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US20110190363A1 - Liquid formulations of bendamustine - Google Patents

Liquid formulations of bendamustine Download PDF

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Publication number
US20110190363A1
US20110190363A1 US13/048,325 US201113048325A US2011190363A1 US 20110190363 A1 US20110190363 A1 US 20110190363A1 US 201113048325 A US201113048325 A US 201113048325A US 2011190363 A1 US2011190363 A1 US 2011190363A1
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Prior art keywords
formulation
bendamustine
pharmaceutically acceptable
less
solvent
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Abandoned
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US13/048,325
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Inventor
Anthony S. Drager
Rachel Y. LaBell
Piyush R. Patel
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Cephalon LLC
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Cephalon LLC
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Priority to US13/048,325 priority Critical patent/US20110190363A1/en
Application filed by Cephalon LLC filed Critical Cephalon LLC
Assigned to CEPHALON, INC. reassignment CEPHALON, INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: DRAGER, ANTHONY S., LABELL, RACHEL Y., PATEL, PIYUSH R.
Publication of US20110190363A1 publication Critical patent/US20110190363A1/en
Priority to US13/362,430 priority patent/US8344006B2/en
Priority to US13/655,498 priority patent/US20130041004A1/en
Priority to US14/084,768 priority patent/US20140080881A1/en
Priority to US14/151,242 priority patent/US20140128443A1/en
Priority to US14/221,422 priority patent/US20140206733A1/en
Priority to US14/814,570 priority patent/US20150335750A1/en
Priority to US15/688,182 priority patent/US20180125824A1/en
Priority to US16/835,562 priority patent/US20210008035A1/en
Priority to US17/015,175 priority patent/US20210113530A1/en
Abandoned legal-status Critical Current

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4164—1,3-Diazoles
    • A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
    • A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/20—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing sulfur, e.g. dimethyl sulfoxide [DMSO], docusate, sodium lauryl sulfate or aminosulfonic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/22—Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
    • A61K47/40—Cyclodextrins; Derivatives thereof
    • 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
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
    • 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
    • A61K9/08—Solutions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/02—Antineoplastic agents specific for leukemia

Definitions

  • the present invention relates to liquid formulations of bendamustine, and the pharmaceutical salts thereof.
  • bendamustine In light of its instability in aqueous solution, bendamustine is currently supplied as a lyophilized powder for injection. Just prior to its infusion, the medical practitioner reconstitutes the powder with Sterile Water for Injection. Reconstitution should yield a clear, colorless to pale yellow solution and the powder should completely dissolve in about 5 minutes. If particulate matter is observed, the reconstituted product should not be used and should be discarded. The reconstituted product is then transferred to a 0.9% Sodium Chloride Injection infusion bag within 30 minutes of reconstitution. This admixture should be a clear and colorless to slightly yellow solution. If the admixture comprises particulate matter or is discolored, it should be discarded and a fresh sample prepared.
  • the present invention is directed to liquid pharmaceutical formulations comprising bendamustine, or a pharmaceutically acceptable salt or prodrug thereof, and a polar aprotic solvent.
  • Certain preferred embodiments include liquid pharmaceutical formulations comprising bendamustine, or a pharmaceutically acceptable salt or prodrug thereof, a polar aprotic solvent, and a non-aqueous polar protic solvent.
  • FIG. 1 is a graph of a stability analysis of bendamustine in various solvents at 25° C.
  • FIG. 2 is a graph of a stability analysis of bendamustine in various solvents at 5° C.
  • FIG. 3 is a graph of bendamustine purity, over time, in 99% propylene glycol, at 5° C. and at 25° C.
  • pharmaceutically acceptable liquid formulations of bendamustine, and the pharmaceutically acceptable salts thereof, in particular the hydrochloride salt can be prepared by combining bendamustine, or the pharmaceutically acceptable salt thereof, with a polar aprotic solvent or mixture of polar aprotic solvents.
  • Polar, aprotic solvents are known in the art and include, for example, 1-methyl-2-pyrrolidone, 1,3-dimethyl-2-imidazolidinone, dimethylacetamide, dimethyl sulfoxide, acetone, tetrahydrofuran, 1,4-dioxane, acetonitrile, dimethyl formamide, propylene carbonate.
  • Organic solvents for pharmaceutical parenterals and embolic liquids include dimethylacetamide, dimethyl sulfoxide, and mixtures thereof.
  • polar, aprotic solvents are sufficiently non-nucleophilic towards bendamustine such that polar aprotic solvent-bendamustine adducts do not form over the course of typical commercial storage conditions.
  • Typical commercial storage conditions include time periods of, for example, about 30 days, about 90 days, about 180 days, and about 365 days (about 1 month, about 3 months, about 6 months, and about 1 year).
  • Typical commercial storage conditions also include temperatures of about 23° C. (ambient room temperature) and refrigerated temperatures below ambient room temperature, for example, about 5° C.
  • the liquid formulations of the present invention are stored at refrigerated temperatures.
  • nonaqueous polar protic solvents include alkyl alcohols, for example, ethanol, ethylene glycol, propylene glycol, butylene glycol, glycerin, polysorbates, for example TWEEN 20, TWEEN 40, and TWEEN 80, and cyclodextrins (such as hydroxypropyl- ⁇ -cyclodextrin), polyalkylene glycols, such as polyethylene glycol, polypropylene glycol, and polybutylene glycol, and primary amides such as niacinamide.
  • alkyl alcohols for example, ethanol, ethylene glycol, propylene glycol, butylene glycol, glycerin
  • polysorbates for example TWEEN 20, TWEEN 40, and TWEEN 80
  • cyclodextrins such as hydroxypropyl- ⁇ -cyclodextrin
  • polyalkylene glycols such as polyethylene glycol, polypropylene glycol, and polybutylene glycol
  • Such formulations will typically comprise 90% or less, by volume of the formulation, of the nonaqueous polar protic solvent. In other preferred embodiments, formulations will comprise between about 20% and about 85%, by volume of the formulation, of the nonaqueous polar protic solvent. In still other embodiments, formulations will comprise between about 30% and about 70%, by volume of the formulation, of the nonaqueous polar protic solvent. In most preferred embodiments, formulations will comprise about 80%, about 67% or about 34%, by volume of the formulation, of the nonaqueous polar protic solvent.
  • formulations of the present invention will comprise 10 moles per liter, or less, of the nonaqueous polar protic solvent.
  • formulations of the present invention will comprise between about 4 moles per liter to about 9.5 moles per liter, of the nonaqueous polar protic solvent.
  • formulations will comprise about 9.1 moles per liter of the nonaqueous polar protic solvent.
  • formulations will comprise about 4.6 moles per liter, of the nonaqueous polar protic solvent.
  • nonaqueous polar protic solvents are of sufficient nucleophilicity to form potentially undesirable polar protic solvent-bendamustine adducts, such adducts will not form during typical commercial storage if the concentration of the polar protic solvent is kept within the scope of the present invention.
  • Liquid formulations of the present invention are stable over the course of a typical commercial storage period.
  • “stable” is defined as no more than about a 10% loss of bendamustine under typical commercial storage conditions.
  • formulations of the present inventions will have no more than about a 10% loss of bendamustine, more preferably, no more than about a 5% loss of bendamustine, under typical commercial storage conditions.
  • Bendamustine converts to non-bendamustine products (i.e., “degrades”) upon exposure to certain nucleophiles, for example, water and alkyene glycols such as propylene glycol. Exposure of bendamustine to water can produce “HP1,” which is undesirable.
  • BM1 dimer Another undesirable compound that bendamustine can convert to over time is “BM1 dimer.”
  • DCE Still another undesirable compound that bendamustine can convert to over time is “DCE.”
  • esters of bendamustine can form, e.g., PG-1 and PG-2.
  • analysis of formulations of the present invention will exhibit 1.50% or less of DCE, as determined by HPLC analysis, after about 1 year (about 365 days) at about 5° C. More preferably, the formulations will exhibit 1.0% or less of DCE, as determined by HPLC analysis, after about 1 year (about 365 days) at about 5° C. Even more preferably, the formulations will exhibit 0.5% or less of DCE, as determined by HPLC analysis, after about 1 year (about 365 days) at about 5° C. Most preferably, the formulations will exhibit about 0.1% or less of DCE, as determined by HPLC analysis, after about 1 year (about 365 days) at about 5° C.
  • analysis of the formulations will exhibit about 0.4% or less of HP1, as determined by HPLC analysis, after about 1 year (about 365 days) at about 5° C.
  • the formulations will exhibit about 0.10% or less of HP1, as determined by HPLC analysis, after about 1 year (about 365 days) at about 5° C.
  • analysis of the formulations will exhibit about 0.70% or less of BM1 dimer, as determined by HPLC analysis, after about 1 year (about 365 days) at about 5° C.
  • the formulations will exhibit about 0.30% or less of dimer, as determined by HPLC analysis, after about 1 year (about 365 days) at about 5° C.
  • the formulations will exhibit about 0.10% or less of BM1 dimer, as determined by HPLC analysis, after about 1 year (about 365 days) at about 5° C.
  • alkylene glycol as the nonaqueous polar protic solvent
  • analysis of those formulations will exhibit 1.5% or less of alkylene glycol esters of bendamustine, as determined by HPLC analysis, after about 1 year (about 365 days) at about 5° C.
  • analysis of those formulations will exhibit 1.5% or less of propylene glycol esters PG-1 and PG-2, as determined by HPLC analysis, after about 1 year (about 365 days) at about 5° C.
  • Analysis of the liquid formulations of the present invention can be performed using techniques known in the art, including, for example, HPLC, gas chromatography, and NMR. After exposure to typical commercial storage conditions, analysis of the formulations of the present invention will indicate that the formulation contains no less than about 90% of the amount of bendamustine present prior to exposure to the storage conditions. Preferably, analysis will indicate that the formulation contains no less than about 95% of the amount of bendamustine present prior to exposure to the storage conditions.
  • analysis of the formulations of the present invention will indicate that the formulation contains no less than about 90% of the amount of bendamustine present prior to exposure to storage conditions that include temperatures of about 5° C. and time periods of about 30 days (about 1 month) to about 365 days (about 1 year).
  • analysis of the formulations of the present invention will indicate that the formulation contains no less than about 90% of the amount of bendamustine present prior to exposure to storage conditions that include temperatures of about 5° C. and time periods of about 30 days (about 1 month), about 90 days (about 3 months), and about 180 days (about 6 months).
  • analysis will indicate that the formulation contains no less than about 95% of the amount of bendamustine present prior to exposure to storage conditions that include temperatures of about 5° C. and time periods of about 30 days (about 1 month) to about 365 days (about 1 year). More preferably, analysis will indicate that the formulation contains no less than about 95% of the amount of bendamustine present prior to exposure to storage conditions that include temperatures of about 5° C. and time periods of about 30 days (about 1 month), about 90 days (about 3 months), and about 180 days (about 6 months).
  • Formulations of the present invention can comprise pharmaceutically useful concentrations of bendamustine, or a pharmaceutically acceptable salt thereof.
  • Useful concentrations include concentrations ranging from about 5 mg/mL to about 200 mg/mL.
  • the concentration of bendamustine, or a pharmaceutically acceptable salt thereof ranges from about 5 mg/mL to about 120 mg/mL.
  • Preferred concentrations include about 5 mg/mL, about 10 mg/mL, about 20 mg/mL, about 30 mg/mL, about 40 mg/mL, about 50 mg/mL, about 60 mg/mL, about 100 mg/mL and about 200 mg/mL of bendamustine, or a pharmaceutically acceptable salt thereof.
  • Greater than 200 mg/ml of bendamustine, or a pharmaceutically acceptable salt thereof, for example, greater than about 300 mg/mL are also within the scope of the present invention, as are saturated solutions of bendamustine, or a pharmaceutically acceptable salt thereof.
  • the term “about” is defined as ⁇ 10%, preferably ⁇ 5%,
  • formulations of the present invention may further comprise other pharmaceutically acceptable excipients.
  • antioxidants e.g., tocopherol (Vitamin E), ascorbic acid, methyl paraben, butylhydroxyanisole (BHA), butylhydroxytoluene (BHT), and propyl gallate
  • surfactants e.g., polysorbates (TWEEN 20, TWEEN 40, TWEEN 80)
  • lipids e.g., dimyristoylphophatidylcholine (DMPC), Dimyristoylphosphatidylglycerol (DMPG), distearoylphophatidylglycerol (DSPG), fillers (e.g., mannitol), organic acids (e.g., citric acid, lactic acid, benzoic acid), hydrophilic polymers (e.g., polyethylene glycols (PEG 300, PEG 400), complexing agents (e.g., niacinamide, nicotinic acid
  • These methods comprise administering to the patient a therapeutically effective amount of a preparation prepared from a pharmaceutical formulation of the present invention.
  • therapeutically effective amount refers to the amount determined to be required to produce the physiological effect intended and associated with a given drug, as measured according to established pharmacokinetic methods and techniques, for the given administration route. Appropriate and specific therapeutically effective amounts can be readily determined by the attending diagnostician, as one skilled in the art, by the use of conventional techniques.
  • the effective dose will vary depending upon a number of factors, including the type and extent of progression of the disease or disorder, the overall health status of the particular patient, the relative biological efficacy of the compound selected, the formulation of the active agent with appropriate excipients, and the route of administration.
  • the liquid formulations of bendamustine described herein are intended to be administered via injection, for example, they may be administered subcutaneously, intracutaneously, intravenously, intramuscularly, intra-articularly, intrasynovially, intrasternally, intrathecally, intralesionally, intracranially or via infusion.
  • the volume of the liquid formulation of the present invention needed for the required dose can be aseptically withdrawn and transferred to an infusion bag of 0.9% Sodium Chloride (or other pharmaceutically acceptable intravenous solution) for injection. After transfer, the contents of the infusion bag are thoroughly mixed.
  • Administration by intravenous infusion is typically provided over a time period of from about 30 to about 60 minutes.
  • Previously described lyophilized formulations of bendamustine required reconstitution of the lyophilized bendamustine prior to mixture with the acceptable intravenous solution before infusion.
  • the pharmaceutical formulations and preparations of the present invention can be administered in combination with one or more anti-neoplastic agents where the anti-neoplastic agent is given prior to, concurrently with, or subsequent to the administration of the formulation or preparation of the present invention.
  • Pharmaceutically acceptable anti-neoplastic agents are known in the art.
  • Preferred anti-neoplastic agents are those disclosed in co-pending U.S. application Ser. No. 11/330,868, filed Jan. 12, 2006, the entirety of which is incorporated herein by reference.
  • the three replicates were combined and mixed well and then pipetted into amber HPLC vials and placed in stability chambers at 25° C. and 5° C. All the samples were clear and colorless except for the DMI sample which was clear and yellow.
  • the 25° C. stability leveled out from about 180 days (about 6 months) to about 365 days (about 12 months, about 1 year). At 5° C., all solutions had a purity greater than 90%.
  • the analysis of stability samples can be seen in the graphs of FIGS. 1 and 2 .
  • bendamustine (BM1) in 99% propylene glycol degrades significantly when stored at 25° C. for less than 100 days. After storage at 5° C. for about 365 days, the purity of the bendamustine is about 80% or less.
  • TREANDA lyophilized mixture of bendamustine hydrochloride and mannitol; 25 mg (bendamustine hydrochloride) vials; 2) a 66% dimethylacetamide (DMA)/34% propylene glycol (PG) (w/w) solution (90 mg (bendamustine hydrochloride)/mL stock); and 3) a 100% DMA solution (45 mg (bendamustine hydrochloride)/mL stock).
  • DMA dimethylacetamide
  • PG propylene glycol
  • the resulting solutions were administered as a bolus via a saphenous vein at a fixed volume of 1.0 mL/kg. There was at least a 7-day washout period separating successive doses.
  • blood samples for pharmacokinetic profiling of bendamustine and its 2 active circulating metabolites, ⁇ -hydroxybendamustine (M3) and N-des-methylbendamustine (M4) were collected via a femoral vein immediately prior to dosing and at preselected timepoints through 12 hr postdose.
  • Concentrations of bendamustine, M3 and M4 in plasma samples were determined using a validated high-performance liquid chromatography method with tandem mass spectrometric detection (LC-MS/MS) as follows. Bendamustine and the M3 and M4 metabolites are extracted from plasma by protein precipitation using acetonitrile. After the extraction, the aliquoted sample is acidified with 1% formic acid and bendamustine with an added carbon in the carboxylic acid chain is added as an internal standard. The samples are evaporated to dryness and the residue is reconstituted with an acetonitrile/water/formic acid/ammonium formate mixture.
  • LC-MS/MS tandem mass spectrometric detection
  • the sample is injected into an HPLC system with LC/MS/MS detection using a Phenomenex Synergi Max-RP column with an acetonitrile/water/formic acid/ammonium formate mobile phase.
  • Pharmacokinetic analyses were performed using noncompartmental methods.
  • C max and AUC bendamustine systemic exposure
  • the respective mean values of C max and AUG, for bendamustine were 6037 ng/mL and 2314 ng ⁇ hr/mL for the TREANDA formulation, 7380 ng/mL and 2854 ng ⁇ hr/mL for the 66% DMA/34% PG formulation and 6209 ng/mL and 2372 ng ⁇ hr/mL for the 100% DMA formulation.
  • Plasma clearance (CL) and volume of distribution (V Z and V SS ) for bendamustine were also comparable between each of the 3 formulations (See Table III).
  • t max , hr is given as Median [range]
  • t 1/2 is given as the Harmonic Mean
  • ⁇ Z is the slope of line in elimination phase used to calculate half-life
  • MRT 0- ⁇ is the mean residence time.
  • Admixtures in 0.9% sodium chloride 500 mL bag were prepared at a high dose (360 mg bendamustine hydrochloride) and purity was determined over time at room temperature for up to 8 hours using HPLC, using a Zorbax Bonus-RP column with a gradient from 93% 0.1% trifluoroacetic acid in water (Mobil Phase A)/7% 0.1% trifluoroacetic acid in acetonitrile (Mobile Phase B) to 10% Mobil Phase A/90% Mobil Phase B.
  • the 66% DMA/34% PG formulation had a concentration of bendamustine hydrochloride of 90 mg/g, so 4 mL was injected into a 500 mL bag of saline, inverted 10 times and sampled at room temperature for 8 hours. After 8 hours the purity was 95.4%. This is within the label requirements for dosing Treanda.
  • This formulation of the present invention could be used for up to 8 hours at room temperature.
  • reconstituted Treanda can only be stored at room temperature for up to 3 hours.
  • the 100% DMA formulation had a concentration of 45 mg/g, so 8 mL was injected into a 500 mL bag of saline, inverted 10 times, and sampled at room temperature for 4 hours. After 4 hours the purity was 97.9%. This formulation of the present invention could be used for more than 4 hours at room temperature.
  • the comparative Treanda admixture purity was 95.0% after 4 hours at 25° C.

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US13/048,325 2008-09-25 2011-03-15 Liquid formulations of bendamustine Abandoned US20110190363A1 (en)

Priority Applications (10)

Application Number Priority Date Filing Date Title
US13/048,325 US20110190363A1 (en) 2008-09-25 2011-03-15 Liquid formulations of bendamustine
US13/362,430 US8344006B2 (en) 2008-09-25 2012-01-31 Liquid formulations of bendamustine
US13/655,498 US20130041004A1 (en) 2008-09-25 2012-10-19 Liquid Formulations Of Bendamustine
US14/084,768 US20140080881A1 (en) 2008-09-25 2013-11-20 Liquid Formulations of Bendamustine
US14/151,242 US20140128443A1 (en) 2008-09-25 2014-01-09 Liquid Formulations Of Bendamustine
US14/221,422 US20140206733A1 (en) 2008-09-25 2014-03-21 Liquid Formulations Of Bendamustine
US14/814,570 US20150335750A1 (en) 2008-09-25 2015-07-31 Liquid Formulations of Bendamustine
US15/688,182 US20180125824A1 (en) 2008-09-25 2017-08-28 Liquid formulations of bendamustine
US16/835,562 US20210008035A1 (en) 2008-09-25 2020-03-31 Liquid formulations of bendamustine
US17/015,175 US20210113530A1 (en) 2008-09-25 2020-09-09 Liquid formulations of bendamustine

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US10007408P 2008-09-25 2008-09-25
PCT/US2009/058023 WO2010036702A1 (en) 2008-09-25 2009-09-23 Liquid formulations of bendamustine
US13/048,325 US20110190363A1 (en) 2008-09-25 2011-03-15 Liquid formulations of bendamustine

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US13/048,325 Abandoned US20110190363A1 (en) 2008-09-25 2011-03-15 Liquid formulations of bendamustine
US13/362,430 Active US8344006B2 (en) 2008-09-25 2012-01-31 Liquid formulations of bendamustine
US13/655,498 Abandoned US20130041004A1 (en) 2008-09-25 2012-10-19 Liquid Formulations Of Bendamustine
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