CN101010281B - 肾素抑制剂的替代合成方法及其中间体 - Google Patents
肾素抑制剂的替代合成方法及其中间体 Download PDFInfo
- Publication number
- CN101010281B CN101010281B CN2005800292634A CN200580029263A CN101010281B CN 101010281 B CN101010281 B CN 101010281B CN 2005800292634 A CN2005800292634 A CN 2005800292634A CN 200580029263 A CN200580029263 A CN 200580029263A CN 101010281 B CN101010281 B CN 101010281B
- Authority
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- China
- Prior art keywords
- formula
- alkyl
- compound
- alkoxy
- give
- 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.)
- Expired - Fee Related
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- 0 Cc(cc1)c(C)cc1C([C@](*)C[C@](*)C*)=O Chemical compound Cc(cc1)c(C)cc1C([C@](*)C[C@](*)C*)=O 0.000 description 6
- JRRUMOVZODPUIU-FHWLQOOXSA-N CC(C)[C@H](C[C@@H]([C@H](CC1)O)NC1=O)Cc(cc1)cc(OCCCOC)c1OC Chemical compound CC(C)[C@H](C[C@@H]([C@H](CC1)O)NC1=O)Cc(cc1)cc(OCCCOC)c1OC JRRUMOVZODPUIU-FHWLQOOXSA-N 0.000 description 1
- VLXZMMYSUDQLCH-FHWLQOOXSA-N CC(C)[C@H](C[C@@H]([C@H](CC1)OC1=O)N)Cc(cc1)cc(OCCCOC)c1OC Chemical compound CC(C)[C@H](C[C@@H]([C@H](CC1)OC1=O)N)Cc(cc1)cc(OCCCOC)c1OC VLXZMMYSUDQLCH-FHWLQOOXSA-N 0.000 description 1
- VAERCXIMEFSDOL-RWPDHJIBSA-N CC(C)[C@H](C[C@@H]([C@H](CC1=C(C)C)OC(OC(C)(C)C)=O)N(C(OC(C)(C)C)=O)C1=O)Cc(cc1)cc(OCCCOC)c1OC Chemical compound CC(C)[C@H](C[C@@H]([C@H](CC1=C(C)C)OC(OC(C)(C)C)=O)N(C(OC(C)(C)C)=O)C1=O)Cc(cc1)cc(OCCCOC)c1OC VAERCXIMEFSDOL-RWPDHJIBSA-N 0.000 description 1
- RKIHBONWUAHQHA-RJZHOWMISA-N CC(C)[C@H](C[C@@H]([C@H](CC1C(C)=C)OC(OC(C)(C)C)=O)N(C(COC(C)(C)C)=O)C1=O)Cc(cc1)cc(OCCCOC)c1OC Chemical compound CC(C)[C@H](C[C@@H]([C@H](CC1C(C)=C)OC(OC(C)(C)C)=O)N(C(COC(C)(C)C)=O)C1=O)Cc(cc1)cc(OCCCOC)c1OC RKIHBONWUAHQHA-RJZHOWMISA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/126—Acids containing more than four carbon atoms
- C07C53/128—Acids containing more than four carbon atoms the carboxylic group being bound to a carbon atom bound to at least two other carbon atoms, e.g. neo-acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/16—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
- C07D207/36—Oxygen or sulfur atoms
- C07D207/38—2-Pyrrolones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D211/74—Oxygen atoms
- C07D211/76—Oxygen atoms attached in position 2 or 6
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D307/32—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyrrole Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0419361.1 | 2004-08-31 | ||
| GBGB0419361.1A GB0419361D0 (en) | 2004-08-31 | 2004-08-31 | Organic compounds |
| PCT/EP2005/009347 WO2006024501A1 (en) | 2004-08-31 | 2005-08-30 | Alternative synthesis of renin inhibitors and intermediates thereof |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2011103045513A Division CN102417464A (zh) | 2004-08-31 | 2005-08-30 | 肾素抑制剂的替代合成方法及其中间体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101010281A CN101010281A (zh) | 2007-08-01 |
| CN101010281B true CN101010281B (zh) | 2011-12-21 |
Family
ID=33155811
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2005800292634A Expired - Fee Related CN101010281B (zh) | 2004-08-31 | 2005-08-30 | 肾素抑制剂的替代合成方法及其中间体 |
| CN2011103045513A Pending CN102417464A (zh) | 2004-08-31 | 2005-08-30 | 肾素抑制剂的替代合成方法及其中间体 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2011103045513A Pending CN102417464A (zh) | 2004-08-31 | 2005-08-30 | 肾素抑制剂的替代合成方法及其中间体 |
Country Status (17)
| Country | Link |
|---|---|
| US (2) | US7910774B2 (enExample) |
| EP (2) | EP1978012A1 (enExample) |
| JP (1) | JP2008511573A (enExample) |
| KR (1) | KR20070045300A (enExample) |
| CN (2) | CN101010281B (enExample) |
| AT (1) | ATE485257T1 (enExample) |
| AU (1) | AU2005279351B2 (enExample) |
| BR (1) | BRPI0514742A (enExample) |
| CA (1) | CA2576749C (enExample) |
| DE (1) | DE602005024282D1 (enExample) |
| ES (1) | ES2354986T3 (enExample) |
| GB (1) | GB0419361D0 (enExample) |
| MX (1) | MX2007002419A (enExample) |
| PL (1) | PL1789377T3 (enExample) |
| PT (1) | PT1789377E (enExample) |
| RU (1) | RU2411230C2 (enExample) |
| WO (1) | WO2006024501A1 (enExample) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0511686D0 (en) * | 2005-06-08 | 2005-07-13 | Novartis Ag | Organic compounds |
| GB0519764D0 (en) | 2005-09-28 | 2005-11-09 | Novartis Ag | Organic compounds |
| GB0521083D0 (en) | 2005-10-17 | 2005-11-23 | Novartis Ag | Organic compounds |
| GB2431649A (en) * | 2005-10-25 | 2007-05-02 | Novartis Ag | Alternative synthesis of aryl-octanoyl amide compounds |
| GB2431651A (en) * | 2005-10-25 | 2007-05-02 | Novartis Ag | Synthesis of aryl-octanoyl amide compounds |
| GB2431648A (en) * | 2005-10-25 | 2007-05-02 | Novartis Ag | Alternative synthesis of aryl-octanoyl amide compounds |
| GB2431653A (en) * | 2005-10-25 | 2007-05-02 | Novartis Ag | Alternative synthesis of aryl-octanoyl amide compounds |
| GB2431642A (en) * | 2005-10-25 | 2007-05-02 | Novartis Ag | Alternative synthesis of aryl-octanoyl amide compounds |
| GB2431646A (en) * | 2005-10-25 | 2007-05-02 | Novartis Ag | Alternative synthesis of aryl-octanoyl amide compounds |
| GB0522789D0 (en) | 2005-11-08 | 2005-12-14 | Novartis Ag | Organic compounds |
| CA2668828A1 (en) * | 2006-11-07 | 2008-05-29 | Novartis Ag | Crystalline forms of aliskiren hemifumarate |
| DE102007049039A1 (de) | 2007-10-11 | 2009-04-16 | Reuter Chemischer Apparatebau Kg | Verfahren zur Herstellung von 8-Hydrazino-8-Aryl-Octanoylderivaten und deren Verwendung |
| EP2062874B1 (en) | 2007-11-20 | 2014-12-17 | KRKA, tovarna zdravil, d.d., Novo mesto | Process and intermediates for the preparation of aliskiren |
| SI2189442T1 (sl) | 2008-11-20 | 2015-03-31 | Krka, Tovarna Zdravil, D.D., Novo Mesto | Postopek in intermediati za pripravo aliskirena |
| CN102686556A (zh) * | 2009-08-11 | 2012-09-19 | 诺瓦提斯公司 | 内酯和内酰胺的开环 |
| US8203005B2 (en) | 2009-10-29 | 2012-06-19 | Carbo Design Llc | Manufacturing process for enantiomerically pure 8-aryloctanoic acids as Aliskiren |
| CN101774986B (zh) * | 2010-01-06 | 2012-03-28 | 浙江天宇药业股份有限公司 | 一种制备阿利克伦及其中间体的方法 |
| CN102329244A (zh) * | 2010-07-13 | 2012-01-25 | 凯瑞斯德生化(苏州)有限公司 | 一种rs-托特罗定的制备方法及中间体化合物 |
| CN102372653A (zh) * | 2010-08-10 | 2012-03-14 | 江苏恒瑞医药股份有限公司 | 二苯甲醇类衍生物、其制备方法及其在医药上的应用 |
| EP2551260A1 (en) | 2011-07-28 | 2013-01-30 | Chemo Ibérica, S.A. | Chemical process for opening ring compounds |
| US8703976B2 (en) | 2011-10-02 | 2014-04-22 | Milan Soukup | Manufacturing process for 8-aryloctanoic acids such as Aliskiren |
| ITMI20120354A1 (it) * | 2012-03-07 | 2013-09-08 | Friulchem Spa | Processo per la produzione di aliskirene |
| CN103044273B (zh) * | 2012-11-29 | 2014-12-24 | 珠海保税区丽珠合成制药有限公司 | 一种酒石酸托特罗定的合成方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1215201A2 (en) * | 2000-12-14 | 2002-06-19 | Speedel Pharma AG | Process for the preparation of aryloctanoyl amides |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL88619A0 (en) * | 1987-12-15 | 1989-07-31 | Pfizer | Non-peptidic renin inhibitors |
| DE3837197A1 (de) | 1988-11-02 | 1990-05-03 | Continental Ag | Vorrichtung zum aufbereiten von unvulkanisiertem kautschuk |
| MY119161A (en) | 1994-04-18 | 2005-04-30 | Novartis Ag | Delta-amino-gamma-hydroxy-omega-aryl-alkanoic acid amides with enzyme especially renin inhibiting activities |
| GB9523493D0 (en) * | 1995-11-16 | 1996-01-17 | British Biotech Pharm | Preparation of allyl succinate derivatives and starting materials therefore |
| CA2414847C (en) | 2000-07-05 | 2009-06-16 | Speedel Pharma Ag | Process for the preparation of substituted octanoyl amides |
| DE122007000077I2 (de) * | 2000-07-25 | 2008-08-21 | Speedel Pharma Ag Hirchgaessle | Verfahren zur herstellung von substituierten octanoyl-amiden |
| US20060154926A1 (en) * | 2002-06-11 | 2006-07-13 | Elan Pharmaceuticals, Inc. | Methods of treating alzheimer's disease using aryl alkanoic acid amides |
-
2004
- 2004-08-31 GB GBGB0419361.1A patent/GB0419361D0/en not_active Ceased
-
2005
- 2005-08-30 CN CN2005800292634A patent/CN101010281B/zh not_active Expired - Fee Related
- 2005-08-30 RU RU2007111752/04A patent/RU2411230C2/ru not_active IP Right Cessation
- 2005-08-30 PL PL05775930T patent/PL1789377T3/pl unknown
- 2005-08-30 AT AT05775930T patent/ATE485257T1/de active
- 2005-08-30 AU AU2005279351A patent/AU2005279351B2/en not_active Ceased
- 2005-08-30 CA CA2576749A patent/CA2576749C/en not_active Expired - Fee Related
- 2005-08-30 PT PT05775930T patent/PT1789377E/pt unknown
- 2005-08-30 EP EP08158568A patent/EP1978012A1/en not_active Withdrawn
- 2005-08-30 CN CN2011103045513A patent/CN102417464A/zh active Pending
- 2005-08-30 US US11/573,790 patent/US7910774B2/en not_active Expired - Fee Related
- 2005-08-30 ES ES05775930T patent/ES2354986T3/es not_active Expired - Lifetime
- 2005-08-30 MX MX2007002419A patent/MX2007002419A/es active IP Right Grant
- 2005-08-30 KR KR1020077004734A patent/KR20070045300A/ko not_active Abandoned
- 2005-08-30 BR BRPI0514742-5A patent/BRPI0514742A/pt not_active IP Right Cessation
- 2005-08-30 JP JP2007528770A patent/JP2008511573A/ja active Pending
- 2005-08-30 WO PCT/EP2005/009347 patent/WO2006024501A1/en not_active Ceased
- 2005-08-30 EP EP05775930A patent/EP1789377B1/en not_active Expired - Lifetime
- 2005-08-30 DE DE602005024282T patent/DE602005024282D1/de not_active Expired - Lifetime
-
2011
- 2011-02-07 US US13/022,243 patent/US8143416B2/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1215201A2 (en) * | 2000-12-14 | 2002-06-19 | Speedel Pharma AG | Process for the preparation of aryloctanoyl amides |
Non-Patent Citations (1)
| Title |
|---|
| Richard Goschke et al."The nonchiral bislactim diethoxy ether as a highly stereo-inducing synthon for sterically hindered,r-branched a-amino acids:A pracical,Large-Scale route to an intermediate of the novel renin inhibitor aliskiren".《helvetica chimica acta》.2003,第86卷 * |
Also Published As
| Publication number | Publication date |
|---|---|
| MX2007002419A (es) | 2007-04-23 |
| KR20070045300A (ko) | 2007-05-02 |
| CA2576749A1 (en) | 2006-03-09 |
| US7910774B2 (en) | 2011-03-22 |
| PT1789377E (pt) | 2011-01-25 |
| AU2005279351A1 (en) | 2006-03-09 |
| AU2005279351B2 (en) | 2009-04-23 |
| CA2576749C (en) | 2012-10-16 |
| ATE485257T1 (de) | 2010-11-15 |
| RU2411230C2 (ru) | 2011-02-10 |
| ES2354986T3 (es) | 2011-03-21 |
| DE602005024282D1 (de) | 2010-12-02 |
| US8143416B2 (en) | 2012-03-27 |
| GB0419361D0 (en) | 2004-10-06 |
| US20110137044A1 (en) | 2011-06-09 |
| EP1978012A1 (en) | 2008-10-08 |
| PL1789377T3 (pl) | 2011-04-29 |
| CN101010281A (zh) | 2007-08-01 |
| CN102417464A (zh) | 2012-04-18 |
| RU2007111752A (ru) | 2008-10-10 |
| EP1789377B1 (en) | 2010-10-20 |
| WO2006024501A1 (en) | 2006-03-09 |
| US20070208055A1 (en) | 2007-09-06 |
| JP2008511573A (ja) | 2008-04-17 |
| BRPI0514742A (pt) | 2008-06-24 |
| EP1789377A1 (en) | 2007-05-30 |
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