NO302735B1 - Fremgangsmåte for fremstilling av farmasöytiske liposompreparater - Google Patents
Fremgangsmåte for fremstilling av farmasöytiske liposompreparater Download PDFInfo
- Publication number
- NO302735B1 NO302735B1 NO911281A NO911281A NO302735B1 NO 302735 B1 NO302735 B1 NO 302735B1 NO 911281 A NO911281 A NO 911281A NO 911281 A NO911281 A NO 911281A NO 302735 B1 NO302735 B1 NO 302735B1
- Authority
- NO
- Norway
- Prior art keywords
- cis
- octadecenoyl
- zinc
- synthetic
- phthalocyanine complex
- Prior art date
Links
- 239000002502 liposome Substances 0.000 title claims abstract description 53
- 238000002360 preparation method Methods 0.000 title claims description 45
- 238000000034 method Methods 0.000 title claims description 29
- 239000006185 dispersion Substances 0.000 claims abstract description 33
- 150000003904 phospholipids Chemical class 0.000 claims abstract description 27
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 29
- 239000002904 solvent Substances 0.000 claims description 19
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
- 238000001990 intravenous administration Methods 0.000 claims description 14
- 239000008346 aqueous phase Substances 0.000 claims description 11
- 239000007788 liquid Substances 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 10
- -1 n-tetradecanoyl Chemical group 0.000 claims description 9
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 7
- 239000011877 solvent mixture Substances 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 3
- 238000007911 parenteral administration Methods 0.000 claims description 3
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 claims description 2
- 239000000872 buffer Substances 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 229910001415 sodium ion Inorganic materials 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 46
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 22
- 239000000203 mixture Substances 0.000 description 20
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 20
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 19
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 19
- 239000008101 lactose Substances 0.000 description 19
- 239000011701 zinc Substances 0.000 description 19
- 229910052725 zinc Inorganic materials 0.000 description 19
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 18
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 18
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- 150000002632 lipids Chemical class 0.000 description 10
- 235000002639 sodium chloride Nutrition 0.000 description 10
- 239000011780 sodium chloride Substances 0.000 description 10
- 239000003960 organic solvent Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000012528 membrane Substances 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 230000001225 therapeutic effect Effects 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 241000282412 Homo Species 0.000 description 4
- 206010028980 Neoplasm Diseases 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 239000012300 argon atmosphere Substances 0.000 description 4
- 238000000502 dialysis Methods 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 238000004108 freeze drying Methods 0.000 description 4
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 108090000623 proteins and genes Proteins 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 102000004169 proteins and genes Human genes 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 231100000331 toxic Toxicity 0.000 description 3
- 230000002588 toxic effect Effects 0.000 description 3
- 201000009030 Carcinoma Diseases 0.000 description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 229930195725 Mannitol Natural products 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical class CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 description 2
- IJCWFDPJFXGQBN-RYNSOKOISA-N [(2R)-2-[(2R,3R,4S)-4-hydroxy-3-octadecanoyloxyoxolan-2-yl]-2-octadecanoyloxyethyl] octadecanoate Chemical class CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCCCCCCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCCCCCCCCCCCC IJCWFDPJFXGQBN-RYNSOKOISA-N 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 238000002512 chemotherapy Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000002523 gelfiltration Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 239000000594 mannitol Substances 0.000 description 2
- 235000010355 mannitol Nutrition 0.000 description 2
- 239000000693 micelle Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 229920001983 poloxamer Polymers 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 238000012552 review Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229950004959 sorbitan oleate Drugs 0.000 description 2
- 229950003429 sorbitan palmitate Drugs 0.000 description 2
- 229950011392 sorbitan stearate Drugs 0.000 description 2
- 229960000391 sorbitan trioleate Drugs 0.000 description 2
- 229960004129 sorbitan tristearate Drugs 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- 230000002110 toxicologic effect Effects 0.000 description 2
- 231100000027 toxicology Toxicity 0.000 description 2
- 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 description 1
- 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
- XZIIFPSPUDAGJM-UHFFFAOYSA-N 6-chloro-2-n,2-n-diethylpyrimidine-2,4-diamine Chemical class CCN(CC)C1=NC(N)=CC(Cl)=N1 XZIIFPSPUDAGJM-UHFFFAOYSA-N 0.000 description 1
- 241000234282 Allium Species 0.000 description 1
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 101100208721 Mus musculus Usp5 gene Proteins 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- PAMIQIKDUOTOBW-UHFFFAOYSA-N N-methylcyclohexylamine Natural products CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 1
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Chemical class 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 239000012506 Sephacryl® Substances 0.000 description 1
- 229920002684 Sepharose Polymers 0.000 description 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
- NWGKJDSIEKMTRX-AAZCQSIUSA-N Sorbitan monooleate Chemical class CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O NWGKJDSIEKMTRX-AAZCQSIUSA-N 0.000 description 1
- IYFATESGLOUGBX-YVNJGZBMSA-N Sorbitan monopalmitate Chemical class CCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O IYFATESGLOUGBX-YVNJGZBMSA-N 0.000 description 1
- HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical class CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 description 1
- 239000004147 Sorbitan trioleate Chemical class 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 210000000683 abdominal cavity Anatomy 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000012062 aqueous buffer Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000002296 dynamic light scattering Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229940088598 enzyme Drugs 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000005429 filling process Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000003791 organic solvent mixture Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000000886 photobiology Effects 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 229940035044 sorbitan monolaurate Drugs 0.000 description 1
- 235000019337 sorbitan trioleate Nutrition 0.000 description 1
- 239000001589 sorbitan tristearate Chemical class 0.000 description 1
- 235000011078 sorbitan tristearate Nutrition 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 238000011146 sterile filtration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- 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
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)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Paper (AREA)
- Materials For Medical Uses (AREA)
- Glass Compositions (AREA)
- Manufacturing Of Micro-Capsules (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH110490 | 1990-04-03 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO911281D0 NO911281D0 (no) | 1991-04-02 |
| NO911281L NO911281L (no) | 1991-10-04 |
| NO302735B1 true NO302735B1 (no) | 1998-04-20 |
Family
ID=4202574
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO911281A NO302735B1 (no) | 1990-04-03 | 1991-04-02 | Fremgangsmåte for fremstilling av farmasöytiske liposompreparater |
Country Status (18)
| Country | Link |
|---|---|
| EP (1) | EP0451103B1 (ja) |
| JP (1) | JPH085793B2 (ja) |
| KR (1) | KR910018014A (ja) |
| AT (1) | ATE108328T1 (ja) |
| AU (1) | AU634644B2 (ja) |
| CA (1) | CA2039477C (ja) |
| DE (1) | DE59102143D1 (ja) |
| DK (1) | DK0451103T3 (ja) |
| ES (1) | ES2056617T3 (ja) |
| FI (1) | FI104951B (ja) |
| HU (1) | HU208485B (ja) |
| IE (1) | IE64990B1 (ja) |
| IL (1) | IL97681A (ja) |
| NO (1) | NO302735B1 (ja) |
| NZ (1) | NZ237631A (ja) |
| PH (1) | PH30330A (ja) |
| PT (1) | PT97215B (ja) |
| ZA (1) | ZA912425B (ja) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6890555B1 (en) | 1992-02-05 | 2005-05-10 | Qlt, Inc. | Liposome compositions of porphyrin photosensitizers |
| CA2087902C (en) * | 1992-02-05 | 2006-10-17 | Narendra Raghunathji Desai | Liposome compositions of porphyrin photosensitizers |
| TW235298B (ja) * | 1992-02-27 | 1994-12-01 | Ciba Geigy | |
| US5616602A (en) * | 1993-07-09 | 1997-04-01 | Ciba-Geigy Corporation | Topically administrable zinc phthalocyanine compositions |
| WO1997010811A1 (en) * | 1995-09-21 | 1997-03-27 | Novartis Ag | Nanoparticles in photodynamic therapy |
| US5715023A (en) * | 1996-04-30 | 1998-02-03 | Kaiser Electro-Optics, Inc. | Plane parallel optical collimating device employing a cholesteric liquid crystal |
| US6010890A (en) * | 1997-04-29 | 2000-01-04 | New York Blood Center, Inc. | Method for viral inactivation and compositions for use in same |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1260393A (en) * | 1984-10-16 | 1989-09-26 | Lajos Tarcsay | Liposomes of synthetic lipids |
| CA1321351C (en) * | 1987-02-23 | 1993-08-17 | Helmut Otmar Hauser | Method of dehydrating vesicle preparations for long-term storage |
-
1991
- 1991-03-26 ES ES91810217T patent/ES2056617T3/es not_active Expired - Lifetime
- 1991-03-26 DK DK91810217.9T patent/DK0451103T3/da active
- 1991-03-26 EP EP91810217A patent/EP0451103B1/de not_active Expired - Lifetime
- 1991-03-26 IL IL9768191A patent/IL97681A/en not_active IP Right Cessation
- 1991-03-26 AT AT91810217T patent/ATE108328T1/de not_active IP Right Cessation
- 1991-03-26 DE DE59102143T patent/DE59102143D1/de not_active Expired - Fee Related
- 1991-03-27 FI FI911501A patent/FI104951B/fi not_active IP Right Cessation
- 1991-03-27 PH PH42213A patent/PH30330A/en unknown
- 1991-03-28 IE IE107691A patent/IE64990B1/en not_active IP Right Cessation
- 1991-03-28 CA CA002039477A patent/CA2039477C/en not_active Expired - Fee Related
- 1991-03-28 NZ NZ237631A patent/NZ237631A/en unknown
- 1991-04-01 PT PT97215A patent/PT97215B/pt not_active IP Right Cessation
- 1991-04-02 ZA ZA912425A patent/ZA912425B/xx unknown
- 1991-04-02 HU HU911070A patent/HU208485B/hu not_active IP Right Cessation
- 1991-04-02 KR KR1019910005252A patent/KR910018014A/ko not_active Application Discontinuation
- 1991-04-02 AU AU74046/91A patent/AU634644B2/en not_active Ceased
- 1991-04-02 JP JP3069856A patent/JPH085793B2/ja not_active Expired - Fee Related
- 1991-04-02 NO NO911281A patent/NO302735B1/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| PT97215A (pt) | 1992-01-31 |
| IL97681A (en) | 1996-01-31 |
| EP0451103A1 (de) | 1991-10-09 |
| CA2039477A1 (en) | 1991-10-04 |
| DK0451103T3 (da) | 1994-08-15 |
| IL97681A0 (en) | 1992-06-21 |
| HU208485B (en) | 1993-11-29 |
| CA2039477C (en) | 2002-09-24 |
| NO911281D0 (no) | 1991-04-02 |
| NZ237631A (en) | 1992-12-23 |
| IE911076A1 (en) | 1991-10-09 |
| PH30330A (en) | 1997-04-02 |
| IE64990B1 (en) | 1995-09-20 |
| AU7404691A (en) | 1991-10-10 |
| EP0451103B1 (de) | 1994-07-13 |
| ES2056617T3 (es) | 1994-10-01 |
| KR910018014A (ko) | 1991-11-30 |
| FI911501A (fi) | 1991-10-04 |
| HU911070D0 (en) | 1991-10-28 |
| DE59102143D1 (de) | 1994-08-18 |
| JPH04221316A (ja) | 1992-08-11 |
| ZA912425B (en) | 1991-11-27 |
| ATE108328T1 (de) | 1994-07-15 |
| NO911281L (no) | 1991-10-04 |
| JPH085793B2 (ja) | 1996-01-24 |
| HUT59009A (en) | 1992-04-28 |
| FI911501A0 (fi) | 1991-03-27 |
| AU634644B2 (en) | 1993-02-25 |
| FI104951B (fi) | 2000-05-15 |
| PT97215B (pt) | 1998-07-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5466468A (en) | Parenterally administrable liposome formulation comprising synthetic lipids | |
| US5270053A (en) | Parenterally administerable liposome formulation comprising synthetic lipid | |
| JP5154296B2 (ja) | 疎水性薬物のための薬物送達系 | |
| JP4890732B2 (ja) | 癌治療用パクリタキセル・リポソーム組成物およびその製造方法 | |
| JP3782112B2 (ja) | ヒドロ−モノベンゾポルフィリン光増感剤を含有するリポソームの作成方法 | |
| CA2442539C (en) | Method and composition for solubilising a biologically active compound with low water solubility | |
| JPH11509834A (ja) | ヒドロ−モノベンゾポルフィリン光増感剤を含有するリポソームの作成方法 | |
| JPH08268893A (ja) | スタウロスポリン誘導体の静脈内投与のための医薬組成物 | |
| KR20050038011A (ko) | 백금 응집체 및 이의 제조 방법 | |
| JP2009507049A (ja) | リン脂質のポリエチレングリコール誘導体に包み込まれたビンカアルカロイド系制癌剤のナノミセル製剤 | |
| WO2004017940A2 (en) | Pharmaceutically active lipid based formulation of sn38 | |
| CA2050679C (en) | Preparation of liposome and lipid complex compositions | |
| WO2007009355A1 (fr) | Injection de paclitaxel et sa méthode de préparation | |
| NO302735B1 (no) | Fremgangsmåte for fremstilling av farmasöytiske liposompreparater | |
| JPH02502719A (ja) | 薬理学的剤‐脂質溶液製剤 | |
| JPS63192716A (ja) | 非経口投与用懸濁液 | |
| CN108578368B (zh) | 一种伊立替康-胆固醇琥珀酸单脂离子对及脂质体和制备方法及应用 | |
| CN103040764B (zh) | 一种盐酸平阳霉素脂质体注射剂 | |
| CN100428937C (zh) | 左西孟旦冷冻干燥组合物 | |
| JP2002518322A (ja) | ブスルファンのリポソーム製剤 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |