CN104004039A - 6,11-桥联的联芳大环内酯类 - Google Patents
6,11-桥联的联芳大环内酯类 Download PDFInfo
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- CN104004039A CN104004039A CN201410219293.2A CN201410219293A CN104004039A CN 104004039 A CN104004039 A CN 104004039A CN 201410219293 A CN201410219293 A CN 201410219293A CN 104004039 A CN104004039 A CN 104004039A
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
-
- 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
- A61P31/04—Antibacterial agents
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/69—Two or more oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/34—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D309/36—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
- C07D309/40—Oxygen atoms attached in positions 3 and 4, e.g. maltol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
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- Chemical Kinetics & Catalysis (AREA)
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Applications Claiming Priority (18)
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| US97301707P | 2007-09-17 | 2007-09-17 | |
| US60/973,017 | 2007-09-17 | ||
| US97320107P | 2007-09-18 | 2007-09-18 | |
| US60/973,201 | 2007-09-18 | ||
| US5186208P | 2008-05-09 | 2008-05-09 | |
| US5185708P | 2008-05-09 | 2008-05-09 | |
| US5187508P | 2008-05-09 | 2008-05-09 | |
| US61/051,875 | 2008-05-09 | ||
| US61/051,857 | 2008-05-09 | ||
| US61/051,862 | 2008-05-09 | ||
| US7621308P | 2008-06-27 | 2008-06-27 | |
| US7620808P | 2008-06-27 | 2008-06-27 | |
| US61/076,213 | 2008-06-27 | ||
| US61/076,208 | 2008-06-27 | ||
| US9510008P | 2008-09-08 | 2008-09-08 | |
| US9511108P | 2008-09-08 | 2008-09-08 | |
| US61/095,100 | 2008-09-08 | ||
| US61/095,111 | 2008-09-08 |
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| CN200880115910.7A Division CN101855219B (zh) | 2007-09-17 | 2008-09-17 | 6，11-桥联的联芳大环内酯类 |
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| CN104004039A true CN104004039A (zh) | 2014-08-27 |
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| CN201410219293.2A Pending CN104004039A (zh) | 2007-09-17 | 2008-09-17 | 6,11-桥联的联芳大环内酯类 |
| CN200880115910.7A Expired - Fee Related CN101855219B (zh) | 2007-09-17 | 2008-09-17 | 6，11-桥联的联芳大环内酯类 |
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| CN200880115910.7A Expired - Fee Related CN101855219B (zh) | 2007-09-17 | 2008-09-17 | 6，11-桥联的联芳大环内酯类 |
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| US (2) | US20090118506A1 (https=) |
| EP (1) | EP2203435B1 (https=) |
| JP (2) | JP5642548B2 (https=) |
| KR (2) | KR20120132577A (https=) |
| CN (2) | CN104004039A (https=) |
| AU (1) | AU2008335668C1 (https=) |
| CA (1) | CA2699733C (https=) |
| ES (1) | ES2691252T3 (https=) |
| MX (1) | MX2010002932A (https=) |
| NZ (2) | NZ584159A (https=) |
| WO (2) | WO2009075923A2 (https=) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2203435B1 (en) * | 2007-09-17 | 2018-07-18 | Enanta Pharmaceuticals, Inc. | 6, 11-bridged biaryl macrolides |
| US8354383B2 (en) * | 2007-09-17 | 2013-01-15 | Enanta Pharmaceuticals, Inc. | 6,11-bridged biaryl macrolides |
| US8273720B2 (en) * | 2007-09-17 | 2012-09-25 | Enanta Pharmaceuticals, Inc. | 6,11-bicyclolides: bridged biaryl macrolide derivatives |
| WO2009137787A1 (en) | 2008-05-09 | 2009-11-12 | Enanta Pharmaceuticals, Inc. | Processes for the preparation of 2-fluoro 6-11 bicyclic erythromycin derivatives |
| WO2009137739A1 (en) * | 2008-05-09 | 2009-11-12 | Enanta Pharmaceuticals, Inc. | Processes for the preparation of o-[5-[4-amino-thiazol-2-yl]-pyridin-2-ylmethyl]-hydroxylamine |
| TW200946109A (en) * | 2008-05-09 | 2009-11-16 | Enanta Pharm Inc | Anti-bacterial activity of 9-hydroxy derivatives 6, 11-bicyclolides |
| PT2673285T (pt) * | 2010-12-09 | 2017-10-19 | Wockhardt Ltd | Resumo |
| US20180318268A1 (en) * | 2015-11-19 | 2018-11-08 | Biohaven Pharmaceutical Holding Company Ltd. | Amine prodrugs of pharmaceutical compounds |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN85103264A (zh) * | 1984-04-13 | 1987-01-14 | 美国辉瑞有限公司 | 9a-氮杂-9a-高红霉素衍生物 |
| CN1244532A (zh) * | 1998-03-03 | 2000-02-16 | 辉瑞产品公司 | 3,6－缩醛和烯醇醚大环内酯抗生素 |
| CN1351606A (zh) * | 1999-05-03 | 2002-05-29 | 普利瓦药物工业公司 | 9－脱氧－9a－氮杂－9a高红霉素A的卤代衍生物 |
| US6878691B2 (en) * | 2002-05-13 | 2005-04-12 | Enanta Pharmaceuticals, Inc. | 6-11 bicyclic ketolide derivatives |
| US20060252712A1 (en) * | 2005-05-04 | 2006-11-09 | Guoqiang Wang | 6-11 Bridged oxime erythromycin derivatives |
| US20070082853A1 (en) * | 2005-10-12 | 2007-04-12 | Or Yat S | 6, 11-bridged tricyclic macrolides |
Family Cites Families (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR960000434B1 (ko) * | 1986-12-17 | 1996-01-06 | 다이쇼 세이야꾸 가부시끼가이샤 | 에리스로마이신 a유도체 및 그의 제조 방법 |
| US4921836A (en) * | 1989-05-17 | 1990-05-01 | Burroughs Wellcome Co. | Substituted glutamic acids |
| IL99995A (en) * | 1990-11-21 | 1997-11-20 | Roussel Uclaf | Erythromycin derivatives, their preparation and pharmaceutical compositions containing them |
| EP0559896B1 (en) * | 1990-11-28 | 1997-08-27 | Taisho Pharmaceutical Co. Ltd | 6-o-methylerythromycin a derivative |
| US5202434A (en) * | 1991-04-05 | 1993-04-13 | Merck & Co., Inc. | 8a-aza-8a-homoerythromycin lactams |
| US5556839A (en) * | 1991-04-29 | 1996-09-17 | Eli Lilly And Company | Form II Dirithromycin |
| ATE135707T1 (de) * | 1992-04-22 | 1996-04-15 | Taisho Pharmaceutical Co Ltd | 5-0-desosaminylerythronolid a derivate |
| US5527780A (en) * | 1992-11-05 | 1996-06-18 | Roussel Uclaf | Erythromycin derivatives |
| US5441939A (en) * | 1994-03-04 | 1995-08-15 | Pfizer Inc. | 3"-desmethoxy derivatives of erythromycin and azithromycin |
| FR2738571B1 (fr) * | 1995-09-11 | 1997-10-17 | Roussel Uclaf | Nouveaux derives de la 5-0-desosaminyl 6-0-methyl- erythronolide a, leur procede de preparation et leur application a la preparation de produits biologiquement actifs |
| US6274715B1 (en) * | 1995-11-08 | 2001-08-14 | Abbott Laboratories | Tricyclic erythromycin derivatives |
| DE69733422T2 (de) * | 1996-09-04 | 2006-05-04 | Abbott Laboratories, Abbott Park | 6-0-substituierte ketoliden mit antibakteriellen wirkung |
| UA51730C2 (uk) * | 1996-09-04 | 2002-12-16 | Ебботт Лабораторіз | 6-o-заміщені кетоліди з антибактеріальною активністю, спосіб їх одержання (варіанти), фармацевтична композиція та спосіб регулювання бактеріальної інфекції у ссавців |
| US5922683A (en) * | 1997-05-29 | 1999-07-13 | Abbott Laboratories | Multicyclic erythromycin derivatives |
| US5780605A (en) * | 1997-09-08 | 1998-07-14 | Abbott Laboratories | 6,9-bridged erythromycin derivatives |
| US6124269A (en) * | 1997-10-29 | 2000-09-26 | Abbott Laboratories | 2-Halo-6-O-substituted ketolide derivatives |
| US6046171A (en) * | 1997-10-29 | 2000-04-04 | Abbott Laboratories | 6,11-bridged erythromycin derivatives |
| US6054435A (en) * | 1999-03-19 | 2000-04-25 | Abbott Laboratories | 6-O-substituted macrolides having antibacterial activity |
| CA2370743A1 (en) * | 1999-04-16 | 2000-10-26 | Dennis Hlasta | Ketolide antibacterials |
| US6590083B1 (en) * | 1999-04-16 | 2003-07-08 | Ortho-Mcneil Pharmaceutical, Inc. | Ketolide antibacterials |
| US6355620B1 (en) * | 1999-05-14 | 2002-03-12 | Abbott Laboratories | C-2 modified erythromycin derivatives |
| US7135573B2 (en) * | 2002-05-13 | 2006-11-14 | Enanta Pharmaceuticals, Inc. | Processes for the preparation of O-(6-Pyrazol-1-yl-pyridin-3-ylmethyl)-hydroxylamine |
| US7273853B2 (en) * | 2002-05-13 | 2007-09-25 | Enanta Pharmaceuticals, Inc. | 6-11 bicyclic ketolide derivatives |
| US6764998B1 (en) * | 2003-06-18 | 2004-07-20 | Enanta Pharmaceuticals, Inc. | 6,11-4C-bicyclic 9a-azalide derivatives |
| US7064110B2 (en) * | 2002-05-13 | 2006-06-20 | Enanta Pharmaceuticals, Inc. | 6-11 bicycle ketolide derivatives |
| US7129221B2 (en) * | 2002-05-13 | 2006-10-31 | Enanta Pharmaceuticals, Inc. | 6,11-bicyclic erythromycin derivatives |
| US7910558B2 (en) * | 2002-05-13 | 2011-03-22 | Enanta Pharmaceuticals, Inc. | Bridged macrocyclic compounds and processes for the preparation thereof |
| US6753318B1 (en) * | 2002-07-25 | 2004-06-22 | Enanta Pharmaceuticals, Inc. | 6,11-4-carbon bridged erythromycin derivatives |
| HRP20041056B1 (en) * | 2002-05-13 | 2009-02-28 | Enanta Pharmaceuticals. Inc. | 6-11 bicyclic ketolide derivatives |
| WO2005070918A1 (en) * | 2002-05-13 | 2005-08-04 | Enanta Pharmaceuticals, Inc. | Process for the preparation of t-11 bicyclic erythromycin derivatives |
| US6841664B2 (en) * | 2002-07-25 | 2005-01-11 | Enanra Pharmaceuticals, Inc. | 6,11-4-carbon bridged ketolides |
| US6645941B1 (en) * | 2003-03-26 | 2003-11-11 | Enanta Pharmaceuticals, Inc. | 6,11-3C-bicyclic 9a-azalide derivatives |
| AU2003295869A1 (en) * | 2003-11-20 | 2005-07-14 | Enanta Pharmaceuticals, Inc. | 6-11 bicyclic ketolide drivatives |
| US7414030B2 (en) * | 2004-01-07 | 2008-08-19 | Enanta Pharmaceuticals, Inc. | 6-11 Bicyclic erythromycin derivatives |
| WO2005070113A2 (en) * | 2004-01-09 | 2005-08-04 | Enanta Pharmaceuticals, Inc. | 9n-substituted 6-11 bicyclic erythromycin derivatives |
| US7384921B2 (en) * | 2004-02-20 | 2008-06-10 | Enanta Pharmaceuticals, Inc. | Polymorphic forms of 6-11 bicyclic ketolide derivatives |
| US20080287376A1 (en) * | 2004-07-28 | 2008-11-20 | Mohammad Salman | Ketolide Derivatives as Antibacterial Agents |
| US7229972B2 (en) * | 2004-12-07 | 2007-06-12 | Enanta Pharmaceuticals, Inc. | 3,6-Bicyclolides |
| US20060252710A1 (en) * | 2005-05-04 | 2006-11-09 | Guoqiang Wang | 6-11 Bridged oxime erythromycin derivatives |
| EP2203435B1 (en) * | 2007-09-17 | 2018-07-18 | Enanta Pharmaceuticals, Inc. | 6, 11-bridged biaryl macrolides |
-
2008
- 2008-09-17 EP EP08859833.9A patent/EP2203435B1/en not_active Not-in-force
- 2008-09-17 AU AU2008335668A patent/AU2008335668C1/en not_active Ceased
- 2008-09-17 NZ NZ584159A patent/NZ584159A/xx not_active IP Right Cessation
- 2008-09-17 JP JP2010525113A patent/JP5642548B2/ja not_active Expired - Fee Related
- 2008-09-17 ES ES08859833.9T patent/ES2691252T3/es active Active
- 2008-09-17 US US12/212,596 patent/US20090118506A1/en not_active Abandoned
- 2008-09-17 CN CN201410219293.2A patent/CN104004039A/zh active Pending
- 2008-09-17 NZ NZ600635A patent/NZ600635A/xx not_active IP Right Cessation
- 2008-09-17 MX MX2010002932A patent/MX2010002932A/es active IP Right Grant
- 2008-09-17 CA CA2699733A patent/CA2699733C/en not_active Expired - Fee Related
- 2008-09-17 WO PCT/US2008/076731 patent/WO2009075923A2/en not_active Ceased
- 2008-09-17 KR KR1020127028347A patent/KR20120132577A/ko not_active Ceased
- 2008-09-17 KR KR1020107008527A patent/KR101223158B1/ko not_active Expired - Fee Related
- 2008-09-17 US US12/212,447 patent/US20090075915A1/en not_active Abandoned
- 2008-09-17 CN CN200880115910.7A patent/CN101855219B/zh not_active Expired - Fee Related
- 2008-09-17 WO PCT/US2008/076681 patent/WO2009039177A1/en not_active Ceased
-
2014
- 2014-10-29 JP JP2014220701A patent/JP2015017139A/ja active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN85103264A (zh) * | 1984-04-13 | 1987-01-14 | 美国辉瑞有限公司 | 9a-氮杂-9a-高红霉素衍生物 |
| CN1244532A (zh) * | 1998-03-03 | 2000-02-16 | 辉瑞产品公司 | 3,6－缩醛和烯醇醚大环内酯抗生素 |
| CN1351606A (zh) * | 1999-05-03 | 2002-05-29 | 普利瓦药物工业公司 | 9－脱氧－9a－氮杂－9a高红霉素A的卤代衍生物 |
| US6878691B2 (en) * | 2002-05-13 | 2005-04-12 | Enanta Pharmaceuticals, Inc. | 6-11 bicyclic ketolide derivatives |
| US20060252712A1 (en) * | 2005-05-04 | 2006-11-09 | Guoqiang Wang | 6-11 Bridged oxime erythromycin derivatives |
| US20070082853A1 (en) * | 2005-10-12 | 2007-04-12 | Or Yat S | 6, 11-bridged tricyclic macrolides |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20100059990A (ko) | 2010-06-04 |
| NZ584159A (en) | 2012-08-31 |
| AU2008335668A1 (en) | 2009-06-18 |
| CA2699733A1 (en) | 2009-06-18 |
| US20090118506A1 (en) | 2009-05-07 |
| WO2009039177A1 (en) | 2009-03-26 |
| CN101855219B (zh) | 2014-06-25 |
| AU2008335668B2 (en) | 2012-07-26 |
| EP2203435B1 (en) | 2018-07-18 |
| JP2010539191A (ja) | 2010-12-16 |
| CN101855219A (zh) | 2010-10-06 |
| NZ600635A (en) | 2013-06-28 |
| AU2008335668C1 (en) | 2013-05-30 |
| EP2203435A4 (en) | 2011-03-02 |
| JP5642548B2 (ja) | 2014-12-17 |
| KR101223158B1 (ko) | 2013-01-17 |
| ES2691252T3 (es) | 2018-11-26 |
| CA2699733C (en) | 2013-01-22 |
| JP2015017139A (ja) | 2015-01-29 |
| WO2009075923A2 (en) | 2009-06-18 |
| KR20120132577A (ko) | 2012-12-05 |
| MX2010002932A (es) | 2010-05-27 |
| US20090075915A1 (en) | 2009-03-19 |
| EP2203435A2 (en) | 2010-07-07 |
| WO2009075923A3 (en) | 2009-09-24 |
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