At Least Two Additional Chalcogens Bonded Directly To The Lactone Ring Patents (Class 549/314)
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Patent number: 11208392Abstract: Provided herein is a process for preparing D-glucaro-6,3-lactone monoamide from D-glucaro-6,3-lactone.Type: GrantFiled: September 28, 2018Date of Patent: December 28, 2021Assignee: BASF SEInventors: Dominik Ohlmann, Boris Tissberger, Thomas Bodenstein
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Publication number: 20150126752Abstract: Disclosed is a process to prepare a ribonolactone compound of Formula (I): comprising the step of reacting a fructosamine compound of Formula (II): in the presence of a calcium salt and a base in a nonaqueous reaction medium, to provide said ribonolactone compound of Formula (I).Type: ApplicationFiled: June 12, 2013Publication date: May 7, 2015Inventors: Sarah Evelyn Steinhardt, Martin D. Eastgate
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Publication number: 20130274479Abstract: The invention relates to a process for the aminohydroxylation of alkenes using N-oxycarbamate reagents, e.g. N-acyloxycarbamate, N-alkyloxycarbonyloxycarbamate and N-aralkoxycarbonyloxycarbamate reagents. The invention particularly relates to an intermolecular aminohydroxylation reaction that can be carried out in the absence of added base. The invention also relates to novel N-oxycarbamate reagents that are stable crystalline materials. The process of the invention is useful in the synthesis of compounds having a vicinal amino alcohol moiety, such as biologically active compounds.Type: ApplicationFiled: June 20, 2011Publication date: October 17, 2013Applicant: INDUSTRIAL RESEARCH LIMITEDInventors: Simon Peter Harold Mee, Andreas Luxenburger, Lawrence Daniel Harris
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Publication number: 20130122110Abstract: What is disclosed in the invention is a preparation method of a supercritical Cinnamomum subavenium extract, which is made from the material, the dried stem of C. subavenium. The extract is obtained by extracting C. subavenium which is pulverized as particles with supercritical carbon dioxide fluid. The C. subavenium extract or its active ingredient, subamolide A, can be used to inhibit the growth of human urothelial carcinoma cell lines. In addition, the C. subavenium extract (or subamolide A) is able to synergistically inhibit the growth of human urothelial carcinoma cell lines with cisplatin (CDDP) or gemcitabine (Gem). Therefore, the C. subavenium extract (or subamolide A) can be an anticancer drug alone, or forms a pharmaceutical composition with CDDP (or Gem) to treat with cancers in respect of urinary system.Type: ApplicationFiled: March 21, 2012Publication date: May 16, 2013Applicant: KAOHSIUNG MEDICAL UNIVERSITYInventors: JIH-HENG LI, A-MEI HUANG, CHUNG-YI CHEN, PEI-JUNG LIEN, CHIUNG-HUI LIU
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Patent number: 8404743Abstract: Disclosed are compounds comprising a zinc oxide molecule chemically bound to one or more molecules having an acidic hydrogen, such as an organic acid. The invention also provides compositions comprising such compounds and methods of preparing such compounds. The compounds of the invention may be provided in, for example, topical skin formulations, pharmaceutical compositions, or delivery systems for active ingredients.Type: GrantFiled: October 31, 2011Date of Patent: March 26, 2013Assignee: Mary Kay Inc.Inventor: James Swanzy
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Publication number: 20110275838Abstract: The present invention relates to a process for obtaining cinatrins C1 and C3 and derivatives thereof which comprises the hydroxylation of a compound of formula (III).Type: ApplicationFiled: May 5, 2009Publication date: November 10, 2011Applicant: CONSEJO SUPERIOR DE INVESTIGACIONES CIENTIFICASInventors: Pedro Noheda Marin, Luis Miguel Lozano Gordillo, Sergio Maroto Quintana
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Patent number: 7601820Abstract: The present invention provides (i) a process for preparing a 2-deoxy-2-fluoro-2-methyl-D-ribonolactone derivative, (ii) conversion of the lactone to nucleosides with potent anti-HCV activity, and their analogues, and (iii) a method to prepare the anti-HCV nucleosides containing the 2-deoxy-2-fluoro-2-C-methyl-?-D-ribofuranosyl nucleosides from a preformed, preferably naturally-occurring, nucleoside.Type: GrantFiled: February 13, 2006Date of Patent: October 13, 2009Assignee: Pharmasset, Inc.Inventors: Peiyuan Wang, Wojciech Stec, Byoung-Kwon Chun, Junxing Shi, Jinfa Du
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Publication number: 20090093459Abstract: The present invention relates to 2-alkoxy-3,4,5-trihydroxyalkylamide benzothiazepine compounds, to pharmaceutical compositions comprising such compounds, to methods of treatment comprising administering such compounds, to processes for the preparation of such compounds and to intermediate precursors to such compounds.Type: ApplicationFiled: November 10, 2008Publication date: April 9, 2009Applicant: SANOFI-AVENTISInventors: Jidong ZHANG, Yannick BENEDETTI, Frederico NARDI, Alain COMMERCON
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Publication number: 20090075971Abstract: The present invention relates to 2-alkoxy-3,4,5-trihydroxyalkylamide derivatives, to pharmaceutical compositions comprising such compounds, to methods of treatment comprising administering such compounds, to processes for the preparation of such compounds, and to intermediate precursors to such compounds.Type: ApplicationFiled: November 10, 2008Publication date: March 19, 2009Applicant: SANOFI-AVENTISInventors: Jidong Zhang, Yannick Benedetti, Alain Commercon
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Patent number: 6891036Abstract: The present invention relates to a new process in 3 steps starting from 2-C-methyl-D-ribopentono-1,4-lactone for the preparation of tetra-acyl ribofuranose derivatives of formula (I): useful in the synthesis of nucleotides.Type: GrantFiled: May 27, 2003Date of Patent: May 10, 2005Assignee: Inalco S.p.A.Inventors: Giancarlo Tamerlani, Liana Salsini, Ilaria Lombardi, Debora Bartalucci, Giovanni Cipolletti
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Publication number: 20030088110Abstract: The present invention relates to a novel chiral compound of Hibiscus acid bearing lactone moiety of formula I, 1Type: ApplicationFiled: September 5, 2001Publication date: May 8, 2003Inventors: Ibrahim Ibnu Saud, Chitra Gopinath, Beena Thomas
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Patent number: 6492534Abstract: Processes for the preparation of pyrrolidones (7 and 8) and pyrrolidines (9 and 10) from tri-O-acetyl-D-erythro-4-pentulosonic acid esters are described. The compounds are aza sugar analogs of D-ribofuranoside and are intermediates to drugs which regulate nucleoside and nucleic acid synthesis.Type: GrantFiled: September 4, 2001Date of Patent: December 10, 2002Assignee: Board of Trustees of Michigan State UniversityInventor: Rawle I. Hollingsworth
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Patent number: 6335464Abstract: A method for selectively oxidizing the primary hydroxyl group of an organic compound which comprises reacting a resin having an amine oxide adsorbed thereon and an electrolytically oxidized product of a halogen-containing compound with the organic compound having the primary hydroxyl group.Type: GrantFiled: March 8, 2000Date of Patent: January 1, 2002Assignee: Chugai Seiyaku Kabushiki KaishaInventors: Kiyoshige Ochi, Hidenori Takahashi, Hideki Tanaka, Hiroshi Sugiyama, Isao Fujisaki, Kazutomo Ori
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Patent number: 6251937Abstract: The invention relates to cleavable surfactants of formula: in which R′ and R, which may be identical or different, represent a hydrogen atom or a linear or branched, saturated or unsaturated alkyl radical, the sum of the carbon atoms of R′ and R being between 5 and 42. The invention also relates to the corresponding derivatives obtained by alkaline hydrolysis or amidation. The invention furthermore relates to the preparation of these surfactants from glucono-1(5)-lactone and a compound of formula R—CO—R′ in the presence of an acid catalyst, R and R′ having the meaning given above. The surfactants are used in particular in emulsion polymerization and in the field of cosmetics.Type: GrantFiled: April 13, 1998Date of Patent: June 26, 2001Assignee: CECA S.A.Inventors: Serge Petit, Stephane Fouquay
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Patent number: 6013244Abstract: Compounds of the pregnane series are described having general formula (I) or their solvates in which R.sub.1 individually represents --OC(.dbd.O)C.sub.1-6 alkyl; R.sub.2 individually represents hydrogen, methyl (which may be in the .alpha. or .beta. configuration) or methylene; or R.sub.1 and R.sub.2 together represent formula (a) where R.sub.5 and R.sub.6 are the same or different and each represents hydrogen or C.sub.1-6 alkyl; R.sub.3 and R.sub.4 are the same or different and each represents hydrogen or halogen; and represents a single or a double bond. Compounds of formula (I) and their solvates are useful as anti-inflammatory or anti-allergic agents.Type: GrantFiled: June 24, 1998Date of Patent: January 11, 2000Assignee: Glaxo Wellcome Inc.Inventors: Keith Biggadike, Rosanne Mary Farrell
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Patent number: 5945547Abstract: The compound 2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate is described and claimed.Type: GrantFiled: March 19, 1997Date of Patent: August 31, 1999Assignee: Eli Lilly and CompanyInventors: Ta-Sen Chou, Perry C. Heath
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Patent number: 5679801Abstract: There are disclosed compounds of the formula: ##STR1## wherein X is --CH.sub.2 R;Y is --O-- or --S--;R.sup.1 and R.sup.2 are each, independently, hydrogen or lower alkyl;or a pharmaceutically acceptable salt thereof;which by virtue of their ability to inhibit PLA.sub.2, are of use as antiinflammatory agents and there is also disclosed a method for the treatment of immunoinflammatory conditions, such as allergy, anaphylaxis, asthma and inflammation in mammals.Type: GrantFiled: May 15, 1995Date of Patent: October 21, 1997Assignee: American Home Products CorporationInventors: Craig E. Caufield, James M. Rinker
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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: 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: 5374744Abstract: An alkynyl group having a triple bond at the carbon atom at the 1-position is introduced to a carbon atom at the 1-position of 2,3-O-isopropylidene-D-ribofuranose. The diol part is then cleaved to obtain a lactol compound. This lactol compound is oxidized to obtain a lactone compound. The ketal part of the lactone compound is hydrolyzed and the compound is further subjected to a reduction reaction. The hydroxyl groups at the 2- and 3-positions are then eliminated, and the double bond between the 2- and 3-positions of the resultant compound is reduced to obtain a 4-substituted-.gamma.-lactone.Type: GrantFiled: October 21, 1992Date of Patent: December 20, 1994Assignees: Japan Tobacco Inc., Fuji Flavor Co., Ltd.Inventors: Koshi Koseki, Hiroshi Kawakami, Takashi Ebata, Hajime Matsushita, Mikio Ono
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Patent number: 5312967Abstract: A single step process for converting aldaric acid salts to activated aldarates utilizing a lower alkanol as both solvent and esterifying agent is described. The activated aldarates are particularly useful as monomers for polymerizations with primary diamines in which the nitrogen atoms are bound to aliphatic carbon atoms to form poly(aldaramides).Type: GrantFiled: August 12, 1992Date of Patent: May 17, 1994Assignee: UAB Research FoundationInventors: Donald E. Kiely, Liang Chen, David W. Morton
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Patent number: 5296615Abstract: Chiral epoxybutyrates are prepared in high yield from novel dihydro-3R-substituted sulfonyloxy-4R-hydroxy-2-(3H)furanones via based catalyzed alcoholysis. The product chiral epoxy butyrates are useful intermediates for the synthesis of 1-carba-1-dethia cephem antibiotics.Type: GrantFiled: February 1, 1993Date of Patent: March 22, 1994Assignee: Eli Lilly and CompanyInventor: Leland O. Weigel
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Patent number: 5242945Abstract: There are disclosed compounds of the formula: ##STR1## wherein X is --CH.sub.2 R;R is ##STR2## and further when Y=S, R may also be --(CH.sub.2).sub.e CH.sub.3 ; Y is --O--or --S--;R.sup.1 and R.sup.2 are each, independently, hydrogen or lower alkyl;R.sup.3 is indolyl, furyl, phenyl or phenyl optionally mono- or disubstituted independently by alkyl of 1-7 carbon atoms, --C(CH.sub.3).sub.3, --C(CH.sub.3).sub.2 CH.sub.2 C(CH.sub.3).sub.3, --C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3, haloloweralkyl, perfluoroalkyl, lower alkoxy, aryl alkoxy, halo or nitro;R.sup.4 and R.sup.5 are, independently, --COCH.sub.2 R.sup.7, --CO.sub.2 R.sup.7, --CONHR.sup.7, geranyl or CH.sub.2 R.sup.3 ;R.sup.6 is hydrogen or lower alkyl;R.sup.7 is geranyl and any moiety selected from R other than ##STR3## A and B are, independently, --O--, --S-- or --NR.sup.6 --; and a is 0-8;b is 1-10 when Y=S, and 2-10 when Y=O;c is 1-3;d is 0-9; ande is 3-18;which by virtue of their ability to inhibit PLA.sub.Type: GrantFiled: April 12, 1991Date of Patent: September 7, 1993Assignee: American Home Products CorporationInventors: Craig E. Caufield, James M. Rinker
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Patent number: 5177220Abstract: Asymmetric hydrogenation of .alpha.-ketocarbonyl compounds, especially .alpha.-ketolactones, to the corresponding, optically active .alpha.-hydroxycarbonyl compounds in the presence of iridium diphosphine complexes as catalyst and dicarboxylic acid imides as co-catalyst.Type: GrantFiled: January 9, 1991Date of Patent: January 5, 1993Assignee: Degussa AktiengesellschaftInventors: Adolf Schafer, Dietrich Arntz
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Patent number: 5099034Abstract: A compound of the formula (I): ##STR1## wherein R.sup.1, R.sup.2, and R.sup.3 are --COOR.sup.4, --COOR.sup.5, and --COOR.sup.6, respectively; R.sup.4, R.sup.5, and R.sup.6 each is hydrogen, lower alkyl, or alkali metal; W is hydroxyl; X, Y, and Z each is hydrogen or hydroxyl; a dotted line indicates the presence or absence of a single bond; or where W/R.sup.3, X/R.sup.1, and/or Z/R.sup.3 may be combined together, a lactone is formed, which compound is useful as a phospholipase A.sub.2 inhibitor. Process for the production of the compound (I) and a cell culture of a microorganism Circinotrichum falcatisporum RF-641 producing the same are also provided.Type: GrantFiled: June 27, 1990Date of Patent: March 24, 1992Assignee: Shionogi & Co., Ltd.Inventors: Tadashi Yoshida, Hiroshi Itazaki, Hitoshi Arita, Yoshimi Kawamura, Koichi Matsumoto
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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: 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: 4855446Abstract: Racemic carboxylic acids are resolved into their enantiomers using optically active enantiomers of four lactones as resolving agents. The four lactones are 2,3-isopropylidene-ribonic acid-1,4-lactone, 1,2-isopropylidene-glucofuranurono-3,6-lactone, 2-hydroxy-3,3-dimethyl-1,4-butyrolactone and 3,4-isopropylidene-arabino-1,5-lactone. Novel diastereoisomeric esters of the acids with the lactones are disclosed.Type: GrantFiled: December 17, 1984Date of Patent: August 8, 1989Assignee: The Sherwin Williams CompanyInventors: Colin C. Duke, Robert J. Wells
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Patent number: 4822897Abstract: Polyfluoro .gamma.-ketoester compounds are obtained by reaction of ethylenic monoolefins, a metal or quaternary ammonium cyanide, and a fluoroester. These compounds, which have a general formula R.sub.F C(O)CFYCF.sub.2 CO.sub.2 R.sup.1, can be copolymerized directly with fluorinated ethylenic monoolefins, or further reacted to form vinyl ether and allyl ether derivatives which may also be copolymerized with ethylenic comonomers, forming solid, moldable copolymers with useful properties determined by the nature of pendant functional groups R.sub.F.Type: GrantFiled: June 3, 1987Date of Patent: April 18, 1989Assignee: E. I. Du Pont de Nemours and CompanyInventor: Carl G. Krespan
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Patent number: 4501908Abstract: Racemic carboxylic acids are resolved into their enantiomers using optically active enantiomers of four lactones as resolving agents. The four lactones are 2,3-isopropylidene-ribonic acid-1,4-lactone, 1,2-isopropylideneglucofuranurono-3,6-lactone, 2-hydroxy-3,3-dimethyl-1,4-butyrolactone and 3,4-isopropylidene-arabino-1,5-lactone. Novel diastereoisomeric esters of the acids with the lactones are disclosed.Type: GrantFiled: March 1, 1982Date of Patent: February 26, 1985Assignee: Hoffmann-La Roche Inc.Inventors: Colin C. Duke, Robert J. Wells
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Patent number: 4337202Abstract: L-gulono gamma lactone is made in a one-step process by the simultaneous hydrolysis and catalytic reduction with hydrogen in acid medium of polyglucuronic acid or a lower alkyl glucuronoside. A use statement--L gulono gamma lactone can be converted chemically or biologically to L-ascorbic acid (vitamin C).Type: GrantFiled: April 16, 1981Date of Patent: June 29, 1982Assignee: Boise Cascade CorporationInventors: William M. Hearon, John F. Witte
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Patent number: 4331605Abstract: Novel sulfonic acid esters containing a lactonic ring comprising compounds in the trans form in the 4- and 5-positions having (4SR, 5RS), (4S, 5R) or (4R, 5S) configuration of the formula ##STR1## wherein Z is selected from the group consisting of alkyl of 1 to 4 carbon atoms and monocyclic aryl optionally substituted with at least one member of the group consisting of alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, halogen and nitro and R is organic residue of an optionally chiral alcohol of the formula ROH and a process for their preparation and a process using the compounds of formula I to prepare compounds of (1RS, 4RS, 5SR), (1S, 4S, 5R) or (1R, 4R, 5S) configuration of the formula ##STR2## wherein X is selected from the group consisting of hydrogen and R. The compounds of V are useful for the preparation of cyclopropane carboxylic acids whose esters are known to be very active insecticides.Type: GrantFiled: July 29, 1980Date of Patent: May 25, 1982Assignee: Roussel UclafInventors: Jacques Martel, Jean Tessier, Jean-Pierre Demoute