CA2520312A1 - Matrix compositions for controlled delivery of drug substances - Google Patents
Matrix compositions for controlled delivery of drug substances Download PDFInfo
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- CA2520312A1 CA2520312A1 CA002520312A CA2520312A CA2520312A1 CA 2520312 A1 CA2520312 A1 CA 2520312A1 CA 002520312 A CA002520312 A CA 002520312A CA 2520312 A CA2520312 A CA 2520312A CA 2520312 A1 CA2520312 A1 CA 2520312A1
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- composition according
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- composition
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- daltons
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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
- A61K9/0087—Galenical forms not covered by A61K9/02 - A61K9/7023
- A61K9/0092—Hollow drug-filled fibres, tubes of the core-shell type, coated fibres, coated rods, microtubules or nanotubes
-
- 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
- A61K9/2027—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
-
- 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
- A61K9/2095—Tabletting processes; Dosage units made by direct compression of powders or specially processed granules, by eliminating solvents, by melt-extrusion, by injection molding, by 3D printing
-
- 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
- A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
- A61K9/2806—Coating materials
- A61K9/2833—Organic macromolecular compounds
- A61K9/286—Polysaccharides, e.g. gums; Cyclodextrin
- A61K9/2866—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
-
- 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
- A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
- A61K9/2893—Tablet coating processes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
-
- 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
Abstract
A novel matrix composition for pharmaceutical use. The matrix composition has been designed so that it is especially suitable in those situation where an improved bioavailability is desired and/or in those situation where a slightly or insoluble active substance is employed. Accordingly, a controlled release pharmaceutical composition for oral use is provided in the form of a coated matrix composition, the matrix composition comprising i) a mixture of a first and a second polymer that have plasticizing properties and which have melting points or melting intervals of a temperature of at the most 200~C, the first polymer being selected from the group consisting of polyethylene glycols and polyethylene oxides, and the second polymer being selected form block copolymer of ethylene oxide and propylene oxide including poly(ethylene-glycol-b-(DL-lactic acid-co-glycolic acid) - b-ethylene glycol (PEG-PLGA PEG), poly((DL-lactic acid-co-glycolic acid) - g-ethylene glycol) (PLGA-g-PEG), poloxamers and polyethylene oxide - polypropylene oxide (PEO-PPO), ii) a therapeutically, prophylactically and/or diagnostically active substance, the matrix composition being provided with a coating having at least one opening exposing at one surface of said matrix, wherein the active substance is released with a substantially zero order release.
Claims (69)
1. A controlled release pharmaceutical composition for oral use in the form of a coated matrix composition, the matrix composition comprising i) a mixture of a first and a second polymer that have plasticizing properties and which have melting points or melting intervals of a temperature of at the most 200 °C, the first polymer being selected from the group consisting of polyethylene glycols and polyethylene oxides, and the second polymer being selected from block copolymer of ethylene oxide and propylene oxide including poly(ethylene-glycol-b-(DL-lactic acid-co-glycolic acid)-b-ethylene glycol (PEG-PLGA PEG), poly((DL-lactic acid-co-glycolic acid)-g-ethylene glycol) (PLGA-g-PEG), poloxamers and polyethylene oxide - polypropylene oxide (PEO-PPO), ii) a therapeutically, prophylactically and/or diagnostically active substance, the matrix composition being provided with a coating having at least one opening exposing at one surface of said matrix, the coating comprising i) a first cellulose derivative which has thermoplastic properties and which is substantially insoluble in the aqueous medium in which the composition is to be used, and at least one of ii) a second cellulose derivative which is soluble or dispersible in water, iii) a plasticizer, and iv) a filler, wherein the active substance is released with a substantially zero order release.
2. A composition according to claim 1, wherein the first polymer is a polyethylene glycol and/or a polyethylene oxide having a molecular weight of at least about 20,000 in crystalline and/or amorphous form or a mixture such polymers.
3. A composition according to claim 1 or 2, wherein the polyethylene glycol and/or polyethylene oxide has a molecular weight of from about 20,000 daltons, such as, e.g., from about 20,000 to about 700,000 daltons, from about 20,000 to about 600,000 daltons, from about 35,000 to about 500,000 daltons, from about 35,000 to about 400,000 daltons, from about 35,000 to about 300,000 daltons, from about 50,000 to about 300,000 daltons, such as, e.g. about 35,000 daltons, about 50,000 daltons, about 75,000 daltons, about 100,000 daltons, about 150,000 daltons, about 200,000 daltons, about 250,000 daltons, about 300,000 daltons or about 400,000 daltons.
4. A composition according to claim 3, wherein the polyethylene oxide has a molecular weight of about 35,000 daltons, about 50,000 daltons, about 100,000 daltons, and about 200,000 daltons.
5. A composition according to any of the preceding claims, wherein the first polymer has a melting point of about 20-120 °C such as, e.g. from about 30 to about 100 °C or from about 40 to about 80 °C.
6. A composition according to any of the preceding claims, wherein the concentration of the first polymer in the matrix composition is from about 10 to about 99.5% such as, e.g., from about 20 to about 99%, from about 30 to about 99% w/w, from about 35 to about 95% w/w, from about 35 to about 90% w/w, from about 35 to about 85% w/w, from about 35 to about 80% w/w, from about 40 to about 75% w/w, from about 45 to about 70% w/w, from about 45 to about 65% w/w. from about 55 to about 85% w/w or from about 60 to about 85% w/w.
7. A composition according to any of the preceding claims, wherein the second polymer has a molecular weight of at least about 2,000 daltons.
8. A composition according to any of the preceding claims, wherein the second polymer is a poloxamer that has the formula HO(C2H4O)a(C3H6O)b(C2H4O)a H, and a is an integer from about 10 to about 150 such as, e.g., from about 30 to about 140, from about 50 to about 100, from about 65 to about 90, from about to about 90 and b is an integer from about 10 to about 80 such as, e.g., from about 15 to about 80, from about 20 to about 60, from about 25 to about 55.
9. A composition according to claim 8, wherein the poloxamer has a molecular weight of from about 2,000 daltons to about 20,000 daltons such as, e.g., from about 4,000 daltons to about 15,000 daltons or from about 6,000 daltons to about 10,000 daltons.
10. A composition according to any of the preceding claims, wherein the second polymer has a melting point of about 20-120 °C such as, e.g. from about 30 to about 100 °C or from about 40 to about 80 °C.
11. A composition according to any of the preceding claims, wherein the second polymer has a HLB value of at least about 18 such as, e.g., at least about 20.
12. A composition according to any of the preceding claims, wherein the concentration of the second polymer in the matrix composition is from about 0.5% to about 95% w/w such as, e.g., from about 1% to about 90% w/w, from about 5% w/w to about 90% w/w, from about 10% to about 90% w/w, from about 10% to about 80% w/w, from about 10% to about 70% w/w, from about 10% to about 60%, from about 10% to about 50%, from about 15% to about 50% w/w, from about 10% to about 45% w/w, from about 10% to about 40% w/w, from about 15% to about 40% w/w, from about 15% to about 35% w/w or from about 15% to about 30% w/w.
13. A pharmaceutical composition according to any of the preceding claims for controlled release of the active substance into an aqueous medium by erosion of at least one surface of the composition.
14. A composition according to any of the preceding claims, wherein the active substance is present in any of its crystalline, polymorphous or amorphous forms or mixtures thereof.
15. A pharmaceutical composition according to any of the preceding claims, wherein the active substance at least partially is present in solid form in the dispersion.
16. A pharmaceutical composition according to any of the preceding claims, wherein the active substance at least partially is present in a molecular dispersion such as, e.g., in the form of a solid or semi-solid solution.
17. A pharmaceutical composition according to claim 16, wherein the active substance is present in a molecular dispersion including a solid solution.
18. A pharmaceutical composition according to claim 16, wherein the active substance at least partially is present in a colloidal dispersion.
19. A pharmaceutical composition according to claim 14, wherein the active substance at least partially is present in a crystalline form.
20. A pharmaceutical composition according to any of the preceding claims, wherein the active substance at least partially is present in amorphous form with a mean particle size of from about 0.01 µm to about 500 µm such as, e.g., from about 0.05 µm to about 500 µm, from about 0.1 µm to about 500 µm, typically from about 0.5 µm to about 300 µm, more typically from about 1 µm to about 200 µm, especially from about 1 µm to about 100 µm.
21. A composition according to any of the preceding claims, wherein the first and the second polymer together form a dispersion medium in which the active substance is contained.
22. A composition according to any of the preceding claims comprising a stabilizing agent.
23. A composition according to claim 22, wherein the stabilizing agent is selected from the group consisting of diffusion and dissolution adjusting agents, pH-adjusting agents, buffering agents, agents that does not increase the mobility of the ingredients in the composition, agents that prevent crystal formation and agents that have antioxidative properties.
24. A composition according to claim 22 or 23, wherein the stabilizing agent is selected from the group consisting of inorganic acids, inorganic bases, inorganic salts, organic acids or bases and pharmaceutically acceptable salts thereof, saccharides, oligosaccharides, polysaccharides, and cellulose and cellulose derivatives, or mixtures thereof.
25. A composition according to claim 24, wherein the organic acid is a mono-, di-oligo, polycarboxylic acid or amino acids such as, e.g. acetic acid, ethanoic acid, succinic acid, citric acid, tartaric acid, acrylic acid, benzoic acid, malic acid, maleic acid, adipic acid, angelic acid, ascorbic acid/vitamin C, carbamic acid, cinnamic acid, citramalic acid, formic acid, fumaric acid, gallic acid, gentisic acid, glutaconic acid, glutaric acid, glyceric acid, glycolic acid, glyoxylic acid, lactic acid, levulinic acid, malonic acid, mandelic acid, oxalic acid, oxamic acid, pimelic acid, pyruvic acid, aspartic and glutamic acid, or mixtures thereof.
26. A composition according to claim 24, wherein the inorganic acid is pyrophosphoric, glycerophosphoric, phosphoric such as ortho or meta phosphoric, boric acid, hydrochloric acid, or sulfuric acid, or mixtures thereof.
27. A composition according to claim 24, wherein the suitable inorganic compounds include aluminium.
28. A composition according to claim 24, wherein the suitable organic bases are selected from the group consisting of p-nitrophenol, succinimide, benzenesulfonamide, 2-hydroxy-2cyclohexenone, imidazole, pyrrole, diethanolamine, ethyleneamine, tris (hydroxymethyl) aminomethane, hydroxylamine and derivates of amines, sodium citrate, aniline, and hydrazine, or mixtures thereof.
29. A composition according to claim 24, wherein the suitable inorganic bases are selected from the group consisting of aluminium oxide such as, e.g., aluminium oxide trihydrate, alumina, sodium hydroxide, potassium hydroxide, calcium carbonate, ammonium carbonate, ammnonium hydroxide, KOH and the like, or mixtures thereof.
30. A composition according to claim 24, wherein the pharmaceutically acceptable salt of an organic acid is e.g. an alkali metal salt or an alkaline earth metal salt such as, e.g. sodium phosphate, sodium dihydrogenphosphate, disodium hydrogenphosphate etc., potassium phosphate, potassium dihydrogenphosphate, potassium hydrogenphosphate etc., calcium phosphate, dicalcium phosphate etc., sodium sulfate, potassium sulfate, calcium sulfate, sodium carbonate, sodium hydrogencarbonate, potassium carbonate, potassium hydrogencarbonate, calcium carbonate, magnesium carbonate etc., sodium acetate, potassium acetate, calcium acetate, sodium succinate, potassium succinate, calcium succinate, sodium citrate, potassium citrate, calcium citrate, sodium tartrate, potassium tartrate, calcium tartrate, zinc gluconate, zinc sulphate etc., or mixtures thereof.
31. A composition according to claim 24, wherein the inorganic salt is sodium chloride, potassium chloride, calcium chloride, magnesium chloride etc., or mixtures thereof.
32. A composition according to claim 24, wherein the pharmaceutically acceptable excipient is selected from glucose and other monosaccharides, ribose, arabinose, xylose, lyxose, allose, altrose, inosito, glucose, sorbitol, mannose, gulose, idose, galactose, talose, mannitol, fructose, lactose, sucrose, and other disaccharides, dextrin, dextran or other polysaccharides, amylose, xylan, cellulose and cellulose derivatives such as, e.g. microcrystalline cellulose, methyl cellulose, ethyl cellulose, ethylhydroxyethyl cellulose, ethylmethylcellulose, hydroxyethylcellulose, hydroxyethylmethyl cellulose, carboxymethyl cellulose, hydroxypropyl cellulose, hydroxymethylpropyl cellulose, hydroxypropylmethyl cellulose, amylopectin, pectin, starch, sodium starch etc.,kaolin, bentonit, acacia, alginic acid, sodium alginate, calcium alginate, gelatin, dextrose, molasses, extract of Irish moss, panwar gum, ghatti gum, mucilage of isapol husk, veegum, glycollate, magnesium stearate, calcium stearate, stearic acid, talc, titanium dioxide, silicium dioxide, clays, croscarmellose, gums, agar etc., or mixtures thereof.
33. A composition according to any of the preceding claims further comprising a pharmaceutically acceptable excipient selected from the group consisting of fillers, diluents, disintegrants, glidants, pH-adjusting agents, viscosity adjusting agents, solubility increasing or decreasing agents, osmotically active agents and solvents.
34. A composition according to claim 24, wherein the stabilizing agent is citric acid including solvates and anhydrates thereof.
35. A composition according to claim 34, wherein the citric acid has a water content of at the most about 15% w/w such as, e.g., at the most about 12% w/w, such as e.g., at the most about 10% w/w, such as e.g., at the most about 8%
w/w, such as e.g., at the most about 5% w/w, such as e.g., at the most about 3%
w/w, such as e.g., at the most about 2% w/w, such as at the most about 1 % w/w or at the most about 0.5% w/w.
w/w, such as e.g., at the most about 5% w/w, such as e.g., at the most about 3%
w/w, such as e.g., at the most about 2% w/w, such as at the most about 1 % w/w or at the most about 0.5% w/w.
36. A composition according to claim 24, wherein the stabilizing agent is a phosphoric acid or a phosphonic acid or a salt thereof.
37. A composition according to claim 36, wherein the phosphoric acid is ortho or meta phoshoric acid or a mixture thereof.
38. A composition according to any of the preceding claims, wherein the concentration of the active substance in the composition corresponds to a concentration of at the most the saturated concentration in component i) at a temperature corresponding to the melting point or the lowest end point of the melting interval of component i).
39. A composition according to any of the preceding claims, wherein the first polymer and/or the second polymer is of a quality that ensures that free radicals formed, if any, do not significantly increase the degradation of the active substance in the composition.
40. A composition according to any of the preceding claims further comprising one or more antioxidants that inhibits the formation of peroxides and/or inactivates any peroxides present.
41. A composition according to any of the preceding claims, wherein the active substance has antioxidant properties.
42. A composition according to any of the preceding claims, wherein the composition is stable with respect to physical stability.
43. A composition according to any of the preceding claims, wherein the composition is stable with respect to in vitro dissolution of the active substance from the composition.
44. A composition according to claim 43, wherein the composition is stable with respect to in vitro dissolution behaviour in such a manner that t50%, i.e. the time for 50% w/w of the active substance to dissolve in a dissolution medium, differs at the most ~ 20% w/w such as, e.g., at the most ~ 15% w/w, at the most ~ 10%
w/w, at the most ~ 7.5% w/w, at the most ~ 5% w/w, at the most ~ 2.5% w/w, at the most ~ 1.5% w/w or at the most 1% w/w when two compositions from the same batch is compared with a time difference of 2 weeks under similar storage and test conditions.
w/w, at the most ~ 7.5% w/w, at the most ~ 5% w/w, at the most ~ 2.5% w/w, at the most ~ 1.5% w/w or at the most 1% w/w when two compositions from the same batch is compared with a time difference of 2 weeks under similar storage and test conditions.
45. A composition according to any of the preceding claims, wherein the composition is stable with respect to chemical stability of the active substance.
46. A composition according to claim 45, wherein the concentration of the active substance in the composition decreases at the most 20% w/w such as, e.g. at the most 15% w/w, at the most 10% w/w, at the most 7.5% w/w or at the most 5% w/w when stored at room temperature for a time period of at least 3 months such as, e.g. 6 months, 12 months, 18 months or 24 months and a relative humidity of at the most 75% such as, e.g., at the most 70%, at the most 65%, at the most 60%, at the most 55%, at the most 50% or at the most 45%.
47. A composition according to any of the preceding claims, wherein the active substance is present in the composition in a concentration of from about 0.1 to about 98% w/w such as, e.g. at the most about 90% w/w, at the most about 85%
w/w, at the most about 80% w/w, at the most about 75% w/w, at the most about 70% w/w, at the most about 65% w/w or at the most about 60% w/w.
w/w, at the most about 80% w/w, at the most about 75% w/w, at the most about 70% w/w, at the most about 65% w/w or at the most about 60% w/w.
48. A composition according to any of the preceding claims, wherein the active substance has a solubility of at the most about 3 mg/ml such as, e.g., at the most about 1 mg/ml, at the most about 0.1 mg/ml, at the most about 0.05 mg/ml such as, e.g. at the most about 0.001 mg/ml in water at ambient temperature.
49. A composition according to any of the preceding claims, wherein any exposed matrix surfaces erode at a substantially constant rate.
50. A composition according to any of the preceding claims, wherein in the aqueous medium in which the composition is to be used, the coating does not completely crumble or erode before the matrix has completely eroded.
51. A composition according to any of the preceding claims, wherein said first cellulose derivative is a cellulose ether which, when heated, is shapeable by molding or extrusion, including injection molding, blow molding and compression molding.
52. A composition according to claim 51 in which the cellulose ether comprises at least one ethylcellulose.
53. A composition according to any of claims 1-51 in which said first cellulose derivative is selected from the group consisting of cellulose acetate, cellulose propionate and cellulose nitrate.
54. A composition according to any of the preceding claims in which said second cellulose derivative is selected from the group consisting of methylcellulose, carboxymethylcellulose and salts thereof, cellulose acetate phthalate, microcrystalline cellulose, ethylhydroxyethylcellulose, ethylmethylcellulose, hydroxyethylcellylose, hydroxyethylmethylcellulose, hydroxypropylcellulose, hydroxymethylcellulose and hydroxymethylpropylcellulose.
55. A composition according to claim 54 in which said salt of carboxymethylcelllulose is selected from the group consisting of alkali metal and alkaline earth metal salts.
56. A composition according to any of the preceding claims, in which said plasticizer is selected from the group consisting of phosphate esters;
phthalate esters; amides; mineral oils; fatty acids and esters thereof with polyethylene glycol, glycerin or sugars; fatty alcohols and ethers thereof with polyethylene glycol, glycerin or sugars; vegetable oils and hydrogenated vegetable oils;
nitrobenzene, carbon disulfide, .beta.-naphtyl salicylate, phthalyl glycolate, diocyl phthalate etc.
phthalate esters; amides; mineral oils; fatty acids and esters thereof with polyethylene glycol, glycerin or sugars; fatty alcohols and ethers thereof with polyethylene glycol, glycerin or sugars; vegetable oils and hydrogenated vegetable oils;
nitrobenzene, carbon disulfide, .beta.-naphtyl salicylate, phthalyl glycolate, diocyl phthalate etc.
57. A composition according to claim 56 in which said fatty alcohol is selected from the group consisting of cetostearyl alcohol, cetyl alcohol, stearyl alcohol, oleyl alcohol and myristyl alcohol.
58. A composition according to any of claims 1-55 in which said plasticizer is a non-ionic surfactant.
59. A composition according to any of the preceding claims, wherein the solid dispersion does not contain polyethylene glycol 2000 monostearate or polyethylene glycol 400 monostearate.
60. A composition according to any of the preceding claims, wherein the first polymer has a molecular weight of at least 100,000 daltons and at the most 400,000 daltons.
61. A composition according to any of the preceding claims, wherein the release of the active substance from the composition is zero order and about 50% w/w of the active substance is released from the composition within 5-6 hours from start of release as measured by the dissolution test described herein.
62. A composition according to any of claims 1-60, wherein the release of the active substance from the composition is zero order and about 50% w/w of the active substance is released from the composition within 4-5 hours from start of release as measured by the dissolution test described herein.
63. A composition according to any of claims 1-60, wherein the release of the active substance from the composition is zero order and about 50% w/w of the active substance is released from the composition within 3-4 hours from start of release as measured by the dissolution test described herein.
64. A composition according to any of claims 1- 60, wherein the release of the active substance from the composition is zero order and about 50% w/w of the active substance is released from the composition Within 2-3 hours from start of release as measured by the dissolution test described herein.
65. A composition according to any of the preceding claims, wherein the release of the active substance from the composition is substantially delayed for 0.25 to 4 hours, e.g. for 0.5 to 3 hours, such as from 1 to 2 hours before the zero order release starts as measured by the dissolution test described herein.
66. A method for preparing a composition according to any of claims 1-65, the method comprises injection moulding of a melted or semi-solid mixture of the individual components making up the composition into a suitable form, application of a coating by means of injection moulding and cooling the thus prepared coated composition to solidify the composition.
67. A method according to claim 66, wherein the method is a substantially single continuous process.
68. A method according to claim 67, Wherein the cooling is performed under controlled conditions to a temperature of from about 0 °C to about 20 °C such as, e.g. from about 5 °C to about 18 °C, from about 10 °C to about 16 °C such as, e.g. about 10 °C, about 12 °C, about 14 °C, about 15 °C or about 16 °C.
69. A method according to claim 66 or 67 comprising a step of heating while the polymer and the active substance is in physical contact with each other.
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
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DKPA200300464 | 2003-03-26 | ||
DKPA200300464 | 2003-03-26 | ||
PCT/DK2003/000765 WO2004041252A1 (en) | 2002-11-08 | 2003-11-07 | Controlled release carvedilol compositions |
DKPCT/DK03/00765 | 2003-11-07 | ||
PCT/DK2004/000217 WO2004084869A1 (en) | 2003-03-26 | 2004-03-26 | Matrix compositions for controlled delivery of drug substances |
Publications (2)
Publication Number | Publication Date |
---|---|
CA2520312A1 true CA2520312A1 (en) | 2004-10-07 |
CA2520312C CA2520312C (en) | 2013-06-18 |
Family
ID=33099580
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA2520312A Expired - Fee Related CA2520312C (en) | 2003-03-26 | 2004-03-26 | Matrix compositions for controlled delivery of drug substances |
Country Status (9)
Country | Link |
---|---|
US (2) | US8298581B2 (en) |
EP (3) | EP2186510B1 (en) |
JP (1) | JP4989217B2 (en) |
AT (2) | ATE454886T1 (en) |
CA (1) | CA2520312C (en) |
DE (2) | DE602004014747D1 (en) |
DK (1) | DK1610768T3 (en) |
ES (1) | ES2307003T3 (en) |
WO (1) | WO2004084869A1 (en) |
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- 2004-03-26 DE DE602004014747T patent/DE602004014747D1/en active Active
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US8298581B2 (en) | 2012-10-30 |
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EP1974726B1 (en) | 2010-01-13 |
EP1974726A2 (en) | 2008-10-01 |
WO2004084869A1 (en) | 2004-10-07 |
ATE454886T1 (en) | 2010-01-15 |
EP1610768A1 (en) | 2006-01-04 |
EP2186510B1 (en) | 2013-07-10 |
JP2006521301A (en) | 2006-09-21 |
JP4989217B2 (en) | 2012-08-01 |
EP2186510A3 (en) | 2010-06-09 |
DE602004014747D1 (en) | 2008-08-14 |
EP1610768B1 (en) | 2008-07-02 |
CA2520312C (en) | 2013-06-18 |
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