CA1283988C - Polyesters containing alkylene oxide blocks as drug delivery systems - Google Patents
Polyesters containing alkylene oxide blocks as drug delivery systemsInfo
- Publication number
- CA1283988C CA1283988C CA000546072A CA546072A CA1283988C CA 1283988 C CA1283988 C CA 1283988C CA 000546072 A CA000546072 A CA 000546072A CA 546072 A CA546072 A CA 546072A CA 1283988 C CA1283988 C CA 1283988C
- Authority
- CA
- Canada
- Prior art keywords
- block
- polymer
- cyclic ester
- oxide
- drug delivery
- 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 - Fee Related
Links
- 238000012377 drug delivery Methods 0.000 title claims abstract description 12
- 229920000728 polyester Polymers 0.000 title abstract description 3
- 125000002947 alkylene group Chemical group 0.000 title description 4
- -1 cyclic ester Chemical class 0.000 claims abstract description 38
- 229920000233 poly(alkylene oxides) Polymers 0.000 claims abstract description 18
- 229920001400 block copolymer Polymers 0.000 claims abstract description 13
- 239000000178 monomer Substances 0.000 claims abstract description 10
- 229920005604 random copolymer Polymers 0.000 claims abstract description 10
- 229940079593 drug Drugs 0.000 claims abstract description 5
- 239000003814 drug Substances 0.000 claims abstract description 5
- 229940061720 alpha hydroxy acid Drugs 0.000 claims abstract description 4
- 150000001280 alpha hydroxy acids Chemical class 0.000 claims abstract description 4
- 229920000642 polymer Polymers 0.000 claims description 55
- YFHICDDUDORKJB-UHFFFAOYSA-N trimethylene carbonate Chemical compound O=C1OCCCO1 YFHICDDUDORKJB-UHFFFAOYSA-N 0.000 claims description 51
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 37
- 108010006025 bovine growth hormone Proteins 0.000 claims description 27
- RKDVKSZUMVYZHH-UHFFFAOYSA-N 1,4-dioxane-2,5-dione Chemical group O=C1COC(=O)CO1 RKDVKSZUMVYZHH-UHFFFAOYSA-N 0.000 claims description 18
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 claims description 18
- 239000000835 fiber Substances 0.000 claims description 16
- 150000004292 cyclic ethers Chemical class 0.000 claims description 14
- 229920001577 copolymer Polymers 0.000 claims description 12
- 229920000359 diblock copolymer Polymers 0.000 claims description 9
- 229960000278 theophylline Drugs 0.000 claims description 9
- 229920000428 triblock copolymer Polymers 0.000 claims description 9
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Natural products OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 4
- 239000004698 Polyethylene Substances 0.000 claims description 4
- 229920000573 polyethylene Polymers 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 description 27
- 239000000017 hydrogel Substances 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 239000010408 film Substances 0.000 description 14
- 238000000034 method Methods 0.000 description 14
- 229920001223 polyethylene glycol Polymers 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 11
- 238000000338 in vitro Methods 0.000 description 9
- 239000000463 material Substances 0.000 description 8
- 239000011149 active material Substances 0.000 description 7
- HQPMKSGTIOYHJT-UHFFFAOYSA-N ethane-1,2-diol;propane-1,2-diol Chemical compound OCCO.CC(O)CO HQPMKSGTIOYHJT-UHFFFAOYSA-N 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- 239000011159 matrix material Substances 0.000 description 7
- 229920001993 poloxamer 188 Polymers 0.000 description 7
- 230000008961 swelling Effects 0.000 description 7
- 229920002065 Pluronic® P 105 Polymers 0.000 description 6
- 229920002594 Polyethylene Glycol 8000 Polymers 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 description 6
- 229920001451 polypropylene glycol Polymers 0.000 description 6
- 241000700159 Rattus Species 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- 238000011068 loading method Methods 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000007853 buffer solution Substances 0.000 description 4
- 239000002274 desiccant Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 229920001519 homopolymer Polymers 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 229920001427 mPEG Polymers 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 229920001169 thermoplastic Polymers 0.000 description 3
- 239000004416 thermosoftening plastic Substances 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000007943 implant Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 238000001226 reprecipitation Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- JJTUDXZGHPGLLC-IMJSIDKUSA-N 4511-42-6 Chemical compound C[C@@H]1OC(=O)[C@H](C)OC1=O JJTUDXZGHPGLLC-IMJSIDKUSA-N 0.000 description 1
- 102220473066 Chemerin-like receptor 2_H20A_mutation Human genes 0.000 description 1
- 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
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000012062 aqueous buffer Substances 0.000 description 1
- 235000021053 average weight gain Nutrition 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000007975 buffered saline Substances 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 230000002301 combined effect Effects 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 239000000599 controlled substance Substances 0.000 description 1
- 150000004699 copper complex Chemical class 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000012738 dissolution medium Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229920006030 multiblock copolymer Polymers 0.000 description 1
- 239000013642 negative control Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000002572 peristaltic effect Effects 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 229920001983 poloxamer Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 229920003169 water-soluble polymer Polymers 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/64—Polyesters containing both carboxylic ester groups and carbonate groups
-
- 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
- A61K9/70—Web, sheet or filament bases ; Films; Fibres of the matrix type containing drug
-
- 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
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/2031—Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, polyethylene oxide, poloxamers
- A61K9/204—Polyesters, e.g. poly(lactide-co-glycolide)
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Polyesters Or Polycarbonates (AREA)
- Medicinal Preparation (AREA)
- Materials For Medical Uses (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/903,797 | 1986-09-05 | ||
| US06/903,801 | 1986-09-05 | ||
| US06/903,801 US4882168A (en) | 1986-09-05 | 1986-09-05 | Polyesters containing alkylene oxide blocks as drug delivery systems |
| US06/903,797 US4716203A (en) | 1986-09-05 | 1986-09-05 | Diblock and triblock copolymers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1283988C true CA1283988C (en) | 1991-05-07 |
Family
ID=27129378
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000546072A Expired - Fee Related CA1283988C (en) | 1986-09-05 | 1987-09-03 | Polyesters containing alkylene oxide blocks as drug delivery systems |
Country Status (13)
| Country | Link |
|---|---|
| EP (1) | EP0258780B1 (enExample) |
| KR (1) | KR880003985A (enExample) |
| AU (1) | AU605172B2 (enExample) |
| BR (1) | BR8704648A (enExample) |
| CA (1) | CA1283988C (enExample) |
| DE (1) | DE3786309T2 (enExample) |
| DK (1) | DK462287A (enExample) |
| ES (1) | ES2058081T3 (enExample) |
| FI (1) | FI873840L (enExample) |
| GR (1) | GR3008526T3 (enExample) |
| HU (1) | HU205711B (enExample) |
| IL (1) | IL83764A (enExample) |
| NZ (1) | NZ221647A (enExample) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL9401703A (nl) * | 1994-10-14 | 1996-05-01 | Rijksuniversiteit | Kauwgom. |
| US5665428A (en) * | 1995-10-25 | 1997-09-09 | Macromed, Inc. | Preparation of peptide containing biodegradable microspheres by melt process |
| US5702717A (en) * | 1995-10-25 | 1997-12-30 | Macromed, Inc. | Thermosensitive biodegradable polymers based on poly(ether-ester)block copolymers |
| DE19726412A1 (de) * | 1997-06-21 | 1998-12-24 | Merck Patent Gmbh | Implantatmaterial mit einer Träger-Wirkstoff-Kombination |
| CN1195788C (zh) * | 1997-10-03 | 2005-04-06 | 麦克罗梅德公司 | 具有可逆热胶凝性质的可生物降解低分子量三嵌段聚(丙交酯－共聚－乙交酯)聚乙二醇共聚物 |
| US6201072B1 (en) | 1997-10-03 | 2001-03-13 | Macromed, Inc. | Biodegradable low molecular weight triblock poly(lactide-co- glycolide) polyethylene glycol copolymers having reverse thermal gelation properties |
| US6117949A (en) * | 1998-10-01 | 2000-09-12 | Macromed, Inc. | Biodegradable low molecular weight triblock poly (lactide-co-glycolide) polyethylene glycol copolymers having reverse thermal gelation properties |
| US6004573A (en) * | 1997-10-03 | 1999-12-21 | Macromed, Inc. | Biodegradable low molecular weight triblock poly(lactide-co-glycolide) polyethylene glycol copolymers having reverse thermal gelation properties |
| US7662409B2 (en) | 1998-09-25 | 2010-02-16 | Gel-Del Technologies, Inc. | Protein matrix materials, devices and methods of making and using thereof |
| US7018645B1 (en) | 2000-04-27 | 2006-03-28 | Macromed, Inc. | Mixtures of various triblock polyester polyethylene glycol copolymers having improved gel properties |
| EA007772B1 (ru) * | 2001-03-23 | 2007-02-27 | Гумлинк А/С | Разлагаемый заменитель смолы для жевательной резинки |
| DE60230020D1 (de) | 2001-03-23 | 2009-01-08 | Gumlinck As | Beschichteter, abbaubarer kaugummi mit verbesserter haltbarkeit sowie verfahren zu seiner herstellung |
| JP2004535431A (ja) | 2001-06-22 | 2004-11-25 | サザン バイオシステムズ， インコーポレイテッド | ゼロ次長期放出同軸インプラント |
| ES2304501T3 (es) | 2002-02-15 | 2008-10-16 | Nektar Therapeutics Al, Corporation | Polimeros a base de oxido de alquileno degradables hidroliticamente. |
| EP1528894B1 (en) | 2002-04-29 | 2015-06-03 | Gel-Del Technologies, Inc. | Biomatrix structural containment and fixation systems |
| BR0309688A (pt) * | 2002-05-03 | 2005-02-22 | Janssen Pharmaceutica Nv | Microemulsões poliméricas |
| US7649023B2 (en) | 2002-06-11 | 2010-01-19 | Novartis Ag | Biodegradable block copolymeric compositions for drug delivery |
| AU2003278764C1 (en) | 2002-09-06 | 2010-09-16 | Cerulean Pharma Inc. | Cyclodextrin-based polymers for therapeutic delivery |
| BR0215890A (pt) | 2002-09-24 | 2005-07-26 | Gumlink As | Goma de mascar biodegradável compreendendo pelo menos um polìmero biodegradável de alto peso molecular |
| CN100471398C (zh) | 2002-09-24 | 2009-03-25 | 古木林科有限公司 | 包括至少两种不同的生物可降解聚合物的口香糖 |
| DK1474995T3 (da) | 2003-05-06 | 2013-02-18 | Gumlink As | Fremgangsmåde til fremstilling af tyggegummigranulater, et gummisammensætningsekstruder- og granuleringssystem og et tyggegummiprodukt |
| ES2312741T3 (es) | 2003-05-06 | 2009-03-01 | Gumlink A/S | Procedimiento para producir granulos de goma de mascar y granulos de goma comprimidos, y un equipo para granular goma de mascar. |
| US8465537B2 (en) | 2003-06-17 | 2013-06-18 | Gel-Del Technologies, Inc. | Encapsulated or coated stent systems |
| US8153591B2 (en) | 2003-08-26 | 2012-04-10 | Gel-Del Technologies, Inc. | Protein biomaterials and biocoacervates and methods of making and using thereof |
| EP1691746B1 (en) | 2003-12-08 | 2015-05-27 | Gel-Del Technologies, Inc. | Mucoadhesive drug delivery devices and methods of making and using thereof |
| JP2010516625A (ja) | 2007-01-24 | 2010-05-20 | インサート セラピューティクス， インコーポレイテッド | 制御された薬物送達のためのテザー基を有するポリマー−薬物コンジュゲート |
| EP2237770A4 (en) | 2007-12-26 | 2011-11-09 | Gel Del Technologies Inc | BIOCOMPATIBLE PROTEIN PARTICLES, PARTICLE DEVICES AND METHODS THEREOF |
| US10016534B2 (en) | 2008-11-17 | 2018-07-10 | Gel-Del Technologies, Inc. | Protein biomaterial and biocoacervate vessel graft systems and methods of making and using thereof |
| AU2010295646B2 (en) | 2009-09-15 | 2016-02-11 | Ellipses Pharma Limited | Treatment of cancer |
| CA2799202C (en) | 2010-05-18 | 2016-07-05 | Cerulean Pharma Inc. | Compositions and methods for treatment of autoimmune and other diseases |
| WO2014055493A1 (en) | 2012-10-02 | 2014-04-10 | Cerulean Pharma Inc. | Methods and systems for polymer precipitation and generation of particles |
| WO2022029220A1 (en) | 2020-08-05 | 2022-02-10 | Ellipses Pharma Ltd | Treatment of cancer using a cyclodextrin-containing polymer-topoisomerase inhibitor conjugate and a parp inhibitor |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3736646A (en) * | 1971-10-18 | 1973-06-05 | American Cyanamid Co | Method of attaching surgical needles to multifilament polyglycolic acid absorbable sutures |
| US4047533A (en) * | 1976-09-20 | 1977-09-13 | American Cyanamid Company | Absorbable surgical sutures coated with polyoxyethylene-polyoxypropylene copolymer lubricant |
| US4429080A (en) * | 1982-07-01 | 1984-01-31 | American Cyanamid Company | Synthetic copolymer surgical articles and method of manufacturing the same |
| US4452973A (en) * | 1982-11-12 | 1984-06-05 | American Cyanamid Company | Poly(glycolic acid)/poly(oxyethylene) triblock copolymers and method of manufacturing the same |
| US4438253A (en) * | 1982-11-12 | 1984-03-20 | American Cyanamid Company | Poly(glycolic acid)/poly(alkylene glycol) block copolymers and method of manufacturing the same |
-
1987
- 1987-08-25 DE DE87112279T patent/DE3786309T2/de not_active Expired - Fee Related
- 1987-08-25 EP EP87112279A patent/EP0258780B1/en not_active Expired - Lifetime
- 1987-08-25 ES ES87112279T patent/ES2058081T3/es not_active Expired - Lifetime
- 1987-09-02 NZ NZ221647A patent/NZ221647A/xx unknown
- 1987-09-03 IL IL83764A patent/IL83764A/xx not_active IP Right Cessation
- 1987-09-03 CA CA000546072A patent/CA1283988C/en not_active Expired - Fee Related
- 1987-09-04 FI FI873840A patent/FI873840L/fi not_active Application Discontinuation
- 1987-09-04 DK DK462287A patent/DK462287A/da not_active Application Discontinuation
- 1987-09-04 HU HU873970A patent/HU205711B/hu not_active IP Right Cessation
- 1987-09-04 KR KR870009842A patent/KR880003985A/ko not_active Ceased
- 1987-09-04 BR BR8704648A patent/BR8704648A/pt not_active Application Discontinuation
- 1987-09-04 AU AU77970/87A patent/AU605172B2/en not_active Ceased
-
1993
- 1993-07-16 GR GR920403165T patent/GR3008526T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FI873840A7 (fi) | 1988-03-06 |
| EP0258780A2 (en) | 1988-03-09 |
| BR8704648A (pt) | 1988-04-26 |
| DE3786309D1 (de) | 1993-07-29 |
| EP0258780A3 (en) | 1988-05-18 |
| AU605172B2 (en) | 1991-01-10 |
| HU205711B (en) | 1992-06-29 |
| AU7797087A (en) | 1988-03-10 |
| DE3786309T2 (de) | 1994-02-10 |
| EP0258780B1 (en) | 1993-06-23 |
| FI873840L (fi) | 1988-03-06 |
| HUT52945A (en) | 1990-09-28 |
| ES2058081T3 (es) | 1994-11-01 |
| DK462287A (da) | 1988-03-06 |
| NZ221647A (en) | 1990-09-26 |
| FI873840A0 (fi) | 1987-09-04 |
| IL83764A0 (en) | 1988-02-29 |
| GR3008526T3 (enExample) | 1993-10-29 |
| DK462287D0 (da) | 1987-09-04 |
| IL83764A (en) | 1991-05-12 |
| KR880003985A (ko) | 1988-05-31 |
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