CN104011018B - 可用于制备吡咯并苯并二氮杂卓的合成方法和中间体 - Google Patents
可用于制备吡咯并苯并二氮杂卓的合成方法和中间体 Download PDFInfo
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- CN104011018B CN104011018B CN201280061966.5A CN201280061966A CN104011018B CN 104011018 B CN104011018 B CN 104011018B CN 201280061966 A CN201280061966 A CN 201280061966A CN 104011018 B CN104011018 B CN 104011018B
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- 0 *C(CC(*)=C1)N1C(c1cc(*)c(*)c(*)c1N*)=O Chemical compound *C(CC(*)=C1)N1C(c1cc(*)c(*)c(*)c1N*)=O 0.000 description 6
- JXORKYUYGAUCBT-VOTSOKGWSA-N CC1(C)OB(/C=C/C(C)=O)OC1(C)C Chemical compound CC1(C)OB(/C=C/C(C)=O)OC1(C)C JXORKYUYGAUCBT-VOTSOKGWSA-N 0.000 description 1
- CUXVXWBQMSPDNN-VOTSOKGWSA-N CC1(C)O[O](/C=C/C(OC)=O)OC1(C)C Chemical compound CC1(C)O[O](/C=C/C(OC)=O)OC1(C)C CUXVXWBQMSPDNN-VOTSOKGWSA-N 0.000 description 1
- UVRSGWXFJXTLPQ-UHFFFAOYSA-N NC[O-]CCOCCNC(CI)=O Chemical compound NC[O-]CCOCCNC(CI)=O UVRSGWXFJXTLPQ-UHFFFAOYSA-N 0.000 description 1
Classifications
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- 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
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/06034—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms
- C07K5/06052—Val-amino acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/20—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- 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
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- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyrrole Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161547207P | 2011-10-14 | 2011-10-14 | |
| US61/547,207 | 2011-10-14 | ||
| PCT/EP2012/070232 WO2013053872A1 (en) | 2011-10-14 | 2012-10-12 | Synthesis method and intermediates useful in the preparation of pyrrolobenzodiazepines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104011018A CN104011018A (zh) | 2014-08-27 |
| CN104011018B true CN104011018B (zh) | 2016-12-14 |
Family
ID=47019019
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201280061966.5A Active CN104011018B (zh) | 2011-10-14 | 2012-10-12 | 可用于制备吡咯并苯并二氮杂卓的合成方法和中间体 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US9102704B2 (enExample) |
| EP (1) | EP2751076B1 (enExample) |
| JP (1) | JP6166728B2 (enExample) |
| CN (1) | CN104011018B (enExample) |
| AU (1) | AU2012322933B2 (enExample) |
| BR (1) | BR112014009070B1 (enExample) |
| CA (1) | CA2850096C (enExample) |
| EA (1) | EA029046B1 (enExample) |
| WO (1) | WO2013053872A1 (enExample) |
Families Citing this family (97)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0819095D0 (en) | 2008-10-17 | 2008-11-26 | Spirogen Ltd | Pyrrolobenzodiazepines |
| NZ602932A (en) | 2010-04-15 | 2014-08-29 | Seattle Genetics Inc | Targeted pyrrolobenzodiazapine conjugates |
| CN102971329B (zh) | 2010-04-15 | 2016-06-29 | 麦迪穆有限责任公司 | 用于治疗增殖性疾病的吡咯并苯并二氮杂卓 |
| CN103987718A (zh) | 2011-09-20 | 2014-08-13 | 斯皮罗根有限公司 | 作为非对称二聚体pbd化合物用于内含在靶向结合物中的吡咯并苯并二氮杂卓 |
| CA2850375C (en) | 2011-10-14 | 2019-07-02 | Seattle Genetics, Inc. | Pyrrolobenzodiazepines and targeted conjugates |
| US9388187B2 (en) | 2011-10-14 | 2016-07-12 | Medimmune Limited | Pyrrolobenzodiazepines |
| JP6393617B2 (ja) | 2011-10-14 | 2018-09-19 | シアトル ジェネティクス,インコーポレーテッド | ピロロベンゾジアゼピンおよび標的コンジュゲート |
| CA2850103C (en) | 2011-10-14 | 2019-09-10 | Spirogen Sarl | Pyrrolobenzodiazepines |
| CA2885305C (en) | 2012-10-12 | 2019-11-12 | Spirogen Sarl | Synthesis and intermediates of pyrrolobenzodiazepine derivatives for conjugation |
| JP6270859B2 (ja) | 2012-10-12 | 2018-01-31 | エイディーシー・セラピューティクス・エス・アー・エール・エルAdc Therapeutics Sarl | ピロロベンゾジアゼピン−抗体結合体 |
| WO2014057073A1 (en) | 2012-10-12 | 2014-04-17 | Spirogen Sàrl | Pyrrolobenzodiazepines and conjugates thereof |
| EP2906297B1 (en) | 2012-10-12 | 2017-12-06 | ADC Therapeutics SA | Pyrrolobenzodiazepine-antibody conjugates |
| LT2906251T (lt) | 2012-10-12 | 2017-12-11 | Adc Therapeutics Sa | Pirolobenzodiazepino-anti-cd22 antikūno konjugatai |
| EP2906250B1 (en) | 2012-10-12 | 2018-05-30 | ADC Therapeutics SA | Pyrrolobenzodiazepine-anti-psma antibody conjugates |
| HUE045435T2 (hu) | 2012-10-12 | 2019-12-30 | Medimmune Ltd | Pirrolobenzodiazepinek és konjugátumaik |
| JP6392764B2 (ja) | 2012-10-12 | 2018-09-19 | エイディーシー・セラピューティクス・エス・アーAdc Therapeutics Sa | ピロロベンゾジアゼピン−抗体結合体 |
| HRP20182129T1 (hr) | 2012-10-12 | 2019-02-08 | Adc Therapeutics Sa | Konjugati protutijelo - pirolobenzodiazepin |
| AU2013366493B2 (en) | 2012-12-21 | 2017-08-24 | Medimmune Limited | Pyrrolobenzodiazepines and conjugates thereof |
| US9567340B2 (en) | 2012-12-21 | 2017-02-14 | Medimmune Limited | Unsymmetrical pyrrolobenzodiazepines-dimers for use in the treatment of proliferative and autoimmune diseases |
| CN105307685B (zh) | 2013-03-13 | 2019-03-08 | 麦迪穆有限责任公司 | 吡咯并苯并二氮杂卓和其结合物 |
| CA2904044C (en) | 2013-03-13 | 2020-03-31 | Medimmune Limited | Pyrrolobenzodiazepines and conjugates thereof |
| KR102306490B1 (ko) | 2013-03-15 | 2021-09-28 | 리제너론 파아마슈티컬스, 인크. | 생물학적 활성 분자, 그의 접합체 및 치료 용도 |
| SG11201601230RA (en) | 2013-08-26 | 2016-03-30 | Regeneron Pharma | Pharmaceutical compositions comprising macrolide diastereomers, methods of their synthesis and therapeutic uses |
| GB201317982D0 (en) | 2013-10-11 | 2013-11-27 | Spirogen Sarl | Pyrrolobenzodiazepines and conjugates thereof |
| WO2015052532A1 (en) | 2013-10-11 | 2015-04-16 | Spirogen Sàrl | Pyrrolobenzodiazepine-antibody conjugates |
| US9950078B2 (en) | 2013-10-11 | 2018-04-24 | Medimmune Limited | Pyrrolobenzodiazepine-antibody conjugates |
| GB201317981D0 (en) | 2013-10-11 | 2013-11-27 | Spirogen Sarl | Pyrrolobenzodiazepines and conjugates thereof |
| US9956299B2 (en) | 2013-10-11 | 2018-05-01 | Medimmune Limited | Pyrrolobenzodiazepine—antibody conjugates |
| KR102399005B1 (ko) | 2014-03-11 | 2022-05-17 | 리제너론 파마슈티칼스 인코포레이티드 | 항-egfrviii 항체 및 그것의 용도 |
| JP6531166B2 (ja) | 2014-09-10 | 2019-06-12 | メドイミューン・リミテッドMedImmune Limited | ピロロベンゾジアゼピン及びそのコンジュゲート |
| GB201416112D0 (en) | 2014-09-12 | 2014-10-29 | Medimmune Ltd | Pyrrolobenzodiazepines and conjugates thereof |
| EP3223854A1 (en) | 2014-11-25 | 2017-10-04 | ADC Therapeutics SA | Pyrrolobenzodiazepine-antibody conjugates |
| CN107995912A (zh) | 2015-03-27 | 2018-05-04 | 里珍纳龙药品有限公司 | 美登素类衍生物、其偶联物和使用方法 |
| GB201506411D0 (en) | 2015-04-15 | 2015-05-27 | Bergenbio As | Humanized anti-axl antibodies |
| GB201506402D0 (en) | 2015-04-15 | 2015-05-27 | Berkel Patricius H C Van And Howard Philip W | Site-specific antibody-drug conjugates |
| KR20180025865A (ko) | 2015-07-06 | 2018-03-09 | 리제너론 파마슈티칼스 인코포레이티드 | 다중특이적 항원 결합 분자 및 이의 용도 |
| MA43416A (fr) | 2015-12-11 | 2018-10-17 | Regeneron Pharma | Méthodes pour ralentir ou empêcher la croissance de tumeurs résistantes au blocage de l'egfr et/ou d'erbb3 |
| MX390630B (es) | 2016-01-25 | 2025-03-21 | Regeneron Pharma | Derivados de maitansinoide, conjugados de los mismos y metodos de uso. |
| GB201601431D0 (en) | 2016-01-26 | 2016-03-09 | Medimmune Ltd | Pyrrolobenzodiazepines |
| GB201602359D0 (en) | 2016-02-10 | 2016-03-23 | Medimmune Ltd | Pyrrolobenzodiazepine Conjugates |
| GB201602356D0 (en) | 2016-02-10 | 2016-03-23 | Medimmune Ltd | Pyrrolobenzodiazepine Conjugates |
| US11352446B2 (en) | 2016-04-28 | 2022-06-07 | Regeneron Pharmaceuticals, Inc. | Methods of making multispecific antigen-binding molecules |
| GB201607478D0 (en) | 2016-04-29 | 2016-06-15 | Medimmune Ltd | Pyrrolobenzodiazepine Conjugates |
| JP2019524687A (ja) | 2016-07-01 | 2019-09-05 | グラクソスミスクライン、インテレクチュアル、プロパティー、ディベロップメント、リミテッドGlaxosmithkline Intellectual Property Development Limited | 抗体薬物複合体およびこれを用いた治療方法 |
| RS64691B1 (sr) | 2016-09-23 | 2023-11-30 | Regeneron Pharma | Bispecifična anti-muc16-cd3 antitela i konjugati anti-muc16 sa lekom |
| AU2017331361B2 (en) | 2016-09-23 | 2024-07-18 | Regeneron Pharmaceuticals, Inc. | Anti-STEAP2 antibodies, antibody-drug conjugates, and bispecific antigen-binding molecules that bind STEAP2 and CD3, and uses thereof |
| GB201617466D0 (en) | 2016-10-14 | 2016-11-30 | Medimmune Ltd | Pyrrolobenzodiazepine conjugates |
| AU2017359043B2 (en) | 2016-11-08 | 2022-06-16 | Regeneron Pharmaceuticals, Inc. | Steroids and protein-conjugates thereof |
| TWI782930B (zh) | 2016-11-16 | 2022-11-11 | 美商再生元醫藥公司 | 抗met抗體,結合met之雙特異性抗原結合分子及其使用方法 |
| KR20200032243A (ko) | 2017-02-08 | 2020-03-25 | 에이디씨 테라퓨틱스 에스에이 | 피롤로벤조디아제핀-항체 컨주게이트 |
| GB201702031D0 (en) | 2017-02-08 | 2017-03-22 | Medlmmune Ltd | Pyrrolobenzodiazepine-antibody conjugates |
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| KR20200007905A (ko) | 2017-05-18 | 2020-01-22 | 리제너론 파마슈티칼스 인코포레이티드 | 사이클로덱스트린 단백질 약물 접합체 |
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| KR102442736B1 (ko) | 2017-06-14 | 2022-09-16 | 에이디씨 테라퓨틱스 에스에이 | 항-cd19 adc의 투여를 위한 투약량 체제 |
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- 2012-10-12 EA EA201490550A patent/EA029046B1/ru unknown
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- 2012-10-12 BR BR112014009070-0A patent/BR112014009070B1/pt active IP Right Grant
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- 2012-10-12 EP EP12772781.6A patent/EP2751076B1/en active Active
- 2012-10-12 AU AU2012322933A patent/AU2012322933B2/en active Active
- 2012-10-12 JP JP2014535096A patent/JP6166728B2/ja active Active
- 2012-10-12 US US14/351,166 patent/US9102704B2/en active Active
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| CA2850096A1 (en) | 2013-04-18 |
| EA201490550A1 (ru) | 2014-09-30 |
| EP2751076A1 (en) | 2014-07-09 |
| JP6166728B2 (ja) | 2017-07-19 |
| US20140275522A1 (en) | 2014-09-18 |
| WO2013053872A1 (en) | 2013-04-18 |
| EP2751076B1 (en) | 2018-04-25 |
| US9102704B2 (en) | 2015-08-11 |
| AU2012322933A1 (en) | 2014-05-29 |
| JP2015502331A (ja) | 2015-01-22 |
| AU2012322933B2 (en) | 2017-02-02 |
| EA029046B1 (ru) | 2018-02-28 |
| CN104011018A (zh) | 2014-08-27 |
| BR112014009070A2 (pt) | 2017-04-18 |
| CA2850096C (en) | 2018-07-03 |
| BR112014009070B1 (pt) | 2021-11-23 |
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