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US 2011 0033545A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2011/0033545 A1 Wang (43) Pub. Date: Feb. 10, 2011 (54) TOPCAL PHARMACEUTICAL Publication Classification PREPARATIONS HAVING BOTH A NANOPARTICLE SOLUTION ANDA (51) Int. Cl. NANOPARTICLE SUSPENSION AND A6II 3/545 (2006.01) METHODS FOR THE TREATMENT OF A6IR 9/14 (2006.01) ACUTE AND CHRONIC PANTHEREWITH A63L/92 (2006.01) A 6LX 3L/97 (2006.01) (75) Inventor: Changjin Wang, San Diego, CA A6IP 29/00 (2006.01) (US) A6IP 23/02 (2006.01) Correspondence Address: (52) U.S. Cl. ...................... 424/489: 514/226.5: 514/570; FOLEY & LARDNER LLP 514/567 975 PAGE MILL ROAD Palo Alto, CA 94304 (US) (57) ABSTRACT (73) Assignee: ABsize, Inc., Osaka (JP) This invention relates to topical pharmaceutical preparations (21) Appl. No.: 12/844,369 and methods for the treatment of acute and chronic pain and inflammation therewith. The preparations have a saturated (22) Filed: Jul. 27, 2010 Solution of an active pharmaceutical ingredient in a solvent therefor in intimate combination and contact with a Suspen Related U.S. Application Data sion of nanoparticles of the active pharmaceutical ingredient (60) Provisional application No. 61/273,473, filed on Aug. in the solvent, and a pharmaceutically acceptable carrier 6, 2009. therefor, and are administered topically. US 2011/0033545 A1 Feb. 10, 2011 TOPCAL PHARMACEUTICAL will result in better clinical efficacy and reduced side effects, PREPARATIONS HAVING BOTH A which allow for longer-term treatment than current therapies. NANOPARTICLE SOLUTION ANDA NANOPARTICLE SUSPENSION AND SUMMARY OF THE INVENTION METHODS FOR THE TREATMENT OF ACUTE AND CHRONIC PANTHEREWITH 0006. This invention relates to pharmaceutical prepara tions as well as to methods for the treatment of acute and chronic pain and inflammation, and their related symptoms. CROSS-REFERENCE TO RELATED 0007. In one embodiment, this invention relates to phar APPLICATION maceutical preparations comprising a therapeutically effec tive amount of a nanosized non-steroidal anti-inflammatory 0001. This application claims the benefit under 35 U.S.C. drug, and a pharmaceutically acceptable carrier therefor Suit S119(e) of U.S. Provisional Patent Application Ser. No. able for topical administration. The preparations are admin 61/273.473 filed Aug. 6, 2009 which application is incorpo istered topically for the treatment of acute and chronic pain rated herein by reference in its entirety. and inflammation, and their related symptoms. 0008. In another embodiment, the pharmaceutical prepa FIELD OF THE PRESENT INVENTION rations of this invention further comprise an effective amount of a local anesthetic. 0002 This invention relates to topical pharmaceutical 0009. The non-steroidal anti-inflammatory drug is nano preparations. This invention also relates to methods for the sized to nanoparticles of less than 1000 nm, predominately in treatment of acute and chronic pain and inflammation there the range of 200-500 nm or 1-200 nm, preferably 10-100 nm. with. The preparations of this invention have a saturated or 50-100 nm, and most preferably having a mean particle Solution of an active pharmaceutical ingredient in a solvent size of about 40-60 nm (as measured along it longest axis). It therefor in intimate combination and contact with a suspen should be understood that the non-steroidal anti-inflamma sion of nanoparticles of the active pharmaceutical ingredient tory drug is itself nanosized, as opposed to where the medici in the solvent, and a pharmaceutically acceptable carrier nal ingredient is absorbed onto an inert nanosized carrier. therefor suitable for topical administration. 0010. The preparations of this invention are useful in the treatment of acute and/or chronic pain as a result of inflam BACKGROUND OF THE PRESENT INVENTION mation associated with, for example, rheumatoid arthritis, osteoarthritis, inflammatory arthropathies, gout and pseudo 0003. The art is replete with the ways of preparing topical gout, dysmenorrhea, metastatic bone pain, headache and pharmaceutical preparations as well as with dealing with pain migraine, postoperative pain, post-herpetic neuralgia, neuro and inflammation, both in humans and animals. The medical pathic pains, Soft-tissue injuries, strains, sprains, contusions, literature and patents around the world describe many ways in tendonitis or bursitis of the shoulder, elbow, wrist or knee, which these conditions can be treated, with greater or lesser Carpal tunnel syndrome, lateral epicondylosis, lower back Success in any given situation. More recently, many research pains and injury, and the like. It is understood that this inven ers have focused on using Small particles of the active phar tion is not directed to novel non-steroidal anti-inflammatory maceutical ingredient in hope of achieving better clinical agents. Rather, this invention is directed to use of known Success with the enhanced administration that the Smaller, so agents that are being nanosized so as to improve their efficacy called nanoparticles, of the active pharmaceutical ingredient for topical administration. It is also understood that this afford. invention is not treating the diseases referenced above but, 0004 For example, US published application No. 2008/ rather, are treating the inflammation and pain associated 0237376 assigned to ABsize Inc. describes a technique for therewith. creating nanoparticles of an active pharmaceutical ingredient with a laser beam. Related published applications assigned to DETAILED DESCRIPTION OF SPECIFIC ABsize are US published applications 20070284769 and EMBODIMENTS OF THE PRESENT 20080217445. Other laser beam nanosizing techniques are INVENTION shown by Kawakami et al. in US published applications 0011. In one embodiment of this invention, the pharma 20060257489, 20070114306 and 20070152360. However, ceutical preparations comprise a therapeutically effective while these publications describe various techniques for cre amount of nanosized particles of a Solid medicament and, in ating nanoparticles, and using them, for example, in prepar particular, a non-steroidal anti-inflammatory drug selected ing injectable agents, they do not describe topical prepara from the group consisting of aceclofenac, alminoprofen, apa tions or how topical preparations can be effectively utilized in Zone, aspirin, benoxaprofen, butibufen, carprofen, dexketo the treatment of acute pain and inflammation. profen, diclofenac, difenpiramide, diflunisal, droxicam, 0005. It is, therefore, an object of the present invention to enbufen, etodolac, fenoprofen, flufenamic acid, flurbiprofen, provide pharmaceutical preparations that are topically ibuprofen, indomethacin, indoprofen, ketoprofen, ketorolac, applied as well as to provide methods for the treatment of lornoxicam, meclofenamic acid, mefenamic acid, meloxi acute and chronic pain and inflammation therewith that have cam, nabumetone, naproxen, oxaprozin, phenylbutaZone, higher concentrations of the active pharmaceutical ingredi piroXicam, pirprofen, pranoprofen, Salicylic acid, Sulindac, ent. It is contemplated that the pharmaceutical preparations of Suprofen, tenoxicam, tiaprofenic acid, and tolmetin, and the this invention will allow lower dosages of the active agent to pharmaceutically acceptable salts, and esters thereof, and a be used in comparison with the doses normally administered pharmaceutically acceptable carrier therefor suitable for topi systemically to achieve efficacious results. It is further con cal administration. The preferred class of the non-steroidal templated that the use of lower dosages of the active agent anti-inflammatory drugs is the oxicam class of NSAIDs. The US 2011/0033545 A1 Feb. 10, 2011 presently preferred non-steroidal anti-inflammatory drugs 0016. With regard to the non-steroidal anti-inflammatory are diclofenac, ketoprofen, ketorolac, and piroxicam, with the drugs listed above, this invention contemplates using about presently preferred non-steroidal anti-inflammatory drug 20 mg to about 2,000 mg/day of aceclofenac, preferably being piroXicam. about 200 mg to about 1,000 mg/day, with a specific dose of 0012. In another embodiment of the present invention, the about 600 mg/day; about 9 mg to about 900 mg/day of almi pharmaceutical preparations have a therapeutically effective noprofen, preferably about 90 mg to about 450 mg/day, with amount of nanosized particles of a non-steroidal anti-inflam a specific dose of about 270 mg/day; about 30 mg to about matory drug as set forth above in combination with a local 3,000 mg/day of apaZone, preferably about 300 mg to about anesthetic selected from the group consisting of articaine, 1,500 mg/day, with a specific dose of about 900 mg/day; benzocaine, bupivacaine, dibucaine, etidocaine, levobupiv about 400 mg to about 40,000 mg/day of aspirin, preferably acaine, lidocaine, mepivacaine, piperocaine, prilocaine, ropi about 4,000 mg to about 20,000 mg/day, with a specific dose vacaine, tetracaine, and trimecaine. The presently preferred of about 12,000 mg/day; about 60 mg to about 6,000 mg/day local anesthetics are bupivacaine, lidocaine, prilocaine, and of benoxaprofen, preferably about 600 mg to about 3,000 tetracaine, with the presently preferred local anesthetic being mg/day, with a specific dose of about 1,800 mg/day; about lidocaine. 300 mg to about 30,000 mg/day of butibufen, preferably 0013 The nanoparticles of the non-steroidal anti-inflam about 3,000 mg to about 15,000 mg/day, with a specific dose matory drug can be
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  • (12) United States Patent (10) Patent No.: US 6,183,779 B1 10 11 12

    (12) United States Patent (10) Patent No.: US 6,183,779 B1 10 11 12

    USOO6183779B1 (12) United States Patent (10) Patent No.: US 6,183,779 B1 Ouali et al. (45) Date of Patent: Feb. 6, 2001 (54) STABILIZED PHARMACEUTICAL 5,698,225 12/1997 Gimet et al. ......................... 424/475 COMPOSITION OF ANONSTEROIDAL ANTI-NFLAMMATORY AGENT AND A FOREIGN PATENT DOCUMENTS PROSTAGLANDIN 91/16895 11/1991 (WO). 99/12524 3/1999 (WO). (75) Inventors: Aomar Ouali, Boisbriand; Abul Kalam 99/65496 12/1999 (WO). Azad, Montreal, both of (CA) 00/01368 1/2000 (WO). 00/15200 3/2000 (WO). (73) Assignee: Pharmascience Inc., Montreal (CA) OTHER PUBLICATIONS (*) Notice: Under 35 U.S.C. 154(b), the term of this Searle HealthNet Prescribing Information for Arthrotec(R) patent shall be extended for 0 days. (downloaded from http://www.searlehealthnet.com/pi/ar throtec.html on Oct. 27, 1998). (21) Appl. No.: 09/273,692 Information for the Patient: ControtecTM. (22) Filed: Mar. 22, 1999 * cited by examiner Primary Examiner James M. Spear (51) Int. Cl. ............................... A61K 9/22; A61 K9/24; (74) Attorney, Agent, or Firm-Dianne E. Reed; J. Elin A61 K9/52; A61 K9/54 Hartrum; Reed & Associates (52) U.S. Cl. .......................... 424/472; 424/451; 424/457; 424/458; 424/465; 424/468; 424/470; 424/474; (57) ABSTRACT 424/489; 514/772.3; 514/781; 514/970 A pharmaceutical composition is provided for the oral (58) Field of Search ..................................... 424/472, 474, administration of an NSAID and a prostaglandin. The com 424/451, 464, 465, 489, 470, 457, 468, position is a solid dosage form wherein the NSAID is 458 enterically coated and the prostaglandin is present along with an effective Stabilizing amount of a prostaglandin (56) References Cited Stabilizing agent Such as hydroxypropyl methylcellulose or U.S.