CA1283988C - Polyesters containing alkylene oxide blocks as drug delivery systems - Google Patents

Polyesters containing alkylene oxide blocks as drug delivery systems

Info

Publication number: CA1283988C
Authority: CA; Canada
Prior art keywords: block; polymer; cyclic ester; oxide; drug delivery
Prior art date: 1986-09-05
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

Application number

CA000546072A

Other languages

English (en)

French (fr)

Inventor

Peter K. Jarrett

Donald J. Casey

Louis Rosati

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Wyeth Holdings LLC

Original Assignee

American Cyanamid Co

Priority date (The priority date 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 date listed.)

1986-09-05

Filing date

1987-09-03

Publication date

1991-05-07

1986-09-05 Priority claimed from US06/903,801 external-priority patent/US4882168A/en

1986-09-05 Priority claimed from US06/903,797 external-priority patent/US4716203A/en

1987-09-03 Application filed by American Cyanamid Co filed Critical American Cyanamid Co

1991-05-07 Application granted granted Critical

1991-05-07 Publication of CA1283988C publication Critical patent/CA1283988C/en

2008-05-07 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

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)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Polyesters Or Polycarbonates (AREA)
Medicinal Preparation (AREA)
Materials For Medical Uses (AREA)

CA000546072A 1986-09-05 1987-09-03 Polyesters containing alkylene oxide blocks as drug delivery systems Expired - Fee Related CA1283988C (en)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
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		1986-09-05
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 (2)
KR (1)	KR880003985A (2)
AU (1)	AU605172B2 (2)
BR (1)	BR8704648A (2)
CA (1)	CA1283988C (2)
DE (1)	DE3786309T2 (2)
DK (1)	DK462287A (2)
ES (1)	ES2058081T3 (2)
FI (1)	FI873840L (2)
GR (1)	GR3008526T3 (2)
HU (1)	HU205711B (2)
IL (1)	IL83764A (2)
NZ (1)	NZ221647A (2)

Families Citing this family (32)

* Cited by examiner, † Cited by third party
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
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
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
CA2305621C (en) *	1997-10-03	2009-01-20	Macromed, Inc.	Biodegradable low molecular weight triblock poly(lactide-co-glycolide) polyethylene glycol copolymers having reverse thermal gelation properties
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
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
DE60230020D1 (de)	2001-03-23	2009-01-08	Gumlinck As	Beschichteter, abbaubarer kaugummi mit verbesserter haltbarkeit sowie verfahren zu seiner herstellung
JP2004524410A (ja) *	2001-03-23	2004-08-12	ガムリンクエー／エス	チューインガム用の分解可能な樹脂置換体
WO2003000156A1 (en)	2001-06-22	2003-01-03	Southern Biosystems, Inc.	Zero-order prolonged release coaxial implants
ES2304501T3 (es) *	2002-02-15	2008-10-16	Nektar Therapeutics Al, Corporation	Polimeros a base de oxido de alquileno degradables hidroliticamente.
AU2003225212A1 (en)	2002-04-29	2003-11-17	Gel-Del Technologies, Inc.	Biomatrix structural containment and fixation systems and methods of use thereof
CN1290893C (zh) *	2002-05-03	2006-12-20	詹森药业有限公司	聚合物微乳状液
US7649023B2 (en)	2002-06-11	2010-01-19	Novartis Ag	Biodegradable block copolymeric compositions for drug delivery
BRPI0314042B8 (pt)	2002-09-06	2021-05-25	Calando Pharmaceuticals Inc	polímeros à base de ciclodextrina para o fornecimento de agentes terapêuticos ligados a eles por covalência
DE60228341D1 (de)	2002-09-24	2008-09-25	Gumlinck As	Biologisch abbaubarer kaugummi enthaltend wenigstens ein biologish abbaubares polymer mit hochmolekularem gewicht
ES2578252T3 (es)	2002-09-24	2016-07-22	Gumlink A/S	Goma de mascar que comprende al menos dos polímeros biodegradables diferentes
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.
EP1474995B1 (en)	2003-05-06	2012-11-14	Gumlink A/S	A method for producing chewing gum granules, a gum composition extruder and granulating system, and a chewing gum product
US8465537B2 (en)	2003-06-17	2013-06-18	Gel-Del Technologies, Inc.	Encapsulated or coated stent systems
EP1660013A4 (en)	2003-08-26	2011-07-20	Gel Del Technologies Inc	BIOMATERIAL AND PROTEIN BIOCOACERVATES, METHODS OF MAKING AND USING THEM
EP1691746B1 (en)	2003-12-08	2015-05-27	Gel-Del Technologies, Inc.	Mucoadhesive drug delivery devices and methods of making and using thereof
US20080176958A1 (en)	2007-01-24	2008-07-24	Insert Therapeutics, Inc.	Cyclodextrin-based polymers for therapeutics delivery
US11890371B2 (en)	2007-12-26	2024-02-06	Petvivo Holdings, Inc.	Biocompatible protein-based particles and methods thereof
WO2010057177A2 (en)	2008-11-17	2010-05-20	Gel-Del Technologies, Inc.	Protein biomaterial and biocoacervate vessel graft systems and methods of making and using thereof
US20110160159A1 (en)	2009-09-15	2011-06-30	John Ryan	Treatment of cancer
AU2011255647A1 (en)	2010-05-18	2012-11-15	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
EP4192509A1 (en)	2020-08-05	2023-06-14	Ellipses Pharma Ltd	Treatment of cancer using a cyclodextrin-containing polymer-topoisomerase inhibitor conjugate and a parp inhibitor

Family Cites Families (5)

* Cited by examiner, † Cited by third party
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 ES ES87112279T patent/ES2058081T3/es not_active Expired - Lifetime
- 1987-08-25 EP EP87112279A patent/EP0258780B1/en not_active Expired - Lifetime
- 1987-08-25 DE DE87112279T patent/DE3786309T2/de not_active Expired - Fee Related
- 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 DK DK462287A patent/DK462287A/da not_active Application Discontinuation
- 1987-09-04 FI FI873840A patent/FI873840L/fi not_active Application Discontinuation
- 1987-09-04 HU HU873970A patent/HU205711B/hu not_active IP Right Cessation
- 1987-09-04 AU AU77970/87A patent/AU605172B2/en not_active Ceased
- 1987-09-04 KR KR870009842A patent/KR880003985A/ko not_active Ceased
- 1987-09-04 BR BR8704648A patent/BR8704648A/pt not_active Application Discontinuation
1993
- 1993-07-16 GR GR920403165T patent/GR3008526T3/el unknown

Also Published As

Publication number	Publication date
DK462287A (da)	1988-03-06
IL83764A0 (en)	1988-02-29
NZ221647A (en)	1990-09-26
GR3008526T3 (2)	1993-10-29
HU205711B (en)	1992-06-29
BR8704648A (pt)	1988-04-26
DE3786309T2 (de)	1994-02-10
AU605172B2 (en)	1991-01-10
KR880003985A (ko)	1988-05-31
EP0258780B1 (en)	1993-06-23
AU7797087A (en)	1988-03-10
DE3786309D1 (de)	1993-07-29
FI873840A7 (fi)	1988-03-06
DK462287D0 (da)	1987-09-04
EP0258780A3 (en)	1988-05-18
EP0258780A2 (en)	1988-03-09
IL83764A (en)	1991-05-12
FI873840L (fi)	1988-03-06
HUT52945A (en)	1990-09-28
ES2058081T3 (es)	1994-11-01
FI873840A0 (fi)	1987-09-04

Legal Events

Date	Code	Title	Description
1995-11-07	MKLA	Lapsed

Publication	Publication Date	Title
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