WO2014192022A1 - Pharmaceutical compositions of rasagiline - Google Patents

Pharmaceutical compositions of rasagiline Download PDF

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Publication number
WO2014192022A1
WO2014192022A1 PCT/IN2014/000336 IN2014000336W WO2014192022A1 WO 2014192022 A1 WO2014192022 A1 WO 2014192022A1 IN 2014000336 W IN2014000336 W IN 2014000336W WO 2014192022 A1 WO2014192022 A1 WO 2014192022A1
Authority
WO
WIPO (PCT)
Prior art keywords
rasagiline
pharmaceutical composition
composition
salts
enantiomer
Prior art date
Application number
PCT/IN2014/000336
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English (en)
French (fr)
Inventor
Sushrut Krishnaji Kulkarni
Pavak Rajnikanth Mehta
Ritesh Kapoor
Original Assignee
Cadila Healthcare 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 Cadila Healthcare Limited filed Critical Cadila Healthcare Limited
Publication of WO2014192022A1 publication Critical patent/WO2014192022A1/en

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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
    • A61K31/13—Amines
    • A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
    • 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
    • A61K9/2054—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16—Anti-Parkinson drugs
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia

Definitions

  • the present invention relates to pharmaceutical compositions of rasagiline, its enantiomer or salts thereof.
  • the invention relates to stabilizer free pharmaceutical compositions of rasagiline, its enantiomer or salts thereof, process of preparation of such compositions and use thereof for treatment of Parkinson's disease, dementia and Alzheimer's disease.
  • Rasagiline is a selective irreversible inhibitor of monoamine oxidase enzyme Type-B (MAO-B) and has the chemical name N-propargyl-l(R)- aminoindan (“(R)-PAI"). Its structural formula is:
  • Rasagiline is an active MAO-B inhibitor while the corresponding S- enantiomer (“(S)-Rasagiline”) shows extremely low MAO-B inhibitory activity (U.S. Patent No. 6,316,504). It has also been found that (R)-Rasagiline has a degree of selectivity for MAO-B inhibition surprisingly higher than that of the corresponding racemic form (U.S. Patent No. 6,316,504). The fact that (R)- Rasagiline is more active than the racemic mixture for the inhibition of MAO-B is a reflection of the extremely low activity of (S)-Rasagiline for inhibition of MAO- B (U.S. Patent No. 6,316,504).
  • Rasagiline its salts, preparation and use for the treatment of Parkinson's disease, Alzheimer's disease, memory disorders, stroke and other disorders have been the subject of numerous patents, including U.S. Patent Nos. 5,387,612, 5,453,446, 5,457,133, 5,668,181, 5,576,353, 5,532,415, 5,599,991, 5,786,390, 5,519,061, 5,891,923, 5,744,500 and 6,316,504, the contents of which are hereby incorporated by reference.
  • a formulation of rasagiline mesylate is currently marketed in US in the form of film coated tablets for the treatment of Parkinson's disease either as monotherapy or as an adjunct with other treatments under trade name Azilect® by Teva Pharmaceuticals.
  • PCT publication No. 95/11016 discloses pharmaceutical formulations of rasagiline.
  • PCT Publication No. 95/11016 were of unacceptable stability.
  • U.S. Patent No. 6,126,968 then proceeds to offer certain alternative formulations of rasagiline intended to provide improved stability relative to the formulations of PCT Publication No. 95/11016.
  • the tablet of R(+)-N-propargyl-l-aminoindane or pharmaceutical acceptable salt thereof disclosed in the patent comprises at least one alcohol selected from the group consisting of pentahydric and hexahydric alcohols such as mannitol, xylitol and sorbitol.
  • PCT publication No. 2010/085354 discloses the delayed release composition of rasagiline, wherein the core comprises atleast one antioxidant, preferably citric acid and malic acid.
  • European Patent No. 0814789 discloses formulations of MAO-B inhibitors which attempt to address some of the known problems.
  • the European patent relies on lyophilization of the MAO-B inhibitor formulations which is a costly process and results in high friability of the product, further increasing cost by necessitating costly special blister-pack packaging.
  • European Patent Application No. 1892233 discloses polymorphic forms of rasagiline oxalate and rasagiline edisilate.
  • the patent application also discloses that mesylate, hydrochloride and phosphate salts of rasagiline show agglomerates after storage even in a closed glass bottle and can also display a slight discoloration and when stored under humid conditions (40°C, 75% relative humidity in an open glass bottle), a sticky powder which is difficult to process forms from said salts of rasagiline.
  • a yet another object of the invention is to provide for embodiments of the invention which may include one or more of the following features for example the pharmaceutical composition may further include one or more pharmaceutically acceptable excipients.
  • the pharmaceutically acceptable excipients may include fillers/diluents, binders, polymers, disintegrants, lubricants, glidants, sweeteners, taste masking agents and flavors.
  • An alternative object of the invention is to provide for, rasagiline, its enantiomer or salts thereof which may have particle size distribution wherein 10th volume percentile particle size (D 10 ) is greater than about 20 ⁇ , the 50th volume percentile particle size (D 50 ) is greater than about 100 ⁇ , 90th volume percentile particle size (D 90 ) is greater than about 250 ⁇ , or any combination thereof.
  • a yet another object of the invention is to provide for a pharmaceutical composition comprising rasagiline, its enantiomer or salts thereof having water content less than 6%.
  • the present invention provides for a pharmaceutical composition
  • a pharmaceutical composition comprising rasagiline, its enantiomer or salts thereof and at least one pharmaceutically acceptable excipient, wherein said composition is free of stabilizer.
  • a preferred embodiment of the present invention provides for a pharmaceutical composition as described above, wherein said pharmaceutically acceptable excipient is selected from diluent, binder, disintegrant, lubricant and/or a combination thereof.
  • compositions as described above wherein said composition comprises 15-95 % of diluent, 1-15% disintegrant, 0-15% binder, 0.1-5% lubricant.
  • Yet another preferred embodiment of the present invention provides for a pharmaceutical composition as described above, wherein said rasagiline is rasagiline besylate.
  • Yet another preferred embodiment of the present invention provides for a pharmaceutical composition as described above, wherein said rasagiline is rasagiline hydrogen phosphate.
  • a further preferred embodiment of the present invention provides for a pharmaceutical composition as described above, wherein the particle size (D90) of rasagiline is greater than 250 ⁇ .
  • the present invention provides for a process of preparing the pharmaceutical composition of claim 1 comprising the steps of:
  • step i) mixing rasagiline, its enantiomer or salts and optionally one or more pharmaceutically acceptable polymer in a suitable solvent; ii) granulating the mixture of step i) with one or more filler, disintegrant, binder;
  • step (iv) blending said granulate of step (iii) with one or more pharmaceutically acceptable excipient; v) formulating the blended granulate of step (iv) into a suitable dosage form.
  • said solvent is aqueous and/or organic solvent.
  • the pharmaceutical composition of the invention is in the form of tablet, capsule, lozenge, powder, film or sachet.
  • the pharmaceutical composition of the invention is free of stabilizer and it retains at least 80% of the potency of rasagiline, its enantiomer or salts thereof in the pharmaceutical composition after storage for three months at 40° C and 75% relative humidity.
  • the pharmaceutical composition of the invention is administered to a patient in need thereof for the treatment of Parkinson's disease, dementia or alzheimer's disease.
  • the inventors of the present invention have formulated stable formulations of rasagiline without any stabilizer and such formulation retains at least 80% of the potency of rasagiline, its enantiomer or salts thereof in the pharmaceutical composition after storage for three months at 40° C and 75% relative humidity. Additionally, the inventors have found that formulations containing besylate salt of rasagiline exhibits significant stability and in particular, possess good formulation characteristics.
  • compositions of rasagiline, its enantiomer or salts thereof comprising one or more pharmaceutical excipients, wherein the composition is free stabilizer.
  • 'rasagiline' is used in broad sense to include not only the rasagiline per se but also its pharmaceutically acceptable salts, pharmaceutically acceptable solvates, pharmaceutically acceptable hydrates, pharmaceutically acceptable enantiomers, pharmaceutically acceptable derivatives, pharmaceutically acceptable polymorphs and pharmaceutically acceptable prodrugs thereof, and their crystalline and amorphous forms.
  • S(-) or R(+) enantiomers of rasagiline and especially the enantiomer R(+) of rasagiline is particularly preferred.
  • Particularly preferred salts of rasagiline or its enantiomer are besylate, mesylate, maleate, fumarate, tartrate, hydrobromide, esylate, tosylate, benzoate, oxalate, edisilate, phosphate, hydrochloride, acetate, sulphate.
  • stabilizers used hereinbefore and throughout the description hereinafter refers to lactose, mannitol, xylitol, fructose, maltitol, isomaltitol, erythritol, lactitol and Sorbitol, citric acid, tartaric acid, lactic acid, butyl hydroxyl toluene, butyl hydroxyl anisole, EDTA and the like.
  • the inventors of the present invention have also found that particle size distributions have a beneficial effect on the uniformity of the solid pharmaceutical composition of Rasagiline.
  • Coarser particle size of rasagiline, its enantiomer or salts thereof provides better uniformity, flowability compared to the finer particle size and suitable for pharmaceutical formulations.
  • a pharmaceutical composition of rasagiline, its enantiomer or salts thereof have 90th volume percentile particle size (D90) greater than about 250 ⁇ .
  • rasagiline, its enantiomer or salts thereof may have particle size distribution, wherein 10th volume percentile particle size (D10) is greater than about 20 ⁇ , the 50th volume percentile particle size (D50) is greater than about 100 ⁇ , and D(90) is greater than about 250 ⁇ , or any combination thereof.
  • rasagiline, its enantiomer or salts thereof may have particle size D(90) greater than 250 microns, and D(50) greater than 150 microns.
  • the pharmaceutical composition of rasagiline, its enantiomer or salts thereof have water content less than 6%, preferably less than 4%.
  • a process for the preparation of pharmaceutical composition of rasagiline, its enantiomer or salts thereof comprises the steps of dissolving rasagiline, its enantiomer or salts thereof alone or in combination with atleast one polymer in suitable solvent (s) and adsorbing the resultant solution on atleast one pharmaceutically acceptable excipient and formulated in to suitable dosage forms by methods known in the art.
  • the process for the preparation of pharmaceutical composition of rasagiline, its enantiomer or salts thereof comprises the steps of i) .
  • Suitable solvents that may be used for preparing the dispersion include organic, aqueous, or a mixture thereof.
  • Organic solvents may be aliphatic alcohols such as methanol, ethanol, n-propanol, and isopropanol; aliphatic ketones such as acetone and methyl ethyl ketone; aliphatic carboxylic esters such as ethyl acetate; aromatic hydrocarbons such as toluene and xylene; aliphatic hydrocarbons such as hexane; aliphatic nitriles such as acetonitrile; chlorinated hydrocarbons such as dichloromethane; aliphatic sulfoxides such as dimethyl sulfoxide; and the like, as well as mixtures comprising at least one of the foregoing organic solvents.
  • Aqueous solvents include solvent comprising water and/or a water-miscible organic solvent such as a lower alcohol, acetonitrile, tetrahydrofuran, dimethylacetamide, dimethyl formamide, and the like. Combination of various solvents can also be used.
  • the polymer that may be used for preparing drug dispersion includes water soluble and/or water insoluble polymer.
  • Suitable polymers that may be used for preparing the dispersion include, but are not limited to, copovidone, ethylcellulose, hydroxypropyl cellulose, hydroxyl propyl methyl cellulose, polyvinyl alcohol, methylcellulose, polyethylene oxide, polyvinylpyrrolidone, povidone, starch, or sodium carboxymethylcellulose and the like.
  • the pharmaceutical composition of rasagiline, its enantiomer or salts thereof can be prepared by any suitable method known in the art such as direct compression, dry granulation or wet granulation using aqueous and/or nonaqueous solvents, fluidized bed granulation, melt extrusion, melt granulation, spray coating, freeze drying, spray drying and solution evaporation.
  • the pharmaceutical composition can be formulated into tablets, pellets, wafers, granules, micro-granules, powders, capsules, lozenges, films, chewables, pellets in capsule, granules in capsule or any other dosage form suitable for oral administration.
  • the pharmaceutical composition is provided as a tablet, which can be film coated with one or more coating agents.
  • Usable coating agents are hypromellose, polyvinyl alcohol, sodium carboxymethyl cellulose and various methacrylic acid polymers.
  • the coating may also contain further such as plasticizers, pigments, pore forming materials.
  • the composition containing rasagiline, its enantiomer or salts thereof can be developed into fast-releasing and delayed- releasing compositions by methods known to the person skilled in the art.
  • compositions of rasagiline comprise one or more diluents, fillers/bulking agents, binders, disintegrants, lubricants, glidants, sweeteners/taste masking agents, colorants and flavors.
  • the pharmaceutically acceptable excipients for use in the pharmaceutical composition of rasagiline contains less than five alcohol (-OH) groups.
  • Suitable diluents/fillers or bulking agents which includes, but are not limited to, saccharides, including monosaccharides, disaccharides, polysaccharides and sugar alcohols having less than five alcohol (-OH) groups, and other bulking agents such as dibasic calcium phosphate and powdered cellulose and derivatives thereof and combinations thereof, preferably dibasic calcium phosphate and/or microcrystalline cellulose.
  • the diluent/filler may be present in an amount from about 1% w/w to about 99% w/w of the total weight of the composition.
  • Suitable binders which includes, but are not limited to, acacia, alginic acid, carbomer copolymer, carbomer interpolymer, copovidone, microcrystalline cellulose, dextrin, ethylcellulose, gelatin, glucose (liquid), guar gum, hydroxypropyl cellulose, polyvinyl alcohol, maltose, methylcellulose, polyethylene oxide, polyvinylpyrrolidone, povidone, starch, or sodium carboxymethylcellulose and the like.
  • the binder may be present in an amount from about 0% w/w to about 15% w/w of the total weight of the composition.
  • Suitable disintegrants which includes, but are not limited to, croscarmellose sodium, crospovidone, sodium starch glycolate, corn starch, potato starch, maize starch, pregelatinized starch and modified starches, calcium silicates, low substituted hydroxy- propylcellulose.
  • the disintegrant may be present in an amount from about 0.1% w/w to about 15% w/w of the total weight of the composition.
  • Suitable lubricants and glidants which may include, but are not limited to, stearic acid and its derivatives or esters like sodium stearate, magnesium stearate, calcium stearate and sodium stearyl fumarate; talc and colloidal silicon dioxide.
  • the lubricant may be present in an amount from about 0.1 % w/w to about 10% w/w of the total weight of the composition.
  • Suitable taste masking agents may include one or more of polymers, surfactants, sweeteners and flavors.
  • polymers include one or more of cellulose acetate, polymethacrylates, cellulose derivatives such as hydroxypropylmethyl cellulose, hydroxypropyl cellulose, hydroxylethyl cellulose; and the like.
  • sweeteners include but not limiting to one or more of aspartame, saccharin, sucralose, glycyrrhizin; and the like.
  • the taste masking agent may be present in an amount from about 0% w/w to about 5% w/w of the total weight of the composition.
  • Suitable sweeteners that may be used, comprises saccharides such as aspartame, sugar derivatives having less than five alcohol (-OH) groups.
  • Other examples of sweeteners comprise sodium saccharin; aspartame; sugarless sweeteners including glycerol, hydrogenated starch hydrolysates, alone or in combination.
  • Suitable flavors that may be used, comprise citric acid, cinnamon, wintergreen, eucalyptus, spearmint, peppermint, menthol, anise as well as fruit flavors such as apple, pear, peach, vanilla, strawberry, cherry, apricot, orange, watermelon, banana and the like; bean-derived flavors, such as coffee, cocoa and the like or mixtures thereof.
  • the flavor may be present in an amount from about 0% w/w to about 5% w/w of the total weight of the composition.
  • Drug solution was prepared by dissolving drug in Isopropyl Alcohol.
  • the drug solution was adsorbed onto mixture of Dibasic calcium phosphate anhydrous, Pregelatinized Starch & Microcrystalline Cellulose in rapid mixture granulator following by drying in fluidized bed dryer at temperature of about 60 °C.
  • Dried granules were sized through suitable screen following by blending with extra-granular Colloidal silicon dioxide arid lubricating with stearic acid. Finally lubricated blend was compressed to form tablets and packed in Alu- Alu Blisters and charged for stability study.
  • Drug solution was prepared by dissolving drug in purified water.
  • the drug solution was adsorbed onto mixture of Dibasic calcium phosphate anhydrous, microcrystalline cellulose & Pregelatinized Starch in rapid mixture granulator following by drying in fluidized bed dryer at temperature of about 60 °C.
  • Dried granules were sized through suitable screen following by blending with extra-granular Colloidal silicon dioxide and lubricating with stearic acid. Finally lubricated blend was compressed to form tablets and packed in Alu-Alu Blisters and charged for stability study.
  • Example 3 Table 3
  • Drug solution was prepared by dissolving drug and povidone in Isopropyl Alcohol.
  • the drug solution was adsorbed onto mixture of Dibasic calcium phosphate anhydrous, Pregelatinized Starch & Microcrystalline Cellulose in rapid mixture granulator following by drying in fluidized bed dryer at temperature of about 60 °C.
  • Dried granules were sized through suitable screen following by blending with extra-granular Colloidal silicon dioxide and lubricating with stearic acid. Finally lubricated blend was compressed to form tablets and packed in Alu-Alu Blisters and charged for stability study.
  • Drug solution was prepared by dissolving drug in Isopropyl alcohol.
  • the drug solution was adsorbed onto mixture of Dibasic calcium phosphate anhydrous, Pregelatinized Starch and part of microcrystalline cellulose in rapid mixture granulator following by drying in fluidized bed dryer at temperature of about 60 °C.
  • Dried granules were sized through suitable screen following by blending with extra-granular microcrystalline cellulose and Colloidal silicon dioxide and lubricating with stearic acid. Finally lubricated blend was compressed to form tablets and packed in Alu-Alu Blisters and charged for stability study.
  • Samples of the formulation are packed in Alu-Alu Blisters and stored at the accelerated stability testing conditions of 40°C and 75% RH.
  • the impurity content is analyzed by HPLC at intervals and results are show below, where values are percentages of the rasagiline label content.

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  • Bioinformatics & Cheminformatics (AREA)
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  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
PCT/IN2014/000336 2013-05-20 2014-05-20 Pharmaceutical compositions of rasagiline WO2014192022A1 (en)

Applications Claiming Priority (2)

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IN1782/MUM/2013 2013-05-20
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024152752A1 (zh) * 2023-01-19 2024-07-25 上海云晟研新生物科技有限公司 甲磺酸雷沙吉兰口溶膜组合物、其制备方法及应用

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EP2764862A1 (en) * 2013-02-06 2014-08-13 Galenicum Health S.L. Immediate release tablets of rasagiline hemitartrate

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DATABASE WPI Section Ch Week 200747, Derwent World Patents Index; Class B05, AN 2007-477668, XP002729614, MOU C; ZONG T: "Solid oral preparation of leishajilan contains rasagiline or its pharmacologic salt, filler and disintegrant" *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024152752A1 (zh) * 2023-01-19 2024-07-25 上海云晟研新生物科技有限公司 甲磺酸雷沙吉兰口溶膜组合物、其制备方法及应用

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