CA2803520C - N-alkoxyamide conjugates as imaging agents - Google Patents
N-alkoxyamide conjugates as imaging agents Download PDFInfo
- Publication number
- CA2803520C CA2803520C CA2803520A CA2803520A CA2803520C CA 2803520 C CA2803520 C CA 2803520C CA 2803520 A CA2803520 A CA 2803520A CA 2803520 A CA2803520 A CA 2803520A CA 2803520 C CA2803520 C CA 2803520C
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- Prior art keywords
- mmol
- pharmaceutically acceptable
- alkyl
- acceptable salt
- compound
- Prior art date
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- 238000000034 method Methods 0.000 claims abstract description 98
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- 239000001257 hydrogen Substances 0.000 claims description 61
- 125000000623 heterocyclic group Chemical group 0.000 claims description 56
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- 125000003545 alkoxy group Chemical group 0.000 claims description 29
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 29
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- 229910052708 sodium Inorganic materials 0.000 description 1
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- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
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- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
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- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
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- RUPAXCPQAAOIPB-UHFFFAOYSA-N tert-butyl formate Chemical compound CC(C)(C)OC=O RUPAXCPQAAOIPB-UHFFFAOYSA-N 0.000 description 1
- FYMXNZMEOFIYEO-HSZRJFAPSA-N tert-butyl n-[(2r)-1-(6-aminohexoxyamino)-1-oxo-3-(4-phenylphenyl)propan-2-yl]carbamate Chemical compound C1=CC(C[C@@H](NC(=O)OC(C)(C)C)C(=O)NOCCCCCCN)=CC=C1C1=CC=CC=C1 FYMXNZMEOFIYEO-HSZRJFAPSA-N 0.000 description 1
- HGYUTLLRMCMCOH-GOSISDBHSA-N tert-butyl n-[(2r)-1-(6-aminohexoxyamino)-1-oxo-4-phenylbutan-2-yl]carbamate Chemical compound NCCCCCCONC(=O)[C@H](NC(=O)OC(C)(C)C)CCC1=CC=CC=C1 HGYUTLLRMCMCOH-GOSISDBHSA-N 0.000 description 1
- OJDRNVRDUSZNBD-CQSZACIVSA-N tert-butyl n-[(2r)-1-(6-aminohexoxyamino)-4-methyl-1-oxopentan-2-yl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@H](CC(C)C)C(=O)NOCCCCCCN OJDRNVRDUSZNBD-CQSZACIVSA-N 0.000 description 1
- RKRQXHOQAJUGJJ-JOCHJYFZSA-N tert-butyl n-[(2r)-1-[3-[4-(aminomethyl)phenyl]propoxyamino]-1-oxo-4-phenylbutan-2-yl]carbamate Chemical compound C([C@@H](NC(=O)OC(C)(C)C)C(=O)NOCCCC=1C=CC(CN)=CC=1)CC1=CC=CC=C1 RKRQXHOQAJUGJJ-JOCHJYFZSA-N 0.000 description 1
- LJDIOSYOJDYZDF-HSZRJFAPSA-N tert-butyl n-[(2r)-1-[3-[4-(aminomethyl)phenyl]propoxyamino]-3-(1h-indol-3-yl)-1-oxopropan-2-yl]carbamate Chemical compound O=C([C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)OC(C)(C)C)NOCCCC1=CC=C(CN)C=C1 LJDIOSYOJDYZDF-HSZRJFAPSA-N 0.000 description 1
- LSPLNWXGQLXOIF-OAHLLOKOSA-N tert-butyl n-[(2r)-1-[[4-(aminomethyl)phenoxy]amino]-4-methyl-1-oxopentan-2-yl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@H](CC(C)C)C(=O)NOC1=CC=C(CN)C=C1 LSPLNWXGQLXOIF-OAHLLOKOSA-N 0.000 description 1
- VQTRQYMBUAHKSN-LJQANCHMSA-N tert-butyl n-[(2r)-1-[[4-(aminomethyl)phenyl]methoxyamino]-1-oxo-3-phenylpropan-2-yl]carbamate Chemical compound C([C@@H](NC(=O)OC(C)(C)C)C(=O)NOCC=1C=CC(CN)=CC=1)C1=CC=CC=C1 VQTRQYMBUAHKSN-LJQANCHMSA-N 0.000 description 1
- MHNSOHQNBYCQOZ-HXUWFJFHSA-N tert-butyl n-[(2r)-1-[[4-(aminomethyl)phenyl]methoxyamino]-1-oxo-4-phenylbutan-2-yl]carbamate Chemical compound C([C@@H](NC(=O)OC(C)(C)C)C(=O)NOCC=1C=CC(CN)=CC=1)CC1=CC=CC=C1 MHNSOHQNBYCQOZ-HXUWFJFHSA-N 0.000 description 1
- SVPHVUGHAFJVRW-LJQANCHMSA-N tert-butyl n-[(2r)-1-[[4-(aminomethyl)phenyl]methoxyamino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]carbamate Chemical compound C([C@@H](NC(=O)OC(C)(C)C)C(=O)NOCC=1C=CC(CN)=CC=1)C1=CC=C(O)C=C1 SVPHVUGHAFJVRW-LJQANCHMSA-N 0.000 description 1
- KFFDHFBTQPJGQX-HSZRJFAPSA-N tert-butyl n-[(2r)-1-[[4-(aminomethyl)phenyl]methoxyamino]-3-naphthalen-2-yl-1-oxopropan-2-yl]carbamate Chemical compound O=C([C@@H](CC=1C=C2C=CC=CC2=CC=1)NC(=O)OC(C)(C)C)NOCC1=CC=C(CN)C=C1 KFFDHFBTQPJGQX-HSZRJFAPSA-N 0.000 description 1
- MHNSOHQNBYCQOZ-FQEVSTJZSA-N tert-butyl n-[(2s)-1-[[4-(aminomethyl)phenyl]methoxyamino]-1-oxo-4-phenylbutan-2-yl]carbamate Chemical compound C([C@H](NC(=O)OC(C)(C)C)C(=O)NOCC=1C=CC(CN)=CC=1)CC1=CC=CC=C1 MHNSOHQNBYCQOZ-FQEVSTJZSA-N 0.000 description 1
- DRDVJQOGFWAVLH-UHFFFAOYSA-N tert-butyl n-hydroxycarbamate Chemical compound CC(C)(C)OC(=O)NO DRDVJQOGFWAVLH-UHFFFAOYSA-N 0.000 description 1
- XBXCNNQPRYLIDE-UHFFFAOYSA-N tert-butylcarbamic acid Chemical compound CC(C)(C)NC(O)=O XBXCNNQPRYLIDE-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 210000001550 testis Anatomy 0.000 description 1
- MHXBHWLGRWOABW-UHFFFAOYSA-N tetradecyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCCCCCCCCCCCCC MHXBHWLGRWOABW-UHFFFAOYSA-N 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 125000000464 thioxo group Chemical group S=* 0.000 description 1
- UIERETOOQGIECD-ONEGZZNKSA-N tiglic acid Chemical compound C\C=C(/C)C(O)=O UIERETOOQGIECD-ONEGZZNKSA-N 0.000 description 1
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 125000006000 trichloroethyl group Chemical group 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- KAKQVSNHTBLJCH-UHFFFAOYSA-N trifluoromethanesulfonimidic acid Chemical compound NS(=O)(=O)C(F)(F)F KAKQVSNHTBLJCH-UHFFFAOYSA-N 0.000 description 1
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 1
- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- BZVJOYBTLHNRDW-UHFFFAOYSA-N triphenylmethanamine Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(N)C1=CC=CC=C1 BZVJOYBTLHNRDW-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
- 210000000689 upper leg Anatomy 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-M valerate Chemical compound CCCCC([O-])=O NQPDZGIKBAWPEJ-UHFFFAOYSA-M 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 201000009371 venous hemangioma Diseases 0.000 description 1
- LVLANIHJQRZTPY-UHFFFAOYSA-N vinyl carbamate Chemical compound NC(=O)OC=C LVLANIHJQRZTPY-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/0497—Organic compounds conjugates with a carrier being an 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
- A61K49/085—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by the carrier conjugated 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/0404—Lipids, e.g. triglycerides; Polycationic carriers
- A61K51/0406—Amines, polyamines, e.g. spermine, spermidine, amino acids, (bis)guanidines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
- C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
- C07C259/06—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Radiology & Medical Imaging (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Pharmacology & Pharmacy (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US22394609P | 2009-07-08 | 2009-07-08 | |
| US61/223,946 | 2009-07-08 | ||
| PCT/US2010/001926 WO2011005322A2 (en) | 2009-07-08 | 2010-07-08 | N-alkoxyamide conjugates as imaging agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2803520A1 CA2803520A1 (en) | 2011-01-13 |
| CA2803520C true CA2803520C (en) | 2019-10-22 |
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|---|---|---|---|
| CA2803520A Expired - Fee Related CA2803520C (en) | 2009-07-08 | 2010-07-08 | N-alkoxyamide conjugates as imaging agents |
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|---|---|
| US (2) | US8877157B2 (https=) |
| EP (1) | EP2451776B1 (https=) |
| JP (1) | JP5676600B2 (https=) |
| CN (1) | CN102781909B (https=) |
| AU (1) | AU2010271097B2 (https=) |
| CA (1) | CA2803520C (https=) |
| WO (1) | WO2011005322A2 (https=) |
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| TWI618544B (zh) | 2006-12-26 | 2018-03-21 | 藍瑟斯醫學影像公司 | 使心臟神經分布顯像之配位體 |
| US8361438B2 (en) | 2008-01-08 | 2013-01-29 | Lantheus Medical Imaging, Inc. | N-alkoxyamide conjugates as imaging agents |
| CA2803520C (en) | 2009-07-08 | 2019-10-22 | Lantheus Medical Imaging, Inc. | N-alkoxyamide conjugates as imaging agents |
| AU2011253052B2 (en) | 2010-05-11 | 2015-05-14 | Lantheus Medical Imaging, Inc. | Compositions, methods and systems for the synthesis and use of imaging agents |
| GB201102189D0 (en) | 2011-02-08 | 2011-03-23 | King S College London | Materials and methods relating to cardiovascular imaging |
| EP2753605B1 (en) * | 2011-09-09 | 2019-03-27 | Lantheus Medical Imaging, Inc. | Compositions, methods, and systems for the synthesis and use of imaging agents |
| US20150023873A1 (en) | 2011-11-11 | 2015-01-22 | Lantheus Medical Imaging, Inc. | Evaluation of presence of and vulnerability to atrial fibrillation and other indications using matrix metalloproteinase-based imaging |
| AU2013203000B9 (en) | 2012-08-10 | 2017-02-02 | Lantheus Medical Imaging, Inc. | Compositions, methods, and systems for the synthesis and use of imaging agents |
| TWI780082B (zh) | 2016-11-18 | 2022-10-11 | 日商安斯泰來製藥股份有限公司 | 新穎抗人類ＭＵＣ１抗體Ｆａｂ片段 |
| TWI795415B (zh) | 2017-07-07 | 2023-03-11 | 日商安斯泰來製藥股份有限公司 | 新穎的抗人類ＣＥＡＣＡＭ５抗體Ｆａｂ片段 |
| MX2020012351A (es) | 2018-05-17 | 2021-01-29 | Astellas Pharma Inc | Complejo que tiene fragmento fab de anticuerpo anti-muc1 de humano, enlazador peptido y/o ligando. |
| CA3115747A1 (en) | 2018-10-10 | 2020-04-16 | Astellas Pharma Inc. | Pharmaceutical composition containing tagged site-antihuman antibody fab fragment complex |
| JPWO2020145228A1 (ja) * | 2019-01-07 | 2021-11-11 | アステラス製薬株式会社 | 配位子及びＣＥＡＣＡＭ５抗体Ｆａｂフラグメントからなる複合体 |
| CN117486698B (zh) * | 2023-10-30 | 2025-08-19 | 国网安徽省电力有限公司电力科学研究院 | 烯醇硅醚类化合物制备c-c键偶联产物的方法与sf6的应用 |
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| JPS5122885A (en) | 1974-08-13 | 1976-02-23 | Sagami Chem Res | Ashiru ll aminosan oo chikanhidorokisamidono seizohoho |
| JPS5910322B2 (ja) | 1975-07-30 | 1984-03-08 | 三井東圧化学株式会社 | 殺草剤 |
| US4859777A (en) | 1981-07-01 | 1989-08-22 | Eastman Kodak Company | Terpyridine chelating agents |
| US4957939A (en) | 1981-07-24 | 1990-09-18 | Schering Aktiengesellschaft | Sterile pharmaceutical compositions of gadolinium chelates useful enhancing NMR imaging |
| EP0247156B1 (en) | 1985-11-18 | 1993-06-23 | Access Pharmaceuticals Inc. | Polychelating agents for image and spectral enhancement (and spectral shift) |
| EP0233607B1 (en) | 1986-02-18 | 1991-03-13 | E.R. Squibb & Sons, Inc. | [(2,2,2-Trichloroethoxy) methoxy]amine |
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-
2010
- 2010-07-08 CA CA2803520A patent/CA2803520C/en not_active Expired - Fee Related
- 2010-07-08 WO PCT/US2010/001926 patent/WO2011005322A2/en not_active Ceased
- 2010-07-08 US US13/382,689 patent/US8877157B2/en active Active
- 2010-07-08 JP JP2012519544A patent/JP5676600B2/ja not_active Expired - Fee Related
- 2010-07-08 EP EP10797455.2A patent/EP2451776B1/en active Active
- 2010-07-08 CN CN201080040596.8A patent/CN102781909B/zh not_active Expired - Fee Related
- 2010-07-08 AU AU2010271097A patent/AU2010271097B2/en not_active Ceased
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2014
- 2014-09-22 US US14/492,896 patent/US9393329B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| EP2451776A4 (en) | 2015-04-15 |
| WO2011005322A2 (en) | 2011-01-13 |
| AU2010271097B2 (en) | 2015-12-10 |
| EP2451776A2 (en) | 2012-05-16 |
| WO2011005322A3 (en) | 2011-04-21 |
| US20120328514A1 (en) | 2012-12-27 |
| JP5676600B2 (ja) | 2015-02-25 |
| US20150078997A1 (en) | 2015-03-19 |
| AU2010271097A1 (en) | 2012-03-01 |
| EP2451776B1 (en) | 2019-09-18 |
| JP2012532868A (ja) | 2012-12-20 |
| HK1178511A1 (en) | 2013-09-13 |
| CN102781909A (zh) | 2012-11-14 |
| US8877157B2 (en) | 2014-11-04 |
| CN102781909B (zh) | 2015-06-17 |
| US9393329B2 (en) | 2016-07-19 |
| CA2803520A1 (en) | 2011-01-13 |
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