TWI288132B - Process for the preparation of 4,6-dimethoxy-2-(methylsulfonyl)-1,3-pyrimidine - Google Patents
Process for the preparation of 4,6-dimethoxy-2-(methylsulfonyl)-1,3-pyrimidine Download PDFInfo
- Publication number
- TWI288132B TWI288132B TW090117644A TW90117644A TWI288132B TW I288132 B TWI288132 B TW I288132B TW 090117644 A TW090117644 A TW 090117644A TW 90117644 A TW90117644 A TW 90117644A TW I288132 B TWI288132 B TW I288132B
- Authority
- TW
- Taiwan
- Prior art keywords
- pyrimidine
- dimethoxy
- organic solvent
- aqueous
- reaction mixture
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 42
- 238000002360 preparation method Methods 0.000 title claims description 10
- 239000003960 organic solvent Substances 0.000 claims abstract description 36
- 239000011541 reaction mixture Substances 0.000 claims abstract description 28
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 17
- 230000003647 oxidation Effects 0.000 claims abstract description 16
- 238000000746 purification Methods 0.000 claims abstract description 15
- -1 alkali metal methoxide Chemical class 0.000 claims abstract description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 10
- 239000003054 catalyst Substances 0.000 claims abstract description 9
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 7
- 239000002585 base Substances 0.000 claims abstract description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 67
- 238000006243 chemical reaction Methods 0.000 claims description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
- 230000002378 acidificating effect Effects 0.000 claims description 15
- 239000007864 aqueous solution Substances 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- 239000000243 solution Substances 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 10
- 239000003444 phase transfer catalyst Substances 0.000 claims description 10
- 238000003756 stirring Methods 0.000 claims description 9
- 230000001590 oxidative effect Effects 0.000 claims description 8
- 239000000543 intermediate Substances 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 claims description 6
- 239000003513 alkali Substances 0.000 claims description 5
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 4
- 150000004945 aromatic hydrocarbons Chemical group 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 4
- 239000008096 xylene Substances 0.000 claims description 4
- 239000012670 alkaline solution Substances 0.000 claims description 3
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 3
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 3
- 125000003944 tolyl group Chemical group 0.000 claims 2
- 125000003158 alcohol group Chemical group 0.000 claims 1
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 1
- 238000009434 installation Methods 0.000 claims 1
- 239000011707 mineral Substances 0.000 claims 1
- 150000002923 oximes Chemical class 0.000 claims 1
- 239000004009 herbicide Substances 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- RRKHIAYNPVQKEF-UHFFFAOYSA-N Pyriftalid Chemical compound COC1=CC(OC)=NC(SC=2C=3C(=O)OC(C)C=3C=CC=2)=N1 RRKHIAYNPVQKEF-UHFFFAOYSA-N 0.000 abstract 1
- 239000008346 aqueous phase Substances 0.000 description 13
- 239000012071 phase Substances 0.000 description 11
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- 239000006227 byproduct Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 238000000926 separation method Methods 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000007800 oxidant agent Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 230000002363 herbicidal effect Effects 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- XMVONEAAOPAGAO-UHFFFAOYSA-N sodium tungstate Chemical compound [Na+].[Na+].[O-][W]([O-])(=O)=O XMVONEAAOPAGAO-UHFFFAOYSA-N 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- OIGXNHYFKZCTCH-UHFFFAOYSA-N 2-methylsulfonylpyrimidine Chemical compound CS(=O)(=O)C1=NC=CC=N1 OIGXNHYFKZCTCH-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 239000003586 protic polar solvent Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000007039 two-step reaction Methods 0.000 description 2
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 1
- FOEMIZSFFWGXHX-UHFFFAOYSA-N 2-methylsulfanylpyrimidine Chemical compound CSC1=NC=CC=N1 FOEMIZSFFWGXHX-UHFFFAOYSA-N 0.000 description 1
- DROUVIKCNOHKBA-UHFFFAOYSA-N 4,6-dichloro-2-methylsulfonylpyrimidine Chemical compound CS(=O)(=O)C1=NC(Cl)=CC(Cl)=N1 DROUVIKCNOHKBA-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- HBCQSNAFLVXVAY-UHFFFAOYSA-N pyrimidine-2-thiol Chemical class SC1=NC=CC=N1 HBCQSNAFLVXVAY-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- PBYZMCDFOULPGH-UHFFFAOYSA-N tungstate Chemical compound [O-][W]([O-])(=O)=O PBYZMCDFOULPGH-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/60—Three or more oxygen or sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH14392000 | 2000-07-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TWI288132B true TWI288132B (en) | 2007-10-11 |
Family
ID=4565478
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW090117644A TWI288132B (en) | 2000-07-21 | 2001-07-19 | Process for the preparation of 4,6-dimethoxy-2-(methylsulfonyl)-1,3-pyrimidine |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US6693194B2 (https=) |
| EP (1) | EP1301491A1 (https=) |
| JP (1) | JP3507483B1 (https=) |
| KR (1) | KR100516535B1 (https=) |
| CN (1) | CN1285581C (https=) |
| AR (1) | AR033677A1 (https=) |
| AU (2) | AU2001289701B2 (https=) |
| BR (1) | BR0112712A (https=) |
| CA (1) | CA2411155C (https=) |
| HU (1) | HUP0301038A3 (https=) |
| IL (1) | IL153662A0 (https=) |
| MX (1) | MXPA03000431A (https=) |
| PL (1) | PL362686A1 (https=) |
| RU (1) | RU2276142C2 (https=) |
| TW (1) | TWI288132B (https=) |
| UA (1) | UA75888C2 (https=) |
| WO (1) | WO2002008207A1 (https=) |
| ZA (1) | ZA200300510B (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT1786430E (pt) * | 2004-08-20 | 2013-06-04 | Buck Inst For Age Res | Pequenas moléculas que substituam ou agonizam a função p53 |
| WO2007117399A2 (en) | 2006-03-31 | 2007-10-18 | Janssen Pharmaceutica N.V. | Benzoimidazol-2-yl pyrimidines and pyrazines as modulators of the histamine h4 receptor |
| US9371311B2 (en) | 2008-06-30 | 2016-06-21 | Janssen Pharmaceutica Nv | Benzoimidazol-2-yl pyrimidine derivatives |
| SG192446A1 (en) | 2008-06-30 | 2013-08-30 | Janssen Pharmaceutica Nv | Process for the preparation of benzoimidazol-2-yl pyrimidine derivatives |
| CN102137672B (zh) | 2008-06-30 | 2014-03-26 | 詹森药业有限公司 | 取代的嘧啶衍生物的制备方法 |
| CN101747283B (zh) * | 2008-12-11 | 2011-06-08 | 中国中化股份有限公司 | 一种制备4，6-二甲氧基-2-甲磺酰基嘧啶的方法 |
| CN105026376B (zh) * | 2013-02-18 | 2018-05-11 | 加尔达化学有限公司 | 用于制备双草醚钠及其中间体的方法 |
| PT2964229T (pt) | 2013-03-06 | 2020-03-23 | Janssen Pharmaceutica Nv | Moduladores de piridina benzimidazol-2-ilo do recetor h4 de histamina |
| CN112552244A (zh) * | 2020-12-22 | 2021-03-26 | 内蒙古科硕新材料科技有限公司 | 一种4,6-二甲氧基-2-甲磺酰基嘧啶的生产工艺 |
| CN115215805B (zh) * | 2022-08-11 | 2024-06-25 | 上海奥萝拉医药科技有限公司 | 一种2-氰基嘧啶的制备工艺 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3525977A1 (de) | 1985-07-20 | 1987-01-29 | Bayer Ag | Verfahren zur herstellung von 2-cyanamino-pyrimidin-derivaten |
| JP2561480B2 (ja) | 1987-08-06 | 1996-12-11 | イハラケミカル工業株式会社 | ４，６−ジアルコキシ−２−アルキルチオピリミジン類の製造方法 |
| US5149357A (en) | 1990-06-19 | 1992-09-22 | Fmc Corporation | Herbicidal substituted benzoylsulfonamides |
| KR100233068B1 (ko) * | 1991-11-26 | 1999-12-01 | 하인즈 모제르 | 2-치환된 4,6-디알콕시피리미딘의 제조방법 |
| TWI220428B (en) * | 1999-02-05 | 2004-08-21 | Syngenta Participations Ag | Method of producing thiobarbituric acid derivatives |
-
2001
- 2001-07-19 IL IL15366201A patent/IL153662A0/xx unknown
- 2001-07-19 US US10/332,248 patent/US6693194B2/en not_active Expired - Lifetime
- 2001-07-19 AU AU2001289701A patent/AU2001289701B2/en not_active Ceased
- 2001-07-19 HU HU0301038A patent/HUP0301038A3/hu not_active Application Discontinuation
- 2001-07-19 UA UA2003021454A patent/UA75888C2/uk unknown
- 2001-07-19 TW TW090117644A patent/TWI288132B/zh not_active IP Right Cessation
- 2001-07-19 PL PL01362686A patent/PL362686A1/xx not_active Application Discontinuation
- 2001-07-19 JP JP2002514113A patent/JP3507483B1/ja not_active Expired - Fee Related
- 2001-07-19 CN CNB018131492A patent/CN1285581C/zh not_active Expired - Fee Related
- 2001-07-19 WO PCT/EP2001/008373 patent/WO2002008207A1/en not_active Ceased
- 2001-07-19 KR KR10-2003-7000881A patent/KR100516535B1/ko not_active Expired - Fee Related
- 2001-07-19 BR BR0112712-8A patent/BR0112712A/pt not_active Application Discontinuation
- 2001-07-19 MX MXPA03000431A patent/MXPA03000431A/es active IP Right Grant
- 2001-07-19 AU AU8970101A patent/AU8970101A/xx active Pending
- 2001-07-19 RU RU2003104800/04A patent/RU2276142C2/ru not_active IP Right Cessation
- 2001-07-19 CA CA002411155A patent/CA2411155C/en not_active Expired - Fee Related
- 2001-07-19 EP EP01969442A patent/EP1301491A1/en not_active Ceased
- 2001-07-20 AR ARP010103448A patent/AR033677A1/es not_active Application Discontinuation
-
2003
- 2003-01-20 ZA ZA200300510A patent/ZA200300510B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HUP0301038A2 (hu) | 2003-08-28 |
| IL153662A0 (en) | 2003-07-06 |
| ZA200300510B (en) | 2004-04-20 |
| US20030135047A1 (en) | 2003-07-17 |
| AU8970101A (en) | 2002-02-05 |
| AR033677A1 (es) | 2004-01-07 |
| JP3507483B1 (ja) | 2004-03-15 |
| RU2276142C2 (ru) | 2006-05-10 |
| BR0112712A (pt) | 2003-05-20 |
| JP2004504387A (ja) | 2004-02-12 |
| MXPA03000431A (es) | 2003-06-24 |
| EP1301491A1 (en) | 2003-04-16 |
| CN1443175A (zh) | 2003-09-17 |
| US6693194B2 (en) | 2004-02-17 |
| HUP0301038A3 (en) | 2004-06-28 |
| KR20030047992A (ko) | 2003-06-18 |
| UA75888C2 (uk) | 2006-06-15 |
| CA2411155C (en) | 2009-12-08 |
| CN1285581C (zh) | 2006-11-22 |
| CA2411155A1 (en) | 2002-01-31 |
| AU2001289701B2 (en) | 2004-06-24 |
| WO2002008207A1 (en) | 2002-01-31 |
| KR100516535B1 (ko) | 2005-09-22 |
| PL362686A1 (en) | 2004-11-02 |
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