JP2013536865A - ホスホン酸エステル誘導体およびその合成方法 - Google Patents

ホスホン酸エステル誘導体およびその合成方法 Download PDF

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JP2013536865A
JP2013536865A JP2013527294A JP2013527294A JP2013536865A JP 2013536865 A JP2013536865 A JP 2013536865A JP 2013527294 A JP2013527294 A JP 2013527294A JP 2013527294 A JP2013527294 A JP 2013527294A JP 2013536865 A JP2013536865 A JP 2013536865A
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propyl
methyl
hexadecyloxy
ester
mono
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JP2013536865A5 (https=
Inventor
ウェア，ロイ・ダブリュー
アーモンド，メリック・アール
ランパート，バーナード・エム
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キメリクス，インコーポレイテッド
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/66—Phosphorus compounds
    • A61K31/675—Phosphorus compounds having nitrogen as a ring hetero atom, e.g. pyridoxal phosphate
    • 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
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/40—Esters thereof
    • C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4021—Esters of aromatic acids (P-C aromatic linkage)
    • 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
    • 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
    • A61P31/16—Antivirals for RNA viruses for influenza or rhinoviruses
    • 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
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/20—Antivirals for DNA viruses
    • 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
    • A61P31/20—Antivirals for DNA viruses
    • A61P31/22—Antivirals for DNA viruses for herpes viruses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • 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
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
    • C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
    • 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
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/40—Esters thereof
    • C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
    • 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
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
    • C07F9/6509—Six-membered rings
    • C07F9/6512—Six-membered rings having the nitrogen atoms in positions 1 and 3
    • 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
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
    • C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
    • C07F9/657163—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom
    • C07F9/657181—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom the ring phosphorus atom and, at least, one ring oxygen atom being part of a (thio)phosphonic acid derivative
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13—Crystalline forms, e.g. polymorphs
    • 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
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
    • 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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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Virology (AREA)
  • Biochemistry (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Biotechnology (AREA)
  • Pulmonology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • AIDS & HIV (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
JP2013527294A 2010-08-31 2011-08-31 ホスホン酸エステル誘導体およびその合成方法 Pending JP2013536865A (ja)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US37874310P 2010-08-31 2010-08-31
US61/378,743 2010-08-31
PCT/US2011/050099 WO2012031045A2 (en) 2010-08-31 2011-08-31 Phosphonate ester derivatives and methods of synthesis thereof

Related Child Applications (1)

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JP2015196930A Division JP2016094388A (ja) 2010-08-31 2015-10-02 ホスホン酸エステル誘導体およびその合成方法

Publications (2)

Publication Number Publication Date
JP2013536865A true JP2013536865A (ja) 2013-09-26
JP2013536865A5 JP2013536865A5 (https=) 2015-08-06

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JP2013527294A Pending JP2013536865A (ja) 2010-08-31 2011-08-31 ホスホン酸エステル誘導体およびその合成方法
JP2015196930A Pending JP2016094388A (ja) 2010-08-31 2015-10-02 ホスホン酸エステル誘導体およびその合成方法
JP2017110073A Pending JP2017214378A (ja) 2010-08-31 2017-06-02 ホスホン酸エステル誘導体およびその合成方法

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JP2015196930A Pending JP2016094388A (ja) 2010-08-31 2015-10-02 ホスホン酸エステル誘導体およびその合成方法
JP2017110073A Pending JP2017214378A (ja) 2010-08-31 2017-06-02 ホスホン酸エステル誘導体およびその合成方法

Country Status (11)

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US (3) US8569321B2 (https=)
EP (2) EP3020720B1 (https=)
JP (3) JP2013536865A (https=)
CN (3) CN105218580A (https=)
AU (1) AU2011295937B2 (https=)
BR (1) BR112013004925B1 (https=)
CA (1) CA2809679C (https=)
ES (2) ES2604137T3 (https=)
IL (4) IL224955A (https=)
RU (2) RU2015141024A (https=)
WO (1) WO2012031045A2 (https=)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2016538326A (ja) * 2013-11-15 2016-12-08 キメリックス インコーポレイテッド ヘキサデシルオキシプロピル−ホスホン酸エステルの形態型

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2604137T3 (es) * 2010-08-31 2017-03-03 Chimerix, Inc. Derivados de éster de fosfonato y métodos de síntesis de los mismos
EA201892769A3 (ru) 2013-03-15 2019-08-30 Дзе Риджентс Оф Дзе Юниверсити Оф Калифорния Сложные диэфиры ациклических нуклеозидфосфонатов
WO2015085256A1 (en) * 2013-12-05 2015-06-11 Chimerix, Inc. Branched chain acyclic nucleoside phosphonate esters and methods of synthesis and uses thereof
CN103951703A (zh) * 2014-04-28 2014-07-30 中国人民解放军军事医学科学院微生物流行病研究所 制备膦酯衍生物的方法
BR112017005111B1 (pt) 2014-09-15 2023-02-14 The Regents Of The University Of California Compostos análogos de nucleotídeo acíclico, composição farmacêutica contendo tais compostos, e usos da composição no tratamento de uma infecção por papilomavírus
EP3212656B1 (en) 2014-10-27 2019-06-05 Concert Pharmaceuticals Inc. Pyrimidine phosphonic acid esters bearing at least one deuterium atom
WO2017048956A1 (en) 2015-09-15 2017-03-23 The Regents Of The University Of California Nucleotide analogs
EP4295853A3 (en) 2016-06-28 2024-03-06 Emergent BioDefense Operations Lansing LLC Formulations of brincidofovir
CA3105038A1 (en) 2018-06-26 2020-01-02 Tsrl, Inc. Metabolically stable prodrugs
CN109021011A (zh) * 2018-08-14 2018-12-18 山东沾化永浩医药科技有限公司 一种合成对甲苯磺酰氧甲基膦酸二乙酯的方法
IL318465A (en) 2022-07-21 2025-03-01 Antiva Biosciences Inc Compositions and dosage forms for the treatment of HPV infection and HPV-induced neoplasia

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH06503807A (ja) * 1990-08-10 1994-04-28 インスティチュート　オブ　オーガニック　ケミストリ　アンド　バイオケミストリ　アカデミー　オブ　サイエンス　オブ　ザ　チェコ　リパブリック ヌクレオチドの新規な製法
JP2004500352A (ja) * 1999-12-03 2004-01-08 ザ　レジェンツ　オブ　ザ　ユニバーシティー　オブ　カリフォルニア　サン　ディエゴ ホスホネート化合物
US20050192246A1 (en) * 2004-02-05 2005-09-01 Hostetler Karl Y. Pharmacologically active agents containing esterified phosphonates and methods for use thereof
WO2005087788A2 (en) * 2004-03-04 2005-09-22 The Regents Of The University Of California Methods for preparation of nucleoside phosphonate esters
JP2009538829A (ja) * 2006-05-03 2009-11-12 キメリクス，インコーポレーテッド 抗ウイルス性または抗増殖性のホスホネート、ヌクレオシドホスホネートおよびヌクレオシドホスフェートの代謝安定性アルコキシアルキルエステル

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4522811A (en) 1982-07-08 1985-06-11 Syntex (U.S.A.) Inc. Serial injection of muramyldipeptides and liposomes enhances the anti-infective activity of muramyldipeptides
EP1123308A1 (en) * 1998-10-23 2001-08-16 Darwin Discovery Limited Single morphic forms of known peptide metalloproteinase inhibitors
DE602004031115D1 (de) * 2003-06-16 2011-03-03 Acad Of Science Czech Republic Pyrimidinverbindungen mit phosphonatgruppen als antivirale nucleotidanaloga
JP2005045073A (ja) 2003-07-23 2005-02-17 Hamamatsu Photonics Kk 裏面入射型光検出素子
WO2006066074A2 (en) * 2004-12-16 2006-06-22 The Regents Of The University Of California Lung-targeted drugs
JP2008535862A (ja) 2005-04-08 2008-09-04 キメリクス，インコーポレイテッド ポックスウイルス感染の治療のための化合物、組成物および方法
JP2008538354A (ja) 2005-04-08 2008-10-23 キメリクス，インコーポレイテッド ウイルス感染症およびその他の内科疾患を治療するための化合物、組成物および方法
WO2008133966A1 (en) * 2007-04-27 2008-11-06 Chimerix, Inc. Methods of reducing nephrotoxicity in subjects administered with nucleoside
US8614200B2 (en) * 2009-07-21 2013-12-24 Chimerix, Inc. Compounds, compositions and methods for treating ocular conditions
WO2011017253A1 (en) 2009-08-03 2011-02-10 Chimerix, Inc. Composition and methods of treating viral infections and viral induced tumors
WO2011053812A1 (en) 2009-10-30 2011-05-05 Chimerix, Inc. Methods of treating viral associated diseases
US20110263536A1 (en) 2010-04-22 2011-10-27 Chimerix, Inc. Methods of Treating Orthopox Virus Infections and Associated Diseases
ES2604137T3 (es) * 2010-08-31 2017-03-03 Chimerix, Inc. Derivados de éster de fosfonato y métodos de síntesis de los mismos
WO2013063436A1 (en) * 2011-10-26 2013-05-02 Chimerix, Inc. Hexadecyloxypropyl cidofovir for the treatment of double-stranded dna virus infection
WO2013163509A1 (en) * 2012-04-27 2013-10-31 Chimerix, Inc. A method of mitigating virus associated end-organ damage
DK2999476T3 (en) * 2013-11-15 2018-09-03 Chimerix Inc MORPHIC FORMS OF HEXADECYLOXYPROPYL PHOSPHONATE TESTERS

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH06503807A (ja) * 1990-08-10 1994-04-28 インスティチュート　オブ　オーガニック　ケミストリ　アンド　バイオケミストリ　アカデミー　オブ　サイエンス　オブ　ザ　チェコ　リパブリック ヌクレオチドの新規な製法
JP2004500352A (ja) * 1999-12-03 2004-01-08 ザ　レジェンツ　オブ　ザ　ユニバーシティー　オブ　カリフォルニア　サン　ディエゴ ホスホネート化合物
US20050192246A1 (en) * 2004-02-05 2005-09-01 Hostetler Karl Y. Pharmacologically active agents containing esterified phosphonates and methods for use thereof
WO2005087788A2 (en) * 2004-03-04 2005-09-22 The Regents Of The University Of California Methods for preparation of nucleoside phosphonate esters
JP2009538829A (ja) * 2006-05-03 2009-11-12 キメリクス，インコーポレーテッド 抗ウイルス性または抗増殖性のホスホネート、ヌクレオシドホスホネートおよびヌクレオシドホスフェートの代謝安定性アルコキシアルキルエステル

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2016538326A (ja) * 2013-11-15 2016-12-08 キメリックス インコーポレイテッド ヘキサデシルオキシプロピル−ホスホン酸エステルの形態型
JP2017200919A (ja) * 2013-11-15 2017-11-09 キメリックス インコーポレイテッド ヘキサデシルオキシプロピル−ホスホン酸エステルの形態型
JP2017200920A (ja) * 2013-11-15 2017-11-09 キメリックス インコーポレイテッド ヘキサデシルオキシプロピル−ホスホン酸エステルの形態型

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IL244076A0 (en) 2016-04-21
JP2016094388A (ja) 2016-05-26
CA2809679A1 (en) 2012-03-08
CN105218580A (zh) 2016-01-06
ES2700117T3 (es) 2019-02-14
AU2011295937B2 (en) 2015-04-16
IL224955A (en) 2016-02-29
WO2012031045A3 (en) 2012-06-21
JP2017214378A (ja) 2017-12-07
US20140046085A1 (en) 2014-02-13
BR112013004925B1 (pt) 2020-09-29
AU2011295937A1 (en) 2013-03-14
EP2611818A4 (en) 2014-02-12
RU2015141024A (ru) 2018-12-26
US8569321B2 (en) 2013-10-29
WO2012031045A2 (en) 2012-03-08
CN103209985A (zh) 2013-07-17
CN103209985B (zh) 2016-08-24
EP3020720A1 (en) 2016-05-18
BR112013004925A2 (pt) 2016-04-26
CN105998039A (zh) 2016-10-12
IL240574A0 (en) 2015-09-24
RU2015141024A3 (https=) 2018-12-26
RU2581045C2 (ru) 2016-04-10
US20150329575A1 (en) 2015-11-19
RU2013114370A (ru) 2014-10-10
IL238217A (en) 2017-07-31
US20120058976A1 (en) 2012-03-08
CA2809679C (en) 2018-03-20
ES2604137T3 (es) 2017-03-03
EP2611818B1 (en) 2016-08-24
EP2611818A2 (en) 2013-07-10
US9303051B2 (en) 2016-04-05
EP3020720B1 (en) 2018-09-19

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