CA2820387A1 - Radiotracer compositions - Google Patents
Radiotracer compositions Download PDFInfo
- Publication number
- CA2820387A1 CA2820387A1 CA2820387A CA2820387A CA2820387A1 CA 2820387 A1 CA2820387 A1 CA 2820387A1 CA 2820387 A CA2820387 A CA 2820387A CA 2820387 A CA2820387 A CA 2820387A CA 2820387 A1 CA2820387 A1 CA 2820387A1
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- CA
- Canada
- Prior art keywords
- composition
- formula
- btm
- peptide
- group
- 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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- 239000000203 mixture Substances 0.000 title claims abstract description 91
- 239000000700 radioactive tracer Substances 0.000 title abstract description 7
- 238000000034 method Methods 0.000 claims abstract description 42
- 239000012216 imaging agent Substances 0.000 claims abstract description 24
- 230000008685 targeting Effects 0.000 claims abstract description 21
- 239000012217 radiopharmaceutical Substances 0.000 claims abstract description 19
- 229940121896 radiopharmaceutical Drugs 0.000 claims abstract description 19
- 230000002799 radiopharmaceutical effect Effects 0.000 claims abstract description 19
- 238000003384 imaging method Methods 0.000 claims abstract description 18
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims abstract description 8
- 238000003745 diagnosis Methods 0.000 claims abstract description 4
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 44
- 150000001875 compounds Chemical class 0.000 claims description 28
- -1 -OH Chemical group 0.000 claims description 27
- 229920001223 polyethylene glycol Polymers 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 230000002285 radioactive effect Effects 0.000 claims description 18
- 239000002202 Polyethylene glycol Substances 0.000 claims description 17
- 150000001413 amino acids Chemical class 0.000 claims description 17
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 16
- 125000002344 aminooxy group Chemical group [H]N([H])O[*] 0.000 claims description 12
- 108090000790 Enzymes Proteins 0.000 claims description 11
- 102000004190 Enzymes Human genes 0.000 claims description 11
- 238000011282 treatment Methods 0.000 claims description 8
- 239000012634 fragment Substances 0.000 claims description 7
- 125000005647 linker group Chemical group 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 108020003175 receptors Proteins 0.000 claims description 7
- 102000005962 receptors Human genes 0.000 claims description 7
- 239000000758 substrate Substances 0.000 claims description 7
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- IYMAXBFPHPZYIK-BQBZGAKWSA-N Arg-Gly-Asp Chemical compound NC(N)=NCCC[C@H](N)C(=O)NCC(=O)N[C@@H](CC(O)=O)C(O)=O IYMAXBFPHPZYIK-BQBZGAKWSA-N 0.000 claims description 6
- 241001465754 Metazoa Species 0.000 claims description 6
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- 229940079593 drug Drugs 0.000 claims description 6
- 239000000556 agonist Substances 0.000 claims description 5
- 239000005557 antagonist Substances 0.000 claims description 5
- 108010072041 arginyl-glycyl-aspartic acid Proteins 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 238000000163 radioactive labelling Methods 0.000 claims description 5
- 230000000694 effects Effects 0.000 claims description 4
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 239000002532 enzyme inhibitor Substances 0.000 claims description 3
- 229940125532 enzyme inhibitor Drugs 0.000 claims description 3
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 2
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 2
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000000732 arylene group Chemical group 0.000 claims description 2
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 2
- 125000005549 heteroarylene group Chemical group 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 239000012535 impurity Substances 0.000 abstract description 22
- 238000001727 in vivo Methods 0.000 abstract description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- 239000000047 product Substances 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 19
- 150000001299 aldehydes Chemical class 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 238000000746 purification Methods 0.000 description 15
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
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- 238000002414 normal-phase solid-phase extraction Methods 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- 238000003786 synthesis reaction Methods 0.000 description 13
- 239000002243 precursor Substances 0.000 description 12
- 102000004196 processed proteins & peptides Human genes 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 11
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- 239000000126 substance Substances 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
- 230000000845 anti-microbial effect Effects 0.000 description 7
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 7
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- 241000894007 species Species 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 150000002576 ketones Chemical group 0.000 description 6
- 230000004060 metabolic process Effects 0.000 description 6
- 230000002829 reductive effect Effects 0.000 description 6
- DDFYFBUWEBINLX-UHFFFAOYSA-M tetramethylammonium bromide Chemical compound [Br-].C[N+](C)(C)C DDFYFBUWEBINLX-UHFFFAOYSA-M 0.000 description 6
- 229920000858 Cyclodextrin Polymers 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 150000001768 cations Chemical class 0.000 description 5
- KRHYYFGTRYWZRS-BJUDXGSMSA-M fluorine-18(1-) Chemical compound [18F-] KRHYYFGTRYWZRS-BJUDXGSMSA-M 0.000 description 5
- 239000008194 pharmaceutical composition Substances 0.000 description 5
- 108090000623 proteins and genes Proteins 0.000 description 5
- 229940124553 radioprotectant Drugs 0.000 description 5
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 4
- WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 description 4
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- OBMZMSLWNNWEJA-XNCRXQDQSA-N C1=CC=2C(C[C@@H]3NC(=O)[C@@H](NC(=O)[C@H](NC(=O)N(CC#CCN(CCCC[C@H](NC(=O)[C@@H](CC4=CC=CC=C4)NC3=O)C(=O)N)CC=C)NC(=O)[C@@H](N)C)CC3=CNC4=C3C=CC=C4)C)=CNC=2C=C1 Chemical compound C1=CC=2C(C[C@@H]3NC(=O)[C@@H](NC(=O)[C@H](NC(=O)N(CC#CCN(CCCC[C@H](NC(=O)[C@@H](CC4=CC=CC=C4)NC3=O)C(=O)N)CC=C)NC(=O)[C@@H](N)C)CC3=CNC4=C3C=CC=C4)C)=CNC=2C=C1 OBMZMSLWNNWEJA-XNCRXQDQSA-N 0.000 description 4
- CZGUSIXMZVURDU-JZXHSEFVSA-N Ile(5)-angiotensin II Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C([O-])=O)NC(=O)[C@@H](NC(=O)[C@H](CCCNC(N)=[NH2+])NC(=O)[C@@H]([NH3+])CC([O-])=O)C(C)C)C1=CC=C(O)C=C1 CZGUSIXMZVURDU-JZXHSEFVSA-N 0.000 description 4
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 4
- 101710176384 Peptide 1 Proteins 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical class CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- 230000021615 conjugation Effects 0.000 description 4
- 238000001514 detection method Methods 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
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- 244000005700 microbiome Species 0.000 description 4
- 239000003002 pH adjusting agent Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 125000006239 protecting group Chemical group 0.000 description 4
- 235000018102 proteins Nutrition 0.000 description 4
- 102000004169 proteins and genes Human genes 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- ZWDVQMVZZYIAHO-COJKEBBMSA-N 2-fluoranylbenzaldehyde Chemical compound [18F]C1=CC=CC=C1C=O ZWDVQMVZZYIAHO-COJKEBBMSA-N 0.000 description 3
- 102400000345 Angiotensin-2 Human genes 0.000 description 3
- 101800000733 Angiotensin-2 Proteins 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 102000011632 Caseins Human genes 0.000 description 3
- 108010076119 Caseins Proteins 0.000 description 3
- 108010067306 Fibronectins Proteins 0.000 description 3
- 102000016359 Fibronectins Human genes 0.000 description 3
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
- 101000629400 Homo sapiens Mesoderm-specific transcript homolog protein Proteins 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 102100026821 Mesoderm-specific transcript homolog protein Human genes 0.000 description 3
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical class C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 125000000539 amino acid group Chemical group 0.000 description 3
- 229950006323 angiotensin ii Drugs 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 150000003935 benzaldehydes Chemical class 0.000 description 3
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 3
- 150000003857 carboxamides Chemical class 0.000 description 3
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- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 description 2
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- 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
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- A61K51/04—Organic compounds
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Landscapes
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- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Optics & Photonics (AREA)
- Physics & Mathematics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US42139010P | 2010-12-09 | 2010-12-09 | |
| US61/421,390 | 2010-12-09 | ||
| PCT/EP2011/072352 WO2012076697A1 (en) | 2010-12-09 | 2011-12-09 | Radiotracer compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2820387A1 true CA2820387A1 (en) | 2012-06-14 |
Family
ID=45346469
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2820387A Abandoned CA2820387A1 (en) | 2010-12-09 | 2011-12-09 | Radiotracer compositions |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US9180213B2 (OSRAM) |
| EP (1) | EP2648767B1 (OSRAM) |
| JP (1) | JP6055417B2 (OSRAM) |
| KR (1) | KR20130124522A (OSRAM) |
| CN (2) | CN103338791A (OSRAM) |
| CA (1) | CA2820387A1 (OSRAM) |
| WO (1) | WO2012076697A1 (OSRAM) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB201202420D0 (en) * | 2012-02-13 | 2012-03-28 | Ge Healthcare Ltd | Radiotracer compositions |
| WO2013176522A1 (ko) * | 2012-05-24 | 2013-11-28 | 서강대학교산학협력단 | 카트리지를 이용한 방사성의약품 제조방법 |
| GB201221266D0 (en) * | 2012-11-27 | 2013-01-09 | Ge Healthcare Ltd | Aldehyde compositions |
| GB201314936D0 (en) | 2013-08-21 | 2013-10-02 | Ge Healthcare Ltd | Radiolabelling method |
| GB201322456D0 (en) | 2013-12-18 | 2014-02-05 | Ge Healthcare Ltd | Radiotracer compositions and methods |
| EP3226884B1 (en) * | 2014-12-04 | 2021-02-17 | GE Healthcare Limited | Method of removing acetaldehyde from radioactive pharmaceuticals |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0305704D0 (en) | 2003-03-13 | 2003-04-16 | Amersham Plc | Radiofluorination methods |
| US7659400B2 (en) * | 2003-07-31 | 2010-02-09 | Washington University | Radiolabelled benzamide analogues, their synthesis and use in diagnostic imaging |
| GB0420344D0 (en) | 2004-09-14 | 2004-10-13 | Amersham Plc | Diagnostic compounds |
| WO2007027385A2 (en) * | 2005-08-31 | 2007-03-08 | Immunomedics, Inc. | F-18 peptides for pre targeted positron emission tomography imaging |
| EP2567711A3 (en) * | 2007-02-07 | 2013-05-01 | Purdue Research Foundation | Positron emission tomography imaging method |
| WO2009002914A2 (en) | 2007-06-25 | 2008-12-31 | Interdigital Technology Corporation | Method and apparatus for supporting inter-frequency and inter-radio access technology handover |
| US8124725B2 (en) | 2007-12-19 | 2012-02-28 | General Electric Company | PDGF-Rβ binders |
| WO2010000409A2 (en) | 2008-07-03 | 2010-01-07 | Bayer Schering Pharma Aktiengesellschaft | Compounds and processes for production of radiopharmaceuticals |
| GB0905438D0 (en) * | 2009-03-30 | 2009-05-13 | Ge Healthcare Ltd | Radiolabelling reagents and methods |
| EP2322500A1 (en) * | 2009-11-11 | 2011-05-18 | Bayer Schering Pharma Aktiengesellschaft | Fluoro-labeled homo-glutamate derivatives and precursors thereof |
| BR112012011786A2 (pt) * | 2009-11-17 | 2019-09-24 | Bayer Pharma AG | "método para a produção de derivados de ácido glutâmico marcados por f-18" |
-
2011
- 2011-12-09 CN CN2011800590925A patent/CN103338791A/zh active Pending
- 2011-12-09 EP EP11794725.9A patent/EP2648767B1/en active Active
- 2011-12-09 WO PCT/EP2011/072352 patent/WO2012076697A1/en not_active Ceased
- 2011-12-09 JP JP2013542563A patent/JP6055417B2/ja active Active
- 2011-12-09 CA CA2820387A patent/CA2820387A1/en not_active Abandoned
- 2011-12-09 CN CN201711237827.4A patent/CN107753962A/zh active Pending
- 2011-12-09 KR KR1020137017594A patent/KR20130124522A/ko not_active Withdrawn
- 2011-12-09 US US13/992,800 patent/US9180213B2/en active Active
-
2015
- 2015-10-07 US US14/877,107 patent/US9987382B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CN103338791A (zh) | 2013-10-02 |
| EP2648767B1 (en) | 2023-03-15 |
| KR20130124522A (ko) | 2013-11-14 |
| US9180213B2 (en) | 2015-11-10 |
| JP6055417B2 (ja) | 2016-12-27 |
| US20130259804A1 (en) | 2013-10-03 |
| JP2014500268A (ja) | 2014-01-09 |
| WO2012076697A1 (en) | 2012-06-14 |
| US9987382B2 (en) | 2018-06-05 |
| EP2648767A1 (en) | 2013-10-16 |
| US20160022847A1 (en) | 2016-01-28 |
| CN107753962A (zh) | 2018-03-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20171211 |