JP2008546645A5 - - Google Patents
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- Publication number
- JP2008546645A5 JP2008546645A5 JP2008515880A JP2008515880A JP2008546645A5 JP 2008546645 A5 JP2008546645 A5 JP 2008546645A5 JP 2008515880 A JP2008515880 A JP 2008515880A JP 2008515880 A JP2008515880 A JP 2008515880A JP 2008546645 A5 JP2008546645 A5 JP 2008546645A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- trifluoromethyl
- imidazole
- solvent
- nitro
- 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
- -1 potassium alkoxide Chemical class 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- WWTGXYAJVXKEKL-UHFFFAOYSA-N 3-(4-methylimidazol-1-yl)-5-(trifluoromethyl)aniline Chemical compound C1=NC(C)=CN1C1=CC(N)=CC(C(F)(F)F)=C1 WWTGXYAJVXKEKL-UHFFFAOYSA-N 0.000 claims description 5
- 239000011591 potassium Substances 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 2
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 claims description 2
- 229910000105 potassium hydride Inorganic materials 0.000 claims description 2
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 2
- 239000012312 sodium hydride Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 17
- 239000002904 solvent Substances 0.000 claims 8
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N 4-methylimidazole Chemical compound CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 claims 6
- 239000003054 catalyst Substances 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 229910052723 transition metal Inorganic materials 0.000 claims 5
- 150000003624 transition metals Chemical class 0.000 claims 5
- JMLCVCGQBRZYOZ-UHFFFAOYSA-N 4-methyl-1-[3-nitro-5-(trifluoromethyl)phenyl]imidazole Chemical compound C1=NC(C)=CN1C1=CC([N+]([O-])=O)=CC(C(F)(F)F)=C1 JMLCVCGQBRZYOZ-UHFFFAOYSA-N 0.000 claims 4
- 239000002798 polar solvent Substances 0.000 claims 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- SLFVYFOEHHLHDW-UHFFFAOYSA-N n-(trifluoromethyl)aniline Chemical compound FC(F)(F)NC1=CC=CC=C1 SLFVYFOEHHLHDW-UHFFFAOYSA-N 0.000 claims 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical group [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 2
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 1
- 229910052792 caesium Inorganic materials 0.000 claims 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 1
- 229940098779 methanesulfonic acid Drugs 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 238000011946 reduction process Methods 0.000 claims 1
- XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- CBHCSTMTFYDOCX-UHFFFAOYSA-N 3-(4-methylimidazol-1-yl)-5-(trifluoromethyl)benzamide Chemical compound C1=NC(C)=CN1C1=CC(C(N)=O)=CC(C(F)(F)F)=C1 CBHCSTMTFYDOCX-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- VVNXEADCOVSAER-UHFFFAOYSA-N lithium sodium Chemical compound [Li].[Na] VVNXEADCOVSAER-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- UKLNMMHNWFDKNT-UHFFFAOYSA-M sodium chlorite Chemical compound [Na+].[O-]Cl=O UKLNMMHNWFDKNT-UHFFFAOYSA-M 0.000 description 1
- 229960002218 sodium chlorite Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US68897605P | 2005-06-09 | 2005-06-09 | |
| US60/688,976 | 2005-06-09 | ||
| PCT/US2006/022154 WO2006135640A2 (en) | 2005-06-09 | 2006-06-07 | Process for the synthesis of organic compounds |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012208775A Division JP2013035855A (ja) | 2005-06-09 | 2012-09-21 | 有機化合物の合成方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008546645A JP2008546645A (ja) | 2008-12-25 |
| JP2008546645A5 true JP2008546645A5 (enExample) | 2009-07-23 |
| JP5225078B2 JP5225078B2 (ja) | 2013-07-03 |
Family
ID=37149980
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008515880A Expired - Fee Related JP5225078B2 (ja) | 2005-06-09 | 2006-06-07 | 有機化合物の合成方法 |
| JP2012208775A Pending JP2013035855A (ja) | 2005-06-09 | 2012-09-21 | 有機化合物の合成方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012208775A Pending JP2013035855A (ja) | 2005-06-09 | 2012-09-21 | 有機化合物の合成方法 |
Country Status (25)
| Country | Link |
|---|---|
| US (2) | US7781597B2 (enExample) |
| EP (3) | EP2292607B1 (enExample) |
| JP (2) | JP5225078B2 (enExample) |
| KR (2) | KR101249199B1 (enExample) |
| CN (6) | CN102174021B (enExample) |
| AR (1) | AR057056A1 (enExample) |
| AT (1) | ATE540931T1 (enExample) |
| AU (3) | AU2006258050B2 (enExample) |
| BR (1) | BRPI0611683A2 (enExample) |
| CA (4) | CA2942046A1 (enExample) |
| DK (2) | DK2266961T3 (enExample) |
| ES (3) | ES2465522T3 (enExample) |
| GT (1) | GT200600202AA (enExample) |
| HU (1) | HUE028024T2 (enExample) |
| IN (2) | IN2014DN08588A (enExample) |
| JO (1) | JO2758B1 (enExample) |
| MX (1) | MX2007015609A (enExample) |
| MY (1) | MY146795A (enExample) |
| PE (3) | PE20100715A1 (enExample) |
| PL (3) | PL2266961T3 (enExample) |
| PT (3) | PT2292607E (enExample) |
| RU (1) | RU2446162C2 (enExample) |
| SI (2) | SI2266961T1 (enExample) |
| TW (1) | TWI380981B (enExample) |
| WO (1) | WO2006135640A2 (enExample) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1930136B (zh) | 2004-03-05 | 2012-02-08 | 日产化学工业株式会社 | 异*唑啉取代苯甲酰胺化合物及有害生物防除剂 |
| MY146795A (en) * | 2005-06-09 | 2012-09-28 | Novartis Ag | Process for the synthesis of organic compounds |
| TW200803740A (en) | 2005-12-16 | 2008-01-16 | Du Pont | 5-aryl isoxazolines for controlling invertebrate pests |
| TWI412322B (zh) | 2005-12-30 | 2013-10-21 | Du Pont | 控制無脊椎害蟲之異唑啉 |
| BRPI0809770B8 (pt) | 2007-06-13 | 2022-12-06 | Du Pont | Composto e composição para controlar uma praga de invertebrados |
| TWI430995B (zh) | 2007-06-26 | 2014-03-21 | Du Pont | 萘異唑啉無脊椎有害動物控制劑 |
| DK2957284T3 (en) | 2007-06-27 | 2018-02-05 | Du Pont | PROCEDURE TO CHECK ANIMALS FOR ANIMALS |
| TWI600639B (zh) | 2007-08-17 | 2017-10-01 | 杜邦股份有限公司 | 製備５-鹵烷基-４，５-二氫異唑衍生物之化合物 |
| KR20100075996A (ko) | 2007-10-03 | 2010-07-05 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 무척추 해충의 방제를 위한 나프탈렌 이속사졸린 화합물 |
| TWI583664B (zh) | 2008-04-09 | 2017-05-21 | 杜邦股份有限公司 | 羰基化合物及其製備方法 |
| US20100016590A1 (en) * | 2008-07-17 | 2010-01-21 | Teva Pharmaceutical Industries Ltd. | Nilotinib intermediates and preparation thereof |
| EP2530081A3 (en) | 2008-11-05 | 2013-04-10 | Teva Pharmaceutical Industries, Ltd. | Nilotinib HCI crystalline forms |
| WO2010060074A1 (en) * | 2008-11-24 | 2010-05-27 | Teva Pharmaceutical Industries Ltd. | Preparation of nilotinib and intermediates thereof |
| US20110053968A1 (en) | 2009-06-09 | 2011-03-03 | Auspex Pharmaceuticals, Inc. | Aminopyrimidine inhibitors of tyrosine kinase |
| MX2012013758A (es) | 2010-05-27 | 2013-01-24 | Du Pont | Forma cristalina de 4-[5-[3-cloro-5-trifluorometil)fenil]-4,5-dihi dro-5-(trifluorometil)-3-isoxazolil]-n-[2-oxo-2-[(2,2,2-trifluoro etil)amino]etil]-1-naftalenocarboxamida. |
| BR112014015720B1 (pt) | 2011-12-30 | 2020-03-17 | Hanmi Pharm. Co., Ltd. | Derivados de tieno[3,2-d]pirimidina, composição farmacêutica e uso dos mesmos para a prevenção ou tratamento de uma doença causada por ativação anormal de uma proteína quinase |
| CN102592837B (zh) * | 2012-03-12 | 2014-01-15 | 河北师范大学 | 制备超级电容器用四氯合金属季铵盐掺杂聚苯胺电极的方法 |
| CN103694176B (zh) * | 2014-01-07 | 2015-02-18 | 苏州立新制药有限公司 | 尼洛替尼中间体的制备方法 |
| CN104592122B (zh) * | 2014-12-09 | 2018-01-23 | 凯莱英医药集团（天津）股份有限公司 | 3‑(4‑甲基‑1h‑咪唑‑1‑基)‑5‑(三氟甲基)苯胺的制备方法 |
| CN105985293B (zh) * | 2015-03-04 | 2018-04-03 | 埃斯特维华义制药有限公司 | 尼洛替尼中间体的制备方法 |
| EP3095782A1 (en) | 2015-05-18 | 2016-11-23 | Esteve Química, S.A. | New method for preparing 3-(4-methyl-1h-imidazol-1-yl)-5-(trifluoromethyl)benzenamine |
| CN107201532B (zh) * | 2017-05-09 | 2019-08-27 | 吉林凯莱英医药化学有限公司 | 芳香化合物的硝化方法 |
| WO2019130254A1 (en) * | 2018-01-01 | 2019-07-04 | Laurus Labs Ltd | An improved process for 3-(4-methyl-1h-imidazol-1-yl)-5-(trifluoromethyl) aniline |
| CN108530364B (zh) * | 2018-04-10 | 2020-01-21 | 江苏创诺制药有限公司 | 一种3-(4-甲基-1h-咪唑-1-基)-5-三氟甲基苯胺单盐酸盐的晶型及其应用 |
| EP3806858A4 (en) | 2018-06-15 | 2022-03-09 | Handa Pharmaceuticals, Inc. | KINA INHIBITOR SALTS AND COMPOSITIONS THEREOF |
| US11014945B2 (en) * | 2019-04-06 | 2021-05-25 | Trinapco, Inc. | Sulfonyldiazoles and N-(fluorosulfonyl)azoles, and methods of making the same |
| EP3904342A1 (en) | 2020-04-28 | 2021-11-03 | Grindeks, A Joint Stock Company | Process for the preparation of 3-(trifluoromethyl)-5-(4-methyl-1h-imidazole-1-yl)-benzeneamine hydrochloride |
| CN114751836B (zh) * | 2021-02-23 | 2024-05-31 | 四川青木制药有限公司 | 3-(4-甲基-1h-咪唑-1-基)-5-(三氟甲基)苯胺合成方法及其中间体 |
| CN114853734A (zh) * | 2022-06-14 | 2022-08-05 | 海南鑫开源医药科技有限公司 | 一种尼洛替尼游离碱的制备方法 |
| CN116478319B (zh) * | 2022-11-07 | 2025-07-01 | 华北电力大学 | 一种离子共价有机聚合物的制备方法及其在碱性环境吸附ReO4-的应用 |
| CN115626880B (zh) * | 2022-11-15 | 2023-11-14 | 常州大学 | 3-硝基-5-氰基三氟甲苯的合成方法 |
| CN118108670B (zh) * | 2023-12-28 | 2025-07-01 | 江苏希迪制药有限公司 | 尼罗替尼中间体3-(4-甲基-1h-咪唑-1-基)-5-(三氟甲基)苯胺的精制纯化方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU1051076A1 (ru) * | 1982-04-09 | 1983-10-30 | Алтайский политехнический институт | Способ получени производных имидазола |
| CA1292234C (en) * | 1984-05-29 | 1991-11-19 | Simon Fraser Campbell | Heterocyclic-substituted quinolone inotropic agents |
| GB8413685D0 (en) * | 1984-05-29 | 1984-07-04 | Pfizer Ltd | Quinolone inotropic agents |
| GB8502267D0 (en) * | 1985-01-30 | 1985-02-27 | Pfizer Ltd | Quinolone inotropic agents |
| HN2001000008A (es) * | 2000-01-21 | 2003-12-11 | Inc Agouron Pharmaceuticals | Compuesto de amida y composiciones farmaceuticas para inhibir proteinquinasas, y su modo de empleo |
| GB0023383D0 (en) * | 2000-09-23 | 2000-11-08 | Synprotec Ltd | 3,5-Bis (Trifluormethyl)Benzene derivatives |
| PE20040522A1 (es) * | 2002-05-29 | 2004-09-28 | Novartis Ag | Derivados de diarilurea dependientes de la cinasa de proteina |
| GB0215676D0 (en) * | 2002-07-05 | 2002-08-14 | Novartis Ag | Organic compounds |
| GB0222514D0 (en) | 2002-09-27 | 2002-11-06 | Novartis Ag | Organic compounds |
| CN1939910A (zh) * | 2004-12-31 | 2007-04-04 | 孙飘扬 | 氨基嘧啶类化合物及其盐和其制备方法与药物用途 |
| GT200600207A (es) * | 2005-06-09 | 2007-01-15 | Novartis Ag | Proceso para la síntesis de compuestos orgánicos |
| MY146795A (en) * | 2005-06-09 | 2012-09-28 | Novartis Ag | Process for the synthesis of organic compounds |
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2006
- 2006-05-31 MY MYPI20062506A patent/MY146795A/en unknown
- 2006-06-06 JO JO2006161A patent/JO2758B1/en active
- 2006-06-07 PT PT101719425T patent/PT2292607E/pt unknown
- 2006-06-07 DK DK10171941.7T patent/DK2266961T3/en active
- 2006-06-07 EP EP10171942.5A patent/EP2292607B1/en active Active
- 2006-06-07 PT PT06772447T patent/PT1896426E/pt unknown
- 2006-06-07 KR KR1020077028642A patent/KR101249199B1/ko not_active Expired - Fee Related
- 2006-06-07 PE PE2010000467A patent/PE20100715A1/es not_active Application Discontinuation
- 2006-06-07 SI SI200632010T patent/SI2266961T1/sl unknown
- 2006-06-07 PE PE2006000628A patent/PE20070109A1/es not_active Application Discontinuation
- 2006-06-07 US US11/915,691 patent/US7781597B2/en active Active
- 2006-06-07 CA CA2942046A patent/CA2942046A1/en not_active Abandoned
- 2006-06-07 EP EP10171941.7A patent/EP2266961B1/en active Active
- 2006-06-07 PE PE2010000468A patent/PE20100716A1/es not_active Application Discontinuation
- 2006-06-07 CN CN2011100581788A patent/CN102174021B/zh not_active Expired - Fee Related
- 2006-06-07 AT AT06772447T patent/ATE540931T1/de active
- 2006-06-07 DK DK10171942.5T patent/DK2292607T3/da active
- 2006-06-07 BR BRPI0611683-3A patent/BRPI0611683A2/pt active Search and Examination
- 2006-06-07 EP EP06772447A patent/EP1896426B1/en active Active
- 2006-06-07 HU HUE10171941A patent/HUE028024T2/en unknown
- 2006-06-07 CN CN200680019924XA patent/CN101189212B/zh not_active Expired - Fee Related
- 2006-06-07 ES ES10171942.5T patent/ES2465522T3/es active Active
- 2006-06-07 IN IN8588DEN2014 patent/IN2014DN08588A/en unknown
- 2006-06-07 PL PL10171941T patent/PL2266961T3/pl unknown
- 2006-06-07 RU RU2007148238/04A patent/RU2446162C2/ru active
- 2006-06-07 CN CN2011100572469A patent/CN102174019B/zh not_active Expired - Fee Related
- 2006-06-07 KR KR1020127011979A patent/KR101283109B1/ko not_active Expired - Fee Related
- 2006-06-07 PL PL06772447T patent/PL1896426T3/pl unknown
- 2006-06-07 ES ES06772447T patent/ES2380489T3/es active Active
- 2006-06-07 AR ARP060102367A patent/AR057056A1/es unknown
- 2006-06-07 IN IN8578DEN2014 patent/IN2014DN08578A/en unknown
- 2006-06-07 WO PCT/US2006/022154 patent/WO2006135640A2/en not_active Ceased
- 2006-06-07 CN CN2011100581769A patent/CN102180796A/zh active Pending
- 2006-06-07 AU AU2006258050A patent/AU2006258050B2/en not_active Ceased
- 2006-06-07 CN CN2011100574125A patent/CN102180836B/zh not_active Expired - Fee Related
- 2006-06-07 CA CA2611280A patent/CA2611280C/en active Active
- 2006-06-07 CA CA2886482A patent/CA2886482C/en active Active
- 2006-06-07 CN CN2011100581773A patent/CN102174020B/zh not_active Expired - Fee Related
- 2006-06-07 PT PT101719417T patent/PT2266961E/pt unknown
- 2006-06-07 MX MX2007015609A patent/MX2007015609A/es active IP Right Grant
- 2006-06-07 PL PL10171942T patent/PL2292607T3/pl unknown
- 2006-06-07 ES ES10171941.7T patent/ES2558696T3/es active Active
- 2006-06-07 JP JP2008515880A patent/JP5225078B2/ja not_active Expired - Fee Related
- 2006-06-07 SI SI200631789T patent/SI2292607T1/sl unknown
- 2006-06-07 CA CA2833394A patent/CA2833394C/en active Active
- 2006-06-08 TW TW095120304A patent/TWI380981B/zh not_active IP Right Cessation
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2010
- 2010-07-12 US US12/834,295 patent/US8008504B2/en not_active Expired - Fee Related
- 2010-11-11 AU AU2010241374A patent/AU2010241374B2/en not_active Ceased
-
2011
- 2011-03-09 AU AU2011201044A patent/AU2011201044A1/en not_active Abandoned
-
2012
- 2012-05-17 GT GT200600202AK patent/GT200600202AA/es unknown
- 2012-09-21 JP JP2012208775A patent/JP2013035855A/ja active Pending
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