BRPI0923336A2 - Copolímeros zwiteriônicos - Google Patents
Copolímeros zwiteriônicosInfo
- Publication number
- BRPI0923336A2 BRPI0923336A2 BRPI0923336A BRPI0923336A BRPI0923336A2 BR PI0923336 A2 BRPI0923336 A2 BR PI0923336A2 BR PI0923336 A BRPI0923336 A BR PI0923336A BR PI0923336 A BRPI0923336 A BR PI0923336A BR PI0923336 A2 BRPI0923336 A2 BR PI0923336A2
- Authority
- BR
- Brazil
- Prior art keywords
- copolymers
- zwiterionic
- compositions
- biological
- zwitterionic
- Prior art date
Links
- 229920001577 copolymer Polymers 0.000 title abstract 3
- 239000003814 drug Substances 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 229920000642 polymer Polymers 0.000 abstract 2
- 239000003124 biologic agent Substances 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 125000005395 methacrylic acid group Chemical class 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 238000010526 radical polymerization reaction Methods 0.000 abstract 1
- 229940124597 therapeutic agent Drugs 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4738—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4745—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems condensed with ring systems having nitrogen as a ring hetero atom, e.g. phenantrolines
-
- 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
- A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
- A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
- A61K31/704—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin attached to a condensed carbocyclic ring system, e.g. sennosides, thiocolchicosides, escin, daunorubicin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/56—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
- A61K47/58—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. poly[meth]acrylate, polyacrylamide, polystyrene, polyvinylpyrrolidone, polyvinylalcohol or polystyrene sulfonic acid resin
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F230/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing phosphorus
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F293/00—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule
- C08F293/005—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule using free radical "living" or "controlled" polymerisation, e.g. using a complexing agent
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F238/00—Copolymers of compounds having one or more carbon-to-carbon triple bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2438/00—Living radical polymerisation
- C08F2438/01—Atom Transfer Radical Polymerization [ATRP] or reverse ATRP
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Molecular Biology (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polyesters Or Polycarbonates (AREA)
Abstract
COPOLÍMEROS ZWITERIÔNICOS. A presente invenção refere-se, de modo geral, a polímeros zwiteriônicos (incluindo copolímeros zwiteriônicos), tais como estruturas polimetacrílicas com porções funcionais pendentes, tais como porções terapêuticas ou biológicas. Mais particularmente, a invenção refere-se a polímeros metacrílicos substituídos por fosforilcolina preparados por polimerização de radical livre e "click chemistry", por exemplo, e composições e produtos compreendendo os mesmos, assim como métodos relacionados e usos das composições, por exemplo, como agentes biológicos ou terapêuticos e na aplicação de medicamentos dos mesmos.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12206508P | 2008-12-12 | 2008-12-12 | |
| US23398209P | 2009-08-14 | 2009-08-14 | |
| PCT/US2009/067665 WO2010068862A2 (en) | 2008-12-12 | 2009-12-11 | Zwitterionic polymers with therapeutic moieties |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BRPI0923336A2 true BRPI0923336A2 (pt) | 2017-07-11 |
Family
ID=42243327
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BRPI0923336A BRPI0923336A2 (pt) | 2008-12-12 | 2009-12-11 | Copolímeros zwiteriônicos |
Country Status (8)
| Country | Link |
|---|---|
| US (3) | US8802738B2 (pt) |
| EP (2) | EP2358770B1 (pt) |
| CN (1) | CN102317332B (pt) |
| AU (1) | AU2009324490A1 (pt) |
| BR (1) | BRPI0923336A2 (pt) |
| CA (2) | CA2745307A1 (pt) |
| IL (1) | IL213448A0 (pt) |
| WO (2) | WO2010068864A2 (pt) |
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| CA2745307A1 (en) | 2008-12-12 | 2010-06-17 | University Of Massachusetts | Polyesters with grafted zwitterions |
| WO2011075185A1 (en) | 2009-12-18 | 2011-06-23 | Oligasis | Targeted drug phosphorylcholine polymer conjugates |
| DK3354665T5 (da) | 2011-06-02 | 2022-09-19 | Massachusetts Inst Technology | Modificerede alginater til celleindkapsling og celleterapi |
| CN102977275B (zh) * | 2011-09-07 | 2014-12-10 | 佛山市博新生物科技有限公司 | 一种经过预处理的含有磷酰胆碱基团的单体改善吸附树脂生物相容性的应用 |
| US9421276B2 (en) * | 2012-08-31 | 2016-08-23 | Virginia Commonwealth University | Clickable polyoxetane carrier for drug delivery |
| US9943624B2 (en) * | 2012-11-30 | 2018-04-17 | University Of Massachusetts | Multi-functional surface coating of implants |
| EP3019559A4 (en) | 2013-08-22 | 2017-04-05 | Sony Corporation | Water soluble fluorescent or colored dyes and methods for their use |
| WO2015035342A2 (en) | 2013-09-08 | 2015-03-12 | Oligasis Llc | Factor viii zwitterionic polymer conjugates |
| US9717797B2 (en) | 2013-12-05 | 2017-08-01 | International Business Machines Corporation | Polycarbonates bearing aromatic N-heterocycles for drug delivery |
| EP3079668A1 (en) | 2013-12-09 | 2016-10-19 | Durect Corporation | Pharmaceutically active agent complexes, polymer complexes, and compositions and methods involving the same |
| CN103755888B (zh) * | 2014-02-10 | 2016-03-23 | 苏州大学 | 一种两亲性聚合物及其制备、磁性中空纳米药物载体和其制备方法 |
| EP3137124B1 (en) * | 2014-04-29 | 2019-01-09 | Microvention, Inc. | Polymers including active agents |
| US9840553B2 (en) | 2014-06-28 | 2017-12-12 | Kodiak Sciences Inc. | Dual PDGF/VEGF antagonists |
| KR102719485B1 (ko) | 2014-08-01 | 2024-10-21 | 메사추세츠 인스티튜트 오브 테크놀로지 | 항-섬유 물질 및 응용을 위한 변형된 알기네이트 |
| WO2016040489A1 (en) | 2014-09-09 | 2016-03-17 | Shaoyi Jiang | Functionalized zwitterionic and mixed charge polymers, related hydrogels, and methds for their use |
| KR20210013299A (ko) | 2014-10-17 | 2021-02-03 | 코디악 사이언시스 인코포레이티드 | 부티릴콜린에스테라제 양성이온성 중합체 컨쥬게이트 |
| US10398788B2 (en) * | 2014-10-24 | 2019-09-03 | Canon Kabushiki Kaisha | Polymer and contrast agent for photoacoustic imaging including the polymer |
| KR102646956B1 (ko) | 2015-02-26 | 2024-03-14 | 소니그룹주식회사 | 페닐에티닐나프탈렌 염료 및 이의 사용 방법 |
| US11827661B2 (en) | 2015-02-26 | 2023-11-28 | Sony Group Corporation | Water soluble fluorescent or colored dyes comprising conjugating groups |
| AU2016344041B2 (en) | 2015-11-01 | 2019-11-07 | Massachusetts Institute Of Technology | Materials with improved properties |
| NZ742800A (en) | 2015-11-01 | 2019-03-29 | Massachusetts Inst Technology | Modified alginates for anti-fibrotic materials and applications |
| KR20250057128A (ko) | 2015-12-30 | 2025-04-28 | 코디악 사이언시스 인코포레이티드 | 항체 및 이의 접합체 |
| CN109415574B (zh) | 2016-04-01 | 2021-05-28 | 索尼公司 | 具有刚性间隔基团的超亮二聚体或聚合物染料 |
| AU2017240154B2 (en) | 2016-04-01 | 2021-08-12 | Sony Group Corporation | Ultra bright dimeric or polymeric dyes |
| WO2017177065A2 (en) | 2016-04-06 | 2017-10-12 | Sony Corporation | Ultra bright dimeric or polymeric dyes with spacing linker groups |
| EP3455299B1 (en) | 2016-05-10 | 2024-01-17 | Sony Group Corporation | Compositions comprising a polymeric dye and a cyclodextrin and uses thereof |
| JP7527537B2 (ja) | 2016-05-10 | 2024-08-05 | ソニーグループ株式会社 | ペプチド骨格を有する超明色ポリマー染料 |
| EP3455300A1 (en) | 2016-05-11 | 2019-03-20 | Sony Corporation | Ultra bright dimeric or polymeric dyes |
| EP3464477A1 (en) | 2016-06-06 | 2019-04-10 | Sony Corporation | Ionic polymers comprising fluorescent or colored reporter groups |
| CA3027200A1 (en) * | 2016-06-13 | 2017-12-21 | Massachusetts Institute Of Technology | Biocompatible zwitterionic polymer coatings and hydrogels for reducing foreign body response and fibrosis |
| JP7312929B2 (ja) | 2016-07-29 | 2023-07-24 | ソニーグループ株式会社 | 超明色二量体またはポリマー色素およびその調製のための方法 |
| JP2020502226A (ja) * | 2016-12-23 | 2020-01-23 | コモンウェルス サイエンティフィック アンド インダストリアル リサーチ オーガナイゼーション | 薬物の標的送達のための生体適合性の親水性ポリマーコンジュゲート |
| DK3570874T3 (da) | 2017-01-17 | 2023-04-11 | Univ Wayne State | Zwitterionisk polymer-insulin-sammensætninger og dertil relaterede fremgangsmåder |
| WO2019071153A1 (en) | 2017-10-05 | 2019-04-11 | Sony Corporation | PROGRAMMABLE DENDRITIC MEDICINES |
| KR20260011205A (ko) | 2017-10-05 | 2026-01-22 | 소니그룹주식회사 | 프로그램가능한 중합체성 약물 |
| US11318231B2 (en) | 2017-11-06 | 2022-05-03 | Massachusetts Institute Of Technology | Anti-inflammatory coatings to improve biocompatibility of neurological implants |
| CN111836645A (zh) | 2017-11-16 | 2020-10-27 | 索尼公司 | 可编程的聚合药物 |
| CN111465608A (zh) * | 2017-12-13 | 2020-07-28 | 索尼公司 | 包含生物学活性化合物的离子型聚合物 |
| CN111565756A (zh) | 2018-01-12 | 2020-08-21 | 索尼公司 | 包含生物活性化合物的具有刚性间隔基团的聚合物 |
| US12539334B2 (en) | 2018-01-12 | 2026-02-03 | Sony Group Corporation | Phosphoalkyl polymers comprising biologically active agents |
| EP3737417B1 (en) | 2018-01-12 | 2025-08-27 | Sony Group Corporation | Phosphoalkyl ribose polymers comprising biologically active compounds |
| EP3758737A4 (en) | 2018-03-02 | 2022-10-12 | Kodiak Sciences Inc. | IL-6 ANTIBODIES AND FUSION CONSTRUCTS AND CONJUGATES THEREOF |
| KR102742386B1 (ko) | 2018-03-19 | 2024-12-16 | 소니그룹주식회사 | 형광 신호 향상을 위한 2가 금속의 사용 |
| CN118480073A (zh) | 2018-03-21 | 2024-08-13 | 索尼公司 | 具有连接体基团的聚合串联染料 |
| JP7580689B2 (ja) | 2018-06-27 | 2024-11-12 | ソニーグループ株式会社 | デオキシリボースを含むリンカー基を有するポリマー色素 |
| KR20210032434A (ko) | 2018-07-13 | 2021-03-24 | 소니 주식회사 | 유기인산염 단위를 포함하는 백본을 갖는 중합체성 염료 |
| US12527871B2 (en) | 2019-06-05 | 2026-01-20 | Boston Scientific Scimed, Inc. | Click chemistry capturable platinum-based antineoplastic agents |
| WO2021062176A2 (en) | 2019-09-26 | 2021-04-01 | Sony Corporation | Polymeric tandem dyes with linker groups |
| EP4038081A1 (en) | 2019-09-30 | 2022-08-10 | Sony Group Corporation | Nucleotide probes |
| CA3157509A1 (en) | 2019-10-10 | 2021-04-15 | Kodiak Sciences Inc. | Methods of treating an eye disorder |
| EP4256078A1 (en) | 2020-12-07 | 2023-10-11 | Sony Group Corporation | Spacing linker group design for brightness enhancement in dimeric or polymeric dyes |
| CN112972428B (zh) * | 2021-03-09 | 2022-03-08 | 石河子大学 | 两性离子聚合物膜包覆的介孔硅基药物载体及制备方法 |
| CN114106297B (zh) * | 2021-12-16 | 2024-01-05 | 香港中文大学(深圳) | 含有两性离子基团的荧光聚合物及其制备方法和应用 |
| CN116217768B (zh) * | 2023-03-27 | 2024-07-16 | 华南理工大学 | 一种两亲性离子聚合物pmpc-oda及其制备方法 |
| AU2024286366A1 (en) * | 2023-06-07 | 2025-12-04 | Kodiak Sciences Inc. | Compositions of conjugated and unconjugated proteins |
| CN116675786A (zh) * | 2023-07-10 | 2023-09-01 | 盐城师范学院 | 一种靶向传递喜树碱的环糊精超分子药物及其制备方法和应用 |
| IL326345A (en) * | 2023-08-03 | 2026-04-01 | Adcentrx Therapeutics Inc | Drug conjugates, methods of their preparation and uses |
| JP2026031534A (ja) * | 2024-08-09 | 2026-02-24 | デンカ株式会社 | トリアゾール骨格含有重合体の製造方法、トリアゾール骨格含有重合体及び組成物 |
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| US6225431B1 (en) * | 1991-07-05 | 2001-05-01 | Biocompatibles Limited | Biocompatibilizing process |
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| ATE245667T1 (de) | 1999-05-27 | 2003-08-15 | Biocompatibles Uk Ltd | Lösungen von polymeren |
| US7632522B2 (en) * | 2000-09-28 | 2009-12-15 | Nanocyte Inc. | Use of stinging cells/capsules for the delivery of active agents to keratinous substances |
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| WO2005087818A1 (en) * | 2004-03-05 | 2005-09-22 | Carnegie Mellon University | Preparation of functional polymers |
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| US20090018646A1 (en) * | 2007-07-10 | 2009-01-15 | Zhao Jonathon Z | Coating Employing an Anti-Thrombotic Conjugate |
| CA2745307A1 (en) | 2008-12-12 | 2010-06-17 | University Of Massachusetts | Polyesters with grafted zwitterions |
-
2009
- 2009-12-11 CA CA2745307A patent/CA2745307A1/en not_active Abandoned
- 2009-12-11 CA CA2745302A patent/CA2745302A1/en not_active Abandoned
- 2009-12-11 CN CN200980156713.4A patent/CN102317332B/zh not_active Expired - Fee Related
- 2009-12-11 WO PCT/US2009/067668 patent/WO2010068864A2/en not_active Ceased
- 2009-12-11 EP EP09832608.5A patent/EP2358770B1/en not_active Not-in-force
- 2009-12-11 US US13/131,662 patent/US8802738B2/en active Active
- 2009-12-11 AU AU2009324490A patent/AU2009324490A1/en not_active Abandoned
- 2009-12-11 BR BRPI0923336A patent/BRPI0923336A2/pt not_active IP Right Cessation
- 2009-12-11 US US13/131,665 patent/US9416210B2/en active Active
- 2009-12-11 WO PCT/US2009/067665 patent/WO2010068862A2/en not_active Ceased
- 2009-12-11 EP EP09832610A patent/EP2356167A4/en not_active Withdrawn
-
2011
- 2011-06-09 IL IL213448A patent/IL213448A0/en unknown
-
2016
- 2016-06-30 US US15/198,372 patent/US10632206B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CN102317332B (zh) | 2014-04-30 |
| AU2009324490A1 (en) | 2011-06-23 |
| WO2010068864A3 (en) | 2010-09-16 |
| CA2745307A1 (en) | 2010-06-17 |
| EP2358770A4 (en) | 2012-07-11 |
| WO2010068862A3 (en) | 2010-09-16 |
| US20110319569A1 (en) | 2011-12-29 |
| WO2010068864A2 (en) | 2010-06-17 |
| EP2356167A2 (en) | 2011-08-17 |
| IL213448A0 (en) | 2011-07-31 |
| EP2356167A4 (en) | 2012-07-11 |
| EP2358770A2 (en) | 2011-08-24 |
| CN102317332A (zh) | 2012-01-11 |
| US20160346400A1 (en) | 2016-12-01 |
| US9416210B2 (en) | 2016-08-16 |
| US20110319570A1 (en) | 2011-12-29 |
| CA2745302A1 (en) | 2010-06-17 |
| WO2010068862A2 (en) | 2010-06-17 |
| US10632206B2 (en) | 2020-04-28 |
| EP2358770B1 (en) | 2017-03-15 |
| US8802738B2 (en) | 2014-08-12 |
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