CH624011A5 - - Google Patents

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Info

Publication number: CH624011A5
Authority: CH; Switzerland
Prior art keywords: solution; liposomes; encapsulated; liquid; aqueous
Prior art date: 1977-08-05

Application number

CH961677A

Other languages

English (en)

French (fr)

Inventor

Michel Schneider

Original Assignee

Battelle Memorial Institute

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.)

1977-08-05

Filing date

1977-08-05

Publication date

1981-07-15

1977-08-05 Application filed by Battelle Memorial Institute filed Critical Battelle Memorial Institute

1977-08-05 Priority to CH961677A priority Critical patent/CH624011A5/fr

1978-07-17 Priority to IL55154A priority patent/IL55154A/xx

1978-08-02 Priority to IE1574/78A priority patent/IE47067B1/en

1978-08-02 Priority to GB7832003A priority patent/GB2001929B/en

1978-08-02 Priority to JP9372978A priority patent/JPS5441279A/ja

1978-08-02 Priority to HU78BA3681A priority patent/HU179672B/hu

1978-08-03 Priority to SE7808356A priority patent/SE433169B/sv

1978-08-03 Priority to ZA00784407A priority patent/ZA784407B/xx

1978-08-03 Priority to DE19782834307 priority patent/DE2834307A1/de

1978-08-03 Priority to FR7822985A priority patent/FR2399242A1/fr

1978-08-03 Priority to LU80071A priority patent/LU80071A1/xx

1978-08-03 Priority to ES472326A priority patent/ES472326A1/es

1978-08-03 Priority to NL787808167A priority patent/NL7808167A/xx

1978-08-03 Priority to IT26441/78A priority patent/IT1097928B/it

1978-08-03 Priority to DK344478A priority patent/DK155036C/da

1978-08-03 Priority to CA308,715A priority patent/CA1098410A/en

1978-08-03 Priority to BE78189678A priority patent/BE869490A/xx

1978-08-04 Priority to SU782649649A priority patent/SU1158031A3/ru

1978-08-04 Priority to AU38666/78A priority patent/AU520916B2/en

1978-08-04 Priority to US05/931,242 priority patent/US4224179A/en

1981-07-15 Publication of CH624011A5 publication Critical patent/CH624011A5/fr

Links

239000002502 liposome Substances 0.000 claims description 74
239000000243 solution Substances 0.000 claims description 55
239000007788 liquid Substances 0.000 claims description 47
238000000034 method Methods 0.000 claims description 44
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 32
150000002632 lipids Chemical class 0.000 claims description 25
239000002904 solvent Substances 0.000 claims description 21
239000007864 aqueous solution Substances 0.000 claims description 19
239000008346 aqueous phase Substances 0.000 claims description 18
150000001875 compounds Chemical class 0.000 claims description 18
239000011780 sodium chloride Substances 0.000 claims description 16
239000002243 precursor Substances 0.000 claims description 14
230000008569 process Effects 0.000 claims description 14
239000004094 surface-active agent Substances 0.000 claims description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
239000000203 mixture Substances 0.000 claims description 12
239000000839 emulsion Substances 0.000 claims description 11
238000001704 evaporation Methods 0.000 claims description 11
239000012071 phase Substances 0.000 claims description 11
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
230000008020 evaporation Effects 0.000 claims description 10
-1 sphin-gomyelin Chemical compound 0.000 claims description 10
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 description 7
239000003814 drug Substances 0.000 claims description 7
229940067606 lecithin Drugs 0.000 claims description 7
239000000787 lecithin Substances 0.000 claims description 7
235000010445 lecithin Nutrition 0.000 claims description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
229940079593 drug Drugs 0.000 claims description 6
JZNWSCPGTDBMEW-UHFFFAOYSA-N Glycerophosphorylethanolamin Natural products NCCOP(O)(=O)OCC(O)CO JZNWSCPGTDBMEW-UHFFFAOYSA-N 0.000 claims description 5
235000012000 cholesterol Nutrition 0.000 claims description 5
239000006185 dispersion Substances 0.000 claims description 5
125000001931 aliphatic group Chemical class 0.000 claims description 4
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 3
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 description 3
ZWZWYGMENQVNFU-UHFFFAOYSA-N Glycerophosphorylserin Natural products OC(=O)C(N)COP(O)(=O)OCC(O)CO ZWZWYGMENQVNFU-UHFFFAOYSA-N 0.000 claims description 3
ZGSPNIOCEDOHGS-UHFFFAOYSA-L disodium [3-[2,3-di(octadeca-9,12-dienoyloxy)propoxy-oxidophosphoryl]oxy-2-hydroxypropyl] 2,3-di(octadeca-9,12-dienoyloxy)propyl phosphate Chemical compound [Na+].[Na+].CCCCCC=CCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCC=CCCCCC)COP([O-])(=O)OCC(O)COP([O-])(=O)OCC(OC(=O)CCCCCCCC=CCC=CCCCCC)COC(=O)CCCCCCCC=CCC=CCCCCC ZGSPNIOCEDOHGS-UHFFFAOYSA-L 0.000 claims description 3
230000000694 effects Effects 0.000 claims description 3
229930195733 hydrocarbon Natural products 0.000 claims description 3
150000002430 hydrocarbons Chemical class 0.000 claims description 3
230000002209 hydrophobic effect Effects 0.000 claims description 3
150000008104 phosphatidylethanolamines Chemical class 0.000 claims description 3
150000003905 phosphatidylinositols Chemical class 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
ASWBNKHCZGQVJV-UHFFFAOYSA-N (3-hexadecanoyloxy-2-hydroxypropyl) 2-(trimethylazaniumyl)ethyl phosphate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(O)COP([O-])(=O)OCC[N+](C)(C)C ASWBNKHCZGQVJV-UHFFFAOYSA-N 0.000 claims description 2
108090000790 Enzymes Proteins 0.000 claims description 2
102000004190 Enzymes Human genes 0.000 claims description 2
REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 claims description 2
CWRILEGKIAOYKP-SSDOTTSWSA-M [(2r)-3-acetyloxy-2-hydroxypropyl] 2-aminoethyl phosphate Chemical compound CC(=O)OC[C@@H](O)COP([O-])(=O)OCCN CWRILEGKIAOYKP-SSDOTTSWSA-M 0.000 claims description 2
229930183167 cerebroside Natural products 0.000 claims description 2
150000001784 cerebrosides Chemical class 0.000 claims description 2
239000002738 chelating agent Substances 0.000 claims description 2
GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims description 2
239000000975 dye Substances 0.000 claims description 2
239000000796 flavoring agent Substances 0.000 claims description 2
235000019634 flavors Nutrition 0.000 claims description 2
239000002304 perfume Substances 0.000 claims description 2
150000003839 salts Chemical class 0.000 claims description 2
229960001295 tocopherol Drugs 0.000 claims description 2
229930003799 tocopherol Natural products 0.000 claims description 2
235000010384 tocopherol Nutrition 0.000 claims description 2
239000011732 tocopherol Substances 0.000 claims description 2
GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 claims description 2
150000003904 phospholipids Chemical class 0.000 claims 2
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 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 claims 1
150000001555 benzenes Chemical class 0.000 claims 1
229910052500 inorganic mineral Inorganic materials 0.000 claims 1
239000011707 mineral Substances 0.000 claims 1
229920001184 polypeptide Polymers 0.000 claims 1
102000004196 processed proteins & peptides Human genes 0.000 claims 1
108090000765 processed proteins & peptides Proteins 0.000 claims 1
239000010410 layer Substances 0.000 description 13
239000000126 substance Substances 0.000 description 10
239000000725 suspension Substances 0.000 description 9
230000015572 biosynthetic process Effects 0.000 description 7
238000004519 manufacturing process Methods 0.000 description 7
239000003960 organic solvent Substances 0.000 description 7
108010073178 Glucan 1,4-alpha-Glucosidase Proteins 0.000 description 6
230000009471 action Effects 0.000 description 6
239000013543 active substance Substances 0.000 description 6
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 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
238000005119 centrifugation Methods 0.000 description 5
238000005538 encapsulation Methods 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
239000008363 phosphate buffer Substances 0.000 description 5
238000000926 separation method Methods 0.000 description 5
238000003756 stirring Methods 0.000 description 5
238000009210 therapy by ultrasound Methods 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
RJURFGZVJUQBHK-UHFFFAOYSA-N actinomycin D Natural products CC1OC(=O)C(C(C)C)N(C)C(=O)CN(C)C(=O)C2CCCN2C(=O)C(C(C)C)NC(=O)C1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)NC4C(=O)NC(C(N5CCCC5C(=O)N(C)CC(=O)N(C)C(C(C)C)C(=O)OC4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-UHFFFAOYSA-N 0.000 description 4
229940107161 cholesterol Drugs 0.000 description 4
239000003599 detergent Substances 0.000 description 4
125000001165 hydrophobic group Chemical group 0.000 description 4
239000002609 medium Substances 0.000 description 4
238000000746 purification Methods 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
102000004877 Insulin Human genes 0.000 description 3
108090001061 Insulin Proteins 0.000 description 3
229920005654 Sephadex Polymers 0.000 description 3
239000012507 Sephadex™ Substances 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
239000012736 aqueous medium Substances 0.000 description 3
230000008901 benefit Effects 0.000 description 3
229940088623 biologically active substance Drugs 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
239000008241 heterogeneous mixture Substances 0.000 description 3
229940125396 insulin Drugs 0.000 description 3
230000016507 interphase Effects 0.000 description 3
239000012528 membrane Substances 0.000 description 3
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
108010092160 Dactinomycin Proteins 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
RJURFGZVJUQBHK-IIXSONLDSA-N actinomycin D Chemical compound C[C@H]1OC(=O)[C@H](C(C)C)N(C)C(=O)CN(C)C(=O)[C@@H]2CCCN2C(=O)[C@@H](C(C)C)NC(=O)[C@H]1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)N[C@@H]4C(=O)N[C@@H](C(N5CCC[C@H]5C(=O)N(C)CC(=O)N(C)[C@@H](C(C)C)C(=O)O[C@@H]4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-IIXSONLDSA-N 0.000 description 2
OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical compound NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 description 2
229960000640 dactinomycin Drugs 0.000 description 2
230000008030 elimination Effects 0.000 description 2
238000003379 elimination reaction Methods 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
239000000499 gel Substances 0.000 description 2
238000005227 gel permeation chromatography Methods 0.000 description 2
NGAZZOYFWWSOGK-UHFFFAOYSA-N heptan-3-one Chemical compound CCCCC(=O)CC NGAZZOYFWWSOGK-UHFFFAOYSA-N 0.000 description 2
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
210000000056 organ Anatomy 0.000 description 2
SSZBUIDZHHWXNJ-UHFFFAOYSA-N palmityl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCCCCCCCCCCCCCCC SSZBUIDZHHWXNJ-UHFFFAOYSA-N 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
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
238000011084 recovery Methods 0.000 description 2
LJRDOKAZOAKLDU-UDXJMMFXSA-N (2s,3s,4r,5r,6r)-5-amino-2-(aminomethyl)-6-[(2r,3s,4r,5s)-5-[(1r,2r,3s,5r,6s)-3,5-diamino-2-[(2s,3r,4r,5s,6r)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-hydroxycyclohexyl]oxy-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxyoxane-3,4-diol;sulfuric ac Chemical compound OS(O)(=O)=O.N[C@@H]1[C@@H](O)[C@H](O)[C@H](CN)O[C@@H]1O[C@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](N)C[C@@H](N)[C@@H]2O)O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)N)O[C@@H]1CO LJRDOKAZOAKLDU-UDXJMMFXSA-N 0.000 description 1
FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 1
ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
FLPJVCMIKUWSDR-UHFFFAOYSA-N 2-(4-formylphenoxy)acetamide Chemical compound NC(=O)COC1=CC=C(C=O)C=C1 FLPJVCMIKUWSDR-UHFFFAOYSA-N 0.000 description 1
RZRILSWMGXWSJY-UHFFFAOYSA-N 2-[bis(2-hydroxyethyl)amino]ethanol;sulfuric acid Chemical compound OS(O)(=O)=O.OCCN(CCO)CCO RZRILSWMGXWSJY-UHFFFAOYSA-N 0.000 description 1
HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 1
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
ZXEFWPPGZZMHBY-UHFFFAOYSA-N C(C)(=O)OCCCC.C(C)(C)OC(C)C Chemical compound C(C)(=O)OCCCC.C(C)(C)OC(C)C ZXEFWPPGZZMHBY-UHFFFAOYSA-N 0.000 description 1
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108010047294 Lamins Proteins 0.000 description 1
239000004166 Lanolin Substances 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
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102000004142 Trypsin Human genes 0.000 description 1
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125000000217 alkyl group Chemical group 0.000 description 1
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125000000129 anionic group Chemical group 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
UREBDLICKHMUKA-DVTGEIKXSA-N betamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-DVTGEIKXSA-N 0.000 description 1
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239000008366 buffered solution Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
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229940074979 cetyl palmitate Drugs 0.000 description 1
230000008859 change Effects 0.000 description 1
OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
229960001231 choline Drugs 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000002537 cosmetic Substances 0.000 description 1
229940104302 cytosine Drugs 0.000 description 1
230000006378 damage Effects 0.000 description 1
230000007547 defect Effects 0.000 description 1
238000000502 dialysis Methods 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
229910000397 disodium phosphate Inorganic materials 0.000 description 1
235000019800 disodium phosphate Nutrition 0.000 description 1
239000002612 dispersion medium Substances 0.000 description 1
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229940043264 dodecyl sulfate Drugs 0.000 description 1
JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
239000003480 eluent Substances 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
235000013305 food Nutrition 0.000 description 1
235000011389 fruit/vegetable juice Nutrition 0.000 description 1
239000007789 gas Substances 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
125000005456 glyceride group Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
PXDJXZJSCPSGGI-UHFFFAOYSA-N hexadecanoic acid hexadecyl ester Natural products CCCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCC PXDJXZJSCPSGGI-UHFFFAOYSA-N 0.000 description 1
230000000968 intestinal effect Effects 0.000 description 1
239000000644 isotonic solution Substances 0.000 description 1
210000005053 lamin Anatomy 0.000 description 1
229940039717 lanolin Drugs 0.000 description 1
235000019388 lanolin Nutrition 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 1
YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
239000002245 particle Substances 0.000 description 1
229960001639 penicillamine Drugs 0.000 description 1
230000035699 permeability Effects 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229940068065 phytosterols Drugs 0.000 description 1
229920000058 polyacrylate Polymers 0.000 description 1
229920000151 polyglycol Polymers 0.000 description 1
239000010695 polyglycol Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
229940090181 propyl acetate Drugs 0.000 description 1
238000011403 purification operation Methods 0.000 description 1
239000005297 pyrex Substances 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
WBHHMMIMDMUBKC-QJWNTBNXSA-M ricinoleate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC([O-])=O WBHHMMIMDMUBKC-QJWNTBNXSA-M 0.000 description 1
229940066675 ricinoleate Drugs 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000002356 single layer Substances 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
150000003432 sterols Chemical class 0.000 description 1
235000003702 sterols Nutrition 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
230000008685 targeting Effects 0.000 description 1
239000004753 textile Substances 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
229940080117 triethanolamine sulfate Drugs 0.000 description 1
239000012588 trypsin Substances 0.000 description 1
238000002604 ultrasonography Methods 0.000 description 1
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
239000003021 water soluble solvent Substances 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/127—Synthetic bilayered vehicles, e.g. liposomes or liposomes with cholesterol as the only non-phosphatidyl surfactant
- A61K9/1277—Preparation processes; Proliposomes
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
- Y10S516/924—Significant dispersive or manipulative operation or step in making or stabilizing colloid system
- Y10S516/929—Specified combination of agitation steps, e.g. mixing to make subcombination composition followed by homogenization

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)
Manufacturing Of Micro-Capsules (AREA)
Medicinal Preparation (AREA)

CH961677A 1977-08-05 1977-08-05 CH624011A5 (is)

Priority Applications (20)

Application Number	Priority Date	Filing Date	Title
CH961677A CH624011A5 (is)	1977-08-05	1977-08-05
IL55154A IL55154A (en)	1977-08-05	1978-07-17	Process for the preparation of liposomes in aqueous solution
IE1574/78A IE47067B1 (en)	1977-08-05	1978-08-02	Process for the preparation of liposomes in aqueous solution
GB7832003A GB2001929B (en)	1977-08-05	1978-08-02	Process for the preparation of liposomes in aqueous solution
JP9372978A JPS5441279A (en)	1977-08-05	1978-08-02	Manufacture of liposome solution or suspension in aqueous medium
HU78BA3681A HU179672B (en)	1977-08-05	1978-08-02	Process for producing aequous solution of liposomes
SE7808356A SE433169B (sv)	1977-08-05	1978-08-03	Forfarande for framstellning av vattenlosningar eller suspensioner av liposomer
ZA00784407A ZA784407B (en)	1977-08-05	1978-08-03	Process for the preparation of liposomes in aqueous solution
DE19782834307 DE2834307A1 (de)	1977-08-05	1978-08-03	Verfahren zur herstellung von liposomen in waessriger loesung
FR7822985A FR2399242A1 (fr)	1977-08-05	1978-08-03	Procede de preparation de liposomes en solution aqueuse
LU80071A LU80071A1 (fr)	1977-08-05	1978-08-03	Procede de preparation de liposomes en solution aqueuse
ES472326A ES472326A1 (es)	1977-08-05	1978-08-03	Procedimiento para la preparacion de liposomas en solucion o suspension acuosa
NL787808167A NL7808167A (nl)	1977-08-05	1978-08-03	Werkwijze voor het bereiden van oplossingen of suspen- sies van liposomen in waterige media.
IT26441/78A IT1097928B (it)	1977-08-05	1978-08-03	Procedimento di preparazione di liposomi in soluzione acquosa
DK344478A DK155036C (da)	1977-08-05	1978-08-03	Fremgangsmaade til fremstilling af oploesninger eller suspensioner af liposomer i vandige medier.
CA308,715A CA1098410A (en)	1977-08-05	1978-08-03	Process for the preparation of liposomes in aqueous solution
BE78189678A BE869490A (fr)	1977-08-05	1978-08-03	Procede de preparation de liposomes en solution aqueuse
SU782649649A SU1158031A3 (ru)	1977-08-05	1978-08-04	Способ получени липосом
AU38666/78A AU520916B2 (en)	1977-08-05	1978-08-04	Preparing liposomes
US05/931,242 US4224179A (en)	1977-08-05	1978-08-04	Process for the preparation of liposomes in aqueous solution

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH961677A CH624011A5 (is)	1977-08-05	1977-08-05

Publications (1)

Publication Number	Publication Date
CH624011A5 true CH624011A5 (is)	1981-07-15

Family

ID=4353843

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH961677A CH624011A5 (is)	1977-08-05	1977-08-05

Country Status (20)

Country	Link
US (1)	US4224179A (is)
JP (1)	JPS5441279A (is)
AU (1)	AU520916B2 (is)
BE (1)	BE869490A (is)
CA (1)	CA1098410A (is)
CH (1)	CH624011A5 (is)
DE (1)	DE2834307A1 (is)
DK (1)	DK155036C (is)
ES (1)	ES472326A1 (is)
FR (1)	FR2399242A1 (is)
GB (1)	GB2001929B (is)
HU (1)	HU179672B (is)
IE (1)	IE47067B1 (is)
IL (1)	IL55154A (is)
IT (1)	IT1097928B (is)
LU (1)	LU80071A1 (is)
NL (1)	NL7808167A (is)
SE (1)	SE433169B (is)
SU (1)	SU1158031A3 (is)
ZA (1)	ZA784407B (is)

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1977
- 1977-08-05 CH CH961677A patent/CH624011A5/fr not_active IP Right Cessation
1978
- 1978-07-17 IL IL55154A patent/IL55154A/xx unknown
- 1978-08-02 HU HU78BA3681A patent/HU179672B/hu unknown
- 1978-08-02 IE IE1574/78A patent/IE47067B1/en unknown
- 1978-08-02 JP JP9372978A patent/JPS5441279A/ja active Granted
- 1978-08-02 GB GB7832003A patent/GB2001929B/en not_active Expired
- 1978-08-03 ES ES472326A patent/ES472326A1/es not_active Expired
- 1978-08-03 DE DE19782834307 patent/DE2834307A1/de not_active Withdrawn
- 1978-08-03 NL NL787808167A patent/NL7808167A/xx not_active Application Discontinuation
- 1978-08-03 BE BE78189678A patent/BE869490A/xx not_active IP Right Cessation
- 1978-08-03 FR FR7822985A patent/FR2399242A1/fr active Granted
- 1978-08-03 LU LU80071A patent/LU80071A1/xx unknown
- 1978-08-03 IT IT26441/78A patent/IT1097928B/it active
- 1978-08-03 ZA ZA00784407A patent/ZA784407B/xx unknown
- 1978-08-03 CA CA308,715A patent/CA1098410A/en not_active Expired
- 1978-08-03 DK DK344478A patent/DK155036C/da not_active IP Right Cessation
- 1978-08-03 SE SE7808356A patent/SE433169B/sv not_active IP Right Cessation
- 1978-08-04 AU AU38666/78A patent/AU520916B2/en not_active Expired
- 1978-08-04 US US05/931,242 patent/US4224179A/en not_active Expired - Lifetime
- 1978-08-04 SU SU782649649A patent/SU1158031A3/ru active

Also Published As

Publication number	Publication date
DE2834307A1 (de)	1979-02-15
IE781574L (en)	1979-02-05
SE433169B (sv)	1984-05-14
GB2001929B (en)	1982-07-28
NL7808167A (nl)	1979-02-07
JPS5441279A (en)	1979-04-02
AU520916B2 (en)	1982-03-04
DK155036B (da)	1989-01-30
GB2001929A (en)	1979-02-14
ES472326A1 (es)	1979-02-16
IE47067B1 (en)	1983-12-14
DK155036C (da)	1989-06-26
SU1158031A3 (ru)	1985-05-23
FR2399242B1 (is)	1983-01-07
SE7808356L (sv)	1979-02-06
DK344478A (da)	1979-02-06
CA1098410A (en)	1981-03-31
IL55154A (en)	1981-09-13
IL55154A0 (en)	1978-09-29
BE869490A (fr)	1979-02-05
US4224179A (en)	1980-09-23
JPS6355978B2 (is)	1988-11-07
IT7826441A0 (it)	1978-08-03
IT1097928B (it)	1985-08-31
FR2399242A1 (fr)	1979-03-02
AU3866678A (en)	1980-02-07
ZA784407B (en)	1979-07-25
LU80071A1 (fr)	1979-05-15
HU179672B (en)	1982-11-29

Publication	Publication Date	Title
CH624011A5 (is)	1981-07-15
CA2066617C (en)	1998-04-14	Paucilamellar lipid vesicles using charge-localized, single chain, nonphospholipid surfactants
EP0344040B1 (fr)	1992-07-01	Vecteur particulaire utile notamment pour le transport de molécules à activité biologique et procédé pour sa préparation
EP0004223B1 (fr)	1981-09-09	Procédé de fabrication de capsules lipidiques renfermant un matériau biologiquement actif, produits obtenus par ce procédé ainsi que leur utilisation
US4485054A (en)	1984-11-27	Method of encapsulating biologically active materials in multilamellar lipid vesicles (MLV)
EP0214055B1 (fr)	1989-12-27	Nouveaux surfactants artificiels, leur préparation et les compositions pharmaceutiques qui les contiennent
KR950002146B1 (ko)	1995-03-14	단일 이중층 리포좀의 제조방법
EP0491921B1 (fr)	1996-02-07	Procede de preparation d'une lipoproteine modifiee par incorporation d'une substance active lipophile
EP0422978B1 (fr)	1993-12-22	Procédé de fabrication d'une dispersion aqueuse de vésicules lipidiques et composition à base de la dispersion ainsi obtenue
US20110150953A1 (en)	2011-06-23	Method for producing vesicle, vesicle obtained by the production method, and w/o/w emulsion for producing vesicle
EP0365868B1 (fr)	1992-10-14	Procédé de séparation des glycolipides d'un mélange lipidique et utilisation des fractions obtenues
EP0349429B1 (fr)	1993-02-24	Procédé de préparation de systèmes colloidaux dispersibles de lipides amphiphiles sous forme de liposomes submicroniques
EP0393049B1 (fr)	1993-02-24	Liposomes, leur procede et application comme vecteur de produits
JP2005298407A (ja)	2005-10-27	ポリカチオン修飾リポソームおよびその製造法
KR800001169B1 (ko)	1980-10-20	수용액 중에서의 리포좀의 제조 방법
FR2561101A1 (fr)	1985-09-20	Procede de preparation de liposomes et liposomes ainsi obtenus
KR800001360B1 (ko)	1980-11-17	리포솜의 제조법
WO1995001163A1 (fr)	1995-01-12	Nouvelles preparations pharmaceutiques a base de peptides pour la voie generale
JPH08311086A (ja)	1996-11-26	リン脂質混合物の製造方法
JPH02103A (ja)	1990-01-05	新規リポソーム及びその製造方法
EP0658102A1 (fr)	1995-06-21	Nouvelles preparations pharmaceutiques a base de peptides pour la voie generale
JP2001139460A (ja)	2001-05-22	リポソームの調製方法
WO2004061457A1 (fr)	2004-07-22	Materiau hybride organique-inorganique, procede pour sa preparation
MXPA97004272A (en)	1998-11-09	Seized agents

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Date	Code	Title	Description
1991-04-30	PL	Patent ceased
2024-10-31	PL	Patent ceased