US20050038039A1 - Formulations - Google Patents

Formulations Download PDF

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Publication number
US20050038039A1
US20050038039A1 US10/501,359 US50135904A US2005038039A1 US 20050038039 A1 US20050038039 A1 US 20050038039A1 US 50135904 A US50135904 A US 50135904A US 2005038039 A1 US2005038039 A1 US 2005038039A1
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United States
Prior art keywords
formulation
composition according
polyol
molecular weight
formulations
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Abandoned
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US10/501,359
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English (en)
Inventor
Domenico Fanara
Monique Berwaer
Anthony Guichaux
Michel Deleers
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UCB Inc
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Individual
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Assigned to UCB PHARMA, INC. reassignment UCB PHARMA, INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: BERWAER, MONIQUE, DELEERS, MICHEL, FANARA, DOMENICO, GUICHAUX, ANTHONY
Publication of US20050038039A1 publication Critical patent/US20050038039A1/en
Assigned to UCB, INC. reassignment UCB, INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: UCB PHARMA, INC.
Priority to US12/230,420 priority Critical patent/US8946229B2/en
Priority to US13/242,378 priority patent/US20120010218A1/en
Abandoned legal-status Critical Current

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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
    • A61K9/0087—Galenical forms not covered by A61K9/02 - A61K9/7023
    • A61K9/0095—Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches
    • 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
    • A61K31/4965—Non-condensed pyrazines
    • 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
    • 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
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
    • A61K9/0056—Mouth soluble or dispersible forms; Suckable, eatable, chewable coherent forms; Forms rapidly disintegrating in the mouth; Lozenges; Lollipops; Bite capsules; Baked products; Baits or other oral forms for animals
    • 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
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
    • A61K9/0056—Mouth soluble or dispersible forms; Suckable, eatable, chewable coherent forms; Forms rapidly disintegrating in the mouth; Lozenges; Lollipops; Bite capsules; Baked products; Baits or other oral forms for animals
    • A61K9/0058—Chewing gums
    • 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
    • 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
    • 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
    • A61K9/2086—Layered tablets, e.g. bilayer tablets; Tablets of the type inert core-active coat
    • 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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/02—Nasal agents, e.g. decongestants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A61P27/14—Decongestants or antiallergics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Definitions

  • the present invention relates to pharmaceutical compositions for oral administration of active compounds.
  • the active compounds contemplated for use in this invention are 2-[4-(diphenylmethyl)-1-piperazinyl]-acetic acids and their amides having the general formula I wherein
  • the compounds according to formula I are orally active and selective histamine H 1 -receptor antagonists. They are described in EP 0 058 146, the contents of which are incorporated herein by reference. Examples of these compounds include cetirizine, in its dihydrochloride form marketed under the tradename Zyrtec®, the (S) enantiomer thereof, levocetirizine, in its dihydrochloride form marketed under the tradename Xyzal® and efletirizine in its dihydrochloride form.
  • U.S. Pat. No. 5,244,881 for example teaches that inclusion into cyclodextrin can mask the bitter taste of the active agent imipramine or its derivative trimipramine.
  • the inclusion complex is prepared by dissolving imipramine or trimipramine and cyclodextrin in a small amount of water or solvent, carefully mixing the mixture obtained and evaporating the said mixture.
  • polyol as used herein includes xylitol, mannitol, sorbitol, dextrose, sucrose, lactose, maltodextrins, alpha cyclodextrins, beta cyclodextrins, gamma cyclodextrins and polysaccharides, but is not limited thereto. Mannitol has proven to be a particularly suitable substance for the improvement of the palatability of preparations containing active compounds of formula I. Such compositions have, however, an important drawback.
  • microcrystalline cellulose impairs the taste of the tablets by the fact that microcrystalline cellulose is not entirely soluble in water and therefore can leave a sand-like feeling in the mouth.
  • the thickness of the coating necessary for avoiding interactions between the active compounds of formula I and the polyol(s) impedes rapid liberation of the drug from the pharmaceutical form.
  • EP 0 811 374 A1 teaches that the entire dosage form must be free of reactive alcohols, including polyols. Therefore, palatability improving polyols may not be used in the entire oral composition according to this disclosure.
  • Example 2 of EP 0 811 374 which is stated to demonstrate a preferred embodiment, clearly shows the absence of palatability improving polyols; the only polyol present in this composition is polyethyleneglycol, a high molecular weight polyol (MW 3350) which has a function different from taste masking. It is the aim of the present invention to overcome this drawback of stability loss in the presence of polyols in a way which is both palatable and avoids disadvantageous changes in product performance.
  • the problem to be solved by the invention was therefore to improve the taste and palatability of oral compositions containing active compounds of formula I and palatability improving polyols whilst at the same time avoiding any stability impairment and maintaining optimal release kinetics for the active compound.
  • Taste masking polyols generally are solid and have a molecular weight of less than 3000.
  • polyols with a low molecular weight such as xylitol, mannitol, sorbitol, dextrose or sucrose (see Table 1) are reactive or very reactive and cause a large amount of undesired reaction products.
  • polyols with a high molecular weight such as cyclodextrins (see Table 1) are very little reactive.
  • Lactose has the same molecular weight as sucrose but shows practically no reactivity with the active compounds of formula I.
  • Very reactive polyols may therefore be defined as those polyols having a molecular weight of less than 300.
  • Reactive polyols are those having a molecular weight between 300 and 950, with the exception of lactose.
  • reactive polyols may be present in any amount in the second layer. Indeed, the presence of solid polyols with a molecular weight of less than 3000 in the second formulation according to the invention is needed for palatability improvement which is essential for pharmaceutical compositions which are chewable or quickly dissolving.
  • EP 0 811 374 A1 is not concerned with taste masking as the dosage form is not intended to be dispersed in the mouth but has to be swallowed in its entirety.
  • the invention relates thus to an oral pharmaceutical composition containing at least two separate formulations:
  • a solid polyol is defined as a polyol which is not liquid at room temperature under atmospheric pressure.
  • the first formulation does not contain polyols having a molecular weight of less than 950 in a molar ratio between polyol and active compound of formula I above 10, with the exception of lactose. Since lactose has no significant reactivity with the active compounds of formula I, it may be present in higher ratios.
  • the first formulation does not contain polyols having a molecular weight of less than 300 in a molar ratio between polyol and active compound of formula I above 5.
  • the first formulation does not contain polyols having a molecular weight of less than 950 in a molar ratio between polyol and active compound of formula I above 5 with the exception of lactose.
  • the first formulation does not contain polyols having a molecular weight of less than 300.
  • the first formulation does not contain polyols having a molecular weight of less than 950, with the exception of lactose.
  • active compounds of formula I as used in this invention relates to 2-[4-(diphenylmethyl)-1-piperazinyl]-acetic acids and their amides having the general formula I as defined above and also to non-toxic, pharmaceutically acceptable salts, geometrical isomers, enantiomers, diastereomers and mixtures thereof (racemates).
  • the active compound in the first formulation is cetirizine dihydrochloride, levocetirizine dihydrochloride or efletirizine dihydrochloride.
  • drug includes the active compounds of formula I as well as any other drug.
  • the oral pharmaceutical composition contains only one active ingredient.
  • Polyols used in the second formulation are typically those which have the ability to reduce the bitter taste of the active compounds of formula I and to improve the palatability of the preparation. Examples include sorbitol, xylitol, maltitol, dextrose, sucrose, polysaccharides and preferably mannitol.
  • the formulations are prepared in the form of powders, granules, solutions or suspensions.
  • Solutions or suspensions are used to carry out a coating.
  • the first and/or second formulation can also contain an alcalinizing agent, preferably sodium citrate. This agent further decreases the production of undesired reaction products between polyols and active compounds of formula I.
  • the first formulation can contain one or more additional excipients such as colloidal anhydrous silica, microcristalline cellulose, magnesium stearate, flavors or colorants or mixtures thereof.
  • additional excipients such as colloidal anhydrous silica, microcristalline cellulose, magnesium stearate, flavors or colorants or mixtures thereof.
  • the first formulation may also contain polyols provided that they do not fall under the provisos of a specific molecular weight in a specific molar ratio as set out above.
  • the first formulation can still further contain non-polyol sweetening agents such as acesulfame K, aspartame, saccharine, saccharine sodium, cyclamate.
  • Flavors suitable for use in the present invention include essential oils and synthetic flavors such as citrus oils, fruit essences, peppermint oil, spearmint oil, clove oil, oil of wintergreen, anise, eucalyptus and the like. Other artificial flavors known to those skilled in the art are also within the scope of this invention.
  • oral composition including tablets, chewing gums, effervescent tablets or dry syrup.
  • a dry syrup is defined as a solid formulation such as for example powder or granules destinated to be administered orally in this form or after addition to a liquid.
  • the present invention relates in a particular embodiment to bi-layer tablets wherein each of the layers is prepared from one of the formulations.
  • compression is defined as the reduction in volume of a powder bed due to the application of stress (see “Pharmaceutical powder compaction technology” edited by Goran Alderbom and Chryster Nyström, p. vii, Marcel Dekker, Inc., New York).
  • the invention in another embodiment, relates to a three-layer tablet wherein an inert layer separates the layers prepared from the two formulations.
  • FIG. 1 For purposes of this invention, a “sandwich” design, wherein an inner layer made from one formulation is coated on both sides by layers made from the other formulation or double tablets having an inner core prepared from one formulation and an outer shell made from the other formulation or multi-layer tablets comprising further layers in addition to a first and second layer prepared from the first and second formulation.
  • a “sandwich” design wherein an inner layer made from one formulation is coated on both sides by layers made from the other formulation or double tablets having an inner core prepared from one formulation and an outer shell made from the other formulation or multi-layer tablets comprising further layers in addition to a first and second layer prepared from the first and second formulation.
  • a further embodiment of the invention relates to a dry syrup made of a mixture of the two formulations prepared in the form of granules, one containing the active compounds of formula I and one containing the polyol(s).
  • the powder formulations are mixed separately and then are compacted, milled and sieved separately and two kinds of granules are obtained. These granules are mixed together to give the final product.
  • compaction is defined as the transformation of a powder into a coherent specimen of defined shape by powder compression (see “Pharmaceutical powder compaction technology” edited by Göran Alderborn and Chryster Nyström, p. vii, Marcel Dekker, Inc., New York).
  • a yet further embodiment of this invention relates to a chewing gum made up for instance of a core made from the first formulation and additionally containing the gum base and a coating made from the second formulation.
  • the chewing gum may be made up of core made from the second formulation and additionally containing the gum base and a coating made from the first formulation.
  • the gum base used in the present invention for the preparation of a chewing gum may be any suitable gum base known in the art, including natural and synthetic gum bases.
  • compositions according to the present invention may contain one or more additional outer coatings.
  • compositions according to the present invention are dispersible in the mouth and do not necessitate the uptake of water in contrast to the dosage form disclosed in EP 0 811 374A1 which has to be swallowed with water.
  • the compositions of the present invention are for example in the form of orodispersible tablets (tablets to be placed in the mouth where they disperse rapidly before swallowing), they may be chewable or destined to be crunched or sucked.
  • compositions according to the present invention which are dispersible in the mouth, are bioequivalent to swallowed dosage forms.
  • the compositions according to the present invention are immediate-release formulations, i.e. pharmaceutical formulations having no or little impact on the rate of disposition of the active ingredient to the site of action.
  • Another embodiment relates to a method of preparing a composition in accordance with the present invention by separately preparing the first formulation, preparing the second formulation and combining the two formulations.
  • the formulations are obtained by usual technologies, such as compression, direct compression, granulation, wet granulation, coating.
  • the technologies are known by the man skilled in the art.
  • the masling properties may be obtained by applying the masking technologies to one or both formulations.
  • composition of the mannitol formulation for bi-layer tablets Components Composition (mg/tablet) Mannitol 241.21 Acesulfam K 4.69 Flavors 1.00 Dyes 0.60 Magnesium stearate 2.50
  • Cetirizine and mannitol formulations were then compressed on a rotary bi-layer tablet press (eg Courtoy 292/43).
  • compositions of the cetirizine.2HCl formulations for dry syrups Composition (mg) Components A B C Cetirizine.2HCl 10.00 10.00 10.00 ⁇ cyclodextrin 82.50 82.50 82.50 Acesulfam K 3.00 3.00 3.00 Microcrystalline cellulose 279.00 83.70 0.00 Lactose monohydrate 0.00 195.30 0.00 Sodium citrate 25.50 25.50 0.00 Total 400.00 400.00 95.50
  • composition for dry syrups.
  • Composition (mg) Components D Mannitol 399.60 Flavor 0.40 Total 400.00
  • compositions A, B, C and D were compacted, milled and sieved separately and granules A′, B′, C′ and D′ were obtained.
  • the final composition of the dry syrups were obtained by mixing the granules A′, B′, C′ and D′ according to the proportions described in table 7. TABLE 7 Dry syrups compositions.
  • Components (mg) Compositions A′, B′ C′ D′ E 400.00 0.00 0.00 400.00 F 0.00 400.00 0.00 400.00 G 0.00 0.00 95.50 404.50 H 100.00 0.00 0.00 200.00
  • composition of a chewing gum made up of a core containing cetirizine, obtained by compression, and a coating containing the polyols is given in table 9. TABLE 9 Composition of the chewing gum.
  • the chewing gum complies with the stability requirements.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Zoology (AREA)
  • Physiology (AREA)
  • Nutrition Science (AREA)
  • Pulmonology (AREA)
  • Ophthalmology & Optometry (AREA)
  • Rheumatology (AREA)
  • Pain & Pain Management (AREA)
  • Immunology (AREA)
  • Otolaryngology (AREA)
  • Dermatology (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
US10/501,359 2002-01-15 2003-01-14 Formulations Abandoned US20050038039A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US12/230,420 US8946229B2 (en) 2002-01-15 2008-08-28 Formulations
US13/242,378 US20120010218A1 (en) 2002-01-15 2011-09-23 Formulations

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP02000871 2002-01-15
EP02/0008710.0 2002-01-15
PCT/EP2003/000260 WO2003059328A1 (en) 2002-01-15 2003-01-14 Formulations

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US12/230,420 Division US8946229B2 (en) 2002-01-15 2008-08-28 Formulations

Publications (1)

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US20050038039A1 true US20050038039A1 (en) 2005-02-17

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US10/501,359 Abandoned US20050038039A1 (en) 2002-01-15 2003-01-14 Formulations
US12/230,420 Active 2026-12-13 US8946229B2 (en) 2002-01-15 2008-08-28 Formulations
US13/242,378 Abandoned US20120010218A1 (en) 2002-01-15 2011-09-23 Formulations

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US12/230,420 Active 2026-12-13 US8946229B2 (en) 2002-01-15 2008-08-28 Formulations
US13/242,378 Abandoned US20120010218A1 (en) 2002-01-15 2011-09-23 Formulations

Country Status (19)

Country Link
US (3) US20050038039A1 (enExample)
EP (1) EP1467715B1 (enExample)
JP (4) JP4724367B2 (enExample)
KR (1) KR101005648B1 (enExample)
CN (2) CN100455287C (enExample)
AT (1) ATE486587T1 (enExample)
AU (3) AU2003201161B2 (enExample)
BR (1) BR0306870A (enExample)
CA (1) CA2472396A1 (enExample)
CO (1) CO5590918A2 (enExample)
DE (1) DE60334773D1 (enExample)
ES (1) ES2354688T3 (enExample)
MX (1) MXPA04006775A (enExample)
NO (1) NO333936B1 (enExample)
NZ (1) NZ534039A (enExample)
PL (1) PL212123B1 (enExample)
RU (1) RU2004123612A (enExample)
WO (1) WO2003059328A1 (enExample)
ZA (1) ZA200404796B (enExample)

Cited By (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060083786A1 (en) * 2004-07-29 2006-04-20 Glenmark Pharmaceuticals Limited Taste masking pharmaceutical composition containing levocetirizine
US20060165777A1 (en) * 2004-05-21 2006-07-27 Lawrence Solomon Dosage forms contained within a capsule or sachet
US20060290417A1 (en) * 2005-06-23 2006-12-28 Samsung Electro-Mechanics Co., Ltd. Exponential function generator and variable gain amplifier using the same
US20070014852A1 (en) * 2005-07-12 2007-01-18 Lawrence Solomon Tablets having a printed separation mark to guide breaking
US20070086974A1 (en) * 2005-10-06 2007-04-19 Gawande Rahul S Cetirizine compositions
US20070134321A1 (en) * 2004-05-21 2007-06-14 Lawrence Solomon Pharmaceutical tablets with height greater than width
US20070141155A1 (en) * 2004-05-21 2007-06-21 Lawrence Solomon Pharmaceutical tablets having height greater than width
US20070190147A1 (en) * 2004-05-21 2007-08-16 Lawrence Solomon Pharmaceutical tablets with active and inactive segments
US20070237815A1 (en) * 2006-04-06 2007-10-11 Lawrence Solomon Dosage forms and methods comprising amlodipine and chlorthalidone
US20080075784A1 (en) * 2004-07-22 2008-03-27 Pfizer Inc. Taste Making Formulation Comprising The Drug In A Dissolution-Retarded Form And/Or Cyclodextrin In A Dissolution-Enhanced Form
US20080233190A1 (en) * 2005-11-18 2008-09-25 Lawrence Solomon Segmented Pharmaceutical Dosage Forms
WO2009006899A1 (en) * 2007-07-11 2009-01-15 Fertin Pharma A/S Compressed chewing gum tablet comprising taste-masking agent
WO2009006898A1 (en) * 2007-07-11 2009-01-15 Fertin Pharma A/S Stable medicated chewing gum comprising cyclodextrin inclusion complex
US20090269393A1 (en) * 2006-06-12 2009-10-29 Jubliant Organosys Limited Chewable Bilayer Tablet Formulation
US20100068271A1 (en) * 2006-11-30 2010-03-18 Accu-Break Technologies, Inc Divisible Osmotic Dosage Forms and Methods of Use
US7713547B2 (en) 2004-05-21 2010-05-11 Accu-Break Pharmaceuticals, Inc. Method of administering a partial dose of a segmented pharmaceutical tablet
US7838031B2 (en) 2004-05-21 2010-11-23 Lawrence Solomon Method of administering a partial dose using a segmented pharmaceutical tablet
US20110070287A1 (en) * 2008-05-26 2011-03-24 Bruno Provstgaard Nielsen Film-Coated Compressed Chewing Gum
US20110086092A1 (en) * 2006-08-08 2011-04-14 Accu-Break Technologies, Inc. Pharmacuetical tablets containing a plurality of active ingredients
WO2011110939A2 (en) 2010-03-11 2011-09-15 Rubicon Research Private Limited Pharmaceutical compositions of substituted benzhydrylpiperazines
US10060860B2 (en) 2007-06-30 2018-08-28 Smp Logic Systems Pharmaceutical dosage forms fabricated with nanomaterials
WO2021156698A1 (en) 2020-02-03 2021-08-12 Johnson & Johnson Consumer Inc. A single layer chewable tablet comprising cetirizine
WO2023224949A1 (en) * 2022-05-16 2023-11-23 Perkinelmer U.S. Llc Compositions and methods relating to loop mediated isothermal amplification (lamp)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ATE388693T1 (de) * 2002-04-04 2008-03-15 Pfizer Prod Inc Wohlschmeckende kautablette
EP2260871B1 (fr) * 2004-04-01 2013-05-15 Pierre Fabre Medicament Complexes d'inclusions comprenant du piroxicam, une cyclodextrine et l'arginine
CA2734691C (en) 2008-09-05 2017-05-16 Mcneil-Ppc, Inc. Method for making cetirizine tablets
WO2010107404A1 (en) 2009-03-16 2010-09-23 Mahmut Bilgic Stable pharmaceutical combinations
WO2011146032A2 (en) * 2010-05-18 2011-11-24 Mahmut Bilgic Effervescent formulations
US20170105988A1 (en) * 2014-03-27 2017-04-20 Ucb Biopharma Sprl Pharmaceutical Compositions Comprising Levocetirizine
JP2016094364A (ja) * 2014-11-14 2016-05-26 ニプロ株式会社 安定化および苦味抑制された口腔内崩壊製剤
JP7049610B2 (ja) * 2018-05-21 2022-04-07 高田製薬株式会社 レボセチリジン固形製剤

Citations (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4238510A (en) * 1979-02-21 1980-12-09 Life Savers, Inc. Sugarless coating for chewing gum and confections and method
US5344659A (en) * 1991-08-02 1994-09-06 Yoshie Kurihara Chewing gum
US5380530A (en) * 1992-12-29 1995-01-10 Whitehill Oral Technologies Oral care composition coated gum
US5419898A (en) * 1992-12-25 1995-05-30 Senju Pharmacuetical Co., Ltd. Antiallergic composition for ophthalmic or nasal use
US5543155A (en) * 1993-12-09 1996-08-06 Egis Gyogyszergyar Rt. Diffusion-osmotic controlled drug-release pharmaceutical composition and process for preparing same
US5711961A (en) * 1994-07-26 1998-01-27 Apr Applied Pharma Research S.A. Pharmaceutical compositions based on chewing gum and a method for the preparation thereof
US5866179A (en) * 1996-05-03 1999-02-02 Avant-Garde Technologies & Products S.A. Medicated chewing gum and a process for preparation thereof
US5876759A (en) * 1993-07-27 1999-03-02 Mcneil-Ppc, Inc. Rapidly disintegrating pharmaceutical dosage form and process for preparation thereof
US6172095B1 (en) * 1996-11-25 2001-01-09 The Procter & Gamble Company Guanidinylamino heterocycle compounds useful as alpha-2 adrenoceptor agonists
US6245353B1 (en) * 1998-03-31 2001-06-12 Asta Medica Ag Solid, rapidly disintegrating cetirizine formulations
US6319513B1 (en) * 1998-08-24 2001-11-20 The Procter & Gamble Company Oral liquid mucoadhesive compounds
US6627234B1 (en) * 1998-12-15 2003-09-30 Wm. Wrigley Jr. Company Method of producing active agent coated chewing gum products
US20030206948A1 (en) * 1997-07-10 2003-11-06 Gerhard Gergely Soluble, gum-containing, coated chewable tablet
US20040028772A1 (en) * 2000-08-14 2004-02-12 Carsten Andersen Method for preparation of chewing gum with customer acceptable taste
US20040170690A1 (en) * 2001-06-28 2004-09-02 Domenico Fanara Tablet comprising cetirizine and pseudoephedrine

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4260596A (en) * 1979-08-13 1981-04-07 Bristol-Myers Company Edible unit dosage form consisting of outer mannitol shell and inner liquid or gel center and method for manufacturing the same
FR2647343B1 (fr) 1989-05-24 1994-05-06 Rhone Poulenc Sante Nouvelle forme pharmaceutique poreuse et sa preparation
US5460825A (en) * 1990-05-23 1995-10-24 Mcneil-Ppc, Inc. Taste mask coatings for preparing chewable pharmaceutical tablets
EP0811374A1 (en) 1996-05-29 1997-12-10 Pfizer Inc. Combination dosage form comprising cetirizine and pseudoephedrine
WO2000035298A1 (en) 1996-11-27 2000-06-22 Wm. Wrigley Jr. Company Chewing gum containing medicament active agents
BE1011251A3 (fr) * 1997-07-03 1999-06-01 Ucb Sa Compositions pharmaceutiques administrables par voie orale, comprenant une substance active et une cyclodextrine.
WO2002049607A2 (en) * 2000-12-20 2002-06-27 Firmenich Sa Flavoured oral drug delivery system
US20030035839A1 (en) * 2001-05-15 2003-02-20 Peirce Management, Llc Pharmaceutical composition for both intraoral and oral administration
ATE388693T1 (de) * 2002-04-04 2008-03-15 Pfizer Prod Inc Wohlschmeckende kautablette

Patent Citations (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4238510A (en) * 1979-02-21 1980-12-09 Life Savers, Inc. Sugarless coating for chewing gum and confections and method
US5344659A (en) * 1991-08-02 1994-09-06 Yoshie Kurihara Chewing gum
US5419898A (en) * 1992-12-25 1995-05-30 Senju Pharmacuetical Co., Ltd. Antiallergic composition for ophthalmic or nasal use
US5380530A (en) * 1992-12-29 1995-01-10 Whitehill Oral Technologies Oral care composition coated gum
US5876759A (en) * 1993-07-27 1999-03-02 Mcneil-Ppc, Inc. Rapidly disintegrating pharmaceutical dosage form and process for preparation thereof
US5543155A (en) * 1993-12-09 1996-08-06 Egis Gyogyszergyar Rt. Diffusion-osmotic controlled drug-release pharmaceutical composition and process for preparing same
US5711961A (en) * 1994-07-26 1998-01-27 Apr Applied Pharma Research S.A. Pharmaceutical compositions based on chewing gum and a method for the preparation thereof
US5866179A (en) * 1996-05-03 1999-02-02 Avant-Garde Technologies & Products S.A. Medicated chewing gum and a process for preparation thereof
US6172095B1 (en) * 1996-11-25 2001-01-09 The Procter & Gamble Company Guanidinylamino heterocycle compounds useful as alpha-2 adrenoceptor agonists
US20030206948A1 (en) * 1997-07-10 2003-11-06 Gerhard Gergely Soluble, gum-containing, coated chewable tablet
US6245353B1 (en) * 1998-03-31 2001-06-12 Asta Medica Ag Solid, rapidly disintegrating cetirizine formulations
US6319513B1 (en) * 1998-08-24 2001-11-20 The Procter & Gamble Company Oral liquid mucoadhesive compounds
US6627234B1 (en) * 1998-12-15 2003-09-30 Wm. Wrigley Jr. Company Method of producing active agent coated chewing gum products
US20040028772A1 (en) * 2000-08-14 2004-02-12 Carsten Andersen Method for preparation of chewing gum with customer acceptable taste
US20040170690A1 (en) * 2001-06-28 2004-09-02 Domenico Fanara Tablet comprising cetirizine and pseudoephedrine

Cited By (41)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8158148B2 (en) 2004-05-21 2012-04-17 Accu-Break Technologies, Inc. Pharmaceutical tablets comprising two or more unitary segments
US7988996B2 (en) 2004-05-21 2011-08-02 Accu-Break Technologies, Inc. Pharmaceutical tablets with height greater than width
US7879352B2 (en) 2004-05-21 2011-02-01 Accu-Break Technologies, Inc. Scored pharmaceutical tablets comprising a plurality of segments
US20080199521A1 (en) * 2004-05-21 2008-08-21 Lawrence Solomon Scored Pharmaceutical Tablets Comprising A Plurality Of Secments
US7713547B2 (en) 2004-05-21 2010-05-11 Accu-Break Pharmaceuticals, Inc. Method of administering a partial dose of a segmented pharmaceutical tablet
US20070134321A1 (en) * 2004-05-21 2007-06-14 Lawrence Solomon Pharmaceutical tablets with height greater than width
US20070141155A1 (en) * 2004-05-21 2007-06-21 Lawrence Solomon Pharmaceutical tablets having height greater than width
US20070190147A1 (en) * 2004-05-21 2007-08-16 Lawrence Solomon Pharmaceutical tablets with active and inactive segments
US8034380B2 (en) 2004-05-21 2011-10-11 Accu•Break Technologies, Inc. Immediate release pharmaceutical tablets with height greater than width
US20080003285A1 (en) * 2004-05-21 2008-01-03 Lawrence Solomon Immediate Release Pharmaceutical Tablets With Height Greater Than Width
US7318935B2 (en) 2004-05-21 2008-01-15 Accu-Break Technologies, Inc. Pharmaceutical tablets with active and inactive segments
US20080233189A1 (en) * 2004-05-21 2008-09-25 Lawrence Solomon Pharmaceutical Tablets Comprising Two or More Unitary Segments
US20060165777A1 (en) * 2004-05-21 2006-07-27 Lawrence Solomon Dosage forms contained within a capsule or sachet
US7622137B2 (en) 2004-05-21 2009-11-24 Accu-Break Technologies, Inc. Dosage forms contained within a capsule or sachet
US7329418B2 (en) 2004-05-21 2008-02-12 Accu Break Technologies, Inc. Pharmaceutical tablets having height greater than width
US20090130207A1 (en) * 2004-05-21 2009-05-21 Solapharm, Inc. Pharmaceutical Tablets Having a Relatively Inactive Segment
US20080241239A1 (en) * 2004-05-21 2008-10-02 Lawrence Solomon Pharmaceutical Tablets Having a Separation Mark Positioned on the Side of Said Tablets
US7838031B2 (en) 2004-05-21 2010-11-23 Lawrence Solomon Method of administering a partial dose using a segmented pharmaceutical tablet
US20080075784A1 (en) * 2004-07-22 2008-03-27 Pfizer Inc. Taste Making Formulation Comprising The Drug In A Dissolution-Retarded Form And/Or Cyclodextrin In A Dissolution-Enhanced Form
US20060083786A1 (en) * 2004-07-29 2006-04-20 Glenmark Pharmaceuticals Limited Taste masking pharmaceutical composition containing levocetirizine
US20060290417A1 (en) * 2005-06-23 2006-12-28 Samsung Electro-Mechanics Co., Ltd. Exponential function generator and variable gain amplifier using the same
US20070014852A1 (en) * 2005-07-12 2007-01-18 Lawrence Solomon Tablets having a printed separation mark to guide breaking
US7780985B2 (en) 2005-07-12 2010-08-24 Accu-Break Technologies, Inc. Tablets having a printed separation mark to guide breaking
US20070086974A1 (en) * 2005-10-06 2007-04-19 Gawande Rahul S Cetirizine compositions
US8231902B2 (en) 2005-11-18 2012-07-31 Accu-Break Technologies, Inc. Segmented pharmaceutical dosage forms
US20080233190A1 (en) * 2005-11-18 2008-09-25 Lawrence Solomon Segmented Pharmaceutical Dosage Forms
US20070237815A1 (en) * 2006-04-06 2007-10-11 Lawrence Solomon Dosage forms and methods comprising amlodipine and chlorthalidone
US20090269393A1 (en) * 2006-06-12 2009-10-29 Jubliant Organosys Limited Chewable Bilayer Tablet Formulation
US20110086092A1 (en) * 2006-08-08 2011-04-14 Accu-Break Technologies, Inc. Pharmacuetical tablets containing a plurality of active ingredients
US20100068271A1 (en) * 2006-11-30 2010-03-18 Accu-Break Technologies, Inc Divisible Osmotic Dosage Forms and Methods of Use
US10060860B2 (en) 2007-06-30 2018-08-28 Smp Logic Systems Pharmaceutical dosage forms fabricated with nanomaterials
WO2009006898A1 (en) * 2007-07-11 2009-01-15 Fertin Pharma A/S Stable medicated chewing gum comprising cyclodextrin inclusion complex
US20100189768A1 (en) * 2007-07-11 2010-07-29 Fertin Pharma A/S Compressed chewing gum tablet comprising taste-masking agent
US20100260818A1 (en) * 2007-07-11 2010-10-14 Fertin Pharma A/S Stable medicated chewing gum comprising cyclodextrin inclusion complex
WO2009006899A1 (en) * 2007-07-11 2009-01-15 Fertin Pharma A/S Compressed chewing gum tablet comprising taste-masking agent
US20130022652A1 (en) * 2007-07-11 2013-01-24 Fertin Pharma A/S Stable medicated chewing gum comprising cyclodextrin inclusion complex
EP2550967A1 (en) * 2007-07-11 2013-01-30 Fertin Pharma A/S Compressed chewing gum tablet comprising taste-masking agent
US20110070287A1 (en) * 2008-05-26 2011-03-24 Bruno Provstgaard Nielsen Film-Coated Compressed Chewing Gum
WO2011110939A2 (en) 2010-03-11 2011-09-15 Rubicon Research Private Limited Pharmaceutical compositions of substituted benzhydrylpiperazines
WO2021156698A1 (en) 2020-02-03 2021-08-12 Johnson & Johnson Consumer Inc. A single layer chewable tablet comprising cetirizine
WO2023224949A1 (en) * 2022-05-16 2023-11-23 Perkinelmer U.S. Llc Compositions and methods relating to loop mediated isothermal amplification (lamp)

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