Plural (x=)n(=x)-x- Groups Containing Patents (Class 558/484)
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Publication number: 20140147529Abstract: 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: ApplicationFiled: December 20, 2011Publication date: May 29, 2014Applicant: DSM IP ASSETS B.V.Inventors: Stephane Duval, Maik Kindermann
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Patent number: 8658818Abstract: 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: GrantFiled: November 23, 2010Date of Patent: February 25, 2014Assignee: Alliant Techsystems Inc.Inventors: Nicholas A. Straessler, Alexander J. Paraskos, Michael P. Kramer
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Publication number: 20120309825Abstract: 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: ApplicationFiled: May 31, 2012Publication date: December 6, 2012Applicant: The Charlotte-Mecklenburg Hospital Authority d/b/a Carolinas Medical CenterInventors: Guqi Wang, Qi Long Lu
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Patent number: 7947855Abstract: 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: GrantFiled: July 2, 2008Date of Patent: May 24, 2011Assignee: Dipharma S.p.A.Inventors: Tiziano Scubla, Nevio Francescutti, Fausto Gorassini, Graziano Castaldi
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Publication number: 20110076730Abstract: 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: ApplicationFiled: July 19, 2007Publication date: March 31, 2011Applicant: Board of Trustees of Michigan State UniversityInventors: John W. Frost, Wei Niu
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Patent number: 7754772Abstract: 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: GrantFiled: May 23, 2005Date of Patent: July 13, 2010Assignee: 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
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Patent number: 6677374Abstract: 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: GrantFiled: March 29, 2002Date of Patent: January 13, 2004Assignee: Queen's University at KingstonInventors: Gregory R. J. Thatcher, Brian M. Bennett, James N. Reynolds, Roland J. Boegman, Khem Jhamandas
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Patent number: 6211233Abstract: 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: GrantFiled: November 8, 1999Date of Patent: April 3, 2001Assignee: Nicox S.A.Inventor: Piero Del Soldato
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Patent number: 6180664Abstract: 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: GrantFiled: June 8, 1999Date of Patent: January 30, 2001Assignee: ISIS Pharma GmbHInventors: Ulrich Hess, Anne-Katrin Windeck, Holger Brosig
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Patent number: 5955629Abstract: 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: GrantFiled: April 26, 1989Date of Patent: September 21, 1999Assignee: Cordant Technologies Inc.Inventors: J. B. Canterberry, W. H. Graham
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Patent number: 5892067Abstract: 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: GrantFiled: June 9, 1997Date of Patent: April 6, 1999Assignee: The United States of America as represented by the Secretary of the NavyInventor: Mostafa A. H. Talukder
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Patent number: 5883122Abstract: 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: GrantFiled: June 3, 1997Date of Patent: March 16, 1999Assignee: Queen's University at KingstonInventors: Gregory R. J. Thatcher, Brian M. Bennett, James N. Reynolds, Roland J. Boegman, Khem Jhamandas
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Patent number: 5807847Abstract: 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: GrantFiled: June 4, 1996Date of Patent: September 15, 1998Assignee: Queen's University at KingstonInventors: Gregory R. J. Thatcher, Brian M. Bennett
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Patent number: 5313000Abstract: 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: GrantFiled: January 27, 1992Date of Patent: May 17, 1994Assignee: The Secretary of State for Defence in her Britannic Majesty's Government of the U.K. of Britain and Northern IrelandInventor: Malcolm J. Stewart
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Patent number: 5310433Abstract: 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: GrantFiled: December 24, 1987Date of Patent: May 10, 1994Assignee: Hercules IncorporatedInventors: Lawrence E. Carosino, Kenneth O. Hartman
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Patent number: 5089652Abstract: 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: GrantFiled: January 17, 1990Date of Patent: February 18, 1992Assignee: Atlas Powder CompanyInventors: Joseph A. Sohara, Randal A. Johnson, William E. Gorton
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Patent number: 5081255Abstract: 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: GrantFiled: May 17, 1991Date of Patent: January 14, 1992Assignee: The United States of America as represented by the Secretary of the NavyInventor: Michael E. Sitzmann
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Patent number: 5049694Abstract: 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: GrantFiled: September 14, 1989Date of Patent: September 17, 1991Assignee: Cedona Pharmaceuticals B.V.Inventors: Jan Bron, Geert J. Sterk, Jan F. van der Werf, Hendrik Timmerman
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Patent number: 4985584Abstract: 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: GrantFiled: October 27, 1986Date of Patent: January 15, 1991Assignee: Secretary of State for DefenceInventors: Ross W. Millar, Norman C. Paul, David H. Richards
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Patent number: 4863949Abstract: 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: GrantFiled: September 21, 1987Date of Patent: September 5, 1989Assignee: Boehringer Mannheim GmbHInventors: Herbert Simon, Helmut Michel, Wolfgang Bartsch, Klaus Strein
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Patent number: 4853157Abstract: 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: GrantFiled: June 14, 1984Date of Patent: August 1, 1989Assignee: AECI LimitedInventor: Anthony J. Stiff
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Patent number: 4820859Abstract: 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: GrantFiled: November 5, 1985Date of Patent: April 11, 1989Assignee: Secretary of State for Defence in Her Majesty's Government of the United KingdomInventors: Ross W. Millar, Norman C. Paul, David H. Richards
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Patent number: 4801596Abstract: 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: GrantFiled: December 2, 1985Date of Patent: January 31, 1989Assignee: Boehringer Mannheim GmbHInventors: Herbert Simon, Helmut Michel, Walter-Gunar Friebe, Wolfgang Bartsch
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Patent number: 4781861Abstract: An energetic azide-terminated azido compound and a method for producing same is disclosed.Type: GrantFiled: December 15, 1987Date of Patent: November 1, 1988Assignee: Rockwell International CorporationInventors: Edgar R. Wilson, Milton B. Frankel
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Patent number: H448Abstract: 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: GrantFiled: July 6, 1987Date of Patent: March 1, 1988Assignee: The United States of America as represented by the Secretary of the NavyInventors: Robert E. Farncomb, Walter A. Carr