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
Links
- 239000002502 liposome Substances 0.000 title claims abstract 59
- 239000013543 active substance Substances 0.000 title claims abstract 26
- 238000000034 method Methods 0.000 claims abstract 10
- 239000000232 Lipid Bilayer Substances 0.000 claims abstract 7
- 150000002632 lipids Chemical class 0.000 claims 28
- 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 22
- 239000012528 membrane Substances 0.000 claims 21
- 239000004094 surface-active agent Substances 0.000 claims 13
- 239000002202 Polyethylene glycol Substances 0.000 claims 11
- 235000012000 cholesterol Nutrition 0.000 claims 11
- 229920001223 polyethylene glycol Polymers 0.000 claims 11
- 229920001477 hydrophilic polymer Polymers 0.000 claims 9
- 229930012538 Paclitaxel Natural products 0.000 claims 8
- 230000004927 fusion Effects 0.000 claims 8
- 229960001592 paclitaxel Drugs 0.000 claims 8
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims 8
- 150000003904 phospholipids Chemical class 0.000 claims 7
- 239000003795 chemical substances by application Substances 0.000 claims 5
- 238000004519 manufacturing process Methods 0.000 claims 5
- 238000009738 saturating Methods 0.000 claims 5
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 claims 4
- 229920000954 Polyglycolide Polymers 0.000 claims 4
- CTSPAMFJBXKSOY-UHFFFAOYSA-N ellipticine Chemical compound N1=CC=C2C(C)=C(NC=3C4=CC=CC=3)C4=C(C)C2=C1 CTSPAMFJBXKSOY-UHFFFAOYSA-N 0.000 claims 4
- 229920000747 poly(lactic acid) Polymers 0.000 claims 4
- 239000004633 polyglycolic acid Substances 0.000 claims 4
- 239000004626 polylactic acid Substances 0.000 claims 4
- 239000002246 antineoplastic agent Substances 0.000 claims 3
- RYCNUMLMNKHWPZ-SNVBAGLBSA-N 1-acetyl-sn-glycero-3-phosphocholine Chemical compound CC(=O)OC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C RYCNUMLMNKHWPZ-SNVBAGLBSA-N 0.000 claims 2
- AOJJSUZBOXZQNB-VTZDEGQISA-N 4'-epidoxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-VTZDEGQISA-N 0.000 claims 2
- STQGQHZAVUOBTE-UHFFFAOYSA-N 7-Cyan-hept-2t-en-4,6-diinsaeure Natural products C1=2C(O)=C3C(=O)C=4C(OC)=CC=CC=4C(=O)C3=C(O)C=2CC(O)(C(C)=O)CC1OC1CC(N)C(O)C(C)O1 STQGQHZAVUOBTE-UHFFFAOYSA-N 0.000 claims 2
- KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 claims 2
- HTIJFSOGRVMCQR-UHFFFAOYSA-N Epirubicin Natural products COc1cccc2C(=O)c3c(O)c4CC(O)(CC(OC5CC(N)C(=O)C(C)O5)c4c(O)c3C(=O)c12)C(=O)CO HTIJFSOGRVMCQR-UHFFFAOYSA-N 0.000 claims 2
- ZIXGXMMUKPLXBB-UHFFFAOYSA-N Guatambuinine Natural products N1C2=CC=CC=C2C2=C1C(C)=C1C=CN=C(C)C1=C2 ZIXGXMMUKPLXBB-UHFFFAOYSA-N 0.000 claims 2
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 claims 2
- ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 claims 2
- 239000004698 Polyethylene Substances 0.000 claims 2
- 239000004372 Polyvinyl alcohol Substances 0.000 claims 2
- SUYXJDLXGFPMCQ-INIZCTEOSA-N SJ000287331 Natural products CC1=c2cnccc2=C(C)C2=Nc3ccccc3[C@H]12 SUYXJDLXGFPMCQ-INIZCTEOSA-N 0.000 claims 2
- JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 claims 2
- 239000002260 anti-inflammatory agent Substances 0.000 claims 2
- 229940121363 anti-inflammatory agent Drugs 0.000 claims 2
- 229960005475 antiinfective agent Drugs 0.000 claims 2
- 239000004599 antimicrobial Substances 0.000 claims 2
- 230000003115 biocidal effect Effects 0.000 claims 2
- VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical compound C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 claims 2
- 229940127093 camptothecin Drugs 0.000 claims 2
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims 2
- 229960004316 cisplatin Drugs 0.000 claims 2
- 229920001577 copolymer Polymers 0.000 claims 2
- STQGQHZAVUOBTE-VGBVRHCVSA-N daunorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 STQGQHZAVUOBTE-VGBVRHCVSA-N 0.000 claims 2
- 229960000975 daunorubicin Drugs 0.000 claims 2
- 229940039227 diagnostic agent Drugs 0.000 claims 2
- 239000000032 diagnostic agent Substances 0.000 claims 2
- VSJKWCGYPAHWDS-UHFFFAOYSA-N dl-camptothecin Natural products C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)C5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-UHFFFAOYSA-N 0.000 claims 2
- 229960003668 docetaxel Drugs 0.000 claims 2
- 229960004679 doxorubicin Drugs 0.000 claims 2
- 229960001904 epirubicin Drugs 0.000 claims 2
- VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 claims 2
- 229960005420 etoposide Drugs 0.000 claims 2
- 229960001680 ibuprofen Drugs 0.000 claims 2
- 239000003018 immunosuppressive agent Substances 0.000 claims 2
- 229940125721 immunosuppressive agent Drugs 0.000 claims 2
- PIDANAQULIKBQS-RNUIGHNZSA-N meprednisone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)CC2=O PIDANAQULIKBQS-RNUIGHNZSA-N 0.000 claims 2
- 229960001810 meprednisone Drugs 0.000 claims 2
- 235000016709 nutrition Nutrition 0.000 claims 2
- -1 polyethylene Polymers 0.000 claims 2
- 229920000573 polyethylene Polymers 0.000 claims 2
- 229920002451 polyvinyl alcohol Polymers 0.000 claims 2
- 229940068984 polyvinyl alcohol Drugs 0.000 claims 2
- 235000019422 polyvinyl alcohol Nutrition 0.000 claims 2
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 claims 2
- 229960004618 prednisone Drugs 0.000 claims 2
- 229960003048 vinblastine Drugs 0.000 claims 2
- JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 claims 2
- 229960004528 vincristine Drugs 0.000 claims 2
- 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 claims 2
- 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 claims 2
- 230000000118 anti-neoplastic effect Effects 0.000 claims 1
- 229940034982 antineoplastic agent Drugs 0.000 claims 1
- 230000000887 hydrating effect Effects 0.000 claims 1
- 238000010253 intravenous injection Methods 0.000 claims 1
- 239000000693 micelle Substances 0.000 claims 1
- 238000009472 formulation Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
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 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) |
Families Citing this family (156)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6200547B1 (en) * | 1994-01-26 | 2001-03-13 | Ferx Incorporated | Magnetically responsive compositions for carrying biologically active substances and methods of production and use |
US6482436B1 (en) | 1993-01-29 | 2002-11-19 | Ferx Incorporated | Magnetically responsive composition |
US7393682B1 (en) | 1993-03-19 | 2008-07-01 | The Johns Hopkins University School Of Medicine | Polynucleotides encoding promyostatin polypeptides |
US6096336A (en) * | 1996-01-30 | 2000-08-01 | The Stehlin Foundation For Cancer Research | Liposomal prodrugs comprising derivatives of camptothecin and methods of treating cancer using these prodrugs |
US5827533A (en) * | 1997-02-06 | 1998-10-27 | Duke University | Liposomes containing active agents aggregated with lipid surfactants |
US6207186B1 (en) * | 1997-02-14 | 2001-03-27 | The Regents Of The University Of California | Lamellar gels and methods for making and using |
US6287591B1 (en) * | 1997-05-14 | 2001-09-11 | Inex Pharmaceuticals Corp. | Charged therapeutic agents encapsulated in lipid particles containing four lipid components |
US6891082B2 (en) | 1997-08-01 | 2005-05-10 | The Johns Hopkins University School Of Medicine | Transgenic non-human animals expressing a truncated activintype II receptor |
ES2373861T3 (en) | 1997-09-18 | 2012-02-09 | Pacira Pharmaceuticals, Inc. | LIPOSOMIAL ANESTHETIC COMPOSITIONS OF SUSTAINED RELEASE. |
US20050003008A1 (en) * | 1997-09-23 | 2005-01-06 | Natalya Rapoport | Method of in vivo drug targeting to solid tumors via acoustically triggered drug delivery in polymeric micelles |
AU752802C (en) | 1997-11-14 | 2006-04-13 | Pacira Pharmaceuticals, Inc. | Production of multivesicular liposomes |
US20030059465A1 (en) * | 1998-05-11 | 2003-03-27 | Unger Evan C. | Stabilized nanoparticle formulations of camptotheca derivatives |
US6726925B1 (en) * | 1998-06-18 | 2004-04-27 | Duke University | Temperature-sensitive liposomal formulation |
ES2325141T3 (en) | 1998-07-17 | 2009-08-26 | Pacira Pharmaceuticals, Inc. | BIODEGRADABLE COMPOSITIONS FOR THE CONTROLLED RELEASE OF ENCAPSULATED SUBSTANCES. |
EP1105096B1 (en) | 1998-08-19 | 2003-10-29 | Skyepharma Canada Inc. | Injectable aqueous dispersions of propofol |
US6352996B1 (en) | 1999-08-03 | 2002-03-05 | The Stehlin Foundation For Cancer Research | Liposomal prodrugs comprising derivatives of camptothecin and methods of treating cancer using these prodrugs |
US6228855B1 (en) | 1999-08-03 | 2001-05-08 | The Stehlin Foundation For Cancer Research | Aromatic esters of camptothecins and methods to treat cancers |
US6511676B1 (en) * | 1999-11-05 | 2003-01-28 | Teni Boulikas | Therapy for human cancers using cisplatin and other drugs or genes encapsulated into liposomes |
US6210611B1 (en) * | 1999-11-30 | 2001-04-03 | Duke University | Methods for producing gas microbubbles having lipid-containing shells formed thereon |
US20040009229A1 (en) * | 2000-01-05 | 2004-01-15 | Unger Evan Charles | Stabilized nanoparticle formulations of camptotheca derivatives |
AU2001258106A1 (en) * | 2000-05-11 | 2001-11-20 | Celator Technologies Inc. | Lipid carrier compositions for improved drug retention |
US20060177416A1 (en) | 2003-10-14 | 2006-08-10 | Medivas, Llc | Polymer particle delivery compositions and methods of use |
ATE413164T1 (en) | 2000-11-09 | 2008-11-15 | Neopharm Inc | SN-38 LIPID COMPLEXES AND METHODS OF USE THEREOF |
CA2430947A1 (en) | 2000-12-08 | 2002-06-13 | Invitrogen Corporation | Methods and compositions for synthesis of nucleic acid molecules using multiple recognition sites |
US6897196B1 (en) * | 2001-02-07 | 2005-05-24 | The Regents Of The University Of California | pH sensitive lipids based on ortho ester linkers, composition and method |
US6534080B2 (en) | 2001-02-12 | 2003-03-18 | Super Gen, Inc. | Method for administering camptothecins via injection of pharmaceutical composition comprising coated particles of a camptothecin |
US6509027B2 (en) | 2001-02-12 | 2003-01-21 | Supergen, Inc. | Injectable pharmaceutical composition comprising coated particles of camptothecin |
US6497896B2 (en) | 2001-02-12 | 2002-12-24 | Supergen, Inc. | Method for administering camptothecins via injection of a pharmaceutical composition comprising microdroplets containing a camptothecin |
US20020150615A1 (en) * | 2001-02-12 | 2002-10-17 | Howard Sands | Injectable pharmaceutical composition comprising microdroplets of a camptothecin |
EP1365705A1 (en) * | 2001-02-12 | 2003-12-03 | SuperGen, Inc. | Injectable pharmaceutical composition comprising microparticles or microdroplets of camptothecin |
US20030157170A1 (en) * | 2001-03-13 | 2003-08-21 | Richard Liggins | Micellar drug delivery vehicles and precursors thereto and uses thereof |
WO2002072150A2 (en) * | 2001-03-13 | 2002-09-19 | Angiotech Pharmaceuticals Inc. | Micellar drug delivery vehicles and uses thereof |
EP1385479A4 (en) * | 2001-03-26 | 2006-12-06 | Alza Corp | Liposome composition for improved intracellular delivery of a therapeutic agent |
DE10117043A1 (en) * | 2001-04-05 | 2002-11-07 | Gerhard Puetz | Process for the elimination of potentially toxic and / or harmful substances |
EP1800670A1 (en) | 2001-04-20 | 2007-06-27 | The University of British Columbia | Micellar drug delivery systems for hydrophobic drugs |
US20050013810A1 (en) * | 2001-05-08 | 2005-01-20 | Waller Edmund K | Regulating immune response using dendritic cells |
SE0101702D0 (en) * | 2001-05-15 | 2001-05-15 | Ardenia Investments Ltd | Novel potentiating compounds |
WO2003030864A1 (en) * | 2001-05-29 | 2003-04-17 | Neopharm, Inc. | Liposomal formulation of irinotecan |
CA2447990C (en) * | 2001-05-31 | 2012-01-31 | Skyepharma Inc. | Encapsulation of nanosuspensions in liposomes and microspheres |
KR100439068B1 (en) * | 2001-09-07 | 2004-07-05 | 주식회사 코리아나화장품 | Stablized cosmetic material containing triple layered retonol |
WO2003022250A2 (en) * | 2001-09-10 | 2003-03-20 | Celator Technologies Inc. | Unilamellar vesicles stabilized with short chain hydrophilic polymers |
US20050227911A1 (en) * | 2001-09-28 | 2005-10-13 | Solubest Ltd. | Hydrophilic dispersions of nanoparticles of inclusion complexes of macromolecules |
US6878693B2 (en) * | 2001-09-28 | 2005-04-12 | Solubest Ltd. | Hydrophilic complexes of lipophilic materials and an apparatus and method for their production |
US20050233003A1 (en) * | 2001-09-28 | 2005-10-20 | Solubest Ltd. | Hydrophilic dispersions of nanoparticles of inclusion complexes of salicylic acid |
US20030152622A1 (en) * | 2001-10-25 | 2003-08-14 | Jenny Louie-Helm | Formulation of an erodible, gastric retentive oral diuretic |
US20030091630A1 (en) * | 2001-10-25 | 2003-05-15 | Jenny Louie-Helm | Formulation of an erodible, gastric retentive oral dosage form using in vitro disintegration test data |
US7700851B2 (en) * | 2001-11-13 | 2010-04-20 | U.S. Smokeless Tobacco Company | Tobacco nicotine demethylase genomic clone and uses thereof |
WO2003041682A2 (en) * | 2001-11-13 | 2003-05-22 | Celator Technologies, Inc. | Lipid carrier compositions and methods for improved drug retention |
US20060078618A1 (en) * | 2001-12-11 | 2006-04-13 | Constantinides Panayiotis P | Lipid particles and suspensions and uses thereof |
US20040186063A1 (en) * | 2002-02-15 | 2004-09-23 | Hans-Jurgen Gutke | Conjugates of biologically active compounds, methods for their preparation and use, formulation and pharmaceutical applications thereof |
CA2476448A1 (en) * | 2002-02-15 | 2003-08-28 | Sympore Gmbh | Antibiotic conjugates |
US20050171342A1 (en) * | 2002-02-15 | 2005-08-04 | Michael Burnet | Conjugates of biologically active compounds, methods for their preparation and use, formulation and pharmaceutical applications thereof |
AU2003215245A1 (en) * | 2002-02-15 | 2003-09-09 | Sympore Gmbh | Conjugates of biologically active compounds, methods for their preparation and use, formulation and pharmaceutical applications thereof |
AU2003220277A1 (en) * | 2002-03-12 | 2003-09-29 | The Johns Hopkins University School Of Medicine | Manganese ion regulation of reverse transcriptase activity and methods of modulating same |
US20030232075A1 (en) * | 2002-05-06 | 2003-12-18 | University Of Minnesota, A Minnesota Corporation | Compositions for producing factor Xa |
AU2003234670B2 (en) | 2002-05-24 | 2010-06-10 | Angiotech International Ag | Compositions and methods for coating medical implants |
AU2003296897A1 (en) * | 2002-08-20 | 2004-05-04 | Neopharm, Inc. | Pharmaceutical formulations of camptothecine derivatives |
US20060030578A1 (en) * | 2002-08-20 | 2006-02-09 | Neopharm, Inc. | Pharmaceutically active lipid based formulation of irinotecan |
AR036316A1 (en) * | 2002-08-29 | 2004-08-25 | Monte Verde S A | A PHARMACEUTICAL COMPOSITION OF SMALL SIZE LIPOSOMES AND PREPARATION METHOD |
US6964778B1 (en) * | 2002-09-06 | 2005-11-15 | Health Research, Inc. | Temperature controlled content release from liposomes |
US6991805B1 (en) * | 2002-09-06 | 2006-01-31 | Health Research, Inc. | Temperature sensitive control of liposome-cell adhesion |
US20040115226A1 (en) * | 2002-12-12 | 2004-06-17 | Wenji Li | Free-flowing solid formulations with improved bio-availability of poorly water soluble drugs and process for making the same |
US8142814B2 (en) * | 2003-02-07 | 2012-03-27 | Ferro Corporation | Method and apparatus for supercritical fluid assisted particle production |
US20040204435A1 (en) * | 2003-04-09 | 2004-10-14 | Joachim Liehr | Alternating treatment with topoisomerase I and topoisomerase II inhibitors |
WO2005005977A2 (en) * | 2003-06-30 | 2005-01-20 | Applera Corporation | Fluorescent phospholipase assays and compositions |
JP4394916B2 (en) * | 2003-09-19 | 2010-01-06 | 独立行政法人科学技術振興機構 | Artificial lipid bilayer membrane formation apparatus, artificial lipid bilayer membrane formation method, and use thereof |
DE602004023765D1 (en) * | 2004-03-12 | 2009-12-03 | Trinity College Dublin | MAGNETORESISTIVE MEDIUM |
US7187286B2 (en) | 2004-03-19 | 2007-03-06 | Applera Corporation | Methods and systems for using RFID in biological field |
US20050238675A1 (en) * | 2004-04-26 | 2005-10-27 | Wenjie Li | Water-soluble formulations of fat soluble vitamins and pharmaceutical agents and their applications |
WO2005112924A2 (en) * | 2004-04-27 | 2005-12-01 | California Institute Of Technology | Methods of treating cancer by inhibiting histone gene expression |
WO2005107712A1 (en) | 2004-05-03 | 2005-11-17 | Hermes Biosciences, Inc. | Liposomes useful for drug delivery |
AP2255A (en) | 2004-06-01 | 2011-07-21 | Yakult Honsha Kk | Irinotecan preparation. |
EP1750671B1 (en) * | 2004-06-03 | 2008-10-15 | Bracco Research S.A. | Liposomal assembly for therapeutic and/or diagnostic use |
JP4433918B2 (en) * | 2004-07-15 | 2010-03-17 | コニカミノルタエムジー株式会社 | Image forming method |
WO2006030523A1 (en) * | 2004-09-17 | 2006-03-23 | Japan Science And Technology Agency | Lipid substitution method in artificial lipid double membrane, artificial lipid double membrane obtained by that method, equipment for producing artificial lipid double membrane, and ion permeation measuring equipment |
US7635754B2 (en) * | 2004-09-22 | 2009-12-22 | Aerovance, Inc. | Interleukin-9 and interleukin-4 chimeric antagonist muteins and methods of using same |
KR100651728B1 (en) * | 2004-11-10 | 2006-12-06 | 한국전자통신연구원 | Compound for an electronic device having a fixing group, an electronic device comprising the same and a method of manufacturing the same |
EP1855669A4 (en) * | 2005-01-28 | 2010-07-07 | Bc Cancer Agency | LIPOSOMAL COMPOSITIONS FOR PARENTERAL ADMINISTRATION OF AGENTS |
EP1907392A1 (en) * | 2005-07-26 | 2008-04-09 | Merckle Gmbh | Macrolide conjugates of pyrrolizine and indolizine compounds as inhibitors of 5-lipooxygenase and cyclooxygenase |
EP1933881B1 (en) * | 2005-09-22 | 2019-03-13 | Medivas, LLC | Solid polymer delivery compositions and methods for use thereof |
JP5192384B2 (en) | 2005-09-22 | 2013-05-08 | メディバス エルエルシー | Bis- (α-amino) -diol-diester-containing poly (ester amide) and poly (ester urethane) compositions and methods of use |
US7875602B2 (en) * | 2005-10-21 | 2011-01-25 | Sutter West Bay Hospitals | Camptothecin derivatives as chemoradiosensitizing agents |
WO2007067744A2 (en) * | 2005-12-07 | 2007-06-14 | Medivas, Llc | Method for assembling a polymer-biologic delivery composition |
US20070197486A1 (en) * | 2005-12-20 | 2007-08-23 | Verus Pharmaceuticals, Inc. | Methods and systems for the delivery of corticosteroids |
US20070249572A1 (en) * | 2005-12-20 | 2007-10-25 | Verus Pharmaceuticals, Inc. | Systems and methods for the delivery of corticosteroids |
US20070185066A1 (en) * | 2005-12-20 | 2007-08-09 | Verus Pharmaceuticals, Inc. | Systems and methods for the delivery of corticosteroids |
US20070178049A1 (en) * | 2005-12-20 | 2007-08-02 | Verus Pharmaceuticals, Inc. | Systems and methods for the delivery of corticosteroids having an enhanced pharmacokinetic profile |
US20070160542A1 (en) * | 2005-12-20 | 2007-07-12 | Verus Pharmaceuticals, Inc. | Methods and systems for the delivery of corticosteroids having an enhanced pharmacokinetic profile |
WO2007095341A2 (en) * | 2006-02-15 | 2007-08-23 | Tika Läkemedel Ab | Sterilization of corticosteroids with reduced mass loss |
US20070292476A1 (en) * | 2006-05-02 | 2007-12-20 | Medivas, Llc | Delivery of ophthalmologic agents to the exterior or interior of the eye |
EP2021141A4 (en) * | 2006-05-09 | 2013-07-03 | Medivas Llc | Biodegradable water soluble polymers |
JP2009539404A (en) | 2006-06-12 | 2009-11-19 | オンコメチローム サイエンシズ エス.エイ. | Methylation markers for early detection and prognosis of colorectal cancer |
BRPI0717800A2 (en) * | 2006-10-06 | 2014-09-09 | Politechnic Inst Univ New York | COMPOSITION OF PH SENSITIVE LIPOSOMES |
US20100047334A1 (en) * | 2006-10-06 | 2010-02-25 | Sofou Stavroula | Ph sensitive liposome compositions for controlling surface topography and binding reactivity in functionalized liposomes |
JP2008214324A (en) * | 2007-02-28 | 2008-09-18 | Hokkaido Univ | Micelle encapsulated liposome |
WO2009006311A2 (en) * | 2007-06-29 | 2009-01-08 | Wisconsin Alumni Research Foundation | Structuring effect of cholesterol in peg-phospholipid micelles, drug delivery of amphotericin b, and combination antifungals |
KR101405417B1 (en) | 2007-07-19 | 2014-06-12 | (주)아모레퍼시픽 | Manufacturing Method of Skin External Composition Controlled Transepidermal Absorption Using Phase Transition of Lysophospholipids based Colloid |
US20090029937A1 (en) * | 2007-07-24 | 2009-01-29 | Cornell University | Biodegradable cationic polymer gene transfer compositions and methods of use |
WO2009026328A2 (en) * | 2007-08-21 | 2009-02-26 | Immune Disease Institute, Inc. | Methods of delivery of agents to leukocytes and endothelial cells |
ES2330295B1 (en) * | 2008-06-06 | 2010-09-23 | Laboratorios Alcala Farma, Sl | TOPIC FORMULATION OF IBUPROFEN. |
US8173621B2 (en) | 2008-06-11 | 2012-05-08 | Gilead Pharmasset Llc | Nucleoside cyclicphosphates |
CA2733686A1 (en) * | 2008-08-13 | 2010-02-18 | Medivas, Llc | Aabb-poly(depsipeptide) biodegradable polymers and methods of use |
AR074897A1 (en) | 2008-12-23 | 2011-02-23 | Pharmasset Inc | NUCLEOSID PHOSPHORAMIDATES |
CA2748034A1 (en) | 2008-12-23 | 2010-07-01 | Pharmasset, Inc. | Purified 2'-deoxy'2'-fluoro-2'-c-methyl-nucleoside-phosphoramidate prodrugs for the treatment of viral infections |
CA2748016A1 (en) | 2008-12-23 | 2010-07-01 | Pharmasset, Inc. | Synthesis of purine nucleosides |
KR101395858B1 (en) * | 2009-04-03 | 2014-05-15 | 우한 도칸 파마슈티컬 컴퍼니 리미티드 | A polysaccharide liposome, the preparation method and use of it |
TWI576352B (en) | 2009-05-20 | 2017-04-01 | 基利法瑪席特有限責任公司 | Nucleoside phosphoramidates |
BRPI1010175A2 (en) * | 2009-06-02 | 2016-03-29 | Keller Brian Charles | "chemical composition including a lipid-peg and liposome conjugate" |
US20110045096A1 (en) * | 2009-08-19 | 2011-02-24 | Pankaj Modi | Solubilized delivery system for topical anesthetics |
CN102048725B (en) * | 2009-10-29 | 2014-07-16 | 中国医学科学院药物研究所 | Taxol-cholesterin complex |
AR093275A1 (en) | 2010-03-17 | 2015-05-27 | Centro De Excelencia En Productos Y Procesos De Cordoba (Ceprocor) | A PHARMACEUTICAL COMPOSITION SOLUBLE IN WATER THAT INCLUDES AT LEAST A THERAPEUTICALLY ACTIVE SUBSTANCE OF HYDROPHOBIC CHARACTERISTICS AND AT LEAST A SELECTED COMPOSITE BETWEEN THE SYMPHOGLIOPHYMPHYLOPHYLOPHYLOPHYLOPHYLOPHYLOPHYLOPHYLOPHYLOPHYLOPHYLOPHYL SOPHYLOPHYLOPHYLOPHYLOSPHYLOPHYLOPHYLOPHYL SINGLE WATER SOLUBLE COMPOSITION IN A WATER SOLUBLE PHARMACEUTICAL COMPOSITION THAT INCLUDES AT LEAST A THERAPEUTICALLY ACTIVE SUBSTANCE OF HYDROPHOBIC CHARACTERISTICS AND AT LEAST A SELECTED COMPOSITE |
US8563530B2 (en) | 2010-03-31 | 2013-10-22 | Gilead Pharmassel LLC | Purine nucleoside phosphoramidate |
PL2552930T3 (en) | 2010-03-31 | 2016-02-29 | Gilead Pharmasset Llc | Crystalline (s)-isopropyl 2-(((s)-(((2r,3r,4r,5r)-5-(2,4-dioxo-3,4-dihydropyrimidin-1-(2h)-yl)-4-fluoro-3-hydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate |
TW201136945A (en) | 2010-03-31 | 2011-11-01 | Pharmasset Inc | Purine nucleoside phosphoramidate |
WO2011148207A1 (en) | 2010-05-28 | 2011-12-01 | Diagon Kft. | Procedure for biphasic preparation of liposomes and application thereof in manufacturing diagnostic reagents |
ES2694556T3 (en) * | 2010-09-02 | 2018-12-21 | The Scripps Research Institute | Delivery of nanoparticle-based drug focused on a tumor |
TW201242974A (en) | 2010-11-30 | 2012-11-01 | Gilead Pharmasset Llc | Compounds |
US10449193B2 (en) * | 2011-06-03 | 2019-10-22 | Signpath Pharma Inc. | Protective effect of DMPC, DMPG, DMPC/DMPG, lysoPG and lysoPC against drugs that cause channelopathies |
US10238602B2 (en) | 2011-06-03 | 2019-03-26 | Signpath Pharma, Inc. | Protective effect of DMPC, DMPG, DMPC/DMPG, LysoPG and LysoPC against drugs that cause channelopathies |
US12004868B2 (en) | 2011-06-03 | 2024-06-11 | Signpath Pharma Inc. | Liposomal mitigation of drug-induced inhibition of the cardiac IKr channel |
US10349884B2 (en) | 2011-06-03 | 2019-07-16 | Sighpath Pharma Inc. | Liposomal mitigation of drug-induced inhibition of the cardiac ikr channel |
WO2012167212A2 (en) | 2011-06-03 | 2012-12-06 | Signpath Pharma Inc. | Liposomal mitigation of drug-induced long qt syndrome and potassium delayed-rectifier current |
US10532045B2 (en) | 2013-12-18 | 2020-01-14 | Signpath Pharma, Inc. | Liposomal mitigation of drug-induced inhibition of the cardiac IKr channel |
CN103619910B (en) | 2011-06-23 | 2016-08-31 | 帝斯曼知识产权资产管理有限公司 | The novel polyester-amide copolymer delivered for medicine |
US9873765B2 (en) | 2011-06-23 | 2018-01-23 | Dsm Ip Assets, B.V. | Biodegradable polyesteramide copolymers for drug delivery |
AU2013203682B2 (en) * | 2011-08-25 | 2016-03-31 | Trophos | Liposome comprising at least one cholesterol derivative |
FR2979239A1 (en) | 2011-08-25 | 2013-03-01 | Trophos | LIPOSOME COMPRISING AT LEAST ONE CHOLESTEROL DERIVATIVE |
WO2013044177A2 (en) | 2011-09-23 | 2013-03-28 | Loma Linda University | Bacterial strains expressing methylase genes and uses thereof |
CN102579350B (en) * | 2012-03-02 | 2013-04-24 | 海南灵康制药有限公司 | Pidotimod liposome solid preparation |
EP4378461A3 (en) * | 2013-03-05 | 2024-09-11 | The Regents of University of California | Lipid bilayer coated mesoporous silica nanoparticles with a high loading capacity for one or more anticancer agents |
WO2014145042A1 (en) | 2013-03-15 | 2014-09-18 | Loma Linda University | Treatment of autoimmune diseases |
ES2942132T3 (en) | 2014-06-03 | 2023-05-30 | Signpath Pharma Inc | Protective effect of DMPC, DMPG, DMPC/DMPG, EGPG, LYSOPG and LYSOPC against drugs that cause channelopathies |
WO2016097297A1 (en) | 2014-12-18 | 2016-06-23 | Dsm Ip Assets B.V. | Drug delivery system for delivery of acid sensitive drugs |
US10596117B1 (en) | 2014-12-31 | 2020-03-24 | Eric Morrison | Lipoleosomes as carriers for aromatic amide anesthetic compounds |
US11007161B1 (en) | 2014-12-31 | 2021-05-18 | Eric Morrison | Ibuprofen nanoparticle carriers encapsulated with hermatic surfactant films |
US10561627B2 (en) | 2014-12-31 | 2020-02-18 | Eric Morrison | Ibuprofen nanoparticle carriers encapsulated with hermetic surfactant films |
AR100034A1 (en) | 2015-01-30 | 2016-09-07 | Consejo Nac De Investig Científicas Y Técnicas (Conicet) | A PHARMACEUTICAL COMPOSITION SOLUBLE IN WATER THAT INCLUDES, AT LEAST, A THERAPEUTICALLY ACTIVE SUBSTANCE AND, AT LEAST, A CAPACITY SUBSTANCE TO FORM MICELAS |
TW201722965A (en) | 2015-08-16 | 2017-07-01 | 葛蘭素史密斯克藍智慧財產發展有限公司 | Compounds for use in antibacterial applications |
BR122021024957B1 (en) | 2015-10-16 | 2023-12-12 | Ipsen Biopharm Ltd | Processes for producing a storage-stabilized liposomal irinotecan composition |
CN108601746B (en) | 2016-01-08 | 2024-09-13 | 加利福尼亚大学董事会 | Mesoporous silica nanoparticles with lipid bilayer coating for cargo delivery |
KR102603673B1 (en) | 2016-04-27 | 2023-11-17 | 사인패스 파마 인코포레이티드 | Prevention of drug-induced atrio-ventricular block |
US11246832B2 (en) | 2016-06-28 | 2022-02-15 | Verily Life Sciences Llc | Serial filtration to generate small cholesterol-containing liposomes |
EP3648758A4 (en) | 2017-07-07 | 2021-04-28 | Drexel University | VOLTAGE ACTIVATED THERAPEUTIC, DIAGNOSTIC AND / OR THERANOSTIC CONSTRUCTS |
US11112416B2 (en) | 2018-01-30 | 2021-09-07 | Life Technologies Corporation | Instruments, devices and consumables for use in a workflow of a smart molecular analysis system |
WO2019165101A1 (en) | 2018-02-22 | 2019-08-29 | Verily Life Sciences Llc | Combining orthogonal chemistries for preparation of multiplexed nanoparticles |
CN108721644B (en) * | 2018-06-05 | 2021-06-08 | 常州金远药业制造有限公司 | Preparation method of taxane medicine liposome |
WO2020058892A1 (en) | 2018-09-20 | 2020-03-26 | Pharmafilm Srl | Deformable liposomes containing micelles |
AU2020287895A1 (en) * | 2019-06-03 | 2021-12-23 | Dropworks, Inc. | Systems and methods for stabilizing emulsions |
US12151024B2 (en) | 2021-01-22 | 2024-11-26 | Pacira Pharmaceuticals, Inc. | Manufacturing of bupivacaine multivesicular liposomes |
US11033495B1 (en) | 2021-01-22 | 2021-06-15 | Pacira Pharmaceuticals, Inc. | Manufacturing of bupivacaine multivesicular liposomes |
US11278494B1 (en) | 2021-01-22 | 2022-03-22 | Pacira Pharmaceuticals, Inc. | Manufacturing of bupivacaine multivesicular liposomes |
US11357727B1 (en) | 2021-01-22 | 2022-06-14 | Pacira Pharmaceuticals, Inc. | Manufacturing of bupivacaine multivesicular liposomes |
EP4415713A1 (en) | 2021-10-14 | 2024-08-21 | Pacira Pharmaceuticals, Inc. | Bupivacaine multivesicular liposome formulations and uses thereof |
US12251468B1 (en) | 2024-05-20 | 2025-03-18 | Pacira Pharmaceuticals, Inc. | Manufacturing of bupivacaine multivesicular liposomes |
US12251472B1 (en) | 2024-05-20 | 2025-03-18 | Pacira Pharmaceuticals, Inc. | Manufacturing of bupivacaine multivesicular liposomes |
US12246092B1 (en) | 2024-05-20 | 2025-03-11 | Pacira Pharmaceuticals, Inc. | Manufacturing of bupivacaine multivesicular liposomes |
Family Cites Families (51)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4489056A (en) * | 1982-06-30 | 1984-12-18 | Merck & Co., Inc. | Acid anhydrides as rate controlling agent for the erosion of polymers which latter polymers have beneficial substances dispersed throughout their matrix or where the polymer matrix surrounds the beneficial substance |
US4551288A (en) * | 1982-08-16 | 1985-11-05 | Sandoz, Inc. | Processes for the preparation of liposome drug delivery systems |
US4544545A (en) * | 1983-06-20 | 1985-10-01 | Trustees University Of Massachusetts | Liposomes containing modified cholesterol for organ targeting |
US4876094A (en) * | 1984-01-13 | 1989-10-24 | Battelle Development Corporation | Controlled release liquid dosage formulation |
US4921706A (en) * | 1984-11-20 | 1990-05-01 | Massachusetts Institute Of Technology | Unilamellar lipid vesicles and method for their formation |
US4762915A (en) * | 1985-01-18 | 1988-08-09 | Liposome Technology, Inc. | Protein-liposome conjugates |
US4921757A (en) * | 1985-04-26 | 1990-05-01 | Massachusetts Institute Of Technology | System for delayed and pulsed release of biologically active substances |
US4900556A (en) * | 1985-04-26 | 1990-02-13 | Massachusetts Institute Of Technology | System for delayed and pulsed release of biologically active substances |
JPH0617309B2 (en) * | 1985-11-29 | 1994-03-09 | 株式会社ビタミン研究所 | Adriamycin embedded liposome preparation |
US4737323A (en) * | 1986-02-13 | 1988-04-12 | Liposome Technology, Inc. | Liposome extrusion method |
US4752425A (en) * | 1986-09-18 | 1988-06-21 | Liposome Technology, Inc. | High-encapsulation liposome processing method |
US4920016A (en) * | 1986-12-24 | 1990-04-24 | Linear Technology, Inc. | Liposomes with enhanced circulation time |
US4837028A (en) * | 1986-12-24 | 1989-06-06 | Liposome Technology, Inc. | Liposomes with enhanced circulation time |
US4839111A (en) * | 1987-02-02 | 1989-06-13 | The University Of Tennessee Research Corporation | Preparation of solid core liposomes |
JPH0825869B2 (en) * | 1987-02-09 | 1996-03-13 | 株式会社ビタミン研究所 | Antitumor agent-embedded liposome preparation |
US5755788A (en) | 1987-02-19 | 1998-05-26 | Rutgers, The State University | Prosthesis and implants having liposomes bound thereto and methods of preparation |
US5628936A (en) * | 1987-03-13 | 1997-05-13 | Micro-Pak, Inc. | Hybrid paucilamellar lipid vesicles |
US5023086A (en) * | 1987-03-13 | 1991-06-11 | Micro-Pak, Inc. | Encapsulated ionophore growth factors |
US4828837A (en) * | 1987-03-30 | 1989-05-09 | Liposome Technology, Inc. | Non-crystalline minoxidil composition, its production and application |
US4921644A (en) * | 1988-02-29 | 1990-05-01 | Technology Unlimited, Inc. | Mucin directed lipsome |
US5160669A (en) * | 1988-03-03 | 1992-11-03 | Micro Vesicular Systems, Inc. | Method of making oil filled paucilamellar lipid vesicles |
ATE77051T1 (en) | 1988-03-04 | 1992-06-15 | Takeda Chemical Industries Ltd | LIPOSOME COMPOSITION. |
US4906476A (en) * | 1988-12-14 | 1990-03-06 | Liposome Technology, Inc. | Novel liposome composition for sustained release of steroidal drugs in lungs |
US5236355A (en) * | 1988-12-22 | 1993-08-17 | American Cyanamid Company | Apparatus for the treatment of periodontal disease |
US5013556A (en) * | 1989-10-20 | 1991-05-07 | Liposome Technology, Inc. | Liposomes with enhanced circulation time |
US5527528A (en) * | 1989-10-20 | 1996-06-18 | Sequus Pharmaceuticals, Inc. | Solid-tumor treatment method |
US5843473A (en) * | 1989-10-20 | 1998-12-01 | Sequus Pharmaceuticals, Inc. | Method of treatment of infected tissues |
US5356633A (en) * | 1989-10-20 | 1994-10-18 | Liposome Technology, Inc. | Method of treatment of inflamed tissues |
US5225212A (en) * | 1989-10-20 | 1993-07-06 | Liposome Technology, Inc. | Microreservoir liposome composition and method |
US5209720A (en) | 1989-12-22 | 1993-05-11 | Unger Evan C | Methods for providing localized therapeutic heat to biological tissues and fluids using gas filled liposomes |
WO1992003123A1 (en) * | 1990-08-28 | 1992-03-05 | Liposome Technology, Inc. | Liposome alternative bilayer formulations |
US5643600A (en) * | 1991-09-17 | 1997-07-01 | Micro-Pak, Inc. | Lipid vesicles containing avocado oil unsaponifiables |
JPH07505408A (en) | 1992-04-08 | 1995-06-15 | キンヌネン,パーボ カイ ヨハネス | Therapeutic and diagnostic compositions and their production methods, and their uses |
US5552156A (en) | 1992-10-23 | 1996-09-03 | Ohio State University | Liposomal and micellular stabilization of camptothecin drugs |
US6764693B1 (en) | 1992-12-11 | 2004-07-20 | Amaox, Ltd. | Free radical quenching composition and a method to increase intracellular and/or extracellular antioxidants |
WO1994016061A1 (en) | 1993-01-15 | 1994-07-21 | Micro Vesicular Systems, Inc. | Method of inhibiting viral reproduction |
US5395619A (en) * | 1993-03-03 | 1995-03-07 | Liposome Technology, Inc. | Lipid-polymer conjugates and liposomes |
US6326353B1 (en) * | 1993-03-23 | 2001-12-04 | Sequus Pharmaceuticals, Inc. | Enhanced circulation effector composition and method |
AU6785094A (en) * | 1993-05-07 | 1994-12-12 | Sequus Pharmaceuticals, Inc. | Subcutaneous liposome delivery method |
AU6833994A (en) * | 1993-05-17 | 1994-12-12 | Liposome Company, Inc., The | Incorporation of taxol into liposomes and gels |
US5478860A (en) | 1993-06-04 | 1995-12-26 | Inex Pharmaceuticals Corp. | Stable microemulsions for hydrophobic compound delivery |
US5534241A (en) * | 1993-07-23 | 1996-07-09 | Torchilin; Vladimir P. | Amphipathic polychelating compounds and methods of use |
WO1995008986A1 (en) | 1993-09-27 | 1995-04-06 | Smithkline Beecham Corporation | Camptothecin formulations |
US5415869A (en) | 1993-11-12 | 1995-05-16 | The Research Foundation Of State University Of New York | Taxol formulation |
EP0734251B1 (en) | 1993-12-17 | 2009-10-14 | Novavax, Inc. | Method of transmitting a biologically active material to a cell |
US5534499A (en) * | 1994-05-19 | 1996-07-09 | The University Of British Columbia | Lipophilic drug derivatives for use in liposomes |
JPH08151333A (en) * | 1994-09-29 | 1996-06-11 | Ryuichi Kamioka | Hybrid type liposome preparation for treating brain tumor |
IL115849A0 (en) * | 1994-11-03 | 1996-01-31 | Merz & Co Gmbh & Co | Tangential filtration preparation of liposomal drugs and liposome product thereof |
WO1996025147A1 (en) | 1995-02-14 | 1996-08-22 | Sequus Pharmaceuticals, Inc. | Liposome composition and method for administering liposome-loadable drugs |
DE19506463C2 (en) * | 1995-02-24 | 1998-11-12 | Boewe Systec Ag | Jam monitoring device for a transport device for paper, in particular for a paper web |
US5827533A (en) * | 1997-02-06 | 1998-10-27 | Duke University | Liposomes containing active agents aggregated with lipid surfactants |
-
1997
- 1997-02-06 US US08/795,100 patent/US5827533A/en not_active Expired - Lifetime
-
1998
- 1998-02-03 US US09/017,984 patent/US6296870B1/en not_active Expired - Lifetime
- 1998-02-05 AU AU63196/98A patent/AU6319698A/en not_active Abandoned
- 1998-02-05 WO PCT/US1998/002154 patent/WO1998034597A1/en active Application Filing
- 1998-08-05 US US09/129,654 patent/US5882679A/en not_active Expired - Lifetime
- 1998-10-19 US US09/174,775 patent/US6143321A/en not_active Expired - Lifetime
Similar Documents
Publication | Publication Date | Title |
---|---|---|
WO1998034597B1 (en) | Liposomes containing active agents | |
US6214375B1 (en) | Phospholipid formulations | |
Perrett et al. | A simple method for the preparation of liposomes for pharmaceutical applications: characterization of the liposomes | |
MacLachlan | Liposomal formulations for nucleic acid delivery | |
Photos et al. | Polymer vesicles in vivo: correlations with PEG molecular weight | |
CA3059714C (en) | Flow channel structure and lipid particle or micelle formation method using same | |
CA2137297C (en) | Reactive vesicle and functional substance-fixed vesicle | |
EP0460720B1 (en) | A method of extruding liposomes | |
US20080181939A1 (en) | Polymersomes and related encapsulating membranes | |
Hirai et al. | Accumulation of liposome with Sialyl Lewis X to inflammation and tumor region: application to in vivo bio-imaging | |
US20050003016A1 (en) | Controlled release polymersomes | |
Sriwongsitanont et al. | Effect of a PEG lipid (DSPE-PEG2000) and freeze-thawing process on phospholipid vesicle size and lamellarity | |
WO1996040061A1 (en) | Method for encapsulating pharmaceutical materials | |
US10117833B2 (en) | Method for producing liposome | |
US7495116B2 (en) | Phospholipid derivative | |
CA2286177C (en) | Composition for gene transfer into cells | |
US20080317840A1 (en) | Compositions and methods for polymer-caged liposomes | |
Silvander | Steric stabilization of liposomes—a review | |
US20050129750A1 (en) | Process for producing liposome suspension and product containing liposome suspension produced thereby | |
US20170027869A1 (en) | Liposomal mupirocin | |
Riché et al. | Novel long-circulating liposomes containing peptide library-lipid conjugates: synthesis and in vivo behavior | |
CA1303990C (en) | Solubilization of hydrophobic materials using lysophospholipids | |
Ozawa et al. | Bilayer-domain formation of thermoresponsive amphiphilic block copolymers in hybrid liposomes for synthetic molecular channels | |
CA2513144C (en) | Phospholipid derivative and method for producing the same | |
Bulbake et al. | Liposomal drug delivery system and its clinically available products |