ES2691094T3 - Nuevos copolímeros basados en poli(etilenimina) para el enlace y liberación de material genético, particularmente de ADN/ARN, así como método para su fabricación y uso - Google Patents
Nuevos copolímeros basados en poli(etilenimina) para el enlace y liberación de material genético, particularmente de ADN/ARN, así como método para su fabricación y uso Download PDFInfo
- Publication number
- ES2691094T3 ES2691094T3 ES14803038.0T ES14803038T ES2691094T3 ES 2691094 T3 ES2691094 T3 ES 2691094T3 ES 14803038 T ES14803038 T ES 14803038T ES 2691094 T3 ES2691094 T3 ES 2691094T3
- Authority
- ES
- Spain
- Prior art keywords
- ethyleneimine
- poly
- release
- genetic material
- units
- 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
- 229920001577 copolymer Polymers 0.000 title claims abstract description 57
- 229920002873 Polyethylenimine Polymers 0.000 title claims abstract description 44
- 108090000623 proteins and genes Proteins 0.000 title claims abstract description 26
- 102000004169 proteins and genes Human genes 0.000 title claims abstract description 25
- 230000027455 binding Effects 0.000 title claims abstract description 18
- 238000000034 method Methods 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims abstract description 22
- 125000003504 2-oxazolinyl group Chemical group O1C(=NCC1)* 0.000 claims abstract description 10
- 239000000178 monomer Substances 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- 239000000017 hydrogel Substances 0.000 claims description 32
- 230000015572 biosynthetic process Effects 0.000 claims description 16
- 238000007306 functionalization reaction Methods 0.000 claims description 16
- 238000003786 synthesis reaction Methods 0.000 claims description 11
- 239000011324 bead Substances 0.000 claims description 8
- 239000002245 particle Substances 0.000 claims description 6
- -1 3-dimethylaminopropyl Chemical group 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 239000011049 pearl Substances 0.000 claims description 3
- 239000000758 substrate Substances 0.000 claims description 3
- 150000008065 acid anhydrides Chemical class 0.000 claims description 2
- 239000007825 activation reagent Substances 0.000 claims description 2
- 150000001718 carbodiimides Chemical class 0.000 claims 1
- 108091032973 (ribonucleotides)n+m Proteins 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 229920000642 polymer Polymers 0.000 description 10
- 150000003573 thiols Chemical class 0.000 description 8
- 238000004132 cross linking Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- 239000000499 gel Substances 0.000 description 6
- 239000002105 nanoparticle Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical group OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 239000011521 glass 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
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 239000004971 Cross linker Substances 0.000 description 3
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 230000001588 bifunctional effect Effects 0.000 description 3
- 150000004662 dithiols Chemical class 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 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
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000006557 surface reaction Methods 0.000 description 3
- 239000003106 tissue adhesive Substances 0.000 description 3
- 230000009466 transformation Effects 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
- 230000004568 DNA-binding Effects 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
- 238000006845 Michael addition reaction Methods 0.000 description 2
- 230000004570 RNA-binding Effects 0.000 description 2
- 230000021736 acetylation Effects 0.000 description 2
- 238000006640 acetylation reaction Methods 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 229920006037 cross link polymer Polymers 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 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 2
- 229960005542 ethidium bromide Drugs 0.000 description 2
- 229960002897 heparin Drugs 0.000 description 2
- 229920000669 heparin Polymers 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 239000000463 material Substances 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
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229920001601 polyetherimide Polymers 0.000 description 2
- 150000003141 primary amines Chemical group 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 230000008719 thickening Effects 0.000 description 2
- 229920003169 water-soluble polymer Polymers 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- OXBLVCZKDOZZOJ-UHFFFAOYSA-N 2,3-Dihydrothiophene Chemical compound C1CC=CS1 OXBLVCZKDOZZOJ-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
- GUXJXWKCUUWCLX-UHFFFAOYSA-N 2-methyl-2-oxazoline Chemical compound CC1=NCCO1 GUXJXWKCUUWCLX-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
- 125000004975 3-butenyl group Chemical group C(CC=C)* 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
- PLLMBEQSVDYVPE-UHFFFAOYSA-N 3h-dithiole;2-[2-(2-sulfanylethoxy)ethoxy]ethanethiol Chemical compound C1SSC=C1.SCCOCCOCCS PLLMBEQSVDYVPE-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241000252203 Clupea harengus Species 0.000 description 1
- 238000000018 DNA microarray Methods 0.000 description 1
- 238000005033 Fourier transform infrared 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
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 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
- 230000003373 anti-fouling effect Effects 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- 239000012455 biphasic mixture 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
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 230000000052 comparative effect Effects 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
- 239000003431 cross linking reagent Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000002708 enhancing effect Effects 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
- 230000002068 genetic effect Effects 0.000 description 1
- 235000019514 herring Nutrition 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 210000004962 mammalian cell Anatomy 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
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 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
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 239000003356 suture material Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229940075469 tissue adhesives Drugs 0.000 description 1
- 238000001890 transfection Methods 0.000 description 1
- 238000005406 washing 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102013016750 | 2013-10-02 | ||
| 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 |
|---|---|
| ES2691094T3 true ES2691094T3 (es) | 2018-11-23 |
Family
ID=51986963
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES14803038.0T Active ES2691094T3 (es) | 2013-10-02 | 2014-10-02 | Nuevos copolímeros basados en poli(etilenimina) para el enlace y liberación de material genético, particularmente de ADN/ARN, así como método para su fabricación y uso |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US10131747B2 (enExample) |
| EP (1) | EP3052545B1 (enExample) |
| JP (1) | JP6431533B2 (enExample) |
| CN (1) | CN105683256B (enExample) |
| CA (1) | CA2926154C (enExample) |
| DE (1) | DE102013016750A1 (enExample) |
| DK (1) | DK3052545T3 (enExample) |
| ES (1) | ES2691094T3 (enExample) |
| HU (1) | HUE040402T2 (enExample) |
| WO (1) | WO2015048940A1 (enExample) |
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 |
| AU2021363584A1 (en) * | 2020-10-19 | 2023-06-08 | Queensland University Of Technology | 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 |
| WO2007084797A1 (en) | 2006-01-23 | 2007-07-26 | Abbott Laboratories | Chemically modified polycation polymer for sirna delivery |
| AU2009214615B2 (en) | 2008-02-13 | 2014-06-12 | Hyperbranch Medical Technology, Inc. | Crosslinked polyalkyleneimine hydrogels with tunable degradation rates |
| US8883211B2 (en) * | 2008-07-10 | 2014-11-11 | Serina Therapeutics, Inc. | Polyoxazolines with inert terminating groups, polyoxazolines prepared from protected initiating groups and related compounds |
| 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 |
| CN103429268B (zh) | 2011-01-04 | 2015-11-25 | 本德尔分析控股有限公司 | 从亲电活化的聚噁唑啉衍生的经交联的聚合物和植入物 |
| ES2955183T3 (es) * | 2011-03-11 | 2023-11-29 | Gore & Ass | Mejoras para las entidades biológicas inmovilizadas |
| AT511386B1 (de) | 2011-05-03 | 2013-03-15 | Ke Kelit Kunststoffwerk Gmbh | Kontaktbiozid |
| JP6178399B2 (ja) * | 2012-03-16 | 2017-08-09 | ベンデル アナリティカル ホールディング ビー．ブイ．Ｂｅｎｄｅｒ Ａｎａｌｙｔｉｃａｌ Ｈｏｌｄｉｎｇ Ｂ．Ｖ． | 求核的に活性化したポリオキサゾリンに由来する架橋ポリマー及び医療製品 |
-
2013
- 2013-10-02 DE DE102013016750.7A patent/DE102013016750A1/de active Granted
-
2014
- 2014-10-02 CA CA2926154A patent/CA2926154C/en active Active
- 2014-10-02 DK DK14803038.0T patent/DK3052545T3/en active
- 2014-10-02 JP JP2016519856A patent/JP6431533B2/ja active Active
- 2014-10-02 EP EP14803038.0A patent/EP3052545B1/de active Active
- 2014-10-02 WO PCT/DE2014/000500 patent/WO2015048940A1/de not_active Ceased
- 2014-10-02 CN CN201480059919.6A patent/CN105683256B/zh active Active
- 2014-10-02 US US15/026,882 patent/US10131747B2/en active Active
- 2014-10-02 HU HUE14803038A patent/HUE040402T2/hu unknown
- 2014-10-02 ES ES14803038.0T patent/ES2691094T3/es active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CN105683256A (zh) | 2016-06-15 |
| US20170166697A1 (en) | 2017-06-15 |
| HUE040402T2 (hu) | 2019-03-28 |
| EP3052545A1 (de) | 2016-08-10 |
| WO2015048940A1 (de) | 2015-04-09 |
| CA2926154A1 (en) | 2015-04-09 |
| DK3052545T3 (en) | 2018-10-29 |
| US10131747B2 (en) | 2018-11-20 |
| EP3052545B1 (de) | 2018-07-25 |
| JP2016533409A (ja) | 2016-10-27 |
| CA2926154C (en) | 2022-08-30 |
| JP6431533B2 (ja) | 2018-11-28 |
| CN105683256B (zh) | 2018-02-23 |
| DE102013016750A1 (de) | 2015-04-02 |
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