Imidate Esters (i.e., Compounds Having The Imidate Group, Hn=ch-o-, Wherein Substitution May Be Made For Hydrogen Only, Bonded Directly To Carbon, Which Carbon May Be Single Bonded To Any Atom But May Be Multiple Bonded Only To Carbon) Patents (Class 558/6)
  • Patent number: 8846899
    Abstract: Disclosed are saccharide and phosphocholine derivatives. The derivatives include azide and alkyne derivatives which form one end of a variable length carbon chain. The opposite end of the variable length carbon chain is covalently linked to the saccharide or phosphocholine. The saccharide may be, for instance, a maltoside. The alkyne and azide derivatives of the saccharides and phosphocholine may be reacted together to form amphiphilic molecules useful in cellular membrane studies and applications. By adjusting the length of the carbon chain, the biochemical and biophysical properties of the resultant 1,4-disubstituted 1,2,3-triazole compounds may be custom tailored for the intended application. Resultant molecules may form micelles, bicelle, lipid bilayers and other like structures useful in the isolation and purification of membrane bound or membrane associated proteins and biochemical components.
    Type: Grant
    Filed: October 12, 2011
    Date of Patent: September 30, 2014
    Assignee: Anatrace Products, LLC
    Inventors: Benjamin R. Travis, Ritesh Mittal, Lijun Huang, Liang Tang
  • Patent number: 8742156
    Abstract: Carbamimidothioic acid esters of formula (I) and 2-nitro-N-[4-(pyridin-4-ylamino)phenyl]-4-(quinolin-4-ylamino)benzamide are used for the treatment of influenza, and for the inhibition of a viral RNA-dependent RNA polymerase. Formulae (I), (II).
    Type: Grant
    Filed: August 12, 2011
    Date of Patent: June 3, 2014
    Assignees: British Columbia Cancer Agency Branch, Versitech Limited
    Inventors: Steven J. Jones, Allan Sik-Yin Lau, Jianghong An, Hing-Yee Law, Chun-Wai Davy Lee
  • Patent number: 8299288
    Abstract: Disclosed is a method for producing a compound represented by Formula (4), the method including Step I of adding a solution in which hydrogen chloride is dissolved in an alcohol, to a mixture containing an organic solvent and a compound represented by Formula (1), and Step II of mixing a compound obtained in Step I, represented by Formula (3), with water.
    Type: Grant
    Filed: August 24, 2009
    Date of Patent: October 30, 2012
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Hajime Ishida, Masaji Hirota
  • Patent number: 8278473
    Abstract: There is provided a compound having an excellent controlling effect on pests, represented by the formula (I): wherein, A and E independently represent a —R1 group, a -L1-R1 group, etc.; G represents a -L2-R1 group, a —S(O)2—R4 group, etc.; X represents a —S—R5 group or a —O—R6 group; Z represents an optionally substituted carbocyclic group or an optionally substituted heterocyclic group; R1 represents an optionally substituted C1-C20 chain hydrocarbon group, etc.; R5 represents a substituted C1-C4 alkyl group, an optionally substituted C5-C10 alkyl group, etc.; R6 represents a substituted C1-C2 alkyl group, an optionally substituted C3-C10 alkyl group, etc.; L1 represents a an oxygen atom, a sulfur atom, a —S(O)— group, or a —S(O)2— group; and L2 represents an oxygen atom or a sulfur atom.
    Type: Grant
    Filed: November 14, 2008
    Date of Patent: October 2, 2012
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Shigeyuki Itoh, Tomohiro Araki
  • Publication number: 20110172427
    Abstract: This invention relates to a new synthesis, intermediates and precursors leading to a mixture of the compounds 11 and 12 as shown below. It also relates to the resolution of the stereoisomeric mixture to provide in substantial stereochemical purity compound 12. The synthesis of the invention involves preparation of compound 7 and compound 10 as shown below and their reaction to prepare a mixture of compound 11 and compound 12.
    Type: Application
    Filed: August 26, 2009
    Publication date: July 14, 2011
    Applicant: EISAI R&D MANAGEMENT CO., LTD.
    Inventors: Taiju Nakamura, Masaaki Matsuda, Yongbo Hu, Daiju Hasegawa, Yorihisa Hoshino, Kazato Inanaga, Minetaka Isomura, Nobuaki Sato, Kazuhiro Yoshizawa, George A. Moniz, Gordon D. Wilkie, Francis G. Fang, Yoshihiro Nishikawa
  • Publication number: 20100240729
    Abstract: There is provided a compound having an excellent controlling effect on pests, represented by the formula (I): wherein, A and E independently represent a —R1 group, a -L1-R1 group, etc.; G represents a -L2-R1 group, a —S(O)2—R4 group, etc.; X represents a —S—R5 group or a —O—R6 group; Z represents an optionally substituted carbocyclic group or an optionally substituted heterocyclic group; R1 represents an optionally substituted C1-C20 chain hydrocarbon group, etc.; R5 represents a substituted C1-C4 alkyl group, an optionally substituted C5-C10 alkyl group, etc.; R6 represents a substituted C1-C2 alkyl group, an optionally substituted C3-C10 alkyl group, etc.; L1 represents a an oxygen atom, a sulfur atom, a —S(O)— group, or a —S(O)2-group; and L2 represents an oxygen atom or a sulfur atom.
    Type: Application
    Filed: November 14, 2008
    Publication date: September 23, 2010
    Applicant: Sumitomo Chemical Company, Limited
    Inventors: Shigeyuki Itoh, Tomohiro Araki
  • Patent number: 7705175
    Abstract: Provided is a method for producing an imide ether compound in high yield. The method is characterized in that a nitrile compound, an alcohol, and a hydrogen halide are continuously introduced into a flow reaction device comprising a mixer and a flow reactor, to be subjected to a reaction. Because a reaction proceeds in a ratio of 1:1 by a flow reactor, selectivity is improved and generation of by-products is decreased, and thus an imide ether compound can be efficiently produced.
    Type: Grant
    Filed: January 18, 2006
    Date of Patent: April 27, 2010
    Assignee: Nippoh Chemicals Co., Ltd.
    Inventors: Hitoshi Mitsui, Yuichiro Kinoshita, Kazuya Nakagawa
  • Publication number: 20080039548
    Abstract: The invention relates to a novel poly(ethylene oxide)imine; a novel amine reactive moiety; a novel moisture activated latent curing adhesive or sealant mixture comprising (1) a ketimine or aldimine, and (2) an amine reactive moiety; and a novel moisture activated latent curing adhesive or sealant comprising the reaction product of (1) and (2).
    Type: Application
    Filed: August 9, 2006
    Publication date: February 14, 2008
    Inventors: Joseph Zavatsky, Binoy K. Bordoloi
  • Patent number: 6806380
    Abstract: Disclosed is a safe, efficient and environmentally friendly method for preparing imidoesters.
    Type: Grant
    Filed: October 2, 2002
    Date of Patent: October 19, 2004
    Assignee: Lexicon Pharmaceuticals, Inc.
    Inventors: Hartmuth C. Kolb, Ramanaiah C. Kanamarlapudi, Paul F. Richardson, Gaznabi Khan
  • Publication number: 20030236426
    Abstract: Benzimidates can be reacted with a large number of nucleophiles, leading to a wide variety of products. The present invention discloses a facile synthesis for ethyl 2,4-dihydroxybenzimidate, and ethers and diethers thereof, from 2,4-dihydroxybenzoic acid or 2,4-dibenzyloxybenzoic acid. The present invention also discloses a method of preparing a class of iron chelating agents related to desferrithiocin, all of which contain a thiazoline ring. In this method, 2,4-dihydroxybenzonitrile is condensed with (S)-2-methylcysteine.
    Type: Application
    Filed: May 15, 2003
    Publication date: December 25, 2003
    Applicant: Genzyme Corporation
    Inventors: Mukund S. Chorghade, Mukund K. Gurjar, Joseph Cherian
  • Publication number: 20030153728
    Abstract: Disclosed is a safe, efficient and environmentally friendly method for preparing imidoesters.
    Type: Application
    Filed: October 2, 2002
    Publication date: August 14, 2003
    Inventors: Hartmuth C. Kolb, Ramanaiah C. Kanamarlapudi, Paul F. Richardson, Gaznabi Khan
  • Patent number: 5877297
    Abstract: Boron compound completing reagents, intermediate reagents of those reagents and methods of synthesizing these reagents. These reagents, including those shown as General Formula CII may be used, after further reactions described herein, to complex with boronic compounds, such as phenylboronic acid or derivatives thereof. ##STR1## In one embodiment, group Z comprises a spacer selected from a saturated or unsaturated chain up to about 0 to 6 carbon equivalents in length, an unbranched saturated or unsaturated chain of from about 6 to 18 carbon equivalents in length with at least one of intermediate amide and disulfide moieties, and a polyethylene glycol chain of from 3 to 12 carbon equivalents in length; group R.sub.2 is one of an alkyl and a methylene with an electronegative moiety; and BAS is a biologically active species.
    Type: Grant
    Filed: October 22, 1997
    Date of Patent: March 2, 1999
    Assignee: Prolinx, Inc.
    Inventors: Mark L. Stowolitz, Robert J. Kaiser, Kevin P. Lund
  • Patent number: 5872224
    Abstract: Boron compound complexing reagents, boron compound complexes, and methods of synthesizing these reagents and complexes are disclosed. These reagents and complexes include those shown in General Formula CIV, and General Formula CVI. In one embodiment, the reagent of General Formula CIV may be used to form a complex with a boron compound, such as a complex shown in General Formula CVI. ##STR1## In one embodiment, group Z comprises a spacer selected from a saturated or unsaturated chain of up to about 6 carbon equivalents in length, an unbranched saturated or unsaturated chain of from about 6 to 18 carbon equivalents in length with at least one of intermediate amide and disulfide moieties, and a polyethylene glycol chain of from about 3 to 12 carbon equivalents in length; group R.sub.3 is selected from one of an H, an alkyl, and a methylene or ethylene moiety with an electronegative substituent; and BAS and BAS* are biologically active species.
    Type: Grant
    Filed: October 22, 1997
    Date of Patent: February 16, 1999
    Assignee: Prolinx, Inc.
    Inventors: Mark L. Stolowitz, Robert J. Kaiser, Kevin P. Lund
  • Patent number: 5869623
    Abstract: Boron compound complexing reagents, intermediate reagents of those reagents, and methods of synthesizing these reagents are disclosed. These reagents, including those shown as General Formula II may be used, after further reactions described herein, to complex with boronic compounds, such as phenylboronic acid or derivatives thereof. ##STR1## In one embodiment, group Z comprises a spacer selected from a saturated or unsaturated chain of up to about 6 carbon equivalents in length, an unbranched saturated or unsaturated chain from about 6 to 18 carbon equivalents in length with at least one intermediate amide or disulfide moieties, and a polyethylene glycol chain of from about 3 to 12 carbon equivalents in length; group R.sub.2 is one of an alkyl and a methylene group with an electronegative moiety; and BAS is a biologically active species.
    Type: Grant
    Filed: October 22, 1997
    Date of Patent: February 9, 1999
    Assignees: Systemix, Prolinx, Inc.
    Inventors: Mark L. Stolowitz, Robert J. Kaiser, Kevin P. Lund, Steven M. Torkelson
  • Patent number: 5859210
    Abstract: Boron compound complexing reagents, boron compound complexes, and methods of synthesizing these reagents and complexes are disclosed. These reagents and complexes include those shown in General Formula IV and General Formula VI. In one embodiment, the reagent of General Formula IV may be used to form a complex with a boron compound, such as a complex shown in General Formula VI. ##STR1## In one embodiment, group Z comprises a spacer selected from a saturated or unsaturated chain of up to about 6 carbon equivalents in length, an unbranched saturated or unsaturated chain of from about 6 to 18 carbon equivalents in length with at least one of intermediate amide or disulfide moieties, and a polyethylene glycol chain of from about 3 to 12 carbon equivalents in length; group R.sub.3 is selected from one of an H, an alkyl, and a methylene or ethylene moiety with an electronegative substituent; and BAS and BAS* are biologically active species.
    Type: Grant
    Filed: October 22, 1997
    Date of Patent: January 12, 1999
    Assignees: Prolinx, Inc., Systemix
    Inventors: Mark L. Stowolitz, Robert J. Kaiser, Kevin P. Lund, Steven M. Torkelson
  • Patent number: 5847192
    Abstract: Boron compound complexing reagents and methods of synthesizing these reagents are disclosed. These reagents, including those shown as General Formula I and General Formula II may be used, after further reactions described herein, to complex with boronic compounds, such as phenylboronic acid or derivatives thereof.
    Type: Grant
    Filed: August 5, 1996
    Date of Patent: December 8, 1998
    Assignees: Prolinx, Inc., Systemix
    Inventors: Mark L. Stolowitz, Robert J. Kaiser, Kevin P. Lund, Steven M. Torkelson
  • Patent number: 5837878
    Abstract: Boron compound complexing reagents, boron compound complexes, and methods of synthesizing these reagents and complexes are disclosed. These reagents and complexes include those shown in General Formula CIII, General Formula CIV, and General Formula CVI. In one embodiment, the reagents of General Formula CIII may be used to produce, after condensation with a bioactive species (BAS), the reagent of General Formula CIV. The reagent of General Formula CIV may be used to form a complex with a boron compound, such as a complex shown in General Formula CVI.
    Type: Grant
    Filed: August 5, 1996
    Date of Patent: November 17, 1998
    Assignee: Prolinx, Inc.
    Inventors: Mark L. Stolowitz, Robert J. Kaiser, Kevin P. Lund
  • Patent number: 5777148
    Abstract: Boron compound complexing reagents, intermediate reagents of those reagents and methods of synthesizing these reagents are disclosed. These reagents, including those shown as General Formula I and General Formula II may be used, after further reactions described herein, to complex with boronic compounds, such as phenylboronic acid or derivatives thereof.
    Type: Grant
    Filed: August 5, 1996
    Date of Patent: July 7, 1998
    Assignee: Prolinx, Inc.
    Inventors: Mark L. Stowolitz, Robert J. Kaiser, Kevin P. Lund
  • Patent number: 5744627
    Abstract: Boron compound complexing reagents, boron compound complexes, and methods of synthesizing these reagents and complexes are disclosed. These reagents and complexes include those shown in General Formula III, General Formula IV, and General Formula VI. In one embodiment, the reagents of General Formula III may be used to produce, after condensation with a bioactive species (BAS), the reagent of General Formula IV. The reagent of General Formula IV may be used to form a complex with a boron compound, such as a complex shown in General Formula VI.
    Type: Grant
    Filed: August 5, 1996
    Date of Patent: April 28, 1998
    Assignees: Prolinx, Inc., Systemix
    Inventors: Mark L. Stowolitz, Robert J. Kaiser, Kevin P. Lund, Steven M. Torkelson
  • Patent number: 5736747
    Abstract: Organic compounds having at least one ethylenically-unsaturated group are described, the organic compounds being suitable for use in coatable compositions as reactive diluents; compounds of the invention preferably have a divalent organic linking moiety devoid of reactive groups other than optional ethylenically-unsaturated groups, and a polar organic moiety and are particularly adept in solubilizing aminoplast resins having radiation-curable pendant groups.
    Type: Grant
    Filed: February 23, 1996
    Date of Patent: April 7, 1998
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Ernest L. Thurber, Eric G. Larson, Alan R. Kirk, Gregg D. Dahlke
  • Patent number: 5652371
    Abstract: The invention relates to novel 3-imino-3-alkoxy-propionic acid lactates and their tautomeric acrylic acid lactates, processes for their preparation and their use as intermediates in the synthesis of 2-amino-substituted 1,4-dihydropyridines.
    Type: Grant
    Filed: August 22, 1995
    Date of Patent: July 29, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Jurgen Stoltefuss, Michael Negele
  • Patent number: 5637749
    Abstract: Water-soluble aryl imidate activated polyalkylene oxides having improved hydrolytic stability and conjugates of the aryl imidate activated polyalkylene oxides with biologically active nucleophiles are disclosed. Methods of preparing the activated polyalkylene oxides and conjugates thereof are also disclosed.
    Type: Grant
    Filed: July 26, 1995
    Date of Patent: June 10, 1997
    Assignee: Enzon, Inc.
    Inventor: Richard B. Greenwald
  • Patent number: 5616546
    Abstract: Improved automatic dishwashing detergent compositions, especially granular detergents, comprising bleach activators which form multiperacids, especially specific monoquaternary substituted bis(peroxycarbonic) acids, upon perhydrolysis are provided.
    Type: Grant
    Filed: October 23, 1995
    Date of Patent: April 1, 1997
    Assignee: The Procter & Gamble Company
    Inventors: Gregory S. Miracle, Mark R. Sivik
  • Patent number: 5609848
    Abstract: Haloaryl compounds are lithiated and thereafter metalated with one of the following organometallic groups: Sn(n--Bu).sub.3 or SnMe.sub.3. The resulting aryltin compound can be transmetalated in site-specific reaction with one of the following organometallic groups: HgX, Hg(OAc).sub.2, BX.sub.3, or BZ.sub.2, wherein X is Cl, Br, or I, and Z is alkyl or alkoxy. The metalated compounds are subsequently radiohalogenated via a demetalation reaction. A functional group suitable for conjugation to protein can be added subsequent or preferably prior to the radiohalogenation.Also compounds of the formula: R.sub.1 --Ar--R.sub.2, wherein R.sub.1 is either a radiohalogen or any one of the organometallic groups stated above, Ar is aromatic or heteroaromatic ring, and R.sub.2 is a short-chain substituent that does not activate the aromatic ring and that bears a functional group, or a precursor thereof, suitable for conjugation to protein under conditions that preserve the biological activity of the protein.
    Type: Grant
    Filed: September 23, 1991
    Date of Patent: March 11, 1997
    Assignee: NeoRx Corporation
    Inventors: D. Scott Wilbur, Alan R. Fritzberg
  • Patent number: 5595967
    Abstract: Improved detergent compositions, especially granular detergents, comprising bleach activators which form multiperacids, especially specific monoquaternary substituted bis(peroxycarbonic) acids, upon perhydrolysis are provided.
    Type: Grant
    Filed: October 23, 1995
    Date of Patent: January 21, 1997
    Assignee: The Procter & Gamble Company
    Inventors: Gregory S. Miracle, Mark R. Sivik, Patti J. Kellett
  • Patent number: 5543541
    Abstract: A method for preparing an alkoxyethylidene-substituted aryl hydrazine having the formula ##STR1## and thereafter cyclizing the same with a cyanate salt under mildly acidic conditions in the presence of an organic solvent, optionally in the presence of a cyclization-aiding amount of water, to form an aryl triazolinone of the formula ##STR2## wherein X is independently hydrogen, halogen, lower alkyl, lower alkoxy, nitro, hydroxy, --NHSO.sub.2 R.sup.1, --NR.sup.1 SO.sub.2 R.sup.1, or --N(SO.sub.2 R.sup.1).sub.2, where R.sup.1 is lower alkyl; R is lower alkyl, and each R is the same; and n is an integer of from 1-3, which triazolinones am useful as intermediates for preparing herbicides.
    Type: Grant
    Filed: April 4, 1995
    Date of Patent: August 6, 1996
    Assignee: FMC Corporation
    Inventor: Jaidev S. Goudar
  • Patent number: 5534180
    Abstract: Improved automatic dishwashing detergent compositions, especially granular detergents, comprising bleach activators which form multiperacids, especially specific monoquaternary substituted bis(peroxycarbonic) acids, upon perhydrolysis are provided.
    Type: Grant
    Filed: February 3, 1995
    Date of Patent: July 9, 1996
    Inventors: Gregory S. Miracle, Mark R. Sivik
  • Patent number: 5534179
    Abstract: Improved detergent compositions, especially granular detergents, comprising bleach activators which form multiperacids, especially specific monoquaternary substituted bis(peroxycarbonic) acids, upon perhydrolysis are provided.
    Type: Grant
    Filed: February 3, 1995
    Date of Patent: July 9, 1996
    Inventors: Gregory S. Miracle, Mark R. Sivik, Patti J. Kellett
  • Patent number: 5523152
    Abstract: Organic compounds having at least one ethylenically-unsaturated group are described, the organic compounds being suitable for use in coatable compositions as reactive diluents; compounds of the invention preferably have a divalent organic linking moiety devoid of reactive groups other than optional ethylenically-unsaturated groups, and a polar organic moiety and are particularly adept in solubilizing aminoplast resins having radiation-curable pendant groups.
    Type: Grant
    Filed: November 4, 1994
    Date of Patent: June 4, 1996
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Ernest L. Thurber, Eric G. Larson, Alan R. Kirk, Gregg D. Dahlke
  • Patent number: 5440065
    Abstract: This invention relates to a novel synthesis of 4-amino-5-hexenoic acid by thermal rearrangements, and to the novel intermediates produced thereby.
    Type: Grant
    Filed: July 22, 1994
    Date of Patent: August 8, 1995
    Assignee: Merrell Dow Pharmaceuticals Inc.
    Inventor: Patrick Casara
  • Patent number: 5380936
    Abstract: This invention relates to a novel synthesis of 4-amino-5-hexenoic acid by thermal rearrangements, and to the novel intermediates produced thereby.
    Type: Grant
    Filed: January 19, 1994
    Date of Patent: January 10, 1995
    Assignee: Merrell Dow Pharmaceuticals Inc.
    Inventor: Patrick Casara
  • Patent number: 5371084
    Abstract: Compounds having the formula (I): ##STR1## and stereoisomers thereof, wherein A is hydrogen, halo, hydroxy, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 haloalkyl, C.sub.1-4 haloalkoxy, C.sub.1-4 alkylcarbonyl, C.sub.1-4 alkoxycarbonyl, phenoxy, nitro or cyano; R.sup.1 and R.sup.2, which may be the same or different, are hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted heterocyclylalkyl, optionally substituted cycloalkylalkyl, optionally substituted aralkyl, optionally substituted heteroarylalkyl, optionally substituted aryloxyalkyl, optionally substituted heteroaryloxyalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted alkoxy, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted aryloxy, optionally substituted heteroaryloxy, nitro, halo, cyano, --NR.sup.3 R.sup.4, --CO.sub.2 R.sup.3, --CONR.sup.3 R.sup.4, --COR.sup.3, --S(O).sub.n R.sup.3 wherein n is 0, 1 or 2, (CH.sub.2).sub.m PO(OR.
    Type: Grant
    Filed: October 28, 1993
    Date of Patent: December 6, 1994
    Assignee: Zeneca Limited
    Inventors: Paul J. de Fraine, Anne Martin
  • Patent number: 5358955
    Abstract: The present invention relates to a compound of the formula ##STR1## or a pharmaceutically acceptable salt thereof wherein W is selected from optionally substituted pyridyl, naphthyl, and quinolyl; which inhibits lipoxygenase enzyme activity and leukotriene biosynthesis and is useful in the treatment of inflammatory disease states; also disclosed are leukotriene biosynthesis inhibiting compositions and a method for inhibiting lipoxygenase enzyme activity and leukotriene biosynthesis.
    Type: Grant
    Filed: June 2, 1993
    Date of Patent: October 25, 1994
    Assignee: Abbott Laboratories
    Inventors: Dee W. Brooks, Teodozy J. Kolasa
  • Patent number: 5354495
    Abstract: A physical property-improving reagent which comprises an alkenoylcarbamate compound of the formula: ##STR1## wherein R is a hydrogen atom or a lower alkyl group, X is an oxygen atom (--O--), a sulfur atom (--S--) or a substituted or unsubstituted imino group (--NR'--), R' being a hydrogen atom or a lower alkyl group, and Y is the residue of an active hydrogen atom-containing compound excluding --X--H therefrom dissolved in an organic solvent having a solubility parameter of not less than 8, which can impart excellent physical properties to a polymer produced with the same.
    Type: Grant
    Filed: March 1, 1990
    Date of Patent: October 11, 1994
    Assignee: Nippon Paint Co., Ltd.
    Inventors: Satoshi Urano, Ryuzo Mizuguchi, Noriyuki Tsuboniwa, Kei Aoki, Yuji Suzuki, Takeyasu Itoh
  • Patent number: 5344970
    Abstract: A ruthenium-phosphite complex having the formula ##STR1## wherein a is from 1 to 3; b is 1 or 2; c is from 0 to 3; and R is hydrogen, alkyl, aryl, halo, amino, acetylamino, or sulfo; and X is ##STR2## where R.sub.1, R.sub.2, and R.sub.3 are the same or different and are hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl.This complex can be used to effect the reduction of unsaturated organic compounds or, when comprised of ligands having optical activity, can be used as the catalyst for effecting the asymmetric reduction of unsaturated organic compounds.
    Type: Grant
    Filed: December 22, 1993
    Date of Patent: September 6, 1994
    Assignee: Albemarle Corporation
    Inventor: Charles H. Kolich
  • Patent number: 5319122
    Abstract: This invention relates to a novel process for preparing benzylformimidates which are useful in the production of certain carbapenem antibiotics. The process of this invention provides a means of producing a high-yield, high-purity product.
    Type: Grant
    Filed: November 12, 1992
    Date of Patent: June 7, 1994
    Assignee: Merck & Co., Inc.
    Inventor: Joel J. Friedman
  • Patent number: 5300681
    Abstract: A process is disclosed for the enantioselective hydrogenation of olefins of the formula: ##STR1## where R is hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl, Z is ##STR2## where R' is hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl, --CN, C(NH)OR" where R" is C.sub.1 to C.sub.6 linear or branched alkyl, or --C(O)NH.sub.2 ; and Ar is phenyl or naphthyl unsubstituted or substituted with benzoyl or substituted benzoyl, C.sub.1 to C.sub.6 linear or branched alkyl, C.sub.1 to C.sub.6 linear or branched alkoxy, halo, or carboxylic acid or C.sub.1 to C.sub.6 linear or branched alkyl ester thereof, which comprises contacting said aromatic-substituted olefin with a catalytically effective amount of a ruthenium phosphite complex.
    Type: Grant
    Filed: June 10, 1993
    Date of Patent: April 5, 1994
    Assignee: Ethyl Corporation
    Inventor: Merrikh Ramezanian
  • Patent number: 5298643
    Abstract: Water-soluble aryl imidate activated polyalkylene oxides having improved hydrolytic stability and conjugates of the aryl imidate activated polyalkylene oxides with biologically active nucleophiles are disclosed. Methods of preparing the activated polyalkylene oxides and conjugates thereof are also disclosed.
    Type: Grant
    Filed: December 22, 1992
    Date of Patent: March 29, 1994
    Assignee: Enzon, Inc.
    Inventor: Richard B. Greenwald
  • Patent number: 5237084
    Abstract: Dialkyl (N-cyanoimido) carbonates are prepared in good yield in a non-aqueous solvent by a process which comprises either (a) adding a cyanogen halide at a controlled rate to a reactor containing an unsubstituted or substituted dialkyl imidocarbonate, an inorganic base and/or a trialkyl amine, or (b) by adding a trialkyl amine to a solution of the unsubstituted or substituted dialkyl imidocarbonate and a cyanogen halide. The dialkyl imidocarbonate precursors are prepared by using a stoichiometric ratio (2:1) of alcohol to cyanogen halide in the presence of an acid acceptor and in a non-aqueous solvent.Dialkyl (N-cyanoimido)carbonates are useful as intermediates for pesticides and pharmaceuticals.
    Type: Grant
    Filed: January 21, 1992
    Date of Patent: August 17, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Michael A. Oliver, Ward H. Oliver
  • Patent number: 5206403
    Abstract: A new diphenyl-methane derivative is useful to inhibit agglomeration of blood and is defined by the formula, including a diphenylethylene derivative and a benzophenone oxime either derivative. ##STR1## in which R1 and R2 each are hydrogen, hydroxyl or a lower alkoxy, U is .dbd.CXY or .dbd.N--O--W,X is hydrogen, cyano or --COR6, R6 being hydroxyl or an amino, Y is --R10--COR6, R3 being hydrogen or a lower alkoxy, R10 being an alkylene having 1 to 3 carbon atoms, straight or branched, --CO--NR4R5, R4 and R5 each being hydrogen, a lower alkyl or a lower arylalkyl, --CH2--NHSO2--C6H5 or --C(R8).dbd.NR7, R7 being a lower alkoxy or an aryl, R8 is --VR9, V being oxygen, sulfur or nitrogen, R9 being an alkyl or an aryl,W is --CH2--CO--CH2--COOR13, R13 being hydrogen or a lower alkyl, --CH2--C(.dbd.
    Type: Grant
    Filed: November 5, 1990
    Date of Patent: April 27, 1993
    Assignee: Eisai Co., Ltd.
    Inventors: Youji Yamagishi, Kozo Akasaka, Takeshi Suzuki, Mitsuaki Miyamoto, Kouji Nakamoto, Kazuo Okano, Shinya Abe, Hironori Ikuta, Kenji Hayashi, Hiroyuki Yoshimura, Tohru Fujimori, Koukichi Harada, Isao Yamatsu
  • Patent number: 5194103
    Abstract: Energetic compounds of the formula ##STR1## wherein R.sub.1 is --OCH.sub.2 CH.sub.2 C(NO.sub.2).sub.3, --OCH.sub.2 C.sub.2).sub.2 CH.sub.3, --OCH.sub.2 C(NO.sub.2).sub.3, --OCH.sub.2 CF(NO.sub.2).sub.2, --OCH.sub.2 CF.sub.2 (NO.sub.2), or --OCH.sub.2 CF.sub.3, and wherein R.sub.2 is --OCH.sub.2 CH.sub.2 C(NO.sub.2).sub.3, --OCH.sub.2 CF(NO.sub.2).sub.2, --OCH.sub.2 CF.sub.2 (NO.sub.2), --OCH.sub.2 CF.sub.3, --NH.sub.2, --NHCH.sub.2 CH.sub.2 ONO.sub.2, or --N(NO.sub.2)CH.sub.2 CH.sub.2 ONO.sub.2.
    Type: Grant
    Filed: April 30, 1991
    Date of Patent: March 16, 1993
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventor: Michael E. Sitzmann
  • Patent number: 5183828
    Abstract: Polyhydroxy-substituted benz, phenylacet and mandelamidines, amidates, amidoximes and hydroxyamidoximes--ribonucleotide reductase inhibitors, and free radical scavengers.
    Type: Grant
    Filed: July 20, 1990
    Date of Patent: February 2, 1993
    Inventors: Bartholomeus van't Riet, Howard L. Elford, Galen L. Wampler
  • Patent number: 5166434
    Abstract: A process is disclosed for preparing aromatic-substituted unsaturated amides. The process comprises treating a compound of the formula ##STR1## where Ar is C.sub.6 to C.sub.10 aryl unsubstituted or substituted with at least one halo, amino, nitro, hydroxy, C.sub.1 to C.sub.12 linear or branched alkyl, C.sub.1 to C.sub.12 linear or branched alkoxy or haloalkyl, the alkyl moiety being C.sub.1 to C.sub.6 linear or branched or the group ##STR2## where Ar' is C.sub.6 to C.sub.10 aryl unsubstituted or substituted with at least one halo, amino, nitro, hydroxy, C.sub.1 to C.sub.12 linear or branched alkyl, C.sub.1 to C.sub.12 alkoxy or haloalkyl, the alkyl moiety being C.sub.1 to C.sub.6 linear or branched; and R and R' are the same or different and are hydrogen or C.sub.1 to C.sub.12 linear or branched alkyl and can also be phenyl unsubstituted or substituted with at least one halo, amino, nitro, hydroxy, C.sub.1 to C.sub.12 linear or branched alkyl, C.sub.1 to C.sub.
    Type: Grant
    Filed: April 1, 1991
    Date of Patent: November 24, 1992
    Assignee: Ethyl Corporation
    Inventor: Kathleen S. Laurenzo
  • Patent number: 5117057
    Abstract: This invention relates to insecticidal compositions containing N'-substituted-N,N'-disubstitutedhydrazines, methods of using such compositions and N'-substituted-N, N'-disubstitutedhydrazines. Specifically, the invention relates to insect growth regulating compositions, and methods of using such compositions, which include compounds having a nucleus of the formula ##STR1## where A', B', D and J are independently any atom or group of atoms; where E is a tertiary carbon containing organic radical, a haloalkyl having a total of at least four carbon and halogen atoms but not more than six halogen atoms, or a non-tertiary carbon containing non-haloalkyl organic or organometallic radical having at least five atoms other than hydrogen, oxygen and halogen, and is attached to the nitrogen shown in the formula by a carbon-to-nitrogen single bond; where one G.sub.1 is C, N, O and S, and both G.sub.2 's and the other G.sub.1 are carbon; or one G.sub.2 is S or P, and both G.sub.1 's and the other G.sub.
    Type: Grant
    Filed: June 14, 1991
    Date of Patent: May 26, 1992
    Assignee: Rohm and Haas Company
    Inventors: Adam C. Hsu, Harold E. Aller, Raymond A. Murphy, Dat P. Le, Donald W. Hamp, Barry Weinstein
  • 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: 5026866
    Abstract: The present invention relates to a new method of synthesis of 2,2'-bis.DELTA..sup.2 -oxazoline, which consists of three steps:in the first step,N,N'-bis-(2-hydroxyethyl)-oxamide (I) is reacted with hydrogen chloride and a nitrile of formula RCN in which R.dbd.H, alkyl, aryl, arylalkyl, alkylaryl, in order to yield the correspondingN,N'-bis-(2-iminoacyloxyethyl)oxamide.2HCl (II).In the second step, the compound (II) is pyrolyzed in order to yieldN,N'-bis-(2-chloroethyl)oxamide (III) which in the third step generates, by means of the treatment with a base, the desired product 2,2'-bis-.DELTA..sup.2 -oxazoline.
    Type: Grant
    Filed: December 21, 1989
    Date of Patent: June 25, 1991
    Assignee: Enichem Anic S.p.A.
    Inventors: Giuseppe Messina, Loreno Lorenzoni, Giovanna Chessa
  • Patent number: 5025102
    Abstract: SF.sub.5 N.dbd.C[OCH.sub.2 CF(NO.sub.2).sub.2 ].sub.2, which is useful as energetic plasticizer in plastic bonded explosives.
    Type: Grant
    Filed: July 18, 1990
    Date of Patent: June 18, 1991
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventor: Michael E. Sitzmann
  • Patent number: 4973726
    Abstract: Herbicidal 3-aminopyrazolin-5-ones of the formula ##STR1## in which R.sup.1 stands for alkyl, alkenyl, halogenoalkyl, halogenoalkenyl, alkoxyalkyl, alkylthioalkyl, cycloalkyl, for optionally substituted aralkyl or for optionally substituted aryl,R.sup.2 stands for hydrogen or alkyl,R.sup.3 stands for hydrogen or alkyl,R.sup.4 stands for hydrogen, alkyl, alkenyl, alkinyl, alkoxyalkyl, alkylthioalkyl, alkoxycarbonylalkyl or alkanoyl, orR.sup.3 and R.sup.4 together stand for an alkylene or alkenylene radical, each of which is divalent, X stands for halogen, alkyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy or halogenoalkylthio, andZ stands for hydrogen, halogen, alkyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy or halogenoalkylthio,and acid addition salts thereof. Intermediates of the formula ##STR2## are also disclosed.
    Type: Grant
    Filed: December 1, 1989
    Date of Patent: November 27, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Uta Jensen-Korte, Hans-Joachim Santel, Robert R. Schmidt, Harry Strang
  • Patent number: 4942253
    Abstract: Polyhydroxy-substituted benz, phenylacet and mandelamidines, amidates, amidoximes and hydroxyamidoximes--ribonucleotide reductase inhibitors, and free radical scavengers.
    Type: Grant
    Filed: September 15, 1986
    Date of Patent: July 17, 1990
    Inventors: Bartholomeus van't Riet, Howard L. Elford, Galen L. Wampler
  • Patent number: 4879249
    Abstract: Novel immunoassay which utilizes an enzyme linked ligand or receptor wherein the enzyme is bacterial luciferase; mercantile kit useful in performing said immunoassay; and compounds utilized in performing said assay.
    Type: Grant
    Filed: March 17, 1986
    Date of Patent: November 7, 1989
    Inventors: Thomas O. Baldwin, Thomas F. Holzman, Paul S. Satoh, Frederick S. Yein