AU2012297589C1 - Liposomal compositions - Google Patents
Liposomal compositions Download PDFInfo
- Publication number
- AU2012297589C1 AU2012297589C1 AU2012297589A AU2012297589A AU2012297589C1 AU 2012297589 C1 AU2012297589 C1 AU 2012297589C1 AU 2012297589 A AU2012297589 A AU 2012297589A AU 2012297589 A AU2012297589 A AU 2012297589A AU 2012297589 C1 AU2012297589 C1 AU 2012297589C1
- Authority
- AU
- Australia
- Prior art keywords
- composition
- liposomes
- chlorite
- glycero
- chlorate
- 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.)
- Ceased
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- 239000000203 mixture Substances 0.000 title claims abstract description 418
- 239000002502 liposome Substances 0.000 claims abstract description 350
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 claims abstract description 321
- 229910001919 chlorite Inorganic materials 0.000 claims abstract description 236
- 229910052619 chlorite group Inorganic materials 0.000 claims abstract description 236
- QBWCMBCROVPCKQ-UHFFFAOYSA-N chlorous acid Chemical compound OCl=O QBWCMBCROVPCKQ-UHFFFAOYSA-N 0.000 claims abstract description 224
- 238000000034 method Methods 0.000 claims abstract description 184
- 239000003814 drug Substances 0.000 claims abstract description 24
- 150000002632 lipids Chemical class 0.000 claims description 193
- 239000000243 solution Substances 0.000 claims description 139
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 97
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 92
- 238000011282 treatment Methods 0.000 claims description 57
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 56
- 239000011780 sodium chloride Substances 0.000 claims description 45
- 238000003860 storage Methods 0.000 claims description 44
- 239000000232 Lipid Bilayer Substances 0.000 claims description 38
- 201000010099 disease Diseases 0.000 claims description 32
- 238000002347 injection Methods 0.000 claims description 27
- 239000007924 injection Substances 0.000 claims description 27
- 206010028980 Neoplasm Diseases 0.000 claims description 26
- 150000002500 ions Chemical class 0.000 claims description 26
- 208000035475 disorder Diseases 0.000 claims description 24
- 239000008194 pharmaceutical composition Substances 0.000 claims description 21
- 229920001223 polyethylene glycol Polymers 0.000 claims description 21
- 150000003904 phospholipids Chemical class 0.000 claims description 20
- BIABMEZBCHDPBV-UHFFFAOYSA-N dipalmitoyl phosphatidylglycerol Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(COP(O)(=O)OCC(O)CO)OC(=O)CCCCCCCCCCCCCCC BIABMEZBCHDPBV-UHFFFAOYSA-N 0.000 claims description 19
- 201000011510 cancer Diseases 0.000 claims description 18
- 210000002540 macrophage Anatomy 0.000 claims description 18
- 239000000047 product Substances 0.000 claims description 17
- 230000008685 targeting Effects 0.000 claims description 17
- 239000000463 material Substances 0.000 claims description 15
- 239000007864 aqueous solution Substances 0.000 claims description 14
- 230000009286 beneficial effect Effects 0.000 claims description 13
- 210000004027 cell Anatomy 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 13
- SUHOQUVVVLNYQR-MRVPVSSYSA-O glycerylphosphorylcholine Chemical compound C[N+](C)(C)CCO[P@](O)(=O)OC[C@H](O)CO SUHOQUVVVLNYQR-MRVPVSSYSA-O 0.000 claims description 12
- 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 description 12
- 230000001225 therapeutic effect Effects 0.000 claims description 11
- AWUCVROLDVIAJX-UHFFFAOYSA-N alpha-glycerophosphate Natural products OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 claims description 10
- 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 10
- 230000028993 immune response Effects 0.000 claims description 10
- 150000003408 sphingolipids Chemical class 0.000 claims description 10
- 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 description 8
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- ZWZWYGMENQVNFU-UHFFFAOYSA-N Glycerophosphorylserin Natural products OC(=O)C(N)COP(O)(=O)OCC(O)CO ZWZWYGMENQVNFU-UHFFFAOYSA-N 0.000 claims description 7
- 206010039085 Rhinitis allergic Diseases 0.000 claims description 7
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- 239000008344 egg yolk phospholipid Substances 0.000 claims description 7
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- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- 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 description 5
- TYAQXZHDAGZOEO-KXQOOQHDSA-N 1-myristoyl-2-stearoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCCC(=O)O[C@@H](COP([O-])(=O)OCC[N+](C)(C)C)COC(=O)CCCCCCCCCCCCC TYAQXZHDAGZOEO-KXQOOQHDSA-N 0.000 claims description 5
- JZNWSCPGTDBMEW-UHFFFAOYSA-N Glycerophosphorylethanolamin Natural products NCCOP(O)(=O)OCC(O)CO JZNWSCPGTDBMEW-UHFFFAOYSA-N 0.000 claims description 5
- 230000001363 autoimmune Effects 0.000 claims description 5
- 210000000481 breast Anatomy 0.000 claims description 5
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- 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 description 4
- DSNRWDQKZIEDDB-SQYFZQSCSA-N 1,2-dioleoyl-sn-glycero-3-phospho-(1'-sn-glycerol) Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@@H](O)CO)OC(=O)CCCCCCC\C=C/CCCCCCCC DSNRWDQKZIEDDB-SQYFZQSCSA-N 0.000 claims description 4
- PZNPLUBHRSSFHT-RRHRGVEJSA-N 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCCC(=O)O[C@@H](COP([O-])(=O)OCC[N+](C)(C)C)COC(=O)CCCCCCCCCCCCCCC PZNPLUBHRSSFHT-RRHRGVEJSA-N 0.000 claims description 4
- MZWGYEJOZNRLQE-KXQOOQHDSA-N 1-stearoyl-2-myristoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCC MZWGYEJOZNRLQE-KXQOOQHDSA-N 0.000 claims description 4
- ATHVAWFAEPLPPQ-VRDBWYNSSA-N 1-stearoyl-2-oleoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/CCCCCCCC ATHVAWFAEPLPPQ-VRDBWYNSSA-N 0.000 claims description 4
- YKIOPDIXYAUOFN-UHFFFAOYSA-N 2,3-di(icosanoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphate Chemical compound CCCCCCCCCCCCCCCCCCCC(=O)OCC(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCCCC YKIOPDIXYAUOFN-UHFFFAOYSA-N 0.000 claims description 4
- 208000026310 Breast neoplasm Diseases 0.000 claims description 4
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 4
- 208000031886 HIV Infections Diseases 0.000 claims description 4
- 208000037357 HIV infectious disease Diseases 0.000 claims description 4
- BPHQZTVXXXJVHI-IADGFXSZSA-N [(2r)-3-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-2-tetradecanoyloxypropyl] tetradecanoate Chemical compound CCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OCC(O)CO)OC(=O)CCCCCCCCCCCCC BPHQZTVXXXJVHI-IADGFXSZSA-N 0.000 claims description 4
- 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 description 4
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- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 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 description 3
- BHYOQNUELFTYRT-UHFFFAOYSA-N Cholesterol sulfate Natural products C1C=C2CC(OS(O)(=O)=O)CCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 BHYOQNUELFTYRT-UHFFFAOYSA-N 0.000 claims description 3
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- 239000002202 Polyethylene glycol Substances 0.000 claims description 3
- BHYOQNUELFTYRT-DPAQBDIFSA-N cholesterol sulfate Chemical compound C1C=C2C[C@@H](OS(O)(=O)=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 BHYOQNUELFTYRT-DPAQBDIFSA-N 0.000 claims description 3
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- 150000008104 phosphatidylethanolamines Chemical class 0.000 claims description 3
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- SDEURMLKLAEUAY-JFSPZUDSSA-N (2-{[(2r)-2,3-bis[(13z)-docos-13-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCC\C=C/CCCCCCCC SDEURMLKLAEUAY-JFSPZUDSSA-N 0.000 claims description 2
- 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 claims description 2
- 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 description 2
- BYSIMVBIJVBVPA-RRHRGVEJSA-N 1-stearoyl-2-palmitoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCC BYSIMVBIJVBVPA-RRHRGVEJSA-N 0.000 claims description 2
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- SXZWBNWTCVLZJN-NMIJJABPSA-N N-tricosanoylsphing-4-enine-1-phosphocholine Chemical compound CCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@@H](COP([O-])(=O)OCC[N+](C)(C)C)[C@H](O)\C=C\CCCCCCCCCCCCC SXZWBNWTCVLZJN-NMIJJABPSA-N 0.000 claims description 2
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- FVJZSBGHRPJMMA-UHFFFAOYSA-N distearoyl phosphatidylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(COP(O)(=O)OCC(O)CO)OC(=O)CCCCCCCCCCCCCCCCC FVJZSBGHRPJMMA-UHFFFAOYSA-N 0.000 claims 2
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| AU2006322076C1 (en) | 2005-12-08 | 2013-11-14 | Insmed Incorporated | Lipid-based compositions of antiinfectives for treating pulmonary infections |
| US9119783B2 (en) | 2007-05-07 | 2015-09-01 | Insmed Incorporated | Method of treating pulmonary disorders with liposomal amikacin formulations |
| WO2014037927A1 (en) * | 2012-09-10 | 2014-03-13 | Nuvo Research Gmbh | Chlorate compositions and use of chlorate for treating radiation exposure |
| ES2743039T3 (es) | 2012-11-29 | 2020-02-18 | Insmed Inc | Formulaciones de vancomicina estabilizada |
| US9603799B2 (en) | 2013-03-15 | 2017-03-28 | Htd Biosystems Inc. | Liposomal vaccine adjuvants and methods of making and using same |
| US20140271815A1 (en) * | 2013-03-15 | 2014-09-18 | Aryo Sorayya | Heat-and freeze-stable vaccines and methods of making and using same |
| EP3466432B1 (en) | 2014-05-15 | 2020-07-08 | Insmed Incorporated | Methods for treating pulmonary non-tuberculous mycobacterial infections |
| JP6900596B2 (ja) * | 2015-08-20 | 2021-07-07 | フリードリッヒ − ヴィルヘルム キューネ | 赤血球疾患およびそれによって媒介される症状を治療するための亜塩素酸塩の使用 |
| TWI719105B (zh) | 2016-01-04 | 2021-02-21 | 中央硏究院 | 基於酯化/皂化用於微脂體負載之方法 |
| US20190142864A1 (en) * | 2017-10-11 | 2019-05-16 | California Institute Of Technology | Methods and systems, for interfering with viability of bacteria and related antimicrobials and compositions |
| EP3752833B1 (en) * | 2018-02-15 | 2025-08-13 | Yeditepe Universitesi | Exosome isolation method by two phase fluid system |
| WO2019191627A1 (en) | 2018-03-30 | 2019-10-03 | Insmed Incorporated | Methods for continuous manufacture of liposomal drug products |
| CN110563829B (zh) * | 2019-09-17 | 2021-03-26 | 中国人民解放军国防科技大学 | 用于调控脂质体囊泡行为、功能的反光蛋白体系及其应用 |
| CN112716973A (zh) * | 2019-10-28 | 2021-04-30 | 卢序 | 一种降低细胞还原应激的氧化剂的用途 |
| TR202012260A2 (tr) * | 2020-08-05 | 2020-10-21 | Emin Zuemruetdal | Oral kullanim i̇çi̇n potasyum hi̇droksi̇t/sodyum hi̇droksi̇t solüsyonu |
| CA3253808A1 (en) * | 2022-05-19 | 2023-11-23 | Neuvivo Inc | BIOMARKERS OF NEURODEGENERATIVE DISEASES |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2000019981A1 (en) * | 1998-10-08 | 2000-04-13 | Karagoezian Hampar L | Synergistic antimicrobial, dermatological and ophthalmic preparations containing chlorite and hydrogen peroxide |
| KR20030072766A (ko) * | 2002-03-06 | 2003-09-19 | (주)인터커머스 | 구취 억제능이 우수한 구강 위생용 조성물 및 그의제조방법 |
| US20070104798A1 (en) * | 1999-10-04 | 2007-05-10 | S.K. Pharmaceuticals, Inc. | Synergistic antimicrobial preparations containing chlorite and hydrogen peroxide |
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| US4241046A (en) | 1978-11-30 | 1980-12-23 | Papahadjopoulos Demetrios P | Method of encapsulating biologically active materials in lipid vesicles |
| DE3213389A1 (de) | 1982-04-10 | 1983-10-20 | Friedrich-Wilhelm Dr. 7107 Neckarsulm Kühne | Stabilisierter aktivierter sauerstoff und arzneimittel, die diesen stabilisierten aktivierten sauerstoff enthalten |
| US4551288A (en) | 1982-08-16 | 1985-11-05 | Sandoz, Inc. | Processes for the preparation of liposome drug delivery systems |
| US4485054A (en) | 1982-10-04 | 1984-11-27 | Lipoderm Pharmaceuticals Limited | Method of encapsulating biologically active materials in multilamellar lipid vesicles (MLV) |
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- 2012-12-21 MX MX2014007664A patent/MX2014007664A/es unknown
- 2012-12-21 WO PCT/IB2012/057645 patent/WO2013093891A1/en not_active Ceased
- 2012-12-21 EP EP12820937.6A patent/EP2793860A1/en not_active Withdrawn
- 2012-12-21 US US13/724,963 patent/US20130177629A1/en not_active Abandoned
- 2012-12-21 IN IN5866DEN2014 patent/IN2014DN05866A/en unknown
- 2012-12-21 BR BR112014015333A patent/BR112014015333A2/pt not_active IP Right Cessation
- 2012-12-21 JP JP2014548324A patent/JP2015502400A/ja active Pending
- 2012-12-21 AU AU2012297589A patent/AU2012297589C1/en not_active Ceased
- 2012-12-21 RU RU2014130080A patent/RU2014130080A/ru not_active Application Discontinuation
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Also Published As
| Publication number | Publication date |
|---|---|
| EP2793860A1 (en) | 2014-10-29 |
| US20130177629A1 (en) | 2013-07-11 |
| CN104125826A (zh) | 2014-10-29 |
| CA2857604A1 (en) | 2013-06-27 |
| AU2012297589A1 (en) | 2013-07-11 |
| BR112014015333A8 (pt) | 2017-06-13 |
| JP2015502400A (ja) | 2015-01-22 |
| IN2014DN05866A (enExample) | 2015-05-22 |
| WO2013093891A1 (en) | 2013-06-27 |
| BR112014015333A2 (pt) | 2017-06-13 |
| MX2014007664A (es) | 2015-05-11 |
| AU2012297589B2 (en) | 2014-10-30 |
| RU2014130080A (ru) | 2016-02-10 |
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