JP2003512456A5 - - Google Patents
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- Publication number
- JP2003512456A5 JP2003512456A5 JP2001533114A JP2001533114A JP2003512456A5 JP 2003512456 A5 JP2003512456 A5 JP 2003512456A5 JP 2001533114 A JP2001533114 A JP 2001533114A JP 2001533114 A JP2001533114 A JP 2001533114A JP 2003512456 A5 JP2003512456 A5 JP 2003512456A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- process according
- compound
- disulfide
- iii
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 description 41
- 150000001875 compounds Chemical class 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 9
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 8
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 6
- 150000002367 halogens Chemical class 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 238000005260 corrosion Methods 0.000 description 4
- 230000007797 corrosion Effects 0.000 description 4
- 125000001188 haloalkyl group Chemical group 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- XYPISWUKQGWYGX-UHFFFAOYSA-N 2,2,2-trifluoroethaneperoxoic acid Chemical compound OOC(=O)C(F)(F)F XYPISWUKQGWYGX-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- RJCQBQGAPKAMLL-UHFFFAOYSA-N bromotrifluoromethane Chemical compound FC(F)(F)Br RJCQBQGAPKAMLL-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000002228 disulfide group Chemical group 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000004438 haloalkoxy group Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- FPPLREPCQJZDAQ-UHFFFAOYSA-N 2-methylpentanedinitrile Chemical compound N#CC(C)CCC#N FPPLREPCQJZDAQ-UHFFFAOYSA-N 0.000 description 1
- ZOCSXAVNDGMNBV-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile Chemical compound NC1=C(S(=O)C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl ZOCSXAVNDGMNBV-UHFFFAOYSA-N 0.000 description 1
- KYWRZLCFDFEWBI-UHFFFAOYSA-N 5-amino-4-[[5-amino-3-cyano-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]pyrazol-4-yl]disulfanyl]-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]pyrazole-3-carbonitrile Chemical compound N#CC1=NN(C=2C(=CC(=CC=2Cl)C(F)(F)F)Cl)C(N)=C1SSC(C(=N1)C#N)=C(N)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl KYWRZLCFDFEWBI-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 0 CC*1c(*(*=C2*)C(C)=C2O)c(*)cc(*)c1 Chemical compound CC*1c(*(*=C2*)C(C)=C2O)c(*)cc(*)c1 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- -1 aromatic nitrile Chemical class 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- FQXWEKADCSXYOC-UHFFFAOYSA-N fipronil-sulfide Chemical compound NC1=C(SC(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl FQXWEKADCSXYOC-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/EP1999/008687 WO2001030760A1 (en) | 1999-10-22 | 1999-10-22 | Process for preparing 4-trifluoromethylsulphinylpyrazole derivative |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2003512456A JP2003512456A (ja) | 2003-04-02 |
| JP2003512456A5 true JP2003512456A5 (https=) | 2006-12-14 |
| JP4666863B2 JP4666863B2 (ja) | 2011-04-06 |
Family
ID=8167491
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001533114A Expired - Fee Related JP4666863B2 (ja) | 1999-10-22 | 1999-10-22 | ４−トリフルオロメチルスルフィニルピラゾール誘導体の調製プロセス |
Country Status (30)
| Country | Link |
|---|---|
| US (2) | US6620943B1 (https=) |
| EP (1) | EP1222173B1 (https=) |
| JP (1) | JP4666863B2 (https=) |
| KR (2) | KR100665599B1 (https=) |
| CN (3) | CN1896066B (https=) |
| AT (1) | ATE273961T1 (https=) |
| AU (1) | AU783139B2 (https=) |
| BG (1) | BG65483B1 (https=) |
| BR (1) | BR9917518B1 (https=) |
| CA (1) | CA2384283C (https=) |
| CZ (1) | CZ299822B6 (https=) |
| DE (1) | DE69919599T2 (https=) |
| DK (1) | DK1222173T3 (https=) |
| EA (1) | EA005077B1 (https=) |
| ES (1) | ES2222743T3 (https=) |
| HR (1) | HRP20020438B1 (https=) |
| HU (1) | HU229393B1 (https=) |
| IL (2) | IL149152A0 (https=) |
| IN (2) | IN2005MU00818A (https=) |
| ME (1) | MEP7808A (https=) |
| MX (1) | MX229662B (https=) |
| NZ (2) | NZ527896A (https=) |
| PL (1) | PL206482B1 (https=) |
| PT (1) | PT1222173E (https=) |
| RO (1) | RO121209B1 (https=) |
| TR (2) | TR200202806T2 (https=) |
| TW (1) | TW553936B (https=) |
| UA (1) | UA73752C2 (https=) |
| WO (1) | WO2001030760A1 (https=) |
| ZA (1) | ZA200201961B (https=) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1160349C (zh) | 1999-06-29 | 2004-08-04 | 日本农药株式会社 | 吡唑衍生物及其制备方法,以及含有该衍生物作为有效成分的有害生物防治剂 |
| WO2005023774A1 (en) * | 2003-09-11 | 2005-03-17 | Cheminova A/S | Process for the preparation of a trifluoromethylthioether |
| CN100586934C (zh) * | 2003-11-07 | 2010-02-03 | 凯米诺瓦有限公司 | 制备三氟甲基硫醚的方法 |
| DE102004020069C5 (de) | 2004-04-24 | 2013-12-05 | Voith Patent Gmbh | Verfahren zum Satinieren einer Papierbahn |
| AU2013203236A1 (en) * | 2005-12-14 | 2013-05-02 | Makhteshim Chemical Works Ltd. | Polymorphs and amorphous forms of 5-amino-1-[2,6- dichloro-4-(trifluoromethyl)phenyl]-4- [(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile |
| WO2007069254A2 (en) | 2005-12-14 | 2007-06-21 | Makhteshim Chemical Works Ltd. | POLYMORPHS AND AMORPHOUS FORMS OF 5-AMINO-l-[2,6- DICHLORO-4-(TRIFLUOROMETHYL)PHENYL]-4- [(TRIFLUOROMETHYL)SULFINYL]-IH-PYRAZOLE-3-CARBONITRILE |
| NZ568025A (en) | 2006-04-25 | 2011-02-25 | Gharda Chemicals Ltd | Process for the preparation of fipronil, an insecticide, and related pyrazoles |
| CN101168529B (zh) * | 2006-10-24 | 2011-03-23 | 温州大学 | 氟虫腈、乙虫腈及其衍生物的合成方法 |
| AU2007316720B2 (en) | 2006-11-10 | 2013-05-09 | Basf Se | Process for the sulfinylation of a pyrazole derivative |
| BRPI0718717A2 (pt) * | 2006-11-10 | 2013-11-26 | Basf Se | Modificação cristalina ii de fipronil, fipronil sólido, processo para preparar a modificação cristalina ii, mistura pesticida ou parasiticida sinergística, composição pesticida ou parasiticida, uso da modificação cristalina ii, ou do fipronil sólido, ou da mistura, ou da composição, métodos para controlar pragas, para proteger uma planta da infestação e ataque por pragas, para proteger semente, e para tratar, controlar, prevenir ou proteger animais contra infestação ou infecção por parasitas, semente, uso da modificação cristalina ii, ou do fipronil sólido, ou da mistura, ou da composição, e, processo para a preparação de uma composição para trtar, controlar, prevenir ou proteger animais contra infestação ou infecção por parasitas |
| US8791046B2 (en) | 2006-11-10 | 2014-07-29 | Basf Se | Crystalline modification of fipronil |
| UA110598C2 (uk) | 2006-11-10 | 2016-01-25 | Басф Се | Спосіб одержання кристалічної модифікації фіпронілу |
| JP5931322B2 (ja) | 2006-11-10 | 2016-06-08 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | フィプロニルの結晶変態 |
| PT2081908E (pt) | 2006-11-10 | 2013-06-28 | Basf Agro B V Arnhem Nl Zurich Branch | Processo de sulfinilação de um derivado pirazolo |
| DK2349987T3 (da) | 2008-10-02 | 2013-03-11 | Basf Se | Fremgangsmåde til fremstilling og oprensning af trifluormethansulfinsyre |
| WO2010049746A1 (en) * | 2008-10-27 | 2010-05-06 | Dynamit Nobel Gmbh Explosivstoff-Und Systemtechnic | Process for the synthesis of fipronil |
| EP2493860B1 (en) * | 2009-10-30 | 2014-01-15 | Basf Se | Process for the preparation of 4-sulfinyl-pyrazole derivatives |
| AU2010100462A4 (en) | 2010-03-03 | 2010-06-17 | Keki Hormusji Gharda | A process for the synthesis of Fipronil |
| IT1400666B1 (it) * | 2010-07-07 | 2013-06-28 | Finchimica Srl | Procedimento per la sintesi di 5-amino, 1-fenil, 3-ciano, 4-trifluorometil sulfinil pirazoli. |
| KR20130124473A (ko) | 2010-07-12 | 2013-11-14 | 얼비타 플랜트 프로텍션, 어 브랜치 오브 셀시우스 프로퍼티 비.브이. | 피프로닐 제조 방법 |
| AU2012100035A4 (en) * | 2011-01-14 | 2012-02-09 | Keki Hormusji Gharda | Polymorphism in 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoro methyl sulfinyl pyrazole |
| US9029564B2 (en) | 2011-05-30 | 2015-05-12 | Keki Hormusji Gharda | Process for synthesis of fipronil |
| CN102633722B (zh) * | 2012-03-20 | 2015-05-06 | 金坛市凌云动物保健品有限公司 | 一种非泼罗尼的制备方法 |
| TWI579274B (zh) | 2012-04-20 | 2017-04-21 | 龍馬躍公司 | 製備１－芳基－５－烷基吡唑化合物的改良方法 |
| CN102690232A (zh) * | 2012-05-30 | 2012-09-26 | 河南中医学院 | 一种氟虫腈中间体的合成方法 |
| US9049860B2 (en) | 2013-04-17 | 2015-06-09 | The Hartz Mountain Corporation | Ectoparasiticidal methods |
| CN105254565A (zh) * | 2015-09-30 | 2016-01-20 | 乐平市康鑫医药化工有限公司 | 由氰基吡唑一锅法合成硫醚的工艺方法 |
| CN106977460A (zh) * | 2017-04-19 | 2017-07-25 | 江苏托球农化股份有限公司 | 1‑(2,6‑二氯‑4‑三氟甲基)苯基‑3‑氰基‑4‑乙巯基‑5‑氨基吡唑的合成 |
| EP3412658A1 (en) | 2017-06-09 | 2018-12-12 | Solvay Sa | Processes for the manufacture of sulfur-substitued pyrazole derivatives |
| EP3412659A1 (en) | 2017-06-09 | 2018-12-12 | Solvay Sa | Processes for the manufacture of sulfur-substituted pyrazole derivatives |
| CN112430213A (zh) * | 2020-12-03 | 2021-03-02 | 江苏优普生物化学科技股份有限公司 | 一种三氟甲硫基吡唑合成工艺 |
| CN113149909B (zh) * | 2021-03-24 | 2022-04-19 | 台州达辰药业有限公司 | 5-氨基-3-氰基-1-(2,6-二氯-4-三氟甲基-苯基)吡唑二硫化物制备方法 |
| CN113480482B (zh) * | 2021-07-05 | 2022-11-18 | 海正药业南通有限公司 | 一种非泼罗尼中间体的合成方法 |
| CN114213330A (zh) * | 2021-12-29 | 2022-03-22 | 天和药业股份有限公司 | 一种氟虫腈精制母液的处理方法 |
| CN121293157A (zh) * | 2025-12-11 | 2026-01-09 | 长青(湖北)生物科技有限公司 | 一种制备氟虫腈及其中间体的工艺 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2716453B1 (fr) * | 1994-02-22 | 1996-03-29 | Rhone Poulenc Agrochimie | Procédé de sulfinylation de composés hétérocycliques. |
| DE3602728A1 (de) * | 1985-05-17 | 1986-11-20 | Bayer Ag, 51373 Leverkusen | Schaedlingsbekaempfungsmittel auf basis von pyrazolderivaten |
| GB8713768D0 (en) * | 1987-06-12 | 1987-07-15 | May & Baker Ltd | Compositions of matter |
| US5232940A (en) | 1985-12-20 | 1993-08-03 | Hatton Leslie R | Derivatives of N-phenylpyrazoles |
| US5547974A (en) * | 1985-12-20 | 1996-08-20 | Rhone-Poulenc Agriculture Ltd. | Derivatives of N-phenylpyrazoles |
| CA2004776C (fr) | 1988-12-13 | 2000-04-25 | Claude Wakselman | Procede de preparation de perfluoroalkylthioethers |
-
1999
- 1999-10-22 HR HR20020438A patent/HRP20020438B1/xx not_active IP Right Cessation
- 1999-10-22 TR TR2002/02806T patent/TR200202806T2/xx unknown
- 1999-10-22 DK DK99955978T patent/DK1222173T3/da active
- 1999-10-22 ES ES99955978T patent/ES2222743T3/es not_active Expired - Lifetime
- 1999-10-22 RO ROA200200317A patent/RO121209B1/ro unknown
- 1999-10-22 CZ CZ20021384A patent/CZ299822B6/cs not_active IP Right Cessation
- 1999-10-22 PT PT99955978T patent/PT1222173E/pt unknown
- 1999-10-22 HU HU0203206A patent/HU229393B1/hu unknown
- 1999-10-22 NZ NZ527896A patent/NZ527896A/en not_active IP Right Cessation
- 1999-10-22 CA CA002384283A patent/CA2384283C/en not_active Expired - Fee Related
- 1999-10-22 CN CN2004101300014A patent/CN1896066B/zh not_active Expired - Lifetime
- 1999-10-22 CN CNB998060828A patent/CN1163488C/zh not_active Expired - Lifetime
- 1999-10-22 UA UA2002054165A patent/UA73752C2/uk unknown
- 1999-10-22 PL PL354611A patent/PL206482B1/pl not_active IP Right Cessation
- 1999-10-22 WO PCT/EP1999/008687 patent/WO2001030760A1/en not_active Ceased
- 1999-10-22 KR KR1020067017067A patent/KR100665599B1/ko not_active Expired - Fee Related
- 1999-10-22 MX MXPA02003944 patent/MX229662B/es active IP Right Grant
- 1999-10-22 KR KR1020027005011A patent/KR100665598B1/ko not_active Expired - Fee Related
- 1999-10-22 IN IN818MU2005 patent/IN2005MU00818A/en unknown
- 1999-10-22 NZ NZ517770A patent/NZ517770A/en not_active IP Right Cessation
- 1999-10-22 AT AT99955978T patent/ATE273961T1/de active
- 1999-10-22 AU AU12707/00A patent/AU783139B2/en not_active Expired
- 1999-10-22 EP EP99955978A patent/EP1222173B1/en not_active Expired - Lifetime
- 1999-10-22 BR BRPI9917518-5A patent/BR9917518B1/pt not_active IP Right Cessation
- 1999-10-22 TR TR2002/01072T patent/TR200201072T2/xx unknown
- 1999-10-22 ME MEP-78/08A patent/MEP7808A/xx unknown
- 1999-10-22 CN CN2008101863366A patent/CN101445483B/zh not_active Expired - Lifetime
- 1999-10-22 DE DE69919599T patent/DE69919599T2/de not_active Expired - Lifetime
- 1999-10-22 EA EA200200481A patent/EA005077B1/ru not_active IP Right Cessation
- 1999-10-22 US US10/111,000 patent/US6620943B1/en not_active Expired - Lifetime
- 1999-10-22 IL IL14915299A patent/IL149152A0/xx active IP Right Grant
- 1999-10-22 JP JP2001533114A patent/JP4666863B2/ja not_active Expired - Fee Related
-
2000
- 2000-10-11 TW TW089121214A patent/TW553936B/zh not_active IP Right Cessation
-
2002
- 2002-03-08 ZA ZA200201961A patent/ZA200201961B/en unknown
- 2002-04-01 IN IN312MU2002 patent/IN2002MU00312A/en unknown
- 2002-04-15 IL IL149152A patent/IL149152A/en not_active IP Right Cessation
- 2002-04-17 BG BG106622A patent/BG65483B1/bg unknown
-
2003
- 2003-07-03 US US10/611,979 patent/US6881848B2/en not_active Expired - Fee Related
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