JP6360895B2 - 多価シアル酸誘導体 - Google Patents
多価シアル酸誘導体 Download PDFInfo
- Publication number
- JP6360895B2 JP6360895B2 JP2016537292A JP2016537292A JP6360895B2 JP 6360895 B2 JP6360895 B2 JP 6360895B2 JP 2016537292 A JP2016537292 A JP 2016537292A JP 2016537292 A JP2016537292 A JP 2016537292A JP 6360895 B2 JP6360895 B2 JP 6360895B2
- Authority
- JP
- Japan
- Prior art keywords
- sialic acid
- acid derivative
- hadv
- formula
- galacto
- 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.)
- Expired - Fee Related
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- SQVRNKJHWKZAKO-OQPLDHBCSA-N sialic acid Chemical class CC(=O)N[C@@H]1[C@@H](O)C[C@@](O)(C(O)=O)OC1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-OQPLDHBCSA-N 0.000 title claims description 101
- 239000000203 mixture Substances 0.000 claims description 57
- 239000008194 pharmaceutical composition Substances 0.000 claims description 55
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 51
- 210000004027 cell Anatomy 0.000 claims description 50
- 150000001875 compounds Chemical class 0.000 claims description 49
- 150000001412 amines Chemical class 0.000 claims description 44
- 239000002253 acid Substances 0.000 claims description 35
- 239000007983 Tris buffer Substances 0.000 claims description 34
- 208000015181 infectious disease Diseases 0.000 claims description 31
- 230000027455 binding Effects 0.000 claims description 30
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims description 25
- 241000700605 Viruses Species 0.000 claims description 23
- 206010001257 Adenoviral conjunctivitis Diseases 0.000 claims description 22
- 208000021373 epidemic keratoconjunctivitis Diseases 0.000 claims description 22
- 201000006476 shipyard eye Diseases 0.000 claims description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- 238000011282 treatment Methods 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- 208000001860 Eye Infections Diseases 0.000 claims description 11
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 230000008878 coupling Effects 0.000 claims description 10
- 238000010168 coupling process Methods 0.000 claims description 10
- 238000005859 coupling reaction Methods 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 8
- 230000002265 prevention Effects 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 239000000654 additive Substances 0.000 claims description 6
- 239000012453 solvate Substances 0.000 claims description 6
- 239000011780 sodium chloride Substances 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 238000002560 therapeutic procedure Methods 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 230000000996 additive effect Effects 0.000 claims description 3
- 239000000644 isotonic solution Substances 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 239000012458 free base Substances 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
- 238000005481 NMR spectroscopy Methods 0.000 description 34
- 238000007429 general method Methods 0.000 description 30
- SQVRNKJHWKZAKO-UHFFFAOYSA-N beta-N-Acetyl-D-neuraminic acid Natural products CC(=O)NC1C(O)CC(O)(C(O)=O)OC1C(O)C(O)CO SQVRNKJHWKZAKO-UHFFFAOYSA-N 0.000 description 28
- 238000000746 purification Methods 0.000 description 26
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 18
- 239000000835 fiber Substances 0.000 description 18
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 17
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- 210000002845 virion Anatomy 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 16
- 238000004440 column chromatography Methods 0.000 description 16
- 125000005629 sialic acid group Chemical group 0.000 description 16
- -1 sialic acid monosaccharides Chemical class 0.000 description 16
- 239000000460 chlorine Substances 0.000 description 15
- 238000003786 synthesis reaction Methods 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 14
- 150000004702 methyl esters Chemical class 0.000 description 14
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
- 241000701161 unidentified adenovirus Species 0.000 description 12
- 150000001540 azides Chemical class 0.000 description 11
- 238000005947 deacylation reaction Methods 0.000 description 11
- 238000006206 glycosylation reaction Methods 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 10
- 230000002441 reversible effect Effects 0.000 description 10
- VSFNBSDITATMOL-UHFFFAOYSA-N 2-azido-n,n-bis(2-azidoethyl)ethanamine Chemical compound [N-]=[N+]=NCCN(CCN=[N+]=[N-])CCN=[N+]=[N-] VSFNBSDITATMOL-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 150000001720 carbohydrates Chemical class 0.000 description 9
- 235000014633 carbohydrates Nutrition 0.000 description 9
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- 125000005647 linker group Chemical group 0.000 description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
- 238000007127 saponification reaction Methods 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- 238000003556 assay Methods 0.000 description 7
- 235000019439 ethyl acetate Nutrition 0.000 description 7
- 235000019253 formic acid Nutrition 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 238000002198 surface plasmon resonance spectroscopy Methods 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000000499 gel Substances 0.000 description 6
- ZHOBJWVNWMQMLF-UHFFFAOYSA-N n,n-bis(prop-2-ynyl)prop-2-yn-1-amine Chemical compound C#CCN(CC#C)CC#C ZHOBJWVNWMQMLF-UHFFFAOYSA-N 0.000 description 6
- 230000003389 potentiating effect Effects 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- 239000002808 molecular sieve Substances 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 239000003755 preservative agent Substances 0.000 description 5
- 238000000159 protein binding assay Methods 0.000 description 5
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 5
- 235000010378 sodium ascorbate Nutrition 0.000 description 5
- PPASLZSBLFJQEF-RKJRWTFHSA-M sodium ascorbate Substances [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RKJRWTFHSA-M 0.000 description 5
- 229960005055 sodium ascorbate Drugs 0.000 description 5
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 4
- NMMHHSLZJLPMEG-UHFFFAOYSA-N 2-(chloroamino)ethanesulfonic acid Chemical compound OS(=O)(=O)CCNCl NMMHHSLZJLPMEG-UHFFFAOYSA-N 0.000 description 4
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
- 230000000840 anti-viral effect Effects 0.000 description 4
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 229920001429 chelating resin Polymers 0.000 description 4
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 description 4
- 208000011323 eye infectious disease Diseases 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 239000003456 ion exchange resin Substances 0.000 description 4
- 229920003303 ion-exchange polymer Polymers 0.000 description 4
- 239000003589 local anesthetic agent Substances 0.000 description 4
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 4
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- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 4
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 4
- 108090000623 proteins and genes Proteins 0.000 description 4
- 102000004169 proteins and genes Human genes 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- QRUBYZBWAOOHSV-UHFFFAOYSA-M silver trifluoromethanesulfonate Chemical compound [Ag+].[O-]S(=O)(=O)C(F)(F)F QRUBYZBWAOOHSV-UHFFFAOYSA-M 0.000 description 4
- PWEBUXCTKOWPCW-UHFFFAOYSA-N squaric acid Chemical compound OC1=C(O)C(=O)C1=O PWEBUXCTKOWPCW-UHFFFAOYSA-N 0.000 description 4
- 229920001059 synthetic polymer Polymers 0.000 description 4
- FANCTJAFZSYTIS-IQUVVAJASA-N (1r,3s,5z)-5-[(2e)-2-[(1r,3as,7ar)-7a-methyl-1-[(2r)-4-(phenylsulfonimidoyl)butan-2-yl]-2,3,3a,5,6,7-hexahydro-1h-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol Chemical compound C([C@@H](C)[C@@H]1[C@]2(CCCC(/[C@@H]2CC1)=C\C=C\1C([C@@H](O)C[C@H](O)C/1)=C)C)CS(=N)(=O)C1=CC=CC=C1 FANCTJAFZSYTIS-IQUVVAJASA-N 0.000 description 3
- SHAHPWSYJFYMRX-GDLCADMTSA-N (2S)-2-(4-{[(1R,2S)-2-hydroxycyclopentyl]methyl}phenyl)propanoic acid Chemical compound C1=CC([C@@H](C(O)=O)C)=CC=C1C[C@@H]1[C@@H](O)CCC1 SHAHPWSYJFYMRX-GDLCADMTSA-N 0.000 description 3
- KAFZOLYKKCWUBI-HPMAGDRPSA-N (2s)-2-[[(2s)-2-[[(2s)-1-[(2s)-3-amino-2-[[(2s)-2-[[(2s)-2-(3-cyclohexylpropanoylamino)-4-methylpentanoyl]amino]-5-methylhexanoyl]amino]propanoyl]pyrrolidine-2-carbonyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]butanediamide Chemical compound N([C@@H](CC(C)C)C(=O)N[C@@H](CCC(C)C)C(=O)N[C@@H](CN)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@@H](CC(N)=O)C(N)=O)C(=O)CCC1CCCCC1 KAFZOLYKKCWUBI-HPMAGDRPSA-N 0.000 description 3
- VIMMECPCYZXUCI-MIMFYIINSA-N (4s,6r)-6-[(1e)-4,4-bis(4-fluorophenyl)-3-(1-methyltetrazol-5-yl)buta-1,3-dienyl]-4-hydroxyoxan-2-one Chemical compound CN1N=NN=C1C(\C=C\[C@@H]1OC(=O)C[C@@H](O)C1)=C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 VIMMECPCYZXUCI-MIMFYIINSA-N 0.000 description 3
- IGVKWAAPMVVTFX-BUHFOSPRSA-N (e)-octadec-5-en-7,9-diynoic acid Chemical compound CCCCCCCCC#CC#C\C=C\CCCC(O)=O IGVKWAAPMVVTFX-BUHFOSPRSA-N 0.000 description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/26—Acyclic or carbocyclic radicals, substituted by hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
- A61K31/7056—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing five-membered rings with nitrogen as a ring hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/08—Solutions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Organic Chemistry (AREA)
- Epidemiology (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Virology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Ophthalmology & Optometry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE1350991-4 | 2013-08-28 | ||
| SE1350991 | 2013-08-28 | ||
| PCT/EP2014/068252 WO2015028548A1 (en) | 2013-08-28 | 2014-08-28 | Multivalent sialic acid derivates |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016529269A JP2016529269A (ja) | 2016-09-23 |
| JP2016529269A5 JP2016529269A5 (enExample) | 2017-09-07 |
| JP6360895B2 true JP6360895B2 (ja) | 2018-07-18 |
Family
ID=51454687
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016537292A Expired - Fee Related JP6360895B2 (ja) | 2013-08-28 | 2014-08-28 | 多価シアル酸誘導体 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US10011628B2 (enExample) |
| EP (1) | EP3039029B1 (enExample) |
| JP (1) | JP6360895B2 (enExample) |
| KR (1) | KR20160073372A (enExample) |
| CN (1) | CN105722849B (enExample) |
| AU (1) | AU2014314212B2 (enExample) |
| CA (1) | CA2921634A1 (enExample) |
| ES (1) | ES2677219T3 (enExample) |
| IL (1) | IL244246B (enExample) |
| MX (1) | MX2016002578A (enExample) |
| PL (1) | PL3039029T3 (enExample) |
| TR (1) | TR201809630T4 (enExample) |
| WO (1) | WO2015028548A1 (enExample) |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE9904289D0 (sv) | 1999-11-26 | 1999-11-26 | Niklas Arnberg | Method and camposition for the treatment of adenovairal ocular infections |
| US20070020620A1 (en) * | 2005-07-14 | 2007-01-25 | Finn M G | Compositions and methods for coupling a plurality of compounds to a scaffold |
| US20080194801A1 (en) * | 2007-02-14 | 2008-08-14 | Swanson Basil I | Robust multidentate ligands for diagnosis and anti-viral drugs for influenza and related viruses |
| BR112012000381A2 (pt) | 2009-07-07 | 2016-03-29 | Adenovir Pharma Ab | novos compostos antivirais úteis para o tratamento ou prevenção de queratoconjuntivite epidêmica |
| KR101217685B1 (ko) | 2010-05-28 | 2013-01-02 | 서강대학교산학협력단 | 서로 다른 실릴기로 보호된 알킨 그룹을 갖는 삼중연결고리 화합물, 이의 제조방법 및 응용 |
| WO2011158068A1 (en) | 2010-06-18 | 2011-12-22 | Centre National De La Recherche Scientifique (Cnrs) | Non covalent molecular structure, device comprising the same and its use for detection of lectin |
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2014
- 2014-08-28 KR KR1020167007981A patent/KR20160073372A/ko not_active Ceased
- 2014-08-28 WO PCT/EP2014/068252 patent/WO2015028548A1/en not_active Ceased
- 2014-08-28 JP JP2016537292A patent/JP6360895B2/ja not_active Expired - Fee Related
- 2014-08-28 EP EP14758353.8A patent/EP3039029B1/en not_active Not-in-force
- 2014-08-28 MX MX2016002578A patent/MX2016002578A/es unknown
- 2014-08-28 CN CN201480047068.3A patent/CN105722849B/zh not_active Expired - Fee Related
- 2014-08-28 CA CA2921634A patent/CA2921634A1/en not_active Abandoned
- 2014-08-28 TR TR2018/09630T patent/TR201809630T4/tr unknown
- 2014-08-28 AU AU2014314212A patent/AU2014314212B2/en not_active Ceased
- 2014-08-28 US US14/914,988 patent/US10011628B2/en not_active Expired - Fee Related
- 2014-08-28 PL PL14758353T patent/PL3039029T3/pl unknown
- 2014-08-28 ES ES14758353.8T patent/ES2677219T3/es active Active
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2016
- 2016-02-23 IL IL244246A patent/IL244246B/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| IL244246B (en) | 2019-02-28 |
| CA2921634A1 (en) | 2015-03-05 |
| KR20160073372A (ko) | 2016-06-24 |
| EP3039029B1 (en) | 2018-04-11 |
| CN105722849B (zh) | 2019-01-29 |
| ES2677219T3 (es) | 2018-07-31 |
| IL244246A0 (en) | 2016-04-21 |
| CN105722849A (zh) | 2016-06-29 |
| WO2015028548A1 (en) | 2015-03-05 |
| US10011628B2 (en) | 2018-07-03 |
| EP3039029A1 (en) | 2016-07-06 |
| MX2016002578A (es) | 2016-09-08 |
| US20160207955A1 (en) | 2016-07-21 |
| AU2014314212A1 (en) | 2016-03-10 |
| AU2014314212B2 (en) | 2018-03-01 |
| PL3039029T3 (pl) | 2018-10-31 |
| JP2016529269A (ja) | 2016-09-23 |
| TR201809630T4 (tr) | 2018-07-23 |
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