CN102803254B - 用于软海绵素b类似物合成的呋喃并[3,2-b]吡喃衍生物 - Google Patents
用于软海绵素b类似物合成的呋喃并[3,2-b]吡喃衍生物 Download PDFInfo
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- CN102803254B CN102803254B CN201180015757.2A CN201180015757A CN102803254B CN 102803254 B CN102803254 B CN 102803254B CN 201180015757 A CN201180015757 A CN 201180015757A CN 102803254 B CN102803254 B CN 102803254B
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- 0 CC*CC(CC1)O[C@]2(C*)[C@@]1(*)O[C@](*)C2 Chemical compound CC*CC(CC1)O[C@]2(C*)[C@@]1(*)O[C@](*)C2 0.000 description 4
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- 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
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/12—Radicals substituted by 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
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US29833710P | 2010-01-26 | 2010-01-26 | |
| US61/298337 | 2010-01-26 | ||
| US61/298,337 | 2010-01-26 | ||
| PCT/US2011/022611 WO2011094339A1 (en) | 2010-01-26 | 2011-01-26 | Furo [3, 2 -b] pyrane derivatives useful in the synthesis of halichondrin b analogs |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102803254A CN102803254A (zh) | 2012-11-28 |
| CN102803254B true CN102803254B (zh) | 2016-09-14 |
Family
ID=43726543
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201180015757.2A Active CN102803254B (zh) | 2010-01-26 | 2011-01-26 | 用于软海绵素b类似物合成的呋喃并[3,2-b]吡喃衍生物 |
Country Status (11)
| Country | Link |
|---|---|
| US (6) | US8203010B2 (https=) |
| EP (1) | EP2528914B1 (https=) |
| JP (1) | JP5800834B2 (https=) |
| CN (1) | CN102803254B (https=) |
| BR (1) | BR112012018232B8 (https=) |
| CA (1) | CA2787919C (https=) |
| IL (1) | IL220913A (https=) |
| MX (1) | MX2012008510A (https=) |
| RU (1) | RU2579511C2 (https=) |
| SG (2) | SG10201500552PA (https=) |
| WO (1) | WO2011094339A1 (https=) |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4454151B2 (ja) | 1998-06-17 | 2010-04-21 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | 大環状類似体及びそれらの使用並びに調製方法 |
| SI2522663T1 (sl) | 2004-06-03 | 2015-08-31 | Eisai R&D Management Co., Ltd. | Vmesne spojine za pripravo halihondrina B |
| BRPI0817909B1 (pt) | 2007-10-03 | 2022-06-21 | Eisai R&D Management Co., Ltd | Métodos de obtenção e de preparação de uma composição diastereomericamente pura, compostos, e método para produzir os referidos compostos |
| CA2720632C (en) | 2008-04-04 | 2016-12-20 | Eisai R&D Management Co., Ltd. | Halichondrin b analogs |
| CN102369008B (zh) | 2009-03-30 | 2014-10-29 | 卫材R&D管理有限公司 | 脂质体组合物 |
| RU2579511C2 (ru) | 2010-01-26 | 2016-04-10 | Эйсай Ар Энд Ди Менеджмент Ко., Лтд. | Производные фуро[3,2-в]пирана, применимые в синтезе аналогов |
| GB2526955B (en) | 2011-09-18 | 2016-06-15 | Touchtunes Music Corp | Digital jukebox device with karaoke and/or photo booth features, and associated methods |
| RU2689977C2 (ru) | 2012-12-04 | 2019-05-30 | Эйсай Ар Энд Ди Менеджмент Ко., Лтд. | Применение эрибулина для лечения рака молочной железы |
| BR112015029386B1 (pt) | 2013-06-26 | 2023-11-14 | Eisai R&D Management Co., Ltd. | Uso de eribulina e lenvatinibe como terapia de combinação e kit |
| EP3016957A4 (en) | 2013-07-03 | 2016-11-30 | Alphora Res Inc | SYNTHETIC METHOD FOR THE PRODUCTION OF CYCLIC C1-KETO ANALOGUE OF HALICHONDRIN B AND USEFUL INTERMEDIATE PRODUCTS, INCLUDING INTERMEDIATE PRODUCTS WITH -SO2- (P-TOLYL) GROUPS |
| CN103483352A (zh) * | 2013-10-18 | 2014-01-01 | 李友香 | 抗肿瘤的药用原料药 |
| BR112016009452B1 (pt) * | 2013-11-04 | 2022-06-07 | Eisai R&D Management Co., Ltd | Métodos de preparar intermediários na síntese de eribulina, métodos de preparar eribulina e mesilato de eribulina, e compostos intermediários |
| EP3077399B1 (en) | 2013-12-06 | 2019-02-20 | Eisai R&D Management Co., Ltd. | Methods useful in the synthesis of halichondrin b analogs |
| US20170100367A1 (en) | 2014-05-28 | 2017-04-13 | Eisai R&D Management Co., Ltd. | Use of eribulin in the treatment of cancer |
| US10556910B2 (en) | 2014-06-30 | 2020-02-11 | President And Fellows Of Harvard College | Synthesis of halichondrin analogs and uses thereof |
| AU2016226157B2 (en) | 2015-03-04 | 2022-01-27 | Eisai R&D Management Co., Ltd. | Combination of a PD-1 antagonist and eribulin for treating cancer |
| KR102662228B1 (ko) | 2015-03-04 | 2024-05-02 | 머크 샤프 앤드 돔 코포레이션 | 암을 치료하기 위한 pd-1 길항제 및 vegfr/fgfr/ret 티로신 키나제 억제제의 조합 |
| US10344038B2 (en) | 2015-04-30 | 2019-07-09 | President And Fellows Of Harvard College | Chromium-mediated coupling and application to the synthesis of halichondrins |
| MX392296B (es) | 2015-05-07 | 2025-03-24 | Eisai R&D Man Co Ltd | Reacciones de macrociclizacion e intermediarios y otros fragmentos utiles en la sintesis de macrolidos de halicondrina. |
| CN108601760A (zh) | 2016-02-12 | 2018-09-28 | 卫材R&D管理有限公司 | 艾日布林的合成中的中间体及相关的合成方法 |
| PE20231050A1 (es) | 2016-03-02 | 2023-07-11 | Eisai Randd Man Co Ltd | Conjugados de anticuerpo y farmaco basados en eribulina y metodos para su uso |
| WO2017188350A1 (ja) | 2016-04-28 | 2017-11-02 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | 腫瘍の成長を抑制する方法 |
| KR102404629B1 (ko) | 2016-06-30 | 2022-06-02 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 할리콘드린 마크롤리드 및 그의 유사체의 합성에 유용한 프린스 반응 및 중간체 |
| WO2018071792A1 (en) | 2016-10-14 | 2018-04-19 | Merck Sharp & Dohme Corp. | Combination of a pd-1 antagonist and eribulin for treating urothelial cancer |
| JP6978758B2 (ja) | 2016-11-11 | 2021-12-08 | プレジデント アンド フェローズ オブ ハーバード カレッジ | パラジウム媒介ケトール化 |
| CN108658956B (zh) * | 2017-03-28 | 2021-02-02 | 上海时莱生物技术有限公司 | 艾日布林中间体及其制备方法 |
| SMT202200455T1 (it) | 2017-04-05 | 2023-01-13 | Harvard College | Composto macrociclico e relativi usi |
| US9938288B1 (en) | 2017-04-05 | 2018-04-10 | President And Fellows Of Harvard College | Macrocyclic compound and uses thereof |
| CN108948064B (zh) * | 2017-05-17 | 2021-02-02 | 上海时莱生物技术有限公司 | 一种艾日布林中间体及其制备方法 |
| US11498892B2 (en) | 2017-07-06 | 2022-11-15 | President And Fellows Of Harvard College | Fe/Cu-mediated ketone synthesis |
| WO2019010363A1 (en) | 2017-07-06 | 2019-01-10 | President And Fellows Of Harvard College | HALICHONDRINES SYNTHESIS |
| US20190046513A1 (en) | 2017-08-10 | 2019-02-14 | Huya Bioscience International, Llc | Combination therapies of hdac inhibitors and tubulin inhibitors |
| WO2019099646A1 (en) | 2017-11-15 | 2019-05-23 | President And Fellows Of Harvard College | Macrocyclic compounds and uses thereof |
| WO2019097073A1 (en) | 2017-11-20 | 2019-05-23 | Basilea Pharmaceutica International AG | Pharmaceutical combinations for use in the treatment of neoplastic diseases |
| IL275729B2 (en) | 2018-01-03 | 2023-09-01 | Eisai R&D Man Co Ltd | Prins reaction and compounds useful in the synthesis of helicondrin macrolides and their analogs |
| US12036204B2 (en) | 2019-07-26 | 2024-07-16 | Eisai R&D Management Co., Ltd. | Pharmaceutical composition for treating tumor |
| US11083705B2 (en) | 2019-07-26 | 2021-08-10 | Eisai R&D Management Co., Ltd. | Pharmaceutical composition for treating tumor |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993017690A1 (en) * | 1992-03-12 | 1993-09-16 | President And Fellows Of Harvard College | Halichondrins and related compounds |
| CN1312804A (zh) * | 1998-06-17 | 2001-09-12 | 卫材株式会社 | 大环类似物及其使用和制备的方法 |
| CN1993342A (zh) * | 2004-06-03 | 2007-07-04 | 卫材株式会社 | 用于制备软海绵素b的中间体 |
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| SU652180A1 (ru) * | 1975-12-16 | 1979-03-15 | Краснодарский политехнический институт | 1(Фурил-2,)-2-(2-,, формилфурил-5,, ) этилен или его метильное производное как промежуточный продукт дл синтеза фуран-2,5-дикарбоновой кислоты и способ его получени |
| US5436238A (en) * | 1992-03-12 | 1995-07-25 | President And Fellows Of Harvard College | Halichondrins and related compounds |
| GB9206244D0 (en) | 1992-03-23 | 1992-05-06 | Pharma Mar Sa | Cytotoxic compound from a marine sponge |
| TW255880B (https=) | 1992-09-09 | 1995-09-01 | Hoechst Ag | |
| AU4255697A (en) | 1996-09-06 | 1998-03-26 | Eli Lilly And Company | Catalytic selective sulfonylation process |
| US8097648B2 (en) | 1998-06-17 | 2012-01-17 | Eisai R&D Management Co., Ltd. | Methods and compositions for use in treating cancer |
| US6653341B1 (en) * | 1998-06-17 | 2003-11-25 | Eisai Co., Ltd. | Methods and compositions for use in treating cancer |
| SI2522663T1 (sl) | 2004-06-03 | 2015-08-31 | Eisai R&D Management Co., Ltd. | Vmesne spojine za pripravo halihondrina B |
| US20060045846A1 (en) | 2004-08-30 | 2006-03-02 | Horstmann Thomas E | Reagents and methods for labeling terminal olefins |
| US20060154312A1 (en) | 2004-12-09 | 2006-07-13 | Sergei Agoulnik | Tubulin isotype screening in cancer therapy using halichondrin B analogs |
| WO2008010776A1 (en) | 2006-07-21 | 2008-01-24 | Agency For Science, Technology And Research | Aigialomycin d and derivatives thereof and their use in treating cancer or malaria or a microbial infection |
| BRPI0817909B1 (pt) | 2007-10-03 | 2022-06-21 | Eisai R&D Management Co., Ltd | Métodos de obtenção e de preparação de uma composição diastereomericamente pura, compostos, e método para produzir os referidos compostos |
| CN101910180A (zh) * | 2007-11-16 | 2010-12-08 | 卫材R&D管理有限公司 | 用于软海绵素b类似物合成的新颖中间体和用于该中间体的新颖脱磺酰化反应 |
| CA2720632C (en) | 2008-04-04 | 2016-12-20 | Eisai R&D Management Co., Ltd. | Halichondrin b analogs |
| RU2579511C2 (ru) | 2010-01-26 | 2016-04-10 | Эйсай Ар Энд Ди Менеджмент Ко., Лтд. | Производные фуро[3,2-в]пирана, применимые в синтезе аналогов |
| WO2012147900A1 (en) | 2011-04-28 | 2012-11-01 | Eisai R&D Management Co., Ltd. | Microreactor process for halichondrin b analog synthesis |
| WO2013078559A1 (en) | 2011-11-30 | 2013-06-06 | Alphora Research Inc. | Process for preparation of (3r)-2,4-di-leaving group-3-methylbut-1-ene |
| US9278979B2 (en) | 2012-03-30 | 2016-03-08 | Alphora Research Inc. | Synthetic process for preparation of macrocyclic C1-keto analogs of halichondrin B and intermediates useful therein |
| EP3016957A4 (en) | 2013-07-03 | 2016-11-30 | Alphora Res Inc | SYNTHETIC METHOD FOR THE PRODUCTION OF CYCLIC C1-KETO ANALOGUE OF HALICHONDRIN B AND USEFUL INTERMEDIATE PRODUCTS, INCLUDING INTERMEDIATE PRODUCTS WITH -SO2- (P-TOLYL) GROUPS |
| BR112016009452B1 (pt) | 2013-11-04 | 2022-06-07 | Eisai R&D Management Co., Ltd | Métodos de preparar intermediários na síntese de eribulina, métodos de preparar eribulina e mesilato de eribulina, e compostos intermediários |
| EP3077399B1 (en) | 2013-12-06 | 2019-02-20 | Eisai R&D Management Co., Ltd. | Methods useful in the synthesis of halichondrin b analogs |
| MX392296B (es) | 2015-05-07 | 2025-03-24 | Eisai R&D Man Co Ltd | Reacciones de macrociclizacion e intermediarios y otros fragmentos utiles en la sintesis de macrolidos de halicondrina. |
| CN108601760A (zh) | 2016-02-12 | 2018-09-28 | 卫材R&D管理有限公司 | 艾日布林的合成中的中间体及相关的合成方法 |
| KR102404629B1 (ko) | 2016-06-30 | 2022-06-02 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 할리콘드린 마크롤리드 및 그의 유사체의 합성에 유용한 프린스 반응 및 중간체 |
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2011
- 2011-01-26 RU RU2012136468/04A patent/RU2579511C2/ru active
- 2011-01-26 MX MX2012008510A patent/MX2012008510A/es unknown
- 2011-01-26 JP JP2012551271A patent/JP5800834B2/ja active Active
- 2011-01-26 EP EP11702900.9A patent/EP2528914B1/en active Active
- 2011-01-26 WO PCT/US2011/022611 patent/WO2011094339A1/en not_active Ceased
- 2011-01-26 BR BR112012018232A patent/BR112012018232B8/pt active IP Right Grant
- 2011-01-26 US US13/014,517 patent/US8203010B2/en active Active
- 2011-01-26 CA CA2787919A patent/CA2787919C/en active Active
- 2011-01-26 CN CN201180015757.2A patent/CN102803254B/zh active Active
- 2011-01-26 SG SG10201500552PA patent/SG10201500552PA/en unknown
- 2011-01-26 SG SG2012053468A patent/SG182612A1/en unknown
-
2012
- 2012-05-22 US US13/477,483 patent/US8350067B2/en active Active
- 2012-07-12 IL IL220913A patent/IL220913A/en active IP Right Grant
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2013
- 2013-01-07 US US13/735,516 patent/US8927597B2/en active Active
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2014
- 2014-12-19 US US14/577,417 patent/US9382262B2/en active Active
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2016
- 2016-06-29 US US15/196,600 patent/US9856276B2/en not_active Expired - Fee Related
-
2017
- 2017-12-13 US US15/840,109 patent/US10494388B2/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993017690A1 (en) * | 1992-03-12 | 1993-09-16 | President And Fellows Of Harvard College | Halichondrins and related compounds |
| CN1312804A (zh) * | 1998-06-17 | 2001-09-12 | 卫材株式会社 | 大环类似物及其使用和制备的方法 |
| CN1993342A (zh) * | 2004-06-03 | 2007-07-04 | 卫材株式会社 | 用于制备软海绵素b的中间体 |
Non-Patent Citations (2)
| Title |
|---|
| "New Syntheses of E7389 C14-C35 and Halichondrin C14-C38 Building Blocks: Double-Inversion Approach";Dae-Shik Kim，等;《J. AM. CHEM. SOC.》;20091006;第131卷(第43期);第15636–15641页 * |
| "Synthetic Studies of Halichondrin B, an Antitumor Polyether Macrolide Isolated from a Marine Sponge. 8. Synthesis of the Lactone Part (C1-C36) via Horner-Emmons Coupling Between C1-C15 and C16-C36 Fragments and Yamaguchi Lactonization.";Kiyoshi Horita，等;《Tetrahedron Letters》;19971229;第38卷(第52期);第8965-8968页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| BR112012018232A2 (pt) | 2016-02-23 |
| SG10201500552PA (en) | 2015-03-30 |
| US20130123519A1 (en) | 2013-05-16 |
| US9856276B2 (en) | 2018-01-02 |
| RU2579511C2 (ru) | 2016-04-10 |
| BR112012018232B8 (pt) | 2023-01-10 |
| US10494388B2 (en) | 2019-12-03 |
| IL220913A (en) | 2016-11-30 |
| US20150175620A1 (en) | 2015-06-25 |
| MX2012008510A (es) | 2012-11-21 |
| US8203010B2 (en) | 2012-06-19 |
| CA2787919C (en) | 2018-07-31 |
| CA2787919A1 (en) | 2011-08-04 |
| CN102803254A (zh) | 2012-11-28 |
| US8927597B2 (en) | 2015-01-06 |
| JP2013518116A (ja) | 2013-05-20 |
| EP2528914A1 (en) | 2012-12-05 |
| SG182612A1 (en) | 2012-08-30 |
| US20110184190A1 (en) | 2011-07-28 |
| EP2528914B1 (en) | 2014-06-11 |
| US8350067B2 (en) | 2013-01-08 |
| RU2012136468A (ru) | 2014-03-10 |
| BR112012018232B1 (pt) | 2022-11-29 |
| US20120289718A1 (en) | 2012-11-15 |
| US9382262B2 (en) | 2016-07-05 |
| WO2011094339A1 (en) | 2011-08-04 |
| US20180162885A1 (en) | 2018-06-14 |
| JP5800834B2 (ja) | 2015-10-28 |
| US20160376294A1 (en) | 2016-12-29 |
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