DK3052545T3 - New poly (ethyleneimine) -based copolymers for binding to and releasing genetic material, especially DNA / RNA, and methods for their preparation and use - Google Patents
New poly (ethyleneimine) -based copolymers for binding to and releasing genetic material, especially DNA / RNA, and methods for their preparation and use Download PDFInfo
- Publication number
- DK3052545T3 DK3052545T3 DK14803038.0T DK14803038T DK3052545T3 DK 3052545 T3 DK3052545 T3 DK 3052545T3 DK 14803038 T DK14803038 T DK 14803038T DK 3052545 T3 DK3052545 T3 DK 3052545T3
- Authority
- DK
- Denmark
- Prior art keywords
- genetic material
- poly
- units
- binding
- ethyleneimine
- Prior art date
Links
- 229920001577 copolymer Polymers 0.000 title claims description 55
- 229920002873 Polyethylenimine Polymers 0.000 title claims description 38
- 108090000623 proteins and genes Proteins 0.000 title claims description 24
- 102000004169 proteins and genes Human genes 0.000 title claims description 23
- 238000000034 method Methods 0.000 title claims description 12
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000000017 hydrogel Substances 0.000 claims description 37
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 26
- 230000015572 biosynthetic process Effects 0.000 claims description 15
- 238000003786 synthesis reaction Methods 0.000 claims description 12
- 239000011324 bead Substances 0.000 claims description 11
- 125000003504 2-oxazolinyl group Chemical group O1C(=NCC1)* 0.000 claims description 9
- 239000000178 monomer Substances 0.000 claims description 7
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 claims description 6
- 239000002245 particle Substances 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000000758 substrate Substances 0.000 claims description 4
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 150000008065 acid anhydrides Chemical class 0.000 claims description 2
- 230000003213 activating effect Effects 0.000 claims description 2
- 238000007306 functionalization reaction Methods 0.000 claims 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- -1 poly(ethyleneimine) Polymers 0.000 description 19
- 229920000642 polymer Polymers 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 108091032973 (ribonucleotides)n+m Proteins 0.000 description 8
- OXBLVCZKDOZZOJ-UHFFFAOYSA-N 2,3-Dihydrothiophene Chemical compound C1CC=CS1 OXBLVCZKDOZZOJ-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000002105 nanoparticle Substances 0.000 description 8
- 125000003277 amino group Chemical group 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000004132 cross linking Methods 0.000 description 5
- 239000003431 cross linking reagent Substances 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical group OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 150000004662 dithiols Chemical class 0.000 description 4
- 239000000499 gel Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- VYYANIUXTTXFJR-UHFFFAOYSA-N 2-but-3-enyl-4,5-dihydro-1,3-oxazole Chemical compound C=CCCC1=NCCO1 VYYANIUXTTXFJR-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000006957 Michael reaction Methods 0.000 description 3
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 150000002466 imines Chemical class 0.000 description 3
- 239000007943 implant Substances 0.000 description 3
- 239000013612 plasmid Substances 0.000 description 3
- 229920000765 poly(2-oxazolines) Polymers 0.000 description 3
- 229920001281 polyalkylene Polymers 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 229920003169 water-soluble polymer Polymers 0.000 description 3
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 2
- HCZMHWVFVZAHCR-UHFFFAOYSA-N 2-[2-(2-sulfanylethoxy)ethoxy]ethanethiol Chemical compound SCCOCCOCCS HCZMHWVFVZAHCR-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- 241000252203 Clupea harengus Species 0.000 description 2
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 2
- 230000021736 acetylation Effects 0.000 description 2
- 238000006640 acetylation reaction Methods 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 230000001588 bifunctional effect Effects 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 229920006037 cross link polymer Polymers 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 229960005542 ethidium bromide Drugs 0.000 description 2
- 238000001879 gelation Methods 0.000 description 2
- 229960002897 heparin Drugs 0.000 description 2
- 229920000669 heparin Polymers 0.000 description 2
- 235000019514 herring Nutrition 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 230000001965 increasing effect Effects 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 230000001404 mediated effect Effects 0.000 description 2
- PSGAAPLEWMOORI-PEINSRQWSA-N medroxyprogesterone acetate Chemical compound C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@](OC(C)=O)(C(C)=O)CC[C@H]21 PSGAAPLEWMOORI-PEINSRQWSA-N 0.000 description 2
- 230000000269 nucleophilic effect Effects 0.000 description 2
- 238000000059 patterning Methods 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 150000003573 thiols Chemical class 0.000 description 2
- 239000003106 tissue adhesive Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 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 description 1
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 1
- ONRREFWJTRBDRA-UHFFFAOYSA-N 2-chloroethanamine;hydron;chloride Chemical compound [Cl-].[NH3+]CCCl ONRREFWJTRBDRA-UHFFFAOYSA-N 0.000 description 1
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 238000000018 DNA microarray Methods 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 108020004459 Small interfering RNA Proteins 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000000266 alpha-aminoacyl group Chemical group 0.000 description 1
- 230000009435 amidation Effects 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003373 anti-fouling effect Effects 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- ZMMJGEGLRURXTF-UHFFFAOYSA-N ethidium bromide Chemical compound [Br-].C12=CC(N)=CC=C2C2=CC=C(N)C=C2[N+](CC)=C1C1=CC=CC=C1 ZMMJGEGLRURXTF-UHFFFAOYSA-N 0.000 description 1
- 238000000799 fluorescence microscopy Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 238000001476 gene delivery Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 238000013090 high-throughput technology Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 210000004962 mammalian cell Anatomy 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229940127554 medical product Drugs 0.000 description 1
- 238000000813 microcontact printing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- QNILTEGFHQSKFF-UHFFFAOYSA-N n-propan-2-ylprop-2-enamide Chemical compound CC(C)NC(=O)C=C QNILTEGFHQSKFF-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 150000002918 oxazolines Chemical class 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 210000004872 soft tissue Anatomy 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003356 suture material Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 238000001890 transfection Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/0206—Polyalkylene(poly)amines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/0206—Polyalkylene(poly)amines
- C08G73/0213—Preparatory process
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/0233—Polyamines derived from (poly)oxazolines, (poly)oxazines or having pendant acyl groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G81/00—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102013016750.7A DE102013016750A1 (de) | 2013-10-02 | 2013-10-02 | Neue Poly(ethylenimin) basierte Copolymere zur Anbindung und Freisetzung von genetischem Material, insbesondere von DNA/RNA, sowie Verfahren zu deren Herstellung und Verwendung |
| PCT/DE2014/000500 WO2015048940A1 (de) | 2013-10-02 | 2014-10-02 | Neue poly(ethylenimin) basierte copolymere zur anbindung und freisetzung von genetischem material, insbesondere von dna/rna, sowie verfahren zu deren herstellung und verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK3052545T3 true DK3052545T3 (en) | 2018-10-29 |
Family
ID=51986963
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK14803038.0T DK3052545T3 (en) | 2013-10-02 | 2014-10-02 | New poly (ethyleneimine) -based copolymers for binding to and releasing genetic material, especially DNA / RNA, and methods for their preparation and use |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US10131747B2 (https=) |
| EP (1) | EP3052545B1 (https=) |
| JP (1) | JP6431533B2 (https=) |
| CN (1) | CN105683256B (https=) |
| CA (1) | CA2926154C (https=) |
| DE (1) | DE102013016750A1 (https=) |
| DK (1) | DK3052545T3 (https=) |
| ES (1) | ES2691094T3 (https=) |
| HU (1) | HUE040402T2 (https=) |
| WO (1) | WO2015048940A1 (https=) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101892955B1 (ko) | 2017-01-25 | 2018-08-29 | 국방과학연구소 | 치환된 Poly[2-(3-butenyl)-2-oxazoline] 및 Nylon-6,6를 포함하는 섬유 및 그 제조방법 |
| EP4229115A1 (en) * | 2020-10-19 | 2023-08-23 | Universiteit Gent | Cross-linkable allylamido polymers |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3251778A (en) * | 1960-08-04 | 1966-05-17 | Petrolite Corp | Process of preventing scale |
| DE19726186A1 (de) * | 1997-06-20 | 1998-12-24 | Boehringer Ingelheim Int | Komplexe für den Transport von Nukleinsäure in höhere eukaryotische Zellen |
| DE10029028A1 (de) * | 2000-06-13 | 2001-12-20 | Basf Ag | Verwendung von acylierten Polyaminen zur Modifizierung von Oberflächen |
| DE20122328U1 (de) * | 2001-12-07 | 2006-02-09 | Sandler Ag | Neue modifizierte Poly-2-oxazoline |
| JP4368183B2 (ja) * | 2003-11-06 | 2009-11-18 | 財団法人川村理化学研究所 | ポリイオン会合体およびポリイオン会合体からなる生体物質キャリアー |
| US20050238825A1 (en) * | 2004-04-26 | 2005-10-27 | Isp Investments Inc. | Crosslinked polymeric composition |
| DE102005039154A1 (de) * | 2005-08-17 | 2007-03-01 | GÖPFERICH, Achim, Prof. Dr. | Bioabbaubare Polymere für den Transport von Nukleinsäuren in Zellen |
| US20070231392A1 (en) * | 2006-01-23 | 2007-10-04 | Ernst Wagner | CHEMICALLY MODIFIED POLYCATION POLYMER FOR siRNA DELIVERY |
| CA2711455C (en) | 2008-02-13 | 2016-06-07 | Hyperbranch Medical Technology, Inc. | Crosslinked polyalkyleneimine hydrogels with tunable degradation rates |
| JP5642673B2 (ja) * | 2008-07-10 | 2014-12-17 | セリナ・セラピユーテイツクス・インコーポレーテツド | 不活性末端基を有するポリオキサゾリン類、保護された開始基から調製されるポリオキサゾリン類及び関連化合物 |
| CN101768276B (zh) * | 2008-12-26 | 2011-11-30 | 中国科学技术大学 | 聚乙二醇单甲醚-聚己内酯-聚乙烯亚胺三嵌段共聚物及其应用 |
| RU2013103347A (ru) * | 2010-06-25 | 2014-07-27 | Торэй Индастриз, Инк. | Водорастворимый полимер и водорастворимый комплекс наночастиц |
| RU2593755C2 (ru) * | 2011-01-04 | 2016-08-10 | Бендер Аналитикал Холдинг Б.В. | Сшитые полимеры и имплантаты, произведенные из электрофильно активированного полиоксазолина |
| EP2683420B1 (en) * | 2011-03-11 | 2018-05-23 | W. L. Gore & Associates, Inc. | Improvements to immobilised biological entities |
| AT511386B1 (de) | 2011-05-03 | 2013-03-15 | Ke Kelit Kunststoffwerk Gmbh | Kontaktbiozid |
| US9416228B2 (en) * | 2012-03-16 | 2016-08-16 | Bender Analytical Holding B.V. | Cross-linked polymers and medical products derived from nucleophilically activated polyoxazoline |
-
2013
- 2013-10-02 DE DE102013016750.7A patent/DE102013016750A1/de active Granted
-
2014
- 2014-10-02 DK DK14803038.0T patent/DK3052545T3/en active
- 2014-10-02 CA CA2926154A patent/CA2926154C/en active Active
- 2014-10-02 EP EP14803038.0A patent/EP3052545B1/de active Active
- 2014-10-02 HU HUE14803038A patent/HUE040402T2/hu unknown
- 2014-10-02 JP JP2016519856A patent/JP6431533B2/ja active Active
- 2014-10-02 ES ES14803038.0T patent/ES2691094T3/es active Active
- 2014-10-02 US US15/026,882 patent/US10131747B2/en active Active
- 2014-10-02 CN CN201480059919.6A patent/CN105683256B/zh active Active
- 2014-10-02 WO PCT/DE2014/000500 patent/WO2015048940A1/de not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| HUE040402T2 (hu) | 2019-03-28 |
| US10131747B2 (en) | 2018-11-20 |
| JP6431533B2 (ja) | 2018-11-28 |
| CA2926154A1 (en) | 2015-04-09 |
| CA2926154C (en) | 2022-08-30 |
| EP3052545B1 (de) | 2018-07-25 |
| CN105683256B (zh) | 2018-02-23 |
| CN105683256A (zh) | 2016-06-15 |
| ES2691094T3 (es) | 2018-11-23 |
| JP2016533409A (ja) | 2016-10-27 |
| DE102013016750A1 (de) | 2015-04-02 |
| US20170166697A1 (en) | 2017-06-15 |
| WO2015048940A1 (de) | 2015-04-09 |
| EP3052545A1 (de) | 2016-08-10 |
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