CH648205A5 - Verfahren zum reinigen von liposomensuspensionen. - Google Patents
Verfahren zum reinigen von liposomensuspensionen. Download PDFInfo
- Publication number
- CH648205A5 CH648205A5 CH370/80A CH37080A CH648205A5 CH 648205 A5 CH648205 A5 CH 648205A5 CH 370/80 A CH370/80 A CH 370/80A CH 37080 A CH37080 A CH 37080A CH 648205 A5 CH648205 A5 CH 648205A5
- Authority
- CH
- Switzerland
- Prior art keywords
- resins
- liposomes
- liposome suspensions
- pharmaceutical composition
- liquid
- Prior art date
Links
- 239000002502 liposome Substances 0.000 title claims description 39
- 239000000725 suspension Substances 0.000 title claims description 25
- 238000000034 method Methods 0.000 title claims description 17
- 238000004140 cleaning Methods 0.000 title claims description 6
- 239000011347 resin Substances 0.000 claims description 22
- 229920005989 resin Polymers 0.000 claims description 22
- 238000004108 freeze drying Methods 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 239000003463 adsorbent Substances 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 229920000642 polymer Polymers 0.000 claims description 4
- MWWSFMDVAYGXBV-RUELKSSGSA-N Doxorubicin hydrochloride Chemical compound Cl.O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 MWWSFMDVAYGXBV-RUELKSSGSA-N 0.000 claims description 3
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims description 3
- 229920001577 copolymer Polymers 0.000 claims description 3
- 229960002949 fluorouracil Drugs 0.000 claims description 3
- 150000002500 ions Chemical class 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 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 claims description 2
- 229960002918 doxorubicin hydrochloride Drugs 0.000 claims description 2
- 239000000839 emulsion Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 claims 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims 2
- 238000009833 condensation Methods 0.000 claims 2
- 230000005494 condensation Effects 0.000 claims 2
- 229920006037 cross link polymer Polymers 0.000 claims 2
- 229930195733 hydrocarbon Natural products 0.000 claims 2
- 150000002430 hydrocarbons Chemical class 0.000 claims 2
- 150000002734 metacrylic acid derivatives Chemical class 0.000 claims 2
- 229920000620 organic polymer Polymers 0.000 claims 2
- 229920001568 phenolic resin Polymers 0.000 claims 2
- 150000003839 salts Chemical group 0.000 claims 2
- 229920001059 synthetic polymer Polymers 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 238000007664 blowing Methods 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000011261 inert gas Substances 0.000 claims 1
- DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical group CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 claims 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 1
- 239000012609 strong anion exchange resin Substances 0.000 claims 1
- 125000001174 sulfone group Chemical group 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 claims 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims 1
- 239000012610 weak anion exchange resin Substances 0.000 claims 1
- 239000012608 weak cation exchange resin Substances 0.000 claims 1
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 8
- 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 description 8
- 230000002209 hydrophobic effect Effects 0.000 description 5
- 150000002632 lipids Chemical class 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 235000012000 cholesterol Nutrition 0.000 description 4
- 229960004679 doxorubicin Drugs 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RNPXCFINMKSQPQ-UHFFFAOYSA-N dicetyl hydrogen phosphate Chemical compound CCCCCCCCCCCCCCCCOP(O)(=O)OCCCCCCCCCCCCCCCC RNPXCFINMKSQPQ-UHFFFAOYSA-N 0.000 description 3
- 229940093541 dicetylphosphate Drugs 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000003456 ion exchange resin Substances 0.000 description 3
- 229920003303 ion-exchange polymer Polymers 0.000 description 3
- 239000008363 phosphate buffer Substances 0.000 description 3
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 3
- 238000005199 ultracentrifugation Methods 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000008344 egg yolk phospholipid Substances 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical group [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- ZXHDFKAHCABVAF-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;methyl 2-methylprop-2-enoate Chemical compound COC(=O)C(C)=C.C=CC1=CC=CC=C1C=C ZXHDFKAHCABVAF-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- PZNPLUBHRSSFHT-RRHRGVEJSA-N 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCCC(=O)O[C@@H](COP([O-])(=O)OCC[N+](C)(C)C)COC(=O)CCCCCCCCCCCCCCC PZNPLUBHRSSFHT-RRHRGVEJSA-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
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 229920002684 Sepharose Polymers 0.000 description 1
- 238000005411 Van der Waals force Methods 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 239000008366 buffered solution Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- -1 cholesterol Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- 229940116441 divinylbenzene Drugs 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000013003 healing agent Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229920013730 reactive polymer Polymers 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 239000008347 soybean phospholipid Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/127—Synthetic bilayered vehicles, e.g. liposomes or liposomes with cholesterol as the only non-phosphatidyl surfactant
- A61K9/1277—Preparation processes; Proliposomes
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)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT19434/79A IT1110989B (it) | 1979-01-19 | 1979-01-19 | Forme farmaceutiche costitutite da liposomi e procedimenti relativi |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH648205A5 true CH648205A5 (de) | 1985-03-15 |
Family
ID=11157905
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH370/80A CH648205A5 (de) | 1979-01-19 | 1980-01-17 | Verfahren zum reinigen von liposomensuspensionen. |
Country Status (21)
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| FR2521565B1 (fr) * | 1982-02-17 | 1985-07-05 | Dior Sa Parfums Christian | Melange pulverulent de constituants lipidiques et de constituants hydrophobes, procede pour le preparer, phases lamellaires lipidiques hydratees et procede de fabrication, compositions pharmaceutiques ou cosmetiques comportant des phases lamellaires lipidiques hydratees |
| FR2553002B1 (fr) * | 1983-10-06 | 1992-03-27 | Centre Nat Rech Scient | Procede perfectionne d'obtention de liposomes unilamellaires de diametres eleves, leur application pharmacologique pour l'encapsulage d'un principe actif en vue de son administration extemporanee et dispositif correspondant |
| CA1270198C (en) * | 1984-08-08 | 1990-06-12 | Marcel B Bally | ENCAPSULATION OF ANTINEOPLASTIC AGENTS IN LIPOSONES |
| US5736155A (en) * | 1984-08-08 | 1998-04-07 | The Liposome Company, Inc. | Encapsulation of antineoplastic agents in liposomes |
| US4755388A (en) * | 1984-11-09 | 1988-07-05 | The Regents Of The University Of California | Liposome-encapsulated 5-fluoropyrimidines and methods for their use |
| IL79114A (en) * | 1985-08-07 | 1990-09-17 | Allergan Pharma | Method and composition for making liposomes |
| US6406713B1 (en) * | 1987-03-05 | 2002-06-18 | The Liposome Company, Inc. | Methods of preparing low-toxicity drug-lipid complexes |
| EP0555229B1 (en) * | 1990-07-31 | 1996-06-05 | The Liposome Company, Inc. | Accumulation of amino acids and peptides into liposomes |
| DE4107153A1 (de) * | 1991-03-06 | 1992-09-10 | Gregor Cevc | Praeparat zur wirkstoffapplikation in kleinsttroepfchenform |
| DE4107152C2 (de) * | 1991-03-06 | 1994-03-24 | Gregor Cevc | Präparate zur nichtinvasiven Verabreichung von Antidiabetica |
| JPH04127874U (ja) * | 1991-05-13 | 1992-11-20 | 株式会社新潟鐵工所 | コンクリートポンプ用輸送管の圧送音緩和装置 |
| JPH04134673U (ja) * | 1991-06-07 | 1992-12-15 | 株式会社フジタ | コンクリート圧送圧変動防止装置 |
| AU676906B2 (en) * | 1993-04-02 | 1997-03-27 | Transave, Inc. | Method of producing liposomes |
| IT1270678B (it) * | 1994-10-20 | 1997-05-07 | Bayer Ag | Liposomi al chetoprofen |
| DE19639811A1 (de) * | 1996-09-27 | 1998-04-02 | Artur Herzog Dr Mesmer | Verwendung einer Liposomenlösung zur Verstärkung der Wirksamkeit und/oder Verminderung der Toxizität von Arzneimitteln |
| JP4283355B2 (ja) * | 1997-11-10 | 2009-06-24 | 久光製薬株式会社 | 薬剤用徐放化剤及びそれを含有した徐放性医薬組成物 |
| CN1278738A (zh) * | 1997-11-10 | 2001-01-03 | 久光制药株式会社 | 药剂用缓释和含有该缓释剂的缓释性药物组合物 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2249552A1 (de) * | 1971-10-12 | 1973-05-30 | Inchema S A | Verfahren zur inkapsulation von insbesondere wasserloeslichen verbindungen |
| JPS5126213A (ja) * | 1974-08-21 | 1976-03-04 | Tanabe Seiyaku Co | Johoseibiryushiseizaino seiho |
| US4131815A (en) * | 1977-02-23 | 1978-12-26 | Oceanography International Corporation | Solid piezoelectric sand detection probes |
| GB1575343A (en) * | 1977-05-10 | 1980-09-17 | Ici Ltd | Method for preparing liposome compositions containing biologically active compounds |
| NL7809709A (nl) * | 1977-09-30 | 1979-04-03 | Farmaceutici Italia | Werkwijze voor het bereiden van injecteerbare liposomen |
-
1979
- 1979-01-19 IT IT19434/79A patent/IT1110989B/it active
-
1980
- 1980-01-09 NL NL8000139A patent/NL8000139A/nl not_active Application Discontinuation
- 1980-01-14 YU YU81/80A patent/YU44003B/xx unknown
- 1980-01-14 JP JP219280A patent/JPS55100313A/ja active Granted
- 1980-01-14 AU AU54581/80A patent/AU536823B2/en not_active Ceased
- 1980-01-14 IL IL59120A patent/IL59120A/xx unknown
- 1980-01-15 FR FR808000801A patent/FR2446635B1/fr not_active Expired
- 1980-01-15 AT AT0019380A patent/AT370623B/de not_active IP Right Cessation
- 1980-01-15 CA CA000343663A patent/CA1148470A/en not_active Expired
- 1980-01-15 CS CS80309A patent/CS227010B2/cs unknown
- 1980-01-16 IE IE91/80A patent/IE49141B1/en unknown
- 1980-01-16 ZA ZA00800269A patent/ZA80269B/xx unknown
- 1980-01-17 GB GB8001545A patent/GB2041871B/en not_active Expired
- 1980-01-17 SU SU802869298A patent/SU1367839A3/ru active
- 1980-01-17 CH CH370/80A patent/CH648205A5/de not_active IP Right Cessation
- 1980-01-17 HU HU8097A patent/HU184714B/hu not_active IP Right Cessation
- 1980-01-17 FI FI800151A patent/FI70672C/fi not_active IP Right Cessation
- 1980-01-18 SE SE8000443A patent/SE445171B/sv not_active IP Right Cessation
- 1980-01-18 DE DE19803001842 patent/DE3001842A1/de active Granted
- 1980-01-18 BE BE0/199021A patent/BE881225A/fr not_active IP Right Cessation
- 1980-01-18 DK DK022380A patent/DK157060C/da not_active IP Right Cessation
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PFA | Name/firm changed |
Owner name: FARMITALIA CARLO ERBA S.R.L. |
|
| PL | Patent ceased | ||
| PL | Patent ceased |