IE60475B1 - Polyester-based composition for the controlled release of medicinal substances - Google Patents
Polyester-based composition for the controlled release of medicinal substancesInfo
- Publication number
- IE60475B1 IE60475B1 IE311088A IE311088A IE60475B1 IE 60475 B1 IE60475 B1 IE 60475B1 IE 311088 A IE311088 A IE 311088A IE 311088 A IE311088 A IE 311088A IE 60475 B1 IE60475 B1 IE 60475B1
- Authority
- IE
- Ireland
- Prior art keywords
- composition according
- copolymer
- medicinal substance
- polymer
- hormone
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 38
- 238000013270 controlled release Methods 0.000 title abstract description 5
- 229920000728 polyester Polymers 0.000 title description 19
- 239000000126 substance Substances 0.000 title description 9
- 229920001577 copolymer Polymers 0.000 claims abstract description 28
- 239000012907 medicinal substance Substances 0.000 claims abstract description 17
- 229920002988 biodegradable polymer Polymers 0.000 claims abstract description 10
- 239000004621 biodegradable polymer Substances 0.000 claims abstract description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 10
- 238000013268 sustained release Methods 0.000 claims abstract description 6
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims abstract description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 5
- 230000004102 tricarboxylic acid cycle Effects 0.000 claims abstract description 5
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000003094 microcapsule Substances 0.000 claims description 19
- 229920000642 polymer Polymers 0.000 claims description 17
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 14
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 12
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 12
- 239000011859 microparticle Substances 0.000 claims description 9
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 9
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 8
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 8
- 229920001184 polypeptide Polymers 0.000 claims description 8
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 8
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 8
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 claims description 6
- 239000001384 succinic acid Substances 0.000 claims description 6
- 239000001530 fumaric acid Substances 0.000 claims description 5
- 238000001727 in vivo Methods 0.000 claims description 5
- 239000000095 Growth Hormone-Releasing Hormone Substances 0.000 claims description 4
- 102000038461 Growth Hormone-Releasing Hormone Human genes 0.000 claims description 4
- XNSAINXGIQZQOO-UHFFFAOYSA-N L-pyroglutamyl-L-histidyl-L-proline amide Natural products NC(=O)C1CCCN1C(=O)C(NC(=O)C1NC(=O)CC1)CC1=CN=CN1 XNSAINXGIQZQOO-UHFFFAOYSA-N 0.000 claims description 4
- 241001465754 Metazoa Species 0.000 claims description 4
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- 101800004623 Thyrotropin-releasing hormone Proteins 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims description 4
- XNSAINXGIQZQOO-SRVKXCTJSA-N protirelin Chemical compound NC(=O)[C@@H]1CCCN1C(=O)[C@@H](NC(=O)[C@H]1NC(=O)CC1)CC1=CN=CN1 XNSAINXGIQZQOO-SRVKXCTJSA-N 0.000 claims description 4
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- 102000055006 Calcitonin Human genes 0.000 claims description 2
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- 230000001430 anti-depressive effect Effects 0.000 claims description 2
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- 230000002785 anti-thrombosis Effects 0.000 claims description 2
- 230000000259 anti-tumor effect Effects 0.000 claims description 2
- 239000003146 anticoagulant agent Substances 0.000 claims description 2
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- BBBFJLBPOGFECG-VJVYQDLKSA-N calcitonin Chemical compound N([C@H](C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(N)=O)C(C)C)C(=O)[C@@H]1CSSC[C@H](N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1 BBBFJLBPOGFECG-VJVYQDLKSA-N 0.000 claims description 2
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- 150000002009 diols Chemical class 0.000 claims description 2
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- 238000002347 injection Methods 0.000 claims description 2
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- 229940125396 insulin Drugs 0.000 claims description 2
- 229940079322 interferon Drugs 0.000 claims description 2
- 239000011159 matrix material Substances 0.000 claims description 2
- 239000003176 neuroleptic agent Substances 0.000 claims description 2
- 230000000701 neuroleptic effect Effects 0.000 claims description 2
- 239000003488 releasing hormone Substances 0.000 claims description 2
- NHXLMOGPVYXJNR-ATOGVRKGSA-N somatostatin Chemical compound C([C@H]1C(=O)N[C@H](C(N[C@@H](CO)C(=O)N[C@@H](CSSC[C@@H](C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2C3=CC=CC=C3NC=2)C(=O)N[C@@H](CCCCN)C(=O)N[C@H](C(=O)N1)[C@@H](C)O)NC(=O)CNC(=O)[C@H](C)N)C(O)=O)=O)[C@H](O)C)C1=CC=CC=C1 NHXLMOGPVYXJNR-ATOGVRKGSA-N 0.000 claims description 2
- 229960000553 somatostatin Drugs 0.000 claims description 2
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- 239000003795 chemical substances by application Substances 0.000 claims 1
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- 150000007513 acids Chemical class 0.000 abstract description 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 description 11
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- 238000000034 method Methods 0.000 description 9
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- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 6
- 235000011044 succinic acid Nutrition 0.000 description 6
- 239000013543 active substance Substances 0.000 description 5
- 235000011087 fumaric acid Nutrition 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- -1 aliphatic diols Chemical class 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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- 125000002524 organometallic group Chemical group 0.000 description 3
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- 150000003839 salts Chemical class 0.000 description 3
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- 229960003604 testosterone Drugs 0.000 description 3
- AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
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- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
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- 241000700159 Rattus Species 0.000 description 1
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- 101000996723 Sus scrofa Gonadotropin-releasing hormone receptor Proteins 0.000 description 1
- 150000001413 amino acids Chemical group 0.000 description 1
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- 239000008280 blood Substances 0.000 description 1
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- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
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- 230000028709 inflammatory response Effects 0.000 description 1
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 description 1
- 229940040129 luteinizing hormone Drugs 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
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- 239000004005 microsphere Substances 0.000 description 1
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Classifications
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- 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)
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
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- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Immunology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Diabetes (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Hematology (AREA)
- Epidemiology (AREA)
- Endocrinology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Transplantation (AREA)
- Rheumatology (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH4022/87A CH672887A5 (enrdf_load_html_response) | 1987-10-14 | 1987-10-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE883110L IE883110L (en) | 1989-04-14 |
| IE60475B1 true IE60475B1 (en) | 1994-07-13 |
Family
ID=4268357
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE311088A IE60475B1 (en) | 1987-10-14 | 1988-10-13 | Polyester-based composition for the controlled release of medicinal substances |
Country Status (14)
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU221294B1 (en) * | 1989-07-07 | 2002-09-28 | Novartis Ag | Process for producing retarde compositions containing the active ingredient in a polymeric carrier |
| CH681425A5 (enrdf_load_html_response) * | 1990-11-14 | 1993-03-31 | Debio Rech Pharma Sa | |
| CH683149A5 (fr) * | 1991-07-22 | 1994-01-31 | Debio Rech Pharma Sa | Procédé pour la préparation de microsphères en matériau polymère biodégradable. |
| ZA936692B (en) * | 1992-09-12 | 1994-04-29 | Dott Ltd Comp | Physiologically active peptide composition |
| GB9310030D0 (en) * | 1993-05-15 | 1993-06-30 | Scras | Dry processed particles and process for the preparation of the same |
| US6440457B1 (en) | 1993-05-27 | 2002-08-27 | Alza Corporation | Method of administering antidepressant dosage form |
| FR2777895A1 (fr) | 1998-04-28 | 1999-10-29 | Debio Rech Pharma Sa | Polymere sequence non-reticule,procede pour sa preparation, et ses utilisations |
| WO2004108792A2 (en) * | 2003-04-10 | 2004-12-16 | Vinod Chintamani Malshe | Novel biodegradable aliphatic polyesters and pharmaceutical compositions and applications thereof |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3978203A (en) * | 1974-07-12 | 1976-08-31 | Dynatech Corporation | Sustained release of pharmaceuticals from polyester matrices |
| DE2856901D2 (de) * | 1977-06-07 | 1980-11-13 | Garching Instrumente | Form of implant medicament and preparation process |
| US4130639A (en) * | 1977-09-28 | 1978-12-19 | Ethicon, Inc. | Absorbable pharmaceutical compositions based on isomorphic copolyoxalates |
| US4186189A (en) * | 1977-09-28 | 1980-01-29 | Ethicon, Inc. | Absorbable pharmaceutical compositions based on poly(alkylene oxalates) |
| US4594407A (en) * | 1983-09-20 | 1986-06-10 | Allied Corporation | Prosthetic devices derived from krebs-cycle dicarboxylic acids and diols |
| US4481353A (en) * | 1983-10-07 | 1984-11-06 | The Children's Medical Center Corporation | Bioresorbable polyesters and polyester composites |
-
1987
- 1987-10-14 CH CH4022/87A patent/CH672887A5/fr not_active IP Right Cessation
-
1988
- 1988-10-10 GB GB8823735A patent/GB2211091B/en not_active Expired - Fee Related
- 1988-10-11 ES ES8803091A patent/ES2009347A6/es not_active Expired
- 1988-10-11 IT IT8805224A patent/IT1227394B/it active
- 1988-10-11 NL NL8802490A patent/NL8802490A/nl active Search and Examination
- 1988-10-13 GR GR880100688A patent/GR1000266B/el not_active IP Right Cessation
- 1988-10-13 IE IE311088A patent/IE60475B1/en not_active IP Right Cessation
- 1988-10-13 PT PT88757A patent/PT88757B/pt active IP Right Grant
- 1988-10-13 FR FR8813487A patent/FR2622105B1/fr not_active Expired - Fee Related
- 1988-10-13 CA CA000579976A patent/CA1332808C/en not_active Expired - Fee Related
- 1988-10-13 DK DK571488A patent/DK571488A/da not_active Application Discontinuation
- 1988-10-14 DE DE3835099A patent/DE3835099A1/de not_active Ceased
- 1988-10-14 JP JP63260364A patent/JP2716747B2/ja not_active Expired - Fee Related
- 1988-10-14 BE BE8801184A patent/BE1001687A5/fr not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JP2716747B2 (ja) | 1998-02-18 |
| DK571488D0 (da) | 1988-10-13 |
| CA1332808C (en) | 1994-11-01 |
| FR2622105B1 (fr) | 1993-05-14 |
| IT1227394B (it) | 1991-04-08 |
| DE3835099A1 (de) | 1989-04-27 |
| GR1000266B (el) | 1992-05-12 |
| CH672887A5 (enrdf_load_html_response) | 1990-01-15 |
| PT88757B (pt) | 1993-01-29 |
| ES2009347A6 (es) | 1989-09-16 |
| FR2622105A1 (fr) | 1989-04-28 |
| NL8802490A (nl) | 1989-05-01 |
| GB2211091A (en) | 1989-06-28 |
| IT8805224A0 (it) | 1988-10-11 |
| GB8823735D0 (en) | 1988-11-16 |
| IE883110L (en) | 1989-04-14 |
| DK571488A (da) | 1989-04-15 |
| BE1001687A5 (fr) | 1990-02-06 |
| JPH01157920A (ja) | 1989-06-21 |
| GB2211091B (en) | 1991-02-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Patent lapsed |