US007790905B2 (12) United States Patent (10) Patent No.: US 7,790,905 B2 Tawa et al. (45) Date of Patent: Sep. 7, 2010 (54) PHARMACEUTICAL PROPYLENE GLYCOL 5,177.262 A 1/1993 Taylor et al. SOLVATE COMPOSITIONS 5,242.942 A 9, 1993 Costanzo et al. (75) Inventors: Mark Tawa, Brighton, MA (US); Orn 30 lso t s Almarsson, Shrewsbury, MA (US); 5.324,351 A 6/1994 OShlack et all Julius Remenar, Framingham, MA (US) - 4 5,332,834 A 7, 1994 Bhattacharya et al. (73) Assignee: McNeil-PPC, Inc., Skillman, NJ (US) 5,338,644 A 8/1994 Taylor et al. 5,354,556 A 10/1994 Sparks et al. (*) Notice: Subject to any disclaimer, the term of this 5,356.467 A 10, 1994 O'Shlack et al. patent is extended or adjusted under 35 5,366,738 A 11/1994 Rork et al. U.S.C. 154(b) by 1554 days. 5,380,867 A 1/1995 Bhattacharya et al. (21) Appl. No.: 10/747,742 5,384.327 A 1/1995 Costanzo et al. 5,412,094. A 5/1995 Amos et al. (22) Filed: Dec. 29, 2003 5,414,997 A 5, 1995 Tailer 5,466,823. A 1 1/1995 Talley et al. (65) Prior Publication Data 5,472,712 A 12/1995 Oshlack et al. US 2007/0015841 A1 Jan. 18, 2007 5,474,997 A 12/1995 Gray et al. 5,510,496 A 4/1996 Talley et al. Related U.S. Application Data 5,521,207 A 5/1996 Graneto (60) Provisional application No. 60/486,713, filed on Jul. 5,523,090 A 6/1996 Znaiden et al. 11, 2003, provisional application No. 60/459,501, 5,563,165 A 10/1996 Talley et al. filed on Apr. 1, 2003, provisional application No. 5,591,767 A 1/1997 Mohr et al. 60/456,608, filed on Mar. 21, 2003, provisional appli- 5,614,342 A 3, 1997 Molaire et al. cation No. 60/456,027, filed on Mar. 18, 2003, provi- 5,631,250 A 5/1997 Bunnell et al. sional application No. 60/441,335, filed on Jan. 21, 5,633,015 A 5, 1997 Gilis et al. 2003, provisional application No. 60/437,516, filed on 5,633,272 A 5/1997 Talley et al. Dec. 30, 2002. 5,639,476 A 6/1997 Oshlack et al. (51) Int. C. 5,641,512 A 6/1997 Cimiluca CO7D 23L/2 (2006.01) 5,661,151 A 8, 1997 Saksena et al. A6 IK 3L/45 (2006.01) 5,674,533 A 10, 1997 Santus et al. (52) U.S. Cl. .................................... 548/375.1: 514/406 5,703,232 A 12/1997 Bunnell et al. (58) Field of Classification Search ................. 424/246; 514/220,557, 406; 548/375.1 See application file for complete search history. (Continued) (56) References Cited FOREIGN PATENT DOCUMENTS U.S. PATENT DOCUMENTS EP 0310.122 B1 4, 1989 2,665,277 A 1/1954 Homeyer et al. 2,711,411 A 6, 1955 Holbert et al. 3,028,420 A 4, 1962 Petrow et al. 3,598,123 A 8, 1971 Zaffaroni (Continued) 3,845,770 A 11/1974 Theeuwes et al. 3,916,899 A 11/1975 Theeuwes et al. OTHER PUBLICATIONS 3,970,651 A * 7/1976 Kaplanet al. ............... 540,226 4,008,321 A 2f1977 Kamishita et al. Gavezzotti, Acc. Chem. Res. 1994, 27, 309-314.* 4,198,507 A 4/1980 Barry et al. 4,267,179 A 5, 1981 Heeres et al. (Continued) 4,368, 197 A 1/1983. Shefter et al. 4.513,006 A 4/1985 Maryanoff et al. Primary Examiner Shaojia Anna Jiang 4,764,604. A 8, 1988 Muller Assistant Examiner—Jonathan S Lau 4,853,379 A 8, 1989 Shroot et al. (74) Attorney, Agent, or Firm Saliwanchik, Lloyd & 4,916,134 A 4, 1990 Heeres et al. Saliwanchik; Laura A. Donnelly 4,925,674. A * 5/1990 Giannini et al. ............. 424/469 4,927,855 A 5, 1990 Lafon (57) ABSTRACT 4,994,604. A 2, 1991 Tung et al. 3,536,809 A 4, 1991 Schaller et al. 5,006,513 A 4, 1991 Hector et al. The invention relates to pharmaceutical compositions com 5,023,092 A 6, 1991 DuROSS rising propvlene glvcol solvates of APIs 5,059,595 A 10/1991 Le Grazie pr1S1ng propylene gly 5,073,543 A 12/1991 Marshall et al. 5, 120,548 A 6, 1992 McClelland et al. 23 Claims, 29 Drawing Sheets US 7,790,905 B2 Page 2 U.S. PATENT DOCUMENTS 2004.0053853 A1 3/2004 Almarsson et al. 2004/0106052 A1 6, 2004 Molaire 5,707,975 A 1/1998 Francois et al. 2004/0106053 A1 6/2004 Molaire et al. 5,733,566 A 3, 1998 Lewis 2004/0106055 A1 6/2004 Molaire et al. 5,736,541. A * 4, 1998 Bunnell et al. .............. 514, 220 2004/O154890 A1 8, 2004 Liu 5,753,688 A 5/1998 Talley et al. 2004/0171062 A1 9, 2004 Hirth et al. 5,753,693 A 5, 1998 Shank 2004/0176335 A1 9, 2004 Childs 5,760,007 A 6, 1998 Shank et al. 2004/0242640 A1 12/2004 Desai et al. 5,760,068 A * 6/1998 Talley et al. ................ 514,403 2005/0070551 A1 3/2005 Remenar et al. 5,932,598 A 8/1999 Talley et al. 2005, 0169982 A1 8/2005 Almarsson et al. 5,935,933 A 8, 1999 Shank et al. 2005/0181041 A1 8/2005 Goldman 5,952,187 A 9/1999 Stenglein et al. 2005/0252649 A1 11/2005 Chiu et al. 5,972,986 A 10/1999 Seibert et al. 2005/0256127 A1 11/2005 Ku et al. 5,985,902 A 1 1/1999 Talley et al. 2006/0134198 A1 6/2006 Tawa et al. 5.998,380 A 12/1999 Ehrenberg et al. 2006/0223794 A1 10/2006 Hickey et al. 5,998.413 A 12/1999 Heeres et al. 2007, OO15841 A1 1/2007 Tawa et al. 6,001,996 A 12/1999 Amos et al. 2007/0021510 A1 1/2007 Hickey et al. 6,054,136 A * 4/2000 Farah et al. ................. 424/400 2007/0059356 A1 3/2007 Almarsson et al. 6,071,537 A 6, 2000 Shank 2007/0293674 Al 12/2007 Scoppettuolo et al. 6,132,420 A 10/2000 Dionne et al. 6,156,781 A 12/2000 Talley et al. FOREIGN PATENT DOCUMENTS 6, 191,117 B1 2/2001 Kozachuk 6,201,010 B1 3/2001 Cottrell EP 0283992 B1 9, 1992 6.245,357 B1 6/2001 Edgren et al. EP 413528 B1 11, 1995 6,268.385 B1 7/2001 Whittle et al. EP 1167355 A1 1/2002 6,270,787 B1 8/2001 Ayer EP 1364649 A1 11, 2003 6.283.953 B1 9/2001 Ayer et al. FR T69586 6, 1934 6,287,295 B1 9/2001 Chen et al. FR 2849029 6, 2004 6,294,192 B1 9/2001 Patel et al. GB 1297 261 12, 1972 6,319,903 B1 1 1/2001 Carrazana et al. GB 2 169601 T 1986 6,323,266 B2 11/2001 Phillips IN 18262O 12/1994 6,333,050 B2 12/2001 Wong et al. IT O13O3251 11, 2000 6,342,249 B1 1/2002 Wong et al. JP 46-33588 10, 1971 6,348,458 B1 2/2002 Hamied et al. JP 54-16494 2, 1979 6,365,185 B1 4/2002 Ritschel et al. JP 54-095589 7/1979 6,368.626 B1 4/2002 Bhatt et al. WO WO94, 16733 A1 8/1994 6,375,978 B1 4/2002 Kleiner et al. WO WO95/17407 A1 6, 1995 6,384,034 B2 5/2002 Simitchieva et al. WO WO95/23596 9, 1995 6,403,640 B1 6/2002 Stoner et al. WO WO 96.07331 A1 3/1996 6,413,965 B1 7/2002 Mylari WO WO96,33193 10, 1996 6.420,394 B1 7/2002 Supersaxo WO WO98,57967 A1 12, 1998 6,488.962 B1 12/2002 Berner et al. WO WOOOf O7583 A2 2?2OOO 6,503,884 B1 1/2003 Ehrenberg et al. WO WOOO,32189 A1 6, 2000 6,559,293 B1 5/2003 Almarsson et al. WO WOOO, SOO2O A2 8, 2000 6,570,036 B1 5/2003 Reuter WO WOOO,53283 A1 9, 2000 6,579,895 B2 6/2003 Karim et al. WO WOOO.72841 A1 12/2000 6,613,790 B2 9, 2003 Carter WO WO 01/13904 A2 3, 2001 6,699,840 B2 3/2004 Almarsson et al. WO WO 01/41536 A2 6, 2001 7,078,526 B2 7/2006 Remenar et al. WO WO 01/41760 A3 6, 2001 7,132,570 B2 11/2006 Neckebrocket al. WO WO 01/42221 A1 6, 2001 7,132,579 B2 11/2006 Neckebrocket al. WO WO 01/42222 A1 6, 2001 7,172,769 B2 2/2007 Kararliet al. WO WOO1? 45706 6, 2001 7.205,413 B2 4/2007 Morissette et al. WO WOO1,51919 A2 7, 2001 7,446,107 B2 11/2008 Remenar et al. WO WOO1.78724 A1 10, 2001 7,452,555 B2 11/2008 Childs WO WOO1f91750 A1 12/2001 7,459,449 B2 12/2008 Keltjens WO WOO1/97853 A1 12/2001 2002/0006951 A1 1/2002 Hageman et al. WO WO O2/OO627 A1 1/2002 2002fOO 13357 A1 1/2002 Nadkarni et al. WO WOO2,101.25 2, 2002 2002fOO15735 A1 2/2002 Hedden et al.