CA2399821A1 - Lipid-based drug delivery systems containing phospholipase a2 degradable lipid derivatives and the therapeutic uses thereof - Google Patents
Lipid-based drug delivery systems containing phospholipase a2 degradable lipid derivatives and the therapeutic uses thereof Download PDFInfo
- Publication number
- CA2399821A1 CA2399821A1 CA002399821A CA2399821A CA2399821A1 CA 2399821 A1 CA2399821 A1 CA 2399821A1 CA 002399821 A CA002399821 A CA 002399821A CA 2399821 A CA2399821 A CA 2399821A CA 2399821 A1 CA2399821 A1 CA 2399821A1
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- Prior art keywords
- lipid
- drug delivery
- delivery system
- liposomes
- drug
- Prior art date
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- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 229960002009 naproxen Drugs 0.000 description 1
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
- 239000013642 negative control Substances 0.000 description 1
- 210000005170 neoplastic cell Anatomy 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 230000009022 nonlinear effect Effects 0.000 description 1
- ABCVHPIKBGRCJA-UHFFFAOYSA-N nonyl 8-[(8-heptadecan-9-yloxy-8-oxooctyl)-(2-hydroxyethyl)amino]octanoate Chemical class OCCN(CCCCCCCC(=O)OC(CCCCCCCC)CCCCCCCC)CCCCCCCC(=O)OCCCCCCCCC ABCVHPIKBGRCJA-UHFFFAOYSA-N 0.000 description 1
- 238000013421 nuclear magnetic resonance imaging Methods 0.000 description 1
- 238000011580 nude mouse model Methods 0.000 description 1
- GYCKQBWUSACYIF-UHFFFAOYSA-N o-hydroxybenzoic acid ethyl ester Natural products CCOC(=O)C1=CC=CC=C1O GYCKQBWUSACYIF-UHFFFAOYSA-N 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 230000001991 pathophysiological effect Effects 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 150000002960 penicillins Chemical class 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 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 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229950004354 phosphorylcholine Drugs 0.000 description 1
- 230000010399 physical interaction Effects 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 239000002459 polyene antibiotic agent Substances 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
- 235000019833 protease Nutrition 0.000 description 1
- 230000009822 protein phosphorylation Effects 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
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- 230000002441 reversible effect Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 150000003870 salicylic acids Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 125000003696 stearoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- MVGSNCBCUWPVDA-MFOYZWKCSA-N sulindac sulfone Chemical compound CC1=C(CC(O)=O)C2=CC(F)=CC=C2\C1=C/C1=CC=C(S(C)(=O)=O)C=C1 MVGSNCBCUWPVDA-MFOYZWKCSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000019364 tetracycline Nutrition 0.000 description 1
- 150000003522 tetracyclines Chemical class 0.000 description 1
- 229940040944 tetracyclines Drugs 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 230000008542 thermal sensitivity Effects 0.000 description 1
- 150000003595 thromboxanes Chemical class 0.000 description 1
- 150000003611 tocopherol derivatives Chemical class 0.000 description 1
- 229960001727 tretinoin Drugs 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- MSRILKIQRXUYCT-UHFFFAOYSA-M valproate semisodium Chemical compound [Na+].CCCC(C(O)=O)CCC.CCCC(C([O-])=O)CCC MSRILKIQRXUYCT-UHFFFAOYSA-M 0.000 description 1
- 229960000604 valproic acid Drugs 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
- 150000003710 vitamin D derivatives Chemical class 0.000 description 1
- 235000005282 vitamin D3 Nutrition 0.000 description 1
- 239000011647 vitamin D3 Substances 0.000 description 1
- QYSXJUFSXHHAJI-YRZJJWOYSA-N vitamin D3 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-YRZJJWOYSA-N 0.000 description 1
- 229940021056 vitamin d3 Drugs 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
- HBOMLICNUCNMMY-XLPZGREQSA-N zidovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 HBOMLICNUCNMMY-XLPZGREQSA-N 0.000 description 1
- 229960002555 zidovudine Drugs 0.000 description 1
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
- A61K9/10—Dispersions; Emulsions
- A61K9/127—Synthetic bilayered vehicles, e.g. liposomes or liposomes with cholesterol as the only non-phosphatidyl surfactant
- A61K9/1271—Non-conventional liposomes, e.g. PEGylated liposomes or liposomes coated or grafted with polymers
- A61K9/1272—Non-conventional liposomes, e.g. PEGylated liposomes or liposomes coated or grafted with polymers comprising non-phosphatidyl surfactants as bilayer-forming substances, e.g. cationic lipids or non-phosphatidyl liposomes coated or grafted with polymers
-
- 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
- A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
- A61K9/1075—Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers
-
- 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—Synthetic bilayered vehicles, e.g. liposomes or liposomes with cholesterol as the only non-phosphatidyl surfactant
- A61K9/1271—Non-conventional liposomes, e.g. PEGylated liposomes or liposomes coated or grafted with polymers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Dispersion Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Molecular Biology (AREA)
- Biophysics (AREA)
- Rheumatology (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Pain & Pain Management (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Pulmonology (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DKPA200000211 | 2000-02-10 | ||
| DKPA200000211 | 2000-02-10 | ||
| DKPA200000616 | 2000-04-12 | ||
| DKPA200000616 | 2000-04-12 | ||
| PCT/DK2001/000092 WO2001058910A2 (en) | 2000-02-10 | 2001-02-09 | Lipid-based drug delivery systems |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2399821A1 true CA2399821A1 (en) | 2001-08-16 |
Family
ID=26068763
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002399821A Abandoned CA2399821A1 (en) | 2000-02-10 | 2001-02-09 | Lipid-based drug delivery systems containing phospholipase a2 degradable lipid derivatives and the therapeutic uses thereof |
Country Status (9)
| Country | Link |
|---|---|
| EP (2) | EP1254143B1 (https=) |
| JP (1) | JP2003522193A (https=) |
| AT (1) | ATE277935T1 (https=) |
| AU (1) | AU778659B2 (https=) |
| CA (1) | CA2399821A1 (https=) |
| DE (1) | DE60105977T2 (https=) |
| ES (1) | ES2230268T3 (https=) |
| PT (1) | PT1254143E (https=) |
| WO (1) | WO2001058910A2 (https=) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2272768T3 (es) * | 2001-10-03 | 2007-05-01 | Celator Pharmaceuticals Inc | Composiciones para la administracion de combinaciones de farmacos. |
| CA2383259A1 (en) | 2002-04-23 | 2003-10-23 | Celator Technologies Inc. | Synergistic compositions |
| US7850990B2 (en) | 2001-10-03 | 2010-12-14 | Celator Pharmaceuticals, Inc. | Compositions for delivery of drug combinations |
| ATE418966T1 (de) * | 2004-11-03 | 2009-01-15 | Liplasome Pharma As | Arzneimittelabgabesysteme auf lipidbasis mit unnatürlichen phospholipase-a2-abbaubaren lipid- derivaten und ihre therapeutische verwendung |
| WO2006086992A2 (en) * | 2005-02-18 | 2006-08-24 | Liplasome Pharma A/S | Drug delivery systems containing phqspholipase a2 degradable lipid prodrug derivatives and the therapeutic uses thereof as. e.g. wound healing agents and peroxisome proliferator activated receptor ligands |
| EP1940355B1 (en) | 2005-09-30 | 2012-12-19 | Auburn University | Targeted drug delivery nanocarrier comprising a targeting landscape phage protein assembly |
| CA2647779A1 (en) * | 2006-03-23 | 2007-09-27 | Liplasome Pharma A/S | Lipid based drug delivery systems comprising phospholipase a2 degradable lipids that perform an intramolecular cyclization reaction upon hydrolysis |
| EP2123258A1 (en) | 2008-05-23 | 2009-11-25 | Liplasome Pharma A/S | Liposomes for drug delivery |
| DK177532B1 (en) * | 2009-09-17 | 2013-09-08 | Bio Bedst Aps | Medical use of sPLA2 hydrolysable liposomes |
| DK177529B1 (en) * | 2009-10-23 | 2013-09-08 | Bio Bedst Aps | Liposomes with improved storage stability |
| EP2343310A1 (en) | 2010-01-08 | 2011-07-13 | Novozymes A/S | Serine hydrolase formulation |
| WO2011098578A2 (en) | 2010-02-12 | 2011-08-18 | Bioneer A/S | Liposome system for ocular administration |
| CZ308596B6 (cs) * | 2017-04-03 | 2020-12-23 | Ústav molekulární genetiky AV ČR, v. v. i. | Deriváty fosfolipidů a jejich použití jako léčiva |
| EP3530266A1 (en) | 2018-02-27 | 2019-08-28 | LipoCoat B.V. | A lipid-based coating composition, and an object having a lipid-based coating |
| EP3530265A1 (en) * | 2018-02-27 | 2019-08-28 | LipoCoat B.V. | Universal method for the preparation of lipid-based coatings |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4622392A (en) * | 1984-06-21 | 1986-11-11 | Health Research Inc. (Roswell Park Division) | Thiophospholipid conjugates of antitumor agents |
| US5153000A (en) * | 1988-11-22 | 1992-10-06 | Kao Corporation | Phosphate, liposome comprising the phosphate as membrane constituent, and cosmetic and liposome preparation comprising the liposome |
| JPH07126166A (ja) * | 1993-10-29 | 1995-05-16 | Sagami Chem Res Center | ホスホリパ−ゼａ２阻害剤 |
| JP3498336B2 (ja) * | 1993-12-06 | 2004-02-16 | 日本油脂株式会社 | リン脂質誘導体 |
| JP3620059B2 (ja) * | 1994-03-04 | 2005-02-16 | 日本油脂株式会社 | 反応性小胞体、形成剤および機能性物質固定化小胞体 |
| DE4408011C1 (de) * | 1994-03-10 | 1995-11-02 | Max Delbrueck Centrum | Pharmazeutisches Mittel zur Tumortherapie |
| US5817856A (en) * | 1995-12-11 | 1998-10-06 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Radiation-protective phospholipid and method |
| JP3778528B2 (ja) * | 1996-11-08 | 2006-05-24 | 三菱化学株式会社 | ミセルに組み込まれた水溶性高分子物質の分析方法 |
| US5827836A (en) * | 1996-11-15 | 1998-10-27 | Clarion Pharmaceuticals Inc. | Retinoid glycerol phospholipid conjugates |
| US6200598B1 (en) * | 1998-06-18 | 2001-03-13 | Duke University | Temperature-sensitive liposomal formulation |
-
2001
- 2001-02-09 EP EP01903609A patent/EP1254143B1/en not_active Expired - Lifetime
- 2001-02-09 CA CA002399821A patent/CA2399821A1/en not_active Abandoned
- 2001-02-09 DE DE60105977T patent/DE60105977T2/de not_active Expired - Lifetime
- 2001-02-09 ES ES01903609T patent/ES2230268T3/es not_active Expired - Lifetime
- 2001-02-09 AU AU31533/01A patent/AU778659B2/en not_active Ceased
- 2001-02-09 JP JP2001558059A patent/JP2003522193A/ja active Pending
- 2001-02-09 EP EP04015791A patent/EP1484332A3/en not_active Withdrawn
- 2001-02-09 AT AT01903609T patent/ATE277935T1/de not_active IP Right Cessation
- 2001-02-09 PT PT01903609T patent/PT1254143E/pt unknown
- 2001-02-09 WO PCT/DK2001/000092 patent/WO2001058910A2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| WO2001058910A3 (en) | 2002-02-21 |
| EP1484332A2 (en) | 2004-12-08 |
| AU778659B2 (en) | 2004-12-16 |
| ATE277935T1 (de) | 2004-10-15 |
| DE60105977T2 (de) | 2006-02-23 |
| AU3153301A (en) | 2001-08-20 |
| EP1484332A3 (en) | 2009-01-21 |
| EP1254143B1 (en) | 2004-09-29 |
| WO2001058910A2 (en) | 2001-08-16 |
| ES2230268T3 (es) | 2005-05-01 |
| JP2003522193A (ja) | 2003-07-22 |
| EP1254143A2 (en) | 2002-11-06 |
| PT1254143E (pt) | 2005-02-28 |
| DE60105977D1 (de) | 2004-11-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |