RU2019109719A - Конъюгаты полимиксин-альгинатных олигомеров - Google Patents
Конъюгаты полимиксин-альгинатных олигомеров Download PDFInfo
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- RU2019109719A RU2019109719A RU2019109719A RU2019109719A RU2019109719A RU 2019109719 A RU2019109719 A RU 2019109719A RU 2019109719 A RU2019109719 A RU 2019109719A RU 2019109719 A RU2019109719 A RU 2019109719A RU 2019109719 A RU2019109719 A RU 2019109719A
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- RU
- Russia
- Prior art keywords
- polymyxin
- alginate oligomer
- conjugate
- antibiotic
- alginate
- Prior art date
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- 229940072056 alginate Drugs 0.000 title claims 55
- 229920000615 alginic acid Polymers 0.000 title claims 55
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 claims 25
- 235000010443 alginic acid Nutrition 0.000 claims 25
- 108010040201 Polymyxins Proteins 0.000 claims 19
- 230000003115 biocidal effect Effects 0.000 claims 16
- 238000000034 method Methods 0.000 claims 11
- 239000003242 anti bacterial agent Substances 0.000 claims 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 7
- -1 methylenedioxy group Chemical group 0.000 claims 6
- 229940024606 amino acid Drugs 0.000 claims 5
- 235000001014 amino acid Nutrition 0.000 claims 5
- 150000001413 amino acids Chemical class 0.000 claims 5
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- 208000035143 Bacterial infection Diseases 0.000 claims 4
- 208000022362 bacterial infectious disease Diseases 0.000 claims 4
- 239000000243 solution Substances 0.000 claims 4
- OGNSCSPNOLGXSM-UHFFFAOYSA-N (+/-)-DABA Natural products NCCC(N)C(O)=O OGNSCSPNOLGXSM-UHFFFAOYSA-N 0.000 claims 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 3
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 claims 3
- 125000003277 amino group Chemical group 0.000 claims 3
- 230000015572 biosynthetic process Effects 0.000 claims 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 3
- 239000011541 reaction mixture Substances 0.000 claims 3
- GVJXGCIPWAVXJP-UHFFFAOYSA-N 2,5-dioxo-1-oxoniopyrrolidine-3-sulfonate Chemical compound ON1C(=O)CC(S(O)(=O)=O)C1=O GVJXGCIPWAVXJP-UHFFFAOYSA-N 0.000 claims 2
- PMNLUUOXGOOLSP-UHFFFAOYSA-N 2-mercaptopropanoic acid Chemical compound CC(S)C(O)=O PMNLUUOXGOOLSP-UHFFFAOYSA-N 0.000 claims 2
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 claims 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims 2
- 241000894006 Bacteria Species 0.000 claims 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims 2
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims 2
- 150000007930 O-acyl isoureas Chemical class 0.000 claims 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 2
- 239000004473 Threonine Substances 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 238000006116 polymerization reaction Methods 0.000 claims 2
- 108700018363 polymyxin B(1) Proteins 0.000 claims 2
- WQVJHHACXVLGBL-GOVYWFKWSA-N polymyxin B1 Polymers N1C(=O)[C@H](CCN)NC(=O)[C@@H](NC(=O)[C@H](CCN)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCN)NC(=O)CCCC[C@H](C)CC)CCNC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCN)NC(=O)[C@H](CCN)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]1CC1=CC=CC=C1 WQVJHHACXVLGBL-GOVYWFKWSA-N 0.000 claims 2
- XDJYMJULXQKGMM-UHFFFAOYSA-N polymyxin E1 Natural products CCC(C)CCCCC(=O)NC(CCN)C(=O)NC(C(C)O)C(=O)NC(CCN)C(=O)NC1CCNC(=O)C(C(C)O)NC(=O)C(CCN)NC(=O)C(CCN)NC(=O)C(CC(C)C)NC(=O)C(CC(C)C)NC(=O)C(CCN)NC1=O XDJYMJULXQKGMM-UHFFFAOYSA-N 0.000 claims 2
- KNIWPHSUTGNZST-UHFFFAOYSA-N polymyxin E2 Natural products CC(C)CCCCC(=O)NC(CCN)C(=O)NC(C(C)O)C(=O)NC(CCN)C(=O)NC1CCNC(=O)C(C(C)O)NC(=O)C(CCN)NC(=O)C(CCN)NC(=O)C(CC(C)C)NC(=O)C(CC(C)C)NC(=O)C(CCN)NC1=O KNIWPHSUTGNZST-UHFFFAOYSA-N 0.000 claims 2
- 229960002898 threonine Drugs 0.000 claims 2
- GMKMEZVLHJARHF-UHFFFAOYSA-N (2R,6R)-form-2.6-Diaminoheptanedioic acid Natural products OC(=O)C(N)CCCC(N)C(O)=O GMKMEZVLHJARHF-UHFFFAOYSA-N 0.000 claims 1
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims 1
- NMDDZEVVQDPECF-LURJTMIESA-N (2s)-2,7-diaminoheptanoic acid Chemical compound NCCCCC[C@H](N)C(O)=O NMDDZEVVQDPECF-LURJTMIESA-N 0.000 claims 1
- VHDOAFBNVURINJ-QMMMGPOBSA-N (2s)-5-amino-2-(dimethylamino)-2-methylpentanoic acid Chemical compound CN(C)[C@](C)(C(O)=O)CCCN VHDOAFBNVURINJ-QMMMGPOBSA-N 0.000 claims 1
- LJRDOKAZOAKLDU-UDXJMMFXSA-N (2s,3s,4r,5r,6r)-5-amino-2-(aminomethyl)-6-[(2r,3s,4r,5s)-5-[(1r,2r,3s,5r,6s)-3,5-diamino-2-[(2s,3r,4r,5s,6r)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-hydroxycyclohexyl]oxy-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxyoxane-3,4-diol;sulfuric ac Chemical compound OS(O)(=O)=O.N[C@@H]1[C@@H](O)[C@H](O)[C@H](CN)O[C@@H]1O[C@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](N)C[C@@H](N)[C@@H]2O)O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)N)O[C@@H]1CO LJRDOKAZOAKLDU-UDXJMMFXSA-N 0.000 claims 1
- LKSDEJBJXXZASB-WCCKRBBISA-N 2,2-diaminobutanoic acid;(2s)-2,5-diaminopentanoic acid Chemical compound CCC(N)(N)C(O)=O.NCCC[C@H](N)C(O)=O LKSDEJBJXXZASB-WCCKRBBISA-N 0.000 claims 1
- ARGOSVDPSCPNGS-UHFFFAOYSA-N 2-(dimethylamino)propane-1-thiol Chemical compound SCC(C)N(C)C ARGOSVDPSCPNGS-UHFFFAOYSA-N 0.000 claims 1
- PECYZEOJVXMISF-UHFFFAOYSA-N 3-aminoalanine Chemical compound [NH3+]CC(N)C([O-])=O PECYZEOJVXMISF-UHFFFAOYSA-N 0.000 claims 1
- 125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 0.000 claims 1
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 claims 1
- AWLMDHXPKGLEQT-UHFFFAOYSA-N 4-amino-1-carbamimidoylpiperidine-4-carboxylic acid Chemical compound NC(=N)N1CCC(N)(C(O)=O)CC1 AWLMDHXPKGLEQT-UHFFFAOYSA-N 0.000 claims 1
- KHABBYNLBYZCKP-UHFFFAOYSA-N 4-aminopiperidin-1-ium-4-carboxylate Chemical compound OC(=O)C1(N)CCNCC1 KHABBYNLBYZCKP-UHFFFAOYSA-N 0.000 claims 1
- 229960000549 4-dimethylaminophenol Drugs 0.000 claims 1
- 239000004475 Arginine Substances 0.000 claims 1
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 claims 1
- 108010078777 Colistin Proteins 0.000 claims 1
- 201000003883 Cystic fibrosis Diseases 0.000 claims 1
- AEMOLEFTQBMNLQ-BZINKQHNSA-N D-Guluronic Acid Chemical compound OC1O[C@H](C(O)=O)[C@H](O)[C@@H](O)[C@H]1O AEMOLEFTQBMNLQ-BZINKQHNSA-N 0.000 claims 1
- 229930182819 D-leucine Natural products 0.000 claims 1
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- AEMOLEFTQBMNLQ-VANFPWTGSA-N D-mannopyranuronic acid Chemical compound OC1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@@H]1O AEMOLEFTQBMNLQ-VANFPWTGSA-N 0.000 claims 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims 1
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- QUOGESRFPZDMMT-UHFFFAOYSA-N L-Homoarginine Natural products OC(=O)C(N)CCCCNC(N)=N QUOGESRFPZDMMT-UHFFFAOYSA-N 0.000 claims 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims 1
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 claims 1
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims 1
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- FFFHZYDWPBMWHY-VKHMYHEASA-N L-homocysteine Chemical compound OC(=O)[C@@H](N)CCS FFFHZYDWPBMWHY-VKHMYHEASA-N 0.000 claims 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims 1
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims 1
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- 239000004472 Lysine Substances 0.000 claims 1
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- MXNRLFUSFKVQSK-QMMMGPOBSA-O N(6),N(6),N(6)-trimethyl-L-lysine Chemical compound C[N+](C)(C)CCCC[C@H]([NH3+])C([O-])=O MXNRLFUSFKVQSK-QMMMGPOBSA-O 0.000 claims 1
- 108010093965 Polymyxin B Proteins 0.000 claims 1
- 206010057190 Respiratory tract infections Diseases 0.000 claims 1
- 108091028664 Ribonucleotide Proteins 0.000 claims 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims 1
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- XDJYMJULXQKGMM-RVYUQJQSSA-N colistin A Polymers CC[C@@H](C)CCCCC(=O)N[C@@H](CCN)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCN)C(=O)N[C@H]1CCNC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCN)NC(=O)[C@H](CCN)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CCN)NC1=O XDJYMJULXQKGMM-RVYUQJQSSA-N 0.000 claims 1
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- JORAUNFTUVJTNG-BSTBCYLQSA-N n-[(2s)-4-amino-1-[[(2s,3r)-1-[[(2s)-4-amino-1-oxo-1-[[(3s,6s,9s,12s,15r,18s,21s)-6,9,18-tris(2-aminoethyl)-3-[(1r)-1-hydroxyethyl]-12,15-bis(2-methylpropyl)-2,5,8,11,14,17,20-heptaoxo-1,4,7,10,13,16,19-heptazacyclotricos-21-yl]amino]butan-2-yl]amino]-3-h Chemical compound CC(C)CCCCC(=O)N[C@@H](CCN)C(=O)N[C@H]([C@@H](C)O)CN[C@@H](CCN)C(=O)N[C@H]1CCNC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCN)NC(=O)[C@H](CCN)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CCN)NC1=O.CCC(C)CCCCC(=O)N[C@@H](CCN)C(=O)N[C@H]([C@@H](C)O)CN[C@@H](CCN)C(=O)N[C@H]1CCNC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCN)NC(=O)[C@H](CCN)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CCN)NC1=O JORAUNFTUVJTNG-BSTBCYLQSA-N 0.000 claims 1
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Classifications
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- A61K47/61—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule the organic macromolecular compound being a polysaccharide or a derivative thereof
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- A—HUMAN NECESSITIES
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1617860.0 | 2016-10-21 | ||
| GBGB1617860.0A GB201617860D0 (en) | 2016-10-21 | 2016-10-21 | Polymyxin-alginate oligomer conjugates |
| GB1714710.9 | 2017-09-13 | ||
| GBGB1714710.9A GB201714710D0 (en) | 2017-09-13 | 2017-09-13 | Polymyxin-alginate oligomer conjugates |
| PCT/EP2017/076927 WO2018073449A1 (en) | 2016-10-21 | 2017-10-20 | Polymyxin-alginate oligomer conjugates |
Publications (2)
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| RU2019109719A true RU2019109719A (ru) | 2020-11-24 |
| RU2019109719A3 RU2019109719A3 (enExample) | 2021-02-20 |
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| RU2019109719A RU2019109719A (ru) | 2016-10-21 | 2017-10-20 | Конъюгаты полимиксин-альгинатных олигомеров |
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| EP (1) | EP3528830B1 (enExample) |
| JP (1) | JP2020503253A (enExample) |
| KR (1) | KR20190072579A (enExample) |
| CN (1) | CN109843315A (enExample) |
| AU (1) | AU2017345295A1 (enExample) |
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| CA (1) | CA3040795A1 (enExample) |
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| ES (1) | ES2933983T3 (enExample) |
| FI (1) | FI3528830T3 (enExample) |
| RU (1) | RU2019109719A (enExample) |
| WO (1) | WO2018073449A1 (enExample) |
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| IL293883A (en) * | 2019-12-14 | 2022-08-01 | Manu Chaudhary | Formulations of polybasic drugs to reduce multi-organ toxicity |
| US20230141981A1 (en) * | 2020-01-21 | 2023-05-11 | Shanghai Micurx Pharmaceuticals Co., Ltd | Novel compounds and composition for targeted therapy of kidney-associated cancers |
| US12037631B2 (en) * | 2020-10-06 | 2024-07-16 | City University Of Hong Kong | System and method for detecting a target enzyme |
| CN113069556B (zh) * | 2021-04-12 | 2022-04-08 | 青岛大学附属医院 | 一种枝接那他霉素的氧化海藻酸纤维膜及其制备方法 |
| CN113081956A (zh) * | 2021-04-12 | 2021-07-09 | 青岛大学附属医院 | 一种氧化海藻酸钠改性的那他霉素滴眼液及其制备方法 |
| CN117693517A (zh) * | 2021-07-21 | 2024-03-12 | 上海盟科药业股份有限公司 | 用于靶向治疗肾癌的新型化合物和组合物 |
| WO2023001223A1 (en) * | 2021-07-21 | 2023-01-26 | Shanghai Micurx Pharmaceutical Co., Ltd. | Compounds and compositions for targeted therapy of renal diseases |
| CN114009731B (zh) * | 2021-11-05 | 2024-01-02 | 恒枫食品科技有限公司 | 一种茶风味基料及其制备方法、应用 |
| CN114752535A (zh) * | 2022-05-16 | 2022-07-15 | 北京昊峰节能环保科技有限公司 | 一种总石油烃污染地下水生物修复剂及其制备方法与应用 |
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|---|---|---|---|---|
| GB976301A (en) * | 1960-10-27 | 1964-11-25 | Calmic Ltd | Preparation and use of alginates |
| US5177059A (en) * | 1989-11-15 | 1993-01-05 | Sandoz Ltd. | Polymyxin B conjugates |
| ATE111746T1 (de) * | 1989-11-15 | 1994-10-15 | Sandoz Ag | Polymyxinkonjugate. |
| GB2270920B (en) * | 1992-09-25 | 1997-04-02 | Univ Keele | Alginate-bioactive agent conjugates |
| US6011008A (en) * | 1997-01-08 | 2000-01-04 | Yissum Research Developement Company Of The Hebrew University Of Jerusalem | Conjugates of biologically active substances |
| HUE034051T2 (en) * | 2007-11-27 | 2018-01-29 | Algipharma As | Use of alginate-containing oligomers to combat biofilms |
| US8815831B2 (en) * | 2009-06-03 | 2014-08-26 | Algipharma As | Treatment of Acinetobacter with alginate oligomers and antibiotics |
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2017
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- 2017-10-20 BR BR112019007927A patent/BR112019007927A2/pt not_active IP Right Cessation
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- 2017-10-20 FI FIEP17791037.9T patent/FI3528830T3/fi active
- 2017-10-20 WO PCT/EP2017/076927 patent/WO2018073449A1/en not_active Ceased
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- 2017-10-20 US US16/343,568 patent/US20190328833A1/en not_active Abandoned
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- 2017-10-20 JP JP2019521049A patent/JP2020503253A/ja active Pending
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| ES2933983T3 (es) | 2023-02-15 |
| KR20190072579A (ko) | 2019-06-25 |
| CA3040795A1 (en) | 2018-04-26 |
| US20190328833A1 (en) | 2019-10-31 |
| FI3528830T3 (fi) | 2023-01-13 |
| WO2018073449A1 (en) | 2018-04-26 |
| DK3528830T3 (da) | 2022-12-19 |
| BR112019007927A2 (pt) | 2019-07-02 |
| AU2017345295A1 (en) | 2019-05-02 |
| EP3528830B1 (en) | 2022-10-05 |
| EP3528830A1 (en) | 2019-08-28 |
| JP2020503253A (ja) | 2020-01-30 |
| CN109843315A (zh) | 2019-06-04 |
| RU2019109719A3 (enExample) | 2021-02-20 |
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