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(12) Patent Application Publication (10) Pub. No.: US 2010/0297252 A1 Cooper Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2010/0297252 A1 Cooper Et Al US 2010O297252A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2010/0297252 A1 Cooper et al. (43) Pub. Date: Nov. 25, 2010 (54) NANOPARTICULATE MELOXICAM Related U.S. Application Data FORMULATIONS (63) Continuation-in-part of application No. 10/784,900, (75) Inventors: Eugene R. Cooper, Berwyn, PA filed on Feb. 24, 2004. (US); Tuula Ryde, Malvern, PA (60) Provisional application No. 60/450,705, filed on Mar. (US); John Pruitt, Suwansee, GA 3, 2003. PA(US); (US) Laura Kline, Harleysville, PublicationO O Classification (51) Int. Cl. Correspondence Address: A6IR 9/14 (2006.01) Elan Drug Delivery, Inc. c/o Foley & Lardner A6II 3/545 (2006.01) 3000 K Street, N.W., Suite 500 A6IP 29/00 (2006.01) Washington, DC 20007-5109 (US) C07D 417/12 (2006.01) (52) U.S. Cl. ......... 424/501: 514/226.5; 544/49;977/773 (73) Assignee: Elan Pharma International Ltd. (57) ABSTRACT 21) Appl. NTNO. 12/7882O39 Thee ppresent 1nVent1Onion 1Sis didirected d to nanopart1Culateparticul COmop sitions comprising meloxicam particles having an effective (22) Filed: May 26, 2010 average particle size of less than about 2000 nm. Patent Application Publication Nov. 25, 2010 Sheet 1 of 5 US 2010/0297252A1 < O5 Oa. Z Q r. O O d w \ \, \ \ \\ cy O o N O d VN cy g CC C s CNd U O N. Y. - o ve O d lo -- t - -- t O O O O O O O O O O O O O O D cy cy CN CN ve ve (uo) ZIS 3 OIL&Wo Patent Application Publication Nov. 25, 2010 Sheet 2 of 5 US 2010/0297252A1 s d O C d O O O O O O O cy CN CN ve- ve (uo) 3ZIS 31OIL&W US 2010/0297252 A1 Nov. 25, 2010 NANOPARTICULATE MELOXCAM Iododipamide Derivatives for Use as X-Ray Contrast FORMULATIONS Agents: 5,525,328 for “Nanoparticulate Diagnostic Diatri Zoxy Ester X-Ray Contrast Agents for Blood Pool and Lym CROSS-REFERENCE TO RELATED phatic System Imaging: 5,543,133 for “Process of Preparing APPLICATIONS X-Ray Contrast Compositions Containing Nanoparticles: 0001. This application is a continuation-in-part of U.S. 5,552,160 for “Surface Modified NSAID Nanoparticles;” patent application Ser. No. 10/784,900, filed Feb. 24, 2004, 5,560.931 for “Formulations of Compounds as Nanoparticu which claims priority to U.S. Provisional Patent Application late Dispersions in Digestible Oils or Fatty Acids: 5,565,188 No. 60/450,705, filed Mar. 3, 2003. The contents of these for “Polyalkylene Block Copolymers as Surface Modifiers applications are incorporated herein by reference in their for Nanoparticles: 5,569,448 for “Sulfated Non-ionic Block entirety. Copolymer Surfactant as Stabilizer Coatings for Nanopar ticle Compositions: 5,571.536 for “Formulations of Com BACKGROUND OF THE INVENTION pounds as Nanoparticulate Dispersions in Digestible Oils or Fatty Acids: 5,573,749 for “Nanoparticulate Diagnostic 0002 Nanoparticulate active agent compositions are Mixed Carboxylic Anydrides as X-Ray Contrast Agents for described in U.S. Pat. No. 5,145,684 (“the 684 patent”) as Blood Pool and Lymphatic System Imaging: 5,573,750 for particles comprising a poorly soluble therapeutic or diagnos “Diagnostic Imaging X-Ray Contrast Agents: 5,573,783 for tic agent having adsorbed onto or associated with the Surface “Redispersible Nanoparticulate Film Matrices With Protec thereof a non-crosslinked surface stabilizer. tive Overcoats: 5,580,579 for “Site-specific Adhesion 0003 Methods of making nanoparticulate active agent Within the GI Tract Using Nanoparticles Stabilized by High compositions are described in, for example, U.S. Pat. Nos. Molecular Weight, Linear Poly(ethylene Oxide) Polymers: 5,518,187 and 5,862.999, both for “Method of Grinding Phar 5,585,108 for “Formulations of Oral Gastrointestinal Thera maceutical Substances: U.S. Pat. No. 5,718,388, for “Con peutic Agents in Combination with Pharmaceutically Accept tinuous Method of Grinding Pharmaceutical Substances: able Clays: 5,587,143 for “Butylene Oxide-Ethylene Oxide and U.S. Pat. No. 5,510,118 for “Process of Preparing Thera Block Copolymers Surfactants as Stabilizer Coatings for peutic Compositions Containing Nanoparticles. Nanoparticulate Compositions: 5,591,456 for “Milled 0004 Nanoparticulate active agent compositions are also Naproxen with Hydroxypropyl Cellulose as Dispersion Sta described, for example, in U.S. Pat. Nos. 5.298,262 for “Use bilizer: 5,593,657 for “Novel Barium Salt Formulations Sta of Ionic Cloud Point Modifiers to Prevent Particle Aggrega bilized by Non-ionic and Anionic Stabilizers;”5,622,938 for tion During Sterilization: 5,302.401 for “Method to Reduce "Sugar Based Surfactant for Nanocrystals: 5,628,981 for Particle Size Growth During Lyophilization: 5,318,767 for “Improved Formulations of Oral Gastrointestinal Diagnostic “X-Ray Contrast Compositions Useful in Medical Imaging: X-Ray Contrast Agents and Oral Gastrointestinal Therapeu 5,326,552 for “Novel Formulation For Nanoparticulate tic Agents: 5,643,552 for “Nanoparticulate Diagnostic X-Ray Blood Pool Contrast Agents Using High Molecular Mixed Carbonic Anhydrides as X-Ray Contrast Agents for Weight Non-ionic Surfactants: 5,328,404 for “Method of Blood Pool and Lymphatic System Imaging; 5,718.388 for X-Ray Imaging Using Iodinated Aromatic Propanedioates: “Continuous Method of Grinding Pharmaceutical Sub 5,336,507 for “Use of Charged Phospholipids to Reduce stances; 5,718,919 for “Nanoparticles Containing the R(-) Nanoparticle Aggregation: 5,340,564 for “Formulations Enantiomer of Ibuprofen; 5,747,001 for Aerosols Contain Comprising Olin 10-G to Prevent Particle Aggregation and ing Beclomethasone Nanoparticle Dispersions; 5,834,025 Increase Stability: 5,346,702 for “Use of Non-Ionic Cloud for “Reduction of Intravenously Administered Nanoparticu Point Modifiers to Minimize Nanoparticulate Aggregation late Formulation Induced Adverse Physiological Reactions: During Sterilization: 5,349,957 for “Preparation and Mag 6,045,829 “Nanocrystalline Formulations of Human Immu netic Properties of Very Small Magnetic-Dextran Particles: nodeficiency Virus (HIV) Protease Inhibitors. Using Cellulo 5,352,459 for “Use of Purified Surface Modifiers to Prevent sic Surface Stabilizers;” 6,068,858 for “Methods of Making Particle Aggregation During Sterilization: 5,399,363 and Nanocrystalline Formulations of Human Immunodeficiency 5,494,683, both for "Surface Modified Anticancer Nanopar Virus (HIV) Protease Inhibitors Using Cellulosic Surface ticles; 5.401,492 for “Water Insoluble Non-Magnetic Man Stabilizers: 6,153,225 for “Injectable Formulations of ganese Particles as Magnetic Resonance Enhancement Nanoparticulate Naproxen; 6,165,506 for “New Solid Dose Agents: 5,429,824 for “Use of Tyloxapol as a Nanoparticu Form of Nanoparticulate Naproxen; 6,221,400 for “Meth late Stabilizer:”5,447,710 for “Method for Making Nanopar ods of Treating Mammals Using Nanocrystalline Formula ticulate X-Ray Blood Pool Contrast Agents Using High tions of Human Immunodeficiency Virus (HIV) Protease Molecular Weight Non-ionic Surfactants; 5.451,393 for Inhibitors: 6,264,922 for “Nebulized Aerosols Containing “X-Ray Contrast Compositions Useful in Medical Imaging: Nanoparticle Dispersions:” 6,267,989 for “Methods for Pre 5,466,440 for “Formulations of Oral Gastrointestinal Diag venting Crystal Growth and Particle Aggregation in Nanopar nostic X-Ray Contrast Agents in Combination with Pharma ticle Compositions: 6,270.806 for “Use of PEG-Derivatized ceutically Acceptable Clays:”5,470,583 for “Method of Pre Lipids as Surface Stabilizers for Nanoparticulate Composi paring Nanoparticle Compositions Containing Charged tions: 6,316,029 for “Rapidly Disintegrating Solid Oral Phospholipids to Reduce Aggregation: 5,472,683 for Dosage Form.” 6,375,986 for “Solid Dose Nanoparticulate “Nanoparticulate Diagnostic Mixed Carbamic Anhydrides as Compositions Comprising a Synergistic Combination of a X-Ray Contrast Agents for Blood Pool and Lymphatic Sys Polymeric Surface Stabilizer and Dioctyl Sodium Sulfosuc tem. Imaging: 5,500.204 for “Nanoparticulate Diagnostic cinate; 6,428,814 for “Bioadhesive Nanoparticulate Com Dimers as X-Ray Contrast Agents for Blood Pool and Lym positions Having Cationic Surface Stabilizers; 6,431,478 for phatic System Imaging: 5,518,738 for “Nanoparticulate “Small Scale Mill:” 6,432,381 for “Methods for Targeting NSAID Formulations: 5,521,218 for “Nanoparticulate Drug Delivery to the Upper and/or Lower Gastrointestinal US 2010/0297252 A1 Nov. 25, 2010 Tract. 6,592.903 for “Nanoparticulate Dispersions Compris et al., Brit. J. Rheumatol. 37:937 (1998), and Dequekeret al., ing a Synergistic Combination of a Polymeric Surface Stabi Brit. J. Rheumatol. 37:946 (1998). lizer and Dioctyl Sodium Sulfosuccinate. 6,582.285 for 0008 Meloxicam exhibits anti-inflammatory, analgesic, Apparatus for sanitary wet milling; 6,656,504 for “Nano and antifebrile activities. Like other NSAIDs, the primary particulate Compositions Comprising Amorphous Cyclospo mechanism of action of meloxicam is via inhibition of the rine;” 6,742,734 for “System and Method for Milling Mate cyclooxygenase (COX-2) enzyme system resulting in rials: 6,745,962 for “Small ScaleMill and Method Thereof.” decreased prostaglandin synthesis. See The Physicians’ Desk 6,811,767 for “Liquid droplet aerosols of nanoparticulate Reference, 56th Ed., pp. 1054 (2002). In contrast, COX-2 is drugs; 6,908,626 for “Compositions having a combination not present in healthy tissue and its expression is induced in of immediate release and controlled release characteristics: certain inflammatory states. See Vane et al., Proc. Natl. Acad. 6,969,529 for “Nanoparticulate compositions comprising Sci. USA,
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