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(12) United States Patent (10) Patent No.: US 7,220,867 B2 Hageman Et Al

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(12) United States Patent (10) Patent No.: US 7,220,867 B2 Hageman Et Al US007220867B2 (12) United States Patent (10) Patent No.: US 7,220,867 B2 Hageman et al. (45) Date of Patent: May 22, 2007 (54) SOLID-STATE FORM OF CELECOXIB 5,892,053 A 4/1999 Zhi et al. HAVING ENHANCED BOAVAILABILITY 6,395,300 B1* 5/2002 Straub et al. ............... 424/489 6,864,373 B2 * 3/2005 Zhuang et al. ........... 548,371.1 (75) Inventors: Michael J. Hageman, Portage, MI 6,964,978 B2 * 1 1/2005 Hageman et al. ........... 514,406 (US); Xiaorong He, Kalamazoo, MI (US); Tugrul T. Kararli, Skokie, IL FOREIGN PATENT DOCUMENTS (US); Lesley A. MacKin, Evanston, IL (US); Patricia J. Miyake, Tower Lakes, WO WOOO,321.89 T 2000 IL (US); Brian R. Rohrs, Scotts, MI WO WOOOf 42021 T 2000 (US); Kevin J. Stefanski, Kalamazoo, MI (US) OTHER PUBLICATIONS (73) Assignee: Pharmacia Corporation (of Pfizer, ed. S. Budavari. The Merck Index, 12th Edition, Therapeutic Inc.), St. Louis, MO (US) Category and Biological Activity Index, (1996), pp. Ther-2 to Ther-3h andd ThTher-12. (*) Notice: Subject to any disclaimer, the term of this Lieberman et al. (1989), Pharmaceutical Dosage Forms: Tablets, patent is extended or adjusted under 35 vol. 1, pp. 34-36. U.S.C. 154(b) by 0 days. k cited. by examiner (21) Appl. No.: 11/189.659 Primary Examiner Golam M. M. Shameem 1-1. (74) Attorney, Agent, or Firm Patricia K. Fitzsimmons; (22) Filed: Jul. 26, 2005 Charles W. Ashbrook (65) Prior Publication Data (57) ABSTRACT US 2005/0267,190 A1 Dec. 1, 2005 O O The selective cyclooxygenase-2 inhibitory drug celecoxib is Related U.S. Application Data provided in amorphous form. Also provided is a celecoxib (60) Division of application No. 09/730,663, filed on Dec. drug substance wherein the celecoxib is present, in at least 6, 2000, now Pat. No. 6,964,978, which is a continu- a detectable amount, as amorphous celecoxib. Also provided ation-in-part of application No. 09/728,040, filed on is a celecoxib-crystallization inhibitor composite comprising Dec. 1, 2000, now abandoned. particles of amorphous celecoxib or a celecoxib drug Sub (60) Provisional9, 1999 application No. 60/169,856, filed on Dec. morestance crysta of S.N.Af 1Zat1On 1nh1 itors,al or exampleNiit. polymers. o Also s provided is a pharmaceutical composition comprising Such (51) Int. Cl a celecoxib-crystallization inhibitor composite and one or cond 23L/10 (2006.01) more excipients. Also provided are processes for preparing (52) U.S. Cl 548/375.1548/356.1: amorphous celecoxib, a celecoxib drug Substance of the Oa - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - 548737 : 548/37 6 invention, a celecoxib-crystallization inhibitor composite of 58) Field of Classification S h 548,356.1 the invention, and a pharmaceutical composition of the (58) Field of Classification ears 4 8373.1. 375.1, 37 6 invention. Also provided is a method of treating a medical S 1 file f 1 . .hh . COnd1t1Onditi Or disorderd1SOrder i1n a Sub1ectb Whereh treatment W1thith a ee application file for complete search history. cyclooxygenase-2 inhibitor is indicated, comprising admin (56) References Cited istering, for example orally, a composition of the invention in a therapeutically effective amount. U.S. PATENT DOCUMENTS 5,466,823. A 11/1995 Talley et al. 6 Claims, 5 Drawing Sheets U.S. Patent May 22, 2007 Sheet 1 of 5 US 7,220,867 B2 4500 4000 35OO 3OOO C1 2500 2000 15OO 1OOO C2 500 5 10 15 20 25 30 35 Degrees 26 Fig. 1 U.S. Patent May 22, 2007 Sheet 2 of 5 US 7,220,867 B2 1250 1 OOO OS 750 Sl CD2 500 E T2 250 T1 O 5 1O 15 20 25 35 Degrees 26 Fig. 2 1000 g 3s 750 e B O O) E 500 T2 250 T1 O 5 10 15 20 25 30 35 Degrees 26 Fig. 3 U.S. Patent May 22, 2007 Sheet 3 of 5 US 7,220,867 B2 50 1OO 150 2OO Temperature (OC) Fig. 4 U.S. Patent May 22, 2007 Sheet 4 of 5 US 7,220,867 B2 1.9 1.8 1.7 1.6 1.5 50 1OO 150 200 Temperature (OC) Fig. 5 U.S. Patent May 22, 2007 Sheet S of 5 US 7,220,867 B2 1.7 1 6 1 5 1.4 50 1OO 150 200 Temperature (°C) Fig. 6 US 7,220,867 B2 1. 2 SOLD-STATE FORM OF CELECOXB However, celecoxib presents certain challenges for for HAVING ENHANCED BOAVAILABILITY mulation as a rapid-onset dosage form, particularly as a rapid-onset oral dosage form. For example, celecoxib has This application is a divisional application of U.S. patent very low solubility in aqueous media and therefore is not application Ser. No. 09/730,663 filed on Dec. 6, 2000, now 5 readily dissolved and dispersed for rapid absorption in the U.S. Pat. No. 6,964,978, which is a continuation-in-part of gastrointestinal tract when administered orally, for example U.S. patent application Ser. No. 09/728,040, now abandoned in tablet or capsule form. In addition, celecoxib has a filed on Dec. 1, 2000, and also claims priority of U.S. relatively high dose requirement further increasing difficul provisional application Ser. No. 60/169,856 filed on Dec. 9, ties of providing a sufficient therapeutically effective dose 1999. 10 for rapid absorption. Celecoxib crystals also present formulation difficulties as FIELD OF THE INVENTION a result of unique physical and chemical characteristics or mechanical properties such as electrostatic and cohesive The present invention relates to the selective cyclooxy properties, low bulk density, low compressibility and poor genase-2 inhibitory drug celecoxib and in particular to 15 flow properties. Due at least in part to these properties, Solid-state forms of that drug, to pharmaceutical composi celecoxib crystals tend to segregate and agglomerate tions comprising Such solid-state forms, and to processes for together during mixing, resulting in a non-uniformly preparing them. The invention further relates to methods of blended composition containing undesirably large, insoluble treatment of cyclooxygenase-2 mediated disorders compris aggregates of celecoxib. For these and other reasons, there ing administering Such solid-state forms or compositions fore, it is difficult to prepare an orally deliverable, rapid thereof to a Subject, and to use of Such solid-state forms in onset composition containing celecoxib that has the desired the manufacture of medicaments. blend uniformity. The bioavailability of an orally administered drug, as BACKGROUND OF THE INVENTION measured by its entry into Systemic circulation in the blood 25 stream, depends on at least two fundamental processes: drug Celecoxib, also known as 4-5-(4-methylphenyl)-3-(trif dissolution in gastrointestinal fluids (in vivo drug release) luoromethyl)-1H-pyrazol-1-ylbenzenesulfonamide (I), the and Subsequent absorption of the dissolved drug. Several active ingredient of Celebrex(R) marketed by Pharmacia factors influence dissolution of a drug from its carrier, Corp., has a therapeutically and prophylactically useful including Surface area of the drug presented to the dissolu selective cyclooxygenase-2 inhibitory effect, and has utility 30 tion solvent medium, solubility of the drug substance in the in treatment and prevention of specific cyclooxygenase-2 Solvent medium, and driving forces of the Saturation con mediated disorders and of Such disorders in general. Cele centration of dissolved materials in the solvent medium. coxib has the structure: When the process of in vivo drug release is slower than the process of absorption, absorption is said to be dissolution 35 rate-limited. Since dissolution precedes absorption in the O (I) overall process, any change in the drug release or dissolution process will Subsequently influence drug absorption. See for H.N/ example Lieberman et al. (1989), Pharmaceutical Dosage / 40 Forms: Tablets, Vol. 1, pp. 34–36. Marcel Dekker, New -N York. It is clear, therefore, that dissolution time determined N N CF for a composition is one of the important fundamental characteristics for consideration when evaluating composi S. tions intended for fast-onset delivery, particularly where 45 drug absorption is dissolution rate-limited. Crystalline Solids, due to their highly organized, lattice H3C like structures, typically require a significant amount of energy for dissolution. The energy required for a drug Processes for preparing celecoxib are set forth in U.S. Pat. molecule to escape from a crystal, for example, is greater No. 5,466,823 to Talley et al. and in U.S. Pat. No. 5,892,053 50 than is required for the same drug molecule to escape from to Zhi & Newaz, both incorporated herein by reference. a non-crystalline, amorphous form. Importantly, however, Co-assigned International Patent Publication No. WO crystalline drug forms which have been transformed into 00/32189, incorporated herein by reference, discloses that amorphous forms tend to revert to a steady state of low celecoxib has a crystal morphology which tends to form energy, namely the crystalline form, over time and thus may long, cohesive needles. Co-assigned International Patent 55 not have an adequate shelf life. An amorphous form of Publication No. WO 00/42021, incorporated herein by ref celecoxib has not hitherto been known in the art. erence, discloses a solvated crystalline form of celecoxib As indicated hereinbelow, treatment with celecoxib is and a method for desolvation of that crystalline form. indicated in a very wide array of cyclooxygenase-2 mediated A need for new forms of celecoxib, in particular forms conditions and disorders. Therefore, if an amorphous form Suitable for preparing rapid-onset compositions, exists. 60 of celecoxib could be prepared, and in particular if a Rapid-onset drug-delivery systems can provide significant storage-stable composition comprising Such an amorphous benefits over conventional dosage forms.
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