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USOO9040O88B2 (12) United States Patent (10) Patent No.: US 9,040,088 B2 Hovey et al. (45) Date of Patent: *May 26, 2015 (54) NANOPARTICULATE MEGESTROL (2013.01); A61 K9/10 (2013.01); A61K 9/145 FORMULATIONS (2013.01); A61 K9/146 (2013.01); A61 K3I/57 (2013.01); A61K 45/06 (2013.01); A61K47/20 (71) Applicant: Alkermes Pharma Ireland Limited, (2013.01); A61 K47/32 (2013.01); A61K47/38 Dublin 4 (IE) (2013.01); A61 K9/08 (2013.01); A61 K3I/573 (2013.01); A61 K47/26 (2013.01); A61K47/34 (72) Inventors: Douglas Hovey, Trooper, PA (US); John (2013.01); A61 K47/42 (2013.01) Pruitt, Suwanee; GA (US); Tuula Ryde (58) Field of Classification search Malvern, PA (US) CPC ........................................................ A61 K9/14 See application file for complete search history. (73) Assignee: ALKERMES PHARMA IRELAND LIMITED, Dublin (IE) (56) References Cited (*) Notice: Subject to any disclaimer, the term of this U.S. PATENT DOCUMENTS patent is extended or adjusted under 35 M U.S.C. 154(b) by 0 days. 4,783,484. A 1 1/1988 Violante et al. This patent is Subject to a terminal dis- 4,826,689 A 5, 1989 Violanto et al. claimer. (Continued) (21) Appl. No.: 14/536,517 FOREIGN PATENT DOCUMENTS 1-1. EP O 338 404 10, 1989 (22) Filed: Nov. 7, 2014 EP 338404 A1 * 10, 1989 (65) Prior Publication Data (Continued) US 2015/OO56286 A1 Feb. 26, 2015 OTHER PUBLICATIONS Related U.S. Application Data Office Action dated Sep. 18, 2008, for related U.S. Appl. No. 10/878,623, 16 pgs. (60) Division of application No. 10/878,623, filed on Jun. pg (Continued) 29, 2004, which is a continuation-in-part of application No. 10/412,669, filed on Apr. 14, 2003, now Pat. No. 7,101,576. Primary Examiner — Carlos Azpuru (60) Provisional application No. 60/371,680, filed on Apr. Assistant Examiner — Casey Hagopian 12, 2002, provisional application No. 60/430,348, (74) Attorney, Agent, or Firm — Foley & Lardner LLP filed on Dec. 3, 2002. (57) ABSTRACT (51) Eiki/4 2006.O1 The present invention is directed to nanoparticulate compo A6 IK9/00 30 6. 8: sitions comprising megestrol. The megestrol particles of the compositionp have an effective averagege pparticle size of less (Continued) than about 2000 nm. (52) U.S. Cl. CPC ................. A61 K9/14 (2013.01); A61 K9/0095 29 Claims, 5 Drawing Sheets 1, 5.0 s 4.0 - - 5 3.0 - uo > - 2.0 -8 -- O 10 - - -e- D O. O co- - O 2O 40 60 8O 1 OO Concentration of Active (mg/ml) US 9,040,088 B2 Page 2 (51) Int. C. 6,045,829 A 4/2000 Liversidge et al. A6 IK 9/10 6,068,858 A 5/2000 Liversidge et al. (2006.01) 6,153,225 A 11/2000 Lee et al. A 6LX3/57 (2006.01) 6,165,504 A 12, 2000 Bell A6 IK 45/06 (2006.01) 6,165,506 A 12/2000 Jain et al. A6 IK 47/20 (2006.01) 6,221,400 B1 4/2001 Liversidge et al. 6,264,922 B1 7/2001 Wood et al. A6 IK 47/32 (2006.01) 6,267,989 B1 7/2001 Liversidge et al. A6 IK 47/38 (2006.01) 6,268,356 B1 7/2001 Ragunathan et al. A6 IK9/08 (2006.01) 6,270.806 B1 8/2001 Liversidge et al. A 6LX3/573 6,316,029 B1 1 1/2001 Jain et al. (2006.01) 6,375,986 B1 4/2002 Ryde et al. A6 IK 47/26 (2006.01) 6,428,814 B1 8, 2002 Bosch A6 IK 47/34 (2006.01) 6,431,478 B1 8, 2002 Reed et al. A6 IK 47/42 (2006.01) 6.432,381 B2 8/2002 Liversidge et al. 6,593,318 B2 7/2003 Ragunathan References Cited 6,593,320 B2 7/2003 Ragunathan (56) 6,656,505 B2 12/2003 Kundu et al. 6,833,373 B1 12/2004 McKearn et al. 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WO WO 2005/044234 5, 2005 5,560,931 10, 1996 Eickhoff et al. 5,560,932 10, 1996 Bagchi et al. OTHER PUBLICATIONS 5,565,188 10, 1996 Wong et al. 5,569,448 10, 1996 Wong et al. European Office Action issues for European Application No. 03723 5,571,536 11, 1996 Eickhoff et al. 991.0 dated Nov. 4, 2008, 9 pgs. 5,573,749 11, 1996 Illig Gaver et al., “Liquid Chromatographic Procedure for the Quantita 5,573,750 11, 1996 Singh tive Analysis of Megestrol Acetate in Human Plasma'. Journal of 5,573,783 11, 1996 Desieno et al. 5,580,579 12, 1996 Ruddy et al. Pharmaceutical Sciences, vol. 74, No. 6, pp. 664-667 (Jun. 1985). 5,585, 108 12, 1996 Ruddy et al. Lindahl et al., “Characterization of Fluids from the Stomach and 5,587,143 12, 1996 Wong Proximal Jejunum in Men and Women', Pharmaceutical Research, 5,591.456 1/1997 Franson et al. vol. 14, No. 4, pp. 497-502 (1997). 5,593,657 1/1997 Ruddy et al. Stedman's Medical Dictionary, 25' Edition, p. 935 (1990). 5,605,889 2, 1997 Curatolo et al. 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US 9,040,088 B2 Page 3 (56) References Cited Bruera, E. K. Macmillan, et al. (1990). “A controlled trial of megestrol acetate on appetite, caloric intake, nutritional status, and OTHER PUBLICATIONS other symptoms in patients with advanced cancer.” Cancer 66(6): 1279-82. U.S. Office Action in related U.S. Appl. No. 10/420,927, dated Dec. Bruera, E. S. Ernst, et al. (1998). “Effectiveness of megestrol acetate 10, 2009. in patients with advanced cancer: a randomized, double-blind, cross Notice of Rejections for JP 2003-583377 dated Dec.
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