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WO2001014576A3 - Process and intermediates for the preparation of isoxazolecaroxamides and analogues - Google Patents

Process and intermediates for the preparation of isoxazolecaroxamides and analogues Download PDF

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Publication number
WO2001014576A3
WO2001014576A3 PCT/US2000/023032 US0023032W WO0114576A3 WO 2001014576 A3 WO2001014576 A3 WO 2001014576A3 US 0023032 W US0023032 W US 0023032W WO 0114576 A3 WO0114576 A3 WO 0114576A3
Authority
WO
WIPO (PCT)
Prior art keywords
preparation
synthetic routes
isoxazolecaroxamides
analogues
intermediates
Prior art date
Application number
PCT/US2000/023032
Other languages
French (fr)
Other versions
WO2001014576A2 (en
WO2001014576A8 (en
WO2001014576B1 (en
Inventor
Junhua Tao
Srinivasan Babu
Raymond Dagnino Jr
Qingping Tian
Travis Paul Remarchuk
Kevin Scott Mcgee
Naresh K Nayyar
Terence Jarold Moran
Original Assignee
Agouron Pharma
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to JP2001518887A priority Critical patent/JP2003511350A/en
Priority to IL14786200A priority patent/IL147862A0/en
Priority to HU0203315A priority patent/HUP0203315A3/en
Priority to AU67970/00A priority patent/AU778062B2/en
Priority to CA002376509A priority patent/CA2376509A1/en
Priority to KR1020027002323A priority patent/KR20020030795A/en
Priority to BR0013323-0A priority patent/BR0013323A/en
Priority to EP00955830A priority patent/EP1206470A2/en
Application filed by Agouron Pharma filed Critical Agouron Pharma
Priority to MXPA02001947A priority patent/MXPA02001947A/en
Publication of WO2001014576A2 publication Critical patent/WO2001014576A2/en
Publication of WO2001014576A3 publication Critical patent/WO2001014576A3/en
Publication of WO2001014576B1 publication Critical patent/WO2001014576B1/en
Publication of WO2001014576A8 publication Critical patent/WO2001014576A8/en
Priority to HK03103445A priority patent/HK1051363A1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/24—Stationary reactors without moving elements inside
    • B01J19/2415—Tubular reactors
    • B01J19/2435—Loop-type reactors
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/24—Stationary reactors without moving elements inside
    • B01J19/2475—Membrane reactors
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/34—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/26—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids
    • C07C303/28—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids by reaction of hydroxy compounds with sulfonic acids or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
    • C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D261/18—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00002—Chemical plants
    • B01J2219/00027—Process aspects
    • B01J2219/00033—Continuous processes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00049—Controlling or regulating processes
    • B01J2219/00051—Controlling the temperature
    • B01J2219/00074—Controlling the temperature by indirect heating or cooling employing heat exchange fluids
    • B01J2219/00087—Controlling the temperature by indirect heating or cooling employing heat exchange fluids with heat exchange elements outside the reactor
    • B01J2219/00099—Controlling the temperature by indirect heating or cooling employing heat exchange fluids with heat exchange elements outside the reactor the reactor being immersed in the heat exchange medium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00049—Controlling or regulating processes
    • B01J2219/00051—Controlling the temperature
    • B01J2219/00074—Controlling the temperature by indirect heating or cooling employing heat exchange fluids
    • B01J2219/00087—Controlling the temperature by indirect heating or cooling employing heat exchange fluids with heat exchange elements outside the reactor
    • B01J2219/00103—Controlling the temperature by indirect heating or cooling employing heat exchange fluids with heat exchange elements outside the reactor in a heat exchanger separate from the reactor
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00049—Controlling or regulating processes
    • B01J2219/00051—Controlling the temperature
    • B01J2219/00159—Controlling the temperature controlling multiple zones along the direction of flow, e.g. pre-heating and after-cooling
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00049—Controlling or regulating processes
    • B01J2219/00162—Controlling or regulating processes controlling the pressure
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00049—Controlling or regulating processes
    • B01J2219/00177—Controlling or regulating processes controlling the pH
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Virology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Communicable Diseases (AREA)
  • Molecular Biology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Oncology (AREA)
  • Veterinary Medicine (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyrrole Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Enzymes And Modification Thereof (AREA)

Abstract

Efficient synthetic routes for the preparation of rhinovirus protease inhibitors of formula (I), particulary (I'), key intermediates useful in those synthetic routes, as well as a continuous membrane reactor useful for those synthetic routes. These compounds of formula (I), as well as pharmaceutical compositions that contain these compounds, are suitable for treating patients or hosts infected with one or more picornaviruses.
PCT/US2000/023032 1999-08-24 2000-08-23 Process and intermediates for the preparation of isoxazolecaroxamides and analogues WO2001014576A2 (en)

Priority Applications (10)

Application Number Priority Date Filing Date Title
BR0013323-0A BR0013323A (en) 1999-08-24 2000-08-23 Useful processes for the preparation of antipicornaviral agents, processes useful for the preparation of a compound, compounds, processes for the preparation of a compound and processes for carrying out a reaction catalyzed by a large catalyst
HU0203315A HUP0203315A3 (en) 1999-08-24 2000-08-23 Process and intermediates for the preparation of isoxazolecaroxamides and analogues
AU67970/00A AU778062B2 (en) 1999-08-24 2000-08-23 Process and intermediates for the preparation of isoxazolecaroxamides and analogues
CA002376509A CA2376509A1 (en) 1999-08-24 2000-08-23 Process and intermediates for the preparation of isoxazolecaroxamides and analogues
KR1020027002323A KR20020030795A (en) 1999-08-24 2000-08-23 Process and Intermediates for the Preparation of Isoxazolecaroxamides and Analogues
JP2001518887A JP2003511350A (en) 1999-08-24 2000-08-23 Process for preparing isoxazole carboxamides and analogs and intermediates
EP00955830A EP1206470A2 (en) 1999-08-24 2000-08-23 Processes and intermediates for the preparation of isoxazolecarboxamides and analogues
IL14786200A IL147862A0 (en) 1999-08-24 2000-08-23 Process and intermediates for the preparation os isoxazolecaroxamides and analogues
MXPA02001947A MXPA02001947A (en) 1999-08-24 2000-08-23 Process and intermediates for the preparation of isoxazolecaroxamides and analogues.
HK03103445A HK1051363A1 (en) 1999-08-24 2003-05-15 Efficient methods for the preparation of rhinovirus protease inhibitors, key intermediates and a continuous membrane reactor useful for preparing the same.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US15036599P 1999-08-24 1999-08-24
US60/150,365 1999-08-24

Publications (4)

Publication Number Publication Date
WO2001014576A2 WO2001014576A2 (en) 2001-03-01
WO2001014576A3 true WO2001014576A3 (en) 2001-08-30
WO2001014576B1 WO2001014576B1 (en) 2001-09-27
WO2001014576A8 WO2001014576A8 (en) 2002-06-20

Family

ID=22534191

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2000/023032 WO2001014576A2 (en) 1999-08-24 2000-08-23 Process and intermediates for the preparation of isoxazolecaroxamides and analogues

Country Status (15)

Country Link
EP (1) EP1206470A2 (en)
JP (1) JP2003511350A (en)
KR (1) KR20020030795A (en)
CN (2) CN1524960A (en)
AU (1) AU778062B2 (en)
BR (1) BR0013323A (en)
CA (1) CA2376509A1 (en)
CZ (1) CZ2002634A3 (en)
HK (1) HK1051363A1 (en)
HU (1) HUP0203315A3 (en)
IL (1) IL147862A0 (en)
MX (1) MXPA02001947A (en)
PL (1) PL357162A1 (en)
WO (1) WO2001014576A2 (en)
ZA (1) ZA200200506B (en)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TR200003159T2 (en) 1998-04-30 2001-09-21 Agouron Pharmaceuticals,Inc. Antipicornaviral compounds, their preparation and uses
BR0012970A (en) 1999-08-04 2002-04-30 Agouron Pharma Antipicornaviral compounds and compositions, their pharmaceutical uses and materials for their synthesis
US6774243B2 (en) 1999-08-24 2004-08-10 Agouron Pharmaceuticals, Inc. Efficient synthetic routes for the preparation of rhinovirus protease inhibitors and key intermediates
PA8507801A1 (en) 1999-12-03 2002-08-26 Agouron Pharma ANTIPICORNAVIRAL COMPOUNDS AND COMPOSITIONS, THEIR PHARMACEUTICAL USES AND THE MATERIALS FOR SYNTHESIS
PE20011277A1 (en) 2000-04-14 2002-01-07 Agouron Pharma ANTIPICORNAVIRAL COMPOUNDS AND COMPOSITIONS, THEIR PHARMACEUTICAL USES AND THE MATERIALS FOR THEIR SYNTHESIS
JP2004503533A (en) 2000-06-14 2004-02-05 アグロン・ファーマシュウティカルズ・インコーポレーテッド Anti-picornavirus compounds and compositions, their pharmaceutical use, and substances for their synthesis
DE10208007A1 (en) * 2002-02-26 2003-09-18 Forschungszentrum Juelich Gmbh Process for the production of alcohols from substrates by means of oxidoreductases, two-phase system comprising an aqueous phase and an organic phase and device for carrying out the process
CN106831657B (en) * 2017-02-23 2019-07-16 江苏工程职业技术学院 A kind of preparation method of glycidic acid potassium

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2426651A1 (en) * 1974-06-01 1975-12-11 Bayer Ag Laevorotatory 3-aryl-2-halo-propionic acid derivs - prepd e.g. by optical resolution of the racemic 2-hydroxy-acids, esterification, and halogenation
US4326031A (en) * 1979-07-25 1982-04-20 Degussa Ag Process for the continuous enzymatic change of water soluble α-ketocarboxylic acids into the corresponding α-hydroxycarboxylic acids
JPS6143136A (en) * 1984-08-07 1986-03-01 Mitsui Toatsu Chem Inc Production of alkali metal salt of alpha-keto acid
JPS62212329A (en) * 1986-03-14 1987-09-18 Sankyo Co Ltd Production of alpha-hydroxycarboxylic acid derivative
FR2686897A1 (en) * 1992-02-05 1993-08-06 Sonertec Process for the continuous manufacture of organic acids
US5360927A (en) * 1994-01-24 1994-11-01 Development Center For Biotechnology Process for the preparation of monohydrated sodium phenylpyruvate
US5869697A (en) * 1994-05-02 1999-02-09 Council Of Scientific & Industrial Research Process for preparing diltiazem

Patent Citations (7)

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DE2426651A1 (en) * 1974-06-01 1975-12-11 Bayer Ag Laevorotatory 3-aryl-2-halo-propionic acid derivs - prepd e.g. by optical resolution of the racemic 2-hydroxy-acids, esterification, and halogenation
US4326031A (en) * 1979-07-25 1982-04-20 Degussa Ag Process for the continuous enzymatic change of water soluble α-ketocarboxylic acids into the corresponding α-hydroxycarboxylic acids
JPS6143136A (en) * 1984-08-07 1986-03-01 Mitsui Toatsu Chem Inc Production of alkali metal salt of alpha-keto acid
JPS62212329A (en) * 1986-03-14 1987-09-18 Sankyo Co Ltd Production of alpha-hydroxycarboxylic acid derivative
FR2686897A1 (en) * 1992-02-05 1993-08-06 Sonertec Process for the continuous manufacture of organic acids
US5360927A (en) * 1994-01-24 1994-11-01 Development Center For Biotechnology Process for the preparation of monohydrated sodium phenylpyruvate
US5869697A (en) * 1994-05-02 1999-02-09 Council Of Scientific & Industrial Research Process for preparing diltiazem

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DRAGOVICH P S ET AL: "Structure-based design, synthesis, and biological evaluation of irreversible human rhinovirus 3C protease inhibitors. 3. Structure-activity studies of ketomethylene-containing peptidomimetics", JOURNAL OF MEDICINAL CHEMISTRY, vol. 42, no. 7, 8 April 1999 (1999-04-08), pages 1203 - 1212, XP002153927 *
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SHAW J P ET AL: "Selective bromination of alpha-chloro and alpha-bromo carboxylic acid derivatives", JOURNAL OF ORGANIC CHEMISTRY, vol. 61, no. 16, 9 August 1996 (1996-08-09), pages 5635 - 5637, XP002153923 *
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THEODORIDIS G ET AL: "A new approach to the synthesis of substituted 2(1H)-quinolinones", JOURNAL OF HETEROCYCLIC CHEMISTRY, vol. 28, 1 June 1991 (1991-06-01), pages 849 - 852, XP002046545, ISSN: 0022-152X *
WOO G-J ET AL: "Maltotetraose production using Pseudomonas stutzeri exo-alpha-amylase in a membrane recycle bioreactor", JOURNAL OF FOOD SCIENCE, vol. 56, no. 4, 1991, pages 1019 - 1023, 1033, XP002161549 *

Also Published As

Publication number Publication date
AU778062B2 (en) 2004-11-11
IL147862A0 (en) 2002-08-14
WO2001014576A2 (en) 2001-03-01
EP1206470A2 (en) 2002-05-22
CN1524960A (en) 2004-09-01
HK1051363A1 (en) 2003-08-01
CZ2002634A3 (en) 2002-09-11
CN1382139A (en) 2002-11-27
PL357162A1 (en) 2004-07-26
WO2001014576A8 (en) 2002-06-20
BR0013323A (en) 2002-04-02
HUP0203315A2 (en) 2003-02-28
CA2376509A1 (en) 2001-03-01
AU6797000A (en) 2001-03-19
CN1157391C (en) 2004-07-14
KR20020030795A (en) 2002-04-25
MXPA02001947A (en) 2002-10-31
WO2001014576B1 (en) 2001-09-27
HUP0203315A3 (en) 2003-12-29
ZA200200506B (en) 2003-06-25
JP2003511350A (en) 2003-03-25

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