DE2818655C2 - Verfahren zur Herstellung eines gefriergetrockneten Gemischs von potentiellen Liposomen, durch dieses Verfahren erhaltenes Gemisch sowie Verfahren zur Herstellung eines wäßrigen Liposompräparats - Google Patents
Verfahren zur Herstellung eines gefriergetrockneten Gemischs von potentiellen Liposomen, durch dieses Verfahren erhaltenes Gemisch sowie Verfahren zur Herstellung eines wäßrigen LiposompräparatsInfo
- Publication number
- DE2818655C2 DE2818655C2 DE2818655A DE2818655A DE2818655C2 DE 2818655 C2 DE2818655 C2 DE 2818655C2 DE 2818655 A DE2818655 A DE 2818655A DE 2818655 A DE2818655 A DE 2818655A DE 2818655 C2 DE2818655 C2 DE 2818655C2
- Authority
- DE
- Germany
- Prior art keywords
- process according
- freeze
- liposomes
- biologically active
- lipid
- 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
Links
- 239000002502 liposome Substances 0.000 title claims description 114
- 238000000034 method Methods 0.000 title claims description 71
- 239000011363 dried mixture Substances 0.000 title claims description 38
- 238000002360 preparation method Methods 0.000 title claims description 35
- 239000000203 mixture Substances 0.000 title claims description 29
- 150000001875 compounds Chemical class 0.000 claims description 61
- 150000002632 lipids Chemical class 0.000 claims description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 31
- 239000012736 aqueous medium Substances 0.000 claims description 18
- 239000012153 distilled water Substances 0.000 claims description 18
- 239000000243 solution Substances 0.000 claims description 18
- 238000004108 freeze drying Methods 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 16
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 14
- 150000003904 phospholipids Chemical class 0.000 claims description 13
- 239000000126 substance Substances 0.000 claims description 13
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical group CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 12
- 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 description 10
- 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 description 10
- 239000000787 lecithin Substances 0.000 claims description 9
- 235000010445 lecithin Nutrition 0.000 claims description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- 239000008344 egg yolk phospholipid Substances 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- 235000012000 cholesterol Nutrition 0.000 claims description 5
- RNPXCFINMKSQPQ-UHFFFAOYSA-N dicetyl hydrogen phosphate Chemical compound CCCCCCCCCCCCCCCCOP(O)(=O)OCCCCCCCCCCCCCCCC RNPXCFINMKSQPQ-UHFFFAOYSA-N 0.000 claims description 5
- 229940093541 dicetylphosphate Drugs 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- PORPENFLTBBHSG-MGBGTMOVSA-N 1,2-dihexadecanoyl-sn-glycerol-3-phosphate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCC PORPENFLTBBHSG-MGBGTMOVSA-N 0.000 claims description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- UPHWVVKYDQHTCF-UHFFFAOYSA-N octadecylazanium;acetate Chemical compound CC(O)=O.CCCCCCCCCCCCCCCCCCN UPHWVVKYDQHTCF-UHFFFAOYSA-N 0.000 claims description 4
- 241000283690 Bos taurus Species 0.000 claims description 3
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical group CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 claims description 3
- 210000004556 brain Anatomy 0.000 claims description 3
- 239000007853 buffer solution Substances 0.000 claims description 3
- 150000002270 gangliosides Chemical class 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- BMBWFDPPCSTUSZ-UHFFFAOYSA-M sodium;2,3-di(hexadecanoyloxy)propyl hydrogen phosphate Chemical group [Na+].CCCCCCCCCCCCCCCC(=O)OCC(COP(O)([O-])=O)OC(=O)CCCCCCCCCCCCCCC BMBWFDPPCSTUSZ-UHFFFAOYSA-M 0.000 claims 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 claims 5
- 229940067606 lecithin Drugs 0.000 claims 5
- 239000012752 auxiliary agent Substances 0.000 claims 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000006185 dispersion Substances 0.000 description 16
- 238000003345 scintillation counting Methods 0.000 description 15
- 150000003431 steroids Chemical class 0.000 description 14
- 239000008363 phosphate buffer Substances 0.000 description 11
- 239000000725 suspension Substances 0.000 description 10
- 239000010408 film Substances 0.000 description 9
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 235000011089 carbon dioxide Nutrition 0.000 description 6
- 238000001228 spectrum Methods 0.000 description 6
- 239000013256 coordination polymer Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 229920001202 Inulin Polymers 0.000 description 4
- 229940029339 inulin Drugs 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 230000000717 retained effect Effects 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- 229950006323 angiotensin ii Drugs 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- JYJIGFIDKWBXDU-MNNPPOADSA-N inulin Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)OC[C@]1(OC[C@]2(OC[C@]3(OC[C@]4(OC[C@]5(OC[C@]6(OC[C@]7(OC[C@]8(OC[C@]9(OC[C@]%10(OC[C@]%11(OC[C@]%12(OC[C@]%13(OC[C@]%14(OC[C@]%15(OC[C@]%16(OC[C@]%17(OC[C@]%18(OC[C@]%19(OC[C@]%20(OC[C@]%21(OC[C@]%22(OC[C@]%23(OC[C@]%24(OC[C@]%25(OC[C@]%26(OC[C@]%27(OC[C@]%28(OC[C@]%29(OC[C@]%30(OC[C@]%31(OC[C@]%32(OC[C@]%33(OC[C@]%34(OC[C@]%35(OC[C@]%36(O[C@@H]%37[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O%37)O)[C@H]([C@H](O)[C@@H](CO)O%36)O)[C@H]([C@H](O)[C@@H](CO)O%35)O)[C@H]([C@H](O)[C@@H](CO)O%34)O)[C@H]([C@H](O)[C@@H](CO)O%33)O)[C@H]([C@H](O)[C@@H](CO)O%32)O)[C@H]([C@H](O)[C@@H](CO)O%31)O)[C@H]([C@H](O)[C@@H](CO)O%30)O)[C@H]([C@H](O)[C@@H](CO)O%29)O)[C@H]([C@H](O)[C@@H](CO)O%28)O)[C@H]([C@H](O)[C@@H](CO)O%27)O)[C@H]([C@H](O)[C@@H](CO)O%26)O)[C@H]([C@H](O)[C@@H](CO)O%25)O)[C@H]([C@H](O)[C@@H](CO)O%24)O)[C@H]([C@H](O)[C@@H](CO)O%23)O)[C@H]([C@H](O)[C@@H](CO)O%22)O)[C@H]([C@H](O)[C@@H](CO)O%21)O)[C@H]([C@H](O)[C@@H](CO)O%20)O)[C@H]([C@H](O)[C@@H](CO)O%19)O)[C@H]([C@H](O)[C@@H](CO)O%18)O)[C@H]([C@H](O)[C@@H](CO)O%17)O)[C@H]([C@H](O)[C@@H](CO)O%16)O)[C@H]([C@H](O)[C@@H](CO)O%15)O)[C@H]([C@H](O)[C@@H](CO)O%14)O)[C@H]([C@H](O)[C@@H](CO)O%13)O)[C@H]([C@H](O)[C@@H](CO)O%12)O)[C@H]([C@H](O)[C@@H](CO)O%11)O)[C@H]([C@H](O)[C@@H](CO)O%10)O)[C@H]([C@H](O)[C@@H](CO)O9)O)[C@H]([C@H](O)[C@@H](CO)O8)O)[C@H]([C@H](O)[C@@H](CO)O7)O)[C@H]([C@H](O)[C@@H](CO)O6)O)[C@H]([C@H](O)[C@@H](CO)O5)O)[C@H]([C@H](O)[C@@H](CO)O4)O)[C@H]([C@H](O)[C@@H](CO)O3)O)[C@H]([C@H](O)[C@@H](CO)O2)O)[C@@H](O)[C@H](O)[C@@H](CO)O1 JYJIGFIDKWBXDU-MNNPPOADSA-N 0.000 description 3
- 102000004169 proteins and genes Human genes 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 102000005862 Angiotensin II Human genes 0.000 description 2
- 101800000733 Angiotensin-2 Proteins 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- CZGUSIXMZVURDU-JZXHSEFVSA-N Ile(5)-angiotensin II Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C([O-])=O)NC(=O)[C@@H](NC(=O)[C@H](CCCNC(N)=[NH2+])NC(=O)[C@@H]([NH3+])CC([O-])=O)C(C)C)C1=CC=C(O)C=C1 CZGUSIXMZVURDU-JZXHSEFVSA-N 0.000 description 2
- 239000000232 Lipid Bilayer Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000000659 freezing mixture Substances 0.000 description 2
- 239000005556 hormone Substances 0.000 description 2
- 229940088597 hormone Drugs 0.000 description 2
- 238000002372 labelling Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000013049 sediment Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 239000011782 vitamin Substances 0.000 description 2
- 229940088594 vitamin Drugs 0.000 description 2
- 229930003231 vitamin Natural products 0.000 description 2
- 235000013343 vitamin Nutrition 0.000 description 2
- 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 description 1
- 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 description 1
- JLPULHDHAOZNQI-ZTIMHPMXSA-N 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC JLPULHDHAOZNQI-ZTIMHPMXSA-N 0.000 description 1
- 244000258044 Solanum gilo Species 0.000 description 1
- VXHYGTFEIKKRRG-CUUJIVLRSA-N [2-[(8s,9s,10r,11s,13s,14s,17r)-11,17-dihydroxy-10,13-dimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] hexadecanoate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)COC(=O)CCCCCCCCCCCCCCC)(O)[C@@]1(C)C[C@@H]2O VXHYGTFEIKKRRG-CUUJIVLRSA-N 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 229960003724 dimyristoylphosphatidylcholine Drugs 0.000 description 1
- KDQPSPMLNJTZAL-UHFFFAOYSA-L disodium hydrogenphosphate dihydrate Chemical compound O.O.[Na+].[Na+].OP([O-])([O-])=O KDQPSPMLNJTZAL-UHFFFAOYSA-L 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000002651 drug therapy Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 229940088598 enzyme Drugs 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000002163 immunogen Effects 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000004001 molecular interaction Effects 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229940083466 soybean lecithin Drugs 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 238000005199 ultracentrifugation Methods 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 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
- A61K9/1277—Processes for preparing; Proliposomes
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Dispersion Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Manufacturing Of Micro-Capsules (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB19510/77A GB1575343A (en) | 1977-05-10 | 1977-05-10 | Method for preparing liposome compositions containing biologically active compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2818655A1 DE2818655A1 (de) | 1978-11-23 |
| DE2818655C2 true DE2818655C2 (de) | 1987-05-14 |
Family
ID=10130587
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2818655A Expired DE2818655C2 (de) | 1977-05-10 | 1978-04-27 | Verfahren zur Herstellung eines gefriergetrockneten Gemischs von potentiellen Liposomen, durch dieses Verfahren erhaltenes Gemisch sowie Verfahren zur Herstellung eines wäßrigen Liposompräparats |
Country Status (19)
Families Citing this family (123)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH621479A5 (US20090163788A1-20090625-C00002.png) * | 1977-08-05 | 1981-02-13 | Battelle Memorial Institute | |
| IT1110989B (it) * | 1979-01-19 | 1986-01-13 | Erba Farmitalia | Forme farmaceutiche costitutite da liposomi e procedimenti relativi |
| FR2416008A1 (fr) * | 1978-02-02 | 1979-08-31 | Oreal | Lyophilisats de liposomes |
| IT1111367B (it) * | 1978-11-17 | 1986-01-13 | Serono Ist Farm | Processo per la preparazione estemporanea di liposomi e liposomi cosi' ottenuti |
| JPS55118415A (en) * | 1979-02-28 | 1980-09-11 | Pii Papahadojiyopo Dometoriosu | Method of encapsulating biologically active substance in lipoid cell |
| DE2914789A1 (de) * | 1979-04-11 | 1980-10-16 | Nattermann A & Cie | Injizierbare arzneimittel mit entzuendungshemmender wirkung |
| DE2914788A1 (de) * | 1979-04-11 | 1980-10-16 | Nattermann A & Cie | Parenteral applizierbare, stabile arzneimittelloesungen mit entzuendungshemmender wirkung |
| JPS55153713A (en) * | 1979-05-02 | 1980-11-29 | Kureha Chem Ind Co Ltd | Pharmaceutical preparation of ribosome containing active substance |
| CA1173360A (en) * | 1979-06-22 | 1984-08-28 | Jurg Schrank | Pharmaceutical preparations |
| US4310505A (en) * | 1979-11-08 | 1982-01-12 | California Institute Of Technology | Lipid vesicles bearing carbohydrate surfaces as lymphatic directed vehicles for therapeutic and diagnostic substances |
| HU184141B (en) * | 1979-12-27 | 1984-07-30 | Human Oltoanyagtermelo | Adjuvant particles compositions containing said particles and biologically active substances adsorbed thereon and a process for the preparation thereof |
| JPS5775916A (en) * | 1980-10-29 | 1982-05-12 | Nippon Chemiphar Co Ltd | Coenzyme q pharmaceutical and its preparation |
| JPS57146710A (en) * | 1981-03-07 | 1982-09-10 | Kunio Yagi | Blood brain-barrier permeating ribosome-like microcapsule |
| US4397846A (en) * | 1981-05-15 | 1983-08-09 | Murray Weiner | Storage-stable lipid vesicles and method of preparation |
| JPS58128318A (ja) * | 1982-01-22 | 1983-07-30 | フアイソンズ・ピ−エルシ− | 薬学的組成物 |
| JPS58222014A (ja) * | 1982-06-18 | 1983-12-23 | Taisho Pharmaceut Co Ltd | プロスタグランジンｅ↓１脂肪乳剤 |
| US4588578A (en) * | 1983-08-08 | 1986-05-13 | The Liposome Company, Inc. | Lipid vesicles prepared in a monophase |
| GB8322178D0 (en) * | 1983-08-17 | 1983-09-21 | Sterwin Ag | Preparing aerosol compositions |
| US4744989A (en) * | 1984-02-08 | 1988-05-17 | E. R. Squibb & Sons, Inc. | Method of preparing liposomes and products produced thereby |
| US5141674A (en) * | 1984-03-08 | 1992-08-25 | Phares Pharmaceutical Research N.V. | Methods of preparing pro-liposome dispersions and aerosols |
| JPS60208910A (ja) * | 1984-03-31 | 1985-10-21 | Green Cross Corp:The | 水難溶性薬物・リン脂質複合体の製造方法 |
| SE8403905D0 (sv) * | 1984-07-30 | 1984-07-30 | Draco Ab | Liposomes and steroid esters |
| US5736155A (en) * | 1984-08-08 | 1998-04-07 | The Liposome Company, Inc. | Encapsulation of antineoplastic agents in liposomes |
| US5077056A (en) * | 1984-08-08 | 1991-12-31 | The Liposome Company, Inc. | Encapsulation of antineoplastic agents in liposomes |
| US4880635B1 (en) * | 1984-08-08 | 1996-07-02 | Liposome Company | Dehydrated liposomes |
| EP0172007B1 (en) * | 1984-08-10 | 1991-05-22 | Syntex (U.S.A.) Inc. | Stable liposomes with aqueous-soluble medicaments and methods for their preparation |
| JPS6150912A (ja) * | 1984-08-16 | 1986-03-13 | Shionogi & Co Ltd | リポソ−ム製剤の製造法 |
| JPS61100518A (ja) * | 1984-10-22 | 1986-05-19 | Ono Pharmaceut Co Ltd | ジミリストイルホスフアチジルコリンを主成分とする凍結乾燥されたリポゾ−ム製剤 |
| US4857319A (en) * | 1985-01-11 | 1989-08-15 | The Regents Of The University Of California | Method for preserving liposomes |
| US4830858A (en) * | 1985-02-11 | 1989-05-16 | E. R. Squibb & Sons, Inc. | Spray-drying method for preparing liposomes and products produced thereby |
| US5409704A (en) * | 1985-06-26 | 1995-04-25 | The Liposome Company, Inc. | Liposomes comprising aminoglycoside phosphates and methods of production and use |
| FR2591105B1 (fr) * | 1985-12-11 | 1989-03-24 | Moet Hennessy Rech | Composition pharmaceutique, notamment dermatologique, ou cosmetique, a base de phases lamellaires lipidiques hydratees ou de liposomes contenant un retinoide ou un analogue structural dudit retinoide tel qu'un carotenoide. |
| US5068198A (en) * | 1986-03-26 | 1991-11-26 | Syntex (U.S.A.) Inc. | Liquid single reagent for assays involving confining gels |
| SE8601457D0 (sv) * | 1986-04-01 | 1986-04-01 | Draco Ab | Compositions of liposomes and b?712-receptor active substances for inhalation |
| FR2597345B1 (fr) * | 1986-04-22 | 1990-08-03 | Oreal | Composition cosmetique ou pharmaceutique a base d'une dispersion aqueuse de spherules lipidiques. |
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| US3549382A (en) * | 1968-05-15 | 1970-12-22 | Francis Frederick Hansen | Method of preparing powdered monoglyceride material |
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| CH558659A (fr) * | 1969-11-26 | 1975-02-14 | Orsymonde | Procede pour la preparation d'une composition lyophilisee a usage hygienique. |
| FR2101044A2 (en) * | 1969-11-26 | 1972-03-31 | Orsymonde | Freeze-dried oil - in - water emulsions - for treatment of mouth , teeth, hair and scalp |
| DE2249552A1 (de) * | 1971-10-12 | 1973-05-30 | Inchema S A | Verfahren zur inkapsulation von insbesondere wasserloeslichen verbindungen |
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| CH588887A5 (US20090163788A1-20090625-C00002.png) * | 1974-07-19 | 1977-06-15 | Battelle Memorial Institute | |
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1977
- 1977-05-10 GB GB19510/77A patent/GB1575343A/en not_active Expired
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1978
- 1978-03-07 IE IE464/78A patent/IE46571B1/en not_active IP Right Cessation
- 1978-03-09 NO NO780838A patent/NO150184C/no unknown
- 1978-03-10 ZA ZA00781416A patent/ZA781416B/xx unknown
- 1978-03-14 NZ NZ186696A patent/NZ186696A/xx unknown
- 1978-03-14 IL IL54270A patent/IL54270A/xx unknown
- 1978-03-17 AU AU34235/78A patent/AU514644B2/en not_active Expired
- 1978-04-03 FI FI781012A patent/FI63856C/fi not_active IP Right Cessation
- 1978-04-07 CA CA300,720A patent/CA1114758A/en not_active Expired
- 1978-04-27 DE DE2818655A patent/DE2818655C2/de not_active Expired
- 1978-05-03 BE BE187387A patent/BE866697A/xx not_active IP Right Cessation
- 1978-05-09 SE SE7805276A patent/SE440725B/sv not_active IP Right Cessation
- 1978-05-09 FR FR7813632A patent/FR2390159A1/fr active Granted
- 1978-05-09 CH CH5038/78A patent/CH650944A5/de not_active IP Right Cessation
- 1978-05-09 CH CH6832/82A patent/CH652615A5/de not_active IP Right Cessation
- 1978-05-09 JP JP5487578A patent/JPS53142514A/ja active Granted
- 1978-05-10 NL NL7805005A patent/NL7805005A/xx active Search and Examination
- 1978-05-10 IT IT23207/78A patent/IT1094811B/it active
- 1978-05-10 DK DK206578A patent/DK156765C/da not_active IP Right Cessation
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- 1979-08-20 US US06/067,948 patent/US4311712A/en not_active Expired - Lifetime
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- 1980-11-13 IL IL61475A patent/IL61475A0/xx unknown
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1981
- 1981-09-18 US US06/303,578 patent/US4370349A/en not_active Expired - Lifetime
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1982
- 1982-03-04 SE SE8201351A patent/SE453962B/sv not_active IP Right Cessation
- 1982-03-04 SE SE8201350A patent/SE454049B/sv not_active IP Right Cessation
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1983
- 1983-11-17 NO NO834219A patent/NO153121C/no unknown
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