US20060134161A1 - Water-swellable polymers - Google Patents

Water-swellable polymers Download PDF

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Publication number
US20060134161A1
US20060134161A1 US10/528,875 US52887505A US2006134161A1 US 20060134161 A1 US20060134161 A1 US 20060134161A1 US 52887505 A US52887505 A US 52887505A US 2006134161 A1 US2006134161 A1 US 2006134161A1
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polymer
water
polymer according
hours
diol
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Janet Halliday
Jukka Tuominen
Mark Livingstone
Frank Koppenhagen
Lilias Currie
Sarah Stewart
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Controlled Therapeutics Scotland Ltd
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Controlled Therapeutics Scotland Ltd
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Assigned to CONTROLLED THERAPEUTICS (SCOTLAND) LIMITED reassignment CONTROLLED THERAPEUTICS (SCOTLAND) LIMITED ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: STEWART, SARAH, KOPPENHAGEN, FRANK, LIVINGSTONE, MARK, CURRIE, LILIAS, HALLIDAY, JANET A., TUOMINEN, JUKKA
Publication of US20060134161A1 publication Critical patent/US20060134161A1/en
Priority to US12/835,436 priority Critical patent/US8557281B2/en
Priority to US13/571,596 priority patent/US8628798B2/en
Priority to US14/099,663 priority patent/US9987364B2/en
Abandoned legal-status Critical Current

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    • 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
    • A61K9/02—Suppositories; Bougies; Bases therefor; Ovules
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
    • C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
    • C08G18/6666—Compounds of group C08G18/48 or C08G18/52
    • C08G18/667—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
    • C08G18/6674—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
    • C08G18/758—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing two or more cycloaliphatic rings
    • 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
    • C08G2210/00—Compositions for preparing hydrogels

Definitions

  • the present invention relates to water-swellable linear polymers, suitable for the production of controlled release compositions for release of pharmaceutically active agents over a prolonged period of time.
  • Certain cross-linked polyurethane polymers are known from European Patent Publication EP0016652 and EP0016654. These patent specifications describe cross-linked polyurethanes formed by reacting a polyethylene oxide of equivalent weight greater than 1500 with a polyfunctional isocyanate and a trifunctional compound reactive therewith, such as an alkane triol. The resultant cross-linked polyurethane polymers are water-swellable to form a hydrogel but are water-insoluble and may be loaded with water-soluble pharmaceutically active agents.
  • One particular polyurethane polymer is the reaction product of polyethylene glycol 8000, Desmodur (DMDI i.e. dicyclohexylmethane-4,4-diisocyanate) and 1,2,6-hexane triol and which has been used commercially for vaginal delivery of prostaglandins.
  • polyurethane polymers possess a number of practical disadvantages. Whilst the use of a triol cross-linking agent is effective in providing polymers of relatively reproducible swelling characteristics, the percent swelling is typically 200-300% (i.e. the increase in weight of the swollen polymer divided by the weight of the dry polymer).
  • Pharmaceutically active agents are loaded by contacting the dry polymer with an aqueous solution of pharmaceutically active agent, such that the solution becomes absorbed into the polymer, forming a hydrogel. The swollen polymer is then dried back to a chosen water content before use.
  • the degree of swelling limits the molecular weight of the pharmaceutically active agent which can be absorbed into the hydrogel structure to below about 3000.
  • a further disadvantage is that only water-soluble pharmaceutically active agents may be used.
  • the conventional cross-linked polyurethane polymer is essentially insoluble in both water and organic solvents, processing of the formed polymer into other solid forms, such as films or coatings, is not possible.
  • the object of the present invention is to provide a polyurethane polymer of the aforementioned type which is not cross-linked but is linear but which still possesses the desirable properties of reproducible swellability found in the prior cross-linked polyurethanes.
  • the present invention is based on the discovery that linear polyurethanes having suitable characteristics may be obtained by reacting a polyoxyethylene glycol with a diol or other difunctional compound and a difunctional isocyanate.
  • the present invention provides a water-swellable linear polymer obtainable by reacting together
  • the invention provides a water-swellable linear polyurethane formed of moieties derived from (a), (b) and (c) bonded together.
  • the linear polymer produced is swellable in water to an enhanced degree, depending upon the ratio of the three components (a), (b) and (c), for example up to 500%, up to 800% or even above 1,000%, thus allowing higher molecular weight pharmaceutically active water-soluble agents to be loaded into the swollen hydrogel derived from the linear polymer.
  • the polymer is swellable to 200% to 2000%, for example 250 to 1700%.
  • swellabilities in the ranges 300-1000, 400-800, 1000-1500, 1100-1300 etc. may be achieved with the polyurethanes of the invention.
  • the linear polymer of the invention is also soluble in certain organic solvents, such as dichloromethane, which allows the polymer to be dissolved and cast into films or coatings. It also allows active agents of poor water solubility but which are soluble in organic solvents, to be loaded into the polymer.
  • organic solvents such as dichloromethane
  • equivalent weight is used as meaning the number average molecular weight divided by the functionality of the compound.
  • Polyethylene oxides contain the repeat unit (CH 2 CH 2 O) and are conveniently prepared by the stepwise addition of ethylene oxide to a compound containing a reactive hydrogen atom.
  • Polyethylene glycols are prepared by the addition of ethylene oxide to ethylene glycol to produce a difunctional polyethylene glycol structure HO(CH 2 CH 2 O) n H wherein n is an integer of varying size depending on the molecular weight of polyethylene oxide.
  • Polyethylene oxides used in the present invention are generally linear polyethylene glycols i.e. diols having an equivalent weight of 1500 to 20,000, particularly 3000 to 10,000 and especially 4000 to 8000. Molecular weights are usually in the region 4000 to 35,000.
  • the difunctional compound is reactive with the difunctional isocyanate, and is typically a difunctional amine or diol.
  • Diols in the range C 5 to C 20 , preferably C 8 to C 15 are preferred.
  • decane diol has been found to produce particularly good results.
  • the diol may be a saturated or unsaturated diol. Branched diols may be used but straight chain diols are preferred.
  • the two hydroxy groups are generally on terminal carbon atoms.
  • preferred diols include 1,6-hexanediol, 1,10-decanediol, 1,12-dodecanediol and 1,16-hexadecanediol.
  • the difunctional isocyanate is generally one of the conventional diisocyanates, such as dicyclohexylmethane-4,4-diisocyanate, diphenylmethane-4,4-diisocyanate, 1,6-hexamethylene diisocyanate etc.
  • the ratio of the components (a) to (b) to (c) is generally in the range 0.1-1.5 to 1 to 1.1-2.5, particularly 0.2-0.9 to 1 to 1.2-1.9. A preferred range is 0.5-0.9 to 1 to 1.5-1.9 Of course, the skilled man through reasonable experimentation would determine the best ratio of ingredients to give the desired properties.
  • the amount of component (c) is generally equal to the combined amounts of (a) and (b) to provide the correct stoichiometry.
  • Polymers produced at extreme ends of the ranges may not necessarily give optimal properties.
  • high amounts of (a) polyethylene oxide may undesirably lead to the polymer being water-soluble. Small amounts may reduce the percentage swelling.
  • the ratio of (a) polyethylene oxide to (b) difunctional compound is preferably 0.1-1.5 to one, preferably 0.2-0.9 to one.
  • the polymers are generally produced by melting the previously dried polyethylene glycol together with the difunctional compound (e.g. diol) at a temperature of around 85° C. A catalyst such as ferric chloride is incorporated. The molten mixture is dried under vacuum to remove excess moisture and the diisocyanate added thereto. The reaction mixture is then poured into billet moulds and cured for a specified time. Thus, the polymer is initially formed as a moulded solid.
  • the linear polymers of the present invention are soluble in certain organic solvents. This allows the polymer to be dissolved and the resultant solution cast to form films.
  • the solution may also be employed for coating granules, tablets etc., in order to modify their release properties. Alternatively, the solution can be poured into a non-solvent so as to precipitate polymer/active microparticles.
  • the invention also provides controlled release compositions comprising the linear polymer together with an active agent.
  • the active agent may be a pharmaceutically active agent for human or animal use. It may also be any other agent where sustained release properties (e.g. algicides, fertilisers etc.) are required.
  • the pharmaceutical solid dosage forms include suppositories, pessaries for vaginal use, buccal inserts for oral administration etc. These dosage forms are generally administered to the patient, retained in place until delivery of active agent has occurred and the spent polymer is then removed.
  • the linear polymer of the present invention may be swollen to a higher degree than the conventional cross-linked polymer and is thus suitable for the uptake of high molecular weight pharmaceutically active agents (up to and exceeding a molecular weight of 3000 e.g. up to 10,000, up to 50,000, up to 100,000 or even up to 200,000 depending on swellability) and is thus particularly suitable for the uptake and delivery of proteins and peptides.
  • a molecular weight of the active agent is in the range 200 to 20,00.
  • a wide variety of water-soluble pharmaceutically active substances such as those listed in EP0016652 may thus be incorporated.
  • linear polymers of the present invention may be loaded with pharmaceutically active agents which are poorly water-soluble, provided that these can be dissolved in a common solvent with the polymer.
  • the resultant solution can then be cast into any desired solid forms.
  • Pharmaceutically active agents of particular interest include:
  • Proteins e.g. interferon alpha, beta and gamma, insulin, human growth hormone, leuprolide; Benzodiazepines e.g. midazolam; Anti-migraine agents e.g. triptophans, ergotamine and its derivatives; Anti-infective agents e.g. azoles, bacterial vaginosis, candida; and opthalmic agents e.g. latanoprost.
  • Benzodiazepines e.g. midazolam
  • Anti-migraine agents e.g. triptophans, ergotamine and its derivatives
  • Anti-infective agents e.g. azoles, bacterial vaginosis, candida
  • opthalmic agents e.g. latanoprost.
  • active agent includes H 2 receptor antagonist, antimuscaririe, prostaglandin analogue, proton pump inhibitor, aminosalycilate, corticosteroid, chelating agent, cardiac glycoside, phosphodiesterase inhibitor, thiazide, diuretic, carbonic anhydrase inhibitor, antihypertensive, anti-cancer, anti-depressant, calcium channel blocker, analgesic, opioid antagonist, antiplatel, anticoagulant, fibrinolytic, statin, adrenoceptor agonist, beta blocker, antihistamine, respiratory stimulant, micolytic, expectorant, benzodiazepine, barbiturate, anxiolytic, antipsychotic, tricyclic antidepressant, 5HT 1 antagonist, opiate, 5HT, agonist, antiemetic, antiepileptic, dopaminergic, antibiotic, antifungal, anthelmintic, antiviral, antiprotozoal, antidiabetic, insulin, thyrotoxin
  • the invention also provides a method of manufacturing the linear polymer by reacting together components (a), (b) and (c).
  • the polymer should be free of air bubbles.
  • Samples were tested for stability at 40° C. over a four-week period. At the specified time point intervals of one, two and four weeks the percentage swelling (24 hours) was calculated and used as an indication of polymer stability.
  • PEG and DD were weighed into a round-bottomed flask balance and melted overnight at a temperature of 85° C.
  • ferric chloride (FeCl 3 ) plus an excess was weighed into a tared 200 mL beaker with spatula. This was made up to 100 g with molten PEG/DD from the previous step. This mixture of PEG/DD/FeCl 3 was stirred vigorously and kept in the oven at 85° C., with frequent stirring, until required.
  • the remaining molten PEG/DD was dried under vacuum at 95° C. for one and a half hours to remove excess moisture.
  • the moisture content of the PEG/DD was tested using the volumetric Karl Fischer titration method with the specification for moisture being set at no more than 0.05%.
  • a mixer set at 427 rpm was used to agitate the contents of the 2 L jug for 150 seconds, and the DMDI was added during the first 30 seconds.
  • This final mixture was then poured from the 2 L jug into billet moulds, placed in an oven at 95° C. and cured for a specified time, which ranged from 10 to 30 hours. After this time, the oven was turned off and the billets left to cool to ambient.
  • the polymer was then demoulded, and the resultant polymer slabs sliced.
  • a dosage form when placed into a vessel containing liquid media will release drug in a defined manner dictated by the formulation.
  • This process known as dissolution can be used as an in vitro marker of the mechanism of release in the body. Sampling is carried out at regular intervals over a period of several hours and the amount of drug in the samples is analysed by spectrophotometer or HPLC. The data are normally represented as the release of labelled content against time.
  • Pilocarpine in vitro release from the units is performed by a USP paddle method at 50 rpm, 37° C.
  • the pilocarpine released is assayed by HPLC as in the potency method.
  • the blank polymer slices are placed in purified water and agitated at about 4° C. for approximately 16-20 hours; the water is then decanted.
  • Water swollen polymer slices are placed in an ethanol:water solution and agitated at about 4° C. for approximately 6-8 hours.
  • the slices are then dried.
  • Pilocarpine is dissolved in water which is then added to the dry polymer slices.
  • the slices and drug loading solution are agitated at approximately 4° C. for approximately 16-20 hours to allow the uptake of drug. At the end of the dosing period the remaining drug solution is decanted and the swollen polymer slices are dried for 18-28 hours.
  • Polymer batch FX02144 was purified (FX02150) and then loaded with pilocarpine (FX02151).
  • FIG. 3 shows normalised graph of percentage Pilocarpine released against time for linear polymer FX02151 compared with original polymer FX01234 and FX01194
  • the blank polymer slices are placed in purified water and agitated at about 4° C. for approximately 6-8 hours, then the water is decanted.
  • the swollen slices are again placed in purified water and agitated at about 4° C. for approximately 16-20 hours; the water is then decanted.
  • Water swollen polymer slices are placed in an ethanol:water solution and agitated at about 4° C. for approximately 6-8 hours.
  • a solution of Dinoprostone is made by dissolving the appropriate amount of Dinoprostone in ethanol.
  • the resulting solution is added to water and ethanol. This makes up the drug loading solution which is then added to the swollen polymer slices to give a 25% w/w ethanol:water mix.
  • the slices and drug loading solution are agitated at, approximately 4° C. for approximately 16-20 hours to allow the uptake of drug.
  • the remaining drug solution is decanted and the swollen polymer slices are dried for 18-28 hours.
  • Prostaglandin E 2 was loaded by an analogous process into a batch of cross-linked polymer (FX02139, loaded FX02159) and a batch of linear polymer (FX02144, loaded FX02157), both with 0.6 mm thick slices.
  • the measured potencies were 9.4 mg (FX02159, control) and 9.7 mg (FX02157) respectively.
  • FIG. 4 shows PGE 2 release profiles of cross-linked polymer and new linear polymer.
  • Durans 1 and 3 were covered with a one-litre glass beaker, and durans 2 and 4 were left uncovered.
  • Films from durans 1 and 3 feel rough to touch, whereas films from durans 2 and 4 are smooth. Film from duran 2 has a rougher patch at one side.
  • the average weight of a film portion used was 0.0272 g; and the average weight of a polymer slice (FX02141) was 0.1381 g.
  • Polymer manufactured with a PEG:DD:DMDI ratio of 0.25:1:1.25 was shown to have the same characteristics as the cross-linked polymer, with all results within the known cross-linked polymer specifications.
  • linear polymer according to the invention meets these specifications and the results are reproducible. Furthermore, the linear polymer is soluble in certain solvents whereas the known cross-linked polymer is insoluble.
  • the known cross-linked polymer with a percentage swelling of around 300%, cannot be loaded with drugs of high molecular weight, such as peptides and proteins.
  • FX02158 PEG:DD:DMDI 0.7:1:1.7
  • FX02158 PEG:DD:DMDI 0.7:1:1.7
  • Polymers with higher PEG:DD ratios have not reach their maximum percentage swelling by 24 hours. This is confirmed by percentage swellings over time curves ( FIG. 2 ). Polymer slices with a PEG:DD ratio of 0.25:1 reach their maximum swelling by around 5 hours when the curve plateaus, however, polymer slices with a higher PEG:DD ratio of 0.7:1 it was seen that the percentage swelling was increasing at 144 hours with the gradient of the curve at this point being positive.
  • Polymer batch FX02144 (PEG:DD:DMDI 0.25:1:1.25) was loaded with pilocarpine and PGE 2 .
  • This polymer has similar characteristics to cross-linked polymer and therefore, release profiles of both drugs from the two different polymers could be compared.
  • FX02144 was insoluble in methanol, whereas other batches tested were soluble in this solvent.
  • a manufactured film was swollen in demineralised water and the swollen form was found to be strong and stretchy. This swollen film was then removed from the water and allowed to dry. Once dried the film regained its shape and strength.
  • the percentage swelling over time of a polymer film produced was calculated, and compared to the percentage swelling over time of the polymer slices used to make the film. As expected, the portions of film reached their maximum percentage swelling much quicker than the polymer slice because the thickness and average weight of the film portions were much less than the polymer slices. This can be used as an indication of release rate of a drug from a polymer film.
  • PEG4000, PEG8000, PEG12000 and PEG35000 are polyethylene glycols having molecular weight of 4000, 8000, 12000 and 35000, respectively;
  • HD is 1,6-hexanediol
  • DD is 1,10-decanediol
  • DDD is 1,12-dodecanediol
  • HDD is 1,16-hexadecanediol;
  • DMDI is dicyclohexylmethane-4,4-diisocyanate and HMDI is 1,6-hexamethylene diisocyanate.
  • Polymers except batch numbers BP03007, BP03014 and BP03015, were produced with the same polymerisation method as in Section A. The only difference was that the melted PEG and diol mixture was mixed for 30 mins. in a rotavapor, before 100 g was taken out to make a catalyst mixture to produce a more homogenous mixture.
  • a two-step polymerisation method was also used to produce more controlled polymer structure (batch number BP03015).
  • PEG was dried overnight using vacuum and 50° C. in a rotavapor.
  • Diisocyanate was first fed to the stirring tank reactor. Then about 40 g PEG with ferric chloride on the top of it was fed to the reactor. The reactor was heated to 95° C. and PEG was fed to the reactor during 3 hours by using about 20 g portions at the each time. Mixing (30 rpm) was turned on when the reactor temperature reached 95° C. Then the diol was fed to the reactor and mixing increased to 60 rpm and mixed for 5 min. Polymer was poured into the preheated mould (95° C.) and kept for 10 hours in an oven at 95° C. After this time, the oven was turned off and the polymer billets were left to cool to room temperature. The polymer billets were then demoulded and sliced.
  • the drug loaded polymer were analysed for in vitro drug release following USP Method XXIII, Apparatus 2 at 37° C., with 50 rpm paddle speed. Drug release was analysed by ultraviolet spectroscopy or high pressure liquid chromatography (HPLC) as appropriate. Various dissolution parameters or settings are summarised in Table 20.
  • FIG. 6 to 10 show the mean dissolution profiles of each drug candidate from the various polymers.
  • Rate of drug release k values of each dissolution profile was determined by calculating the slope of graph % drug release versus square root time. All the linear relationship between % drug release and square root time has R 2 correlation value >0.95%. Rate of drug release k from the dissolution profiles of each drug candidate from various pessaries are shown in Table 21.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (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)
  • Emergency Medicine (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Inorganic Chemistry (AREA)
  • Medicinal Preparation (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
US10/528,875 2002-09-27 2003-09-26 Water-swellable polymers Abandoned US20060134161A1 (en)

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US12/835,436 US8557281B2 (en) 2002-09-27 2010-07-13 Water-swellable polymers
US13/571,596 US8628798B2 (en) 2002-09-27 2012-08-10 Water-swellable polymers
US14/099,663 US9987364B2 (en) 2002-09-27 2013-12-06 Water-swellable polymers

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20080146716A1 (en) * 2006-12-14 2008-06-19 Ppg Industries Ohio, Inc. Organic-Inorganic Polymer Composites and their Preparation By Liquid Infusion
US20080160065A1 (en) * 2006-07-12 2008-07-03 Janet Anne Halliday Drug delivery polymer with hydrochloride salt of clindamycin
US20090291120A1 (en) * 2006-07-05 2009-11-26 Jukka Tuominen Hydrophilic Polyurethane Compositions
US20090324692A1 (en) * 2006-07-08 2009-12-31 Controlled Therapeutics (Scotland) Limited Polyurethane Elastomers
US20110091488A1 (en) * 2002-09-27 2011-04-21 Controlled Therapeutics (Scotland) Limited Water-swellable polymers
US8460707B2 (en) 2004-08-05 2013-06-11 Ferring B.V. Stabilised prostaglandin composition
US8524254B2 (en) 2006-10-18 2013-09-03 Ferring B.V. Bioresorbable polymers

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EP2520280A3 (en) 2015-01-07
EP1543058B1 (en) 2017-03-22
AU2003267653A1 (en) 2004-04-19
JP4612419B2 (ja) 2011-01-12
US20110091488A1 (en) 2011-04-21
US9987364B2 (en) 2018-06-05
JP2006500456A (ja) 2006-01-05
US8557281B2 (en) 2013-10-15
EP1543058A1 (en) 2005-06-22
HK1072950A1 (zh) 2005-09-16
US8628798B2 (en) 2014-01-14
EP2520280A2 (en) 2012-11-07
US20140107195A1 (en) 2014-04-17
GB0222522D0 (en) 2002-11-06
US20120302635A1 (en) 2012-11-29
WO2004029125A1 (en) 2004-04-08
CA2495341A1 (en) 2004-04-08
CA2495341C (en) 2011-12-06

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