CA1270599A - Process for preparing microparticles of hydrophilic polymers with a polymeric stabilizer of water-in-oil emulsions - Google Patents
Process for preparing microparticles of hydrophilic polymers with a polymeric stabilizer of water-in-oil emulsionsInfo
- Publication number
- CA1270599A CA1270599A CA000504763A CA504763A CA1270599A CA 1270599 A CA1270599 A CA 1270599A CA 000504763 A CA000504763 A CA 000504763A CA 504763 A CA504763 A CA 504763A CA 1270599 A CA1270599 A CA 1270599A
- Authority
- CA
- Canada
- Prior art keywords
- water
- poly
- alkyl
- stabilizer
- benzyl
- 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
- 239000003381 stabilizer Substances 0.000 title claims abstract description 23
- 239000011859 microparticle Substances 0.000 title claims abstract description 13
- 229920001477 hydrophilic polymer Polymers 0.000 title claims description 5
- 239000000839 emulsion Substances 0.000 title abstract description 5
- 238000004519 manufacturing process Methods 0.000 title 1
- 229920000642 polymer Polymers 0.000 claims abstract description 19
- 239000000178 monomer Substances 0.000 claims abstract description 13
- 238000002360 preparation method Methods 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
- 239000001301 oxygen Substances 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 2
- 239000008346 aqueous phase Substances 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 229920001577 copolymer Polymers 0.000 claims description 5
- 239000007762 w/o emulsion Substances 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000004990 dihydroxyalkyl group Chemical group 0.000 claims description 3
- -1 poly(.beta.-benzyl-L-aspartate) Polymers 0.000 claims description 3
- 229920003169 water-soluble polymer Polymers 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- BGGHCRNCRWQABU-JTQLQIEISA-N (2s)-2-amino-5-oxo-5-phenylmethoxypentanoic acid Chemical compound OC(=O)[C@@H](N)CCC(=O)OCC1=CC=CC=C1 BGGHCRNCRWQABU-JTQLQIEISA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract description 4
- 239000002245 particle Substances 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 16
- 238000003756 stirring Methods 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000012071 phase Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000007863 gel particle Substances 0.000 description 3
- 230000006641 stabilisation Effects 0.000 description 3
- 238000011105 stabilization Methods 0.000 description 3
- 230000000087 stabilizing effect Effects 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 238000004220 aggregation Methods 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 239000008363 phosphate buffer Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000007711 solidification Methods 0.000 description 2
- 230000008023 solidification Effects 0.000 description 2
- 239000012798 spherical particle Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 230000002110 toxicologic effect Effects 0.000 description 2
- 231100000027 toxicology Toxicity 0.000 description 2
- WTFUTSCZYYCBAY-SXBRIOAWSA-N 6-[(E)-C-[[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]methyl]-N-hydroxycarbonimidoyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C/C(=N/O)/C1=CC2=C(NC(O2)=O)C=C1 WTFUTSCZYYCBAY-SXBRIOAWSA-N 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000371 Esterases Proteins 0.000 description 1
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 229940024606 amino acid Drugs 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 238000007098 aminolysis reaction Methods 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 229960005215 dichloroacetic acid Drugs 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 229960000587 glutaral Drugs 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/08—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from amino-carboxylic acids
- C08G69/10—Alpha-amino-carboxylic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/34—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Polyamides (AREA)
- Medicinal Preparation (AREA)
- Colloid Chemistry (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS206285A CS252559B1 (en) | 1985-03-22 | 1985-03-22 | Polymer stabilizer of emulsion type water in oil |
| CSPV2062-85 | 1985-03-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1270599A true CA1270599A (en) | 1990-06-19 |
Family
ID=5356631
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000504763A Expired CA1270599A (en) | 1985-03-22 | 1986-03-21 | Process for preparing microparticles of hydrophilic polymers with a polymeric stabilizer of water-in-oil emulsions |
Country Status (4)
| Country | Link |
|---|---|
| CA (1) | CA1270599A (cs) |
| CS (1) | CS252559B1 (cs) |
| DE (1) | DE3610912A1 (cs) |
| GB (1) | GB2174097B (cs) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2909500B2 (ja) * | 1989-03-23 | 1999-06-23 | ベルレックス、ラボラトリーズ、レンコーポレイテッド | 水溶性抗高脂質血症剤として有用な官能化側鎖を有するポリアミド |
| CA2056035A1 (en) * | 1991-06-18 | 1992-12-19 | Walton B. Caldwell | Polyamides bearing functionalized side chains useful as water soluble hopolipidemic agents |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB834227A (en) * | 1955-01-22 | 1960-05-04 | Fred Mayer | Poly-n-quaternary ammonium electrolytes and í¡í¡ thereof |
| GB996760A (en) * | 1962-09-28 | 1965-06-30 | Asahi Chemical Ind | A process for polymerising n-carboxy- -amino acid anhydrides |
| GB1030801A (en) * | 1963-01-10 | 1966-05-25 | Asahi Chemical Ind | A process for the production of polypeptide fibres |
| NL128181C (cs) * | 1964-01-06 | |||
| FR1603159A (cs) * | 1967-07-20 | 1971-03-22 | ||
| GB1221469A (en) * | 1967-11-22 | 1971-02-03 | Kyowa Hakko Kogyo Kk | Glutamic acid polymer coatings |
| GB1294141A (en) * | 1969-05-07 | 1972-10-25 | Kyowa Hakko Kogyo Kk | Solutions of polyglutamic acid derivatives |
| GB1298617A (en) * | 1969-06-18 | 1972-12-06 | Kyowa Hakko Kogyo Kk | POLYMERISATION OF alpha-AMINO ACID N-CARBOXYANHYDRIDES |
| IT1045109B (it) * | 1969-07-03 | 1980-05-10 | Inst Sieroterapico E Vaccino G | Foli idrossi etil asparagina e metodo per la sua produzione |
| DE2015510A1 (de) * | 1970-04-01 | 1971-10-21 | ESPE Fabrik pharmazeutischer Präparate GmbH, 8031 Seefeld | Spül- und Reinigungsmittel für Schleimhäute |
| JPS4836198B1 (cs) * | 1970-04-15 | 1973-11-01 | ||
| JPS5031905B1 (cs) * | 1971-07-05 | 1975-10-16 | ||
| FR2182667B1 (cs) * | 1972-05-03 | 1978-03-03 | Rhone Poulenc Ind | |
| GB1402758A (en) * | 1972-06-23 | 1975-08-13 | Honny Chemicals Ltd | Polyglutamic esters |
| FR2206321B1 (cs) * | 1972-11-13 | 1976-06-25 | Kyowa Hakko Kogyo Kk | |
| GB1506217A (en) * | 1975-08-26 | 1978-04-05 | Taiho Pharmaceutical Co Ltd | Oral antilipemic composition |
| EP0130935B1 (fr) * | 1983-07-01 | 1987-04-15 | Battelle Memorial Institute | Polypeptide biodégradable et son utilisation pour le relargage progressif de médicaments |
-
1985
- 1985-03-22 CS CS206285A patent/CS252559B1/cs unknown
-
1986
- 1986-03-17 GB GB08606561A patent/GB2174097B/en not_active Expired
- 1986-03-21 CA CA000504763A patent/CA1270599A/en not_active Expired
- 1986-03-24 DE DE19863610912 patent/DE3610912A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| GB2174097A (en) | 1986-10-29 |
| GB8606561D0 (en) | 1986-04-23 |
| CS252559B1 (en) | 1987-09-17 |
| GB2174097B (en) | 1988-09-07 |
| DE3610912A1 (de) | 1986-09-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed |