CS227010B2 - Suspensions of Drug- containing Liposomes - Google Patents
Suspensions of Drug- containing Liposomes Download PDFInfo
- Publication number
- CS227010B2 CS227010B2 CS80309A CS30980A CS227010B2 CS 227010 B2 CS227010 B2 CS 227010B2 CS 80309 A CS80309 A CS 80309A CS 30980 A CS30980 A CS 30980A CS 227010 B2 CS227010 B2 CS 227010B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- resins
- suspensions
- liposome
- suspension
- groups
- Prior art date
Links
- 239000002502 liposome Substances 0.000 title claims abstract description 47
- 239000000725 suspension Substances 0.000 title claims abstract description 45
- 239000011347 resin Substances 0.000 claims abstract description 36
- 229920005989 resin Polymers 0.000 claims abstract description 36
- 239000003814 drug Substances 0.000 claims abstract description 18
- 229940079593 drug Drugs 0.000 claims abstract description 15
- 239000002904 solvent Substances 0.000 claims abstract description 5
- 239000011261 inert gas Substances 0.000 claims abstract 3
- 238000000034 method Methods 0.000 claims description 23
- 229920000642 polymer Polymers 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 10
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 4
- 239000003463 adsorbent Substances 0.000 claims description 4
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- 239000000839 emulsion Substances 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- 229920001568 phenolic resin Polymers 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 230000000087 stabilizing effect Effects 0.000 claims description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 150000002500 ions Chemical class 0.000 claims description 3
- 150000002734 metacrylic acid derivatives Chemical class 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 2
- 239000013043 chemical agent Substances 0.000 claims description 2
- DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical group CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 claims description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 2
- 239000000377 silicon dioxide Substances 0.000 claims description 2
- 238000001179 sorption measurement Methods 0.000 claims description 2
- 239000012609 strong anion exchange resin Substances 0.000 claims description 2
- 125000001174 sulfone group Chemical group 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 2
- 239000012610 weak anion exchange resin Substances 0.000 claims description 2
- 239000012608 weak cation exchange resin Substances 0.000 claims description 2
- 230000002051 biphasic effect Effects 0.000 claims 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims 1
- 229920001577 copolymer Polymers 0.000 claims 1
- 125000000524 functional group Chemical group 0.000 claims 1
- 125000003473 lipid group Chemical group 0.000 claims 1
- 229920000620 organic polymer Polymers 0.000 claims 1
- 229920001059 synthetic polymer Polymers 0.000 claims 1
- 238000001914 filtration Methods 0.000 abstract description 4
- 239000003456 ion exchange resin Substances 0.000 abstract description 4
- 229920003303 ion-exchange polymer Polymers 0.000 abstract description 4
- 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 abstract 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 abstract description 2
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 abstract description 2
- 239000002250 absorbent Substances 0.000 abstract description 2
- 230000002745 absorbent Effects 0.000 abstract description 2
- 238000001704 evaporation Methods 0.000 abstract description 2
- 230000008020 evaporation Effects 0.000 abstract description 2
- 229960002949 fluorouracil Drugs 0.000 abstract description 2
- 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 abstract 1
- 125000000129 anionic group Chemical group 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 125000002091 cationic group Chemical group 0.000 abstract 1
- 238000004090 dissolution Methods 0.000 abstract 1
- 229960002918 doxorubicin hydrochloride Drugs 0.000 abstract 1
- 238000004945 emulsification Methods 0.000 abstract 1
- 239000007971 pharmaceutical suspension Substances 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 13
- 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 10
- 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
- 238000004108 freeze drying Methods 0.000 description 8
- 150000002632 lipids Chemical class 0.000 description 7
- 239000000243 solution Substances 0.000 description 6
- 235000012000 cholesterol Nutrition 0.000 description 5
- -1 cholesterol Chemical class 0.000 description 4
- 229960004679 doxorubicin Drugs 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 230000002209 hydrophobic effect Effects 0.000 description 4
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 3
- 229920005654 Sephadex Polymers 0.000 description 3
- 239000012507 Sephadex™ Substances 0.000 description 3
- 229920002684 Sepharose Polymers 0.000 description 3
- 239000008344 egg yolk phospholipid Substances 0.000 description 3
- 239000002808 molecular sieve Substances 0.000 description 3
- 239000008363 phosphate buffer Substances 0.000 description 3
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 3
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 238000000502 dialysis Methods 0.000 description 2
- RNPXCFINMKSQPQ-UHFFFAOYSA-N dicetyl hydrogen phosphate Chemical compound CCCCCCCCCCCCCCCCOP(O)(=O)OCCCCCCCCCCCCCCCC RNPXCFINMKSQPQ-UHFFFAOYSA-N 0.000 description 2
- 229940093541 dicetylphosphate Drugs 0.000 description 2
- 229940116441 divinylbenzene Drugs 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 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 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 238000005411 Van der Waals force Methods 0.000 description 1
- XLLNINGEDIOQGQ-UHFFFAOYSA-N [acetyloxy(hydroxy)phosphoryl] acetate Chemical compound CC(=O)OP(O)(=O)OC(C)=O XLLNINGEDIOQGQ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 239000008366 buffered solution Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000002523 gelfiltration Methods 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000002563 ionic surfactant Substances 0.000 description 1
- DKYWVDODHFEZIM-UHFFFAOYSA-N ketoprofen Chemical compound OC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 DKYWVDODHFEZIM-UHFFFAOYSA-N 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- ASHGTUMKRVIOLH-UHFFFAOYSA-L potassium;sodium;hydrogen phosphate Chemical compound [Na+].[K+].OP([O-])([O-])=O ASHGTUMKRVIOLH-UHFFFAOYSA-L 0.000 description 1
- 239000011541 reaction mixture Substances 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
- 239000010409 thin film Substances 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 238000010626 work up procedure 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 |
|---|---|
| CS227010B2 true CS227010B2 (en) | 1984-04-16 |
Family
ID=11157905
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS80309A CS227010B2 (en) | 1979-01-19 | 1980-01-15 | Suspensions of Drug- containing Liposomes |
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
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