JP5752789B2 - Ｈｉｖ成熟阻害剤としての修飾ｃ−３ベツリン酸誘導体 - Google Patents
Ｈｉｖ成熟阻害剤としての修飾ｃ−３ベツリン酸誘導体 Download PDFInfo
- Publication number
- JP5752789B2 JP5752789B2 JP2013513339A JP2013513339A JP5752789B2 JP 5752789 B2 JP5752789 B2 JP 5752789B2 JP 2013513339 A JP2013513339 A JP 2013513339A JP 2013513339 A JP2013513339 A JP 2013513339A JP 5752789 B2 JP5752789 B2 JP 5752789B2
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- JP
- Japan
- Prior art keywords
- compound
- group
- cyclopenta
- coor
- pentamethyl
- 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 *OC(c1ccccc1)=O Chemical compound *OC(c1ccccc1)=O 0.000 description 3
- HCXUOUGXYJPDST-XNNWPPRGSA-N CC(C)([C@@H]1CC2)C(c3ccc(C(O)=O)c(Cl)c3)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@@]2(C)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]1(CO)CC2 Chemical compound CC(C)([C@@H]1CC2)C(c3ccc(C(O)=O)c(Cl)c3)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@@]2(C)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]1(CO)CC2 HCXUOUGXYJPDST-XNNWPPRGSA-N 0.000 description 3
- IFLFEIAIYVETFD-VJBSNJLKSA-N CC(C)([C@@H]1CC2)C(OS(C(F)(F)F)(=O)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@@]2(C)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]1(COC(c1ccccc1)=O)CC2 Chemical compound CC(C)([C@@H]1CC2)C(OS(C(F)(F)F)(=O)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@@]2(C)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]1(COC(c1ccccc1)=O)CC2 IFLFEIAIYVETFD-VJBSNJLKSA-N 0.000 description 1
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- OJXAUTDCWNZCLO-MIYVCLLESA-N CC(C)([C@@H]1CC2)C(c(cc3)ccc3NC(CCC(O)=O)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1C([C@@H](CC1)C(C)=C)[C@@]21C(O)=O Chemical compound CC(C)([C@@H]1CC2)C(c(cc3)ccc3NC(CCC(O)=O)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1C([C@@H](CC1)C(C)=C)[C@@]21C(O)=O OJXAUTDCWNZCLO-MIYVCLLESA-N 0.000 description 1
- RIXYGFSCYAEKKT-SLLAXXTQSA-N CC(C)([C@@H]1CC2)C(c(cc3)ccc3S(C)(=O)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21C(O)=O Chemical compound CC(C)([C@@H]1CC2)C(c(cc3)ccc3S(C)(=O)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21C(O)=O RIXYGFSCYAEKKT-SLLAXXTQSA-N 0.000 description 1
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- ILGQKWCERDYWAC-XNNWPPRGSA-N CC(C)([C@@H]1CC2)C(c(ccc(C(O)=O)c3)c3F)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@@]2(C)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]1(CO)CC2 Chemical compound CC(C)([C@@H]1CC2)C(c(ccc(C(O)=O)c3)c3F)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@@]2(C)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]1(CO)CC2 ILGQKWCERDYWAC-XNNWPPRGSA-N 0.000 description 1
- OTKAMDGGHKJIGH-IYFAHJLCSA-N CC(C)([C@@H]1CC2)C(c3cc(-c4n[nH]nn4)ccc3)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21C(O)=O Chemical compound CC(C)([C@@H]1CC2)C(c3cc(-c4n[nH]nn4)ccc3)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21C(O)=O OTKAMDGGHKJIGH-IYFAHJLCSA-N 0.000 description 1
- CBGIGRZNUSJXHN-DGFPWVBQSA-N CC(C)([C@@H]1CC2)C(c3cc(C(O)=O)n[o]3)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@@]2(C)C1[C@@H]([C@@H](CC1)C(C)=C)[C@@]1(CO)CC2 Chemical compound CC(C)([C@@H]1CC2)C(c3cc(C(O)=O)n[o]3)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@@]2(C)C1[C@@H]([C@@H](CC1)C(C)=C)[C@@]1(CO)CC2 CBGIGRZNUSJXHN-DGFPWVBQSA-N 0.000 description 1
- VOBAPTBAJDSMFV-SLLAXXTQSA-N CC(C)([C@@H]1CC2)C(c3cc(NS(C)(=O)=O)ccc3)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21C(O)=O Chemical compound CC(C)([C@@H]1CC2)C(c3cc(NS(C)(=O)=O)ccc3)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21C(O)=O VOBAPTBAJDSMFV-SLLAXXTQSA-N 0.000 description 1
- JPNIHRUJLQVTLS-BORONXEDSA-N CC(C)([C@@H]1CC2)C(c3ccc(/C=C/C(O)=O)cc3)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21C(O)=O Chemical compound CC(C)([C@@H]1CC2)C(c3ccc(/C=C/C(O)=O)cc3)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21C(O)=O JPNIHRUJLQVTLS-BORONXEDSA-N 0.000 description 1
- AMDLFQTWXJDEPS-CNYWEUNBSA-N CC(C)([C@@H]1CC2)C(c3ccc(C(O)=O)c(Cl)c3)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21C(O)=O Chemical compound CC(C)([C@@H]1CC2)C(c3ccc(C(O)=O)c(Cl)c3)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21C(O)=O AMDLFQTWXJDEPS-CNYWEUNBSA-N 0.000 description 1
- PMSBJRSKUCXXTO-LRAKCVRGSA-N CC(C)([C@@H]1CC2)C(c3ccc(C4(CC4)C(O)=O)cc3)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1C([C@@H](CC1)C(C)=C)[C@@]21C(O)=O Chemical compound CC(C)([C@@H]1CC2)C(c3ccc(C4(CC4)C(O)=O)cc3)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1C([C@@H](CC1)C(C)=C)[C@@]21C(O)=O PMSBJRSKUCXXTO-LRAKCVRGSA-N 0.000 description 1
- XTVQPZUKCIKKGW-JKOHZOSMSA-N CC(C)([C@@H]1CC2)C(c3cccc(S(NC)(=O)=O)c3)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1C([C@@H](CC1)C(C)=C)[C@@]21C(O)=O Chemical compound CC(C)([C@@H]1CC2)C(c3cccc(S(NC)(=O)=O)c3)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1C([C@@H](CC1)C(C)=C)[C@@]21C(O)=O XTVQPZUKCIKKGW-JKOHZOSMSA-N 0.000 description 1
- AQJIQMVLTLKQMX-JWTSRXDFSA-N CC(C)[C@H](CC1)[C@H]([C@H]2CC3)C1(CO)CC[C@@]2(C)[C@](C)(CC1)[C@H]3[C@]2(C)[C@@H]1C(C)(C)C(c(cc1)ccc1C(O)=O)=CC2 Chemical compound CC(C)[C@H](CC1)[C@H]([C@H]2CC3)C1(CO)CC[C@@]2(C)[C@](C)(CC1)[C@H]3[C@]2(C)[C@@H]1C(C)(C)C(c(cc1)ccc1C(O)=O)=CC2 AQJIQMVLTLKQMX-JWTSRXDFSA-N 0.000 description 1
- SVMWRLNUJOVLPB-BMSVDXQESA-N CCOC(c1n[o]c(C(C(C)(C)[C@@H]2CC3)=CC[C@]2(C)[C@@H](CC2)[C@]3(C)[C@@]3(C)C2[C@@H]([C@@H](CC2)C(C)=C)[C@@]2(COC(c2ccccc2)=O)CC3)c1)=O Chemical compound CCOC(c1n[o]c(C(C(C)(C)[C@@H]2CC3)=CC[C@]2(C)[C@@H](CC2)[C@]3(C)[C@@]3(C)C2[C@@H]([C@@H](CC2)C(C)=C)[C@@]2(COC(c2ccccc2)=O)CC3)c1)=O SVMWRLNUJOVLPB-BMSVDXQESA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
- C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
-
- 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
- A61P31/18—Antivirals for RNA viruses for HIV
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Virology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Immunology (AREA)
- Molecular Biology (AREA)
- Tropical Medicine & Parasitology (AREA)
- AIDS & HIV (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US35133810P | 2010-06-04 | 2010-06-04 | |
| US61/351,338 | 2010-06-04 | ||
| PCT/US2011/038879 WO2011153315A1 (en) | 2010-06-04 | 2011-06-02 | Modified c-3 betulinic acid derivatives as hiv maturation inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013527242A JP2013527242A (ja) | 2013-06-27 |
| JP2013527242A5 JP2013527242A5 (https=) | 2014-07-17 |
| JP5752789B2 true JP5752789B2 (ja) | 2015-07-22 |
Family
ID=44627236
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013513339A Expired - Fee Related JP5752789B2 (ja) | 2010-06-04 | 2011-06-02 | Ｈｉｖ成熟阻害剤としての修飾ｃ−３ベツリン酸誘導体 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US8754068B2 (https=) |
| EP (1) | EP2576585B8 (https=) |
| JP (1) | JP5752789B2 (https=) |
| CN (1) | CN103038245B (https=) |
| AR (1) | AR081637A1 (https=) |
| BR (1) | BR112012030818A2 (https=) |
| CA (1) | CA2801487C (https=) |
| EA (1) | EA022393B1 (https=) |
| ES (1) | ES2612452T3 (https=) |
| MX (1) | MX2012013703A (https=) |
| TW (1) | TW201201793A (https=) |
| WO (1) | WO2011153315A1 (https=) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11090313B2 (en) | 2010-05-20 | 2021-08-17 | University Of Iowa Research Foundation | Methods for inhibiting muscle atrophy |
| WO2011146768A1 (en) | 2010-05-20 | 2011-11-24 | University Of Iowa Research Foundation | Methods for inhibiting muscle atrophy |
| PL2670764T3 (pl) * | 2011-01-31 | 2016-02-29 | Bristol Myers Squibb Co | C-28 aminy zmodyfikowanych C-3 pochodnych kwasu betulinowego jako inhibitory dojrzewania HIV |
| KR101886467B1 (ko) * | 2011-01-31 | 2018-08-07 | 비브 헬스케어 유케이 (넘버4) 리미티드 | Hiv 성숙 억제 활성을 갖는 c-17 및 c-3 변형 트리테르페노이드 |
| AU2012268036B2 (en) | 2011-06-06 | 2017-04-06 | THE UNITED STATES OF AMERICA as represented by THE SECRETARY OF STATE OF THE DEPARTMENT OF VETERANS AFFAIRS | Methods of inhibiting muscle atrophy |
| WO2013043778A1 (en) | 2011-09-21 | 2013-03-28 | Bristol-Myers Squibb Company | Novel betulinic acid derivatives with antiviral activity |
| US8906889B2 (en) * | 2012-02-15 | 2014-12-09 | Bristol-Myers Squibb Company | C-3 cycloalkenyl triterpenoids with HIV maturation inhibitory activity |
| US8889854B2 (en) | 2012-05-07 | 2014-11-18 | Bristol-Myers Squibb Company | C-17 bicyclic amines of triterpenoids with HIV maturation inhibitory activity |
| US9637516B2 (en) | 2012-12-31 | 2017-05-02 | Hetero Research Foundation | Betulinic acid proline derivatives as HIV inhibitors |
| SG11201505639SA (en) * | 2013-02-06 | 2015-08-28 | Bristol Myers Squibb Co | C-19 modified triterpenoids with hiv maturation inhibitory activity |
| SG11201506445PA (en) * | 2013-02-25 | 2015-09-29 | Bristol Myers Squibb Co | C-3 alkyl and alkenyl modified betulinic acid derivatives useful in the treatment of hiv |
| SI3129392T1 (sl) | 2014-04-11 | 2020-11-30 | VIIV Healthcare UK(No.4) Limited | Triterpenoidi z inhibitorno aktivnostjo maturacije HIV-a, substituirani na položaju 3 z nearomatskim obročem, ki nosi haloalkilni substituent |
| WO2015195776A1 (en) | 2014-06-19 | 2015-12-23 | Bristol-Myers Squibb Company | Betulinic acid derivatives with hiv maturation inhibitory activity |
| US20170129916A1 (en) | 2014-06-26 | 2017-05-11 | Hetero Research Foundation | Novel betulinic proline imidazole derivatives as hiv inhibitors |
| CN107250153A (zh) * | 2014-11-14 | 2017-10-13 | Viiv保健英国第五有限公司 | 氧代羽扇豆烯衍生物 |
| EP3218388A1 (en) | 2014-11-14 | 2017-09-20 | VIIV Healthcare UK (No.5) Limited | C17-aryl substituted betulinic acid analogs |
| KR20170092580A (ko) * | 2014-11-14 | 2017-08-11 | 비브 헬스케어 유케이 (넘버5) 리미티드 | 연장된 베툴린산 유사체 |
| MA40886B1 (fr) | 2015-02-09 | 2020-03-31 | Hetero Research Foundation | Nouveau triterpénone en c-3 avec des dérivés d'amide inverse en c-28 en tant qu'inhibiteurs du vih |
| US10370405B2 (en) | 2015-03-16 | 2019-08-06 | Hetero Labs Limited | C-3 novel triterpenone with C-28 amide derivatives as HIV inhibitors |
| RU2018105352A (ru) | 2015-07-28 | 2019-08-29 | ГлаксоСмитКлайн Интеллекчуал Проперти (N2) Лимитед | Производные бетулина для предупреждения или лечения ВИЧ-инфекций |
| WO2017017609A1 (en) | 2015-07-28 | 2017-02-02 | Glaxosmithkline Intellectual Property (No.2) Limited | Betuin derivatives for preventing or treating hiv infections |
| RU2018112958A (ru) | 2015-09-24 | 2019-10-28 | ГлаксоСмитКлайн Интеллекчуал Проперти (N2) Лимитед | Соединения с ингибирующей созревание ВИЧ активностью |
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| US20190307776A1 (en) | 2016-06-30 | 2019-10-10 | Viiv Healthcare Uk (No. 5) Limited | Aza-substituted inhibitors of human immunodeficiency virus replication |
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| US5869535A (en) | 1995-03-21 | 1999-02-09 | The Board Of Trustees Of The University Of Illinois | Method and composition for selectively inhibiting melanoma |
| US5679828A (en) * | 1995-06-05 | 1997-10-21 | Biotech Research Labs, Inc. | Betulinic acid and dihydrobetulinic acid derivatives and uses therefor |
| AU762404B2 (en) * | 1998-03-02 | 2003-06-26 | Panacos Pharmaceuticals, Inc. | Acylated betulin and dihydrobetulin derivatives, preparation thereof and use thereof |
| US20040110785A1 (en) | 2001-02-02 | 2004-06-10 | Tao Wang | Composition and antiviral activity of substituted azaindoleoxoacetic piperazine derivatives |
| WO2004028455A2 (en) * | 2002-09-26 | 2004-04-08 | Panacos Pharmaceuticals, Inc. | Monoacylated betulin and dihydrobetulin derivatives, preparation thereof and use thereof |
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| JP4722031B2 (ja) * | 2003-02-11 | 2011-07-13 | ノベリックス・ファーマシューティカルズ・インコーポレイテッド | 腫瘍増殖を阻害するための医薬 |
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| EP1730163A4 (en) * | 2004-03-17 | 2009-12-30 | Panacos Pharmaceuticals Inc | Pharmaceutical salts of 3-O- (3,3-dimethylsuccinyl) betulinic acid |
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| US20090062243A1 (en) * | 2007-08-03 | 2009-03-05 | Advanced Life Sciences, Inc. | Lupane-Type Triterpenoids Modified at 30-Position and Analogues Thereof |
| WO2009042166A1 (en) | 2007-09-25 | 2009-04-02 | Panacos Pharmaceuticals, Inc. | Liquid bevirimat dosage forms for oral administration |
| CA2714049A1 (en) | 2008-02-14 | 2009-08-20 | Virochem Pharma Inc. | Novel 17.beta. lupane derivatives |
| WO2009114083A2 (en) | 2008-03-03 | 2009-09-17 | Panacos Pharmaceuticals, Inc. | Determinants of antiviral response |
| RS55631B1 (sr) * | 2008-04-18 | 2017-06-30 | Reata Pharmaceuticals Inc | Antioksidansni modulatori upale: c-17 homologisani derivati oleanolinske kiseline |
| CN102883608A (zh) * | 2010-02-11 | 2013-01-16 | 葛兰素史密丝克莱恩有限责任公司 | 白桦脂醇衍生物 |
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| BR112012030818A2 (pt) | 2019-09-24 |
| US20120142707A1 (en) | 2012-06-07 |
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| CA2801487C (en) | 2017-12-05 |
| ES2612452T3 (es) | 2017-05-17 |
| US8754068B2 (en) | 2014-06-17 |
| CN103038245A (zh) | 2013-04-10 |
| AR081637A1 (es) | 2012-10-10 |
| EP2576585A1 (en) | 2013-04-10 |
| EA022393B1 (ru) | 2015-12-30 |
| WO2011153315A1 (en) | 2011-12-08 |
| JP2013527242A (ja) | 2013-06-27 |
| EP2576585B1 (en) | 2016-10-12 |
| TW201201793A (en) | 2012-01-16 |
| MX2012013703A (es) | 2012-12-17 |
| CA2801487A1 (en) | 2011-12-08 |
| EP2576585B8 (en) | 2016-12-21 |
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