AR058570A1 - Procedimiento mejorado par la preparacion de 4-(benzimidazolilmetilamino)-benzamidinas y sus sales - Google Patents
Procedimiento mejorado par la preparacion de 4-(benzimidazolilmetilamino)-benzamidinas y sus salesInfo
- Publication number
- AR058570A1 AR058570A1 ARP060105632A ARP060105632A AR058570A1 AR 058570 A1 AR058570 A1 AR 058570A1 AR P060105632 A ARP060105632 A AR P060105632A AR P060105632 A ARP060105632 A AR P060105632A AR 058570 A1 AR058570 A1 AR 058570A1
- Authority
- AR
- Argentina
- Prior art keywords
- group
- formula
- alkyl
- optionally substituted
- meaning indicated
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
- C07D271/07—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Reivindicacion 2: Procedimiento segun la reivindicacion 1 para la preparacion de una 4-(bencimidazol-2-ilmetilamino)-benzamidina eventualmente sustituida de la formula (1) en la cualR1 representa un grupo alquilo C1-6 o cicloalquilo C3-7, R2 (i) representa un grupo alquilo C1-6, un grupo cicloalquilo C3-7 eventualmente sustituido con un grupo alquilo C1-3, en donde el grupo alquilo C1-3 puede estar sustituido adicionalmente con un grupo carboxilo o con un grupo transformable in-vivo en un grupo carboxi, o (ii) representa un grupo R21NR22, en el que R21 significa un grupo alquilo C1-6, que puede estar sustituido con un grupo carboxi, alcoxi C1-6-carbonilo, benciloxicarbonilo, alquil C1-3-sulfonilaminocarbonilo, fenilsulfonilaminocarbonilo, trifluorosulfonilamino, trifluorosulfonilaminocarbonilo o 1H-tetrazolilo, un grupo alquilo C2-4, sustituido con un grupo hidroxi, fenil-alcoxi C1-3, carboxi-alquil C1-3-amino, alcoxi C1-3-amino, N-(alquil C1-3)- carboxi- alquil C1-3-amino o N-(alquil C1-3)-alcoxi C1-3-carbonil-alquil C1-3-amino, en donde en donde en los grupos precedentemente mencionados el átomo de carbono alfa vecino al átomo de nitrogeno no puede estar sustituido, o un grupo piperidinilo eventualmente sustituido con un grupo alquilo C1-3, y R22 significa un átomo de hidrogeno, un grupo alquilo C1-6, un grupo cicloalquilo C3-7, eventualmente sustituido con un grupo alquilo C1-3, un grupo alquenilo C3-6 o alquinilo C3-6, en donde la parte insaturada no puede estar enlazada directamente con el átomo de nitrogeno del grupo R21NR22, un grupo fenilo eventualmente sustituido con un átomo de fluor, cloro o bromo, con un grupo alquilo C1-3 o alcoxi C1-3, un grupo bencilo, oxazolilo, isoxazolilo, tiazolilo, isotiazolilo, pirazolilo, piridinilo, pirimidinilo, pirazinilo, piridazinilo, pirrolilo, tienilo o imidazolilo, eventualmente sustituido con un grupo alquilo C1-3, o R21 y R22, junto con el átomo de nitrogeno situado entremedias, representan un grupo cicloalquilenimino de 5 a 7 miembros, eventualmente sustituido con un grupo carboxi o alcoxi C1-4-carbonilo, al que adicionalmente puede estar condensado un anillo de fenilo, y R3 representa un átomo de hidrogeno, un grupo alcoxi C1-9-carbonilo, ciclohexiloxicarbonilo, fenil-alcoxi C1-3-carbonilo, benzoílo, p-alquil C1-3-benzoílo o piridinoílo, en donde la parte de etoxi en la posicion 2 del grupo alcoxi C1-9-carbonilo precedentemente mencionado puede estar sustituida adicionalmente con un grupo alquil C1-3-sulfonilo o 2-(alcoxi C1-3)-etilo, en donde en la etapa (a) una fenildiamina de la formula (2) en donde R1 y R2 presentan el significado indicado para la formula 1, se hace reaccionar con ácido 2-[4- (1,2,4-oxadiazol-5-on-3-il)-fenilamino]-acético, el producto obtenido de la formula (3) en donde R1 y R2 presentan el significado indicado para la formula 1, se hidrogena en la etapa (b)i) y, a continuacion, sin previo aislamiento del producto de hidrogenacion, eventualmente el compuesto de la formula 1, así obtenido, en donde R3 significa hidrogeno, se hace reaccionar en la etapa (b)ii) con un compuesto de la formula R3-X en donde R3 presenta el significado indicado para la formula 1 y X representa un grupo lábil adecuado. Reivindicacion 8: Procedimiento segun la reivindicacion 7 para la preparacion de una sal de una 4-(bencimidazol-2-ilmetilamino)-benzamidina eventualmente sustituida de la formula (1) en la que R1 a R3 están definidos como se menciona en la reivindicacion 2, abarca las siguientes etapas: (a) reaccion de una fenildiamina de la formula (2) en donde R1 y R2 presentan el significado indicado para la formula 1, con ácido 2-[4-(1,2,4-oxadiazol-5-on-3-il)- fenilamino]-acético, (b) hidrogenacion del producto de la formula (3) así obtenido en donde R1 y R2 presentan el significado indicado para la formula (1), y (c)i) reaccion del compuesto de la formula 1, así obtenido, en donde R3 significa hidrogeno, con un compuesto de la formula R3-X en donde R3 presenta el significado indicado para la formula (1), y X representa un grupo lábil adecuado, y ii) precipitacion de la sal deseada del compuesto de la formula 1 así obtenido, sin aislar de antemano el producto de carbonilacion.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102005061623A DE102005061623A1 (de) | 2005-12-21 | 2005-12-21 | Verbessertes Verfahren zur Herstellung von 4-(Benzimidazolylmethylamino)-Benzamidinen und deren Salzen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR058570A1 true AR058570A1 (es) | 2008-02-13 |
Family
ID=37945425
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP060105632A AR058570A1 (es) | 2005-12-21 | 2006-12-20 | Procedimiento mejorado par la preparacion de 4-(benzimidazolilmetilamino)-benzamidinas y sus sales |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US20070185333A1 (es) |
| EP (1) | EP1966171A1 (es) |
| JP (1) | JP5317701B2 (es) |
| KR (1) | KR101408709B1 (es) |
| CN (1) | CN101346360A (es) |
| AR (1) | AR058570A1 (es) |
| AU (1) | AU2006326979B2 (es) |
| BR (1) | BRPI0620204A2 (es) |
| CA (1) | CA2631832C (es) |
| DE (1) | DE102005061623A1 (es) |
| IL (1) | IL192241A (es) |
| NZ (1) | NZ569851A (es) |
| RU (1) | RU2455292C2 (es) |
| TW (1) | TWI391382B (es) |
| WO (1) | WO2007071742A1 (es) |
| ZA (1) | ZA200804030B (es) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030181488A1 (en) * | 2002-03-07 | 2003-09-25 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Administration form for the oral application of 3-[(2-{[4-(hexyloxycarbonylamino-imino-methyl)-phenylamino]-methyl}-1-methyl-1H-benzimidazol-5-carbonyl)-pyridin-2-yl-amino]-propionic acid ethyl ester and the salts thereof |
| DE10339862A1 (de) * | 2003-08-29 | 2005-03-24 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | 3-[(2-{[4-(Hexyloxycarbonylamino-imino-methyl)- phenylamino]-methyl}-1-methyl-1H-benzimidazol-5-carbonyl)-pyridin-2-yl-amino]-propionsäure-ethylester-Methansulfonat und dessen Verwendung als Arzneimittel |
| DE102005061624A1 (de) * | 2005-12-21 | 2007-06-28 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Verbessertes Verfahren zur Herstellung von Salzen von 4-(Benzimidazolylmethylamino)-Benzamidinen |
| DE102006054005A1 (de) * | 2006-11-16 | 2008-05-21 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Polymorphe von 3-[(2-{[4-(Hexyloxycarbonylamino-imino-methyl)-phenylamino]-methyl}-1-methyl-1H-benzimidazol-5-carbonyl)-pyridin-2-yl-amino]-propionsäure-ethylester |
| CZ305085B6 (cs) * | 2008-03-14 | 2015-04-29 | Zentiva, K.S. | Způsob přípravy dabigatranu |
| CN101980697A (zh) * | 2008-03-28 | 2011-02-23 | 贝林格尔.英格海姆国际有限公司 | 制备口服给药的达比加群制剂的方法 |
| BRPI0914788B1 (pt) * | 2008-06-16 | 2020-04-07 | Boehringer Ingelheim Int | processo para produção de um produto intermediário de etexilato de dabigatran |
| NZ589746A (en) | 2008-07-14 | 2012-10-26 | Boehringer Ingelheim Int | Method for manufacturing medicinal compounds containing dabigatran |
| CZ2008669A3 (cs) * | 2008-10-24 | 2010-05-05 | Zentiva, A. S. | Zpusob prípravy dabigatranu a jeho meziprodukty |
| CN102209544A (zh) | 2008-11-11 | 2011-10-05 | 贝林格尔.英格海姆国际有限公司 | 使用达比加群酯或其盐治疗或预防血栓形成且与常规的华法林疗法相比具有改良安全性的方法 |
| US8399678B2 (en) | 2009-11-18 | 2013-03-19 | Boehringer Ingelheim International Gmbh | Process for the manufacture of dabigatran etexilate |
| HUP1000069A2 (en) * | 2010-02-02 | 2012-05-02 | Egis Gyogyszergyar Nyilvanosan M Kod Ruszvunytarsasag | New salts for the preparation of pharmaceutical composition |
| US9006448B2 (en) | 2010-12-06 | 2015-04-14 | Msn Laboratories Private Limited | Process for the preparation of benzimidazole derivatives and its salts |
| HUP1100244A2 (hu) * | 2011-05-11 | 2012-11-28 | Egis Gyogyszergyar Nyilvanosan Muekoedoe Reszvenytarsasag | Gyógyszeripari intermedierek és eljárás elõállításukra |
| EP2522662A1 (en) | 2011-05-11 | 2012-11-14 | Medichem, S.A. | Dabigatran etexilate and related substances, processes and compositions, and use of the substances as reference standards and markers |
| CN102993175B (zh) * | 2011-09-08 | 2014-08-13 | 天津药物研究院 | 达比加群的酯衍生物及其制备方法和用途 |
| US9212166B2 (en) | 2012-01-20 | 2015-12-15 | Cadila Healthcare Limited | Process for the preparation of dabigatran etexilate mesylate and polymorphs of intermediates thereof |
| EP2631234A1 (en) * | 2012-02-23 | 2013-08-28 | Esteve Química, S.A. | Solid forms of dabigatran etexilate mesylate and processes for their preparation |
| WO2013150545A2 (en) | 2012-04-02 | 2013-10-10 | Msn Laboratories Limited | Process for the preparation of benzimidazole derivatives and salts thereof |
| CN102850325B (zh) * | 2012-06-19 | 2014-03-26 | 上海现代制药海门有限公司 | 一种达比加群酯关键中间体的制备方法 |
| CN102850327B (zh) * | 2012-06-19 | 2014-07-16 | 上海现代制药股份有限公司 | 一种制备达比加群酯的中间体及其制备方法和应用 |
| CN102850326B (zh) * | 2012-06-19 | 2014-04-09 | 上海现代制药股份有限公司 | 一种达比加群酯中间体及其制备方法和应用 |
| EP2872500A4 (en) * | 2012-07-12 | 2016-03-30 | Rao Davuluri Ramamohan | IMPROVED METHOD FOR THE PRODUCTION OF DABIGATRANETEXILATE MESYLATE AND INTERMEDIATE PRODUCTS THEREOF |
| US9150542B2 (en) | 2012-08-31 | 2015-10-06 | Ranbaxy Laboratories Limited | Process for the preparation of crystalline form I of methanesulfonate salt of dabigatran etexilate |
| WO2014068587A2 (en) * | 2012-10-29 | 2014-05-08 | Biophore India Pharmaceuticals Pvt. Ltd. | An improved process for the synthesis of dabigatran and its intermediates |
| US10077251B2 (en) | 2012-10-29 | 2018-09-18 | Biophore India Pharmaceuticals Pvt. Ltd. | Process for the synthesis of Dabigatran Etexilate and its intermediates |
| WO2014151929A1 (en) | 2013-03-15 | 2014-09-25 | Proteus Digital Health, Inc. | Personal authentication apparatus system and method |
| EP2835370A1 (en) | 2013-08-08 | 2015-02-11 | Medichem, S.A. | New crystals of dabigatran etexilate mesylate |
| CN104031031B (zh) * | 2014-05-05 | 2017-01-11 | 南通常佑药业科技有限公司 | 一种制备达比加群酯的方法 |
| CN103992241B (zh) * | 2014-06-05 | 2016-08-24 | 雅本化学股份有限公司 | N-取代苯基甘氨酸的制备方法 |
| CN105461686A (zh) * | 2014-08-25 | 2016-04-06 | 江苏豪森药业股份有限公司 | 制备高纯度甲磺酸达比加群酯晶型的方法 |
| US10138236B2 (en) | 2014-09-24 | 2018-11-27 | Bayer Pharma Aktiengesellschaft | Factor xia-inhibiting pyridobenzazepine and pyridobenzazocine derivatives |
| CN111253369A (zh) * | 2018-11-30 | 2020-06-09 | 上海医药集团股份有限公司 | 一种苯磺酸盐、其制备方法及其在制备达比加群酯中的应用 |
| CN111595828B (zh) * | 2019-02-21 | 2022-10-14 | 香港科技大学深圳研究院 | 一种纳米氧化锌溶出的监测方法 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6087380A (en) * | 1949-11-24 | 2000-07-11 | Boehringer Ingelheim Pharma Kg | Disubstituted bicyclic heterocycles, the preparations and the use thereof as pharmaceutical compositions |
| PE121699A1 (es) * | 1997-02-18 | 1999-12-08 | Boehringer Ingelheim Pharma | Heterociclos biciclicos disustituidos como inhibidores de la trombina |
| TWI248435B (en) * | 1998-07-04 | 2006-02-01 | Boehringer Ingelheim Pharma | Benzimidazoles, the preparation thereof and their use as pharmaceutical compositions |
| US6248770B1 (en) * | 1998-07-09 | 2001-06-19 | Boehringer Ingelheim Pharma Kg | Benzimidazoles having antithrombotic activity |
| US6451832B2 (en) * | 1999-12-23 | 2002-09-17 | Boehringer Ingelheim Pharma Kg | Benzimidazoles with antithrombotic activity |
| DE19962329A1 (de) * | 1999-12-23 | 2001-06-28 | Boehringer Ingelheim Pharma | Benzimidazole, deren Herstellung und deren Verwendung als Arzneimittel |
| JP3866715B2 (ja) * | 2002-03-07 | 2007-01-10 | ベーリンガー インゲルハイム ファルマ ゲゼルシャフト ミット ベシュレンクテル ハフツング ウント コンパニー コマンディトゲゼルシャフト | ３−［（２−｛［４−（ヘキシルオキシカルボニルアミノ−イミノ−メチル）−フェニルアミノ］−メチル｝−１−メチル−１ｈ−ベンゾイミダゾール−５−カルボニル）−ピリジン−２−イル−アミノ］−プロピオン酸エチルエステル及びその塩の経口適用の投与形態 |
| EP1609784A1 (de) * | 2004-06-25 | 2005-12-28 | Boehringer Ingelheim Pharma GmbH & Co.KG | Verfahren zur Herstellung von 4-(Benzimidazolylmethylamino)-Benzamidinen |
| DE102005061624A1 (de) * | 2005-12-21 | 2007-06-28 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Verbessertes Verfahren zur Herstellung von Salzen von 4-(Benzimidazolylmethylamino)-Benzamidinen |
| EP1956018A1 (de) | 2007-02-06 | 2008-08-13 | Boehringer Ingelheim Pharma GmbH & Co. KG | Verfahren zur Herstellung eines Benzimidazolderivats |
| EP2271317B1 (de) | 2008-03-28 | 2017-04-19 | Boehringer Ingelheim International GmbH | Verfahren zur herstellung von säurepellets |
| CN101980697A (zh) | 2008-03-28 | 2011-02-23 | 贝林格尔.英格海姆国际有限公司 | 制备口服给药的达比加群制剂的方法 |
| BRPI0914788B1 (pt) | 2008-06-16 | 2020-04-07 | Boehringer Ingelheim Int | processo para produção de um produto intermediário de etexilato de dabigatran |
| EP2300431B1 (en) | 2008-06-16 | 2016-01-06 | Boehringer Ingelheim International GmbH | Process for the manufacture of an intermediate in the synthesis of dabigatran |
| NZ589746A (en) | 2008-07-14 | 2012-10-26 | Boehringer Ingelheim Int | Method for manufacturing medicinal compounds containing dabigatran |
-
2005
- 2005-12-21 DE DE102005061623A patent/DE102005061623A1/de not_active Withdrawn
-
2006
- 2006-12-20 EP EP06841529A patent/EP1966171A1/en not_active Withdrawn
- 2006-12-20 BR BRPI0620204-7A patent/BRPI0620204A2/pt not_active Application Discontinuation
- 2006-12-20 TW TW095148025A patent/TWI391382B/zh not_active IP Right Cessation
- 2006-12-20 JP JP2008546455A patent/JP5317701B2/ja not_active Expired - Fee Related
- 2006-12-20 KR KR1020087017722A patent/KR101408709B1/ko not_active IP Right Cessation
- 2006-12-20 RU RU2008129376/04A patent/RU2455292C2/ru not_active IP Right Cessation
- 2006-12-20 NZ NZ569851A patent/NZ569851A/en not_active IP Right Cessation
- 2006-12-20 AU AU2006326979A patent/AU2006326979B2/en not_active Ceased
- 2006-12-20 CA CA2631832A patent/CA2631832C/en not_active Expired - Fee Related
- 2006-12-20 CN CNA200680048944XA patent/CN101346360A/zh active Pending
- 2006-12-20 AR ARP060105632A patent/AR058570A1/es unknown
- 2006-12-20 WO PCT/EP2006/070033 patent/WO2007071742A1/en active Application Filing
- 2006-12-21 US US11/614,304 patent/US20070185333A1/en not_active Abandoned
-
2008
- 2008-05-12 ZA ZA2008/04030A patent/ZA200804030B/en unknown
- 2008-06-17 IL IL192241A patent/IL192241A/en not_active IP Right Cessation
-
2010
- 2010-04-29 US US12/769,718 patent/US8354543B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CN101346360A (zh) | 2009-01-14 |
| ZA200804030B (en) | 2009-02-25 |
| AU2006326979A1 (en) | 2007-06-28 |
| AU2006326979B2 (en) | 2013-03-28 |
| RU2455292C2 (ru) | 2012-07-10 |
| US8354543B2 (en) | 2013-01-15 |
| DE102005061623A1 (de) | 2007-06-28 |
| IL192241A (en) | 2014-01-30 |
| JP2009520765A (ja) | 2009-05-28 |
| CA2631832A1 (en) | 2007-06-28 |
| US20070185333A1 (en) | 2007-08-09 |
| CA2631832C (en) | 2014-04-15 |
| NZ569851A (en) | 2011-10-28 |
| KR20080077029A (ko) | 2008-08-20 |
| KR101408709B1 (ko) | 2014-06-17 |
| TW200804302A (en) | 2008-01-16 |
| IL192241A0 (en) | 2008-12-29 |
| WO2007071742A1 (en) | 2007-06-28 |
| EP1966171A1 (en) | 2008-09-10 |
| US20100210845A1 (en) | 2010-08-19 |
| TWI391382B (zh) | 2013-04-01 |
| JP5317701B2 (ja) | 2013-10-16 |
| BRPI0620204A2 (pt) | 2011-11-01 |
| RU2008129376A (ru) | 2010-01-27 |
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