tract.Type: GrantFiled: June 10, 1988Date of Patent: July 4, 1989Assignee: Takeda Chemical Industries, Ltd.Inventors: Kunio Takanohashi, Mitsutaka Tanaka, Toru Yamano
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Patent number: 4786725Abstract: There are described platinum-polyhydroxylated amine compounds which exhibit anti-tumor activity in mammalian species. The products are highly soluble in aqueous solutions and they may be administered either orally or in parenteral form.Type: GrantFiled: March 3, 1986Date of Patent: November 22, 1988Assignee: Engelhard CorporationInventors: Alan R. Amundsen, Eric W. Stern
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Patent number: 4780549Abstract: An ascorbic acid derivative of the formula: ##STR1## wherein R.sub.1 is an organic residue having a molecular weight of from 58 to 400 is novel compound and is useful as antioxidant agent for food.Type: GrantFiled: January 28, 1988Date of Patent: October 25, 1988Assignee: Takeda Chemical Industries, Ltd.Inventors: Shinji Terao, Minoru Hirata
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Patent number: 4778902Abstract: A method of purifying L-ascorbic acid which comprises: bringing an acidic aqueous solution of L-ascorbic acid which contains a cationic surfactant into contact with active carbon activated by chemicals.The method is in particular useful for removing a cationic surfactant from a reaction mixture of diacetone-2-keto-L-gulonic acid or 2-keto-L-gulonic acid with a mineral acid in the presence of an inert solvent and a cationic surfactant, to produce L-ascorbic acid.Type: GrantFiled: July 1, 1986Date of Patent: October 18, 1988Assignee: Takeda Chemical Industries, Ltd.Inventors: Yoshitaka Fujiwara, Tetsuji Kaizu, Masami Shinohara
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Patent number: 4767870Abstract: A method of purifying L-ascorbic acid which comprises: subjecting an acidic aqueous solution of L-ascorbic acid which contains salts of an inorganic acid to electrodialysis to remove the salt therefrom.The method is in particular useful for removing salts of an inorganic acid from an aqueous mixture of L-ascorbic acid and the inorganic salt resulting from the production of L-ascorbic acid in which diacetone-2-keto-L-gulonic acid or 2-keto-L-gulonic acid is heated in the presence of an inorganic acid, or an alkyl ester of 2-keto-L-gulonic acid is enolized and lactonized in the presence of a base.Type: GrantFiled: July 1, 1986Date of Patent: August 30, 1988Assignee: Takeda Chemical Industries, Ltd.Inventors: Yoshitaka Fujiwara, Tetsuji Kaizu
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Patent number: 4749790Abstract: H.sub.2 -receptor antagonist ascorbate compounds, derived from the lactone form of 3-ketohexuronic acid of Formula ##STR1## where (X) may be 1, 2 or 3 and (Y) may be 1 or 2, R.sub.1 and R.sub.2 are both hydrogen or R.sub.1 may be hydroxyl, R.sub.2 hydrogen or the O-alkylidene, 5,6-diacyl, 6-acyl derivatives thereof having two to sixteen carbon atoms, or a 6-phosphate, R.sub.3 being an organic base or a salt thereof having one or more basic functional groups, having H.sub.2 -receptor antagonist properties and capable of reacting with nitrous acid, and a process for the preparation of said compounds.Type: GrantFiled: June 18, 1986Date of Patent: June 7, 1988Assignee: Barisintex, S.AInventors: Antonio L. Palomo-Coll, Montserrat Ballester-Rodes, Francisco E. Polamo-Nicolau
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Patent number: 4745199Abstract: Compounds having the general formula: ##STR1## wherein X is an alkylene radical containing from 1 to 3 carbon atoms and Y is a residue of L-ascorbic acid or D-isoascorbic acid, or the corresponding salts thereof. The compound may be prepared by esterifying L-ascorbic acid or D-isoascorbic acid with the appropriate acid under acid conditions.Type: GrantFiled: November 4, 1985Date of Patent: May 17, 1988Assignee: Nestec S.A.Inventor: Thommy Carlson
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Patent number: 4634584Abstract: Stabilized solutions of hydroxylamine or its salts in water or alcohols, containing the lactone of the formula ##STR1## and their preparation.Type: GrantFiled: December 17, 1984Date of Patent: January 6, 1987Assignee: BASF AktiengesellschaftInventors: Otto-Alfred Grosskinsky, Elmar Frommer, Josef Ritz, Erwin Thomas, Franz-Josef Weiss
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Patent number: 4552888Abstract: Ethers of ascorbic and isoascorbic acid and ketals and acetals thereof, angiogenesis inhibitors.Type: GrantFiled: September 28, 1983Date of Patent: November 12, 1985Assignee: Eli Lilly and CompanyInventors: Gary A. Koppel, Russell L. Barton, Jesse R. Bewley, Stephen L. Briggs, Joseph W. Parton
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Patent number: 4502994Abstract: A novel enantiomeric synthesis from ascorbic acid of (3S,4S)-3-amino-4-carbamoyloxymethyl-2-azetidinone-1-sulfate, an intermediate for an antibiotic compound.Type: GrantFiled: December 9, 1982Date of Patent: March 5, 1985Assignee: Hoffmann-La Roche Inc.Inventors: Chung-Chen Wei, Manfred Weigele
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Patent number: 4500465Abstract: There are described platinum-polyhydroxylated amine compounds which exhibit anti-tumor activity in mammalian species. The products are highly soluble in aqueous solutions and they may be administered either orally or in parenteral form.Type: GrantFiled: June 28, 1982Date of Patent: February 19, 1985Assignee: Engelhard CorporationInventors: Alan R. Amundsen, Eric W. Stern
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Patent number: 4491668Abstract: L-ascorbic acid is prepared from sodium 2-keto-L-gulonate by introducing gaseous hydrogen chloride in a molar ratio of about 1.5-2.0 to the sodium-2-keto-L-gulonate into a mixture composed of the sodium 2-keto-L-gulonate, ethanol and acetone at a ratio of 1:0.25-1.00:0.5-2.5 by weight at a temperature of about 25.degree.-75.degree. C. until precipitation of sodium chloride ends, removing the precipitated sodium chloride before L-ascorbic acid begins to crystalize out, maintaining the filtrate or supernatant at a temperature of about 25.degree.-75.degree. C. for a period of 5-100 hours and cooling it to yield crystals of L-ascorbic acid as a final product. A solvent inert to the L-ascorbic acid and 2-keto-L-gulonate may be added to the filtrate or supernatant with a favorable result in obtaining purer intended product.Type: GrantFiled: March 23, 1983Date of Patent: January 1, 1985Assignee: Shionogi & Co., Ltd.Inventors: Kenji Ikawa, Kanji Tokuyama, Masumi Kiyokawa
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Patent number: 4423236Abstract: Novel condensation products between enediol ketolactones such as 5,6-0-isopropylidene ascorbic acid and 2-chloroethyl isocyanates are shown to have potent antitumor activity probably without the release of alkylating agents in vivo. While the structures of the products are not readily elucidated, activity is found to exceed that of BCNU (bis-(2-chloroethyl)-N-nitrosourea) and parallel that of the toxic and highly effective nitrosourea, MeCCNU (1-(4-trans-methylcyclohexyl)-3-(2-chloroethyl)-3-nitrosourea). Preferred compounds are condensation products of ##STR1## wherein R.sub.2 and R.sub.3 are a lower alkyl group containing 1 to 3 carbon atoms or H andhal--CH.sub.2 --CH.sub.2 --N.dbd.C.dbd.O (B)wherein hal is I, Br or Cl.Type: GrantFiled: October 23, 1981Date of Patent: December 27, 1983Assignee: National Foundation for Cancer Research, Inc.Inventor: Andrew J. Welebir