WO2001024777A1 - Coated solid dosage forms - Google Patents
Coated solid dosage forms Download PDFInfo
- Publication number
- WO2001024777A1 WO2001024777A1 PCT/EP2000/009576 EP0009576W WO0124777A1 WO 2001024777 A1 WO2001024777 A1 WO 2001024777A1 EP 0009576 W EP0009576 W EP 0009576W WO 0124777 A1 WO0124777 A1 WO 0124777A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- released
- drug
- hours
- hours exposure
- solid dose
- Prior art date
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- 0 C*C(C(*)C(C)N=O)C(C(C(*)C(C)*)O)O Chemical compound C*C(C(*)C(C)N=O)C(C(C(*)C(C)*)O)O 0.000 description 2
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
- A61K9/20—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
- A61K9/284—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone
- A61K9/2846—Poly(meth)acrylates
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- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/167—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction with an outer layer or coating comprising drug; with chemically bound drugs or non-active substances on their surface
- A61K9/1676—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction with an outer layer or coating comprising drug; with chemically bound drugs or non-active substances on their surface having a drug-free core with discrete complete coating layer 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
- A61K9/2072—Pills, tablets, discs, rods characterised by shape, structure or size; Tablets with holes, special break lines or identification marks; Partially coated tablets; Disintegrating flat shaped forms
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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
- A61K9/20—Pills, tablets, discs, rods
- A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
- A61K9/2886—Dragees; Coated pills or tablets, e.g. with film or compression coating having two or more different drug-free coatings; Tablets of the type inert core-drug layer-inactive layer
Definitions
- the present invention relates to novel pharmaceutical compositions such as oral formulations for once a day administration of a drug/medicament and to novel solid dose units for incorporation therein.
- the solid dose units provide a phased release of drug to target or prolong the pharmaceutical effect.
- the compositions are particularly useful for multiphase delivery of proton pump inhibitors such as lansoprazole, pantoprazole, omeprazole, perprazole, etc.
- compositions capable of delivering drug at timed periods during 24 hours when a condition and/or symptom occurs or reoccurs in particular formulations capable of providing pulsed release of a drug, where the drug is released in at least two pulses, the second pulse releases drug when the effect of the first release is at least partially diminished and, if applicable, any further pulses also release drug when the effects of the previous pulse are at least partially diminished.
- pharmaceutical formulations capable of providing a single daily dose of a drug affecting gastric pH such as a proton pump inhibitor
- formulations capable of maintaining the gastric pH above about above 3.0, preferably above 4.0, for a period of about 24 hours after a single daily dose e.g. formulations capable of delivering drug at timed periods during 24 hours when an increase in pH is expected.
- sustained release formulations can be used, e.g. before the patient goes to bed, but they often result in the use of more drug than required.
- delayed release formulations capable of releasing drug in anticipation of symptoms.
- the formulation could suitably include multiple doses such that it can be taken to provide immediate relief followed by further relief after a predetermined period of time.
- rheumatoid arthritis One condition which could be treated with such a formulation is rheumatoid arthritis. Patients suffering from rheumatoid arthritis experience difficulty in moving when they wake and so it would be advantageous to provide a formulation which could be taken at night and which would release the drug the following morning so that its effects are achieved before the patient wakes.
- the formulation could suitably include multiple doses such that it can be taken during the day to provide immediate relief in addition to relief the following morning.
- delayed release formulations capable of releasing drug after a predetermined delay, preferably being such that the delayed release of the drug coincides with and /or anticipates the occurrence or reoccurrence of the symptom or condition to be treated.
- the present invention addresses one or more of the problems discussed above. It has been found that the inclusion of a disintegrant in the core of a solid dose unit, surrounded by an outer semi-permeable membrane comprising a permeable water insoluble polymer and at least 50 % by weight glidant surprisingly provides the desired delay and subsequent release profile.
- the novel formulation is capable of delaying the release in a largely pH independent manner. After the period of delay, drug release is immediately initiated.
- the delay and the subsequent release profile can be manipulated by the selection of the composition and /or thickness of the semi-permeable membrane and /or the composition and /or amount of disintegrant included in the core.
- T e arrangement of the disintegrant in the core can also be adapted to influence the delay and subsequent release profile, e.g. it can be included as a separate outer layer of the core.
- a first aspect of the invention provides a solid dose unit for the delayed release of a drug comprising:
- a core comprising the drug and at least one disintegrant
- an outer semi-permeable membrane surrounding the core which comprises a permeable water insoluble polymer and at least 50 % by weight glidant.
- the solid dose units may suitably be pellets, mini-tablets, granules, tablets etc. which are well known in the art.
- the drug may be included in the units by any suitable conventional means, e.g. it may be incorporated in the core material or it may be applied to a seed core as a coat, with or without other constituents which make up the unit.
- the drug and the disintegrant may be included as separate layers of the core or they may be mixed together in the core.
- the units are preferably such that when they are subjected to in-vitro exposure to simulated intestinal fluid minimal drug is released until after at least four hours exposure and substantially all of the drug is released after 24 hours exposure.
- Preferred embodiments are those wherein minimal drug is released until after at least six hours in-vitro exposure to simulated intestinal fluid.
- Further embodiments of the invention are those which provide minimal drug release until after at least 8, 9, 10, 11 and 12 hours in-vitro exposure to simulated intestinal fluid respectively.
- substantially all of the drug is released after 24 hours in-vitro exposure to simulated intestinal fluid, more preferably substantially all of the drug is released after 22 hours in-vitro exposure to simulated intestinal fluid.
- the in-vitro dissolution profile may be determined by techniques known in the art, for example using USP apparatus IV at 16 ml/min in 0.5M phosphate buffer pH 6.5, temperature 37°C. The results should vary only a little depending on the method of measurement.
- less than 10% of the drug is released after four hours in-vitro exposure to simulated intestinal fluid, at least 30% is released after ten hours exposure and at least 70% is released after 24 hours exposure, preferably at least 70% is released after 20 hours exposure.
- these measurements are cumulative, i.e. the term "is released after” indicates the total amount of released drug that is measured at the stated time, i.e. after 4, 10 or 20 hours in-vitro exposure to simulated intestinal fluid.
- less than 5% of the drug is released after four hours in- vitro exposure to simulated intestinal fluid, at least 35% is released after ten hours exposure and at least 75% is released after is released after 24 hours exposure, preferably at least 75% is released after 20 hours exposure. In a further embodiment less than 5% of the drug is released after four hours in-vitro exposure to simulated intestinal fluid, at least 40% is released after ten hours exposure and at least 80% is released after 20 hours exposure.
- less than 10% of the drug is released after six hours in-vitro exposure, at least 30% is released after ten hours and at least 70% is released after 24 hours, preferably at least 70% is released after 20 hours.
- less than 5% of the drug is released after six hours in-vitro exposure, at least 35% is released after ten hours and at least 75% is released after 20 hours.
- less than 5% of the drug is released after six hours in-vitro exposure, at least 40% is released after ten hours and at least 80% is released after 20 hours.
- less than 10% of the drug is released after 8 hours in-vitro exposure, at least 30% is released after 12 hours and at least 70% is released after 24 hours, preferably at least 70% is released after 20 hours.
- less than 5% of the drug is released after 8 hours in- vitro exposure, at least 35% is released after 12 hours and at least 75% is released after 20 hours.
- less than 5% of the drug is released after 8 hours in-vitro exposure, at least 40% is released after ten hours and at least 80% is released after 20 hours.
- less than 10% of the drug is released after 10 hours in-vitro exposure, at least 30% is released after 14 hours and at least 70% is released after 24 hours exposure, preferably at least 70% is released after 22 hours.
- less than 5% of the drug is released after 10 hours in-vitro exposure, at least 35% is released after 14 hours and at least 75% is released after 22 hours.
- less than 5% of the drug is released after 10 hours in-vitro exposure, at least 40% is released after 14 hours and at least 80% is released after 22 hours.
- less than 10% of the drug is released after 12 hours in-vitro exposure, at least 30% is released after 16 hours and at least 70% is released after 24 hours. In a further embodiment less than 5% of the drug is released after 12 hours in-vitro exposure, at least 35% is released after 16 hours and at least 75% is released after 24 hours. In a further embodiment less than 5% of the drug is released after 12 hours in-vitro exposure, at least 40% is released after 16 hours and at least 80% is released after 24 hours.
- Suitable disintegrants include croscarmellose sodium, crospovidone, sodium starch glycolate etc. These materials result in swelling and disintegration of the dosage unit.
- the semi-permeable membrane comprises a permeable water insoluble polymer and at least 50 % by weight glidant The weight of the glidant accounts for at least 50% of the total weight of the membrane.
- the semi-permeable membrane may optionally comprise further components, but preferred embodiments are those wherein the membrane comprises the permeable water insoluble polymer and the glidant only.
- the semi-permeable membrane preferably comprises at least 55% glidant, more preferablv at least 60% glidant and most preferably at least 65% glidant
- Particular embodiments of the invention include a semi-permeable membrane which comprises at least 66 % glidant
- Suitable ghdants include talc, silicon dioxide, kaolin, glycerol monostearate, metal stearates such as magnesium stearate, titanium dioxide and starch preferred ghdants are talc, silicon dioxide and kaolin
- the most preferred glidant is talc
- Pharmaceutical compositions usually comprise less than 30% ghdants such as talc, however the function of the glidant in the present invention is completely different from the conventional function, the high level of glidant mcluded in the semi-permeable membrane affects the mechanical and physical properties of the membrane.
- Suitable polymers include methacrylic acid polymers such as Eudragits, addition polymers such as PVAP, PVP and PVA, cellulose derivatives such as cellulose acetate, ethylcellulose, cellulose acetate succmate, cellulose acetate phthalate, hydroxypropylmethylcellulose and suitable resins such as shellac.
- Preferred polymers are methacrylic acid derivatives, ethylcellulose and cellulose acetate.
- the most preferred polymers are methacrylic acid polymers such as Eudragits, particularly Eudragit RS.
- the membrane preferably lacks a plasticiser.
- the semi-permeable membrane is surprisingly capable of resisting pressure from the swelling of the disintegrant material until a critical point at which it ruptures and drug release immediately commences.
- the units preferably release the drug in a non-osmotic, largely pH independent manner.
- the units preferably lack protection from the environment of the stomach, e.g. they lack an enteric coat.
- the units preferably lack osmotic modifiers.
- the units are particularly suitable for the controlled release of proton pump inhibitors, preferably lansoprazole, pantoprazole, omeprazole, perprazole, etc. They may be included in formulations suitable for the treatment of duodenal ulcers, peptic ulcers and reflux oesophagitis.
- the units are also suitable for the controlled delivery of other drugs, e.g. drugs that are conventionally administered in multiple doses or when timing is important for the reasons discussed above.
- Drugs which may be included in the units include, e.g. proton pump inhibitors, anti-inflammatories, antihypertensives, antibiotics, hormonal drugs and drugs which are active on the endocrine system.
- proton pump inhibitor when used herein refers not only to the active compounds but also to appropriate prodrugs and derivatives. The term also covers appropriate salts of the compounds, prodrugs and derivatives.
- the cores may suitably comprise one or more of the following: a stabiliser such as magnesium carbonate; a binder such as hydroxypropylcellulose LF grade or EXF grade; a disintegrant such as hydroxypropylcellulose (low substituted) 1- hpc 31; a binder or diluent such as sucrose, maize starch; and/or a lubricant such as magnesium stearate.
- a stabiliser such as magnesium carbonate
- a binder such as hydroxypropylcellulose LF grade or EXF grade
- a disintegrant such as hydroxypropylcellulose (low substituted) 1- hpc 31
- a binder or diluent such as sucrose, maize starch
- a lubricant such as magnesium stearate.
- a second aspect of the invention provides a plurality of solid dose units as described above which collectively exhibit the following in-vitro dissolution profile when subjected to in-vitro exposure to simulated intestinal fluid:
- intestinal fluid less than 10% of the drug is released, preferably less than 7% is released, more preferably less than 5% is released and most preferably less than 2% is released.
- Further embodiments of the invention are those wherein after at least 8, 9, 10, 11 and 12 hours in-vitro exposure to simulated intestinal fluid respectively less than 10% of the drug is released, preferably less than 7% is released, more preferably less than 5% is released and most preferably less than 2% is released.
- For each of these embodiments after ten hours in-vitro exposure to simulated intestinal fluid at least 50% of the drug is released, preferably at least 55% is released, more preferably at least 60% is released and most preferably at least 65% is released.
- For each of these embodiments after 24 hours in-vitro exposure to a simulated intestinal fluid at least 70% of the drug is released, preferably at least 75% is released, more preferably at least 80% is released.
- less than 10% of the drug is released after four hours in-vitro exposure, at least 30% is released after ten hours and at least 70% is released after 20 hours. In a further embodiment less than 5% of the drug is released after four hours in-vitro exposure, at least 35% is released after ten hours and at least 75% is released after 20 hours. In a further embodiment less than 5% of the drug is released after four hours in-vitro exposure, at least 40% is released after ten hours and at least 80% is released after 20 hours.
- less than 10% of the drug is released after six hours in-vitro exposure, at least 30% is released after ten hours and at least 70% is released after 20 hours. In a further embodiment less than 5% of the drug is released after six hours in-vitro exposure, at least 35% is released after ten hours and at least 75% is released after 20 hours. In a further embodiment less than 5% of the drug is released after six hours in-vitro exposure, at least 40% is released after ten hours and at least 80% is released after 20 hours.
- less than 10% of the drug is released after 8 hours in-vitro exposure, at least 30% is released after 12 hours and at least 70% is released after 20 hours. In a further embodiment less than 5% of the drug is released after 8 hours in-vitro exposure, at least 35% is released after 12 hours and at least 75% is released after 20 hours. In a further embodiment less than 5% of the drug is released after 8 hours in-vitro exposure, at least 40% is released after ten hours and at least 80% is released after 20 hours. In yet another embodiment of the invention less than 10% of the drug is released after 10 hours in-vitro exposure, at least 30% is released after 14 hours and at least 70% is released after 22 hours.
- less than 5% of the drug is released after 10 hours in-vitro exposure, at least 35% is released after 14 hours and at least 75% is released after 22 hours. In a further embodiment less than 5% of the drug is released after 10 hours in-vitro exposure, at least 40% is released after 14 hours and at least 80% is released after 22 hours.
- less than 10% of the drug is released after 12 hours in-vitro exposure, at least 30% is released after 16 hours and at least 70% is released after 24 hours. In a further embodiment less than 5% of the drug is released after 12 hours in-vitro exposure, at least 35% is released after 16 hours and at least 75% is released after 24 hours. In a further embodiment less than 5% of the drug is released after 12 hours in-vitro exposure, at least 40% is released after 16 hours and at least 80% is released after 24 hours.
- a third aspect of the invention provides an oral formulation for the controlled release of a drug which comprises solid dose units as described above.
- These include oral formulations for the controlled release of a drug which comprises a first population of solid dose units comprising the drug and a second population of solid dose units comprising the drug wherein the first population comprises units which exhibit the following in-vitro dissolution profile when subjected to in-vitro exposure to simulated intestinal fluid:
- the units of the first population are preferably such that after two hours in-vitro exposure to simulated intestinal fluid at least 65% of the total drug included in the first population is released, more preferably at least 70% is released, most preferably at least 75% is released.
- the units of the first population are preferably such that after three hours in-vitro exposure to simulated intestinal fluid at least 80% of the total proton pump drug included in the first population is released, more preferably at least 85% is released, most preferably at least 90% is released.
- the units of the invention may be included in any suitable oral formulation, e.g. tablets, capsules and microcapsules.
- suitable oral formulation e.g. tablets, capsules and microcapsules.
- suitable excipients and for inclusion in the formulations will be apparent to a person of skill in the art, as will suitable excipients and for inclusion in the formulations.
- the units of the first population preferably release the drug when the formulation or the units pass from the stomach into the intestine as a result of the change in pH. This may be achieved by known means, e.g. by coating the units with an enteric coat. The change in pH when the environment of the duodenum is reached causes the enteric coat to dissolve and release the drug.
- Suitable materials from which enteric coats may be prepared are well known in the art, e.g. cellulose acetate phthalate, hydroxypropylmethylcellulose phthalate,
- Preferred materials are Eudragit S100, Eudragit L 100, Eudragit L 100.55 and
- Eudragit L30D-55 most preferably Eudragit L30D-55.
- the formulations are suitable for the multiphase delivery of proton pump inhibitors, preferably lansoprazole, pantoprazole, omeprazole or perprazole. These formulations are suitable for the treatment of duodenal ulcers, peptic ulcers and reflux oesophagitis.
- the formulations are also suitable for the phased delivery of other drugs, e.g. drugs that are conventionally administered in multiple doses or at as sustained release formulations for the reasons discussed above.
- Drugs which may be included in the formulations include, e.g. proton pump inhibitors, anti-inflammatories, antihypertensives, antibiotics, hormonal drugs and drugs which are active on the endocrine system.
- the drug included in the first and second populations of units may be different or identical.
- Preferred formulations are those in which the drug included in the first and second populations of units are identical.
- the amount of drug included in the first and second populations of units may be different or identical.
- the units may suitably be incorporated in a delivery system which provides multiphased delivery of a drug, i.e. which provides at least two phases of delivery from a single dosage formulation. Further phases of delivery can be provided by including further populations of solid dose units adapted to deliver drug after a different period of delay.
- the time interval between phases can be manipulated by the selection of the composition of the units, i.e. the selection of the composition and /or thickness of the semi-permeable membrane and /or the composition and/or amount of disintegrant included in the core and/or the arrangement of the disintegrant in the core of each population.
- the formulations are preferably suitable for once daily administration. They are preferably suitable for controlling gastric pH over a 24 hour period. Particularly preferred formulations are those capable of controlling gastric pH over a 24 hour period so as to prevent the pH falling below 4.0 over this period.
- the present invention also provides a composition comprising a permeable water insoluble polymer and at least 50 % by weight of glidant which is suitable in the preparation of the solid dose units described above.
- the composition more preferably comprises at least 55% by weight glidant, even more preferably at least 60% glidant and most preferably at least 65% by weight glidant.
- Particular embodiments of the invention include at least 66 % by weight glidant.
- Preferred glidant materials include talc, silicon dioxide, kaolin, glycerol monostearate, magnesium stearate and other metal stearates, the most preferred glidant is talc.
- the polymer may suitably be a methacrylic acid polymers, e.g. a Eudragit.
- the present invention still further provides a method for the preparation of the solid dose units described above which comprises coating a core comprising a drug and a disintegrant with a composition comprising a permeable water insoluble polymer and at least 50 % by weight glidant.
- the present invention also provides a method for the preparation of the oral formulations described above which comprises bringing solid dose units as described above into association with suitable components to provide a pellet, mini-tablet, granule or tablet.
- Figure 1. is a graph showing the in-vitro release profile of the type A lansoprazole pellets of Example 1 in pH 6.5 phosphate buffer.
- Figure 2. is a graph showing the in-vitro release profile of the type B lansoprazole pellets of Example 1 in pH 6.5 phosphate buffer.
- Figure 3 is a graph showing the in-vitro release profile of lansoprazole formulations A and B of Example 2 in pH 6.5 phosphate buffer.
- Figure 4. is a graph showing the in-vivo release profile of lansoprazole formulations A and B of Example 2.
- Figure 5 is a graph showing the in-vitro release profile of a single lansoprazole minitablet of Example 3 in pH 6.5 phosphate buffer.
- Example 1 Preparation of pellets containing lansoprazole
- the resulting drug containing cores were sieved and returned to the rotor A suspension of hydroxypropylcellulose in isopropylalcohol and croscarmellose sodium and was sprayed onto the cores to provide disintegrant layered cores having the following composition:
- the disintegrant coated cores were sieved and placed in a fluidisation chamber operating m a W ⁇ rster mode.
- a polymer coat consisting of Eudragit RS and suspended talc was sprayed onto the cores continuously to provide pellets having the following compositions:
- Disintegrant layered core 57.9 % Type B w/w
- Example 2 Preparation of a mixture of: pellets according to Example 1 and immediate release pellets
- Titanium dioxide 1.2 %
- Formulation A Type A pellets and Immediate release pellets
- Formulation B Type B pellets and Immediate release pellets
- a dry granulation was prepared from lansoprazole, lactose, microcrystalline cellulose and magnesium stearate by mixing and dry granulation.
- a second granulation containing magnesium carbonate, crospovidone and hydroxyporpylcellulose was prepared by wet granulation .
- the wet granulation product was dried and milled to an appropriate size before mixing with the product of the dry granulation.
- the resultant blend was compressed into minitablets of 4 mm diameter using standard tooling on a Kilian LX tablet press.
- Microcrystalline Cellulose (Avicel PH101) 11.225 37.42 % Magnesium stearate 0.21 0.70 %
- the uncoated minitablets were coated, as described in Example 1, with Eudragit and talc: w/w Eudragit RS 7.5%
Abstract
Description
Claims
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
HU0203311A HUP0203311A3 (en) | 1999-10-04 | 2000-09-29 | New pharmaceutical compositions of prolonged effect |
JP2001527776A JP2003510346A (en) | 1999-10-04 | 2000-09-29 | New pharmaceutical composition |
CA002383306A CA2383306A1 (en) | 1999-10-04 | 2000-09-29 | Novel pharmaceutical compositions |
NZ518033A NZ518033A (en) | 1999-10-04 | 2000-09-29 | Delayed release/slow release drugs lacking enteric coat |
MXPA02003440A MXPA02003440A (en) | 1999-10-04 | 2000-09-29 | Coated solid dosage forms. |
EP00971305A EP1217992A1 (en) | 1999-10-04 | 2000-09-29 | Coated solid dosage forms |
AU10206/01A AU783911B2 (en) | 1999-10-04 | 2000-09-29 | Coated solid dosage forms |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GBGB9923436.1A GB9923436D0 (en) | 1999-10-04 | 1999-10-04 | Pharmaceutical compositions |
GB9923436.1 | 1999-10-04 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2001024777A1 true WO2001024777A1 (en) | 2001-04-12 |
Family
ID=10862090
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2000/009576 WO2001024777A1 (en) | 1999-10-04 | 2000-09-29 | Coated solid dosage forms |
Country Status (13)
Country | Link |
---|---|
EP (1) | EP1217992A1 (en) |
JP (1) | JP2003510346A (en) |
CN (1) | CN1402630A (en) |
AR (1) | AR025938A1 (en) |
AU (1) | AU783911B2 (en) |
CA (1) | CA2383306A1 (en) |
GB (1) | GB9923436D0 (en) |
HU (1) | HUP0203311A3 (en) |
MX (1) | MXPA02003440A (en) |
NZ (1) | NZ518033A (en) |
TW (1) | TWI233363B (en) |
WO (1) | WO2001024777A1 (en) |
ZA (1) | ZA200203486B (en) |
Cited By (21)
Publication number | Priority date | Publication date | Assignee | Title |
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KR100434904B1 (en) * | 2002-05-30 | 2004-06-11 | 주식회사 대웅 | Enteric formulations containing stabilized lansoprazole |
EP1462097A1 (en) * | 2003-03-28 | 2004-09-29 | Acme Drugs S.r.l. | Process for the preparation of enteric-coated and /or controlled-release medicaments containing active principles sensitive to gastrointestinal environment |
WO2005020954A2 (en) * | 2003-09-03 | 2005-03-10 | Agi Therapeutics Limited | Proton pump inhibitor formulations, and methods of preparing and using such formulations |
WO2006049564A1 (en) * | 2004-11-04 | 2006-05-11 | Astrazeneca Ab | New modified release pellet formulations for proton pump inhibitors |
WO2006049565A1 (en) * | 2004-11-04 | 2006-05-11 | Astrazeneca Ab | New modified release tablet formulations for proton pump inhibitors |
EP1762231A1 (en) * | 2005-08-19 | 2007-03-14 | Verla-Pharm Arzneimittelfabrik Apotheker H.J. von Ehrlich GmbH & Co. KG | Sustained release magnesium microtablets |
WO2008002567A2 (en) * | 2006-06-27 | 2008-01-03 | Alza Corporation | Methods of treating conditions by sustained release administration of benzimidazole derivatives |
US7790755B2 (en) | 2002-10-16 | 2010-09-07 | Takeda Pharmaceutical Company Limited | Controlled release preparation |
US8852636B2 (en) | 2001-06-01 | 2014-10-07 | Pozen Inc. | Pharmaceutical compositions for the coordinated delivery of NSAIDs |
US8945621B2 (en) | 2009-06-25 | 2015-02-03 | Pozen Inc. | Method for treating a patient at risk for developing an NSAID-associated ulcer |
US9023391B2 (en) | 1999-06-22 | 2015-05-05 | Dexcel Ltd. | Stable benzimidazole formulation |
US9220698B2 (en) | 2008-09-09 | 2015-12-29 | Pozen Inc. | Method for delivering a pharmaceutical composition to patient in need thereof |
US9238029B2 (en) | 2004-06-16 | 2016-01-19 | Takeda Pharmaceuticals U.S.A., Inc. | Multiple PPI dosage form |
US9539214B2 (en) | 2011-12-28 | 2017-01-10 | Pozen Inc. | Compositions and methods for delivery of omeprazole plus acetylsalicylic acid |
EP2827845B1 (en) | 2012-03-22 | 2018-12-26 | Novo Nordisk A/S | Compositions comprising a delivery agent and preparation thereof |
US10933120B2 (en) | 2012-03-22 | 2021-03-02 | Novo Nordisk A/S | Compositions of GLP-1 peptides and preparation thereof |
US10960052B2 (en) | 2010-12-16 | 2021-03-30 | Novo Nordisk A/S | Solid compositions comprising a GLP-1 agonist and a salt of N-(8-(2-hydroxybenzoyl) amino) caprylic acid |
US11034746B2 (en) | 2011-04-12 | 2021-06-15 | Novo Nordisk A/S | Double-acylated GLP-1 derivatives |
US11033499B2 (en) | 2012-06-20 | 2021-06-15 | Novo Nordisk A/S | Tablet formulation comprising a GLP-1 peptide and a delivery agent |
US11123296B2 (en) | 2012-03-22 | 2021-09-21 | Novo Nordisk A/S | Compositions comprising a delivery agent and preparation thereof |
US11833248B2 (en) | 2018-02-02 | 2023-12-05 | Novo Nordisk A/S | Solid compositions comprising a GLP-1 agonist and a salt of N-(8-(2-hydroxybenzoyl)amino)caprylic acid |
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WO2010096814A1 (en) * | 2009-02-23 | 2010-08-26 | Eurand, Inc. | Controlled-release compositions comprising a proton pump inhibitor |
CN102846571A (en) * | 2012-09-29 | 2013-01-02 | 南京正科制药有限公司 | Esomeprazole magnesium micro-tablet |
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- 2000-09-29 JP JP2001527776A patent/JP2003510346A/en active Pending
- 2000-09-29 EP EP00971305A patent/EP1217992A1/en not_active Withdrawn
- 2000-09-29 HU HU0203311A patent/HUP0203311A3/en unknown
- 2000-09-29 MX MXPA02003440A patent/MXPA02003440A/en not_active Application Discontinuation
- 2000-09-29 CN CN00816583.1A patent/CN1402630A/en active Pending
- 2000-09-29 NZ NZ518033A patent/NZ518033A/en unknown
- 2000-09-29 AU AU10206/01A patent/AU783911B2/en not_active Ceased
- 2000-09-29 WO PCT/EP2000/009576 patent/WO2001024777A1/en active IP Right Grant
- 2000-10-02 AR ARP000105197A patent/AR025938A1/en not_active Application Discontinuation
- 2000-10-03 TW TW089120543A patent/TWI233363B/en not_active IP Right Cessation
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US9345695B2 (en) | 2001-06-01 | 2016-05-24 | Pozen Inc. | Pharmaceutical compositions for the coordinated delivery of NSAIDs |
US9198888B2 (en) | 2001-06-01 | 2015-12-01 | Pozen Inc. | Pharmaceutical compositions for the coordinated delivery of NSAIDs |
US9161920B2 (en) | 2001-06-01 | 2015-10-20 | Pozen Inc. | Pharmaceutical compositions for the coordinated delivery of NSAIDs |
US8865190B2 (en) | 2001-06-01 | 2014-10-21 | Pozen Inc. | Pharmaceutical compositions for the coordinated delivery of NSAIDs |
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US7790755B2 (en) | 2002-10-16 | 2010-09-07 | Takeda Pharmaceutical Company Limited | Controlled release preparation |
EP1462097A1 (en) * | 2003-03-28 | 2004-09-29 | Acme Drugs S.r.l. | Process for the preparation of enteric-coated and /or controlled-release medicaments containing active principles sensitive to gastrointestinal environment |
WO2005020954A3 (en) * | 2003-09-03 | 2005-11-03 | Agi Therapeutics Ltd | Proton pump inhibitor formulations, and methods of preparing and using such formulations |
WO2005020954A2 (en) * | 2003-09-03 | 2005-03-10 | Agi Therapeutics Limited | Proton pump inhibitor formulations, and methods of preparing and using such formulations |
US9889152B2 (en) | 2004-06-16 | 2018-02-13 | Takeda Pharmaceuticals U.S.A., Inc. | Multiple PPI dosage form |
US9238029B2 (en) | 2004-06-16 | 2016-01-19 | Takeda Pharmaceuticals U.S.A., Inc. | Multiple PPI dosage form |
WO2006049565A1 (en) * | 2004-11-04 | 2006-05-11 | Astrazeneca Ab | New modified release tablet formulations for proton pump inhibitors |
WO2006049564A1 (en) * | 2004-11-04 | 2006-05-11 | Astrazeneca Ab | New modified release pellet formulations for proton pump inhibitors |
EP1762231A1 (en) * | 2005-08-19 | 2007-03-14 | Verla-Pharm Arzneimittelfabrik Apotheker H.J. von Ehrlich GmbH & Co. KG | Sustained release magnesium microtablets |
WO2008002567A3 (en) * | 2006-06-27 | 2008-09-12 | Alza Corp | Methods of treating conditions by sustained release administration of benzimidazole derivatives |
WO2008002567A2 (en) * | 2006-06-27 | 2008-01-03 | Alza Corporation | Methods of treating conditions by sustained release administration of benzimidazole derivatives |
US9801824B2 (en) | 2008-09-09 | 2017-10-31 | Pozen Inc. | Method for delivering a pharmaceutical composition to patient in need thereof |
US9393208B2 (en) | 2008-09-09 | 2016-07-19 | Pozen Inc. | Method for delivering a pharmaceutical composition to patient in need thereof |
US9220698B2 (en) | 2008-09-09 | 2015-12-29 | Pozen Inc. | Method for delivering a pharmaceutical composition to patient in need thereof |
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Also Published As
Publication number | Publication date |
---|---|
NZ518033A (en) | 2003-11-28 |
AR025938A1 (en) | 2002-12-18 |
AU783911B2 (en) | 2005-12-22 |
JP2003510346A (en) | 2003-03-18 |
EP1217992A1 (en) | 2002-07-03 |
HUP0203311A2 (en) | 2004-05-28 |
CA2383306A1 (en) | 2001-04-12 |
TWI233363B (en) | 2005-06-01 |
AU1020601A (en) | 2001-05-10 |
CN1402630A (en) | 2003-03-12 |
ZA200203486B (en) | 2003-08-04 |
MXPA02003440A (en) | 2004-09-10 |
HUP0203311A3 (en) | 2004-06-28 |
GB9923436D0 (en) | 1999-12-08 |
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