EP2464344A2 - Pharmazeutische tablette mit rosuvastatin-calcium - Google Patents
Pharmazeutische tablette mit rosuvastatin-calciumInfo
- Publication number
- EP2464344A2 EP2464344A2 EP10739873A EP10739873A EP2464344A2 EP 2464344 A2 EP2464344 A2 EP 2464344A2 EP 10739873 A EP10739873 A EP 10739873A EP 10739873 A EP10739873 A EP 10739873A EP 2464344 A2 EP2464344 A2 EP 2464344A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- tablet
- core
- rosuvastatin
- barrier layer
- calcium phosphate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
Classifications
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
-
- 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
- A61K9/2009—Inorganic compounds
-
- 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
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
- A61K9/2054—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
- A61K9/2095—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
- A61K9/284—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone
-
- 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
Definitions
- the present invention relates to pharmaceutical tablets comprising the active agent rosuvastatin calcium.
- Rosuvastatin is a pharmaceutically active compound that acts as a competitive inhibitor of 3-hydroxy- 3-methylglutarylcoenzyme A reductase (HMG CoA reductase).
- HMG CoA reductase 3-hydroxy- 3-methylglutarylcoenzyme A reductase
- Rosuvastatin was disclosed in EP 521471 and US 5,260,440 (reissued as RE37,314) by Shionogi Seiyaku Kabushiki Kaisha. Rosuvastatin is marketed as a calcium salt by AstraZeneca under the brand name CRESTOR®.
- EP 1223918 and US 6,316,460 indicate that rosuvastatin undergoes degradation under certain conditions, which can make formulating a stable pharmaceutical composition difficult.
- EP 1223918/US 6,316,460 teach that the major degradation products are the corresponding (3R, 5S) lactone and an oxidation product, in which the hydroxy group adjacent to the carbon-carbon double bond is oxidized to a ketone.
- These patents purport to reduce these degradation products by the use of tribasic phosphate salts; e.g., tribasic calcium phosphate, tribasic magnesium phosphate or tribasic aluminium phosphate.
- Example 1 reports that a 2.5 mg direct compression tablet containing tribasic calcium phosphate developed only 0.50% lactone after 1 week at 7O 0 C under 80% humidity whereas replacement of the tribasic with dibasic calcium phosphate resulted in 15.61% lactone.
- Example 4 where tablets are compressed after wet granulation and fluid bed drying, replacement of the tribasic with dibasic calcium phosphate results in 28.15 % lactone after 1 week 7O 0 C at 80% humidity compared to 0.28 %. All of the tablets in these examples are uncoated.
- a first aspect of the invention relates to a tablet comprising i) a compressed core, which comprises rosuvastatin calcium, a dibasic calcium phosphate, and at least one pharmaceutically acceptable excipient; and ii) moisture barrier layer around said core, which comprises a polyvinyl alcohol.
- the polyvinyl alcohol can be partially hydrolyzed.
- the barrier layer can contain other ingredients including pigments and dyes. Generally the barrier layer coating weight is from 2 to 7%, more typically 3 to 6% the weight of the compressed core.
- the compressed core contains a dibasic calcium phosphate, preferred tablets of the invention have stability that is similar or superior to the commercial CRESTOR® coated tablets.
- Another aspect of the invention relates to a process for making a stable pharmaceutical tablet comprising rosuvastatin calcium which comprises:
- Another aspect of the invention relates to the use acts as a competitive inhibitor of 3-hydroxy-3-methylglutarylcoenzyme A reductase (HMG CoA reductase) in medicine, such as in the treatment of hypercholesterolemia, hyperlipidemia, mixed dyslipidaemia and atherosclerosis
- HMG CoA reductase 3-hydroxy-3-methylglutarylcoenzyme A reductase
- the present invention is based on the discovery that a sufficient moisture barrier layer around a rosuvastatin tablet can minimize degradation, especially the formation of the lactone degradation product.
- This moisture barrier layer can permit the use of dibasic calcium phosphate in forming a tablet with good storage stability, despite the admonition to avoid dibasic calcium phosphate shown in EP 1223918/US 6,316,460.
- the moisture barrier layer used in the present invention generally contains a polyvinyl alcohol.
- a polyvinyl alcohol includes hydrolyzed, such as partially hydrolyzed polyvinyl alcohol, as well as unhydrolyzed forms.
- the moisture barrier layer can contain, and typically does contain, additional excipients as is conventional in the art. Typically such excipients may include a plasticizer, a lubricant, a filler, and/or a colorant. Examples of such excipients include talc, lecithin, triacetin, xanthan gum, lactose monohydrate, titanium dioxide, and iron oxide.
- the polyvinyl alcohol generally accounts for at least 15% and more typically at least 20% of the moisture barrier layer, by weight.
- the moisture barrier layer contains a colorant.
- a colorant can be useful in protecting the rosuvastatin from photodegradation.
- Colorant is used in a broad sense to embrace coloring materials as well as opacifiers and includes pigments and/or dyes.
- the dye can be in free form or associated with a substrate, i.e., in "lake" form.
- one or more pigments e.g., metal oxides such titanium dioxide and/or iron oxide(s) are contained in the moisture barrier layer, optionally with one or more dyes.
- the moisture barrier layer can be formed from commercially available products such as Colorcon's OPADRY® II 85-series (a PVA-based coating) or OP ADR Y® amb (Aqueous Moisture Barrier); the latter being a preferred barrier material.
- the moisture barrier layer is generally applied to a weight of 2 to 7%, preferably 3 to 6%, of the weight of the compressed core, e.g., the uncoated tablet.
- Such coatings include enteric coatings (e.g. coatings that contain enteroresistant polymers) and non-enteric coatings (e.g. enterosoluble coatings); the latter being preferred.
- Suitable polymers may include polymethacrylates and copolymers thereof, and polyvinylacetates including esters thereof such as
- polyvinylacetate phthalates Such polymers may be used instead of, or in addition to, polyvinyl alcohol in the moisture barrier layer.
- polyvinyl alcohol in the moisture barrier layer.
- hydroxypropyl in this regard, hydroxypropyl
- methylcellulose-based coatings generally provide insufficient moisture barrier resistance for purposes of the present invention and thus are not a suitable replacement for polyvinyl alcohol. Any of the above-mentioned polymers can be used in combination with polyvinyl alcohol.
- the moisture barrier layer is coated on a compressed core that contains rosuvastatin calcium, a dibasic calcium phosphate, and at least one pharmaceutically acceptable excipient.
- the compressed core tablet typically contains from 1 to 100 mg of rosuvastatin calcium (expressed in terms of the weight of rosuvastatin base), particularly 5, 10, 15, 20, or 40 mg of rosuvastatin calcium.
- the conventional pharmaceutically acceptable dibasic calcium phosphate is either an anhydrate or a dihydrate. Either or both forms may be used in making the compositions of the present invention.
- the dibasic calcium phosphate is an anhydrous form, i.e. with a water content of 2 weight % or less.
- the rosuvastatin calcium is present in an amount from 3 to 15 weight per cent and the dibasic calcium phosphate is present in an amount from 6 to 10 weight per cent, based on the total weight of the compressed core. More particularly, the ratio between the rosuvastatin calcium and the dibasic calcium phosphate is typically between 0.5:1 and 1.5: 1 by weight.
- the remaining excipients in the compressed core typically total from 75 to 89 weight per cent.
- Pharmaceutically acceptable excipients typically include binders, diluents or fillers, lubricants, and/or disintegrants. A particular excipient may act both as a binder and a diluent, or both as a binder and a disintegrant, etc.
- binders include polyvinylpyrrolidone, lactose, starch, modified starch, waxes, cellulose, and modified cellulose (methyl cellulose, carboxymethyl cellulose, hydroxypropyl cellulose, or hydroxypropylmethyl cellulose).
- diluents include calcium phosphates, lactose, mannitol, sorbitol, xylitol, starch, a modified starch, cellulose, a modified cellulose, etc.
- Suitable lubricants include, for example, magnesium stearate, stearic acid, talc, calcium stearate, hydrogenated castor oil, sodium stearyl fumarate.
- Typical disintegrants include sodium starch glycolate and crosspovidone.
- excipients include preservatives, colorants, flow conditioners, etc.
- inert excipients The list of inert excipients presented above is not exhaustive; other suitable excipients may be found, e.g., in Handbook of Pharmaceutical Excipients edited by Arthur H. Kibbe, 3rd Edition, American Pharmaceutical Association.
- the compressed core comprises rosuvastatin calcium; a dibasic calcium phosphate; a binder such as microcrystalline cellulose; a water-soluble diluent such as lactose (including lactose monohydrate), mannitol, sorbitol, or xylitol; a disintegrant such as crosspovidone; and a lubricant such as magnesium stearate.
- the total amount of water present in the compressed core prior to applying the moisture barrier layer is less than 6.0%, measured as the loss on drying or by K. Fischer method.
- a pH- adjustor i.e. an acid, a base and/or a salt thereof
- such an excipient is not required and is preferably omitted from the composition.
- the tablets of the present invention can be made by conventional techniques known in the art.
- the active substance and the excipients are formed into a tablet blend which is then compressed to form a tablet.
- This tablet serves as the compressed core of the present invention.
- the tablet blend can be made by any convenient method.
- the active substance and at least one pharmaceutically acceptable excipient are, after optional sieving, blended together in one or more steps.
- the blend is optionally screened.
- a lubricant such as magnesium stearate is added in the last blending step, as is common in the art, to form the final tablet blend; i.e., a powder blend that contains all the ingredients of the compressed core in a homogeneous mixture.
- the tablet blend is then compressed into a tablet which is then used as the compressed core of the present invention.
- a wet granulation technique may be used in making the tablet blend.
- the active substance and at least one excipient are, after optional sieving, blended together in a granulator and then granulated with a small volume of purified water.
- the granulate includes a dibasic calcium phosphate as well as a diluent and/or binder.
- the granulate is dried and typically passed through a mill and/or sieved.
- Lubricant and, optionally, all or part of a disintegrant are blended with the granulate, and the obtained homogeneous mixture is compressed into tablets.
- the tablets are subsequently coated with a polyvinyl alcohol-containing composition to form the moisture barrier layer.
- a sub-coat may be applied before forming the moisture barrier layer, but such a sub-coat is generally avoided in tablets of the invention.
- the coating of the tablet cores can be performed by any suitable technique including the conventional techniques of spray coating and pan coating.
- the coating step involves applying an aqueous or non-aqueous solution or suspension of polyvinyl alcohol and auxilliary excipients onto the tablets and drying to form a moisture barrier layer around a compressed core.
- the tablets may be packed in a suitable package material, preferably in a blister package, to provide the final dosage form for administration of rosuvastatin by patients in need thereof.
- the invention is further illustrated by some non-limiting examples.
- Opadry® AMB is a combination of Polyvinyl alcohol - part, hydrolyzed, Titanium dioxide, Talc, Lecithin (soya), Xanthan gum, iron oxide yellow
- a pre-mixture of rosuvastatin calcium and microcrystalline cellulose was made in a tumbling blender.
- the pre-mixture was sieved through 0.5 mm mesh and also a part of the lactose (approx. half of the lactose) was sieved to drag the remainder of the drug substance.
- the rest of the excipients were added to the blend, except Mg stearate, and mixed for 30 min in a free fall blender. Finally, Mg stearate was added and mixed for 5 min.
- the lubricated blend was compressed in a tablet press.
- a 15 % ( w/w) suspension of Opadry® AMB Yellow in purified water was prepared. Tablet cores were transferred into t a standard perforated pan system and coated with the suspension of Opadry® AMB Yellow to a theoretical weight gain of 4%.
- Opadry® AMB is a combination of Polyvinyl alcohol - part, hydrolyzed, Titanium dioxide, Talc, Lecithin (soya), Xanthan gum, iron oxide red, FD&C yellow #6/Sunset yellow FCF, Aluminium lake, iron oxide yellow.
- a pre-mixture of rosuvastatin calcium and microcrystalline cellulose was made in a tumbling blender.
- the pre-mixture was sieved through 0.5 mm mesh and also a part of the lactose (approx. half of the lactose) was sieved to drag the remainder of the drug substance.
- the rest of the excipients were added to the blend, except Mg stearate, and mixed for 30 min in a free fall blender. Finally, Mg stearate was added and mixed for 5 min.
- the lubricated blend was compressed in a tablet press.
- a 15 % (w/w) suspension of Opadry® AMB Pink in purified water was prepared. Tablet cores were transferred into a standard perforated pan system and coated with the suspension of Opadry® AMB Pink to a theoretical weight gain of 4%.
- Rosuvastatin tablets were prepared containing dibasic calcium phosphate dihydrate and coated with various coatings; namely Opadry II 31 K32626 (HPMC-based coating same composition as CRESTOR®), Opadry AMB (moisture barrier coating system, based on PVA) and Opadry ns-g (based on CMC Na). Each coating was applied to achieve 4% weight gain.
- the tablet composition was as follows:
- the coated tablets were put in stability at 70°C/80% RH for two weeks, in open dish.
- the lactone content both initially and at the conclusion of two weeks, is shown below as percentage of the active.
- PVA polyvinyl alcohol
- hydroxypropyl methylcellulose HPMC
- CMC- Na sodium carboxymethyl cellulose
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Inorganic Chemistry (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US23354209P | 2009-08-13 | 2009-08-13 | |
PCT/EP2010/004796 WO2011018185A2 (en) | 2009-08-13 | 2010-07-29 | Pharmaceutical tablet comprising rosuvastatin calcium |
Publications (1)
Publication Number | Publication Date |
---|---|
EP2464344A2 true EP2464344A2 (de) | 2012-06-20 |
Family
ID=43334705
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP10739873A Withdrawn EP2464344A2 (de) | 2009-08-13 | 2010-07-29 | Pharmazeutische tablette mit rosuvastatin-calcium |
Country Status (4)
Country | Link |
---|---|
EP (1) | EP2464344A2 (de) |
AU (1) | AU2010281913A1 (de) |
EA (1) | EA201270269A1 (de) |
WO (1) | WO2011018185A2 (de) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2805714A1 (de) | 2013-04-25 | 2014-11-26 | Antibiotice S.A. | Stabile pharmazeutische Zusammensetzung mit amorphem Rosuvastatincalcium |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104473899B (zh) * | 2014-12-19 | 2017-10-03 | 河南润弘制药股份有限公司 | 一种瑞舒伐他汀钙片剂及其制备方法 |
BR112019009709A2 (pt) * | 2016-11-15 | 2019-08-13 | Lg Chemical Ltd | preparação de combinação. |
GB2622822A (en) | 2022-09-28 | 2024-04-03 | Novumgen Ltd | A rapidly disintegrating tablet of rosuvastatin and its process of preparation |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2008075320A2 (en) * | 2006-12-21 | 2008-06-26 | Ranbaxy Laboratories Limited | Antilipidemic pharmaceutical compositions and process for preparation thereof |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2648897B2 (ja) | 1991-07-01 | 1997-09-03 | 塩野義製薬株式会社 | ピリミジン誘導体 |
GB0001621D0 (en) | 2000-01-26 | 2000-03-15 | Astrazeneca Ab | Pharmaceutical compositions |
JP2006513186A (ja) * | 2002-12-20 | 2006-04-20 | ファイザー・プロダクツ・インク | Cetp阻害剤およびhmg−coaレダクターゼ阻害剤を含む剤形 |
JP2008528542A (ja) * | 2005-01-31 | 2008-07-31 | チバ ホールディング インコーポレーテッド | ロスバスタチンカルシウム塩の結晶形 |
-
2010
- 2010-07-29 AU AU2010281913A patent/AU2010281913A1/en not_active Abandoned
- 2010-07-29 WO PCT/EP2010/004796 patent/WO2011018185A2/en active Application Filing
- 2010-07-29 EA EA201270269A patent/EA201270269A1/ru unknown
- 2010-07-29 EP EP10739873A patent/EP2464344A2/de not_active Withdrawn
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2008075320A2 (en) * | 2006-12-21 | 2008-06-26 | Ranbaxy Laboratories Limited | Antilipidemic pharmaceutical compositions and process for preparation thereof |
Non-Patent Citations (1)
Title |
---|
See also references of WO2011018185A2 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2805714A1 (de) | 2013-04-25 | 2014-11-26 | Antibiotice S.A. | Stabile pharmazeutische Zusammensetzung mit amorphem Rosuvastatincalcium |
Also Published As
Publication number | Publication date |
---|---|
EA201270269A1 (ru) | 2012-09-28 |
WO2011018185A3 (en) | 2011-11-24 |
WO2011018185A2 (en) | 2011-02-17 |
AU2010281913A1 (en) | 2012-04-05 |
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