CA2052164A1 - Structures de membranes lipidiques pour administration par voie orale - Google Patents
Structures de membranes lipidiques pour administration par voie oraleInfo
- Publication number
- CA2052164A1 CA2052164A1 CA 2052164 CA2052164A CA2052164A1 CA 2052164 A1 CA2052164 A1 CA 2052164A1 CA 2052164 CA2052164 CA 2052164 CA 2052164 A CA2052164 A CA 2052164A CA 2052164 A1 CA2052164 A1 CA 2052164A1
- Authority
- CA
- Canada
- Prior art keywords
- membrane
- structures
- lipid membrane
- lipid
- mannan
- 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.)
- Abandoned
Links
- 150000002632 lipids Chemical class 0.000 title claims abstract description 46
- 239000012528 membrane Substances 0.000 claims abstract description 68
- 210000001986 peyer's patch Anatomy 0.000 claims abstract description 52
- 229920000057 Mannan Polymers 0.000 claims abstract description 32
- 229940079593 drug Drugs 0.000 claims abstract description 29
- 239000003814 drug Substances 0.000 claims abstract description 29
- 150000002703 mannose derivatives Chemical class 0.000 claims abstract description 14
- TZCPCKNHXULUIY-RGULYWFUSA-N 1,2-distearoyl-sn-glycero-3-phosphoserine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)CCCCCCCCCCCCCCCCC TZCPCKNHXULUIY-RGULYWFUSA-N 0.000 claims abstract description 12
- ZWZWYGMENQVNFU-UHFFFAOYSA-N Glycerophosphorylserin Natural products OC(=O)C(N)COP(O)(=O)OCC(O)CO ZWZWYGMENQVNFU-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000004615 ingredient Substances 0.000 claims abstract 2
- -1 mannobiose fatty acid esters Chemical class 0.000 claims description 10
- 210000001035 gastrointestinal tract Anatomy 0.000 claims description 9
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical group 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 description 8
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 8
- 239000000194 fatty acid Substances 0.000 claims description 8
- 229930195729 fatty acid Natural products 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 150000004665 fatty acids Chemical class 0.000 claims description 5
- 235000012000 cholesterol Nutrition 0.000 claims description 4
- 239000000787 lecithin Substances 0.000 claims description 4
- 235000010445 lecithin Nutrition 0.000 claims description 4
- 125000000311 mannosyl group Chemical group C1([C@@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical group 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 claims description 3
- DKXNBNKWCZZMJT-UHFFFAOYSA-N O4-alpha-D-Mannopyranosyl-D-mannose Natural products O=CC(O)C(O)C(C(O)CO)OC1OC(CO)C(O)C(O)C1O DKXNBNKWCZZMJT-UHFFFAOYSA-N 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 229940067606 lecithin Drugs 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims description 3
- JZNWSCPGTDBMEW-UHFFFAOYSA-N Glycerophosphorylethanolamin Natural products NCCOP(O)(=O)OCC(O)CO JZNWSCPGTDBMEW-UHFFFAOYSA-N 0.000 claims description 2
- 150000001841 cholesterols Chemical class 0.000 claims description 2
- 150000008104 phosphatidylethanolamines Chemical class 0.000 claims description 2
- 239000003381 stabilizer Substances 0.000 claims description 2
- 239000002502 liposome Substances 0.000 abstract description 57
- 239000000839 emulsion Substances 0.000 abstract description 7
- 239000000693 micelle Substances 0.000 abstract description 7
- 210000000813 small intestine Anatomy 0.000 abstract description 4
- 238000009826 distribution Methods 0.000 description 25
- 238000012360 testing method Methods 0.000 description 19
- 239000006185 dispersion Substances 0.000 description 17
- 210000001519 tissue Anatomy 0.000 description 14
- 239000004417 polycarbonate Substances 0.000 description 13
- 150000008106 phosphatidylserines Chemical class 0.000 description 8
- 239000007924 injection Substances 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- BELBBZDIHDAJOR-UHFFFAOYSA-N Phenolsulfonephthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2S(=O)(=O)O1 BELBBZDIHDAJOR-UHFFFAOYSA-N 0.000 description 5
- 238000011835 investigation Methods 0.000 description 5
- 239000003550 marker Substances 0.000 description 5
- 229960003531 phenolsulfonphthalein Drugs 0.000 description 5
- 239000000654 additive Substances 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 230000001976 improved effect Effects 0.000 description 4
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 235000010469 Glycine max Nutrition 0.000 description 3
- 244000068988 Glycine max Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 210000002969 egg yolk Anatomy 0.000 description 3
- 239000002504 physiological saline solution Substances 0.000 description 3
- 239000012085 test solution Substances 0.000 description 3
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- KLFKZIQAIPDJCW-HTIIIDOHSA-N Dipalmitoylphosphatidylserine Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)CCCCCCCCCCCCCCC KLFKZIQAIPDJCW-HTIIIDOHSA-N 0.000 description 2
- 102000002322 Egg Proteins Human genes 0.000 description 2
- 108010000912 Egg Proteins Proteins 0.000 description 2
- 102000004877 Insulin Human genes 0.000 description 2
- 108090001061 Insulin Proteins 0.000 description 2
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 2
- 229920001214 Polysorbate 60 Polymers 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 235000013345 egg yolk Nutrition 0.000 description 2
- 150000004676 glycans Chemical class 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 229940125396 insulin Drugs 0.000 description 2
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 2
- 229920001282 polysaccharide Polymers 0.000 description 2
- 239000005017 polysaccharide Substances 0.000 description 2
- 229920000136 polysorbate Polymers 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000008685 targeting Effects 0.000 description 2
- CITHEXJVPOWHKC-UUWRZZSWSA-N 1,2-di-O-myristoyl-sn-glycero-3-phosphocholine Chemical group CCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCC CITHEXJVPOWHKC-UUWRZZSWSA-N 0.000 description 1
- BZTDTCNHAFUJOG-UHFFFAOYSA-N 6-carboxyfluorescein Chemical compound C12=CC=C(O)C=C2OC2=CC(O)=CC=C2C11OC(=O)C2=CC=C(C(=O)O)C=C21 BZTDTCNHAFUJOG-UHFFFAOYSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 1
- IIUZTXTZRGLYTI-UHFFFAOYSA-N Dihydrogriseofulvin Natural products COC1CC(=O)CC(C)C11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 IIUZTXTZRGLYTI-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 102000001690 Factor VIII Human genes 0.000 description 1
- 108010054218 Factor VIII Proteins 0.000 description 1
- UXWOXTQWVMFRSE-UHFFFAOYSA-N Griseoviridin Natural products O=C1OC(C)CC=C(C(NCC=CC=CC(O)CC(O)C2)=O)SCC1NC(=O)C1=COC2=N1 UXWOXTQWVMFRSE-UHFFFAOYSA-N 0.000 description 1
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 1
- 206010061307 Neck deformity Diseases 0.000 description 1
- DDUHZTYCFQRHIY-UHFFFAOYSA-N Negwer: 6874 Natural products COC1=CC(=O)CC(C)C11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 241000700157 Rattus norvegicus Species 0.000 description 1
- 229920005654 Sephadex Polymers 0.000 description 1
- 239000012507 Sephadex™ Substances 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229930182558 Sterol Natural products 0.000 description 1
- 241000194017 Streptococcus Species 0.000 description 1
- 229930003448 Vitamin K Natural products 0.000 description 1
- 210000001132 alveolar macrophage Anatomy 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 239000000427 antigen Substances 0.000 description 1
- 102000036639 antigens Human genes 0.000 description 1
- 108091007433 antigens Proteins 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 229920002988 biodegradable polymer Polymers 0.000 description 1
- 239000004621 biodegradable polymer Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 210000002421 cell wall Anatomy 0.000 description 1
- 208000037516 chromosome inversion disease Diseases 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000012377 drug delivery Methods 0.000 description 1
- 239000012149 elution buffer Substances 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- DDUHZTYCFQRHIY-RBHXEPJQSA-N griseofulvin Chemical compound COC1=CC(=O)C[C@@H](C)[C@@]11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-RBHXEPJQSA-N 0.000 description 1
- 229960002867 griseofulvin Drugs 0.000 description 1
- 229920000669 heparin Polymers 0.000 description 1
- 229960002897 heparin Drugs 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000001900 immune effect Effects 0.000 description 1
- 230000000091 immunopotentiator Effects 0.000 description 1
- 229960003444 immunosuppressant agent Drugs 0.000 description 1
- 239000003018 immunosuppressive agent Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 210000002751 lymph Anatomy 0.000 description 1
- 210000003097 mucus Anatomy 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 229940126701 oral medication Drugs 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- SHUZOJHMOBOZST-UHFFFAOYSA-N phylloquinone Natural products CC(C)CCCCC(C)CCC(C)CCCC(=CCC1=C(C)C(=O)c2ccccc2C1=O)C SHUZOJHMOBOZST-UHFFFAOYSA-N 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
- 150000003432 sterols Chemical class 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 235000019168 vitamin K Nutrition 0.000 description 1
- 239000011712 vitamin K Substances 0.000 description 1
- 150000003721 vitamin K derivatives Chemical class 0.000 description 1
- 229940046010 vitamin k Drugs 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/127—Synthetic bilayered vehicles, e.g. liposomes or liposomes with cholesterol as the only non-phosphatidyl surfactant
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/127—Synthetic bilayered vehicles, e.g. liposomes or liposomes with cholesterol as the only non-phosphatidyl surfactant
- A61K9/1271—Non-conventional liposomes, e.g. PEGylated liposomes or liposomes coated or grafted with polymers
- A61K9/1272—Non-conventional liposomes, e.g. PEGylated liposomes or liposomes coated or grafted with polymers comprising non-phosphatidyl surfactants as bilayer-forming substances, e.g. cationic lipids or non-phosphatidyl liposomes coated or grafted with polymers
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Dispersion Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3132385A JP2922017B2 (ja) | 1991-03-25 | 1991-03-25 | 経口用脂質膜構造体 |
| JP132385/1991 | 1991-03-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2052164A1 true CA2052164A1 (fr) | 1992-09-26 |
Family
ID=15080154
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2052164 Abandoned CA2052164A1 (fr) | 1991-03-25 | 1991-09-24 | Structures de membranes lipidiques pour administration par voie orale |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JP2922017B2 (fr) |
| CA (1) | CA2052164A1 (fr) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000024377A1 (fr) * | 1998-10-23 | 2000-05-04 | Idea Innovative Dermale Applikationen Gmbh | Procede pour mettre au point, tester et utiliser des produits resultant de l'association de macromolecules et d'agregats de complexes, en vue d'ameliorer la charge utile et de reguler les vitesses de dissociation/association |
| US7175850B2 (en) | 1998-12-23 | 2007-02-13 | Idea Ag | Formulation for topical non-invasive application in vivo |
| US7459171B2 (en) | 1999-07-05 | 2008-12-02 | Idea Ag | Method for the improvement of transport across adaptable semi-permeable barriers |
| US7473432B2 (en) | 2002-10-11 | 2009-01-06 | Idea Ag | NSAID formulations, based on highly adaptable aggregates, for improved transport through barriers and topical drug delivery |
| US7867480B1 (en) | 1999-01-27 | 2011-01-11 | Gregor Cevc | Non-invasive vaccination through the skin |
| US7927622B1 (en) | 1999-01-27 | 2011-04-19 | Gregor Cevc | Methods of transnasal transport/immunization with highly adaptable carriers |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005119986A (ja) * | 2003-10-15 | 2005-05-12 | Japan Science & Technology Agency | 生理活性物質の投与方法、生理活性物質含有乳化液、及び生理活性物質含有乳化液の製造方法 |
| WO2014188861A1 (fr) | 2013-05-20 | 2014-11-27 | ユーハ味覚糖株式会社 | Composition de type gel présentant une teneur élevée en ubiquinol |
-
1991
- 1991-03-25 JP JP3132385A patent/JP2922017B2/ja not_active Expired - Fee Related
- 1991-09-24 CA CA 2052164 patent/CA2052164A1/fr not_active Abandoned
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000024377A1 (fr) * | 1998-10-23 | 2000-05-04 | Idea Innovative Dermale Applikationen Gmbh | Procede pour mettre au point, tester et utiliser des produits resultant de l'association de macromolecules et d'agregats de complexes, en vue d'ameliorer la charge utile et de reguler les vitesses de dissociation/association |
| AU765385B2 (en) * | 1998-10-23 | 2003-09-18 | Idea Ag | Method for developing, testing and using associates of macromolecules and complex aggregates for improved payload and controllable de/association rates |
| AU765385C (en) * | 1998-10-23 | 2004-05-20 | Idea Ag | Method for developing, testing and using associates of macromolecules and complex aggregates for improved payload and controllable de/association rates |
| US7175850B2 (en) | 1998-12-23 | 2007-02-13 | Idea Ag | Formulation for topical non-invasive application in vivo |
| US7867480B1 (en) | 1999-01-27 | 2011-01-11 | Gregor Cevc | Non-invasive vaccination through the skin |
| US7927622B1 (en) | 1999-01-27 | 2011-04-19 | Gregor Cevc | Methods of transnasal transport/immunization with highly adaptable carriers |
| US7459171B2 (en) | 1999-07-05 | 2008-12-02 | Idea Ag | Method for the improvement of transport across adaptable semi-permeable barriers |
| US7591949B2 (en) | 1999-07-05 | 2009-09-22 | Idea Ag | Method for the improvement of transport across adaptable semi-permeable barriers |
| US7473432B2 (en) | 2002-10-11 | 2009-01-06 | Idea Ag | NSAID formulations, based on highly adaptable aggregates, for improved transport through barriers and topical drug delivery |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0517344A (ja) | 1993-01-26 |
| JP2922017B2 (ja) | 1999-07-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0140085B1 (fr) | Préparation à base de vésicules lipidiques contenant un médicament et procédé de leur fabrication | |
| JP3571335B2 (ja) | リポゾームマイクロレシーバー組成物および方法 | |
| RU2100030C1 (ru) | Водная суспензия, содержащая микрокристаллы фармакологически активного водонерастворимого лекарственного вещества, покрытые мембранообразующим липидом (варианты), и лиофилизированный препарат водной суспензии | |
| EP0591492B1 (fr) | Composition pharmaceutique contenant un systeme defini de lipides | |
| JPS60155109A (ja) | リポソ−ム製剤 | |
| WO1995008986A1 (fr) | Compositions de camptothecine | |
| CA2052164A1 (fr) | Structures de membranes lipidiques pour administration par voie orale | |
| US20020058060A1 (en) | Liposome for incorporating large amounts of hydrophobic substances | |
| EP4275676B1 (fr) | Composition de liposome d'utidélone, procédé de préparation associé et utilisation associée | |
| US5932242A (en) | Ether lipid-containing pharmaceutical compositions and therapeutic uses thereof | |
| JP4874097B2 (ja) | 水難溶性カンプトテシン含有リポソーム製剤 | |
| AU780548B2 (en) | Pharmaceutical compositions for oral administration | |
| KR20200065961A (ko) | 서방형 리포좀 제제의 제조방법 | |
| WO2000009071A2 (fr) | Nouvelle preparation a base de liposomes utilisable dans la traitement du cancer et d'autres maladies proliferantes | |
| US20100260830A1 (en) | Liposomal Formulations of Tocopheryl Amides | |
| JPH06183954A (ja) | リポソーム製剤 | |
| WO2011037252A1 (fr) | Préparation liposomale contenant un dérivé de spicamycine | |
| WO2010118200A2 (fr) | Préparations à liposomes d'amides de tocophéryle | |
| JP2911550B2 (ja) | リポソーム製剤 | |
| JPH11171772A (ja) | 抗腫瘍薬のリポソーム化製剤 | |
| JPH10505818A (ja) | リポソーム製剤 | |
| KR20190050697A (ko) | 혼합 세라마이드를 포함하는 화장료 조성물 제조방법 및 상기 방법에 의해 제조한 화장료 조성물 | |
| HAGA et al. | Effects of preparing and ligand-binding methods of small unilamellar liposomes on their blood elimination and tissue distribution in rats | |
| HK1021622A1 (en) | Preparation for the transport of an active substance across barriers | |
| MXPA98009147A (en) | Pharmaceutical prepared in the form of liposo |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Dead |