JPWO2020252589A5 - - Google Patents
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- Publication number
- JPWO2020252589A5 JPWO2020252589A5 JP2021574974A JP2021574974A JPWO2020252589A5 JP WO2020252589 A5 JPWO2020252589 A5 JP WO2020252589A5 JP 2021574974 A JP2021574974 A JP 2021574974A JP 2021574974 A JP2021574974 A JP 2021574974A JP WO2020252589 A5 JPWO2020252589 A5 JP WO2020252589A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- alkenyl
- independently
- alkynyl
- bond
- 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.)
- Granted
Links
- 229910052739 hydrogen Inorganic materials 0.000 claims 21
- 125000000217 alkyl group Chemical group 0.000 claims 17
- 229910052799 carbon Inorganic materials 0.000 claims 10
- 239000000203 mixture Substances 0.000 claims 10
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 9
- 150000002632 lipids Chemical class 0.000 claims 9
- 150000001875 compounds Chemical class 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 6
- 125000000304 alkynyl group Chemical group 0.000 claims 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 4
- 239000003381 stabilizer Substances 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims 3
- 125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims 3
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims 3
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims 3
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims 3
- 125000001843 C4-C10 alkenyl group Chemical group 0.000 claims 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 3
- -1 polyoxyethylene Polymers 0.000 claims 3
- 125000006833 (C1-C5) alkylene group Chemical group 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- CMCBDXRRFKYBDG-UHFFFAOYSA-N 1-dodecoxydodecane Chemical compound CCCCCCCCCCCCOCCCCCCCCCCCC CMCBDXRRFKYBDG-UHFFFAOYSA-N 0.000 claims 2
- HBXWUCXDUUJDRB-UHFFFAOYSA-N 1-octadecoxyoctadecane Chemical compound CCCCCCCCCCCCCCCCCCOCCCCCCCCCCCCCCCCCC HBXWUCXDUUJDRB-UHFFFAOYSA-N 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 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 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000006730 (C2-C5) alkynyl group Chemical group 0.000 claims 1
- 125000006661 (C4-C6) heterocyclic group Chemical group 0.000 claims 1
- LVNGJLRDBYCPGB-LDLOPFEMSA-N (R)-1,2-distearoylphosphatidylethanolamine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[NH3+])OC(=O)CCCCCCCCCCCCCCCCC LVNGJLRDBYCPGB-LDLOPFEMSA-N 0.000 claims 1
- 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 1
- SNKAWJBJQDLSFF-NVKMUCNASA-N 1,2-dioleoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/CCCCCCCC SNKAWJBJQDLSFF-NVKMUCNASA-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
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- GZDFHIJNHHMENY-UHFFFAOYSA-N Dimethyl dicarbonate Chemical compound COC(=O)OC(=O)OC GZDFHIJNHHMENY-UHFFFAOYSA-N 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 235000012000 cholesterol Nutrition 0.000 claims 1
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims 1
- DTPCFIHYWYONMD-UHFFFAOYSA-N decaethylene glycol Polymers OCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO DTPCFIHYWYONMD-UHFFFAOYSA-N 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 239000002105 nanoparticle Substances 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 239000002245 particle Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 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 1
- 229940113116 polyethylene glycol 1000 Drugs 0.000 claims 1
- 229920000642 polymer Polymers 0.000 claims 1
- 235000011185 polyoxyethylene (40) stearate Nutrition 0.000 claims 1
- 239000001194 polyoxyethylene (40) stearate Substances 0.000 claims 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 claims 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 claims 1
- 229920000053 polysorbate 80 Polymers 0.000 claims 1
- 229940068968 polysorbate 80 Drugs 0.000 claims 1
- 150000003431 steroids Chemical class 0.000 claims 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- 229960000984 tocofersolan Drugs 0.000 claims 1
- 239000002076 α-tocopherol Substances 0.000 claims 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 claims 1
- 235000004835 α-tocopherol Nutrition 0.000 claims 1
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201962864064P | 2019-06-20 | 2019-06-20 | |
| US62/864,064 | 2019-06-20 | ||
| US201962877536P | 2019-07-23 | 2019-07-23 | |
| US62/877,536 | 2019-07-23 | ||
| US202063009104P | 2020-04-13 | 2020-04-13 | |
| US63/009,104 | 2020-04-13 | ||
| PCT/CA2020/050854 WO2020252589A1 (en) | 2019-06-20 | 2020-06-19 | Ionizable lipids for nucleic acid delivery |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2022537305A JP2022537305A (ja) | 2022-08-25 |
| JPWO2020252589A5 true JPWO2020252589A5 (da) | 2023-06-26 |
| JP7416096B2 JP7416096B2 (ja) | 2024-01-17 |
Family
ID=74036881
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021574974A Active JP7416096B2 (ja) | 2019-06-20 | 2020-06-19 | 核酸送達のためのイオン化可能な脂質 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US20220396548A1 (da) |
| EP (1) | EP3986866B1 (da) |
| JP (1) | JP7416096B2 (da) |
| KR (1) | KR102568997B1 (da) |
| CN (1) | CN114746401B (da) |
| CA (1) | CA3143577C (da) |
| DK (1) | DK3986866T3 (da) |
| ES (1) | ES2973521T3 (da) |
| WO (1) | WO2020252589A1 (da) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT3864163T (pt) | 2018-10-09 | 2024-04-30 | Univ British Columbia | Composições e sistemas que compreendem vesículas competentes para transfeção isentas de solventes orgânicos e detergentes e métodos relacionados com as mesmas |
| EP4251170A1 (en) | 2020-11-25 | 2023-10-04 | Akagera Medicines, Inc. | Lipid nanoparticles for delivery of nucleic acids, and related methods of use |
| CN114149337B (zh) * | 2021-07-07 | 2022-04-29 | 天津键凯科技有限公司 | 一种用于核酸递送的新型可电离脂质及其lnp组合物 |
| EP4379055A1 (en) | 2021-07-27 | 2024-06-05 | SK Bioscience Co., Ltd. | Mrna for protein expression and template therefor |
| CN115772089A (zh) * | 2021-09-07 | 2023-03-10 | 广州谷森制药有限公司 | 新型阳离子脂质化合物 |
| US11510975B1 (en) | 2021-11-29 | 2022-11-29 | Replicate Bioscience, Inc. | Compositions and methods for inducing ESR1, PI3K, HER2, and HER3 immune responses |
| US12064479B2 (en) | 2022-05-25 | 2024-08-20 | Akagera Medicines, Inc. | Lipid nanoparticles for delivery of nucleic acids and methods of use thereof |
| WO2024006863A1 (en) | 2022-06-30 | 2024-01-04 | Precision NanoSystems ULC | Lipid nanoparticle formulations for vaccines |
| WO2024126423A1 (en) | 2022-12-12 | 2024-06-20 | Precision NanoSystems ULC | Lipid nanoparticles lyophilization methods and compositions |
| KR20240096964A (ko) * | 2022-12-19 | 2024-06-27 | 주식회사 녹십자 | 핵산 전달용 사이클로알칸계 지질 화합물 및 이를 포함하는 지질 나노입자 |
| WO2024133635A1 (en) | 2022-12-23 | 2024-06-27 | Biontech Delivery Technologies Gmbh | Composition |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1539268A (en) * | 1976-12-23 | 1979-01-31 | Ici Ltd | Prostane derivatives |
| JPH0822830B2 (ja) * | 1988-10-19 | 1996-03-06 | 長谷川香料株式会社 | ２（ｚ）−ペンテニル置換シクロペンタン類およびその新規中間体 |
| JP2743198B2 (ja) * | 1989-09-26 | 1998-04-22 | 長谷川香料株式会社 | シクロペンタン類 |
| WO2008109238A1 (en) | 2007-03-02 | 2008-09-12 | Janssen Pharmaceutica N.V. | Substituted cyclopentyl piperidine ccr2 antagonists |
| EP3100718B1 (en) | 2008-01-02 | 2019-11-27 | Arbutus Biopharma Corporation | Improved compositions and methods for the delivery of nucleic acids |
| EP3808177A1 (en) * | 2008-11-10 | 2021-04-21 | Arbutus Biopharma Corporation | Novel lipids and compositions for the delivery of therapeutics |
| JP2014001142A (ja) | 2010-10-05 | 2014-01-09 | Astellas Pharma Inc | シクロアルカン化合物 |
| WO2018232502A1 (en) * | 2017-06-20 | 2018-12-27 | Rjh Biosciences Inc. | TRANSFECTION REAGENTS FOR NUCLEIC ACID ADMINISTRATION |
| WO2019182527A1 (en) | 2018-03-21 | 2019-09-26 | T.C. Istanbul Medipol Universitesi | Methyl jasmonate derivatives as possible drug candidates for use in treatment of cancer |
-
2020
- 2020-06-19 US US17/620,575 patent/US20220396548A1/en active Pending
- 2020-06-19 ES ES20826513T patent/ES2973521T3/es active Active
- 2020-06-19 DK DK20826513.2T patent/DK3986866T3/da active
- 2020-06-19 KR KR1020227002023A patent/KR102568997B1/ko active IP Right Grant
- 2020-06-19 JP JP2021574974A patent/JP7416096B2/ja active Active
- 2020-06-19 CA CA3143577A patent/CA3143577C/en active Active
- 2020-06-19 EP EP20826513.2A patent/EP3986866B1/en active Active
- 2020-06-19 WO PCT/CA2020/050854 patent/WO2020252589A1/en active Application Filing
- 2020-06-19 CN CN202080045008.3A patent/CN114746401B/zh active Active
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