WO2007123955A2 - Stable hydroalcoholic oral spray formulations and methods - Google Patents

Stable hydroalcoholic oral spray formulations and methods Download PDF

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Publication number
WO2007123955A2
WO2007123955A2 PCT/US2007/009496 US2007009496W WO2007123955A2 WO 2007123955 A2 WO2007123955 A2 WO 2007123955A2 US 2007009496 W US2007009496 W US 2007009496W WO 2007123955 A2 WO2007123955 A2 WO 2007123955A2
Authority
WO
WIPO (PCT)
Prior art keywords
composition
meloxicam
spray
formulations
group
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/US2007/009496
Other languages
English (en)
French (fr)
Other versions
WO2007123955A3 (en
Inventor
Frank E. Blondino
Howard Malitz
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.)
Flemington Pharmaceutical Corp
Original Assignee
Flemington Pharmaceutical Corp
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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=38625570&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=WO2007123955(A2) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Flemington Pharmaceutical Corp filed Critical Flemington Pharmaceutical Corp
Priority to CA2649895A priority Critical patent/CA2649895C/en
Priority to JP2009506564A priority patent/JP2009534387A/ja
Priority to EP07755674.4A priority patent/EP2015632B1/en
Publication of WO2007123955A2 publication Critical patent/WO2007123955A2/en
Publication of WO2007123955A3 publication Critical patent/WO2007123955A3/en
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
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
    • A61K9/006—Oral mucosa, e.g. mucoadhesive forms, sublingual droplets; Buccal patches or films; Buccal sprays
    • 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
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • 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
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
    • A61K31/404—Indoles, e.g. pindolol
    • A61K31/405—Indole-alkanecarboxylic acids; Derivatives thereof, e.g. tryptophan, indomethacin
    • 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
    • A61K31/415—1,2-Diazoles
    • 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
    • A61K31/54—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 sulfur as the ring hetero atoms, e.g. sulthiame
    • A61K31/5415—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 sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with carbocyclic ring systems, e.g. phenothiazine, chlorpromazine, piroxicam
    • 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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • A61K38/22—Hormones
    • A61K38/28—Insulins
    • 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
    • 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
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • 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
    • A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Definitions

  • the field of the this invention is hydroalcoholic oral spray pharmaceutical
  • Metabolism by the liver may also decrease the available dosage. Metabolism by the liver may also decrease the available dosage. Metabolism by the liver may also decrease the available dosage. Metabolism by the liver may also decrease the available dosage. Metabolism by the liver may also decrease the available dosage. Metabolism by the liver may also decrease the available dosage. Metabolism by the liver may also decrease the available dosage. Metabolism by the liver may also decrease the available dosage. Metabolism by the liver may also be performed by the liver.
  • spray formulations must produce spray patterns of a suitable ovality and particle
  • oral spray compositions comprising an active pharmaceutical agent, a solvent, and a
  • viscosity modifying agent wherein when a unit dose volume of about 25 to 400 mcL
  • the spray has a median particle size
  • the invention provides stable, hydroalcoholic oral spray
  • hydroalcoholic 1%, and most preferably about 0.47% w/w.
  • meloxicam formulation embodiment comprises meloxicam, boric acid, potassium
  • Another embodiment of the invention provides a pharmaceutical
  • composition comprising about 0.1 to 2% w/w of meloxicam, about 1 to 10 mg/g
  • Additional embodiments of the invention provide methods of treating
  • composition according to the invention Preferred embodiments administer a spray
  • the spray volume is about 100 mcL to the oral mucosa. In another embodiment the spray volume is
  • the volume of spray preferably contains a dose of meloxicam in the
  • Preferred embodiments of the present invention provide hydroalcoholic
  • oral spray compositions comprising an active pharmaceutical agent, a solvent, and a
  • viscosity modifying agent wherein when a unit dose volume of about 25 to 400 mcl
  • the spray has a median particle size
  • compositions which are hydroalcoholic
  • solutions comprising a therapeutically effective amount of meloxicam.
  • compositions do not resort to use of a preservative, but instead achieve inhibition of microbial growth by including an alcohol, preferably at least about 10%
  • meloxicam is defined as 4-hydroxy-2-methyl-N-(5-Methyl-l / 3-thiazol-2-
  • embodiments of the invention relate to meloxicam, additional or other active
  • compositions can be used in the spray delivery vehicles and methods of the
  • formulations according to the invention may also contain additional ingredients
  • meloxicam such as, for example, analgesics, non-steroidal anti-inflammatory drugs
  • inflammatory drugs such as alosetron, anakinra, beclomethasone, betamethasone,
  • budesonide celecoxib, clobetasol, cromolyn, desoximetasone, dexamethasone,
  • methotrexate methotrexate, methylprednisolone, mometasone, montelukast, nedocromil,
  • terbutaline triamcinolone, valdecoxib, zafirlukast, including salts and mixtures thereof can also be included as active pharmaceutical agents in formulations of the
  • Celecoxib is a highly selective COX-2 inhibitor which is more selective for
  • Celecoxib can reduce inflammation and pain while
  • invention may contain celecoxib.
  • methods of co ⁇ may contain celecoxib.
  • formulations of the invention include analgesics such as
  • NSAIDS such as aspirin, diclofenac, etodolac, ibuprofen,
  • sulindac including salts thereof; corticosteroids such as betamethasone,
  • opioids such as codeine, hydrocodone, hydromorphone,
  • formulations of the invention include, but are not limited to, ondansetron,
  • meloxicam is believed to be due to the evaporation of alcohol.
  • storage stability is determined at a temperature range from about
  • storage stability is determined at a relative humidity (“RH”) range
  • Preferred time intervals for measuring storage stability range from
  • Preferred formulations of the invention contain about 15% ethanol and
  • a viscosity modifying (or enhancing) agent such as polyvinyl alcohol.
  • parabens for example, butylparaben, methylparaben
  • phenol for example, phenoxyethanol
  • phenylethyl alcohol and propylene glycol, may be used in place of ethanol for this
  • a preferred antimicrobial agent is sodium benzoate.
  • buffers include
  • ammonium hydroxide carbonate, citrate, glycine, maleate, and phosphate
  • Preferred embodiments of the invention are directed to buccal spray
  • formulations of the invention maximize absorption to the systemic circulatory
  • the size of the spray particles contributes to whether the particle
  • the percentage of the particles (droplets) of the spray is the percentage of the particles (droplets) of the spray
  • formulation e.g., after actuation of a spray pump having a diameter of less than ten
  • microns is less than about 10%, more preferably less than about 5%.
  • the median diameter of the spray particles is from about 20 microns to
  • microns e.g., Tables 4 and 5
  • the ovality of the spray pattern indicates whether the spray is
  • a hydroalcoholic solution preferably, water, borate buffer, and
  • solvents e.g., ammonium hydroxide buffer, carbonate, citrate, glycine, maleate, and phosphate, including salts thereof
  • solvents e.g., ammonium hydroxide buffer, carbonate, citrate, glycine, maleate, and phosphate, including salts thereof
  • colloidal silicon dioxide ethylcellulose, gelatin, guar gum, hydroxyethyl cellulose,
  • formulations also may contain an optional propellant for delivery as
  • Suitable propellants include, but are not limited to, hydrocarbons (butane, propane, etc.) / chlorofluorocarbons (CFC-Il, CFC-12, etc.), hydrofluorocarbons
  • Optional sweetening, taste masking, or flavoring agents such as
  • Examples include beef, bubble gum, chicken, fish, fruit,
  • formulations of the present invention can be prepared by various combinations
  • meloxicam is dissolved in a strongly alkaline solution to achieve dissolution at the
  • amber glass can be utilized but may not be
  • the bottle may be opaque to
  • the product is preferably dispensed using a
  • metered pump device capable of delivering between 25 and 400 mcL.
  • the actuator may include an extension to allow for delivery to the buccal
  • the present invention also provides methods of treating various aspects of
  • osteoarthritis e.g., osteoarthritis, rheumatoid arthritis, inflammation, gout,
  • the methods include administering to a subject in need of treatment a
  • subject is a human; in another embodiment the subject is a non-human mammal,
  • the preferred storage stable meloxicam compositions can be administered to a
  • the impurity appeared at a concentration 0.1% at
  • the initial Meloxicam concentration in Formula 2 was 95.0%.
  • the concentration of Impurity B was less than 0.1% through 8 weeks.
  • concentration of Impurity B was 0.2% at 12 weeks and 0.5% at 4 months. The level
  • Impurity B was 0.1% at 12 weeks and 0.4% at 4 months.
  • the concentration of Impurity B was 0.1% at 12 weeks and 0.4% at 4 months. The concentration of
  • Impurity B is Formula 3 was lower than that observed for Formulas 1 and 2.
  • Impurity A was less than 0.05% through 2 months.
  • Impurity B is Formula 4 was lower than that observed for Formulas 1, 2, and 3.
  • Formula 5 has a concentration of 0.5%
  • PVA and Formula 6 has a concentration of 0.25% PVA.
  • concentration 0.25% PVA.
  • than 10 ⁇ m may indicate the percentage of the particles at risk of being inhaled into
  • the amount of particles less than 10 ⁇ m is 1.6% for the
  • the Dv (50) and Dv (90) values are size values corresponding to the

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Rheumatology (AREA)
  • Immunology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Diabetes (AREA)
  • Endocrinology (AREA)
  • Zoology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Pain & Pain Management (AREA)
  • Physiology (AREA)
  • Emergency Medicine (AREA)
  • Nutrition Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Molecular Biology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
PCT/US2007/009496 2006-04-19 2007-04-19 Stable hydroalcoholic oral spray formulations and methods Ceased WO2007123955A2 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
CA2649895A CA2649895C (en) 2006-04-19 2007-04-19 Stable hydroalcoholic oral spray formulations and methods
JP2009506564A JP2009534387A (ja) 2006-04-19 2007-04-19 安定な含水アルコール性経口噴霧調剤物および方法
EP07755674.4A EP2015632B1 (en) 2006-04-19 2007-04-19 Stable hydroalcoholic oral spray formulations and methods

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US79294206P 2006-04-19 2006-04-19
US60/792,942 2006-04-19

Publications (2)

Publication Number Publication Date
WO2007123955A2 true WO2007123955A2 (en) 2007-11-01
WO2007123955A3 WO2007123955A3 (en) 2008-10-09

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PCT/US2007/009496 Ceased WO2007123955A2 (en) 2006-04-19 2007-04-19 Stable hydroalcoholic oral spray formulations and methods

Country Status (5)

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US (2) US20070248548A1 (enExample)
EP (1) EP2015632B1 (enExample)
JP (2) JP2009534387A (enExample)
CA (1) CA2649895C (enExample)
WO (1) WO2007123955A2 (enExample)

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US7872049B2 (en) 2008-03-14 2011-01-18 G. Pohl-Boskamp Gmbh & Co. Kg Long-term stable pharmaceutical preparation containing the active ingredient glyceryl trinitrate
EP2124897A4 (en) * 2006-12-22 2012-05-09 Novadel Pharma Inc SPRAYING, ORAL, STABLE, SPRAY PREPARATIONS AND ASSOCIATED METHODS
WO2013053015A1 (en) * 2011-10-14 2013-04-18 Troy Laboratories Pty Limited Meloxicam based formulations for providing analgesia in sheep
WO2014108657A1 (fr) 2013-01-14 2014-07-17 ROSSELLO, Raphaël Forme galenique pour l'administration d'un principe actif
US9101592B2 (en) 2011-02-25 2015-08-11 G. Pohl-Boskamp Gmbh & Co. Kg Stabilized granules containing glyceryl trinitrate
US9180109B2 (en) 2010-08-03 2015-11-10 G. Pohl-Boskamp Gmbh & Co. Kg Use of glyceryl trinitrate for treating traumatic edema
EP2015632B1 (en) 2006-04-19 2015-12-02 Mist Pharmaceuticals, LLC Stable hydroalcoholic oral spray formulations and methods
US9248099B2 (en) 2012-05-31 2016-02-02 Desmoid Aktiengesellschaft Use of stabilized granules containing glyceryl trinitrate for arteriogenesis
US10034850B2 (en) 2013-11-29 2018-07-31 G. Pohl-Boskamp Gmbh & Co. Kg Sprayable aqueous composition comprising glyceryl trinitrate
WO2020075183A1 (en) 2018-10-08 2020-04-16 Troikaa Pharmaceuticals Limited Oromucosal solutions of zolpidem or pharmaceutically acceptable salts thereof
US11166931B2 (en) 2012-05-31 2021-11-09 G. Pohl-Boskamp Gmbh & Co. Kg Induction of arteriogenesis with an NO (nitric oxide) donor
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US20070248548A1 (en) 2007-10-25
JP2013177469A (ja) 2013-09-09
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EP2015632A2 (en) 2009-01-21
EP2015632A4 (en) 2011-03-23
CA2649895C (en) 2013-03-26
US20110280916A1 (en) 2011-11-17
CA2649895A1 (en) 2007-11-01
WO2007123955A3 (en) 2008-10-09

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