ZA200200938B - Process for the preparation of 2-cyanopyridines. - Google Patents
Process for the preparation of 2-cyanopyridines. Download PDFInfo
- Publication number
- ZA200200938B ZA200200938B ZA200200938A ZA200200938A ZA200200938B ZA 200200938 B ZA200200938 B ZA 200200938B ZA 200200938 A ZA200200938 A ZA 200200938A ZA 200200938 A ZA200200938 A ZA 200200938A ZA 200200938 B ZA200200938 B ZA 200200938B
- Authority
- ZA
- South Africa
- Prior art keywords
- cyanide
- activating agent
- process according
- compound
- formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 25
- 238000002360 preparation method Methods 0.000 title claims description 5
- FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical class N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 title description 3
- 230000003213 activating effect Effects 0.000 claims description 19
- 239000003795 chemical substances by application Substances 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 18
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical group CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 14
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 12
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- -1 alkali metal cyanide Chemical class 0.000 claims description 7
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical group N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 claims description 7
- 238000003756 stirring Methods 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
- 239000002798 polar solvent Substances 0.000 claims description 5
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical group N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 4
- 230000000269 nucleophilic effect Effects 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
- ICAIHGOJRDCMHE-UHFFFAOYSA-O ammonium cyanide Chemical class [NH4+].N#[C-] ICAIHGOJRDCMHE-UHFFFAOYSA-O 0.000 claims description 2
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 claims description 2
- 150000003222 pyridines Chemical class 0.000 claims description 2
- 150000003512 tertiary amines Chemical group 0.000 claims description 2
- 125000005270 trialkylamine group Chemical group 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- ABNQGNFVSFKJGI-UHFFFAOYSA-N 2,3-dichloro-5-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CN=C(Cl)C(Cl)=C1 ABNQGNFVSFKJGI-UHFFFAOYSA-N 0.000 description 4
- 125000001188 haloalkyl group Chemical group 0.000 description 4
- 150000002367 halogens Chemical group 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical class CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 239000012038 nucleophile Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 150000005759 2-chloropyridine Chemical class 0.000 description 1
- FUPKVFJSGNZICR-UHFFFAOYSA-N 3-chloro-5-(trifluoromethyl)pyridine-2-carbonitrile Chemical compound FC(F)(F)C1=CN=C(C#N)C(Cl)=C1 FUPKVFJSGNZICR-UHFFFAOYSA-N 0.000 description 1
- RGUKYNXWOWSRET-UHFFFAOYSA-N 4-pyrrolidin-1-ylpyridine Chemical class C1CCCN1C1=CC=NC=C1 RGUKYNXWOWSRET-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 238000007333 cyanation reaction Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000011143 downstream manufacturing Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- NLEUXPOVZGDKJI-UHFFFAOYSA-N nickel(2+);dicyanide Chemical compound [Ni+2].N#[C-].N#[C-] NLEUXPOVZGDKJI-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical class [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/61—Halogen atoms or nitro radicals
-
- 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
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Catalysts (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9920959.5A GB9920959D0 (en) | 1999-09-07 | 1999-09-07 | Novel process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200200938B true ZA200200938B (en) | 2003-07-30 |
Family
ID=10860382
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200200938A ZA200200938B (en) | 1999-09-07 | 2002-02-01 | Process for the preparation of 2-cyanopyridines. |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US6699993B1 (fr) |
| EP (1) | EP1210331B1 (fr) |
| JP (1) | JP4764586B2 (fr) |
| KR (1) | KR100714146B1 (fr) |
| CN (1) | CN1147474C (fr) |
| AT (1) | ATE446952T1 (fr) |
| AU (1) | AU781641B2 (fr) |
| BR (1) | BR0013799B1 (fr) |
| CA (1) | CA2381176A1 (fr) |
| DE (1) | DE60043228D1 (fr) |
| GB (1) | GB9920959D0 (fr) |
| HK (1) | HK1048814A1 (fr) |
| HU (1) | HUP0202865A3 (fr) |
| IL (2) | IL148161A0 (fr) |
| MX (1) | MXPA02001945A (fr) |
| PL (1) | PL353926A1 (fr) |
| RU (1) | RU2222530C2 (fr) |
| TW (1) | TWI274054B (fr) |
| WO (1) | WO2001017970A1 (fr) |
| ZA (1) | ZA200200938B (fr) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR0113259B1 (pt) | 2000-08-25 | 2014-09-02 | Bayer Cropscience Sa | Processo para a preparação de um composto 2-aminometilpiridina de fórmula (I) |
| CN102239160A (zh) * | 2008-11-13 | 2011-11-09 | 拜尔农科股份公司 | 作为杀真菌剂的取代的(吡啶基)-嗪基胺衍生物 |
| CN106905231A (zh) * | 2015-12-23 | 2017-06-30 | 联化科技股份有限公司 | 3-氯-5-三氟甲基吡啶类化合物及中间体的制备方法 |
| CN106117131B (zh) * | 2016-06-29 | 2018-09-04 | 天津市均凯化工科技有限公司 | 一种制备2-氨基-3-氯-5-三氟甲基吡啶的方法 |
| CN106349159B (zh) * | 2016-08-29 | 2019-03-22 | 山东省联合农药工业有限公司 | 一种3-氯-2-氰基-5-三氟甲基吡啶的制备方法 |
| CN112390747A (zh) * | 2020-11-03 | 2021-02-23 | 内蒙古佳瑞米精细化工有限公司 | 2-氰基-3-氯-5-三氟甲基吡啶与丁二腈的联合制备方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1601761A (en) * | 1978-02-07 | 1981-11-04 | May M A | Swimming pool accessory |
| JPS56118066A (en) * | 1980-02-21 | 1981-09-16 | Ishihara Sangyo Kaisha Ltd | 2-cyano-3-halogeno-5-trifluoromethylpyridine and its preparation |
| JPS56118065A (en) * | 1980-02-21 | 1981-09-16 | Ishihara Sangyo Kaisha Ltd | 5-trifluoromethylpyridine-2-carboxylic acid, its salt, and their preparation |
| DE3165316D1 (en) * | 1980-02-21 | 1984-09-13 | Ishihara Sangyo Kaisha | 2-substituted-5-trifluoromethylpyridines and a process for producing the same |
| US4766219A (en) * | 1985-06-03 | 1988-08-23 | The Dow Chemical Company | Preparation of 2-cyano-6-chloropyridine compounds |
| US4776219A (en) * | 1987-04-06 | 1988-10-11 | Jaromir Friedrich | Pressure transducer |
| US4829164A (en) | 1987-11-02 | 1989-05-09 | Western Pacific Industries Inc. | Counter |
| NZ242290A (en) * | 1991-04-15 | 1994-12-22 | Zeneca Ltd | Pyridyl and pyrimidinyl substituted oxime-o-benzyl ether derivatives; preparatory processes, fungicidal compositions and an intermediate |
-
1999
- 1999-09-07 GB GBGB9920959.5A patent/GB9920959D0/en not_active Ceased
-
2000
- 2000-08-30 IL IL14816100A patent/IL148161A0/xx active IP Right Grant
- 2000-08-30 WO PCT/EP2000/009148 patent/WO2001017970A1/fr active IP Right Grant
- 2000-08-30 JP JP2001521717A patent/JP4764586B2/ja not_active Expired - Lifetime
- 2000-08-30 CA CA002381176A patent/CA2381176A1/fr not_active Abandoned
- 2000-08-30 CN CNB008124655A patent/CN1147474C/zh not_active Expired - Lifetime
- 2000-08-30 US US10/070,505 patent/US6699993B1/en not_active Expired - Lifetime
- 2000-08-30 MX MXPA02001945A patent/MXPA02001945A/es active IP Right Grant
- 2000-08-30 RU RU2002108720/04A patent/RU2222530C2/ru not_active IP Right Cessation
- 2000-08-30 DE DE60043228T patent/DE60043228D1/de not_active Expired - Lifetime
- 2000-08-30 BR BRPI0013799-5A patent/BR0013799B1/pt not_active IP Right Cessation
- 2000-08-30 AT AT00962505T patent/ATE446952T1/de not_active IP Right Cessation
- 2000-08-30 AU AU74202/00A patent/AU781641B2/en not_active Ceased
- 2000-08-30 PL PL00353926A patent/PL353926A1/xx not_active Application Discontinuation
- 2000-08-30 EP EP00962505A patent/EP1210331B1/fr not_active Expired - Lifetime
- 2000-08-30 HU HU0202865A patent/HUP0202865A3/hu unknown
- 2000-08-30 KR KR1020027001995A patent/KR100714146B1/ko active IP Right Grant
- 2000-09-06 TW TW089118221A patent/TWI274054B/zh not_active IP Right Cessation
-
2002
- 2002-02-01 ZA ZA200200938A patent/ZA200200938B/en unknown
- 2002-02-14 IL IL148161A patent/IL148161A/en unknown
-
2003
- 2003-02-12 HK HK03101001A patent/HK1048814A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CN1147474C (zh) | 2004-04-28 |
| RU2222530C2 (ru) | 2004-01-27 |
| EP1210331A1 (fr) | 2002-06-05 |
| HUP0202865A3 (en) | 2005-01-28 |
| HUP0202865A2 (hu) | 2002-12-28 |
| MXPA02001945A (es) | 2002-08-20 |
| KR100714146B1 (ko) | 2007-05-02 |
| IL148161A0 (en) | 2002-09-12 |
| WO2001017970A1 (fr) | 2001-03-15 |
| JP4764586B2 (ja) | 2011-09-07 |
| IL148161A (en) | 2006-12-31 |
| DE60043228D1 (de) | 2009-12-10 |
| HK1048814A1 (en) | 2003-04-17 |
| AU781641B2 (en) | 2005-06-02 |
| BR0013799A (pt) | 2002-05-21 |
| CA2381176A1 (fr) | 2001-03-15 |
| GB9920959D0 (en) | 1999-11-10 |
| US6699993B1 (en) | 2004-03-02 |
| CN1372550A (zh) | 2002-10-02 |
| BR0013799B1 (pt) | 2011-07-12 |
| KR20020021409A (ko) | 2002-03-20 |
| PL353926A1 (en) | 2003-12-15 |
| EP1210331B1 (fr) | 2009-10-28 |
| AU7420200A (en) | 2001-04-10 |
| JP2003508520A (ja) | 2003-03-04 |
| ATE446952T1 (de) | 2009-11-15 |
| TWI274054B (en) | 2007-02-21 |
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