JP2010503694A5 - - Google Patents
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- Publication number
- JP2010503694A5 JP2010503694A5 JP2009528433A JP2009528433A JP2010503694A5 JP 2010503694 A5 JP2010503694 A5 JP 2010503694A5 JP 2009528433 A JP2009528433 A JP 2009528433A JP 2009528433 A JP2009528433 A JP 2009528433A JP 2010503694 A5 JP2010503694 A5 JP 2010503694A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- salt
- lithium
- converting
- 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
- 150000001875 compounds Chemical class 0.000 claims description 49
- 238000000034 method Methods 0.000 claims description 35
- -1 salt compound Chemical class 0.000 claims description 9
- 239000003153 chemical reaction reagent Substances 0.000 claims description 8
- 150000002642 lithium compounds Chemical class 0.000 claims description 5
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 claims description 2
- KJJBSBKRXUVBMX-UHFFFAOYSA-N magnesium;butane Chemical compound [Mg+2].CCC[CH2-].CCC[CH2-] KJJBSBKRXUVBMX-UHFFFAOYSA-N 0.000 claims description 2
- YHNWUQFTJNJVNU-UHFFFAOYSA-N magnesium;butane;ethane Chemical compound [Mg+2].[CH2-]C.CCC[CH2-] YHNWUQFTJNJVNU-UHFFFAOYSA-N 0.000 claims description 2
- 150000002902 organometallic compounds Chemical class 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 9
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 6
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 4
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 claims 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims 4
- 239000001103 potassium chloride Substances 0.000 claims 4
- 235000011164 potassium chloride Nutrition 0.000 claims 4
- SIOVKLKJSOKLIF-HJWRWDBZSA-N trimethylsilyl (1z)-n-trimethylsilylethanimidate Chemical compound C[Si](C)(C)OC(/C)=N\[Si](C)(C)C SIOVKLKJSOKLIF-HJWRWDBZSA-N 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical group OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 3
- 150000004796 dialkyl magnesium compounds Chemical class 0.000 claims 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 2
- ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical group COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 claims 2
- XCOBLONWWXQEBS-KPKJPENVSA-N N,O-bis(trimethylsilyl)trifluoroacetamide Chemical compound C[Si](C)(C)O\C(C(F)(F)F)=N\[Si](C)(C)C XCOBLONWWXQEBS-KPKJPENVSA-N 0.000 claims 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims 2
- 239000003638 chemical reducing agent Substances 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 229910001629 magnesium chloride Inorganic materials 0.000 claims 2
- 150000002900 organolithium compounds Chemical class 0.000 claims 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims 2
- 239000003880 polar aprotic solvent Substances 0.000 claims 2
- 229910000077 silane Inorganic materials 0.000 claims 2
- 239000011780 sodium chloride Substances 0.000 claims 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 2
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical group CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 claims 2
- ZWDVQMVZZYIAHO-UHFFFAOYSA-N 2-fluorobenzaldehyde Chemical compound FC1=CC=CC=C1C=O ZWDVQMVZZYIAHO-UHFFFAOYSA-N 0.000 claims 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N Butanol Natural products CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 1
- KKUZFMJIXIFTND-UHFFFAOYSA-N CCCCCC[Mg] Chemical compound CCCCCC[Mg] KKUZFMJIXIFTND-UHFFFAOYSA-N 0.000 claims 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 1
- 239000013078 crystal Substances 0.000 claims 1
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- NWYYWIJOWOLJNR-RXMQYKEDSA-N l-valinol Chemical compound CC(C)[C@H](N)CO NWYYWIJOWOLJNR-RXMQYKEDSA-N 0.000 claims 1
- 159000000003 magnesium salts Chemical class 0.000 claims 1
- 150000002736 metal compounds Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 150000004791 alkyl magnesium halides Chemical class 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- YAOZCMANASAVFN-UHFFFAOYSA-N 3-chloro-2-fluorobenzaldehyde Chemical compound FC1=C(Cl)C=CC=C1C=O YAOZCMANASAVFN-UHFFFAOYSA-N 0.000 description 1
- NEGXJEZDASAQHQ-UHFFFAOYSA-N CCCCO.CCCC[Mg]CC Chemical compound CCCCO.CCCC[Mg]CC NEGXJEZDASAQHQ-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US84402006P | 2006-09-12 | 2006-09-12 | |
| US60/844,020 | 2006-09-12 | ||
| US90536507P | 2007-03-07 | 2007-03-07 | |
| US60/905,365 | 2007-03-07 | ||
| PCT/US2007/078157 WO2008033836A2 (en) | 2006-09-12 | 2007-09-11 | Process and intermediates for preparing integrase inhibitors |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012230583A Division JP2013047248A (ja) | 2006-09-12 | 2012-10-18 | インテグラーゼ阻害剤を調製するためのプロセスおよび中間体 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010503694A JP2010503694A (ja) | 2010-02-04 |
| JP2010503694A5 true JP2010503694A5 (https=) | 2012-06-28 |
| JP5221544B2 JP5221544B2 (ja) | 2013-06-26 |
Family
ID=39092311
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009528433A Expired - Fee Related JP5221544B2 (ja) | 2006-09-12 | 2007-09-11 | インテグラーゼ阻害剤を調製するためのプロセスおよび中間体 |
| JP2012230583A Withdrawn JP2013047248A (ja) | 2006-09-12 | 2012-10-18 | インテグラーゼ阻害剤を調製するためのプロセスおよび中間体 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012230583A Withdrawn JP2013047248A (ja) | 2006-09-12 | 2012-10-18 | インテグラーゼ阻害剤を調製するためのプロセスおよび中間体 |
Country Status (23)
| Country | Link |
|---|---|
| US (3) | US7825252B2 (https=) |
| EP (2) | EP2069280B1 (https=) |
| JP (2) | JP5221544B2 (https=) |
| KR (2) | KR101555089B1 (https=) |
| CN (4) | CN105315154A (https=) |
| AP (1) | AP3004A (https=) |
| AR (1) | AR063710A1 (https=) |
| AU (1) | AU2007296555B2 (https=) |
| BR (1) | BRPI0716752A2 (https=) |
| CA (1) | CA2661943C (https=) |
| EA (1) | EA022099B1 (https=) |
| ES (1) | ES2536923T3 (https=) |
| HK (2) | HK1221454A1 (https=) |
| HR (1) | HRP20090213B1 (https=) |
| IL (2) | IL197527A (https=) |
| MX (1) | MX2009002689A (https=) |
| NO (1) | NO342907B1 (https=) |
| NZ (1) | NZ575542A (https=) |
| PT (1) | PT2069280E (https=) |
| SG (2) | SG10201501782UA (https=) |
| TW (1) | TWI411602B (https=) |
| WO (1) | WO2008033836A2 (https=) |
| ZA (1) | ZA200901576B (https=) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SK2662004A3 (sk) * | 2002-11-20 | 2005-06-02 | Japan Tobacco, Inc. | Zlúčenina s obsahom 4-oxochinolínu a jej použitie ako inhibítora integráz |
| EP1976517A1 (en) * | 2005-12-30 | 2008-10-08 | Gilead Sciences, Inc. | Methods for improving the pharmacokinetics of hiv integrase inhibitors |
| WO2007102499A1 (ja) | 2006-03-06 | 2007-09-13 | Japan Tobacco Inc. | ４－オキソキノリン化合物の製造方法 |
| ES2531190T3 (es) | 2006-03-06 | 2015-03-11 | Japan Tobacco Inc | Método para producir un compuesto de 4-oxoquinolina |
| WO2008033836A2 (en) | 2006-09-12 | 2008-03-20 | Gilead Sciences, Inc. | Process and intermediates for preparing integrase inhibitors |
| AR067184A1 (es) * | 2007-06-29 | 2009-09-30 | Gilead Sciences Inc | Uso de 6-(3-cloro-2-fluorbencil)-1-[(2s)-1-hidroxi-3-metilbutan-2-il]-7-metoxi-4-oxo-1,4-dihidroquinolina-3-carboxilico. composicion farmaceutica |
| US20100331331A1 (en) * | 2007-06-29 | 2010-12-30 | Therapeutic Compositons And Use Thereof | Therapeutic compositions and the use thereof |
| AR068403A1 (es) * | 2007-09-11 | 2009-11-18 | Gilead Sciences Inc | Proceso e intermediarios para la preparacion de inhibidores de integrasa |
| ES3018133T3 (en) | 2011-11-30 | 2025-05-14 | Univ Emory | Jak inhibitors for use in the prevention or treatment of a viral disease caused by a coronaviridae |
| CN102603499A (zh) * | 2012-03-01 | 2012-07-25 | 南京药石药物研发有限公司 | 1-溴-4-氟-5-异丙基-2-甲氧基苯的合成方法 |
| CN102746143A (zh) * | 2012-07-24 | 2012-10-24 | 上海灏翔生物科技有限公司 | L-薄荷羧酸的一种高立体选择性合成方法 |
| AU2013296289B2 (en) | 2012-08-03 | 2017-10-05 | Gilead Sciences, Inc. | Process and intermediates for preparing integrase inhibitors |
| CZ304983B6 (cs) | 2012-10-12 | 2015-03-11 | Zentiva, K.S. | Způsob výroby a nové intermediáty syntézy elvitegraviru |
| CZ304984B6 (cs) | 2012-10-12 | 2015-03-11 | Zentiva, K.S. | Zlepšený způsob výroby a nové intermediáty syntézy elvitegraviru |
| EA030003B1 (ru) | 2012-12-21 | 2018-06-29 | Джилид Сайэнс, Инк. | Полициклическое карбамоилпиридоновое соединение и его фармацевтическое применение для лечения вич-инфекции |
| CZ307255B6 (cs) * | 2013-07-11 | 2018-05-02 | Zentiva, K.S. | Nový způsob přípravy elvitegraviru |
| NO2865735T3 (https=) | 2013-07-12 | 2018-07-21 | ||
| ES2859102T3 (es) | 2013-07-12 | 2021-10-01 | Gilead Sciences Inc | Compuestos de carbamoilpiridona policíclica y su uso para el tratamiento de infecciones por VIH |
| TW201613936A (en) | 2014-06-20 | 2016-04-16 | Gilead Sciences Inc | Crystalline forms of(2R,5S,13aR)-8-hydroxy-7,9-dioxo-n-(2,4,6-trifluorobenzyl)-2,3,4,5,7,9,13,13a-octahydro-2,5-methanopyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazepine-10-carboxamide |
| TWI677489B (zh) | 2014-06-20 | 2019-11-21 | 美商基利科學股份有限公司 | 多環型胺甲醯基吡啶酮化合物之合成 |
| NO2717902T3 (https=) | 2014-06-20 | 2018-06-23 | ||
| TWI695003B (zh) | 2014-12-23 | 2020-06-01 | 美商基利科學股份有限公司 | 多環胺甲醯基吡啶酮化合物及其醫藥用途 |
| KR20190057158A (ko) | 2015-04-02 | 2019-05-27 | 길리애드 사이언시즈, 인코포레이티드 | 폴리시클릭-카르바모일피리돈 화합물 및 그의 제약 용도 |
| CN112661698A (zh) * | 2021-01-14 | 2021-04-16 | 浙江海森药业股份有限公司 | 一种艾维雷韦的制备方法 |
Family Cites Families (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US36684A (en) * | 1862-10-14 | Improvement in tailors press-board holders | ||
| US93467A (en) * | 1869-08-10 | Improved machine for bending car-hooks | ||
| US93482A (en) * | 1869-08-10 | Improved roofing-composition | ||
| US999366A (en) * | 1910-09-30 | 1911-08-01 | John M Gilmore | Device for the manufacture of dental crowns. |
| DE3501247A1 (de) * | 1985-01-16 | 1986-07-17 | Bayer Ag, 5090 Leverkusen | Aminoacrylsaeure-derivate |
| MXPA03005338A (es) * | 2000-12-14 | 2003-10-06 | Procter & Gamble | Etapa de ciclizacion en el procedimiento de elaboracion de quinolonas y naftiridinas. |
| TW200300349A (en) | 2001-11-19 | 2003-06-01 | Sankyo Co | A 4-oxoqinoline derivative |
| AU2003235447A1 (en) | 2002-05-31 | 2003-12-19 | Banyu Pharmaceutical Co., Ltd. | Method of substituent introduction through halogen-metal exchange reaction |
| US6803469B2 (en) * | 2002-08-05 | 2004-10-12 | The Procter & Gamble Company | Process for preparing quinolone antibiotic intermediates |
| TW200409759A (en) | 2002-09-25 | 2004-06-16 | Wyeth Corp | Substituted 4-(indazol-3-yl)phenols |
| CN100375742C (zh) * | 2002-11-20 | 2008-03-19 | 日本烟草产业株式会社 | 4-氧代喹啉化合物及其用途 |
| SK2662004A3 (sk) * | 2002-11-20 | 2005-06-02 | Japan Tobacco, Inc. | Zlúčenina s obsahom 4-oxochinolínu a jej použitie ako inhibítora integráz |
| EP1582523A1 (en) | 2004-04-02 | 2005-10-05 | Ludwig-Maximilians-Universität München | Method of preparing organomagnesium compounds |
| EP1582524B1 (en) | 2004-04-02 | 2008-08-13 | Ludwig Maximilians Universität | Method of preparing organomagnesium compounds |
| US7531554B2 (en) * | 2004-05-20 | 2009-05-12 | Japan Tobacco Inc. | 4-oxoquinoline compound and use thereof as HIV integrase inhibitor |
| MY134672A (en) | 2004-05-20 | 2007-12-31 | Japan Tobacco Inc | Stable crystal of 4-oxoquinoline compound |
| EP1758581A1 (en) | 2004-05-21 | 2007-03-07 | Japan Tobacco, Inc. | Combinations comprising a 4-isoquinolone derivative and anti-hiv agents |
| WO2007063869A1 (ja) | 2005-11-30 | 2007-06-07 | Japan Tobacco Inc. | 高純度キノロン化合物の製造方法 |
| US20090233964A1 (en) * | 2005-12-30 | 2009-09-17 | Gilead Sciences, Inc. | Methods for improving the pharmacokinetics of hiv integrase inhibitors |
| ES2531190T3 (es) * | 2006-03-06 | 2015-03-11 | Japan Tobacco Inc | Método para producir un compuesto de 4-oxoquinolina |
| WO2007102499A1 (ja) | 2006-03-06 | 2007-09-13 | Japan Tobacco Inc. | ４－オキソキノリン化合物の製造方法 |
| TW200811153A (en) * | 2006-06-23 | 2008-03-01 | Japan Tobacco Inc | 6-(heterocyclyl-substituted benzyl)-4-oxoquinoline compound and use thereof as HIV integrase inhibitor |
| WO2008033836A2 (en) * | 2006-09-12 | 2008-03-20 | Gilead Sciences, Inc. | Process and intermediates for preparing integrase inhibitors |
| US20100331331A1 (en) | 2007-06-29 | 2010-12-30 | Therapeutic Compositons And Use Thereof | Therapeutic compositions and the use thereof |
| AR067184A1 (es) | 2007-06-29 | 2009-09-30 | Gilead Sciences Inc | Uso de 6-(3-cloro-2-fluorbencil)-1-[(2s)-1-hidroxi-3-metilbutan-2-il]-7-metoxi-4-oxo-1,4-dihidroquinolina-3-carboxilico. composicion farmaceutica |
| AR068403A1 (es) * | 2007-09-11 | 2009-11-18 | Gilead Sciences Inc | Proceso e intermediarios para la preparacion de inhibidores de integrasa |
-
2007
- 2007-09-11 WO PCT/US2007/078157 patent/WO2008033836A2/en not_active Ceased
- 2007-09-11 CN CN201510922236.5A patent/CN105315154A/zh active Pending
- 2007-09-11 EA EA200900441A patent/EA022099B1/ru not_active IP Right Cessation
- 2007-09-11 EP EP07842242.5A patent/EP2069280B1/en active Active
- 2007-09-11 AU AU2007296555A patent/AU2007296555B2/en not_active Ceased
- 2007-09-11 SG SG10201501782UA patent/SG10201501782UA/en unknown
- 2007-09-11 ES ES07842242.5T patent/ES2536923T3/es active Active
- 2007-09-11 EP EP13174174.6A patent/EP2644587A3/en not_active Withdrawn
- 2007-09-11 JP JP2009528433A patent/JP5221544B2/ja not_active Expired - Fee Related
- 2007-09-11 MX MX2009002689A patent/MX2009002689A/es active IP Right Grant
- 2007-09-11 US US11/853,606 patent/US7825252B2/en active Active
- 2007-09-11 NZ NZ575542A patent/NZ575542A/en not_active IP Right Cessation
- 2007-09-11 SG SG2011064623A patent/SG174787A1/en unknown
- 2007-09-11 CA CA2661943A patent/CA2661943C/en not_active Expired - Fee Related
- 2007-09-11 AR ARP070104017A patent/AR063710A1/es unknown
- 2007-09-11 HR HRP20090213AA patent/HRP20090213B1/hr not_active IP Right Cessation
- 2007-09-11 CN CN201510922511.3A patent/CN105503721A/zh active Pending
- 2007-09-11 BR BRPI0716752-0A2A patent/BRPI0716752A2/pt not_active IP Right Cessation
- 2007-09-11 KR KR1020127031758A patent/KR101555089B1/ko not_active Expired - Fee Related
- 2007-09-11 AP AP2009004831A patent/AP3004A/xx active
- 2007-09-11 CN CN2007800339076A patent/CN101516819B/zh not_active Expired - Fee Related
- 2007-09-11 TW TW096133911A patent/TWI411602B/zh not_active IP Right Cessation
- 2007-09-11 PT PT78422425T patent/PT2069280E/pt unknown
- 2007-09-11 KR KR1020097007377A patent/KR101565169B1/ko not_active Expired - Fee Related
- 2007-09-11 CN CN201210224990.8A patent/CN102766098B/zh not_active Expired - Fee Related
-
2009
- 2009-03-05 ZA ZA2009/01576A patent/ZA200901576B/en unknown
- 2009-03-11 IL IL197527A patent/IL197527A/en active IP Right Grant
- 2009-04-07 NO NO20091415A patent/NO342907B1/no not_active IP Right Cessation
-
2010
- 2010-09-28 US US12/892,682 patent/US8324244B2/en active Active
-
2012
- 2012-06-12 IL IL220311A patent/IL220311A/en active IP Right Grant
- 2012-09-14 US US13/619,297 patent/US8796459B2/en active Active
- 2012-10-18 JP JP2012230583A patent/JP2013047248A/ja not_active Withdrawn
-
2016
- 2016-08-10 HK HK16109486.4A patent/HK1221454A1/zh unknown
- 2016-10-08 HK HK16111670.6A patent/HK1223370A1/zh unknown
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