Substituted Patents (Class 560/266)
  • Patent number: 10246400
    Abstract: The present invention relates to a method for the acetylation of an aqueous solution of lactic acid to (S)-2-acetyloxypropionic acid. The process comprises in particular removing water from the solution of lactic acid and reacting lactic acid with acetic anhydride in the presence of acetic acid.
    Type: Grant
    Filed: April 5, 2018
    Date of Patent: April 2, 2019
    Assignee: Bracco Imaging S.P.A.
    Inventors: Roberta Fretta, Pietro Delogu, Fernanda Di Giorgio, Alfonso Nardelli, Stefano Sguassero, Carlo Felice Viscardi
  • Patent number: 9963416
    Abstract: The present invention relates to a method for the acetylation of an aqueous solution of lactic acid to (S)-2-acetyloxypropionic acid. The process comprises in particular removing water from the solution of lactic acid and reacting lactic acid with acetic anhydride in the presence of acetic acid.
    Type: Grant
    Filed: June 10, 2015
    Date of Patent: May 8, 2018
    Assignee: Bracco Imaging S.P.A.
    Inventors: Roberta Fretta, Pietro Delogu, Fernanda Di Giorgio, Alfonso Nardelli, Stefano Sguassero, Carlo Felice Viscardi
  • Patent number: 9090556
    Abstract: The disclosure relates to a process for forming an acyloxy carboxylic acid or a derivative of the acid. A hydroxy acid compound is reacted with a carboxylic acid in a reaction vessel and in the presence of a catalyst, such as in a reactive distillation column containing the catalyst. The reaction product formed in the reaction vessel includes an acyloxy carboxylic acid compound, which can be removed continuously from the vessel in a product stream. Another product stream containing unreacted (excess) carboxylic acid and/or reaction byproducts such as water can be separately removed continuously from the reaction vessel.
    Type: Grant
    Filed: December 7, 2012
    Date of Patent: July 28, 2015
    Assignee: BOARD OF TRUSTEES OF MICHIGAN STATE UNIVERSITY
    Inventors: Dennis Miller, Carl T. Lira, Lars Peereboom, Aspi K. Kolah
  • Publication number: 20150132702
    Abstract: A method for fabricating a semiconductor product includes applying a photo-resist layer to a substrate, the photo-resist layer including a higher acid concentration at an upper portion of the photo-resist layer than at a lower portion of the photo-resist layer. The method also includes exposing the photo-resist layer to a light source through a mask including a feature, the photo-resist layer including a floating, diffusing acid that will diffuse into a region of the photo-resist layer affected by the feature while not diffusing into a feature formed by the mask.
    Type: Application
    Filed: January 16, 2015
    Publication date: May 14, 2015
    Inventors: Ching-Yu Chang, Ming-Feng Shieh, Wen-Hung Tseng
  • Publication number: 20140275603
    Abstract: A process for making a 2-nitro-1-ethanol derivative of formula III: wherein R3 is as described herein is provided. Novel 2-nitro-1-ethanol derivatives provided.
    Type: Application
    Filed: March 26, 2012
    Publication date: September 18, 2014
    Applicant: ANGUS Chemical Company
    Inventors: Raymond J. Swedo, George David Green, Charles E. Coburn
  • Publication number: 20140256928
    Abstract: A protecting group for 1-nitrogen atom of an indole group including a sulfonylethyl carbamate group, wherein the protecting group is represented by the following General Formula (I) and capable of being removed from the 1-nitrogen atom of the indole group in an aprotic solvent: where R represents an alkyl group, a derivative of the alkyl group, a phenyl group or a derivative of the phenyl group.
    Type: Application
    Filed: May 9, 2014
    Publication date: September 11, 2014
    Applicant: APTA BIOSCIENCES LTD.
    Inventor: Tsuyoshi FUJIHARA
  • Patent number: 8829231
    Abstract: The present invention relates to a new way for the production of 4-acetoxy-2-methyl-butanal, wherein a non-acidic catalytic system is used.
    Type: Grant
    Filed: January 16, 2012
    Date of Patent: September 9, 2014
    Assignee: DSM IP Assets B.V.
    Inventors: Werner Bonrath, Jan Schütz
  • Patent number: 8741966
    Abstract: The present disclosure relates to lipid compounds of formula (I): wherein: R1 is chosen from a C10-C21 alkyl, a C10-C21 alkenyl having 1-6 double bonds, and a C10-C21 alkynyl having 1-6 triple bonds; R2 and R3 are the same or different and are chosen from hydrogen and a C1-C6 alkyl; X is chosen from O, S, SO, SO2, Si, and Se; n=1 or 3; and P1 is chosen from hydrogen; a C10-C21 alkyl, a C10-C21 alkenyl having 1-6 double bonds, a C10-C21 alkynyl having 1-6 triple bonds, optionally substituted; a group of formula (II) or formula (III), wherein P2, P3, and P4 are chosen from hydrogen, an alkyl, an alkenyl, and an alkynyl, optionally substituted; and a group of formula (IV) or formula (V), wherein P5 is chosen from hydrogen and a C1-C6 alkyl; or a pharmaceutically acceptable salt, complex, or solvate thereof.
    Type: Grant
    Filed: November 6, 2008
    Date of Patent: June 3, 2014
    Assignee: Pronova Biopharma Norge AS
    Inventor: Anne Kristin Holmeide
  • Publication number: 20140081042
    Abstract: The present invention relates to a new way for the production of 4-acetoxy-2-methyl-butanal, wherein a non-acidic catalytic system is used.
    Type: Application
    Filed: January 16, 2012
    Publication date: March 20, 2014
    Applicant: DSM IP ASSETS B.V.
    Inventors: Werner Bonrath, Jan Schütz
  • Publication number: 20130295229
    Abstract: The present invention relates to the use of 3-mercaptoheptyl carboxylate in the form of any one of its stereoisomers or in the form of a mixture thereof. The compounds of the invention are valuable flavoring ingredients capable of imparting fruity, citrus and/or teas aftertaste with a well-balanced long-lastingness. The present invention also concerns the compositions or articles containing the compound.
    Type: Application
    Filed: July 11, 2013
    Publication date: November 7, 2013
    Inventors: Sina Dorothea Escher, Yvan Niclass, Lionel Saudan
  • Publication number: 20130150619
    Abstract: The disclosure relates to a process for forming an acyloxy carboxylic acid or a derivative of the acid. A hydroxy acid compound is reacted with a carboxylic acid in a reaction vessel and in the presence of a catalyst, such as in a reactive distillation column containing the catalyst. The reaction product formed in the reaction vessel includes an acyloxy carboxylic acid compound, which can be removed continuously from the vessel in a product stream. Another product stream containing unreacted (excess) carboxylic acid and/or reaction byproducts such as water can be separately removed continuously from the reaction vessel.
    Type: Application
    Filed: December 7, 2012
    Publication date: June 13, 2013
    Applicant: BOARD OF TRUSTEES OF MICHIGAN STATE UNIVERSITY
    Inventor: BOARD OF TRUSTEES OF MICHIGAN STATE UNIVERSITY
  • Publication number: 20120197036
    Abstract: A method for manufacturing a ketone, includes oxidizing an internal olefin or a cyclic olefin having a functional group containing a hetero atom and one carbon-carbon double bond or more at a position other than terminals of a molecule thereof in an amide-based solvent in the presence of water, a palladium catalyst, and molecular oxygen, without oxidizing the functional group, thereby bonding an oxo group to at least one of the carbon atoms constituting the carbon-carbon double bond. The amide-based solvent is represented by formula (1): wherein R1 represents an alkyl group having 1 to 4 carbon atoms; R2 and R3 each independently represent an alkyl group having 1 to 4 carbon atoms or an aryl group; and when R1 and R2 are alkyl groups, R1 and R2 may be bonded to each other to form a ring structure.
    Type: Application
    Filed: October 8, 2010
    Publication date: August 2, 2012
    Applicants: Osaka University, JX NIPPON OIL & ENERGY CORPORATION
    Inventors: Kiyotomi Kaneda, Hisashi Sone
  • Publication number: 20120083619
    Abstract: Described herein is a process for the manufacture of hydrofluoroalkanols of the structure RfCFClCHROH. Also described herein are methods of manufacturing hydrofluoroalkenes of the structure RfCF?CHR from halofluorocarbons of the structure RfCFX2. In particular, 2,3,3,3,-tetrafluoro-1-propene may be manufactured with this process. Also described are compounds of the formula RfCFClCHROC(?O)R?.
    Type: Application
    Filed: October 11, 2011
    Publication date: April 5, 2012
    Applicant: E.I. DU PONT DE NEMOURS AND COMPANY
    Inventors: Mario Joseph Nappa, Xuehui Sun, Lev Moiseevich Yagupolskii, Andrey Anatolievich Filatov, Vladimir Nikolaevich Boiko, Yurii Lvovich Yagupolskii
  • Patent number: 8143440
    Abstract: There is provided a method for separating and collecting at least alcohol with a high purity from an azeotropic mixture of olefin and alcohol.
    Type: Grant
    Filed: January 9, 2009
    Date of Patent: March 27, 2012
    Assignee: Daikin Industries, Ltd.
    Inventors: Yuuki Matsuda, Kazuyoshi Ichihara, Takeomi Hirasaka, Takuya Ichida
  • Patent number: 8124805
    Abstract: A process for the production of 4-acetoxybutyraldehyde is described. The process comprises reacting allyl acetate with a mixture of carbon monoxide and hydrogen in the presence of a solvent and a catalyst comprising a rhodium complex and a diphosphine. The diphoshine is a substituted or unsubstituted 2,2?-bis(dihydrocarbylphosphino)diphenyl ether. The process gives a high ratio of 4-acetoxybutyraldehyde:3-acetoxy-2-methylpropionaldehyde.
    Type: Grant
    Filed: November 25, 2009
    Date of Patent: February 28, 2012
    Assignee: Lyondell Chemical Technology, L.P.
    Inventor: Daniel F. White
  • Publication number: 20110178323
    Abstract: Provided is a method for producing a tetrafluoro nitrogen-containing heterocyclic compound such as tetrafluoropyrrolidine in good yield and at low cost. The method comprises the steps of: (A) reacting a compound represented by the formula (I) with fluorine gas to produce a tetrafluoro compound represented by the formula (II), (B) converting the tetrafluoro derivative represented by the formula (II) to a compound represented by the formula (III), and (C) reacting the compound represented by the formula (III) with an amine compound represented by the formula NH2R9 to produce a tetrafluoro nitrogen-containing heterocyclic compound represented by the formula (IV) or salt thereof.
    Type: Application
    Filed: October 2, 2009
    Publication date: July 21, 2011
    Applicant: NIPPON SODA CO., LTD.
    Inventor: Yasuhiro Miyashita
  • Publication number: 20110118455
    Abstract: A protecting group for 1-nitrogen atom of an indole group including a sulfonylethyl carbamate group, wherein the protecting group is represented by the following General Formula (I) and capable of being removed from the 1-nitrogen atom of the indole group in an aprotic solvent: where R represents an alkyl group, a derivative of the alkyl group, a phenyl group or a derivative of the phenyl group.
    Type: Application
    Filed: November 19, 2010
    Publication date: May 19, 2011
    Applicant: FUJITSU LIMITED
    Inventor: Tsuyoshi FUJIHARA
  • Publication number: 20100280109
    Abstract: The present disclosure relates to lipid compounds of formula (I): wherein: R1 is chosen from a C10-C21 alkyl, a C10-C21 alkenyl having 1-6 double bonds, and a C10-C21 alkynyl having 1-6 triple bonds; R2 and R3 are the same or different and are chosen from hydrogen and a C1-C6 alkyl; X is chosen from O, S, SO, SO2, Si, and Se; n=1 or 3; and P1 is chosen from hydrogen; a C10-C21 alkyl, a C10-C21 alkenyl having 1-6 double bonds, a C10-C21 alkynyl having 1-6 triple bonds, optionally substituted; a group of formula (II) or formula (III), wherein P2, P3, and P4 are chosen from hydrogen, an alkyl, an alkenyl, and an alkynyl, optionally substituted; and a group of formula (IV) or formula (V), wherein P5 is chosen from hydrogen and a C1-C6 alkyl; or a pharmaceutically acceptable salt, complex, or solvate thereof.
    Type: Application
    Filed: November 6, 2008
    Publication date: November 4, 2010
    Inventor: Anne Kristin Holmeide
  • Publication number: 20100209827
    Abstract: There is disclosed a sulfonate shown by the following general formula (2). R1—COOC(CF3)2—CH2SO3?M+??(2) (In the formula, R1 represents a linear, a branched, or a cyclic monovalent hydrocarbon group having 1 to 50 carbon atoms optionally containing a hetero atom. M+ represents a cation.) There can be provided: a novel sulfonate which is effective for a chemically amplified resist composition having a sufficiently high solubility (compatibility) in a resist solvent and a resin, a good storage stability, a PED stability, a further wider depth of focus, a good sensitivity, in particular a high resolution and a good pattern profile form; a photosensitive acid generator; a resist composition using this; a photomask blank, and a patterning process.
    Type: Application
    Filed: February 16, 2010
    Publication date: August 19, 2010
    Applicant: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Masaki OHASHI, Takeshi KINSHO, Youichi OHSAWA
  • Patent number: 7544831
    Abstract: The present invention provides a green catalytic process for the synthesis of acetyl salicylic acid using solid acid catalysts at atmospheric pressure. The invention involve the solid acid catalyst such as sulfated transition metal oxides namely nano-crystalline sulfated zirconia, sulfated titania; modified zeolites namely zeolite H-beta, H-Y, H-ZSM-5 and K-10 montmorillonite clay in a solvent free environment using salicylic acid and acetic anhydride with yield about 95% and high selectivity (100%). The solid acid catalysts can be recovered, regenerated and reused.
    Type: Grant
    Filed: September 21, 2007
    Date of Patent: June 9, 2009
    Assignee: Council of Scientific and Industrial Research
    Inventors: Raksh Vir Jasra, Beena Tyagi, Manish Kumar Mishra
  • Patent number: 6444842
    Abstract: The present invention provides an improved method for the preparation of carboxylic acid esters of alkylene glycol monoalkyl ethers by the acid catalyzed esterification of the monoalkyl ether with a carboxylic acid. In a preferred embodiment of the invention, the carboxylic acid and alcohol are reacted in a reactor/column and the resulting ester product is distilled into an overhead decanter/extractor as a single phase. A small amount of solvent, preferably a hydrocarbon is added to the mixture causing the resulting distillate to separate into two phases, one phase containing the desired product, the other containing primarily water. The process described is applicable to both batch and continuous operation and is not constrained by the difficulty of separating closely boiling azeotropes and results in substantially higher production rates than achieved by current processes.
    Type: Grant
    Filed: April 19, 2000
    Date of Patent: September 3, 2002
    Assignee: Celanese International Corporation
    Inventors: H. Robert Gerberich, R. Jay Warner
  • Patent number: 6348622
    Abstract: There is provided a compound of the formula[I]: wherein R represents a hydrogen atom or a protective group for a hydroxyl group; and A represents a hydrogen atom, a halogen atom or a group of the formula A1: Q represents Q3: when A represents a halogen atom or a protective group for a hydroyl group, A represents Q4:  wherein R1 and R2 represent a hydrogen atom or a protective group for a hydroxyl group; and when A represents a hydrogen atom, Q is Q2:
    Type: Grant
    Filed: February 9, 2000
    Date of Patent: February 19, 2002
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Toshiya Takahashi, Shinzo Seko, Takashi Miki
  • Patent number: 6323174
    Abstract: The invention provides a chain diene compound with desirable regioselectivity, in the presence of a specific ruthenium compound. This chain diene compound is a promising raw material for terpene. It has a structure represented by the general formula (I): wherein R1 represents H, a C1-C6 alkyl group which may be substituted or a C2-C6 alkenyl group which may be substituted, R2 represents a phenyl group which may have a C1-C4 alkyl group or a C1-C12 acyloxy group which may have a phenyl group or a naphthyl group, or a benzyl group or R2 is a hydroxy group which reversibly forms an aldehyde group through shifting of the position of the double bond adjacent to said hydroxy group. The chain diene compound is produced by reacting 2-substituted-1,3-butadienes with terminal olefins in the presence of a ruthenium compound in a hydrophilic solvent.
    Type: Grant
    Filed: May 16, 2000
    Date of Patent: November 27, 2001
    Assignee: Takasago International Corporation
    Inventors: Mitsuhiko Fujiwhara, Takenobu Nishikawa, Yoji Hori, Toshimitsu Hagiwara, Hisao Iwai, Takashi Miura
  • Patent number: 6288285
    Abstract: A process for producing dichloroacetoxypropane comprising reacting allyl acetate with chlorine in a gaseous phase in the presence of a catalyst comprising an element of Group 16 of the long-form Periodic Table or in the absence of a catalyst. The dichloroacetoxypropane obtained may be converted to dichloropropanol and epichlorohydrin.
    Type: Grant
    Filed: March 29, 2000
    Date of Patent: September 11, 2001
    Assignee: Showa Denko K.K.
    Inventors: Takanori Aoki, Takami Ohe, Haruki Ishikami
  • Patent number: 6124270
    Abstract: A cationic amphipathic compound of formula (I), ##STR1## wherein A is a single bond, an NH--R' grouping or (a), wherein --R'-- is a straight or branched, optionally substituted, saturated or unsaturated C.sub.1-22 aliphatic chain optionally interrupted by one or more O, S or N heteroatoms and one or more saturated, unsaturated or aromatic carbocyclic or heterocyclic radicals; each of R.sub.1, R.sub.2 and R.sub.3, which are the same or different, is a higher acyl or alkyl grouping; each of R.sub.7, R.sub.8 and R.sub.9, which are the same or different, is a (CH.sub.2).sub.n alkylene radical where 1.ltoreq.N.ltoreq.6; each of R.sub.4, R.sub.5 and R.sub.6, which are the same or different, is a hydrogen atom or an optionally substituted C.sub.1-22 alkyl, alkenyl, alkynyl or acyl radical optionally interrupted by one or more heteroatoms selected from), S and N, or one or more saturated, unsaturated or aromatic carbocyclic or heterocyclic radicals, or else at least two of the groupings R.sub.4, R.sub.5 and R.sub.
    Type: Grant
    Filed: March 3, 1997
    Date of Patent: September 26, 2000
    Assignee: Pasteur Merieux Serums et Vaccins
    Inventor: Jean Haensler
  • Patent number: 6118030
    Abstract: A process for producing dichloroacetoxypropane comprising reacting allyl acetate with chlorine in a gaseous phase in the presence of a catalyst. The dichloroacetoxypropane obtained may be converted to dichloropropanol and epichlorohydrin.
    Type: Grant
    Filed: February 16, 1999
    Date of Patent: September 12, 2000
    Assignee: Showa Denko K.K.
    Inventors: Takanori Aoki, Takami Ohe, Haruki Ishikami, Taketoshi Naitoh, Tatsuharu Arai
  • Patent number: 5777140
    Abstract: Process for the preparation of acyloxyalkanesulfonates having improved properties The acyloxyalkanesulfonates are obtained in accordance with the invention by direct esterification in which at least one fatty acid is esterified with at least one ammonium hydroxyalkanesulfonate of the formula HO-A-SO.sub.3.sup.- + NR.sup.1 R.sup.2 R.sup.3 R.sup.4 in which A is a C.sub.2 -C.sub.4 -alkylene and R.sup.1.sub.1 R.sup.2.sub.1 R.sup.3 and R.sup.4 are hydrogen or a C.sub.1 -C.sub.4 -alkylene group in the presence of an esterification catalyst at a temperature of not more than 200.degree. C., with removal of the water present. This process gives a product of high acyloxyalkane-ammonium sulfonate content without the need for a consistency regulator to be added.
    Type: Grant
    Filed: March 27, 1996
    Date of Patent: July 7, 1998
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Dirk Buhring
  • Patent number: 5665877
    Abstract: The present invention provides a novel synthesis of the compounds of Formula (I): ##STR1## The compounds are produced in high yield and without utilizing expensive chromatographic separations. The synthesis is particularly advantageous because it is stereoselective.
    Type: Grant
    Filed: May 17, 1996
    Date of Patent: September 9, 1997
    Assignee: Eli Lilly and Company
    Inventors: Margaret M. Faul, Michael R. Jirousek, Leonard L. Winneroski, II
  • Patent number: 5648513
    Abstract: The invention relates to a method of suppressing human body malodor by utilizing a deodorant composition containing a competitive substrate for the enzymatic creation of axillary body malodor. The compound is present in a dermatologically acceptable vehicle, and in an amount effective to reduce the conversion of malodor producing precursor. The present invention also relates to novel O-acylated serine compounds and method for the production thereof.
    Type: Grant
    Filed: November 22, 1995
    Date of Patent: July 15, 1997
    Inventor: Judith Wolfe Laney
  • Patent number: 5635571
    Abstract: Polyoxazolines having the structural formula: ##STR1## wherein R is phenylene or alkylene containing 2 to 18 carbon atoms, R.sup.2 is C.sub.1-4 alkyl and R.sub.1 is selected from the group consisting of C.sub.1-12 alkyl, vinyl, isopropylidene, pentafluoroethyl, phenyl, hydroxyphenyl which is optionally interrupted by up to 20 ethylene oxide groups, C.sub.1-2 -alkoxyphenyl which is optionally interrupted by up to 20 ethylene oxide groups and .paren open-st.CH.sub.2 CH.sub.2 --O.paren close-st..sub.r CH.sub.3 in which r ranges from 1-20, X is NH.sub.2 or OH, n ranges from 2 to 50 and m ranges from 0 to 50, wherein R.sub.1 is hydroxyphenyl optionally interrupted by up to 20 ethylene oxide groups only when X is NH.sub.2, are polymerizable to form hyperbranched polymers which have a number average molecular weight ranging from 5,000 to 150,000, a weight average molecular weight ranging from 5,500 to 5,000,000 and a polydispersity ranging from 1.
    Type: Grant
    Filed: June 5, 1996
    Date of Patent: June 3, 1997
    Assignee: Cornell Research Foundation, Inc.
    Inventors: Jean M. J. Frechet, Koji Yui
  • 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: 5614647
    Abstract: The present invention provides a novel synthesis of the compounds of Formula (I): ##STR1## The compounds are produced in high yield and without utilizing expensive chromatographic separations. The synthesis is particularly advantageous because it is stereoselective.
    Type: Grant
    Filed: May 25, 1995
    Date of Patent: March 25, 1997
    Assignee: Eli Lilly and Company
    Inventors: Margaret M. Faul, Michael R. Jirousek, Leonard L. Winneroski, II
  • Patent number: 5541347
    Abstract: The present invention provides a novel synthesis of the compounds of Formula (I): ##STR1## The compounds are produced in high yield and without utilizing expensive chromatographic separations. The synthesis is particularly advantageous because it is stereoselective.
    Type: Grant
    Filed: October 3, 1994
    Date of Patent: July 30, 1996
    Assignee: Eli Lilly and Company
    Inventors: Margaret M. Faul, Michael R. Jirousek, Leonard L. Winneroski II
  • Patent number: 5491145
    Abstract: Novel compound of the general formula: ##STR1## wherein R.sup.1 stands for a hydrogen atom, an optionally substituted lower alkyl group or a halogen atom; R.sup.2 and R.sup.3 respectively stand for a hydrogen atom or an optionally substituted lower alkyl group, provided that either R.sup.2 or R.sup.3 is a hydrogen atom, the other being an optionally substituted lower alkyl group, or R.sup.2 and R.sup.3 may, taken together with the adjacent --C=C-- group, form a 5- to 7-membered ring; X stands for an oxygen atom or S(O).sub.p (p stands for an integer from 0 to 2; Y stands for a group of the formula: ##STR2## (R.sup.4 and R.sup.5 respectively stand for a hydrogen atom or an optionally substituted lower alkyl group) or a divalent group derived from an optionally substituted 3- to 7-membered homocyclic or heterocyclic ring; R.sup.6 and R.sup.7 each stands for a hydrogen atom, an optionally substituted lower lakyl group, an optionally substituted cycloalkyl group or an optionally substituted aryl group, or R.sup.
    Type: Grant
    Filed: November 21, 1994
    Date of Patent: February 13, 1996
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Akio Miyake, Yasuhiko Kawano, Yasuko Ashida
  • Patent number: 5488135
    Abstract: The invention concerns the compounds of formula I ##STR1## wherein the substituents have various significances, in free form and, where such forms exist, in salt form. The compounds have potent antihyperproliferative/antiinflammatory and anticancer activity.
    Type: Grant
    Filed: October 16, 1992
    Date of Patent: January 30, 1996
    Assignee: Sandoz Ltd.
    Inventors: Peter Nussbaumer, Anton Stutz
  • Patent number: 5455371
    Abstract: A process for producing difluoromethyl ethers and esters by reacting an ether or an acid with a cadmium, zinc or bismuth compound containing the CF.sub.3 group and selected from the group consisting of Cd(CF.sub.3).sub.2, Zn(CF.sub.3).sub.2,Bi(CF.sub.3).sub.3, CdHal(CF.sub.3), ZnHal(CF.sub.3), BiHal(CF.sub.3).sub.2 and BiHal.sub.2 (CF.sub.3) in the presence of a Lewis acid.
    Type: Grant
    Filed: June 15, 1993
    Date of Patent: October 3, 1995
    Assignee: Solvay Fluor und Derivative GmbH
    Inventors: Dieter Naumann, Wieland Tyrra, Regina Moeckel
  • Patent number: 5360938
    Abstract: This invention relates to asymmetric syntheses in which a prochiral or chiral compound is contacted in the presence of an optically active metal-ligand complex catalyst to produce an optically active product.
    Type: Grant
    Filed: July 16, 1992
    Date of Patent: November 1, 1994
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: James E. Babin, Gregory T. Whiteker
  • Patent number: 5359128
    Abstract: The invention comprises compositions and methods for the treatment of psoriasis.
    Type: Grant
    Filed: February 11, 1993
    Date of Patent: October 25, 1994
    Inventor: Izhak Blank
  • Patent number: 5344952
    Abstract: A method for enzyme immunoassay for a ligand suspected to be present in a liquid sample includes signal amplification by use of at least two enzymes and a blocked modulator for one of the enzymes. Ligand present in the liquid binds to an antiligand and an enzyme-labeled tracer. The resulting bound fraction is separated and the enzyme in the tracer removes the blocking group from the blocked modulator. The modulator activates or inhibits a second enzyme which catalyzes the conversion of a substrate to a product. The presence or absence of the ligand in the liquid is indicated by a signal, such as a color change or a rate of color change, associated with the product. The invention includes a new class of enzyme inhibitors and blocked inhibitors and a kit of materials useful for performing the method of the invention.
    Type: Grant
    Filed: March 22, 1993
    Date of Patent: September 6, 1994
    Assignee: Becton, Dickinson and Company
    Inventors: Patrick D. Mize, James P. O'Connell
  • Patent number: 5231221
    Abstract: Compounds of the formula ##STR1## can advantageously be prepared by reacting compounds the formula II ##STR2## in which the substituents R.sup.1 -R.sup.4 have the meanings given, with the anhydride of the formula III ##STR3## in the presence of dimethyl sulfoxide and the acid corresponding to the anhydride of the formula III.
    Type: Grant
    Filed: March 18, 1991
    Date of Patent: July 27, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Winfried Hertzsch, Gerhard Jahne
  • Patent number: 5210315
    Abstract: A process for producing an .alpha.-hydroxyketone represented by formula (I): ##STR1## wherein R.sup.1 represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or an alkoxycarbonyl group; and R.sup.2 and R.sup.3 each represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aralkyl group, provided that they do not simultaneously represent a hydrogen atom; or a pair of R.sup.1 and R.sup.2, a pair of R.sup.1 and R.sup.3, or a pair of R.sup.2 and R.sup.3 is taken together to form a ring; and the pair of R.sup.1 and R.sup.2 and the pair of R.sup.2 and R.sup.3 may form a ring simultaneously, is disclosed, comprising reacting a compound represented by formula (II): ##STR2## wherein R.sup.1, R.sup.2, and R.sup.3 are as defined above, with an oxidizing agent in the presence of a ruthenium compound and water. .alpha.-Hydroxyketones useful as physiologically active substances are produced with good selectivity and in high yield.
    Type: Grant
    Filed: October 18, 1991
    Date of Patent: May 11, 1993
    Assignee: Takasago International Corporation
    Inventors: Takao Saito, Hidenori Kumobayashi, Shunichi Murahashi
  • Patent number: 5175348
    Abstract: The invention relates to a novel process for the preparation of halogenated carboxylic acid esters of formula I ##STR1## wherein R.sub.1 is alkyl, alkenyl, alkynyl, cycloalkyl, aralkyl or aryl, R.sub.2 hydrogen is alkyl or cycloalkyl, and R.sub.3 is halogen having an atomic number of from 9 up to and including 53, which process comprises reacting an acylal of formula II ##STR2## with a hydrogen halide of the formula H--R.sub.3 (III).
    Type: Grant
    Filed: March 10, 1992
    Date of Patent: December 29, 1992
    Assignee: Saurefabrik Schweizerhall
    Inventors: Pasquale Gallegra, Gerhard Degischer
  • Patent number: 5171879
    Abstract: The invention relates to a novel process for the preparation of chlorinated carboxylic acid esters of formula I ##STR1## wherein R.sub.1 is alkyl, alkenyl, alkynyl, cycloalkyl, aralkyl or aryl and R.sub.2 hydrogen is alkyl or cycloalkyl, which process comprises reacting an acylal of formula II ##STR2## with thionyl chloride.
    Type: Grant
    Filed: March 10, 1992
    Date of Patent: December 15, 1992
    Assignee: Saurefabrik Schweizerhall
    Inventors: Pasquale Gallegra, Gerhard Degischer
  • Patent number: 5155256
    Abstract: An improved process for preparing 2-bromoethyl acetate involves reacting ethylene glycol with an aqueous solution of hydrogen bromide and acetic acid in the presence of a solvent such as toluene which forms an azeotrope with water but not with 2-bromoethyl acetate. The resulting reaction mixture is heated under reflux conditions to separate toluene and water therefrom and acetic anhydride or acetic acid is added to convert bromoethanol in the reaction mixture to additional 2-bromoethyl acetate.
    Type: Grant
    Filed: June 21, 1991
    Date of Patent: October 13, 1992
    Assignee: Mallinckrodt Medical, Inc.
    Inventor: Robert C. Chapman
  • Patent number: 5130462
    Abstract: Cyclobutane derivatives of the formulas ##STR1## wherein P is a hydroxy protecting group and X is a leaving group are useful intermediates in the preparation of antiviral compounds.
    Type: Grant
    Filed: February 19, 1991
    Date of Patent: July 14, 1992
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: William A. Slusarchyk, Robert Zahler
  • Patent number: 5117045
    Abstract: The invention relates to a method for producing solvent-soluble chlorinated ethylene-vinyl acetate copolymer by conducting homogeneous chlorination of ethylene-vinyl acetate copolymer in aqueous suspension by irradiation or by organic or inorganic radical generation, which method comprises conducting the chlorination upon a powder of ethylene-vinyl acetate copolymer containing 5 to 35 wt % of vinyl acetate and having a specific surface area of not less than 300 cm.sup.2 /g at a reaction temperature dependent upon the content of vinyl acetate as expressed in the relationship:20.ltoreq.[reaction temperature (.degree. C.)].ltoreq.60-[vinyl acetate content (wt. %)].
    Type: Grant
    Filed: November 5, 1990
    Date of Patent: May 26, 1992
    Assignee: Sanyo-Kokusaku Pulp Co., Ltd.
    Inventors: Yoshitatsu Nishijima, Terumasa Fujitaka, Kazuo Shimizu
  • Patent number: 5091598
    Abstract: Process of preparation of alcohols by the reaction of an organic halide with a carbonyl compound in an organic solvent, in the presence of metallic manganese, followed by hydrolysis of the reaction product; the reaction is initiated and activated by an ester present in the reaction medium.
    Type: Grant
    Filed: December 28, 1988
    Date of Patent: February 25, 1992
    Assignee: Societe Nationale Elf Aquitaine
    Inventors: Gerard Cahiez, Pierre-Yves Chavant, Pierre Tozzolino
  • Patent number: 5091560
    Abstract: A method for synthesizing an acyloxycarboxylic acid by providing a reaction chamber, establishing sources of an .alpha.-hydroxycarboxylic acid and an acid chloride, and repeatedly contacting substantially equal molar amounts of the .alpha.-hydroxycarboxylic acid and the acid chloride within the reaction chamber. The acyloxycarboxylic acid so synthesized is useful as a starting material for conversion to various esters which, when placed in aqueous solution with a source of hydrogen peroxide, result in a peracid and are useful for bleaching applications.
    Type: Grant
    Filed: December 21, 1990
    Date of Patent: February 25, 1992
    Assignee: The Clorox Company
    Inventor: Richard R. Rowland
  • Patent number: 5004569
    Abstract: The invention relates to a process for the production of carboxylic acid esters from carboxylic acids and alcohols which is characterized in that neutral phosphites containing oxetane groups are used as esterification catalysts.
    Type: Grant
    Filed: December 6, 1988
    Date of Patent: April 2, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Helmut-Martin Meier, Klaus Kircher, Klaus Berg
  • Patent number: 4959187
    Abstract: The invention provides novel bleaching compositions comprising peracid precursors with the general structure ##STR1## with R, R', R" and L as defined in the specification. Novel peracids and precursors are also herein disclosed. These peracid precursors provide new, proficient and cost-effective compounds for fabric bleaching.
    Type: Grant
    Filed: October 14, 1988
    Date of Patent: September 25, 1990
    Assignee: The Clorox Company
    Inventors: Ronald A. Fong, Sheldon N. Lewis, Richard J. Wiersema, Alfred G. Zielske