Nitrate Esters Or Chalcogen Analogues Thereof (i.e., Compounds Having (x=)n(=x)-x- Bonded Directly To Carbon, Which Carbon May Be Single Bonded To Any Atom But May Be Multiple Bonded Only To Carbon; The X's May Be The Same Or Diverse Chalcogens) Patents (Class 558/480)
  • Patent number: 10612779
    Abstract: Sorbent compositions containing halogen and either nitrates or nitrites are added to coal to mitigate the release of mercury and/or other harmful elements into the environment during combustion of coal containing natural levels of mercury.
    Type: Grant
    Filed: April 4, 2018
    Date of Patent: April 7, 2020
    Assignee: NOx II, Ltd.
    Inventor: Douglas C. Comrie
  • Patent number: 10562873
    Abstract: Methods of producing glycidyl nitrate. The method comprises reacting glycerol and nitric acid in a microfluidic reactor to form a nitrated glycerol compound. The microfluidic reactor comprises a reaction volume of the microfluidic reactor of less than about 20 ml and an inner diameter of a reaction channel of the microfluidic reactor of less than or equal to about 1000 ?m. The nitrated glycerol compound is reacted with a base in the microfluidic reactor to form glycidyl nitrate. Additional methods of producing glycidyl nitrate are also disclosed.
    Type: Grant
    Filed: December 7, 2018
    Date of Patent: February 18, 2020
    Assignee: Northrop Grumman Innovation Systems, Inc.
    Inventors: Joseph J. Scavuzzo, Melissa L. Mileham
  • Patent number: 10266480
    Abstract: The invention relates to a method and to a device for removing contaminants arising during the production of aliphatic or alicyclic nitric acid esters, in particular for removing contaminants from nitrated crude nitric acid esters, which nitrated crude nitric acid esters arise during the nitration of monovalent or multivalent aliphatic or alicyclic alcohols capable of nitration, after the separation of the final nitrating acid, and to a production system for nitrating monovalent or multivalent aliphatic alcohols capable of nitration with subsequent purification of the nitrated nitric acid esters.
    Type: Grant
    Filed: June 25, 2014
    Date of Patent: April 23, 2019
    Assignee: Josef Meissner GmbH & Co. KG
    Inventors: Jurgen Pohlmann, Heinrich Hermann, Mirko Handel, Jurgen Gebauer
  • Patent number: 10017457
    Abstract: A process for synthesizing isooctyl nitrate in a continuous flow reactor comprises flowing a H2SO4-HNO3 mixture within a flow reactor, flowing isooctyl alcohol into said flow reactor so as to mix the isooctyl alcohol with the H2SO4-HNO3 mixture and produce a reaction mixture stream flowing in said reactor, maintaining the reaction mixture stream flowing in said flow reactor at a reaction temperature within in the range ?10° to 35° C. inclusive, and wherein the residence time of the reaction mixture stream in the flow reactor is greater than or equal to 5 seconds and less than or equal to 40 seconds, and wherein the H2SO4 of the H2SO4-HNO3 mixture is H2SO4 having a concentration of in the range of 85 to 95% inclusive, more desirably 88 to 92% inclusive, most desirably of 90%.
    Type: Grant
    Filed: March 5, 2015
    Date of Patent: July 10, 2018
    Assignee: Corning Incorporated
    Inventors: Bing Ma, Wei Shen, Yanhua Wang, Mo Zhang
  • Patent number: 9023890
    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, or CH2CH2CH3, or H; R2 is ONO2, CH2ONO2, Cn?H2n?+1OH, Cn?H2n?+1OH, CH2CH2CH3 or H; and R3 is ONO2, CH2ONO2, Cn??H2n?+1OH, Cn?H2n?+1OH, 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: Grant
    Filed: December 2, 2009
    Date of Patent: May 5, 2015
    Assignee: The Charlotte-Mecklenburg Hospital Authority
    Inventors: Guqi Wang, Qi Long Lu
  • Publication number: 20150031909
    Abstract: The present invention provides a method for producing alkyl nitrate. The centrifugal extraction equipment acts as the esterification separator; a mixed acid solution containing sulfuric acid and nitric acid enters from the heavy phase inlet of the centrifugal extraction equipment; alkyl alcohol enters from the light phase inlet of the centrifugal extraction equipment; the feeding molar ratio of alkyl alcohol and nitric acid equals to 1:1.0-3.0; esterification reaction occurs with the mixed acid and alkyl alcohol at a temperature of 10˜60° C.
    Type: Application
    Filed: December 21, 2012
    Publication date: January 29, 2015
    Inventors: Deliang Xu, Hengtao Mao
  • Patent number: 8536366
    Abstract: A process for the continuous production of a compound of Formula (II), HO—R1—ONO2 (II) wherein R1 is a straight chain alkyl radical having from 3 to 6 carbon atoms, in a two-phase solvent system, comprising contacting a compound of Formula (I), HO—R1—OH (I) wherein R1 is as defined above, with nitric acid in the presence of a first solvent, wherein the compound of Formula (II) is continuously extracted into a second solvent, and the reaction is carried out in a mixing microreactor which provides a power loss of at least 1.3 times the power loss provided under identical conditions by a circular cross-section straight-channel microreactor having an internal diameter equal to the average hydraulic diameter of the mixing microreactor and a length equal to the length of the mixing microreactor.
    Type: Grant
    Filed: December 19, 2008
    Date of Patent: September 17, 2013
    Assignee: DSM Fine Chemicals Austria NFG GmbH & Co KG
    Inventors: Sascha Braune, Stefan Steinhofer, Peter Poechlauer, Rafael Wilhelmus E. G. Reintjens, Nicole Theodora W. Linssen, Mehul Thathagar
  • Publication number: 20110130455
    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, or CH2CH2CH3, or H; R2 is ONO2, CH2ONO2, Cn?H2n?+1OH, Cn?H2n?+1OH, CH2CH2CH3 or H; and R3 is ONO2, CH2ONO2, Cn??H2n?+1OH, Cn?H2n?+1OH, 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: December 2, 2009
    Publication date: June 2, 2011
    Inventors: Guqi Wang, Qi Long Lu
  • Patent number: 7883714
    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: December 11, 2009
    Date of Patent: February 8, 2011
    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
  • Publication number: 20100190985
    Abstract: This invention is related to heteroatom containing diamondoids (i.e., “heterodiamondoids”) which are compounds having a diamondoid nucleus in which one or more of the diamondoid nucleus carbons has been substitutionally replaced with a noncarbon atom. These heteroatom substituents impart desirable properties to the diamondoid. In addition, the heterodiamondoids are functionalized affording compounds carrying one or more functional groups covalently pendant therefrom. This invention is further related to polymerizable functionalized heterodiamondoids. In a preferred aspect of this invention the diamondoid nuclei are triamantane and higher diamondoid nuclei. In another preferred aspect, the heteroatoms are selected to give rise to diamondoid materials which can serve as n- and p-type materials in electronic devices can serve as optically active materials.
    Type: Application
    Filed: December 14, 2009
    Publication date: July 29, 2010
    Applicant: Chevron U.S.A. Inc.
    Inventors: Shenggao Liu, Robert M. Carlson, Jeremy E. Dahl
  • Patent number: 7745496
    Abstract: A process for preparing a compound of formula (I) X-(CH2)n-ONO2??(I) wherein: X is a halogen atom selected from Cl, Br, I; n is an integer from 3 to 6; said process comprising the slow addition of a compound of formula (II) X-(CH2)n-OH??(II) wherein X and n are as defined above to a nitrating agent selected from the group consisting of concentrated nitric acid/concentrated sulfuric acid (sulfonitric mixture), nitric acid alone, NaNO2 in trifluoroacetic acid, nitronium salts such as NO2BF4 and an organic solvent selected from the group consisting of CH2Cl2, CHCl3, CCl4, perfluorohexane, perfluoroheptane. The invention refers also to solutions containing: a compound of general formula (I) and a solvent selected from the group consisting of CH2Cl2, CHCl3, CCl4, perfluorohexane, perfluoroheptane, characterized in that the compound of formula (I) is present in a concentration not higher than 20% by weight.
    Type: Grant
    Filed: November 9, 2005
    Date of Patent: June 29, 2010
    Assignee: Nicox S.A.
    Inventors: Romano Rivolta, Peter Finlander
  • Patent number: 7723382
    Abstract: The present invention refers to a process for preparing a compound of general formula (A), as reported in the description, wherein R is a radical of a drug and R1-R12 are hydrogen or alkyl groups, m, n, o, q, r and s are each independently an integer from 0 to 6, and p is 0 or 1, and X is O, S, SO, SO2, NR13 or PR13 or an aryl, heteroaryl group, said process comprising reacting a compound of formula (B) R—COOZ (B) wherein R is as defined above and Z is hydrogen or a cation selected from: Li+, Na+, K+, Ca++, Mg++, tetralkylammonium, tetralkylphosphonium, with a compound of formula (C), as reported in the description, wherein R1-R12 and m, n, o, p, q, r, s are as defined above and Y is a suitable leaving group.
    Type: Grant
    Filed: August 6, 2003
    Date of Patent: May 25, 2010
    Assignee: Nicox S.A.
    Inventors: Piero del Soldato, Giancarlo Santus, Francesca Benedini
  • Publication number: 20090320354
    Abstract: Branched decyl nitrates of the formula R1R2CH—CH2—O—NO2 in which R1 is an n-propyl or isopropyl radical and R2 is a linear or branched alkyl radical having 5 carbon atoms are suitable as combustion improvers and/or cetane number improvers in fuels.
    Type: Application
    Filed: January 25, 2008
    Publication date: December 31, 2009
    Applicant: BASF SE
    Inventors: Claudius Kormann, Uwe Rebholz, Gero Nordmann, Jörn Karl, Lothar Karrer
  • Patent number: 7632960
    Abstract: The present invention relates to a process for the preparation of nitric esters of monohydric alcohols wherein a monohydric alcohol or a mixture of monohydric alcohols is converted with nitric acid to the corresponding nitric esters under adiabatic reaction conditions in the presence of sulfuric acid.
    Type: Grant
    Filed: November 20, 2006
    Date of Patent: December 15, 2009
    Inventors: Jürgen Pöhlmann, Frank Pottharst, Heinrich Hermann, Peter Konieczny, Mirko Händel, Jürgen Gebauer
  • Publication number: 20090170934
    Abstract: The present invention relates to a new process for the preparation of NO-donating compounds using a sulfonated intermediate. The invention relates to new intermediates prepared therein suitable for large scale manufacturing of NO-donating compounds. The invention further relates to the use of the new intermediates for the manufacturing of pharmaceutically active NO-donating compounds. The invention further relates to a substantially crystalline form of NO-donating NSAIDs, especially 2-[2-(nitrooxy)ethoxy]ethyl {2-[(2,6-dichlorophenyl)amino]phenyl}acetate, the preparation thereof and to pharmaceutical formulations containing said crystalline form and to the use of said crystalline form in the preparation of a medicament.
    Type: Application
    Filed: June 20, 2008
    Publication date: July 2, 2009
    Inventors: Johan ANDERSSON, Aldo BELLI, Vincenzo CANNATA, Martin HEDBERG, Andreas PALMGREN, Sigrid SCHULDEI, Marika STROM, Marco VILLA
  • Patent number: 7335789
    Abstract: A process for the preparation of compounds of formula (I): HO-A-ONO2??(I) wherein A is a C2-C6 alkylene chain, the compounds of formula (I) being synthesized by nitration of the corresponding alkanediols with “stabilized” nitric acid is herein disclosed. The process is safer to operators and allows to obtain advantageous yields on an industrial scale.
    Type: Grant
    Filed: November 6, 2003
    Date of Patent: February 26, 2008
    Assignee: Dipharma S.p.A.
    Inventors: Nevio Francescutti, Tiziano Scubla, Fausto Gorassini, Graziano Castaldi
  • Patent number: 7282519
    Abstract: The invention describes novel nitrosated and/or nitrosylated diuretic compounds or pharmaceutically acceptable salts thereof, and novel compositions comprising at least one nitrosated and/or nitrosylated diuretic compound, and, optionally, at least one nitric oxide donor and/or at least one therapeutic agent. The invention also provides novel compositions and kits comprising at least one diuretic compound of the invention, that is optionally nitrosated and/or nitrosylated, and, optionally, at least one nitric oxide donor compound and/or at least one therapeutic agent.
    Type: Grant
    Filed: August 20, 2004
    Date of Patent: October 16, 2007
    Assignee: NitroMed, Inc.
    Inventors: David S. Garvey, L. Gordon Letts, Manuel Worcel, Richard A. Earl, Maiko Ezawa, Xinqin Fang, Subhash P. Khanapure, Chia-En Lin, Ramani R. Ranatunge, Cheri A. Stevenson
  • Publication number: 20040171683
    Abstract: The invention provides the combined use of an inhibitor of formation or release of &bgr;-amyloid and a nitric oxide releaser for the treatment or prevention of Alzheimer's disease.
    Type: Application
    Filed: February 27, 2004
    Publication date: September 2, 2004
    Inventor: Jose Luis Castro Pineiro
  • Publication number: 20040014720
    Abstract: The present invention relates to nitric oxide-releasing amidine diazeniumdiolates, compositions comprising same, methods of using same, and a method for preparing same from imidate diazeniumdiolates and primary or secondary amines.
    Type: Application
    Filed: July 18, 2002
    Publication date: January 22, 2004
    Applicants: Government of the United States of America, represented by the Secretary, Department of Health and Human Services
    Inventors: Joseph A. Hrabie, Larry K. Keefer, Ernst V. Arnold
  • Publication number: 20030203915
    Abstract: The invention describes novel nitric oxide donors and novel compositions comprising at least one nitric oxide donor. The invention also provides novel compositions comprising at least one nitric oxide donor, and, optionally, at least one therapeutic agent. The compounds and compositions of the invention can also be bound to a matrix. The invention also provides methods for treating cardiovascular diseases, for the inhibition of platelet aggregation and platelet adhesion caused by the exposure of blood to a medical device, for treating pathological conditions resulting from abnormal cell proliferation; transplantation rejections, autoimmune, inflammatory, proliferative, hyperproliferative, vascular diseases; for reducing scar tissue or for inhibiting wound contraction, particularly the prophylactic and/or therapeutic treatment of restenosis by administering the nitric oxide donor optionally in combination with at least one therapeutic agent.
    Type: Application
    Filed: April 7, 2003
    Publication date: October 30, 2003
    Inventors: Xinqin Fang, David S. Garvey, Ricky D. Gaston, Chia-En Lin, Ramani R. Ranatunga, Stewart K. Richardson, Tiansheng Wang, Weiheng Wang, Shiow-Jyi Wey
  • Publication number: 20030176724
    Abstract: An alkyl nitrite is produced with high efficiency by bringing a nitrogen monoxide gas into contact with an aqueous solution of an alkyl alcohol and nitric acid in a reactor 2, which aqueous solution may be a liquid fraction generated in an alkyl nitrite-production process in which an alkyl alcohol is reacted with nitrogen monoxide and oxygen in a reaction column 1.
    Type: Application
    Filed: March 13, 2003
    Publication date: September 18, 2003
    Applicant: Ube Industries, Ltd.
    Inventors: Ryoji Sugise, Shuji Tanaka, Hirofumi Ii, Kazuaki Mii
  • Publication number: 20030096862
    Abstract: Disclosed are novel NO-releasing compounds which comprise a stabilized S-nitrosyl group and a free alcohol or a free thiol group. Also disclosed is a method of preparing the NO-releasing compounds. The method comprises reacting a polythiol or a thioalcohol with a nitrosylating agent. Also disclosed are medical devices coated with the disclosed compounds, methods of delivering NO to treatments sites in a subject by utilizing the medical devices and methods of sterilizing surfaces.
    Type: Application
    Filed: August 12, 2002
    Publication date: May 22, 2003
    Applicant: Duke University
    Inventors: Eric J. Toone, Jonathan S. Stamler
  • Patent number: 6359182
    Abstract: A C-nitroso compound having a molecular weight ranging from about 225 to about 1,000 (from about 225 to about 600 for oral administration) on a monomeric basis wherein a nitroso group is attached to a tertiary carbon, which is obtained by nitrosylation of a carbon acid having a pKa less than about 25, is useful as an NO donor. When the compound is obtained from a carbon acid with a pKa less than about 10, it provides vascular relaxing effect when used at micromolar concentrations and this activity is potentiated by glutathione to be obtained at nanomolar concentrations. When the compound is obtained from a carbon acid with a pKa ranging from about 15 to about 20, vascular relaxing effect is obtained at nanomolar concentrations without glutathione. The compound is preferably water-soluble and preferably contains a carbon alpha to the nitrosylated carbon which is part of a ketone group.
    Type: Grant
    Filed: October 26, 2000
    Date of Patent: March 19, 2002
    Assignee: Duke University
    Inventors: Jonathan S. Stamler, Eric J. Toone
  • 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: 6072071
    Abstract: 1,2 and 1,3-dinitrate esters are prepared from polyols containing 1,2- or 1,3-diol fragments using an alkyl or aryl boronic acid to form a cyclic boronate ester derivative which is then reacted with dinitrogen pentoxide to directly generate the dinitrate ester. In the cyclic ester from the 1,2- or 1,3-hydroxyl groups are protected and other reactions may then be carried out on other parts of the molecule of which the fragment form a part, leaving the dinitrate ester to be produced subsequently in the final step. High yields are obtained at both stages.
    Type: Grant
    Filed: March 3, 1999
    Date of Patent: June 6, 2000
    Assignee: The Secretary of State for Defence in her Britannic Majesty's Goverment of the United Kingdom of Great Britain and Northern Ireland
    Inventors: Martin E Colclough, Andrew Pelter
  • Patent number: 5861426
    Abstract: New compounds and their compositions having anti-inflammatory, analgesic and anti-thrombotic activities, of the general formula: A--X.sub.1 --NO.sub.2 or their salts, wherein: A is R(COX.sub.u).sub.t, wherein t is zero or 1 and u is zero or 1; and X is O, NH or NR.sub.1C wherein R.sub.1C is C.sub.1 -C.sub.10 alkyl; and R is(Ia) wherein R.sub.1 is acetoxoy, preferably n ortho-position with respect to --CO-- and R.sub.2 is hydrogen; or derivatives of acetylsalylsalicyclic acid; and X.sub.1 is --YO-- wherein Y is C.sub.1 -C.sub.20 alkylene, C.sub.5 -C.sub.7 cycloalkylene, oxy-alkyl derivatives and oxy-methyl benzyl derivatives.
    Type: Grant
    Filed: March 6, 1997
    Date of Patent: January 19, 1999
    Assignee: Nicox S.A.
    Inventors: Piero Del Soldato, Francesco Sannicolo
  • 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: 5454842
    Abstract: The present invention is directed to materials which improve the cetane number of diesel fusel when added in an amount in the range of 0.01 to 2 wt % to such fuel. The materials are the nitration product of alcohols obtained by the reduction of tall oil fatty acids, tall oil fatty acid esters, vegetable oils and mixtures thereof.
    Type: Grant
    Filed: December 2, 1994
    Date of Patent: October 3, 1995
    Assignee: Exxon Research & Engineering Co.
    Inventors: Marc-Andre Poirier, David E. Steere, James A. Krogh
  • Patent number: 5380777
    Abstract: This invention is first, a difunctional poly(glycidyl nitrate) oligomer (PGN oligomer), second, nitrated PGN oligomer and third, the use of the nitrated PGN oligomer as a plasticizer, particularly as a plasticizer for binders used in and/or as energetic formulations. Examples of energetic formulations are propellants, pyrotechnics and explosives and other such compositions. More particularly, this invention is a difunctional poly(glycidyl nitrate) oligomer of the formula ##STR1## where n is 0 to 3, having a M.sub.n of from about 304 to about 994. Another embodiment is the nitrated difunctional poly(glycidyl nitrate) oligomer of the formula ##STR2## where n is 0 to 3, having a M.sub.n of from about 394 to about 1084.
    Type: Grant
    Filed: March 28, 1994
    Date of Patent: January 10, 1995
    Assignee: Thiokol Corporation
    Inventors: Rodney Willer, Alfred G. Stern, Robert S. Day
  • Patent number: 5214189
    Abstract: N-(2-Hydroxyethyl nitrate)-2,4,6-trinitrobenzamide which is an explosive h good thermal stability at 150.degree. C.
    Type: Grant
    Filed: June 15, 1992
    Date of Patent: May 25, 1993
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventor: Michael E. Sitzmann
  • 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: 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: 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: 4745208
    Abstract: 2,2,2-trinitroethyl 2-nitroxyethyl ether (TNEN), C(NO.sub.2).sub.3 CH.sub.2 CH.sub.2 CH.sub.2 ONO.sub.2, which is prepared by the following reaction sequence:C(NO.sub.2).sub.3.sup.- K.sup.+ +ClCH.sub.2 OCH.sub.2 CH.sub.2 BR.fwdarw.C(NO.sub.2).sub.3 CH.sub.2 OCH.sub.2 CH.sub.2 Br C(NO.sub.2).sub.3 CH.sub.2 OCH.sub.2 CH.sub.2 Br+AgNO.sub.3 .fwdarw.C(NO.sub.2).sub.3 CH.sub.2 OCH.sub.2 CH.sub.2 ONO.sub.2.2,2,2-trinitroethyl 2-nitroxyethyl ether is useful an an energetic plasticizer, for example in LOVA gun propellants.
    Type: Grant
    Filed: April 27, 1987
    Date of Patent: May 17, 1988
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Horst G. Adolph, Kyung E. Kim