WO2009003001A2 - Préparation d'hémi-pentahydrate de risédronate de sodium - Google Patents

Préparation d'hémi-pentahydrate de risédronate de sodium Download PDF

Info

Publication number
WO2009003001A2
WO2009003001A2 PCT/US2008/068110 US2008068110W WO2009003001A2 WO 2009003001 A2 WO2009003001 A2 WO 2009003001A2 US 2008068110 W US2008068110 W US 2008068110W WO 2009003001 A2 WO2009003001 A2 WO 2009003001A2
Authority
WO
WIPO (PCT)
Prior art keywords
pentahydrate
hemi
risedronate sodium
solvent
sodium
Prior art date
Application number
PCT/US2008/068110
Other languages
English (en)
Other versions
WO2009003001A3 (fr
Inventor
Vijaya Bhaskar Bolugoddu
Srinivasa Reddy Bhimavarapu
Alekhya Donthula
Shakil Sait
Naresh Tondepu
Chandra Sekhar Ravi Ram Elati
Vara Prasad Sree Naga Venkata Lakshmi Vakamudi
Original Assignee
Dr. Reddy's Laboratories Ltd.
Dr. Reddy's Laboratories, Inc.
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
Priority claimed from IN1384CH2007 external-priority patent/IN2007CH01384A/en
Application filed by Dr. Reddy's Laboratories Ltd., Dr. Reddy's Laboratories, Inc. filed Critical Dr. Reddy's Laboratories Ltd.
Publication of WO2009003001A2 publication Critical patent/WO2009003001A2/fr
Publication of WO2009003001A3 publication Critical patent/WO2009003001A3/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/576—Six-membered rings
    • C07F9/58—Pyridine rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
    • A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis

Definitions

  • the present patent application relates to processes for preparing risedronic acid or its sodium salt. More specifically, the present application relates to processes for the preparation of risedronate sodium hemi-pentahydrate.
  • risedronic acid [1 -hydroxy-2-(3- pyhdinyl)ethylidene]bis(phosphonic acid).
  • the monosodium salt (hereinafter referred to by the officially adopted name "risedronate sodium") that is currently approved for use is a hemi-pentahydrate, which is structurally represented by
  • ACTONEL ® is also indicated for treatment to increase bone mass in men with osteoporosis, glucocorticoid-induced osteoporosis in men and women, and Paget's disease of bone in men and women.
  • Each ACTONEL ® tablet contains the equivalent of 5, 30, 35, 75, or 150 mg of anhydrous risedronate sodium.
  • U.S. Patent No. 5,583,122 discloses risedronic acid, salts or esters thereof, pharmaceutical compositions, and their use.
  • Risedronic acid or its salts are generally prepared by the bisphosphonation of 3-pyridylacetic acid, followed by treating with an appropriate base.
  • U.S. Patent No. 6,410,520 discloses a process for preparation of risedronate sodium hemi-pentahydrate, or monohydrate, or their mixtures.
  • U.S. Patent No. 7,002,014 discloses a process for the preparation of risedronate sodium in hemi-pentahydrate crystal form. W. R.
  • 2003/0195170 A1 discloses risedronate sodium polymorphs, pseudopolymorphs, and processes for their preparation.
  • International Application Publication No. WO 2006/051553 A1 describes processes for preparing two crystalline risedronate sodium monohydrate and hemi-pentahydrate forms.
  • International Application Publication No. WO 2008/004000 A1 describes risedronate sodium hemi-pentahydrate with a HPLC purity of more than 99.5% and a process for its preparation.
  • International Application Publication No. WO 2008/044245 A2 describes a process for the preparation of risedronate sodium hemi-pentahydrate comprising a treatment of risedronic acid with sodium hydroxide in the presence of a mixture of water and dimethylsulfoxide.
  • the present invention provides processes for the preparation of risedronate sodium in the crystalline hemi-pentahydrate form, an embodiment comprising:
  • step (b) treating the combination obtained in step (a) with a sodium base;
  • risedronate sodium hemi-pentahydrate wherein a solvent comprises an alcohol, water or mixtures thereof.
  • the invention provides risedronate sodium hemi-pentahydrate prepared according to the processes.
  • the invention provides pharmaceutical compositions comprising risedronate sodium hemi-pentahydrate prepared according to the processes.
  • Fig. 1 is an X-ray powder diffraction (XRPD) pattern of a sample of risedronate sodium hemi-pentahydrate, as prepared in Example 5.
  • Fig. 2 is a thermogravimetric analysis (TGA) curve of a sample of risedronate sodium hemi-pentahydrate.
  • Fig. 3 is a differential scanning calorimetry (DSC) curve of a sample of risedronate sodium hemi-pentahydrate.
  • Fig. 4 is a Fourier-transform infrared (FTIR) absorption spectrum of a sample of risedronate sodium hemi-pentahydrate.
  • FTIR Fourier-transform infrared
  • Fig. 5 is an XRPD pattern of risedronic acid, as prepared in Example 2.
  • pure When a molecule or other material is identified herein as “pure,” it generally means, unless specified otherwise, that the material is about 99% pure or higher. In general, this refers to purity with regard to unwanted residual solvents, reaction by-products, impurities and unreacted starting materials. “Substantially” pure means the same as “pure,” except that the material is about 95% pure or higher. “Essentially” pure means the same as “substantially” pure except that the material is about 90% pure or higher.
  • the present inventors found that the use of alcohols at low temperatures for isolation of risedronate sodium produces pure risedronate sodium hemi- pentahydrate with good yields.
  • step (b) treating the combination obtained in step (a) with a sodium base; and (c) forming risedronate sodium hemi-pentahydrate; wherein a solvent comprises an alcohol, water or mixtures thereof.
  • Step a) involves providing a combination of risedronic acid and a solvent.
  • the combination comprising risedronic acid may be obtained by combining risedronic acid with a solvent, or the combination may be obtained directly from a reaction in which risedronic acid is formed.
  • Solvents that may be utilized for this step include but are not limited to: water; and mixtures of water with CrC 4 alcohols such as methanol, ethanol, isopropanol, n-butanol, and 2-butanol, or glycols such as ethylene glycol and propylene glycol, in various proportions.
  • Step a) may be performed at temperatures from about 10 0 C to about 40 0 C, or from about 15°C to about 35°C, or from about 20 0 C to about 30°C.
  • Step b) involves treatment of the combination provided in step (a) with a sodium base.
  • This step involves adjustment of the pH of the reaction mass with a sodium base.
  • Suitable sodium bases that may be utilized for adjusting the pH of the reaction mass may be any inorganic bases such as sodium carbonate, sodium hydroxide and sodium bicarbonate, either as solids or their aqueous solutions.
  • the pH is adjusted to be within a range of about 4 to 6, or about 4.4 to about 5.2, or about 4.5 to about 5.1 , or about 4.6 to about 5.
  • the combination may be cooled to about 0 0 C to about 30 0 C, or about 5°C to about 25°C, or about 10 0 C to about 20°C, before the addition of sodium base.
  • the resulting solution may optionally be treated with carbon and filtered to produce a particle-free solution.
  • Step c) involves the precipitation of risedronate sodium hemi-pentahydrate.
  • an anti-solvent can be added at about 0 0 C to about 30 0 C, or about 5°C to about 25°C, or about 10 0 C to about 20°C.
  • the anti-solvents that may be utilized for this step are same as the solvents that are used in step a), except water.
  • the quantity of anti-solvent used in this step may range from about 1 to 20 milliliters, per gram of hsedronic acid.
  • the mass after the addition of anti-solvent may be stirred for any desired time period, such as about 1 -4 hours, or about 1 -3 hours, or about 1 -2 hours. Longer times are also useful.
  • a small quantity of seed crystals may be added to the mass to generate the desired crystalline form.
  • the mass may be further cooled to between about -10 0 C to about 10 0 C, or between about 0 0 C to about 5°C.
  • An anti-solvent may be additionally added to the mass to enhance the crystallization of risedronate sodium.
  • the anti-solvents that may be utilized for this are same as those solvents that are used in step a), except water.
  • the quantity of anti-solvent used in this step may range from about 3 to 20, or from about 5 to 15, milliliters per gram of risedronic acid.
  • the mass after the addition of additional anti-solvent may be stirred for about 1 -10 hours, or about 1 -5 hours, or about 1 -3 hours. Longer times also may be used.
  • the ratios of anti-solvent to water in the mass before separation of a solid product may range from about 25:75 to about 75:25, by volume.
  • the methods by which a solid product can be recovered from the final mixture can be any of techniques such as decantation, filtration by gravity or by suction, centrifugation, and the like.
  • the crystals so isolated can carry a small proportion of occluded mother liquor containing impurities, and the crystals may be washed with the anti-solvent to reduce the impurity concentrations.
  • the recovered product may be further dried. Drying may be carried out in a tray dryer, vacuum oven, air oven, fluidized bed drier, spin flash dryer, flash dryer and the like. The drying may be carried out at temperatures from about 25°C to about 50 0 C, with or without vacuum, and in the presence or absence of an inert atmosphere like nitrogen, argon, neon, and helium. The drying may be carried out for any desired time periods to achieve the desired product purity, such as from about 1 hour to about 15 hours, or longer. If desired, risedronate sodium hemi-pentahydrate obtained above may be further purified by slurrying or recrystallizing in a solvent or mixture of solvents.
  • the solvents that can be utilized for this purification step include, but are not limited to: CrC 4 alcohols such as methanol, ethanol, isopropanol, n-butanol, and 2-butanol; glycols such as ethylene glycol and propylene glycol; and their mixtures with water in various proportions.
  • CrC 4 alcohols such as methanol, ethanol, isopropanol, n-butanol, and 2-butanol
  • glycols such as ethylene glycol and propylene glycol
  • the purification of risedronate sodium hemi- pentahydrate may enhance the chemical and polymorphic purities.
  • the material that is subjected to purification may be either in a wet form or in a dry form.
  • Purification by slurrying may be performed at temperatures ranging from about -10 0 C to about 40 0 C, or from about 0°C to about 30 0 C, or from about 10°C to about 20°C.
  • the slurrying may be carried out for about 5 minutes to about 5 hours, or about 5 minutes to about 3 hours, or about 10 minutes to about 1 hour. Longer time periods also are useful.
  • the purification by recrystallization may be performed by dissolving risedronate sodium hemi-pentahydrate in the solvent and isolating the product by cooling the reaction mass.
  • the dissolution step may be performed at temperatures ranging from about 30°C to about the reflux temperature of the solvent.
  • the solution may be cooled to between about -10°C and about 30°C, or between about 0°C and about 20°C, or between about 0 0 C and about 10 0 C.
  • the product after purification may be isolated and dried using the methods described above.
  • Risedronate sodium hemi-pentahydrate obtained by the processes of the present invention contains less than about 5%, or less than about 2%, or less than about 0.5% of risedronate sodium monohydrate. In certain instances, the risedronate sodium monohydrate content is below the limit of detection.
  • Methods known to persons skilled in the art may be used for the determination of risedronate sodium monohydrate in risedronate sodium hemi- pentahydrate.
  • the general methods that are useful for the quantification of one polymorphic form in another form include XRPD, FTIR, Raman spectroscopy, solid state NMR, DSC, etc. Any of these methods may be used for the quantification of risedronate sodium monohydrate in risedronate sodium hemi- pentahydrate.
  • Risedronate sodium hemi-pentahydrate of the present application may contain less than about 0.5% of total impurities, as determined by high performance liquid chromatography (HPLC). In embodiments, the total impurities are less than about 0.2%, or less than about 0.1 %, or less than about 0.05%.
  • HPLC method An example of a HPLC method that can be used for the analysis includes an lnertsil ODS 3V, 250*4.6 mm, 5 ⁇ m or equivalent column. Additional method parameters are given in the table below:
  • risedronate sodium hemi-pentahydrate obtained by processes of the present invention has a particle size distribution where D(0.9) is less than about 250 microns, often less than about 150 microns.
  • D(0.9) is a particle size value, for which 90 percent of the particles in a mixture are smaller.
  • a desired particle size distribution may be obtained directly from the process or may be obtained by using techniques known to persons skilled in the art, such as milling, grinding, spray-drying, etc.
  • the techniques that may be used for the determination of particle sizes include sieve analysis, sedimentation, electrozone sensing (CoulterTM counter), microscopy, and low angle laser light scattering (LALLS). Methods most commonly used in the pharmaceutical industry include laser diffraction and sieve analysis.
  • Risedronic acid used for the preparation of risedronate sodium hemi- pentahydrate may have a crystalline or amorphous form, may be a mixture of forms.
  • the starting material i.e., risedronic acid, used herein may be prepared by any process, including the processes described in documents mentioned above or the process described hereinbelow.
  • Risedronic acid may be prepared by the reaction of 3-pyridylacetic acid with phosphorous acid and a halophosphorous compound, in the presence of diethyl carbonate as a solvent and methanesulfonic acid as co-diluent.
  • the halophosphorous compound may comprise any of PCI 3 , PCI 5 , POCI 3 , PBr 3 , POBr 3 and PBr 5 .
  • 3-Pyridylacetic acid, phosphorous acid and diethyl carbonate may be added in any order followed by addition of a halophosphorous compound.
  • Methanesulfonic acid may be added before or after the addition of a halophosphorous compound.
  • the reaction may be carried out at temperatures of about 40°C to about 100°C, or about 60 0 C to about 80 0 C.
  • the reaction may be carried out for a period of about 1 -15 hours, or about 2-10 hours, or about 3-8 hours. Longer time periods may also be used.
  • the phosphorous acid is used in amounts of about 1 to 10 moles, or about 1 to 5 moles, per mole of 3-pyridylacetic acid.
  • the halophosphorous compound is used in amounts of about 1 to 10 moles, or about 1 to 5 moles, per mole of 3- pyridylacetic acid.
  • the methanesulfonic acid is used in amounts of about 0.5 to 10 times, or about 1 to 5 times, by volume to the weight of 3-pyridylacetic acid.
  • the diethyl carbonate is used in an amount of about 1 to 10 times, or about 1 to 5 times, by volume to the weight of 3-pyridylacetic acid.
  • the reaction mass obtained as described above is diluted with water and the layers obtained may be separated.
  • the aqueous layer may be further heated to temperatures about 60 0 C to about the reflux temperature and maintained for about 1 -20 hours, or longer.
  • An inorganic acid such as hydrochloric acid may be added to the aqueous layer before heating.
  • the reaction mass may then be cooled to about 0 0 C to about 30 0 C, or, about 10 0 C to about 20°C, and pH of the reaction mass adjusted to between 1 -2 using a base such as sodium hydroxide or potassium hydroxide.
  • a solvent may be added to the reaction mass before or after the pH adjustment with a base.
  • Solvents that may be added to the reaction mass include but are not limited to: water; d-C 4 alcohols such as methanol, ethanol, isopropanol, n-butanol, and 2-butanol; glycols such as ethylene glycol and propylene glycol; and mixtures thereof in various proportions.
  • the method by which a solid product is recovered from the final mixture can be any of techniques such as decantation, filtration by gravity or by suction, centrifugation, and the like.
  • the crystals so isolated will carry a small proportion of occluded mother liquor containing a higher percentage of impurities, and the crystals may be washed with a solvent to get rid of the impurities.
  • the recovered product may be further dried. Drying may be carried out in a tray dryer, vacuum oven, air oven, fluidized bed drier, spin flash dryer, flash dryer and the like. The drying may be carried out at temperatures from about 25°C to about 80°C, with or without vacuum, and in the presence or absence of an inert atmosphere like nitrogen, argon, neon, and helium. The drying may be carried out for any desired time periods to achieve the desired product purity, from about 1 hour to about 15 hours, or longer.
  • risedronic acid obtained above may be further purified by slurrying in a solvent or mixture of solvents.
  • the material obtained above is subjected to purification may be either in wet form or in dry form. This step may be performed at temperatures ranging from about -10 0 C to about 4O 0 C or from about 0 0 C to about 20 0 C, or from about 0 0 C to about 10 0 C.
  • Solvents that may be used for this purification by slurrying include but are not limited to: water; CrC 4 alcohols such as methanol, ethanol, isopropanol, n- butanol, and 2-butanol; glycols such as ethylene glycol and propylene glycol; and mixtures thereof in various proportions.
  • risedronic acid so prepared may contain less than about 2% of total impurities, as determined by HPLC. In instances, the total impurities are less than about 1 %, or less than about 0.5%.
  • the above-prepared formulations may be in the form of immediate release, delayed release or modified release.
  • Immediate release compositions may be conventional, dispersible, chewable, mouth dissolving, or flash melt preparations.
  • Modified release compositions may include hydrophilic or hydrophobic, or combinations of hydrophilic and hydrophobic, release rate controlling substances to form matrix or reservoir systems or combinations of matrix and reservoir systems.
  • the compositions may be prepared by direct blending, dry granulation or wet granulation or by extrusion and spheronization.
  • the compositions may be presented as uncoated, film coated, sugar coated, powder coated, enteric coated or modified release coated.
  • compositions that find use in the present patent application include, but are not limited to: diluents such as starch, pregelatinized starch, lactose, powdered cellulose, microcrystalline cellulose, dicalcium phosphate, tricalcium phosphate, mannitol, sorbitol, sugar and the like; binders such as acacia, guar gum, tragacanth, gelatin, polyvinylpyrrolidones, hydroxypropyl celluloses, hydroxypropyl methylcelluloses, pregelatinized starches, and the like; disintegrants such as starch, sodium starch glycolate, pregelatinized starch, crospovidones, croscarmellose sodium, colloidal silicon dioxide and the like; lubricants such as stearic acid, magnesium stearate, zinc stearate and the like; glidants such as colloidal silicon dioxide and the like; solubility or wetting enhancers such as anionic or cationic
  • compositions that are of use include but are not limited to film formers, plasticizers, colorants, flavoring agents, sweeteners, viscosity enhancers, preservatives, antioxidants and the like.
  • the X-ray powder diffraction patterns described herein were determined using a Bruker AXS D8 Advance powder X-ray diffractometer with a copper K- alpha radiation source.
  • DSC analysis was performed with a Perkin Elmer, Pyris 6 DSC instrument. Sample masses for analysis were 1 to 3 mg, weighed into aluminum sample pans. The samples were encapsulated into closed aluminum pans and subsequently crimped to ensure a tight seal. The thermograms were recorded from 40 to 25O 0 C under a nitrogen atmosphere of 50 mL/minute, at a heating rate of 10°C/minute. TGA analysis was carried out on a TGA Q500 from TA Instruments. The sample mass was placed in a platinum pan with nitrogen gas purge at a flow rate of 40 mL/minute for balance and 60 mL/minute for sample. The TG analysis was recorded with a ramp rate of 10°C/minute up to 250 0 C. FTIR analysis was performed with a Perking Elmer Spectrum One FTIR spectrometer. The spectrum was collected in the scan range of 400-4000 cm "1 and the samples were in KBr pellets.
  • the pH of the reaction mass was adjusted to 1.8 by addition of caustic lye solution (47-50% w/w NaOH, 183 ml) at 10-15 0 C and maintained at the same temperature for about 1 hour.
  • the formed solid was filtered and washed with isopropanol (50 ml).
  • the obtained solid was dried under vacuum at 66°C to a constant weight, to afford 100 g of the title compound. HPLC purity: 99.28%.
  • the pH of the reaction mass was adjusted to 1.8 by addition of aqueous sodium hydroxide solution (81 ml of caustic lye solution diluted with 81 ml of water) at 8-13 0 C and maintained at the same temperature for about 2 hours.
  • the formed solid was filtered and washed with isopropanol (50 ml).
  • the obtained solid was dried under vacuum at 50-58 0 C to a constant weight, to afford 92.1 g of the title compound.
  • the crystalline form of risedronic acid obtained by the above process is characterized by its XRPD pattern having characteristic peaks at approximately 8.5, 10.4, 12.4, 13.0, 16.6, 17.8, 20.4, 21 .2, 26.1 , and 28.8, ⁇ 0.2 degrees two- theta.
  • the crystalline form of risedronic acid is also characterized by its XRPD pattern, substantially in accordance with the pattern of Fig. 5.
  • EXAMPLE 3 Preparation of [1 -Hydroxy-2-(3-pyridinyl)ethylidene]bis(phosphonic acid).
  • 3-pyridylacetic acid (50 g) and diethyl carbonate (150 ml) were charged into a round bottom flask and stirred for 5 minutes and then phosphorous acid (44.9 g) was added.
  • Phosphorous trichloride (96 ml) was added to the reaction mass and then the mass was heated.
  • Methanesulfonic acid (75 ml) was added to the reaction mass slowly between 43-45 0 C. The reaction mass was maintained at 60- 62 0 C for about 1 hour and then maintained at 70-72 0 C for about 5 hours.
  • Chilled water (50 ml) was added to the reaction mass at 70-79 0 C and then the mass was cooled.
  • the reaction mass was further cooled to and maintained at 3-4 0 C for 2 hours.
  • the reaction mass was filtered and the solid was suction-dried.
  • the wet solid and water (175 ml) were charged into a round bottom flask, stirred for about 30 minutes at 25-26 0 C and filtered.
  • the wet cake was washed with a chilled mixture of water (25 ml) and isopropanol (25 ml) and suction dried.
  • the wet material was dried in an oven at 53 0 C to a constant weight to obtain 98.3 g of risedronic acid. Yield: 95.2%.
  • the loss on drying (LOD) at 140 0 C infrared moisture balance, 10 minutes) was found to be 0.6% w/w.
  • HPLC purity 99.59%.
  • the mass was maintained at the same temperature for about 2 hours and filtered.
  • the solid was suction dried and then dried under vacuum to afford 0.4 of the title compound as a second crop.
  • a crystalline form of hsedronate sodium hemi-pentahydrate obtained by the above process is characterized by its XRPD pattern having characteristic peaks at approximately 8.9, 12.2, 12.9, 13.5, 15.3, 15.7, 19.7, 24.5, 27.8, 31 .1 , and 36.5, ⁇ 0.2 degrees two-theta.
  • a crystalline form of risedronate sodium hemi- pentahydrate is also characterized by its XRPD pattern, substantially in accordance with the pattern of Fig. 1 .
  • Fig. 2 is a TGA curve for the product
  • Fig. 3 is its DSC curve.
  • the filtrate was placed in a round bottom flask and cooled to 16 0 C, and isopropanol (112 ml) was added to the reaction mass over about 10 minutes at the same temperature.
  • the reaction mass was maintained at 16-17°C for about 2 hours.
  • the reaction mass was further cooled and maintained for about 1 hour at 0-4°C.
  • Chilled isopropanol (700 ml) was added to the reaction mass over 35 minutes at 0-4 0 C and the reaction mass was maintained at the same temperature for about 1-1.5 hours.
  • the formed solid was filtered.
  • the wet solid obtained was placed into a fresh round bottom flask containing water (385 ml) and isopropanol (315 ml) at 16°C.

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Rheumatology (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Behavior & Ethology (AREA)
  • Engineering & Computer Science (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

L'invention porte sur des procédés de préparation d'hémi-pentahydrate de risédronate de sodium.
PCT/US2008/068110 2007-06-27 2008-06-25 Préparation d'hémi-pentahydrate de risédronate de sodium WO2009003001A2 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
IN1384/CHE/2007 2007-06-27
IN1384CH2007 IN2007CH01384A (fr) 2004-10-04 2007-06-27
US3615608P 2008-03-13 2008-03-13
US61/036,156 2008-03-13

Publications (2)

Publication Number Publication Date
WO2009003001A2 true WO2009003001A2 (fr) 2008-12-31
WO2009003001A3 WO2009003001A3 (fr) 2009-04-02

Family

ID=40186266

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2008/068110 WO2009003001A2 (fr) 2007-06-27 2008-06-25 Préparation d'hémi-pentahydrate de risédronate de sodium

Country Status (1)

Country Link
WO (1) WO2009003001A2 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8076483B2 (en) 2006-05-11 2011-12-13 M/S. Ind Swift Laboratories Limited Process for the preparation of pure risedronic acid or salts

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004037252A1 (fr) * 2002-10-25 2004-05-06 Zentiva, A.S. Nouvelle forme cristalline de sel de sodium d'acide 3-pyridyl-1-hydroxyethylidene-1,1-biphosphonique
WO2005066190A1 (fr) * 2004-01-02 2005-07-21 Hexal A/S Nouveaux sels de risedronate
WO2007036688A1 (fr) * 2005-09-30 2007-04-05 Pliva Hrvatska D.O.O. Sels et hydrates pharmaceutiquement acceptables de l’acide risédronique

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004037252A1 (fr) * 2002-10-25 2004-05-06 Zentiva, A.S. Nouvelle forme cristalline de sel de sodium d'acide 3-pyridyl-1-hydroxyethylidene-1,1-biphosphonique
WO2005066190A1 (fr) * 2004-01-02 2005-07-21 Hexal A/S Nouveaux sels de risedronate
WO2007036688A1 (fr) * 2005-09-30 2007-04-05 Pliva Hrvatska D.O.O. Sels et hydrates pharmaceutiquement acceptables de l’acide risédronique

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8076483B2 (en) 2006-05-11 2011-12-13 M/S. Ind Swift Laboratories Limited Process for the preparation of pure risedronic acid or salts

Also Published As

Publication number Publication date
WO2009003001A3 (fr) 2009-04-02

Similar Documents

Publication Publication Date Title
JP4559431B2 (ja) 固体及び結晶イバンドロネートナトリウム及びその調製方法
CA2717326C (fr) Preparation de lenalidomide
US7642353B2 (en) Process of making crystalline aripiprazole
US8063074B2 (en) Polymorphic forms of esomeprazole sodium
WO2007032808A1 (fr) Trihydrate cristallin de l'acide zolédronique
US7112577B2 (en) Pharmaceutically acceptable alendronate salts in amorphous form
EP1014987B1 (fr) Compositions orales de levosimendan
US7977478B2 (en) Polymorphic forms of vardenafil
AU2002334200A1 (en) Pharmaceutically acceptable alendronate salts in amorphous form
WO2007074475A2 (fr) Nouvelles formes polymorphes de l'ibandronate
EP2311794B1 (fr) Polymorphes du bromfénac sodium et procédé pour leur préparation
WO2007103711A2 (fr) Formes polymorphes du rimonabant
WO2009147529A1 (fr) Déférasirox pratiquement pur et ses procédés de préparation
EP1375497B1 (fr) Sel de magnésium de S-omeprazole
WO2009003001A2 (fr) Préparation d'hémi-pentahydrate de risédronate de sodium
EP2316840A1 (fr) Formes polymorphes de l'ibandronate sodium
WO2010091169A2 (fr) Préparation de valsartan
WO2006025939A1 (fr) Formes cristallines de vitamine d21,24(s)-dihydroxy
WO2007092758A2 (fr) Formes cristallines de périndopril erbumine
WO2022081502A1 (fr) Formes à l'état solide de lorécivivint
WO2021165995A1 (fr) Nouveaux sels et/ou co-cristaux de ténofovir alafénamide
EP2610239A1 (fr) Préparation de rasagiline hémitartrate
SPECIFICATION CRYSTALLINE FORMS OF MIRABEGRON AND PROCESS FOR THEIR PREPARATION

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 08771880

Country of ref document: EP

Kind code of ref document: A2

NENP Non-entry into the national phase in:

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 08771880

Country of ref document: EP

Kind code of ref document: A2