CA2433195A1 - Composition and methods for synthesis of novel tracers for detecting amphetamine and methamphetamine in samples - Google Patents
Composition and methods for synthesis of novel tracers for detecting amphetamine and methamphetamine in samples Download PDFInfo
- Publication number
- CA2433195A1 CA2433195A1 CA002433195A CA2433195A CA2433195A1 CA 2433195 A1 CA2433195 A1 CA 2433195A1 CA 002433195 A CA002433195 A CA 002433195A CA 2433195 A CA2433195 A CA 2433195A CA 2433195 A1 CA2433195 A1 CA 2433195A1
- Authority
- CA
- Canada
- Prior art keywords
- group
- tracer
- amphetamine
- sample
- immunoassay
- 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.)
- Abandoned
Links
- 229940025084 amphetamine Drugs 0.000 title claims abstract description 49
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 title claims abstract description 46
- 238000000034 method Methods 0.000 title claims abstract description 37
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 title claims abstract description 29
- 229960001252 methamphetamine Drugs 0.000 title claims abstract description 29
- 230000015572 biosynthetic process Effects 0.000 title abstract description 20
- 238000003786 synthesis reaction Methods 0.000 title abstract description 20
- 239000000203 mixture Substances 0.000 title description 32
- 239000000700 radioactive tracer Substances 0.000 claims abstract description 78
- 238000003018 immunoassay Methods 0.000 claims abstract description 48
- 150000001875 compounds Chemical class 0.000 claims description 28
- 239000000523 sample Substances 0.000 claims description 21
- 210000003296 saliva Anatomy 0.000 claims description 12
- 239000000427 antigen Substances 0.000 claims description 8
- 102000036639 antigens Human genes 0.000 claims description 8
- 108091007433 antigens Proteins 0.000 claims description 8
- 239000012472 biological sample Substances 0.000 claims description 8
- 210000002700 urine Anatomy 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 102000004190 Enzymes Human genes 0.000 claims description 2
- 108090000790 Enzymes Proteins 0.000 claims description 2
- 210000004369 blood Anatomy 0.000 claims description 2
- 239000008280 blood Substances 0.000 claims description 2
- 239000000084 colloidal system Substances 0.000 claims description 2
- 239000007850 fluorescent dye Substances 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 210000002381 plasma Anatomy 0.000 claims description 2
- 210000002966 serum Anatomy 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 4
- 239000007787 solid Substances 0.000 claims 3
- 239000012491 analyte Substances 0.000 abstract description 29
- 238000006073 displacement reaction Methods 0.000 abstract description 18
- 239000000599 controlled substance Substances 0.000 abstract description 12
- 239000007858 starting material Substances 0.000 abstract description 12
- 238000001514 detection method Methods 0.000 abstract description 9
- 230000002194 synthesizing effect Effects 0.000 abstract description 6
- 229940125368 controlled substance Drugs 0.000 abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 238000002360 preparation method Methods 0.000 description 19
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- 229940079593 drug Drugs 0.000 description 14
- 239000003814 drug Substances 0.000 description 14
- 150000002148 esters Chemical class 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- -1 succinimidyl Chemical group 0.000 description 11
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000000872 buffer Substances 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- 229920005989 resin Polymers 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 238000004809 thin layer chromatography Methods 0.000 description 8
- 239000012043 crude product Substances 0.000 description 7
- 239000002117 illicit drug Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 239000000377 silicon dioxide Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 6
- 238000003556 assay Methods 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 229960000074 biopharmaceutical Drugs 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 230000009260 cross reactivity Effects 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 150000007925 phenylethylamine derivatives Chemical class 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- HDTRYLNUVZCQOY-UHFFFAOYSA-N α-D-glucopyranosyl-α-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(CO)O1 HDTRYLNUVZCQOY-UHFFFAOYSA-N 0.000 description 2
- NRKYWOKHZRQRJR-UHFFFAOYSA-N 2,2,2-trifluoroacetamide Chemical compound NC(=O)C(F)(F)F NRKYWOKHZRQRJR-UHFFFAOYSA-N 0.000 description 2
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- HDTRYLNUVZCQOY-WSWWMNSNSA-N Trehalose Natural products O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-WSWWMNSNSA-N 0.000 description 2
- HDTRYLNUVZCQOY-LIZSDCNHSA-N alpha,alpha-trehalose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-LIZSDCNHSA-N 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000003068 molecular probe Substances 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 239000007790 solid phase Substances 0.000 description 2
- 239000000021 stimulant Substances 0.000 description 2
- 229940014800 succinic anhydride Drugs 0.000 description 2
- 210000004243 sweat Anatomy 0.000 description 2
- WECUIGDEWBNQJJ-UHFFFAOYSA-N 4-phenylbutan-2-amine Chemical compound CC(N)CCC1=CC=CC=C1 WECUIGDEWBNQJJ-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 1
- 239000002269 analeptic agent Substances 0.000 description 1
- 230000036528 appetite Effects 0.000 description 1
- 235000019789 appetite Nutrition 0.000 description 1
- PFYXSUNOLOJMDX-UHFFFAOYSA-N bis(2,5-dioxopyrrolidin-1-yl) carbonate Chemical compound O=C1CCC(=O)N1OC(=O)ON1C(=O)CCC1=O PFYXSUNOLOJMDX-UHFFFAOYSA-N 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000010339 dilation Effects 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 description 1
- 210000004209 hair Anatomy 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- TWXDDNPPQUTEOV-FVGYRXGTSA-N methamphetamine hydrochloride Chemical compound Cl.CN[C@@H](C)CC1=CC=CC=C1 TWXDDNPPQUTEOV-FVGYRXGTSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- PUAUJIPHHQUZGF-UHFFFAOYSA-N n-methyl-4-phenylbutan-2-amine Chemical compound CNC(C)CCC1=CC=CC=C1 PUAUJIPHHQUZGF-UHFFFAOYSA-N 0.000 description 1
- 210000000282 nail Anatomy 0.000 description 1
- 210000001428 peripheral nervous system Anatomy 0.000 description 1
- 210000001747 pupil Anatomy 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 230000002889 sympathetic effect Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/94—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving narcotics or drugs or pharmaceuticals, neurotransmitters or associated receptors
- G01N33/946—CNS-stimulants, e.g. cocaine, amphetamines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C331/00—Derivatives of thiocyanic acid or of isothiocyanic acid
- C07C331/16—Isothiocyanates
- C07C331/28—Isothiocyanates having isothiocyanate groups bound to carbon atoms of six-membered aromatic rings
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S436/00—Chemistry: analytical and immunological testing
- Y10S436/815—Test for named compound or class of compounds
- Y10S436/816—Alkaloids, amphetamines, and barbiturates
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Molecular Biology (AREA)
- Urology & Nephrology (AREA)
- Immunology (AREA)
- Biomedical Technology (AREA)
- Hematology (AREA)
- Medicinal Chemistry (AREA)
- Analytical Chemistry (AREA)
- Cell Biology (AREA)
- Pharmacology & Pharmacy (AREA)
- Food Science & Technology (AREA)
- Biotechnology (AREA)
- Physics & Mathematics (AREA)
- Microbiology (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/730,095 | 2000-12-04 | ||
| US09/730,095 US6472228B2 (en) | 2000-12-04 | 2000-12-04 | Composition and methods for synthesis of novel tracers for detecting amphetamine and methamphetamine in samples |
| PCT/US2001/045024 WO2002057739A2 (en) | 2000-12-04 | 2001-11-29 | Composition and methods for synthesis of novel tracers for detecting amphetamine and methamphetamine in samples |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2433195A1 true CA2433195A1 (en) | 2002-07-25 |
Family
ID=24933880
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002433195A Abandoned CA2433195A1 (en) | 2000-12-04 | 2001-11-29 | Composition and methods for synthesis of novel tracers for detecting amphetamine and methamphetamine in samples |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US6472228B2 (https=) |
| EP (1) | EP1340081A4 (https=) |
| JP (1) | JP2004525359A (https=) |
| CA (1) | CA2433195A1 (https=) |
| WO (1) | WO2002057739A2 (https=) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7314569B2 (en) * | 2003-04-04 | 2008-01-01 | Arrowhead Center, Inc. | Treatment of arsenic-contaminated water using akaganeite adsorption |
| MXPA05012850A (es) * | 2003-05-29 | 2006-05-17 | New River Pharmaceuticals Inc | Compuestos de anfetamina resistentes al abuso. |
| US7341841B2 (en) * | 2003-07-12 | 2008-03-11 | Accelr8 Technology Corporation | Rapid microbial detection and antimicrobial susceptibility testing |
| US20120077206A1 (en) | 2003-07-12 | 2012-03-29 | Accelr8 Technology Corporation | Rapid Microbial Detection and Antimicrobial Susceptibility Testing |
| ES2661168T3 (es) | 2003-07-12 | 2018-03-27 | Accelerate Diagnostics, Inc. | Biodetección sensible y rápida |
| US20050136405A1 (en) * | 2003-12-17 | 2005-06-23 | James Linder | Novel method for the detection of cancer biomarkers in cervical specimens |
| US7037669B2 (en) * | 2004-03-22 | 2006-05-02 | Dade Behring Inc. | Assays for amphetamine and methamphetamine using stereospecific reagents |
| GB2404022B (en) | 2004-06-14 | 2005-08-10 | Cozart Bioscience Ltd | Competitive assays for the detection of methamphetamine group drugs |
| GB2404023B (en) | 2004-07-02 | 2005-07-06 | Cozart Bioscience Ltd | Delta-9-tetrahydrocannabinol detection method |
| JP2008533167A (ja) | 2005-03-15 | 2008-08-21 | アプレラ コーポレイション | 分析物の検出のための、抗体の代替抗原系の使用 |
| WO2012122314A2 (en) | 2011-03-07 | 2012-09-13 | Accelr8 Technology Corporation | Rapid cell purification systems |
| US10254204B2 (en) | 2011-03-07 | 2019-04-09 | Accelerate Diagnostics, Inc. | Membrane-assisted purification |
| US9677109B2 (en) | 2013-03-15 | 2017-06-13 | Accelerate Diagnostics, Inc. | Rapid determination of microbial growth and antimicrobial susceptibility |
| AU2016243656A1 (en) | 2015-03-30 | 2017-11-09 | Accelerate Diagnostics, Inc. | Instrument and system for rapid microorganism identification and antimicrobial agent susceptibility testing |
| US10253355B2 (en) | 2015-03-30 | 2019-04-09 | Accelerate Diagnostics, Inc. | Instrument and system for rapid microorganism identification and antimicrobial agent susceptibility testing |
| CN114890958B (zh) * | 2022-02-23 | 2023-10-20 | 四川警察学院 | 双光子染料化合物、其制备方法及其应用 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4868132A (en) | 1987-02-03 | 1989-09-19 | Abbott Laboratories | Fluorescence polarization immunoassay for amphetamine/methamphetamine |
| DE68924243T2 (de) | 1988-10-28 | 1996-03-28 | Abbott Lab | Verfahren und Reagenzien zum Nachweis von Amphetamin und/oder d-Methamphetamin in biologischen Proben. |
| US5135863A (en) | 1988-12-23 | 1992-08-04 | Syntex (U.S.A.) Inc. | Compositions and methods for determining the presence of amphetamines in a sample suspected of containing amphetamine and/or methamphetamine |
| DK0386644T3 (da) | 1989-03-10 | 1997-10-13 | Hoffmann La Roche | Reagenser til bestemmelse af lægemidler |
| US5101015A (en) * | 1989-04-10 | 1992-03-31 | Abbott Laboratories | Reagents for an amphetamine-class fluorescence polarization immunoassay |
| US5183740A (en) | 1990-02-23 | 1993-02-02 | The United States Of America As Represented By The Secretary Of The Navy | Flow immunosensor method and apparatus |
| CA2096495C (en) * | 1992-06-16 | 2002-07-09 | Kathy Palmer Ordonez | Dual analyte immunoassay |
| US6020209A (en) | 1997-04-28 | 2000-02-01 | The United States Of America As Represented By The Secretary Of The Navy | Microcapillary-based flow-through immunosensor and displacement immunoassay using the same |
-
2000
- 2000-12-04 US US09/730,095 patent/US6472228B2/en not_active Expired - Fee Related
-
2001
- 2001-11-29 WO PCT/US2001/045024 patent/WO2002057739A2/en not_active Ceased
- 2001-11-29 JP JP2002557773A patent/JP2004525359A/ja not_active Withdrawn
- 2001-11-29 CA CA002433195A patent/CA2433195A1/en not_active Abandoned
- 2001-11-29 EP EP01993187A patent/EP1340081A4/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| US20020090661A1 (en) | 2002-07-11 |
| WO2002057739A2 (en) | 2002-07-25 |
| EP1340081A4 (en) | 2005-08-03 |
| EP1340081A2 (en) | 2003-09-03 |
| WO2002057739A3 (en) | 2003-01-23 |
| JP2004525359A (ja) | 2004-08-19 |
| US6472228B2 (en) | 2002-10-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |