WO1998034597B1 - Liposomes containing active agents - Google Patents
Liposomes containing active agentsInfo
- Publication number
- WO1998034597B1 WO1998034597B1 PCT/US1998/002154 US9802154W WO9834597B1 WO 1998034597 B1 WO1998034597 B1 WO 1998034597B1 US 9802154 W US9802154 W US 9802154W WO 9834597 B1 WO9834597 B1 WO 9834597B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- liposome
- lipid
- active agent
- polyethylene glycol
- derivatized
- 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
Links
Abstract
Liposomes formulations are designed to maximize the amount of poorly water-soluble active agent that can be carried by the liposome. Liposomes containing active agent in the lipid bilayer of the liposome, and/or entrapped within the liposome interior space in a micellar preparation are described. Methods of making such liposomes are presented.
Claims
AMENDED CLAIMS
[received by the International Bureau on 7 August 1998 (07.08.98); new claims 37-67 added; original claims unchanged (6 pages)]
32. A method of making a liposome containing paclitaxel in the lipid bilayer and containing a micellar preparation of paclitaxel in the liposome interior space, comprising: a) preparing a phospholipid film containing paclitaxel, cholesterol and a surfactant, said surfactant having a low Critical Micelle Concentration; and b) hydrating said lipid film with a micellar preparation of paclitaxel, wherein said cholesterol is contained in the phospholipid film in an amount sufficient to increase the stability of the liposome compared to that which would occur in the absence of cholesterol.
33. A method of making a liposome according to claim 32, wherein said phospholipid film contains a saturating amount of surfactant.
34. A method of making a liposome according to claim 32, wherein said phospholipid film contains a saturating amount of paclitaxel.
35. A method of making a liposome according to claim 32 wherein said phospholipid, said surfactant and said cholesterol are present in a ratio that maximizes the amount of active agent carried by said liposome.
36. A method of making a liposome according to claim 32, wherein said phospholipid film comprises phospholipid, lysophosphatidylcholine, and cholesterol in a mole ratio of about 8:4:3.
37. A liposome containing an active agent, said liposome having a lipid bilayer membrane comprising vesicle-forming lipid and vesicle-forming lipid derivatized with hydrophilic polymer, said active agent aggregated with lipid surfactant and entrapped within said liposome, wherein the liposome membrane contains polymer-derivatized lipid in an amount sufficient to inhibit fusion of the liposome membrane with the active agent-
108 lipid surfactant aggregate entrapped therein, compared to fusion that would occur in the absence of polymer-derivatized lipid.
38. A liposome according to claim 37, wherein said hydrophilic polymer is selected from the group consisting of polyethylene glycol, polylactic acid, polyglycolic acid, copolymers of polylactic acid and polyglycolic acid, and poly vinyl alcohol.
39. A liposome according to claim 37, wherein the liposome membrane contains said polymer-derivatized lipid in a saturating amount.
40. A liposome according to claim 37, wherein said hydrophilic polymer is polyethylene glycol having a molecular weight of between about 300 daltons and 10,000 daltons.
41. A liposome according to claim 37, wherein said hydrophilic polymer is polyethylene glycol having a molecular weight of 750 daltons and contained in the liposome membrane in an amount of from 1 mole percent to 22 mole percent.
42. A liposome according to claim 37 wherein said hydrophilic polymer has a cloud temperature within physiologic range.
43. A liposome containing an active agent, said liposome having a lipid bilayer membrane comprising vesicle-forming lipid and vesicle-forming lipid derivatized with polyethylene glycol, said active agent aggregated with lipid surfactant and entrapped within said liposome, wherein the liposome membrane contains polyethylene-derivatized lipid in an amount sufficient to inhibit fusion of the liposome membrane with the active agent-
109
lipid surfactant aggregate entrapped therein, compared to fusion that would occur in the absence of poly ethyleneglycol-derivatized lipid.
44. A liposome according to claim 43, wherein said polyethylene glycol has a molecular weight of between about 300 daltons and 10,000 daltons.
45. A liposome according to claim 43 , wherein said polyethylene glycol has a molecular weight of 750 daltons and the liposome membrane contains polyethylene glycol-derivatized lipid in an amount from 1 mole percent to 22 mole percent.
46. A liposome having a lipid bilayer membrane comprising a vesicle-forming lipid and from 1 mole percent to 22 mole percent vesicle-forming lipid derivatized with polyethylene glycol, said polyethylene glycol having a molecular weight of 750 daltons, and containing a micellar preparation of paclitaxel entrapped therein.
47. A method for preparing an active agent suitable for intravenous injection, comprising:
(a) obtaining a preparation of active agent aggregated with lipid surfactant;
(b) entrapping said preparation of step (a) in a liposome having a lipid bilayer membrane comprising vesicle-forming lipids and vesicle-forming lipids derivatized with a hydrophilic polymer, wherein said polymer-derivatized lipid is contained in the liposome membrane in an amount sufficient to inhibit fusion of the membrane with said active agent-lipid aggregates contained therein, compared to fusion that would occur in the absence of polymer-derivatized lipid.
110
48. A method according to claim 47, wherein said active agent is in micellar form.
49. A method according to claim 47, wherein said hydrophilic polymer is selected from the group consisting of polyethylene glycol, polylactic acid, polyglycolic acid, copolymers of polylactic acid and polyglycolic acid, and polyvinyl alcohol.
50. A liposome according to claim 47, wherein the liposome membrane contains said polymer-derivatized lipid in a saturating amount.
51. A liposome according to claim 47, wherein said hydrophilic polymer is polyethylene glycol having a molecular weight of between about 300 daltons and 10,000 daltons.
52. A method according to claim 47, wherein said polyethylene glycol has a molecular weight of 750 daltons and the liposome membrane contains polyethylene glycol-derivatized lipid in an amount from 1 mole percent to 22 mole percent.
53. A method according to claim 47, wherein said hydrophilic polymer has a cloud temperature within physiologic range.
54. A method according to claim 47, wherein said active agent is a pharmacologically active agent, a diagnostic agent, or a nutritional agent.
55. A method according to claim 47, wherein said active agent is a pharmacologically active agent selected from the group consisting of antineoplastic
111
agents, anti-inflammatory agents, anti-tumor agents, immunosuppressive agents, antibiotic agents and anti-infective agents.
56. A method according to claim 47, wherein said active agent is selected from the group consisting of doxorubicin, epirubicin, daunorubicin, vincristine, vinblastine, etoposide, ellipticine, camptothecin, paclitaxel, docetaxol, cisplatin, prednisone, methyl-prednisone, and ibuprofen.
57. A liposome containing an active agent, said liposome having a lipid bilayer membrane comprising vesicle-forming lipid and cholesterol, said active agent aggregated with lipid surfactant and entrapped within said liposome, wherein said liposome membrane contains cholesterol in an amount sufficient to inhibit fusion of the membrane with said active agent-lipid surfactant aggregate entrapped therein, compared to fusion that would occur in the absence of cholesterol.
58. A liposome according to claim 57, wherein the liposome membrane contains a saturating amount of cholesterol.
59. A liposome according to claim 57, wherein the liposome membrane contains from 3 mole percent to 60 mole percent cholesterol.
60. A liposome according to claim 57, wherein the liposome membrane contains about 3 mole percent cholesterol.
112
61. A liposome according to claim 37 or 57, wherein said lipid surfactant aggregated with said active agent is a lysolipid.
62. A liposome according to claim 37 or 57, wherein said lipid surfactant aggregated with said active agent is lysophosphatidylcholine.
63. A liposome according to claim 37, 43, or 57, wherein said active agent is in micellar form.
64. A liposome according to claim 37, 43 or 57, wherein said active agent is a pharmacologically active agent, a diagnostic agent, or a nutritional agent.
65. A liposome according to claim 37, 43 or 57, wherein said active agent is a pharmacologically active agent selected from the group consisting of antineoplastic agents, anti-inflammatory agents, anti-tumor agents, immunosuppressive agents, antibiotic agents and anti- infective agents.
66. A method according to claim 37, 43 or 57, wherein said active agent is selected from the group consisting of doxorubicin, epirubicin, daunorubicin, vincristine, vinblastine, etoposide, ellipticine, camptothecin, paclitaxel, docetaxol, cisplatin, prednisone, methyl-prednisone, and ibuprofen.
67. A liposome preparation comprising a plurality of liposomes according to claim 37, 43 or 57.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU63196/98A AU6319698A (en) | 1997-02-06 | 1998-02-05 | Liposomes containing active agents |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/795,100 | 1997-02-06 | ||
| US08/795,100 US5827533A (en) | 1997-02-06 | 1997-02-06 | Liposomes containing active agents aggregated with lipid surfactants |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO1998034597A1 WO1998034597A1 (en) | 1998-08-13 |
| WO1998034597B1 true WO1998034597B1 (en) | 1998-10-01 |
Family
ID=25164667
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US1998/002154 Ceased WO1998034597A1 (en) | 1997-02-06 | 1998-02-05 | Liposomes containing active agents |
Country Status (3)
| Country | Link |
|---|---|
| US (4) | US5827533A (en) |
| AU (1) | AU6319698A (en) |
| WO (1) | WO1998034597A1 (en) |
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