DK2980098T3 - (sukkerkæde)-polypeptidkompleks - Google Patents
(sukkerkæde)-polypeptidkompleks Download PDFInfo
- Publication number
- DK2980098T3 DK2980098T3 DK14778631.3T DK14778631T DK2980098T3 DK 2980098 T3 DK2980098 T3 DK 2980098T3 DK 14778631 T DK14778631 T DK 14778631T DK 2980098 T3 DK2980098 T3 DK 2980098T3
- Authority
- DK
- Denmark
- Prior art keywords
- sugar chain
- amino acid
- polypeptide
- ala
- residue
- Prior art date
Links
- 235000000346 sugar Nutrition 0.000 title claims description 448
- 229920001184 polypeptide Polymers 0.000 claims description 334
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 280
- 230000015572 biosynthetic process Effects 0.000 claims description 224
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 198
- 239000000017 hydrogel Substances 0.000 claims description 123
- 125000000539 amino acid group Chemical group 0.000 claims description 109
- 229940024606 amino acid Drugs 0.000 claims description 63
- 235000001014 amino acid Nutrition 0.000 claims description 63
- 150000001413 amino acids Chemical class 0.000 claims description 59
- 230000007935 neutral effect Effects 0.000 claims description 35
- 125000003275 alpha amino acid group Chemical group 0.000 claims description 30
- 210000004899 c-terminal region Anatomy 0.000 claims description 30
- DBTMGCOVALSLOR-UHFFFAOYSA-N 32-alpha-galactosyl-3-alpha-galactosyl-galactose Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(OC2C(C(CO)OC(O)C2O)O)OC(CO)C1O DBTMGCOVALSLOR-UHFFFAOYSA-N 0.000 claims description 23
- RXVWSYJTUUKTEA-UHFFFAOYSA-N D-maltotriose Natural products OC1C(O)C(OC(C(O)CO)C(O)C(O)C=O)OC(CO)C1OC1C(O)C(O)C(O)C(CO)O1 RXVWSYJTUUKTEA-UHFFFAOYSA-N 0.000 claims description 23
- FYGDTMLNYKFZSV-UHFFFAOYSA-N mannotriose Natural products OC1C(O)C(O)C(CO)OC1OC1C(CO)OC(OC2C(OC(O)C(O)C2O)CO)C(O)C1O FYGDTMLNYKFZSV-UHFFFAOYSA-N 0.000 claims description 23
- 238000013270 controlled release Methods 0.000 claims description 22
- 125000003295 alanine group Chemical group N[C@@H](C)C(=O)* 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 21
- FYGDTMLNYKFZSV-BYLHFPJWSA-N β-1,4-galactotrioside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@H](CO)O[C@@H](O[C@@H]2[C@@H](O[C@@H](O)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O FYGDTMLNYKFZSV-BYLHFPJWSA-N 0.000 claims description 18
- 239000011159 matrix material Substances 0.000 claims description 17
- 239000007864 aqueous solution Substances 0.000 claims description 16
- 229920000858 Cyclodextrin Polymers 0.000 claims description 15
- 230000002439 hemostatic effect Effects 0.000 claims description 13
- BNABBHGYYMZMOA-AHIHXIOASA-N alpha-maltoheptaose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)O[C@H](O[C@@H]2[C@H](O[C@H](O[C@@H]3[C@H](O[C@H](O[C@@H]4[C@H](O[C@H](O[C@@H]5[C@H](O[C@H](O[C@@H]6[C@H](O[C@H](O)[C@H](O)[C@H]6O)CO)[C@H](O)[C@H]5O)CO)[C@H](O)[C@H]4O)CO)[C@H](O)[C@H]3O)CO)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O BNABBHGYYMZMOA-AHIHXIOASA-N 0.000 claims description 8
- 239000001116 FEMA 4028 Substances 0.000 claims description 7
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 claims description 7
- 235000011175 beta-cyclodextrine Nutrition 0.000 claims description 7
- 229960004853 betadex Drugs 0.000 claims description 7
- GDSRMADSINPKSL-HSEONFRVSA-N gamma-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO GDSRMADSINPKSL-HSEONFRVSA-N 0.000 claims description 6
- 229940080345 gamma-cyclodextrin Drugs 0.000 claims description 6
- 230000003252 repetitive effect Effects 0.000 claims description 6
- 125000000637 arginyl group Chemical group N[C@@H](CCCNC(N)=N)C(=O)* 0.000 claims description 4
- 125000000613 asparagine group Chemical group N[C@@H](CC(N)=O)C(=O)* 0.000 claims description 4
- CKLJMWTZIZZHCS-REOHCLBHSA-L aspartate group Chemical group N[C@@H](CC(=O)[O-])C(=O)[O-] CKLJMWTZIZZHCS-REOHCLBHSA-L 0.000 claims description 4
- 125000000151 cysteine group Chemical group N[C@@H](CS)C(=O)* 0.000 claims description 4
- WHUUTDBJXJRKMK-VKHMYHEASA-L glutamate group Chemical group N[C@@H](CCC(=O)[O-])C(=O)[O-] WHUUTDBJXJRKMK-VKHMYHEASA-L 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- COLNVLDHVKWLRT-QMMMGPOBSA-N phenylalanine group Chemical group N[C@@H](CC1=CC=CC=C1)C(=O)O COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims description 4
- 238000001338 self-assembly Methods 0.000 claims description 4
- 125000000341 threoninyl group Chemical group [H]OC([H])(C([H])([H])[H])C([H])(N([H])[H])C(*)=O 0.000 claims description 4
- OVRNDRQMDRJTHS-UHFFFAOYSA-N N-acelyl-D-glucosamine Natural products CC(=O)NC1C(O)OC(CO)C(O)C1O OVRNDRQMDRJTHS-UHFFFAOYSA-N 0.000 claims description 3
- MBLBDJOUHNCFQT-LXGUWJNJSA-N N-acetylglucosamine Natural products CC(=O)N[C@@H](C=O)[C@@H](O)[C@H](O)[C@H](O)CO MBLBDJOUHNCFQT-LXGUWJNJSA-N 0.000 claims description 3
- 125000001360 methionine group Chemical group N[C@@H](CCSC)C(=O)* 0.000 claims description 3
- 125000000404 glutamine group Chemical group N[C@@H](CCC(N)=O)C(=O)* 0.000 claims description 2
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 claims description 2
- 125000000487 histidyl group Chemical group [H]N([H])C(C(=O)O*)C([H])([H])C1=C([H])N([H])C([H])=N1 0.000 claims description 2
- 125000000741 isoleucyl group Chemical group [H]N([H])C(C(C([H])([H])[H])C([H])([H])C([H])([H])[H])C(=O)O* 0.000 claims description 2
- 125000001909 leucine group Chemical group [H]N(*)C(C(*)=O)C([H])([H])C(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 claims description 2
- 125000001500 prolyl group Chemical group [H]N1C([H])(C(=O)[*])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000000430 tryptophan group Chemical group [H]N([H])C(C(=O)O*)C([H])([H])C1=C([H])N([H])C2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 2
- 125000001493 tyrosinyl group Chemical group [H]OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 claims description 2
- 125000002987 valine group Chemical group [H]N([H])C([H])(C(*)=O)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- FWMNVWWHGCHHJJ-SKKKGAJSSA-N 4-amino-1-[(2r)-6-amino-2-[[(2r)-2-[[(2r)-2-[[(2r)-2-amino-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoyl]amino]hexanoyl]piperidine-4-carboxylic acid Chemical compound C([C@H](C(=O)N[C@H](CC(C)C)C(=O)N[C@H](CCCCN)C(=O)N1CCC(N)(CC1)C(O)=O)NC(=O)[C@H](N)CC=1C=CC=CC=1)C1=CC=CC=C1 FWMNVWWHGCHHJJ-SKKKGAJSSA-N 0.000 claims 1
- OVRNDRQMDRJTHS-RTRLPJTCSA-N N-acetyl-D-glucosamine Chemical compound CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O OVRNDRQMDRJTHS-RTRLPJTCSA-N 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 382
- 238000003786 synthesis reaction Methods 0.000 description 219
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 212
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- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 56
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- 238000005406 washing Methods 0.000 description 56
- 238000006243 chemical reaction Methods 0.000 description 54
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 52
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 51
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- 125000003277 amino group Chemical group 0.000 description 40
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 39
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 36
- 239000008363 phosphate buffer Substances 0.000 description 36
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 34
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 33
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Claims (17)
- (SUKKE RKÆDE)-POLYPEPTIDKOMPLEKS1. Sukkerkædepolypeptidkompleks, hvor polypeptidet er et polypeptid, der omfatter en aminosyresekvens, der består af 8 - 34 aminosyrerester, hvori polære og ikke-polære aminosyrerester er anbragt skiftevis, og én eller flere sukkerkæder er bundet til polypeptidet, kendetegnet ved, at det totale antal sukkerrester, der er til stede i den ene eller flere sukkerkæder, der er bundet til polypeptidet, er 5 eller flere.
- 2. Sukkerkædepolypeptidkompleks ifølge krav 1, kendetegnet ved, at sukkerkædepolypeptidkomplekset kan danne en hydrogel, der omfatter en β-pladestruktur ved selvsamling i en vandig opløsning med et omtrent neutralt pH.
- 3. Sukkerkædepolypeptidkompleks ifølge krav 1, kendetegnet ved, at hver af aminosyreresterne er en aminosyrerest, der er valgt fra gruppen bestående af en aspartatrest, en glutamatrest, en argininrest, en lysinrest, en histidinrest, en tyrosinrest, en serinrest, en threoninrest, en asparaginrest, en glutaminrest og en cysteinrest.
- 4. Sukkerkædepolypeptidkompleks ifølge krav 1 eller 3, kendetegnet ved, at hver af de ikke-polære aminosyrerester er en aminosyrerest, der er valgt fra gruppen bestående af en alaninrest, en valinrest, en leucinrest, en isoleucinrest, en methioninrest, en phenylalaninrest, en tryptophanrest, en prolinrest og en glycinrest.
- 5. Sukkerkædepolypeptidkompleks ifølge krav 4, kendetegnet ved, at hver af de polære aminosyrerester er en aminosyrerest, der er valgt fra gruppen bestående af en aspartatrest, en glutamatrest, en argininrest og en threoninrest, og hver af de ikke-polære aminosyrer er en alaninrest.
- 6. Sukkerkædepolypeptidkompleks ifølge krav 1, kendetegnet ved, at aminosyresekvensen er en repetitiv sekvens "RADA" eller en repetitiv sekvens "RATARAEA".
- 7. Sukkerkædepolypeptidkompleks ifølge krav 6, kendetegnet ved, at aminosyresekvensen er en aminosyresekvens valgt fra gruppen bestående af RADARADARADARADA (SEQ ID NO: 1), RADARAD ARAD ARAD ARADA (SEQ ID NO: 2), og RATARAEARATARAEA (SEQ ID NO: 3).
- 8. Sukkerkædepolypeptidkompleks ifølge krav 1 kendetegnet ved, at antallet af sukkerkæder, der er bundet til polypeptidet, er 1, 2 eller 3.
- 9. Sukkerkædepolypeptidkompleks ifølge krav 1, kendetegnet ved, at sukkerkæder er bundet til hver aminosyre op til position x, der tælles fra aminosyreresten placeret ved polypeptidets N-terminal, og hver aminosyre op til position y, der tælles fra aminosyreresten placeret ved C-terminalen (hvor x og y er heltal, x > 0, y > 0, og x + y er det totale antal sukkerkæder, der er bundet til polypeptidet).
- 10. Sukkerkædepolypeptidkompleks ifølge krav 9, kendetegnet ved, at antallet af sukkerkæder, der er bundet til polypeptidet, er 1, 2 eller 3, hvor, når antallet af sukkerkæder, der er bundet til polypeptidet, er 1, den ene sukkerkæde er bundet til aminosyreresten placeret ved polypeptidets N-terminal eller aminosyreresten placeret ved C-terminalen, når antallet af sukkerkæder, der er bundet til polypeptidet, er 2, de to sukkerkæder er bundet til aminosyrerester valgt fra gruppen bestående af nedenstående (1) - (3): (1) den første og den anden aminosyrerest, der tælles fra aminosyreresten placeret ved polypeptidets N-terminal, (2) den første og den anden aminosyrerest, der tælles fra aminosyreresten placeret ved polypeptidets C-terminal, og (3) aminosyreresten placeret ved polypeptidets N-terminal og aminosyreresten placeret ved polypeptidets C-terminal, og når antallet af sukkerkæder, der er bundet til polypeptidet, er 3, de tre sukkerkæder er bundet til en hvilken som helst aminosyrerest valgt fra gruppen bestående af nedenstående (1)-(4): (1) den første, anden og tredje aminosyrerester, der tælles fra aminosyreresten placeret ved polypeptidets N-terminal, (2) den første, anden og tredje aminosyrerest, der tælles fra aminosyreresten placeret ved polypeptidets C-terminal, (3) den første og den anden aminosyrerest, der tælles fra aminosyreresten placeret ved polypeptidets N-terminal, såvel som aminosyreresten placeret ved polypeptidets C-terminal, og (4) aminosyreresten placeret ved polypeptidets N-terminal, såvel som aminosyrerester placeret ved position 1 og 2, der tælles fra polypeptidets C-terminal.
- 11. Sukkerkædepolypeptidkompleks ifølge krav 1, kendetegnet ved, at sukkerkæden er en sukkerkæde med en forgrening.
- 12. Sukkerkædepolypeptidkompleks ifølge krav 1, kendetegnet ved, at sukkerkæden er en sukkerkæde, der er valgt fra gruppen bestående af en disialosukkerkæde, en asialosukkerkæde, en diGlcNAc-sukkerkæde, en dimannosesukkerkæde, en GlcNAc-sukkerkæde, en maltotriosesukkerkæde, en maltosesukkerkæde, en maltotetraosesukkerkæde, en maltoheptaosesukkerkæde, β-cyclodextrin og γ-cyclodextrin.
- 13. Sammensætning for hydrogeldannelse, der omfatter et sukkerkædepolypeptidkompleks ifølge et hvilket som helst af kravene 1 til 12.
- 14. Sammensætning, der omfatter et sukkerkædepolypeptidkompleks ifølge et hvilket som helst af kravene 1 til 12, kendetegnet ved, at sammensætningen er i en hydrogeltilstand.
- 15. Hæmostatisk farmaceutisk sammensætning, der omfatter en sammensætning ifølge krav 13 eller 14.
- 16. Sammensætning til styret frigivelsesbærer, der omfatter en sammensætning ifølge krav 13 eller 14.
- 17. Sammensætning til dyrkningsmatrix, der omfatter en sammensætning ifølge krav 13 eller 14.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2013075493 | 2013-03-30 | ||
| PCT/JP2014/057927 WO2014162906A1 (ja) | 2013-03-30 | 2014-03-21 | 糖鎖－ポリペプチド複合体 |
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| Publication Number | Publication Date |
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| DK2980098T3 true DK2980098T3 (da) | 2019-01-28 |
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| DK14778631.3T DK2980098T3 (da) | 2013-03-30 | 2014-03-21 | (sukkerkæde)-polypeptidkompleks |
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| US (1) | US9981059B2 (da) |
| EP (1) | EP2980098B1 (da) |
| JP (1) | JP6460978B2 (da) |
| KR (1) | KR102186698B1 (da) |
| CN (1) | CN105408346B (da) |
| AU (1) | AU2014247614B2 (da) |
| BR (1) | BR112015024502A2 (da) |
| CA (1) | CA2908136C (da) |
| DK (1) | DK2980098T3 (da) |
| ES (1) | ES2703979T3 (da) |
| MY (1) | MY169123A (da) |
| PH (1) | PH12015502235B1 (da) |
| RU (1) | RU2664539C2 (da) |
| SG (1) | SG11201508032RA (da) |
| TW (1) | TWI639617B (da) |
| WO (1) | WO2014162906A1 (da) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| EP2987863A4 (en) * | 2013-04-19 | 2017-04-19 | Glytech, Inc. | Method for producing activated sugar-chain derivative, and activated sugar-chain derivative |
| JPWO2015145797A1 (ja) * | 2014-03-28 | 2017-04-13 | 大塚化学株式会社 | 止血用医薬組成物 |
| KR20180132093A (ko) | 2016-03-30 | 2018-12-11 | 컨바텍 테크놀러지스 인크 | 개조된 상처 드레싱 |
| CN107529533B (zh) * | 2017-09-07 | 2020-10-30 | 中国药科大学 | 一类可自组装成水凝胶的pH敏感多肽及其作为装载药物材料的应用 |
| CN108553683B (zh) * | 2018-05-21 | 2021-06-01 | 中国石油大学(华东) | 基于天然多糖/短肽的复合纳米止血材料及其制备方法 |
| JP7142286B2 (ja) * | 2018-07-13 | 2022-09-27 | 慶應義塾 | セレン含有アミノ酸を含む糖鎖－ポリペプチド複合体、および、その医薬用途 |
| KR102248381B1 (ko) | 2020-11-26 | 2021-05-06 | 박시형 | 벨 테스터기 |
| JP2023163607A (ja) * | 2022-04-28 | 2023-11-10 | 国立大学法人京都大学 | ポリサルコシン及びその用途 |
| CN116212098B (zh) * | 2023-03-14 | 2024-08-13 | 四川大学 | 一种酸性环境快速响应型多肽粘合剂的制备方法 |
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| US5670483A (en) * | 1992-12-28 | 1997-09-23 | Massachusetts Insititute Of Technology | Stable macroscopic membranes formed by self-assembly of amphiphilic peptides and uses therefor |
| EP2322533A1 (en) | 2001-06-19 | 2011-05-18 | Otsuka Chemical Co., Ltd. | Process for producing sugar chain asparagine derivative |
| US7943763B2 (en) | 2002-07-05 | 2011-05-17 | Otsuka Chemical Holdings Co., Ltd. | Process for preparing glycopeptides having asparagine-linked oligosaccharides, and the glycopeptides |
| TWI330641B (en) | 2002-12-24 | 2010-09-21 | Yasuhiro Kajihara | Sugar chain asparagine derivatives |
| JP4790271B2 (ja) | 2002-12-26 | 2011-10-12 | 康宏 梶原 | ３分岐型糖鎖アスパラギン誘導体、該糖鎖アスパラギン、該糖鎖およびそれらの製造方法 |
| US7955819B2 (en) | 2003-02-04 | 2011-06-07 | Otsuka Chemical Holdings Co., Ltd. | Process for producing sugar chain asparagine derivative |
| WO2005010053A1 (ja) | 2003-07-28 | 2005-02-03 | Otsuka Chemical Co., Ltd. | アミノ化複合型糖鎖誘導体及びその製造方法 |
| US8299032B2 (en) * | 2005-06-27 | 2012-10-30 | Menicon Co., Ltd. | Self-assembling peptide and gel produced from the same |
| TWI466897B (zh) | 2005-07-19 | 2015-01-01 | Glytech Inc | 癌細胞之檢測方法、糖鏈之構造解析方法，以及糖鏈衍生物 |
| JP2007217376A (ja) | 2006-02-17 | 2007-08-30 | Nagoya Institute Of Technology | 自己組織化ペプチド組成物 |
| US9415084B2 (en) | 2007-03-14 | 2016-08-16 | Arch Biosurgery, Inc. | Treatment of leaky or damaged tight junctions and enhancing extracellular matrix |
| EP4183425A1 (en) | 2008-10-06 | 2023-05-24 | 3-D Matrix Ltd. | Tissue plug |
| JP2012082180A (ja) * | 2010-10-14 | 2012-04-26 | Nagoya Univ | 骨再生用自己組織化ペプチドハイドロゲル |
| JP5845250B2 (ja) | 2011-04-27 | 2016-01-20 | 株式会社メニコン | 人工硝子体材料 |
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- 2014-03-21 CA CA2908136A patent/CA2908136C/en active Active
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- 2014-03-21 JP JP2015510007A patent/JP6460978B2/ja active Active
- 2014-03-21 SG SG11201508032RA patent/SG11201508032RA/en unknown
- 2014-03-21 CN CN201480019280.9A patent/CN105408346B/zh not_active Expired - Fee Related
- 2014-03-21 WO PCT/JP2014/057927 patent/WO2014162906A1/ja not_active Ceased
- 2014-03-21 DK DK14778631.3T patent/DK2980098T3/da active
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Also Published As
| Publication number | Publication date |
|---|---|
| ES2703979T3 (es) | 2019-03-13 |
| JP6460978B2 (ja) | 2019-01-30 |
| EP2980098A1 (en) | 2016-02-03 |
| RU2664539C2 (ru) | 2018-08-20 |
| CN105408346B (zh) | 2019-05-03 |
| SG11201508032RA (en) | 2015-10-29 |
| MY169123A (en) | 2019-02-18 |
| CN105408346A (zh) | 2016-03-16 |
| KR102186698B1 (ko) | 2020-12-07 |
| US20160129150A1 (en) | 2016-05-12 |
| TWI639617B (zh) | 2018-11-01 |
| RU2015146739A (ru) | 2017-05-05 |
| EP2980098B1 (en) | 2018-10-03 |
| TW201533061A (zh) | 2015-09-01 |
| PH12015502235B1 (en) | 2019-08-30 |
| PH12015502235A1 (en) | 2016-02-01 |
| JPWO2014162906A1 (ja) | 2017-02-16 |
| KR20160002835A (ko) | 2016-01-08 |
| US9981059B2 (en) | 2018-05-29 |
| CA2908136A1 (en) | 2014-10-09 |
| AU2014247614A1 (en) | 2015-09-24 |
| CA2908136C (en) | 2021-06-29 |
| WO2014162906A1 (ja) | 2014-10-09 |
| BR112015024502A2 (pt) | 2017-07-18 |
| EP2980098A4 (en) | 2016-11-09 |
| AU2014247614B2 (en) | 2017-09-21 |
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