Three Or More Ring Hetero Atoms In The Hetero Ring Patents (Class 549/34)
  • Patent number: 12221429
    Abstract: Disclosed is a method for synthesizing 1,3,2-dioxathiolane 2,2-dioxide (DTD) by in-situ catalytic oxidation. A titanium silicon (TS)-1 molecular sieve is modified with a Pd salt and an Au salt to obtain an Au—Pd/TS-1 molecular sieve, which catalyzes oxygen and hydrogen to form hydrogen peroxide, and oxidizes glycol sulfite in situ in a reactor to synthesize DTD. An Au—Pd/TS-1 molecular sieve catalyst prepared by the present disclosure, which has two catalytic activities of catalytic synthesis of hydrogen peroxide and catalytic oxidation of sulfite, can significantly increase the reaction rate, enable the complete conversion of raw materials in a shorter residence time, and effectively inhibit the hydrolysis of products, and a high-purity DTD product can be obtained by washing and evaporatively crystallizing an organic phase.
    Type: Grant
    Filed: July 11, 2024
    Date of Patent: February 11, 2025
    Assignee: Shandong Normal University
    Inventors: Qikui Liu, Xiaomeng Zhang
  • Patent number: 10793540
    Abstract: The present invention provides an industrially applicable method for production of a fluorine-containing cyclopropane carboxylic acid compound useful as an intermediate for pharmaceutical and agrichemical products. A fluorine-containing cyclopropane monoester is obtained by: forming a fluorine-containing cyclic sulfate with the use of a fluorine-containing diol compound and sulfuryl fluoride (as a cyclic sulfuric esterification step); reacting the fluorine-containing cyclic sulfate with a malonic diester, thereby forming a fluorine-containing cyclopropane diester (as a cyclopropanation step); and hydrolyzing the fluorine-containing cyclopropane diester (as a hydrolysis step).
    Type: Grant
    Filed: September 5, 2019
    Date of Patent: October 6, 2020
    Assignee: Central Glass Company, Limited
    Inventors: Takashi Kashiwaba, Takako Yamazaki, Shoko Ishii, Shunsuke Mimura, Masanori Fushimi, Ryuichi Okamoto, Haruki Kobayashi, Manabu Yasumoto
  • Patent number: 10450291
    Abstract: The present invention provides an industrially applicable method for production of a fluorine-containing cyclopropane carboxylic acid compound useful as an intermediate for pharmaceutical and agrichemical products. A fluorine-containing cyclopropane monoester is obtained by: forming a fluorine-containing cyclic sulfate with the use of a fluorine-containing dial compound and sulfuryl fluoride (as a cyclic sulfuric esterification step); reacting the fluorine-containing cyclic sulfate with a malonic diester, thereby forming a fluorine-containing cyclopropane diester (as a cyclopropanation step); and hydrolyzing the fluorine-containing cyclopropane diester (as a hydrolysis step).
    Type: Grant
    Filed: June 24, 2016
    Date of Patent: October 22, 2019
    Assignee: Central Glass Company, Limited
    Inventors: Takashi Kashiwaba, Takako Yamazaki, Shoko Ishii, Shunsuke Mimura, Masanori Fushimi, Ryuichi Okamoto, Haruki Kobayashi, Manabu Yasumoto
  • Publication number: 20140370375
    Abstract: The present invention provides an organic electrolyte that improve the organic electrolyte storage battery of an electric vehicle in the initial storage capacity that affects the possible cruising range, which electrolyte comprises a compound having no rotational symmetry axis of the compounds represented by formula (1) below: wherein R1 to R5 are each independently hydrogen, an alkyl group, a halogenated alkyl group, or halogen, R6 is an alkylene group or a halogenated alkylene group and R7 is a phenyl group having no substituent or having a substituent (a straight-chain or branched alkyl group having one to four carbon atoms, halogen-containing straight-chain or branched alkyl group having one to four carbon atoms, or halogen) bonded thereto.
    Type: Application
    Filed: December 18, 2012
    Publication date: December 18, 2014
    Applicant: JX NIPPON OIL & ENERGY CORPORATION
    Inventors: Takeshi Nishizawa, Atsuo Omaru
  • Patent number: 8673963
    Abstract: The present invention is directed to provide an efficient production method which is capable of not only obtaining a cyclic sulfonic acid ester (sultone) at low cost and in high yield, but also the sulfonic acid ester (sultone) stably even in a commercial scale. The present invention relates to a method for producing hydroxysultone comprising a first step where a diol having a specified structure and a thionyl halide are reacted to obtain a cyclic sulfite having a specified structure, and a second step where the cyclic sulfite is reacted with water or/and alcohol; a method for producing an unsaturated sultone having a specified structure comprising a third step where a hydroxylsultone having a specified structure is reacted with an acid halide or an acid anhydride to obtain an intermediate, subsequently the intermediate is treated with a base; as well as a cyclic sulfite having a specified structure.
    Type: Grant
    Filed: August 3, 2010
    Date of Patent: March 18, 2014
    Assignee: Wako Pure Chemical Industries, Ltd.
    Inventors: Ayako Kuramoto, Kuniaki Okamoto, Tsutomu Watahiki, Motoshige Sumino
  • Publication number: 20130338349
    Abstract: The present invention provides (i) processes for preparing a 2?-deoxy-2?-fluoro-2?-methyl-D-ribonolactone derivatives, (ii) conversion of intermediate lactones to nucleosides with potent anti-HCV activity, and their analogues, and (iii) methods 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: Application
    Filed: June 13, 2013
    Publication date: December 19, 2013
    Inventors: Byoung-Kwon Chun, Peiyuan Wang, Jinfa Du, Suguna Rachakonda
  • Publication number: 20130171514
    Abstract: A non-aqueous electrolyte solution containing a cyclic sulfate compound represented by formula (I) is provided, wherein in formula (I), R1 represents a group represented by formula (II) or a group represented by formula (III); R2 represents a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms, a group represented by formula (II), or a group represented by formula (III); and in formula (II), R3 represents a halogen atom, an alkyl group having from 1 to 6 carbon atoms, a halogenated alkyl group having from 1 to 6 carbon atoms, an alkoxy group having from 1 to 6 carbon atoms, or a group represented by formula (IV).
    Type: Application
    Filed: October 21, 2011
    Publication date: July 4, 2013
    Applicant: Mitsui Chemicals, Inc.
    Inventors: Shigeru Mio, Mitsuo Nakamura, Kaichiro Haruta, Hidenobu Nogi, Satoko Fujiyama, Takashi Hayashi, Hidetoshi Tsunoda
  • Publication number: 20130004862
    Abstract: An object of the present invention is to provide a nonaqueous electrolytic solution capable of improving low-temperature load characteristics after high temperature charging storage, an electrochemical element using it, and a 1,2-dioxypropane compound used for it. The nonaqueous electrolytic solution of the present invention comprises an electrolyte salt dissolved in a nonaqueous solvent, and contains a 1,2-dioxypropane compound represented by the above-mentioned general formula (I). (wherein R1 and R2 each represent a hydrogen atom, or an alkyl group having from 1 to 6 carbon atoms; X1 represents a group selected from —S(?O)—, —S(?O)2—, —C(?O)—, —CR3R4—, —P(?O)(OR5)— and —SiR6R7—; R3 and R4 each represent a hydrogen atom, or an alkyl group having from 1 to 6 carbon atoms; R5 to R7 each represent an alkyl group having from 1 to 6 carbon atoms.
    Type: Application
    Filed: March 24, 2011
    Publication date: January 3, 2013
    Applicant: UBE Industries LTD
    Inventors: Kazuhiro Miyoshi, Yuichi Kotou, Shoji Shikita
  • Publication number: 20120130089
    Abstract: The present invention is directed to provide an efficient production method which is capable of not only obtaining a cyclic sulfonic acid ester (sultone) at low cost and in high yield, but also the sulfonic acid ester (sultone) stably even in a commercial scale. The present invention relates to a method for producing hydroxysultone comprising a first step where a diol having a specified structure and a thionyl halide are reacted to obtain a cyclic sulfite having a specified structure, and a second step where the cyclic sulfite is reacted with water or/and alcohol; a method for producing an unsaturated sultone having a specified structure comprising a third step where a hydroxylsultone having a specified structure is reacted with an acid halide or an acid anhydride to obtain an intermediate, subsequently the intermediate is treated with a base; as well as a cyclic sulfite having a specified structure.
    Type: Application
    Filed: August 3, 2010
    Publication date: May 24, 2012
    Applicant: WAKO PURE CHEMICAL INDUSTRIES, LTD.
    Inventors: Ayako Kuramoto, Kuniaki Okamoto, Tsutomu Watahiki, Motoshige Sumino
  • Patent number: 8183281
    Abstract: The present invention relates to compounds of formula (I) with the substituents as defined herein, and uses thereof.
    Type: Grant
    Filed: June 4, 2008
    Date of Patent: May 22, 2012
    Assignee: Novartis AG
    Inventors: Neil John Press, Simon James Watson
  • Patent number: 7781673
    Abstract: This disclosure relates to a polymer containing a first comonomer repeat unit and a second comonomer repeat unit. The first comonomer repeat unit includes a cyclopentadithiophene moiety. The second comonomer repeat unit includes a thienothiophene moiety, a thienothiophene tetraoxide moiety, a dithienothiophene moiety, a dithienothiophene dioxide moiety, a dithienothiophene tetraoxide moiety, or a tetrahydroisoindole moiety. The polymer can be used as a photoactive material in a photovoltaic cell. This disclosure also relates to such photovoltaic cells, as well as modules containing such photovoltaic cells.
    Type: Grant
    Filed: June 9, 2006
    Date of Patent: August 24, 2010
    Assignee: Konarka Technologies, Inc.
    Inventors: Russell Gaudiana, Richard Kingsborough, David Waller, Zhengguo Zhu
  • Patent number: 7417156
    Abstract: In only two steps and in 65% overall yield, natural trioxane artemisinin (I) was converted on gram scale into C-10-carba trioxane dimer (3). This new, very stable dimer was then transformed easily in one additional step into four different dimers (4-7). Alcohol and diol dimers (4 and 5) and ketone dimer (7) are 10 times more antimalarially potent in vitro than artemisinin (I), and alcohol and diol dimers (4 and 5) are strongly inhibitory but not cytotoxic toward several human cancer cell lines. Water-soluble carboxylic acid derivatives (8a-10c and 12) were easily prepared from dimers (4-6); they are thermally stable even at 60° C. for 24 hours, are more orally efficacious as antimalarials than either artelinic acid or sodium artesunate, and have potent and selective anticancer activities.
    Type: Grant
    Filed: September 26, 2003
    Date of Patent: August 26, 2008
    Assignee: Johns Hopkins University
    Inventors: Gary H. Posner, Theresa A. Shapiro, Surojit Sur, Tanzina Labonte, Kristina Borstnik, Ik-Hyeon Paik, Andrew J. McRiner
  • Patent number: 6995276
    Abstract: A compound capable of giving optical materials that may be high in both refractive index and Abbe's number and may be excellent in heat resistance and transparency, and a process that may produce the same with good efficiency are disclosed. The compound may be a cyclic disulfide compound including a structure represented by the following general formula (1) or (2) and having a sulfur content of from 50 to 85% by weight: wherein X represents a chain having carbon and/or sulfur as a skeleton, inclusive of cyclic ones; and the number of elements constituting X is from 1 to 4.
    Type: Grant
    Filed: February 6, 2003
    Date of Patent: February 7, 2006
    Assignee: Hoya Corporation
    Inventors: Tsuyoshi Okubo, Ken Takamatsu
  • Patent number: 6992196
    Abstract: Refined ethylene sulfite exhibits an excellent storage stability when used as a constituent of an electrolyte. A method of producing same has a step of reacting ethylene glycol and thionyl chloride to producing raw ethylene sulfite, a rectifying step for rectifying the raw ethylene sulfite, and a refining process for refining the raw ethylene sulfite or the rectified ethylene sulfite conducted before or after the rectifying step. The refining process is at least one process selected from the group consisting of a washing process, a dehydration process by total reflux distillation, a second rectifying process, and an absorbing process. Refined ethylene sulfite produced according to the method contains chloroethanol in an amount of not more than 1000 ppm.
    Type: Grant
    Filed: August 26, 2002
    Date of Patent: January 31, 2006
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Toshimitsu Kato, Norioki Mine, Minoru Kotato
  • Patent number: 6566525
    Abstract: A process for the preparation of N-substituted-hydroxycycloalkylamine derivatives, that are useful intermediates for the synthesis of various organic chemicals including pharmaceutical and agrochemical compounds, represented by formula (1), by reacting a 1,2-dihydroxalkyl alcohol, represented by the following formula (2), with a thionyl halide to produce an intermediate 1,2-cyclosulfinylalkyl halide represented by the following formula (3); and then cyclizing that intermediate with an amine compounds represented by the following formula (4). In the above structural formuli, * represents an asymmetric carbon atom; R1 is hydrogen or an amino-protecting group; m is an integer of 1-3; and X is halogen.
    Type: Grant
    Filed: April 7, 2001
    Date of Patent: May 20, 2003
    Assignee: Samsung Fine Chemicals Co., Ltd.
    Inventors: Seong Jin Kim, Keon Il Kim, Kyoung Youl Yang
  • Publication number: 20030080322
    Abstract: The invention relates to reactive thienothiophenes, their use as semiconductors or charge transport materials, in optical, electrooptical or electronic devices like for example organic field effect transistors (FET or OFET) for thin film transistor liquid crystal displays and integrated circuit devices such as RFID tags, electroluminescent devices in flat panel displays, and in photovoltaic and sensor devices, and to a field effect transistor, light emitting device or ID tag comprising the reactive thienothiophenes.
    Type: Application
    Filed: July 9, 2002
    Publication date: May 1, 2003
    Applicant: Merck Patent GmbH
    Inventors: Louise Farrand, Marcus Thompson, Mark Giles, Mark Goulding, Martin Heeney, Steven Tierney, Maxim Shkunov, David Sparrowe, Iain McCulloch
  • Patent number: 6469146
    Abstract: The invention concerns radiopharmaceutical products suitable for the selective labeling of lymphomas containing a metal complex with the formula: [M(R1CS2)(R1CS3)2] in which M is chosen from among 99mTc, 186Re and 188Re, and R1 represents an alkyl, cycloalkyl, aralkyl or aryl group, optionally substituted, obtained by reaction of a pertechnetate or a perrhenate with a reducing agent such as SnCl2ZP2O in the presence of a dithiocarboxylate having the formula: (R1CS2)−Z2+.
    Type: Grant
    Filed: May 31, 2000
    Date of Patent: October 22, 2002
    Assignee: Cis Bio International
    Inventors: Roberto Pasqualini, Emmanuel Bellande, Franck Mevellec, Alain Roucoux, Nicolas Noiret, Henri Patin
  • Patent number: 6392067
    Abstract: HIV protease inhibitors inhibit or block the biological activity of the HIV protease enzyme, causing the replication of the HIV virus to terminate. These compounds can be prepared by the novel methods of the present invention using the novel inventive intermediates.
    Type: Grant
    Filed: May 21, 2001
    Date of Patent: May 21, 2002
    Assignees: Agouron Pharmaceuticals, Inc., Japan Tobacco Inc.
    Inventors: Srinivasan Babu, Bennett C. Borer, Travis P. Remarchuk, Robert J. Szendroi, Kathleen R. Whitten, Juliette K. Busse, Kim F. Albizati
  • Patent number: 6316180
    Abstract: Detectable compounds comprising a chemically-transformable first compound covalently linked to an electrochemiluminescent compound are provided. Such compounds are useful in processes and kits that monitor the status of the first compound and derive information from such monitoring. A rapid single step assay suitable for the detection or quantification of &bgr;-lactam antibiotics and &bgr;-lactamases. The assay can be performed directly on samples of food, such as milk and meat, blood or serum and is useful in determining the suitability of a particular antibiotic in treating a particular bacterial infection and in diagnosis of a bacterial infection. The assay is also useful in determining and quantifying &bgr;-lactam antibiotic resistance. The assay can be performed on an IGEN OrigenR Analyzer.
    Type: Grant
    Filed: June 23, 1997
    Date of Patent: November 13, 2001
    Assignee: IGEN International, Inc.
    Inventor: Mark T. Martin
  • Patent number: 5917056
    Abstract: The present invention relates to novel 10-deacetyl-14.beta.-hydroxybaccatine III derivatives. The novel derivatives, having cytotoxic and antitumour activity, are prepared from this synton after functionalization of the hydroxyls at 1-, 14- as thiocarbonate, iminocarbonate and sulfite and possible oxidation of the hydroxyl at C.sub.10. These derivatives are subjected to a subsequent esterification at position 13- with a variously substituted isoserine chain. The products of the invention can be administered by the injective or oral route, when suitably formulated.
    Type: Grant
    Filed: August 5, 1997
    Date of Patent: June 29, 1999
    Assignee: INDENA S.p.A.
    Inventor: Ezio Bombardelli
  • Patent number: 5869697
    Abstract: A compound of formula (IV) ##STR1## wherein R.sup.1 is hydrogen, an alkyl, alkoxy, alkylamino, alkylthio, aryl, aryloxy, or halogen residue; R is an alkyl, or aryl residue, and X is S or C, which is a valuable intermediate for producing Diltiazem.
    Type: Grant
    Filed: July 7, 1997
    Date of Patent: February 9, 1999
    Assignee: Council of Scientific & Industrial Research
    Inventors: Lohray Braj Bhushan, Balakrishnan Ezhuthachan Jayachandran, Lohray Vidya Bhushan, Ravindranathan Thottappillil
  • Patent number: 5643713
    Abstract: Detectable compounds comprising a chemically-transformable first compound covalently linked to an electrochemiluminescent compound are provided. Such compounds are useful in processes and kits that monitor the status of the first compound and derive information from such monitoring.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: July 1, 1997
    Inventors: Pam Liang, Mark T. Martin, Liwen Dong
  • Patent number: 5641623
    Abstract: A rapid single step assay suitable for the detection or quantification of .beta.-lactam antibiotics and .beta.-lactamases. The assay can be performed directly on samples of food, such as milk and meat, blood or serum and is useful in determining the suitability of a particular antibiotic in treating a particular bacterial infection and in diagnosis of a bacterial infection. The assay is also useful in determining and quantifying .beta.-lactam antibiotic resistance. The assay can be performed on an IGEN Origen.sup.R Analyzer.
    Type: Grant
    Filed: January 4, 1995
    Date of Patent: June 24, 1997
    Inventor: Mark T. Martin
  • Patent number: 5488115
    Abstract: Novel alcohols of the formula ##STR1## wherein R.sup.a is azido or phthalimido, R.sup.4 is alkyl, cycloalkyl, cycloalkylalkyl, aryl or aralkyl, R.sup.7 and R.sup.8 together are a trimethylene or tetramethylene group which is optionally substituted by hydroxy, alkoxycarbonylamino or acylamino or in which one --CH.sub.2 -- group is replaced by --NH--, --N(alkoxycarbonyl)--, --N(acyl)-- or --S-- or which carries a fused cycloalkane, aromatic or heteroaromatic ring, and R.sup.9 is alkoxycarbonyl, monoalkylcarbamoyl, monoaralkylcarbamoyl, monoarylcarbamoyl or a group of the formula ##STR2## in which R.sup.10 and R.sup.11 each is alkyl, are described along with a process for their manufacture. These alcohols are useful as intermediates, for example in the manufacture of amino acid derivatives having antiviral activity.
    Type: Grant
    Filed: May 12, 1995
    Date of Patent: January 30, 1996
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Kevin E. B. Parkes, Sally Redshaw, Gareth J. Thomas
  • Patent number: 5336683
    Abstract: The invention is concerned with novel antioxidants, namely the [R] and, respectively, [S] compounds of the formula ##STR1## wherein R.sup.1 and R.sup.2 together represent the --S(O)-- group and R.sup.3 and R.sup.4 represent hydrogen, or R.sup.3 and R.sup.4 together represent the --S(O)-- group and R.sup.1 and R.sup.2 represent hydrogen.
    Type: Grant
    Filed: January 13, 1993
    Date of Patent: August 9, 1994
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Horst Pauling, Christof Wehrli
  • Patent number: 5321143
    Abstract: A ruthenium catalyzed method to synthesize cyclic sulfate compounds from the corresponding cyclic sulfites, and the cyclic sulfate reaction products obtained by this method. These cyclic sulfates further react with selected nucleophiles to give various substituted products. The method is an efficient means for the synthesis of chiral building blocks from tartaric acid enantiomers in high yields using an overall two-stage, one-pot reaction procedure. The chiral compounds can be transformed by nucleophilic reactions into chiral building blocks useful for the synthesis of natural biologically active products, such as antibiotics and pheromones.
    Type: Grant
    Filed: June 7, 1991
    Date of Patent: June 14, 1994
    Assignee: Massachusetts Institute of Technology
    Inventors: K. Barry Sharpless, Yun Gao
  • Patent number: 5286899
    Abstract: An efficient and commercially-viable method for the stereoselective transformation of a diol to an alcohol is disclosed. The present method is particularly well-suited for the preparation of the unnatural D-isomer of malic acid or its derivatives from the abundant naturally occurring L-tartaric acid or derivatives thereof.
    Type: Grant
    Filed: August 27, 1992
    Date of Patent: February 15, 1994
    Assignee: Sepracor, Inc.
    Inventor: Yun Gao
  • Patent number: 5274123
    Type: Grant
    Filed: December 10, 1992
    Date of Patent: December 28, 1993
    Assignee: Rhone-Poulenc Rorer, S.A.
    Inventors: Roger Deruelle, Michel Guinard, Gerard Perrier
  • Patent number: 5223531
    Abstract: Disclosed is a 1,3,2-dioxathiolan-S-oxide derivative as represented by the general formula (I): ##STR1## (where R.sub.1 and R.sub.2 are identical to or different from each other and each is a hydrogen atom or a lower alkyl group;X is a halogen atom, a cyano group, a lower alkyl group, a haloalkyl group or a phenyl group;m is 0 or an integer from 1 to 5; and when small m is greater than 1 each x can be the same or different andn is 1 or 2).A 1,3,2-dioxathiolan-2-oxide derivative of the compound as represented by the general formula (I-I) is prepared by reacting a hydroxymethylcyclopentanol derivative with thionyl chloride; and a 1,3,2-dioxathiolan-2,2-dioxide derivative (I-II) thereof is prepared by oxidizing the compound (I-I). The compounds (I) can be employed as fungicides and intermediate compounds for the preparation of azolylmethylcyclopentanol derivatives.
    Type: Grant
    Filed: August 20, 1992
    Date of Patent: June 29, 1993
    Assignee: Kureha Chemical Industry Co., Ltd.
    Inventors: Satoru Kumazawa, Masanori Minoguchi
  • Patent number: 5214056
    Abstract: A 1,3,2-dioxathiolane oxide derivative is represented by the following formula: ##STR1## wherein X represents --S(O)-- or --S(O).sub.2 --;R.sup.1 represents a hydrogen atom, an alkali metal atom, a benzyl group, or a lower alkyl group;R.sup.2 represents a lower alkyl group which may be substituted with a methylthio group, or a benzyl group, andR.sup.3 and R.sup.4 may be the same or different and independently represent a hydrogen atom, an alkyl group having one to ten carbon atoms, a lower alkyl group substituted with a guanidyl group, a cycloalkyl group having 3 to 6 carbon atoms, a phenyl group, a benzyl group, or a phenethyl group, or together form an alkylene group.
    Type: Grant
    Filed: August 20, 1991
    Date of Patent: May 25, 1993
    Assignee: Japan Tobacco Inc.
    Inventors: Jun-ichi Haruta, Masahiro Tanaka, Itsuo Uchida, Akira Ohta, Shin Hara
  • Patent number: 5189200
    Abstract: An efficient and commerically-viable method for the stereoselective transformation of a diol to an alcohol is disclosed. The present method is particularly well-suited for the preparation of the unnatural D-isomer of malic acid or its derivatives from the abundant naturally occurring L-tartaric acid or derivatives thereof.
    Type: Grant
    Filed: December 21, 1990
    Date of Patent: February 23, 1993
    Assignee: Sepracor, Inc.
    Inventor: Yun Gao
  • Patent number: 5162554
    Abstract: Stable, optically active enantiomers of substituted glyceraldehydes or glycidaldehydes are synthesized by using osmium-catalyzed asymmetric dihydroxylation of an olefin which is a substituted 1,5-dihydro-3H-2,4-benzodioxepine. For example, the protected glyceraldehyde, 3-(1,2-dihydroxyethyl)-1,5-dihydro-3H-2,4-benzodioxepine and the protected glycidaldehyde, 3-(1,2-epoxyethyl)-1,5-dihydro-3H-2,4-benzodioxepine have been synthesized and the optical enantiomer has been recovered. In the synthetic and isolation methods, enantiomers with high enantiomeric excess are recovered from the mother liquor following a recrystallization step.
    Type: Grant
    Filed: June 18, 1991
    Date of Patent: November 10, 1992
    Assignee: Massachusetts Institute of Technology
    Inventors: K. Barry Sharpless, Ryu Oi
  • Patent number: 5116999
    Abstract: Cyclic sulphates of formula: ##STR1## are prepared by oxidation of a cyclic sulphite of formula: ##STR2## with a hypohalite of an alkali or alkaline-earth metal and a catalytic quantity of a ruthernium derivative (RuO.sub.2, RuCl.sub.3). In formulae (I) and (II), R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are identical or different and each represents hydrogen, halogen, alkyl, alkoxy, aryl, aryloxy or alkoxycarbonyl.
    Type: Grant
    Filed: April 12, 1990
    Date of Patent: May 26, 1992
    Assignee: Rhone Poulenc Sante
    Inventors: Pierre Le Roy, Bernadette Mandard-Cazin
  • Patent number: 5112990
    Abstract: A ruthenium catalyzed method to synthesize cyclic sulfate compounds from the corresponding cyclic sulfites, and the cyclic sulfate reaction products obtained by this method. These cyclic sulfates further react with selected nucleophiles to give various substituted products. The method is an efficient means for the synthesis of chiral building blocks from tartaric acid enantiomers in high yields using an overall two-stage, one-pot reaction procedure. The chiral compounds can be transformed by nucleophilic reactions into chiral building blocks useful for the synthesis of natural biologically active products, such as antibiotics and pheromones.
    Type: Grant
    Filed: June 21, 1989
    Date of Patent: May 12, 1992
    Assignee: Massachusetts Institute of Technology
    Inventors: K. Barry Sharpless, Yun Gao
  • Patent number: 5023342
    Abstract: A ruthenium catalyzed method to synthesize cyclic sulfate compounds from the corresponding cyclic sulfites, and the cyclic sulfate reaction products obtained by this method. These cyclic sulfates further react with selected nucleophiles to give various substituted products. The method is an efficient means for the synthesis of chiral building blocks from tartaric acid enantiomers in high yields using an overall two-stage, one-pot reaction procedure. The chiral compounds can be transformed by nucleophilic reactions into chiral building blocks useful for the synthesis of natural biologically active products, such as antibiotics and pheromones.
    Type: Grant
    Filed: May 26, 1988
    Date of Patent: June 11, 1991
    Assignee: Massachusetts Institute of Technology
    Inventors: K. Barry Sharpless, Yun Gao
  • Patent number: 4960904
    Abstract: Cyclic sulphates of formula: ##STR1## are prepared by oxidation of a cyclic sulphite of formula: ##STR2## with a hypohalite of an alkali or alkaline-earth metal and a catalytic quantity of a ruthernium derivative (RuO.sub.2, RuCl.sub.3). In formulae (I) and (II), R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are identical or different and each represents hydrogen, halogen, alkyl, alkoxy, aryl, aryloxy or alkoxycarbonyl.
    Type: Grant
    Filed: September 6, 1989
    Date of Patent: October 2, 1990
    Assignee: Rhone-Poulenc Sante
    Inventors: Pierre Le Roy, Bernadette Mandard-Cazin
  • Patent number: 4924007
    Abstract: Cyclic sulphates of formula ##STR1## in which R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, and R.sub.6, which are identical or different, each denote hydrogen, halogen, alkyl, alkoxy, aryloxy or alkoxycarbonyl and n is 0 or 1, are prepared by rapid reaction, at a temperature of 150.degree. to 250.degree. C.
    Type: Grant
    Filed: May 15, 1989
    Date of Patent: May 8, 1990
    Assignee: Rhone-Poulenc Sante
    Inventors: Viviane Massonneau, Michel Mulhauser
  • Patent number: 4841070
    Abstract: The novel 5,6-sulfinyl-L-ascorbic acid and its stereoisomers, their manufacture by sulfinylating L-ascorbic acid or corresponding stereoisomers, compositions having oxidation-inhibiting properties which contain 5,6-sulfinyl-L-ascorbic acid or a stereoisomer thereof as well as the use of 5,6-sulfinyl-L-ascorbic acid or a stereoisomer thereof as an antioxidant are described.
    Type: Grant
    Filed: June 24, 1988
    Date of Patent: June 20, 1989
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Horst Pauling, Christof Wehrli
  • Patent number: 4761486
    Abstract: Cyclohexenone derivatives of the formula ##STR1## where R.sup.1, R.sup.2, A and X have the meanings given in the disclosure, a process for their manufacture, herbicidal and plant growth-regulating agents containing the novel active ingredients, and methods of combating unwanted plant growth and of regulating plant growth.
    Type: Grant
    Filed: January 14, 1987
    Date of Patent: August 2, 1988
    Assignee: BASF Aktiengesellschaft, Patentabteilung
    Inventors: Bernd Zeeh, Dieter Jahn, Michael Keil, Dieter Kolassa, Bruno Wuerzer, Norbert Meyer, Wilhelm Rademacher, Johann Jung
  • Patent number: 4725682
    Abstract: Sulfur-containing bis-amino carbamate compounds exhibit outstanding acaricidal, nematocidal and insecticidal activity.
    Type: Grant
    Filed: December 2, 1986
    Date of Patent: February 16, 1988
    Assignee: Rhone-Poulenc Nederland, B.V.
    Inventor: Themistocles D. J. D'Silva
  • Patent number: 4666502
    Abstract: The invention provides 5-membered heteroaromatic compounds of formula IArN(Y)COCH.sub.2 Cl Iwherein Ar is a 5-membered heteroaromatic group comprising 1 or 2 heteroatoms selected from O, S and N and linked by a ring C-atom to the N-atom of the N(Y)COCH.sub.2 Cl group to which it is bound, whereby where Ar is pyrazolyl, said N(Y)COCH.sub.2 Cl group is in the 4-position,and Y is as specified in the description,the use of these compounds as herbicides, compositions for facilitating such use and the preparation of the chloroacetamides.
    Type: Grant
    Filed: February 3, 1983
    Date of Patent: May 19, 1987
    Assignee: Sandoz Ltd.
    Inventors: Karl Seckinger, Fred Kuhnen, Karlheinz Milzner
  • Patent number: 4617151
    Abstract: 2- or 2,3-substituted 5,6,11,12-tetraseleneotetracene or -tetrathiotetracene of the formula ##STR1## in which X is S or Se, R is alkoxy, hydroxyalkoxy, aryloxy, cycloalkoxy, aralkoxy, --OH, --NH.sub.2, --Cl, --Br or substituted amino and Y is hydrogen or --COR. The compounds can be bonded as side groups to polymers. The polymers and the compounds combine with electron acceptors to form charge transfer complexes which can be used as electrically conductive layers.
    Type: Grant
    Filed: March 15, 1985
    Date of Patent: October 14, 1986
    Assignee: Ciba-Geigy Corporation
    Inventors: Carl W. Mayer, Vratislav Kvita, Josef Pfeifer
  • Patent number: 4386214
    Abstract: Cyclic perfluoroaliphaticdisulfonic acid anhydrides, sulfonamide derivatives thereof, a process for making the same, curable compositions containing cyclic perfluoroaliphaticdisulfonic acid anhydrides or sulfonamide derivatives thereof and cationically-sensitive monomers, and a process for using cyclic perfluoroaliphaticdisulfonic acid anhydrides or sulfonamide derivatives thereof as catalysts for the cure of cationically-sensitive monomers.
    Type: Grant
    Filed: December 1, 1981
    Date of Patent: May 31, 1983
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: Fred E. Behr
  • Patent number: 4329478
    Abstract: Cyclic perfluoroaliphaticdisulfonic acid anhydrides, sulfonamide derivatives thereof, a process for making the same, curable compositions containing cyclic perfluoroaliphaticdisulfonic acid anhydrides or sulfonamide derivatives thereof and cationically-sensitive monomers, and a process for using cyclic perfluoroaliphaticdisulfonic acid anhydrides or sulfonamide derivatives thereof as catalysts for the cure of cationically-sensitive monomers.
    Type: Grant
    Filed: January 30, 1981
    Date of Patent: May 11, 1982
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: Fred E. Behr
  • Patent number: 4259507
    Abstract: 3,5-di-(2-methylpropyl)-1,2,4-trithiolane having the formula: ##STR1## and its "cis" and "trans" isomers represented by the structures: ##STR2## and described as being useful in augmenting or enhancing the organoleptic properties (taste and aroma) of foodstuffs.
    Type: Grant
    Filed: August 3, 1979
    Date of Patent: March 31, 1981
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Chi-Kuen Shu, Braja D. Mookherjee, Manfred H. Vock