JPH0326166B2 - - Google Patents
Info
- Publication number
- JPH0326166B2 JPH0326166B2 JP58181629A JP18162983A JPH0326166B2 JP H0326166 B2 JPH0326166 B2 JP H0326166B2 JP 58181629 A JP58181629 A JP 58181629A JP 18162983 A JP18162983 A JP 18162983A JP H0326166 B2 JPH0326166 B2 JP H0326166B2
- Authority
- JP
- Japan
- Prior art keywords
- hydrocarbon group
- carbon atoms
- vesicles
- ion
- group
- 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.)
- Expired - Lifetime
Links
- 239000000203 mixture Substances 0.000 claims description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 22
- 239000004094 surface-active agent Substances 0.000 claims description 18
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 150000002500 ions Chemical class 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- -1 halogen ion Chemical class 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 229910001413 alkali metal ion Inorganic materials 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- ZXVOCOLRQJZVBW-UHFFFAOYSA-N azane;ethanol Chemical compound N.CCO ZXVOCOLRQJZVBW-UHFFFAOYSA-N 0.000 claims description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-O bis(2-hydroxyethyl)azanium Chemical compound OCC[NH2+]CCO ZBCBWPMODOFKDW-UHFFFAOYSA-O 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical compound OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 claims description 2
- 238000000034 method Methods 0.000 description 17
- 239000000243 solution Substances 0.000 description 16
- 239000002502 liposome Substances 0.000 description 14
- 239000000126 substance Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000012528 membrane Substances 0.000 description 6
- 239000003814 drug Substances 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000003937 drug carrier Substances 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 206010028980 Neoplasm Diseases 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 201000011510 cancer Diseases 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 210000000056 organ Anatomy 0.000 description 3
- 150000003904 phospholipids Chemical class 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000002246 antineoplastic agent Substances 0.000 description 2
- 229940041181 antineoplastic drug Drugs 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- REZZEXDLIUJMMS-UHFFFAOYSA-M dimethyldioctadecylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC REZZEXDLIUJMMS-UHFFFAOYSA-M 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 210000002472 endoplasmic reticulum Anatomy 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000013112 stability test Methods 0.000 description 2
- 230000007332 vesicle formation Effects 0.000 description 2
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- CSILTOSWFXCNOW-UHFFFAOYSA-N 2-hydroxyethyl-methyl-dioctadecylazanium Chemical class CCCCCCCCCCCCCCCCCC[N+](C)(CCO)CCCCCCCCCCCCCCCCCC CSILTOSWFXCNOW-UHFFFAOYSA-N 0.000 description 1
- JGFDZZLUDWMUQH-UHFFFAOYSA-N Didecyldimethylammonium Chemical class CCCCCCCCCC[N+](C)(C)CCCCCCCCCC JGFDZZLUDWMUQH-UHFFFAOYSA-N 0.000 description 1
- 208000030453 Drug-Related Side Effects and Adverse reaction Diseases 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- COQLPRJCUIATTQ-UHFFFAOYSA-N Uranyl acetate Chemical compound O.O.O=[U]=O.CC(O)=O.CC(O)=O COQLPRJCUIATTQ-UHFFFAOYSA-N 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- XUXZYMCUMKODKW-UHFFFAOYSA-N didecyl-(2-hydroxyethyl)-methylazanium Chemical class CCCCCCCCCC[N+](C)(CCO)CCCCCCCCCC XUXZYMCUMKODKW-UHFFFAOYSA-N 0.000 description 1
- QQJDHWMADUVRDL-UHFFFAOYSA-N didodecyl(dimethyl)azanium Chemical class CCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCC QQJDHWMADUVRDL-UHFFFAOYSA-N 0.000 description 1
- XYEVCZCWQFVWDJ-UHFFFAOYSA-N didodecyl-(2-hydroxyethyl)-methylazanium Chemical class CCCCCCCCCCCC[N+](C)(CCO)CCCCCCCCCCCC XYEVCZCWQFVWDJ-UHFFFAOYSA-N 0.000 description 1
- SWSFKKWJEHRFFP-UHFFFAOYSA-N dihexadecyl(dimethyl)azanium Chemical class CCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCC SWSFKKWJEHRFFP-UHFFFAOYSA-N 0.000 description 1
- KQSBAORQSXKBIP-UHFFFAOYSA-N dihexadecyl-(2-hydroxyethyl)-methylazanium Chemical class CCCCCCCCCCCCCCCC[N+](C)(CCO)CCCCCCCCCCCCCCCC KQSBAORQSXKBIP-UHFFFAOYSA-N 0.000 description 1
- OGQYPPBGSLZBEG-UHFFFAOYSA-N dimethyl(dioctadecyl)azanium Chemical class CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC OGQYPPBGSLZBEG-UHFFFAOYSA-N 0.000 description 1
- CJBMLKNLJXFFGD-UHFFFAOYSA-N dimethyl-di(tetradecyl)azanium Chemical class CCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCC CJBMLKNLJXFFGD-UHFFFAOYSA-N 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 238000001493 electron microscopy Methods 0.000 description 1
- 210000003743 erythrocyte Anatomy 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- IYDGMDWEHDFVQI-UHFFFAOYSA-N phosphoric acid;trioxotungsten Chemical compound O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.OP(O)(O)=O IYDGMDWEHDFVQI-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000007447 staining method Methods 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 239000003021 water soluble solvent Substances 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—Liposomes
- A61K9/1271—Non-conventional liposomes, e.g. PEGylated liposomes, liposomes coated with polymers
- A61K9/1272—Non-conventional liposomes, e.g. PEGylated liposomes, liposomes coated with polymers with substantial amounts of non-phosphatidyl, i.e. non-acylglycerophosphate, surfactants as bilayer-forming substances, e.g. cationic lipids
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Molecular Biology (AREA)
- Dispersion Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Biophysics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Preparation (AREA)
- Manufacturing Of Micro-Capsules (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58181629A JPS6072831A (ja) | 1983-09-29 | 1983-09-29 | ベシクル用組成物 |
| GB08422628A GB2147263B (en) | 1983-09-29 | 1984-09-07 | Compositions for making vesticles |
| DE19843435516 DE3435516A1 (de) | 1983-09-29 | 1984-09-27 | Massen zur ausbildung von vesikeln |
| FR8414910A FR2552679B1 (fr) | 1983-09-29 | 1984-09-28 | Compositions vesiculaires a base de sel d'ammonium quaternaire et d'agent tensio-actif |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58181629A JPS6072831A (ja) | 1983-09-29 | 1983-09-29 | ベシクル用組成物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6072831A JPS6072831A (ja) | 1985-04-24 |
| JPH0326166B2 true JPH0326166B2 (US06811534-20041102-M00003.png) | 1991-04-10 |
Family
ID=16104113
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58181629A Granted JPS6072831A (ja) | 1983-09-29 | 1983-09-29 | ベシクル用組成物 |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS6072831A (US06811534-20041102-M00003.png) |
| DE (1) | DE3435516A1 (US06811534-20041102-M00003.png) |
| FR (1) | FR2552679B1 (US06811534-20041102-M00003.png) |
| GB (1) | GB2147263B (US06811534-20041102-M00003.png) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4911928A (en) * | 1987-03-13 | 1990-03-27 | Micro-Pak, Inc. | Paucilamellar lipid vesicles |
| US5234767A (en) * | 1987-03-13 | 1993-08-10 | Micro-Pak, Inc. | Hybrid paucilamellar lipid vesicles |
| US4855090A (en) * | 1987-03-13 | 1989-08-08 | Micro-Pak, Inc. | Method of producing high aqueous volume multilamellar vesicles |
| US5628936A (en) * | 1987-03-13 | 1997-05-13 | Micro-Pak, Inc. | Hybrid paucilamellar lipid vesicles |
| US4942038A (en) * | 1987-03-13 | 1990-07-17 | Micro Vesicular Systems, Inc. | Encapsulated humectant |
| US5000960A (en) * | 1987-03-13 | 1991-03-19 | Micro-Pak, Inc. | Protein coupling to lipid vesicles |
| US4917951A (en) * | 1987-07-28 | 1990-04-17 | Micro-Pak, Inc. | Lipid vesicles formed of surfactants and steroids |
| US5023086A (en) * | 1987-03-13 | 1991-06-11 | Micro-Pak, Inc. | Encapsulated ionophore growth factors |
| US4853228A (en) * | 1987-07-28 | 1989-08-01 | Micro-Pak, Inc. | Method of manufacturing unilamellar lipid vesicles |
| US5019392A (en) * | 1988-03-03 | 1991-05-28 | Micro-Pak, Inc. | Encapsulation of parasiticides |
| US5019174A (en) * | 1988-03-03 | 1991-05-28 | Micro Vesicular Systems, Inc. | Removing oil from surfaces with liposomal cleaner |
| US5104736A (en) * | 1988-03-03 | 1992-04-14 | Micro-Pak, Inc. | Reinforced paucilamellar lipid vesicles |
| US5160669A (en) * | 1988-03-03 | 1992-11-03 | Micro Vesicular Systems, Inc. | Method of making oil filled paucilamellar lipid vesicles |
| US5032457A (en) * | 1988-03-03 | 1991-07-16 | Micro Vesicular Systems, Inc. | Paucilamellar lipid vesicles using charge-localized, single chain, nonphospholipid surfactants |
| DE4107152C2 (de) * | 1991-03-06 | 1994-03-24 | Gregor Cevc | Präparate zur nichtinvasiven Verabreichung von Antidiabetica |
| DE4107153A1 (de) * | 1991-03-06 | 1992-09-10 | Gregor Cevc | Praeparat zur wirkstoffapplikation in kleinsttroepfchenform |
| US5164191A (en) * | 1991-02-12 | 1992-11-17 | Micro Vesicular Systems, Inc. | Lipid vesicles having an alkyd as a wall-forming material |
| US5213805A (en) * | 1991-07-25 | 1993-05-25 | Micro Vesicular Systems, Inc. | Lipid vesicles having n,n-dimethylamide derivatives as their primary lipid |
| US5405615A (en) * | 1991-09-17 | 1995-04-11 | Micro Vesicular Systems, Inc. | Sucrose distearate lipid vesicles |
| US5260065A (en) * | 1991-09-17 | 1993-11-09 | Micro Vesicular Systems, Inc. | Blended lipid vesicles |
| US5643600A (en) * | 1991-09-17 | 1997-07-01 | Micro-Pak, Inc. | Lipid vesicles containing avocado oil unsaponifiables |
| US5439967A (en) * | 1991-09-17 | 1995-08-08 | Micro Vesicular Systems, Inc. | Propylene glycol stearate vesicles |
| FR2687313A1 (fr) * | 1992-02-17 | 1993-08-20 | Oreal | Dispersion de vesicules a base de betauines et compositions cosmetiques et/ou pharmaceutiques contenant ladite dispersion. |
| US5753613A (en) * | 1994-09-30 | 1998-05-19 | Inex Pharmaceuticals Corporation | Compositions for the introduction of polyanionic materials into cells |
| DE69527206T2 (de) * | 1994-09-30 | 2003-02-27 | Inex Pharmaceuticals Corp., Vancouver | Mittel zum einbringen polyanionischer materialien in zellen |
| US7749520B2 (en) | 2004-07-07 | 2010-07-06 | Statens Serum Institut | Compositions and methods for stabilizing lipid based adjuvant formulations using glycolipids |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS50105997A (US06811534-20041102-M00003.png) * | 1974-01-11 | 1975-08-21 | ||
| JPS5394694A (en) * | 1977-01-29 | 1978-08-18 | Lion Fat Oil Co Ltd | Fiber softening composition |
| JPS53134784A (en) * | 1977-04-28 | 1978-11-24 | Kao Corp | Production of small hollow cell-containing material consisting of double layers of surface active agent |
| JPS5626071A (en) * | 1979-06-05 | 1981-03-13 | Procter & Gamble | Liquid fabric conditioning composition |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3753990A (en) * | 1972-01-17 | 1973-08-21 | Procter & Gamble | Phenylbismuth bis(2-pyridinethiol 1-oxide) |
| FR2315991A1 (fr) * | 1975-06-30 | 1977-01-28 | Oreal | Procede de fabrication de dispersions aqueuses de spherules lipidiques et nouvelles compositions correspondantes |
| FR2416008A1 (fr) * | 1978-02-02 | 1979-08-31 | Oreal | Lyophilisats de liposomes |
| ATE8584T1 (de) * | 1980-01-16 | 1984-08-15 | Hans Georg Prof. Dr. Weder | Verfahren und dialysiereinrichtung zur herstellung von bilayer-vesikeln und verwendung der bilayer-vesikel. |
| GR77320B (US06811534-20041102-M00003.png) * | 1980-12-22 | 1984-09-11 | Procter & Gamble | |
| EP0067635A3 (en) * | 1981-06-15 | 1984-02-22 | THE PROCTER & GAMBLE COMPANY | Shampoo compositions |
| EP0102324A3 (de) * | 1982-07-29 | 1984-11-07 | Ciba-Geigy Ag | Lipide und Tenside in wässriger Phase |
-
1983
- 1983-09-29 JP JP58181629A patent/JPS6072831A/ja active Granted
-
1984
- 1984-09-07 GB GB08422628A patent/GB2147263B/en not_active Expired
- 1984-09-27 DE DE19843435516 patent/DE3435516A1/de not_active Withdrawn
- 1984-09-28 FR FR8414910A patent/FR2552679B1/fr not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS50105997A (US06811534-20041102-M00003.png) * | 1974-01-11 | 1975-08-21 | ||
| JPS5394694A (en) * | 1977-01-29 | 1978-08-18 | Lion Fat Oil Co Ltd | Fiber softening composition |
| JPS53134784A (en) * | 1977-04-28 | 1978-11-24 | Kao Corp | Production of small hollow cell-containing material consisting of double layers of surface active agent |
| JPS5626071A (en) * | 1979-06-05 | 1981-03-13 | Procter & Gamble | Liquid fabric conditioning composition |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2552679B1 (fr) | 1993-06-11 |
| GB2147263A (en) | 1985-05-09 |
| FR2552679A1 (fr) | 1985-04-05 |
| JPS6072831A (ja) | 1985-04-24 |
| GB8422628D0 (en) | 1984-10-10 |
| GB2147263B (en) | 1987-03-25 |
| DE3435516A1 (de) | 1985-04-18 |
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