RU2010129913A - Способ получения производных 2-амино-5-цианобензойной кислоты - Google Patents
Способ получения производных 2-амино-5-цианобензойной кислоты Download PDFInfo
- Publication number
- RU2010129913A RU2010129913A RU2010129913/04A RU2010129913A RU2010129913A RU 2010129913 A RU2010129913 A RU 2010129913A RU 2010129913/04 A RU2010129913/04 A RU 2010129913/04A RU 2010129913 A RU2010129913 A RU 2010129913A RU 2010129913 A RU2010129913 A RU 2010129913A
- Authority
- RU
- Russia
- Prior art keywords
- formula
- compound
- reagent
- alkyl
- mixture
- Prior art date
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- HQNZNIJPAYTWJK-UHFFFAOYSA-N 2-amino-5-cyanobenzoic acid Chemical class NC1=CC=C(C#N)C=C1C(O)=O HQNZNIJPAYTWJK-UHFFFAOYSA-N 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 35
- 238000000034 method Methods 0.000 claims abstract 26
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract 25
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims abstract 9
- 229910052751 metal Inorganic materials 0.000 claims abstract 9
- 239000002184 metal Substances 0.000 claims abstract 9
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 claims abstract 8
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims abstract 8
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical class [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 claims abstract 7
- NURQLCJSMXZBPC-UHFFFAOYSA-N 3,4-dimethylpyridine Chemical compound CC1=CC=NC=C1C NURQLCJSMXZBPC-UHFFFAOYSA-N 0.000 claims abstract 6
- HWWYDZCSSYKIAD-UHFFFAOYSA-N 3,5-dimethylpyridine Chemical compound CC1=CN=CC(C)=C1 HWWYDZCSSYKIAD-UHFFFAOYSA-N 0.000 claims abstract 6
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 claims abstract 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract 4
- 125000006450 cyclopropyl cyclopropyl group Chemical group 0.000 claims abstract 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract 4
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims abstract 4
- 125000006431 methyl cyclopropyl group Chemical group 0.000 claims abstract 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims abstract 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract 3
- VJXRKZJMGVSXPX-UHFFFAOYSA-N 4-ethylpyridine Chemical compound CCC1=CC=NC=C1 VJXRKZJMGVSXPX-UHFFFAOYSA-N 0.000 claims abstract 2
- XQABVLBGNWBWIV-UHFFFAOYSA-N 4-methoxypyridine Chemical compound COC1=CC=NC=C1 XQABVLBGNWBWIV-UHFFFAOYSA-N 0.000 claims abstract 2
- QJWQYVJVCXMTJP-UHFFFAOYSA-N 4-pyridin-4-ylmorpholine Chemical compound C1COCCN1C1=CC=NC=C1 QJWQYVJVCXMTJP-UHFFFAOYSA-N 0.000 claims abstract 2
- RGUKYNXWOWSRET-UHFFFAOYSA-N 4-pyrrolidin-1-ylpyridine Chemical compound C1CCCN1C1=CC=NC=C1 RGUKYNXWOWSRET-UHFFFAOYSA-N 0.000 claims abstract 2
- YSHMQTRICHYLGF-UHFFFAOYSA-N 4-tert-butylpyridine Chemical compound CC(C)(C)C1=CC=NC=C1 YSHMQTRICHYLGF-UHFFFAOYSA-N 0.000 claims abstract 2
- 229910021595 Copper(I) iodide Inorganic materials 0.000 claims abstract 2
- 150000001879 copper Chemical class 0.000 claims abstract 2
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 claims abstract 2
- 230000003993 interaction Effects 0.000 claims abstract 2
- ODKLEQPZOCJQMT-UHFFFAOYSA-N n,n-diethylpyridin-4-amine Chemical compound CCN(CC)C1=CC=NC=C1 ODKLEQPZOCJQMT-UHFFFAOYSA-N 0.000 claims abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 2
- 125000001424 substituent group Chemical group 0.000 claims abstract 2
- 239000000203 mixture Substances 0.000 claims 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 9
- 239000003960 organic solvent Substances 0.000 claims 7
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims 6
- GWHJZXXIDMPWGX-UHFFFAOYSA-N 1,2,4-trimethylbenzene Chemical compound CC1=CC=C(C)C(C)=C1 GWHJZXXIDMPWGX-UHFFFAOYSA-N 0.000 claims 4
- AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 claims 4
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 claims 4
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 3
- 239000008096 xylene Substances 0.000 claims 3
- 150000003738 xylenes Chemical class 0.000 claims 3
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 claims 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims 2
- UOCPQZOXOQZEGV-UHFFFAOYSA-N 2-amino-5-cyano-n,3-dimethylbenzamide Chemical compound CNC(=O)C1=CC(C#N)=CC(C)=C1N UOCPQZOXOQZEGV-UHFFFAOYSA-N 0.000 claims 1
- -1 alkali metal cyanides Chemical class 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims 1
- 229940071870 hydroiodic acid Drugs 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 claims 1
- GTSHREYGKSITGK-UHFFFAOYSA-N sodium ferrocyanide Chemical compound [Na+].[Na+].[Na+].[Na+].[Fe+2].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] GTSHREYGKSITGK-UHFFFAOYSA-N 0.000 claims 1
- 235000012247 sodium ferrocyanide Nutrition 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 239000012265 solid product Substances 0.000 claims 1
- AWDBHOZBRXWRKS-UHFFFAOYSA-N tetrapotassium;iron(6+);hexacyanide Chemical compound [K+].[K+].[K+].[K+].[Fe+6].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] AWDBHOZBRXWRKS-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 3
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 abstract 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 101100294106 Caenorhabditis elegans nhr-3 gene Proteins 0.000 abstract 1
Classifications
-
- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/14—Preparation of carboxylic acid nitriles by reaction of cyanides with halogen-containing compounds with replacement of halogen atoms by cyano groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D231/16—Halogen atoms or nitro radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Toxicology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US845807P | 2007-12-19 | 2007-12-19 | |
| US61/008,458 | 2007-12-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2010129913A true RU2010129913A (ru) | 2012-01-27 |
Family
ID=40521896
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2010129913/04A RU2010129913A (ru) | 2007-12-19 | 2008-12-17 | Способ получения производных 2-амино-5-цианобензойной кислоты |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US8247570B2 (https=) |
| EP (1) | EP2231592B1 (https=) |
| JP (1) | JP5398734B2 (https=) |
| KR (1) | KR101587296B1 (https=) |
| CN (1) | CN101970397B (https=) |
| AR (1) | AR069838A1 (https=) |
| AU (1) | AU2008343227B2 (https=) |
| BR (1) | BRPI0819568B1 (https=) |
| CA (1) | CA2709952A1 (https=) |
| CL (1) | CL2008003756A1 (https=) |
| CO (1) | CO6300860A2 (https=) |
| IL (1) | IL206390A (https=) |
| RU (1) | RU2010129913A (https=) |
| TW (1) | TWI432421B (https=) |
| WO (1) | WO2009085816A1 (https=) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8242140B2 (en) | 2007-08-03 | 2012-08-14 | Boehringer Ingelheim International Gmbh | Viral polymerase inhibitors |
| EP2234977A4 (en) | 2007-12-19 | 2011-04-13 | Boehringer Ingelheim Int | VIRAL POLYMERASE INHIBITORS |
| TWI431000B (zh) | 2008-03-05 | 2014-03-21 | Du Pont | 製備２－胺基－５－氰基苯甲酸衍生物之方法 |
| TW201247631A (en) | 2011-04-28 | 2012-12-01 | Du Pont | Herbicidal pyrazinones |
| US9169198B2 (en) | 2011-07-08 | 2015-10-27 | Bayer Intellectual Property Gmbh | Method for the production of 2-amino-5-cyano-N,3-dimethylbenzamide |
| BR112014003186A2 (pt) | 2011-08-12 | 2017-04-04 | Basf Se | composto da fórmula geral (i), combinação pesticida, composição agrícola ou veterinária, método para combater ou controlar pragas invertebradas, método para a proteção de plantas e sementes, semente, uso de um composto e método para tratar um animal |
| JP2014522872A (ja) | 2011-08-12 | 2014-09-08 | ビーエーエスエフ ソシエタス・ヨーロピア | Ｎ−チオ−アントラニルアミド化合物、及び殺有害生物剤としてのそれらの使用 |
| ES2558166T3 (es) | 2011-08-12 | 2016-02-02 | Basf Se | Compuestos de N-tio-antranilamida y su uso como pesticidas |
| JP2014529587A (ja) | 2011-08-12 | 2014-11-13 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | Ｎ−チオ−アントラニルアミド化合物、及び殺有害生物剤としてのそれらの使用 |
| EP2793885A1 (en) | 2011-12-21 | 2014-10-29 | Basf Se | N-thio-anthranilamide compounds and their use as pesticides |
| WO2013113789A1 (en) | 2012-02-02 | 2013-08-08 | Basf Se | N-thio-anthranilamide compounds and their use as pesticides |
| KR102032979B1 (ko) | 2012-02-07 | 2019-10-16 | 바이엘 인텔렉쳐 프로퍼티 게엠베하 | 치환된 안트라닐산 유도체의 제조방법 |
| CN104003976B (zh) * | 2014-05-07 | 2016-03-16 | 肇庆市真格生物科技有限公司 | 多取代吡啶基吡唑酰胺及其制备方法和用途 |
| TWI678354B (zh) | 2014-05-29 | 2019-12-01 | 新加坡商艾佛艾姆希農業新加坡有限公司 | 藉空氣氧化製備３-甲基-２-硝基苯甲酸之製程 |
| CN105461683B (zh) * | 2015-11-18 | 2019-01-15 | 江苏省农用激素工程技术研究中心有限公司 | 邻氨基苯甲酰胺化合物的制备方法 |
| EA202191554A1 (ru) * | 2018-12-03 | 2021-09-02 | Фмк Корпорейшн | Способ получения n-фенилпиразол-1-карбоксамидов |
| CN113692406B (zh) | 2019-02-18 | 2024-07-23 | Pi工业有限公司 | 制备邻甲酰胺基苯甲酰胺类化合物及其中间体的方法 |
| MX2021010098A (es) | 2019-02-22 | 2021-09-28 | Pi Industries Ltd | Un proceso para la sintesis de compuestos de diamida antranilica y compuestos intermedios de los mismos. |
| AR123593A1 (es) | 2020-09-26 | 2022-12-21 | Pi Industries Ltd | Un proceso para la síntesis de compuestos antranílicos de ácido / amida e intermedios de los mismos |
| US20240308988A1 (en) | 2021-08-05 | 2024-09-19 | Syngenta Crop Protection Ag | Method For Controlling Diamide Resistant Pests and Compounds Therefor |
| US20260055052A1 (en) | 2022-08-16 | 2026-02-26 | Adama Makhteshim Ltd. | Process for preparing cyantraniliprole via amino-cyano-benzene derivative |
| WO2024116197A1 (en) * | 2022-11-30 | 2024-06-06 | Natco Pharma Limited | An improved process for the preparation of intermediate of cyantraniliprole |
| WO2026047667A1 (en) | 2024-08-26 | 2026-03-05 | Adama Makhteshim Ltd. | Process for preparing amino-cyano-benzene derivatives |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20050032107A (ko) | 2002-08-02 | 2005-04-06 | 메사추세츠 인스티튜트 오브 테크놀로지 | 구리를 촉매로 한 탄소-헤테로원자 결합 및 탄소-탄소결합 형성방법 |
| SI1599463T1 (sl) | 2003-01-28 | 2013-10-30 | E.I. Du Pont De Nemours And Company | Ciano antranilamidni insekticidi |
| MY140912A (en) * | 2004-07-26 | 2010-01-29 | Du Pont | Mixtures of anthranilamide invertebrate pest control agents |
| TWI363756B (en) * | 2004-12-07 | 2012-05-11 | Du Pont | Method for preparing n-phenylpyrazole-1-carboxamides |
| DE102006042439A1 (de) | 2006-09-09 | 2008-03-27 | Saltigo Gmbh | Verfahren zur katalytischen Herstellung von aromatischen oder heteroaromatischen Nitrilen |
| TWI415827B (zh) | 2006-12-21 | 2013-11-21 | Du Pont | 製備２-胺基-５-氰基苯甲酸衍生物之方法 |
| TWI431000B (zh) | 2008-03-05 | 2014-03-21 | Du Pont | 製備２－胺基－５－氰基苯甲酸衍生物之方法 |
-
2008
- 2008-12-16 TW TW097149061A patent/TWI432421B/zh active
- 2008-12-17 RU RU2010129913/04A patent/RU2010129913A/ru unknown
- 2008-12-17 BR BRPI0819568-4A patent/BRPI0819568B1/pt active IP Right Grant
- 2008-12-17 JP JP2010539729A patent/JP5398734B2/ja active Active
- 2008-12-17 US US12/809,072 patent/US8247570B2/en active Active
- 2008-12-17 EP EP08868511.0A patent/EP2231592B1/en active Active
- 2008-12-17 AU AU2008343227A patent/AU2008343227B2/en active Active
- 2008-12-17 WO PCT/US2008/087151 patent/WO2009085816A1/en not_active Ceased
- 2008-12-17 CA CA2709952A patent/CA2709952A1/en not_active Abandoned
- 2008-12-17 CL CL2008003756A patent/CL2008003756A1/es unknown
- 2008-12-17 KR KR1020107015703A patent/KR101587296B1/ko active Active
- 2008-12-17 CN CN200880126979.XA patent/CN101970397B/zh active Active
- 2008-12-19 AR ARP080105556A patent/AR069838A1/es unknown
-
2010
- 2010-06-15 IL IL206390A patent/IL206390A/en active IP Right Grant
- 2010-06-18 CO CO10073860A patent/CO6300860A2/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| CO6300860A2 (es) | 2011-07-21 |
| US8247570B2 (en) | 2012-08-21 |
| IL206390A0 (en) | 2010-12-30 |
| IL206390A (en) | 2014-06-30 |
| CA2709952A1 (en) | 2009-07-09 |
| JP5398734B2 (ja) | 2014-01-29 |
| TW200934770A (en) | 2009-08-16 |
| EP2231592B1 (en) | 2016-02-17 |
| BRPI0819568B1 (pt) | 2018-02-06 |
| AU2008343227A1 (en) | 2009-07-09 |
| CN101970397A (zh) | 2011-02-09 |
| KR101587296B1 (ko) | 2016-01-21 |
| CN101970397B (zh) | 2014-04-16 |
| CL2008003756A1 (es) | 2009-11-27 |
| EP2231592A1 (en) | 2010-09-29 |
| KR20100098443A (ko) | 2010-09-06 |
| BRPI0819568A2 (pt) | 2017-07-04 |
| JP2011507872A (ja) | 2011-03-10 |
| AU2008343227B2 (en) | 2013-08-01 |
| WO2009085816A1 (en) | 2009-07-09 |
| TWI432421B (zh) | 2014-04-01 |
| US20120130080A1 (en) | 2012-05-24 |
| AR069838A1 (es) | 2010-02-24 |
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