US20050269722A1 - Process for the preparation of pharmaceutical microcapsules with enhanced taste-masking and high dissolution rate - Google Patents

Process for the preparation of pharmaceutical microcapsules with enhanced taste-masking and high dissolution rate Download PDF

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Publication number
US20050269722A1
US20050269722A1 US10/521,598 US52159805A US2005269722A1 US 20050269722 A1 US20050269722 A1 US 20050269722A1 US 52159805 A US52159805 A US 52159805A US 2005269722 A1 US2005269722 A1 US 2005269722A1
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United States
Prior art keywords
drug
microcapsules
coating
process according
comprised
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.)
Abandoned
Application number
US10/521,598
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English (en)
Inventor
Stefano De Luigi Brushci
Luigi Mapelli
Leonardo Rabaglia
Luigi Boltri
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Allergan Pharmaceuticals Holdings Ireland ULC
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Eurand Pharmaceuticals 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
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Application filed by Eurand Pharmaceuticals Ltd filed Critical Eurand Pharmaceuticals Ltd
Assigned to EURAND PHARMACEUTICALS LTD. reassignment EURAND PHARMACEUTICALS LTD. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: DE LUIGI BRUSCHI, STEFANO, MAPELLI, LUIGI GIOVANNI, RABAGLIA, LEONARDO
Publication of US20050269722A1 publication Critical patent/US20050269722A1/en
Assigned to APTALIS PHARMA LIMITED reassignment APTALIS PHARMA LIMITED CHANGE OF NAME (SEE DOCUMENT FOR DETAILS). Assignors: EURAND PHARMACEUTICALS LIMITED
Abandoned legal-status Critical Current

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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
    • B01J13/02—Making microcapsules or microballoons
    • B01J13/06—Making microcapsules or microballoons by phase separation
    • B01J13/08—Simple coacervation, i.e. addition of highly hydrophilic material
    • 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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/08—Bronchodilators
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/24—Antidepressants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/10—Antioedematous agents; Diuretics
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
    • B01J13/02—Making microcapsules or microballoons
    • B01J13/06—Making microcapsules or microballoons by phase separation

Definitions

  • the present invention relates to the field of microencapsulation of active principles. A new process is described allowing to obtain pharmaceutical microcapsules with enhanced taste masking and an optimal dissolution profile.
  • Achieving an effective encapsulation of active principles is important for the preparation of a variety of compositions; when microparticles of an active principle must be singly provided with an external coating, microencapsulation techniques are employed.
  • the microencapsulation process consists in coating small drug cores (microparticles) with a layer of polymer.
  • the polymer layering may be achieved by different techniques; in particular the microencapsulation by phase separation (or coacervation), proved very reliable in obtaining coated microparticles (M. Calanchi, “Taste Masking of oral formulations”, Pharmaceutical Manufacturing International , pp. 139-141, 1996; L. Dobetti, S. De Luigi, “Developments in Microencapsulation”, Pharmaceutical Manufacturing and Packaging Sourcer , p. 39-40, Dec. 1988).
  • microencapsulation of active principles is applied in particular to prepare pharmaceutical multiparticulate compositions such as syrups, permanent or temporary suspensions, chewable or fast melting tablets, etc.
  • the microencapsulation is used in particular to mask the taste of those drugs characterised by bitterness, throat-burning, saltiness and localised numbing of the tongue, etc.
  • FIG. 1 Caffeine, microscope image of lot. B1, described in the experimental part, showing an evident aggregation phenomena.
  • FIG. 2 Teophylline, particle size distribution of microcapsules of invention (lot. C2)
  • FIG. 3 Fluoxetine, microscope image of lot. C3, representing the microcapsules of the invention.
  • FIG. 4 Caffeine, microscope image of lot. C1, representing the microcapsules of the invention.
  • a first objective of the present invention is a process for the production of microcapsules containing a drug, characterised by the following steps:
  • phase separation can be summarised in the following, non limitative, step sequence: (i) dispersion: the creation of a two phase system in which a liquid phase (e.g. ethylcellulose solution in cyclohexane) and a solid phase (drug particles) are present simultaneously; (ii) phase separation: thanks to the action of the coacervation-inducing agent (e.g. an ethylene polymer like epolene) a third phase is formed.
  • This phase called coacervate is a highly concentrated polymer solution in solvent which spreads onto the surface of the suspended drug cores.
  • fluid droplets of coacervate coalesce and enwrap the drug cores with a continuous layer of membrane (gel phase).
  • the deposition of the polymeric membrane is promoted by a reduction of the total free interfacial energy brought about by the decrease of the coating material surface area during the coalescence of the liquid droplets;
  • hardening the fluid polymeric film is hardened by cooling down the suspension to room temperature;
  • separation microcapsules are separated from the liquid medium by settling. The supernatant is then removed and the microcapsules can be washed with fresh solvent to remove the residues of phase separation agent. Finally the microcapsules are filtered, dried and sifted.
  • next step b. is also performed by fluidized bed coating
  • the overall process is particularly advantageous in that it can be performed in the same reactor by simply changing the coating solution when passing from step a. to b.
  • the product of step a. is an ethylcellulose microcapsule containing the drug.
  • the obtained microcapsule has a drug/ethylcellulose weight ratio comprised between 1:1 and 30:1, more preferably between 3:1 and 15:1.
  • the drug/ethylcellulose weight ratio is herein referred as PR (phase ratio).
  • the microcapsules obtained in step a. are suspended in a fluidised bed and sprayed with a solution or suspension of the acrylic polymer.
  • the solvent used to form this solution or suspension is an acidic aqueous solvent, a hydroalcoholic solvent, an organic solvent, or mixtures thereof.
  • a hydroalcoholic solution it preferably comprises the following weight percentages of components, calculated with respect to the total weight of the solution:
  • the acrylic polymer can be layered indifferently during one or more layering steps: in the latter case a multilayered acrylic coating is obtained.
  • the product of step b. has an acrylic polymer content comprised between 5% and 40% by weight; an optimal range of this polymer is 10-25%
  • the acrylic polymer used in step b. is chosen among acrylic polymers for pharmaceutical use: they are well-known in pharmaceutical technology, and can be indifferently linear, branched and/or cross-linked polymers of acrylic and/or methacrylic acid; the chosen polymer must be soluble at acidic pH, (e.g. 1 g dissolves in 1N HCl); Representative, but not limitative examples of these polymers are the products of the class comprising Eudragit E (cationic copolymer based on dimethylaminoethyl methacrylate and neutral methacrylic esters).
  • a further object of the present invention are the microcapsules obtained by the process above described.
  • the process according to the present invention allows to obtain small taste-masked microcapsules (i.e. having a weight median diameter comprised between 20-800 ⁇ m, preferably 100-400 ⁇ m, with potency (i.e. mg drug/g of the end product of step b.) comprised between 400 and 950 mg/g, and capable to release at least 80% of the drug contained therein within 30 minutes, preferably in 10 minutes in a simulated gastric fluid test or in acidic media.
  • potency i.e. mg drug/g of the end product of step b.
  • the high level of potency is a pharmaceutically advantageous feature which allows to obtain, at constancy of drug content, smaller tablets or capsules, (i.e.
  • the reduction in the amounts of coating polymers involves the further advantage that the present compositions can dissolve in water without forming thickened viscous solutions around the drug cores: this further eases the drug diffusion and the establishing of a fast onset of action.
  • the obtained microcapsules further show the advantage of an improved suspendability in water, i.e. they do not form aggregates, do not float on the surface of a suspending medium, nor they adhere to side walls of a glass: therefore they do not require a separated wetting treatment with surfactants, such as instead required in case of ethylcellulose microcapsules.
  • microcapsules show the capability of maintaining the taste masking properties when suspended in neutral or basic aqueous media.
  • the use of resuspended dosage form is often required for easiness and effectiveness of administration (e.g. dosage form as monodose sachet and dry powders for extemporaneous suspension).
  • microcapsules simultaneously ensuring elevated taste masking/elevated potency/elevated dissolution rate, are new and represent a further object of the present invention.
  • These microcapsules can be further processed, optionally in presence of suitable pharmaceutical excipients, into suitable pharmaceutical formulations, e.g. dry powders for extemporaneous suspensions, tablets, minitablets, microcapsule-containing capsules, monodose sachets, fast disintegrating tablets, syrups, etc.
  • suitable pharmaceutical formulations e.g. dry powders for extemporaneous suspensions, tablets, minitablets, microcapsule-containing capsules, monodose sachets, fast disintegrating tablets, syrups, etc.
  • Active ingredients useful with this invention include antibiotic and antibacterial agents such as ketolides; antiviral agents, analgesics, anesthetics, anorexics, antiarthritics, antiasthmatic agents, anticonvulsants, antidepressants, antidiabetic agents, antidiarrheals, antihistamines, anti-inflammatory agents, antiemetics, antineoplastics, antiparkinsonism drugs, antipruritics, antipsychotics, antipyretics, antispasmodics, H2 antagonists, cardiovascular drugs, antiarrhythmics, antihypertensives, ACE inhibitors, diuretics, vasodilators, hormones, hypnotics, immunosuppressives, muscle relaxants, parasympatholytics, parasympathomimetics, psychostimulants
  • the stirring rate was then increased to 500 rpm.
  • the system was then heated to 80° C. to cause the ethylcellulose solubilisation in cyclohexane.
  • the final microcapsules were dried in an oven overnight at 40° C. and sifted by 500 ⁇ m screen.
  • a fixed amount microcapsules obtained as described in the previous paragraph were loaded in a Glatt GPCG 1 fluid-bed equipped with 4′′ Wurster insert, plate type B, spraying nozzle 1.0 mm, and sprayed with a coating suspension having the following qualitative composition:
  • the second layer of coating suspension were subsequently applied.
  • the final product was sifted by 500 ⁇ m screen.
  • the coating level obtained was calculated as microcapsules theoretical weight gain.
  • Residual cyclohexane, residual ethanol and residual polyethylene were well within the acceptance limits for pharmaceuticals.
  • a fixed amount of microcapsules was evaluated as is or after suspension in a appropriate aqueous media.
  • the coating i.e. ethylcellulose
  • the drug microparticles were first coated with a layer of ethylcellulose and further with a layer of an acrylic polymer, according to what described in the present invention.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Dispersion Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Epidemiology (AREA)
  • Psychiatry (AREA)
  • Pain & Pain Management (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Pulmonology (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
US10/521,598 2002-07-17 2002-07-17 Process for the preparation of pharmaceutical microcapsules with enhanced taste-masking and high dissolution rate Abandoned US20050269722A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/EP2002/007961 WO2004009058A1 (fr) 2002-07-17 2002-07-17 Procede pour la preparation de microcapsules pharmaceutiques avec masquage ameliore du gout et taux de dissolution eleve

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US20050269722A1 true US20050269722A1 (en) 2005-12-08

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US (1) US20050269722A1 (fr)
EP (1) EP1534251A1 (fr)
JP (1) JP4357422B2 (fr)
AU (1) AU2002368090A1 (fr)
CA (1) CA2492789C (fr)
WO (1) WO2004009058A1 (fr)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8071128B2 (en) 1996-06-14 2011-12-06 Kyowa Hakko Kirin Co., Ltd. Intrabuccally rapidly disintegrating tablet and a production method of the tablets
US8367111B2 (en) 2002-12-31 2013-02-05 Aptalis Pharmatech, Inc. Extended release dosage forms of propranolol hydrochloride
US8580313B2 (en) 2009-12-02 2013-11-12 Aptalis Pharma Limited Fexofenadine microcapsules and compositions containing them
US8747895B2 (en) 2004-09-13 2014-06-10 Aptalis Pharmatech, Inc. Orally disintegrating tablets of atomoxetine
US9040086B2 (en) 2001-10-04 2015-05-26 Aptalis Pharmatech, Inc. Timed, sustained release systems for propranolol
US9161919B2 (en) 2005-05-02 2015-10-20 Adare Pharmaceuticals, Inc. Timed, pulsatile release systems
US9884014B2 (en) 2004-10-12 2018-02-06 Adare Pharmaceuticals, Inc. Taste-masked pharmaceutical compositions
US10426734B2 (en) 2014-02-25 2019-10-01 Orbis Biosciences, Inc. Taste masking drug formulations
US10471017B2 (en) 2004-10-21 2019-11-12 Adare Pharmaceuticals, Inc. Taste-masked pharmaceutical compositions with gastrosoluble pore-formers

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070098746A1 (en) * 2005-11-02 2007-05-03 Nichols William M Multi-layered coating technology for taste masking
CN103655483A (zh) * 2012-09-26 2014-03-26 扬州市星斗药业有限公司 一种含有替比培南的颗粒及其制备方法
EP2749273B1 (fr) * 2012-12-28 2021-04-07 I.P.S. International Products & Services S.r.l. Préparation solide orale à libération modifiée
CN103893150B (zh) * 2014-03-28 2016-06-08 北京联合大学 一种青霉素v钾微囊及其制备方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6136347A (en) * 1992-01-15 2000-10-24 Bayer Aktiengesellschaft Flavor-masked pharmaceutical compositions
US6238703B1 (en) * 1998-06-29 2001-05-29 Andrx Pharmaceuticals, Inc. Controlled release oral dosage form of ketoprofen

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3900811A1 (de) * 1989-01-13 1990-07-19 Kali Chemie Pharma Gmbh Neue arzneiform
JP2002530322A (ja) * 1998-11-25 2002-09-17 シーマ・ラブス・インコーポレイテッド 味隠蔽迅速放出コーティング系
FR2795962B1 (fr) * 1999-07-08 2003-05-09 Prographarm Laboratoires Procede de fabrication de granules enrobes a gout masque et liberation immediate du principe actif
US6419956B1 (en) * 1999-12-30 2002-07-16 Ancile Pharmaceuticals Odor-masking coating for a pharmaceutical preparation
US6451345B1 (en) * 2000-01-20 2002-09-17 Eurand Pharmaceuticals Ltd. Functional coating of linezolid microcapsules for taste-masking and associated formulation for oral administration

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6136347A (en) * 1992-01-15 2000-10-24 Bayer Aktiengesellschaft Flavor-masked pharmaceutical compositions
US6238703B1 (en) * 1998-06-29 2001-05-29 Andrx Pharmaceuticals, Inc. Controlled release oral dosage form of ketoprofen

Cited By (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8357396B2 (en) 1996-06-14 2013-01-22 Kyowa Hakko Kirin Co., Ltd. Intrabuccally rapidly disintegrating tablet and a production method of the tablets
US8071128B2 (en) 1996-06-14 2011-12-06 Kyowa Hakko Kirin Co., Ltd. Intrabuccally rapidly disintegrating tablet and a production method of the tablets
US8945618B2 (en) 1996-06-14 2015-02-03 Kyowa Hakko Kirin Co., Ltd. Intrabuccally rapidly disintegrating tablet and a production method of the tablets
US8956650B2 (en) 1996-06-14 2015-02-17 Kyowa Hakko Kirin Co., Ltd. Intrabuccally rapidly disintegrating tablet and a production method of the tablets
US9358214B2 (en) 2001-10-04 2016-06-07 Adare Pharmaceuticals, Inc. Timed, sustained release systems for propranolol
US9040086B2 (en) 2001-10-04 2015-05-26 Aptalis Pharmatech, Inc. Timed, sustained release systems for propranolol
US8367111B2 (en) 2002-12-31 2013-02-05 Aptalis Pharmatech, Inc. Extended release dosage forms of propranolol hydrochloride
US8747895B2 (en) 2004-09-13 2014-06-10 Aptalis Pharmatech, Inc. Orally disintegrating tablets of atomoxetine
US11452689B2 (en) 2004-10-12 2022-09-27 Adare Pharmaceuticals, Inc. Taste-masked pharmaceutical compositions
US10568832B2 (en) 2004-10-12 2020-02-25 Adare Pharmaceuticals, Inc. Taste-masked pharmaceutical compositions
US9884014B2 (en) 2004-10-12 2018-02-06 Adare Pharmaceuticals, Inc. Taste-masked pharmaceutical compositions
US10130580B2 (en) 2004-10-12 2018-11-20 Adare Pharmaceuticals, Inc. Taste-masked pharmaceutical compositions
US10471017B2 (en) 2004-10-21 2019-11-12 Adare Pharmaceuticals, Inc. Taste-masked pharmaceutical compositions with gastrosoluble pore-formers
US10952971B2 (en) 2004-10-21 2021-03-23 Adare Pharmaceuticals, Inc. Taste-masked pharmaceutical compositions with gastrosoluble pore-formers
US9566249B2 (en) 2005-05-02 2017-02-14 Adare Pharmaceuticals, Inc. Timed, pulsatile release systems
US10045946B2 (en) 2005-05-02 2018-08-14 Adare Pharmaceuticals, Inc. Timed, pulsatile release systems
US9579293B2 (en) 2005-05-02 2017-02-28 Adare Pharmaceuticals, Inc. Timed, pulsatile release systems
US10500161B2 (en) 2005-05-02 2019-12-10 Adare Pharmaceuticals, Inc. Timed, pulsatile release systems
US9161918B2 (en) 2005-05-02 2015-10-20 Adare Pharmaceuticals, Inc. Timed, pulsatile release systems
US9161919B2 (en) 2005-05-02 2015-10-20 Adare Pharmaceuticals, Inc. Timed, pulsatile release systems
US11147772B2 (en) 2005-05-02 2021-10-19 Adare Pharmaceuticals, Inc. Timed, pulsatile release systems
US10166220B2 (en) 2009-12-02 2019-01-01 Adare Pharmaceuticals S.R.L. Fexofenadine microcapsules and compositions containing them
US9233105B2 (en) 2009-12-02 2016-01-12 Adare Pharmaceuticals S.R.L. Fexofenadine microcapsules and compositions containing them
US10729682B2 (en) 2009-12-02 2020-08-04 Adare Pharmaceuticals S.R.L. Fexofenadine microcapsules and compositions containing them
US8580313B2 (en) 2009-12-02 2013-11-12 Aptalis Pharma Limited Fexofenadine microcapsules and compositions containing them
US10426734B2 (en) 2014-02-25 2019-10-01 Orbis Biosciences, Inc. Taste masking drug formulations
US11026893B2 (en) 2014-02-25 2021-06-08 Adare Pharmaceuticals Usa, Inc. Taste masking drug formulations

Also Published As

Publication number Publication date
JP4357422B2 (ja) 2009-11-04
AU2002368090A1 (en) 2004-02-09
EP1534251A1 (fr) 2005-06-01
CA2492789C (fr) 2012-07-03
WO2004009058A1 (fr) 2004-01-29
CA2492789A1 (fr) 2004-01-29
JP2005537270A (ja) 2005-12-08

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