Plural (x=)n(=x)-x- Groups Containing Patents (Class 558/484)
  • Publication number: 20140147529
    Abstract: The present invention relates to a method for reducing the production of methane emanating from the digestive activities of a ruminant and/or for improving ruminant animal performance by using, as active compound at least one organic molecule substituted at any position with at least one nitrooxy group, or a salt thereof, which is administrated to the animal together with the feed. The invention also relates to the use of these compounds in feed and feed additives such as premix, concentrates and total mixed ration (TMR) or in the form of a bolus.
    Type: Application
    Filed: December 20, 2011
    Publication date: May 29, 2014
    Applicant: DSM IP ASSETS B.V.
    Inventors: Stephane Duval, Maik Kindermann
  • Patent number: 8658818
    Abstract: Methods of forming a nitrate ester include combining at least one nitrate salt and sulfuric acid to form a nitrating solution and adding an aliphatic polyol to the nitrating solution. Nitrate esters formed by this method may be, for example, triethylene glycol dinitrate (TEGDN), pentaerythritol tetranitrate (PETN), diglycerol tetranitrate (DGTN), 1,1,1-tris(methylol)ethane trinitrate (TMETN), 1,2,4-butanetriol trinitrate (BTTN), nitroglycerin (NG), diethylene glycol dinitrate (DEGDN), ethylene glycol dinitrate (EGDN), metriol trinitrate (MTN), nitrocellulose (NC), or 1,2-propanediol dinitrate (PDDN).
    Type: Grant
    Filed: November 23, 2010
    Date of Patent: February 25, 2014
    Assignee: Alliant Techsystems Inc.
    Inventors: Nicholas A. Straessler, Alexander J. Paraskos, Michael P. Kramer
  • Publication number: 20120309825
    Abstract: Alkyl nitrate ester compounds are provided for the delivery of nitric oxide to targeted muscle tissues, and in particular, to normal and dystrophic muscles. In one aspect, nitrate ester compounds are provided having the following formula: wherein, R1 is ONO2, CH2ONO2, CnH2n+1OH, CnH2n+1OH, CH3, CH2CH3, CH2CH2CH3, or H; R2 is ONO2, CH2ONO2, Cn?H2n?+1OH, Cn?H2n?+1OH, CH3, CH2CH3, CH2CH2CH3, or H; R3 is ONO2, CH2ONO2, Cn??H2n?+1OH, Cn?H2n?+1OH, CH3, CH2CH3, CH2CH2CH3, or H; and R4 is ONO2, CH2ONO2, Cn??H2n?+1OH, Cn?H2n?+1OH, CH3, CH2CH3, CH2CH2CH3, or H; wherein n is an integer from 0 to 9, n? is an integer from 0 to 9, and n? is an integer from 0 to 9, and n+n?+n??9, and wherein at least one of R1, R2, and R3 is an ester nitrate selected from the group consisting of ONO2, CH2ONO2, and combinations thereof.
    Type: Application
    Filed: May 31, 2012
    Publication date: December 6, 2012
    Applicant: The Charlotte-Mecklenburg Hospital Authority d/b/a Carolinas Medical Center
    Inventors: Guqi Wang, Qi Long Lu
  • Patent number: 7947855
    Abstract: A process for the purification of 1,4-butanediol mononitrate from 1,4-butanediol dinitrate and 1,4-butanediol, by selective extraction with solvents is herein disclosed.
    Type: Grant
    Filed: July 2, 2008
    Date of Patent: May 24, 2011
    Assignee: Dipharma S.p.A.
    Inventors: Tiziano Scubla, Nevio Francescutti, Fausto Gorassini, Graziano Castaldi
  • Publication number: 20110076730
    Abstract: Improved enzyme systems, recombinant cells, and processes employing the same to produce biosynthetic D-1,2,4-butanetriol; D-1,2,4-butanetriol prepared thereby and derivatives thereof; D-1,2,4-butanetriol trinitrate prepared therefrom; and enzymes and genes useful in the enzyme systems and recombinant cells.
    Type: Application
    Filed: July 19, 2007
    Publication date: March 31, 2011
    Applicant: Board of Trustees of Michigan State University
    Inventors: John W. Frost, Wei Niu
  • Patent number: 7754772
    Abstract: The invention describes novel nitrosated nonsteroidal antiinflammatory drugs (NSAIDs) and pharmaceutically acceptable salts thereof, and novel compositions comprising at least one nitrosated NSAID, and, optionally, at least one compound that donates, transfers or releases nitric oxide, stimulates endogenous synthesis of nitric oxide, elevates endogenous levels of endothelium-derived relaxing factor or is a substrate for nitric oxide synthase, and/or at least one therapeutic agent. The invention also provides novel compositions comprising at least one nitrosated NSAID, and at least one compound that donates, transfers or releases nitric oxide, elevates endogenous levels of endothelium-derived relaxing factor, stimulates endogenous synthesis of nitric oxide or is a substrate for nitric oxide synthase and/or at least one therapeutic agent. The invention also provides novel kits comprising at least one nitrosated NSAID, and, optionally, at least one nitric oxide donor and/or at least one therapeutic agent.
    Type: Grant
    Filed: May 23, 2005
    Date of Patent: July 13, 2010
    Assignee: NicOx, S.A.
    Inventors: Richard A. Earl, Maiko Ezawa, Xinqin Fang, David S. Garvey, Ricky D. Gaston, Subhash P. Khanapure, L. Gordon Letts, Chia-En Lin, Ramani R. Ranatunge, Stewart K. Richardson, Joseph D. Schroeder, Cheri A. Stevenson, Shiow-Jyi Wey
  • Patent number: 6677374
    Abstract: Compounds and methods for mitigating neurodegeneration, effecting neuroprotection and/or effecting cognition enhancement in a subject are described. Neurological or cognitive conditions are treated by administering to a subject an effective amount of a therapeutic compound comprising a nitrate ester, or a pharmaceutically acceptable salt or ester thereof.
    Type: Grant
    Filed: March 29, 2002
    Date of Patent: January 13, 2004
    Assignee: Queen's University at Kingston
    Inventors: Gregory R. J. Thatcher, Brian M. Bennett, James N. Reynolds, Roland J. Boegman, Khem Jhamandas
  • Patent number: 6211233
    Abstract: Compounds of the general formula A—X1—NO2, or their pharmaceutical compositions, wherein A contains a prostaglandin residue, X1 is a bivalent connecting bridge.
    Type: Grant
    Filed: November 8, 1999
    Date of Patent: April 3, 2001
    Assignee: Nicox S.A.
    Inventor: Piero Del Soldato
  • Patent number: 6180664
    Abstract: The invention describes novel compounds derived from pentaerythritol of general formula I, XIV, XVI, XIX and XXII, the substituents being as defined in the description, which can be used as pharmaceutical active substances, especially for the treatment of cardiovascular diseases.
    Type: Grant
    Filed: June 8, 1999
    Date of Patent: January 30, 2001
    Assignee: ISIS Pharma GmbH
    Inventors: Ulrich Hess, Anne-Katrin Windeck, Holger Brosig
  • Patent number: 5955629
    Abstract: Liquid nitromalonate polyesters and methods for their preparation are disclosed. Solid propellants are provided which employ as the binder a nitromalonate polyester. These propellants are resistant to plasticizer syneresis and crystallization and provide an increase in the specific impulse of the propellant.
    Type: Grant
    Filed: April 26, 1989
    Date of Patent: September 21, 1999
    Assignee: Cordant Technologies Inc.
    Inventors: J. B. Canterberry, W. H. Graham
  • Patent number: 5892067
    Abstract: Synthesis of a vinyl terminated polymer by reacting a cationically polymeable monomer in the form of a cyclic ether with an acid chloride in a suitable solvent and in the presence of a Lewis acid. The vinyl-terminated polymers can be polymerized with other appropriate monomers resulting in thermoplastic elastomers having suitable properties for use as binders for explosives and propellants.
    Type: Grant
    Filed: June 9, 1997
    Date of Patent: April 6, 1999
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventor: Mostafa A. H. Talukder
  • Patent number: 5883122
    Abstract: Aliphatic nitrate esters having a sulfur or phosphorus atom .beta. or .gamma. to a nitrate group and their congeners having efficacy as neuroprotective agents are described. Preferred nitrate esters may be synthesized by nitration of a 3-bromo-1,2-propanediol, and subsequent reaction to yield the desired mono-, di- or tetra-nitrate ester.
    Type: Grant
    Filed: June 3, 1997
    Date of Patent: March 16, 1999
    Assignee: Queen's University at Kingston
    Inventors: Gregory R. J. Thatcher, Brian M. Bennett, James N. Reynolds, Roland J. Boegman, Khem Jhamandas
  • Patent number: 5807847
    Abstract: Aliphatic Nitrate esters having a sulfur or phosphorus atom .beta. or .gamma. to a nitrate group having efficacy as vasodilators are described. Preferred nitrate esters may be synthesized by nitration of a 3-bromo-1,2-propanediol, and subsequent reaction to yield the desired mono, di or tetra nitrate ester.
    Type: Grant
    Filed: June 4, 1996
    Date of Patent: September 15, 1998
    Assignee: Queen's University at Kingston
    Inventors: Gregory R. J. Thatcher, Brian M. Bennett
  • Patent number: 5313000
    Abstract: This invention relates to the production of hydroxy-terminated polymers in the 2,000-20,000 MW range suitable for use as prepolymers in curing reactions with isocyanates to produce elastomers. The process involves the continuous addition over periods of 25-50 hours of an oxirane (monoepoxide) or a mixture of an oxirane and an oxetane to a reaction mixture, consisting of stoichiometric excesses of oxonium ion-forming catalyst such as BF.sub.3 -etherate and a diol initiator dissolved in an inert solvent. Under these conditions, chain extension of the diol occurs and the formation of cyclic oligomers and other impurities is minimised. The mole ratio of the initiator to catalyst is maintained at above 10:1 to suppress the formation of cationic terminal species on the growing polymer chain.
    Type: Grant
    Filed: January 27, 1992
    Date of Patent: May 17, 1994
    Assignee: The Secretary of State for Defence in her Britannic Majesty's Government of the U.K. of Britain and Northern Ireland
    Inventor: Malcolm J. Stewart
  • Patent number: 5310433
    Abstract: An efficient method for preparing nitrated glycerol glycol ether useful as a high energy plasticizer, by using as nitrator feed, the reaction products of an alkali metal bisulfate-catalyzed reaction of ethylene oxide and a stoichiometric excess of glycerol.
    Type: Grant
    Filed: December 24, 1987
    Date of Patent: May 10, 1994
    Assignee: Hercules Incorporated
    Inventors: Lawrence E. Carosino, Kenneth O. Hartman
  • Patent number: 5089652
    Abstract: The process of the present invention provides a method of obtaining a high yield of water or acid soluble nitrate esters without the use of organic solvents in the nitration reaction or the production of unstable products or by-products. The process involves the nitration of an organic hydroxy-containing compound with a suitable nitrating agent such as nitric acid in the absence of organic solvents in the nitration reaction. The reaction mixture is neutralized, causing the nitrate esters to precipitate or separate from the neutralized nitrate solution. The nitrate ester is then recovered, and any dissolved nitrate salts can be removed therefrom by gentle washing with water or a dilute halide solution. As provided by the process of the present invention, no organic solvents are used in the nitration reaction and average yields range from about 80% to about 95%.
    Type: Grant
    Filed: January 17, 1990
    Date of Patent: February 18, 1992
    Assignee: Atlas Powder Company
    Inventors: Joseph A. Sohara, Randal A. Johnson, William E. Gorton
  • Patent number: 5081255
    Abstract: A nitrate ester which is 2,4,6-trinitro-1-(2-hydroxyethylamino)-3- (2-hydyethylnitramino)benzenedinitrate; 2,4,6-trinitro-1,3,5-tris(2-hydroxyethylamino)benzenetrinitrate; 2,2',4,4',6,6'-hexanitro-3-(2-hydroxyethylnitramino)stilbenitrate; 2,5-bis[3-(hydroxyethylaminonitrate)-2,4,6-trinitrophenyl]1,3,4-oxadiazole ; or 2,5-bis[3-(hydroxyethylaminonitrate)-5- (hydroxyethylnitraminonitrate)-2,4,6-trinitrophenyl]-1,3,4-oxiazole and a process for preparing these compounds.
    Type: Grant
    Filed: May 17, 1991
    Date of Patent: January 14, 1992
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventor: Michael E. Sitzmann
  • Patent number: 5049694
    Abstract: The invention relates to pharmaceutical compositions containing novel nitrate esters, of which it was found that they are useful for the treatment of ischemiatic heart diseases, decompensatio cordis, myocardial infarction and hypertension.
    Type: Grant
    Filed: September 14, 1989
    Date of Patent: September 17, 1991
    Assignee: Cedona Pharmaceuticals B.V.
    Inventors: Jan Bron, Geert J. Sterk, Jan F. van der Werf, Hendrik Timmerman
  • Patent number: 4985584
    Abstract: A process for the production of a high energy nitrate ester involves reacting, in an inert organic solvent, a heterocyclic compound, selected from oxiranes, oxetanes, N-substituted aziridines and N-substituted azetidines, with either N.sub.2 O.sub.4 or N.sub.2 O.sub.5, and when the compound is reacted with N.sub.2 O.sub.4, oxidizing the O- or N-nitrate substituents or substituent in the product to O- or N-nitrate substituent or substituents. The remaining ring carbon atoms on the heterocyclic compound may be substituted or unsubstituted. Preferred substituent groups for the C and/or N ring atoms on the compound include alkyl, cyanoalkyl, haloalkyl, nitroalkyl, and substituted aryl.Several novel nitrate ester are also provided, including nitrated derivatives of polybutadiene, in which between 1% and 25% of the carbon atoms in the polymer are substituted by vicinal nitrate ester (--ONO.sub.2) groups.
    Type: Grant
    Filed: October 27, 1986
    Date of Patent: January 15, 1991
    Assignee: Secretary of State for Defence
    Inventors: Ross W. Millar, Norman C. Paul, David H. Richards
  • Patent number: 4863949
    Abstract: The present invention provides compounds of the general formula: ##STR1## wherein Ar is a substituted or unsubstituted aromatic or heteroaromatic radical, A is a straight-chained or branched alkylene chain containing up to 8 carbon atoms, a --CH.sub.2 -- group of which can be replaced by a cycloalkylene radical containing 3 to 7 carbon atoms, B is a straight-chained mono- or bicyclic, optionally branched, saturated or unsaturated alkylene chain containing up to 12 carbon atoms, a --CH.sub.2 -- group of which can be replaced by a cycloalkylene radical containing 3 to 7 carbon atoms and/or up to two --CH.sub.2 -- groups of which can be replaced by an oxygen or a sulphur atom or by an --S(.dbd.O) or --S(.dbd.O).sub.2 group, X is a valency bond, an oxygen atom or an --NR.sup.1 group, in which R.sup.1 is a hydrogen atom or a straight-chained or branched, saturated or unsaturated alkyl or nitroxyalkyl radical containing up to 6 carbon atoms or R.sup.1, together with the nitrogen atom of the --NR.sup.
    Type: Grant
    Filed: September 21, 1987
    Date of Patent: September 5, 1989
    Assignee: Boehringer Mannheim GmbH
    Inventors: Herbert Simon, Helmut Michel, Wolfgang Bartsch, Klaus Strein
  • Patent number: 4853157
    Abstract: A process for the preparation of nitric acid esters of organic hydroxy compounds by reacting an organic hydroxy compound with nitric acid in the presence of both sulphuric acid and in a solvent, followed by separating off the spent acid, substantially neutralizing the residual acidity of the organic solution, and removing solvent to leave the organic nitrate. From 95% to 220% of the stoichiometric requirement of nitric acid for complete nitration is used. The mole ratio of water to sulphuric acid at the end of the reaction is from 0.2:1 to 2.5:1. From 200 to 2000 ml of solvent per mole of hydroxy group is present. Yields of at least 92% are obtained. The invention is particularly suitable for the preparation of alkyl nitrates, alkylene or polyalkylene glycol, monoalkyl ether mononitrates, alkylene or polyalkylene glycol dinitrates, diol nitrates, nitrates containing homocyclic or heterocyclic rings, or nitrates derived from polyols.
    Type: Grant
    Filed: June 14, 1984
    Date of Patent: August 1, 1989
    Assignee: AECI Limited
    Inventor: Anthony J. Stiff
  • Patent number: 4820859
    Abstract: A process for the production of a high energy material involves reacting, in an inert organic solvent, a heterocyclic compound selected from oxirane, aziridine, oxetane or azetidine with a nitrogen oxide selected from dinitrogen tetroxide (N.sub.2 O.sub.4) and dinitrogen pentoxide (N.sub.2 O.sub.5) and, when the nitrogen oxide is N.sub.2 O.sub.4, oxidizing the O- or N- nitroso substituent or substituents in the product obtained to O- or N- nitro substituent or substituents. The heterocyclic compounds may be substituents or unsubstituted. In the former case the preferred substituents groups are halogen, alkyl, alkenyl, nitro and epoxy (as in epoxidized polybutadiene). The solvent is preferably a chlorinated alkane.Novel nitrated derivatives of polybutadiene, in which between 1% and 25% of the carbon atoms in the polymer are substituted by nitrate (ONO.sub.2), are also provided. These novel materials are liquid rubbers when the polybutadiene starting material has a molecular weight between 2000 and 10000.
    Type: Grant
    Filed: November 5, 1985
    Date of Patent: April 11, 1989
    Assignee: Secretary of State for Defence in Her Majesty's Government of the United Kingdom
    Inventors: Ross W. Millar, Norman C. Paul, David H. Richards
  • Patent number: 4801596
    Abstract: The present invention provides new aminopropanol derivatives of the general formula: ##STR1## wherein A is a direct bond, a straight-chained or branched alkylene chain containing up to 3 carbon atoms or a --CO--CH.sub.2 -- group; X is a direct bond or a carbonyl group; B is a straight-chained or branched, saturated or unsaturated alkylene chain containing up to 12 carbon atoms, in which one or two --CH.sub.2 -- groups can also be replaced by a saturated or unsaturated alkylene ring containing 3 to 7 carbon atoms and/or by an oxygen or sulphur atom or an --S(.dbd.O)-- or --S(.dbd.O).sub.2 -- group, n is 1, 2 or 3; R.sub.1 is a hydrogen atom or a straight-chained or branched, saturated or unsaturated alkyl radical containing up to 6 carbon atoms or a --B--(ONO.sub.2).sub.n group, in which B and n have the same meanings as above, or when A is a --CO--CH.sub.2 -- group and X is a direct bond, R.sub.
    Type: Grant
    Filed: December 2, 1985
    Date of Patent: January 31, 1989
    Assignee: Boehringer Mannheim GmbH
    Inventors: Herbert Simon, Helmut Michel, Walter-Gunar Friebe, Wolfgang Bartsch
  • Patent number: 4781861
    Abstract: An energetic azide-terminated azido compound and a method for producing same is disclosed.
    Type: Grant
    Filed: December 15, 1987
    Date of Patent: November 1, 1988
    Assignee: Rockwell International Corporation
    Inventors: Edgar R. Wilson, Milton B. Frankel
  • Patent number: H448
    Abstract: A process for preparing an energetic mixture of 1,2,4-butanetroil trinitr and nitroglycerin by forming a polyol mixture of 1,2,4-butanetriol and glycerin, and then nitrating the polyol mixture with a mixture of nitric and sulfuric acids.
    Type: Grant
    Filed: July 6, 1987
    Date of Patent: March 1, 1988
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Robert E. Farncomb, Walter A. Carr