Additional Nitrogen Or Chalcogen Containing Patents (Class 558/483)
  • Patent number: 10377916
    Abstract: Embodiments provide ice adhesion mitigating surface coatings and methods for generating the same. Embodiments may provide anti-icing coating with at least one monomeric species exhibiting molecular flexibility. The molecular flexibility in the monomeric species may be imparted through an aliphatic or heteroaliphatic chain that may exist as a portion of the monomer backbone, as a pendant group, or as both the portion of the monomer backbone and the pendant group. In various embodiments epoxy coatings including an epoxy resin and an amine-terminated hardener may be generated. At least a portion of the amine-terminated hardener may include at least a monomeric species that exhibits molecular flexibility arising from an aliphatic chain or heteroaliphatic chain that may be within the polymer backbone and/or may persist as a pendant group.
    Type: Grant
    Filed: September 1, 2016
    Date of Patent: August 13, 2019
    Assignee: United States of America as represented by the Administrator of NASA
    Inventors: Christopher J. Wohl, Jr., Joseph G. Smith, Jr.
  • Patent number: 10232341
    Abstract: An apparatus for producing polyethylene glycol dinitrate. The apparatus includes providing continuously an acid composition and a glycol composition to a reaction apparatus; reacting the acid composition and the glycol composition in the reaction apparatus in a continuous manner to generate a reaction composition; using an alkaline composition to at least partially neutralize the reaction composition to cause at least a portion of the polyethylene glycol dinitrate to deposit from a solution of the reaction composition; and extracting the deposit of polyethylene glycol dinitrate.
    Type: Grant
    Filed: February 15, 2016
    Date of Patent: March 19, 2019
    Assignee: AVOCET IP LIMITED
    Inventors: James Robert Jennings, Glyn David Short
  • 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
  • Publication number: 20140134282
    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 nitrooxy alkanoic acid and/or derivative 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: January 21, 2014
    Publication date: May 15, 2014
    Applicant: DSM IP ASSETS B.V.
    Inventors: Stephane DUVAL, Maik KINDERMANN
  • Publication number: 20140135389
    Abstract: The present invention relates to nitric oxide donor compounds having a quinone based structure, to processes for their preparation and to their use in the treatment of pathological conditions where a deficit of NO plays an important role in their pathogenesis.
    Type: Application
    Filed: January 22, 2014
    Publication date: May 15, 2014
    Inventors: Gael RONSIN, Laura STORONI, Francesca BENEDINI
  • Publication number: 20140057873
    Abstract: There is provided amino acid ester compounds comprising at least one nitric oxide releasing group, pharmaceutically acceptable salts thereof and compositions thereof. These compounds involve an amino acid side-chain or an amino acid derivative thereof and a nitric oxide releasing group as depicted in the following structures: wherein R1 is either an ethyl or an amino acid side-chain group or an amino acid derivative thereof and R2 is an amino acid side-chain group or an amino acid derivative thereof and n is an integer from 1 to 10.
    Type: Application
    Filed: November 1, 2013
    Publication date: February 27, 2014
    Inventor: Michael Farber
  • 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: 20120315339
    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 nitrooxy alkanoic acid and/or derivative 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 10, 2010
    Publication date: December 13, 2012
    Inventors: Stephane Duval, Maik Kindermann
  • Publication number: 20120232257
    Abstract: The invention relates to a nitration method having the following principles: a phosgene species is converted with two equivalent silver nitrates into a double-mixed anhydride of carbonic acid and nitric acid, known here as carbonic acid dinitrate (I). Said operation is carried out in situ, and the formed dinitrate decomposes spontaneously. In addition to carbon dioxide, nitrate ions and nitronium ions are formed, said ions comprising electrophiles which are necessary for nitration. The solution which is used is acetonitrile, and is insignificant if the alcohol species is dissolved or suspended. The necessary equivalent silver nitrates are introduced into the system and optionally heated or cooled to the desired temperature. Subsequently, the acid chloride is introduced slowly, drop by drop or slowly little by little. Phosgene, diphosgene, triphosgene and chloroformic acid ester can be used as carbonic acid dichloride and monochloride, and their thiocarbonic acid analogues.
    Type: Application
    Filed: October 4, 2010
    Publication date: September 13, 2012
    Applicant: SYNOVO GMBH
    Inventor: Nikolas Pietrzik
  • Publication number: 20120130115
    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: Application
    Filed: November 23, 2010
    Publication date: May 24, 2012
    Applicant: ALLIANT TECHSYSTEMS INC.
    Inventors: Nicholas A. Straessler, Alexander J. Paraskos, Michael P. Kramer
  • Publication number: 20120108838
    Abstract: Preparation of an energetic nitrate ester compound and related intermediates is provided.
    Type: Application
    Filed: September 24, 2009
    Publication date: May 3, 2012
    Applicant: US Department of Energy
    Inventors: David E. Chavez, Darren L. Naud, Michael A. Hiskey
  • Patent number: 8058243
    Abstract: A clonogenic neurosphere assay is described that carries out high throughput screens (HTS) to identify potent and/or selective modulators of proliferation, differentiation and/or renewal of neural precursor cells, neural progenitor cells and/or self-renewing and multipotent neural stem cells (NSCs). Compositions comprising the identified modulators and methods of using the modulators and compositions, in particular to treat neurological disorders (e.g. brain or CNS cancer) or damage are also disclosed.
    Type: Grant
    Filed: October 12, 2007
    Date of Patent: November 15, 2011
    Assignees: HSC Research and Development Limited Partnership, Mount Sinai Hospital
    Inventors: Mike Tyers, Phedias Diamandis, Peter B. Dirks
  • Publication number: 20110195935
    Abstract: There is provided amino acid ester compounds comprising at least one nitric oxide releasing group, pharmaceutically acceptable salts thereof and compositions thereof. These compounds involve an amino acid side-chain or an amino acid derivative thereof and a nitric oxide releasing group as depicted in the following structures: wherein R1 is either an ethyl or an amino acid side-chain group or an amino acid derivative thereof and R2 is an amino acid side-chain group or an amino acid derivative thereof and n is an integer from 1 to 10.
    Type: Application
    Filed: September 24, 2009
    Publication date: August 11, 2011
    Inventor: Michael Farber
  • 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: 20110034720
    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: Application
    Filed: December 19, 2008
    Publication date: February 10, 2011
    Inventors: Sascha Braune, Stefan Steinhofer, Peter Poechlauer, Rafael Wilhelmus E.G. Reintjens, Nicole Theodora W. Linssen, Mehul Thathagar
  • Publication number: 20100311780
    Abstract: There is provided novel amino acid ester compounds comprising at least one nitric oxide releasing group and pharmaceutically acceptable salts thereof, and novel compositions comprising at least one amino acid ester compound comprising at least one nitric oxide releasing group, and, optionally, at least one nitric oxide donor and/or at least one therapeutic agent. Also provided are compositions for increasing nitric oxide physiological levels in a subject, methods for increasing nitric oxide physiological levels in a subject, methods for improving a subject's muscle strength, athletic performances and/or lean body mass gain and or performance in a subject.
    Type: Application
    Filed: August 13, 2010
    Publication date: December 9, 2010
    Applicant: Oral Delivery Technology LTD.
    Inventor: Michael Farber
  • Publication number: 20100312003
    Abstract: The present invention relates to a process for the preparation of organic nitrates having at least one nitryloxy and at least one hydroxy group, wherein the at least one hydroxy group may be present in form of an esterified hydroxy residue, the latter being esterified with an acid other than nitric acid.
    Type: Application
    Filed: October 10, 2008
    Publication date: December 9, 2010
    Inventors: Walter Brieden, Dominique Michel, Wilhelm Quittmann, Fabio Rainone, Jie-Hui Pan, Hang-Bing Fang, Ying-Xia Song
  • Patent number: 7745656
    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: Grant
    Filed: March 14, 2006
    Date of Patent: June 29, 2010
    Assignee: Duke University
    Inventors: Eric J. Toone, Jonathan S. Stamler
  • 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: 20090182044
    Abstract: The present invention is directed to methods and compositions which include nitrate amino acid chelates that can increase the metabolic activity or metal concentration in animals and that can increase metabolic activity and nitrogen content in plants. In one embodiment, a nitrate-complexed amino acid composition can comprise a metal, an amino acid ligand, and a nitrate, wherein the amino acid ligand is chelated to the metal forming an amino acid chelate and the nitrate is complexed to the amino acid chelate. In another embodiment, a nitrate-chelated amino acid composition can comprise a metal, an amino acid ligand, and a nitrate, wherein the amino acid ligand and the nitrate are chelated to the metal forming a nitrate-chelated amino acid chelate.
    Type: Application
    Filed: January 9, 2009
    Publication date: July 16, 2009
    Inventors: H. DeWayne Ashmed, Charlie Thompson
  • Publication number: 20080293961
    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: Application
    Filed: July 2, 2008
    Publication date: November 27, 2008
    Applicant: DIPHARMA S.P.A.
    Inventors: Tiziano Scubla, Nevio Francescutti, Fausto Gorassini, Graziano Castaldi
  • Patent number: 7399878
    Abstract: Compounds or their salts of general formula (I): A-B-N(O)s wherein: s is an integer equal to 1 or 2; A=R-T1-, wherein R is the drug radical and T1=(CO)t or (X)t?, wherein X=O, S, NR1c, R1c is H or a linear or branched alkyl or a free valence, t and t? are integers and equal to zero or 1, with the proviso that t=1 when t?=0; t=0 when t?=1; B=-TB-X2—O— wherein TB=(CO) when t=0, TB=X when t?=0, X being as above defined; X2 is equal to R1B-X-R2B radical wherein X is as above defined, R1B and R2B, equal to or different from each other, are linear or branched C1-C6 alkylenes, or X2 is a radical wherein two alkylene chains C1-C4 are linked to nonadjacent positions of a central ring having 4 or 6 atoms, said ring being an unsaturated cycloaliphatic ring, or a saturated or aromatic heterocylic ring, containing one or two heteroatoms, equal or different, selected from O, S, N; wherein the unsaturated cycloaliphatic ring does not have aromatic character according to Huckel's rule.
    Type: Grant
    Filed: December 21, 2006
    Date of Patent: July 15, 2008
    Assignee: Nicox S.A.
    Inventor: Piero Del Soldato
  • Publication number: 20080146830
    Abstract: A process for the preparation of compounds of formula HO-A-ONO2 ??(I) wherein A is a C2-C6 alkylene chain by nitration of the corresponding alkanediols with “stabilised” nitric acid is herein disclosed. The process is safer to operators and allows to obtain advantageous yields on an industrial scale.
    Type: Application
    Filed: February 25, 2008
    Publication date: June 19, 2008
    Applicant: DIPHARMA S.P.A.
    Inventors: Nevio FRANCESCUTTI, Tiziano SCUBLA, Fausto GORASSINI, Graziano CASTALDI
  • 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: 7297808
    Abstract: Statin nitroderivatives having improved pharmacological activity and enhanced tolerability are described. They can be employed for treating and/or preventing several diseases, in particular coronary syndromes, neurodegenerative disorders as well as for reducing cholesterol levels.
    Type: Grant
    Filed: November 1, 2006
    Date of Patent: November 20, 2007
    Assignee: Nicox S.A.
    Inventors: Francesca Benedini, Ennio Ongini, Piero Del Soldato
  • Patent number: 7238829
    Abstract: A process for obtaining nitroxyalklesters of the 2(S)(6-methoxy-2-naphthyl)-propanoic acid having an enantiomeric excess higher than or equal to 95%, preferably higher than or equal to 98%, characterized in that an halide of the 2-(S)-(6 methoxy-2-naphthyl)propanoic acid of formula A-Hal, wherein A is the acid acyl residue, is reacted in an inert organic solvent with an aliphatic nitroxyalkanol HO—Y—ONO2, wherein Y is a C2-C20 alkylene or a cycloalkylene from 3 to 8 carbon atoms, or an alkylene as defined containing a cycloalkylene as defined, in the presence of an inorganic base.
    Type: Grant
    Filed: July 24, 2003
    Date of Patent: July 3, 2007
    Assignee: Nicox S.A.
    Inventors: Francesca Benedini, Erminio Oldani, Graziano Castaldi, Antonio Tarquini
  • Patent number: 7186753
    Abstract: Compounds or their salts of general formula (I): A—B—N(O)s wherein: s is an integer equal to 1 or 2; A=R—T1—, wherein R is the drug radical and T1=(CO)t or (X)t?, wherein X=O, S, NR1c, R1c is H or a linear or branched alkyl or a free valence, t and t? are integers and equal to zero or 1, with the proviso that t=1 when t?=0; t=0 when t?=1; B=—TB—X2—O— wherein TB=(CO) when t=0, TB=X when t?=0, X being as above defined; X2 is equal to R1B—X—R2B radical wherein X is as above defined, R1B and R2B, equal to or different from each other, are linear or branched C1–C6 alkylenes, or X2 is a radical wherein two alkylene chains C1–C4 are linked to nonadjacent positions of a central ring having 4 or 6 atoms, said ring being an unsaturated cycloaliphatic ring, or a saturated or aromatic heterocylic ring, containing one or two heteroatoms, equal or different, selected from O, S, N; wherein the unsaturated cycloaliphatic ring does not have aromatic character according to Huckel's rule.
    Type: Grant
    Filed: July 27, 2000
    Date of Patent: March 6, 2007
    Assignee: Nicox S.A.
    Inventor: Piero Del Soldato
  • Patent number: 7160920
    Abstract: Disclosed are (i) compounds of a steroid, a ?-agonist, an anticholinergic, a mast cell stabilizer and a phosphodiesterase (PDE) inhibitor directly or indirectly linked to a NO or NO2 group or a group which stimulates endogenous production of NO or EDRF in vivo; (ii) compositions of steroids, ?-agonists, anticholinergics, mast cell stabilizers and PDE inhibitors, which can optionally be substituted with at least one NO or NO2 moiety or a group which stimulates endogenous production of NO or EDRF in vivo, and a compound that donates, transfers or releases nitric oxide as a charged species, i.e., nitrosonium (NO+) or nitroxyl (NO?), or as the neutral species, nitric oxide (NO.) or that stimulates endogenous production of NO or EDRF in vivo; and (iii) uses for them in preventing and/or treating respiratory disorders.
    Type: Grant
    Filed: May 5, 2003
    Date of Patent: January 9, 2007
    Assignee: NitroMed, Inc.
    Inventors: David S. Garvey, L. Gordon Letts, H. Burt Renfroe, Stewart K. Richardson
  • Publication number: 20040029929
    Abstract: The present invention provides novel aminoadamantane derivatives, methods of making the derivatives, compositions including the novel aminoadamantane derivatives, and methods for the treatment and prevention of neurological diseases using the derivatives and compositions.
    Type: Application
    Filed: August 4, 2003
    Publication date: February 12, 2004
    Inventors: Yuqiang Wang, Wenqing Ye, James W. Larrick, Jonathan S. Stamler, Stuart A. Lipton
  • 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
  • Publication number: 20030092764
    Abstract: Carboxylic-gated-nitroxide (CGN) compounds and their esterified derivatives are discovered and disclosed as compositions and shown to have the potential in treating a variety of acute and chronic diseases and disorders resulting from reactive oxygen species (ROS) injury. Compositions for treating tissue damage from ROS injury containing CGN, or active derivatives thereof, in a suitable pharmaceutical, cosmetic, and diagnostic formulations are described.
    Type: Application
    Filed: September 9, 2002
    Publication date: May 15, 2003
    Inventors: Jen-Chang Hsia, Li Ma
  • Patent number: 6548693
    Abstract: Carnitine derivatives of formula (I) are described in racemic and/or optically active form, as well as the process for their preparation and their use as pharmaceutical anti-angina active ingredients for the treatment of ischaemic heart disease. Also described is a process for producing the (R)-carnitine enantiomer from (S)-carnitine (or vice versa), using the derivatives of formula (I).
    Type: Grant
    Filed: April 11, 2002
    Date of Patent: April 15, 2003
    Assignee: Sigma-Tau Industrie Farmaceutiche Riunite S.p.A.
    Inventors: Oreste Piccolo, Roberto Castagnani, Paolo De Witt
  • Publication number: 20020119965
    Abstract: Carnitine derivatives of formula (I) are described in racemic and/or optically active form, as well as the process for their preparation and their use as pharmaceutical anti-angina active ingredients for the treatment of ischaemic heart disease.
    Type: Application
    Filed: April 11, 2002
    Publication date: August 29, 2002
    Applicant: SIGMA-TAU INDUSTRIE FARMACEUTICHE RIUNITE S.p.A.
    Inventors: Oreste Piccolo, Roberto Castagnani, Paolo De Witt
  • Patent number: 6325876
    Abstract: A compound has the structure of 3,3-bis(difluoroamino)-1,5-dinitratopentane and is useful in energetic materials.
    Type: Grant
    Filed: March 2, 2000
    Date of Patent: December 4, 2001
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Horst G. Adolph, Nirupam J. Trivedi
  • Publication number: 20010025052
    Abstract: The present invention relates to nitric oxide-releasing amidine- and enamine-derived diazeniumdiolates, compositions comprising such compounds, methods of using such compounds and compositions, and to a method for the preparation of nitric oxide-releasing amidine and enamine derived diazeniumdiolates via the direct reaction of nitric oxide with amidines and enamines, and to a method of converting amines into such compounds.
    Type: Application
    Filed: April 3, 2001
    Publication date: September 27, 2001
    Inventors: Joseph A. Hrabie, Larry K. Keefer
  • 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: 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: 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: 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: 5705527
    Abstract: An amino acid compound of the formula: R.sup.1 NH--CH(R.sup.2)--COHN--A--ONO.sub.2, wherein R.sup.1 represents a hydrogen atom, a C.sub.1 -C.sub.7 alkanoyl group, a C.sub.1 -C.sub.6 alkoxycarbonyl group, a C.sub.6 -C.sub.10 arylcarbonyl group, a C.sub.7 -C.sub.13 aralkylcarbonyl group, a C.sub.7 -C.sub.13 aralkyloxycarbonyl group or a 5- or 6-membered aromatic heterocyclic carbonyl group; R.sup.2 represents a substituted C.sub.1 -C.sub.6 alkyl group; and A represents a C.sub.2 -C.sub.5 alkylene group; and pharmacologically acceptable salts thereof. The amino acid compound has an excellent vasodilator action for collateral vessels and is useful for treating angina pectoris.
    Type: Grant
    Filed: April 20, 1995
    Date of Patent: January 6, 1998
    Assignee: Sankyo Company, Limited
    Inventors: Sadao Ishihara, Fujio Saito, Takao Yoshioka, Hiroyuki Koike, Shigeki Miyake, Hiroshi Mizuno
  • Patent number: 5700947
    Abstract: This invention is directed to nitric esters of derivatives of propionic acid, 1-(p-chlorobenzoyl)-5-methoxy-2-methyl-3-indolylacetic acid, 5-benzoyl-1,2-dihydro-3H-pyrrolo?1,2-a!pyrrole-1-carboxylic acid, 6-methoxy-2-napthylacetic acid, characterized in that they have the following general formula: ##STR1## These nitric ester derivatives may be formulated into pharmaceutical compositions and administered for their anti-inflammatory and/or analgesic activity.
    Type: Grant
    Filed: April 5, 1996
    Date of Patent: December 23, 1997
    Assignee: NICOX S.A.
    Inventor: Piero Del Soldato
  • Patent number: 5661129
    Abstract: The invention relates to novel nitrates containing a disulphide group, and to processes for their preparation. The compounds can be used for the therapy of disorders of the cardiovascular system.
    Type: Grant
    Filed: December 5, 1995
    Date of Patent: August 26, 1997
    Assignee: Schwarz Pharma AG
    Inventors: Martin Feelisch, Hilmar Bokens, Jochen Lehmann, Claus Meese, Klaus Sandrock
  • Patent number: 5597847
    Abstract: Object of this invention are nitric esters of derivatives of the 2-(2,6-di-halophenylamino)phenylacetic acid, having the following general formula: ##STR1## wherein: A and B are selected from among hydrogen and linear or branched, substituted or non substituted alkyl chains, X is a halogen selected from among chlorine and bromine, Y is selected from among oxygen, NH and NR.sub.1, wherein R.sub.1 is a linear or branched alkyl group, and n is comprised between 1 and 10 as well as their pharmaceutical utilization and process for their preparation.
    Type: Grant
    Filed: March 31, 1994
    Date of Patent: January 28, 1997
    Assignees: Corlay S.L., Metgrove Ltd.
    Inventors: Jose A. Matji, Antonio Alcaide
  • 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: 5428061
    Abstract: New organic nitrate compounds, formed by condensing a nitrato alkanoic acid with a sulfur-containing amino acid or peptide, which prevent nitrate tolerance or overcome existing tolerance and which are useful for the treatment of cardiac diseases including circulatory diseases, high blood pressure, cardiac insufficiency and for dilating the peripheral vessels.
    Type: Grant
    Filed: September 7, 1993
    Date of Patent: June 27, 1995
    Assignee: Schwarz Pharma AG
    Inventors: Klaus Sandrock, Joachim Hutter, Eike Noack
  • 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: 5284872
    Abstract: New organic nitrate compounds, formed by condensing a nitrato alkanoic acid with a sulfur-containing amino acid or peptide followed by the reaction of the resulting product with an amino acid, N-acylamino acid, peptide or an N-acyl peptide to produce a thio ester thereof, which prevent nitrate tolerance or overcome existing tolerance and which are useful for the treatment of cardiac diseases including circulatory diseases, coronary dilation, high blood pressure, cardiac insufficiency and for dilating the peripheral vessels.
    Type: Grant
    Filed: April 5, 1991
    Date of Patent: February 8, 1994
    Assignee: Schwarz Pharma AG
    Inventors: Klaus Sandrock, Eike Noack, Edgar Fritschi, Ralf Kanzler, Martin Feelisch
  • Patent number: 5264596
    Abstract: Isotactic poly(glycidyl nitrate) useful in solid propellants is produced by polymerizing chiral (R) glycidyl nitrate or its enantiomer, (S) glycidyl nitrate. Chiral (R) glycidyl nitrate or its enantiomer is prepared by sequential treatment of chiral (S) glycidyl tosylate or its enantiomer with nitric acid and sodium hydroxide. Chiral (S) glycidyl tosylate or its enantiomer, (R) glycidyl tosylate, can be produced by Sharpless epoxidation of allyl alcohol or by direct tosylation or commercially available chiral glycidol. Likewise, chiral (R) glycidyl nitrate or its enantiomer, (S) glycidyl nitrate, can be prepared directly via nitration of (S) or (R) glycidol, respectively.
    Type: Grant
    Filed: August 13, 1992
    Date of Patent: November 23, 1993
    Assignee: Thiokol Corporation
    Inventors: Rodney L. Willer, Alfred G. Stern, Robert S. Day
  • Patent number: 5099042
    Abstract: Polymers are produced from 4 and 5 member cyclic ethers, which polymers have hydroxyl functionalities of 4.
    Type: Grant
    Filed: March 14, 1989
    Date of Patent: March 24, 1992
    Assignee: Thiokol Corporation
    Inventors: Robert B. Wardle, Jerald C. Hinshaw