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WO2015124995A1 - Formes galéniques solides de rivaroxaban - Google Patents

Formes galéniques solides de rivaroxaban Download PDF

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Publication number
WO2015124995A1
WO2015124995A1 PCT/IB2015/000196 IB2015000196W WO2015124995A1 WO 2015124995 A1 WO2015124995 A1 WO 2015124995A1 IB 2015000196 W IB2015000196 W IB 2015000196W WO 2015124995 A1 WO2015124995 A1 WO 2015124995A1
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WIPO (PCT)
Prior art keywords
rivaroxaban
dosage form
solution
granules
iii
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/IB2015/000196
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English (en)
Inventor
Saravanan Kannusamy
Venkata Vijaya Narasimha Kishan JAYANTHY
Taqiuddin Aman MOHAMMED
Jayant KARAJGI
Sivakumaran Meenakshisunderam
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.)
Aurobindo Pharma Ltd
Original Assignee
Aurobindo Pharma 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 Aurobindo Pharma Ltd filed Critical Aurobindo Pharma Ltd
Publication of WO2015124995A1 publication Critical patent/WO2015124995A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • 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
    • 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
    • A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/5375—1,4-Oxazines, e.g. morpholine
    • A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
    • 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
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2072—Pills, tablets, discs, rods characterised by shape, structure or size; Tablets with holes, special break lines or identification marks; Partially coated tablets; Disintegrating flat shaped forms
    • A61K9/2086—Layered tablets, e.g. bilayer tablets; Tablets of the type inert core-active coat
    • A61K9/209—Layered tablets, e.g. bilayer tablets; Tablets of the type inert core-active coat containing drug in at least two layers or in the core and in at least one outer layer
    • 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
    • A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
    • A61K9/2806—Coating materials
    • A61K9/2833—Organic macromolecular compounds
    • A61K9/286—Polysaccharides, e.g. gums; Cyclodextrin
    • A61K9/2866—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose

Definitions

  • the present invention relates to a process for preparing solid dosage form of oxazolidinone derivative compound. More particularly, the present invention relates to a process for preparing solid dosage form of rivaroxaban.
  • Oral solid composition of oxazolidinone derivative compound are used for the prophylaxis, secondary prophylaxis and/or treating thromboembolic disorders.
  • Rivaroxaban is a oxazolidinone derivative compound, chemically known as 5-Chloro-N-( ⁇ (5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]- l ,3- oxazo-lidin-5-yl ⁇ methyl)-2-thiophenecarboxamide and is disclosed in US 7, 157,456, US 7,585,860 and US 7,592,339.
  • Rivaroxaban is soluble in organic solvents (e.g., acetone, polyethylene glycol
  • XARELTO ® tablets are available coated tablets containing rivaroxaban as active ingredients and lactose monohydrate, croscarmellose sodium, hypromellose, microcrystalline cellulose, magnesium stearate, sodium lauryl sulfate, polyethylene glycol, titanium dioxide, ferric oxide red, polyvinyl alcohol and talc as inactive ingredients.
  • the pharmaceutical industry employs various methods for compounding pharmaceutical agents in tablet formulations. In particular granulation is one of the most prevalent methods.
  • Granulation is a process whereby granules are formed from a bulk drug substance with or without excipients to improve the properties of the bulk drug or formulation.
  • Granules are preparations consisting of solid, dry agglomerates of powder particles sufficiently robust to withstand handling.
  • Wet granulation is distinguished from dry granulation in that a granulating liquid, such as water, organic liquids or mixtures thereof, are used in wet granulation to produce granules.
  • the advantages of wet granulation include improvement of the cohesiveness and compatibility of powders, increase in density and good distribution providing uniform content of micronized or finely milled low-dosage drugs, reduction of dust and airborne contamination, and prevention of segregation of components.
  • US 7, 767,702 discloses combination comprising rivaroxaban and platelet aggregation inhibitor such as, for example, aspirin, ticlopidin (Ticlid), clopidogrel (Plavix); fibrinogen receptor antagonists.
  • platelet aggregation inhibitor such as, for example, aspirin, ticlopidin (Ticlid), clopidogrel (Plavix); fibrinogen receptor antagonists.
  • US 8,586,082 discloses solid pharmaceutical dosage forms of rivaroxaban in multiparticulate form, which can be prepared by melting the active agent with one or more excipients.
  • US 2008/0026057 disclose process for the preparation of a solid, orally administrable pharmaceutical composition comprising rivaroxaban in hydrophilized form, in which (a) first granules comprising the active compound (1) in hydrophilized form are prepared by moist granulation (b) and the granules are then converted into the pharmaceutical composition, if appropriate with addition of pharmaceutically suitable additives.
  • US 201 1/0189279 discloses composition comprising rivaroxaban, solubilizer, pseudo-emulsifier (natural gum), non-erodible polymer and pore-forming substance. US '279 further discloses modified release composition comprising pellet core coating with solution or suspension onto the pellet core and optionally blending the pellets with further excipients, compressing the resulting mixture into tablets. US 2012/0231076 discloses process of preaparing immediate release composition comprising rivaroxaban prepared by melt-granulation. The process for producing tablets comprising rivaroxaban and excipients, melting the mixture the mixture, granulating the melted mixture and compressing the mixture into tablets.
  • US 2013/0064888 discloses a pharmaceutical dosage form in the form of a tablet comprising: (a) a compressed inert core (b) an optional subcoat over the compressed inert core (c) a drug layer over the compressed core (a) or optional subcoat (b) comprising a drug having a water solubility at 25 °C of about 100 mg/1 or less, a coating polymer and optionally a surfactant, and (d) optionally one or more layers coating the drug layer.
  • US 2013/0281457 discloses pharmaceutical compositions of rivaroxaban comprising a solubilizer and a pseudo-emulsifier as excipients.
  • the solubilizer can be a surfactant
  • the pseudo-emulsifier is a natural product, such as a natural gum.
  • US '457 further discloses that the compositions can be prepared by dry granulation, by pellet layering to form a multiparticulate, by melting followed by grinding, or by co- precipitation with an antisolvent. These processes are said to form primary pharmaceutical compositions in the form of granules which are then further processed into a dosage form by mixing with further excipients and compressing to provide tablets.
  • WO 2010/146179 discloses solid pharmaceutical compositions of rivaroxaban, prepared by dry mixing or dry granulation of the rivaroxaban with at least one excipient, co-milling rivaroxaban with the excipients, hot melt granulation with a molten excipient, or hot melt extrusion with an excipient.
  • the mixture may then be agglomerated, granulated with a granulation liquid, or milled before compressing to form a tablet.
  • melt processing is not a particularly desirable procedure as it restricts the excipients that can be used and further entails operation at suitably high temperatures to enable the production of a melt.
  • This increases the risk of drug decomposition and polymorphic changes, as well as drug-excipient reactions, potentially leading to the presence of decomposition products in the final dosage form.
  • the above prior art references discloses different process for the preparation of solid oral dosage form of rivaroxaban.
  • the inventors of the present invention have endeavored to develop simple, cost effective alternate process which is more advantageous by means of comparable dissolution and bioavailability with respect to the marketed formulation of Xarelto® tablets.
  • the main objective of the present invention is to provide oral solid dosage form of rivaroxaban its solvates, hydrates and/or pharmaceutically acceptable salts and one or more pharmaceutically acceptable excipients.
  • Yet another, objective of the present invention is to provide oral solid dosage form of rivaroxaban in such a way that the dosage forms will comply with the reference product in terms of in terms of in vivo parameters like C max , T max and AUC and in vitro parameters like content uniformity, dissolution, disintegration and etc.
  • One embodiment of the present invention relates to oral solid composition comprising rivaroxaban its solvates, hydrates and/or pharmaceutically acceptable salts and one or more pharmaceutically acceptable excipients, wherein the ratio of rivaroxaban to excipient is in the range of 1 :2 to 1 :8.
  • another embodiment of the present invention relates to oral solid composition comprising rivaroxaban its solvates, hydrates and/or pharmaceutically acceptable salts, binder and one or more pharmaceutically acceptable excipients, wherein the percentage of binder is less than 1.0% by weight.
  • oral solid composition comprising rivaroxaban its solvates, hydrates and/or pharmaceutically acceptable salts, binder and one or more pharmaceutically acceptable excipients, wherein the percentage of binder is more than 15.0% by weight.
  • step (iii) granulating the blend of step (i) with the solution of step (ii).
  • the present invention provides a process for preparing oral solid dosage form of rivaroxaban comprising the steps of:
  • step (iii) spraying the solution or suspension of step (ii) onto the compressed core of step (i).
  • One embodiment of the present . invention relates to oral solid composition
  • rivaroxaban its solvates, hydrates and/or pharmaceutically acceptable salts and one or more pharmaceutically acceptable excipients wherein the ratio of rivaroxaban to excipient is in the range of 1 :2 to 1 :8.
  • the composition according to the invention comprises rivaroxaban its solvates, hydrates and/or pharmaceutically acceptable salts thereof, as active ingredient.
  • rivaroxaban can be used in any crystalline, partly crystalline, amorphous form or modification form.
  • the active ingredient (a) of the pharmaceutical composition of the present invention has a volume mean particle size (D50) of 0.1 to 10 ⁇ , more preferably of 0.5 to 5 ⁇ , still more preferably of 1.0 to 4 ⁇ .
  • the D90 value of the volume mean particle size distribution is from 1 to 15 ⁇ , preferably from 2 to 10 ⁇ , more preferably from 3 to 8 ⁇ .
  • the D10 value of the volume mean particle size distribution is from 0.01 to 5 ⁇ , preferably from 0.1 to 2.0 ⁇ , more preferably from 0.5 to 1.0 ⁇ .
  • pharmaceutically acceptable excipient refers to additives useful for converting pharmacologically active compounds into pharmaceutical dosage forms which are suitable for administration to patients. Suitable excipients include diluents, binders, disintegrants , surfactants, lubricants, glidants and coloring agents. Other pharmaceutically acceptable excipients can also be included. In another embodiment the solid matrix may contain one or more excipients selected from diluents, binders, surfactant, disintegrants, lubricants and pH adjusting agent.
  • Suitable "diluents" used according to the present invention are selected from water soluble or water insoluble or combination thereof.
  • Suitable water soluble diluents include sucrose, dextrose, lactose, mannitol, sorbitol and the like and water insoluble diluents include starch, microcrystalline cellulose, silicified microcrystalline cellulose, calcium silicate and the like or combination thereof.
  • the amount of diluent may range from about 20% to 95% by weight.
  • Suitable binders used according to the present invention are selected from the group comprising of hydroxypropylmethylcellulose, maize starch, povidone, hydroxypropylcellulose, pregelatinized starch and the like or combination thereof.
  • the amount of binder may range from about 0% to 22% by weight. In one embodiment the percentage of binder is less than 1% or greater than 17% by weight of the composition.
  • Suitable surfactants are selected from Tyloxapol , Triton X- 100 , polysorbates, polyoxyl 35 castor oil, polyoxyl 40 hydrogenated castor oil, polyoxyl 40 stearates, sorbitan monolaureates, sodium lauryl sulphate, polyethylene-propylene glycol copolymer (poloxamer), cremophor-40, propylene glycol and mixtures thereof.
  • the amount of surfactant may range from about 0.00 to 10.0% by weight.
  • Suitable disintegrants used according to the present invention are selected from starch, crospovidone, sodium starch glycolate, croscarmellose sodium and the like or combination thereof.
  • the amount of disintegrant may range from about 1 % to 10% by weight.
  • Suitable lubricants used according to the present invention are selected from magnesium stearate, hydrogenated castor oil, calcium stearate, sodium stearyl fumarate, talc, vegetable oils, stearic acid, fumaric acid and the like.
  • Suitable film coating polymers used according to the present invention are selected from povidone, ethylcellulose, hydroxypropylcellulose, hydroxypropylmethyl cellulose, polyvinyl alcohol and the like or mixtures thereof.
  • the amount of polymer may range from about 0.001 to 5.0 w/v%.
  • Suitable anti-sticking agents used according to the present invention are selected from talc, magnesium stearate and the like or a mixture thereof.
  • the amount of polymer may range from about 0.001 to 3.0 w/v%.
  • the composition is prepared either by moist granulation or direct compression.
  • oral solid composition comprising rivaroxaban its solvates, hydrates and/or pharmaceutically acceptable salts, binder selected from hydroxypropylmethylcellulose, maize starch, povidone, hydroxypropylcellulose, pregelatinized starch and one or more pharmaceutically acceptable excipients, wherein the percentage of binder is less than 1.0% by weight.
  • oral solid composition comprising rivaroxaban its solvates, hydrates and/or pharmaceutically acceptable salts, binder selected from hydroxypropylmethylcellulose, maize starch, povidone, hydroxypropylcellulose, pregelatinized starch and one or more pharmaceutically acceptable excipients, wherein the percentage of binder is more than 15.0% by weight.
  • the present invention provides a process for preparing oral solid dosage form of rivaroxaban comprising the steps of:
  • step (iii) granulating the blend of step (i) with the solution of step (ii),
  • step (iv) blending the granules of step (iii) with one or more extragranular excipients
  • step (v) formulating the blend obtained in step (iv) into solid dosage form.
  • the present invention also provides a process for preparing oral solid dosage form of rivaroxaban comprising the steps of:
  • step (iii) granulating the blend of step (i) with the solution of step (ii),
  • step (iv) blending the granules of step (iii) with one or more extragranular excipients selected from diluent, disintegrant and lubricant.
  • step (v) formulating the blend obtained in step (iv) into solid dosage form.
  • the present invention provides a process for preparing oral solid dosage form of rivaroxaban comprising the steps of:
  • excipients comprising about 20% to about 95% of diluents selected from sucrose, dextrose, lactose, mannitol, sorbitol, starch, microcrystalline cellulose, silicified microcrystalline cellulose, calcium silicate; about 1 % to about 10% of disintegrant selected from croscarmellose sodium, sodium starch glycolate, crospovidone in rapid mixer granulator and optionally rivaroxaban,
  • step (iii) granulating the blend of step (i) with the solution of step (ii), (iv) blending the granules of step (iii) with one or more extragranular excipients comprising about 20% to about 95% of diluent, about 0.01% to 10% of disintegrant, and about 0.001% to 5% of lubricant,
  • step (v) formulating the blend obtained in step (iv) into solid dosage form.
  • the present invention provides a process for preparing oral solid dosage form of rivaroxaban comprising the steps of:
  • step (iii) spraying the solution or suspension of step (ii) onto the compressed core of step (i).
  • the present invention provides preparing oral solid dosage form of rivaroxaban comprising the steps of:
  • a compressed core comprising rivoroxaban and one or more pharmaceutically acceptable excipients comprising about 20% to about 95% of diluent, about 0% to about
  • step (iii) spraying the solution or suspension of step (ii) onto the compressed core of step (i).
  • the present invention provides preparing oral solid dosage form of rivaroxaban comprising the steps of:
  • step-iii prepare separate solution of 0.20% to about 2.00% hypromellose with purified water, add this solution to step-ii) and homogenized.
  • step-iv formulating the granules of step-i) blend using the solution of step-iii) and the wet mass was dried in fluidized bed drier, mill the oversized granules and sifted, (v) the granules of step-iv were then lubricated with 0.10% to about 2.50% magnesium stearate and compressed into tablets.
  • the present invention provides a process for producing a pharmaceutical composition, comprising the steps of
  • a compressed core comprising rivaroxaban and one or more pharmaceutically acceptable excipients comprising about 20% to about 95% of diluent selected from one or more of sucrose, dextrose, lactose, mannitol, sorbitol, starch, microcrystalline cellulose, silicified microcrystalline cellulose, calcium silicate, about 0% to about 10% of binder selected from hydroxypropylmethylcellulose, maize starch, povidone, hydroxypropylcellulose, pregelatinized starch; about 0.01% to about 10% of disintegrant selected from starch, crospovidone, sodium starch glycolate, croscarmellose sodium; about 0.001 % to about 5% of lubricant selected from magnesium stearate, hydrogenated castor oil, calcium stearate, sodium stearyl fumarate, talc and 0% to about 10% of surfactant selected from Tyloxapol ® , Triton X-100 ® , polysorbates, polyoxyl 35
  • step (iii) spraying the solution or suspension of step (ii) onto the compressed core of step (i).
  • the compressed core is prepared either by direct compression or by granulation.
  • the solvents used according to present invention may be selected from isopropyl alcohol, methanol, ethanol, water, acetone, methylene chloride and the like or mixtures thereof.
  • the solid dosage forms include tablets and capsules.
  • the tablets may be uncoated or optionally coated.
  • film coating composition comprises a solution / suspension of film coating polymers and one or more excipients such as lactose, titanium dioxide, solubilizing agent and antisticking agent.
  • Suitable film coating polymers used according to the present invention are selected from ethylcellulose, hydroxypropylcellulose, hydroxypropylmethyl cellulose and the like or mixtures thereof.
  • Suitable anti-sticking agents used according to the present invention are selected from talc, magnesium stearate and the like or a mixture thereof.
  • solvent may be water or organic solvent.
  • solvent may be water or organic solvent.
  • step (iii) the blend of step (a) was granulated using the solution of step (b) and the wet mass was dried, milled and sifted, (iv) granules of step (iii) were blended with microcrystalline cellulose/ lactose, and croscarmellose sodium,
  • step (v) the granules of step (iv) was then lubricated with magnesium stearate and was compressed into tablets,
  • solvent may be water or organic solvent
  • lactose, microcrystalline cellulose and croscarmellose sodium were sifted and blended in rapid mixer granulator, (ii) hydroxypropylcellulose/ hydroxypropylmethyl cellulose/povidone, sodium lauryl sulfate, lactose/ mannitol were dissolved in a solvent,
  • step (iii) the blend of step (a) was granulated using the solution of step (b) and the wet mass was dried, milled and sifted,
  • step (iv) granules of step (iii) were blended with microcrystalline cellulose/ lactose, and croscarmellose sodium,
  • step (v) the blend of step (iv) was then lubricated with magnesium stearate and was compressed into tablets,
  • solvent may be water or organic solvent
  • step (iii) the blend of step (i) was granulated using the solution of step (ii) and the wet mass was dried, milled and sifted,
  • step (iv) granules of step (iii) were blended with microcrystalline cellulose/ lactose, and croscarmellose sodium,
  • step (v) the granules of step (iv) was then lubricated with magnesium stearate and was compressed into tablets,
  • step (vi) the compressed tablets obtained in step (v) were then coated with coating dispersion.
  • step (iii) blend of step (i) and step (ii) were mixed in geometrical proportions
  • step (iv) blend of step (iii) was then lubricated with magnesium stearate and compressed to tablet,
  • step (vi) the tablets of step (iv) was coated using the solution of step (v) and then dried,
  • step (iii) the blend of step (a) was granulated using the solution of step (b) and the wet mass was dried, milled and sifted,
  • step (iv) granules of step (iii) were blended with microcrystalline cellulose/ lactose, and croscarmellose sodium,
  • step (v) the granules of step (iv) was then lubricated with magnesium stearate and was compressed into tablets,
  • step (vii) the tablets of step (v) was coated using the solution of step (vi) and then dried,
  • step-iii granulate the step-i blend using the solution of step-iii and the wet mass was dried in fluidized bed drier, mill the oversized granules and sifted,
  • Example-7 the granules of step-iv was then lubricated with magnesium stearate and was compressed into tablets.
  • step-iv granulate the step-i blend using the solution of step-iii and the wet mass was dried in fluidized bed drier, mill the oversized granules and sifted, (v) the granules of step-iv was then lubricated with magnesium stearate and was compressed into tablets.
  • Example-8 Example-8, Example-8a, Example-8b, Example-8c, Example-8d & Example-8e
  • step-iii granulate the step-i blend using the solution of step-iii and the wet mass was dried in fluidized bed drier, mill the oversized granules and sifted,
  • step-iv the granules of step-iv was then lubricated with magnesium stearate and was compressed into tablets.

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Abstract

L'invention concerne un procédé de préparation de forme galénique solide de composé dérivé d'oxazolidinone. L'invention concerne plus particulièrement un procédé de préparation de forme galénique solide de rivaroxaban.
PCT/IB2015/000196 2014-02-19 2015-02-17 Formes galéniques solides de rivaroxaban Ceased WO2015124995A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN785CH2014 2014-02-19
IN785/CHE/2014 2014-02-19

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Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105267169A (zh) * 2015-12-07 2016-01-27 石家庄康贺威药业有限公司 一种利伐沙班片剂及其制备方法
WO2017146709A1 (fr) * 2016-02-25 2017-08-31 Mylan Inc. Procédé unique de granulation sous fort cisaillement améliorant la biodisponibilité du rivaroxaban
CN109157517A (zh) * 2018-10-15 2019-01-08 吉林省中晟制药有限公司 一种利伐沙班颗粒剂及制备方法
GR1009619B (el) * 2018-05-09 2019-10-23 Φαρμαζακ Α.Φ.Ε.Β.Ε. Φαρμακευτικη συνθεση που περιεχει ριβαροξαβανη και μεθοδος για την παρασκευη αυτης
CN112451531A (zh) * 2020-12-09 2021-03-09 乐普药业股份有限公司 一种阿司匹林和利伐沙班复方制剂及其制备方法
US20210267908A1 (en) * 2020-03-02 2021-09-02 Mankind Pharma Ltd. Pharmaceutical compositions of rivaroxaban
CN113425729A (zh) * 2021-06-24 2021-09-24 上海奥全生物医药科技有限公司 一种含有利伐沙班的药物组合物及其应用
WO2022049602A1 (fr) * 2020-09-05 2022-03-10 Inventia Healthcare Limited Compositions de rivaroxaban
CN114767647A (zh) * 2022-03-22 2022-07-22 新发药业有限公司 一种利伐沙班口服固体制剂的制备方法
CN114886867A (zh) * 2022-06-16 2022-08-12 北京四环制药有限公司 一种高稳定性的利伐沙班药物组合物及其制备方法
WO2022259118A1 (fr) * 2021-06-10 2022-12-15 Shilpa Medicare Limited Préparation de film oral à dissolution rapide comprenant du rivaroxaban
CN115969797A (zh) * 2021-10-15 2023-04-18 成都百裕制药股份有限公司 一种利伐沙班片及其制备方法

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US20070026065A1 (en) * 2004-12-24 2007-02-01 Bayer Healthcare Ag Solid, modified-release pharmaceutical dosage forms which can be administered orally
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