(10) Patent No.: US 7790905 B2

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(10) Patent No.: US 7790905 B2 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. 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