JP2002542341A5 - - Google Patents
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- JP2002542341A5 JP2002542341A5 JP2000611949A JP2000611949A JP2002542341A5 JP 2002542341 A5 JP2002542341 A5 JP 2002542341A5 JP 2000611949 A JP2000611949 A JP 2000611949A JP 2000611949 A JP2000611949 A JP 2000611949A JP 2002542341 A5 JP2002542341 A5 JP 2002542341A5
- Authority
- JP
- Japan
- Prior art keywords
- formulation
- lipid
- compound
- group
- peg
- 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
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- 239000000203 mixture Substances 0.000 description 51
- 150000001875 compounds Chemical class 0.000 description 48
- 150000002632 lipids Chemical group 0.000 description 40
- 238000009472 formulation Methods 0.000 description 38
- 229920001223 polyethylene glycol Polymers 0.000 description 20
- 239000013583 drug formulation Substances 0.000 description 14
- 238000000034 method Methods 0.000 description 10
- 239000012867 bioactive agent Substances 0.000 description 8
- -1 phospho Chemical class 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 229920001477 hydrophilic polymer Polymers 0.000 description 5
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- 229920000954 Polyglycolide Polymers 0.000 description 4
- 241000700605 Viruses Species 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 230000002163 immunogen Effects 0.000 description 4
- 108020004707 nucleic acids Proteins 0.000 description 4
- 150000007523 nucleic acids Chemical class 0.000 description 4
- 102000039446 nucleic acids Human genes 0.000 description 4
- 229920000747 poly(lactic acid) Polymers 0.000 description 4
- 239000004633 polyglycolic acid Substances 0.000 description 4
- 239000004626 polylactic acid Substances 0.000 description 4
- 238000001890 transfection Methods 0.000 description 4
- 241000726103 Atta Species 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 3
- 229940024606 amino acid Drugs 0.000 description 3
- 235000001014 amino acid Nutrition 0.000 description 3
- 150000001413 amino acids Chemical class 0.000 description 3
- 125000002091 cationic group Chemical group 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 239000002502 liposome Substances 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- 230000000087 stabilizing effect Effects 0.000 description 3
- 239000004475 Arginine Substances 0.000 description 2
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 2
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 description 2
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 2
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 2
- 239000004472 Lysine Substances 0.000 description 2
- 108091034117 Oligonucleotide Proteins 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- RJURFGZVJUQBHK-UHFFFAOYSA-N actinomycin D Natural products CC1OC(=O)C(C(C)C)N(C)C(=O)CN(C)C(=O)C2CCCN2C(=O)C(C(C)C)NC(=O)C1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)NC4C(=O)NC(C(N5CCCC5C(=O)N(C)CC(=O)N(C)C(C(C)C)C(=O)OC4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 239000002246 antineoplastic agent Substances 0.000 description 2
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 2
- 229960001230 asparagine Drugs 0.000 description 2
- 235000009582 asparagine Nutrition 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000002068 genetic effect Effects 0.000 description 2
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 2
- 230000003834 intracellular effect Effects 0.000 description 2
- 210000004088 microvessel Anatomy 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 108010092160 Dactinomycin Proteins 0.000 description 1
- OOFLZRMKTMLSMH-UHFFFAOYSA-N H4atta Chemical compound OC(=O)CN(CC(O)=O)CC1=CC=CC(C=2N=C(C=C(C=2)C=2C3=CC=CC=C3C=C3C=CC=CC3=2)C=2N=C(CN(CC(O)=O)CC(O)=O)C=CC=2)=N1 OOFLZRMKTMLSMH-UHFFFAOYSA-N 0.000 description 1
- FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 description 1
- 101710163270 Nuclease Proteins 0.000 description 1
- JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 description 1
- RJURFGZVJUQBHK-IIXSONLDSA-N actinomycin D Chemical group C[C@H]1OC(=O)[C@H](C(C)C)N(C)C(=O)CN(C)C(=O)[C@@H]2CCCN2C(=O)[C@@H](C(C)C)NC(=O)[C@H]1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)N[C@@H]4C(=O)N[C@@H](C(N5CCC[C@H]5C(=O)N(C)CC(=O)N(C)[C@@H](C(C)C)C(=O)O[C@@H]4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-IIXSONLDSA-N 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 229940045799 anthracyclines and related substance Drugs 0.000 description 1
- 229940034982 antineoplastic agent Drugs 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229960003067 cystine Drugs 0.000 description 1
- 229960000640 dactinomycin Drugs 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 229960000485 methotrexate Drugs 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- 239000002777 nucleoside Substances 0.000 description 1
- 150000003833 nucleoside derivatives Chemical class 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 150000003058 platinum compounds Chemical class 0.000 description 1
- 125000000561 purinyl group Chemical class N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 229960003048 vinblastine Drugs 0.000 description 1
- JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 1
- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 1
- 229960004528 vincristine Drugs 0.000 description 1
- OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 1
- 239000000277 virosome Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13015199P | 1999-04-20 | 1999-04-20 | |
| US60/130,151 | 1999-04-20 | ||
| PCT/CA2000/000451 WO2000062813A2 (en) | 1999-04-20 | 2000-04-20 | Cationic peg-lipids and methods of use |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012017765A Division JP2012122075A (ja) | 1999-04-20 | 2012-01-31 | カチオン性ｐｅｇ脂質および使用方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2002542341A JP2002542341A (ja) | 2002-12-10 |
| JP2002542341A5 true JP2002542341A5 (enExample) | 2007-06-07 |
| JP5117648B2 JP5117648B2 (ja) | 2013-01-16 |
Family
ID=22443303
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000611949A Expired - Fee Related JP5117648B2 (ja) | 1999-04-20 | 2000-04-20 | カチオン性ｐｅｇ脂質および使用方法。 |
| JP2012017765A Pending JP2012122075A (ja) | 1999-04-20 | 2012-01-31 | カチオン性ｐｅｇ脂質および使用方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012017765A Pending JP2012122075A (ja) | 1999-04-20 | 2012-01-31 | カチオン性ｐｅｇ脂質および使用方法 |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP1173600A2 (enExample) |
| JP (2) | JP5117648B2 (enExample) |
| AU (1) | AU783647B2 (enExample) |
| CA (1) | CA2370690A1 (enExample) |
| WO (1) | WO2000062813A2 (enExample) |
Families Citing this family (64)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69841002D1 (de) | 1997-05-14 | 2009-09-03 | Univ British Columbia | Hochwirksame verkapselung von nukleinsäuren in lipidvesikeln |
| JP2004508012A (ja) * | 2000-04-20 | 2004-03-18 | ザ ユニバーシティ オブ ブリティッシュ コロンビア | エンドソーム膜不安定剤を用いたｓｐｌｐ媒介性トランスフェクションの強化方法 |
| US7189705B2 (en) | 2000-04-20 | 2007-03-13 | The University Of British Columbia | Methods of enhancing SPLP-mediated transfection using endosomal membrane destabilizers |
| AU2002214854A1 (en) * | 2000-10-25 | 2002-05-06 | Inex Pharmaceuticals Corporation | Lipid formulations for target delivery |
| US6610322B1 (en) * | 2000-12-20 | 2003-08-26 | Brian Charles Keller | Self forming, thermodynamically stable liposomes and their applications |
| US7901708B2 (en) | 2002-06-28 | 2011-03-08 | Protiva Biotherapeutics, Inc. | Liposomal apparatus and manufacturing methods |
| WO2004082626A2 (en) * | 2003-03-18 | 2004-09-30 | Ethicon, Inc. | Aromatase inhibitor diagnosis and therapy |
| SG190613A1 (en) | 2003-07-16 | 2013-06-28 | Protiva Biotherapeutics Inc | Lipid encapsulated interfering rna |
| EP1664316B1 (en) * | 2003-09-15 | 2012-08-29 | Protiva Biotherapeutics Inc. | Polyethyleneglycol-modified lipid compounds and uses thereof |
| FR2870741B1 (fr) * | 2004-05-25 | 2008-03-14 | Coletica Sa | Phase lamellaires hydratees ou liposomes, contenant une monoamine grasse ou un polymere cationique favorisant la penetration intercellulaire, et composition cosmetique ou pharmaceutique la contenant. |
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| US8765181B2 (en) * | 2005-09-09 | 2014-07-01 | Beijing Diacrid Medical Technology Co., Ltd | Nano anticancer micelles of vinca alkaloids entrapped in polyethylene glycolylated phospholipids |
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| US10077232B2 (en) | 2010-05-12 | 2018-09-18 | Arbutus Biopharma Corporation | Cyclic cationic lipids and methods of use |
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| AU2011268146A1 (en) | 2010-06-17 | 2013-01-10 | Actogenix Nv | Compositions and methods for treating inflammatory conditions |
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| EP4653462A2 (en) | 2016-08-22 | 2025-11-26 | Arbutus Biopharma Corporation | Anti-pd-1 antibodies, or fragments thereof, for treating hepatitis b |
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| AU2023275780A1 (en) | 2022-05-25 | 2024-12-05 | Akagera Medicines, Inc. | Lipid nanoparticles for delivery of nucleic acids and methods of use thereof |
| WO2024214632A1 (ja) * | 2023-04-14 | 2024-10-17 | 国立大学法人 東京大学 | ホスホニウム基を有するカチオン性ポリマーおよびこれを含むポリマー粒子または医薬組成物 |
| WO2025052278A1 (en) | 2023-09-05 | 2025-03-13 | Genevant Sciences Gmbh | Pyrrolidine based cationic lipids for lipid nanoparticle delivery of therapeutics to hepatic stellate cells |
| WO2025158420A1 (en) | 2024-01-25 | 2025-07-31 | Nanocell Therapeutics Holdings B.V. | Methods and composition for inducing activation and dna expression in t-cells |
| WO2025169168A1 (en) | 2024-02-09 | 2025-08-14 | Nanocell Therapeutics Holdings B.V. | Extracorporeal transfection of immune effector cells |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69632401T2 (de) * | 1995-06-07 | 2005-05-19 | Imarx Pharmaceutical Corp., Tucson | Neue zielgerichtete mittel zur diagnostischen und therapeutischen verwendung |
| EP0932390A1 (en) * | 1996-10-11 | 1999-08-04 | Sequus Pharmaceuticals, Inc. | Therapeutic liposome composition and method |
| TW520297B (en) * | 1996-10-11 | 2003-02-11 | Sequus Pharm Inc | Fusogenic liposome composition and method |
| WO1998046208A1 (en) * | 1997-04-17 | 1998-10-22 | The Regents Of The University Of Michigan | Hair follicle dna delivery system |
| AU7490098A (en) * | 1997-05-15 | 1998-12-08 | Genzyme Corporation | Cationic amphiphile formulations |
| US6395713B1 (en) * | 1997-07-23 | 2002-05-28 | Ribozyme Pharmaceuticals, Inc. | Compositions for the delivery of negatively charged molecules |
| US6110745A (en) * | 1997-07-24 | 2000-08-29 | Inex Pharmaceuticals Corp. | Preparation of lipid-nucleic acid particles using a solvent extraction and direct hydration method |
| WO1999065461A2 (en) * | 1998-06-19 | 1999-12-23 | Genzyme Corporation | Cationic amphiphile micellar complexes |
| AU2620000A (en) * | 1999-01-21 | 2000-08-07 | Georgetown University | Ligand-peg post-coating stabilized lipoplex and polyplex for targeted gene delivery |
| EP1046394A3 (en) * | 1999-04-19 | 2001-10-10 | ImaRx Pharmaceutical Corp. | Novel compositions useful for delivering compounds into a cell |
| AU2001236062A1 (en) * | 2000-03-02 | 2001-09-12 | Yasuo Ikeda | Gpib-lipid bond construct and use thereof |
-
2000
- 2000-04-20 AU AU40962/00A patent/AU783647B2/en not_active Ceased
- 2000-04-20 WO PCT/CA2000/000451 patent/WO2000062813A2/en not_active Ceased
- 2000-04-20 CA CA002370690A patent/CA2370690A1/en not_active Abandoned
- 2000-04-20 EP EP00920309A patent/EP1173600A2/en not_active Withdrawn
- 2000-04-20 JP JP2000611949A patent/JP5117648B2/ja not_active Expired - Fee Related
-
2012
- 2012-01-31 JP JP2012017765A patent/JP2012122075A/ja active Pending
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