WO2010134025A2 - Compositions orales de celecoxib - Google Patents

Compositions orales de celecoxib Download PDF

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Publication number
WO2010134025A2
WO2010134025A2 PCT/IB2010/052210 IB2010052210W WO2010134025A2 WO 2010134025 A2 WO2010134025 A2 WO 2010134025A2 IB 2010052210 W IB2010052210 W IB 2010052210W WO 2010134025 A2 WO2010134025 A2 WO 2010134025A2
Authority
WO
WIPO (PCT)
Prior art keywords
pharmaceutical composition
celecoxib
sodium
starch
calcium
Prior art date
Application number
PCT/IB2010/052210
Other languages
English (en)
Other versions
WO2010134025A3 (fr
Inventor
Ravindra Agarwal
Piyush Kansagra
Rajeev Raghuvanshi
Original Assignee
Ranbaxy Laboratories Limited
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 Ranbaxy Laboratories Limited filed Critical Ranbaxy Laboratories Limited
Priority to CA2762388A priority Critical patent/CA2762388A1/fr
Priority to EP10722778.7A priority patent/EP2432459A2/fr
Priority to AU2010250800A priority patent/AU2010250800A1/en
Publication of WO2010134025A2 publication Critical patent/WO2010134025A2/fr
Publication of WO2010134025A3 publication Critical patent/WO2010134025A3/fr
Priority to ZA2011/08413A priority patent/ZA201108413B/en

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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
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/4841—Filling excipients; Inactive ingredients
    • A61K9/4858—Organic compounds
    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/415—1,2-Diazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/4841—Filling excipients; Inactive ingredients
    • A61K9/4866—Organic macromolecular compounds

Definitions

  • the present invention relates to disintegrant free oral compositions of celecoxib. It also relates to the processes for preparing such compositions. Further, it relates to method of treating cyclooxygenase-2 mediated disorders using compositions of the present invention.
  • Celecoxib is a non-steroidal anti-inflammatory drug belonging to the class of selective cyclooxygenase-2 inhibitors. Chemically it is 4-[5-(4-methylphenyl)-3- (trifluoromethyl) pyrazol-1-yl] benzenesulfonamide.
  • Celecoxib as a compound is disclosed in U.S. Patent No. 5,466,823 assigned to G.D. Searle & Co. This patent describes a class of 1,5-diaryl pyrazoles and their salts together with processes for the preparation of such compounds.
  • U.S. Patent No. 5,760,068 assigned to G.D. Searle & Co. describes the use of 1,5- diaryl pyrazolyl benzenesulfonamide compounds (including celecoxib) in the treatment of pathological conditions associated with rheumatoid arthritis and osteoarthritis.
  • Celecoxib has unique physical and chemical properties, which present various problems in formulating effective oral compositions of celecoxib.
  • Celecoxib has a low solubility in aqueous media. Further it is a fluffy material, with relatively low bulk and tap densities.
  • celecoxib has certain undesirable flow characteristics, for example, it is sticky and can adhere to surfaces.
  • Celecoxib shows a pH dependent solubility, wherein its solubility increases in highly basic pH. These properties present a challenge in developing a formulation of celecoxib effective for oral administration.
  • Presently celecoxib is being marketed by Pharmacia Corporation under the trade name Celebrex® in a capsule dosage form containing either 100 mg or 200 mg of the drug.
  • EP Patent No. 1 049 467 Bl covers the marketed formulation of celecoxib. It describes orally deliverable compositions of celecoxib comprising particulate celecoxib in an intimate mixture with one or more pharmaceutically acceptable excipients, wherein said pharmaceutically acceptable excipients include a diluent, binder, disintegrant, surfactant and lubricant.
  • the celecoxib availability from the wet granulated solid compositions can be improved by reducing the particle size, increasing the wetting properties of celecoxib (by including a wetting agent like sodium lauryl sulphate in the granulating fluid) and improving dispersibility (by including disintegrant like croscarmellose sodium in the granulation).
  • Disintegrants constitute an important part of the formulation of tablets and capsules of a poorly soluble, fluffy and sticky drug like celecoxib.
  • a disintegrant facilitates break- up or disintegration of a tablet into particles after administration.
  • Disintegrants also improve the drug dissolution from encapsulated dosage forms. Encapsulation of solid material often times results in a plug formation, which delays the disintegration and dissolution of the drug from the capsules.
  • Disintegrants improve the dissolution of the contents of the capsule by promoting liquid penetration into the plug and breaking the plug into smaller particles. But the addition of another excipient (i.e. disintegrant) further leads to an increase in the cost of the dosage form.
  • the present inventors have developed a disintegrant free oral composition comprising celecoxib. It provides a reduction in total dosage form weight as well as decreasing the cost; without compromising the dissolution properties of the dosage form.
  • the present formulation releases at least 70% of celecoxib in one-hour without the use of a disintegrant.
  • the present invention provides a simple and economical method for preparing orally effective compositions of celecoxib.
  • the present invention provides for a pharmaceutical composition, which includes celecoxib or a pharmaceutically acceptable salt thereof, wherein the pharmaceutical composition is free of disintegrant.
  • a pharmaceutical composition which includes celecoxib or a pharmaceutically acceptable salt thereof, wherein the pharmaceutical composition is free of disintegrant.
  • the d 09 of the celecoxib particles is less than 200 ⁇ m, less than 150 ⁇ m, or less than 25 ⁇ m.
  • the celecoxib is present in an amount of about 10 mg to about 1000 mg and may include one or more pharmaceutically acceptable excipients selected from one or more of diluents, binders, wetting agents, lubricants, anti- adherents or mixtures thereof.
  • Suitable diluents may be lactose USP; lactose USP, anyhydrous; lactose USP, spray dried; starch USP; directly compressible starch; mannitol USP; sorbitol; dextrose monohydrate; microcrystalline cellulose NF; dibasic calcium phosphate dihydrate NF; sucrose-based diluents; confectioner's sugar; monobasic calcium sulfate monohydrate; calcium sulfate dihydrate NF; calcium lactate trihydrate granular NF; dextrates, NF (e.g., Emdex®); Celutab®; dextrose (e.g., Cerelose®); inositol; hydrolyzed cereal solids such as the Maltrons and Mor-RexTM; amylose; Rexcel®; powdered cellulose; calcium carbonate; glycine; bentonite; and/or polyvinylpyrrolidone.
  • Suitable binders
  • Tylose® alginic acid and salts of alginic acid; magnesium aluminum silicate; polyethylene glycol; guar gum; polysaccharide acids; bentonites; polyvinylpyrrolidone; polymethacrylates; hydroxypropylmethylcellulose (HPMC); hydroxypropylcellulose (Klucel®); ethylcellulose (Ethocel®); and/or pregelatinized starch (such as National 1511 and Starch 1500).
  • HPMC hydroxypropylmethylcellulose
  • Klucel® hydroxypropylcellulose
  • Ethocel® ethylcellulose
  • pregelatinized starch such as National 1511 and Starch 1500.
  • Suitable wetting agents may be oleic acid; glyceryl monostearate; sorbitan monooleate; sorbitan monolaurate; triethanolamine oleate; polyoxyethylene sorbitan monooleate; polyoxyethylene sorbitan monolaurate; sodium oleate; and sodium lauryl sulfate.
  • Suitable lubricants/ antidherents may be glyceryl behapate (Compritol® 888); stearates (magnesium, calcium, and sodium); stearic acid; hydrogenated vegetable oils (e.g., Sterotex®); talc; waxes: StearowetTM; boric acid; sodium benzoate; sodium acetate; sodium fumarate; sodium chloride; DL-leucine; polyethylene glycols (e.g., Carbowax® 4000 and Carbowax® 6000); sodium oleate; sodium lauryl sulfate; and magnesium lauryl sulfate.
  • glyceryl behapate Compritol® 888
  • stearates magnesium, calcium, and sodium
  • stearic acid hydrogenated vegetable oils
  • hydrogenated vegetable oils e.g., Sterotex®
  • talc talc
  • waxes StearowetTM
  • boric acid sodium benzoate
  • the pharmaceutical composition is in the form of tablets, pills, capsules, lozenges, sachets or pastilles.
  • the pharmaceutical compositions may be tablets or capsules.
  • the pharmaceutical composition should release not less than 70 % of celecoxib within one hour.
  • method for the treatment or prophylaxis of a cyclooxgenase-2 mediated condition or disorder includes administering a pharmaceutical composition which includes celecoxib or a pharmaceutically acceptable salt thereof, wherein the pharmaceutical composition is free of disintegrant.
  • the present invention is directed to disintegrant free oral compositions comprising celecoxib. It further relates to processes for preparing such compositions.
  • Suitable pharmaceutically acceptable acid addition salts of celecoxib may be prepared from an inorganic acid or from an organic acid.
  • inorganic acids include hydrochloric, hydrobromic, hydroiodic, nitric, carbonic, sulfuric and phosphoric acid.
  • organic acids include aliphatic, cycloaliphatic, aromatic, araliphatic, heterocyclic, carboxylic and sulfonic classes of organic acids, such as formic, acetic, propionic, succinic, glycolic, gluconic, lactic, malic, tartaric, citric, ascorbic, glucuronic, maleic, fumaric, pyruvic, aspartic, glutamic, benzoic, anthranilic, mesylic, salicyclic, p- hydroxybenzoic, phenylacetic, mandelic, embonic, methanesulfonic, ethanesulfonic, benzenesulfonic, pantothenic, 2-hydroxyethanesulfonic, toluenesulfonic, sulfanilic, cyclohexylaminosulfonic, stearic, algenic, b-hydroxybutyric, salicyclic, galactaric and galacturonic
  • Suitable pharmaceutically-acceptable base addition salts of celecoxib include metallic salts made from aluminum, calcium, lithium, magnesium, potassium, sodium and zinc or organic salts made from N,N'-dibenzylethylenediamine, chloroprocaine, choline, diethanolamine, ethylenediamine, meglumine (N-methylglucamine) and procaine.
  • Particularly compositions of the invention comprise celecoxib in its free form.
  • di 9 as used herein with reference to the size of celecoxib particles, indicate that about 90% of particles measured have a size less than the defined d 0 9 value, and that about 10% of particles measured have a size greater than the defined d 0 9 value.
  • disintegrant free oral compositions refers to the oral compositions of celecoxib, which do not contain any disintegrant. However, when the compositions of the present invention are in the form of a tablet an extragranular disintegrant may be added.
  • compositions of the present invention comprise celecoxib having a d 0 9 less than 200 ⁇ m, particularly less than 150 ⁇ m, more particularly less than 50 ⁇ m and most particularly less than 25 ⁇ m.
  • Celecoxib is present in an amount of 10 mg to 1000 mg; 50 mg to 800 mg; 75 mg to 400 mg; and/or 100 mg to 200 mg in the compositions of the present invention.
  • the disintegrant free oral compositions of the present invention further include one or more pharmaceutically acceptable excipients selected from the group consisting of diluents, binders, wetting agents, lubricants and anti- adherents.
  • diluents include, either individually or in combination, lactose USP; lactose USP, anyhydrous; lactose USP, spray dried; starch USP; directly compressible starch; mannitol USP; sorbitol; dextrose monohydrate; microcrystalline cellulose NF; dibasic calcium phosphate dihydrate NF; sucrose-based diluents; confectioner's sugar; monobasic calcium sulfate monohydrate; calcium sulfate dihydrate NF; calcium lactate trihydrate granular NF; dextrates, NF (e.g., Emdex®); Celutab®; dextrose (e.g., Cerelose®); inositol; hydrolyzed cereal solids such as the Maltrons and Mor-RexTM; amylose; Rexcel®; powdered cellulose; calcium carbonate; glycine; bentonite; polyvinylpyrrolidone; and the like
  • binding agents include, either individually or in combination, acacia; tragacanth; sucrose; gelatin; glucose; starch; cellulose materials such as, methylcellulose and sodium carboxymethylcellulose (e.g., Tylose®); alginic acid and salts of alginic acid; magnesium aluminum silicate; polyethylene glycol; guar gum; polysaccharide acids; bentonites; polyvinylpyrrolidone; polymethacrylates; hydroxypropylmethylcellulose (HPMC); hydroxypropylcellulose (Klucel®); ethylcellulose (Ethocel®); pregelatinized starch (such as National 1511 and Starch 1500).
  • Polyvinylpyrrolidone is a preferred binding agent.
  • wetting agents include, individually or in combination, oleic acid; glyceryl monostearate; sorbitan monooleate; sorbitan monolaurate; triethanolamine oleate; polyoxyethylene sorbitan monooleate; polyoxyethylene sorbitan monolaurate; sodium oleate; and sodium lauryl sulfate.
  • Wetting agents that are anionic surfactants are preferred.
  • Compositions of the present invention include sodium lauryl sulfate.
  • Suitable lubricants and/or glidants include, either individually or in combination, glyceryl behapate (Compritol® 888); stearates (magnesium, calcium, and sodium); stearic acid; hydrogenated vegetable oils (e.g., Sterotex®); talc; waxes: Stear-o-wetTM; boric acid; sodium benzoate; sodium acetate; sodium fumarate; sodium chloride; DL-leucine; polyethylene glycols (e.g., Carbowax® 4000 and Carbowax® 6000); sodium oleate; sodium lauryl sulfate; and magnesium lauryl sulfate.
  • Magnesium stearate is a preferred lubricant being used in the compositions of the present invention.
  • compositions of the present invention include, but not limited to, anti-adherent agents, colorants, flavors, sweeteners and preservatives.
  • the disintegrant free oral compositions of the present invention are in the form of tablets, pills, capsules, lozenges, sachets or pastilles.
  • composition of the present invention may be prepared in accordance with methods well known to the person skilled in the field of pharmacy. For example, wet granulation, dry granulation, compaction or encapsulation method can be employed to prepare the compositions of the present invention. Particularly, the compositions of the present invention are prepared by wet granulation or dry compaction.
  • the disintegrant free oral compositions of the present invention show a similar release profile at four different pH values i.e., highly basic pH 12, very slightly acidic pH 6.8, slightly acidic pH 4.5 and highly acidic pH 1.2.
  • the present invention also relates to a method of treating a disorder where treatment with cyclooxygenase-2 inhibitor is indicated (for example, osteoarthritis, rheumatoid arthritis and ankylosing spondylitis) by administering an effective amount of a composition of the present invention to a patient in need of such treatment.
  • the methods of utilizing the pharmaceutical compositions of the present invenction can include one or more of the following embodiments.
  • the method further comprises concurrently or sequentially administering one or more of pregabalin, cyclophosphamide, capecitabine, temozolomide, statins and other anticancer agents.
  • the composition further comprises one or more of pregabalin, cyclophosphamide, capecitabine, temozolomide, statins and other anticancer agents.
  • Celecoxib, polyvinylpyrrolidone and lactose were sifted through a sieve.
  • step 2 Material of step 1 was then mixed in a high shear mixer.
  • step 3 Sodium lauryl sulphate was dissolved in purified water to prepare a solution. 4. Material of step 2 was granulated using the solution of step 3. 5. Wet mass of step 4 was then dried in a fluid bed dryer. 6. The dried granules were then sifted and milled.
  • Drug release was determined in 1000 ml of disodium phosphate buffer (containing 1% sodium lauryl sulphate; pH 12) at 37 0 C using USP apparatus II with paddle speed at 50 rpm.
  • Drug release was determined in 1000 ml of acetate buffer (containing 1% sodium lauryl sulphate; pH 4.5) at 37 0 C using USP apparatus II with paddle speed at 50 rpm.
  • Drug release was determined in 1000 ml of 0.1 N HCl (containing 1% sodium lauryl sulphate; pH 1.2) at 37 0 C using USP apparatus II with paddle speed at 50 rpm.
  • Drug release was determined in 1000 ml of sodium phosphate buffer (containing 1% sodium lauryl sulphate; pH 6.8) at 37 0 C using USP apparatus II with paddle speed at 50 rpm.

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  • 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)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)

Abstract

La présente invention concerne des compositions orales sans désagrégeant comprenant du celecoxib. Elle concerne également des procédés de préparation de ces compositions, et des méthodes utilisant celles-ci pour le traitement de troubles médiés par la cyclo-oxygénase-2.
PCT/IB2010/052210 2009-05-20 2010-05-18 Compositions orales de celecoxib WO2010134025A2 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
CA2762388A CA2762388A1 (fr) 2009-05-20 2010-05-18 Compositions orales de celecoxib
EP10722778.7A EP2432459A2 (fr) 2009-05-20 2010-05-18 Compositions orales de celecoxib
AU2010250800A AU2010250800A1 (en) 2009-05-20 2010-05-18 Oral compositions of celecoxib
ZA2011/08413A ZA201108413B (en) 2009-05-20 2011-11-16 Oral compositions of celecoxib

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN1036DE2009 2009-05-20
IN1036/DEL/2009 2009-05-20

Publications (2)

Publication Number Publication Date
WO2010134025A2 true WO2010134025A2 (fr) 2010-11-25
WO2010134025A3 WO2010134025A3 (fr) 2011-11-10

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PCT/IB2010/052210 WO2010134025A2 (fr) 2009-05-20 2010-05-18 Compositions orales de celecoxib

Country Status (5)

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EP (1) EP2432459A2 (fr)
AU (1) AU2010250800A1 (fr)
CA (1) CA2762388A1 (fr)
WO (1) WO2010134025A2 (fr)
ZA (1) ZA201108413B (fr)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013082706A1 (fr) * 2011-12-07 2013-06-13 Pharmascience Inc. Formulation de doxylamine et de pyridoxine à libération prolongée sans délitant et procédé de fabrication associé
WO2015044961A3 (fr) * 2013-09-30 2015-06-04 Intas Pharmaceuticals Limited Composition pharmaceutique comprenant de la capécitabine et du cyclophosphamide
WO2016046797A1 (fr) * 2014-09-26 2016-03-31 Intas Pharmaceuticals Ltd. Composition pharmaceutique présentant une uniformité de teneur améliorée
US10350171B2 (en) 2017-07-06 2019-07-16 Dexcel Ltd. Celecoxib and amlodipine formulation and method of making the same
US11793230B2 (en) 2019-12-09 2023-10-24 Nicoventures Trading Limited Oral products with improved binding of active ingredients
US11826462B2 (en) 2019-12-09 2023-11-28 Nicoventures Trading Limited Oral product with sustained flavor release
US11872231B2 (en) 2019-12-09 2024-01-16 Nicoventures Trading Limited Moist oral product comprising an active ingredient
US11969502B2 (en) 2019-12-09 2024-04-30 Nicoventures Trading Limited Oral products

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1049467A1 (fr) * 1998-11-30 2000-11-08 G.D. Searle & Co. Compositions a base de celecoxib
WO2002005799A2 (fr) * 2000-07-13 2002-01-24 Pharmacia Corporation Composes vasomodulateurs et inhibiteurs selectifs de la cyclo-oxygenase-2 pour le traitement des douleurs generalisees et des cephalees
WO2009063367A1 (fr) * 2007-11-15 2009-05-22 Pfizer Products Inc. Formes galéniques comprenant du célécoxib permettant un soulagement de la douleur à la fois rapide et prolongé

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1049467A1 (fr) * 1998-11-30 2000-11-08 G.D. Searle & Co. Compositions a base de celecoxib
WO2002005799A2 (fr) * 2000-07-13 2002-01-24 Pharmacia Corporation Composes vasomodulateurs et inhibiteurs selectifs de la cyclo-oxygenase-2 pour le traitement des douleurs generalisees et des cephalees
WO2009063367A1 (fr) * 2007-11-15 2009-05-22 Pfizer Products Inc. Formes galéniques comprenant du célécoxib permettant un soulagement de la douleur à la fois rapide et prolongé

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013082706A1 (fr) * 2011-12-07 2013-06-13 Pharmascience Inc. Formulation de doxylamine et de pyridoxine à libération prolongée sans délitant et procédé de fabrication associé
WO2015044961A3 (fr) * 2013-09-30 2015-06-04 Intas Pharmaceuticals Limited Composition pharmaceutique comprenant de la capécitabine et du cyclophosphamide
WO2016046797A1 (fr) * 2014-09-26 2016-03-31 Intas Pharmaceuticals Ltd. Composition pharmaceutique présentant une uniformité de teneur améliorée
US10016447B2 (en) 2014-09-26 2018-07-10 Intas Pharmaceuticals Ltd. Pharmaceutical composition having improved content uniformity
US10350171B2 (en) 2017-07-06 2019-07-16 Dexcel Ltd. Celecoxib and amlodipine formulation and method of making the same
US11793230B2 (en) 2019-12-09 2023-10-24 Nicoventures Trading Limited Oral products with improved binding of active ingredients
US11826462B2 (en) 2019-12-09 2023-11-28 Nicoventures Trading Limited Oral product with sustained flavor release
US11872231B2 (en) 2019-12-09 2024-01-16 Nicoventures Trading Limited Moist oral product comprising an active ingredient
US11969502B2 (en) 2019-12-09 2024-04-30 Nicoventures Trading Limited Oral products

Also Published As

Publication number Publication date
AU2010250800A1 (en) 2012-01-12
CA2762388A1 (fr) 2010-11-25
WO2010134025A3 (fr) 2011-11-10
ZA201108413B (en) 2012-09-26
EP2432459A2 (fr) 2012-03-28

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