CA2627657A1 - A method for preparing liposomes and uses thereof - Google Patents
A method for preparing liposomes and uses thereof Download PDFInfo
- Publication number
- CA2627657A1 CA2627657A1 CA002627657A CA2627657A CA2627657A1 CA 2627657 A1 CA2627657 A1 CA 2627657A1 CA 002627657 A CA002627657 A CA 002627657A CA 2627657 A CA2627657 A CA 2627657A CA 2627657 A1 CA2627657 A1 CA 2627657A1
- Authority
- CA
- Canada
- Prior art keywords
- liposome
- liposomes
- lipid
- agent
- forming lipid
- 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.)
- Abandoned
Links
- 239000002502 liposome Substances 0.000 title claims abstract description 220
- 238000000034 method Methods 0.000 title claims abstract description 78
- 150000002632 lipids Chemical class 0.000 claims abstract description 161
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 56
- 239000000203 mixture Substances 0.000 claims abstract description 44
- 239000000243 solution Substances 0.000 claims abstract description 37
- 239000000725 suspension Substances 0.000 claims abstract description 32
- 150000002500 ions Chemical class 0.000 claims abstract description 26
- 239000003960 organic solvent Substances 0.000 claims abstract description 24
- 239000002253 acid Substances 0.000 claims abstract description 23
- 239000006185 dispersion Substances 0.000 claims abstract description 23
- 239000007864 aqueous solution Substances 0.000 claims abstract description 19
- 239000002691 unilamellar liposome Substances 0.000 claims abstract description 8
- 238000001035 drying Methods 0.000 claims abstract description 5
- 238000004513 sizing Methods 0.000 claims abstract description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 28
- 239000012528 membrane Substances 0.000 claims description 18
- 150000003904 phospholipids Chemical class 0.000 claims description 18
- 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 description 16
- 238000010257 thawing Methods 0.000 claims description 9
- 235000012000 cholesterol Nutrition 0.000 claims description 8
- 150000003863 ammonium salts Chemical class 0.000 claims description 7
- 230000008014 freezing Effects 0.000 claims description 7
- 238000007710 freezing Methods 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 159000000021 acetate salts Chemical class 0.000 claims description 4
- 238000011534 incubation Methods 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 3
- 150000008105 phosphatidylcholines Chemical class 0.000 claims description 2
- 239000003814 drug Substances 0.000 abstract description 50
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- 238000011068 loading method Methods 0.000 abstract description 29
- 239000013543 active substance Substances 0.000 abstract description 11
- LEBVLXFERQHONN-UHFFFAOYSA-N 1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide Chemical compound CCCCN1CCCCC1C(=O)NC1=C(C)C=CC=C1C LEBVLXFERQHONN-UHFFFAOYSA-N 0.000 description 31
- 229960003150 bupivacaine Drugs 0.000 description 30
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- 239000002202 Polyethylene glycol Substances 0.000 description 12
- 229920001223 polyethylene glycol Polymers 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- 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 description 11
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- 238000002474 experimental method Methods 0.000 description 9
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- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 8
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- PFNFFQXMRSDOHW-UHFFFAOYSA-N spermine Chemical compound NCCCNCCCCNCCCN PFNFFQXMRSDOHW-UHFFFAOYSA-N 0.000 description 8
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- LRYZPFWEZHSTHD-HEFFAWAOSA-O 2-[[(e,2s,3r)-2-formamido-3-hydroxyoctadec-4-enoxy]-hydroxyphosphoryl]oxyethyl-trimethylazanium Chemical class CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](NC=O)COP(O)(=O)OCC[N+](C)(C)C LRYZPFWEZHSTHD-HEFFAWAOSA-O 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
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- CITHEXJVPOWHKC-UUWRZZSWSA-N 1,2-di-O-myristoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCC CITHEXJVPOWHKC-UUWRZZSWSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
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- 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 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
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- PORPENFLTBBHSG-MGBGTMOVSA-N 1,2-dihexadecanoyl-sn-glycerol-3-phosphate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCC PORPENFLTBBHSG-MGBGTMOVSA-N 0.000 description 2
- IRQUJNVGEAJGSD-WUOGMODZSA-N 4-[[(8r,9s,10r,13s,14s,17s)-13-methyl-3-oxo-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-17-yl]oxy]-4-oxobutanoic acid Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@H](CC4)OC(=O)CCC(O)=O)[C@@H]4[C@@H]3CCC2=C1 IRQUJNVGEAJGSD-WUOGMODZSA-N 0.000 description 2
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/127—Liposomes
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/127—Liposomes
- A61K9/1277—Processes for preparing; Proliposomes
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Dispersion Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Manufacturing Of Micro-Capsules (AREA)
Applications Claiming Priority (3)
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|---|---|---|---|
| US73004505P | 2005-10-26 | 2005-10-26 | |
| US60/730,045 | 2005-10-26 | ||
| PCT/IL2006/001229 WO2007049278A2 (en) | 2005-10-26 | 2006-10-26 | A method for preparing liposomes and uses thereof |
Publications (1)
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|---|---|
| CA2627657A1 true CA2627657A1 (en) | 2007-05-03 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002627657A Abandoned CA2627657A1 (en) | 2005-10-26 | 2006-10-26 | A method for preparing liposomes and uses thereof |
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| EP (1) | EP1954243A2 (ja) |
| JP (1) | JP2009513621A (ja) |
| AU (1) | AU2006307460A1 (ja) |
| CA (1) | CA2627657A1 (ja) |
| WO (1) | WO2007049278A2 (ja) |
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| JP5107573B2 (ja) | 2003-04-25 | 2012-12-26 | ザ ペン ステイト リサーチ ファウンデーション | 増殖抑制性脂質由来生物活性化合物の全身送達方法およびシステム |
| EP2368627A4 (en) * | 2008-12-24 | 2015-01-14 | Biomedcore Inc | METHOD FOR MANUFACTURING LIPOSOME AND METHOD FOR DISSOLVING CHOLESTEROL |
| US20130052259A1 (en) * | 2010-02-01 | 2013-02-28 | Yechezkel Barenholz | Liposomes comprising amphipathic drugs and method for their preparation |
| US10610486B2 (en) | 2010-10-28 | 2020-04-07 | Pacira Pharmaceuticals, Inc. | Sustained release formulation of a non-steroidal anti-inflammatory drug |
| BR112013024663A2 (pt) * | 2011-03-25 | 2016-12-20 | Terumo Corp | composição de lipossomas de liberação controlada de longa duração e método para produção da mesma |
| JPWO2014046191A1 (ja) * | 2012-09-21 | 2016-08-18 | テルモ株式会社 | 局所麻酔薬持続徐放性リポソーム製剤 |
| ES2777223T3 (es) * | 2013-03-15 | 2020-08-04 | Taiwan Liposome Co Ltd | Composición de liposoma para liberación controlada de fármaco |
| US10220095B2 (en) | 2013-03-15 | 2019-03-05 | Taiwan Liposome Company, Ltd | Controlled drug release liposome compositions and methods thereof |
| CN104906586A (zh) * | 2014-03-10 | 2015-09-16 | 中国科学院上海药物研究所 | 一种盐酸伊立替康复合磷脂组合物、制备方法及其应用 |
| JP6866060B2 (ja) * | 2014-10-27 | 2021-04-28 | 花王株式会社 | 精製茶抽出物の製造方法 |
| EP3302435B1 (en) | 2015-05-26 | 2023-03-08 | Plumb Pharmaceuticals, Inc. | Liposome loading |
| CN106619516B (zh) * | 2016-10-10 | 2020-07-03 | 常州金远药业制造有限公司 | 一种小分子靶向药物脂质体制剂的制备方法 |
| CN109983013A (zh) | 2016-11-18 | 2019-07-05 | 帕西拉制药有限公司 | 美洛昔康锌复合物微粒多囊脂质体制剂及其制备方法 |
| US11964050B2 (en) * | 2017-07-24 | 2024-04-23 | Pharmosa Biopharm Inc. | Liposome compositions comprising weak acid drugs and uses thereof |
| EP3790554A4 (en) | 2018-05-07 | 2022-03-30 | Pharmosa Biopharm Inc. | CONTROLLED RELEASE PHARMACEUTICAL COMPOSITION FOR TREPROSTINIL |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4485054A (en) * | 1982-10-04 | 1984-11-27 | Lipoderm Pharmaceuticals Limited | Method of encapsulating biologically active materials in multilamellar lipid vesicles (MLV) |
| US5169637A (en) * | 1983-03-24 | 1992-12-08 | The Liposome Company, Inc. | Stable plurilamellar vesicles |
| GB8322178D0 (en) * | 1983-08-17 | 1983-09-21 | Sterwin Ag | Preparing aerosol compositions |
| SE8603812D0 (sv) * | 1986-09-12 | 1986-09-12 | Draco Ab | Administration of liposomes to mammals |
| US5702722A (en) * | 1994-09-30 | 1997-12-30 | Bracco Research S.A. | Liposomes with enhanced entrapment capacity, method and use |
-
2006
- 2006-10-26 JP JP2008537312A patent/JP2009513621A/ja active Pending
- 2006-10-26 EP EP06809790A patent/EP1954243A2/en not_active Withdrawn
- 2006-10-26 WO PCT/IL2006/001229 patent/WO2007049278A2/en active Application Filing
- 2006-10-26 AU AU2006307460A patent/AU2006307460A1/en not_active Abandoned
- 2006-10-26 CA CA002627657A patent/CA2627657A1/en not_active Abandoned
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| WO2007049278A3 (en) | 2007-09-13 |
| WO2007049278A2 (en) | 2007-05-03 |
| JP2009513621A (ja) | 2009-04-02 |
| EP1954243A2 (en) | 2008-08-13 |
| AU2006307460A1 (en) | 2007-05-03 |
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