TWI266766B - Process for preparing 3,4-dichloro-N-(2-cyanophenyl)-5-isothiazolecarboxamide - Google Patents
Process for preparing 3,4-dichloro-N-(2-cyanophenyl)-5-isothiazolecarboxamide Download PDFInfo
- Publication number
- TWI266766B TWI266766B TW092117350A TW92117350A TWI266766B TW I266766 B TWI266766 B TW I266766B TW 092117350 A TW092117350 A TW 092117350A TW 92117350 A TW92117350 A TW 92117350A TW I266766 B TWI266766 B TW I266766B
- Authority
- TW
- Taiwan
- Prior art keywords
- patent application
- dichloro
- chloride
- carried out
- ministry
- Prior art date
Links
- WLPCAERCXQSYLQ-UHFFFAOYSA-N isotianil Chemical compound ClC1=NSC(C(=O)NC=2C(=CC=CC=2)C#N)=C1Cl WLPCAERCXQSYLQ-UHFFFAOYSA-N 0.000 title abstract description 10
- 238000004519 manufacturing process Methods 0.000 title description 2
- 238000000034 method Methods 0.000 claims abstract description 28
- 239000002253 acid Substances 0.000 claims abstract description 9
- 239000012024 dehydrating agents Substances 0.000 claims abstract description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 14
- -1 3,4-dichloro-N-(2-cyanophenyl)-5-isothiazole carboxamide Amine Chemical class 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 5
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 4
- 239000000010 aprotic solvent Substances 0.000 claims description 3
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical compound C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 claims 3
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 2
- 150000007942 carboxylates Chemical class 0.000 claims 1
- QQVDYSUDFZZPSU-UHFFFAOYSA-M chloromethylidene(dimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)=CCl QQVDYSUDFZZPSU-UHFFFAOYSA-M 0.000 claims 1
- PXBFMLJZNCDSMP-UHFFFAOYSA-N 2-Aminobenzamide Chemical compound NC(=O)C1=CC=CC=C1N PXBFMLJZNCDSMP-UHFFFAOYSA-N 0.000 abstract description 14
- 239000003085 diluting agent Substances 0.000 abstract description 6
- VSCBEYLFHZIKQA-UHFFFAOYSA-N n-(2-carbamoylphenyl)-3,4-dichloro-1,2-thiazole-5-carboxamide Chemical compound NC(=O)C1=CC=CC=C1NC(=O)C1=C(Cl)C(Cl)=NS1 VSCBEYLFHZIKQA-UHFFFAOYSA-N 0.000 abstract description 3
- MSSXWKAJMRSAGF-UHFFFAOYSA-N 3,4-dichloro-1,2-thiazole-5-carbonyl chloride Chemical compound ClC(=O)C=1SN=C(Cl)C=1Cl MSSXWKAJMRSAGF-UHFFFAOYSA-N 0.000 abstract description 2
- 239000007787 solid Substances 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 238000003756 stirring Methods 0.000 description 8
- 239000000725 suspension Substances 0.000 description 7
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- HLCPWBZNUKCSBN-UHFFFAOYSA-N 2-aminobenzonitrile Chemical compound NC1=CC=CC=C1C#N HLCPWBZNUKCSBN-UHFFFAOYSA-N 0.000 description 3
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 230000002079 cooperative effect Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- YWWNNLPSZSEZNZ-UHFFFAOYSA-N n,n-dimethyldecan-1-amine Chemical compound CCCCCCCCCCN(C)C YWWNNLPSZSEZNZ-UHFFFAOYSA-N 0.000 description 3
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- OAYOAFHPHUZYBF-UHFFFAOYSA-N [SH3+].[SH3+].[Cl-].[Cl-] Chemical compound [SH3+].[SH3+].[Cl-].[Cl-] OAYOAFHPHUZYBF-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- DXVWRJRZCMCNEU-UHFFFAOYSA-N dimercaptoamine Chemical compound SNS DXVWRJRZCMCNEU-UHFFFAOYSA-N 0.000 description 2
- 229940113088 dimethylacetamide Drugs 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- SJHPCNCNNSSLPL-CSKARUKUSA-N (4e)-4-(ethoxymethylidene)-2-phenyl-1,3-oxazol-5-one Chemical compound O1C(=O)C(=C/OCC)\N=C1C1=CC=CC=C1 SJHPCNCNNSSLPL-CSKARUKUSA-N 0.000 description 1
- OHVWVLZTMSRHBE-UHFFFAOYSA-N 1-sulfanylpiperidine Chemical compound SN1CCCCC1 OHVWVLZTMSRHBE-UHFFFAOYSA-N 0.000 description 1
- UNIDEFGBIDZCJO-UHFFFAOYSA-N 1-sulfanylpurine Chemical compound SN1C=NC2=NC=NC2=C1 UNIDEFGBIDZCJO-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- UHSIFVSUKUKIAV-UHFFFAOYSA-N 2-N-(2-aminophenyl)benzene-1,2-dicarboxamide Chemical compound NC1=C(C=CC=C1)NC(C=1C(C(=O)N)=CC=CC=1)=O UHSIFVSUKUKIAV-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- GMJHZZCVWDJKFB-UHFFFAOYSA-N 4-(4-aminophenyl)benzene-1,3-diamine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1N GMJHZZCVWDJKFB-UHFFFAOYSA-N 0.000 description 1
- OIUUZGZQBBPSEU-UHFFFAOYSA-N C(=O)(Cl)Cl.ClC1=NSC=C1Cl Chemical compound C(=O)(Cl)Cl.ClC1=NSC=C1Cl OIUUZGZQBBPSEU-UHFFFAOYSA-N 0.000 description 1
- OFZCBCZTEFGVKM-UHFFFAOYSA-N C(CCCCCCCC)C1=C(CCCCCCCCC1)CCCCCCCCC Chemical compound C(CCCCCCCC)C1=C(CCCCCCCCC1)CCCCCCCCC OFZCBCZTEFGVKM-UHFFFAOYSA-N 0.000 description 1
- WZGDDTQPNYDKMD-UHFFFAOYSA-N C1=CC=C(C(=C1)C(=O)N)N2C(C(=C(S2)C(=O)O)Cl)Cl Chemical compound C1=CC=C(C(=C1)C(=O)N)N2C(C(=C(S2)C(=O)O)Cl)Cl WZGDDTQPNYDKMD-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- BAVYZALUXZFZLV-UHFFFAOYSA-O Methylammonium ion Chemical compound [NH3+]C BAVYZALUXZFZLV-UHFFFAOYSA-O 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- KBGIVZVDRZTOOE-UHFFFAOYSA-N aminomethanedithiol Chemical compound NC(S)S KBGIVZVDRZTOOE-UHFFFAOYSA-N 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- DNOSZYUZVCJLMM-UHFFFAOYSA-N carbamimidoylazanium;benzoate Chemical class NC(N)=[NH2+].[O-]C(=O)C1=CC=CC=C1 DNOSZYUZVCJLMM-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 125000004802 cyanophenyl group Chemical group 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- HYHSFFFCLDOXCJ-UHFFFAOYSA-N dimethyl(methylidene)azanium Chemical compound C[N+](C)=C HYHSFFFCLDOXCJ-UHFFFAOYSA-N 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 229930004069 diterpene Natural products 0.000 description 1
- 150000004141 diterpene derivatives Chemical class 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-O hydron;1,3-oxazole Chemical compound C1=COC=[NH+]1 ZCQWOFVYLHDMMC-UHFFFAOYSA-O 0.000 description 1
- MQUPWTBHHPUUMC-UHFFFAOYSA-N isoindole Chemical compound C1=CC=C[C]2C=NC=C21 MQUPWTBHHPUUMC-UHFFFAOYSA-N 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 231100000989 no adverse effect Toxicity 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
- C07D275/03—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10228732A DE10228732A1 (de) | 2002-06-27 | 2002-06-27 | Verfahren zur Herstellung von 3,4-Dichlor-N-(2-cyano-phenyl)-5-isothiazolcarboxamid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200409762A TW200409762A (en) | 2004-06-16 |
| TWI266766B true TWI266766B (en) | 2006-11-21 |
Family
ID=29723489
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW092117350A TWI266766B (en) | 2002-06-27 | 2003-06-26 | Process for preparing 3,4-dichloro-N-(2-cyanophenyl)-5-isothiazolecarboxamide |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP1519926B1 (https=) |
| JP (1) | JP4551762B2 (https=) |
| KR (1) | KR101069222B1 (https=) |
| CN (1) | CN1325483C (https=) |
| AT (1) | ATE308530T1 (https=) |
| AU (1) | AU2003238510A1 (https=) |
| DE (2) | DE10228732A1 (https=) |
| TW (1) | TWI266766B (https=) |
| WO (1) | WO2004002968A1 (https=) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102005035617A1 (de) * | 2005-07-29 | 2007-02-15 | Bayer Cropscience Ag | Verfahren zur Herstellung von 3,4-Dichlor-N-(2-cyano-phenyl)-5-isothiazolcarboxamid |
| CN103483287B (zh) * | 2013-10-12 | 2015-07-08 | 南开大学 | 一类含3,4-二氯异噻唑的双酰胺类化合物及其制备方法和用途 |
| WO2018228984A1 (en) | 2017-06-14 | 2018-12-20 | Bayer Aktiengesellschaft | Process for preparing 3,4-dichloro-n-(2-cyanophenyl)-5-isothiazolecarboxamide |
| WO2019192988A1 (de) | 2018-04-06 | 2019-10-10 | Bayer Aktiengesellschaft | Verfahren zur herstellung von 3,4-dichlor-n-(2-cyanophenyl)-5-isothiazolcarboxamid |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2115625B2 (de) * | 1971-03-31 | 1978-07-06 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von N-o-Cyanophenyl-N', N'-disubstituierten Formamidinen und deren Salzen |
| DE2115624A1 (de) * | 1971-03-31 | 1972-10-12 | Badische Anilin & Soda Fabrik AG, 6700 Ludwigshafen | Verfahren zur Herstellung von o Amino benzonitrilen |
| DE19750012A1 (de) * | 1997-11-12 | 1999-05-20 | Bayer Ag | Isothiazolcarbonsäureamide |
-
2002
- 2002-06-27 DE DE10228732A patent/DE10228732A1/de not_active Withdrawn
-
2003
- 2003-06-17 AT AT03732578T patent/ATE308530T1/de not_active IP Right Cessation
- 2003-06-17 JP JP2004516609A patent/JP4551762B2/ja not_active Expired - Lifetime
- 2003-06-17 AU AU2003238510A patent/AU2003238510A1/en not_active Abandoned
- 2003-06-17 KR KR1020047021038A patent/KR101069222B1/ko not_active Expired - Lifetime
- 2003-06-17 CN CNB038203294A patent/CN1325483C/zh not_active Expired - Lifetime
- 2003-06-17 WO PCT/EP2003/006360 patent/WO2004002968A1/de not_active Ceased
- 2003-06-17 DE DE50301572T patent/DE50301572D1/de not_active Expired - Lifetime
- 2003-06-17 EP EP03732578A patent/EP1519926B1/de not_active Expired - Lifetime
- 2003-06-26 TW TW092117350A patent/TWI266766B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JP2005530847A (ja) | 2005-10-13 |
| CN1325483C (zh) | 2007-07-11 |
| DE50301572D1 (de) | 2005-12-08 |
| DE10228732A1 (de) | 2004-01-15 |
| AU2003238510A1 (en) | 2004-01-19 |
| EP1519926A1 (de) | 2005-04-06 |
| EP1519926B1 (de) | 2005-11-02 |
| ATE308530T1 (de) | 2005-11-15 |
| CN1678595A (zh) | 2005-10-05 |
| WO2004002968A1 (de) | 2004-01-08 |
| JP4551762B2 (ja) | 2010-09-29 |
| KR101069222B1 (ko) | 2011-09-30 |
| TW200409762A (en) | 2004-06-16 |
| KR20050008853A (ko) | 2005-01-21 |
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