JP5241728B2 - C型肝炎ウイルス阻害剤としての大環状ペプチド - Google Patents
C型肝炎ウイルス阻害剤としての大環状ペプチド Download PDFInfo
- Publication number
- JP5241728B2 JP5241728B2 JP2009537352A JP2009537352A JP5241728B2 JP 5241728 B2 JP5241728 B2 JP 5241728B2 JP 2009537352 A JP2009537352 A JP 2009537352A JP 2009537352 A JP2009537352 A JP 2009537352A JP 5241728 B2 JP5241728 B2 JP 5241728B2
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- Japan
- Prior art keywords
- alkyl
- cycloalkyl
- tert
- mmol
- compound
- 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
Links
- 0 CC(*)(*C(C1)[C@]1(C(*)=O)NC([C@](CC(*)(*)C1)N1C1=O)=O)[C@@]1N(*)* Chemical compound CC(*)(*C(C1)[C@]1(C(*)=O)NC([C@](CC(*)(*)C1)N1C1=O)=O)[C@@]1N(*)* 0.000 description 6
- LFKDJXLFVYVEFG-UHFFFAOYSA-N CC(C)(C)OC(N)=O Chemical compound CC(C)(C)OC(N)=O LFKDJXLFVYVEFG-UHFFFAOYSA-N 0.000 description 1
- KIEPKKVYVRBQKN-UHFFFAOYSA-N CC(C)(C)OC(NS(CC(Nc1c(C)[o]nc1C)=O)(=O)=O)=O Chemical compound CC(C)(C)OC(NS(CC(Nc1c(C)[o]nc1C)=O)(=O)=O)=O KIEPKKVYVRBQKN-UHFFFAOYSA-N 0.000 description 1
- FXASRRCVDHFKJQ-YOUBHCOFSA-N CC(C)(C)OC(N[C@@H](CCCCCC=C)C(N(C[C@@](C1)(c(cc2)ccc2-c2cccc(CC(C)(C)OC(N[C@@H](CCCCC/C=C\C(C3)[C@]3(C(NS(C3CC3)=O)=O)NC([C@H](C3)N4C[C@@H]3c3ccccc3)=O)C4=O)=O)c2)O)[C@@H]1C(NC1(CC1)C(NS(C1CC1)(=O)=O)=O)=O)O)O Chemical compound CC(C)(C)OC(N[C@@H](CCCCCC=C)C(N(C[C@@](C1)(c(cc2)ccc2-c2cccc(CC(C)(C)OC(N[C@@H](CCCCC/C=C\C(C3)[C@]3(C(NS(C3CC3)=O)=O)NC([C@H](C3)N4C[C@@H]3c3ccccc3)=O)C4=O)=O)c2)O)[C@@H]1C(NC1(CC1)C(NS(C1CC1)(=O)=O)=O)=O)O)O FXASRRCVDHFKJQ-YOUBHCOFSA-N 0.000 description 1
- JDVZQFKEWTYPPG-UHFFFAOYSA-N CCCC1(CC1)S(N)(=O)=O Chemical compound CCCC1(CC1)S(N)(=O)=O JDVZQFKEWTYPPG-UHFFFAOYSA-N 0.000 description 1
- QPOCDFSJBNGOLR-UHFFFAOYSA-N NS(C1(CC2CC2)CC1)(=O)=O Chemical compound NS(C1(CC2CC2)CC1)(=O)=O QPOCDFSJBNGOLR-UHFFFAOYSA-N 0.000 description 1
- HUMNYLRZRPPJDN-UHFFFAOYSA-N O=Cc1ccccc1 Chemical compound O=Cc1ccccc1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07D498/02—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 two hetero rings
- C07D498/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
- C07K5/0802—Tripeptides with the first amino acid being neutral
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
- C07K5/0815—Tripeptides with the first amino acid being basic
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Gastroenterology & Hepatology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Virology (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US86612006P | 2006-11-16 | 2006-11-16 | |
| US60/866,120 | 2006-11-16 | ||
| US11/939,753 | 2007-11-14 | ||
| US11/939,753 US8003604B2 (en) | 2006-11-16 | 2007-11-14 | Hepatitis C virus inhibitors |
| PCT/US2007/084777 WO2008064057A1 (en) | 2006-11-16 | 2007-11-15 | Macrocyclic peptides as hepatitis c virus inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010510967A JP2010510967A (ja) | 2010-04-08 |
| JP2010510967A5 JP2010510967A5 (enExample) | 2010-12-24 |
| JP5241728B2 true JP5241728B2 (ja) | 2013-07-17 |
Family
ID=39251294
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009537352A Expired - Fee Related JP5241728B2 (ja) | 2006-11-16 | 2007-11-15 | C型肝炎ウイルス阻害剤としての大環状ペプチド |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8003604B2 (enExample) |
| EP (1) | EP2089020B1 (enExample) |
| JP (1) | JP5241728B2 (enExample) |
| AT (1) | ATE492559T1 (enExample) |
| DE (1) | DE602007011493D1 (enExample) |
| NO (1) | NO20091846L (enExample) |
| WO (1) | WO2008064057A1 (enExample) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MY140680A (en) | 2002-05-20 | 2010-01-15 | Bristol Myers Squibb Co | Hepatitis c virus inhibitors |
| US8178564B2 (en) * | 2006-11-06 | 2012-05-15 | Poniard Pharmaceuticals, Inc. | Use of picoplatin to treat colorectal cancer |
| WO2009099596A2 (en) * | 2008-02-04 | 2009-08-13 | Idenix Pharamaceuticals, Inc. | Macrocyclic serine protease inhibitors |
| US8207341B2 (en) | 2008-09-04 | 2012-06-26 | Bristol-Myers Squibb Company | Process or synthesizing substituted isoquinolines |
| UY32099A (es) | 2008-09-11 | 2010-04-30 | Enanta Pharm Inc | Inhibidores macrocíclicos de serina proteasas de hepatitis c |
| TW201040181A (en) | 2009-04-08 | 2010-11-16 | Idenix Pharmaceuticals Inc | Macrocyclic serine protease inhibitors |
| US8232246B2 (en) * | 2009-06-30 | 2012-07-31 | Abbott Laboratories | Anti-viral compounds |
| CA2769652A1 (en) | 2009-08-05 | 2011-02-10 | Idenix Pharmaceuticals, Inc. | Macrocyclic serine protease inhibitors useful against viral infections, particularly hcv |
| WO2012040242A1 (en) * | 2010-09-22 | 2012-03-29 | Intermune, Inc. | Substituted proline inhibitors of hepatitis c virus replication |
| JP5918264B2 (ja) | 2010-12-22 | 2016-05-18 | アッヴィ・インコーポレイテッド | C型肝炎阻害剤およびその使用 |
| CA2822556A1 (en) | 2010-12-30 | 2012-07-05 | Enanta Pharmaceuticals, Inc | Macrocyclic hepatitis c serine protease inhibitors |
| CN103380132B (zh) | 2010-12-30 | 2016-08-31 | 益安药业 | 菲啶大环丙型肝炎丝氨酸蛋白酶抑制剂 |
| 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 |
| US8957203B2 (en) | 2011-05-05 | 2015-02-17 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US10201584B1 (en) | 2011-05-17 | 2019-02-12 | Abbvie Inc. | Compositions and methods for treating HCV |
| US8691757B2 (en) | 2011-06-15 | 2014-04-08 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| SI2909205T1 (sl) | 2012-10-19 | 2017-02-28 | Bristol-Myers Squibb Company | 9-metil substituiran heksadekahidrociklopropa(e)pirolo(1,2-A)(1,4)diazaciklopentadecinil karbamat derivati kot nestrukturalni 3 (NS3) proteazni inhibitorji za zdravljenje hepatitis C virusnih infekcij |
| EP2914598B1 (en) | 2012-11-02 | 2017-10-18 | Bristol-Myers Squibb Company | Hepatitis c virus inhibitors |
| WO2014070964A1 (en) | 2012-11-02 | 2014-05-08 | Bristol-Myers Squibb Company | Hepatitis c virus inhibitors |
| US9643999B2 (en) | 2012-11-02 | 2017-05-09 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US9409943B2 (en) | 2012-11-05 | 2016-08-09 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| JP6342922B2 (ja) | 2013-03-07 | 2018-06-13 | ブリストル−マイヤーズ スクイブ カンパニーBristol−Myers Squibb Company | C型肝炎ウイルス阻害剤 |
| EP3089757A1 (en) | 2014-01-03 | 2016-11-09 | AbbVie Inc. | Solid antiviral dosage forms |
| BR112016028801A2 (pt) | 2014-06-12 | 2017-08-22 | Allocyte Pharmaceuticals Ag | inibidores de moléculas pequenas de lfa-1 |
Family Cites Families (98)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0475255A3 (en) | 1990-09-12 | 1993-04-14 | F. Hoffmann-La Roche Ag | Process for the preparation of optically pure (s)-alpha-((tert-butylsulfonyl)methyl)hydro cinnamic acid |
| DE69709671T2 (de) | 1996-10-18 | 2002-08-22 | Vertex Pharmaceuticals Inc., Cambridge | Inhibitoren von serinproteasen, insbesondere von ns3-protease des hepatitis-c-virus |
| JP4452401B2 (ja) | 1997-08-11 | 2010-04-21 | ベーリンガー インゲルハイム (カナダ) リミテッド | C型肝炎ウイルス阻害ペプチドアナログ |
| EP1003775B1 (en) | 1997-08-11 | 2005-03-16 | Boehringer Ingelheim (Canada) Ltd. | Hepatitis c inhibitor peptides |
| AR022061A1 (es) | 1998-08-10 | 2002-09-04 | Boehringer Ingelheim Ca Ltd | Peptidos inhibidores de la hepatitis c, una composicion farmaceutica que los contiene, el uso de los mismos para preparar una composicion farmaceutica, el uso de un producto intermedio para la preparacion de estos peptidos y un procedimiento para la preparacion de un peptido analogo de los mismos. |
| US6323180B1 (en) | 1998-08-10 | 2001-11-27 | Boehringer Ingelheim (Canada) Ltd | Hepatitis C inhibitor tri-peptides |
| UA74546C2 (en) | 1999-04-06 | 2006-01-16 | Boehringer Ingelheim Ca Ltd | Macrocyclic peptides having activity relative to hepatitis c virus, a pharmaceutical composition and use of the pharmaceutical composition |
| ATE461207T1 (de) | 2000-07-21 | 2010-04-15 | Schering Corp | Peptide als inhibitoren der ns3-serinprotease des hepatitis c virus |
| US7244721B2 (en) | 2000-07-21 | 2007-07-17 | Schering Corporation | Peptides as NS3-serine protease inhibitors of hepatitis C virus |
| PE20020707A1 (es) | 2000-11-20 | 2002-08-11 | Bristol Myers Squibb Co | Compuestos tripeptidicos como inhibidores de la proteasa ns3 del virus de hepatitis c |
| US6867185B2 (en) | 2001-12-20 | 2005-03-15 | Bristol-Myers Squibb Company | Inhibitors of hepatitis C virus |
| CA2369711A1 (en) | 2002-01-30 | 2003-07-30 | Boehringer Ingelheim (Canada) Ltd. | Macrocyclic peptides active against the hepatitis c virus |
| CA2370396A1 (en) | 2002-02-01 | 2003-08-01 | Boehringer Ingelheim (Canada) Ltd. | Hepatitis c inhibitor tri-peptides |
| CA2369970A1 (en) | 2002-02-01 | 2003-08-01 | Boehringer Ingelheim (Canada) Ltd. | Hepatitis c inhibitor tri-peptides |
| US6828301B2 (en) | 2002-02-07 | 2004-12-07 | Boehringer Ingelheim International Gmbh | Pharmaceutical compositions for hepatitis C viral protease inhibitors |
| US20060199773A1 (en) | 2002-05-20 | 2006-09-07 | Sausker Justin B | Crystalline forms of (1R,2S)-N-[(1,1-dimethylethoxy)carbonyl]-3-methyl-L-valyl-(4R)-4-[(6-methoxy-1-isoquinolinyl)oxy]-L-prolyl-1-amino-N-(cyclopropylsulfonyl)-2-ethenyl-cyclopropanecarboxamide, monopotassium salt |
| DE60334205D1 (en) | 2002-05-20 | 2010-10-28 | Bristol Myers Squibb Co | Heterocyclische sulfonamid-hepatitis-c-virus-hemmer |
| PL215228B1 (pl) | 2002-05-20 | 2013-11-29 | Bristol Myers Squibb Co | Zwiazki tripeptydowe, ich zastosowanie i kompozycja farmaceutyczna je zawierajaca oraz jej zastosowanie |
| DE60324552D1 (en) | 2002-05-20 | 2008-12-18 | Bristol Myers Squibb Co | Substituierte cycloalkyl p1' hepatitis c virus inhibitoren |
| MY140680A (en) | 2002-05-20 | 2010-01-15 | Bristol Myers Squibb Co | Hepatitis c virus inhibitors |
| US20040033959A1 (en) | 2002-07-19 | 2004-02-19 | Boehringer Ingelheim Pharmaceuticals, Inc. | Pharmaceutical compositions for hepatitis C viral protease inhibitors |
| US20050075279A1 (en) | 2002-10-25 | 2005-04-07 | Boehringer Ingelheim International Gmbh | Macrocyclic peptides active against the hepatitis C virus |
| US7601709B2 (en) | 2003-02-07 | 2009-10-13 | Enanta Pharmaceuticals, Inc. | Macrocyclic hepatitis C serine protease inhibitors |
| CN1771050A (zh) | 2003-02-07 | 2006-05-10 | 益安药业 | 丙型肝炎丝氨酸蛋白酶的大环抑制剂 |
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| KR20050108420A (ko) | 2003-04-02 | 2005-11-16 | 베링거 인겔하임 인터내셔날 게엠베하 | C형 간염 바이러스 프로테아제 억제제를 위한 약제학적조성물 |
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| BRPI0509467A (pt) | 2004-03-30 | 2007-09-11 | Intermune Inc | compostos macrocìclicos como inibidores de replicação viral |
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| KR101294467B1 (ko) | 2005-07-25 | 2013-09-09 | 인터뮨, 인크. | C형 간염 바이러스 복제의 신규 거대고리형 억제제 |
| JO2768B1 (en) | 2005-07-29 | 2014-03-15 | تيبوتيك فارماسيوتيكالز ليمتد | Large cyclic inhibitors of hepatitis C virus |
| RU2419619C2 (ru) | 2005-07-29 | 2011-05-27 | Медивир Аб | Макроциклические ингибиторы вируса гепатита с |
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| AU2006274861B2 (en) | 2005-07-29 | 2012-11-08 | Medivir Ab | Macrocyclic inhibitors of hepatitis C virus |
| PT1912997E (pt) | 2005-07-29 | 2011-12-19 | Tibotec Pharm Ltd | Inibidores macrocíclicos do vírus da hepatite c |
| PE20070343A1 (es) | 2005-07-29 | 2007-05-12 | Medivir Ab | Inhibidores macrociclicos del virus de la hepatitis c |
| PE20070210A1 (es) | 2005-07-29 | 2007-04-16 | Tibotec Pharm Ltd | Compuestos macrociclicos como inhibidores del virus de hepatitis c |
| US8183277B2 (en) | 2005-07-29 | 2012-05-22 | Tibotec Pharmaceuticals Ltd. | Macrocylic inhibitors of hepatitis C virus |
| PE20070211A1 (es) | 2005-07-29 | 2007-05-12 | Medivir Ab | Compuestos macrociclicos como inhibidores del virus de hepatitis c |
| RU2441870C2 (ru) | 2005-07-29 | 2012-02-10 | Тиботек Фармасьютикалз Лтд. | Макроциклические ингибиторы вируса гепатита с |
| ES2456617T3 (es) | 2005-07-29 | 2014-04-23 | Janssen R&D Ireland | Inhibidores macrocíclicos del virus de la hepatitis C |
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| EP1915382A2 (en) | 2005-08-01 | 2008-04-30 | Phenomix Corporation | Hepatitis c serine protease inhibitors and uses therefor |
| AR055395A1 (es) | 2005-08-26 | 2007-08-22 | Vertex Pharma | Compuestos inhibidores de la actividad de la serina proteasa ns3-ns4a del virus de la hepatitis c |
| DE602006019323D1 (de) | 2005-10-11 | 2011-02-10 | Intermune Inc | Verbindungen und verfahren zur inhibierung der replikation des hepatitis-c-virus |
| US7772183B2 (en) | 2005-10-12 | 2010-08-10 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US7741281B2 (en) | 2005-11-03 | 2010-06-22 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| WO2007082131A1 (en) | 2006-01-09 | 2007-07-19 | Bristol-Myers Squibb Company | Process for the preparation of hydroxy substituted heterocycles |
| JP2009528353A (ja) | 2006-03-03 | 2009-08-06 | シェーリング コーポレイション | Hcvのプロテアーゼ阻害剤およびires阻害剤の医薬的組み合わせ |
| GB0609492D0 (en) | 2006-05-15 | 2006-06-21 | Angeletti P Ist Richerche Bio | Therapeutic agents |
| US7635683B2 (en) | 2006-08-04 | 2009-12-22 | Enanta Pharmaceuticals, Inc. | Quinoxalinyl tripeptide hepatitis C virus inhibitors |
| US7605126B2 (en) | 2006-08-11 | 2009-10-20 | Enanta Pharmaceuticals, Inc. | Acylaminoheteroaryl hepatitis C virus protease inhibitors |
| US7582605B2 (en) | 2006-08-11 | 2009-09-01 | Enanta Pharmaceuticals, Inc. | Phosphorus-containing hepatitis C serine protease inhibitors |
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2007
- 2007-11-14 US US11/939,753 patent/US8003604B2/en active Active
- 2007-11-15 AT AT07864430T patent/ATE492559T1/de not_active IP Right Cessation
- 2007-11-15 EP EP07864430A patent/EP2089020B1/en active Active
- 2007-11-15 JP JP2009537352A patent/JP5241728B2/ja not_active Expired - Fee Related
- 2007-11-15 DE DE602007011493T patent/DE602007011493D1/de active Active
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Also Published As
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|---|---|
| EP2089020A1 (en) | 2009-08-19 |
| NO20091846L (no) | 2009-06-08 |
| JP2010510967A (ja) | 2010-04-08 |
| WO2008064057A1 (en) | 2008-05-29 |
| ATE492559T1 (de) | 2011-01-15 |
| EP2089020B1 (en) | 2010-12-22 |
| DE602007011493D1 (de) | 2011-02-03 |
| US20080159982A1 (en) | 2008-07-03 |
| US8003604B2 (en) | 2011-08-23 |
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