CA1122077A - Low temperature preparation of polymer microspheres - Google Patents
Low temperature preparation of polymer microspheresInfo
- Publication number
- CA1122077A CA1122077A CA000309884A CA309884A CA1122077A CA 1122077 A CA1122077 A CA 1122077A CA 000309884 A CA000309884 A CA 000309884A CA 309884 A CA309884 A CA 309884A CA 1122077 A CA1122077 A CA 1122077A
- Authority
- CA
- Canada
- Prior art keywords
- polymer
- core material
- solvent
- phase separation
- process according
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- 229920000642 polymer Polymers 0.000 title claims abstract description 67
- 239000004005 microsphere Substances 0.000 title claims abstract description 28
- 238000002360 preparation method Methods 0.000 title description 4
- 239000011162 core material Substances 0.000 claims abstract description 34
- 229940079593 drug Drugs 0.000 claims abstract description 33
- 239000003814 drug Substances 0.000 claims abstract description 33
- 238000005191 phase separation Methods 0.000 claims abstract description 30
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 25
- 239000006185 dispersion Substances 0.000 claims abstract description 12
- 239000002904 solvent Substances 0.000 claims description 54
- 238000000034 method Methods 0.000 claims description 39
- 239000003094 microcapsule Substances 0.000 claims description 35
- 239000002245 particle Substances 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 6
- 239000011248 coating agent Substances 0.000 claims description 5
- 238000000576 coating method Methods 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 150000005846 sugar alcohols Polymers 0.000 claims description 4
- 239000004621 biodegradable polymer Substances 0.000 claims description 3
- 229920001577 copolymer Polymers 0.000 claims description 3
- 239000008240 homogeneous mixture Substances 0.000 claims description 3
- 229920000954 Polyglycolide Polymers 0.000 claims description 2
- 229920002988 biodegradable polymer Polymers 0.000 claims description 2
- 239000011859 microparticle Substances 0.000 claims description 2
- 239000004633 polyglycolic acid Substances 0.000 claims description 2
- SJZRECIVHVDYJC-UHFFFAOYSA-N 4-hydroxybutyric acid Chemical compound OCCCC(O)=O SJZRECIVHVDYJC-UHFFFAOYSA-N 0.000 claims 1
- 229920000747 poly(lactic acid) Polymers 0.000 claims 1
- 239000004626 polylactic acid Substances 0.000 claims 1
- 230000002776 aggregation Effects 0.000 abstract description 8
- 238000005054 agglomeration Methods 0.000 abstract description 7
- 150000002894 organic compounds Chemical class 0.000 abstract 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 52
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 42
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 229960004592 isopropanol Drugs 0.000 description 26
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 18
- KLBQZWRITKRQQV-UHFFFAOYSA-N Thioridazine Chemical compound C12=CC(SC)=CC=C2SC2=CC=CC=C2N1CCC1CCCCN1C KLBQZWRITKRQQV-UHFFFAOYSA-N 0.000 description 11
- 239000000047 product Substances 0.000 description 10
- 239000002775 capsule Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 229920001244 Poly(D,L-lactide) Polymers 0.000 description 8
- 238000007710 freezing Methods 0.000 description 7
- 230000008014 freezing Effects 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- GGNALUCSASGNCK-UHFFFAOYSA-N carbon dioxide;propan-2-ol Chemical compound O=C=O.CC(C)O GGNALUCSASGNCK-UHFFFAOYSA-N 0.000 description 6
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 239000012456 homogeneous solution Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002861 polymer material Substances 0.000 description 3
- 239000006228 supernatant Substances 0.000 description 3
- -1 ~odenticides Substances 0.000 description 3
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-REOHCLBHSA-N L-lactic acid Chemical compound C[C@H](O)C(O)=O JVTAAEKCZFNVCJ-REOHCLBHSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 239000008186 active pharmaceutical agent Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 235000011089 carbon dioxide Nutrition 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 229940088679 drug related substance Drugs 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000005538 encapsulation Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 229940035429 isobutyl alcohol Drugs 0.000 description 2
- 239000004848 polyfunctional curative Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- OZVBMTJYIDMWIL-AYFBDAFISA-N bromocriptine Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@]2(C(=O)N3[C@H](C(N4CCC[C@H]4[C@]3(O)O2)=O)CC(C)C)C(C)C)C2)=C3C2=C(Br)NC3=C1 OZVBMTJYIDMWIL-AYFBDAFISA-N 0.000 description 1
- 229960002802 bromocriptine Drugs 0.000 description 1
- 238000004581 coalescence Methods 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000002781 deodorant agent Substances 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 229960000807 dihydroergotamine mesylate Drugs 0.000 description 1
- ADYPXRFPBQGGAH-UMYZUSPBSA-N dihydroergotamine mesylate Chemical compound CS(O)(=O)=O.C([C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@@](C(N21)=O)(C)NC(=O)[C@H]1CN([C@H]2[C@@H](C=3C=CC=C4NC=C(C=34)C2)C1)C)C1=CC=CC=C1 ADYPXRFPBQGGAH-UMYZUSPBSA-N 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 238000002194 freeze distillation Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 230000001965 increasing effect Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- JZQKKSLKJUAGIC-UHFFFAOYSA-N pindolol Chemical compound CC(C)NCC(O)COC1=CC=CC2=C1C=CN2 JZQKKSLKJUAGIC-UHFFFAOYSA-N 0.000 description 1
- 229960002508 pindolol Drugs 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229960002784 thioridazine Drugs 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/26—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests in coated particulate form
- A01N25/28—Microcapsules or nanocapsules
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/0241—Containing particulates characterized by their shape and/or structure
- A61K8/025—Explicitly spheroidal or spherical shape
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/85—Polyesters
-
- 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
- A61K9/50—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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q13/00—Formulations or additives for perfume preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q15/00—Anti-perspirants or body deodorants
-
- 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
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/56—Compounds, absorbed onto or entrapped into a solid carrier, e.g. encapsulated perfumes, inclusion compounds, sustained release forms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/60—Particulates further characterized by their structure or composition
- A61K2800/61—Surface treated
- A61K2800/62—Coated
- A61K2800/624—Coated by macromolecular compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/60—Particulates further characterized by their structure or composition
- A61K2800/65—Characterized by the composition of the particulate/core
- A61K2800/654—The particulate/core comprising macromolecular material
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Birds (AREA)
- Pest Control & Pesticides (AREA)
- Toxicology (AREA)
- Zoology (AREA)
- General Chemical & Material Sciences (AREA)
- Wood Science & Technology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Dentistry (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Dispersion Chemistry (AREA)
- Manufacturing Of Micro-Capsules (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US82771077A | 1977-08-25 | 1977-08-25 | |
| US827,710 | 1977-08-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1122077A true CA1122077A (en) | 1982-04-20 |
Family
ID=25249947
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000309884A Expired CA1122077A (en) | 1977-08-25 | 1978-08-23 | Low temperature preparation of polymer microspheres |
Country Status (21)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20110070442A1 (en) * | 2008-05-21 | 2011-03-24 | Toray Industries, Inc. | Method for producing polymer fine particle |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6045845B2 (ja) * | 1979-10-31 | 1985-10-12 | 田辺製薬株式会社 | 医薬物質含有マイクロカプセルの製法 |
| US4384975A (en) * | 1980-06-13 | 1983-05-24 | Sandoz, Inc. | Process for preparation of microspheres |
| PH19942A (en) * | 1980-11-18 | 1986-08-14 | Sintex Inc | Microencapsulation of water soluble polypeptides |
| DE3045135A1 (de) * | 1980-11-29 | 1982-06-09 | Sandoz-Patent-GmbH, 7850 Lörrach | Pharmazeutische kompositionen enthaltende bioabbaubare polymere |
| JPS5933214A (ja) * | 1982-08-19 | 1984-02-23 | Mitsui Toatsu Chem Inc | 微小球に製剤された制ガン剤の製造方法 |
| AT382076B (de) * | 1982-10-15 | 1987-01-12 | Chemie Linz Ag | Verfahren zur herstellung von presslingen mit retardierter wirkstofffreisetzung |
| DE3417576A1 (de) * | 1984-05-11 | 1985-11-14 | Lentia GmbH Chem. u. pharm. Erzeugnisse - Industriebedarf, 8000 München | Retardformen des alpha-(2,5-dimethoxy-phenyl)-ss-glycinamidoaethanols und verfahren zu ihrer herstellung |
| DE3428372A1 (de) * | 1984-08-01 | 1986-02-13 | Hoechst Ag, 6230 Frankfurt | Mikrokapseln von regulatorischen peptiden mit kontrollierter freisetzung, verfahren zu ihrer herstellung und injektionszubereitungen |
| CH660302A5 (fr) * | 1984-10-17 | 1987-04-15 | Debiopharm Sa | Procede de micro-encapsulation en phase heterogene de substances medicamenteuses hydrosolubles. |
| CH669506A5 (en) * | 1986-01-13 | 1989-03-31 | Hugo Degen | Oscillating and reclining furniture |
| DE3712095A1 (de) * | 1987-04-10 | 1988-10-20 | Lentia Gmbh | Bindemittelfreies granulat mit verzoegerter wirkstoffabgabe |
| US4861627A (en) * | 1987-05-01 | 1989-08-29 | Massachusetts Institute Of Technology | Preparation of multiwall polymeric microcapsules |
| HU221294B1 (en) * | 1989-07-07 | 2002-09-28 | Novartis Ag | Process for producing retarde compositions containing the active ingredient in a polymeric carrier |
| FR2657255B1 (fr) * | 1989-12-27 | 1992-04-24 | Sederma Sa | Description de preparations cosmetiques originales dont les principes actifs sont pieges dans un reseau polymerique greffe a la surface de particules de silice. |
| DE4127757A1 (de) * | 1991-02-06 | 1992-08-13 | Hoechst Ag | Neue pflanzenschutzmittel-formulierungen |
| US6204308B1 (en) | 1999-03-01 | 2001-03-20 | Novartis Ag | Organic compounds |
| US6969480B2 (en) | 2000-05-12 | 2005-11-29 | Matregen Corp. | Method of producing structures using centrifugal forces |
| DE60121170T2 (de) * | 2000-05-12 | 2007-05-16 | Matregen Corp., Toronto | Verfahren zur herstellung von strukturen durch gebrauch von zentrifugalen kräften |
| US6824822B2 (en) * | 2001-08-31 | 2004-11-30 | Alkermes Controlled Therapeutics Inc. Ii | Residual solvent extraction method and microparticles produced thereby |
| US20110027376A1 (en) * | 2007-12-11 | 2011-02-03 | Nanyang Technological University | Hollow Multi-Layered Microspheres for Delivery of Hydrophilic Active Compounds |
| CN103828801B (zh) * | 2014-01-15 | 2016-01-27 | 福建农林大学 | 多杀菌素/甲氨基阿维菌素苯甲酸盐微球及其制备方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT631615A (enrdf_load_stackoverflow) * | 1960-02-26 | |||
| US3427250A (en) * | 1963-03-25 | 1969-02-11 | Polaroid Corp | Microscopic capsules and process for their preparation |
| US3531418A (en) * | 1965-08-18 | 1970-09-29 | Ncr Co | En masse encapsulation process |
| FR1497584A (fr) * | 1966-08-11 | 1967-10-13 | Roussel Uclaf | Procédé de fabrication de microcapsules |
| US3703474A (en) * | 1967-08-21 | 1972-11-21 | Ncr Co | Encapsulation process |
| US3773919A (en) * | 1969-10-23 | 1973-11-20 | Du Pont | Polylactide-drug mixtures |
| JPS51125675A (en) * | 1975-02-13 | 1976-11-02 | Asahi Chem Ind Co Ltd | A porous capsule structvre and a process for manufacturing turing it |
-
1978
- 1978-08-15 CH CH867978A patent/CH644768A5/de not_active IP Right Cessation
- 1978-08-15 CH CH310/84A patent/CH649217A5/de not_active IP Right Cessation
- 1978-08-16 FI FI782501A patent/FI64899C/fi not_active IP Right Cessation
- 1978-08-16 DK DK361878A patent/DK361878A/da not_active Application Discontinuation
- 1978-08-17 DE DE19782836044 patent/DE2836044A1/de active Granted
- 1978-08-18 SE SE7808759A patent/SE431942B/sv unknown
- 1978-08-21 NL NL7808613A patent/NL7808613A/xx active Search and Examination
- 1978-08-22 GB GB7834199A patent/GB2003108B/en not_active Expired
- 1978-08-23 NZ NZ188232A patent/NZ188232A/xx unknown
- 1978-08-23 AT AT0612478A patent/AT372019B/de not_active IP Right Cessation
- 1978-08-23 ES ES472800A patent/ES472800A1/es not_active Expired
- 1978-08-23 BE BE190031A patent/BE869915A/xx not_active IP Right Cessation
- 1978-08-23 IL IL55418A patent/IL55418A/xx unknown
- 1978-08-23 IT IT26961/78A patent/IT1098111B/it active
- 1978-08-23 CA CA000309884A patent/CA1122077A/en not_active Expired
- 1978-08-23 IE IE1708/78A patent/IE47255B1/en unknown
- 1978-08-24 PT PT68473A patent/PT68473A/pt unknown
- 1978-08-24 JP JP10237078A patent/JPS5455717A/ja active Granted
- 1978-08-24 FR FR7824597A patent/FR2400950A1/fr active Granted
- 1978-08-24 AU AU39236/78A patent/AU522215B2/en not_active Expired
- 1978-08-25 PH PH21539A patent/PH15447A/en unknown
- 1978-08-25 ZA ZA784855A patent/ZA784855B/xx unknown
-
1989
- 1989-12-07 DK DK618189A patent/DK618189D0/da not_active Application Discontinuation
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20110070442A1 (en) * | 2008-05-21 | 2011-03-24 | Toray Industries, Inc. | Method for producing polymer fine particle |
| US8574669B2 (en) * | 2008-05-21 | 2013-11-05 | Toray Industries, Inc. | Method for producing polymer fine particle comprising contacting an emulsion with a poor solvent |
| US9410004B2 (en) | 2008-05-21 | 2016-08-09 | Toray Industries, Inc. | Aromatic polyethersulfone microparticles having narrow particle diameter distribution index |
| US10239970B2 (en) | 2008-05-21 | 2019-03-26 | Toray Industries, Inc. | Method of producing fine particles of non-vinyl thermoplastic polymer |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1122077A (en) | Low temperature preparation of polymer microspheres | |
| US4166800A (en) | Processes for preparation of microspheres | |
| CA1336068C (en) | Multiwall polymeric microcapsules | |
| Arshady | Microspheres and microcapsules: A survey of manufacturing techniques. Part 1: Suspension cross‐linking | |
| US4615881A (en) | Pharmaceutical compositions | |
| US3190837A (en) | Making individual capsules by dual deposition | |
| US4898734A (en) | Polymer composite for controlled release or membrane formation | |
| Agnihotri et al. | Microencapsulation–a novel approach in drug delivery: a review | |
| US4169069A (en) | Silicon dioxide-containing compositions and process for their preparation and use | |
| CA1218306A (en) | Injectable, long-acting microparticle formulation for the delivery of anti-inflammatory agents | |
| Khandbahale | Microencapsulation-A novel approach in drug delivery: A review | |
| US20010044026A1 (en) | Zero order release and temperature-controlled microcapsules and process for the preparation thereof | |
| JPH10511596A (ja) | 封入された活性材料及びその製造方法 | |
| US4107071A (en) | Method of producing microcapsules and resulting product | |
| Tarun et al. | Patented microencapsulation techniques and its application | |
| Pekarek et al. | One‐step preparation of double‐walled microspheres | |
| WO1990002655A1 (en) | Realease assist microcapsules | |
| US3533958A (en) | Process for making minute capsules | |
| NL192249C (nl) | Werkwijze voor het micro-inkapselen door fasescheiding van in water oplosbare geneeskrachtige stoffen. | |
| JPS6163613A (ja) | 顆粒状に調整された徐放性製剤 | |
| US3205175A (en) | Method of making ethyl-cellulose-lined liquid-containing minute capsules | |
| Jalil et al. | Microencapsulation using poly (DL-lactic acid) IV: effect of storage on the microcapsule characteristics | |
| Nande et al. | Sustained release microspheres of diclofenac sodium using PEGylated rosin derivatives | |
| Sheorey et al. | Effect of solvents on the characteristics of rosin walled microcapsules prepared by a solvent evaporation technique | |
| Sun et al. | Research progress on temperature-controlled release microcapsules |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |