WO2011010324A1 - Compositions pharmaceutiques orales stables comprenant de la rasagiline et procédé - Google Patents

Compositions pharmaceutiques orales stables comprenant de la rasagiline et procédé Download PDF

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Publication number
WO2011010324A1
WO2011010324A1 PCT/IN2010/000309 IN2010000309W WO2011010324A1 WO 2011010324 A1 WO2011010324 A1 WO 2011010324A1 IN 2010000309 W IN2010000309 W IN 2010000309W WO 2011010324 A1 WO2011010324 A1 WO 2011010324A1
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WO
WIPO (PCT)
Prior art keywords
rasagiline
pharmaceutically acceptable
composition
oral pharmaceutical
pharmaceutical composition
Prior art date
Application number
PCT/IN2010/000309
Other languages
English (en)
Inventor
Arun Prasad
Krishna Prasad
Vemula Sathyanarayana
Ashok Rampal
Original Assignee
Alkem Laboratories Ltd.
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 Alkem Laboratories Ltd. filed Critical Alkem Laboratories Ltd.
Priority to AU2010274589A priority Critical patent/AU2010274589A1/en
Publication of WO2011010324A1 publication Critical patent/WO2011010324A1/fr

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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
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2013—Organic compounds, e.g. phospholipids, fats
    • A61K9/2018—Sugars, or sugar alcohols, e.g. lactose, mannitol; Derivatives thereof, e.g. polysorbates
    • 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
    • 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

Definitions

  • the present invention relates to stable oral pharmaceutical compositions comprising rasagiline or a pharmaceutically acceptable salt thereof and process for the preparing thereof.
  • Rasagiline is a propargylamine-based drug which is a selective irreversible inhibitor of the enzyme monoamine oxidase (hereinafter MAO) and provides the R(+) enantiomer of N-propargyl-1-aminoindan which is a selective irreversible inhibitor of the B-form of monoamine oxidase enzyme (hereinafter MAO-B).
  • MAO monoamine oxidase
  • MAO-B B-form of monoamine oxidase enzyme
  • Rasagiline is used as a monotherapy in early Parkinson's disease or as an adjunct therapy in more advanced cases.
  • Human cells contain two forms of monoamine oxidase, MAO-A and MAO-B. Both are found in the brain, but MAO-B is far more prevalent and is responsible for the breakdown of dopamine after its release into the synapse.
  • Parkinson's disease is characterized by the death of cells that use dopamine to transmit their signals, this result in a decrease in synaptic signal strength and concomitant symptomology.
  • rasagiline permits the signaling neurons to reabsorb more of it for reuse later, somewhat compensating for the diminished quantities manufactured.
  • the subject invention is in the field of selective irreversible inhibitors of the enzyme
  • the subject invention also provides pharmaceutical compositions containing rasagiline which are
  • Rasagiline is currently administered orally in the form of a conventional tablet designed to be swallowed whole and is presently marketed in US as Azilect® by Teva Pharma AZILECT® (rasagiline tablets) is indicated for the treatment of the signs and symptoms of idiopathic Parkinson's disease as initial monotherapy and as adjunct therapy to levodopa.
  • US6126968 discloses a pharmaceutical composition in tablet form comprising rasagiline or its acceptable salt as an active ingredient and atleast one alcohol selected from group of pentahydric or hexahydric alcohols like mannitol, xylitol and sorbitol
  • EP0814789 discloses formulations of MAO-B inhibitors which attempt to address some of the known problems. However, it carries out lyophilization of the MAO-B inhibitor formulations which is an expensive process and results in high friability of the product, further increasing cost.
  • US20060188581A1 discloses a mixture of particles of a pharmaceutically acceptable salt of R(+)-N-propargyl-l-aminoindan, wherein more than 90% of the total amount by volume of R(+)-N-propargyl-l-aminoindan salt particles have a size of less than 250 microns along with a solid composition comprising thereof and a carrier.
  • WO2009122301A2 discloses rasagiline mesylate having a 90 volume-percent of the particles (D90) with a size of about 600 microns to about 1500 microns. It also relates to a substantially pure rasagiline mesylate and a process for controlling the particle size of rasagiline mesylate to obtain rasagiline mesylate having a D90 particle size of about 255 microns to about 1400 microns and a pharmaceutical composition comprising rasagiline mesylate having a 90 volume- percent of the particles (D90) with a size of about 255 microns to about 1500 microns and one or more pharmaceutically acceptable excipients
  • oral pharmaceutical compositions which are stable and bioequivalent to the commercially available formulation in US i.e Azilect® tablets can be prepared without using the pentahydric or hexahydric alcohols as used by the prior arts
  • It is an object of the present invention to provide a stable oral pharmaceutical composition comprising rasagiline or its pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier, wherein the said composition is free of pentahydric or hexahydric alcohols which affords an excellent composition while avoiding afore mentioned disadvantages
  • It is also an object of the present invention to provide a process for the preparation of a stable oral pharmaceutical composition comprising rasagiline or its pharmaceutically acceptable salt thereof, wherein the said composition is free of pentahydric or hexahydric alcohols
  • the present invention relates to a stable oral pharmaceutical composition
  • a pharmaceutically acceptable carrier wherein the carrier is selected from a polyhydric alcohol, disaccharide(s) and polysaccharide(s) or mixtures thereof, and wherein the said composition is free of pentahydric or hexahydric alcohols.
  • the present invention relates to a process for the preparation of a stable oral pharmaceutical composition of rasagiline or a pharmaceutically acceptable salt thereof comprising:
  • a suitable pharmaceutically acceptable carrier selected from a polyhydric alcohol, disaccharide(s) and polysaccharides) or mixtures thereof,
  • a stable oral pharmaceutical composition comprising rasagiline or its pharmaceutically acceptable salt thereof with a pharmaceutically acceptable carrier, wherein the carrier is selected from a polyhydric alcohol, disaccharide(s) and polysaccharide ⁇ ) or mixtures thereof, and wherein the said composition is free of pentahydric or hexahydric alcohols.
  • B A stable oral pharmaceutical composition as in A above, wherein the said composition is bioequivalent to the commercially available formulation in US i.e. Azilect® tablets.
  • composition as in A above, wherein the said composition relates to a stable oral pharmaceutical composition comprising rasagiline or its pharmaceutically acceptable salt thereof with a pharmaceutically acceptable polysaccharide(s) wherein the composition is free of pentahydric or hexahydric alcohols.
  • a process for the preparation of a stable oral pharmaceutical composition of rasagiline or a pharmaceutically acceptable salt thereof comprising:
  • a suitable pharmaceutically acceptable carrier selected from a polyhydric alcohol, disaccharide(s) and polysaccharide ⁇ ) or mixtures thereof,
  • 'rasagiline' or 'rasagiline or a pharmaceutically acceptable salt thereof as used herein refers to rasagiline free base or any pharmaceutically acceptable salt of rasagiline
  • a particularly preferred pharmaceutically acceptable salt of rasagiline is rasagiline mesylate.
  • 'stable' refers to chemical stability of rasagiline in solid dosage forms wherein there is no change in impurities percentages and dissolution profile when kept at 40°C k 75% RH foi 3 months
  • oral pharmaceutical compositions which are stable and bioequivalent to the commercially available formulation in US, i.e. Azilect® tablets can be prepared without using the pentahydric or hexahydric alcohols as used by the prior arts
  • prior arts relate to rasagiline of particular particle size to provide an acceptable formulation
  • US2006018858 IAl relates to rasagiline particles with d(90) of less than 250 microns to provide content uniformity
  • WO2009122301A2 discloses rasagiline mesylate having d(90) with a size of about 600 microns to about 1500 microns to achieve homogeneous distribution of the drug substance in a tablet blend, good flow properties, better dissolution and solubility properties with greater bioavailability
  • stable oral pharmaceutical compositions of rasagiline or its pharmaceutically acceptable salt thereof can be prepared irrespective of particle size used to achieve considerable physicochemical properties with desired drug content uniformity for pharmaceutical dosage units.
  • the present invention relates to a stable oral pharmaceutical composition
  • a stable oral pharmaceutical composition comprising rasagiline or its pharmaceutically acceptable salt thereof with a pharmaceutically acceptable carrier, wherein the carrier is selected from a polyhydric alcohol, disaccharide(s) and polysaccharide(s) or mixtures thereof, and wherein the said composition is free of pentahydric or hexahydric alcohols.
  • the present invention relates to a process for the preparation of a stable oral pharmaceutical composition of rasagiline or a pharmaceutically acceptable salt thereof comprising:
  • a suitable pharmaceutically acceptable carrier selected from a polyhydric alcohol, disaccharide(s) and polysaccharide ⁇ ) or mixtures thereof,
  • This invention provides a stable oral pharmaceutical composition comprising rasagiline or a pharmaceutically acceptable salt thereof which is bioequivalent to the commercially available formulation in US i.e. Azilect® tablets.
  • the carriers used in the present invention are selected from a polyhydric alcohol, disaccharide(s) and polysaccharide(s) or mixtures thereof
  • the carriers used in the present invention are free of pentahydric or hexahydric alcohols.
  • the polyhydric alcohol may be selected from maltitol or lactitol. More preferably the polyhydric alcohol is maltitol, consisting of one glucose unit linked with one sorbitol unit via an alpha (1,4) bond.
  • Di saccharides may be selected from sucrose or maltose.
  • Polysaccharides may be selected from polydextrose composed of randomly cross linked glucose with all types of glucosidic bonds (1,6 predominate) like starches; or crystalline cellulose like microcrystalline cellulose which is purified, partially depolymerized cellulose.
  • the carriers may be present in the composition in an amount of from about 20 % w/w to about 70 % w/w of the composition.
  • composition of the present invention may optionally also include conventional additives such as disintegrants, binders, lubricants, glidants, and the like, all as known per se.
  • disintegrants which may be used in accordance with the present invention are pre gelatinized starch, sodium starch glycolate, croscarmellose sodium and the like thereof.
  • binders which may be used in accordance with the present invention are starch, polyvinyl pyrrolidine (PVP), hydroxy propyl methyl cellulose
  • the present invention relates to the use of solvents that may be used in the present process for the preparation of a stable oral pharmaceutical composition of rasagiline or a pharmaceutically acceptable salt thereof Any solvent can be used which can dissolve rasagiline mesylate with more than lOmg/mL solubility
  • solvents that may be used include but not limited to isopropyl alcohol, water, ethanol or mixtures thereof
  • the present invention relates to a stable oral pharmaceutical composition
  • a stable oral pharmaceutical composition comprising rasagiline or its pharmaceutically acceptable salt thereof, wherein the pharmaceutical dosage forms may include solid oral dosage forms such as, but not limited to, powders, granules, pellets, tablets, and capsules
  • the present invention relates to a stable oral pharmaceutical composition
  • a stable oral pharmaceutical composition comprising rasagiline or its pharmaceutically acceptable salt thereof with a pharmaceutically acceptable carrier, wherein the carrier is selected from a polyhydric alcohol, disaccharide(s) and polysaccharide(s) or mixtures thereof, and wherein the said composition is free of pentahydric or hexahydric alcohols.
  • the said pharmaceutical compositions may be prepared by the conventional processes such as wet granulation, dry granulation or direct compression.
  • rasagiline or its pharmaceutically acceptable salt thereof is mixed with a carrier material which is free of pentahydric and hexahydric alcohols along with the excipients Granulation may occur in the presence of purified water or other alcoholic solvents.
  • Dry granulation can be done by two processes: (1) slugging, which involves mixing the rasagiline or its pharmaceutically acceptable salt thereof with a carrier which is free of pentahydric and hexahydric alcohols and further mixing with the excipients, slugging, dry screening, lubrication and compression, or (2) roller compaction process.
  • Direct, compression involves compressing tablets directly from ⁇ the physical mixture of rasagiline or its pharmaceutically acceptable salt thereof with a carrier which is free of pentahydric and hexahydric alcohols, with the excipients.
  • the pharmaceutical compositions of the present invention' may be obtained by preparing placebo granules comprising the suitable carrier material and pharmaceutically acceptable excipients, and mixing these with rasagiline to obtain a blend, which may be encapsulated or compressed into tablets These methods afford excellent compositions of rasagiline or its pharmaceutically acceptable salt thereof.
  • compositions of the present invention be prepared by solubilizing rasagiline in a suitable solvent and using the rasagiline solution to prepare a suitable pharmaceutical dosage form by the conventional processes such as wet granulation or solvent coating.
  • pharmaceutical compositions of the present invention were prepared by a solubilization process wherein rasagiline was solubilised in a suitable solvent. Drug content uniformity is a unique requirement for all dosage forms. When following the solubilization process of the present invention, consequently favorable content uniformity of the blend as well as of dosage units was obtained Thus, pharmaceutical compositions of the present invention were prepared by solubilizing rasagiline in a suitable solvent and using the rasagiline solution to prepare a suitable pharmaceutical dosage form by wet granulation.
  • rasagiline or its pharmaceutically acceptable salt thereof was dissolved in a solvent; further this solution was added to the binder solution and stirred.
  • the carrier material which is free of pentahydric and hexahydric alcohols was mixed with the disintegrant Granulation may occur in the presence of purified water or other alcoholic solvents.
  • the above dry mix was granulated with the rasagiline solution using Fluid bed processor or Rapid mixer granulator and blended with the extra granular material. The lubricant was added, mixed and compressed into tablets.
  • compositions of the present invention were prepared by solubilizing rasagiline in a suitable solvent and using the rasagiline solution to prepare a suitable pharmaceutical dosage form by solvent coating methods
  • solvent coating methods pharmaceutical compositions of the present invention were prepared by coating the rasagiline solution over the carrier which is free of pentahydric and hexahydric alcohols and converting into a suitable pharmaceutical dosage form or by compressing the placebo tablets comprising the carrier which is free of pentahydric and hexahydric alcohols and coating the rasagiline solution over the placebo tablets or by coating the placebo pellets comprising the carrier which is free of pentahydric and hexahydric alcohols with the rasagiline solution which may be encapsulated or compressed into tablets.
  • present invention involves wet granulation process of preparation wherein rasagiline or its pharmaceutically acceptable salt thereof and all other ingredients were screened; dry mixed the intra granular material with a carrier which is free of pentahydric and hexahydric alcohols in a rapid mixer granulator. Further the prepared binder solution was added to the intragranular material and granulated. And the above dried granules were blended with extragranular material and then lubricant was added, mixed and compressed into tablets.
  • Example 1 Composition and preparation of 0.5 mg tablet of Rasagiline
  • Process of preparation involves rasagiline or its pharmaceutically acceptable salt thereof and all other ingredients are screened; dry mix the intra granular material with a carrier such as a polyhydric alcohol which is free of pentahydric and hexahydric alcohols in a Rapid mixer granulator. Further the prepared binder solution was added to the intragranular material and granulated. Blend above dried granules with extragranular material and then lubricant was added and mixed for 5 min and compressed into tablets.
  • a carrier such as a polyhydric alcohol which is free of pentahydric and hexahydric alcohols
  • Example 9 Composition and preparation of 1 mg tablet of Rasagiline
  • Process of preparation involves rasagiline or its pharmaceutically acceptable salt thereof and all other ingredients are screened; dry mix the intra granular material with a carrier such as a polyhydric alcohol which is free of pentahydric and hexahydric alcohols in a Rapid mixer granulator. Further the prepared binder solution was added to the intragranular material and granulated. Blend above dried granules with extragranular material and then lubricant was added and mixed for 5 min and compressed into tablets.
  • a carrier such as a polyhydric alcohol which is free of pentahydric and hexahydric alcohols
  • Example 10 Composition and preparation of 0.5 mg and 1 mg tablets of Rasagiline
  • Example 12 Tablets parameters as prepared in example 10
  • Example 13 Uniformity of dosage units as prepared in example 10
  • Example 14 Stability data of the tablets as prepared in example 10
  • composition prepared in example 10 was subjected to bioequivalence studies An open label, randomized two-treatment, two period, two sequence, two way cross over, single dose, comparative oral bio-availability study i e composition of example 10 (1 mg) with Azilect ® (Rasagiline tablets- 1 mg) of Teva, United States of America under fasting conditions was carried out. Study design: A balanced, open label, randomized, two-treatment, two-period, two sequence, single dose, crossover comparative bioavailability study under fasting conditions
  • Test product Rasagiline tablets 1 mg (Example 10)
  • Drug administration After an overnight fast of at least 10 hrs, dosing was done with 240 ml of water at ambient temperature. In each study period a single dose of Rasagiline tablet (1 mg) was administered to the subjects. Subjects receiving the test product in one study period received the reference product (Azilect® 1 mg) in the other period. Subjects were instructed not to chew or crush the tablets. Blood Sample collection: A total of 17 samples were taken per period at 0.16, 0.33, 0.50, 0.67, 0.87, 1.0, 1.25, 1.5, 2.0, 3.0, 4.0, 5.0, 6.0, 8.0, 10.0 and 12.0 hrs post dose.
  • Pharmacokinetic parameters Employing the estimated plasma concentration time profile of rasagiline, pharmacokinetic parameters like C max, AUC o-t, AUC o-inf, were calculated
  • composition of the present invention is bioequivalent to the commercially available Rasagiline tablet in the United States of America i.e. Azilect ® .

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Biophysics (AREA)
  • Molecular Biology (AREA)
  • Medicinal Preparation (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

L'invention concerne une composition pharmaceutique orale stable comprenant de la rasagiline ou son sel pharmaceutiquement acceptable ainsi qu'un vecteur pharmaceutiquement acceptable sélectionné dans le groupe comprenant alcool polyhydrique, disaccharide(s) et polysaccharide(s) ou leurs mélanges. Cette composition est dépourvue d'alcools pentahydriques ou hexahydriques
PCT/IN2010/000309 2009-07-23 2010-05-14 Compositions pharmaceutiques orales stables comprenant de la rasagiline et procédé WO2011010324A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2010274589A AU2010274589A1 (en) 2009-07-23 2010-05-14 Oral pharmaceutical composition of rasagiline and process for preparing thereof

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN1704/MUM/2009 2009-07-23
IN1704MU2009 2009-07-23

Publications (1)

Publication Number Publication Date
WO2011010324A1 true WO2011010324A1 (fr) 2011-01-27

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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7968749B2 (en) 2008-06-19 2011-06-28 Teva Pharmaceutical Industries, Ltd. Process for preparing and drying solid rasagiline base
US8080584B2 (en) 2009-01-23 2011-12-20 Teva Pharmaceuticals Industries, Ltd. Delayed release rasagiline citrate formulation
US8188149B2 (en) 2007-09-17 2012-05-29 Teva Pharmaceutical Industries, Ltd. Use of R(+)-N-propargy1-1-aminoindan to treat or prevent hearing loss
WO2013107441A1 (fr) * 2012-01-18 2013-07-25 Stada Arzneimittel Ag Procédé permettant de préparer une composition pharmaceutique solide contenant le principe actif rasagiline
WO2013175493A1 (fr) 2012-04-09 2013-11-28 Cadila Healthcare Limited Compositions pharmaceutiques orales stables
US8809310B2 (en) 2006-02-21 2014-08-19 Teva Pharmaceutical Industries, Ltd. Use of rasagiline for the treatment of multiple system atrophy
WO2014192022A1 (fr) * 2013-05-20 2014-12-04 Cadila Healthcare Limited Compositions pharmaceutiques de rasagiline
US8946300B2 (en) 2006-04-03 2015-02-03 Teva Pharmaceutical Industries, Ltd. Use of rasagilline for the treatment of restless legs syndrome
US10292947B2 (en) * 2016-03-26 2019-05-21 Dr. Reddy's Laboratories Ltd. Pharmaceutical compositions for N-propargylamine derivative

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1892233A1 (fr) * 2006-08-18 2008-02-27 Ratiopharm GmbH De nouveaux sels de la substance active rasagiline
WO2010111264A2 (fr) * 2009-03-24 2010-09-30 Dr. Reddy's Laboratories Ltd. Préparations de rasagiline

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1892233A1 (fr) * 2006-08-18 2008-02-27 Ratiopharm GmbH De nouveaux sels de la substance active rasagiline
WO2010111264A2 (fr) * 2009-03-24 2010-09-30 Dr. Reddy's Laboratories Ltd. Préparations de rasagiline

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8809310B2 (en) 2006-02-21 2014-08-19 Teva Pharmaceutical Industries, Ltd. Use of rasagiline for the treatment of multiple system atrophy
US8946300B2 (en) 2006-04-03 2015-02-03 Teva Pharmaceutical Industries, Ltd. Use of rasagilline for the treatment of restless legs syndrome
US8188149B2 (en) 2007-09-17 2012-05-29 Teva Pharmaceutical Industries, Ltd. Use of R(+)-N-propargy1-1-aminoindan to treat or prevent hearing loss
US7968749B2 (en) 2008-06-19 2011-06-28 Teva Pharmaceutical Industries, Ltd. Process for preparing and drying solid rasagiline base
US8163960B2 (en) 2008-06-19 2012-04-24 Teva Pharmaceutical Industries, Ltd. Process for preparing and drying solid rasagiline base
US8080584B2 (en) 2009-01-23 2011-12-20 Teva Pharmaceuticals Industries, Ltd. Delayed release rasagiline citrate formulation
WO2013107441A1 (fr) * 2012-01-18 2013-07-25 Stada Arzneimittel Ag Procédé permettant de préparer une composition pharmaceutique solide contenant le principe actif rasagiline
WO2013175493A1 (fr) 2012-04-09 2013-11-28 Cadila Healthcare Limited Compositions pharmaceutiques orales stables
WO2014192022A1 (fr) * 2013-05-20 2014-12-04 Cadila Healthcare Limited Compositions pharmaceutiques de rasagiline
US10292947B2 (en) * 2016-03-26 2019-05-21 Dr. Reddy's Laboratories Ltd. Pharmaceutical compositions for N-propargylamine derivative

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