WO2003093302A3 - Process for the synthesis of peptides amides by side-chain attachement to a solid phase - Google Patents

Process for the synthesis of peptides amides by side-chain attachement to a solid phase Download PDF

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Publication number
WO2003093302A3
WO2003093302A3 PCT/GB2003/001949 GB0301949W WO03093302A3 WO 2003093302 A3 WO2003093302 A3 WO 2003093302A3 GB 0301949 W GB0301949 W GB 0301949W WO 03093302 A3 WO03093302 A3 WO 03093302A3
Authority
WO
WIPO (PCT)
Prior art keywords
chain
synthesis
attachement
solid phase
amides
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/GB2003/001949
Other languages
French (fr)
Other versions
WO2003093302A2 (en
Inventor
David John Evans
Dean Steven Anthony Simpkin
Donald Alfred Wellings
Eric Atherton
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Avecia Ltd
Original Assignee
Avecia Ltd
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 claimed from GB0210185A external-priority patent/GB0210185D0/en
Priority claimed from GBGB0210183.0A external-priority patent/GB0210183D0/en
Priority claimed from GB0210184A external-priority patent/GB0210184D0/en
Priority to US10/513,285 priority Critical patent/US7691968B2/en
Priority to EP03725369A priority patent/EP1504022B1/en
Priority to JP2004501441A priority patent/JP2006501150A/en
Application filed by Avecia Ltd filed Critical Avecia Ltd
Priority to DE60309019T priority patent/DE60309019T2/en
Priority to MXPA04010910A priority patent/MXPA04010910A/en
Priority to CA2484594A priority patent/CA2484594C/en
Priority to AU2003227907A priority patent/AU2003227907A1/en
Publication of WO2003093302A2 publication Critical patent/WO2003093302A2/en
Publication of WO2003093302A3 publication Critical patent/WO2003093302A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
    • 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
    • C07C271/20—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 nitrogen atoms not being part of nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C279/04—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton
    • C07C279/14—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton being further substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/60—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D209/20—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals substituted additionally by nitrogen atoms, e.g. tryptophane
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
    • C07K1/003—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by transforming the C-terminal amino acid to amides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • C07K14/745—Blood coagulation or fibrinolysis factors
    • C07K14/75—Fibrinogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
    • C07K7/04—Linear peptides containing only normal peptide links
    • C07K7/06—Linear peptides containing only normal peptide links having 5 to 11 amino acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
    • C07C2603/18—Fluorenes; Hydrogenated fluorenes
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Biophysics (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Medicinal Chemistry (AREA)
  • Biochemistry (AREA)
  • Analytical Chemistry (AREA)
  • Hematology (AREA)
  • Toxicology (AREA)
  • Zoology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Peptides Or Proteins (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

A process is provided for the solid-phase synthesis of a peptide amide which comprises attaching a α-nitrogen protected Cα-carboxamide amino acid to a solid support by its side chain, removing the α-nitrogen protecting group, assembling a peptide chain on said α-nitrogen and then cleaving the assembled peptide amide from the solid support. Novel amino acid analogues, peptide amides and solid-phase supports are also provided.
PCT/GB2003/001949 2002-05-03 2003-05-02 Process for the synthesis of peptides amides by side-chain attachement to a solid phase Ceased WO2003093302A2 (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
AU2003227907A AU2003227907A1 (en) 2002-05-03 2003-05-02 Process for the synthesis of peptides amides by side-chain attachement to a solid phase
CA2484594A CA2484594C (en) 2002-05-03 2003-05-02 Process for the synthesis of peptides
MXPA04010910A MXPA04010910A (en) 2002-05-03 2003-05-02 Process for the synthesis of peptides.
EP03725369A EP1504022B1 (en) 2002-05-03 2003-05-02 Process for the synthesis of peptide amides by side-chain attachment to a solid phase
JP2004501441A JP2006501150A (en) 2002-05-03 2003-05-02 Process for peptide synthesis
US10/513,285 US7691968B2 (en) 2002-05-03 2003-05-02 Process for the synthesis of peptides amides by side-chain attachment to a solid phase
DE60309019T DE60309019T2 (en) 2002-05-03 2003-05-02 METHOD FOR THE PRODUCTION OF PEPTIDAMIDES BY SIDE-CHAIN TAPPING ON A SOLID PHASE

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
GB0210185.5 2002-05-03
GB0210185A GB0210185D0 (en) 2002-05-03 2002-05-03 Process
GB0210183.0 2002-05-03
GB0210184.8 2002-05-03
GB0210184A GB0210184D0 (en) 2002-05-03 2002-05-03 Process
GBGB0210183.0A GB0210183D0 (en) 2002-05-03 2002-05-03 Process

Publications (2)

Publication Number Publication Date
WO2003093302A2 WO2003093302A2 (en) 2003-11-13
WO2003093302A3 true WO2003093302A3 (en) 2004-01-08

Family

ID=29407323

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB2003/001949 Ceased WO2003093302A2 (en) 2002-05-03 2003-05-02 Process for the synthesis of peptides amides by side-chain attachement to a solid phase

Country Status (9)

Country Link
US (1) US7691968B2 (en)
EP (1) EP1504022B1 (en)
JP (1) JP2006501150A (en)
AT (1) ATE342273T1 (en)
AU (1) AU2003227907A1 (en)
CA (1) CA2484594C (en)
DE (1) DE60309019T2 (en)
MX (1) MXPA04010910A (en)
WO (1) WO2003093302A2 (en)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PT2204383E (en) * 2004-04-08 2011-10-31 Millennium Pharm Inc Processes for preparing eptifibatide and pertinent intermediate compounds
AU2004320599A1 (en) * 2004-06-14 2005-12-22 Usv Limited Process for the preparation of peptides
US7897724B2 (en) * 2004-10-10 2011-03-01 Usv, Ltd. Solid phase Fmoc chemistry process to prepare peptides
CN101094867B (en) 2004-10-19 2011-08-24 隆萨股份公司 Method for solid phase peptide synthesis
DE602005018952D1 (en) * 2004-10-19 2010-03-04 Lonza Ag PEPTIDE CYCLISING ON RESIN
ES2336826T3 (en) * 2005-05-03 2010-04-16 Novetide, Ltd. PROCEDURES FOR THE PRODUCTION OF A PEPTIDE THAT PRESENTS A C-TERMINAL AMIDA.
CN1858060B (en) * 2005-05-08 2010-09-29 周达明 Preparation method of solid-phase polypeptide synthesis effibat
NL2000126C2 (en) * 2005-07-15 2008-01-29 Solvay Process for the manufacture of eptifibatide.
EP2074134A1 (en) * 2006-10-05 2009-07-01 Lonza Ag Method for peptide synthesis
US8815807B2 (en) 2008-06-03 2014-08-26 President And Fellows Of Harvard College Peptides and peptide compositions having osteoinductive activity
WO2009150657A1 (en) * 2008-06-09 2009-12-17 Natco Pharma Limited Improved process for preparation of eptifibatide by fmoc solid phase synthesis
CN105102427B (en) 2013-03-21 2018-09-07 赛诺菲-安万特德国有限公司 Synthesis of Peptide Products Containing Cyclic Imides
HUE034308T2 (en) 2013-03-21 2018-02-28 Sanofi Aventis Deutschland Synthesis of hydantoin containing peptide products
GB201310921D0 (en) * 2013-06-19 2013-07-31 Chemical & Biopharmaceutical Lab Of Patras S A Peptide-resin conjugate and use thereof
GB201315335D0 (en) 2013-08-29 2013-10-09 Of Singapore Amino diacids containing peptide modifiers
EP3239169B1 (en) * 2014-12-26 2024-04-17 BGI Agricultural and Circular Economic Tech Co., Ltd. Conotoxin peptide -cptx-btl05, preparation method therefor, and uses thereof
CN110498834A (en) * 2018-05-16 2019-11-26 深圳翰宇药业股份有限公司 A kind of method of eptifibatide solid phase preparation

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1990015620A1 (en) * 1989-06-16 1990-12-27 Cor Therapeutics, Inc. Platelet aggregation inhibitors
WO2000026262A2 (en) * 1998-11-05 2000-05-11 Mitokor Functionalized polymeric substrates for binding molecular moieties

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4033940A (en) 1975-11-12 1977-07-05 Armour Pharmaceutical Company Cyclization of peptides
US5807828A (en) 1989-06-16 1998-09-15 Cor Therapeutics, Inc. Platelet aggregation inhibitors
GB9112825D0 (en) 1991-06-14 1991-07-31 Ici Plc Process for making peptides
US6008058A (en) 1993-06-18 1999-12-28 University Of Louisville Cyclic peptide mixtures via side chain or backbone attachment and solid phase synthesis
GB9313330D0 (en) 1993-06-28 1993-08-11 Fujisawa Pharmaceutical Co New compound and its preparation
US7312358B2 (en) * 2000-10-17 2007-12-25 Laboratoires Serono Sa Pharmaceutically active sulfanilide derivatives

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1990015620A1 (en) * 1989-06-16 1990-12-27 Cor Therapeutics, Inc. Platelet aggregation inhibitors
US5318899A (en) * 1989-06-16 1994-06-07 Cor Therapeutics, Inc. Platelet aggregation inhibitors
WO2000026262A2 (en) * 1998-11-05 2000-05-11 Mitokor Functionalized polymeric substrates for binding molecular moieties

Non-Patent Citations (9)

* Cited by examiner, † Cited by third party
Title
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; BUI, CHINH T. ET AL: "Solid phase synthesis of C-terminal peptide amides: development of a new aminoethyl-polystyrene linker on the multipin solid support", XP002259357, retrieved from STN Database accession no. 133:164315 CA *
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; DELAET, N. G. J. ET AL: "Convenient solid phase synthesis method for the preparation of cysteine C-terminally derivatized peptides", XP002259358, retrieved from STN Database accession no. 124:317846 CA *
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; KOMINAMI, GORO ET AL: "A highly specific and sensitive radioimmunoassay of caerulein, an analog of cholecystokinin-8", XP002259359, retrieved from STN Database accession no. 110:88774 CA *
G LIU ET AL.: "Solid-phase synthesis of muramyl dipeptide (MDP) derivatives using a multipin method", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 10, no. 19, 2000, OXFORD, GB, pages 1361 - 1363, XP004207005, ISSN: 0960-894X *
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Z YAO ET AL.: "Preparation of L-N-alpha-FMOC-4-[di-(tert-butyl)-phosphonomethyl]phenylalanine from L-tyrosine", TETRAHEDRON: ASYMMETRY., vol. 10, 1999, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM., NL, pages 3727 - 3734, XP002259356, ISSN: 0957-4166 *
Z YAO ET AL.: "Synthesis of FMOC-protected 4-carboxydifluoromethyl-L-phenylalanine: a phosphotyrosylmimetic of potential use for signal transduction studies", TETRAHEDRON., vol. 55, 1999, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM., NL, pages 2865 - 2874, XP004157124, ISSN: 0040-4020 *

Also Published As

Publication number Publication date
US7691968B2 (en) 2010-04-06
EP1504022B1 (en) 2006-10-11
JP2006501150A (en) 2006-01-12
EP1504022A2 (en) 2005-02-09
CA2484594C (en) 2012-06-26
US20050266520A1 (en) 2005-12-01
DE60309019D1 (en) 2006-11-23
DE60309019T2 (en) 2007-05-16
AU2003227907A1 (en) 2003-11-17
ATE342273T1 (en) 2006-11-15
AU2003227907A8 (en) 2003-11-17
MXPA04010910A (en) 2005-01-25
CA2484594A1 (en) 2003-11-13
WO2003093302A2 (en) 2003-11-13

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