WO2010112965A1 - Revêtement isolant de comprimés de diclofénac - Google Patents

Revêtement isolant de comprimés de diclofénac Download PDF

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Publication number
WO2010112965A1
WO2010112965A1 PCT/IB2009/051322 IB2009051322W WO2010112965A1 WO 2010112965 A1 WO2010112965 A1 WO 2010112965A1 IB 2009051322 W IB2009051322 W IB 2009051322W WO 2010112965 A1 WO2010112965 A1 WO 2010112965A1
Authority
WO
WIPO (PCT)
Prior art keywords
glycerol
coating
cellulose
mixtures
starch
Prior art date
Application number
PCT/IB2009/051322
Other languages
English (en)
Inventor
Farhad Farshi
Levent KANDEMİR
Zerrin Ozge Samuk
Serdar Soylemez
Fikret Koc
Original Assignee
Abdi Ibrahim Ilac Sanayi Ve Ticaret Anonim Sirketi
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Abdi Ibrahim Ilac Sanayi Ve Ticaret Anonim Sirketi filed Critical Abdi Ibrahim Ilac Sanayi Ve Ticaret Anonim Sirketi
Priority to PCT/IB2009/051322 priority Critical patent/WO2010112965A1/fr
Publication of WO2010112965A1 publication Critical patent/WO2010112965A1/fr

Links

Classifications

    • 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
    • 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
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
    • A61K31/196—Carboxylic acids, e.g. valproic acid having an amino group the amino group being directly attached to a ring, e.g. anthranilic acid, mefenamic acid, diclofenac, chlorambucil
    • 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
    • A61K9/282—Organic compounds, e.g. fats
    • 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
    • A61K9/282—Organic compounds, e.g. fats
    • A61K9/2826—Sugars or sugar alcohols, e.g. sucrose; Derivatives thereof
    • 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

  • This invention is related to using of combination of a glycerol ester of fatty acid or mixtures thereof and an agent selected from group consisting of ethyl cellulose, car- boxymethylcellulose sodium, chitosan hydrochloride, carrageenan, alginic acid, agar , povidone, copovidone, gelatin,cellulose acetate, cellulose acetate phthalate, hypromellose,hypromellose acetate succinate, hypromellose phthalate,hydroxypropyl cellulose,maltodextrin,methylcellulose,shellac,polyvinyl acetate phthalate or mixtures thereof in coating of diclofenac tablet core.
  • an agent selected from group consisting of ethyl cellulose, car- boxymethylcellulose sodium, chitosan hydrochloride, carrageenan, alginic acid, agar , povidone, copovidone, gelatin,cellulose acetate, cellulose acetate phthalate,
  • EP 383967 delineates a pelleted oral diclofenac preparation with a prolonged action and an improved shell resistant to gastric juice by preparation consisting partly of quick-release diclofenac and partly of pellets with a shell resistant to gastric juice.
  • the shell is made up of 100 parts of methaacrylic acid/methyl methacrylate copolymer, 3-40 parts of glycerol fatty acid ester and 1-150 parts of talc.
  • This invention is different from EP 383967 since according to this invention sugar coated tablet is not long acting tablet and glycerol fatty acid ester should be used in combination with an agent selected from a group, which is pointed out below, to obtain of similarity of test product when compared with reference product .
  • Diclofenac is an effective analgesic, anti-pyretic, anti-phlogistic, antirheumatic and anti- arthritic non-steroidal anti-inflammatory drug (NSAID). It is available, as diclofenac sodium, and also diclofenac potassium as sugar coated tablets along with other pharmaceutical administration forms .
  • NSAID non-steroidal anti-inflammatory drug
  • Voltarol ® Rapid includes diclofenac potassium which is on the market as a reference drug.
  • the present invention concerns a sugar coated tablet comprising (i) a tablet core including diclofenac or a pharmaceutically acceptable salt thereof and suitable pharmaceutical excipient or excipients, and (ii) at least one isolation coating comprising a glycerol ester of fatty acid or mixtures thereof and an agent selected from group consisting of ethyl cellulose , carboxymethylcellulose sodium, chitosan hydrochloride, carrageenan, alginic acid, agar , povidone, copovidone, gelatin, cellulose acetate, cellulose acetate phthalate, hypromellose, hypromellose acetate succinate, hypromellose phthalate, hydroxypropyl cellulose,maltodextrin,methylcellulose,shellac, polyvinyl acetate phthalate or mixtures thereof.
  • Said combination in (ii) is used in isolation coating.
  • this invention is related to combination of glycerol esters of fatty acids and an agent selected from group consisting of ethyl cellulose carboxymethylcellulose sodium, chitosan hydrochloride, carrageenan, alginic acid, agar , povidone, copovidone, gelatin, cellulose acetate, cellulose acetate phthalate, hypromellose, hypromellose acetate succinate, hypromellose phthalate, hydroxypropyl cellulose,maltodextrin,methylcellulose,shellac,polyvinyl acetate phthalate or mixtures thereof in coating of diclofenac or a pharmaceutically acceptable salt thereof.
  • preferred embodiment of compressed dosage form is sugar coated tablet (dragee).
  • Diclofenac may be in the form of free acid or pharmaceutically acceptable salts thereof such as, but not limited, diclofenac sodium, diclofenac potassium etc. In this invention, diclofenac potassium is particularly preferred.
  • Glycerol fatty acids and their derivatives may be used.
  • Glycerol esters of fatty acids are, but not limited to, glycerol fatty acid ester, glycerol acetic acid fatty acid ester, glycerol lactic acid fatty acid ester, glycerol citric acid fatty acid ester, glycerol succinic acid fatty acid ester, glycerol diacetyl tartaric acid fatty acid ester, glycerol acetic acid ester or whatsoever.
  • Glycerol esters of fatty acids may be glycerol oleate, glycerol monostearate, glycerol stearate, glycerol palmitate, glyceryl caprate, glyceryl caprylate, glyceryl caprylate/caprate, glycerol linoleate, glyceryl lauropalmitooleate etc.
  • glycerol esters of fatty acids may also be used. In this invention glycerol oleate is preferred.
  • Glycerol ester of fatty acid or mixtures of glycerol esters of fatty acids is/are usedin the range of 0.1-90 % by weight of total isolation coating. In calculation, if there is, evaporated agents used in isolation coating are ruled out.
  • aglycerol ester of fatty acid or mixtures of glycerol esters of fatty acids is/are used in combination with an agent selected from group consistingof ethyl cellulose, carboxymethylcellulose sodium, chitosan hydrochloride, carrageenan,alginic acid, agar , povidone, copovidone, gelatin, cellulose acetate, cellulose acetate phthalate, hypromellose, hypromellose acetate succinate, hypromellose phthalate, hydroxypropyl cellulose,maltodextrin,methylcellulose,shellac, polyvinyl acetate phthalate.
  • An agent or mixtures of agents from the said group is/are
  • glycerol oleate can be used to sustain the release of various water soluble drugs.
  • ethylcellulose is used to modify the release of a drug as a coating agent.
  • both glycerol oleate and ethyl- cellulose are used so as to provideimmediate release tablet formulation.
  • Diclcofenac potassium is a water soluble drug.
  • Experiment disclosed in figure 2 is carried out under conditions of dissolution method ; USP- Metot II - Pedal, dissolution environment ; pH 7.5, temperature ; 37 0 C, dissolution volume ; 900 ml, dissolution speed ; 50 rpm . If glycerol oleate and ethyl cellulose is used as a combination in isolation coating, dissolution curves of test tablets and reference tablets are overlapped in pH 7.5 medium ( Figure 3). Experiment disclosed in figure 3 is carried out under conditions of dis- solution method ; USP- Metot II - Pedal, temperature ; 37 0 C, dissolution volume ; 900 ml, dissolution speed ; 50 rpm .
  • Coating may contain further suitable excipients such as, but not limited, micro- crystalline cellulose,hydroxypropylmethylcellulose, polyethylene glycol, iron oxide, polyvinylpyrrolidone, talc, sugar, deionized water (evaporated in final coating) , ethyl alcohol (evaporated in final coating) .
  • excipients such as, but not limited, micro- crystalline cellulose,hydroxypropylmethylcellulose, polyethylene glycol, iron oxide, polyvinylpyrrolidone, talc, sugar, deionized water (evaporated in final coating) , ethyl alcohol (evaporated in final coating) .
  • Coating has four steps as (i) isolation coating, (ii) talc coating, (iii)sugar coating and (iv) polishing.
  • the tiers of first step's are : a. Dissolving ethylcellulose in ethyl alcohol, b. Adding HPMC and mixing until it dissolves, c. Adding Oleate Glycerol and then mixing, d. Coating of tablets.
  • the tiers of second step's(talc coating) are : a. Taking deionized water in a solution preparation tank and heating, b. Adding and dissolving sugar ,c. Adding and mixing PEG and Polyvinylpyrrolidone, d. Adding and mixing microcrystalline cellulose and Talc, e. Adding and mixing red iron oxide, f. Coating of isolation coated tablet
  • the tiers of third step's are : a. Taking deionized water ,b. Adding and mixing sugar until it dissolves,c. Adding and mixing red iron oxide,d. Coating of talc coated tablet.
  • the tiers of fourth step's are : a. adding and dissolving sugar, b.
  • Dissolution profiles of reference tablets and test tablets should be same or identical in different dissolution mediums. Desired dissolution profile means that in targeted dissolution mediums f2 value should be at least 50 to 100 when compared to the reference dissolution profile.
  • the similarity factor f2 is a measurement of the similarity through a point by point comparison as shown in equation 1.
  • n is the number of sampling time points
  • R is the amount drug released from a reference batch at time t
  • Tt is the amount drug released from a test batch at time t.
  • f2 values are greater than 50, it ensures sameness of the performance of the reference product and test product so as to obtain bioequivalance.
  • the aim of this invention is to obtain a tablet core formulation.
  • the tablet core formulation can include suitable excipients , but are not limited to, lubricants, diluents, binders, fillers, disintegrants and the like which might be needed for the preparation of tablet core formulation.
  • Fillers are selected from the group consisting of, but not limited to, lactose, micro- crystalline cellulose, silicified microcrystalline cellulose, powdered cellulose, calcium carbonate, dibasic calcium phosphate, tribasic calcium phosphate, sucrose, glucose, dextrates, dextrins, dextrose, fructose, lactitol, mannitol, sorbitol, starch or mixtures thereof.
  • Preferred filler is microcrystalline cellulose.
  • Lubricants used in the tablet core according to the present invention may be selected from the group consisting of, but not limited to, magnesium stearate, magnesium lauryl sulphate,sodium stearyl fumarate, polyethylene glycol, stearic acid, colloidal silicon dioxide or mixtures thereof.
  • Preferred lubricant is magnesium stearate.
  • Disintegrants are selected from the group consisting of, but not limited to, modified starches, croscarmallose sodium, carboxymethylcellulose calcium, sodium starch glycolate ,crospovidone or mixtures thereof.
  • Preferred disintegrant is sodium starch glycolate.
  • Binders are selected from the group consisting of, but not limited to starch, polyvinylpyrrolidone, sodium alginate, ethylcellulose, pregelatinized starch, gelatin or mixtures thereof.
  • Preferred binder is polyvinylpyrrolidone .
  • Diluents are selected from the group consisting of, but not limited to, starches,maizestarch, potato starch, rice starch, wheat starch, pregelatinized starch,starch 1500, , fully pregelatinized starch , lactose, mannitol , cellulose derivatives, confectioner's sugar or mixtures thereof.
  • Preferred diluent is maize starch.

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  • Health & Medical Sciences (AREA)
  • Epidemiology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Preparation (AREA)

Abstract

Cette invention porte sur un revêtement isolant de diclofénac comprenant un ester de glycérol d'acide gras ou des mélanges de plusieurs de ceux-ci et un agent choisi dans le groupe constitué par l'éthylcellulose, la carboxyméthylcellulose sodique, le chlorhydrate de chitosane, le carraghénane, l'acide alginique, l'agar-agar, la polyvinylpirrolidone, un copolymère de vinylpyrrolidone-acétate de vinyle (copovidone), la gélatine, l'acétate de cellulose, l'acétate phtalate de cellulose, l'hypromellose, l'acétate succinate d'hypromellose, le phtalate d'hypromellose, l'hydroxypropylcellulose, la maltodextrine, la méthylcellulose, la gomme laque, le poly(acétate phtalate de vinyle) ou des mélanges de ceux-ci.
PCT/IB2009/051322 2009-03-30 2009-03-30 Revêtement isolant de comprimés de diclofénac WO2010112965A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PCT/IB2009/051322 WO2010112965A1 (fr) 2009-03-30 2009-03-30 Revêtement isolant de comprimés de diclofénac

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/IB2009/051322 WO2010112965A1 (fr) 2009-03-30 2009-03-30 Revêtement isolant de comprimés de diclofénac

Publications (1)

Publication Number Publication Date
WO2010112965A1 true WO2010112965A1 (fr) 2010-10-07

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2017509691A (ja) * 2014-01-21 2017-04-06 ビーピーエスアイ ホールディングス， エルエルシー 中鎖グリセリドを含有する即時放出フィルムコーティング、及びそれによってコーティングされている基材
CN111973565A (zh) * 2020-07-07 2020-11-24 南京海纳医药科技股份有限公司 一种含有富马酸沃诺拉赞的片剂及其溶出度测定方法
CN114306268A (zh) * 2021-12-28 2022-04-12 恒诚制药集团淮南有限公司 一种吡喹酮薄膜包衣制剂及其制备方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001049270A2 (fr) * 1999-12-30 2001-07-12 Ancile Pharmaceuticals, Inc. Enrobage masquant les odeurs pour preparation pharmaceutique
WO2005115352A1 (fr) * 2004-05-24 2005-12-08 Mepha Ag Procede de revetement a sec
US20060188565A1 (en) * 1996-05-17 2006-08-24 Giorgio Reiner Rapidly bioavailable tablet and capsule formulations of diclofenac
US20080096979A1 (en) * 2004-11-08 2008-04-24 Rubicon Research Pvt. Ltd. Aqueous Pharmaceutical Coating

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060188565A1 (en) * 1996-05-17 2006-08-24 Giorgio Reiner Rapidly bioavailable tablet and capsule formulations of diclofenac
WO2001049270A2 (fr) * 1999-12-30 2001-07-12 Ancile Pharmaceuticals, Inc. Enrobage masquant les odeurs pour preparation pharmaceutique
WO2005115352A1 (fr) * 2004-05-24 2005-12-08 Mepha Ag Procede de revetement a sec
US20080096979A1 (en) * 2004-11-08 2008-04-24 Rubicon Research Pvt. Ltd. Aqueous Pharmaceutical Coating

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
"Remington's Pharmaceutical Sciences", 1 January 1980, REMINGTON'S PHARMACEUTICAL SCIENCES; [REMINGTON'S PHARMACEUTICAL SCIENCES], EASTON, MACK PUB, US, PAGE(S) 1585 - 1593, XP002304983 *
MICHAEL E AULTON ED - AULTON M E: "Pharmaceutics: The Science of Dosage Form Design, TABLET COATING", 1 January 1988, PHARMACEUTICS : THE SCIENCE OF DOSAGE FORM DESIGN, CHURCHILL LIVINGSTONE, PAGE(S) 669 - 677, ISBN: 9780443036439, XP002513493 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2017509691A (ja) * 2014-01-21 2017-04-06 ビーピーエスアイ ホールディングス， エルエルシー 中鎖グリセリドを含有する即時放出フィルムコーティング、及びそれによってコーティングされている基材
CN111973565A (zh) * 2020-07-07 2020-11-24 南京海纳医药科技股份有限公司 一种含有富马酸沃诺拉赞的片剂及其溶出度测定方法
CN114306268A (zh) * 2021-12-28 2022-04-12 恒诚制药集团淮南有限公司 一种吡喹酮薄膜包衣制剂及其制备方法

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