RU2490272C2 - Макроциклические ингибиторы серинпротеазы - Google Patents
Макроциклические ингибиторы серинпротеазы Download PDFInfo
- Publication number
- RU2490272C2 RU2490272C2 RU2010136973/04A RU2010136973A RU2490272C2 RU 2490272 C2 RU2490272 C2 RU 2490272C2 RU 2010136973/04 A RU2010136973/04 A RU 2010136973/04A RU 2010136973 A RU2010136973 A RU 2010136973A RU 2490272 C2 RU2490272 C2 RU 2490272C2
- Authority
- RU
- Russia
- Prior art keywords
- compound according
- alkyl
- optionally substituted
- substituents
- heterocyclyl
- Prior art date
Links
- 239000003001 serine protease inhibitor Substances 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract 65
- 241000711549 Hepacivirus C Species 0.000 claims abstract 15
- 238000000034 method Methods 0.000 claims abstract 13
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 7
- 230000002401 inhibitory effect Effects 0.000 claims abstract 5
- 239000000203 mixture Substances 0.000 claims abstract 5
- 102000012479 Serine Proteases Human genes 0.000 claims abstract 4
- 108010022999 Serine Proteases Proteins 0.000 claims abstract 4
- 208000015181 infectious disease Diseases 0.000 claims abstract 4
- 230000029812 viral genome replication Effects 0.000 claims abstract 3
- 108091005804 Peptidases Proteins 0.000 claims abstract 2
- 239000004365 Protease Substances 0.000 claims abstract 2
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 claims abstract 2
- 230000000840 anti-viral effect Effects 0.000 claims abstract 2
- 239000003937 drug carrier Substances 0.000 claims abstract 2
- 230000000694 effects Effects 0.000 claims abstract 2
- 208000019423 liver disease Diseases 0.000 claims abstract 2
- 208000024891 symptom Diseases 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims 33
- 125000001424 substituent group Chemical group 0.000 claims 33
- 125000000623 heterocyclic group Chemical group 0.000 claims 32
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 29
- 125000003118 aryl group Chemical group 0.000 claims 29
- 229910052739 hydrogen Inorganic materials 0.000 claims 28
- 239000001257 hydrogen Substances 0.000 claims 28
- 125000001072 heteroaryl group Chemical group 0.000 claims 27
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 25
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 22
- 150000002431 hydrogen Chemical class 0.000 claims 14
- 229910052736 halogen Inorganic materials 0.000 claims 13
- 150000002367 halogens Chemical class 0.000 claims 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- -1 isopropylamino Chemical group 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000002993 cycloalkylene group Chemical group 0.000 claims 3
- 125000004450 alkenylene group Chemical group 0.000 claims 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000006574 non-aromatic ring group Chemical group 0.000 claims 2
- 239000006186 oral dosage form Substances 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 101800001838 Serine protease/helicase NS3 Proteins 0.000 claims 1
- 241000700605 Viruses Species 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 1
- 239000003443 antiviral agent Substances 0.000 claims 1
- 239000002775 capsule Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 239000006207 intravenous dosage form Substances 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 239000006201 parenteral dosage form Substances 0.000 claims 1
- 125000003367 polycyclic group Chemical group 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- 239000003814 drug Substances 0.000 abstract 1
- 150000002678 macrocyclic compounds Chemical class 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 0 CC1C=C=NN(C)/C=C/C1* Chemical compound CC1C=C=NN(C)/C=C/C1* 0.000 description 2
- ZSMPXLJQCKPGFF-UHFFFAOYSA-N CC(C)Nc1nc(C)c[s]1 Chemical compound CC(C)Nc1nc(C)c[s]1 ZSMPXLJQCKPGFF-UHFFFAOYSA-N 0.000 description 1
- ICKWWMZNJUIKOM-UHFFFAOYSA-N CC(C)c(cc1)n[n]1-c1cc(I)c(ccc(OC)c2C)c2n1 Chemical compound CC(C)c(cc1)n[n]1-c1cc(I)c(ccc(OC)c2C)c2n1 ICKWWMZNJUIKOM-UHFFFAOYSA-N 0.000 description 1
- CJGVHFQKTSHCCU-UHFFFAOYSA-N CC(C)c1c[s]c(-c(cc(C)c2ccc3OC)nc2c3Cl)n1 Chemical compound CC(C)c1c[s]c(-c(cc(C)c2ccc3OC)nc2c3Cl)n1 CJGVHFQKTSHCCU-UHFFFAOYSA-N 0.000 description 1
- TWYDGLMZCKQWDK-UHFFFAOYSA-N CC(C)c1nc(-c2cc(I)c(ccc(OC)c3)c3n2)c[s]1 Chemical compound CC(C)c1nc(-c2cc(I)c(ccc(OC)c3)c3n2)c[s]1 TWYDGLMZCKQWDK-UHFFFAOYSA-N 0.000 description 1
- YJTKWISIRVHDCJ-UHFFFAOYSA-N CC(C)c1nc(-c2cc(I)c3c(OC)cc(OC)cc3n2)c[s]1 Chemical compound CC(C)c1nc(-c2cc(I)c3c(OC)cc(OC)cc3n2)c[s]1 YJTKWISIRVHDCJ-UHFFFAOYSA-N 0.000 description 1
- DOKWSYPYNIIVEP-UHFFFAOYSA-N COc(ccc(c1nc(-[n]2nc(C(F)(F)F)cc2)c2)c2I)c1Cl Chemical compound COc(ccc(c1nc(-[n]2nc(C(F)(F)F)cc2)c2)c2I)c1Cl DOKWSYPYNIIVEP-UHFFFAOYSA-N 0.000 description 1
- TYQWMXPWYZEFPG-UHFFFAOYSA-N COc(ccc(c1nc(-c2nc(C3CCC3)c[s]2)c2)c2I)c1Cl Chemical compound COc(ccc(c1nc(-c2nc(C3CCC3)c[s]2)c2)c2I)c1Cl TYQWMXPWYZEFPG-UHFFFAOYSA-N 0.000 description 1
- MTARYKBXGGNUQY-UHFFFAOYSA-N Cc1c(ccc(OC)c2C)c2nc(-c2c[s]c(C(F)(F)F)n2)c1 Chemical compound Cc1c(ccc(OC)c2C)c2nc(-c2c[s]c(C(F)(F)F)n2)c1 MTARYKBXGGNUQY-UHFFFAOYSA-N 0.000 description 1
- WLKYXMNPVZPLQH-UHFFFAOYSA-N Cc1nc(C2CCC2)c[s]1 Chemical compound Cc1nc(C2CCC2)c[s]1 WLKYXMNPVZPLQH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/08—Bridged systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Virology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2608608P | 2008-02-04 | 2008-02-04 | |
| US61/026,086 | 2008-02-04 | ||
| US8386708P | 2008-07-25 | 2008-07-25 | |
| US61/083,867 | 2008-07-25 | ||
| PCT/US2009/000688 WO2009099596A2 (en) | 2008-02-04 | 2009-02-03 | Macrocyclic serine protease inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2010136973A RU2010136973A (ru) | 2012-03-20 |
| RU2490272C2 true RU2490272C2 (ru) | 2013-08-20 |
Family
ID=40568607
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2010136973/04A RU2490272C2 (ru) | 2008-02-04 | 2009-02-03 | Макроциклические ингибиторы серинпротеазы |
Country Status (21)
| Country | Link |
|---|---|
| US (2) | US8003659B2 (enExample) |
| EP (1) | EP2250174B1 (enExample) |
| JP (1) | JP5574982B2 (enExample) |
| KR (1) | KR20100118991A (enExample) |
| CN (1) | CN101977915B (enExample) |
| AR (1) | AR070413A1 (enExample) |
| AU (1) | AU2009210789B2 (enExample) |
| BR (1) | BRPI0908021A2 (enExample) |
| CA (1) | CA2712971A1 (enExample) |
| CO (1) | CO6501153A2 (enExample) |
| CR (1) | CR11618A (enExample) |
| EC (1) | ECSP10010413A (enExample) |
| ES (1) | ES2437147T3 (enExample) |
| IL (1) | IL207333A0 (enExample) |
| MX (1) | MX2010008523A (enExample) |
| NI (1) | NI201000136A (enExample) |
| NZ (1) | NZ587133A (enExample) |
| RU (1) | RU2490272C2 (enExample) |
| TW (1) | TW200936131A (enExample) |
| WO (1) | WO2009099596A2 (enExample) |
| ZA (1) | ZA201005318B (enExample) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MY140680A (en) * | 2002-05-20 | 2010-01-15 | Bristol Myers Squibb Co | Hepatitis c virus inhibitors |
| RU2008152171A (ru) * | 2006-07-05 | 2010-08-10 | Интермьюн, Инк. (Us) | Новые ингибиторы вирусной репликации гепатита с |
| CA2686546A1 (en) | 2007-05-10 | 2008-11-20 | Intermune, Inc. | Novel peptide inhibitors of hepatitis c virus replication |
| WO2009142842A2 (en) | 2008-04-15 | 2009-11-26 | Intermune, Inc. | Novel macrocyclic inhibitors of hepatitis c virus replication |
| UY32099A (es) | 2008-09-11 | 2010-04-30 | Enanta Pharm Inc | Inhibidores macrocíclicos de serina proteasas de hepatitis c |
| AU2009293493B2 (en) | 2008-09-17 | 2014-09-18 | Boehringer Ingelheim International Gmbh | Combination of HCV NS3 protease inhibitor with interferon and ribavirin |
| JP5602161B2 (ja) | 2009-02-03 | 2014-10-08 | イデニク プハルマセウティカルス，インコーポレイテッド | ホスフィナートルテニウム錯体 |
| AR075584A1 (es) | 2009-02-27 | 2011-04-20 | Intermune Inc | COMPOSICIONES TERAPEUTICAS QUE COMPRENDEN beta-D-2'-DESOXI-2'-FLUORO-2'-C-METILCITIDINA Y UN DERIVADO DE ACIDO ISOINDOL CARBOXILICO Y SUS USOS. COMPUESTO. |
| JP2012520891A (ja) * | 2009-03-19 | 2012-09-10 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | スルホニルキノリンの製造方法 |
| TW201040181A (en) | 2009-04-08 | 2010-11-16 | Idenix Pharmaceuticals Inc | Macrocyclic serine protease inhibitors |
| PE20120322A1 (es) | 2009-07-07 | 2012-04-14 | Boehringer Ingelheim Int | Composicion farmaceutica que comprende faldaprevir o una sal del mismo en un vehiculo auto-emulsionante |
| UY32826A (es) | 2009-08-04 | 2011-02-28 | Takeda Pharmaceutical | Compuestos heterocíclicos |
| AR077712A1 (es) * | 2009-08-05 | 2011-09-14 | Idenix Pharmaceuticals Inc | Inhibidores de serina proteasa macrociclica |
| KR20120106942A (ko) | 2009-10-30 | 2012-09-27 | 베링거 인겔하임 인터내셔날 게엠베하 | Ｂｉ２０１３３５, 인터페론 알파 및 리바비린을 포함하는 ｈｃｖ 병용 치료요법을 위한 투여 용법 |
| MY159958A (en) | 2009-12-18 | 2017-02-15 | Idenix Pharmaceuticals Inc | 5,5-fused arylene or heteroarylene hepatitis c virus inhibitors |
| EP2593105A1 (en) * | 2010-07-14 | 2013-05-22 | Vertex Pharmaceuticals Incorporated | Palatable pharmaceutical composition comprising vx-950 |
| CN103534256B (zh) * | 2010-12-30 | 2016-08-10 | 益安药业 | 大环丙型肝炎丝氨酸蛋白酶抑制剂 |
| KR20140003521A (ko) | 2010-12-30 | 2014-01-09 | 이난타 파마슈티칼스, 인코포레이티드 | 페난트리딘 매크로사이클릭 ｃ형 간염 세린 프로테아제 억제제 |
| TW201309690A (zh) | 2011-02-10 | 2013-03-01 | Idenix Pharmaceuticals Inc | 巨環絲胺酸蛋白酶抑制劑，其醫藥組合物及其於治療ｈｃｖ感染之用途 |
| US20120252721A1 (en) | 2011-03-31 | 2012-10-04 | Idenix Pharmaceuticals, Inc. | Methods for treating drug-resistant hepatitis c virus infection with a 5,5-fused arylene or heteroarylene hepatitis c virus inhibitor |
| US10201584B1 (en) | 2011-05-17 | 2019-02-12 | Abbvie Inc. | Compositions and methods for treating HCV |
| EP2802595B1 (en) | 2012-01-11 | 2016-01-06 | AbbVie Inc. | Processes for making hcv protease inhibitors |
| UA119315C2 (uk) | 2012-07-03 | 2019-06-10 | Гіліад Фармассет Елелсі | Інгібітори вірусу гепатиту с |
| BR112015007887A2 (pt) | 2012-10-08 | 2017-07-04 | Abbvie Inc | compostos úteis para produzir inibidores hcv protease |
| JP6511432B2 (ja) | 2013-03-15 | 2019-05-15 | ギリアード サイエンシーズ， インコーポレイテッド | Ｃ型肝炎ウイルスの大環状二環式阻害剤 |
| EP3046924A1 (en) | 2013-09-20 | 2016-07-27 | IDENIX Pharmaceuticals, Inc. | Hepatitis c virus inhibitors |
| WO2015103490A1 (en) | 2014-01-03 | 2015-07-09 | Abbvie, Inc. | Solid antiviral dosage forms |
| US20170135990A1 (en) | 2014-03-05 | 2017-05-18 | Idenix Pharmaceuticals Llc | Pharmaceutical compositions comprising a 5,5-fused heteroarylene flaviviridae inhibitor and their use for treating or preventing flaviviridae infection |
| WO2015134560A1 (en) | 2014-03-05 | 2015-09-11 | Idenix Pharmaceuticals, Inc. | Solid forms of a flaviviridae virus inhibitor compound and salts thereof |
| WO2017197046A1 (en) | 2016-05-10 | 2017-11-16 | C4 Therapeutics, Inc. | C3-carbon linked glutarimide degronimers for target protein degradation |
| CN121974842A (zh) | 2016-05-10 | 2026-05-05 | C4医药公司 | 用于靶蛋白降解的胺连接的c3-戊二酰亚胺降解决定子体 |
| CN109562113A (zh) | 2016-05-10 | 2019-04-02 | C4医药公司 | 用于靶蛋白降解的螺环降解决定子体 |
| CN109562107A (zh) | 2016-05-10 | 2019-04-02 | C4医药公司 | 用于靶蛋白降解的杂环降解决定子体 |
| EP4717317A3 (en) | 2017-06-20 | 2026-06-03 | C4 Therapeutics, Inc. | N/o-linked degrons and degronimers for protein degradation |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2515216A1 (en) * | 2003-02-07 | 2004-08-26 | Enanta Pharmaceuticals, Inc. | Macrocyclic hepatitis c serine protease inhibitors |
| WO2004093798A2 (en) * | 2003-04-18 | 2004-11-04 | Enanta Pharmaceuticals, Inc. | Quinoxalinyl macrocyclic hepatitis c serine protease inhibitors |
| WO2007014926A1 (en) * | 2005-07-29 | 2007-02-08 | Tibotec Pharmaceuticals Ltd. | Macrocyclic inhibitors of hepatitis c virus |
| RU2006110934A (ru) * | 2003-09-05 | 2007-10-10 | Вертекс Фармасьютикалз Инкорпорейтед (Us) | 2-амидо-4-арилокси-1-карбонилпирролидиновые производные в качестве ингибиторов серинпротеаз, в частности, протеазы ns3-ns4a hcv |
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| GB9806815D0 (en) | 1998-03-30 | 1998-05-27 | Hoffmann La Roche | Amino acid derivatives |
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| MXPA03004299A (es) | 2000-11-20 | 2004-02-12 | Bristol Myers Squibb Co | Inhibidores de tripeptido de hepatitis c. |
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| AU2009210789A1 (en) | 2009-08-13 |
| US20100016578A1 (en) | 2010-01-21 |
| CR11618A (es) | 2011-01-31 |
| HK1144198A1 (en) | 2011-02-02 |
| CN101977915B (zh) | 2014-08-13 |
| RU2010136973A (ru) | 2012-03-20 |
| ECSP10010413A (es) | 2010-11-30 |
| NI201000136A (es) | 2011-03-23 |
| CO6501153A2 (es) | 2012-08-15 |
| MX2010008523A (es) | 2010-08-31 |
| JP5574982B2 (ja) | 2014-08-20 |
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| AU2009210789B2 (en) | 2014-01-30 |
| EP2250174B1 (en) | 2013-08-28 |
| IL207333A0 (en) | 2010-12-30 |
| NZ587133A (en) | 2012-10-26 |
| BRPI0908021A2 (pt) | 2015-07-21 |
| US8093379B2 (en) | 2012-01-10 |
| JP2011520772A (ja) | 2011-07-21 |
| CA2712971A1 (en) | 2009-08-13 |
| ES2437147T3 (es) | 2014-01-09 |
| AR070413A1 (es) | 2010-04-07 |
| US8003659B2 (en) | 2011-08-23 |
| US20090202480A1 (en) | 2009-08-13 |
| CN101977915A (zh) | 2011-02-16 |
| KR20100118991A (ko) | 2010-11-08 |
| EP2250174A2 (en) | 2010-11-17 |
| TW200936131A (en) | 2009-09-01 |
| ZA201005318B (en) | 2011-10-26 |
| WO2009099596A3 (en) | 2009-12-03 |
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