EP3723736A2 - Tolperison und selektive cox-2 inhibitorkombinationen - Google Patents

Tolperison und selektive cox-2 inhibitorkombinationen

Info

Publication number
EP3723736A2
EP3723736A2 EP18915012.1A EP18915012A EP3723736A2 EP 3723736 A2 EP3723736 A2 EP 3723736A2 EP 18915012 A EP18915012 A EP 18915012A EP 3723736 A2 EP3723736 A2 EP 3723736A2
Authority
EP
European Patent Office
Prior art keywords
weight
pharmaceutical composition
tablet
composition according
tolperisone
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.)
Pending
Application number
EP18915012.1A
Other languages
English (en)
French (fr)
Other versions
EP3723736A4 (de
Inventor
Ali TÜRKYILMAZ
Nur PEHLIVAN AKALIN
Seyhan TÜRKKAN
Melda MISIRLI
Emine TUNCAY
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
Publication of EP3723736A2 publication Critical patent/EP3723736A2/de
Publication of EP3723736A4 publication Critical patent/EP3723736A4/de
Pending legal-status Critical Current

Links

Classifications

    • 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
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/18—Sulfonamides
    • 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
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/4453—Non condensed piperidines, e.g. piperocaine only substituted in position 1, e.g. propipocaine, diperodon
    • 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
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2022—Organic macromolecular compounds
    • A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
    • A61K9/2059—Starch, including chemically or physically modified derivatives; Amylose; Amylopectin; Dextrin
    • 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
    • A61K9/2077—Tablets comprising drug-containing microparticles in a substantial amount of supporting matrix; Multiparticulate tablets

Definitions

  • the present invention relates to pharmaceutical combinations comprising tolperisone or a pharmaceutically acceptable salt, solvate, polymorph, isomer, enantiomer or rasemic mixture thereof and selective COX-2 inhibitors or pharmaceutically acceptable salts, solvates, polymorphs, isomers, enantiomers or rasemic mixtures thereof.
  • a muscle relaxant is a drug that affects skeletal muscle function and decreases the muscle tone. It may be used to alleviate symptoms such as muscle spasms, pain, and hyperreflexia.
  • the term "muscle relaxant” is used to refer to two major therapeutic groups: neuromuscular blockers and spasmolytics. Neuromuscular blockers act by interfering with transmission at the neuromuscular end plate and have no central nervous system (CNS) activity. They are often used during surgical procedures and in intensive care and emergency medicine to cause temporary paralysis. Spasmolytics, also known as centrally acting muscle relaxants, are used to alleviate musculoskeletal pain and spasms and to reduce spasticity in a variety of neurological conditions. While both neuromuscular blockers and spasmolytics are often grouped together as muscle relaxants, the term is commonly used to refer to spasmolytics only.
  • Tolperisone is a centrally acting muscle relaxant that has been used for the symptomatic treatment of spasticity and muscle spasm. It acts at the reticular formation in the brain stem by blocking voltage-gated sodium and calcium channels and it is marketed unders trade names including Biocalm, Muscodol, Mydeton, Mydocalm, Mydoflex, Myolax, Myoxan and Viveo.
  • NSAIDs non-steroidal anti-inflammatory drugs
  • COX cyclooxygenase
  • COX-1 The cyclooxygenase (COX) enzyme is actually present in two different forms, COX-1 and COX-2, each with a similar but distinct set of actions.
  • COX-2 is the enzyme responsible for inflammation and fever, whereas COX-1 actually performs other functions such as protecting the gastric mucosa (the lining of the stomach) from the acid that the stomach naturally produces.
  • COX-1 also plays a role in making platelets stick together to form clots. Both reduce blood flow to the kidneys.
  • NSAIDs block both types of the COX enzyme, so while inflammation and pain were reduced, so were some of the good effects of prostaglandins such as protection of the stomach lining.
  • NSAIDs namely selective COX-2 inhibitors, which only target the COX-2 enzyme that is responsible for pain and inflammation, without impacting the production of protective factors for the stomach.
  • selective COX-2 inhibitors are much more safe drugs, comparing with the classical non-selective NSAIDs in the treatment of inflammatory diseases.
  • tolperisone and an active agent selected from NSAIDs or other than NSAIDs are also present in the prior art.
  • EP1610785B1 reveals the combined effect of tolperisone and dextromethorphan on the treatment of spasticity and pain.
  • EP1677787B1 the combination of tolperisone and flupirtin is suggested for the treatment of pains accompanied by an increase in muscle tone.
  • a dosage form comprising tolperisone and a selective COX-2 inhibitor combination which enhance the therapeutic effect on spasmodic and arthritic disorders and ensures the gastrointestinal and cardiovascular safety and compliance of the patient at the same time.
  • the main object of the present invention is to obtain combinations comprising tolperisone or a pharmaceutically acceptable salt, solvate, polymorph, isomer, enantiomer of rasemic mixture thereof and selective COX-2 inhibitors or pharmaceutically acceptable salts, solvates, polymorphs, isomers, enantiomers of rasemic mixtures thereof, eliminating all aforesaid problems and bringing additional advantages over the relevant prior art.
  • Another object of the present invention is to obtain compositions of tolperisone and selective COX-2 inhibitors ensuring cardiovascular and gastrointestinal safety and patient compliance, accordingly.
  • a further object of the present invention is to develop compositions of tolperisone and selective COX-2 inhibitors ensuring high stability, bioavalibility.
  • a further object of the present invention is to develop compositions of tolperisone and selective COX-2 inhibitors having an improved level of dissolution rate and solubility.
  • Another object of the present invention is to provide a tablet dosage form comprising tolperisone and a selective COX-2 inhibitor for use in the treatment and prevention of spasmodic and arthritic disorders.
  • the present invention relates to pharmaceutical compositions comprising tolperisone or a pharmaceutically acceptable salt, solvate, polymorph, isomer, enantiomer or rasemic mixture thereof in combination with a selective COX-2 inhibitor or a pharmaceutically acceptable salt, solvate, polymorph, isomer, enantiomer or rasemic mixture thereof.
  • the said selective COX-2 inhibitor is selected from the group comprising nimesulide, etoricoxib, lumiracoxib, meloxicam, parecoxib, parecoxib sodium, celecoxib or valdecoxib or mixtures tehreof.
  • the said selective COX-2 inhibitor is nimesulide.
  • the oral pharmaceutical composition comprises tolperisone and nimesulide as combined active agents.
  • the amount of tolperisone is between 1 -50% by weight of the total composition. Preferably this amount is between 5-40% by weight of the total composition. More preferably tolperisone is present between 15-35% by weight in the total composition.
  • the weight ratio of nimesulide to tolperisone is in the range of 1 :0.025 to 1 :50 and preferably 1 :0.1 to 1 :5. In the most preferred embodiment, this ratio is 1 :0.5 or 1 :1.5.
  • the amount of nimesulide is between 1 -40% by weight of the total composition. Preferably this amount is between 5-30% by weight of the total composition. More preferably nimesulide is present between 10-20% by weight in the total composition.
  • tolperisone is present in an amount of 1 to 500 mg, more preferably 5 to 250 mg in the total composition.
  • nimesulide is present in an amount of 1 to 300 mg, more preferably 50 to 150 mg in the total composition.
  • the composition comprises at least one pharmaceutically acceptable excipient selected from diluents, disintegrants, binders, lubricants, glidants, buffering agents or mixtures thereof.
  • the oral pharmaceutical composition comprises at least one diluent which is selected from the group comprising lactose monohydrate, microcrystalline cellulose, lactose, dibasic calcium phosphate, mannitol, spray-dried mannitol, dextrose, sucrose, fructose, maltose, sorbitol, xylitol, inositol, kaolin, inorganic salts, calcium salts, polysaccharides, dicalcium phosphate, sodium chloride, dextrates, lactitol, maltodextrin, sucrose-maltodextrin mixture, trehalose, sodium carbonate, sodium bicarbonate, calcium carbonate or mixtures thereof.
  • diluent which is selected from the group comprising lactose monohydrate, microcrystalline cellulose, lactose, dibasic calcium phosphate, mannitol, spray-dried mannitol, dextrose, sucrose, fructose, maltos
  • the oral pharmaceutical composition comprises three diluents which are lactose monohydrate, microcrystalline cellulose and lactose.
  • the amount of lactose monohydrate is between 1 -50%, preferably 5-30% and more preferably 10-20% by weight of the total composition.
  • the amount of microcrystalline cellulose is between 1 -50%, preferably 5-30% and more preferably 10-20% by weight of the total composition.
  • the amount of lactose is between 1 -50%, preferably 5-30% and more preferably 10-20% by weight of the total composition.
  • the oral pharmaceutical composition comprises at least one disintegrant which is selected from the group comprising sodium starch glycolate, croscarmellose sodium, sodium carbonate, hydroxylpropyl cellulose (HPC), cross-linked polyvinylpyrrolidone (crospovidon), copovidon, polycarbophil, low- substitue poloxamer, alginic acid and alginates, ion-exchange resins, magnesium aluminum silica, sodium dodecyl sulphate, sodium carboxy methyl cellulose, carboxy methyl cellulose calcium, docusate sodium, guar gum, polyacrylin potasium, sodium alginate, sodium glysin carbonate, sodium lauryl sulphate or mixtures thereof.
  • disintegrant which is selected from the group comprising sodium starch glycolate, croscarmellose sodium, sodium carbonate, hydroxylpropyl cellulose (HPC), cross-linked polyvinylpyrrolidone (crospovidon), copovidon, polycarbophil, low
  • the oral pharmaceutical composition comprises one disintegrant which is sodium starch glycolate.
  • the amount of sodium starch glycolate is between 1 -30%, preferably 5-15% by weight of the total composition.
  • the oral pharmaceutical composition comprises at least one binder which is selected from the group comprising hydroxypropyl cellulose (HPC), copovidone, copolyvidone, polyvinylpyrrolidone (PVP), povidone K30, carnauba wax, hydroxypropyl methyl cellulose (hypromellose, HPMC), pullulan, polymethacrylate, glyceryl behenate, carboxymethyl cellulose (CMC), methyl cellulose (MC), hydroxyethyl cellulose, sodium carboxymethyl cellulose (Na CMC), ethyl cellulose, microcrystalline cellulose, polymetacrylates, polyethylene oxide, polyvinyl alcohol, polycarbophil, polyvinyl acetate and its copolymers, gelatin, xanthan gum, guar gum, alginate, carrageen, kollagen, agar, pectin, hyaluronic acid, carbomer, cellulose acetate phthalate, hydroxyethyl methylcellulose (HPC
  • the oral pharmaceutical composition comprises one binder which is hydroxypropyl cellulose (HPC).
  • HPC hydroxypropyl cellulose
  • the amount of HPC is between 0.01 -5%, preferably 0.05-0.5% by weight of the total composition.
  • the oral pharmaceutical composition comprises at least one buffering agent which is selected from the group comprising citric acid anhydrate, alkali metal citrate, citric acid/sodium citrate, tartaric acid, fumaric acid, sorbic acid, citric acid, succinic acid, adipic acid, ascorbic acid, glutaric acid, potassium hydrogen tartrate, sodium hydrogen tartrate, potassium hydrogen phthalate, sodium hydrogen phthalate, potassium dihydrogen phosphate, sodium dihydrogen phosphate, disodium hydrogen phosphate, hydrochloric acid/sodium hydroxide or mixtures thereof.
  • buffering agent which is selected from the group comprising citric acid anhydrate, alkali metal citrate, citric acid/sodium citrate, tartaric acid, fumaric acid, sorbic acid, citric acid, succinic acid, adipic acid, ascorbic acid, glutaric acid, potassium hydrogen tartrate, sodium hydrogen tartrate, potassium hydrogen phthalate, sodium hydrogen phthalate, potassium dihydrogen phosphate, sodium dihydr
  • the oral pharmaceutical composition comprises one buffering agent which is citric acid anhydrate.
  • the amount of citric acid anhydrate is between 0.5-10%, preferably 1 -5% by weight of the total composition.
  • the oral pharmaceutical composition comprises at least one lubricant and one glidant which are selected from the group comprising sodium stearyl fumarate, colloidal silicon dioxide, sodium lauryl sulphate, magnesium stearate, zinc stearate, calcium stearate, mineral oil, talc, polyethylene glycol, glyceryl monostearate, glyceryl palmitostearate, magnesium lauryl sulphate, fumaric acid, zinc stearate, stearic acid, hydrogenated natural oils, silica, paraffin or mixtures thereof.
  • lubricant and one glidant which are selected from the group comprising sodium stearyl fumarate, colloidal silicon dioxide, sodium lauryl sulphate, magnesium stearate, zinc stearate, calcium stearate, mineral oil, talc, polyethylene glycol, glyceryl monostearate, glyceryl palmitostearate, magnesium lauryl sulphate, fumaric acid, zinc stea
  • the solid oral pharmaceutical composition comprises two lubricants which are sodium stearyl fumarate and talc.
  • the amount of sodium stearyl fumarate is between 0.1 -10%, preferably 1 -5% by weight of the total composition.
  • the amount of talc is between 0.05-5%, preferably 0.1 -1% by weight of the total composition.
  • the solid oral pharmaceutical composition comprises one glidant which is colloidal silicon dioxide.
  • the amount of colloidal silicon dioxide is between 0.05-5%, preferably 0.1 -1 % by weight of the total composition.
  • the composition is in the form of of tablet, coated tablet, film-coated tablet, trilayer tablet, bilayer tablet, multilayer tablet, orally disintegrating tablet, mini tablet, tablet in tablet, inlay tablet, buccal tablet, sublingual tablet, effervescent tablet, immediate release tablet, modified release tablet, , gastric disintegrating tablet, pellet, sugar pellet, pill, capsule, oral granule, powder, coated bead system, microsphere, dragee, sachet or orally administrable film.
  • the composition is preferably in the form of a tablet, coated tablet, film-coated tablet; more preferably film-coated tablet.
  • the solid oral pharmaceutical composition comprises at least one coating layer to protect the composition against the moisture and maintain the stability.
  • Suitable coating ingredients are selected from the group comprising hydroxypropylmethyl cellulose (hypromellose), lactose monohydrate, hydroxypropyl cellulose, polyvinyl alcohol (PVA), polyethylene glycol (PEG), talc, polyvinyl alcohol- polyethylene glycol copolymers (Kollicoat IR), ethylcellulose dispersions (Surelease), polyvinylprolidone, polyvinylprolidone-vinyl acetate copolymer (PVP-VA) and all kinds of OpadryTM, pigments, dyes, titanium dioxide, iron oxide or polymethylmetacrylate copolymers and mixtures thereof.
  • coating layer is Opadry II yellow which comprises hydroxypropylmethyl cellulose (hypromellose), hydroxypropyl cellulose, titanium dioxide, quinoline yellow dye (D&C yellow no.10).
  • the composition comprises;
  • microcrystalline cellulose — 1 -50% by weight of microcrystalline cellulose
  • Example 1 Film-coated tablet formulation
  • Example 2 Film-coated tablet formulation

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Medicinal Preparation (AREA)
  • Steroid Compounds (AREA)
EP18915012.1A 2017-12-13 2018-12-12 Tolperison und selektive cox-2 inhibitorkombinationen Pending EP3723736A4 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
TR2017/20289A TR201720289A2 (tr) 2017-12-13 2017-12-13 Tolperizon Ve Selektif COX-2 İnhibitörü Kombinasyonları
PCT/TR2018/050798 WO2019203751A2 (en) 2017-12-13 2018-12-12 Tolperisone and selective cox-2 inhibitor combinations

Publications (2)

Publication Number Publication Date
EP3723736A2 true EP3723736A2 (de) 2020-10-21
EP3723736A4 EP3723736A4 (de) 2021-07-14

Family

ID=67952522

Family Applications (1)

Application Number Title Priority Date Filing Date
EP18915012.1A Pending EP3723736A4 (de) 2017-12-13 2018-12-12 Tolperison und selektive cox-2 inhibitorkombinationen

Country Status (3)

Country Link
EP (1) EP3723736A4 (de)
TR (1) TR201720289A2 (de)
WO (1) WO2019203751A2 (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TR201906487A1 (tr) * 2019-04-30 2020-11-23 Sanovel Ilac Sanayi Ve Ticaret Anonim Sirketi Tolperi̇zon ve ni̇mesuli̇d kombi̇nasyonlari i̇çeren farmasöti̇k kompozi̇syonlar

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040204413A1 (en) * 2001-01-26 2004-10-14 Joaquina Faour Pharmaceutical compositions containing a COX-II inhibitor and a muscle relaxant
HUP0300929A3 (en) * 2003-04-09 2005-06-28 Richter Gedeon Vegyeszet Analgetic and/or muscle relaxant pharmaceutical composition
CN102438597A (zh) * 2009-03-09 2012-05-02 丁内沙·沙蒂尔阿尔·帕特尔 一种选自中枢性作用肌弛缓药类型的化合物的新型缓释制剂

Also Published As

Publication number Publication date
EP3723736A4 (de) 2021-07-14
WO2019203751A3 (en) 2019-11-28
WO2019203751A2 (en) 2019-10-24
TR201720289A2 (tr) 2019-06-21

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