CN103038245B - 作为hiv成熟抑制剂的c-3经修饰的桦木酸衍生物 - Google Patents
作为hiv成熟抑制剂的c-3经修饰的桦木酸衍生物 Download PDFInfo
- Publication number
- CN103038245B CN103038245B CN201180038211.9A CN201180038211A CN103038245B CN 103038245 B CN103038245 B CN 103038245B CN 201180038211 A CN201180038211 A CN 201180038211A CN 103038245 B CN103038245 B CN 103038245B
- Authority
- CN
- China
- Prior art keywords
- compound
- acid
- pentamethyl
- coor
- prop
- 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 C(C1)C2C3*1C23 Chemical compound C(C1)C2C3*1C23 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N C1CCCCC1 Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- IMTBDSQLGYVBOP-ZWFVINSSSA-N CC(C)([C@@H]1CC2)C(OS(C(F)(F)F)(=C)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC[C@]2(CC[C@H]3C(C)=C)C(OCc4ccccc4)=O)C1[C@]23O Chemical compound CC(C)([C@@H]1CC2)C(OS(C(F)(F)F)(=C)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC[C@]2(CC[C@H]3C(C)=C)C(OCc4ccccc4)=O)C1[C@]23O IMTBDSQLGYVBOP-ZWFVINSSSA-N 0.000 description 1
- PMSBJRSKUCXXTO-PGPCFDHNSA-N CC(C)([C@@H]1CC2)C(c3ccc(C4(CC4)C(O)=O)cc3)=CC[C@]1(C)[C@@H](CC1)C2(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(C4(CC4)C(O)=O)cc3)=CC[C@]1(C)[C@@H](CC1)C2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21C(O)=O PMSBJRSKUCXXTO-PGPCFDHNSA-N 0.000 description 1
- PXBODXNDLNXCMI-LYOFKBFXSA-N CC(C)([C@H](CC[C@]1(C)[C@H]2CC3)O)[C@@H]1C=C[C@@]2(C)[C@](C)(CC1)[C@H]3[C@@H]([C@@H](CC2)C(C)=C)[C@@]12C(OCC1=CCCC=C1)=O Chemical compound CC(C)([C@H](CC[C@]1(C)[C@H]2CC3)O)[C@@H]1C=C[C@@]2(C)[C@](C)(CC1)[C@H]3[C@@H]([C@@H](CC2)C(C)=C)[C@@]12C(OCC1=CCCC=C1)=O PXBODXNDLNXCMI-LYOFKBFXSA-N 0.000 description 1
- OTFZXWUAALORHZ-OVSZAUSVSA-N CC(C)C(C)[C@H](CC1)[C@H]([C@@H](CC2)[C@@](C)(CC3)C(C)(CC4)[C@H]2[C@]2(C)[C@@H]4C(C)(C)C(OS(C(F)(F)F)(=O)=O)=CC2)[C@]13C(OCc1ccccc1)=O Chemical compound CC(C)C(C)[C@H](CC1)[C@H]([C@@H](CC2)[C@@](C)(CC3)C(C)(CC4)[C@H]2[C@]2(C)[C@@H]4C(C)(C)C(OS(C(F)(F)F)(=O)=O)=CC2)[C@]13C(OCc1ccccc1)=O OTFZXWUAALORHZ-OVSZAUSVSA-N 0.000 description 1
- ANWZSGLQQCEVJB-CIJSWPNXSA-N CC(C)C(C)[C@H](CC1)[C@H]([C@H]2CC3)[C@@]1(COC(c1ccccc1)=O)CC[C@@]2(C)[C@](C)(CC1)[C@H]3[C@]2(C)[C@@H]1C(C)(C)C(OS(C(F)(F)F)(=O)=O)=CC2 Chemical compound CC(C)C(C)[C@H](CC1)[C@H]([C@H]2CC3)[C@@]1(COC(c1ccccc1)=O)CC[C@@]2(C)[C@](C)(CC1)[C@H]3[C@]2(C)[C@@H]1C(C)(C)C(OS(C(F)(F)F)(=O)=O)=CC2 ANWZSGLQQCEVJB-CIJSWPNXSA-N 0.000 description 1
- CIELMWPDLMIOOB-AGBFSWHTSA-N CC(C)C(CC1)[C@H]([C@@H](CC2)[C@@](C)(CC3)[C@](C)(CC4)[C@H]2[C@@](C)(CC2)[C@@H]4C(C)(C)[C@H]2c2cc(C(O)=O)ccc2)[C@]13C(O)=O Chemical compound CC(C)C(CC1)[C@H]([C@@H](CC2)[C@@](C)(CC3)[C@](C)(CC4)[C@H]2[C@@](C)(CC2)[C@@H]4C(C)(C)[C@H]2c2cc(C(O)=O)ccc2)[C@]13C(O)=O CIELMWPDLMIOOB-AGBFSWHTSA-N 0.000 description 1
- QSKVQTFKQHSJOK-MWQOIRCHSA-N CC(C)[C@H](CC1)[C@H]([C@@H](CC2)[C@@](C)(CC3)[C@](C)(CC4)[C@H]2[C@]2(C)[C@@H]4C(C)(C)C(c4ccc(CCC(O)=O)cc4)=CC2)[C@]13C(OCc1ccccc1)=O Chemical compound CC(C)[C@H](CC1)[C@H]([C@@H](CC2)[C@@](C)(CC3)[C@](C)(CC4)[C@H]2[C@]2(C)[C@@H]4C(C)(C)C(c4ccc(CCC(O)=O)cc4)=CC2)[C@]13C(OCc1ccccc1)=O QSKVQTFKQHSJOK-MWQOIRCHSA-N 0.000 description 1
- JDQCBLNHSOABRA-IENJZNRTSA-N CC(C)[C@H](CC[C@@]1(CC2)C(O)=O)C1[C@@](C)(CC1)[C@]2(C)[C@](C)(CC2C)[C@H]1[C@@](C)(CC1)C2C(C)(C)[C@H]1c(cc1)ccc1C(O)=O Chemical compound CC(C)[C@H](CC[C@@]1(CC2)C(O)=O)C1[C@@](C)(CC1)[C@]2(C)[C@](C)(CC2C)[C@H]1[C@@](C)(CC1)C2C(C)(C)[C@H]1c(cc1)ccc1C(O)=O JDQCBLNHSOABRA-IENJZNRTSA-N 0.000 description 1
- OSZAUGOVBJBTJZ-MVQLEZEISA-N CCC(C)CC[C@@H](C)[C@@H]([C@@H](CC1)C(C)=C)[C@]1(CCC(C)C)C(OCc1ccccc1)=O Chemical compound CCC(C)CC[C@@H](C)[C@@H]([C@@H](CC1)C(C)=C)[C@]1(CCC(C)C)C(OCc1ccccc1)=O OSZAUGOVBJBTJZ-MVQLEZEISA-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)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Virology (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Immunology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Molecular Biology (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 (2)
| Publication Number | Publication Date |
|---|---|
| CN103038245A CN103038245A (zh) | 2013-04-10 |
| CN103038245B true CN103038245B (zh) | 2015-03-25 |
Family
ID=44627236
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201180038211.9A Expired - Fee Related CN103038245B (zh) | 2010-06-04 | 2011-06-02 | 作为hiv成熟抑制剂的c-3经修饰的桦木酸衍生物 |
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 |
| WO2012170546A1 (en) | 2011-06-06 | 2012-12-13 | University Of Iowa Research Foundation | Methods of inhibiting muscle atrophy |
| CN103037692B (zh) | 2010-05-20 | 2015-02-25 | 爱荷华大学研究基金会 | 用于抑制肌萎缩的方法 |
| US8846647B2 (en) * | 2011-01-31 | 2014-09-30 | Bristol-Myers Squibb Company | C-17 and C-3 modified triterpenoids with HIV maturation inhibitory activity |
| HUE026371T2 (en) * | 2011-01-31 | 2016-05-30 | Bristol Myers Squibb Co | C-28 amines from modified C-3 betulinic acid derivatives as anti-HIV matrices |
| MX2014002936A (es) | 2011-09-21 | 2014-04-25 | Bristol Myers Squibb Co | Nuevos derivados de acido betulinico con actividad antiviral. |
| 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 |
| JP6186010B2 (ja) * | 2013-02-06 | 2017-08-23 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | Ｈｉｖ成熟阻害活性を有するｃ−１９修飾トリテルペノイド類 |
| KR20150121712A (ko) * | 2013-02-25 | 2015-10-29 | 브리스톨-마이어스 스큅 컴퍼니 | Hiv의 치료에 유용한 c-3 알킬 및 알케닐 개질된 베툴린산 유도체 |
| UY36070A (es) | 2014-04-11 | 2015-10-30 | Bristol Myers Squibb Company Una Corporación Del Estado De Delaware | Triterpenoides con actividad inhibidora de la maduración de hiv |
| 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 |
| CN107250152A (zh) | 2014-11-14 | 2017-10-13 | Viiv保健英国第五有限公司 | C17‑芳基取代的桦木酸类似物 |
| US9969767B2 (en) | 2014-11-14 | 2018-05-15 | VIIV Healthcare UK (No.5) Limited | Oxolupene derivatives |
| AU2015346314B2 (en) * | 2014-11-14 | 2018-04-12 | VIIV Healthcare UK (No.5) Limited | Extended betulinic acid analogs |
| 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 |
| US20180194799A1 (en) | 2015-07-28 | 2018-07-12 | Glaxosmithkline Intellectual Property (No.2) Limited | Betuin derivatives for preventing or treating hiv infections |
| WO2017017609A1 (en) | 2015-07-28 | 2017-02-02 | Glaxosmithkline Intellectual Property (No.2) Limited | Betuin derivatives for preventing or treating hiv infections |
| KR20180054826A (ko) | 2015-09-24 | 2018-05-24 | 글락소스미스클라인 인털렉츄얼 프로퍼티 (넘버 2) 리미티드 | Hiv 성숙 억제 활성을 갖는 화합물 |
| EP3405474A1 (en) | 2016-01-20 | 2018-11-28 | Glaxosmithkline Intellectual Property (No. 2) Limited | Amine derivatives of lupanes with hiv maturation inhibitory activity |
| AR107512A1 (es) | 2016-02-04 | 2018-05-09 | VIIV HEALTHCARE UK Nº 5 LTD | Triterpenoides modificados en c-3 y c-17 como inhibidores del vih-1 |
| EP3478703A1 (en) * | 2016-06-30 | 2019-05-08 | ViiV Healthcare UK (No.5) Limited | Triterpenoid inhibitors of human immunodeficiency virus replication |
| JP6936820B2 (ja) * | 2016-06-30 | 2021-09-22 | ヴィーブ ヘルスケア ユーケー（ナンバー５）リミテッド | ヒト免疫不全ウイルス複製の阻害剤としてのアザデカリン誘導体 |
| EP3478661A1 (en) | 2016-06-30 | 2019-05-08 | ViiV Healthcare UK (No.5) Limited | Aza-substituted inhibitors of human immunodeficiency virus replication |
| ES2970042T3 (es) | 2018-04-24 | 2024-05-24 | Viiv Healthcare Uk No 5 Ltd | Compuestos con actividad inhibidora de la maduración del VIH |
| PL237998B1 (pl) | 2018-05-28 | 2021-06-28 | Narodowy Inst Lekow | Fosfonowe pochodne kwasu 3-karboksyacylobetulinowego, sposób ich otrzymywania oraz ich zastosowanie |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999045025A1 (en) * | 1998-03-02 | 1999-09-10 | The University Of North Carolina At Chapel Hill | Acylated betulin and dihydrobetulin derivatives, preparation thereof and use thereof |
| WO2005112929A2 (en) * | 2004-05-20 | 2005-12-01 | Cornell Research Foundation, Inc. | Anti-hiv-1 activity of betulinol derivatives |
| CN1747964A (zh) * | 2003-02-11 | 2006-03-15 | 诺瓦利克斯制药公司 | 抑制肿瘤生长的药物 |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5413999A (en) | 1991-11-08 | 1995-05-09 | Merck & Co., Inc. | HIV protease inhibitors useful for the treatment of AIDS |
| US5962527A (en) | 1995-03-21 | 1999-10-05 | The Board Of Trustees Of The University Of Illinois | Method and composition for treating cancers |
| 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 |
| US20040110785A1 (en) | 2001-02-02 | 2004-06-10 | Tao Wang | Composition and antiviral activity of substituted azaindoleoxoacetic piperazine derivatives |
| US7365221B2 (en) | 2002-09-26 | 2008-04-29 | Panacos Pharmaceuticals, Inc. | Monoacylated betulin and dihydrobetulin derivatives, preparation thereof and use thereof |
| AU2003278930A1 (en) * | 2002-09-26 | 2004-04-19 | Niigata University Of Pharmacy And Applied Science | Monoacylated betulin and dihydrobetulin derivatives, preparation thereof and use thereof |
| WO2004089357A2 (en) | 2003-04-02 | 2004-10-21 | Regents Of The University Of Minnesota | Anti-fungal formulation of triterpene and essential oil |
| US7745625B2 (en) | 2004-03-15 | 2010-06-29 | Bristol-Myers Squibb Company | Prodrugs of piperazine and substituted piperidine antiviral agents |
| BRPI0508854A (pt) | 2004-03-17 | 2007-08-28 | Panacos Pharmaceuticals Inc | sais farmacêuticos de ácido-3-o-(3',3'-dimetilsuccinil) betulìnico |
| TW200628161A (en) * | 2004-11-12 | 2006-08-16 | Panacos Pharmaceuticals Inc | Novel betulin derivatives, preparation thereof and use thereof |
| EP1986654A2 (en) * | 2006-02-21 | 2008-11-05 | Achillion Pharmaceuticals, Inc. | Substituted taraxastanes useful for treating viral infections |
| WO2008127364A2 (en) | 2006-10-13 | 2008-10-23 | Myriad Genetics, Inc. | Antiviral compounds and use thereof |
| WO2008115281A2 (en) * | 2006-10-16 | 2008-09-25 | Myriad Genetics, Inc. | Compounds for treating viral infections |
| WO2009020732A1 (en) * | 2007-08-03 | 2009-02-12 | 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 |
| MX2010011439A (es) * | 2008-04-18 | 2011-01-25 | Reata Pharmaceuticals Inc | Moduladores de inflamacion antioxidantes: derivados del acido oleanolico homologacion c-17. |
| WO2011100308A1 (en) * | 2010-02-11 | 2011-08-18 | Glaxosmithkline Llc | Derivatives of betulin |
-
2011
- 2011-06-02 US US13/151,706 patent/US8754068B2/en not_active Expired - Fee Related
- 2011-06-02 CN CN201180038211.9A patent/CN103038245B/zh not_active Expired - Fee Related
- 2011-06-02 CA CA2801487A patent/CA2801487C/en not_active Expired - Fee Related
- 2011-06-02 EP EP11726563.7A patent/EP2576585B8/en not_active Not-in-force
- 2011-06-02 WO PCT/US2011/038879 patent/WO2011153315A1/en not_active Ceased
- 2011-06-02 MX MX2012013703A patent/MX2012013703A/es active IP Right Grant
- 2011-06-02 ES ES11726563.7T patent/ES2612452T3/es active Active
- 2011-06-02 EA EA201270780A patent/EA022393B1/ru not_active IP Right Cessation
- 2011-06-02 BR BR112012030818A patent/BR112012030818A2/pt not_active IP Right Cessation
- 2011-06-02 JP JP2013513339A patent/JP5752789B2/ja not_active Expired - Fee Related
- 2011-06-03 TW TW100119644A patent/TW201201793A/zh unknown
- 2011-06-03 AR ARP110101944A patent/AR081637A1/es not_active Application Discontinuation
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999045025A1 (en) * | 1998-03-02 | 1999-09-10 | The University Of North Carolina At Chapel Hill | Acylated betulin and dihydrobetulin derivatives, preparation thereof and use thereof |
| CN1747964A (zh) * | 2003-02-11 | 2006-03-15 | 诺瓦利克斯制药公司 | 抑制肿瘤生长的药物 |
| WO2005112929A2 (en) * | 2004-05-20 | 2005-12-01 | Cornell Research Foundation, Inc. | Anti-hiv-1 activity of betulinol derivatives |
Non-Patent Citations (1)
| Title |
|---|
| Synthesis and Anti-HIV Activity of Oleanolic Acid Derivatives;Yong-Ming Zhu,et al.;《Bioorganic & Medicinal Chemistry Letters》;20011231;第11卷;3115–3118 * |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2013527242A (ja) | 2013-06-27 |
| CA2801487A1 (en) | 2011-12-08 |
| EA022393B1 (ru) | 2015-12-30 |
| CN103038245A (zh) | 2013-04-10 |
| TW201201793A (en) | 2012-01-16 |
| WO2011153315A1 (en) | 2011-12-08 |
| CA2801487C (en) | 2017-12-05 |
| EA201270780A1 (ru) | 2013-04-30 |
| JP5752789B2 (ja) | 2015-07-22 |
| MX2012013703A (es) | 2012-12-17 |
| ES2612452T3 (es) | 2017-05-17 |
| EP2576585A1 (en) | 2013-04-10 |
| US8754068B2 (en) | 2014-06-17 |
| EP2576585B8 (en) | 2016-12-21 |
| US20120142707A1 (en) | 2012-06-07 |
| BR112012030818A2 (pt) | 2019-09-24 |
| EP2576585B1 (en) | 2016-10-12 |
| AR081637A1 (es) | 2012-10-10 |
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