WO2008006216A1 - Chronothérapie anti-inflammatoire et cytoprotectrice - Google Patents

Chronothérapie anti-inflammatoire et cytoprotectrice Download PDF

Info

Publication number
WO2008006216A1
WO2008006216A1 PCT/CA2007/001241 CA2007001241W WO2008006216A1 WO 2008006216 A1 WO2008006216 A1 WO 2008006216A1 CA 2007001241 W CA2007001241 W CA 2007001241W WO 2008006216 A1 WO2008006216 A1 WO 2008006216A1
Authority
WO
WIPO (PCT)
Prior art keywords
chronotherapy
pharmacologically active
tablet
inflammatory
composition
Prior art date
Application number
PCT/CA2007/001241
Other languages
English (en)
Inventor
Bertrand Bolduc
Alain Desjardins
Nevine Rizkalla
Original Assignee
Mistral Pharma, Inc.
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 Mistral Pharma, Inc. filed Critical Mistral Pharma, Inc.
Publication of WO2008006216A1 publication Critical patent/WO2008006216A1/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
    • A61K9/2072—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
    • A61K9/209—Layered tablets, e.g. bilayer tablets; Tablets of the type inert core-active coat containing drug in at least two layers or in the core and in at least one outer 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
    • 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
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis

Definitions

  • Prostaglandins and leukotrienes are lipid mediators produced in a variety of inflammatory disease states, including inflammatory conditions of the joint. Both are products of metabolism of arachidonic acid. Cyclooxygenases (COX-1 and COX-2) are the enzymes that catalyze the conversion of arachidonic acid to prostaglandins. 5-Lipoxygenase (5-LO) catalyzes the conversion of arachidonic acid to leukotrienes.
  • Oral administration refers to oral administration of the chronotherapy tablet, per se.
  • a chronotherapy tablet of the present invention is configured structurally to deliver a specific dosage of at least one anti-inflammatory active agent at at least one predetermined period of time relative to the time of oral administration.
  • Chronotherapy tablets of the present invention are specifically constructed for oral administration particularly to release at least one anti-inflammatory active agent in at least one coordinated pulse, particularly for treating arthritis (osteoarthritis and rheumatoid arthritis, for example) or osteoarthritis in combination with a cytoprotective agent.
  • Embodiments of the present invention for example, provide a plurality of pulses of pharmacological compositions (including combinations) within 24 hours.
  • a preferred embodiment of the present invention is a chronotherapy tablet comprised of a substantially round core comprising a first end and a second end.
  • the core is comprised of at least two layers of different compositions, an anti-inflammatory composition and a cytoprotective composition, with an interface between each layer.
  • composition(s) by itself, is used herein to refer to both delay compositions (inactive materials) without drug(s) and pharmacological compositions comprising one or more drugs for delivery.
  • At least two of the layers is of a pharmacologically active composition, one being of an anti-inflammatory composition and one of a cytoprotective composition.
  • the chronotherapy tablet further comprises a coating which completely covers the core except for one exposed release face of a first layer at one end of the core.
  • the delay layer(s) are preferably substantially impenetrable to solvent or enclosed drug compounds within an adjacent layer until the delay layer has substantially completely dissolved.
  • the delay layer(s) may be comprised of well known diluent/s, dissolution rate modifier/s, lubricant/s, polymer/s, surfactant/s and/or plasticizer/s commonly used in the art of pharmacy and formulations related thereto.
  • the drug is blended with a slow dissolving polymer which comprises the shaped core.
  • a soluble diluent may also be added.
  • the blend is subsequently granulated with water or an organic solvent or a mixture of water and an organic solvent.
  • a slow dissolving or colloidal dispersion forming polymer may be dissolved or dispersed in a solvent and added to the blend while mixing continuously.
  • the mixture thus granulated is then dried at a suitable temperature and milled through a screen with an appropriate opening.
  • the granules prepared are then mixed with a soluble or insoluble lubricant.
  • Layers B in FIG. 1 may comprise well known therapeutically inactive diluent/s, and/or binder/s, and/or disintegrant/s, and/or lubricant/s, and/or dissolution rate modifier/s, and/or polymer/s, and/or surfactant/s commonly used in the art of pharmacy and formulations related thereto.
  • dissolution rate modifiers that either alone or in combination may be used in the present invention as polymers either as soluble polymers or polymers that produce clear colloidal dispersion in water, include but are not limited to hydroxypropyl cellulose, hydroxyethyl cellulose, hydroxypropyl methylcellulose; polyvinylpyrrolidone, methyl cellulose, soluble modified starches, gelatin, acacia, polyethyleneoxide, and polyethyleneglycol.
  • Water insoluble polymers that may be used in the present invention, includes but are not limited to cellulose acetate, cellulose acetate butyrate, polyvinyl alcohol, ethyl cellulose, methacrylic acid copolymers, insoluble modified starches, and polypropylene oxide.
  • Biodegradable polymers that may be used in the present invention include but are not limited to polyglycolide, poly-L-lactide, poly-D,L-lactide, caprolactone, polyamino acids, polyorthoesters and polyanhydrides.
  • polyglycolide poly-L-lactide
  • poly-D,L-lactide poly-D,L-lactide
  • caprolactone polyamino acids
  • polyorthoesters polyanhydrides
  • pH sensitive diluents examples include cellulose acetate phthalate, hydroxypropyl methylcellulose phthalate, polyvinylacetate phthalate and polymethacrylate.
  • suitable insoluble diluents include, but are not limited to, calcium sulfate, dicalcium phosphate, microcrystalline cellulose, insoluble modified starches and starch.
  • Delay layer compositions may be formulated in wet granulation by blending diluents with slow dissolving polymer/s.
  • Pharmacologically active composition layers may similarly be formulated with active compound. The blend is subsequently granulated with water or an organic solvent or a mixture of water and an organic solvent.
  • the study will be an open-label, randomised, two- way crossover, comparative bioavailability / bioequivalence study conducted in 12 normal healthy non-smoking male subjects in the fasted state.
  • Single oral doses of the combination test product will be compared to single oral doses of the two reference products.
  • the dose of diclofenac and omeprazole administered for test and reference products will be the same.
  • the objective of the study is to assess the comparative bioavailability / bioequivalence of diclofenac and omeprazole following a single dose of a diclofenac 100mg /omeperazole 40mg extended release (ER) combination test product and single doses of a diclofenac 100mg extended release (ER) reference product tablet plus two omeprazole 20mg immediate release (IR) reference product capsules (40mg in total).
  • ER extended release
  • IR immediate release
  • Test (A) consists of Diclofenac 100mg / Omeprazole 40mg ER Tablets (diclofenac sodium 100mg + omeprazole magnesium equivalent to omeprazole 40mg) provided by Mistral Pharma Inc., Canada.
  • layer A contains about 50 mg of diclofenac which takes about 4-
  • CYP2C19 Due to the major role played by CYP2C19, there is some polymorphic metabolism as 3% of Caucasians and 20% of Asians are poor metabolizers with respect to this enzyme. Less than 1 % is excreted unchanged in the urine and approximately 80% is excreted as inactive metabolites in the urine. The remainder is excreted as inactive metabolites in the feces.
  • One oral dose of the extended release test product will be compared to single doses of the two reference products with both reference products administered at the same time. All subjects will fast from 10 hours prior to dosing until 4 hours after dosing when they will be given a standard meal. Additional meals and snacks will be served as described: food and fluid intake will be standardised from the time subjects check in at the clinic until the 24 hour post-dose sample. Subjects will receive a well-balanced meal approximately 12 hours prior to the start of dosing (19h00) and a light snack and caffeine-free beverage no later than 10 hours prior to the start of dosing. Subjects will fast from 10 hours prior to the scheduled start of dosing until 4 hours post-dose, when they will be given a standard meal.
  • Blood samples will be collected from study subjects at predetermined intervals after the administration of the test or reference products and samples will be analysed for diclofenac and omeprazole. Comparative bioavailability / bioequivalence will be assessed following determination of the pharmacokinetic parameters of AUC O - T and C max by statistical analysis thereof.
  • AUCO- T The cumulative area under the plasma concentration vs. time curve from time zero to the last measured or measurable concentration, determined using the trapezoidal rule.
  • Blood samples (10 ml_) will be collected into syringes via an intravenous cannula inserted into an arm vein then transferred directly into 10 ml_ Vacutainer® tubes with K-EDTA. Samples will be collected by repeat venipuncture if necessary or if requested by the subject. Samples will be withdrawn at the time of cannulation (pre-dose, 0.0) then at the following time points: i) Following dosing with Test product (A): 0.5, 1.0, 1.5, 2.0, 3.0, 4.0, 5.0, 6.0, 7.0, 8.0, 9.0,10,11 ,12,13,14,15,16,18,20,24 and 30 hours after dosing.
  • Test product (A) 0.5, 1.0, 1.5, 2.0, 3.0, 4.0, 5.0, 6.0, 7.0, 8.0, 9.0,10,11 ,12,13,14,15,16,18,20,24 and 30 hours after dosing.
  • the study physician will remain at the clinic from the commencement of dosing until 4 hours after the first dose has been administered, and be contactable by phone for the duration of the study. Blood pressure and pulse will be checked just prior to dosing then 4 and 8 hours after dosing. No other monitoring is required during the study. Subjects will be asked open-ended questions about their health at the time of each sample in order to obtain information on adverse events without making suggestions to subjects. Clinic nursing staff will observe and be in attendance to ensure that subjects adhere to the restrictions regarding posture, movement and the consumption of food and beverages while at the clinic.
  • Omeprazole 0.0, 0.5, 1.0, 1.5, 2.0, 2.5, 3.0, 4.0, 5.0, 6.0, 7.0, 8.0, 10 and 12 hours after dosing i.e. 14 samples. Results

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  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Epidemiology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Rheumatology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Immunology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

La présente invention concerne un comprimé pour chronothérapie qui comprend : un noyau pratiquement rond ayant une première extrémité et une seconde extrémité, le noyau comprenant au moins deux couches superposées de compositions différentes avec une interface entre chaque couche; au moins une desdites couches comprenant une composition anti-inflammatoire pharmacologiquement active et au moins un desdites couches comprenant une composition cytoprotectrice pharmacologiquement active; un enrobage qui enveloppe le noyau excepté sur au moins une face du noyau découverte au niveau d'au moins une extrémité du noyau pour libérer lesdites compositions. Après administration orale, le comprimé pour chronothérapie permet un minutage correct de la délivrance de ladite composition anti-inflammatoire pharmacologiquement active et de ladite composition cytoprotectrice pharmacologiquement active par rapport au moment de l'administration orale.
PCT/CA2007/001241 2006-07-14 2007-07-12 Chronothérapie anti-inflammatoire et cytoprotectrice WO2008006216A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US80738306P 2006-07-14 2006-07-14
US60/807,383 2006-07-14

Publications (1)

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WO2008006216A1 true WO2008006216A1 (fr) 2008-01-17

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US8580954B2 (en) 2006-03-28 2013-11-12 Hospira, Inc. Formulations of low dose diclofenac and beta-cyclodextrin
WO2015154656A1 (fr) * 2014-04-08 2015-10-15 闻晓光 Préparation solide à libération contrôlée avec revêtement partiel
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CN110124059A (zh) * 2019-06-25 2019-08-16 常州大学 一种缓释抑菌剂的制备方法
US10471014B2 (en) 2017-01-04 2019-11-12 Axsome Therapeutics, Inc. Pharmaceutical compositions comprising meloxicam
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US10688102B2 (en) 2017-06-29 2020-06-23 Axsome Therapeutics, Inc. Combination treatment for migraine and other pain
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US8580954B2 (en) 2006-03-28 2013-11-12 Hospira, Inc. Formulations of low dose diclofenac and beta-cyclodextrin
US10413514B2 (en) 2014-04-08 2019-09-17 Overseas Pharmaceuticals, Ltd. Controlled-release solid preparation with partial coating
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JP2017510654A (ja) * 2014-04-08 2017-04-13 シャオガン ウェン、 一部がコーティングされた放出制御固形製剤
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