Reactant Having Nitrogen Attached Indirectly To Phosphorus By Nonionic Bonding Patents (Class 558/145)
  • Patent number: 9035088
    Abstract: The invention relates to a method for producing mono-aminofunctionalized dialkylphosphinic acids and esters and salts thereof by means of acrylnitriles, characterized in that a) a phosphinic acid source (I) is reacted with olefins (IV) to yield an alkylphosphonic acid, salt or ester (II) thereof in the presence of a catalyst A, b) the thus obtained alkylphosphonic acid, salt or ester (II) thereof is reacted with an acrylnitrile of formula (V) to yield a mono-functionalized dialkylphosphinic acid derivative (VI) in the presence of a catalyst B, and c) the thus obtained mono-functionalized dialkylphosphinic acid derivative (VI) is reacted to yield a mono-aminofunctionalized dialkylphosphinic acid derivative (III) in the presence of a catalyst C or a reduction agent, wherein R1, R2, R3, R4, R5, R6, R7 are the same or different and stand independently of each other, among other things, for H, C1-C18 alkyl, C6-C18 aryl, C6-C18 aralkyl, C6-C18 alkylaryl and X stands for H, C1-C18 alkyl, C6-C18 aryl, C6-C18 aralkyl,
    Type: Grant
    Filed: October 6, 2009
    Date of Patent: May 19, 2015
    Assignee: Clariant Finance (BVI) Limited
    Inventors: Michael Hill, Werner Krause, Martin Sicken
  • Patent number: 8987495
    Abstract: Provided is an efficient technology for synthesizing diamino acids (diamino acid derivatives). Disclosed is a manufacturing method for diamino acid derivatives wherein the fluorenyl groups of the diamino acid derivative starting materials represented by General Formula [II] or [IV] are removed.
    Type: Grant
    Filed: September 11, 2013
    Date of Patent: March 24, 2015
    Assignee: Japan Science and Technology Agency
    Inventors: Shu Kobayashi, Yasuhiro Yamashita, Kazutaka Seki
  • Publication number: 20140163136
    Abstract: Hydrophilic, biocidal coating compositions and methods to make and use the compositions are disclosed. The coatings include compounds with quaternary amine polyethylene glycol groups and polyaminoalkyl biguanide groups as substituents. The compounds when incorporated in paints provide hydrophilic, self-cleaning and biocidal property to the coating.
    Type: Application
    Filed: December 10, 2012
    Publication date: June 12, 2014
    Applicant: EMPIRE TECHNOLOGY DEVELOPMENT LLC
    Inventors: Glen Leon Brizius, Phillip Kent Montgomery
  • Publication number: 20140012016
    Abstract: Provided is an efficient technology for synthesizing diamino acids (diamino acid derivatives). Disclosed is a manufacturing method for diamino acid derivatives wherein the fluorenyl groups of the diamino acid derivative starting materials represented by General Formula [II] or [IV] are removed.
    Type: Application
    Filed: September 11, 2013
    Publication date: January 9, 2014
    Applicant: Japan Science and Technology Agency
    Inventors: Shu KOBAYASHI, Yasuhiro YAMASHITA, Kazutaka SEKI
  • Patent number: 8604232
    Abstract: The invention relates to method for producing mono amino-functionalised dialkylphosphonic acids esters and salts, characterized in that a) a phosphinic acid source (I) is reacted with olefins (IV) in the presence of a catalyst A to give an alkylphosphonous acid, the salt or ester thereof (II), b) the alkylphosphonous acid, the salt or ester thereof (II) produced above is reacted with an allylamine of formula (V) in the presence of a catalyst B to give mono amino-functionalised dialkylphosphinic acid derivatives (III) where, R1, R2, R3, R4, R5, R6, R7, R8, R9 independently=amongst others, H, C1-C18 alkyl, C6-C18 aryl, C6-C18 aralkyl, C6-C18 alkylaryl and X?H, C1-C18 alkyl, C6-C18 aryl, C6-C18 aralkyl, C6-C18 alkylaryl, Mg, Ca, Al, Sb, Sn, Ge, Ti, Fe, Zr, Zn, Ce, Bi, Sr, Mn, Cu, Ni, Li, Na, K and/or a protonated nitrogen base and Y=a mineral acid, a carboxylic acid, a Lewis acid or organic acid, where n=a whole or fractional number from 0 to 4, catalyst A is a transition metal and/or transition metal compound a
    Type: Grant
    Filed: October 6, 2009
    Date of Patent: December 10, 2013
    Assignee: Clariant Finance (BVI) Limited
    Inventors: Michael Hill, Werner Krause, Martin Sicken
  • Publication number: 20130310591
    Abstract: Provided are amino group-containing phosphorylcholine compound and a method for production thereof, that has a highly active amino group efficiently reactive with a wide variety of functional groups and the like under mild conditions, and is capable of introducing a phosphorylcholine-like group to various substrate surfaces to provide functionalities of the group. The amino group-containing phosphorylcholine compound of the present invention is represented by at least one of formulae (1) and (1?), and may be used as a compound, or a material thereof, capable of introducing a phosphorylcholine-like group to the surface of various substrates, such as medical instruments, cosmetics materials, and medicinal substances.
    Type: Application
    Filed: December 22, 2011
    Publication date: November 21, 2013
    Applicant: NOF CORPORATION
    Inventors: Nobuyuki Yoshioka, Nobuyuki Sakamoto, Yosuke Matsuoka, Norio Iwakiri
  • Patent number: 8580995
    Abstract: The present invention provides processes for synthesizing lysine based compounds of the formula; wherein R1 may be, for example, (HO)2P(O)—, (NaO)2P(O)—, wherein X may be, for example, NH2, Y may be H, F, Cl, or Br, and wherein n, X?, Y?, R2, R3, R4, R5 and R6 are as defined herein.
    Type: Grant
    Filed: June 19, 2008
    Date of Patent: November 12, 2013
    Assignee: TaiMed Biologics, Inc.
    Inventors: Guy Milot, Stephane Branchaud, Brent R. Stranix
  • Publication number: 20130244982
    Abstract: Conjugates of drugs suitable for use in the treatment of inflammatory bowel disease and phospholipids, and their use in the treatment of inflammatory bowel disease, are disclosed. The disclosed conjugates serve as targeted prodrugs which are suitable for oral administration, and which are capable of releasing the drug selectively at the diseased tissue upon activation by PLA2.
    Type: Application
    Filed: December 1, 2011
    Publication date: September 19, 2013
    Applicant: Bengurion University of the Negev Research and Development Authority
    Inventor: Arik Dahan
  • Publication number: 20130131311
    Abstract: Improved methods of native chemical ligation are provided. The methods involve reacting a thioacid (e.g. a peptide thioacid) with an aziridinyl compound (e.g. an aziridinyl peptide) under mild conditions without the use of protecting groups, and without requiring that a cysteine residue be present in the ligation product. Initial coupling of the thioacid and the aziridinyl compound yields a ligation product which contains an aziridinyl ring. Subsequent opening of the aziridinyl ring (e.g. via a nucleophilic attack) produces a linearized and modified ligation product.
    Type: Application
    Filed: November 13, 2012
    Publication date: May 23, 2013
    Applicant: WASHINGTON STATE UNIVERSITY
    Inventor: Washington State University
  • Publication number: 20120059183
    Abstract: A phosphorylcholine group-containing compound that is a structure having a phosphorylcholine group represented by the following formula 1 and an amino group or a group derived from an amino group in an identical compound. (In the formula, m is 2 or more and 6 or less and p is 1 or 2. Each of X1, X2 and X3 is an alkyl group whose carbon number is 1 or more and 6 or less.
    Type: Application
    Filed: November 2, 2011
    Publication date: March 8, 2012
    Applicant: SHISEIDO COMPANY, LTD.
    Inventors: Kazuyuki MIYAZAWA, Yukimitsu Suda
  • Publication number: 20110213078
    Abstract: The invention relates to a method for producing mono-aminofunctionalized dialkylphosphinic acids and esters and salts thereof by means of acrylnitriles, characterized in that a) a phosphinic acid source (I) is reacted with olefins (IV) to yield an alkylphosphonic acid, salt or ester (II) thereof in the presence of a catalyst A, b) the thus obtained alkylphosphonic acid, salt or ester (II) thereof is reacted with an acrylnitrile of formula (V) to yield a mono-functionalized dialkylphosphinic acid derivative (VI) in the presence of a catalyst B, and c) the thus obtained mono-functionalized dialkylphosphinic acid derivative (VI) is reacted to yield a mono-aminofunctionalized dialkylphosphinic acid derivative (III) in the presence of a catalyst C or a reduction agent, wherein R1, R2, R3, R4, R5, R6, R7 are the same or different and stand independently of each other, among other things, for H, C1-C18 alkyl, C6-C18 aryl, C6-C18 aralkyl, C6-C18 alkylaryl and X stands for H, C1-C18 alkyl, C6-C18 aryl, C6-C18 aralkyl,
    Type: Application
    Filed: October 6, 2009
    Publication date: September 1, 2011
    Applicant: CLARIANT FINANCE (BVI) LIMITED
    Inventors: Michael Hill, Werner Krause, Martin Sicken
  • Publication number: 20110213061
    Abstract: The invention relates to a method for producing mono-aminofunctionalized dialkylphosphinic acids and esters and salts thereof, characterized in that a) a phosphinic acid source (I) is reacted with olefins (IV) to yield an alkylphosphonic acid, salt or ester (II) thereof in the presence of a catalyst A, b) the thus obtained alkylphosphonic acid, salt or ester (II) thereof is reacted with acetylenic compounds of formula (V) to yield a mono-functionalized dialkylphosphinic acid derivative (VI) in the presence of a catalyst B, and c) the thus obtained mono-functionalized dialkylphosphinic acid derivative (VI) is reacted with a hydrogen cyanide source to yield a mono-functionalized dialkylphosphinic acid derivative (VII) in the presence of a catalyst C, and d) the thus obtained mono-functionalized dialkylphosphinic acid derivative (VII); is reacted to yield a mono-aminofunctionalized dialkylphosphinic acid derivative (III) in the presence of a catalyst D or a reduction agent, wherein R1, R2, R3, R4, R5, R6 are the
    Type: Application
    Filed: October 6, 2009
    Publication date: September 1, 2011
    Applicant: CLARIANT FINANCE (BVI) LIMITED
    Inventors: Michael Hill, Werner Krause, Martin Sicken
  • Publication number: 20110213079
    Abstract: The invention relates to method for producing mono amino-functionalised dialkylphosphonic acids esters and salts, characterised in that a) a phosphinic acid source (I) is reacted with olefins (IV) in the presence of a catalyst A to give an alkylphosphonous acid, the salt or ester thereof (II), b) the alkylphosphonous acid, the salt or ester thereof (II) produced above is reacted with an allylamine of formula (V) in the presence of a catalyst B to give mono amino-functionalised dialkylphosphinic acid derivatives (III) where, R1, R2, R3, R4, R5, R6, R7, R8, R9 independently=amongst others, H, C1-C18 alkyl, C6-C18 aryl, C6-C18 aralkyl, C6-C18 alkylaryl and X?H, C1-C18 alkyl, C6-C18 aryl, C6-C18 aralkyl, C6-C18 alkylaryl, Mg, Ca, Al, Sb, Sn, Ge, Ti, Fe, Zr, Zn, Ce, Bi, Sr, Mn, Cu, Ni, Li, Na, K and/or a protonated nitrogen base and Y=a mineral acid, a carboxylic acid, a Lewis acid or organic acid, where n=a whole or fractional number from 0 to 4, catalyst A is a transition metal and/or transition metal compound a
    Type: Application
    Filed: October 6, 2009
    Publication date: September 1, 2011
    Applicant: CLARIANT FINANCE (BVI) LIMITED
    Inventors: Michael Hill, Werner Krause, Martin Sicken
  • Patent number: 7795464
    Abstract: A method for efficiently producing L-2-amino-4-(hydroxymethylphosphinyl)-butanoic acid, useful as a herbicide, by a catalytic asymmetric synthesis reaction with a high asymmetric yield. The method includes a step in which a compound represented by the below formula (1) and a benzylamine are reacted in the presence of dehydrating agent, then the resulting mass is reacted with hydrogen cyanide in the presence of an asymmetric catalyst, followed by acid hydrolysis, further followed by elimination of a protective group. [chemical formula 1] (1) (where, R1 represents a C1-4 alkyl group).
    Type: Grant
    Filed: September 19, 2007
    Date of Patent: September 14, 2010
    Assignee: Meiji Seika Kaisha Ltd.
    Inventors: Nobuto Minowa, Nozomu Nakanishi, Masaaki Mitomi
  • Publication number: 20090270647
    Abstract: A method for efficiently producing L-2-amino-4-(hydroxymethylphosphinyl)-butanoic acid, useful as a herbicide, by a catalytic asymmetric synthesis reaction with a high asymmetric yield. The method includes a step in which a compound represented by the below formula (1) and a benzylamine are reacted in the presence of dehydrating agent, then the resulting mass is reacted with hydrogen cyanide in the presence of an asymmetric catalyst, followed by acid hydrolysis, further followed by elimination of a protective group. [chemical formula 1] (1) (where, R1 represents a C1-4 alkyl group.
    Type: Application
    Filed: September 19, 2007
    Publication date: October 29, 2009
    Applicant: MEIJI SEIKA KAISHA LTD.
    Inventors: Nobuto Minowa, Nozomu Nakanishi, Masaaki Mitomi
  • Publication number: 20090253926
    Abstract: The present invention provides processes for synthesizing lysine based compounds of the formula; wherein R1 may be, for example, (HO)2P(O)—, (NaO)2P(O)—, wherein X may be, for example, NH2, Y may be H, F, Cl, or Br, and wherein n, X?, Y?, R2, R3, R4, R5 and R6 are as defined herein.
    Type: Application
    Filed: June 19, 2008
    Publication date: October 8, 2009
    Applicant: Ambrilla Biopharma Inc.
    Inventors: Guy Milot, Stephane Branchaud, Brent R. Stranix
  • Publication number: 20090163725
    Abstract: A phosphonic acid diester derivative represented by the following general formula (1): wherein at least one of R1 and R2 denotes a leaving group.
    Type: Application
    Filed: November 30, 2006
    Publication date: June 25, 2009
    Inventors: Jun Hiratake, Kanzo Sakata, Liyou Han
  • Patent number: 7452487
    Abstract: A phosphorus-acid-group-containing (meth)acrylamide polymer having high electrolytic group density and excellent conductivity is obtained by introducing a phosphorus acid group into a (meth)acrylamide monomer which may be N-substituted, and polymerizing the resultant monomer. This polymer is usable for conductive resins, proton-conductive polymer electrolyte membranes and coating agents.
    Type: Grant
    Filed: February 23, 2005
    Date of Patent: November 18, 2008
    Assignee: Uni-Chemical Co., Ltd.
    Inventor: Yoshio Kanzaki
  • Patent number: 7390920
    Abstract: This invention relates to the field of heterogeneous catalysis, and more particularly to catalysts including carbon supports having formed thereon compositions which comprise a transition metal in combination with nitrogen and/or carbon. The invention further relates to the fields of catalytic oxidation, including the preparation of secondary amines by the catalytic oxidation of tertiary amines.
    Type: Grant
    Filed: August 20, 2004
    Date of Patent: June 24, 2008
    Assignee: Monsanto Technology LLC
    Inventors: James P. Coleman, Martin P. McGrath, Fuchen Liu, Juan Arhancet
  • Patent number: 7375244
    Abstract: To present a reaction system that efficiently catalyzes an enantio selective asymmetric nucleophilic addition reaction of an ?-iminophosphonic acid ester. An optically active ?-amino-?-oxophosphonic acid derivative is produced through an asymmetric addition reaction of an ?-iminophosphonic acid ester and a nucleophilic agent (for example, a silyl enol ether).
    Type: Grant
    Filed: March 7, 2005
    Date of Patent: May 20, 2008
    Assignee: Japan Science and Technology Agency
    Inventor: Shu Kobayashi
  • Patent number: 7129373
    Abstract: An oxidation catalyst is prepared by pyrolyzing a source of iron and a source of nitrogen on a carbon support. Preferably, a noble metal is deposited over the modified support which comprises iron and nitrogen bound to the carbon support. The catalyst is effective for oxidation reactions such as the oxidative cleavage of tertiary amines to produce secondary amines, especially the oxidation of N-(phosphonomethyl)iminodiacetic acid to N-(phosphonomethyl)glycine.
    Type: Grant
    Filed: February 14, 2003
    Date of Patent: October 31, 2006
    Assignee: Monsanto Technology LLC
    Inventors: James P. Coleman, Martin P. McGrath
  • Patent number: 6864218
    Abstract: A process for oxidizing a hydroxymethylphosphonic acid compound to produce a formylphosphonic acid compound is described. The oxidation reaction is carried out in the presence of an oxidant and a catalyst. For example, hydroxymethylphosphonic acid (HMPA) is oxidized by oxygen or hydrogen peroxide in the presence of a copper-containing catalyst to give formylphosphonic acid (FPA). Formylphosphonic acid can then be reacted with glycine to produce a condensation product which, upon hydrogenation, yields glyphosate. Glyphosate can be incorporated into various formulations for use as a herbicide. In addition to glycine, formylphosphonic acid can also be reacted with ammonia, ethanolamine, or other primary amines to form a precursor compound, which can be converted to glyphosate.
    Type: Grant
    Filed: July 9, 2002
    Date of Patent: March 8, 2005
    Assignee: Monsanto Technology LLC
    Inventor: Thaddeus S. Franczyk, II
  • Patent number: 6700007
    Abstract: A process for preparing alkoxyamines in a biphasic medium comprises mixing an ionic liquid, an organic solvent, a metal salt, a ligand for the metal, a halocarbon compound ZX and a nitroxide, keeping the reaction medium stirring at a temperature of between 20° C. and 90° C. until the nitroxide has disappeared, separating the mixture by decantation, recovering the organic phase, and optionally washing it with water and then isolating the alkoxyamine by evaporating the organic solvent under reduced pressure.
    Type: Grant
    Filed: August 8, 2002
    Date of Patent: March 2, 2004
    Assignee: Atofina
    Inventors: Jean-Luc Couturier, Olivier Guerret
  • Publication number: 20030078446
    Abstract: A process for oxidizing a hydroxymethylphosphonic acid compound to produce a formylphosphonic acid compound is described. The oxidation reaction is carried out in the presence of an oxidant and a catalyst. For example, hydroxymethylphosphonic acid (HMPA) is oxidized by oxygen or hydrogen peroxide in the presence of a copper-containing catalyst to give formylphosphonic acid (FPA). Formylphosphonic acid can then be reacted with glycine to produce a condensation product which, upon hydrogenation, yields glyphosate. Glyphosate can be incorporated into various formulations for use as a herbicide. In addition to glycine, formylphosphonic acid can also be reacted with ammonia, ethanolamine, or other primary amines to form a precursor compound, which can be converted to glyphosate.
    Type: Application
    Filed: July 9, 2002
    Publication date: April 24, 2003
    Applicant: Monsanto Technology LLC
    Inventor: Thaddeus S. Franczyk
  • Patent number: 6242615
    Abstract: Processes for preparing compounds of the formula (I) are described: P1OOC—CH(OH)—CHR1—CONH—Z wherein P1 is hydrogen or a protecting group, Z is a group —CHR2COOP2 or —CHR2CONR3R4 wherein P2 is hydrogen or a protecting group and R1-R4 are values known in the TNF-inhibitor art. The compounds of the formula (I) are useful in inhibiting TNF and one or more matrix metalloproteinase enzymes. One intermediate in a process of the invention is formula (II).
    Type: Grant
    Filed: September 28, 1999
    Date of Patent: June 5, 2001
    Assignees: Zeneca Limited, Zeneca Pharma S.A.
    Inventors: Jacques Pelleter, Marie-Jeanne Pasquet, Thomas Geoffrey Colerick Bird
  • Patent number: 6218563
    Abstract: The present invention provides a process for preparing a cyanophosphonamide comprising contacting phosphoric anhydride and a cyanide, preferably in the presence of a Lewis base, to produce a cyanophosphonate intermediate, and subsequently contacting the cyanophosphonate intermediate with an amino compound.
    Type: Grant
    Filed: November 29, 1999
    Date of Patent: April 17, 2001
    Assignee: Monsanto Company
    Inventors: Patrick J. Lennon, Serge G. Vulfson
  • Patent number: 6147245
    Abstract: A unique method for the synthesis of substantially pure .alpha.-keto bisphosphonate esters and the usage of these esters in reactions with C, N, O, or P nucleophiles for synthesis of .alpha.-functionalized bisphosphonates. The method starts with a reaction mixture formed of an .alpha.-diazo methanediphosphonate ester, including tert-butylchlorite, a polar aprotic organic solvent, and an effective amount of water. After synthesis is complete, a water trapping reagent may be added to remove any excess water. The present invention provides a versatile pathway to new .alpha.-substituted bisphosphonate derivatives and could be readily adapted to combinatorial drug discovery synthetic strategies. The .alpha.-keto bisphosphonate esters can be converted to the corresponding acids by acid hydrolysis or mild silyldealkylation.
    Type: Grant
    Filed: July 13, 1999
    Date of Patent: November 14, 2000
    Assignee: University of Southern California University Park
    Inventors: Charles E. McKenna, Boris A. Kashcmirov
  • Patent number: 6005140
    Abstract: This invention is directed to process for making a composition having the formula (I): ##STR1## wherein R.sup.3, R.sup.4, and R.sup.5 are independently hydrogen, substituted or unsubstituted hydrocarbyl, or an agronomically acceptable cation. The process comprises contacting a solution with a noble metal catalyst and introducing oxygen into the solution. The solution contains an N-substituted glyphosate having the formula (II): ##STR2## wherein R.sup.1 and R.sup.2 are independently hydrogen, halogen, --PO.sub.3 H.sub.2, --SO.sub.3 H, --NO.sub.2, or substituted or unsubstituted hydrocarbyl other than --CO.sub.2 H. R.sup.3, R.sup.4, and R.sup.5 are as defined for formula (I).This invention also relates to an oxidation catalyst comprising a noble metal having a hydrophobic electroactive molecular species adsorbed thereon.
    Type: Grant
    Filed: February 12, 1998
    Date of Patent: December 21, 1999
    Assignee: Monsanto Company
    Inventors: David A. Morgenstern, Yvette M. Fobian
  • Patent number: 5990337
    Abstract: The invention relates to a process for the preparation of phosphorus-containing compounds of the formula (I) ##STR1## where R.sup.1 and R.sup.2 are identical or different and are a straight-chain or branched alkyl radical having 1 to 8 carbon atoms, a cyclohexyl-, cyclopentyl-, aryl-, halogen-, (C.sub.1 -C.sub.6)-alkyl- or (C.sub.1 -C.sub.6)-alkoxy-substituted aryl radical, where R.sup.1 and R.sup.2, together with the phosphorus atom and the oxygen atom, can also form a ring, in particular an oxaphosphorin ring, which comprises metering acrylonitrile at elevated temperature into a compound of the formula (II) ##STR2## where R.sup.1 and R.sup.2 are as defined above.
    Type: Grant
    Filed: August 26, 1997
    Date of Patent: November 23, 1999
    Assignee: Ticona GmbH
    Inventor: Hanss-Jerg Kleiner
  • Patent number: 5905163
    Abstract: A novel process for preparing aminomethylphosphonate derivatives involves the hydrogenation of cyanophosphonate derivatives in the presence of a catalyst to produce aminomethylphosphonate derivatives.
    Type: Grant
    Filed: December 23, 1997
    Date of Patent: May 18, 1999
    Assignee: Monsanto Company
    Inventor: Patrick J. Lennon
  • Patent number: 5861525
    Abstract: A process for preparing cyanophosphonate derivatives involves contacting a phosphate ester and cyanide in a reaction mixture under conditions sufficient to produce a cyanophosphonate derivative. That cyanophosphonate derivative product can subsequently be hydrogenated to produce an aminomethylphosphonate derivative.
    Type: Grant
    Filed: December 23, 1997
    Date of Patent: January 19, 1999
    Assignee: Monsanto Company
    Inventors: Patrick J. Lennon, Sergey G. Vulfson
  • Patent number: 5858317
    Abstract: A process for preparing cyanophosphonate derivatives involves contacting phosphoric anhydride (P.sub.4 O.sub.10) and a cyanide, preferably in the presence of a Lewis base, in a reaction mixture under sufficient conditions to produce a cyanophosphonate derivative. The cyanophosphonate derivative can be subsequently hydrogenated to produce an aminomethylphosphonate derivative.
    Type: Grant
    Filed: December 23, 1997
    Date of Patent: January 12, 1999
    Assignee: Monsanto Company
    Inventors: Patrick J. Lennon, Sergey G. Vulfson
  • Patent number: 5859278
    Abstract: A process for preparing cyanophosphonate derivatives involves contacting a pyrophosphate ester or a polyphosphate ester and cyanide in a reaction mixture under conditions sufficient to produce the cyanophosphonate derivative. The cyanophosphonate derivative product can subsequently be hydrogenated to produce an aminomethylphosphonate derivative.
    Type: Grant
    Filed: December 23, 1997
    Date of Patent: January 12, 1999
    Assignee: Monsanto Company
    Inventors: Patrick J. Lennon, Sergey G. Vulfson
  • Patent number: 5824809
    Abstract: Novel .alpha.-aminophosphonates are provided along with processes and intermediates for their preparation. In preferred embodiments, scalemic .alpha.-aminophosphonates are prepared by the stereoselective addition of phosphite salts to chiral imines.
    Type: Grant
    Filed: April 15, 1996
    Date of Patent: October 20, 1998
    Assignee: The Trustees of the University of Pennsylvania
    Inventors: Amos B. Smith, III, Kraig M. Yager, Carol M. Taylor
  • Patent number: 5760270
    Abstract: A method of producing an ether-type thio-phospholipid of the formula (I): ##STR1## wherein: n is an integer of 13 to 17;A is C.sub.14 -C.sub.20 acyl group;G is a group selected from the group consisting of: ##STR2## which is useful as synthetic substrate of cytosolic phospholipase A.sub.2 inhibitors, said method being applicable to mass production of the compound (I), intermediates therefor and the preparation of the same are provided.
    Type: Grant
    Filed: April 23, 1997
    Date of Patent: June 2, 1998
    Assignee: Shionogi & Co., Ltd.
    Inventors: Mitsuaki Ohtani, Masahiro Fuji
  • Patent number: 5648509
    Abstract: The addition of acid diesters of phosphorous acid onto alpha,beta-unsaturated carboxylic acid derivatives under basic catalysis is achieved with good yields if it is carried out in the presence of alkali metal alcoholates or phenolates and in the presence of halides, oxides or hydroxides of divalent metals. Co-use of these metal compounds allows relatively small mounts of metal alcoholates or phenolates to be used. The resulting reaction mixtures do not contain relatively large amounts of troublesome by-products.
    Type: Grant
    Filed: July 27, 1995
    Date of Patent: July 15, 1997
    Assignee: Ciba-Geigy Corporation
    Inventors: Salman Dermeik, Martina Wanner, Karl-Heinz Lemmer, Reinhold Braun
  • Patent number: 5608098
    Abstract: Novel bis(aminomethyl)phosphinic acid derivatives and process for the preparation of bis(aminomethyl)phosphinic acid derivativesCompounds of the formula VI ##STR1## can be prepared by reaction of a compound of the formula IV ##STR2## with a base to give a compound of the formula Va or Vb ##STR3## and subsequent reaction with carbon nucleophiles; alternatively the compound of the formula VI is prepared by direct reaction of the compound of the formula IV e.g. with R.sup.2 Cu(CN)Li.sub.2, the above substituents having the meanings mentioned.
    Type: Grant
    Filed: September 28, 1995
    Date of Patent: March 4, 1997
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Anuschirwan Peyman, J org Spanig, Karl-Heinz Budt
  • Patent number: 5578190
    Abstract: A process for preparing glyphosate and other secondary amines of related structure in which a precursor primary amine such as aminomethylphosphonic acid is condensed with glyoxylic acid, or a related aldehyde compound, and the condensation product reduced without isolation to produce the desired product.
    Type: Grant
    Filed: April 7, 1995
    Date of Patent: November 26, 1996
    Assignee: Monsanto Company
    Inventors: Thomas E. Rogers, Lowell R. Smith
  • Patent number: 5530142
    Abstract: Process for the preparation of optically active 4-(phosphinoethyl)-1,3-oxazolidin-5-one derivatives.The invention relates to a process for preparing optically active compounds of formula (IV) ##STR1## in which the radicals R.sub.1, R.sub.2, R.sub.3 ', R.sub.7, n and m are as defined in the main claim,which comprises reacting a compound of formula (II) ##STR2## with a compound of formula (III) ##STR3## in the presence of catalytical amounts of a radical former.
    Type: Grant
    Filed: September 20, 1994
    Date of Patent: June 25, 1996
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Hans-Joachim Zeiss
  • Patent number: 5510504
    Abstract: A process for the preparation of .alpha.- or .alpha.,.alpha.'-substituted derivatives of the bis(aminomethyl)phosphinic acid of the formula I and their acid or basic salts, ##STR1## in which R.sup.1, R.sup.2 and R.sup.3 are defined as in the description, wherein a bis(aminomethyl)phosphinate is converted into the corresponding bisimine, which is alkylated by R.sup.2 and R.sup.3 in the .alpha.- and/or .alpha.,.alpha.'-position after reaction with a base, and is converted into a compound of the formula I by subsequent treatment with an acid.
    Type: Grant
    Filed: January 4, 1995
    Date of Patent: April 23, 1996
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Anuschirwan Peyman, Karl-Heinz Budt, Jorg Spanig, Jian-Qi Li, Bernd Stowasser
  • Patent number: 5424441
    Abstract: N-aralkyl- and N-heteroaralkyl-aminoalkanephosphinic acids of formula I ##STR1## wherein R is an aliphatic, cycloaliphatic, cycloaliphatic-aliphatic, araliphatic or heteroarylaliphatic radical having at least 2 carbon atoms, R.sub.1 is hydrogen or hydroxy, R.sub.2 is an araliphatic or heteroarylaliphatic radical substituted by free or functionally modified carboxy that is bonded directly or by way of a spacer, and R.sub.3 is hydrogen, lower alkyl or a group R.sub.2, and the salts thereof have valuable nootropic and anti-epileptic properties and can be used in the preparation of a nootropic or anti-epileptic medicament.
    Type: Grant
    Filed: May 4, 1994
    Date of Patent: June 13, 1995
    Assignee: Ciba-Geigy Corporation
    Inventors: Stuart J. Mickel, Wolfgang Frostl, Pascal Furet
  • Patent number: 5391800
    Abstract: A method of inhibiting tumor cell chemotactic and/or chemoinvasion motility comprising contacting the tumor cell with an inhibitory amount of an agent selected from the group consisting of sphingosine-1-phosphate, derivatives of sphingosine-1-phosphate and mimetics of the sphingosine-1-phosphate or of the derivatives. A method of inhibiting phagokinetic activity of tumor cells and neutrophils comprising contacting the cells with a phagokinetic inhibitory amount of an agent selected from the group consisting of sphingosine-1-phosphate, derivatives of sphingosine-1-phosphate, and mimetics of the sphingosine-1-phosphate or of the derivatives. A method of inhibiting tumor cell metastasis comprising administering to a host in need of treatment a metastasis inhibitory amount of an agent selected from the group consisting of sphingosine-1-phosphate, derivatives of sphingosine-1-phosphate, and mimetics of the sphingosine-1-phosphate or of the derivatives, and pharmaceutically acceptable salts of the agent.
    Type: Grant
    Filed: August 9, 1993
    Date of Patent: February 21, 1995
    Assignee: The Biomembrane Institute
    Inventors: Yasuyuki Igarashi, Fuqiang Ruan, Yoshito Sadahira, Shigeyuki Kawa, Sen-itiroh Hakomori
  • Patent number: 5321153
    Abstract: This invention is selected novel chiral (essentially pure) alpha-amino phosphonates, process for the preparation which is a catalytic asymmetric hydrogenation of olefins and novel intermediates therefor. The alpha-amino phosphonates are useful as antibiotics and/or as intermediates in the preparation of phosphorus-containing analogs of peptides, i.e., phosphonopeptides or pseudopeptides having known uses, such as in antibiotics, antibiotic enhancers, or enzyme inhibitors.
    Type: Grant
    Filed: June 15, 1992
    Date of Patent: June 14, 1994
    Assignee: Monsanto Company
    Inventor: John J. Talley
  • Patent number: 5315023
    Abstract: A process for the preparation of highly pure deacylated glycerophosphorylcholine, glycerophosphorylethanolamine and glicerophosphorylserine starting from mixtures of the corresponding acylated derivatives.The process according to the invention is characterized in that the deacylation reaction, by means of alcoholysis, and the fractionation are carried out in a single step in a reactor containing a basic ion-exchange resin.
    Type: Grant
    Filed: March 8, 1993
    Date of Patent: May 24, 1994
    Assignee: Chemi S.p.A.
    Inventors: Lorenzo De Ferra, Fausto Bonifacio, Guido Cifarelli, Pietro Massardo, Oreste Piccolo
  • Patent number: 5288418
    Abstract: Amine coupled condensation products of hindered phenols and phosphites have been found to be effective antioxidant/antiwear additives for lubricants.
    Type: Grant
    Filed: December 3, 1992
    Date of Patent: February 22, 1994
    Assignee: Mobil Oil Corporation
    Inventors: Liehpao O. Farng, Andrew G. Horodysky, William F. Olszewski
  • Patent number: 5051525
    Abstract: N-acyl-2-amino acid amides containing phosphinic esters, process for their preparation, and N-acyl-2-amino acid nitriles as precursorsPhosphorus-containing N-acyl-2-amino acid amides of the general formula (I) ##STR1## where R.sup.1 is alkyl, optionally substituted by halogen or alkoxy, or is benzyl or phenyl, each of which is optionally substituted by alkyl, alkoxy, halogen, nitro or CF.sub.3, or is cycloalkyl, andR.sup.2 is H, or alkyl, optionally substituted by halogen or alkoxy, or is (CH.sub.2).sub.n -phenyl, optionally substituted in the phenyl ring by alkyl, alkoxy, halogen, nitro or CF.sub.3, where n=0, 1, 2 or 3,are valuable intermediates for the preparation of L-phosphinothricin by enzymatic cleavage, and can be obtained from the corresponding N-acyl-2-amino acid nitrile by selective acid hydrolysis.
    Type: Grant
    Filed: February 2, 1990
    Date of Patent: September 24, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Lothar Willms
  • Patent number: 5051524
    Abstract: Compounds of the formula I ##STR1## wherein R denotes an aliphatic, cycloaliphatic, cycloaliphatic-aliphatic or araliphatic radical having 2 or more carbon atoms, and wherein one of the groups R.sup.1, R.sup.2 and R.sup.3 represents hydrogen or an aliphatic, cycloaliphatic, araliphatic or aromatic radical, another one of R.sup.1, R.sup.2 and R.sup.3 is hydrogen or, in the case of R.sup.1 and R.sup.2, is hydroxy, and the remaining one of R.sup.1, R.sup.2 and R.sup.3 is hydrogen, or wherein R denotes methyl, R.sub.1 denotes hydrogen or hydroxy, R.sub.2 denotes an aromatic radical and R.sub.3 represents hydrogen, and their salts have GABA.sub.B -antagonistic properties and can be used as GABA.sub.B -antagonists. They are obtained when in a compound of formula II ##STR2## in which R, R.sup.1, R.sup.2 and R.sup.3 have their previous significances, Z represents --NH.sub.2 and R.sup.4 denotes a hydroxy-protective group R.sup.5 or, when R.sup.1 and R.sup.3 denote hydrogen and R.sup.
    Type: Grant
    Filed: February 26, 1990
    Date of Patent: September 24, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Eric K. Baylis, Helmut Bittiger, Wolfgang Frostl, Roger G. Hall, Ludwig Maier, Stuart J. Mickel, Hans-Rudolf Olpe
  • Patent number: 5043474
    Abstract: The invention relates to rhodium complexes of the formula[A--O--(CH.sub.2 CH.sub.2 O).sub.n --A].sup.2+ 2X.sup.- (Ia)and[A--O--(CH.sub.2 CH.sub.2 O).sub.m --CH.sub.3 ].sup.+ X.sup.-(Ib)in whichn=5-1,000,m=5-250,X.sup.- denotes a tetrafluoroborate, hexafluorophosphate or per-chlorate anion,A denotes a radical of the formula ##STR1## (en).sub.2 denotes two molecules of a monoolefin or one molecule of a diolefinAr denotes phenyl or phenyl which is substituted by one or two alkyl groups having 1 or 2 carbon atoms andR.sup.1 denotes an arylene or alkylene bridge,and their use for the preparation of L-phosphinothricin and its derivatives by enantioselective catalytic hydrogenation of 2,3-dehydrophosphinothricin (derivatives).
    Type: Grant
    Filed: January 17, 1990
    Date of Patent: August 27, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Wolf-Dieter Muller, Hans-Jerg Kleiner
  • Patent number: 4933470
    Abstract: A method is described for producing vicinal diamines comprising the steps of converting a compound, possessing a leaving group on a carbon atom interposed between carbon atoms containing amino groups, to an aziridine-containing compound and reacting the latter compound with a nucleophile to form a vicinal diamine. The compound chosen for the rearrangement reaction may be selected from a wide range of compounds, including those with halide, heteroatom and aryl substituents. The amino groups may be blocked or unblocked. A variety of functional groups, including those which extend the carbon backbone, may be incorporated via opening of the aziridine-containing compound by addition of a selected nuclepohile. Aziridine-containing compositions and vicinal diamine compositions are disclosed. Functionalized vicinal diamines have numerous uses, including as intermediates for radionuclide-chelating ligands for use in the diagnosis and therapy of cancer.
    Type: Grant
    Filed: October 5, 1987
    Date of Patent: June 12, 1990
    Assignee: NeoRx Corporation
    Inventor: David S. Jones
  • Patent number: 4922006
    Abstract: The process for the preparation of L-phosphinothricine (derivatives) by homogeneous asymmetric hydrogenation of 2,3-dehydrophospinothricine (derivatives) by means of suitable ruthenium, rhodium or iridium catalysts.
    Type: Grant
    Filed: March 20, 1987
    Date of Patent: May 1, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Hans-Joachim Zeiss