JP2021059555A5 - - Google Patents
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- JP2021059555A5 JP2021059555A5 JP2020203413A JP2020203413A JP2021059555A5 JP 2021059555 A5 JP2021059555 A5 JP 2021059555A5 JP 2020203413 A JP2020203413 A JP 2020203413A JP 2020203413 A JP2020203413 A JP 2020203413A JP 2021059555 A5 JP2021059555 A5 JP 2021059555A5
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- JP
- Japan
- Prior art keywords
- group
- transfection complex
- complex according
- bromide
- methyl
- 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.)
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- 238000001890 transfection Methods 0.000 claims 14
- 229910052757 nitrogen Inorganic materials 0.000 claims 13
- 150000002632 lipids Chemical class 0.000 claims 8
- SLKDGVPOSSLUAI-PGUFJCEWSA-N 1,2-dihexadecanoyl-sn-glycero-3-phosphoethanolamine zwitterion Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OCCN)OC(=O)CCCCCCCCCCCCCCC SLKDGVPOSSLUAI-PGUFJCEWSA-N 0.000 claims 7
- 150000001875 compounds Chemical class 0.000 claims 7
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims 6
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 claims 6
- 230000008685 targeting Effects 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 5
- KILNVBDSWZSGLL-KXQOOQHDSA-N 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCC KILNVBDSWZSGLL-KXQOOQHDSA-N 0.000 claims 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims 4
- 150000008104 phosphatidylethanolamines Chemical class 0.000 claims 4
- 108090000765 processed proteins & peptides Proteins 0.000 claims 4
- -1 (9-octadecenyloxy)- Chemical class 0.000 claims 3
- 108091032973 (ribonucleotides)n+m Proteins 0.000 claims 3
- BIABMEZBCHDPBV-MPQUPPDSSA-N 1,2-palmitoyl-sn-glycero-3-phospho-(1'-sn-glycerol) Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@@H](O)CO)OC(=O)CCCCCCCCCCCCCCC BIABMEZBCHDPBV-MPQUPPDSSA-N 0.000 claims 3
- KWVJHCQQUFDPLU-YEUCEMRASA-N 2,3-bis[[(z)-octadec-9-enoyl]oxy]propyl-trimethylazanium Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(C[N+](C)(C)C)OC(=O)CCCCCCC\C=C/CCCCCCCC KWVJHCQQUFDPLU-YEUCEMRASA-N 0.000 claims 3
- JZNWSCPGTDBMEW-UHFFFAOYSA-N Glycerophosphorylethanolamin Natural products NCCOP(O)(=O)OCC(O)CO JZNWSCPGTDBMEW-UHFFFAOYSA-N 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 125000002091 cationic group Chemical group 0.000 claims 3
- 235000012000 cholesterol Nutrition 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 claims 2
- HEBKCHPVOIAQTA-QWWZWVQMSA-N D-arabinitol Chemical compound OC[C@@H](O)C(O)[C@H](O)CO HEBKCHPVOIAQTA-QWWZWVQMSA-N 0.000 claims 2
- XULFJDKZVHTRLG-JDVCJPALSA-N DOSPA trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.CCCCCCCC\C=C/CCCCCCCCOCC(C[N+](C)(C)CCNC(=O)C(CCCNCCCN)NCCCN)OCCCCCCCC\C=C/CCCCCCCC XULFJDKZVHTRLG-JDVCJPALSA-N 0.000 claims 2
- KLFKZIQAIPDJCW-HTIIIDOHSA-N Dipalmitoylphosphatidylserine Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)CCCCCCCCCCCCCCC KLFKZIQAIPDJCW-HTIIIDOHSA-N 0.000 claims 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
- ATBOMIWRCZXYSZ-XZBBILGWSA-N [1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-hexadecanoyloxypropan-2-yl] (9e,12e)-octadeca-9,12-dienoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(COP(O)(=O)OCC(O)CO)OC(=O)CCCCCCC\C=C\C\C=C\CCCCC ATBOMIWRCZXYSZ-XZBBILGWSA-N 0.000 claims 2
- AWUCVROLDVIAJX-UHFFFAOYSA-N alpha-glycerophosphate Natural products OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 claims 2
- 125000000656 azaniumyl group Chemical group [H][N+]([H])([H])[*] 0.000 claims 2
- 230000000975 bioactive effect Effects 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 230000004927 fusion Effects 0.000 claims 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 108020004707 nucleic acids Proteins 0.000 claims 2
- 102000039446 nucleic acids Human genes 0.000 claims 2
- 150000007523 nucleic acids Chemical class 0.000 claims 2
- 102000004196 processed proteins & peptides Human genes 0.000 claims 2
- 108090000623 proteins and genes Proteins 0.000 claims 2
- 102000004169 proteins and genes Human genes 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- XMGQYMWWDOXHJM-JTQLQIEISA-N (+)-α-limonene Chemical compound CC(=C)[C@@H]1CCC(C)=CC1 XMGQYMWWDOXHJM-JTQLQIEISA-N 0.000 claims 1
- QFMZQPDHXULLKC-UHFFFAOYSA-N 1,2-bis(diphenylphosphino)ethane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 QFMZQPDHXULLKC-UHFFFAOYSA-N 0.000 claims 1
- PORPENFLTBBHSG-MGBGTMOVSA-N 1,2-dihexadecanoyl-sn-glycerol-3-phosphate Chemical group CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCC PORPENFLTBBHSG-MGBGTMOVSA-N 0.000 claims 1
- NRJAVPSFFCBXDT-HUESYALOSA-N 1,2-distearoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCC NRJAVPSFFCBXDT-HUESYALOSA-N 0.000 claims 1
- TZCPCKNHXULUIY-RGULYWFUSA-N 1,2-distearoyl-sn-glycero-3-phosphoserine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)CCCCCCCCCCCCCCCCC TZCPCKNHXULUIY-RGULYWFUSA-N 0.000 claims 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 claims 1
- LDGWQMRUWMSZIU-LQDDAWAPSA-M 2,3-bis[(z)-octadec-9-enoxy]propyl-trimethylazanium;chloride Chemical compound [Cl-].CCCCCCCC\C=C/CCCCCCCCOCC(C[N+](C)(C)C)OCCCCCCCC\C=C/CCCCCCCC LDGWQMRUWMSZIU-LQDDAWAPSA-M 0.000 claims 1
- WALUVDCNGPQPOD-UHFFFAOYSA-M 2,3-di(tetradecoxy)propyl-(2-hydroxyethyl)-dimethylazanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCOCC(C[N+](C)(C)CCO)OCCCCCCCCCCCCCC WALUVDCNGPQPOD-UHFFFAOYSA-M 0.000 claims 1
- 125000005999 2-bromoethyl group Chemical group 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- 229960000549 4-dimethylaminophenol Drugs 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
- UVDZEXDYRJVBEI-UHFFFAOYSA-N CCCCCCCCCCCCCCCCCCNCCCCCCCCCCCCCCCCCC.NCCCNCCCCNCCCN(C(CN)=O)C(O)=O Chemical compound CCCCCCCCCCCCCCCCCCNCCCCCCCCCCCCCCCCCC.NCCCNCCCCNCCCN(C(CN)=O)C(O)=O UVDZEXDYRJVBEI-UHFFFAOYSA-N 0.000 claims 1
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 1
- 241000755712 Diores Species 0.000 claims 1
- ZWZWYGMENQVNFU-UHFFFAOYSA-N Glycerophosphorylserin Natural products OC(=O)C(N)COP(O)(=O)OCC(O)CO ZWZWYGMENQVNFU-UHFFFAOYSA-N 0.000 claims 1
- BACYUWVYYTXETD-UHFFFAOYSA-N N-Lauroylsarcosine Chemical compound CCCCCCCCCCCC(=O)N(C)CC(O)=O BACYUWVYYTXETD-UHFFFAOYSA-N 0.000 claims 1
- 108010079855 Peptide Aptamers Proteins 0.000 claims 1
- 108091027967 Small hairpin RNA Proteins 0.000 claims 1
- 108020004459 Small interfering RNA Proteins 0.000 claims 1
- 108091060271 Small temporal RNA Proteins 0.000 claims 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims 1
- HIHOWBSBBDRPDW-PTHRTHQKSA-N [(3s,8s,9s,10r,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3-yl] n-[2-(dimethylamino)ethyl]carbamate Chemical compound C1C=C2C[C@@H](OC(=O)NCCN(C)C)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HIHOWBSBBDRPDW-PTHRTHQKSA-N 0.000 claims 1
- 125000002015 acyclic group Chemical group 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 150000003863 ammonium salts Chemical class 0.000 claims 1
- VJLOFJZWUDZJBX-UHFFFAOYSA-N bis(2-hydroxyethyl)azanium;chloride Chemical compound [Cl-].OCC[NH2+]CCO VJLOFJZWUDZJBX-UHFFFAOYSA-N 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 229940106189 ceramide Drugs 0.000 claims 1
- 150000001783 ceramides Chemical class 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- UMGXUWVIJIQANV-UHFFFAOYSA-M didecyl(dimethyl)azanium;bromide Chemical compound [Br-].CCCCCCCCCC[N+](C)(C)CCCCCCCCCC UMGXUWVIJIQANV-UHFFFAOYSA-M 0.000 claims 1
- 235000014113 dietary fatty acids Nutrition 0.000 claims 1
- OSZGJYNGVGNCGA-IZNNDHRXSA-N dihexadecyl-methyl-[(2r,3s,4r)-2,3,4,5-tetrahydroxypentyl]azanium Chemical compound CCCCCCCCCCCCCCCC[N+](C)(C[C@@H](O)[C@H](O)[C@H](O)CO)CCCCCCCCCCCCCCCC OSZGJYNGVGNCGA-IZNNDHRXSA-N 0.000 claims 1
- OSZGJYNGVGNCGA-YXWIYCFASA-N dihexadecyl-methyl-[(2s,3r,4r)-2,3,4,5-tetrahydroxypentyl]azanium Chemical compound CCCCCCCCCCCCCCCC[N+](C)(C[C@H](O)[C@@H](O)[C@H](O)CO)CCCCCCCCCCCCCCCC OSZGJYNGVGNCGA-YXWIYCFASA-N 0.000 claims 1
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 claims 1
- ZGSPNIOCEDOHGS-UHFFFAOYSA-L disodium [3-[2,3-di(octadeca-9,12-dienoyloxy)propoxy-oxidophosphoryl]oxy-2-hydroxypropyl] 2,3-di(octadeca-9,12-dienoyloxy)propyl phosphate Chemical compound [Na+].[Na+].CCCCCC=CCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCC=CCCCCC)COP([O-])(=O)OCC(O)COP([O-])(=O)OCC(OC(=O)CCCCCCCC=CCC=CCCCCC)COC(=O)CCCCCCCC=CCC=CCCCCC ZGSPNIOCEDOHGS-UHFFFAOYSA-L 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 229930195729 fatty acid Natural products 0.000 claims 1
- 239000000194 fatty acid Substances 0.000 claims 1
- 150000004676 glycans Chemical class 0.000 claims 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol Substances OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 1
- 150000002314 glycerols Chemical class 0.000 claims 1
- MVYQJCPZZBFMLF-UHFFFAOYSA-N hydron;propan-1-amine;bromide Chemical compound [Br-].CCC[NH3+] MVYQJCPZZBFMLF-UHFFFAOYSA-N 0.000 claims 1
- 229940067606 lecithin Drugs 0.000 claims 1
- 239000000787 lecithin Substances 0.000 claims 1
- 235000010445 lecithin Nutrition 0.000 claims 1
- 108020004999 messenger RNA Proteins 0.000 claims 1
- 108091070501 miRNA Proteins 0.000 claims 1
- 239000002679 microRNA Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 claims 1
- 230000007935 neutral effect Effects 0.000 claims 1
- 108091008104 nucleic acid aptamers Proteins 0.000 claims 1
- 230000030648 nucleus localization Effects 0.000 claims 1
- 150000008105 phosphatidylcholines Chemical class 0.000 claims 1
- 229940067605 phosphatidylethanolamines Drugs 0.000 claims 1
- 229920001282 polysaccharide Polymers 0.000 claims 1
- 239000005017 polysaccharide Substances 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 239000002924 silencing RNA Substances 0.000 claims 1
- 239000004055 small Interfering RNA Substances 0.000 claims 1
- 150000003408 sphingolipids Chemical class 0.000 claims 1
- 0 CNCC(CO)NC*CCCCC=*CC* Chemical compound CNCC(CO)NC*CCCCC=*CC* 0.000 description 6
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2022141466A JP7512335B2 (ja) | 2010-11-15 | 2022-09-06 | アミン含有トランスフェクション試薬ならびにそれを生成および使用するための方法 |
Applications Claiming Priority (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US41390510P | 2010-11-15 | 2010-11-15 | |
| US61/413,905 | 2010-11-15 | ||
| US201161437503P | 2011-01-28 | 2011-01-28 | |
| US61/437,503 | 2011-01-28 | ||
| US201161438903P | 2011-02-02 | 2011-02-02 | |
| US61/438,903 | 2011-02-02 | ||
| US201161543242P | 2011-10-04 | 2011-10-04 | |
| US61/543,242 | 2011-10-04 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018146564A Division JP6807900B2 (ja) | 2010-11-15 | 2018-08-03 | アミン含有トランスフェクション試薬ならびにそれを生成および使用するための方法 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2022141466A Division JP7512335B2 (ja) | 2010-11-15 | 2022-09-06 | アミン含有トランスフェクション試薬ならびにそれを生成および使用するための方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2021059555A JP2021059555A (ja) | 2021-04-15 |
| JP2021059555A5 true JP2021059555A5 (https=) | 2021-08-05 |
| JP7138692B2 JP7138692B2 (ja) | 2022-09-16 |
Family
ID=45217672
Family Applications (6)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013539959A Pending JP2014508102A (ja) | 2010-11-15 | 2011-11-15 | アミン含有トランスフェクション試薬ならびにそれを生成および使用するための方法 |
| JP2016183855A Pending JP2017031186A (ja) | 2010-11-15 | 2016-09-21 | アミン含有トランスフェクション試薬ならびにそれを生成および使用するための方法 |
| JP2017248675A Active JP6383480B2 (ja) | 2010-11-15 | 2017-12-26 | アミン含有トランスフェクション試薬ならびにそれを生成および使用するための方法 |
| JP2018146564A Active JP6807900B2 (ja) | 2010-11-15 | 2018-08-03 | アミン含有トランスフェクション試薬ならびにそれを生成および使用するための方法 |
| JP2020203413A Active JP7138692B2 (ja) | 2010-11-15 | 2020-12-08 | アミン含有トランスフェクション試薬ならびにそれを生成および使用するための方法 |
| JP2022141466A Active JP7512335B2 (ja) | 2010-11-15 | 2022-09-06 | アミン含有トランスフェクション試薬ならびにそれを生成および使用するための方法 |
Family Applications Before (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013539959A Pending JP2014508102A (ja) | 2010-11-15 | 2011-11-15 | アミン含有トランスフェクション試薬ならびにそれを生成および使用するための方法 |
| JP2016183855A Pending JP2017031186A (ja) | 2010-11-15 | 2016-09-21 | アミン含有トランスフェクション試薬ならびにそれを生成および使用するための方法 |
| JP2017248675A Active JP6383480B2 (ja) | 2010-11-15 | 2017-12-26 | アミン含有トランスフェクション試薬ならびにそれを生成および使用するための方法 |
| JP2018146564A Active JP6807900B2 (ja) | 2010-11-15 | 2018-08-03 | アミン含有トランスフェクション試薬ならびにそれを生成および使用するための方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2022141466A Active JP7512335B2 (ja) | 2010-11-15 | 2022-09-06 | アミン含有トランスフェクション試薬ならびにそれを生成および使用するための方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (5) | US20120136073A1 (https=) |
| EP (2) | EP2640700B1 (https=) |
| JP (6) | JP2014508102A (https=) |
| CN (3) | CN108358812B (https=) |
| BR (1) | BR122022001262B1 (https=) |
| DK (1) | DK2640700T3 (https=) |
| ES (1) | ES2702428T3 (https=) |
| WO (1) | WO2012068176A1 (https=) |
Families Citing this family (114)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7901708B2 (en) | 2002-06-28 | 2011-03-08 | Protiva Biotherapeutics, Inc. | Liposomal apparatus and manufacturing methods |
| NZ592917A (en) * | 2003-09-15 | 2012-12-21 | Protiva Biotherapeutics Inc | Stable polyethyleneglycol (PEG) dialkyloxypropyl (DAA) lipid conjugates |
| US7799565B2 (en) | 2004-06-07 | 2010-09-21 | Protiva Biotherapeutics, Inc. | Lipid encapsulated interfering RNA |
| CA2587411A1 (en) * | 2004-11-17 | 2006-05-26 | Protiva Biotherapeutics, Inc. | Sirna silencing of apolipoprotein b |
| US8101741B2 (en) | 2005-11-02 | 2012-01-24 | Protiva Biotherapeutics, Inc. | Modified siRNA molecules and uses thereof |
| WO2009082817A1 (en) * | 2007-12-27 | 2009-07-09 | Protiva Biotherapeutics, Inc. | Silencing of polo-like kinase expression using interfering rna |
| WO2009086558A1 (en) * | 2008-01-02 | 2009-07-09 | Tekmira Pharmaceuticals Corporation | Improved compositions and methods for the delivery of nucleic acids |
| AU2009238175C1 (en) | 2008-04-15 | 2023-11-30 | Arbutus Biopharma Corporation | Novel lipid formulations for nucleic acid delivery |
| CN104119242B (zh) | 2008-10-09 | 2017-07-07 | 泰米拉制药公司 | 改善的氨基脂质和递送核酸的方法 |
| CA2750561C (en) | 2009-01-26 | 2017-10-10 | Protiva Biotherapeutics, Inc. | Compositions and methods for silencing apolipoprotein c-iii expression |
| US8569256B2 (en) | 2009-07-01 | 2013-10-29 | Protiva Biotherapeutics, Inc. | Cationic lipids and methods for the delivery of therapeutic agents |
| ES2613498T3 (es) | 2009-07-01 | 2017-05-24 | Protiva Biotherapeutics Inc. | Nuevas formulaciones de lípidos para el suministro de agentes terapéuticos a tumores sólidos |
| US9018187B2 (en) | 2009-07-01 | 2015-04-28 | Protiva Biotherapeutics, Inc. | Cationic lipids and methods for the delivery of therapeutic agents |
| WO2011011447A1 (en) | 2009-07-20 | 2011-01-27 | Protiva Biotherapeutics, Inc. | Compositions and methods for silencing ebola virus gene expression |
| US8455455B1 (en) | 2010-03-31 | 2013-06-04 | Protiva Biotherapeutics, Inc. | Compositions and methods for silencing genes involved in hemorrhagic fever |
| WO2012000104A1 (en) | 2010-06-30 | 2012-01-05 | Protiva Biotherapeutics, Inc. | Non-liposomal systems for nucleic acid delivery |
| US8466122B2 (en) | 2010-09-17 | 2013-06-18 | Protiva Biotherapeutics, Inc. | Trialkyl cationic lipids and methods of use thereof |
| US20120136073A1 (en) | 2010-11-15 | 2012-05-31 | Life Technologies Corporation | Amine-Containing Transfection Reagents and methods for making and using same |
| US20140308304A1 (en) * | 2011-12-07 | 2014-10-16 | Alnylam Pharmaceuticals, Inc. | Lipids for the delivery of active agents |
| EP2788006B1 (en) | 2011-12-07 | 2026-01-07 | Alnylam Pharmaceuticals, Inc. | Biodegradable lipids for the delivery of active agents |
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| US9011903B2 (en) * | 2011-06-08 | 2015-04-21 | Nitto Denko Corporation | Cationic lipids for therapeutic agent delivery formulations |
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2011
- 2011-11-15 US US13/297,231 patent/US20120136073A1/en not_active Abandoned
- 2011-11-15 BR BR122022001262-0A patent/BR122022001262B1/pt active IP Right Grant
- 2011-11-15 CN CN201810144659.2A patent/CN108358812B/zh active Active
- 2011-11-15 DK DK11793580.9T patent/DK2640700T3/en active
- 2011-11-15 WO PCT/US2011/060877 patent/WO2012068176A1/en not_active Ceased
- 2011-11-15 CN CN202110421347.3A patent/CN113214102A/zh active Pending
- 2011-11-15 JP JP2013539959A patent/JP2014508102A/ja active Pending
- 2011-11-15 EP EP11793580.9A patent/EP2640700B1/en active Active
- 2011-11-15 EP EP18202571.8A patent/EP3470395A1/en active Pending
- 2011-11-15 ES ES11793580T patent/ES2702428T3/es active Active
- 2011-11-15 CN CN201180060664.1A patent/CN103380113B/zh active Active
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2014
- 2014-07-24 US US14/340,395 patent/US9901642B2/en active Active
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2016
- 2016-09-21 JP JP2016183855A patent/JP2017031186A/ja active Pending
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2017
- 2017-12-15 US US15/844,380 patent/US10406237B2/en active Active
- 2017-12-26 JP JP2017248675A patent/JP6383480B2/ja active Active
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2018
- 2018-08-03 JP JP2018146564A patent/JP6807900B2/ja active Active
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2019
- 2019-08-30 US US16/557,967 patent/US11464863B2/en active Active
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- 2020-12-08 JP JP2020203413A patent/JP7138692B2/ja active Active
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2022
- 2022-08-19 US US17/821,122 patent/US12458700B2/en active Active
- 2022-09-06 JP JP2022141466A patent/JP7512335B2/ja active Active
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