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(12) United States Patent (10) Patent No.: US 8,557,285 B2 Plachetka (45) Date of Patent: *Oct

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(12) United States Patent (10) Patent No.: US 8,557,285 B2 Plachetka (45) Date of Patent: *Oct US008557285B2 (12) United States Patent (10) Patent No.: US 8,557,285 B2 Plachetka (45) Date of Patent: *Oct. 15, 2013 (54) PHARMACEUTICAL COMPOSITIONS FOR (56) References Cited THE COORONATED DELVERY OF NSAIDS U.S. PATENT DOCUMENTS (75) Inventor: John R. Plachetka, Chapel Hill, NC 4,198.390 A 4, 1980 Rider ............................ 424/471 (US) 4.255.431 A 3/1981 Junggren et al. .............. 514,338 (73) Assignee: Pozen Inc., Chapel Hill, NC (US) (Continued) (*) Notice: Subject to any disclaimer, the term of this FOREIGN PATENT DOCUMENTS patent is extended or adjusted under 35 AU 2006235929 11, 2006 U.S.C. 154(b) by 0 days. CA 2139653 T 2001 This patent is Subject to a terminal dis (Continued) claimer. OTHER PUBLICATIONS (21) Appl. No.: 13/215,855 Goldstein et al., “PN400 significantly improves upper (22) Filed: Aug. 23, 2011 gastrointestinal tolerability compared with enteric-coated naproxen alone in patients requiring chronic NSAID therapy: Results from (65) Prior Publication Data Two Prospective, Randomized, Controlled Trials.” POZEN Inc. sponsored study, 2009. (Document D15 from Letter to European US 2012/OO64156A1 Mar. 15, 2012 Patent Office for counterpart European Application No. 02734602.2, Related U.S. Application Data regarding Oral Proceedings dated Dec. 18, 2009). (60) Division of application No. 12/553,804, filed on Sep. (Continued) 3, 2009, now abandoned, which is a division of application No. 11/129,320, filed on May 16, 2005, Primary Examiner — Nissa Westerberg now Pat. No. 8,206,741, which is a (74) Attorney, Agent, or Firm — Parker Highlander PLLC continuation-in-part of application No. 10/158,216, filed on May 31, 2002, now Pat. No. 6,926,907. (57) ABSTRACT (60) Provisional application No. 60/294,588, filed on Jun. The present invention is directed to drug dosage forms that 1, 2001. release an agent that raises the pH of a patient's gastrointes (51) Int. C. tinal tract, followed by a non-steroidal anti-inflammatory A6 IK 9/22 (2006.01) drug. The dosage form is designed so that the NSAID is not A6 IK9/32 (2006.01) released until the intragastric pH has been raised to a safe A61 K9/24 (2006.01) level. The invention also encompasses methods of treating A61 K9/52 (2006.01) patients by administering this coordinated release, gastropro U.S. C. tective, antiarthritic/analgesic combination unit dosage form (52) to achieve pain and symptom relief with a reduced risk of USPC ........... 424/472: 424/457; 424/463; 424/468; developing gastrointestinal damage such as ulcers, erosions 424/474; 424/482 and hemorrhages. (58) Field of Classification Search None See application file for complete search history. 4 Claims, 2 Drawing Sheets BARRERF COAT NAPROXENSODIUM CORE TABLET ENERC FM COAT ACED INHIBITOR COAT US 8,557,285 B2 Page 2 (56) References Cited 6,632,451 B2 10/2003 Penhasi et al. ................ 424/464 6,641,838 B2 11/2003 Pather et al. ... 424/466 U.S. PATENT DOCUMENTS 6,645,988 B2 11/2003 Phillips ........ ... 514,338 6,673,819 B2 1/2004 Bergman et al. .............. 514,338 4,344,929 A 8, 1982 Bonsen et al. ................ 424/466 6,685,964 B1 2/2004 Bartholomaeus et al. ... 424/489 4,508,905 A 4, 1985 Junggren et al. 546,273.7 6,699,885 B2 3/2004 Phillips .................. ... 514,338 4.554.276 A 1 1/1985 LaMattina .................... 514,272 6,713,089 B1 3/2004 Bertelsen et al. ... 424/489 4562.26. A 12/1985 Hirata et al... 548.184 6,749,867 B2 6/2004 Robinson et al. ... 424/489 4,619,934. A 10/1986 Sunshine et al. 514,277 6,780,882 B2 8/2004 Phillips ... ... 514,338 4,676.984 A 6, 1987 Wu et al. ..... 424,689 6,787,164 B2 9, 2004 Gelber et al. ... 424,729 4704.278 A 1/1987 Wietal. 424,688 6,797.283 B1 9/2004 Edgren et al. ... 424/472 4726.951 A 2f1988 Panoz et all 424/465 6,869,615 B2 3/2005 Chen et al. .................... 424/464 4,738,974. A 4, 1988 Brandstrom ... 514,338 6,875,872 B1 4/2005 Lindberg et al. 4,757,060 A 7, 1988 Lukacsko et al. 514,160 6,926,907 B2 8/2005 Plachetka ..................... 424,472 4,758,579 A 7, 1988 Kohl et al. ......... 514,338 7,029,701 B2 4/2006 Chen ............... ... 424/489 4,766,117 A 8, 1988 Crawford et al. ............. 514,219 7,030,162 B2 4/2006 Plachetka et al. ... 514,619 4.786,505 A 1 1/1988 Lovgren et al. ............... 424/468 7,060,694 B2 6/2006 Plachetka et al. 514,177 4,853,230 A 8/1989 Lovgren et al. 424/466 7,094,425 B2 8/2006 Scott et al. ...... ... 424/451 4,865,847. A 9, 1989 Gosswein .......... 424/439 7,332,183 B2 2/2008 Plachetka et al. ... 424/472 4.948,581 A 8/1990 Sawayanagi et al. ......... 424/497 7,399,772 B2 7/2008 Phillips ........................ 514,338 4,965,065. A 10/1990 Lukacsko et al. .. 514,162 7,411,070 B2 8/2008 Cotton et al. 5,026,560 A 6, 1991 Makino et al. 424/494 7488,497 B2 2/2009 Depui et al. .................. 424,472 5,035,899 A 7/1991 Saeki et al. ... 424/480 7,745,466 B2 6/2010 Cotton et al. 5,037,815 A 8, 1991 Lukacsko et al. .. 514,162 7,785,626 B2 8/2010 Pettersson et al. ............ 424/471 5,043,358 A 8, 1991 Lukacsko et al. .. 514,653 7,846,914 B2 12/2010 Petrus ............................. 51462 5,051.262 A 9, 1991 Panoz et al. .... 424/468 8,206,741 B2 6/2012 Plachetka et al. 5,093,132 A 3, 1992 Makino et al. 424/475 2001 OO25107 A1 9, 2001 Barberich et al. ......... 546,273.7 5,204.18 A 4, 1993 Goldman et al. .. 424/489 2002/0012676 A1 1/2002 Lundberg et al. ... 424/468 5,260.333 A 11, 1993 Lukacsko et al. ............. 514,471 2002fOO42433 A1 4/2002 Yelle et al. ...... ... 514,100 5,364,616 A 1 1/1994 Singer et al. .................... 424,52 2002fOO44962 A1 4/2002 Cherukuri et al. ... 424/426 5,373,022 A 12/1994 Fawzi et al. 514,570 2002/0045184 A1 4/2002 Chen ............... ... 435/6.16 5,409,709 A 4/1995 Ozawa et al. .. 424/464 2002fOO86029 A1 7/2002 Lundberg et al. ... 424/468 5417,980 A 5, 1995 Goldman et al. 424/464 2002/0090395 A1 7, 2002 Woolfe et al. ... ... 424/400 5,466.436 A 11/1995 Stables ....... 514, 161 2002/011 1370 A1 8/2002 Bergman et al. ... 514,338 5,514,663 A 5, 1996 Mandel .... ... 514/33 2002/0155153 A1 10/2002 Depui et al. .................. 424/452 5,601,843. A 2f1997 Gilmet ......... 424/475 2002fO16004.6 A1 10, 2002 Robinson et al. ............. 424/469 5,631,022 A 5/1997 Mandel et al. 424/456 2003, OOO8903 A1 1/2003 Barberich et al. ............ 514/100 5.643,960 A 7, 1997 Breitner et al. ............... 514/57O 2003/0040537 A1 2/2003 Plachetka et al. ............. 514,406 5,667.803 A 9/1997 Grimberg ...................... 424/464 2003.01.13375 A1 6/2003 Lundberg et al. ... 424/468 5.679.376 A 10, 1997 Stevens et al. 424/472 2003/0129235 A1 7/2003 Chen et al. ... 424/470 5686.105. A 1/1997 Kelmetal. 424/452 2003/0215527 A1 1 1/2003 Phillips ........ ... 424/747 5,690,960 A 11/1997 Bengtsson et al. 2003/0232080 A1 12/2003 Pather et al. ... 424/434 5,702,723 A 12, 1997 Griffin .......................... 424/463 2003/0232876 A1 12/2003 Pachetka .... ... 514,419 5,714,504 A 2/1998 Lindberg et al. 2004/0022846 A1 2/2004 Depui et al. .................. 424/452 5,716,648 A 2, 1998 Halskov et al. ............... 424,682 2004/0048896 A1 3/2004 Phillips ......................... 424/468 5,750,531 A 5, 1998 Lee et al. ........... 514,256 2004/O121004 A1 6/2004 Taneja . ... 424/464 5,817.338 A 10/1998 Bergstrand et al. 424/468 2004/0131676 Al 72004 Taneja . ... 424/468 5,817,340 A 10, 1998 Roche et al. ... 424/470 2004/0171646 A1 9/2004 Phillips ........ 514,340 5,840,737 A 1 1/1998 Phillips ....... 514,338 2004/0180089 A1 9, 2004 Plachetka et al. ... 424/4 5.872,145 A 2f1999 Plachetka ... 514,415 2005, 00041.71 A1 1/2005 Phillips ........ 514,340 5,877.192 A * 3/1999 Lindberget al. 514,338 2005/0042304 A1 2/2005 Phillips. ... 424/747 5,900,424 A 5, 1999 Kallstrom et al. 2005.0054682 A1 3/2005 Phillips ........ ... 514,340 5,955.451 A 9/1999 Lichtenberger et al. ........ 514,78 2005, 01476.68 A1 7/2005 Bertelsen et al. ... 424/489 6,013,281 A 1/2000 Lundberg et al. ..... 424/468 2005, 0163847 A1 7/2005 Cheng et al. ... ... 424/464 6.025.395 A 2/2000 Breitner et al. 514,570 2005/0227949 A1 10/2005 Edalatpour etal ... 514,338 6,060,499 A 5, 2000 Plachetka ... 514,415 2005/0249806 A1 11/2005 Proehl et al. .... ... 514,338 6,095.734 A 7/2000 Garst et al. .. 514,338 2005/0249811 A1 11/2005 Plachetka ..................... 424,472 6.132.768 A 10, 2000 Sachs et al. 424/458 2006/O165797 A1 7/2006 Plachetka ..................... 514,165 65277 A 10/2000 Depui et al. 424/468 2006/0177504 A1 8/2006 Sundharadas ..
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