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WO2001032185A1 - Composition pharmaceutique renfermant au moins un acide bisphosphonique ou un de ses sels et son procede de preparation - Google Patents

Composition pharmaceutique renfermant au moins un acide bisphosphonique ou un de ses sels et son procede de preparation Download PDF

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Publication number
WO2001032185A1
WO2001032185A1 PCT/IN1999/000060 IN9900060W WO0132185A1 WO 2001032185 A1 WO2001032185 A1 WO 2001032185A1 IN 9900060 W IN9900060 W IN 9900060W WO 0132185 A1 WO0132185 A1 WO 0132185A1
Authority
WO
WIPO (PCT)
Prior art keywords
bisphosphonic acid
core
salt
pharmaceutical composition
seal coating
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.)
Ceased
Application number
PCT/IN1999/000060
Other languages
English (en)
Inventor
Amar Lulla
Geena Malhotra
Chiloo Bugtani
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Cipla Ltd
Original Assignee
Cipla Ltd
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 Cipla Ltd filed Critical Cipla Ltd
Priority to PCT/IN1999/000060 priority Critical patent/WO2001032185A1/fr
Priority to AU21272/00A priority patent/AU2127200A/en
Publication of WO2001032185A1 publication Critical patent/WO2001032185A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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
    • A61K31/66—Phosphorus compounds
    • A61K31/662—Phosphorus acids or esters thereof having P—C bonds, e.g. foscarnet, trichlorfon
    • A61K31/663—Compounds having two or more phosphorus acid groups or esters thereof, e.g. clodronic acid, pamidronic acid
    • 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
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/5073—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals having two or more different coatings optionally including drug-containing subcoatings
    • 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
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/5073—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals having two or more different coatings optionally including drug-containing subcoatings
    • A61K9/5078—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals having two or more different coatings optionally including drug-containing subcoatings with drug-free core

Definitions

  • the present invention relates to a pharmaceutical composition, and to a process of preparation thereof, and more particularly to a pharmaceutical composition containing bisphosphonic acid(s) or salts(s) thereof, which composition will be used for the treatment of osteoporosis.
  • the present pharmaceutical composition comprises by weight, about 5- 40% by weight of an active ingredient selected from the group consisting of:
  • the preferred bisphosphonic acid is 4-amino- 1- hydroxybutlidene-1, 1 -bisphosphomc acid, i.e., alendronic acid; more preferable is its monosodium salt trihydrate, viz., alendronate sodium trihydrate, or other bisphosphonic acid(s) or salts(s) thereof, viz., etidronate, clodronate, pamidronate or ibandronate.
  • Method of preparation pf bisphosphonic acids may be found in e.g., U.S.Pat. No.3,962,432; U.S.Pat.No.4,954,598; U.S.Pat.No.4267,108; U.S. Pat. No.4,327,039; U.S.Pat.No.4,407,761; U.S.Pat.No.4,621,077; U.S. Pat.
  • the disadvantages of all the above inventions are that the compositions release the active almost instantaneously causing oesophageal discomfort and ulceritis due to the release of the active in the upper Gastro Intestinal Tract (GIT).
  • GIT Gastro Intestinal Tract
  • the medication has to be taken on arising for the day atleast 30 minutes before the first food, beverages or medication of the day with a full glass (200ml) of plain water only.
  • the patients are advised to sit upright for about 30 minutes after ingestion of medication and until their first food of the day. Patients are not allowed to take medication at bedtime or before arising on the day.
  • a pharmaceutical composition for oral administration substantially comprising a core having bisphosphonic acids and salts thereof, coated with an acid resistant coat thereby releasing the active only in the alkaline environment of the lower GIT.
  • the purpose of the enteric coating employed in the present invention is to resist the acidic environment of the stomach, thus avoiding oesophaeal irritation. Accordingly, the disadvantage of the prescribed method of taking the medication, as explained above, can be overcome by the present invention.
  • the core containing of bisphosphonic acid(s) or salt(s) thereof can be coated with a hydrophilic polymer known in the art (seal coating) Example Hydroxy Proply Methyl Cellulose (HPMC), Hydroxy Propyl Cellulose (HPC), Polyvinyl Pyrrolidone (PVP), Shellac, cellulose gums, xanthan gums, thereupon being coated with the enteric polymer.
  • enteric coatings may be employed in the present invention, including for example: cellulose acetate phthalate, Hydroxy propyl methyl cellulose phthalate (HPMCP); hydroxypropyl cellulose acetyl succinate; polyvinyl acetate phthalate; copolymerised methacrylic acid/methacrylic acid methyl esters, such as Eudragit L 12.5, Eudragit L 100 55 or Eudragit S 100; and mixtures thereof.
  • the enteric coating may contain conventional plasticisers, pigments and/or dispersants, including for example polyethylene glycols, triacetin, triethyl citrate, and Citroflex, dibutyl sebacate.
  • the enteric coating can be applied in any suitable manner, for example in the form of an aqueous dispersion in water, or other dispersing medium, or in the form of a solution. It is preferred that a dispersion or solution of the enteric coating is treated with an alkali in order to neutralise at least part of any free acid content.
  • the alkali may be for example, a carbonate or hydroxide of sodium, potassium, magnesium or calcium.
  • compositions according to the present invention may comprise one or more additives.
  • particularly useful additives include a diluent to aid dissolution of the pharmaceutically active ingredient, and a lubricant to aid flow of the active ingredient during manufacture.
  • the diluent may be, for example, lactose.
  • the lubricant may be, for example, magnesium streate and/or talcum. It will be appreciated that the pharmaceutical compositions of the invention may contain any one or more other additives conventionally used in the formulation of pharmaceutical compositions.
  • excipients known in the art of manufacturing these dosage forms include lactose, microcrystalline cellulose, dicalcium phosphate, starch, sugar, disintegrants such as starch and derivatives of starch, sodium carboxy methyl cellulose and it's derivatives, crospovidone, etc.
  • the pharmaceutical composition as per the present invention may take the form of, tablets or peltabs or pellets in a capsule.
  • the bisphosphonic acid or salt thereof is present in the core.
  • the core of the pharmaceutical composition comprises a plurality of compressed granules of the bisphosphonic acid.
  • This embodiment is particularly useful when it is desired to provide the pharmaceutical composition in tablets form, and there is further provided by the present invention a tablet which comprises pharmaceutical composition substantially as herein described, wherein the inert core is formed from a plurality of granules comprising the bisphosphonic acid, which granules are compressed together to form the core.
  • the seal is applied around the active core, then the enteric coating is suitably provided around the seal coated active core.
  • the bisphosphomc acid or salt thereof is present in the active core.
  • This embodiment of the invention is particularly applicable for the inclusion of a plurality of pellets in a capsule.
  • the active cores of the pellets may typically be non-pareils and suitably provided in the form of sugar beads or sugar/starch beads.
  • the bisphosphonic acid can be supplied as a spray.
  • the bisphosphonic acid or salt thereof may be mixed with one or more additives before being loaded on the inert cores.
  • the additives may include, for example, a solubiliser and/or a lubricant.
  • the inert cores can be loaded with the bisphosphonic acid (together with any additives), and sprayed with a binder, in a centrifugal coating apparatus.
  • the seal coating is applied around the active core of each of the pellets to be provided in a capsule, and the enteric coating is suitably provided around the seal coating on each of the active cores.
  • a capsule which comprises a capsule shell containing a plurality of pellets.
  • bisphosphonic acid or salt thereof is present in the active core.
  • This embodiment of the invention is particularly applicable for the compression of a plurality of pellets in a tablet form.
  • the active cores of the pellets may typically be non-pareils and suitably provided in the form of sugar beads or sugar/starch beads.
  • the seal coating is applied around the active core of each of the pellets, and the enteric coating is suitably provided around the seal coating on each of the active cores.
  • These plurality of pellets together with conventional excipients such as disintegrants and binders are compressed into tablets, generally known as peltabs.
  • the active drug is bisphosphonic acid or salt thereof, unless indicated otherwise.
  • sucrose sucrose
  • other binding agents such as polyvinylpyrrolidone, shellac or xanthan gum, may be used instead.
  • a plurality of particles containing the active drug are prepared from the following materials:
  • Non-pareil seeds 95.00mg.
  • Titanium dioxide 2.18mg.
  • the active drug, the sucrose, the corn starch and the talcum are blended thoroughly to yield a dusting powder.
  • the non-pareil seeds are loaded into a centrifugal coating apparatus, and then coated with the dusting powder while spraying the HPMC (hydroxypropyl methyl cellulose) solution, which results in the production of a plurality of discrete particles containing the active ingredients.
  • the particles so obtained are dried using conventional tray dryers/fluid bed dryers to an outlet temperature of 45°C. These particles are then seal coated using HPMC solution and further enteric coated in suitable Wurster coating apparatus.
  • a plurality of particles containing the active drug are prepared as follows:
  • Non-pareil seeds 95.00mg.
  • Titanium dioxide 1.75mg.
  • the active drug, the sucrose, the corn starch and the talcum are blended thoroughly to yield a dusting powder.
  • the non-pareil seeds are loaded into a centrifugal coating apparatus, and then coated with the dusting powder while spraying the HPMC solution, which results in the production of a plurality of discrete particles containing the active ingredients.
  • the particles so obtained are dried using conventional tray dryers/fluid bed dryers to an outlet temperature of 45°C. These particles are then seal coated using HPMC solution and further enteric coated in suitable Wurster coating apparatus.
  • a plurality of a particles containing the active drug are prepared from the following materials:
  • Titanium dioxide 2.18mg.
  • the active drug, the sucrose, the corn starch and the talcum are blended thoroughly to yield a dusting powder.
  • the non-pareil seeds are loaded into a centrifugal coating apparatus, and then coated with the dusting powder while spraying the HPC-L Klucel (hydroxypropyl cellulose) solution, which results in the production of a plurality of discrete particles containing the active ingredient.
  • the particles so obtained are dried using conventional tray dryers/fluid bed dryers to an outlet temperature of 45°C. These particles are then seal coated using HPMC solution and further enteric coated in suitable Wurster coating apparatus, and is then suitably diluted with binders and disintegrants, and compressed by conventional means.
  • HPC-L Klucel hydroxypropyl cellulose
  • Tablet cores containing an active drug are prepared from the following materials:
  • Titanium dioxide 0.655mg.
  • the active drug is blended with the MCC, lactose and croscarmellose sodium in a suitable mixer.
  • the blend containing the active drag is lubricated with magnesium stearate.
  • the blend is compressed into a suitable shape for a tablet core using conventional compression equipment.
  • the resulting tablet core is then coated using HPMC solution. These seal coated tablets are then enteric coated.
  • Tablet cores containing an active drug are prepared from the following materials:
  • Titanium dioxide 0.436mg.
  • the active drug is blended with the MCC, lactose and croscarmellose sodium in a suitable mixer.
  • the blend containing the active drag is lubricated with magnesium stearate.
  • the blend is compressed into a suitable shape for a tablet core using conventional compression equipment.
  • the resulting tablet core is then coated using HPMC solution. These seal coated tablets are then enteric coated.

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

Abstract

L'invention concerne une composition pharmaceutique renfermant au moins un acide bisphosphonique ou un de ses sels, tel que du trihydrate, del'etidronate, du clodronate, du pamidronate ou de l'ibandronate de sodium d'alendronate, destinée à être utilisée dans le traitement de l'ostéoporose. L'invention concerne également une préparation de cette composition consistant à prendre un noyau composé d'acide bisphosphonique ou d'un de ses sels situé à l'intérieur du noyau ou sur sa surface, à appliquer un revêtement d'étanchéité autour du noyau et à appliquer un revêtement gastro-résistant autour du revêtement d'étanchéité.
PCT/IN1999/000060 1999-11-02 1999-11-02 Composition pharmaceutique renfermant au moins un acide bisphosphonique ou un de ses sels et son procede de preparation Ceased WO2001032185A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
PCT/IN1999/000060 WO2001032185A1 (fr) 1999-11-02 1999-11-02 Composition pharmaceutique renfermant au moins un acide bisphosphonique ou un de ses sels et son procede de preparation
AU21272/00A AU2127200A (en) 1999-11-02 1999-11-02 A pharmaceutical composition containing bisphosphonic acid(s) or salt(s) thereofand a process of preparing thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/IN1999/000060 WO2001032185A1 (fr) 1999-11-02 1999-11-02 Composition pharmaceutique renfermant au moins un acide bisphosphonique ou un de ses sels et son procede de preparation

Publications (1)

Publication Number Publication Date
WO2001032185A1 true WO2001032185A1 (fr) 2001-05-10

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PCT/IN1999/000060 Ceased WO2001032185A1 (fr) 1999-11-02 1999-11-02 Composition pharmaceutique renfermant au moins un acide bisphosphonique ou un de ses sels et son procede de preparation

Country Status (2)

Country Link
AU (1) AU2127200A (fr)
WO (1) WO2001032185A1 (fr)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005030177A3 (fr) * 2003-09-29 2005-12-22 Cipla Ltd Formulation pharmaceutique a stabilite amelioree
WO2005115331A3 (fr) * 2004-05-24 2006-01-19 Procter & Gamble Formes de posologies de diphosphonates
US7645460B2 (en) 2004-05-24 2010-01-12 The Procter & Gamble Company Dosage forms of risedronate
US7645459B2 (en) 2004-05-24 2010-01-12 The Procter & Gamble Company Dosage forms of bisphosphonates
WO2012124982A3 (fr) * 2011-03-16 2012-11-08 현대약품 주식회사 Préparation orale ayant un enrobage entérique
US8409615B2 (en) 2004-05-24 2013-04-02 Warner Chilcott Company, Llc Low dosage forms of risedronate or its salts
US8409614B2 (en) 2004-05-24 2013-04-02 Warner Chilcott Company, Llc Low dosage forms of risedronate or its salts
US8697124B2 (en) 2006-08-24 2014-04-15 Arrow International Limited Solid dosage form of coated bisphosphonate particles

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0421921A1 (fr) * 1989-09-07 1991-04-10 Ciba-Geigy Ag Granulés doubles revêtus
WO1993009785A1 (fr) * 1991-11-22 1993-05-27 Procter & Gamble Pharmaceuticals, Inc. Compositions de risedronate a liberation lente
WO1995008331A1 (fr) * 1993-09-21 1995-03-30 Merck Frosst Canada Inc. Compositions orales a enrobage enterique contenant des derives d'acide bisphosphonique
WO1998052564A1 (fr) * 1997-05-23 1998-11-26 Cipla Limited Composition pharmaceutique contenant du benzimidazole et procede de preparation
WO1999009995A2 (fr) * 1997-08-26 1999-03-04 Unipharm Ltd. Procede de preparation de formes posologiques solides a administration par voie orale renfermant de l'acide alendronique
WO1999048498A1 (fr) * 1998-03-20 1999-09-30 A/S Gea Farmaceutisk Fabrik Formulation pharmaceutique comportant un 2- [[(2- pyridinyl) methyl] sulfinyl] benzimidazole dote d'une activite anti-ulcereuse et procede de preparation de cette formulation

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0421921A1 (fr) * 1989-09-07 1991-04-10 Ciba-Geigy Ag Granulés doubles revêtus
WO1993009785A1 (fr) * 1991-11-22 1993-05-27 Procter & Gamble Pharmaceuticals, Inc. Compositions de risedronate a liberation lente
WO1995008331A1 (fr) * 1993-09-21 1995-03-30 Merck Frosst Canada Inc. Compositions orales a enrobage enterique contenant des derives d'acide bisphosphonique
WO1998052564A1 (fr) * 1997-05-23 1998-11-26 Cipla Limited Composition pharmaceutique contenant du benzimidazole et procede de preparation
WO1999009995A2 (fr) * 1997-08-26 1999-03-04 Unipharm Ltd. Procede de preparation de formes posologiques solides a administration par voie orale renfermant de l'acide alendronique
WO1999048498A1 (fr) * 1998-03-20 1999-09-30 A/S Gea Farmaceutisk Fabrik Formulation pharmaceutique comportant un 2- [[(2- pyridinyl) methyl] sulfinyl] benzimidazole dote d'une activite anti-ulcereuse et procede de preparation de cette formulation

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005030177A3 (fr) * 2003-09-29 2005-12-22 Cipla Ltd Formulation pharmaceutique a stabilite amelioree
AU2004275569B2 (en) * 2003-09-29 2011-04-21 Cipla Limited Pharmaceutical formulation with improved stability
EP2283825A1 (fr) * 2004-05-24 2011-02-16 Warner Chilcott Company, LLC Formes orales entériques solides de dosage d'un diphosphonate avec un agent chélatant
WO2005115331A3 (fr) * 2004-05-24 2006-01-19 Procter & Gamble Formes de posologies de diphosphonates
US7645460B2 (en) 2004-05-24 2010-01-12 The Procter & Gamble Company Dosage forms of risedronate
US7645459B2 (en) 2004-05-24 2010-01-12 The Procter & Gamble Company Dosage forms of bisphosphonates
JP2010275319A (ja) * 2004-05-24 2010-12-09 Ajinomoto Co Inc キレート剤を含有するビスホスホネートの腸溶性で固形の経口剤形
EP2269584A1 (fr) * 2004-05-24 2011-01-05 Warner Chilcott Company, LLC Formes orales entériques solides de dosage d'un diphosphonate avec un agent chelatant
JP2008500339A (ja) * 2004-05-24 2008-01-10 ザ プロクター アンド ギャンブル カンパニー キレート剤を含有するビスホスホネートの腸溶性で固形の経口剤形
AU2005247299B2 (en) * 2004-05-24 2008-05-15 Allergan Pharmaceuticals International Limited Enteric solid oral dosage form of bisphosphonate containing a chelating agent
US8246989B2 (en) 2004-05-24 2012-08-21 Warner Chilcott Company, Llc Dosage forms of bisphosphonates
US8535718B2 (en) 2004-05-24 2013-09-17 Warner Chilcott Company, Llc. Dosage forms of bisphosphonates
US8409615B2 (en) 2004-05-24 2013-04-02 Warner Chilcott Company, Llc Low dosage forms of risedronate or its salts
US8409614B2 (en) 2004-05-24 2013-04-02 Warner Chilcott Company, Llc Low dosage forms of risedronate or its salts
US8697124B2 (en) 2006-08-24 2014-04-15 Arrow International Limited Solid dosage form of coated bisphosphonate particles
US10420725B2 (en) 2006-08-24 2019-09-24 Allergan Pharmaceuticals International Limited Solid dosage form of coated bisphosphonate particles
WO2012124982A3 (fr) * 2011-03-16 2012-11-08 현대약품 주식회사 Préparation orale ayant un enrobage entérique

Also Published As

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