ZA200201543B - Process for encapsulating active materials by coacervation of polymers in non-chlorinated organic solvent. - Google Patents
Process for encapsulating active materials by coacervation of polymers in non-chlorinated organic solvent. Download PDFInfo
- Publication number
- ZA200201543B ZA200201543B ZA200201543A ZA200201543A ZA200201543B ZA 200201543 B ZA200201543 B ZA 200201543B ZA 200201543 A ZA200201543 A ZA 200201543A ZA 200201543 A ZA200201543 A ZA 200201543A ZA 200201543 B ZA200201543 B ZA 200201543B
- Authority
- ZA
- South Africa
- Prior art keywords
- polymer
- solvent
- curing agent
- coacervation
- active principle
- Prior art date
Links
- 229920000642 polymer Polymers 0.000 title claims description 89
- 238000000034 method Methods 0.000 title claims description 50
- 238000005354 coacervation Methods 0.000 title claims description 37
- 230000008569 process Effects 0.000 title claims description 31
- 239000003960 organic solvent Substances 0.000 title claims description 9
- 239000011149 active material Substances 0.000 title description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 102
- 239000002904 solvent Substances 0.000 claims description 102
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 64
- 239000003795 chemical substances by application Substances 0.000 claims description 61
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 42
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 36
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 35
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 33
- 239000004005 microsphere Substances 0.000 claims description 27
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 23
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 23
- 229960004063 propylene glycol Drugs 0.000 claims description 23
- 235000013772 propylene glycol Nutrition 0.000 claims description 23
- 239000004094 surface-active agent Substances 0.000 claims description 20
- 229920000136 polysorbate Polymers 0.000 claims description 19
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 14
- 238000003756 stirring Methods 0.000 claims description 12
- 230000015572 biosynthetic process Effects 0.000 claims description 11
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 10
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical group CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 10
- 229920002988 biodegradable polymer Polymers 0.000 claims description 9
- 239000004621 biodegradable polymer Substances 0.000 claims description 9
- 239000002245 particle Substances 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 claims description 6
- 239000006185 dispersion Substances 0.000 claims description 5
- 239000004310 lactic acid Substances 0.000 claims description 5
- 235000014655 lactic acid Nutrition 0.000 claims description 5
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 5
- 125000003158 alcohol group Chemical group 0.000 claims description 4
- -1 sorbitan ester Chemical class 0.000 claims description 4
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 3
- 230000008021 deposition Effects 0.000 claims description 3
- 238000004807 desolvation Methods 0.000 claims description 3
- 230000009477 glass transition Effects 0.000 claims description 3
- 238000002604 ultrasonography Methods 0.000 claims description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 239000007888 film coating Substances 0.000 claims description 2
- 238000009501 film coating Methods 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 229960004592 isopropanol Drugs 0.000 description 29
- 239000011859 microparticle Substances 0.000 description 17
- 239000000243 solution Substances 0.000 description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 238000007792 addition Methods 0.000 description 10
- 238000005538 encapsulation Methods 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- RKDVKSZUMVYZHH-UHFFFAOYSA-N 1,4-dioxane-2,5-dione Chemical compound O=C1COC(=O)CO1 RKDVKSZUMVYZHH-UHFFFAOYSA-N 0.000 description 8
- 238000010907 mechanical stirring Methods 0.000 description 8
- 238000009792 diffusion process Methods 0.000 description 7
- 238000003760 magnetic stirring Methods 0.000 description 7
- 238000004220 aggregation Methods 0.000 description 6
- 230000002829 reductive effect Effects 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 230000002776 aggregation Effects 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 239000002609 medium Substances 0.000 description 5
- 239000008385 outer phase Substances 0.000 description 5
- 238000013268 sustained release Methods 0.000 description 5
- 239000012730 sustained-release form Substances 0.000 description 5
- JJTUDXZGHPGLLC-IMJSIDKUSA-N 4511-42-6 Chemical compound C[C@@H]1OC(=O)[C@H](C)OC1=O JJTUDXZGHPGLLC-IMJSIDKUSA-N 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 229960005150 glycerol Drugs 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- ZFMQKOWCDKKBIF-UHFFFAOYSA-N bis(3,5-difluorophenyl)phosphane Chemical compound FC1=CC(F)=CC(PC=2C=C(F)C=C(F)C=2)=C1 ZFMQKOWCDKKBIF-UHFFFAOYSA-N 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 231100000053 low toxicity Toxicity 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 239000003570 air Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 229960002949 fluorouracil Drugs 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000007970 homogeneous dispersion Substances 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 230000000670 limiting effect Effects 0.000 description 2
- 238000000399 optical microscopy Methods 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229920000747 poly(lactic acid) Polymers 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000001069 triethyl citrate Substances 0.000 description 2
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 2
- 235000013769 triethyl citrate Nutrition 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
- OXOWWPXTTOCKKU-UHFFFAOYSA-N 2-propoxybenzoic acid Chemical compound CCCOC1=CC=CC=C1C(O)=O OXOWWPXTTOCKKU-UHFFFAOYSA-N 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 229920001661 Chitosan Polymers 0.000 description 1
- 108010035532 Collagen Proteins 0.000 description 1
- 102000008186 Collagen Human genes 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 1
- CTKXFMQHOOWWEB-UHFFFAOYSA-N Ethylene oxide/propylene oxide copolymer Chemical compound CCCOC(C)COCCO CTKXFMQHOOWWEB-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- SHBUUTHKGIVMJT-UHFFFAOYSA-N Hydroxystearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OO SHBUUTHKGIVMJT-UHFFFAOYSA-N 0.000 description 1
- 206010022528 Interactions Diseases 0.000 description 1
- 206010029350 Neurotoxicity Diseases 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 229920001244 Poly(D,L-lactide) Polymers 0.000 description 1
- 229920002732 Polyanhydride Polymers 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 229920001710 Polyorthoester Polymers 0.000 description 1
- 241000985694 Polypodiopsida Species 0.000 description 1
- NWGKJDSIEKMTRX-AAZCQSIUSA-N Sorbitan monooleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O NWGKJDSIEKMTRX-AAZCQSIUSA-N 0.000 description 1
- 206010044221 Toxic encephalopathy Diseases 0.000 description 1
- 239000012080 ambient air Substances 0.000 description 1
- 239000003080 antimitotic agent Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000002238 attenuated effect Effects 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 235000013405 beer Nutrition 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 229940098773 bovine serum albumin Drugs 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 229920001436 collagen Polymers 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 229940072106 hydroxystearate Drugs 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000011866 long-term treatment Methods 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004001 molecular interaction Effects 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 238000002663 nebulization Methods 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 230000007135 neurotoxicity Effects 0.000 description 1
- 231100000228 neurotoxicity Toxicity 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 238000010587 phase diagram Methods 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 229920001983 poloxamer Polymers 0.000 description 1
- 229920001993 poloxamer 188 Polymers 0.000 description 1
- 229940044519 poloxamer 188 Drugs 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 231100000683 possible toxicity Toxicity 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 229940032159 propylene carbonate Drugs 0.000 description 1
- 238000001046 rapid expansion of supercritical solution Methods 0.000 description 1
- 238000012958 reprocessing Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000006104 solid solution Substances 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229950004959 sorbitan oleate Drugs 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000005563 spheronization Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
- B01J13/02—Making microcapsules or microballoons
- B01J13/06—Making microcapsules or microballoons by phase separation
- B01J13/08—Simple coacervation, i.e. addition of highly hydrophilic material
-
- 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
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1629—Organic macromolecular compounds
- A61K9/1641—Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, poloxamers
- A61K9/1647—Polyesters, e.g. poly(lactide-co-glycolide)
-
- 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
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1682—Processes
- A61K9/1694—Processes resulting in granules or microspheres of the matrix type containing more than 5% of excipient
-
- 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
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4841—Filling excipients; Inactive ingredients
- A61K9/4866—Organic macromolecular compounds
-
- 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
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
- A61K9/5089—Processes
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9910854A FR2797784B1 (fr) | 1999-08-27 | 1999-08-27 | Procede d'encapsulation de matieres actives par coacervation de polymeres en solvant organique non-chlore |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200201543B true ZA200201543B (en) | 2002-11-27 |
Family
ID=9549384
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200201543A ZA200201543B (en) | 1999-08-27 | 2002-02-26 | Process for encapsulating active materials by coacervation of polymers in non-chlorinated organic solvent. |
Country Status (18)
| Country | Link |
|---|---|
| EP (1) | EP1216091B9 (de) |
| JP (1) | JP5217070B2 (de) |
| KR (1) | KR100661093B1 (de) |
| CN (1) | CN1317064C (de) |
| AT (1) | ATE261338T1 (de) |
| AU (1) | AU776959B2 (de) |
| CA (1) | CA2382697C (de) |
| DE (1) | DE60008894T2 (de) |
| DK (1) | DK1216091T3 (de) |
| ES (1) | ES2215718T3 (de) |
| FR (1) | FR2797784B1 (de) |
| HU (1) | HU228747B1 (de) |
| IL (2) | IL148316A0 (de) |
| MX (1) | MXPA02002250A (de) |
| NO (1) | NO322106B1 (de) |
| PT (1) | PT1216091E (de) |
| WO (1) | WO2001015799A1 (de) |
| ZA (1) | ZA200201543B (de) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1404516A2 (de) | 2000-12-13 | 2004-04-07 | Purdue Research Foundation | Mikroverkapselung von arzneistoffen durch lösungsmittelaustausch |
| US6767637B2 (en) | 2000-12-13 | 2004-07-27 | Purdue Research Foundation | Microencapsulation using ultrasonic atomizers |
| EP1343480B2 (de) † | 2000-12-21 | 2016-02-17 | Alrise Biosystems GmbH | Verfahren umfassend einen induzierten phasenübergang zur herstellung von hydrophobe wirkstoffe enthaltenden mikropartikeln |
| FR2824756B1 (fr) * | 2001-05-16 | 2005-07-08 | Mainelab | Microcapsules a base de proteines vegetales |
| FR2832312B1 (fr) * | 2001-11-21 | 2004-01-16 | Inst Nat Sante Rech Med | Procede de preparation de microparticules sans solvant toxique, microparticules obtenues selon ce procede, utilisations et compositions pharmaceutiques |
| US9480631B2 (en) | 2008-11-10 | 2016-11-01 | Colgate-Palmolive Company | Shelf stable capsules |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4389330A (en) * | 1980-10-06 | 1983-06-21 | Stolle Research And Development Corporation | Microencapsulation process |
| JPS5966425A (ja) * | 1982-10-08 | 1984-04-14 | Mitsui Toatsu Chem Inc | 生体分解性重合体を用いた微小粒子の製造方法 |
| JPS62213840A (ja) * | 1986-03-14 | 1987-09-19 | Snow Brand Milk Prod Co Ltd | マイクロカプセルの乾燥方法 |
| JPS6365945A (ja) * | 1986-09-05 | 1988-03-24 | Eisai Co Ltd | マイクロカプセルの製造方法 |
| US5234520A (en) * | 1987-03-20 | 1993-08-10 | Morgan Adhesives Co. | Method of making an adhesive construction |
| JP2670680B2 (ja) * | 1988-02-24 | 1997-10-29 | 株式会社ビーエムジー | 生理活性物質含有ポリ乳酸系微小球およびその製造法 |
| US5324520A (en) * | 1988-12-19 | 1994-06-28 | Vipont Pharmaceutical, Inc. | Intragingival delivery systems for treatment of periodontal disease |
| JP3114245B2 (ja) * | 1991-06-03 | 2000-12-04 | 藤沢薬品工業株式会社 | 持続性製剤の製造方法 |
| DK0674506T3 (da) * | 1992-12-02 | 2001-01-08 | Alkermes Inc | Væksthormonholdige mikrosfærer med styret frigivelse |
| ES2172574T5 (es) * | 1993-11-19 | 2012-11-29 | Alkermes, Inc. | Preparación de micropartículas biodegradables que contienen un agente biológicamente activo |
| US5650173A (en) * | 1993-11-19 | 1997-07-22 | Alkermes Controlled Therapeutics Inc. Ii | Preparation of biodegradable microparticles containing a biologically active agent |
| ES2236700T3 (es) * | 1993-11-19 | 2005-07-16 | Janssen Pharmaceutica N.V. | 1,2-benzazoles microencapsulados. |
| US5792477A (en) * | 1996-05-07 | 1998-08-11 | Alkermes Controlled Therapeutics, Inc. Ii | Preparation of extended shelf-life biodegradable, biocompatible microparticles containing a biologically active agent |
-
1999
- 1999-08-27 FR FR9910854A patent/FR2797784B1/fr not_active Expired - Fee Related
-
2000
- 2000-08-25 KR KR1020027002467A patent/KR100661093B1/ko not_active IP Right Cessation
- 2000-08-25 ES ES00958741T patent/ES2215718T3/es not_active Expired - Lifetime
- 2000-08-25 DK DK00958741T patent/DK1216091T3/da active
- 2000-08-25 MX MXPA02002250A patent/MXPA02002250A/es active IP Right Grant
- 2000-08-25 JP JP2001520202A patent/JP5217070B2/ja not_active Expired - Lifetime
- 2000-08-25 EP EP00958741A patent/EP1216091B9/de not_active Expired - Lifetime
- 2000-08-25 IL IL14831600A patent/IL148316A0/xx active IP Right Grant
- 2000-08-25 AT AT00958741T patent/ATE261338T1/de active
- 2000-08-25 WO PCT/FR2000/002376 patent/WO2001015799A1/fr active IP Right Grant
- 2000-08-25 AU AU70168/00A patent/AU776959B2/en not_active Ceased
- 2000-08-25 PT PT00958741T patent/PT1216091E/pt unknown
- 2000-08-25 CA CA002382697A patent/CA2382697C/fr not_active Expired - Fee Related
- 2000-08-25 CN CNB008121311A patent/CN1317064C/zh not_active Expired - Fee Related
- 2000-08-25 DE DE60008894T patent/DE60008894T2/de not_active Expired - Lifetime
- 2000-09-25 HU HU0203199A patent/HU228747B1/hu not_active IP Right Cessation
-
2002
- 2002-02-21 IL IL148316A patent/IL148316A/en not_active IP Right Cessation
- 2002-02-22 NO NO20020881A patent/NO322106B1/no not_active IP Right Cessation
- 2002-02-26 ZA ZA200201543A patent/ZA200201543B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO20020881L (no) | 2002-04-25 |
| ATE261338T1 (de) | 2004-03-15 |
| CA2382697A1 (fr) | 2001-03-08 |
| FR2797784B1 (fr) | 2001-11-30 |
| PT1216091E (pt) | 2004-08-31 |
| IL148316A0 (en) | 2002-09-12 |
| HU0203199D0 (de) | 2002-10-28 |
| CN1317064C (zh) | 2007-05-23 |
| CA2382697C (fr) | 2009-05-05 |
| ES2215718T3 (es) | 2004-10-16 |
| HU228747B1 (en) | 2013-05-28 |
| FR2797784A1 (fr) | 2001-03-02 |
| EP1216091B9 (de) | 2005-01-19 |
| WO2001015799A1 (fr) | 2001-03-08 |
| JP2003508195A (ja) | 2003-03-04 |
| MXPA02002250A (es) | 2003-08-20 |
| KR20020046284A (ko) | 2002-06-20 |
| AU776959B2 (en) | 2004-09-30 |
| NO322106B1 (no) | 2006-08-14 |
| DE60008894D1 (de) | 2004-04-15 |
| IL148316A (en) | 2006-10-31 |
| EP1216091A1 (de) | 2002-06-26 |
| AU7016800A (en) | 2001-03-26 |
| DK1216091T3 (da) | 2004-07-12 |
| KR100661093B1 (ko) | 2006-12-22 |
| CN1371301A (zh) | 2002-09-25 |
| EP1216091B1 (de) | 2004-03-10 |
| HUP0203199A2 (en) | 2003-03-28 |
| NO20020881D0 (no) | 2002-02-22 |
| JP5217070B2 (ja) | 2013-06-19 |
| DE60008894T2 (de) | 2005-03-03 |
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