US20110192500A1 - Resorbable magnesium alloy - Google Patents
Resorbable magnesium alloy Download PDFInfo
- Publication number
- US20110192500A1 US20110192500A1 US12/995,767 US99576709A US2011192500A1 US 20110192500 A1 US20110192500 A1 US 20110192500A1 US 99576709 A US99576709 A US 99576709A US 2011192500 A1 US2011192500 A1 US 2011192500A1
- Authority
- US
- United States
- Prior art keywords
- alloy
- percent
- magnesium
- weight
- magnesium alloy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C22—METALLURGY; FERROUS OR NON-FERROUS ALLOYS; TREATMENT OF ALLOYS OR NON-FERROUS METALS
- C22C—ALLOYS
- C22C23/00—Alloys based on magnesium
- C22C23/04—Alloys based on magnesium with zinc or cadmium as the next major constituent
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/02—Inorganic materials
- A61L27/04—Metals or alloys
- A61L27/047—Other specific metals or alloys not covered by A61L27/042 - A61L27/045 or A61L27/06
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
- A61L31/02—Inorganic materials
- A61L31/022—Metals or alloys
-
- C—CHEMISTRY; METALLURGY
- C22—METALLURGY; FERROUS OR NON-FERROUS ALLOYS; TREATMENT OF ALLOYS OR NON-FERROUS METALS
- C22C—ALLOYS
- C22C23/00—Alloys based on magnesium
- C22C23/06—Alloys based on magnesium with a rare earth metal as the next major constituent
Definitions
- Inventive subject matter described herein relates to a magnesium alloy, implants made from the alloy, methods of manufacture and methods of use of the alloy.
- implants are used for a broad range of applications, for example for orthopedic purposes, as support for vessels, and for attaching or fixing tissues or bones. Often the implants have only a temporary function until completion of the healing process. In order to avoid complications resulting from these implants remaining permanently in the body, they often must be operatively removed or made of a biocorrodible material which will be gradually degraded by the body.
- biocorrodible materials based on polymers or alloys are known. Of special interest are alloys made of biodegradable metals such as magnesium, iron and tungsten.
- European Patent 1 270 023 describes a magnesium alloy which is reportedly suitable for the manufacture of endovascular or orthopedic implants.
- the alloy contains more than 50% magnesium and up to 5% rare earth metals.
- Other elements like aluminum, lithium and iron may also be contained in the disclosed alloy.
- Application WO2008/035948 describes a biodegradable magnesium based alloy, comprising up to 40 atomic percent calcium as well as up to 40 atomic percent of one or more trace elements.
- the disclosed trace elements include Zr, Mo, Nb, Ta, Ti, Sr, Cr, Mn, Zn, Si, P, Ni and Fe.
- the degradation rate of the magnesium alloy is reportedly varied.
- Biodegradable magnesium alloys are also known to contain yttrium.
- WO02/100452 describes an alloy optionally comprising 0.01 to 7% by weight of yttrium and 0.01 to 8% by weight of rare earth metals.
- the alloy may also contain lithium and/or aluminum.
- Ytterbium has been used as radiopaque marker element in implants.
- US2008/0033530 describes a marker alloy comprising 40 to 90 atomic percent of ytterbium, as well as 10 to 60 atomic percent magnesium and 0 to 10 atomic percent of one or several elements selected from the group of Ag, Zn, Au, Ga, Pd, Pt, Al, Sn, Ca, Nd, Ba, Si, and Ge.
- the alloy thus has a sufficient X-ray density at low material thicknesses.
- the degradation of ytterbium is reported as being approximately equal to the degradation of the main body.
- Patent Application JP2004099940 describes a lightweight magnesium based alloy reportedly combining high strength with high ductility.
- the composition of the alloy comprises 0.5 to 5 atomic percent rare earth elements selected from Y, La, Ce, Pr, Nd, Pm, Sm, Eu, Gd, Tb, Dy, Ho, Er, Tm, Yb, Lu and miscl. metal.
- the alloy further comprises 0.2 to 4 atomic percent zinc.
- Inventive subject matter described herein includes a biocorrodible and age-hardenable alloy, comprised essentially of magnesium, ytterbium, zinc and calcium.
- Inventive subject matter also includes an implant incorporating an age-hardenable magnesium alloy, comprising ytterbium, zinc and calcium.
- the magnesium alloy includes ytterbium, calcium and zinc.
- the three elements are present in following amounts:
- ytterbium containing magnesium alloys show a significantly increased age-hardenability if zinc and calcium are present. Moreover, such alloy embodiments also exhibit favorable corrosion properties in chlorine containing aqueous environments.
- This alloy is produced, in some embodiments, by a micro-alloying process embodiment, such as is conventionally known.
- the micro-alloying process in combination with the chosen elements of embodiments described herein, which have a high grain growth restriction factor, enables the manufacture of an alloy having very good cold-forming properties and a low mechanical anisotropy.
- Composition described herein induce a fine grained structure in the alloy during solidification as well as during subsequent hot-forming processes. This is mainly due to the formation of fine precipitations of these elements which restrict undesirable grain growth during recrystallization.
- the ytterbium containing magnesium alloy as described herein may contain further elements, that include manganese, zirconium, aluminum and elements from the group of rare earths. From this group, scandium and yttrium are used in some embodiments.
- the amount of each of these additional elements in the alloy is up to 4.0 weight percent, for some embodiments, up to 3.0 weight percent for some embodiments, up to 2.0 weight percent for some embodiments, and up to 1.0 weight percent for some embodiments.
- any combination of these elements may be added, each of which makes up to 4.0 weight percent, for some embodiments up to 3.0 weight percent, for some embodiments up to 2.0 weight percent, and for some embodiments up to 1.0 weight percent of the total weight of the alloy.
- rare earths as used herein includes scandium, yttrium, lanthanum, cerium, praseodymium, neodymium, promethium, samarium, europium, gadolinium, terbium, dysprosium, holmium, erbium, thulium, ytterbium, and lutetium. It should be understood that additional elements in the alloy are not limited to those listed above, but that other elements, especially from the group of metals and transition metals, may be added as well.
- An implant containing the alloy as disclosed herein may be produced using techniques known in the art.
- the implant may be in any form, especially in the form of a plate, specifically a bone plate, a screw, a nail, a bone nail, a stent, a rod. Implants made of the specified alloy are suitable for implantation in animal or human body.
- Novel magnesium alloys containing 4 wt-% Yb, 0.8 wt-% Zn and 0.25 wt % Ca were melted and cast in an induction furnace in Ar-atmosphere.
- the billets were extruded at a temperature of 350° C. to an end-diameter of 8.6 mm, which corresponds to an extrusion-ratio of 12.5.
- the microstructure of the extruded alloys showed a very fine-grained structure with a grain size of approximately 5 ⁇ m.
- This material featured an average yield strength of 150 MPa, tensile strength of 250 MPa, uniform elongation of 20% and elongation to fracture of 28%.
- Hardness measurements indicated an age hardening response, where the values increased from approximately 50 HV5 in the solution heat-treated state to approximately 70 HV5 in the age hardened state.
Abstract
Description
- This patent application claims the priority benefit of U.S. Provisional Patent Application Ser. No. 61/059,370 filed Jun. 6, 2008 and entitled “RESORBABLE MAGNESIUM ALLOY”, the content of which is incorporated herein by reference in its entirety.
- Inventive subject matter described herein relates to a magnesium alloy, implants made from the alloy, methods of manufacture and methods of use of the alloy.
- In modem medical technology, implants are used for a broad range of applications, for example for orthopedic purposes, as support for vessels, and for attaching or fixing tissues or bones. Often the implants have only a temporary function until completion of the healing process. In order to avoid complications resulting from these implants remaining permanently in the body, they often must be operatively removed or made of a biocorrodible material which will be gradually degraded by the body. A growing number of such biocorrodible materials based on polymers or alloys are known. Of special interest are alloys made of biodegradable metals such as magnesium, iron and tungsten.
- European Patent 1 270 023 describes a magnesium alloy which is reportedly suitable for the manufacture of endovascular or orthopedic implants. The alloy contains more than 50% magnesium and up to 5% rare earth metals. Other elements like aluminum, lithium and iron may also be contained in the disclosed alloy.
- Application WO2008/035948 describes a biodegradable magnesium based alloy, comprising up to 40 atomic percent calcium as well as up to 40 atomic percent of one or more trace elements. The disclosed trace elements include Zr, Mo, Nb, Ta, Ti, Sr, Cr, Mn, Zn, Si, P, Ni and Fe. Through the addition of the trace elements the degradation rate of the magnesium alloy is reportedly varied.
- Biodegradable magnesium alloys are also known to contain yttrium. WO02/100452 describes an alloy optionally comprising 0.01 to 7% by weight of yttrium and 0.01 to 8% by weight of rare earth metals. The alloy may also contain lithium and/or aluminum.
- Ytterbium has been used as radiopaque marker element in implants. US2008/0033530 describes a marker alloy comprising 40 to 90 atomic percent of ytterbium, as well as 10 to 60 atomic percent magnesium and 0 to 10 atomic percent of one or several elements selected from the group of Ag, Zn, Au, Ga, Pd, Pt, Al, Sn, Ca, Nd, Ba, Si, and Ge. The alloy thus has a sufficient X-ray density at low material thicknesses. The degradation of ytterbium is reported as being approximately equal to the degradation of the main body.
- Patent Application JP2004099940 describes a lightweight magnesium based alloy reportedly combining high strength with high ductility. The composition of the alloy comprises 0.5 to 5 atomic percent rare earth elements selected from Y, La, Ce, Pr, Nd, Pm, Sm, Eu, Gd, Tb, Dy, Ho, Er, Tm, Yb, Lu and miscl. metal. The alloy further comprises 0.2 to 4 atomic percent zinc.
- Inventive subject matter described herein includes a biocorrodible and age-hardenable alloy, comprised essentially of magnesium, ytterbium, zinc and calcium.
- Inventive subject matter also includes an implant incorporating an age-hardenable magnesium alloy, comprising ytterbium, zinc and calcium.
- According to one exemplary embodiment, the magnesium alloy includes ytterbium, calcium and zinc. The three elements are present in following amounts:
-
- Ytterbium: 0.5 to 8.0 weight percent
- Zinc: 0.2 to 6.0 weight percent
- Calcium: 0.1 to 2.0 weight percent
The balance up to 100 weight percent includes magnesium as well as unavoidable impurities. For example, such impurities may stem from the production process of the alloy or from impurities already contained in the source material.
- Surprisingly it was found that ytterbium containing magnesium alloys show a significantly increased age-hardenability if zinc and calcium are present. Moreover, such alloy embodiments also exhibit favorable corrosion properties in chlorine containing aqueous environments.
- This alloy is produced, in some embodiments, by a micro-alloying process embodiment, such as is conventionally known. The micro-alloying process in combination with the chosen elements of embodiments described herein, which have a high grain growth restriction factor, enables the manufacture of an alloy having very good cold-forming properties and a low mechanical anisotropy. Composition described herein induce a fine grained structure in the alloy during solidification as well as during subsequent hot-forming processes. This is mainly due to the formation of fine precipitations of these elements which restrict undesirable grain growth during recrystallization.
- According to another exemplary embodiment, the ytterbium containing magnesium alloy as described herein may contain further elements, that include manganese, zirconium, aluminum and elements from the group of rare earths. From this group, scandium and yttrium are used in some embodiments. The amount of each of these additional elements in the alloy is up to 4.0 weight percent, for some embodiments, up to 3.0 weight percent for some embodiments, up to 2.0 weight percent for some embodiments, and up to 1.0 weight percent for some embodiments. The skilled artisan understands that any combination of these elements may be added, each of which makes up to 4.0 weight percent, for some embodiments up to 3.0 weight percent, for some embodiments up to 2.0 weight percent, and for some embodiments up to 1.0 weight percent of the total weight of the alloy. The collective term “rare earths” as used herein includes scandium, yttrium, lanthanum, cerium, praseodymium, neodymium, promethium, samarium, europium, gadolinium, terbium, dysprosium, holmium, erbium, thulium, ytterbium, and lutetium. It should be understood that additional elements in the alloy are not limited to those listed above, but that other elements, especially from the group of metals and transition metals, may be added as well.
- An implant containing the alloy as disclosed herein may be produced using techniques known in the art. The implant may be in any form, especially in the form of a plate, specifically a bone plate, a screw, a nail, a bone nail, a stent, a rod. Implants made of the specified alloy are suitable for implantation in animal or human body.
- The foregoing description of embodiments has been provided for the purposes of illustration and description. It is not intended to be exhaustive or to limit the invention to the precise forms disclosed. Obviously, many modifications and variations will be apparent to practitioners skilled in the art. It is intended that the scope of the invention be defined by the following claims and their equivalents.
- Novel magnesium alloys containing 4 wt-% Yb, 0.8 wt-% Zn and 0.25 wt % Ca were melted and cast in an induction furnace in Ar-atmosphere. The billets were extruded at a temperature of 350° C. to an end-diameter of 8.6 mm, which corresponds to an extrusion-ratio of 12.5. The microstructure of the extruded alloys showed a very fine-grained structure with a grain size of approximately 5 μm. This material featured an average yield strength of 150 MPa, tensile strength of 250 MPa, uniform elongation of 20% and elongation to fracture of 28%. Hardness measurements indicated an age hardening response, where the values increased from approximately 50 HV5 in the solution heat-treated state to approximately 70 HV5 in the age hardened state.
Claims (9)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US12/995,767 US20110192500A1 (en) | 2008-06-06 | 2009-05-21 | Resorbable magnesium alloy |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US5937008P | 2008-06-06 | 2008-06-06 | |
US12/995,767 US20110192500A1 (en) | 2008-06-06 | 2009-05-21 | Resorbable magnesium alloy |
PCT/US2009/003138 WO2009148515A1 (en) | 2008-06-06 | 2009-05-21 | Resorbable magnesium alloy |
Publications (1)
Publication Number | Publication Date |
---|---|
US20110192500A1 true US20110192500A1 (en) | 2011-08-11 |
Family
ID=41398381
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US12/995,767 Abandoned US20110192500A1 (en) | 2008-06-06 | 2009-05-21 | Resorbable magnesium alloy |
Country Status (11)
Country | Link |
---|---|
US (1) | US20110192500A1 (en) |
EP (1) | EP2294236B1 (en) |
JP (2) | JP2011524465A (en) |
KR (1) | KR101722918B1 (en) |
CN (1) | CN102057068B (en) |
AU (1) | AU2009255698B2 (en) |
BR (1) | BRPI0912151A2 (en) |
CA (1) | CA2726572C (en) |
ES (1) | ES2540742T3 (en) |
PL (1) | PL2294236T3 (en) |
WO (1) | WO2009148515A1 (en) |
Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2013052791A3 (en) * | 2011-10-06 | 2013-05-30 | University Of Pittsburgh-Of The Commonwealth System Of Higher Education | Biodegradable metal alloys |
KR20150050586A (en) * | 2012-08-31 | 2015-05-08 | 신세스 게엠바하 | Ultrapure magnesium alloy with adjustable degradation rate |
WO2017035072A1 (en) * | 2015-08-21 | 2017-03-02 | University Of Pittsburgh-Of The Commonwealth System Of Higher Education | Degradable magnesium-based implant devices for bone fixation |
US9863020B2 (en) | 2014-04-03 | 2018-01-09 | University of Pittsburgh—of the Commonwealth System of Higher Education | Biodegradable metal alloys |
US20180030578A1 (en) * | 2015-02-25 | 2018-02-01 | In-Young Lee | Plastic deformation magnesium alloy having excellent thermal conductivity and flame retardancy, and preparation method |
CN108236495A (en) * | 2018-03-30 | 2018-07-03 | 西安卓恰医疗器械有限公司 | Low alloying degradable miniature interior fixation kit, magnesium alloy preparation method and magnesium alloy materials |
WO2018132134A1 (en) * | 2017-01-11 | 2018-07-19 | The Boeing Company | Calcium-bearing magnesium and rare earth element alloy and method for manufacturing the same |
US20180207327A1 (en) * | 2017-01-18 | 2018-07-26 | The Chinese University Of Hong Kong | Hybrid Implant System and Manufacturing Method Therefor |
US10246763B2 (en) | 2012-08-24 | 2019-04-02 | The Regents Of The University Of California | Magnesium-zinc-strontium alloys for medical implants and devices |
US10344365B2 (en) | 2012-06-26 | 2019-07-09 | Biotronik Ag | Magnesium-zinc-calcium alloy and method for producing implants containing the same |
US10358709B2 (en) | 2012-06-26 | 2019-07-23 | Biotronik Ag | Magnesium-zinc-calcium alloy, method for production thereof, and use thereof |
US10478529B2 (en) | 2013-03-14 | 2019-11-19 | DePuy Synthes Products, Inc. | Magnesium alloy with adjustable degradation rate |
US10895000B2 (en) | 2012-06-26 | 2021-01-19 | Biotronik Ag | Magnesium alloy, method for the production thereof and use thereof |
US10995398B2 (en) | 2012-06-26 | 2021-05-04 | Biotronik Ag | Corrosion resistant stent |
US11732334B2 (en) * | 2017-04-12 | 2023-08-22 | University Of Pittsburgh-Of The Commonwealth System Of Higher Education | Properties and parameters of novel biodegradable metallic alloys |
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EP2224032A1 (en) * | 2009-02-13 | 2010-09-01 | Nederlandse Organisatie voor toegepast -natuurwetenschappelijk onderzoek TNO | Process for manufacturing magnesium alloy based products |
AT510087B1 (en) * | 2010-07-06 | 2012-05-15 | Ait Austrian Institute Of Technology Gmbh | MAGNESIUM ALLOY |
WO2012033689A1 (en) | 2010-09-08 | 2012-03-15 | Synthes Usa, Llc | Fixation device with magnesium core |
JP5981930B2 (en) | 2010-11-09 | 2016-08-31 | トランスルミナル テクノロジーズ リミテッド ライアビリティー カンパニー | Specially designed magnesium-aluminum alloy and its use in medicine in hemodynamic environment |
DE102012006454A1 (en) * | 2012-03-30 | 2013-10-02 | Heraeus Medical Gmbh | Anti-infective spacer for osteosynthesis plates |
PL2857536T3 (en) * | 2013-10-03 | 2016-08-31 | Weinberg Annelie Martina | Implant for patients in growth, method for its preparation and use |
KR101670043B1 (en) * | 2015-03-17 | 2016-10-27 | 전북대학교산학협력단 | Calcium added magnesium alloy and its manufacturing method |
US10883158B2 (en) | 2016-06-02 | 2021-01-05 | Unist (Ulsan National Institute Of Science And Technology) | Magnesium alloy materials and method for producing the same |
CN106435315B (en) * | 2016-10-17 | 2018-03-16 | 南京镐极信息技术有限公司 | High-strength cast magnesium alloy containing europium and preparation method thereof |
CN106544563B (en) * | 2016-11-04 | 2018-06-19 | 哈尔滨理工大学 | A kind of biodegradable Mg-Ca-Mn-Sn magnesium alloy materials and preparation method and application |
CN109457130B (en) * | 2019-01-14 | 2020-11-20 | 兰州理工大学 | High-toughness biomedical magnesium alloy and preparation method thereof |
CN109778197A (en) * | 2019-03-07 | 2019-05-21 | 洛阳理工学院 | One kind anode magnesium alloy containing Yb and the preparation method and application thereof |
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- 2009-05-21 BR BRPI0912151A patent/BRPI0912151A2/en not_active Application Discontinuation
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- 2009-05-21 JP JP2011512450A patent/JP2011524465A/en active Pending
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- 2009-05-21 KR KR1020107026910A patent/KR101722918B1/en active IP Right Grant
- 2009-05-21 WO PCT/US2009/003138 patent/WO2009148515A1/en active Application Filing
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Cited By (24)
Publication number | Priority date | Publication date | Assignee | Title |
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US9510932B2 (en) | 2011-10-06 | 2016-12-06 | University Of Pittsburgh-Of The Commonwealth System Of Higher Education | Biodegradable metal alloys |
WO2013052791A3 (en) * | 2011-10-06 | 2013-05-30 | University Of Pittsburgh-Of The Commonwealth System Of Higher Education | Biodegradable metal alloys |
US10995398B2 (en) | 2012-06-26 | 2021-05-04 | Biotronik Ag | Corrosion resistant stent |
US10358709B2 (en) | 2012-06-26 | 2019-07-23 | Biotronik Ag | Magnesium-zinc-calcium alloy, method for production thereof, and use thereof |
US11499214B2 (en) | 2012-06-26 | 2022-11-15 | Biotronik Ag | Magnesium-zinc-calcium alloy and method for producing implants containing the same |
US10895000B2 (en) | 2012-06-26 | 2021-01-19 | Biotronik Ag | Magnesium alloy, method for the production thereof and use thereof |
US10344365B2 (en) | 2012-06-26 | 2019-07-09 | Biotronik Ag | Magnesium-zinc-calcium alloy and method for producing implants containing the same |
US10246763B2 (en) | 2012-08-24 | 2019-04-02 | The Regents Of The University Of California | Magnesium-zinc-strontium alloys for medical implants and devices |
KR102275471B1 (en) | 2012-08-31 | 2021-07-13 | 신세스 게엠바하 | Ultrapure magnesium alloy with adjustable degradation rate |
KR20150050586A (en) * | 2012-08-31 | 2015-05-08 | 신세스 게엠바하 | Ultrapure magnesium alloy with adjustable degradation rate |
US10213522B2 (en) | 2012-08-31 | 2019-02-26 | DePuy Synthes Products, Inc. | Ultrapure magnesium alloy with adjustable degradation rate |
US10478529B2 (en) | 2013-03-14 | 2019-11-19 | DePuy Synthes Products, Inc. | Magnesium alloy with adjustable degradation rate |
US9863020B2 (en) | 2014-04-03 | 2018-01-09 | University of Pittsburgh—of the Commonwealth System of Higher Education | Biodegradable metal alloys |
US10604827B2 (en) | 2014-04-03 | 2020-03-31 | University of Pittsburgh—Of the Commonwealth System of Higher Educatiion | Biodegradable metal alloys |
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Also Published As
Publication number | Publication date |
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JP2011524465A (en) | 2011-09-01 |
AU2009255698B2 (en) | 2015-03-26 |
KR20110014617A (en) | 2011-02-11 |
CN102057068A (en) | 2011-05-11 |
ES2540742T3 (en) | 2015-07-13 |
JP5913459B2 (en) | 2016-04-27 |
CA2726572C (en) | 2017-09-12 |
AU2009255698A1 (en) | 2009-12-10 |
PL2294236T3 (en) | 2015-09-30 |
JP2014205920A (en) | 2014-10-30 |
EP2294236A1 (en) | 2011-03-16 |
EP2294236B1 (en) | 2015-04-08 |
CA2726572A1 (en) | 2009-12-10 |
CN102057068B (en) | 2012-08-29 |
EP2294236A4 (en) | 2011-10-26 |
WO2009148515A1 (en) | 2009-12-10 |
KR101722918B1 (en) | 2017-04-04 |
BRPI0912151A2 (en) | 2018-11-06 |
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