DK2207779T3 - Fremgangsmåde til syntese af morpholinooligomerer - Google Patents
Fremgangsmåde til syntese af morpholinooligomererInfo
- Publication number
- DK2207779T3 DK2207779T3 DK08850132.5T DK08850132T DK2207779T3 DK 2207779 T3 DK2207779 T3 DK 2207779T3 DK 08850132 T DK08850132 T DK 08850132T DK 2207779 T3 DK2207779 T3 DK 2207779T3
- Authority
- DK
- Denmark
- Prior art keywords
- synthesis
- morpholine oligomers
- morpholine
- oligomers
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/18—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 one oxygen and one nitrogen atom, e.g. guanine
-
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
- A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
- A61K31/7064—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines
-
- 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 Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Saccharide Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US98820007P | 2007-11-15 | 2007-11-15 | |
US98819207P | 2007-11-15 | 2007-11-15 | |
PCT/US2008/012804 WO2009064471A1 (en) | 2007-11-15 | 2008-11-14 | Method of synthesis of morpholino oligomers |
Publications (1)
Publication Number | Publication Date |
---|---|
DK2207779T3 true DK2207779T3 (da) | 2014-07-14 |
Family
ID=40293764
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DK08850132.5T DK2207779T3 (da) | 2007-11-15 | 2008-11-14 | Fremgangsmåde til syntese af morpholinooligomerer |
Country Status (14)
Country | Link |
---|---|
EP (1) | EP2207779B1 (da) |
JP (3) | JP5512533B2 (da) |
KR (1) | KR101617472B1 (da) |
CN (1) | CN101861318A (da) |
BR (2) | BR122019021332A8 (da) |
CA (2) | CA2704261C (da) |
DK (1) | DK2207779T3 (da) |
ES (1) | ES2479393T3 (da) |
HK (1) | HK1144424A1 (da) |
HR (1) | HRP20140646T1 (da) |
IL (1) | IL205776A0 (da) |
MX (1) | MX2010004955A (da) |
RU (1) | RU2606627C2 (da) |
WO (1) | WO2009064471A1 (da) |
Families Citing this family (86)
Publication number | Priority date | Publication date | Assignee | Title |
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AU2006213686A1 (en) | 2005-02-09 | 2006-08-17 | Avi Bio Pharma, Inc. | Antisense composition and method for treating muscle atrophy |
US8067571B2 (en) | 2005-07-13 | 2011-11-29 | Avi Biopharma, Inc. | Antibacterial antisense oligonucleotide and method |
EP2438168B1 (en) | 2009-06-01 | 2020-02-12 | Halo-Bio Rnai Therapeutics, Inc. | Polynucleotides for multivalent rna interference, compositions and methods of use thereof |
KR101944119B1 (ko) | 2009-11-13 | 2019-01-30 | 사렙타 쎄러퓨틱스 인코퍼레이티드 | 안티센스 항바이러스 화합물 및 인플루엔자 바이러스 감염을 치료하는 방법 |
WO2011150408A2 (en) | 2010-05-28 | 2011-12-01 | Avi Biopharma, Inc. | Oligonucleotide analogues having modified intersubunit linkages and/or terminal groups |
TWI541024B (zh) | 2010-09-01 | 2016-07-11 | 日本新藥股份有限公司 | 反義核酸 |
WO2012031243A2 (en) | 2010-09-03 | 2012-03-08 | Avi Biopharma, Inc. | dsRNA MOLECULES COMPRISING OLIGONUCLEOTIDE ANALOGS HAVING MODIFIED INTERSUBUNIT LINKAGES AND/OR TERMINAL GROUPS |
JP5831455B2 (ja) | 2010-09-30 | 2015-12-09 | 日本新薬株式会社 | モルホリノ核酸誘導体 |
EP2638161A1 (en) | 2010-11-12 | 2013-09-18 | Sarepta Therapeutics, Inc. | Antisense antibacterial compounds and methods |
EP2704749A1 (en) | 2011-05-05 | 2014-03-12 | Sarepta Therapeutics, Inc. | Peptide oligonucleotide conjugates |
WO2013012752A2 (en) | 2011-07-15 | 2013-01-24 | Sarepta Therapeutics, Inc. | Methods and compositions for manipulating translation of protein isoforms from alternative initiation start sites |
US20130085139A1 (en) | 2011-10-04 | 2013-04-04 | Royal Holloway And Bedford New College | Oligomers |
US9278987B2 (en) | 2011-11-18 | 2016-03-08 | Sarepta Therapeutics, Inc. | Functionally-modified oligonucleotides and subunits thereof |
JP6496549B2 (ja) | 2011-11-30 | 2019-04-03 | サレプタ セラピューティクス, インコーポレイテッド | 脊髄性筋萎縮症における誘発されたエクソン包含 |
US10066228B2 (en) | 2011-11-30 | 2018-09-04 | Sarepta Therapeutics, Inc. | Oligonucleotides for treating expanded repeat diseases |
ES2935606T3 (es) | 2011-12-08 | 2023-03-08 | Sarepta Therapeutics Inc | Análogos de oligonucleótidos dirigidos a LMNA humana |
RU2619184C2 (ru) * | 2011-12-28 | 2017-05-12 | Ниппон Синяку Ко., Лтд. | Антисмысловые нуклеиновые кислоты |
ES2706198T3 (es) | 2012-03-20 | 2019-03-27 | Sarepta Therapeutics Inc | Conjugados de ácido borónico de análogos de oligonucleótidos |
CN102702265A (zh) * | 2012-05-14 | 2012-10-03 | 天津特安化学科技有限公司 | 一种固相合成磷酰二胺吗啉代寡核苷酸及方法 |
EP2946013A1 (en) | 2013-01-16 | 2015-11-25 | Iowa State University Research Foundation, Inc. | A deep intronic target for splicing correction on spinal muscular atrophy gene |
EP3015467A4 (en) | 2013-05-24 | 2016-11-02 | Ajinomoto Kk | PROCESS FOR THE PRODUCTION OF MORPHOLINO-OLIGONUCLEOTIDE |
CN111235149B (zh) | 2013-09-05 | 2024-04-16 | 萨罗塔治疗公司(美国) | 酸性α-葡糖苷酶中反义诱导的外显子2纳入 |
EP3868772A1 (en) | 2013-09-30 | 2021-08-25 | Geron Corporation | Phosphorodiamidate backbone linkage for oligonucleotides |
PL3118311T3 (pl) | 2014-03-12 | 2019-09-30 | Nippon Shinyaku Co., Ltd. | Antysensowny kwas nukleinowy |
EP3143141B1 (en) | 2014-05-16 | 2019-10-02 | Oregon State University | Antisense antibacterial compounds and methods |
JP6687542B2 (ja) | 2014-05-19 | 2020-04-22 | オレゴン ステート ユニバーシティ | アンチセンス抗菌化合物および方法 |
CN106661577B (zh) | 2014-06-17 | 2020-05-12 | 日本新药株式会社 | 反义核酸 |
EP3208277A4 (en) | 2014-10-14 | 2018-06-13 | Ajinomoto Co., Inc. | Morpholino oligonucleotide manufacturing method |
CA2972653A1 (en) | 2014-12-31 | 2016-07-07 | Board Of Regents, The University Of Texas System | Antisense antibacterial compounds and methods |
MA41795A (fr) | 2015-03-18 | 2018-01-23 | Sarepta Therapeutics Inc | Exclusion d'un exon induite par des composés antisens dans la myostatine |
JP6954843B2 (ja) | 2015-05-19 | 2021-10-27 | サレプタ セラピューティクス,インコーポレイテッド | ペプチドオリゴヌクレオチドコンジュゲート |
MA50829A (fr) | 2015-06-01 | 2018-04-11 | Sarepta Therapeutics Inc | Exclusion d'exon induite pat technologie antisens dans le collagène de type vii |
US11020417B2 (en) | 2015-06-04 | 2021-06-01 | Sarepta Therapeutics, Inc | Methods and compounds for treatment of lymphocyte-related diseases and conditions |
PL3331891T3 (pl) * | 2015-08-05 | 2022-03-28 | Eisai R&D Management Co., Ltd. | Sposób wytwarzania zasadniczo czystego diastereoizomerycznie oligomeru amidofosforanowego, oligomer amidofosforanowy wytworzony takim sposobem oraz kompozycja farmaceutyczna zawierająca taki oligomer amidofosforanowy |
WO2017035278A1 (en) | 2015-08-24 | 2017-03-02 | Halo-Bio Rnai Therapeutics, Inc. | Polynucleotide nanoparticles for the modulation of gene expression and uses thereof |
KR102473431B1 (ko) | 2015-09-15 | 2022-12-01 | 니뽄 신야쿠 가부시키가이샤 | 안티센스 핵산 |
US10563199B2 (en) | 2015-09-16 | 2020-02-18 | Nippon Shinyaku Co., Ltd. | Antisense nucleic acid for treating amyotrophy |
WO2017062835A2 (en) | 2015-10-09 | 2017-04-13 | Sarepta Therapeutics, Inc. | Compositions and methods for treating duchenne muscular dystrophy and related disorders |
MX2018007307A (es) | 2015-12-15 | 2019-03-14 | Sarepta Therapeutics Inc | Conjugados de peptidos y oligonucleotidos. |
EP3394261A4 (en) | 2015-12-23 | 2019-11-27 | Oregon State University | ANTISENSE ANTIBACTERIAL COMPOUNDS AND ASSOCIATED METHODS |
US11142764B2 (en) | 2015-12-23 | 2021-10-12 | Board Of Regents, The University Of Texas System | Antisense antibacterial compounds and methods |
EA201892366A1 (ru) | 2016-04-18 | 2019-03-29 | Сарепта Терапьютикс, Инк. | Антисмысловые олигомеры и способы их применения для лечения заболеваний, связанных с геном кислой альфа-глюкозидазы |
EA201892467A1 (ru) | 2016-04-29 | 2019-05-31 | Сарепта Терапьютикс, Инк. | Олигонуклеотидные аналоги, нацеленные на lmna человека |
JP7008642B2 (ja) * | 2016-05-24 | 2022-01-25 | サレプタ セラピューティクス, インコーポレイテッド | オリゴマー調製のためのプロセス |
BR112018074340A2 (pt) | 2016-05-24 | 2019-03-06 | Sarepta Therapeutics, Inc. | processos para preparar oligômeros morfolino fosforodiamidato |
MA45155A (fr) | 2016-05-24 | 2019-04-10 | Sarepta Therapeutics Inc | Procédés de préparation d'oligomères morpholino de phosphorodiamidate |
TW201805002A (zh) | 2016-05-24 | 2018-02-16 | 美商薩羅塔治療公司 | 磷醯二胺嗎啉代寡聚物醫藥組合物 |
US11472824B2 (en) | 2016-05-24 | 2022-10-18 | Sarepta Therapeutics, Inc. | Processes for preparing phosphorodiamidate morpholino oligomers |
MA45362A (fr) | 2016-05-24 | 2019-04-10 | Sarepta Therapeutics Inc | Procédés de préparation d'oligomères morpholino de phosphorodiamidate |
JP7022079B2 (ja) * | 2016-06-30 | 2022-02-17 | サレプタ セラピューティクス, インコーポレイテッド | ホスホロジアミダートモルホリノオリゴマーを調製するためのプロセス |
CN116804031A (zh) * | 2016-09-20 | 2023-09-26 | 科罗拉多州立大学董事会法人团体 | 使用亚磷酰胺化学法合成主链修饰的吗啉代寡核苷酸和嵌合体 |
HUE059905T2 (hu) | 2016-12-19 | 2023-01-28 | Sarepta Therapeutics Inc | Exonátugró oligomerkonjugátumok izomdisztrófiára |
BR112019012651A2 (pt) | 2016-12-19 | 2020-01-28 | Sarepta Therapeutics Inc | conjugados de oligômero de salto de éxon para distrofia muscular |
MX2019006882A (es) | 2016-12-19 | 2019-08-16 | Sarepta Therapeutics Inc | Conjugados de oligomeros de omision de exon para distrofia muscular. |
JP2020517638A (ja) | 2017-04-20 | 2020-06-18 | エータイアー ファーマ, インコーポレイテッド | 肺の炎症を治療するための組成物および方法 |
EA201991450A1 (ru) | 2017-09-22 | 2019-12-30 | Сарепта Терапьютикс, Инк. | Конъюгаты олигомеров для пропуска экзона при мышечной дистрофии |
MA49986A (fr) * | 2017-09-25 | 2020-07-01 | Massachusetts Inst Technology | Procédés de préparation d'oligomères morpholino phosphorodiamidate par l'intermédiaire d'une synthèse à flux rapide |
EP3697910A4 (en) | 2017-10-18 | 2021-07-14 | Sarepta Therapeutics, Inc. | ANTISENSE OLIGOMERIC COMPOUNDS |
CA3099778A1 (en) | 2018-05-10 | 2019-11-14 | Nippon Shinyaku Co., Ltd. | Method for preparing oligonucleic acid compound |
US10758629B2 (en) | 2018-05-29 | 2020-09-01 | Sarepta Therapeutics, Inc. | Exon skipping oligomer conjugates for muscular dystrophy |
EP4219717A3 (en) | 2018-06-13 | 2023-12-20 | Sarepta Therapeutics, Inc. | Exon skipping oligomers for muscular dystrophy |
AU2019293687A1 (en) | 2018-06-26 | 2021-01-07 | Nippon Shinyaku Co., Ltd. | Composition comprising antisense oligonucleotide and use thereof for treatment of Duchenne muscular dystrophy |
TW202020153A (zh) | 2018-07-27 | 2020-06-01 | 美商薩羅塔治療公司 | 用於肌肉萎縮症之外顯子跳躍寡聚物 |
KR20210104759A (ko) | 2018-12-13 | 2021-08-25 | 사렙타 쎄러퓨틱스 인코퍼레이티드 | 근 이영양증을 위한 엑손 스키핑 올리고머 접합체 |
GB201821269D0 (en) | 2018-12-28 | 2019-02-13 | Nippon Shinyaku Co Ltd | Myostatin signal inhibitor |
WO2021025899A1 (en) | 2019-08-02 | 2021-02-11 | Sarepta Therapeutics, Inc. | Phosphorodiamidate morpholino oligomer pharmaceutical compositions |
KR20220098217A (ko) | 2019-11-13 | 2022-07-11 | 니뽄 신야쿠 가부시키가이샤 | 올리고 핵산 화합물의 제조 방법 |
JPWO2021095875A1 (da) | 2019-11-13 | 2021-05-20 | ||
IL293997A (en) | 2019-12-19 | 2022-08-01 | Nippon Shinyaku Co Ltd | Antistrand nucleic acids that allow exon skipping |
KR20220122673A (ko) | 2019-12-26 | 2022-09-02 | 니뽄 신야쿠 가부시키가이샤 | 엑손 50의 스키핑을 유도하는 안티센스 핵산 |
US20230140736A1 (en) | 2020-02-28 | 2023-05-04 | Nippon Shinyaku Co., Ltd. | Antisense nucleic acid inducing skipping of exon 51 |
KR20230035623A (ko) * | 2020-07-10 | 2023-03-14 | 창저우 신더올 파마슈티컬스 컴퍼니 리미티드 | 올리고뉴클레오티드의 제조 방법 |
WO2022230954A1 (ja) | 2021-04-28 | 2022-11-03 | 日本新薬株式会社 | オリゴ核酸化合物の製造方法 |
JPWO2022239863A1 (da) | 2021-05-13 | 2022-11-17 | ||
CA3221758A1 (en) | 2021-05-28 | 2022-12-01 | Sumitomo Pharma Co., Ltd. | Antisense nucleic acid |
WO2022270585A1 (ja) | 2021-06-23 | 2022-12-29 | 日本新薬株式会社 | アンチセンスオリゴマーの組み合わせ |
WO2023282345A1 (ja) | 2021-07-08 | 2023-01-12 | 日本新薬株式会社 | 腎毒性軽減剤 |
IL310001A (en) | 2021-07-08 | 2024-03-01 | Nippon Shinyaku Co Ltd | sediment suppressant |
JPWO2023282344A1 (da) | 2021-07-08 | 2023-01-12 | ||
EP4389893A1 (en) | 2021-08-21 | 2024-06-26 | Takeda Pharmaceutical Company Limited | Human transferrin receptor binding peptide-drug conjugate |
EP4387676A2 (en) | 2021-09-03 | 2024-06-26 | Sarepta Therapeutics, Inc. | Delivery of anitsense oligomers by mirror image peptides |
WO2023055774A1 (en) | 2021-09-30 | 2023-04-06 | Sarepta Therapeutics, Inc. | Antisense oligonucleotides having one or more abasic units |
WO2023070086A1 (en) | 2021-10-22 | 2023-04-27 | Sarepta Therapeutics, Inc. | Morpholino oligomers for treatment of peripheral myelin protein 22 related diseases |
WO2023167908A1 (en) * | 2022-03-01 | 2023-09-07 | Eisai R&D Management Co., Ltd. | Bis-protected, activated guanine monomers |
WO2024064237A2 (en) | 2022-09-21 | 2024-03-28 | Sarepta Therapeutics, Inc. | Dmd antisense oligonucleotide-mediated exon skipping efficiency |
CN117586307B (zh) * | 2024-01-19 | 2024-04-16 | 凯莱英生命科学技术(天津)有限公司 | Pmo鸟苷单体的合成方法 |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH577464A5 (da) * | 1972-09-22 | 1976-07-15 | Ciba Geigy Ag | |
US5185444A (en) * | 1985-03-15 | 1993-02-09 | Anti-Gene Deveopment Group | Uncharged morpolino-based polymers having phosphorous containing chiral intersubunit linkages |
JP3398378B2 (ja) * | 1989-12-20 | 2003-04-21 | アンチビラルス・インコーポレイテツド | リン含有キラルインターサブユニットリンケージを有する非電荷モルホリノ―基体ポリマー |
WO1991018898A1 (fr) * | 1990-06-01 | 1991-12-12 | Nippon Shinyaku Co., Ltd. | Homologue d'acide nucleique |
US5510476A (en) | 1994-07-07 | 1996-04-23 | Isis Pharmaceuticals, Inc. | Carbocation scavenging during oligonucleotide synthesis |
UA48150C2 (uk) * | 1994-11-02 | 2002-08-15 | Ай-Сі-Ен Фармасьютикалз | Похідні амінокислот або аміноспиртів, олігонуклеотид |
US7790694B2 (en) * | 2005-07-13 | 2010-09-07 | Avi Biopharma Inc. | Antisense antibacterial method and compound |
HUE036995T2 (hu) * | 2006-05-10 | 2018-08-28 | Sarepta Therapeutics Inc | Az alegységek között kationos kötéssel rendelkezõ oligonukleotid analógok |
-
2008
- 2008-11-14 MX MX2010004955A patent/MX2010004955A/es active IP Right Grant
- 2008-11-14 KR KR1020107009620A patent/KR101617472B1/ko active IP Right Grant
- 2008-11-14 EP EP08850132.5A patent/EP2207779B1/en active Active
- 2008-11-14 WO PCT/US2008/012804 patent/WO2009064471A1/en active Application Filing
- 2008-11-14 CA CA2704261A patent/CA2704261C/en active Active
- 2008-11-14 BR BR122019021332A patent/BR122019021332A8/pt not_active Application Discontinuation
- 2008-11-14 BR BRPI0819828A patent/BRPI0819828A8/pt not_active Application Discontinuation
- 2008-11-14 JP JP2010534042A patent/JP5512533B2/ja active Active
- 2008-11-14 CN CN200880116219A patent/CN101861318A/zh active Pending
- 2008-11-14 CA CA2884340A patent/CA2884340C/en active Active
- 2008-11-14 ES ES08850132.5T patent/ES2479393T3/es active Active
- 2008-11-14 DK DK08850132.5T patent/DK2207779T3/da active
- 2008-11-14 RU RU2010123958A patent/RU2606627C2/ru not_active Application Discontinuation
-
2010
- 2010-05-13 IL IL205776A patent/IL205776A0/en unknown
- 2010-11-18 HK HK10110758.9A patent/HK1144424A1/xx unknown
-
2014
- 2014-03-26 JP JP2014063314A patent/JP6178744B2/ja active Active
- 2014-07-07 HR HRP20140646AT patent/HRP20140646T1/hr unknown
-
2016
- 2016-06-30 JP JP2016129716A patent/JP2016196494A/ja active Pending
Also Published As
Publication number | Publication date |
---|---|
CN101861318A (zh) | 2010-10-13 |
HK1144424A1 (en) | 2011-02-18 |
BRPI0819828A2 (pt) | 2015-05-26 |
JP6178744B2 (ja) | 2017-08-09 |
IL205776A0 (en) | 2010-11-30 |
BR122019021332A2 (da) | 2015-05-26 |
RU2010123958A (ru) | 2011-12-20 |
ES2479393T3 (es) | 2014-07-24 |
MX2010004955A (es) | 2010-06-30 |
JP2016196494A (ja) | 2016-11-24 |
KR101617472B1 (ko) | 2016-05-02 |
JP5512533B2 (ja) | 2014-06-04 |
CA2704261A1 (en) | 2009-05-22 |
EP2207779A1 (en) | 2010-07-21 |
BRPI0819828A8 (pt) | 2022-12-27 |
WO2009064471A1 (en) | 2009-05-22 |
CA2884340C (en) | 2017-07-25 |
AU2008321409A1 (en) | 2009-05-22 |
CA2884340A1 (en) | 2009-05-22 |
AU2008321409B2 (en) | 2014-08-14 |
RU2606627C2 (ru) | 2017-01-10 |
HRP20140646T1 (hr) | 2014-09-26 |
EP2207779B1 (en) | 2014-04-09 |
CA2704261C (en) | 2015-05-26 |
JP2011503184A (ja) | 2011-01-27 |
BR122019021332A8 (pt) | 2022-12-06 |
JP2014159432A (ja) | 2014-09-04 |
KR20100090681A (ko) | 2010-08-16 |
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