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(12) United States Patent (10) Patent No.: US 8,642,801 B2 Kong Et Al

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(12) United States Patent (10) Patent No.: US 8,642,801 B2 Kong Et Al USOO86428O1B2 (12) United States Patent (10) Patent No.: US 8,642,801 B2 Kong et al. (45) Date of Patent: Feb. 4, 2014 (54) METHODS AND COMPOSITIONS FOR 4,528, 184 A 7, 1985 Kurono et al. TREATING AMYLOID-RELATED DISEASES 4,540,564 A 9, 1985 Bodor 4,563,470 A 1/1986 Durlach 4,593,045 A 6, 1986 Flork et al. (75) Inventors: Xianqi Kong, Dollard-des-Ormeaux 4,713,376 A 12/1987 Kuzuya et al. (CA); David Migneault, Laval (CA); 4,737,353 A 4, 1988 Flanigen et al. Isabelle Valade, Laval (CA); Xinfu Wu, 4,737,357 A 4, 1988 Lehmann et al. 4,812,512 A 3, 1989 Buendia et al. Laval (CA); Francine Gervais, Ile 4,847,082 A 7, 1989 Sabin Bizard (CA) 4.956,347 A 9, 1990 Ban et al. 5,017,566 A 5, 1991 Bodor (73) Assignee: BHI Limited Partnership, Laval, 5,023,252 A 6, 1991 HSeih Quebec (CA) 5,024,998 A 6, 1991 Bodor 5,039,794. A 8, 1991 Wier et al. 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(63) Continuation of application No. 1 1/316,694, filed on 5,318,958 A 6/1994 Kisilevsky Dec. 21, 2005, now abandoned, which is a 5,342,977 A 8/1994 Baschang et al. continuation-in-part of application No. 10/871,514, 5,374,548 A 12/1994 Caras filed on Jun. 18, 2004, now Pat. No. 7,414,076. (Continued) (60) Provisional application No. 60/480,906, filed on Jun. FOREIGN PATENT DOCUMENTS 23, 2003, provisional application No. 60/512,047, filed on Oct. 17, 2003, provisional application No. CA 10953.06 A1 2, 1981 60/638,819, filed on Dec. 22, 2004. CA 2031433 A1 6, 1991 (Continued) (51) Int. C. C07C 309/19 (2006.01) OTHER PUBLICATIONS A6 IK3I/85 (2006.01) (52) U.S. C. Abderhalden et al. (CAPLUS Abstract of Fermentforschung (1930), USPC ............................................. 562/44; 514/576 12, 180-222).* Wermuth, The Practice of Medicinal Chemsitry, 2d ed. (2003), 768 (58) Field of Classification Search pages. Chapters 9-10 provided.* USPC ............................................. 562/44; 514/576 IUPAC. Compendium of Chemical Terminology, 2nded. (The “Gold See application file for complete search history. Book”). Compiled by A. D. McNaught and A. Wilkinson. Blackwell Scientific Publications, Oxford (1997). "Amino-acid residue” defi (56) References Cited nition provided.* Cerovsky et al., 1994, Int. J. Peptide & Protein Res., 44(5), 466-471. U.S. PATENT DOCUMENTS De Bont et al., 1996, Bioorg & Med. Chem. 6(24), 3035-3040. 2,376,911 A 5, 1945 Graenacher et al. Higashiura et al., 1992, J. Chem. Res., Synopsis, (8), 250-251. 2,531,468 A 1 1/1950 Reynolds et al. Hollowood, C.J., 2003, Org. & Biomolec. Chem., 1(10), 1664-1675. 3,218,352 A 11, 1965 Freifelder et al. 3,236,881 A 2f1966 Distler et al. (Continued) 3,453,309 A 7, 1969 Westland 3,580,936 A 5, 1971 Patchett et al. 3,658,966 A 4, 1972 Tsunoo et al. Primary Examiner — Robert Havlin 3,872,125 A 3, 1975 Houlihan et al. 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