NO303205B1 - FremgangsmÕte for fremstilling av lipidkompleksoppslemming - Google Patents
FremgangsmÕte for fremstilling av lipidkompleksoppslemming Download PDFInfo
- Publication number
- NO303205B1 NO303205B1 NO913816A NO913816A NO303205B1 NO 303205 B1 NO303205 B1 NO 303205B1 NO 913816 A NO913816 A NO 913816A NO 913816 A NO913816 A NO 913816A NO 303205 B1 NO303205 B1 NO 303205B1
- Authority
- NO
- Norway
- Prior art keywords
- lipid
- compound
- slurry
- solution
- solvent
- Prior art date
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- 150000002632 lipids Chemical class 0.000 title claims abstract description 147
- 238000000034 method Methods 0.000 title claims abstract description 46
- 239000002002 slurry Substances 0.000 title claims description 35
- 238000002360 preparation method Methods 0.000 title description 39
- 230000008569 process Effects 0.000 title description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims abstract description 107
- 239000002502 liposome Substances 0.000 claims abstract description 80
- 150000001875 compounds Chemical class 0.000 claims abstract description 66
- 239000002245 particle Substances 0.000 claims abstract description 66
- 239000000243 solution Substances 0.000 claims abstract description 49
- 239000000010 aprotic solvent Substances 0.000 claims abstract description 21
- 239000007864 aqueous solution Substances 0.000 claims abstract description 20
- 239000002904 solvent Substances 0.000 claims description 45
- APKFDSVGJQXUKY-KKGHZKTASA-N Amphotericin-B Natural products O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1C=CC=CC=CC=CC=CC=CC=C[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-KKGHZKTASA-N 0.000 claims description 34
- 229960003942 amphotericin b Drugs 0.000 claims description 34
- APKFDSVGJQXUKY-INPOYWNPSA-N amphotericin B Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-INPOYWNPSA-N 0.000 claims description 31
- 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 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 20
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 18
- 238000005538 encapsulation Methods 0.000 claims description 16
- -1 lipid compound Chemical class 0.000 claims description 15
- 239000011877 solvent mixture Substances 0.000 claims description 14
- 235000012000 cholesterol Nutrition 0.000 claims description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 150000001413 amino acids Chemical class 0.000 claims description 9
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 8
- 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 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 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 6
- 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 6
- 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 6
- 229960000988 nystatin Drugs 0.000 claims description 6
- VQOXZBDYSJBXMA-NQTDYLQESA-N nystatin A1 Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/CC/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 VQOXZBDYSJBXMA-NQTDYLQESA-N 0.000 claims description 6
- 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 claims description 5
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 5
- 150000001298 alcohols Chemical class 0.000 claims description 5
- 229960003724 dimyristoylphosphatidylcholine Drugs 0.000 claims description 5
- 229960005160 dimyristoylphosphatidylglycerol Drugs 0.000 claims description 5
- BPHQZTVXXXJVHI-AJQTZOPKSA-N ditetradecanoyl phosphatidylglycerol Chemical compound CCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@@H](O)CO)OC(=O)CCCCCCCCCCCCC BPHQZTVXXXJVHI-AJQTZOPKSA-N 0.000 claims description 5
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- UVAJCDOUVGWEFK-UHFFFAOYSA-N 1-methyl-2,3-dihydropyrrole Chemical compound CN1CCC=C1 UVAJCDOUVGWEFK-UHFFFAOYSA-N 0.000 claims description 4
- AVTXVDFKYBVTKR-DPAQBDIFSA-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] dihydrogen phosphate Chemical compound C1C=C2C[C@@H](OP(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 AVTXVDFKYBVTKR-DPAQBDIFSA-N 0.000 claims description 4
- 150000008282 halocarbons Chemical class 0.000 claims description 4
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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 claims description 3
- AWUCVROLDVIAJX-UHFFFAOYSA-N alpha-glycerophosphate Natural products OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 claims description 3
- WLNARFZDISHUGS-MIXBDBMTSA-N cholesteryl hemisuccinate Chemical compound C1C=C2C[C@@H](OC(=O)CCC(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 WLNARFZDISHUGS-MIXBDBMTSA-N 0.000 claims description 3
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- 102000019197 Superoxide Dismutase Human genes 0.000 claims description 2
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- MWEZHNCHKXEIBJ-ISGTVXCRSA-N [(3s,8s,10r,13r)-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] 2-(trimethylazaniumyl)ethyl phosphate Chemical compound C1C=C2C[C@@H](OP([O-])(=O)OCC[N+](C)(C)C)CC[C@]2(C)C2[C@@H]1C1CCC([C@H](C)CCCC(C)C)[C@@]1(C)CC2 MWEZHNCHKXEIBJ-ISGTVXCRSA-N 0.000 claims description 2
- JLCPHMBAVCMARE-UHFFFAOYSA-N [3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methyl [5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate Polymers Cc1cn(C2CC(OP(O)(=O)OCC3OC(CC3OP(O)(=O)OCC3OC(CC3O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c3nc(N)[nH]c4=O)C(COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3CO)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cc(C)c(=O)[nH]c3=O)n3cc(C)c(=O)[nH]c3=O)n3ccc(N)nc3=O)n3cc(C)c(=O)[nH]c3=O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)O2)c(=O)[nH]c1=O JLCPHMBAVCMARE-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
-
- 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
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1617—Organic compounds, e.g. phospholipids, fats
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/54—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic compound
- A61K47/543—Lipids, e.g. triglycerides; Polyamines, e.g. spermine or spermidine
- A61K47/544—Phospholipids
-
- 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)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Biophysics (AREA)
- Dispersion Chemistry (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Manufacturing Of Micro-Capsules (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US33260989A | 1989-03-31 | 1989-03-31 | |
| US33405589A | 1989-04-05 | 1989-04-05 | |
| PCT/US1990/001646 WO1990011780A1 (en) | 1989-03-31 | 1990-03-28 | Preparation of liposome and lipid complex compositions |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO913816D0 NO913816D0 (no) | 1991-09-27 |
| NO913816L NO913816L (no) | 1991-11-26 |
| NO303205B1 true NO303205B1 (no) | 1998-06-15 |
Family
ID=26988293
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO913816A NO303205B1 (no) | 1989-03-31 | 1991-09-27 | FremgangsmÕte for fremstilling av lipidkompleksoppslemming |
Country Status (12)
| Country | Link |
|---|---|
| EP (1) | EP0467954B1 (ja) |
| JP (1) | JP2798302B2 (ja) |
| AT (1) | ATE137403T1 (ja) |
| AU (1) | AU638245B2 (ja) |
| CA (1) | CA2050679C (ja) |
| DE (1) | DE69026820T2 (ja) |
| DK (1) | DK0467954T3 (ja) |
| ES (1) | ES2087151T3 (ja) |
| HK (1) | HK1000912A1 (ja) |
| HU (1) | HU208070B (ja) |
| NO (1) | NO303205B1 (ja) |
| WO (1) | WO1990011780A1 (ja) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5178875A (en) * | 1991-01-14 | 1993-01-12 | The Board Of Regents, The University Of Texas System | Liposomal-polyene preliposomal powder and method for its preparation |
| JPH0363298A (ja) * | 1989-07-31 | 1991-03-19 | Green Cross Corp:The | コロニー形成刺激因子・脂質複合体 |
| FR2653015B1 (fr) * | 1989-10-12 | 1993-10-29 | Oreal | Composition cosmetique ou pharmaceutique pour application topique contenant au moins un derive retinouide et au moins un derive de pyrimidine, son utilisation comme medicament et procede de traitement correspondant. |
| DE4238779A1 (de) * | 1992-11-12 | 1994-05-19 | Max Delbrueck Centrum | Lyotrophe Mesophasen und ihre Anwendung in der Pharmazie, der Kosmetik und der Dermatologie |
| ATE199640T1 (de) | 1993-07-08 | 2001-03-15 | Liposome Co Inc | Verfahren zum kontrollieren der liposomengrösse |
| CA2150453A1 (en) * | 1993-09-29 | 1995-04-06 | Ferdinand Theodorus Joseph Van Rijn | A novel antifungal composition |
| JPH11507815A (ja) * | 1995-06-07 | 1999-07-13 | ジンタ・インコーポレイテッド | ホスホン酸基本カチオン性脂質 |
| JP2002532535A (ja) * | 1998-12-22 | 2002-10-02 | アメリカ合衆国 | 水不溶性薬剤送達システム |
| US6511676B1 (en) * | 1999-11-05 | 2003-01-28 | Teni Boulikas | Therapy for human cancers using cisplatin and other drugs or genes encapsulated into liposomes |
| EP1334718A4 (en) * | 2000-10-26 | 2007-07-18 | Senju Pharma Co | DRUG COMPOSITION CONTAINING DIPEPTIDYL ALDEHYDE COMPOUND |
| AU2002219998B2 (en) * | 2000-12-01 | 2006-03-02 | Biomira, Inc. | Preparation of large liposomes by infusion into peg |
| IS6389A (is) * | 2001-08-31 | 2003-03-03 | Heraeus Kulzer Gmbh & Co. Kg | Reynsla af sýklalyfjahúðun skrokka, sem í eru örholrými, og einnig af þannig húðuðum skrokkum og notkun þeirra |
| CA2681302C (en) * | 2007-03-19 | 2013-07-23 | Dhiraj Khattar | Proliposomal and liposomal compositions of poorly water-soluble compounds |
| WO2009064696A1 (en) * | 2007-11-14 | 2009-05-22 | The Regents Of The University Of California | Sterol-modified amphiphilic lipids |
| DK2344198T3 (da) | 2008-09-27 | 2020-11-30 | Jina Pharmaceuticals Inc | Lipidbaserede farmaceutiske præparater til topisk anvendelse |
| EP2594281B1 (en) * | 2010-07-14 | 2019-08-28 | Institute Of Materia Medica, Chinese Academy Of Medical Sciences | Insulin-lipid complex, preparation method therefor, and preparation thereof |
| AU2015301234A1 (en) | 2014-08-04 | 2017-06-15 | Zoneone Pharma, Inc. | Remote loading of sparingly water-soluble drugs into lipid vesicles |
| CN113616798A (zh) * | 2021-09-06 | 2021-11-09 | 天津农学院 | 一种甲苯咪唑脂质复合物、制备方法和应用 |
| CN115177590A (zh) * | 2022-04-20 | 2022-10-14 | 南昌大学抚州医学院 | 一种甲苯达唑类脂质体的制备方法及应用 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4588578A (en) * | 1983-08-08 | 1986-05-13 | The Liposome Company, Inc. | Lipid vesicles prepared in a monophase |
| JPS60240634A (ja) | 1984-05-08 | 1985-11-29 | 関 則雄 | 飲み干し容易なコツプ |
| US4619913A (en) * | 1984-05-29 | 1986-10-28 | Matrix Pharmaceuticals, Inc. | Treatments employing drug-containing matrices for introduction into cellular lesion areas |
| AU598002B2 (en) * | 1986-07-15 | 1990-06-14 | Cilag Ltd. | Method of preparing single bilayered liposomes |
| US4804539A (en) | 1986-07-28 | 1989-02-14 | Liposome Technology, Inc. | Ophthalmic liposomes |
| US4839175A (en) * | 1986-07-28 | 1989-06-13 | Liposome Technology, Inc. | Liposomes with enhanced retention on mucosal tissue |
| US4812312A (en) * | 1987-03-03 | 1989-03-14 | Board Of Regents Of The University Of Texas System | Liposome-incorporated nystatin |
| NZ223660A (en) * | 1987-03-05 | 1990-11-27 | Liposome Co Inc | Low toxicity drug-lipid complexes; methods of making them; and method of determining their toxicity |
-
1990
- 1990-03-28 DE DE69026820T patent/DE69026820T2/de not_active Expired - Fee Related
- 1990-03-28 JP JP2506114A patent/JP2798302B2/ja not_active Expired - Fee Related
- 1990-03-28 AT AT90906530T patent/ATE137403T1/de not_active IP Right Cessation
- 1990-03-28 CA CA002050679A patent/CA2050679C/en not_active Expired - Fee Related
- 1990-03-28 AU AU54345/90A patent/AU638245B2/en not_active Ceased
- 1990-03-28 WO PCT/US1990/001646 patent/WO1990011780A1/en active IP Right Grant
- 1990-03-28 DK DK90906530.2T patent/DK0467954T3/da active
- 1990-03-28 EP EP90906530A patent/EP0467954B1/en not_active Expired - Lifetime
- 1990-03-28 ES ES90906530T patent/ES2087151T3/es not_active Expired - Lifetime
- 1990-03-28 HU HU903559A patent/HU208070B/hu not_active IP Right Cessation
-
1991
- 1991-09-27 NO NO913816A patent/NO303205B1/no unknown
-
1997
- 1997-12-19 HK HK97102512A patent/HK1000912A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ES2087151T3 (es) | 1996-07-16 |
| HU208070B (en) | 1993-08-30 |
| NO913816D0 (no) | 1991-09-27 |
| NO913816L (no) | 1991-11-26 |
| EP0467954B1 (en) | 1996-05-01 |
| CA2050679A1 (en) | 1990-10-01 |
| HUT59818A (en) | 1992-07-28 |
| HU903559D0 (en) | 1991-12-30 |
| AU638245B2 (en) | 1993-06-24 |
| JPH04506207A (ja) | 1992-10-29 |
| CA2050679C (en) | 1998-09-22 |
| JP2798302B2 (ja) | 1998-09-17 |
| ATE137403T1 (de) | 1996-05-15 |
| DK0467954T3 (da) | 1996-05-28 |
| AU5434590A (en) | 1990-11-05 |
| HK1000912A1 (en) | 1998-05-08 |
| WO1990011780A1 (en) | 1990-10-18 |
| EP0467954A4 (en) | 1992-06-03 |
| DE69026820D1 (de) | 1996-06-05 |
| EP0467954A1 (en) | 1992-01-29 |
| DE69026820T2 (de) | 1996-11-28 |
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