The Bicyclo Ring System Consists Of Two Five-membered Rings Patents (Class 549/311)
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Patent number: 9823563Abstract: To provide an alcohol compound containing fewer impurities at a high yield by conducting the following steps: a hydroboration process in which a reaction mixture is obtained by reacting in a solvent a compound represented by formula (C) and a boron agent selected from a group of diborane and borane complexes; and an oxidation process in which the pH of the reaction mixture is set at 0.5 to 4, which is conducted after treating the reaction mixture with hydrogen peroxide. In the formula, A1 to A6 are each independently a hydrogen atom, methyl group or ethyl group, and X is an oxygen atom, sulfur atom, methylene group or ethylene group.Type: GrantFiled: June 14, 2012Date of Patent: November 21, 2017Assignee: Mitsubishi Chemical CorporationInventors: Satoshi Sakuma, Masashi Serizawa, Atsushi Yasuda, Nobuhisa Yada, Shinichi Maeda
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Publication number: 20130217898Abstract: The present invention relates to a method for manufacturing an ester from a ketone or an aldehyde, which is a reactive substrate, by a Baeyer-Villiger oxidation reaction using hydrogen peroxide, and in this method, as a catalyst, M(BAr4)n, which is a metal borate, is used (M represents an alkali metal or an alkaline earth metal; Ar represents an aryl; and n is the same number as the valence of M). For example, when cyclohexanone was used as the reactive substrate, and Sr[B(3,5-CF3C6H3)4]2 was used as the catalyst, ?-caprolactone was obtained at an isolated yield of 82%.Type: ApplicationFiled: October 11, 2011Publication date: August 22, 2013Applicant: NATIONAL UNIVERSITY CORPORATION NAGOYA UNIVERSITYInventors: Kazuaki Ishihara, Muhammet Uyanik
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Publication number: 20130197077Abstract: A class of bicyclic brominated furanone structures that have reduced toxicity and high activity for inhibiting biofilm formation and quorum sensing by microbes. The molecules have two fused cyclic alkyl groups that provide a structural framework that retain one or more bromine groups on the structure. The bicyclic furanones have reduced toxicity to mammalian cells as compared to other brominated furanones but retain the ability to inhibit biofilm formation in bacterial populations.Type: ApplicationFiled: January 25, 2013Publication date: August 1, 2013Applicant: SYRACUSE UNIVERSITYInventor: Syracuse University
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Publication number: 20120209011Abstract: This invention relates to novel process for the preparation of prostaglandin compounds having formula (K), wherein R is selected from the group consisting of C1-C7 alkyl; C7-C17 aralkyl wherein the aryl group is unsubstituted or substituted with one to three substituents selected from the group consisting of C1-C6 alkyl, halo and CF3; and (CH2)nOR2 wherein n is from 1 to 3 and R2 represents a C6-C10 aryl group which is unsubstituted or substituted with one to three substituents selected from the group consisting of C1-C6 alkyl, halo and CF3; and R1 is selected from OR3 and NHR3 wherein R3 is C1-C6 alkyl, H; and dashed lines represents a double bond or a single bond, is disclosed. Novel intermediates are also disclosed.Type: ApplicationFiled: December 21, 2009Publication date: August 16, 2012Inventors: Chandrashekar Aswathanarayanappa, Pullela Venkata Srinivas, Divya Kangath, Thilak Gregory Soundararajan, Anegondi Sreenivasa Prasad, Suriyan Masinaickenpatty Raghavendran
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Publication number: 20120088160Abstract: The present technology relates to stabilizing additives and electrolytes containing the same for use in electrochemical devices such as lithium ion batteries and capacitors. The stabilizing additives include triazinane triones and bicyclic compounds comprising succinic anhydride, such as compounds of Formulas I and II described herein.Type: ApplicationFiled: October 7, 2010Publication date: April 12, 2012Inventors: Lu Zhang, Zhengcheng Zhang, Khalil Amine
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Publication number: 20120058430Abstract: A positive resist composition including a base component (A) which exhibits changed solubility in an alkali developing solution under the action of acid and an acid-generator component (B) which generates acid upon exposure, wherein the acid-generator component (B) includes an acid generator (B1) containing a compound represented by general formula (b1-1) shown below (wherein Z+ represents an organic cation).Type: ApplicationFiled: September 1, 2011Publication date: March 8, 2012Applicant: Tokyo Ohka Kogyo Co., Ltd.Inventors: Yoshiyuki Utsumi, Takehiro Seshimo
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Publication number: 20110201809Abstract: A process of making entecavir comprising converting a compound of formula (M5) to entecavir, wherein the two PGs on the formula (M5) are taken together to form an optionally substituted six- or seven-member cyclic ring.Type: ApplicationFiled: February 15, 2011Publication date: August 18, 2011Inventors: Tsung-Cheng Hu, Hung-Tsung Huang
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Publication number: 20110092368Abstract: The present invention relates to novel 2,4,6-phenyl-substituted cyclic ketoenols of the formula (I) in which W, X, Y and CKE have the meanings given in the disclosure, to a plurality of processes for their preparation and to their use as pesticides and/or herbicides. The invention further relates to selectively herbicidal compositions containing 2,4,6-phenyl-substituted cyclic ketoenols and a compound which improves crop plant tolerance.Type: ApplicationFiled: December 17, 2010Publication date: April 21, 2011Inventors: Reiner Fischer, Klaus Kunz, Stefan Lehr, Michael Ruther, Udo Schneider, Markus Dollinger, Mark Wilhelm Drewes, Dieter Feucht, Jörg Konze, Ulrike Wachendorff-Neumann, Guido Bojack, Thomas Auler, Martin Jeffrey Hills, Thomas Bretschneider, Olga Malsam, Christoph Erdelen, Angelika Lubos-Erdelen, Alfred Angermann, Hein Kehne, Christopher Hugh Rosinger
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Publication number: 20100041889Abstract: The present invention relates to synthesis procedures and intermediates of a compound of formula: and the salts thereof.Type: ApplicationFiled: February 1, 2008Publication date: February 18, 2010Inventors: Andras Horvath, Dominique Paul Michel Depré, Dominic John Ormerod
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Patent number: 7595408Abstract: The present invention relates to methods for the preparation of diastereomerically pure (3R,3aS,6aR) hexahydro-furo[2,3-b]furan-3-ol as well as a novel intermediate, (3aR,4S,6aS) 4-methoxy-tetrahydro-furo[3,4-b]furan-2-one for use in said methods. More in particular the invention relates to a stereoselective method for the preparation of diastereomerically pure (3R,3aS,6aR) hexahydro-furo[2,3-b]furan-3-ol, as well as methods for the crystallization of (3aR,4S,6aS) 4-methoxy-tetrahydro-furo[3,4-b]furan-2-one and for the epimerization of (3aR,4R,6aS) 4-methoxy-tetrahydro-furo[3,4-b]-furan-2-one to (3aR,4S,6aS) 4-methoxy-tetrahydro-furo[3,4-b]furan-2-one.Type: GrantFiled: March 31, 2005Date of Patent: September 29, 2009Assignee: Tibotec Pharmaceuticals, Ltd.Inventors: Peter Jan Leonard Mario Quaedflieg, Bart Rudolf Romanie Kesteleyn, Robert Jan Vijn, Constantinus Simon Maria Liebregts, Jacob Hermanus Matheus Hero Kooistra, Franciscus Alphons Marie Lommen
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Patent number: 7276089Abstract: Compositions for the oxidative dyeing of keratin fibers, comprising a medium suitable for dyeing and at least one bicyclic fused 5-5-membered aza heteroaromatic keratin dyeing compound with an N-hydroxy or N-amino group and derivatives thereof. A method for oxidative dyeing of keratin fibers, comprising applying such compositions in the presence of an oxidizing agent, for a period sufficient to develop the desired coloration.Type: GrantFiled: August 23, 2005Date of Patent: October 2, 2007Assignee: The Procter & Gamble CompanyInventors: Robert Wayne Glenn, Jr., Mu'Ill Lim
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Patent number: 6784302Abstract: An optically active lactone compound is produced by using a Zr(salen) complex of the following formula (I) or its enantiomer as a catalyst and subjecting a cyclic ketone compound to a Baeyer-Villiger reaction with at least one oxidizer selected from hydrogen peroxide, aqueous hydrogen peroxide and urea-hydrogen peroxide adduct in a solvent: wherein Ar1 is an aryl group having a carbon number of 10 to 16 and Y is a phenoxy group or an alkoxy group having a carbon number of 1 to 10.Type: GrantFiled: April 3, 2003Date of Patent: August 31, 2004Assignee: Kyushu UniversityInventors: Tsutomu Katsuki, Akira Watanabe, Tatsuya Uchida
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Patent number: 6462074Abstract: The present invention relates to novel substituted (&agr;,&bgr;-fused butyrolactones, to processes for their preparation and to their use for the prevention and/or treatment of disorders caused by hyper- or hypofunction of the glutamatergic system, in particular of cerebral ischaemias, craniocerebral trauma, states of pain or CNS-mediated spasms.Type: GrantFiled: July 14, 2000Date of Patent: October 8, 2002Assignee: Bayer AktiengesellschaftInventors: Andreas Stolle, Horst-Peter Antonicek, Stephen Lensky, Arnd Voerste, Thomas Müller, Jörg Baumgarten, Karsten von dem Bruch, Gerhard Müller, Udo Stropp, Ervin Horváth, Jean-Marie-Viktor de Vry, Rudy Schreiber
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Patent number: 6268514Abstract: The use of nitroethane derivatives of the formula I where: R1 is hydrogen, unsubstituted or substituted C1-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, halogen, cyano or thiocyanato; R2 is hydrogen, formyl; halogen- or C1-C3-alkoxy-substituted or unsubstituted C1-C6-alkylcarbonyl, C2-C6-alkenylcarbonyl, C4-C6-alkyldienylcarbonyl or C2-C6-alkynylcarbonyl; A is unsubstituted or substituted phenyl, naphthyl, quinolyl, quinazolyl, quinoxalyl, 1-methylindolyl, 1-methylbenzimidazolyl, 2-methylindazolyl, benzofuranyl, benzothienyl, benzoxazolyl, benzothiazolyl, furyl, thienyl, pyrrolyl, isoxazolyl, isothiazolyl, pyrazolyl, oxazolyl, thiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl or triazinyl, pyranyl or thiopyranyl; as microbicides is described.Type: GrantFiled: June 13, 2000Date of Patent: July 31, 2001Assignee: BASF AktiengesellschaftInventors: Gerhard Hamprecht, John-Bryan Speakman, Gisela Lorenz, Kurt Eger, Mathias Schmidt, Uta Witt
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Patent number: 5912361Abstract: Trehalose is oxidized to give oxidized trehalose which then is hydrolyzed to produce D-glucuronolactone which is thereafter recovered to realize high-yield and low-cost production of D-glucuronolactone.Type: GrantFiled: March 9, 1998Date of Patent: June 15, 1999Assignees: Chugoku Kayaku Kabushiki Kaisha, Hayashibara Biochemical Laboratories, Inc.Inventors: Toshiki Tsuchioka, Tadashi Yamaguchi, Kunihiko Yuuen, Hiroto Chaen
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Patent number: 5840923Abstract: An optically-purified enantiomer of the lactone 4-hydroxy-2-oxabicyclo-?3.3.0!oct-7-en-3-one or an acylate thereof can be obtained by biotransformation. It is a useful synthon in the preparation of an enantiomer of 3-hydroxymethyl-2-hydroxycyclopentene that can be used to prepare carbocyclic nucleosides as a desired enantiomer.Type: GrantFiled: October 21, 1994Date of Patent: November 24, 1998Assignee: Chiroscience LimitedInventors: Stanley Michael Roberts, Horacio F. Olivo, Raymond McCague
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Patent number: 5717098Abstract: A process for the preparation of a .gamma.-lactone of the formula ##STR1## which can be used to produce a single enantiomer of aminoazanoradamantane which is coupled to aromatic acid moieties to produce compounds useful as 5-HT agonists or antagonists.Type: GrantFiled: July 22, 1996Date of Patent: February 10, 1998Assignee: G. D. Searle & Co.Inventors: Daniel Paul Becker, Daniel Lee Flynn, Alan Edward Moormann, Clara Ines Villamil
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Patent number: 5541344Abstract: The present invention is directed to intermediates of the formula ##STR1## which are useful in a process for the preparation of aminoazanoradamanatanes.Type: GrantFiled: May 19, 1995Date of Patent: July 30, 1996Assignee: G. D. Searle & Co.Inventors: Daniel P. Becker, Daniel L. Flynn, Alan E. Moormann, Clara I. Villamil
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Patent number: 5538995Abstract: A difluoroprostacyclin of the following formula (V), its lower alkanol ester or its pharmaceutically acceptable salt: ##STR1## wherein A is an ethylene group, a vinylene group or an ethynylene group, R is a substituted or unsubstituted C.sub.1-10 alkyl group, a substituted or unsubstituted C.sub.1-10 alkenyl group, a substituted or unsubstituted C.sub.1-10 alkynyl group, a substituted or unsubstituted C.sub.3-8 cycloalkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryloxy group, Q is a substituted or unsubstituted C.sub.1-10 alkyl group, a substituted or unsubstituted C.sub.1-10 alkenyl group, a substituted or unsubstituted C.sub.1-10 alkynyl group, a substituted or unsubstituted C.sub.3-8 cycloalkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryl group.Type: GrantFiled: February 17, 1995Date of Patent: July 23, 1996Assignee: Asahi Glass Company Ltd.Inventors: Yasushi Matsumura, Takashi Nakano, Mayumi Makino, Yoshitomi Morizawa
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Patent number: 5442079Abstract: There are described improved processes for the synthesis of a desired lactone useful as a synthon, the improved processes comprising oxidizing a protected arene diol with permanganate and periodate or subjecting a substituted epoxydiol to periodate oxidation to yield the desired lactone.Type: GrantFiled: May 10, 1993Date of Patent: August 15, 1995Assignee: Virginia Polytechnic Institute and State UniversityInventors: Tomas Hudlicky, Martin Mandel
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Patent number: 5374745Abstract: The invention relates to a process for the production of prostaglandin precursors of formula I ##STR1## as well as their enantiomers in which X is A--W or W--A,A is a --C.tbd.C-- group,W is a hydroxymethylene group, in which the OH group can be functionally modified by etherification or esterification,D is a straight-chain or branched-chain alkylene group with 2-5 C atoms each or a ##STR2## group, n i s 1 to 3,E is a --C.tbd.C-- group or a --CR.sub.3 .dbd.CR.sub.4 group with R.sub.3 and R.sub.4 each meaning a hydrogen atom or a C.sub.1 -C.sub.4 alkyl group,R.sub.1 is a hydrogen atom or a hydroxy group, which can be functionally modified as in W,R.sub.2 is a straight-chain or branched-chain alkyl group with 1-7 C atoms, characterized in that vinyl bromides of formula II ##STR3## in which Z means the group ##STR4## and R.sub.1, W, D, E and R.sub.2 have the above-indicated meanings and hydroxy groups unprotected in R.sub.1 and W or represented by an optionally substituted benzoyl radical, a C.sub.1 -C.sub.Type: GrantFiled: September 29, 1992Date of Patent: December 20, 1994Assignee: Schering AktiengesellschaftInventor: Ulrich Klar
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Patent number: 5274097Abstract: Novel 1,3-disubstituted pyrrolidines active on the central nervous system of the formula ##STR1## wherein A--denotes phenyl or hetaryl, which is optionally fused with aromatic, saturated or unsaturated cyclic or heterocyclic hydrocarbons, where this radical can optionally be substituted,X--denotes --O--CH.sub.2 --, --CH.sub.2 --O-- or --O--,n--denotes a number from 1 to 19, andB--denotes cyano or a group of the formula --COOR.sup.1, --CONR.sup.2 R.sup.3, --SO.sub.2 NR.sup.2 R.sup.3, --SO.sub.m R.sup.4, --NR.sup.5 R.sup.6, or --C.tbd.C--CH.sub.2 --NR.sup.5 R.sup.6,and salts thereof.Type: GrantFiled: April 9, 1991Date of Patent: December 28, 1993Assignee: Bayer AktiengesellschaftInventors: Rudolf Schohe, Peter-Rudolf Seidel, Jorg Traber, Thomas Glaser
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Patent number: 5219743Abstract: The primary hydroxy group of Corey lactone diols is optically selectively acylated to obtain the desired optically active ester and/or diol. The mixture of Corey lactone diols of formulae (Ia) and (Ib): ##STR1## is reacted with an acylating agent optically selectively in the presence of an enzyme and/or a microorganism thereby to acylate, isolate and purify the primary alcohol.Type: GrantFiled: February 18, 1992Date of Patent: June 15, 1993Assignee: Nissan Chemical Industries, Ltd.Inventors: Seiichi Takano, Tsutomu Sugahara
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Patent number: 4973713Abstract: A process for the production of esters or lactones, comprising reacting in the presence of a catalyst and under hydrogenation conditions hydrogen and an acyclic or cyclic carboxylic anhydride to produce the corresponding ester or lactone, wherein the catalyst is a supported catalyst comprising:(a) a group VIII metal, Re and Fe;(b) a group VIII metal on TiO.sub.2 ;(c) Ru and at least one of Re, Ag or Cu; or(d) Pd and Fe.Preferably, the anhydride has the formula ##STR1## and is reacted to form an ester of the formula ##STR2## or a lactone of the formula ##STR3## wherein R and R.sup.1 independently are lower alkyl or cycloalkyl; R.sup.2, R.sup.3, R.sup.4, R.sup.5 independently are hydrogen, lower alkyl, cycloalkyl or aryl; and wherein R.sup.3 and R.sup.4 taken together may form a saturated or unsaturated ring, or an aromatic ring. The more preferred starting material is phthalic anhydride.Type: GrantFiled: November 28, 1989Date of Patent: November 27, 1990Assignee: E. I. du Pont de Nemours and CompanyInventor: William H. Manogue
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Patent number: 4808734Abstract: 16-Cycloalkyl-7-fluoro prostacyclins having a 16 lower alkyl or fluoro substituent useful as blood platelet anti-aggregating agent, vasodilators, cyto protective lowering agents, anti-ulcerogenic agent and for treating peripheral vascular diseases such as schleroderma.Type: GrantFiled: December 1, 1986Date of Patent: February 28, 1989Assignee: Hoffmann-La Roche Inc.Inventors: George W. Holland, Perry Rosen, Hans Maag, Ferdinand Lee
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Patent number: 4772728Abstract: A method for making a bicyclic lactone comprising heating under aqueous acidic conditions a beta, gamma unsaturated cyclic nitrile and an aldehyde, for a length of time sufficient to convert at least a portion of the reactants to a bicyclic lactone of the formula ##STR1## wherein R.sub.3 is --H; R.sub.4, R.sub.5, and R.sub.6 are independently selected from the group consisting of --H, --CH.sub.3 ; R.sub.2 is selected from the group consisting of --H, --CH.sub.3, and --CH.sub.3, and --C.sub.2 H.sub.5 ; R.sub.8 is --H or --CH.sub.3 ; m is an integer from 1 to 5; o is 0, 1, 2, or 3; and p is 0, 1, or 2; provided that the sum of m+o+p is an integer from 3 to 5; either R.sub.3 or R.sub.8 together with R.sub.7 represents a carbon-carbon bond. The method uses commercially available and relatively inexpensive raw materials as reactants.Type: GrantFiled: August 19, 1985Date of Patent: September 20, 1988Assignee: Angus Chemical CompanyInventors: Stephan Korte, Craig W. Coulston, Friedhelm Korte
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Patent number: 4707555Abstract: New optically active intermediates and processes thereto are provided for use in synthesizing therapeutically active prostaglandins of the formula: ##STR1## wherein R.sup.1 is hydrogen or lower alkyl; from a compound of the formula: ##STR2## wherein R.sup.1 is as above and R.sup.2 is hydrogen or a carboxy blocking group convertible to an acid by hydrolysis.Type: GrantFiled: July 12, 1985Date of Patent: November 17, 1987Assignee: Hoffmann-La Roche Inc.Inventors: David L. Coffen, George W. Holland, W. Harry Mandeville, Perry Rosen, Frederick Wong
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Patent number: 4672132Abstract: A process for producing 3-oxo-6-formyl-2-oxabicyclo[3.3.0]-6-octene useful as an intermediate for producing prostaglandins, via a few steps from raw materials which can be relatively easily prepared. The process comprises subjecting 2,2-dimethyl-1,3-dioxin-4-one and cis-2-cyclopenten-1,4-diol to addition reaction in a solvent, preferably under a photo-irradiation, removing the solvent from the reaction mixture, adding water to the resulting adducts and reacting the resulting mixture on heating.Type: GrantFiled: February 28, 1986Date of Patent: June 9, 1987Assignee: Chisso CorporationInventors: Chikara Kaneko, Masayuki Sato
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Patent number: 4661286Abstract: This invention is directed to oxaspirododecane derivatives, the preparation thereof, and perfume compositions containing same.Type: GrantFiled: March 24, 1986Date of Patent: April 28, 1987Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Ulf A. Schaper, Siegfried Bloesl, Klaus Bruns
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Patent number: 4558140Abstract: New optically active intermediates and processes thereto are provided for use in synthesizing therapeutically active prostaglandins of the formula: ##STR1## wherein R.sup.1 is hydrogen or lower alkyl; from a compound of the formula: ##STR2## wherein R.sup.1 is as above and R.sup.2 is hydrogen or a carboxy blocking group convertible to an acid by hydrolysis.Type: GrantFiled: March 6, 1984Date of Patent: December 10, 1985Assignee: Hoffmann-La Roche Inc.Inventors: David L. Coffen, George W. Holland, Perry Rosen, Frederick Wong
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Patent number: 4485245Abstract: Process for selective homogeneous catalytic hydrogenation of carboxylic acid anhydrides to ester or lactones at an improved rate and to obtain improved yields wherein the catalyst is a ruthenium trichlorostannate complex of the formula: ##STR1## wherein X is hydrogen, chlorine, bromine, iodine or lower alkyl; m is the integer 1 or 2; n is an integer of from 0 to 3 but when n is 2 or 3, X may be the same or different; M is P, As or Sb; R.sup.6, R.sup.7 and R.sup.8 independently are lower alkyl, cycloalkyl, aryl, benzyl or a bidentate legand; x is an integer of from 1 to 4 but when x is 2 or more, M may be the same or different; L is a neutral ligand, olefin, CO or (R.sup.9).sub.2 CO wherein R.sup.9 is lower alkyl; y is an integer of from 0 to 3 but when y is 2 or 3, L may be the same or different; and the sum of x and y is at least 2.Type: GrantFiled: October 29, 1982Date of Patent: November 27, 1984Assignee: Sun Tech, Inc.Inventors: Chao-Yang Hsu, James E. Lyons
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Patent number: 4485246Abstract: The rate of selective hydrogenation of carboxylic acid anhydrides to esters or lactones in the presence of a ruthenium organophosphorous catalyst which contains or liberates a hydrogen halide during the hydrogenation, is improved by providing in the reaction medium prior to or during the hydrogenation a basic amino compound to remove the hydrogen halide.Type: GrantFiled: October 29, 1982Date of Patent: November 27, 1984Assignee: Sun Tech, Inc.Inventor: James E. Lyons
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Patent number: 4463183Abstract: A method is provided for preparing compounds of the formulae ##STR1## wherein A may be --C.dbd.C-- or --C.tbd.C--, by reducing an epoxy lactone of the structure ##STR2## to form the corresponding epoxy hemiacetal, reacting the epoxy hemiacetal with a silyl compound to form an epoxy silyl acetal, reacting the epoxy silyl acetal with an acetylenic derivative to form a silyl acetal, removing the silyl protecting group to form a hemiacetal, reacting the hemiacetal compound with an appropriate Wittig reagent to form a protected difluoro PGF.sub.2.alpha. type compound, removing the protecting group, reacting the difluoro PGF.sub.2.alpha. with an iodine compound to form an iodoether and reacting the iodoether with a base to form the desired compounds.Novel intermediates produced in the above method are also provided.Type: GrantFiled: April 25, 1983Date of Patent: July 31, 1984Assignee: E. R. Squibb & Sons, Inc.Inventor: Martin F. Haslanger