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 | |
| US61/298,337 | 2010-01-26 | ||
| US61/298337 | 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) | SG182612A1 (https=) |
| WO (1) | WO2011094339A1 (https=) |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6214865B1 (en) | 1998-06-17 | 2001-04-10 | Eisai Co., Ltd. | Macrocyclic analogs and methods of their use and preparation |
| EP2522663B1 (en) | 2004-06-03 | 2015-04-01 | Eisai R&D Management Co., Ltd. | Intermediates for the preparation of halichondrin B |
| RU2489437C2 (ru) | 2007-10-03 | 2013-08-10 | Эйсай Ар Энд Ди Менеджмент Ко., Лтд. | Промежуточные соединения и способы синтеза аналогов галихондрина в |
| CN105801599A (zh) | 2008-04-04 | 2016-07-27 | 卫材R&D管理有限公司 | 软海绵素b类似物 |
| ES2593027T3 (es) | 2009-03-30 | 2016-12-05 | Eisai R&D Management Co., Ltd. | Composición liposomal |
| WO2011094339A1 (en) | 2010-01-26 | 2011-08-04 | Eisai R&D Management Co., Ltd. | Furo [3, 2 -b] pyrane derivatives useful in the synthesis of halichondrin b analogs |
| CN110097416B (zh) | 2011-09-18 | 2022-05-10 | 踏途音乐公司 | 具有卡拉ok和照相亭功能的数字点播设备及相关方法 |
| MX2015007185A (es) | 2012-12-04 | 2017-09-05 | Eisai R&D Man Co Ltd | Uso de eribulina en el tratamiento de cancer de pecho. |
| KR102265952B1 (ko) | 2013-06-26 | 2021-06-16 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 암 치료 병용요법으로서 에리불린 및 렌바티닙의 용도 |
| CA2916537C (en) | 2013-07-03 | 2021-07-27 | Alphora Research Inc. | Synthetic process for preparation of macrocyclic c1-keto analogs of halichondrin b and intermediates useful therein including intermediates containing -so2-(p-tolyl) groups |
| CN103483352A (zh) * | 2013-10-18 | 2014-01-01 | 李友香 | 抗肿瘤的药用原料药 |
| EP3689881B1 (en) * | 2013-11-04 | 2022-01-12 | Eisai R&D Management Co., Ltd. | Macrocyclization reactions and intermediates useful in the synthesis of analogs of halichondrin b |
| MX384292B (es) | 2013-12-06 | 2025-03-14 | Eisai R&D Man Co Ltd | Metodos utiles en la sintesis de analogos de halicondrina b. |
| RU2699545C2 (ru) | 2014-05-28 | 2019-09-06 | ЭЙСАЙ Ар ЭНД Ди МЕНЕДЖМЕНТ КО., ЛТД | Применение эрибулина в лечении рака |
| US10556910B2 (en) | 2014-06-30 | 2020-02-11 | President And Fellows Of Harvard College | Synthesis of halichondrin analogs and uses thereof |
| 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 |
| CA2978311A1 (en) | 2015-03-04 | 2016-09-09 | Merck Sharp & Dohme Corp. | Combination of a pd-1 antagonist and eribulin for treating cancer |
| US10344038B2 (en) | 2015-04-30 | 2019-07-09 | President And Fellows Of Harvard College | Chromium-mediated coupling and application to the synthesis of halichondrins |
| KR102743950B1 (ko) * | 2015-05-07 | 2024-12-18 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 할리콘드린 마크롤라이드의 합성에 유용한 마크로고리화 반응 및 중간체 및 기타 단편 |
| EP3413887B1 (en) | 2016-02-12 | 2021-04-07 | Eisai R&D Management Co., Ltd. | Intermediates in the synthesis of eribulin and related methods of synthesis |
| EP3423105B1 (en) | 2016-03-02 | 2021-05-05 | Eisai R&D Management Co., Ltd. | Eribulin-based antibody-drug conjugates and methods of use |
| US12029724B2 (en) | 2016-04-28 | 2024-07-09 | Eisai R&D Management Co., Ltd. | Method for inhibiting tumor growth |
| US11136335B2 (en) | 2016-06-30 | 2021-10-05 | Eisai R&D Management Co., Ltd. | Prins reaction and intermediates useful in the synthesis of halichondrin macrolides and analogs thereof |
| BR112019007145A2 (pt) | 2016-10-14 | 2019-07-02 | Eisai R&D Man Co Ltd | combinação de um antagonista de pd-1 e eribulina para o tratamento de câncer urotelial |
| 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 |
| ES2931533T3 (es) | 2017-04-05 | 2022-12-30 | Harvard College | Compuesto macrocíclico y usos del mismo |
| 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 |
| HUE061306T2 (hu) | 2017-07-06 | 2023-06-28 | Harvard College | Halikondrinok szintézise |
| US20190046513A1 (en) | 2017-08-10 | 2019-02-14 | Huya Bioscience International, Llc | Combination therapies of hdac inhibitors and tubulin inhibitors |
| CN111566113B (zh) | 2017-11-15 | 2024-01-09 | 哈佛大学的校长及成员们 | 大环化合物及其用途 |
| US11419856B2 (en) | 2017-11-20 | 2022-08-23 | Basilea Pharmaceutica International AG | Pharmaceutical combinations for use in the treatment of neoplastic diseases |
| SG11202005548WA (en) | 2018-01-03 | 2020-07-29 | Eisai R&D Man Co Ltd | Prins reaction and compounds useful in the synthesis of halichondrin macrolides and analogs thereof |
| US11083705B2 (en) | 2019-07-26 | 2021-08-10 | Eisai R&D Management Co., Ltd. | Pharmaceutical composition for treating tumor |
| US12036204B2 (en) | 2019-07-26 | 2024-07-16 | 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 | |
| WO1998009942A1 (en) | 1996-09-06 | 1998-03-12 | Eli Lilly And Company | Catalytic selective sulfonylation process |
| US6653341B1 (en) * | 1998-06-17 | 2003-11-25 | Eisai Co., Ltd. | Methods and compositions for use in treating cancer |
| US8097648B2 (en) | 1998-06-17 | 2012-01-17 | Eisai R&D Management Co., Ltd. | Methods and compositions for use in treating cancer |
| EP2522663B1 (en) | 2004-06-03 | 2015-04-01 | Eisai R&D Management Co., Ltd. | Intermediates for the preparation of halichondrin B |
| US20060045846A1 (en) | 2004-08-30 | 2006-03-02 | Horstmann Thomas E | Reagents and methods for labeling terminal olefins |
| EP1831697A4 (en) | 2004-12-09 | 2011-01-26 | Eisai R&D Man Co Ltd | SEARCH FOR TUBULINISOTYPES IN CANCER THERAPY USING HALICHONDRIN B ANALOG |
| 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 |
| RU2489437C2 (ru) | 2007-10-03 | 2013-08-10 | Эйсай Ар Энд Ди Менеджмент Ко., Лтд. | Промежуточные соединения и способы синтеза аналогов галихондрина в |
| RU2010118063A (ru) * | 2007-11-16 | 2011-12-27 | ЭЙСАЙ Ар энд Ди МЕНЕДЖМЕНТ КО., ЛТД. (JP) | Новое промежуточное соединение для синтеза аналога галихондрина в и новая реакция десульфонилирования, применяемая для получения промежуточного соединения |
| CN105801599A (zh) | 2008-04-04 | 2016-07-27 | 卫材R&D管理有限公司 | 软海绵素b类似物 |
| WO2011094339A1 (en) | 2010-01-26 | 2011-08-04 | Eisai R&D Management Co., Ltd. | Furo [3, 2 -b] pyrane derivatives useful in the synthesis of halichondrin b analogs |
| WO2012147900A1 (en) | 2011-04-28 | 2012-11-01 | Eisai R&D Management Co., Ltd. | Microreactor process for halichondrin b analog synthesis |
| EP2785687B1 (en) | 2011-11-30 | 2019-02-20 | Sandoz AG | Process for preparation of (3r)-2,4-di-leaving group-3-methylbut-1-ene |
| WO2013142999A1 (en) | 2012-03-30 | 2013-10-03 | Alphora Research Inc. | Synthetic process for preparation of macrocyclic c1-keto analogs of halichondrin b and intermediates useful therein |
| CA2916537C (en) | 2013-07-03 | 2021-07-27 | Alphora Research Inc. | Synthetic process for preparation of macrocyclic c1-keto analogs of halichondrin b and intermediates useful therein including intermediates containing -so2-(p-tolyl) groups |
| EP3689881B1 (en) | 2013-11-04 | 2022-01-12 | Eisai R&D Management Co., Ltd. | Macrocyclization reactions and intermediates useful in the synthesis of analogs of halichondrin b |
| MX384292B (es) | 2013-12-06 | 2025-03-14 | Eisai R&D Man Co Ltd | Metodos utiles en la sintesis de analogos de halicondrina b. |
| KR102743950B1 (ko) | 2015-05-07 | 2024-12-18 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 할리콘드린 마크롤라이드의 합성에 유용한 마크로고리화 반응 및 중간체 및 기타 단편 |
| EP3413887B1 (en) | 2016-02-12 | 2021-04-07 | Eisai R&D Management Co., Ltd. | Intermediates in the synthesis of eribulin and related methods of synthesis |
| US11136335B2 (en) | 2016-06-30 | 2021-10-05 | Eisai R&D Management Co., Ltd. | Prins reaction and intermediates useful in the synthesis of halichondrin macrolides and analogs thereof |
-
2011
- 2011-01-26 WO PCT/US2011/022611 patent/WO2011094339A1/en not_active Ceased
- 2011-01-26 RU RU2012136468/04A patent/RU2579511C2/ru active
- 2011-01-26 CA CA2787919A patent/CA2787919C/en active Active
- 2011-01-26 EP EP11702900.9A patent/EP2528914B1/en active Active
- 2011-01-26 SG SG2012053468A patent/SG182612A1/en unknown
- 2011-01-26 SG SG10201500552PA patent/SG10201500552PA/en unknown
- 2011-01-26 JP JP2012551271A patent/JP5800834B2/ja active Active
- 2011-01-26 CN CN201180015757.2A patent/CN102803254B/zh active Active
- 2011-01-26 MX MX2012008510A patent/MX2012008510A/es unknown
- 2011-01-26 BR BR112012018232A patent/BR112012018232B8/pt active IP Right Grant
- 2011-01-26 US US13/014,517 patent/US8203010B2/en active Active
-
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
-
2013
- 2013-01-07 US US13/735,516 patent/US8927597B2/en active Active
-
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 |
|---|---|
| EP2528914B1 (en) | 2014-06-11 |
| JP5800834B2 (ja) | 2015-10-28 |
| BR112012018232B8 (pt) | 2023-01-10 |
| CN102803254A (zh) | 2012-11-28 |
| BR112012018232A2 (pt) | 2016-02-23 |
| US20130123519A1 (en) | 2013-05-16 |
| RU2012136468A (ru) | 2014-03-10 |
| CA2787919A1 (en) | 2011-08-04 |
| US20180162885A1 (en) | 2018-06-14 |
| US10494388B2 (en) | 2019-12-03 |
| US20160376294A1 (en) | 2016-12-29 |
| IL220913A (en) | 2016-11-30 |
| SG182612A1 (en) | 2012-08-30 |
| US20110184190A1 (en) | 2011-07-28 |
| US20120289718A1 (en) | 2012-11-15 |
| JP2013518116A (ja) | 2013-05-20 |
| WO2011094339A1 (en) | 2011-08-04 |
| EP2528914A1 (en) | 2012-12-05 |
| SG10201500552PA (en) | 2015-03-30 |
| MX2012008510A (es) | 2012-11-21 |
| US8927597B2 (en) | 2015-01-06 |
| US9856276B2 (en) | 2018-01-02 |
| RU2579511C2 (ru) | 2016-04-10 |
| CA2787919C (en) | 2018-07-31 |
| US8350067B2 (en) | 2013-01-08 |
| BR112012018232B1 (pt) | 2022-11-29 |
| US20150175620A1 (en) | 2015-06-25 |
| US8203010B2 (en) | 2012-06-19 |
| US9382262B2 (en) | 2016-07-05 |
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