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WO2014125085A1 - Formulations pharmaceutiques orales comprenant du nimésulide et du thiocolchicoside - Google Patents

Formulations pharmaceutiques orales comprenant du nimésulide et du thiocolchicoside Download PDF

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Publication number
WO2014125085A1
WO2014125085A1 PCT/EP2014/052948 EP2014052948W WO2014125085A1 WO 2014125085 A1 WO2014125085 A1 WO 2014125085A1 EP 2014052948 W EP2014052948 W EP 2014052948W WO 2014125085 A1 WO2014125085 A1 WO 2014125085A1
Authority
WO
WIPO (PCT)
Prior art keywords
formulation according
tablet formulation
sodium
thiocolchicoside
nimesulide
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/EP2014/052948
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English (en)
Inventor
Ali TÜRKYILMAZ
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.)
Sanovel Ilac Sanayi ve Ticaret AS
Original Assignee
Sanovel Ilac Sanayi ve Ticaret AS
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 Sanovel Ilac Sanayi ve Ticaret AS filed Critical Sanovel Ilac Sanayi ve Ticaret AS
Priority to EP14705127.0A priority Critical patent/EP2956125A1/fr
Publication of WO2014125085A1 publication Critical patent/WO2014125085A1/fr
Anticipated expiration legal-status Critical
Ceased 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
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/63—Compounds containing para-N-benzenesulfonyl-N-groups, e.g. sulfanilamide, p-nitrobenzenesulfonyl hydrazide
    • 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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
    • A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
    • A61K31/704—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin attached to a condensed carbocyclic ring system, e.g. sennosides, thiocolchicosides, escin, daunorubicin
    • 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

Definitions

  • the present invention relates to a novel pharmaceutical combination comprising nimesulide or a pharmaceutically acceptable salt thereof and thiocolchicoside or a pharmaceutically acceptable salt thereof with anti-inflammatory, analgesic and myorelaxant effects.
  • the present invention more particularly relates to a pharmaceutical combination in the form of a multilayer oral tablet comprising nimesulide and thiocolchicoside with antiinflammatory, analgesic and myorelaxant effects.
  • Nimesulide is a non-steroidal anti-inflammatory drug (NSAID) molecule with the chemical structure illustrated in Formula 1 below.
  • NSAID non-steroidal anti-inflammatory drug
  • Nimesulide selectively inhibits the cyclooxygenase-2 (COX-2) enzyme. It has antipyretic, analgesic, and anti-inflammatory effects. It is used in osteoarthritis and extraarticular rheumatic diseases, post-traumatic and post-operative inflammations and painful symptoms, high fever, and in dysmenorrhea!.
  • COX-2 cyclooxygenase-2
  • Thiocolchicoside is a myorelaxant with the structure illustrated in Formula 2 below.
  • Thiocolchicoside is a semi-synthetic sulfur salt, obtained from colchicoside, a natural glycoside found in Anatolian Colchicum Autumnale (Autumn crocuses). This natural glycoside has muscle relaxant, anti-inflammatory and analgesic effects. Thiocolchicoside exerts the myorelaxant effect by activating the gamma-aminobutyric acid (GABA) and glycine receptors at the spinal level. Furthermore, glycinomimetic effects of thiocolchicoside are seen in the nerve system at varying levels. It does not have a curarizing effect. It does not give rise to motor plaque paralysis, and no inhalation-related problems are encountered. It does not have effects on the cardiovascular system either.
  • GABA gamma-aminobutyric acid
  • Muscle relaxants also reduce the muscle tonus and are used in treating muscle spasms and contractures.
  • Muscle spasm is one of the main factors held responsible for chronic pains; in addition to rheumatic inflammatory and degenerative orthopedic pathologies, it defines various pathologies of the locomotor system as well; when it affects the joints, it does not cause pain only, but it leads to stiffness that reduces the mobility and flexibility of joints at the affected site.
  • Muscle contractures also characterizes various pathologies of the locomotor system, and is one of the main causes, which is deemed responsible for the persistency of pain associated with such pathologies.
  • Muscle relaxants are used in neuromuscular and muscle-skeleton system injuries. There are two main types of muscle relaxants: centrally-acting muscle relaxants and directly- acting muscle relaxants. Centrally-acting muscle relaxants typically act on the central nervous system (CNS) in a selective manner and are primarily used for alleviating painful muscle spasms and the strains occurring during muscle-skeleton system and neuromuscular damages. The action mechanisms thereof are associated with the causes of the CNS-suppressing activities.
  • CNS central nervous system
  • muscle relaxants and antispasmodic molecules constitute a subject matter which is still clinically significant.
  • Muscle relaxants are used alone or together with customary analgesics in treating pain.
  • a pharmaceutical combination may give complex or unforeseeable outcomes; but so far, nimesulide has never been used together with thiocolchicoside in a pharmaceutical combination for treating inflammatory, pain, and muscle-skeletal system diseases.
  • Researching the patent literature may result in various patents which relate to nimesulide and thiocolchicoside.
  • the patent EP0853476B1 discloses a pharmaceutical preparation comprising as active agent nimesulide or a pharmaceutically acceptable salt thereof, characterized in that the preparation's base contains one phospholipid and at least one substance with acid reaction, specifically an acid.
  • the patent FR 2 725 134 B1 discloses a novel pharmaceutical composition comprising ibuprofen or a pharmaceutically acceptable salt thereof and thiocolchicoside or a pharmaceutically acceptable salt thereof in a ratio ranging from around 1 :50 to around 1 :200. According to that invention, said pharmaceutical composition is useful in treating painful muscle syndromes and more specifically in treating lumbagos.
  • the patent EP 0 837 684 B1 discloses a pharmaceutical composition comprising, in solid form, a diclofenac salt and thiocolchicoside, combined with at least one pharmaceutically acceptable carrier, for use in therapy. According to that invention, the muscle relaxant drug used in combination with flurbiprofen is metocarbamol and this combination is particularly used in treating influenza and common cold symptoms involving sore throat.
  • the basic difficulties encountered when two or more molecules are combined in the same pharmaceutical dosage form are (a) ensuring compatibility between different active agents and/or among the active agents and the excipients used, (b) providing therapeutic compatibility between the active agents, taking into account the pharmacokinetic and/or biopharmaceutical properties such as the posology of the respective combination to obtain efficient and reliable plasma levels of both active agents.
  • Conventional analgesic and myorelaxant treatments typically comprise administrating one or more different analgesic and muscle relaxant drug(s) in the form of a pharmaceutical composition.
  • analgesic and muscle relaxant drugs are not always more convenient than immediate release formulations as to the reduced dosage schedule in terms of higher compatibility and higher patient compliance. Therefore, there is a need to develop a formulation having an immediate release layer comprising nimesulide and an immediate release layer or a controlled release layer comprising thiocolchicoside for providing an efficient treatment of pain, spasticity, inflammatory symptoms and painful muscle spasms, as well as an improved side effect profile and increased patient compliance.
  • Figure 1 illustrates an oral solid multilayer tablet formulation having i) a first layer (a) comprising a first active agent, ii) a second layer (b) comprising a second active agent, and iii) a barrier layer (c) separating these two layers from each other.
  • the present invention relates to an easily administrable nimesulide and thiocolchicoside combination, eliminating all aforesaid problems and brining additional advantages to the relevant prior art.
  • the main object of the present invention is to obtain a multilayer tablet formulation comprising a stable and well-soluble combination of nimesulide and thiocolchicoside with anti-inflammatory, analgesic, and myorelaxant effects.
  • the layer comprising nimesulide and the layer comprising thiocolchicoside are separated using an inert layer such that the incompatibility of these agents is eliminated and efficient and safe plasma levels are obtained. While the layer (a) comprising nimesulide provides immediate release, the layer (b) comprising thiocolchicoside provides either immediate release or controlled release. These two layers are separated using an inert layer (c).
  • the present invention preferably comprises nimesulide in the immediate release layer and thiocolchicoside in the immediate release layer.
  • the layers comprising nimesulide and thiocolchicoside are separated by an inert layer so as to give a multilayer tablet formulation.
  • an inert layer By virtue of using a cellulosic polymer in the inert layer, the efficient and safe plasma levels of both active agents are achieved rapidly. Thus, the absorption and the bioavailability of the pharmaceutical formulation are increased as well.
  • the cellulosic polymers used are preferably hydroxypropyl cellulose and microcrystalline cellulose.
  • Another object of the present invention is to obtain a formulation which dissolves well in the gastrointestinal fluid. It was surprisingly found that the ratio of the disintegrants used in the active agent-comprising layers has a substantial influence on the release properties of the tablet.
  • the amount of the disintegrant is 1 .0 to 30.0%, preferably 2.0 to 20.0% in the nimesulide-comprising layer and the amount of the disintegrant is 3.0 to 35.0%, preferably 5.0 to 25.0% in the thiocolchicoside-comprising layer; thus the different ratios of the disintegrant in the different layers provide well dissolving the multilayer tablet formulation in the gastrointestinal fluid and improve the absorption thereof.
  • Suitable disintegrants for use in the formulation according to the present invention are alginic acid and alginates, ion-exchange resins, magnesium aluminum silicate, sodium dodecyl sulfate, sodium carboxymethyl cellulose, croscarmellose sodium, cross linked polyvinylpyrrolidone, carboxymethylcellulose calcium, docusate sodium, guar gum, corn starch, polacrilin potassium, poloxamer, povidone, sodium alginate, sodium glycine carbonate, sodium lauryl sulfate, sodium starch glycolate, or the mixtures thereof.
  • compositions according to the present invention may further comprise one or more pharmaceutically acceptable excipient(s).
  • the pharmaceutically acceptable excipients comprise at least one selected from the group consisting of fillers, binders, lubricants and glidants, flavoring agents, sweeteners and coloring agents.
  • Suitable fillers for use in the formulation according to the present invention are mannitol, spray-dried mannitol; polysaccharides such as microcrystalline cellulose; dibasic calcium phosphate dihydrate, lactose, sugars, sorbitol, lactose monohydrate; a mixture of microcrystalline cellulose and guar gum (Avicel CE-15); a mixture of mannitol, polyplasdone and syolid (Pharmaburst); a mixture of mannitol, crospovidone and polyvinyl acetate (Ludiflash); inorganic salts such as isomalt, sucrose, calcium salts, or the mixtures thereof.
  • the amount of the filler is 2.0 to 90.0%, preferably 10.0 to 85.0%, and more preferably 15.0 to 80.0% of the total weight of the tablet.
  • Suitable binders for use in the formulation according to the present invention are natural gums, starch, gelatin, polyvinylpyrrolidone, polymethacrylates; collagen, proteins such as gelatin; semisynthetic polymers such as agar, alginate, sodium alginate, pectin, starch, carboxymethyl cellulose, hydroxypropyl cellulose, hydroxypropyl methylcellulose, methyl cellulose; synthetic polymers such as carbomer, poloxamer, polyacrylamide, polyvinyl alcohol; inorganic substances such as aluminum hydroxide, bentonite, laponite; starch mucilage, acacia mucilage, polydextrose, polyethylene oxide, or the mixtures thereof.
  • the amount of the binder is 0.001 to 55.0%, preferably 0.1 to 30.0% of the total weight of the tablet.
  • Suitable lubricants and glidants for use in the formulation according to the present invention are sodium stearyl fumarate, magnesium stearate, polyethylene glycol, colloidal silicon dioxide, stearic acid, talk, metal stearates, boric acid, sodium chloride benzoate and acetate, sodium or magnesium lauryl sulfate, or the mixtures thereof.
  • the total amount of the lubricant and the glidant is 0.01 to 20.0%, preferably 0.1 to 10.0% of the total weight of the tablet.
  • Suitable sweeteners for use in the formulation according to the present invention are sucralose, acesulfame-K, aspartame, saccharine or saccharine sodium and calcium salts, sodium cyclamate, sucrose, fructose, glucose, sorbitol, or the mixtures thereof.
  • the amount of the sweetener is 0.01 to 15.0% of the total weight of the tablet.
  • Suitable flavoring agents for use in the formulation according to the present invention are fruit aromas such as orange, banana, strawberry, cherry, wild cherry, lemon; cardamom, anis, mint, menthol, vanillin, and ethyl vanillin, and other similar aromas, or the mixtures thereof.
  • the amount of the flavoring agent is 0.01 to 10.0% of the total weight of the tablet.
  • the present invention is used for treating osteoarthritis, pain associated with tissue trauma following osteoarthritis surgery, psoriatic arthritis, rheumatoid arthritis, myalgia, bone pain, arthralgia, muscle spasms, soft tissue traumas, lumbago, back pain, sciatica and torticollis.
  • nimesulide, lactose monohydrate, microcrystalline cellulose PH 101 , and sodium starch glycolate are taken to a fluidized bed dryer.
  • An aqueous solution of hydroxypropyl cellulose (Klucell LF) is prepared, this solution is sprayed to the fluidized bed dryer (spray granulation), dried, the dried granules are ground, transferred to an intermediate bulk container (IBC), magnesium stearate is introduced to the mixture and stirred for 5 more minutes.
  • IBC intermediate bulk container
  • the multilayer tablets are made using the amounts given above for each layer.

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

Abstract

La présente invention concerne une nouvelle combinaison pharmaceutique comprenant du nimésulide ou un sel pharmaceutiquement acceptable de celui-ci et du thiocolchicoside ou un sel pharmaceutiquement acceptable de celui-ci ayant des effets anti-inflammatoires, analgésiques et myorelaxants. La présente invention concerne particulièrement une combinaison pharmaceutique sous la forme d'un comprimé oral multicouche comprenant du nimésulide et du thiocolchicoside ayant des effets anti-inflammatoires, analgésiques et myorelaxants.
PCT/EP2014/052948 2013-02-15 2014-02-14 Formulations pharmaceutiques orales comprenant du nimésulide et du thiocolchicoside Ceased WO2014125085A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP14705127.0A EP2956125A1 (fr) 2013-02-15 2014-02-14 Formulations pharmaceutiques orales comprenant du nimésulide et du thiocolchicoside

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
TR2013/01875 2013-02-15
TR201301875 2013-02-15

Publications (1)

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WO2014125085A1 true WO2014125085A1 (fr) 2014-08-21

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EP (1) EP2956125A1 (fr)
WO (1) WO2014125085A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3173077A1 (fr) 2015-11-30 2017-05-31 Sanovel Ilac Sanayi ve Ticaret A.S. Formulations de comprimés de nimésulide et de thiocolchicoside
WO2020222714A1 (fr) * 2019-04-30 2020-11-05 Sanovel Ilac Sanayi Ve Ticaret Anonim Sirketi Compositions pharmaceutiques comprenant des combinaisons de tolpérisone et de nimésulide

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112393827A (zh) * 2019-08-12 2021-02-23 南京理工大学 一种可生物降解的压电力传感器的制备方法

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2725134B1 (fr) 1994-10-04 1996-12-20 Lederle Lab Nouvelle association pharmaceutique a base d'ibuprofene et de thiocolchicoside
EP0853476B1 (fr) 1996-07-05 2002-04-03 Errekappa Euroterapici S.p.a. Preparation pharmaceutique contenant du nimesulide pour usage topique
EP0837684B1 (fr) 1995-06-13 2002-04-17 Sanofi-Synthelabo Compositions pharmaceutiques a base d'un sel de diclofenac et de thiocolchicoside
US20090175938A1 (en) * 2007-12-26 2009-07-09 Sanovel Ilac Sanayi Ve Ticaret A.S. Controlled Release Flurbiprofen and Muscle Relaxant Combinations
WO2010120253A1 (fr) * 2009-04-17 2010-10-21 Mustafa Nevzat Ilac Sanayii A.S. Combinaisons de thiocolchicoside et de médicament anti-inflammatoire non stéroïdien
WO2011112161A1 (fr) * 2010-03-12 2011-09-15 Ali Raif Ilac Sanayi Ve Ticaret A.S. Comprimés de thiocolchicoside à libération prolongée

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2725134B1 (fr) 1994-10-04 1996-12-20 Lederle Lab Nouvelle association pharmaceutique a base d'ibuprofene et de thiocolchicoside
EP0837684B1 (fr) 1995-06-13 2002-04-17 Sanofi-Synthelabo Compositions pharmaceutiques a base d'un sel de diclofenac et de thiocolchicoside
EP0853476B1 (fr) 1996-07-05 2002-04-03 Errekappa Euroterapici S.p.a. Preparation pharmaceutique contenant du nimesulide pour usage topique
US20090175938A1 (en) * 2007-12-26 2009-07-09 Sanovel Ilac Sanayi Ve Ticaret A.S. Controlled Release Flurbiprofen and Muscle Relaxant Combinations
WO2010120253A1 (fr) * 2009-04-17 2010-10-21 Mustafa Nevzat Ilac Sanayii A.S. Combinaisons de thiocolchicoside et de médicament anti-inflammatoire non stéroïdien
WO2011112161A1 (fr) * 2010-03-12 2011-09-15 Ali Raif Ilac Sanayi Ve Ticaret A.S. Comprimés de thiocolchicoside à libération prolongée

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3173077A1 (fr) 2015-11-30 2017-05-31 Sanovel Ilac Sanayi ve Ticaret A.S. Formulations de comprimés de nimésulide et de thiocolchicoside
WO2017093212A1 (fr) 2015-11-30 2017-06-08 Sanovel Ilac Sanayi Ve Ticaret A.S. Formulations de comprimé comprenant du nimésulide et du thiocolchicoside
WO2020222714A1 (fr) * 2019-04-30 2020-11-05 Sanovel Ilac Sanayi Ve Ticaret Anonim Sirketi Compositions pharmaceutiques comprenant des combinaisons de tolpérisone et de nimésulide
EP3962459A4 (fr) * 2019-04-30 2023-01-25 Sanovel Ilac Sanayi Ve Ticaret Anonim Sirketi Compositions pharmaceutiques comprenant des combinaisons de tolpérisone et de nimésulide

Also Published As

Publication number Publication date
EP2956125A1 (fr) 2015-12-23

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