Forming The Phosphorus Ester Group Patents (Class 558/89)
  • Patent number: 11773118
    Abstract: A new process to synthesis of compound OBI-3424 R-form and S-form products is provided. The “R-form” compound OBI-3423 was first synthesized with 48% overall yield from compound OBI-3424-5 by installation of the labile phosphate motif at later stage. The stereo chemistry is established by 5 steps chemo-enzyme combination synthesis to afford 99% optical purity. After then, the “S-form” compound OBI-3424 is prepared with improving overall yield of 54% from compound OBI-3424-5. The stereo chemistry is established by 4 steps combination of chemo-enzyme synthesis with excellent optical purity of 99%.
    Type: Grant
    Filed: February 21, 2020
    Date of Patent: October 3, 2023
    Assignee: OBI PHARMA, INC.
    Inventors: Cheng-Der Tony Yu, Yih-Huang Hsieh, Shu-Yi Lin, Chin-Sheng Chao, Yin-Cheng Hsieh, Ming-Tain Lai
  • Patent number: 8921343
    Abstract: The present invention is directed to fluorophosphates, and pharmaceutical compositions thereof, which are inhibitors of intestinal apical sodium/phosphate co-transport and are useful in the treatment of hyperphosphatemia, in reducing blood phosphate levels, and in treating hypertension.
    Type: Grant
    Filed: March 4, 2011
    Date of Patent: December 30, 2014
    Assignee: Duophos
    Inventors: Brian Peerce, Larry Slomowitz
  • Publication number: 20140316154
    Abstract: The present invention includes methods for the synthesis of sphingomyelins and dihydrosphingomyelins. The present invention also includes methods for the synthesis of sphingosines and dihydrosphingosines. The present invention further includes methods for the synthesis of ceramides and dihydroceramides.
    Type: Application
    Filed: March 14, 2014
    Publication date: October 23, 2014
    Inventors: Daniela Carmen ONICIU, Stefan Heckhoff, Benoit Oswald, Peter Rebmann, Andreas Peer, Miguel Gonzalez, Patrik Sauter
  • Patent number: 8841475
    Abstract: The invention relates to a method for producing phosphoric acid triesters of formula (I). According to said method, phosphoric acid or a phosphoric acid derivative selected from orthophosphoric acid, tetraphosphoric decaoxide and polyphosphoric acid is reacted with alkoxylated alcohols of formulae (II) R1—(OA1)x—OH, (III) R2—(OA2)y—OH, and (IV) R3—(OA3)z—OH, in the molar ratio phosphoric acid or phosphoric acid derivative to alkoxylated alcohol of 1:2.5 to 1:3.3, at between 200 and 240° C.
    Type: Grant
    Filed: February 5, 2013
    Date of Patent: September 23, 2014
    Assignee: Clariant Finance (BVI) Limited
    Inventors: Peter Klug, Franz-Xaver Scherl, Waltraud Simsch, Adelgunde Oberhauser
  • Publication number: 20140155286
    Abstract: The present invention relates to a method and tools which allow the kinetic monitoring of hydrolase enzyme activity. The present invention also aims to provide synthetic peptides and peptide residues modified such that they can be used in assays for monitoring hydrolase enzyme activity, and preferably phosphatase activity. Also claimed are modified tyrosine amino acid derivatives of formula (IV), wherein Y is chosen from —POy2? with y equal to 2 or 3 and esters thereof, —SOz? with z equal to 2 or 3 and esters thereof, a carbohydrate or carbohydrate derivatives; and; wherein X1 and/or X2 is selected from —N3, —NO2, —CI, or —CN, —SCN, a C1 to C8 alkyl, or H, wherein either X1 or X2 is not H.
    Type: Application
    Filed: May 18, 2012
    Publication date: June 5, 2014
    Applicant: PamGene B.V.
    Inventors: Robby Ruijtenbeek, Jeroen van Ameijde, Robertus Matthias Joseph Liskamp
  • Publication number: 20130085120
    Abstract: Phosphate ester compound of hydroxy acid substituted phenyl ester, preparation method and medical use thereof are provided. The title compound is shown in formula (I), in which Y=C1-4 straight carbon chain, M1 and/or M2=H, alkali metal ion, protonated amine or protonated amino acid. The compound has good water solubility and high stability in its aqueous solution, and it can release 2,6-diisopropylphenol rapidly under the action of enzymes in vivo, which has the effects of sedation, hypnosis and/or anesthesia. By protecting hydroxyl of 2,6-diisopropylphenol in compound of formula (I), the first-pass metabolic activity of 2,6-diisopropylphenol is reduced, so that the synthetic compound can be used for sedation, hypnosis and/or anesthesia.
    Type: Application
    Filed: October 13, 2010
    Publication date: April 4, 2013
    Applicants: Yichang Humanwell Pharmaceutical Co., Ltd., West China Hospital, Sichuan University
    Inventors: Wensheng Zhang, Jun Yang, Jin Liu
  • Publication number: 20130059822
    Abstract: The present invention is directed to fluorophosphates, and pharmaceutical compositions thereof, which are inhibitors of intestinal apical sodium/phosphate co-transport and are useful in the treatment of hyperphosphatemia, in reducing blood phosphate levels, and in treating hypertension.
    Type: Application
    Filed: March 4, 2011
    Publication date: March 7, 2013
    Applicant: DUOPHOS
    Inventors: Brian Peerce, Slomowitz Larry
  • Patent number: 8389756
    Abstract: The invention relates to a method for producing phosphoric acid triesters of formula (I). According to said method, phosphoric acid or a phosphoric acid derivative selected from orthophosphoric acid, tetraphosphoric decaoxide and polyphosphoric acid is reacted with alkoxylated alcohols of formulae (II) R1—(OA1)x-OH, (III) R2—(OA2)y-OH, and (IV) R3—(OA3)Z-OH, in the molar ratio phosphoric acid or phosphoric acid derivative to alkoxylated alcohol of 1:2.5 to 1:3.3, at between 200 and 240° C.
    Type: Grant
    Filed: July 29, 2008
    Date of Patent: March 5, 2013
    Assignee: Clariant Finance (BVI) Limited
    Inventors: Peter Klug, Franz-Xaver Scherl, Waltraud Simsch, Adelgunde Oberhauser
  • Patent number: 8378135
    Abstract: Multifunctional alcohols, polyols derived from cardanol containing at least 3 hydroxyl groups are disclosed. Such alcohols allow for synthesis of multifunctional crosslinkers such as acrylates, epoxies, and vinyl ethers and flame retardants such as >phosphates. The multifunctional alcohols or polyols can be used in polyurethanes and polycarbonates. The multifunctional crosslinkers can be used in optical coating and waveguide compositions to increase curing speed and crosslink density. The multifunctional phosphates can be used in flame resistant plastics as the highly pendant phosphorus containing phosphate non-halogen flame retardant additives.
    Type: Grant
    Filed: December 30, 2005
    Date of Patent: February 19, 2013
    Assignee: Council of Scientific and Industrial Research
    Inventors: Vadakkethonippurathu Sivankutty Nair Prasad, Chennakkattu Krishna Sadasivan Pillai
  • Patent number: 8293938
    Abstract: The invention relates to alkylphosphonous acids, salts and esters of formula (I) A-P(?O)(OX)—H (I) wherein A is C2-C20alkyl, C2-C20alkylene, and C8-C20 alkaryl are optionally substituted, and X is H, alkyl, aryl, alkylaryl, alkenyl, substituted alkyl, aryl, alkaryl, alkenyl, ammonium, primary, secondary, tertiary, quaternary alkyl and/or aryl ammonium, an alkali metal, an alkaline earth metal, a metal of the third and fourth main group and the second, fourth and eight sub-group or a metal of the lanthanoid group. The invention also relates to methods for producing same and to the uses of said compounds.
    Type: Grant
    Filed: July 2, 2008
    Date of Patent: October 23, 2012
    Assignee: Clariant Finance (BVI) Limited
    Inventors: Michael Hill, Harald Bauer, Werner Krause
  • Publication number: 20110306088
    Abstract: A honeycomb body is disclosed having cells extending along a common direction, a first plurality of the cells being open at both ends of the body and a second plurality of the cells being closed at one or both ends of the body, the second plurality of cells arranged in one or more groups of cells cooperating to define one or more fluid passages extending through the body at least in part perpendicularly to the common direction, wherein, in a plane perpendicular to the common direction, the ratio of the area of cells of the first plurality to the area of cells of the second plurality varies along the length of at least one of the one or more fluid passages.
    Type: Application
    Filed: February 26, 2010
    Publication date: December 15, 2011
    Inventors: Peng Chen, Yi Jiang, James Scott Sutherland, Andrew David Woodfin
  • Publication number: 20110245385
    Abstract: The invention relates to a process for preparing mono-carboxy-functionalized dialkylphosphinic acids, dialkylphosphinic esters and dialkylphosphinic salts by means of alkylene oxides, characterized in that a) a phosphinic acid source (I) is reacted with olefins (IV) in the presence of a catalyst A to form an alkylphosphonous acid, its salt or ester (II), b) the resultant alkylphosphonous acid, its salt or ester (II) is reacted with alkylene oxides of the formula (V) in the presence of a catalyst B, to give a mono-functionalized dialkylphosphinic acid derivative (VI), and c) the resultant mono-functionalized dialkylphosphinic acid derivative (VI) is reacted in the presence a catalyst C to give the mono-carboxy-functionalized dialkylphosphinic acid derivative (III), where R1,R2,R3,R4,R5, and R6 are identical or different and independently of one another are inter alia H, C1-C18-alkyl, C6-C18-aryl, C6-C18-aralkyl or C6-C18-alkylaryl, and X and Y are identical or different and independently of one another are H,
    Type: Application
    Filed: October 6, 2009
    Publication date: October 6, 2011
    Applicant: CLARIANT FINANCE (BVI) LIMITED
    Inventors: Michael Hill, Mathias Dietz, Werner Krause, Martin Sicken
  • Patent number: 8022239
    Abstract: A novel class of compounds to inactivate autotaxin enzymes is provided. Such compounds include mono- and di-fluoromethylphenyl C12-C18 phosphodiesters and exhibit reactivity with autotaxin to ultimately reduce the size of the reactive sites thereon to prevent conversion of lysophosphatidyl choline to lysophophatidic acid. Furthermore, such compounds are non-cytotoxic, and can be incorporated within delivery forms for human ingestion. As such, these compounds accord an excellent manner of potentially reducing generation of certain cancers attributable to the presence of naturally occurring autotaxin within the human body. Methods of producing such novel compounds are encompassed within this invention as well as methods of inactivating autotaxin to certain degrees therewith.
    Type: Grant
    Filed: October 2, 2009
    Date of Patent: September 20, 2011
    Assignee: The University of Memphis Research Foundation
    Inventors: Abby Louise Parrill-Baker, Daniel Lee Baker, Louis Edward Montedonico
  • Publication number: 20110218260
    Abstract: New highly-effective non-halogen, low VOC, low fogging, and cost-effective oligomeric polyphosphonate flame retardants for flexible polyurethane foams as well as for other flame retardant applications are described. In addition, methods for the preparation and uses of such new highly effective flame retardants are described.
    Type: Application
    Filed: October 20, 2009
    Publication date: September 8, 2011
    Applicant: ALBEMARLE CORPORATION
    Inventors: Arthur G. Mack, Techen Tsao
  • Publication number: 20110118210
    Abstract: Compounds of formula I: wherein R1, R2, n and m are as defined in the specification, processes for their production, their uses and pharmaceutical compositions containing them.
    Type: Application
    Filed: January 28, 2011
    Publication date: May 19, 2011
    Inventors: Rainer ALBERT, Eric Francotte, Frédéric Zecri, Markus Zollinger
  • Publication number: 20100291118
    Abstract: The present invention relates to a new class of compounds having ?? T cells activating properties of Formula (I), a composition comprising these compounds and methods for regulating an immune response in a subject comprising the step of administering these compounds.
    Type: Application
    Filed: July 28, 2010
    Publication date: November 18, 2010
    Applicant: INNATE PHARMA
    Inventors: Christian Belmant, Patrice Nury
  • Patent number: 7829737
    Abstract: The present invention provides compounds of Formula (I) and Formula (II) that are useful for modulating the biological activity of the protein tyrosine phosphatase-1b (PTP1B) enzyme. Compounds of this invention can be used to treat diseases and/or conditions in which the PTP1B enzyme is a factor. Such diseases and/or conditions include, but are not limited to, Type 1 diabetes, Type 2 diabetes, inadequate glucose tolerance, insulin resistance, obesity, hyperlipidemia, hypertriglyceridemia, hypercholesterolemia, low HDL levels, atherosclerosis, vascular restenosis, inflammatory bowel disease, pancreatitis, adipose cell tumors, adipose cell carcinoma, liposarcoma, dyslipidemia, cancer, and neurodegenerative diseases.
    Type: Grant
    Filed: March 6, 2008
    Date of Patent: November 9, 2010
    Assignee: Ceptyr, Inc.
    Inventors: Mark Arnold Thomas Blaskovich, Ted Baughman, Thomas Little, Maher Qabar, Lauri Marie Schultz, Feng Hong, William Patt, Gangadhar Nagula, Jennifer Lynn Gage, James Jeffry Howbert
  • Publication number: 20100228045
    Abstract: The present invention relates to a suspension stabilizer for dispersing inorganic nanoparticles into aqueous medium. More particularly, the present invention is directed to a biocompatible suspension stabilizer which comprises phosphoryl domain having an affinity to the surface of an inorganic nanoparticle and poly(ethylene glycol) having an affinity to the aqueous medium, and which is prepared by reacting a biocompatible poly(ethylene glycol)-derivatized polymer with phosphine oxide having a leaving group.
    Type: Application
    Filed: October 15, 2008
    Publication date: September 9, 2010
    Applicant: SEOUL NATIONAL UNIVERSITY INDUSTRY FOUNDATION
    Inventors: Taeghwan Hyeon, Sang-Wook Kim, Hyon-Bin Na
  • Publication number: 20100136650
    Abstract: A novel class of compounds to inactivate autotaxin enzymes is provided. Such compounds include mono- and di-fluoromethylphenyl C12-C18 phosphodiesters and exhibit reactivity with autotaxin to ultimately reduce the size of the reactive sites thereon to prevent conversion of lysophosphatidyl choline to lysophophatidic acid. Furthermore, such compounds are non-cytotoxic, and can be incorporated within delivery forms for human ingestion. As such, these compounds accord an excellent manner of potentially reducing generation of certain cancers attributable to the presence of naturally occurring autotaxin within the human body. Methods of producing such novel compounds are encompassed within this invention as well as methods of inactivating autotaxin to certain degrees therewith.
    Type: Application
    Filed: October 2, 2009
    Publication date: June 3, 2010
    Inventors: Abby Louise Parrill-Baker, Daniel Lee Baker, Louis Edward Montedonico
  • Patent number: 7728162
    Abstract: A novel process for preparing in a high purity and in a high yield phosphorus compounds having a phosphate-phosphonate bond within one molecule, along with only a small amount of a by-product, without being restricted by the kind of a phosphonate having an alcoholic hydroxyl group which is a raw material, without using a catalyst such as magnesium chloride, but only using a nitrogen-containing basic compound.
    Type: Grant
    Filed: October 18, 2005
    Date of Patent: June 1, 2010
    Assignee: Daihachi Chemical Industry Co., Ltd.
    Inventors: Kazuo Fujimoto, Sakiko Tanaka
  • Patent number: 7557234
    Abstract: The invention relates to a new process for the production of alkyl dialkoxyalkylphosphinates. A hypophosphite salt is used in the process.
    Type: Grant
    Filed: September 12, 2005
    Date of Patent: July 7, 2009
    Assignee: AstraZeneca AB
    Inventors: Maths Nilsson, Mats Thelin, Johanna Wachtmeister
  • Patent number: 7534776
    Abstract: A process for making water-soluble phosphonooxymethyl ethers of hindered alcohol and phenol containing pharmaceuticals, such as camptothecin, propofol, etoposide, Vitamin E and Cyclosporin A. In particular, the process for preparing water-soluble phosphonooxymethyl derivatives comprises the steps of: R—OH represents an alcohol- or phenol-containing drug, n represents an integer of 1 or 2, R1 is hydrogen, an alkali metal ion, or a pharmaceutically acceptable cation, and R2 is hydrogen, an alkali metal ion, or a pharmaceutically acceptable cation.
    Type: Grant
    Filed: October 26, 2006
    Date of Patent: May 19, 2009
    Assignee: Eisai Corporation of North America
    Inventors: George Bonneville, Greg Delahanty, Andrew J. Walz
  • Patent number: 7504389
    Abstract: The present invention provides compounds of Formula (I) and Formula (II) that are useful for modulating the biological activity of the protein tyrosine phosphatase-1b (PTP1B) enzyme. Compounds of this invention can be used to treat diseases and/or conditions in which the PTP1B enzyme is a factor. Such diseases and/or conditions include, but are not limited to, Type 1 diabetes, Type 2 diabetes, inadequate glucose tolerance, insulin resistance, obesity, hyperlipidemia, hypertriglyceridemia, hypercholesterolemia, low HDL levels, atherosclerosis, vascular restenosis, inflammatory bowel disease, pancreatitis, adipose cell tumors, adipose cell carcinoma, liposarcoma, dyslipidemia, cancer, and neurodegenerative diseases.
    Type: Grant
    Filed: November 15, 2005
    Date of Patent: March 17, 2009
    Assignee: Ceptyr, Inc.
    Inventors: Mark Arnold Thomas Blaskovich, Ted Baughman, Thomas Little, William Patt, Maher Qabar, Lauri Mario Schultz, Gangadhar Nagula, Jennifer Lynn Gage, James Jeffry Howbert
  • Publication number: 20080200679
    Abstract: The present invention relates to a method for preparing ?-hydroxy, ?-substituted methylenebisphosphonates and phosphonoacetates via addition of Grignard or organoindium reagents to tetraalkyl carbonylbisphosphonates and trialkyl carbonylphosphonoacetates. Also disclosed are compounds so synthesized.
    Type: Application
    Filed: January 22, 2008
    Publication date: August 21, 2008
    Applicant: UNIVERSITY OF SOUTHERN CALIFORNIA
    Inventors: Charles E. McKenna, Boris A. Kashemirov, Gregorio V. Sanchez
  • Patent number: 7312251
    Abstract: Stable rare earth tris (organophosphate) solutions comprise a rare earth tris (organophosphate) and a hydrocarbon solvent. From about 2% to about 10% rare earth element, preferably from about 3% to about 8%, is present in the solutions. The rare earth tris (organophosphate) solutions are stable from precipitation of the rare earth tris (organophosphate) for at least about fifteen (15) days, preferably for at least about twenty (20) days and most preferably at least about thirty (30) days. A process for preparing these solutions is described herein. A stabilizing additive, acid, glycol or mixtures thereof, is utilized to inhibit precipitation. The molar ratios of free acid, glycol and/or water to the rare earth element are controlled to inhibit precipitation.
    Type: Grant
    Filed: April 7, 2004
    Date of Patent: December 25, 2007
    Assignee: Rhodia Rare Earths, Inc.
    Inventors: Kenan Yunlu, Min He
  • Patent number: 7229978
    Abstract: A process for making water-soluble phosphonooxymethyl ethers of hindered alcohol and phenol containing pharmaceuticals, such as camptothecin, propofol, etoposide, Vitamin E and Cyclosporin A.
    Type: Grant
    Filed: December 20, 2002
    Date of Patent: June 12, 2007
    Assignee: MGI GP, Inc.
    Inventors: George Bonneville, Greg Delahanty, Andrew J. Walz
  • Patent number: 7214811
    Abstract: A derivative of phosphoric acid ester salt or adduct or a mixture thereof is obtained from a reaction product, polycondensed with at least one aldehyde, of at least one polyol phosphoric acid ester with at least one organic nitrogen base. The derivative is advantageously used as a flame-inhibiting and/or intumescent treatment in plastic mouldings, on porous carriers or in paint or coating systems. The production of the derivative or a mixture thereof by reacting at least one polyol with phosphorus pentoxide and reacting the polyol phosphoric acid ester obtained in that way with at least one organic nitrogen base forming a phosphoric acid ester salt or adduct, is characterized in that the amount of phosphorus pentoxide required for the esterification operation is suspended in an amount of the ester or ester mixture to be produced, then at a temperature in the range of 20–180° C.
    Type: Grant
    Filed: February 28, 2002
    Date of Patent: May 8, 2007
    Assignee: Chemische Fabrik Budenheim KG
    Inventors: Karl Götzmann, Thomas Futterer, Hans-Dieter Nägerl, Vincent Mans
  • Patent number: 7135583
    Abstract: A novel process for preparation of alkenylphosphine oxides or alkenylphosphinic acid esters provided by which the objective compounds can be easily, safely and efficiently synthesized and easily separated and purified with little formation of by-products. Specifically, a process of conducting the addition reaction of an easily available secondary phosphine oxide or hydrogen phosphinic acid ester with an acetylene compound with a catalyst containing a Group 9 or 10 metal of the periodic table to thereby obtain the corresponding alkenylphosphine oxide or alkenylphosphinic acid ester.
    Type: Grant
    Filed: February 12, 2002
    Date of Patent: November 14, 2006
    Assignees: Japan Science and Technology Corporation, National Institute of Advanced Industrial Science & Technology
    Inventors: Li-biao Han, Chang-qiu Zhao, Masato Tanaka
  • Patent number: 7018987
    Abstract: The present invention relates to novel water-soluble, stable derivatives of combretastatin A-4, and novel synthesis methods therefore. The combretastatin A-4 prodrugs described herein appear to be useful in the treatment of neoplastic disease.
    Type: Grant
    Filed: January 8, 1999
    Date of Patent: March 28, 2006
    Assignee: Arizona Broad of Regents acting for and on behalf of Arizona State University
    Inventors: George R. Pettit, Monie R. Rhodes
  • Patent number: 6949667
    Abstract: Novel alkenylphosphonic acid esters of the following general formula (I): R1CH?CR2[P(O)(OCR3R4CR5R6O)]??(I) and a simple process for the preparation thereof are provided by the use of secondary cyclic phosphonic acid esters as the starting material.
    Type: Grant
    Filed: December 28, 2000
    Date of Patent: September 27, 2005
    Assignee: National Institute of Advanced Industrial Science and Technology
    Inventors: Li-Biao Han, ChangQiu Zhao, Masato Tanaka
  • Patent number: 6909010
    Abstract: A facile synthesis of symmetric esters of C1-C10 alkylenebisphopsphonic acids is disclosed in which a C1-C10 alkylenebis(phosphonic dichloride) is reacted with an alcohol in the presence of a catalytic amount of 1H-tetrazole and a base in an aprotic solvent to form a first reaction mixture. The first reaction mixture is maintained for a time period sufficient to form a C1-C10 alkylenebis(chloro ester phosphonate) that is reacted under basic conditions with an excess of a hydroxylated compound to form a second reaction mixture that is itself maintained for a time period sufficient to form a C1-C10 alkylenebis(ester phosphonate) partial ester, homoleptic tetraester or mixed tetraester. The material so formed can be recovered or used as is.
    Type: Grant
    Filed: April 5, 2002
    Date of Patent: June 21, 2005
    Assignee: Loyola University of Chicago
    Inventors: Albert W. Herlinger, Dominique C. Stepinski
  • Patent number: 6815558
    Abstract: The invention relates to a process for the preparation of (metal) salts of alkylphosphonous acids, which comprises reacting elemental yellow phosphorus with alkyl halides in the presence of carbonates, bicarbonates, amides, alkoxides, amine bases and/or solid hydroxides as bases. The invention also relates to the use of the (metal) salts of alkylphosphonous acids prepared by this process.
    Type: Grant
    Filed: May 25, 2000
    Date of Patent: November 9, 2004
    Assignee: Clariant GmbH
    Inventor: Norbert Weferling
  • Patent number: 6806383
    Abstract: The invention relates to a process for the preparation of (metal) salts of alkylphosphonous acids, which comprises reacting elemental yellow phosphorus with halogen-free alkylating agents in the presence of at least one base. The invention also relates to the use of the (metal) salts of alkylphosphonous acids prepared by this process.
    Type: Grant
    Filed: May 25, 2000
    Date of Patent: October 19, 2004
    Assignee: Clariant GmbH
    Inventors: Norbert Weferling, Martin Sicken
  • Patent number: 6790928
    Abstract: 100 parts by weight of the polycarbonate produce by melt polycondensation of a carbonic acid diester and a dihydroxy compound and 0.0001 to 0.1 part by weight of a phosphite compound represented by following Formula (I) are formulated: wherein Rs are each one of a hydrogen atom, an alkyl group, an aryl group, and an oxyalkyl group, where the two Rs are not concurrently hydrogen atoms. The process of the invention can yield polycarbonate molding materials that have satisfactory hue and can be used in a wide variety of applications such for optical materials.
    Type: Grant
    Filed: March 18, 2003
    Date of Patent: September 14, 2004
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Shu Yoshida, Hiroaki Tanaka
  • Patent number: 6770779
    Abstract: The present invention relates to a process for the preparation of alkylphosphonous acid esters which comprises a) reacting elemental yellow phosphorus with alkylating agents in the presence of a base to give a mixture which comprises, as principal constituents, the (metal) salts of alkylphosphonous, phosphorous and hypophosphorous acids, b) esterifying the principal constituents of the mixture from a) to give an ester mixture, c) isolating the ester of the alkylphosphonous acid from the ester mixture. The invention likewise relates to the use of the alkylphosphonous acid esters prepared by this process as precursors for further syntheses, inter alia for the preparation of crop protection agents.
    Type: Grant
    Filed: May 24, 2000
    Date of Patent: August 3, 2004
    Assignee: Clariant GmbH
    Inventors: Norbert Weferling, Martin Sicken, Hans-Peter Schmitz, Günter Kolbe
  • Patent number: 6767927
    Abstract: Stable rare earth tris (organophosphate) solutions comprise a rare earth tris (organophosphate) and a hydrocarbon solvent. From about 2% to about 10% rare earth element, preferably from about 3% to about 8%, is present in the solutions. The rare earth tris (organophosphate) solutions are stable from precipitation of the rare earth tris (organophosphate) for at least about fifteen (15) days, preferably for at least about twenty (20) days and most preferably at least about thirty (30) days. A process for preparing these solutions is described herein. A stabilizing additive, acid, glycol or mixtures thereof, is utilized to inhibit precipitation. The molar ratios of free acid, glycol and/or water to the rare earth element are controlled to inhibit precipitation.
    Type: Grant
    Filed: April 25, 2000
    Date of Patent: July 27, 2004
    Assignee: Rhodia Rare Earths Inc.
    Inventors: Kenan Yunlu, Min He
  • Publication number: 20040059146
    Abstract: A novel process for preparation of alkenylphosphine oxides or alkenylphosphinic acid esters provided by which the objective compounds can be easily, safely and efficiently synthesized and easily separated and purified with little formation of by-products. Specifically, a process of conducting the addition reaction of an easily available secondary phosphine oxide or hydrogen phosphinic acid ester with an acetylene compound with a catalyst containing a Group 9 or 10 metal of the periodic table to thereby obtain the corresponding alkenylphosphine oxide or alkenylphosphinic acid ester.
    Type: Application
    Filed: August 8, 2003
    Publication date: March 25, 2004
    Inventors: Li-biao Han, Chang-qiu Zhao, Masato Tanaka
  • Publication number: 20030105345
    Abstract: The present invention relates to a new manufacturing method for phosphonate esters, which have utility as a carbon-carbon binding formation agent, as well as a synthesis intermediate for biologically active substances such as medical drugs and agri-chemicals.
    Type: Application
    Filed: July 30, 2002
    Publication date: June 5, 2003
    Inventors: Li-Biao Han, Farzad Mirzaei, Masato Tanaka
  • Patent number: 6566545
    Abstract: The present invention provides a menthol derivative represented by the following Formula 1 and a method for preparing the menthol derivative. The menthol derivative represented by the Formula 1 is prepared by reacting menthol and phosphorous oxychloride with an equivalence ratio of 1:1˜1.3 in an organic solvent in the presence of organic base to obtain dichloro[5-methyl-2(mehtylethyl)cylclohexyloxy]phosphino-1-one; and reacting above obtained dichloro[5-methyl-2(mehtylethyl)cylclohexyloxy]phosphino-1-one with 3-amino propanol in the organic solvent in the presence of the organic; then hydrolyzing and crystallizing the product with polar organic solvent.
    Type: Grant
    Filed: August 23, 2002
    Date of Patent: May 20, 2003
    Assignee: Pacific Corporation
    Inventors: Jae Won Yoo, Duck Hee Kim, Seong Joon Moon, Min Soo Noh, Soo Hyun Kim, Su Sun An, Jin Seon Lee
  • Publication number: 20020119951
    Abstract: Methods of synthesizing a phosphate ester of combretastat-in A-4 and trans-isomers thereof in which combretastatin A-4 is reacted with dibenzylphosphite in the presence of carbon tetrabromide, or with 2,2,2-trichloroethyl phosphorodichloridate, to form a phosphate ester of combretastatin A-4 with protecting groups thereon.
    Type: Application
    Filed: July 17, 2001
    Publication date: August 29, 2002
    Inventors: Faye Seyedi, Jonathan Gale, Reem Haider, John Hoare, Amy Baldwin
  • Patent number: 6417383
    Abstract: The present invention relates to novel cyclotriphosphazene derivatives represented by Formula (1) and a preparation method thereof wherein HNA is an amino acid group selected from glycine group(—NHCH2COO−), aminomalonic acid group(—NHCH(COO−)2), aspartic acid group (—NHCH(CH2COO−)COO−) and glutamic acid group (—NHCH(CH2CH2COO−)COO−), m is a repeating unit of poly(alkoxyethyleneglycol) selected from 2, 7, 12 and 16, and n is an integer representing number of alkyl carbons and selected from 0, 1, and 3.
    Type: Grant
    Filed: July 5, 2001
    Date of Patent: July 9, 2002
    Assignee: Korea Institute of Science and Technology
    Inventors: Youn Soo Sohn, Soo-Chang Song, Sang Beom Lee
  • Patent number: 6359171
    Abstract: The invention relates to a process for the preparation of dialkylphosphinic acids and salts thereof, which comprises a) reacting elemental yellow phosphorus with alkylating agents in the presence of a base to give a mixture which comprises, as principal constituents, the (metal) salts of alkylphosphonous, phosphorous and hypophosphorous acids, b) esterifying the principal constituents of the mixture from a) to give an ester mixture, c) isolating the ester of the alkylphosphonous acid from the ester mixture, d) preparing the corresponding ester of the dialkylphosphinic acid from the ester of the alkylphosphonous acid by free-radical-initiated reaction with olefins, e) converting the ester of the dialkylphosphinic acid into the free acid or into the dialkylphosphinic acid salts of metals from groups IA, IIA, IIIA, IVA, VA, IIB, IVB, VIIB or VIIIB of the Periodic Table or of cerium.
    Type: Grant
    Filed: May 24, 2000
    Date of Patent: March 19, 2002
    Assignee: Clariant GmbH
    Inventors: Norbert Weferling, Martin Sicken, Günter Kolbe, Hans-Peter Schmitz
  • Patent number: 5650502
    Abstract: Disclosed are ribozyme analogs having the ability to endonucleolytically cleave a sequence of 3' to 5' linked ribonucleotides. The ribozyme analogs include a plurality of 3' to 5' covalently-linked nucleotides, and a rigid molecular linker having at least one non-nucleotidic molecule covalently linked to two of the nucleotides. Also disclosed are methods of preparing and utilizing the ribozyme analogs of the invention, and pharmaceutical formulations and kits containing such ribozyme analogs.
    Type: Grant
    Filed: November 9, 1994
    Date of Patent: July 22, 1997
    Assignee: Hybridon, Inc.
    Inventors: John Goodchild, Thomas E. Leonard
  • Patent number: 5618803
    Abstract: The invention provides compounds of the formula ##STR1## or a pharmaceutically acceptable salt thereof, wherein [D] is the residue of a drug having a reactive functional group, said functional group being attached, directly or through a bridging group, via an oxygen-phosphorus bond to the phosphorus atom of the ##STR2## moiety; R.sub.1 is C.sub.1 -C.sub.8 alkyl, C.sub.6 -C.sub.10 aryl or C.sub.7 -C.sub.12 aralkyl; R.sub.2 is hydrogen, C.sub.1 -C.sub.8 alkyl, C.sub.6 -C.sub.10 aryl, C.sub.4 -C.sub.9 heteroaryl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.3 -C.sub.7 cycloheteroalkyl or C.sub.7 -C.sub.12 aralkyl; and R.sub.3 is selected from the group consisting of C.sub.1 -C.sub.8 alkyl; C.sub.2 -C.sub.8 alkenyl having one or two double bonds; (C.sub.3 -C.sub.7 cycloalkyl)-C.sub.r H.sub.2r -- wherein r is zero, one, two or three, the cycloalkyl portion being unsubstituted or bearing 1 or 2 C.sub.1 -C.sub.4 alkyl substituents on the ring portion; (C.sub.6 -C.sub.10 aryloxy)C.sub.1 -C.sub.
    Type: Grant
    Filed: November 15, 1994
    Date of Patent: April 8, 1997
    Assignee: University of Florida
    Inventor: Nicholas S. Bodor
  • Patent number: 5581006
    Abstract: A convergent synthesis of 19-nor-vitamin D compounds, specifically 19-nor-1.alpha.,25-dihydroxyvitamin D.sub.3, is disclosed. The synthesis can also readily be utilized for preparing other 1.alpha.-hydroxylated 19-nor-vitamin D compounds. The key step in the synthesis is a suitable application of Lythgoe's procedure i.e. a Horner-Wittig reaction of the lithium anion of a phosphine oxide with a Windaus Grundmann ketone to give, after any necessary deprotection, the desired 19-nor-vitamin D compound.
    Type: Grant
    Filed: May 16, 1995
    Date of Patent: December 3, 1996
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Hector F. DeLuca, Heinrich K. Schnoes, Kato L. Perlman, Rolf E. Swenson
  • Patent number: 5565440
    Abstract: The present invention discloses a methane diphosphonate derivative, a process for producing said derivative and its pharmaceutical applications, said methane diphosphonate derivative indicated with general formula (1): ##STR1## (wherein, R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are independently a pharmacologically acceptable cation, a hydrogen atom or a straight chain or branched alkyl group having 1-4 carbon atoms, R.sub.5 is a hydrogen atom or a trialkylsilyl group, m is an integer of 0 to 3, n is an integer of 1 to 3, R.sub.6 and R.sub.7 are independently a hydrogen atom or an alkyl group, and X represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group or an alkylthio group).
    Type: Grant
    Filed: June 28, 1994
    Date of Patent: October 15, 1996
    Assignee: Toray Industries, Inc.
    Inventors: Keijiro Takanishi, Norio Kawabe, Teruo Nakadate
  • Patent number: 5498740
    Abstract: Compositions which, in the form of aqueous dispersions or of solutions in organic solvents, are suitable for the treatment of fiber materials can be obtained by reaction of organic phosphites and quinones and subsequent reaction with mono-, di- or polyisocyanates. Flame-retardant properties having a good permanence are imparted, above all, to fabrics comprising polyester fibers by this procedure.
    Type: Grant
    Filed: March 5, 1993
    Date of Patent: March 12, 1996
    Assignee: Ciba-Geigy Corporation
    Inventors: Salman Dermeik, Martina Wanner, Karl-Heinz Lemmer, Reinhold Braun
  • Patent number: 5478960
    Abstract: Heterosubstituted acetals of the formula ##STR1## can be obtained by reacting vinyl compounds of the formulaCH.sub.2 .dbd.CH-A.sup.1 (II)with alkyl nitrites of the formulaR.sup.1 --ONO (III.)The reaction is performed in the presence of palladium in metallic or bonded form and in alcohols or ethers as reaction medium at from 0.degree. to 120.degree. C.
    Type: Grant
    Filed: March 22, 1995
    Date of Patent: December 26, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventors: Heinz Landscheidt, Alexander Klausener
  • Patent number: 5166385
    Abstract: Process for the preparation of phosphino compounds Phosphorus-containing compounds of the formula (I)(R.sup.1)(R.sup.2)P(O)--CR.sup.3 R.sup.4 --CHR.sup.5 R.sup.6 (I)in whichR.sup.1 and R.sup.2 are alkyl, alkoxy or optionally substituted phenyl,R.sup.3 and R.sup.5 are H, R, optionally substituted phenyl, ROCO--, RO--CO--RO--, halogen, CN, RO--, RO--RO--R-CO--, H.sub.2 NCO--, RNHCO-- or RRNCO--, in which R is alkyl,R.sup.4 and R.sup.6 have the same meaning as defined for R.sup.1 and R.sup.2 or are a divalent radical--CO--R.sup.7 --COin whichR.sup.7 is oxygen, NR* or sulfur, and R* is H, optionally substituted phenyl or alkyl,are precursors for plant protection agents and fire retardants. According to the invention they can be prepared in high yields and high purity by reacting a compound (R.sup.1)(R.sup.2)P--OR.sup.8, in which R.sup.8 is alkyl or optionally substituted phenyl, with an alkene of the formula R.sup.3 R.sup.4 C.dbd.CR.sup.5 R.sup.
    Type: Grant
    Filed: November 25, 1991
    Date of Patent: November 24, 1992
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gunter Scheffel, Stephen Lachhein
  • Patent number: 5151539
    Abstract: Glycol bisphosphate compounds are formed by first hydrolytically condensing a dihydrocarbylhalophosphate to form a tetrahydrocarbyl pyrophosphate and then reacting the pyrophosphate with a cyclic ether to form the glycol bisphosphate.
    Type: Grant
    Filed: May 28, 1991
    Date of Patent: September 29, 1992
    Assignee: Akzo America Inc.
    Inventors: Danielle A. Bright, Alan M. Aaronson