CA2564120A1 - Procede servant a utiliser des lipides neutres afin de modifier la liberation in vivo depuis des liposomes a vesicules multiples - Google Patents
Procede servant a utiliser des lipides neutres afin de modifier la liberation in vivo depuis des liposomes a vesicules multiples Download PDFInfo
- Publication number
- CA2564120A1 CA2564120A1 CA002564120A CA2564120A CA2564120A1 CA 2564120 A1 CA2564120 A1 CA 2564120A1 CA 002564120 A CA002564120 A CA 002564120A CA 2564120 A CA2564120 A CA 2564120A CA 2564120 A1 CA2564120 A1 CA 2564120A1
- Authority
- CA
- Canada
- Prior art keywords
- release rate
- neutral lipid
- component
- lipid
- active compound
- 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.)
- Granted
Links
- 150000002632 lipids Chemical class 0.000 title claims abstract 83
- 230000007935 neutral effect Effects 0.000 title claims abstract 69
- 238000001727 in vivo Methods 0.000 title claims abstract 11
- 238000000034 method Methods 0.000 title claims 27
- 239000002502 liposome Substances 0.000 title claims 15
- 150000001875 compounds Chemical class 0.000 claims abstract 18
- 239000000203 mixture Substances 0.000 claims abstract 15
- 238000009472 formulation Methods 0.000 claims abstract 5
- 229940093609 tricaprylin Drugs 0.000 claims 11
- VLPFTAMPNXLGLX-UHFFFAOYSA-N trioctanoin Chemical compound CCCCCCCC(=O)OCC(OC(=O)CCCCCCC)COC(=O)CCCCCCC VLPFTAMPNXLGLX-UHFFFAOYSA-N 0.000 claims 11
- BAECOWNUKCLBPZ-HIUWNOOHSA-N Triolein Natural products O([C@H](OCC(=O)CCCCCCC/C=C\CCCCCCCC)COC(=O)CCCCCCC/C=C\CCCCCCCC)C(=O)CCCCCCC/C=C\CCCCCCCC BAECOWNUKCLBPZ-HIUWNOOHSA-N 0.000 claims 8
- PHYFQTYBJUILEZ-UHFFFAOYSA-N Trioleoylglycerol Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCCCCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC PHYFQTYBJUILEZ-UHFFFAOYSA-N 0.000 claims 8
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 claims 8
- 229940117972 triolein Drugs 0.000 claims 8
- SKGWNZXOCSYJQL-BUTYCLJRSA-N 1,2,3-tripalmitoleoylglycerol Chemical compound CCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCC)COC(=O)CCCCCCC\C=C/CCCCCC SKGWNZXOCSYJQL-BUTYCLJRSA-N 0.000 claims 7
- SKGWNZXOCSYJQL-UHFFFAOYSA-N tripalmitoleoyl-sn-glycerol Natural products CCCCCCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCCCCCC)COC(=O)CCCCCCCC=CCCCCCC SKGWNZXOCSYJQL-UHFFFAOYSA-N 0.000 claims 7
- 239000000839 emulsion Substances 0.000 claims 6
- 238000002844 melting Methods 0.000 claims 6
- 230000008018 melting Effects 0.000 claims 6
- 239000003960 organic solvent Substances 0.000 claims 6
- 239000002904 solvent Substances 0.000 claims 6
- MAYCICSNZYXLHB-UHFFFAOYSA-N tricaproin Chemical compound CCCCCC(=O)OCC(OC(=O)CCCCC)COC(=O)CCCCC MAYCICSNZYXLHB-UHFFFAOYSA-N 0.000 claims 5
- VMPHSYLJUKZBJJ-UHFFFAOYSA-N trilaurin Chemical compound CCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCC)COC(=O)CCCCCCCCCCC VMPHSYLJUKZBJJ-UHFFFAOYSA-N 0.000 claims 4
- SNKAWJBJQDLSFF-NVKMUCNASA-N 1,2-dioleoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/CCCCCCCC SNKAWJBJQDLSFF-NVKMUCNASA-N 0.000 claims 3
- LADGBHLMCUINGV-UHFFFAOYSA-N tricaprin Chemical compound CCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCC)COC(=O)CCCCCCCCC LADGBHLMCUINGV-UHFFFAOYSA-N 0.000 claims 3
- 229940093633 tricaprin Drugs 0.000 claims 3
- -1 trimyristolein Chemical compound 0.000 claims 3
- SDEURMLKLAEUAY-JFSPZUDSSA-N (2-{[(2r)-2,3-bis[(13z)-docos-13-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCC\C=C/CCCCCCCC SDEURMLKLAEUAY-JFSPZUDSSA-N 0.000 claims 2
- NRJAVPSFFCBXDT-HUESYALOSA-N 1,2-distearoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCC NRJAVPSFFCBXDT-HUESYALOSA-N 0.000 claims 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims 2
- HRTBOPUWPUXROO-VCZQVZGSSA-N (2-{[(2r)-2,3-bis(docosanoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium Chemical compound CCCCCCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCCCCCC HRTBOPUWPUXROO-VCZQVZGSSA-N 0.000 claims 1
- YKIOPDIXYAUOFN-YACUFSJGSA-N (2-{[(2r)-2,3-bis(icosanoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium Chemical compound CCCCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCCCC YKIOPDIXYAUOFN-YACUFSJGSA-N 0.000 claims 1
- 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 1
- AEUCYCQYAUFAKH-DITNKEBASA-N 1,2-di-[(11Z)-eicosenoyl]-sn-glycero-3-phosphocholine Chemical compound CCCCCCCC\C=C/CCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCC\C=C/CCCCCCCC AEUCYCQYAUFAKH-DITNKEBASA-N 0.000 claims 1
- 229940083937 1,2-diarachidoyl-sn-glycero-3-phosphocholine Drugs 0.000 claims 1
- 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 1
- BIABMEZBCHDPBV-BEBVUIBBSA-N 1,2-dihexadecanoyl-sn-glycero-3-phosphoglycerol Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OCC(O)CO)OC(=O)CCCCCCCCCCCCCCC BIABMEZBCHDPBV-BEBVUIBBSA-N 0.000 claims 1
- IJFVSSZAOYLHEE-SSEXGKCCSA-N 1,2-dilauroyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCC IJFVSSZAOYLHEE-SSEXGKCCSA-N 0.000 claims 1
- DSNRWDQKZIEDDB-SQYFZQSCSA-N 1,2-dioleoyl-sn-glycero-3-phospho-(1'-sn-glycerol) Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@@H](O)CO)OC(=O)CCCCCCC\C=C/CCCCCCCC DSNRWDQKZIEDDB-SQYFZQSCSA-N 0.000 claims 1
- GPWHCUUIQMGELX-VHQDNGOZSA-N 1,2-dipalmitoleoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCC\C=C/CCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/CCCCCC GPWHCUUIQMGELX-VHQDNGOZSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 150000001840 cholesterol esters Chemical class 0.000 claims 1
- 238000011534 incubation Methods 0.000 abstract 1
Landscapes
- Medicinal Preparation (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA2692302A CA2692302C (fr) | 1997-01-31 | 1998-01-29 | Procede servant a utiliser des lipides neutres afin de modifier la libe ation in vivo depuis des liposomes a vesicules multiples |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/792,566 US5891467A (en) | 1997-01-31 | 1997-01-31 | Method for utilizing neutral lipids to modify in vivo release from multivesicular liposomes |
| US08/792,566 | 1997-01-31 | ||
| CA002277956A CA2277956C (fr) | 1997-01-31 | 1998-01-29 | Procede servant a utiliser des lipides neutres afin de modifier la liberation in vivo depuis des liposomes a vesicules multiples |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002277956A Division CA2277956C (fr) | 1997-01-31 | 1998-01-29 | Procede servant a utiliser des lipides neutres afin de modifier la liberation in vivo depuis des liposomes a vesicules multiples |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2692302A Division CA2692302C (fr) | 1997-01-31 | 1998-01-29 | Procede servant a utiliser des lipides neutres afin de modifier la libe ation in vivo depuis des liposomes a vesicules multiples |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2564120A1 true CA2564120A1 (fr) | 1998-08-06 |
| CA2564120C CA2564120C (fr) | 2010-04-13 |
Family
ID=37480474
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2564120A Expired - Lifetime CA2564120C (fr) | 1997-01-31 | 1998-01-29 | Procede servant a utiliser des lipides neutres afin de modifier la liberation in vivo depuis des liposomes a vesicules multiples |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA2564120C (fr) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1189597A1 (fr) * | 1999-06-04 | 2002-03-27 | SkyePharma Inc. | Compositions a noyau huileux destinees a la liberation prolongee de medicaments hydrophobes |
| WO2013064837A1 (fr) * | 2011-11-03 | 2013-05-10 | Isis Innovation Limited | Multisomes: réseaux de gouttelettes encapsulées |
| EP2813220A3 (fr) * | 2010-04-09 | 2015-06-17 | Pacira Pharmaceuticals, Inc. | Procédé de formulation de vésicules membranaires synthétiques de grand diamètre |
| US9831010B2 (en) | 2012-10-25 | 2017-11-28 | Oxford University Innovation Limited | Hydrogel network |
| US10950376B2 (en) | 2012-10-25 | 2021-03-16 | Oxford University Innovation Limited | Droplet assembly method |
| US11213797B2 (en) | 2012-12-07 | 2022-01-04 | Oxford University Innovation Limited | Droplet assembly by 3D printing |
-
1998
- 1998-01-29 CA CA2564120A patent/CA2564120C/fr not_active Expired - Lifetime
Cited By (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003501376A (ja) * | 1999-06-04 | 2003-01-14 | スカイファーマ インコーポレーテッド | 疎水性薬物の持続性放出のための油コア組成物 |
| EP1189597A4 (fr) * | 1999-06-04 | 2008-06-18 | Pacira Pharmaceuticals Inc | Compositions a noyau huileux destinees a la liberation prolongee de medicaments hydrophobes |
| EP1189597A1 (fr) * | 1999-06-04 | 2002-03-27 | SkyePharma Inc. | Compositions a noyau huileux destinees a la liberation prolongee de medicaments hydrophobes |
| US10045941B2 (en) | 2010-04-09 | 2018-08-14 | Pacira Pharmaceuticals, Inc. | Method for formulating large diameter synthetic membrane vesicles |
| US10398648B2 (en) | 2010-04-09 | 2019-09-03 | Pacira Pharmaceuticals, Inc. | Method for formulating large diameter synthetic membrane vesicles |
| EP2813220A3 (fr) * | 2010-04-09 | 2015-06-17 | Pacira Pharmaceuticals, Inc. | Procédé de formulation de vésicules membranaires synthétiques de grand diamètre |
| US9724302B2 (en) | 2010-04-09 | 2017-08-08 | Pacira Pharmaceuticals, Inc. | Method for formulating large diameter synthetic membrane vesicles |
| US9730892B2 (en) | 2010-04-09 | 2017-08-15 | Pacira Pharmaceuticals, Inc. | Method for formulating large diameter synthetic membrane vesicles |
| US9737483B2 (en) | 2010-04-09 | 2017-08-22 | Pacira Pharmaceuticals, Inc. | Method for formulating large diameter synthetic membrane vesicles |
| US9737482B2 (en) | 2010-04-09 | 2017-08-22 | Pacira Pharmaceuticals, Inc. | Method for formulating large diameter synthetic membrane vesicles |
| US9757336B2 (en) | 2010-04-09 | 2017-09-12 | Pacira Pharmaceuticals, Inc. | Method for formulating large diameter synthetic membrane vesicles |
| US9808424B2 (en) | 2010-04-09 | 2017-11-07 | Pacira Pharmaceuticals, Inc. | Method for formulating large diameter synthetic membrane vesicles |
| AU2012330894B2 (en) * | 2011-11-03 | 2017-07-13 | Oxford University Innovation Limited | Multisomes: encapsulated droplet networks |
| WO2013064837A1 (fr) * | 2011-11-03 | 2013-05-10 | Isis Innovation Limited | Multisomes: réseaux de gouttelettes encapsulées |
| US10548852B2 (en) | 2011-11-03 | 2020-02-04 | Oxford University Innovation Limited | Multisomes: encapsulated droplet networks |
| US11406603B2 (en) | 2011-11-03 | 2022-08-09 | Oxford University Innovation Limited | Multisomes: encapsulated droplet networks |
| US11998642B2 (en) | 2011-11-03 | 2024-06-04 | Oxford University Innovation Limited | Multisomes: encapsulated droplet networks |
| US9831010B2 (en) | 2012-10-25 | 2017-11-28 | Oxford University Innovation Limited | Hydrogel network |
| US10950376B2 (en) | 2012-10-25 | 2021-03-16 | Oxford University Innovation Limited | Droplet assembly method |
| US10978218B2 (en) | 2012-10-25 | 2021-04-13 | Oxford University Innovation Limited | Hydrogel network |
| US12073966B2 (en) | 2012-10-25 | 2024-08-27 | Oxford University Innovation Limited | Droplet assembly method |
| US11213797B2 (en) | 2012-12-07 | 2022-01-04 | Oxford University Innovation Limited | Droplet assembly by 3D printing |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2564120C (fr) | 2010-04-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20180129 |