Oxirane Ring Formed Patents (Class 549/518)
  • Publication number: 20020095061
    Abstract: The present invention provides a method for enantioselectively producing a nonracemic 6,7-dihydroxy geranyloxy compound from a geranyloxy compound. In particular, methods of the present invention involve enantioselectively epoxidizing the geranyloxy compound and hydrolyzing the epoxide moiety under conditions sufficient to produce the nonracemic 6,7-dihydroxy geranyloxy compound.
    Type: Application
    Filed: December 20, 2001
    Publication date: July 18, 2002
    Applicant: DSM CATALYTICA PHARMACEUTICALS, INC.
    Inventors: Robert Seemayer, Yian Shi
  • Patent number: 6407150
    Abstract: A process for producing phenol resin having good color tone, which process comprises reacting hydroxyl group-containing aromatic compound and unsaturated cyclic hydrocarbon under the condition that the moisture is 100 ppm or less and the concentration of Friedel-Crafts catalyst is 0.07 mass % or less in a reaction system and a process for producing epoxy resin having good color tone, which process comprises reacting the obtained phenol resin and epihalohydrin in the presence of base catalyst, removing remaining catalyst and further removing unreacted epihalohydrin.
    Type: Grant
    Filed: August 10, 2000
    Date of Patent: June 18, 2002
    Assignee: Nippon Petrochemicals Company, Limited
    Inventors: Satoshi Mori, Fumiaki Oshimi, Masato Hattori
  • Publication number: 20020058825
    Abstract: Highly pure optically active threo-3-amino-1,2-epoxy compounds appropriate for materials for manufacturing drugs and a process for producing the same on an industrial scale. An optically active threo-3-amino-1,2-diol derivative is subjected in an organic solvent in the presence of a base to alkylsufonylation or arylsulfonylation to thereby give the corresponding optically active threo-3-amino-2-hydroxy-1-sulfonyloxy compound. Next, the resultant product is subjected to epoxidation in the presence of a base to give the corresponding optically active threo-3-amino-1,2-epoxy compound. The thus obtained epoxy compound is purified by using an organic solvent and water, thus giving a highly pure epoxy compound.
    Type: Application
    Filed: November 30, 2001
    Publication date: May 16, 2002
    Inventors: Yukihiro Sagawa, Jouji Sekine, Hisao Sato
  • Patent number: 6376685
    Abstract: Highly pure optically active threo-3-amino-1,2-epoxy compounds appropriate for materials for manufacturing drugs and a process for producing the same on an industrial scale. An optically active threo-3-amino-1,2-diol derivative is subjected in an organic solvent in the presence of a base to alkylsufonylation or arylsulfonylation to thereby give the corresponding optically active threo-3-amino-2-hydroxy-1-sulfonyloxy compound. Next, the resultant product is subjected to epoxidation in the presence of a base to give the corresponding optically active threo-3-amino-1,2-epoxy compound. The thus obtained epoxy compound is purified by using an organic solvent and water, thus giving a highly pure epoxy compound.
    Type: Grant
    Filed: July 12, 2000
    Date of Patent: April 23, 2002
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Yukihiro Sagawa, Jouji Sekine, Hisao Sato
  • Patent number: 6353122
    Abstract: The present invention provides a process for the expoxidation of a protected 3-methylene-(trans)-1,2,-hydroxymethylcyclopropane with cyclohexanone and potassium peroxymonosulfate and subsequent rearrangement to provide the corresponding cyclobutanone.
    Type: Grant
    Filed: February 4, 1998
    Date of Patent: March 5, 2002
    Assignee: Bristol-Myers Squibb Company
    Inventors: Paul R. Brodfuehrer, Thomas R. Sattleberg, Sr.
  • Patent number: 6313060
    Abstract: A resilient polyurethane foam produced by using a polyether polyol produced by reacting alkylene oxides with a polyhydroxy compound having at least 2 hydroxyl groups as an initiator in the presence of the catalyst for alkylene oxide ring-opening polymerization of the present invention, which is excellent in foam physical properties, vibration characteristics and molding properties.
    Type: Grant
    Filed: March 8, 2000
    Date of Patent: November 6, 2001
    Assignee: Asahi Glass Company, Limited
    Inventors: Kayoko Sugiyama, Hiroki Fukuda, Akio Horie, Hiroshi Wada
  • Patent number: 6288248
    Abstract: Epichlorohydrin-based product containing at least 99.9% by weight of epichlorohydrin and a total amount of chloro impurities of less than or equal to 150 ppm by weight, and process for manufacturing this product by reaction of allyl chloride with a peroxide compound in the presence of water, a catalyst and a diluent in at least one reactor, and separation of the epichlorohydrin formed.
    Type: Grant
    Filed: November 25, 1998
    Date of Patent: September 11, 2001
    Assignee: Solvay (Société Anonyme)
    Inventors: Michel Strebelle, Patrick Gilbeau, Jean-Pierre Catinat
  • Patent number: 6262278
    Abstract: The present invention relates to a process for stereoselective or regioselective chemical synthesis which generally comprises reacting a nucleophile and a chiral or prochiral cyclic substrate in the presence of a non-racemic, chiral catalyst to produce a stereoisomerically- and/or regioisomerically-enriched product. The present invention also relates to hydrolytic kinetic resolutions of racemic and diastereomeric mixtures of epoxides.
    Type: Grant
    Filed: August 14, 1998
    Date of Patent: July 17, 2001
    Assignee: President and Fellows of Harvard College
    Inventors: Eric N. Jacobsen, Makoto Tokunaga, Jay F. Larrow
  • Patent number: 6235870
    Abstract: Process for the preparation of compounds of the formula wherein Hal represents chlorine, bromine or iodine and preferably chlorine, wherein Ra represents hydrogen or a residue comprising one or more additional groups of the formula, from compounds wherein R2 represents hydrogen or a residue comprising one or more additional groups of the formula by reaction with gaseous hydrogen halide in the presence of a catalytic amount of an organic acid; process for the preparation of epoxy compounds starting from the reaction to produce a compound of formula (III) which is converted to a compound of formula (A) that is dehydrohalogenated to form the epoxy rings of a diepoxy compound.
    Type: Grant
    Filed: September 29, 1999
    Date of Patent: May 22, 2001
    Assignee: Shell Oil Company
    Inventors: Jozef Jacobus Titus Smits, Judith Johanna Berendina Walhof
  • Patent number: 6232478
    Abstract: The present invention relates to a process for the preparation of chiral 3,4-epoxybutyric acid expressed by formula (1) and the salt thereof, wherein (S)-3-activated-hydroxybutyrolactone expressed by formula (2) is subjected to a ring-opening reaction to obtain 4-hydroxy-3-activated hydroxybutyric acid expressed by formula (3), which is subjected to an epoxydation with an inversion of the chiral center.
    Type: Grant
    Filed: January 14, 2000
    Date of Patent: May 15, 2001
    Inventors: Il Suk Byun, Kyung Il Kim, Yoon Hwan Choi
  • Patent number: 6229023
    Abstract: According to the inventive co-oxidation process of organic compounds, (A) a compound selected from (A1) a compound having a non-aromatic ethylenic bond and (A2) a ketone or an alcohol corresponding to the ketone is oxidized by molecular oxygen in the presence of N-hydroxyphthalimide or another imide compound and in the coexistence of (B) a compound oxidizable by the imide compound and oxygen and different from the compound (A). As the compound (B), (a) primary or secondary alcohols (e.g., benzhydrol, cyclohexanol), (b) compounds each having a carbon-hydrogen bond at the adjacent position to an unsaturated bond (e.g., tetralin, ethylbenzene) and the like can be used. According to this process, a corresponding epoxy compound from the compound (A1) having a non-aromatic ethylenic bond, and a corresponding ester or lactone from the ketone or its corresponding alcohol (A2) can be obtained in satisfactory yields.
    Type: Grant
    Filed: November 22, 1999
    Date of Patent: May 8, 2001
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Yasutaka Ishii, Tatsuya Nakano
  • Patent number: 6204357
    Abstract: The invention is directed to new double metal cyanide (DMC) catalysts, a process for the preparation of these catalysts, and to a process for the preparation of polyetherpolyols by the polyaddition of alkylene oxides to starter compounds which contain active hydrogen atoms, wherein the catalyst comprises the novel double metal cyanide (DMC) catalyst of the present invention. These new double metal cyanide (DMC) catalysts comprise a) one or more double metal cyanide compounds, b) one or more organic complex ligands, and c) one or more cyclodextrins, with the proviso that b) and c) are different compounds. The catalysts of this invention exhibit greatly increased activity during preparation of a polyetherpolyol.
    Type: Grant
    Filed: February 10, 2000
    Date of Patent: March 20, 2001
    Assignee: Bayer Aktiengesellschaft
    Inventors: Pieter Ooms, Jörg Hofmann, Pramod Gupta, Lambertus Groenendaal
  • Patent number: 6156915
    Abstract: A reactive and durable anti-static agent and the method of preparing the anti-static agent comprises: a compound with an amine group and a compound with an epoxide group added into the flask, stirred under the gradual raised temperature, reacted into an anti-static agent with a reactive functional group under proper temperature. The characteristics of the invention is that the reaction of preparing the anti-static agent is very active, and the preparing method is easy. With the reactive functional groups and polymer additives which enable the reaction in polymer, in addition to the endurance and a long lifetime, the surface property of the anti-static agent is improved. Therefore, the anti-static prepared according to the invention is broadly in use of industry.
    Type: Grant
    Filed: June 19, 1997
    Date of Patent: December 5, 2000
    Assignee: Industrial Technology Research Institute
    Inventors: Yuung-Ching Sheen, Ling-Yu Cheng, Juh-Shyong Lee, Tsai-Wie Tseng
  • Patent number: 6121468
    Abstract: A process for producing amide derivatives represented by general formula (XV) ##STR1## or enantiomers thereof, novel intermediate compounds useful for producing these compounds, etc., and a process for producing the same, wherein each symbol is as defined in the specification. Compared with the conventional processes, the above process can be very easily effected and enables an efficient production of the compounds (XV), i.e., those involving the compounds (XVI) having an HIV protease inhibitory effect in high yields. The novel intermediates are highly advantageous as intermediates for producing not only the above compounds (XVI) but also those which are useful as an X-ray contrast medium, etc.
    Type: Grant
    Filed: May 19, 1998
    Date of Patent: September 19, 2000
    Assignees: Japan Tobacco Inc., Agouron Pharmaceuticals, Inc.
    Inventors: Takashi Inaba, Yasuki Yamada, James Shanley, Michael Deason
  • Patent number: 6100412
    Abstract: A process for the production of an epoxide and/or its corresponding vicinal diol by a reaction of an olefinic compound with hydrogen peroxide, wherein the reaction is performed in the presence of a carbon dioxide phase at a temperature and a pressure above the critical point of carbon dioxide.
    Type: Grant
    Filed: September 10, 1999
    Date of Patent: August 8, 2000
    Assignee: Degussa-Huls AG
    Inventors: Georg Thiele, Shane A. Nolan, James S. Brown, Jie Lu, Brandon C. Eason, Charles A. Eckert, Charles L. Liotta
  • Patent number: 6087514
    Abstract: Disclosed are novel crystalline molecular sieves having the framework of ETS-10 titanium silicate which contain both octahedral and tetrahedral titanium atoms and are in acid form. The sieves are prepared by adding a complexing agent such as hydrogen peroxide during synthesis or by treating a synthesized titanium silicate molecular sieve with a reagent that replaces tetrahedral silicon with tetrahedral titanium atoms.
    Type: Grant
    Filed: October 20, 1998
    Date of Patent: July 11, 2000
    Assignee: Engelhard Corporation
    Inventors: Appadurai Thangaraj, Steven M. Kuznicki, Gerald S. Koermer
  • Patent number: 6087299
    Abstract: The present invention relates to silver-containing and optionally promoter-containing supported catalysts and catalyst intermediates, processes for their preparation and their use for preparing alkylene oxides by oxidation of alkenes with oxygen. The catalysts are prepared by treatment of a support with a lactic acid containing silver ions, nitrate ions and optionally promoter metal ions, drying, predecomposition in a virtually oxygen-free atmosphere and subsequent activation by heating in an oxygen-containing atmosphere while precisely controlling the temperature conditions and the feeding-in of oxygen. The catalyst intermediates obtainable by treatment, drying and only predecomposition can be activated in a temporally and physically separate process step to form the actual catalysts. Suitable promoters are alkaline earth metal compounds and/or alkali metal compounds. High activities and high selectivities are achieved when using the catalysts of the invention for preparing alkylene oxides.
    Type: Grant
    Filed: January 26, 1999
    Date of Patent: July 11, 2000
    Assignee: EC Erdolchemie GmbH
    Inventors: Joachim Grub, Werner Volprecht, Matthias Baum, Alfred Reimer
  • Patent number: 6063941
    Abstract: The invention relates to a process for the regeneration of a catalyst of titanium silicalite type used in particular in reactions for the oxidation of saturated hydrocarbons or for the epoxidation of olefins by treatment with a liquid solution containing an oxidizing agent.
    Type: Grant
    Filed: April 20, 1999
    Date of Patent: May 16, 2000
    Assignee: Solvay (Societe Anonyme)
    Inventor: Patrick Gilbeau
  • Patent number: 6040464
    Abstract: A process for producing protected 3-amino-1,2-dihydroxypropane acetal, particularly in chiral forms, for use as an intermediate in the preparation of various 3-carbon compounds which are chiral. In particular, the present invention relates to the process for preparation of 3-amino-1,2-dihydroxypropane isopropylidene acetal. The protected 3-amino-1,2-dihydroxypropane acetal is a key intermediate to the preparation of chiral 3-carbon compounds which in turn are intermediates to various pharmaceuticals.
    Type: Grant
    Filed: May 27, 1999
    Date of Patent: March 21, 2000
    Assignee: Board of Trustees operating Michigan State University
    Inventors: Rawle I. Hollingsworth, Guijun Wang
  • Patent number: 6031115
    Abstract: A process for preparing compounds of formula (B) wherein:one of A.sub.1 ' or A.sub.2 ' represents hydrogen and the other represents a group CF.sub.3 --Y-- wherein Y represents --CF.sub.2 --, >C.dbd.O, or --CH(OH)--, or A.sub.1 ' and A.sub.2 ' are groups convertible to A.sub.1 and A.sub.2 respectively.Y.sub.1 represents --O--, --CH.sub.2 -- or NR.sup.O wherein R.sup.O is hydrogen, alkyl or alkylcarbonyl; R.sub.1 and R.sub.2 independently represent hydrogen or alkyl; orR.sub.1 and R.sub.2 together represent a C.sub.2-7 polymethylene moiety;R.sub.3 represents hydrogen, hydroxy, alkoxy or acyloxy and R.sub.4 is hydrogen or R.sub.3 and R.sub.4 together represent a bond;which process comprises reacting a compound of formula (C): ##STR1## wherein the variable A.sub.1 ', A.sub.2 ', Y.sub.1, R.sub.1 and R.sub.2 are as defined above, in the presence of an oxygen source and a chiral catalyst as defined in WO/91/14694.
    Type: Grant
    Filed: July 2, 1998
    Date of Patent: February 29, 2000
    Assignee: SmithKline Beecham plc
    Inventors: David Bell, Michael Fedouloff, Gillian Turner
  • Patent number: 6013666
    Abstract: This invention relates to a novel oxirane carboxylic acid derivative and thereof manufacturing method. Based on thereof mechanism to inhibit the CPT I, oxirane carboxylic acid derivative of this invention has blood glucose lowering effects so that the derivative may be effectively used as an antidiabetic agent having remarkable antidiabetic activity and less side effects.
    Type: Grant
    Filed: May 11, 1999
    Date of Patent: January 11, 2000
    Assignees: Sang Sup Jew, Kang Ho Kang, Bak Kwang Kim
    Inventors: Sang Sup Jew, Suk Ku Kang, Deuk Joon Kim, Won Ki Kim, Hwa Jung Kim, Chang Kiu Moon, Jeong Hill Park, Young Ger Suh, Bong Jin Lee, Jee Woo Lee, Ki Hwa Jung, Moon Woo Chun, Hoon Huh, Eung Seok Lee, Hyung Ook Kim, Eun Kyung Kim, Sung Jin Kim, Jae Hoon Cheong, Kwang Ho Ko, Bak Kwang Kim
  • Patent number: 6008386
    Abstract: The present invention is related to a novel class of decarboxylase enzyme inhibitors consisting of .alpha.-oxiranyl amino acids and derivatives thereof and a method of synthesizing such compounds.
    Type: Grant
    Filed: July 22, 1997
    Date of Patent: December 28, 1999
    Assignee: Board of Regents University of Nebraska-Lincoln
    Inventors: David B. Berkowitz, Michelle L. Pedersen
  • Patent number: 6001954
    Abstract: Process for the preparation of compounds of the formula ##STR1## wherein Hal represents chlorine, bromine or iodine and preferably chlorine, wherein R.sub.a represents hydrogen or a residue comprising one or more additional groups of the formula, ##STR2## from compounds ##STR3## wherein R.sub.2 represents hydrogen or a residue comprising one or more additional groups of the formula ##STR4## by reaction with gaseous hydrogen halide in the presence of a catalytic amount of an organic acid. Epoxy resins are prepared via the reaction of a compound of formula (A) in the presence of a basic compound.
    Type: Grant
    Filed: February 6, 1998
    Date of Patent: December 14, 1999
    Assignee: Shell Oil Company
    Inventors: Jozef Jacobus Titus Smits, Judith Johanna Berendina Walhof
  • Patent number: 5998637
    Abstract: A process for preparing an optically active trans-3-substituted glycidic acid ester compound of the formula (I): ##STR1## wherein ring A is a substituted or unsubstituted benzene ring, and R.sup.1 is an ester residue, which comprises:preparing a solution of one optical isomer (A) and the other optical isomer (B) of the ester compound (I), both of which are the optical isomers due to the asymmetric carbons at 2- and 3-positions, and an ester compound (B') which is different from the isomer (B) only in the ester residue R.sup.
    Type: Grant
    Filed: February 27, 1998
    Date of Patent: December 7, 1999
    Assignee: Tanabe Seiyaku Co., Ltd.
    Inventors: Masakatsu Furui, Toshiyuki Furutani
  • Patent number: 5962704
    Abstract: A method for producing an amide derivative of the formula ?XV! ##STR1## wherein each symbol is as defined in the specification, and an enantiomer thereof, a novel intermediate useful for producing said compound and a production method thereof. The production method of the present invention is extremely easy and simple as compared to the conventional methods, and enables effective production of compound ?XV! at high yields, which includes compound ?XVI! having an HIV protease inhibitory action. In addition, the novel intermediates of the present invention are extremely useful as intermediates for producing not only the aforementioned compound ?XVI! but also compounds useful as X-ray contrast media.
    Type: Grant
    Filed: March 25, 1998
    Date of Patent: October 5, 1999
    Assignees: Japan Tobacco Inc., Agouron Pharmaceuticals, Inc.
    Inventors: Takashi Inaba, Yasuki Yamada
  • Patent number: 5929232
    Abstract: The present invention relates to a process for stereoselective or regioselective chemical synthesis which generally comprises reacting a nucleophile and a chiral or prochiral cyclic substrate in the presence of a non-racemic chiral catalyst to produce a stereoisomerically or regioselectively enriched product.
    Type: Grant
    Filed: March 25, 1996
    Date of Patent: July 27, 1999
    Assignee: President and Fellows of Harvard College
    Inventors: Eric N. Jacobsen, James L. Leighton, Luis E. Martinez
  • Patent number: 5892104
    Abstract: This invention relates to a compound having the formula I: ##STR1## wherein n is an integer of from 0 to 1; when n is 1, one of dashed lines a and b is a single bond and the other of dashed lines a and b is a double bond, dashed line c is not present, and dashed line d is a single bond; when n is 0, dashed lines a, b, c and d are single bonds or one of dashed lines a and b is a single bond and the other of dashed lines a and b is a double bond, dashed line c is not present, and dashed line d is a double bond; R.sub.1, R.sub.2 and R.sub.3 are, independently, lower branched or straight chain alkyl, alkenyl or alkynyl of C.sub.1 -C.sub.6 ; and R.sub.4 is hydrogen, lower branched or straight chain alkyl, alkenyl or alkynyl of C.sub.1 -C.sub.5, or C(O)R.sub.5, wherein R.sub.5 is hydrogen or lower branched or straight chain alkyl, alkenyl or alkynyl of C.sub.1 -C.sub.4 ; wherein the sum of the carbon atoms in R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is less than or equal to eight carbon atoms.
    Type: Grant
    Filed: February 14, 1997
    Date of Patent: April 6, 1999
    Assignee: Millenium Specialty Chemicals, Inc.
    Inventors: Bernard J. Kane, Henri M. Hoffmann
  • Patent number: 5859284
    Abstract: The present invention provides new synthetic methods and compositions. In particular, new methods of preparing intermediates useful in the synthesis of neuraminidase inhibitors and compositions useful as intermediates that are themselves useful in the synthesis of neuraminidase inhibitors are provided.
    Type: Grant
    Filed: August 23, 1996
    Date of Patent: January 12, 1999
    Assignee: Gilead Sciences, Inc.
    Inventors: Kenneth M. Kent, Choung U. Kim, Lawrence R. McGee, John D. Munger, Jr., Ernest J. Prisbe, Michael J. Postich, John C. Rohloff, Daphne E. St. John, Matthew A. Williams, Lijun Zhang
  • Patent number: 5811599
    Abstract: A process for the oxidation of hydrocarbons and their derivatives having the general formula RX, wherein R is from n-alkyl, iso-alkyl, benzyl, cyclohexyl, mono, di or tricyclic aryl, or alkenic groups and X is selected from H, OH or Cl to compounds having formula R.sup.1 XY wherein R.sup.1 =(R--H), X has the meaning defined as above and Y=OH; which comprises of reacting the appropriate hydrocarbon or it's derivative of the formula RX where R and X have the meaning given above, with a solution of aqueous hydrogen peroxide at a temperature in the range of 10.degree.-100.degree. C. in the presence of an amorphous titanium-silicate catalyst having molar chemical composition in terms of the anhydrous oxides of TiO.sub.2 : (5-400) SiO.sub.2, having an average micropore radius between 10 and 40 .ANG., an absorption band around 220 nm in the ultraviolet region, a band around 960 cm.sup.-1 in the infrared region, interatomic vectors around 1.6-1.7, 2.7-2.8, 4.1-4.2 and 5.0-5.2 .ANG.
    Type: Grant
    Filed: August 2, 1995
    Date of Patent: September 22, 1998
    Inventors: Keshavaraja Alive, Ramaswamy Arumugamangalam Venkataraman, Ratnasamy Paul
  • Patent number: 5780672
    Abstract: A process for the preparation of compounds of the formula (1) in which R.sup.1, R.sup.2 and R.sup.3 are as defined in the specification, which includes reacting alcohols or carboxylic acids of the formula (2) in which R.sup.1, R.sup.2 and R.sup.3 are as defined in the specification, with a fluorinating agent of the formula (3) as defined in the specification.
    Type: Grant
    Filed: July 11, 1996
    Date of Patent: July 14, 1998
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Sergej Pasenok, Wolfgang Appel
  • Patent number: 5756862
    Abstract: A process for producing optically active 2-halo-1-(substituted phenyl)ethanol of a formula (Ia) or optically active styrene oxide of a formula (Ib). The process comprises the steps of reacting a compound of a formula (II) with phthalic anhydride to give a compound of a formula (III), performing optical resolution on the resulting compound using an optically active organic amine as a resolving agent, and finally performing hydrolysis or alcoholysis on the optically resolved compound (Ia) or (Ib). The scheme of the above process is: ##STR1## wherein X represents a halogen atom, Y represents a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkoxy group, a C.sub.1 -C.sub.6 haloalkyl group or a C.sub.1 -C.sub.6 haloalkoxy group, Z represents a hydrogen atom, a halogen atom or a C.sub.1 -C.sub.6 alkyl group, n is 0 or an integer of 1 to 3 and m is 0 or an integer of 1 to 2. The resulting optically active compounds are useful as an intermediate for medicines.
    Type: Grant
    Filed: August 19, 1996
    Date of Patent: May 26, 1998
    Assignee: Nihon Nohyaku Co., Ltd.
    Inventors: Hiroki Kodama, Takuya Motokawa, Hiroshi Yamaguchi, Masanori Yoshida
  • Patent number: 5717116
    Abstract: The present invention provides a process for producing (R)-styrene oxides represented by the formula (1): ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and X are as defined in the specification, which comprises treating a mixture of (R)- and (S)-phenylhalogenomethylcarbinols with a lipase in the presence of a carboxylate to preferentially convert the (S)-phenylhalogenomethylcarbinols, and treating a mixture of the formed carbinol alkylates (3) and (R)-phenylhalogenomethylcarbinols with a base to cyclize the (R)-phenylhalogenomethylcarbinols, and also provides an industrially excellent process for producing (R)-styrene oxides (1) which comprises using a mixture enriched with (R)-phenylhalogenomethylcarbinols as the mixture of (R)- and (S)-phenylhalogenomethylcarbinols (2).
    Type: Grant
    Filed: March 29, 1996
    Date of Patent: February 10, 1998
    Assignee: Sumika Fine Chemicals Company, Limited
    Inventors: Kenji Saito, Norio Kometani, Azusa Fujiwara, Yukio Yoneyoshi, Gohfu Suzukamo
  • Patent number: 5705660
    Abstract: The present invention is related to a novel class of decarboxylase enzyme inhibitors consisting of .alpha.-oxiranyl amino acids and derivatives thereof and a method of synthesizing such compounds.
    Type: Grant
    Filed: August 22, 1994
    Date of Patent: January 6, 1998
    Assignee: Board of Regents, University of Nebraska-Lincoln
    Inventors: David B. Berkowitz, Michelle L. Pedersen
  • Patent number: 5693847
    Abstract: The present invention relates to functionalized ketones and novel processes for synthesizing those ketones. The processes of this invention are especially well suited for synthesizing .alpha.-methyl leaving group functionalized ketones. This invention also relates to processes for using .alpha.-methyl leaving group functionalized ketones to produce other compounds and intermediates useful in those processes.
    Type: Grant
    Filed: April 19, 1995
    Date of Patent: December 2, 1997
    Assignee: Vertex Pharmaceuticals Incorporated
    Inventors: Roger D. Tung, Thomas E. D'Ambra
  • Patent number: 5637738
    Abstract: Described herein is a process for the preparation of (1S,2R)-1,2-epoxy-1,2,3,4-tetrahydronaphthalene having the Formula (I): ##STR1## which comprises the steps of (a) hydrogenating the compound of Formula (II) to form cis-(1R, 2S)-1,2-dihydroxy-1,2,3,4-tetrahydronaphthalene having the Formula (V): ##STR2## (b) reacting the dihydroxy compound of Formula (V) with a sulphonyl halide of formula R.sup.1 SO.sub.2 Z wherein R.sup.1 is methyl, ethyl, trifluoromethyl, phenyl or p-tolyl, and Z is fluorine, chlorine, bromine or iodine to give a bis-sulphonyl ester of formula (X): ##STR3## and (c) treating the bis-sulphonyl ester (X) with an alkali metal carbonate or alkali metal hydroxide to give the compound of Formula (I).
    Type: Grant
    Filed: August 25, 1995
    Date of Patent: June 10, 1997
    Assignee: Zeneca Limited
    Inventors: Andrew J. Blacker, Stephen M. Brown, Derek R. Boyd, Gary N. Sheldrake
  • Patent number: 5629423
    Abstract: A process for synthesizing enantiomerically pure chiral secondary alcohol compounds linked to a heterocyclic core moiety, using a natural chiral molecule starting material. The inventive process is particularly useful for bulk manufacturing of chiral secondary alcohol compounds.
    Type: Grant
    Filed: May 23, 1995
    Date of Patent: May 13, 1997
    Assignee: Cell Therapeutics, Inc.
    Inventors: J. Peter Klein, Alistair J. Leigh, John Michnick, Anil M. Kumar, Gail E. Underiner
  • Patent number: 5488118
    Abstract: The present invention relates to a process for producing an optically active erythro-3-amino-1,2-epoxy compound represented by the following general formula (3): ##STR1## wherein R1 represents a hydrocarbon residue having 3 to 12 carbon atoms; and R2 represents optionally protected amino, provided that when the carbon atom at the *3-position has an S configuration, then the carbon atom at the *2-position has an S configuration, and when the carbon atom at the *3-position has an R configuration, then the carbon atom at the *2-position has an R configuration.
    Type: Grant
    Filed: November 28, 1994
    Date of Patent: January 30, 1996
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Taichi Koshigoe, Hitoshi Satoh, Kenichi Yamamoto
  • Patent number: 5451689
    Abstract: There is provided a method of preparing an epoxide (1a) or (1b) shown below: ##STR1## where R.sup.1, R.sup.2, R.sup.3, and R.sup.4 represent a hydrogen atom, an alkyl group, an alkenyl group, an aryl group, an alkoxy group, an aryloxy group, an acyl group, an alkyloxycarbonyl group, an aryloxycarbonyl group, allalkyl group, a silyl group, and a silyloxy group; the groups may be bonded with each other to form rings in the case where these groups can be bivalent; these groups may be the same or different, may have substituting groups, or may be branched; and each form (isomer) has a structure in which one side of the plane constituted by double bonds, R.sup.1, R.sup.2, R.sup.3 and R.sup.4, is more seterically hindered in comparison with the other side;characterized in that:an olefin represented by the formula (2) below, is reacted with iodine in the presence of compound generating acyloxy ion, ##STR2## where R.sup.1, R.sup.2, R.sup.3 and R.sup.
    Type: Grant
    Filed: December 30, 1993
    Date of Patent: September 19, 1995
    Assignee: Japan Tobacco, Inc.
    Inventors: Katsuya Matsumoto, Takashi Ebata, Koshi Koseki, Koji Okano, Hiroshi Kawakami, Hajime Matsushita
  • Patent number: 5440004
    Abstract: A method for the production of an alkylene carbonate at high yields and high selectivity by a reaction between an alkylene glycol and urea, the method being capable to preventing the deposition of a white crystal in the reflux condenser used in a conventional method for the production of alkylene carbonate and the subsequent decrease in the yield, wherein:a gas washing member and a cooling member are disposed above a reaction portion where alkylene glycol and urea are allowed to react,ammonia-containing steam exhausted from the reaction portion is downwardly introduced into the cooling member through the gas washing member,condensate and ammonia gas exhausted from a bottom of the cooling member are gas-liquid separated,the condensate is introduced into the gas washing member, andthe ammonia gas is removed from the reaction system.
    Type: Grant
    Filed: May 5, 1994
    Date of Patent: August 8, 1995
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Masaharu Doya, Yutaka Kanbara, Ken-ichi Kimizuka, Takashi Okawa
  • Patent number: 5292891
    Abstract: There are provided novel and optically active 2,2-dimethyl-1,3-dioxin-4-ones which are useful as starting materials for physiologically active compounds, functional materials or the like. Provided are optically active 5,6-epoxyhexanoic acid esters and novel optically active 6-substituted tetrahydropyran-2-one derivatives.
    Type: Grant
    Filed: December 15, 1992
    Date of Patent: March 8, 1994
    Assignee: Chisso Corporation
    Inventors: Chikara Kaneko, Masayuki Sato
  • Patent number: 5256800
    Abstract: There are provided novel and optically active 2,2-dimethyl-1,3-dioxin-4-ones which are useful as starting materials for physiologically active compounds, functional materials or the like. Furthermore, a method for preparing an optically active compound comprises reacting a racemic 1,3-dioxin-4-one with vinylacetate in the presence of lipase to resolve the racemic compound into optically active compound represented by the formula (3) ##STR1## and an optically active compound represented by the formula (4) ##STR2## which is an antipode of the compound represented by the formula (3).
    Type: Grant
    Filed: February 18, 1992
    Date of Patent: October 26, 1993
    Assignee: Chisso Corporation
    Inventors: Chikara Kaneko, Masayuki Sato
  • Patent number: 5243096
    Abstract: An optically active pentane compound of the general formula (I): ##STR1## wherein R.sub.1 represents a lower alkyl group having 1 to 4 carbon atoms, R.sub.2 represents a lower alkoxycarbonyl group having an alkoxy moiety of 1 to 4 carbon atoms, or a straight-chain or branched alkyl group having 1 to 7 carbon atoms which is unsubstituted or substituted with a hydroxy or protected hydroxy group, A represents a halogen atom, hydroxy, protected hydroxy, or ethynyl group, or a group of the formula ##STR2## B represents a hydrogen atom, hydroxy, protected hydroxy or acyloxy group, D represents a hydrogen atom, or A and B together can form an acetal or epoxy group, A and D together can form an ethylidene group, and B and D together can form a carbon-carbon direct bond, and the chiral central carbon atoms marked with symbols *, # and .thrfore.
    Type: Grant
    Filed: April 30, 1992
    Date of Patent: September 7, 1993
    Assignee: Asahi Denka Kogyo K.K.
    Inventors: Seiichi Takano, Kunio Ogasawara
  • Patent number: 5214167
    Abstract: Process comprising heating a dioxole at 100.degree.-400.degree. C. for a sufficient time to convert the dioxole to an epoxide, for example, bis-2,2-trifluoromethyl-4,5-difluoro-1,3-dioxole to 2,3-epoxy-3-trifluoromethyl-4-trifluorobutyryl fluoride.
    Type: Grant
    Filed: February 18, 1992
    Date of Patent: May 25, 1993
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Ming-Hong Hung, Paul R. Resnick
  • Patent number: 5043458
    Abstract: A continuous, gas-assisted atmospheric process for preparing cyclic esters of alpha-hydroxycarboxylic acids, such as lactide, which comprises feeding the reactants into a reactor having means for introducing an inert gas at the operating temperature, forming a reaction mass having cyclic esters in the reactor, passing a flow of said inert gas through said reactor whereby cyclic esters are swept from the reaction mass into a gaseous product stream, and recovering the cyclic esters therefrom.
    Type: Grant
    Filed: May 3, 1990
    Date of Patent: August 27, 1991
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Kamlesh K. Bhatia
  • Patent number: 5023349
    Abstract: A gas-assisted continuous process for the rapid conversion of oligomers of alpha-hydroxycarboxylic acids, esters or salts thereof to cyclic esters in high yields and high states of purity.
    Type: Grant
    Filed: May 8, 1990
    Date of Patent: June 11, 1991
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Kamlesh K. Bhatia
  • Patent number: 5011954
    Abstract: Process comprising heating a dioxole at 100.degree.-400.degree. C. for a sufficient time to convert the dioxole to an epoxide, for example, bis-2,2-trifluoromethyl-4,5-difluoro-1,3-dioxole to 2,3-epoxy-3-trifluoromethyl-4-trifluorobutyryl fluoride.
    Type: Grant
    Filed: August 30, 1989
    Date of Patent: April 30, 1991
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Ming-Hong Hung, Paul R. Resnick
  • Patent number: 5003084
    Abstract: Disclosed is a process for preparing alkylene carbonates which comprises reacting the corresponding alkylene glycol and urea, optionally in the presence of a catalyst comprising a tin-containing compound, and represented by the equation: ##STR1## where R represents an alkyl group containing 1 to 16 carbons.
    Type: Grant
    Filed: February 20, 1990
    Date of Patent: March 26, 1991
    Assignee: Texaco Chemical Company
    Inventors: Wei-Yang Su, George P. Speranza
  • Patent number: 4894467
    Abstract: Disclosed is a process for making styrene oxide which comprises contacting styrene in the vapor phase with a molecular oxygen-containing gas over a silver metal catalyst containing a promoting amount of at least one alkali metal hydroxide selected from sodium, potassium and lithium hydroxides, on an inert solid inorganic support at contact times of from 0.6 to 10 seconds and temperatures from 200.degree. to 350.degree. C.
    Type: Grant
    Filed: October 16, 1986
    Date of Patent: January 16, 1990
    Assignee: The Standard Oil Company
    Inventor: Patricia R. Blum
  • Patent number: 4885374
    Abstract: A process for producing an alkylene oxide or mixture of alkylene oxides by a reaction which comprises reacting an alkane or alkylaromatic compound mixture thereof with an oxygen-containing gas in the presence of at least one molten nitrate salt catalyst.
    Type: Grant
    Filed: August 31, 1988
    Date of Patent: December 5, 1989
    Assignee: Olin Corporation
    Inventor: B. Timothy Pennington
  • Patent number: 4851555
    Abstract: An alkylene oxide, e.g. ethylene oxide, is prepared from the corresponding alkylene carbonate, e.g. ethylene carbonate, in the presence of an effective amount of a quaternary arsonium halide. The quaternary arsonium halides are also effective catalysts for the reverse reaction, that is, to form alkylene carbonates from the corresponding epoxide and carbon dioxide.
    Type: Grant
    Filed: October 25, 1984
    Date of Patent: July 25, 1989
    Assignee: Scientific Design Company, Inc.
    Inventor: Robert M. Weinstein