CA2441922C - Solid phase synthesis supports and methods - Google Patents
Solid phase synthesis supports and methods Download PDFInfo
- Publication number
- CA2441922C CA2441922C CA2441922A CA2441922A CA2441922C CA 2441922 C CA2441922 C CA 2441922C CA 2441922 A CA2441922 A CA 2441922A CA 2441922 A CA2441922 A CA 2441922A CA 2441922 C CA2441922 C CA 2441922C
- Authority
- CA
- Canada
- Prior art keywords
- linker
- group
- support
- functionalized
- functionalized support
- 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.)
- Expired - Fee Related
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- 238000010532 solid phase synthesis reaction Methods 0.000 title claims abstract description 36
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- 125000000962 organic group Chemical group 0.000 claims description 67
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 45
- 229910052739 hydrogen Inorganic materials 0.000 claims description 44
- 239000001257 hydrogen Substances 0.000 claims description 44
- 238000006243 chemical reaction Methods 0.000 claims description 42
- 125000003118 aryl group Chemical group 0.000 claims description 39
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
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- 238000009792 diffusion process Methods 0.000 description 1
- 238000012674 dispersion polymerization Methods 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 229920001600 hydrophobic polymer Polymers 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052752 metalloid Inorganic materials 0.000 description 1
- 150000002738 metalloids Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000004005 microsphere Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 description 1
- UZJLYRRDVFWSGA-UHFFFAOYSA-N n-benzylacetamide Chemical compound CC(=O)NCC1=CC=CC=C1 UZJLYRRDVFWSGA-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004971 nitroalkyl group Chemical group 0.000 description 1
- 238000002414 normal-phase solid-phase extraction Methods 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000000816 peptidomimetic Substances 0.000 description 1
- NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical group OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920005547 polycyclic aromatic hydrocarbon Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- KWGRBVOPPLSCSI-WCBMZHEXSA-N pseudoephedrine Chemical compound CN[C@@H](C)[C@@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WCBMZHEXSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000004964 sulfoalkyl group Chemical group 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- MBYLVOKEDDQJDY-UHFFFAOYSA-N tris(2-aminoethyl)amine Chemical compound NCCN(CCN)CCN MBYLVOKEDDQJDY-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C40—COMBINATORIAL TECHNOLOGY
- C40B—COMBINATORIAL CHEMISTRY; LIBRARIES, e.g. CHEMICAL LIBRARIES
- C40B50/00—Methods of creating libraries, e.g. combinatorial synthesis
- C40B50/14—Solid phase synthesis, i.e. wherein one or more library building blocks are bound to a solid support during library creation; Particular methods of cleavage from the solid support
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H21/00—Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids
- C07H21/04—Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids with deoxyribosyl as saccharide radical
-
- 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
- C07K1/04—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length on carriers
- C07K1/042—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length on carriers characterised by the nature of the carrier
-
- 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
- B01J2219/00274—Sequential or parallel reactions; Apparatus and devices for combinatorial chemistry or for making arrays; Chemical library technology
- B01J2219/00277—Apparatus
- B01J2219/00497—Features relating to the solid phase supports
-
- 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
- B01J2219/00274—Sequential or parallel reactions; Apparatus and devices for combinatorial chemistry or for making arrays; Chemical library technology
- B01J2219/00277—Apparatus
- B01J2219/00497—Features relating to the solid phase supports
- B01J2219/005—Beads
-
- 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
- B01J2219/00274—Sequential or parallel reactions; Apparatus and devices for combinatorial chemistry or for making arrays; Chemical library technology
- B01J2219/00277—Apparatus
- B01J2219/00497—Features relating to the solid phase supports
- B01J2219/00527—Sheets
-
- 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
- B01J2219/00274—Sequential or parallel reactions; Apparatus and devices for combinatorial chemistry or for making arrays; Chemical library technology
- B01J2219/00583—Features relative to the processes being carried out
- B01J2219/00596—Solid-phase processes
-
- 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
- C07B2200/11—Compounds covalently bound to a solid support
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Structural Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Analytical Chemistry (AREA)
- Biophysics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Peptides Or Proteins (AREA)
- Physical Or Chemical Processes And Apparatus (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/827,107 US6787635B2 (en) | 2001-04-05 | 2001-04-05 | Solid phase synthesis supports and methods |
| US09/827,107 | 2001-04-05 | ||
| PCT/US2002/006367 WO2002081078A2 (en) | 2001-04-05 | 2002-02-28 | Solid phase synthesis supports and methods |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2441922A1 CA2441922A1 (en) | 2002-10-17 |
| CA2441922C true CA2441922C (en) | 2011-04-19 |
Family
ID=25248329
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2441922A Expired - Fee Related CA2441922C (en) | 2001-04-05 | 2002-02-28 | Solid phase synthesis supports and methods |
Country Status (6)
| Country | Link |
|---|---|
| US (3) | US6787635B2 (https=) |
| EP (1) | EP1373167B1 (https=) |
| JP (1) | JP4689941B2 (https=) |
| AU (1) | AU2002247242A1 (https=) |
| CA (1) | CA2441922C (https=) |
| WO (1) | WO2002081078A2 (https=) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2005295757A1 (en) * | 2004-10-15 | 2006-04-27 | 3M Innovative Properties Company | Pleated multi-layer filter media and cartridge |
| US20060258875A1 (en) * | 2005-05-10 | 2006-11-16 | Clementine Reyes | Methods for manufacturing supported nanocatalysts and methods for using supported nanocatalysts |
| US20060260677A1 (en) * | 2005-05-23 | 2006-11-23 | Cornell Research Foundation, Inc. | Polypropylene silicate nanocomposites |
| US8097229B2 (en) * | 2006-01-17 | 2012-01-17 | Headwaters Technology Innovation, Llc | Methods for manufacturing functionalized inorganic oxides and polymers incorporating same |
| WO2009158071A2 (en) | 2008-06-26 | 2009-12-30 | 3M Innovative Properties Company | Solid support with a grafted chain |
Family Cites Families (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3730922A (en) * | 1971-08-09 | 1973-05-01 | Shell Oil Co | Cyclic ether polymerization process |
| US4350628A (en) * | 1979-10-01 | 1982-09-21 | Research Corporation | Preparation of dehydropeptides |
| US4996243A (en) * | 1981-10-29 | 1991-02-26 | Minnesota Mining And Manufacturing Company | Curable acrylamido oligomer compositions with initiator, and cured products |
| US4485236A (en) * | 1982-09-27 | 1984-11-27 | Minnesota Mining And Manufacturing Company | Azlactone-functional compounds |
| US4918231A (en) | 1984-07-30 | 1990-04-17 | Minnesota Mining And Manufacturing Company | Process for the production of 1,2-amino alcohols |
| US4871824A (en) | 1987-03-13 | 1989-10-03 | Minnesota Mining And Manufacturing Company | Variably crosslinked polymeric supports |
| US5336742A (en) | 1987-03-13 | 1994-08-09 | Minnesota Mining And Manufacturing Company | Polymeric supports |
| US5262484A (en) | 1989-04-10 | 1993-11-16 | Minnesota Mining And Manufacturing Company | Azlactone graft copolymers |
| US5200471A (en) * | 1990-11-05 | 1993-04-06 | Minnesota Mining And Manufacturing Company | Biomolecules covalently immobilized with a high bound specific biological activity and method of preparing same |
| US5198531A (en) | 1991-06-14 | 1993-03-30 | Research Diagnostic Antibodies | Polymeric resin for peptide synthesis |
| US5993935A (en) | 1991-10-11 | 1999-11-30 | 3M Innovative Properties Company | Covalently reactive particles incorporated in a continous porous matrix |
| US5344701A (en) | 1992-06-09 | 1994-09-06 | Minnesota Mining And Manufacturing Company | Porous supports having azlactone-functional surfaces |
| US5292514A (en) | 1992-06-24 | 1994-03-08 | Minnesota Mining And Manufacturing Company | Azlactone-functional substrates, corneal prostheses, and manufacture and use thereof |
| US5750245A (en) | 1993-01-29 | 1998-05-12 | Minnesota Mining And Manufacturing Company | Thermally induced phase separated azlactone membrane |
| CA2158056A1 (en) | 1993-03-29 | 1994-10-13 | William H. Velander | Method of coupling ligands within porous supports (p.e. azlactone) and uses thereof |
| US5576419A (en) | 1993-06-30 | 1996-11-19 | Regents Of The University Of Minnesota | Mild solid-phase synthesis of aligned branched triple-helical peptides |
| US5408002A (en) | 1993-09-09 | 1995-04-18 | Minnesota Mining And Manufacturing Company | Azlactone-functional polymer blends, articles produced therefrom and methods for preparing both |
| US5561097A (en) | 1994-04-28 | 1996-10-01 | Minnesota Mining And Manufacturing Company | Method of controlling density of ligand coupled onto supports and products produced therefrom |
| US5510421A (en) | 1994-05-26 | 1996-04-23 | Minnesota Mining And Manufacturing Company | Azlactone-functional membranes and methods of preparing and using same |
| US5695760A (en) * | 1995-04-24 | 1997-12-09 | Boehringer Inglehiem Pharmaceuticals, Inc. | Modified anti-ICAM-1 antibodies and their use in the treatment of inflammation |
| US5656707A (en) | 1995-06-16 | 1997-08-12 | Regents Of The University Of Minnesota | Highly cross-linked polymeric supports |
| EP0801083A3 (en) | 1996-04-08 | 1999-12-29 | Pfizer Inc. | Improved functionalized resin for chemical synthesis |
| US5917015A (en) | 1996-06-18 | 1999-06-29 | Regents Of The University Of Minnesota | Support material for solid phase organic synthesis |
| GB9716456D0 (en) | 1997-08-05 | 1997-10-08 | Univ St Andrews | Modified ethylene polymer |
| WO2000012515A1 (en) * | 1998-08-31 | 2000-03-09 | Smithkline Beecham Corporation | Vinyl substituted cyclic products of the ene-yne reaction |
| GB9821669D0 (en) * | 1998-10-05 | 1998-12-02 | Glaxo Group Ltd | Chemical constructs and their uses |
| WO2000026262A2 (en) | 1998-11-05 | 2000-05-11 | Mitokor | Functionalized polymeric substrates for binding molecular moieties |
| GB9923577D0 (en) * | 1999-10-05 | 1999-12-08 | Glaxo Group Ltd | Chemical constructs |
-
2001
- 2001-04-05 US US09/827,107 patent/US6787635B2/en not_active Expired - Lifetime
-
2002
- 2002-02-28 CA CA2441922A patent/CA2441922C/en not_active Expired - Fee Related
- 2002-02-28 EP EP02715021.8A patent/EP1373167B1/en not_active Expired - Lifetime
- 2002-02-28 AU AU2002247242A patent/AU2002247242A1/en not_active Abandoned
- 2002-02-28 WO PCT/US2002/006367 patent/WO2002081078A2/en not_active Ceased
- 2002-02-28 JP JP2002579111A patent/JP4689941B2/ja not_active Expired - Fee Related
-
2004
- 2004-07-27 US US10/900,240 patent/US7166696B2/en not_active Expired - Lifetime
-
2006
- 2006-10-27 US US11/553,775 patent/US7820785B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| AU2002247242A1 (en) | 2002-10-21 |
| JP4689941B2 (ja) | 2011-06-01 |
| US7166696B2 (en) | 2007-01-23 |
| US6787635B2 (en) | 2004-09-07 |
| US20020173051A1 (en) | 2002-11-21 |
| CA2441922A1 (en) | 2002-10-17 |
| US20040265899A1 (en) | 2004-12-30 |
| EP1373167A2 (en) | 2004-01-02 |
| US20070049728A1 (en) | 2007-03-01 |
| JP2005500993A (ja) | 2005-01-13 |
| WO2002081078A3 (en) | 2003-03-27 |
| US7820785B2 (en) | 2010-10-26 |
| WO2002081078A2 (en) | 2002-10-17 |
| EP1373167B1 (en) | 2015-12-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20130228 |