Additional Carbonyl Attached Indirectly To The Cyano Group By Nonionic Bonding Patents (Class 558/442)
  • Patent number: 11793732
    Abstract: Dental material which comprises at least one compound of formula I, in which R1 is a linear, branched or cyclic aliphatic C1-C30 hydrocarbon radical or an aromatic C6-C30 hydrocarbon radical, wherein the aliphatic or aromatic hydrocarbon radical can be substituted or unsubstituted and wherein aliphatic hydrocarbon radicals can be interrupted by one or more urethane groups, ester groups, oxygen atoms and/or sulfur atoms; X, Y, Z independently of each other in each case are —COOR2, —CON(R3R4)—, an aromatic C6-C10 hydrocarbon radical or CN, wherein R2, R3, R4 in each case independently of each other is hydrogen, a linear, branched or cyclic aliphatic C1-C30 hydrocarbon radical or an aromatic C6-C30 hydrocarbon radical, wherein the aliphatic or aromatic hydrocarbon radical can be substituted or unsubstituted and wherein aliphatic hydrocarbon radicals can be interrupted by one or more oxygen atoms, and m is 2 or 3.
    Type: Grant
    Filed: February 3, 2021
    Date of Patent: October 24, 2023
    Assignee: Ivoclar Vivadent AG
    Inventors: Iris Lamparth, Norbert Moszner, Robert Liska, Christian Gorsche, Yohann Catel, Gernot Peer
  • Patent number: 11499019
    Abstract: The present application relates to a curable composition. The present application provides a curable composition comprising an internal heat source for generating heat by application of an alternate-current magnetic field from the outside, together with a phthalonitrile compound and a curing agent therefor. The curable composition can precisely control the heat generated from the internal heat source according to the strength of the alternate-current magnetic field to precisely control curing conditions of the curable composition.
    Type: Grant
    Filed: November 29, 2017
    Date of Patent: November 15, 2022
    Assignee: LG CHEM, LTD.
    Inventors: Jin Kyu Lee, Seung Hee Lee, Sang Woo Kim, Sang Bum Ahn
  • Patent number: 11299652
    Abstract: This invention relates to cyanoacrylate-containing compositions that include (a) a beta-alkoxy cyanoacrylate component, (b) a cyanoacrylate component selected from butyl cyanoacrylates, octyl cyanoacrylates, and combinations thereof; (c) a rubber toughening component (d) a surface modified component; and (e) an adhesion promoter. Cured products of the inventive cyanoacrylate compositions demonstrate improved toughness without an odor typically found with cyanoacrylate-containing compositions.
    Type: Grant
    Filed: April 26, 2020
    Date of Patent: April 12, 2022
    Assignee: Henkel AG & Co. KGaA
    Inventors: Rory B. Barnes, Rachel Hersee, Barry N. Burns
  • Patent number: 9657120
    Abstract: This invention relates to cyanoacrylate-containing compositions, which when cured provide improved heat resistance.
    Type: Grant
    Filed: September 6, 2011
    Date of Patent: May 23, 2017
    Assignee: Henkel IP & Holding GmbH
    Inventors: Marisa Phelan, Cormac Duffy, John Killoran, Barry N. Burns, John Guthrie, Bernard Ryan, Ciara Goff
  • Patent number: 9046775
    Abstract: A composition for forming a liquid immersion upper layer film includes a polymer component including a polymer having a structural unit represented by a formula (1); and a solvent. R1 represents a carboxy group or a group represented by a formula (2); X represents a single bond, a divalent hydrocarbon group having 1 to 20 carbon atoms or a divalent fluorinated hydrocarbon group having 1 to 20 carbon atoms; R2 represents a hydrocarbon group having 1 to 20 carbon atoms and a valency of (n+1), a fluorinated hydrocarbon group having 1 to 20 carbon atoms and a valency of (n+1), or one of these groups each including between adjacent two carbon atoms thereof —CO—, —COO—, —O—, —NR?—, —CS—, —S—, —SO—, —SO2— or a combination thereof; and R3 represents a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms.
    Type: Grant
    Filed: September 20, 2013
    Date of Patent: June 2, 2015
    Assignee: JSR CORPORATION
    Inventors: Shinya Minegishi, Kiyoshi Tanaka, Kazunori Kusabiraki
  • Patent number: 8927759
    Abstract: The present invention relates to a process for producing 2-cyanoacetic acid anhydride, comprising the steps of a) preparing a reaction mixture, containing as reactants 2-cyanoacetic acid, and at least one C4-20 carboxylic acid anhydride in at least one organic solvent, wherein the molar ratio of 2-cyanoacetic acid to C4-20 carboxylic acid anhydride in said reaction mixture is greater than 1.5:1, and b) subjecting the reaction mixture to a temperature of 0° C. to 100° C. to form 2-cyanoacetic acid anhydride. The present invention also relates to process for producing 2-cyanoacetic acid esters, 2-cyanoacetic acid amides and/or 2-cyanoacetic acid thioesters from 2-cyanoacetic acid anhydride.
    Type: Grant
    Filed: January 18, 2013
    Date of Patent: January 6, 2015
    Assignee: Henkel IP & Holding GmbH
    Inventor: Stephen Hynes
  • Patent number: 8927557
    Abstract: The compounds of Formula (I), wherein R1, R2, R21, R22, R23, R24, Y and R3 have the meanings as given in the description, the salts thereof, the stereoisomers of the compounds and the salts thereof are effective inhibitors of the type 5 phosphodiesterase.
    Type: Grant
    Filed: August 24, 2010
    Date of Patent: January 6, 2015
    Assignee: Takeda GmbH
    Inventors: Josef Stadlwieser, Beate Schmidt, Heiko Bernsmann, Torsten Dunkern, Ewald Benediktus, Andreas Pahl, Ragna Hussong, Olaf Nimz, Matthias Mueller, Martin Viertelhaus
  • Patent number: 8829225
    Abstract: An improvement in the production of 1,1-disubstituted ethylenes is attained by contacting a 1,1-disubstituted ethylene with alumina and separating the alumina to obtain a 1,1-disubstituted ethylene with a good combination of cost, purity, shelf life and cure rate.
    Type: Grant
    Filed: January 28, 2013
    Date of Patent: September 9, 2014
    Assignee: OptMed, Inc.
    Inventors: Francis McConville, John Gregory Reid, Murugappa Vedachalam
  • Publication number: 20140051869
    Abstract: A continuous process for producing compounds having the general formula (6) is provided: wherein R is a straight or branched chain alkyl group, R1 is a straight or branched chain alkyl group substituted with a nitrile group, a hydroxy group or a halogen atom, R2 is a hydroxy group or a keto group, and each R3 is, independently, hydrogen or a straight or branched chain alkyl group, comprising providing a continuous stream of an alkyl acetate and a continuous stream of an alkali metal or alkaline earth metal amide base and contacting the continuous streams to yield an enolate compound, providing a continuous stream of a compound of formula (5): wherein R1 is as previously defined, and contacting the continuous stream of compound (5) with a continuous stream of the enolate above 20° C. to yield an intermediate compound and treating the intermediate compound with an acid.
    Type: Application
    Filed: October 25, 2013
    Publication date: February 20, 2014
    Applicant: Phoenix Chemicals Limited
    Inventors: Peter McCormack, Antony John Warr, Elliot Latham
  • Publication number: 20140024815
    Abstract: A dendritic structure includes a core and repeating units, wherein the repeating units comprise units of the type ABxCy, wherein x is 2, 3, or 4, wherein y is 1, 2, or 3, wherein C is selected from the group consisting of azides and alkynes, and wherein every repeating unit is bound to at least one other unit with at least one bond selected from the group consisting of the group consisting of an ester, an amide, a thioether, an ether, a urethane, an amine, and an imine. Advantages include that a “one-pot” growth of the dendritic structure is possible. It is possible to have more functional groups in a dendritic structure. It is possible to add different functional groups simultaneously both to an inner layer and to an outer layer in a dendritic structure.
    Type: Application
    Filed: September 25, 2013
    Publication date: January 23, 2014
    Applicant: POLYMER FACTORY SWEDEN AB
    Inventors: Anders HULT, Michael MALKOCH, Per ANTONI
  • Publication number: 20130131370
    Abstract: The present invention relates to a process for producing 2-cyanoacetic acid anhydride, comprising the steps of a) preparing a reaction mixture, containing as reactants 2-cyanoacetic acid, and at least one C4-20 carboxylic acid anhydride in at least one organic solvent, wherein the molar ratio of 2-cyanoacetic acid to C4-20 carboxylic acid anhydride in said reaction mixture is greater than 1.5:1, and b) subjecting the reaction mixture to a temperature of 0° C. to 100° C. to form 2-cyanoacetic acid anhydride. The present invention also relates to process for producing 2-cyanoacetic acid esters, 2-cyanoacetic acid amides and/or 2-cyanoacetic acid thioesters from 2-cyanoacetic acid anhydride.
    Type: Application
    Filed: January 18, 2013
    Publication date: May 23, 2013
    Applicant: Loctite (R&D) Limited Ltd.
    Inventor: Loctite (R&D) Limited Ltd.
  • Publication number: 20130116465
    Abstract: An allyl 2-cyanoacrylate prepolymer, a preparation method thereof, and a bioadhesive composition including the prepolymer thus produced are provided, and more particularly, an allyl 2-cyanoacrylate prepolymer having a structure, in which at least one double bond in a molecule remains at an adjacent site to a cyano group prepared by causing a prepolymerization in a double bond moiety of an allyl group by pre-polymerizing through heating 2-cyanoacrylate having at least two double bonds in a molecule such as allyl 2-cyanoacrylate, a method for preparing the same, and a bioadhesive composition including the prepolymer thus produced are provided.
    Type: Application
    Filed: November 6, 2012
    Publication date: May 9, 2013
    Applicant: UNIVERSITY-INDUSTRY COOPERATION GROUP OF KYUNG HEE UNIVERSITY
    Inventor: University-Industry Cooperation Group of Kyung
  • Publication number: 20130064871
    Abstract: The present invention relates to a cosmetic composition comprising the combination i) of at least one screening agent of the dibenzoylmethane derivative type and ii) of at least one specific merocyanine dicyano or cyanoacetate derivative. It also relates to a method for the photostabilization, with regard to radiation, of at least one screening agent of the dibenzoylmethane derivative type by an effective amount of at least one specific merocyanine dicyano or cyanoacetate derivative.
    Type: Application
    Filed: March 7, 2011
    Publication date: March 14, 2013
    Applicant: L'OREAL
    Inventors: Herve Richard, Benoit Muller
  • Patent number: 8329936
    Abstract: The present invention relates to a method for producing cyanoacrylic acid esters. The method is based substantially on a transesterification reaction, wherein the transesterification reaction is performed in the presence of at least one transition metal catalyst that is formed by reacting at least one hydroxyl group-containing support material with at least one transition metal alkoxide.
    Type: Grant
    Filed: January 3, 2012
    Date of Patent: December 11, 2012
    Assignee: Henkel AG & Co. KGaA
    Inventors: Carsten Friese, Andreas Kirschning, Ludovic Coutable
  • Publication number: 20120215023
    Abstract: A method for performing a chemical reaction to produce a target compound by heating a reaction medium containing a reactant in a reactor, the reaction medium being brought into contact with a solid heating medium that can be heated by electromagnetic induction and that is located inside the reactor and surrounded by the reaction medium and the heating medium being heated by electromagnetic induction with the aid of an inductor, causing the target compound to form, and the target compound being separated from the heating medium, wherein the target compound has a lower molar mass than the reactant and at least one covalent bond of the reactant is cleaved in order to produce said target compound from the reactant.
    Type: Application
    Filed: February 21, 2012
    Publication date: August 23, 2012
    Inventors: Carsten Friese, Andreas Kirschning, Sascha Volkan Ceylan, Juergen Wichelhaus
  • Publication number: 20120171581
    Abstract: Disclosed are a nonaqueous electrolytic solution of an electrolyte dissolved in a nonaqueous solvent, which contains a carboxylate represented by the following general formula (I) in an amount of from 0.01 to 10% by mass of the nonaqueous electrolytic solution; and an electrochemical element using it.
    Type: Application
    Filed: September 14, 2010
    Publication date: July 5, 2012
    Applicant: UBE INDUSTRIES, LTD.
    Inventors: Koji Abe, Shoji Shikita, Kazuyuki Kawabe, Masahide Kondo, Tatsuo Fujino
  • Publication number: 20120082934
    Abstract: [Problem] To reduce the time required for a film to exhibit decreased hydrophobicity after liquid immersion lithography while allowing the surface of a film to exhibit high hydrophobicity during liquid immersion lithography. [Solution] A radiation-sensitive resin composition including (A) a polymer that includes a repeating unit (a1) and a fluorine atom, and (B) a photoacid generator, the repeating unit (a1) including a group shown by any of the following formulas (1-1) to (1-3).
    Type: Application
    Filed: September 23, 2011
    Publication date: April 5, 2012
    Applicant: JSR Corporation
    Inventors: Kazuo Nakahara, Mitsuo Sato, Yusuke Asano
  • Patent number: 8119829
    Abstract: The present invention is directed to compositions of specific carboxylic acid, fatty acid or oil derivatives containing nitrile groups and methods of their preparation. The preparation involves a hydrocyanation reaction. A method of hydrogenating the nitrile containing carboxylic acid acids obtained by above hydrocyanation to produce amine containing carboxylic acids is also disclosed in this invention.
    Type: Grant
    Filed: April 12, 2010
    Date of Patent: February 21, 2012
    Assignee: Invista North America S.A.R.L.
    Inventors: Alan Martin Allgeier, Christian Peter Lenges
  • Publication number: 20110092729
    Abstract: The present invention is directed to compositions of specific carboxylic acid, fatty acid or oil derivatives containing nitrile groups and methods of their preparation. The preparation involves a hydrocyanation reaction. A method of hydrogenating the nitrile containing carboxylic acid acids obtained by above hydrocyanation to produce amine containing carboxylic acids is also disclosed in this invention.
    Type: Application
    Filed: April 12, 2010
    Publication date: April 21, 2011
    Applicant: INVISTA NORTH AMERICA S.A.R.L.
    Inventors: Alan Martin Allgeier, Christian Peter Lenges
  • Publication number: 20110052696
    Abstract: A dendritic structure includes a core and repeating units, wherein the repeating units comprise units of the type ABxCy, wherein x is 2, 3, or 4, wherein y is 1, 2, or 3, wherein C is selected from the group consisting of azides and alkynes, and wherein every repeating unit is bound to at least one other unit with at least one bond selected from the group consisting of the group consisting of an ester, an amide, a thioether, an ether, a urethane, an amine, and an imine. Advantages include that a “one-pot” growth of the dendritic structure is possible. It is possible to have more functional groups in a dendritic structure. It is possible to add different functional groups simultaneously both to an inner layer and to an outer layer in a dendritic structure.
    Type: Application
    Filed: May 6, 2009
    Publication date: March 3, 2011
    Applicant: POLYMER FACTORY SWEDEN AB
    Inventors: Anders Hult, Michael Malkoch, Per Antoni
  • Publication number: 20100286433
    Abstract: Novel improved processes for the production and isolation of methylidene malonates via direct and indirect adduct processes.
    Type: Application
    Filed: May 6, 2010
    Publication date: November 11, 2010
    Inventors: Bernard M. Malofsky, Chris Mariotti
  • Publication number: 20100210788
    Abstract: This invention relates to novel electron deficient olefins, such as certain 2-cyanoacrylates and methylidene malonates, prepared using an imine or an iminium salt.
    Type: Application
    Filed: April 23, 2010
    Publication date: August 19, 2010
    Applicant: Loctite (R&D) Limited
    Inventors: Ciaran B. McArdle, Ligang Zhao, Stefano Gherardi, Kevin Murnaghan
  • Publication number: 20100199888
    Abstract: This invention relates to novel compounds with ester linkage(s) capped with either electron deficient olefinic linkage(s) or group(s) or reactive functional groups (termed herein as “active methylene reagents”), and curable compositions prepared therefrom.
    Type: Application
    Filed: April 23, 2010
    Publication date: August 12, 2010
    Applicant: Loctite (R&D) Limited
    Inventors: Ciaran B. McArdle, Ligang Zhao, Stefano Gherardi, Kevin Murnaghan
  • Patent number: 7557238
    Abstract: In one aspect, the present invention provides a novel process for the preparation of tert-butyl 6-cyano-5-hydroxy-3-oxohexanoate, a key intermediate for the preparation of HMG-CoA reductase inhibitor.
    Type: Grant
    Filed: September 18, 2003
    Date of Patent: July 7, 2009
    Assignee: Biocon Limited
    Inventors: Sumithra Srinath, Tom Thomas Puthiaparampil, Sambasivam Ganesh
  • Patent number: 7534907
    Abstract: A monomer composition comprising at least one polymerizable alkyl ester ?-cyanoacrylate monomer. Specifically, the ?-cyanoacrylate monomer is an alkyl ester ?-cyanoacrylate monomer of the general formula having a spacer R1: n is from 2 to 12; R3 and R4 are each an alkyl group or a hydrogen, and at least one of R3 or R4 is an alkyl group (e.g. linear or branched, or cyclic) having from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 and 13 carbon atoms; R2 is an alkyl group (e.g. linear or branched, or cyclic) having from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 and 13 carbon atoms; and the combined number of carbon atoms (N) in the spacer R1 is at least n+1.
    Type: Grant
    Filed: May 30, 2007
    Date of Patent: May 19, 2009
    Assignee: Ethichon, Inc.
    Inventor: Hongbo Liu
  • Patent number: 7514563
    Abstract: A process for producing cyano substituted arene boranes is described. The compounds are useful intermediates to pharmaceutical compounds using the cyano group as a reactant.
    Type: Grant
    Filed: June 8, 2006
    Date of Patent: April 7, 2009
    Assignee: Board of Trustees of Michigan State University
    Inventors: Milton R. Smith, III, Robert E. Maleczka, Ghayoor A. Chotana
  • Patent number: 7238828
    Abstract: A monomer composition comprising at least one polymerizable alkyl ester ?-cyanoacrylate monomer. Specifically, the ?-cyanoacrylate monomer is an alkyl ester ?-cyanoacrylate monomer of the general formula having a spacer R1: wherein n is from 2 to 12; R3 and R4 are each an alkyl group or a hydrogen, and at least one of R3 or R4 is an alkyl group (e.g. linear or branched, or cyclic) having from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 and 13 carbon atoms; R2 is an alkyl group (e.g. linear or branched, or cyclic) having from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 and 13 carbon atoms; and the combined number of carbon atoms (N) in the spacer R1 is at least n+1.
    Type: Grant
    Filed: March 24, 2005
    Date of Patent: July 3, 2007
    Assignee: Ethicon, Inc.
    Inventor: Hongbo Liu
  • Patent number: 7223745
    Abstract: The present invention provides boronic acid compounds, boronic esters, and compositions thereof that can modulate apoptosis such as by inhibition of proteasome activity. The compounds and compositions can be used in methods of inducing apoptosis and treating diseases such as cancer and other disorders associated directly of indirectly with proteasome activity.
    Type: Grant
    Filed: August 12, 2004
    Date of Patent: May 29, 2007
    Assignee: Cephalon, Inc.
    Inventors: Sankar Chatterjee, Mohamed Iqbal, Ernesto Menta, Ambrogio Oliva
  • Patent number: 7193101
    Abstract: A bromine/nitro moiety linked into the backbone of an ester or other compound over a wide range of occurrence rates provides antimicrobial, bio-resistant and fungal resistant properties for metal working fluids (MWF)s, coatings, plastics, and medical devices. The moiety can be have the bromo and nitro groups linked to the same or different carbon atoms. The present invention also relates to urethanes, urea, amides, imides, carbonates, ethers, siloxanes, and many other types of linkages essential to MWF bases.
    Type: Grant
    Filed: August 23, 2005
    Date of Patent: March 20, 2007
    Assignee: TPAT IP
    Inventor: Thomas Daly
  • Patent number: 7102027
    Abstract: An adamantanetricarboxylic acid derivative is represented by following Formula (1): wherein X is a hydrogen atom or a hydrocarbon group; and R1, R2 and R3 may be the same as or different from one another and are each a carboxyl group which may be protected by a protecting group, or a carbonyl halide group, wherein at least one of R1, R2 and R3 is a carboxyl group which is protected by a protecting group, or a carbonyl halide group.
    Type: Grant
    Filed: March 24, 2004
    Date of Patent: September 5, 2006
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Shinya Nagano, Jiichiro Hashimoto
  • Patent number: 6828456
    Abstract: The present invention relates to 2-amino-2-alkyl-3 hexenoic and hexynoic acid derivatives and their use in therapy, in particular their use as nitric oxide synthase inhibitors.
    Type: Grant
    Filed: September 15, 2001
    Date of Patent: December 7, 2004
    Assignee: Pharmacia Corporation
    Inventors: Donald W. Hansen, Jr., Ronald Keith Webber
  • Patent number: 6781009
    Abstract: There are provided a method for producing a 4-cyano-3-oxobutanoate by reacting a 4-halo-3-oxobutanoate with an alkaline metal cyanide in methanol, a process for producing 4-cyano-3-hydroxybutanoate therefrom.
    Type: Grant
    Filed: October 29, 2001
    Date of Patent: August 24, 2004
    Assignee: Sumitomo Chemical Company, Limited
    Inventor: Ryuhei Wakita
  • Patent number: 6730803
    Abstract: The &bgr;-keto ester compound, &bgr;-hydroxy acid compound and acetonide form of a 1,3-diol derivative of the formulas (I), (V) and (VIII) wherein each symbol is as defined in the specification, are useful as a synthetic intermediate for an epothilone derivative being developed as a pharmaceutical agent having an antitumor activity.
    Type: Grant
    Filed: September 30, 2002
    Date of Patent: May 4, 2004
    Assignee: Sumika Fine Chemicals Co., Ltd.
    Inventors: Mitsuhiro Iwasaki, Kiyoshi Sugi, Hideto Miyamoto, Nobushige Itaya
  • Publication number: 20030105347
    Abstract: There are provided a method for producing a 4-cyano-3-oxobutanoate by reacting a 4-halo-3-oxobutanoate with an alkaline metal cyanide in methanol, a process for producing 4-cyano-3-hydroxybutanoate therefrom.
    Type: Application
    Filed: October 29, 2001
    Publication date: June 5, 2003
    Inventors: Ryuhei Wakita, Nobuya Ito
  • Publication number: 20030004360
    Abstract: Disclosed are intermediates and processes for preparing epoxides of the formula: 1
    Type: Application
    Filed: April 23, 2002
    Publication date: January 2, 2003
    Inventor: Michael R. Reeder
  • Patent number: 6359061
    Abstract: Amide compounds of formula (I), combinatorial libraries of amide compounds and methods of preparing the same are provided. Libraries of the invention are useful for screening in biological assays in order to identify pharmaceutically useful compounds.
    Type: Grant
    Filed: March 19, 1999
    Date of Patent: March 19, 2002
    Assignee: ISIS Pharmaceuticals, Inc.
    Inventors: Eric Edward Swayze, Peter William Davis
  • Patent number: 6288263
    Abstract: Compounds represented by the formula wherein R and R1 independently represent H, —CH2CN or —CH2CO2X, with the proviso that R and R1 can not be both H or —CH2CO2X; and X represents hydrogen, an alkali metal or alkaline earth metal are disclosed. These compounds are useful as intermediate compounds in the preparation of N-[2-(carboxymethoxy)ethyl]-N-(carboxy-methyl)glycine. These intermediates can be formed by contacting 3-morpholinone with glycolonitrile under alkaline conditions to form an aminonitrile which can be hydrolyzed and contacted with additional glycolonitrile to form the nitrile intermediate which can be converted to N-[2-(carboxymethoxy)ethyl]-N-(carboxymethyl)glycine via hydrolysis.
    Type: Grant
    Filed: May 25, 2000
    Date of Patent: September 11, 2001
    Assignee: The Dow Chemical Company
    Inventors: Phillip S. Athey, David A. Wilson
  • Patent number: 6046353
    Abstract: A method of making (.+-.)-3-(aminomethyl)-5-methylhexanoic acid that comprises condensing isovaleraldehyde with ##STR1## to form primarily ##STR2## reacting the ##STR3## with a cyanide source to form ##STR4## decarboxylating the ##STR5## to form ##STR6## hydrolyzing the ##STR7## with an alkali or alkaline earth metal hydroxide to form an alkali or alkaline earth metal carboxylate salt; and hydrogenating the alkali or alkaline earth metal carboxylate salt to form (.+-.)-3-(aminomethyl)-5-methylhexanoic acid, wherein R.sub.1 and R.sub.2 are the same or different and are hydrogen, C.sub.1 -C.sub.6 alkyl, aryl, benzyl, or C.sub.3 -C.sub.6 cycloalkyl. The present invention also provides a method of making (.+-.
    Type: Grant
    Filed: August 26, 1998
    Date of Patent: April 4, 2000
    Assignee: Warner-Lambert Company
    Inventors: Todd Michel Grote, Brian Keith Huckabee, Thomas Mulhern, Denis Martin Sobieray, Robert Daniel Titus
  • Patent number: 5817603
    Abstract: Substituted cyclohexene-1,2-dicarboxylic acid derivatives I ##STR1## where R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are herein defined, or the agriculturally useful salts of Ia and Ib and intermediates for their preparation, which compounds are useful as herbicides and for the desiccation/defoliation of plants.
    Type: Grant
    Filed: February 11, 1997
    Date of Patent: October 6, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Ralf Klintz, Elisabeth Heistracher, Peter Schaefer, Gerhard Hamprecht, Peter Plath, Uwe Kardorff, Matthias Gerber, Karl-Otto Westphalen, Helmut Walter
  • Patent number: 5559218
    Abstract: 2-Aroylcyclohexanediones I ##STR1## (A is C.sub.1 -C.sub.6 -alkylene; R.sup.1 is substituted phenyl or hetaryl which may furthermore carry a fused ring; R.sup.2 -R.sup.5 are each hydrogen or C.sub.1 -C.sub.4 -alkyl; R.sup.6 is H, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxycarbonyl and R.sup.7 is C.sub.1 -C.sub.4 -alkyl,with the proviso that R.sup.1 is not mono- or dihalophenyl)and the agriculturally useful salts thereof and the esters of I with C.sub.1 -C.sub.10 -carboxylic acids or inorganic acids.The 2-aroylcyclohexanediones I are suitable as herbicides and plant growth regulators.
    Type: Grant
    Filed: February 6, 1995
    Date of Patent: September 24, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: J urgen Kast, Wolfgang von Deyn, Christoph N ubling, Helmut Walter, Matthias Gerber, Karl-Otto Westphalen
  • Patent number: 5481018
    Abstract: A novel intermediate useful in the synthesis of alpha-alanine diacetic acid or its salts is disclosed. The intermediate can be formed by contacting alanine with glycolonitrile under alkaline conditions or glycine with lactonitrile to form an aminonitrile which can be hydrolyzed and then contacted with additional glycolonitrile to form the nitrile intermediate which can be converted to alpha-alanine diacetic acid via hydrolysis.
    Type: Grant
    Filed: March 31, 1995
    Date of Patent: January 2, 1996
    Assignee: The Dow Chemical Company
    Inventors: Phillip S. Athey, David A. Wilson, Druce K. Crump
  • Patent number: 5468870
    Abstract: Dye-donor element for use according to thermal dye sublimation transfer comprising a support having thereon a dye layer containing a dye corresponding to the following formula ##STR1## wherein Z represents CN, COOR.sup.1 or CONR.sup.2 R.sup.3 ;R.sup.1, R.sup.2 and R.sup.3 each independently represent hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or R.sup.2 and R.sup.3 together represent the necessary atoms to close a heterocyclic nucleus or substituted heterocyclic nucleus;Y represents OR.sup.4 or NR.sup.5 R.sup.6 or CN;R.sup.4 represents hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, SO.sub.2 R.sup.7, COR.sup.7, CSR.sup.7, POR.sup.7 R.sup.8 ;R.sup.5 and R.sup.6 each independently has one of the significances given to R.sup.4 or represent substituted or unsubstituted amino, or R.sup.5 and R.sup.
    Type: Grant
    Filed: October 20, 1994
    Date of Patent: November 21, 1995
    Assignee: AGFA-GAVAERT, N.V.
    Inventor: Luc J. Vanmaele
  • Patent number: 5412146
    Abstract: For the preparation of 2-cyanoacetoxypropionic esters, a mixture of lactic ester and cyanoacetic ester is introduced, an alkali metal alcoholate is added as catalyst and the mixture is heated while the alcohol eliminated during the course of the reaction is distilled off. The course of the reaction is followed by means of gas chromatographic analysis and the reaction is terminated prior to eliminating the theoretical amount of alcohol by destroying the catalyst by acidification. The reaction mixture is worked up by distillation and the product easily separated from the reaction mass due to the substantial absence of high boiling components.
    Type: Grant
    Filed: June 3, 1994
    Date of Patent: May 2, 1995
    Assignee: Huels Aktiengesellschaft
    Inventors: Manfred Kaufhold, Marcel Feld
  • Patent number: 5411987
    Abstract: Combating fungi with substituted amine acid derivatives of the formula ##STR1## in which R.sup.1 represents alkyl, alkenyl, alkinyl, halogenoalkyl, halogenoalkenyl, halogenoalkinyl, cycloalkyl or cycloalkenyl,R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are identical or different and represent hydrogen, cycloalkyl or alkyl, orR.sup.3 and R.sup.4, together with the carbon atom to which they are bonded, form a cycloalkyl ring, andR.sup.6 represents hydrogen, alkyl, alkenyl, alkinyl, cyanoalkyl, unsubstituted or substituted phenylalkyl, unsubstituted or substituted phenyl or unsubstituted or substituted cycloalkyl, or represents unsubstituted or substituted heterocyclyl or heterocyclylalkyl,orR.sup.5 and R.sup.6, together with the nitrogen atom to which they are bonded, represent a heterocyclyl radical, which can contain further hetero atoms.
    Type: Grant
    Filed: February 25, 1993
    Date of Patent: May 2, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventors: Detlef Wollweber, Thomas Seitz, Wilhelm Brandes
  • Patent number: 5380850
    Abstract: Compounds having the formula I: ##STR1## are inhibitors of leukotriene biosynthesis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents. They are also useful in treating diarrhea, hypertension, angina, platelet aggregation, cerebral spasm, premature labor, spontaneous abortion, dysmenorrhea, and migraine.
    Type: Grant
    Filed: December 16, 1993
    Date of Patent: January 10, 1995
    Assignee: Merck Frosst Canada, Inc.
    Inventors: Petpiboon Prasit, Rejean Fortin, John H. Hutchinson, Michel L. Belley, Serge Leger, Richard Frenette, John Gillard
  • Patent number: 5312956
    Abstract: A non-functional liquid rubber is prepared by the solution polymerization of vinyl monomers. The polymer may be a homopolymer or a copolymer. As a copolymer the preferred monomers are a conjugated diene and a vinyl substituted nitrile such as acrylonitrile or methacrylonitrile. A non-functional initiator is employed that is either an azo initiator or a peroxide initiator.
    Type: Grant
    Filed: November 17, 1992
    Date of Patent: May 17, 1994
    Assignee: The B. F. Goodrich Company
    Inventor: Robert J. Bertsch
  • Patent number: 5286893
    Abstract: Alkenoic acid compounds are described. The compounds which are dehydropeptidase inactivators contain a ##STR1## moiety which is substituted with a halomethylene or a cyano moiety as R.sub.3. The enzyme deprotonates the alpha --CH.sub.2 group and then the intermediate compound forms a covalent bond with enzymic residue in the active site, resulting in irreversible inactivation of the enzyme. The compounds are particularly inactivators of renal dipeptidases.
    Type: Grant
    Filed: January 28, 1992
    Date of Patent: February 15, 1994
    Assignee: Board of Governors of Wayne State University
    Inventor: Shahriar Mobashery
  • Patent number: 5210271
    Abstract: A method of producing diethanolamine derivatives or acid salts thereof according to the reaction scheme: ##STR1## wherein X stands for a leaving group; and R.sup.1 stands for an alkylcarbamoyl group, which provides an industrially advantageous method of preparing the subject matter useful as an antiarrhythmic agent.
    Type: Grant
    Filed: August 23, 1991
    Date of Patent: May 11, 1993
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Yukio Mizuno, Miichiro Arita
  • 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: 5177243
    Abstract: A novel intermediate useful in the synthesis of ethylenediaminetriacetic acid (ED3A) or its salts. A salt of N,N'-ethylenediaminediacetic acid (ED2AH.sub.2) is condensed with formaldehyde to form a stable 5-membered ring intermediate. The addition of cyanide across this cyclic material forms ethylenediamine N,N'-diacetic acid-N'-cyanomethyl or salts thereof (mononitrile-diacid), which is useful intermediate in the production of ED3A. The nitrile in aqueous solutions may be spontaneously cyclized to form 2-oxo-1,4-piperazindeiacetic acid (3KP) or salts thereof. In the presence of excess base, salts of ED3A are formed in excellent yield and purity.
    Type: Grant
    Filed: December 21, 1991
    Date of Patent: January 5, 1993
    Assignee: W. R. Grace & Co.-Conn.
    Inventor: Brian A. Parker