ES2550604T3 - Sales ventajosas de péptidos de receptores opioides mu - Google Patents
Sales ventajosas de péptidos de receptores opioides mu Download PDFInfo
- Publication number
- ES2550604T3 ES2550604T3 ES14189232.3T ES14189232T ES2550604T3 ES 2550604 T3 ES2550604 T3 ES 2550604T3 ES 14189232 T ES14189232 T ES 14189232T ES 2550604 T3 ES2550604 T3 ES 2550604T3
- Authority
- ES
- Spain
- Prior art keywords
- salt
- salts
- peptide
- endotherm
- maleate
- 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.)
- Active
Links
- 150000003839 salts Chemical class 0.000 title abstract description 57
- 108090000765 processed proteins & peptides Proteins 0.000 title abstract description 23
- 102000004196 processed proteins & peptides Human genes 0.000 title description 3
- 102000003840 Opioid Receptors Human genes 0.000 title 1
- 108090000137 Opioid Receptors Proteins 0.000 title 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical group CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract description 3
- 241000282693 Cercopithecidae Species 0.000 description 15
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 15
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 14
- 238000000113 differential scanning calorimetry Methods 0.000 description 13
- 239000012535 impurity Substances 0.000 description 13
- 230000004580 weight loss Effects 0.000 description 13
- 239000012458 free base Substances 0.000 description 12
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 238000002411 thermogravimetry Methods 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 229940009098 aspartate Drugs 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 230000004927 fusion Effects 0.000 description 8
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 229940049920 malate Drugs 0.000 description 5
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 5
- 229940095064 tartrate Drugs 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 239000012062 aqueous buffer Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 230000000007 visual effect Effects 0.000 description 4
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 150000002688 maleic acid derivatives Chemical class 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
- 239000010452 phosphate Substances 0.000 description 3
- 238000012216 screening Methods 0.000 description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 3
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 2
- 206010012735 Diarrhoea Diseases 0.000 description 2
- -1 Dionex DX-600 ion Chemical class 0.000 description 2
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
- 208000018522 Gastrointestinal disease Diseases 0.000 description 2
- QIAFMBKCNZACKA-UHFFFAOYSA-N N-benzoylglycine Chemical compound OC(=O)CNC(=O)C1=CC=CC=C1 QIAFMBKCNZACKA-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical group [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 230000036592 analgesia Effects 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 206010013663 drug dependence Diseases 0.000 description 2
- 229940050410 gluconate Drugs 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 230000035800 maturation Effects 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 208000011117 substance-related disease Diseases 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 238000001757 thermogravimetry curve Methods 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- 239000003039 volatile agent Substances 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- IVQQMDVEFNHDQA-UHFFFAOYSA-N C(CCC(=O)O)(=O)O.S(=O)(=O)(O)O.C(CCC(=O)O)(=O)O Chemical compound C(CCC(=O)O)(=O)O.S(=O)(=O)(O)O.C(CCC(=O)O)(=O)O IVQQMDVEFNHDQA-UHFFFAOYSA-N 0.000 description 1
- 206010008631 Cholera Diseases 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- BYMMIQCVDHHYGG-UHFFFAOYSA-N Cl.OP(O)(O)=O Chemical compound Cl.OP(O)(O)=O BYMMIQCVDHHYGG-UHFFFAOYSA-N 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- 238000001157 Fourier transform infrared spectrum Methods 0.000 description 1
- 206010064147 Gastrointestinal inflammation Diseases 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000005102 attenuated total reflection Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 235000011167 hydrochloric acid Nutrition 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 229940001447 lactate Drugs 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical class CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 238000000386 microscopy Methods 0.000 description 1
- 238000011275 oncology therapy Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000000399 optical microscopy Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000634 powder X-ray diffraction Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 108020001612 μ-opioid receptors Proteins 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/10—Tetrapeptides
- C07K5/1002—Tetrapeptides with the first amino acid being neutral
- C07K5/1016—Tetrapeptides with the first amino acid being neutral and aromatic or cycloaliphatic
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/36—Opioid-abuse
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/10—Tetrapeptides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Addiction (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Rheumatology (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicinal Preparation (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US761707P | 2007-12-13 | 2007-12-13 | |
| US7617P | 2007-12-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2550604T3 true ES2550604T3 (es) | 2015-11-11 |
Family
ID=40755912
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES14189232.3T Active ES2550604T3 (es) | 2007-12-13 | 2008-12-15 | Sales ventajosas de péptidos de receptores opioides mu |
Country Status (7)
| Country | Link |
|---|---|
| US (6) | US20110190214A1 (https=) |
| EP (2) | EP2826786B1 (https=) |
| JP (1) | JP5647002B2 (https=) |
| AU (1) | AU2008334941B2 (https=) |
| CA (2) | CA2984218C (https=) |
| ES (1) | ES2550604T3 (https=) |
| WO (1) | WO2009076672A1 (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20110065648A1 (en) * | 2009-09-15 | 2011-03-17 | Maione Theodore E | Advantageous mu-opiate receptor peptide compounds |
| WO2011146922A2 (en) * | 2010-05-21 | 2011-11-24 | Cytogel Pharma, Llc | Materials and methods for treatment of inflammation |
| WO2013173730A2 (en) * | 2012-05-18 | 2013-11-21 | Cytogel Pharma, Llc. | Novel therapeutic uses of mu-opiate receptor peptides |
| CN110769843A (zh) * | 2017-06-12 | 2020-02-07 | 内布拉斯加大学董事会 | C5a受体激动剂肽的盐酸盐 |
| US10975121B2 (en) | 2017-06-24 | 2021-04-13 | Cytogel Pharma, Llc | Analgesic mu-opioid receptor binding peptide pharmaceutical formulations and uses thereof |
| JP2021503481A (ja) | 2017-11-17 | 2021-02-12 | サイトジェル ファーマ リミテッド ライアビリティ カンパニー | μオピオイド受容体のポリマーアゴニスト |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6235496B1 (en) * | 1993-03-08 | 2001-05-22 | Advanced Research & Technology Institute | Nucleic acid encoding mammalian mu opioid receptor |
| US5942492A (en) * | 1996-11-12 | 1999-08-24 | Angstrom Pharmaceuticals, Inc. | Cyclic peptides that bind to urokinase-type plasminogen activator receptor |
| US5885958A (en) * | 1997-03-25 | 1999-03-23 | Administrators Of The Tulane Educational Fund | Mu-opiate receptor peptides |
| JPH10330398A (ja) * | 1997-05-28 | 1998-12-15 | Asahi Glass Co Ltd | 新規環状ペプチド |
| SE9800865D0 (sv) * | 1998-03-16 | 1998-03-16 | Astra Ab | New Process |
| JPWO2002102833A1 (ja) * | 2001-06-15 | 2004-09-30 | 千寿製薬株式会社 | 新規エンドモルフィン誘導体 |
| EP1427438A2 (en) | 2001-09-03 | 2004-06-16 | The University of Bristol | Inflammation modulatory compound comprising an endomorphin |
| CN100436449C (zh) * | 2001-11-29 | 2008-11-26 | 先灵公司 | 作为ccr5-拮抗剂用于治疗aids和相关的hiv感染的药用盐的制备 |
-
2008
- 2008-12-15 ES ES14189232.3T patent/ES2550604T3/es active Active
- 2008-12-15 EP EP14189232.3A patent/EP2826786B1/en active Active
- 2008-12-15 CA CA2984218A patent/CA2984218C/en not_active Expired - Fee Related
- 2008-12-15 JP JP2010538227A patent/JP5647002B2/ja not_active Expired - Fee Related
- 2008-12-15 EP EP08858817.3A patent/EP2229400B1/en not_active Not-in-force
- 2008-12-15 CA CA2707733A patent/CA2707733C/en not_active Expired - Fee Related
- 2008-12-15 US US12/744,859 patent/US20110190214A1/en not_active Abandoned
- 2008-12-15 AU AU2008334941A patent/AU2008334941B2/en not_active Ceased
- 2008-12-15 WO PCT/US2008/086838 patent/WO2009076672A1/en not_active Ceased
-
2013
- 2013-10-17 US US14/056,496 patent/US8940704B2/en active Active
-
2014
- 2014-12-15 US US14/570,432 patent/US20150152137A1/en not_active Abandoned
-
2018
- 2018-06-22 US US16/016,165 patent/US20180291060A1/en not_active Abandoned
-
2020
- 2020-07-15 US US16/929,994 patent/US20200339628A1/en not_active Abandoned
-
2021
- 2021-12-17 US US17/554,421 patent/US20220324908A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| JP5647002B2 (ja) | 2014-12-24 |
| HK1206363A1 (en) | 2016-01-08 |
| EP2229400A1 (en) | 2010-09-22 |
| EP2229400B1 (en) | 2014-11-19 |
| JP2011508727A (ja) | 2011-03-17 |
| CA2984218C (en) | 2019-12-31 |
| US20180291060A1 (en) | 2018-10-11 |
| EP2229400A4 (en) | 2012-01-04 |
| US8940704B2 (en) | 2015-01-27 |
| US20150152137A1 (en) | 2015-06-04 |
| AU2008334941A1 (en) | 2009-06-18 |
| US20140142050A1 (en) | 2014-05-22 |
| CA2984218A1 (en) | 2009-06-18 |
| EP2826786B1 (en) | 2015-09-23 |
| CA2707733A1 (en) | 2009-06-18 |
| EP2826786A1 (en) | 2015-01-21 |
| US20110190214A1 (en) | 2011-08-04 |
| WO2009076672A1 (en) | 2009-06-18 |
| AU2008334941B2 (en) | 2013-02-14 |
| CA2707733C (en) | 2018-01-02 |
| US20220324908A1 (en) | 2022-10-13 |
| US20200339628A1 (en) | 2020-10-29 |
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