CH658001A5 - Liposom. - Google Patents

Liposom. Download PDF

Info

Publication number: CH658001A5
Authority: CH; Switzerland
Prior art keywords: liposome; liposome according; glucoside; beta; lipid
Prior art date: 1981-10-29

Application number

CH1532/83A

Other languages

German (de)

English (en)

Inventor

Masanobu Kawamata

Koichi Ushimaru

Shuji Yamane

Original Assignee

Nippon Shinyaku Co Ltd

Priority date (The priority date 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 date listed.)

1981-10-29

Filing date

1983-03-21

Publication date

1986-10-15

1983-03-21 Application filed by Nippon Shinyaku Co Ltd filed Critical Nippon Shinyaku Co Ltd

1986-10-15 Publication of CH658001A5 publication Critical patent/CH658001A5/de

Links

239000002502 liposome Substances 0.000 claims description 50
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 38
229930182478 glucoside Natural products 0.000 claims description 20
150000008131 glucosides Chemical class 0.000 claims description 20
150000002632 lipids Chemical class 0.000 claims description 20
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 14
239000000126 substance Substances 0.000 claims description 10
238000000034 method Methods 0.000 claims description 9
229930182558 Sterol Natural products 0.000 claims description 8
150000003432 sterols Chemical class 0.000 claims description 8
235000003702 sterols Nutrition 0.000 claims description 8
235000012000 cholesterol Nutrition 0.000 claims description 7
VWDLOXMZIGUBKM-PLWLBJPKSA-N Stigmasteryl glucoside Chemical compound O([C@@H]1CC2=CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)/C=C/[C@@H](CC)C(C)C)[C@@H]1OC(CO)[C@@H](O)C(O)C1O VWDLOXMZIGUBKM-PLWLBJPKSA-N 0.000 claims description 6
239000004480 active ingredient Substances 0.000 claims description 6
239000003795 chemical substances by application Substances 0.000 claims description 6
239000012528 membrane Substances 0.000 claims description 6
-1 be-ta-sitosterol Chemical compound 0.000 claims description 5
LGJMUZUPVCAVPU-UHFFFAOYSA-N beta-Sitostanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 LGJMUZUPVCAVPU-UHFFFAOYSA-N 0.000 claims description 5
REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical group CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
235000016831 stigmasterol Nutrition 0.000 claims description 4
229940032091 stigmasterol Drugs 0.000 claims description 4
BFDNMXAIBMJLBB-UHFFFAOYSA-N stigmasterol Natural products CCC(C=CC(C)C1CCCC2C3CC=C4CC(O)CCC4(C)C3CCC12C)C(C)C BFDNMXAIBMJLBB-UHFFFAOYSA-N 0.000 claims description 4
OILXMJHPFNGGTO-UHFFFAOYSA-N (22E)-(24xi)-24-methylcholesta-5,22-dien-3beta-ol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(C)C(C)C)C1(C)CC2 OILXMJHPFNGGTO-UHFFFAOYSA-N 0.000 claims description 3
OQMZNAMGEHIHNN-UHFFFAOYSA-N 7-Dehydrostigmasterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CC(CC)C(C)C)CCC33)C)C3=CC=C21 OQMZNAMGEHIHNN-UHFFFAOYSA-N 0.000 claims description 3
HZYXFRGVBOPPNZ-UHFFFAOYSA-N UNPD88870 Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)=CCC(CC)C(C)C)C1(C)CC2 HZYXFRGVBOPPNZ-UHFFFAOYSA-N 0.000 claims description 3
FWNZEKQVBDXWKA-NYENXMMQSA-N campesterol 3-beta-D-glucoside Chemical compound CC(C)[C@H](C)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@H](CC[C@]4(C)[C@H]3CC[C@]12C)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O FWNZEKQVBDXWKA-NYENXMMQSA-N 0.000 claims description 3
FSMCJUNYLQOAIM-UQBZCTSOSA-N cholesteryl beta-D-glucoside Chemical compound O([C@@H]1CC2=CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O FSMCJUNYLQOAIM-UQBZCTSOSA-N 0.000 claims description 3
RNPXCFINMKSQPQ-UHFFFAOYSA-N dicetyl hydrogen phosphate Chemical compound CCCCCCCCCCCCCCCCOP(O)(=O)OCCCCCCCCCCCCCCCC RNPXCFINMKSQPQ-UHFFFAOYSA-N 0.000 claims description 3
229950005143 sitosterol Drugs 0.000 claims description 3
HCXVJBMSMIARIN-PHZDYDNGSA-N stigmasterol 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)/C=C/[C@@H](CC)C(C)C)[C@@]1(C)CC2 HCXVJBMSMIARIN-PHZDYDNGSA-N 0.000 claims description 3
238000003756 stirring Methods 0.000 claims description 3
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 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 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims 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 claims description 2
230000005855 radiation Effects 0.000 claims description 2
239000003381 stabilizer Substances 0.000 claims description 2
229960001701 chloroform Drugs 0.000 claims 3
241000446313 Lamella Species 0.000 claims 2
239000008348 synthetic phosphatidyl choline Substances 0.000 claims 2
HVVJCLFLKMGEIY-UHFFFAOYSA-N 2,3-dioctadecoxypropyl 2-(trimethylazaniumyl)ethyl phosphate Chemical compound CCCCCCCCCCCCCCCCCCOCC(COP([O-])(=O)OCC[N+](C)(C)C)OCCCCCCCCCCCCCCCCCC HVVJCLFLKMGEIY-UHFFFAOYSA-N 0.000 claims 1
229960003724 dimyristoylphosphatidylcholine Drugs 0.000 claims 1
125000005539 phosphatidic acid group Chemical group 0.000 claims 1
239000000243 solution Substances 0.000 description 41
238000002347 injection Methods 0.000 description 22
239000007924 injection Substances 0.000 description 22
150000001875 compounds Chemical class 0.000 description 14
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
239000000203 mixture Substances 0.000 description 13
230000000144 pharmacologic effect Effects 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
241000196324 Embryophyta Species 0.000 description 7
239000000787 lecithin Substances 0.000 description 6
229940067606 lecithin Drugs 0.000 description 6
235000010445 lecithin Nutrition 0.000 description 6
239000002904 solvent Substances 0.000 description 6
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 5
QXMNTPFFZFYQAI-IMDKZJJXSA-N beta-sitosterol 3-O-beta-D-glucopyranoside Natural products CC[C@H](CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@H](CC[C@]4(C)[C@H]3CC[C@]12C)O[C@@H]5C[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)C(C)C QXMNTPFFZFYQAI-IMDKZJJXSA-N 0.000 description 5
QHKKPRDTANXCBJ-UHFFFAOYSA-N beta-sitosterol-delta-glucopyranoside Natural products CCC(CCC(C)C1CCC2C3CC=C4CC(CCC4(C)C3CCC12C)OC5OC(OC)C(O)C(O)C5O)C(C)C QHKKPRDTANXCBJ-UHFFFAOYSA-N 0.000 description 5
YCHQFVUAIVWDNL-UHFFFAOYSA-N beta-sitosteryl-beta-D-glucoside Natural products CCC(CCC(C)C1CCC2C3CC=C4CC(CCC4(C)C3CCC2(C)C1)OC5OC(CO)C(O)C(O)C5O)C(C)C YCHQFVUAIVWDNL-UHFFFAOYSA-N 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
239000003708 ampul Substances 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
235000012343 cottonseed oil Nutrition 0.000 description 4
230000002439 hemostatic effect Effects 0.000 description 4
238000010253 intravenous injection Methods 0.000 description 4
239000000463 material Substances 0.000 description 4
239000008177 pharmaceutical agent Substances 0.000 description 4
230000001954 sterilising effect Effects 0.000 description 4
244000068988 Glycine max Species 0.000 description 3
235000010469 Glycine max Nutrition 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
230000000703 anti-shock Effects 0.000 description 3
229910001873 dinitrogen Inorganic materials 0.000 description 3
239000003814 drug Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000011148 porous material Substances 0.000 description 3
238000004659 sterilization and disinfection Methods 0.000 description 3
210000004243 sweat Anatomy 0.000 description 3
210000002268 wool Anatomy 0.000 description 3
PORPENFLTBBHSG-MGBGTMOVSA-N 1,2-dihexadecanoyl-sn-glycerol-3-phosphate Chemical group CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCC PORPENFLTBBHSG-MGBGTMOVSA-N 0.000 description 2
SGNBVLSWZMBQTH-FGAXOLDCSA-N Campesterol Natural products O[C@@H]1CC=2[C@@](C)([C@@H]3[C@H]([C@H]4[C@@](C)([C@H]([C@H](CC[C@H](C(C)C)C)C)CC4)CC3)CC=2)CC1 SGNBVLSWZMBQTH-FGAXOLDCSA-N 0.000 description 2
235000010523 Cicer arietinum Nutrition 0.000 description 2
244000045195 Cicer arietinum Species 0.000 description 2
240000000560 Citrus x paradisi Species 0.000 description 2
BTEISVKTSQLKST-UHFFFAOYSA-N Haliclonasterol Natural products CC(C=CC(C)C(C)(C)C)C1CCC2C3=CC=C4CC(O)CCC4(C)C3CCC12C BTEISVKTSQLKST-UHFFFAOYSA-N 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
239000003125 aqueous solvent Substances 0.000 description 2
229940076810 beta sitosterol Drugs 0.000 description 2
NJKOMDUNNDKEAI-UHFFFAOYSA-N beta-sitosterol Natural products CCC(CCC(C)C1CCC2(C)C3CC=C4CC(O)CCC4C3CCC12C)C(C)C NJKOMDUNNDKEAI-UHFFFAOYSA-N 0.000 description 2
230000000740 bleeding effect Effects 0.000 description 2
210000004204 blood vessel Anatomy 0.000 description 2
SGNBVLSWZMBQTH-PODYLUTMSA-N campesterol 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)CC[C@@H](C)C(C)C)[C@@]1(C)CC2 SGNBVLSWZMBQTH-PODYLUTMSA-N 0.000 description 2
235000000431 campesterol Nutrition 0.000 description 2
239000000470 constituent Substances 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
238000011835 investigation Methods 0.000 description 2
235000021374 legumes Nutrition 0.000 description 2
239000007788 liquid Substances 0.000 description 2
230000004526 pharmaceutical effect Effects 0.000 description 2
239000008363 phosphate buffer Substances 0.000 description 2
KZJWDPNRJALLNS-VJSFXXLFSA-N sitosterol 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)CC[C@@H](CC)C(C)C)[C@@]1(C)CC2 KZJWDPNRJALLNS-VJSFXXLFSA-N 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
230000003381 solubilizing effect Effects 0.000 description 2
125000002328 sterol group Chemical group 0.000 description 2
239000004094 surface-active agent Substances 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
KILNVBDSWZSGLL-UHFFFAOYSA-O 2-[2,3-di(hexadecanoyloxy)propoxy-hydroxyphosphoryl]oxyethyl-trimethylazanium Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(COP(O)(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCC KILNVBDSWZSGLL-UHFFFAOYSA-O 0.000 description 1
BBTIMXAYZRWPNG-UHFFFAOYSA-N 3beta,Delta4-stigmasten-3-ol Natural products C1CC2=CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 BBTIMXAYZRWPNG-UHFFFAOYSA-N 0.000 description 1
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
239000003513 alkali Substances 0.000 description 1
QADVIPISOOQJMJ-WLKYTNTRSA-N beta-stigmasterol Natural products CCC(CC)C=C[C@@H](C)[C@H]1CC[C@@H]2[C@@H]1CC[C@H]3[C@H]2CC=C4C[C@@H](O)CC[C@]34C QADVIPISOOQJMJ-WLKYTNTRSA-N 0.000 description 1
239000012496 blank sample Substances 0.000 description 1
239000000872 buffer Substances 0.000 description 1
239000007853 buffer solution Substances 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000004359 castor oil Substances 0.000 description 1
235000019438 castor oil Nutrition 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
229940107161 cholesterol Drugs 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
238000001914 filtration Methods 0.000 description 1
150000002270 gangliosides Chemical class 0.000 description 1
238000002523 gelfiltration Methods 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
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
238000002372 labelling Methods 0.000 description 1
229960003511 macrogol Drugs 0.000 description 1
239000002075 main ingredient Substances 0.000 description 1
229940126601 medicinal product Drugs 0.000 description 1
229910000403 monosodium phosphate Inorganic materials 0.000 description 1
235000019799 monosodium phosphate Nutrition 0.000 description 1
239000012454 non-polar solvent Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
150000002942 palmitic acid derivatives Chemical class 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
239000002504 physiological saline solution Substances 0.000 description 1
235000002378 plant sterols Nutrition 0.000 description 1
238000012545 processing Methods 0.000 description 1
239000000047 product Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000000926 separation method Methods 0.000 description 1
AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
HCXVJBMSMIARIN-UHFFFAOYSA-N stigmasterol Chemical compound C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(CC)C(C)C)C1(C)CC2 HCXVJBMSMIARIN-UHFFFAOYSA-N 0.000 description 1
238000005728 strengthening Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000012360 testing method Methods 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
229910000406 trisodium phosphate Inorganic materials 0.000 description 1
235000019801 trisodium phosphate Nutrition 0.000 description 1
238000005199 ultracentrifugation Methods 0.000 description 1
238000002604 ultrasonography Methods 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1
230000000304 vasodilatating effect Effects 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil 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—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
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
- A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
- A61K31/704—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin attached to a condensed carbocyclic ring system, e.g. sennosides, thiocolchicosides, escin, daunorubicin
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/12—Carboxylic acids; Salts or anhydrides thereof

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Dispersion Chemistry (AREA)
Oil, Petroleum & Natural Gas (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Preparation (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Manufacturing Of Micro-Capsules (AREA)

CH1532/83A 1981-10-29 1983-03-21 Liposom. CH658001A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP56173944A JPS5874619A (ja)	1981-10-29	1981-10-29	リポソ−ム及びその製法

Publications (1)

Publication Number	Publication Date
CH658001A5 true CH658001A5 (de)	1986-10-15

Family

ID=15969954

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1532/83A CH658001A5 (de)	1981-10-29	1983-03-21	Liposom.

Country Status (7)

Country	Link
JP (1)	JPS5874619A (fr)
KR (1)	KR840001278A (fr)
BE (1)	BE896217A (fr)
CH (1)	CH658001A5 (fr)
DE (1)	DE3309076C2 (fr)
FR (1)	FR2542999B1 (fr)
GB (1)	GB2135878B (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE4107153A1 (de) *	1991-03-06	1992-09-10	Gregor Cevc	Praeparat zur wirkstoffapplikation in kleinsttroepfchenform
DE4107152A1 (de) *	1991-03-06	1992-09-10	Gregor Cevc	Praeparate zur nichtinvasiven verabreichung von antidiabetica

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6251425B1 (en) *	1998-10-02	2001-06-26	Igen, Inc.	Glucoside paucilamellar vesicles
US20070196436A1 (en) *	2006-02-23	2007-08-23	Conopco, Inc., D/B/A Unilever	Process for preparing an edible composition comprising steroidal glycosides
US10251839B2 (en)	2008-01-22	2019-04-09	Igi Laboratories, Inc.	Lipid vesicles derived from olive oil fatty acids
US9775853B2 (en)	2013-03-15	2017-10-03	Biomet Manufacturing, Llc.	Hemostatic compositions and methods

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ZA72698B (en) *	1972-02-03	1973-09-26	Liebenberg R W	Method of preparing medicinal compositions
US3966918A (en) *	1973-12-12	1976-06-29	Nippon Shinyaku Co., Ltd.	Method of preparing aqueous solutions of sterol glycosides and their ester derivatives
JPS51139613A (en) *	1975-05-24	1976-12-02	Nippon Shinyaku Co Ltd	An absorbable non-crystalline sterol glycoside monopalmitate ester and a method for preparing its pharmaceutical
GB1491549A (en) *	1975-05-26	1977-11-09	Nippon Shinyaku Co Ltd	Haemostatics vascular stabilisers and anti-shock agents
DE2759171A1 (de) *	1977-12-31	1979-07-12	Roecar Holdings Nv	Arzneimittel mit wirkung als prostaglandinsynthetaseninhibitor
SE7900458L (sv) *	1978-01-27	1979-07-28	Sandoz Ag	Liposom-avgivningssystem for lekemedel
US4254111A (en) *	1978-07-05	1981-03-03	Roecar Holdings (Netherlands Antilles) Nv	Sterolin products
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

1981
- 1981-10-29 JP JP56173944A patent/JPS5874619A/ja active Pending
1982
- 1982-09-08 KR KR1019820004068A patent/KR840001278A/ko not_active Ceased
1983
- 1983-03-07 GB GB08306237A patent/GB2135878B/en not_active Expired
- 1983-03-14 DE DE3309076A patent/DE3309076C2/de not_active Expired
- 1983-03-18 BE BE0/210362A patent/BE896217A/fr not_active IP Right Cessation
- 1983-03-21 CH CH1532/83A patent/CH658001A5/de not_active IP Right Cessation
- 1983-03-21 FR FR8304592A patent/FR2542999B1/fr not_active Expired

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE4107153A1 (de) *	1991-03-06	1992-09-10	Gregor Cevc	Praeparat zur wirkstoffapplikation in kleinsttroepfchenform
DE4107152A1 (de) *	1991-03-06	1992-09-10	Gregor Cevc	Praeparate zur nichtinvasiven verabreichung von antidiabetica

Also Published As

Publication number	Publication date
FR2542999A1 (fr)	1984-09-28
DE3309076A1 (de)	1984-09-20
GB2135878B (en)	1987-07-22
GB2135878A (en)	1984-09-12
GB8306237D0 (en)	1983-04-13
KR840001278A (ko)	1984-04-30
FR2542999B1 (fr)	1987-09-25
DE3309076C2 (de)	1986-06-12
JPS5874619A (ja)	1983-05-06
BE896217A (fr)	1983-07-18

Legal Events

Date	Code	Title	Description
1994-11-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
US4614796A (en)	1986-09-30	Liposome and method of manufacture therefor
DE3886970T2 (de)	1994-05-26	Natürliches oberflächenwirksames Lungenpräparat, Verfahren zu seiner Herstellung und pharmazeutische Zusammensetzungen.
EP0021337B1 (fr)	1983-12-07	Préparations pour l'administration parentérale de médicaments liposolubles
DE2946601C2 (de)	1990-05-31	Verfahren zum extemporierten Herstellen von Liposomen
DE3751258T2 (de)	1995-09-07	Mikrokristalle, die eine aktive Substanz mit phospholipidischer Affinität enthalten und mindestens ein Phospholipid, Verfahren zur Herstellung.
DE60118395T2 (de)	2006-12-07	Pharmazeutische zusammensetzungen mit verzögerter freisetzung für die parenterale applikation von hydrophilen wirkstoffen
DE2747378A1 (de)	1978-04-27	Liposomen, verfahren zu ihrer herstellung und sie enthaltende arzneimittel
CH657049A5 (de)	1986-08-15	Kuenstliches oberflaechenaktives mittel fuer die lunge und heilmittel fuer syndrome von atemnot, die dieses als aktive komponente enthalten.
DE3021006A1 (de)	1981-01-08	Neues oberflaechenaktives material, verfahren zur herstellung desselben und dieses material enthaltendes pharmazeutisches mittel gegen hyalin-membran-erkrankung
EP0461559B1 (fr)	1997-09-10	Liposomes sans agent actif pour le traitement l'athérosclérose
DD144719A5 (de)	1980-11-05	Verfahren zur gewinnung einer natuerlichen polarfraktion mit antipsoriatischer wirksamkeit
DE3201865A1 (de)	1982-08-19	Pharmazeutisches mittel und dessen verwendung fuer die behandlung der osteopathie
EP0145005B1 (fr)	1989-04-12	Tensio-actif pulmonaire, procédé de préparation et utilisation pharmaceutique
CH658001A5 (de)	1986-10-15	Liposom.
DE69937574T2 (de)	2008-09-04	Verwendung des pharmazeutischen präparates "histochrome" zur behandlung des akuten herzinfarkts und ischämischer herzerkrankungen
DE60011625T2 (de)	2005-07-07	Cisplatin enthaltende parenterale emulsion
DE68927163T2 (de)	1997-04-03	Zytotropische heterogene molekulare Lipide und Verfahren für ihre Zubereitung
DE69209335T2 (de)	1996-08-29	Mittel zur Zersetzung von Gallensteinen
WO1991011993A1 (fr)	1991-08-22	Composition phospholipidique aqueuse sous forme de gel a teneur en alcool, son utilisation et preparations topiques la renfermant
DE1668171A1 (de)	1974-08-29	Verfahren zur herstellung von stabilen waessrigen loesungen neuer komplexer organosiliciumverbindungen
DE2262427A1 (de)	1973-07-12	Immunostimulierendes mittel und verfahren zu dessen herstellung
DE2546001A1 (de)	1976-04-15	Immunostimulierende phospholipide und sie enthaltende arzneimittel
DE19522693A1 (de)	1997-01-02	Zusammensetzung zur Herstellung feindisperser Systeme und Verfahren zu ihrer Herstellung
DE10015814A1 (de)	2001-10-11	Arzneimittel zur Stimulierung der Leukopoese, zur Behandlung von Tumor- und Protozoenerkrankungen und Verfahren zu seiner Herstellung
DE69019759T2 (de)	1995-10-26	Liposomale zusammensetzungen.

CH658001A5 - Liposom. - Google Patents

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