AU2011325112B2 - Cest systems exhibiting a concentration independent responsiveness - Google Patents
Cest systems exhibiting a concentration independent responsiveness Download PDFInfo
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- AU2011325112B2 AU2011325112B2 AU2011325112A AU2011325112A AU2011325112B2 AU 2011325112 B2 AU2011325112 B2 AU 2011325112B2 AU 2011325112 A AU2011325112 A AU 2011325112A AU 2011325112 A AU2011325112 A AU 2011325112A AU 2011325112 B2 AU2011325112 B2 AU 2011325112B2
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- AU
- Australia
- Prior art keywords
- iii
- cest
- complex
- lanthanide
- ratiometric
- 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.)
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- 229920001429 chelating resin Polymers 0.000 description 1
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- 239000003153 chemical reaction reagent Substances 0.000 description 1
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- 150000001805 chlorine compounds Chemical class 0.000 description 1
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- 230000007423 decrease Effects 0.000 description 1
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- 238000001514 detection method Methods 0.000 description 1
- 238000007435 diagnostic evaluation Methods 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
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- 230000029142 excretion Effects 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- DPNNNPAKRZOSMO-UHFFFAOYSA-K gadoteridol Chemical compound [Gd+3].CC(O)CN1CCN(CC([O-])=O)CCN(CC([O-])=O)CCN(CC([O-])=O)CC1 DPNNNPAKRZOSMO-UHFFFAOYSA-K 0.000 description 1
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 150000002307 glutamic acids Chemical class 0.000 description 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
- 229960002449 glycine Drugs 0.000 description 1
- BASWNCIBQYFVNL-UHFFFAOYSA-N henicosylhydrazine Chemical compound C(CCCCCCCCCCCCCCCCC)CCCNN BASWNCIBQYFVNL-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011503 in vivo imaging Methods 0.000 description 1
- 238000012623 in vivo measurement Methods 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 238000001361 intraarterial administration Methods 0.000 description 1
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- 238000010253 intravenous injection Methods 0.000 description 1
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- 238000011835 investigation Methods 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- XQZXYNRDCRIARQ-LURJTMIESA-N iopamidol Chemical compound C[C@H](O)C(=O)NC1=C(I)C(C(=O)NC(CO)CO)=C(I)C(C(=O)NC(CO)CO)=C1I XQZXYNRDCRIARQ-LURJTMIESA-N 0.000 description 1
- 229960004647 iopamidol Drugs 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910021644 lanthanide ion Inorganic materials 0.000 description 1
- 229910000311 lanthanide oxide Inorganic materials 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229960003646 lysine Drugs 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 101150016833 mec-3 gene Proteins 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229960003104 ornithine Drugs 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 125000001749 primary amide group Chemical group 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 235000020046 sherry Nutrition 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000001542 size-exclusion chromatography Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000000264 spin echo pulse sequence Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
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- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 229960003080 taurine Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000003325 tomography Methods 0.000 description 1
- YDJXDYKQMRNUSA-UHFFFAOYSA-N tri(propan-2-yl)silane Chemical compound CC(C)[SiH](C(C)C)C(C)C YDJXDYKQMRNUSA-UHFFFAOYSA-N 0.000 description 1
- LEYFXTUKPKKWMP-UHFFFAOYSA-K trichloroytterbium;hexahydrate Chemical compound O.O.O.O.O.O.Cl[Yb](Cl)Cl LEYFXTUKPKKWMP-UHFFFAOYSA-K 0.000 description 1
- 238000010200 validation analysis Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/06—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations
- A61K49/08—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by the carrier
- A61K49/10—Organic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/06—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations
- A61K49/08—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by the carrier
- A61K49/10—Organic compounds
- A61K49/101—Organic compounds the carrier being a complex-forming compound able to form MRI-active complexes with paramagnetic metals
- A61K49/106—Organic compounds the carrier being a complex-forming compound able to form MRI-active complexes with paramagnetic metals the complex-forming compound being cyclic, e.g. DOTA
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/06—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations
- A61K49/08—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by the carrier
- A61K49/10—Organic compounds
- A61K49/12—Macromolecular compounds
- A61K49/124—Macromolecular compounds dendrimers, dendrons, hyperbranched compounds
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01R—MEASURING ELECTRIC VARIABLES; MEASURING MAGNETIC VARIABLES
- G01R33/00—Arrangements or instruments for measuring magnetic variables
- G01R33/20—Arrangements or instruments for measuring magnetic variables involving magnetic resonance
- G01R33/44—Arrangements or instruments for measuring magnetic variables involving magnetic resonance using nuclear magnetic resonance [NMR]
- G01R33/48—NMR imaging systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/06—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations
- A61K49/08—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by the carrier
- A61K49/10—Organic compounds
- A61K49/101—Organic compounds the carrier being a complex-forming compound able to form MRI-active complexes with paramagnetic metals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/06—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations
- A61K49/08—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by the carrier
- A61K49/10—Organic compounds
- A61K49/101—Organic compounds the carrier being a complex-forming compound able to form MRI-active complexes with paramagnetic metals
- A61K49/106—Organic compounds the carrier being a complex-forming compound able to form MRI-active complexes with paramagnetic metals the complex-forming compound being cyclic, e.g. DOTA
- A61K49/108—Organic compounds the carrier being a complex-forming compound able to form MRI-active complexes with paramagnetic metals the complex-forming compound being cyclic, e.g. DOTA the metal complex being Gd-DOTA
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01R—MEASURING ELECTRIC VARIABLES; MEASURING MAGNETIC VARIABLES
- G01R33/00—Arrangements or instruments for measuring magnetic variables
- G01R33/20—Arrangements or instruments for measuring magnetic variables involving magnetic resonance
- G01R33/44—Arrangements or instruments for measuring magnetic variables involving magnetic resonance using nuclear magnetic resonance [NMR]
- G01R33/48—NMR imaging systems
- G01R33/54—Signal processing systems, e.g. using pulse sequences ; Generation or control of pulse sequences; Operator console
- G01R33/56—Image enhancement or correction, e.g. subtraction or averaging techniques, e.g. improvement of signal-to-noise ratio and resolution
- G01R33/5601—Image enhancement or correction, e.g. subtraction or averaging techniques, e.g. improvement of signal-to-noise ratio and resolution involving use of a contrast agent for contrast manipulation, e.g. a paramagnetic, super-paramagnetic, ferromagnetic or hyperpolarised contrast agent
Landscapes
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Physics & Mathematics (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Radiology & Medical Imaging (AREA)
- Chemical & Material Sciences (AREA)
- High Energy & Nuclear Physics (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- General Physics & Mathematics (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Magnetic Resonance Imaging Apparatus (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10190161A EP2457594A1 (en) | 2010-11-05 | 2010-11-05 | Cest systems exhibiting a concentration independent responsiveness |
| EP10190161.9 | 2010-11-05 | ||
| PCT/EP2011/069406 WO2012059576A1 (en) | 2010-11-05 | 2011-11-04 | Cest systems exhibiting a concentration independent responsiveness |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2011325112A1 AU2011325112A1 (en) | 2013-05-02 |
| AU2011325112B2 true AU2011325112B2 (en) | 2016-03-31 |
Family
ID=43530158
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2011325112A Ceased AU2011325112B2 (en) | 2010-11-05 | 2011-11-04 | Cest systems exhibiting a concentration independent responsiveness |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US10232060B2 (https=) |
| EP (2) | EP2457594A1 (https=) |
| JP (2) | JP2013542948A (https=) |
| KR (1) | KR20130138807A (https=) |
| CN (1) | CN103260652B (https=) |
| AU (1) | AU2011325112B2 (https=) |
| CA (1) | CA2816948C (https=) |
| IL (1) | IL226123A (https=) |
| MX (1) | MX349239B (https=) |
| RU (1) | RU2605823C2 (https=) |
| WO (1) | WO2012059576A1 (https=) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014165719A1 (en) | 2013-04-05 | 2014-10-09 | The Trustees Of The University Of Pennsylvania | Non-invasive imaging of tissue redox state by mri |
| KR101653064B1 (ko) | 2014-12-26 | 2016-09-09 | 에스티팜 주식회사 | 가도부트롤의 제조방법 |
| WO2016123446A1 (en) * | 2015-01-30 | 2016-08-04 | The Johns Hopkins University | Label-free mr imaging of tumor malignancy |
| EP3101012A1 (en) | 2015-06-04 | 2016-12-07 | Bayer Pharma Aktiengesellschaft | New gadolinium chelate compounds for use in magnetic resonance imaging |
| LT3386954T (lt) * | 2015-12-10 | 2021-04-12 | Bracco Imaging Spa | Dimeriniai kontrastiniai agentai |
| JP6964583B2 (ja) * | 2015-12-23 | 2021-11-10 | ブラッコ・イメージング・ソシエタ・ペル・アチオニBracco Imaging S.P.A. | レシオメトリックパルスｃｅｓｔイメージング |
| RU2755181C2 (ru) | 2016-11-28 | 2021-09-14 | Байер Фарма Акциенгезельшафт | Новые хелатные соединения гадолиния с высокой релаксивностью для применения в магнитно-резонансной визуализации |
| FR3069245B1 (fr) * | 2017-07-21 | 2019-07-26 | Guerbet | Ligands macrocycliques lipophiles, leurs complexes ainsi que leurs utilisations medicales |
| CN108047151B (zh) * | 2018-01-03 | 2020-08-04 | 广州康瑞泰药业有限公司 | 一种高收率钆布醇的制备方法 |
| CN113164628A (zh) | 2018-11-23 | 2021-07-23 | 拜耳股份有限公司 | 造影介质制剂及其制备方法 |
| WO2020127154A1 (en) | 2018-12-18 | 2020-06-25 | Bracco Imaging Spa | Pharmaceutical compositions comprising gd-complexes and polyarylene additives |
| US20200397924A1 (en) * | 2019-01-28 | 2020-12-24 | Hubei Tianshu Pharmaceutical Co., Ltd | Preparation method of intermediate of gadolinium-based ionic contrast agent and use thereof |
| US12529739B2 (en) | 2022-07-26 | 2026-01-20 | Canon Medical Systems Corporation | pH calculating apparatus, magnetic resonance imaging apparatus, and pH calculating method |
| CN120609858A (zh) * | 2025-05-30 | 2025-09-09 | 中国科学院精密测量科学与技术创新研究院 | 镧系金属配合物作为31p cest高场造影剂在识别atp中的应用 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4009119A1 (de) | 1990-03-19 | 1991-09-26 | Schering Ag | 1,4,7,10-tetraazacyclododecan-butyltriole, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische mittel |
| GB9504910D0 (en) | 1995-03-10 | 1995-04-26 | Nycomed Imaging As | Compounds |
| EP1178837A2 (en) | 1999-04-21 | 2002-02-13 | THE GOVERNMENT OF THE UNITED STATES OF AMERICA, as represented by THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES | Method for enhancing contrast produced by mri |
| WO2002043775A2 (en) * | 2000-11-20 | 2002-06-06 | GODFREY, Cullen, M. | Paramagnetic metal ion-based macrocyclic contrast agents |
| EP1331012A1 (en) | 2002-01-29 | 2003-07-30 | BRACCO IMAGING S.p.A. | Responsive paramagnetic MRI contrast agents |
| EP1466629A1 (en) * | 2003-04-11 | 2004-10-13 | BRACCO IMAGING S.p.A. | Adducts between magnetic resonance shift reagents and substrates containing exchangeable protons for "CEST" applications |
| JP2008513533A (ja) * | 2004-09-23 | 2008-05-01 | ゲルベ | Ｃｅｓｔイメージング用の造影剤封入システム |
| US8463358B2 (en) * | 2006-06-09 | 2013-06-11 | Koninklijke Philips Electronics N.V. | Elimination of contrast agent concentration dependency in MRI |
| US20100247445A1 (en) * | 2007-12-07 | 2010-09-30 | Koninklijke Philips Electronics N.V. | Polymeric drug carrier for image-guided delivery |
| EP2067485A1 (en) * | 2007-12-07 | 2009-06-10 | Koninklijke Philips Electronics N.V. | Drug carrier providing MRI contrast enhancement |
-
2010
- 2010-11-05 EP EP10190161A patent/EP2457594A1/en not_active Withdrawn
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2011
- 2011-11-04 KR KR1020137014354A patent/KR20130138807A/ko not_active Withdrawn
- 2011-11-04 MX MX2013004825A patent/MX349239B/es active IP Right Grant
- 2011-11-04 AU AU2011325112A patent/AU2011325112B2/en not_active Ceased
- 2011-11-04 RU RU2013125778/15A patent/RU2605823C2/ru active
- 2011-11-04 CA CA2816948A patent/CA2816948C/en active Active
- 2011-11-04 EP EP11778892.7A patent/EP2635311B1/en active Active
- 2011-11-04 US US13/879,083 patent/US10232060B2/en active Active
- 2011-11-04 JP JP2013537145A patent/JP2013542948A/ja active Pending
- 2011-11-04 WO PCT/EP2011/069406 patent/WO2012059576A1/en not_active Ceased
- 2011-11-04 CN CN201180053033.7A patent/CN103260652B/zh not_active Expired - Fee Related
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2013
- 2013-05-02 IL IL226123A patent/IL226123A/en active IP Right Grant
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2016
- 2016-12-15 JP JP2016243189A patent/JP6542748B2/ja not_active Expired - Fee Related
-
2019
- 2019-01-24 US US16/256,749 patent/US10328162B1/en active Active
Non-Patent Citations (2)
| Title |
|---|
| RANGANTHAN, R.S. et al.: "New Multimeric Magnetic Resonance Imaging Agents" Investigative Radiology, 1998, vol. 33, no. 11, pp. 779-797 * |
| WOODS M. et al.: "Europium(lll) Macrocyclic Complexes with Alcohol Pendant Groups as Chemical Exchange Saturation Transfer Agents", J. AM. CHEM SOC., vol. 128, 14 July 2006, pages 10155-10162 * |
Also Published As
| Publication number | Publication date |
|---|---|
| JP6542748B2 (ja) | 2019-07-10 |
| IL226123A0 (en) | 2013-06-27 |
| CA2816948C (en) | 2016-04-05 |
| RU2013125778A (ru) | 2014-12-10 |
| CN103260652B (zh) | 2016-10-12 |
| US20130195768A1 (en) | 2013-08-01 |
| CN103260652A (zh) | 2013-08-21 |
| MX349239B (es) | 2017-07-18 |
| US10328162B1 (en) | 2019-06-25 |
| IL226123A (en) | 2016-02-29 |
| AU2011325112A1 (en) | 2013-05-02 |
| MX2013004825A (es) | 2013-06-03 |
| EP2635311B1 (en) | 2017-08-16 |
| WO2012059576A1 (en) | 2012-05-10 |
| US10232060B2 (en) | 2019-03-19 |
| US20190209713A1 (en) | 2019-07-11 |
| EP2635311A1 (en) | 2013-09-11 |
| EP2457594A1 (en) | 2012-05-30 |
| CA2816948A1 (en) | 2012-05-10 |
| KR20130138807A (ko) | 2013-12-19 |
| JP2013542948A (ja) | 2013-11-28 |
| RU2605823C2 (ru) | 2016-12-27 |
| JP2017078080A (ja) | 2017-04-27 |
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Legal Events
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| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |