(19) United States (12) Reissued Patent (10) Patent Number: US RE40,667 E Roth (45) Date of Reissued Patent: Mar
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USO0RE40667E (19) United States (12) Reissued Patent (10) Patent Number: US RE40,667 E Roth (45) Date of Reissued Patent: Mar. 17, 2009 (54) [R-(R*R")]-2-(4-FLUOROPHENYL)-[3,6 FOREIGN PATENT DOCUMENTS DIHYDROXY-S-(l-METHYLETHYL-3 AU 601981 9/1990 PHENYL-4-[(PHENYLAMINO)CARBONYL] AU 621874 3/1992 lH-PYRROLE-l-HEPTANOIC ACID, ITS CA 1161380 1/1984 LACTONE FORM AND SALTS THEREOF CA 1268768 5/1990 CA 1304080 6/1992 (75) Inventor: Bruce Roth, San Jose, CA (US) CA 1330441 6/1994 CA 2021546 4/1997 (73) Assignee: Warner-Lambert Company LLC, New CA 2465565 12/2004 York, NY (US) DK 01 171588 12/1987 DK 171588 B1 2/1997 EP 0 024 348 3/1981 (21) Appl.No.: 11/653,830 EP 0 114 027 A1 7/1984 EP 0171588 A1 2/1986 (22) Filed: Jan. 16, 2007 EP 0211416 2/1987 EP 0 221025 A1 5/1987 Related US. Patent Documents EP 0 232 997 8/1987 Reissue of: EP 0 247 633 12/1987 (64) Patent No.: 5,273,995 EP 0 251625 1/1988 Issued: Dec. 28, 1993 EP 0 259 086 3/1988 Appl. No.: 07/660,976 EP 0 319 856 A2 6/1989 Filed: Feb. 26, 1991 EP 0 330 172 8/1989 EP 891030785 8/1989 US. Applications: EP 0409 281 1/1991 IE 1197/87 L 11/1987 IE 890391 8/1989 JP 2240/1982 1/1982 (63) Continuation of application No. 07/384, 187, ?led on Jul. 21, JP 10572/1983 1/1983 1989, now abandoned. JP 62-289577 12/1987 (51) Int. Cl. JP 72652/1988 4/1988 A61K 31/40 (2006.01) KR 1987-5372 2/1994 A61K 31/35 (2006.01) W0 WO 84/02131 6/1984 C07D 207/327 (2006.01) WO PT84975 6/1987 W0 WO 88/07582 10/1988 W0 WO 89/07598 8/1989 (52) US. Cl. ...................... .. 514/422; 514/423; 548/517; WO PT89774 10/1989 548/537 W0 WO 90/00553 1/1990 (58) Field of Classi?cation Search ................ .. 514/422, W0 W0 97 03959 2/1997 514/423; 548/517, 537 W0 WO 99/47138 9/1999 See application ?le for complete search history. OTHER PUBLICATIONS (56) References Cited Hall and Roush, J. Org. Chem, 47: 4611*4621 (1982). Roush and Gillis, J. Org. Chem, 47: 4825*4829 (1982). U.S. PATENT DOCUMENTS Sit et al, J. Med. Chem, 33:2982 (1990). Amin et al., J. Pharmacology 46:13 (1993). 3,808,254 A 4/1974 Matthews 3,965,129 A 6/1976 Perry et al. Underberg et al., J Pharm. BiomedAnal. 8(8il2): 681*683 3,983,140 A 9/1976 Endo et al. (1990). 4,072,698 A 2/1978 Hylton et al. Stinson, Chemical and Engineering News, 70(39): 46*79 4,137,322 A 1/1979 Endo et al. (1992). 4,139,555 A 2/1979 Zerbes Stinson, Chemical and Engineering News, 71(39): 38*64 4,171,359 A 10/1979 Weinstock (1993). 4,192,872 A 3/1980 Weinstock 4,231,938 A 11/1980 Monaghan et a1. (Continued) 4,281,132 A 7/1981 Ward 4,282,155 A 8/1981 Smith et al. Primary ExamineriJoseph K. McKane 4,293,496 A 10/1981 Willard Assistant ExamineriJoseph R Kosack 4,319,039 A 3/1982 Albers-Schonberg (74) Attorney, Agent, or Firm4Connolly, Bove Lodge & 4,342,761 A 8/1982 Ward HutZ LLP 4,342,767 A 8/ 1982 Albers-Schonberg et al. 4,346,227 A 8/1982 Terahara et al. (57) ABSTRACT 4,374,829 A 2/1983 Harris et al. 4,374,844 A 2/1983 McCombie [R-(R* ,R*)]-2-(4-?uorophenyl)-[3,6-dihydroxy-5 -((1 4,375,475 A 3/1983 Willard et al. methylethyl)-3 -phenyl-4-[(phenylamino)-carbonyl)]-1H 4,444,784 A 4/1984 Hoffman et al. pyrrole-l -heptanoic acid or (2R-trans)-5-(4-?uoro-phenyl) 4,450,171 A 5/1984 Hoffman et al. 2-(1 -methylethyl-N,4-diphenyl-1 -[2-(tetrahydro-4-hydroxy 4,474,971 A 10/1984 Wareing 6-oxo-2H-pyran-2-yl)ethyl]-1H-pyrrole-3 -carboxamide; 4,495,103 A 1/1985 Terashima et al. and pharmaceutically acceptable salts thereof. 4,555,511 A 11/1985 Schnorrenberg et a1. (Continued) 3 Claims, No Drawings US RE40,667 E Page 2 US. PATENT DOCUMENTS Seeman, P. Drug Receptors. Kalant H. et al. eds., Principles of Medical Pharmacology, 4’hEdition, University of Toronto 4,611,067 A 9/1986 Volante et al. 4,613,610 A 9/1986 Wareing Press: Toronto, 1985. 4,647,576 A 3/1987 Hoe?e etal. Lachman et al., Proformulation, The Theory and Practice of 4,681,893 A 7/1987 Roth Industrial Pharmacy, 3rd Edition, Lea & Febiger: Philadel 4,697,036 A 9/1987 Giordano et al. phia, 1986. 4,735,958 A 4/1988 Roth etal. Lieberman et al., eds. Pharmaceutical Dosage Forms Tab 4,739,073 A 4/1988 Kathawala lets, 2'” Edition (vol. 1), Marcel Dekker: NeW York, 1989. 4,743,450 A 5/1988 Harris et al. 4,775,681 A 10/1988 HeifetZ Gennaro, Remington's Pharmaceutical Sciences, 18”’ Ed., 4,786,505 A 11/1988 Lovgren et al. Mack Printing Company: Easton, Pennsylvania, 1990. 4,804,679 A 2/1989 Anderson Banker, Rhodes, eds., Modern Pharmaceutics, 3rd Edition, 4,847,306 A 7/1989 Lee et al. Marcel Dekker, Inc.: NeW York, 1996. 4,851,427 A 7/1989 Wareing Kibbe, A.H., ed., Handbook ofPharmaceutical Excipients, 4,853,230 A 8/1989 Lovgren et al. 3rd Ed., Pharmaceutical Press: London, 2000. 4,864,038 A 9/1989 Hoffman etal. 4,866,090 A 9/1989 Hoffman et al. The Merck Index, 10”’ Edition (1983), entry 5949: NiMeth 4,870,187 A 9/1989 Sitet al. ylglucamine, pp. 870*871. 4,897,490 A 1/1990 Sit et al. The Merck Index, 12”’ Edition (1996), entry 897: Atorvasta 4,898,868 A 2/1990 Bergmann et al. tin, p. 146. 4,898,949 A 2/1990 Wright et al. Transcript of evidence given by Dr. Scallen in US trial of 4,906,624 A 3/1990 ChucholoWski et al. Prizer, Inc., et al. v Ranbaxy Laboratories Limited wt. al., 4,939,159 A 7/1990 Anderson et al. Court ?le No. 03*209*JJF, on Dec. 3, 2004. 4,940,727 A 7/1990 Inamine et al. 4,950,775 A 8/1990 Heathcock et al. Guideline for Submitting Supporting Documentation in 4,962,115 A 10/1990 Van Daele Drug Applications for the Manufacture of Drug Substances, 4,963,538 A 10/1990 Duggan et al. Feb. 1987. 4,968,689 A 11/1990 Angerbauer et al. Stein et al., The LovastatiniNiacin Trial: Effects on Lipo 4,976,949 A 12/1990 Meyer et al. proteins. Arteriosclerosis and Thrombosis 11: 1458a (1991). 4,978,791 A 12/1990 Volker et al. Dujovne et al., The LovastatiniNiacin Trial: Adverse 4,992,462 A 2/1991 Hubsch et al. Events. Arteriosclerosis and Thrombosis 11: 1458a (1991). 5,001,255 A 3/1991 Kathawalaetal. 5,003,080 A 3/1991 Butler et al. Frost, P.H. et al., Lipid Metabolism. In PA Fitzgerald, Ed., 5,004,651 A 4/1991 Becker Handbook of Clinical Endocrinology, 2'” Edition, Appleton 5,006,530 A 4/1991 Angerbaueret al. and Lange, 1991. 5,024,999 A 6/1991 Fujikawaet al. Frost, P.H. et al., LovastatiniNiacin Comparative Trial. 5,026,708 A 6/1991 Fujikawaet al. JACC 19, 374A, 1992. 5,030,447 A 7/1991 Joshietal. Lovastatin Study Groups I through IV. Lovastatin 5*year 5,045,321 A 9/1991 Makino etal. 5,055,484 A 10/1991 Jendrallaet al. safety and ef?cacy study. Arch. Intren. Med. 153: 5,061,722 A 10/1991 TeetZ etal. 107941087 (1993). 5,093,132 A 3/1992 Makino et al. IllingWorth, D.R. et al., Comparative effects of lovastatin 5,097,045 A 3/1992 Butler et al. and niacin in primary hypercholesterolemia: A prospective 5,124,482 A 6/1992 Butler et al. trial. Arch. Intern. Med. 154: 158641595 (1994). 5,149,837 A 9/1992 Butler et al. Stein, EA. et al., Ef?cacy and tolerability of lowidose sim 5,151,433 A 9/1992 Fulbreth et al. 5,208,258 A 5/1993 Heathcock et al. vastatin and niacin, alone and in combination, in patients 5,216,174 A 6/1993 Butler et al. With combined hyperlipidemia: a prospective trial. J. Car 5,245,047 A 9/1993 Butler et al. diovasc. Pharmacol. Therapeut. 1: 107*116 (1996). 5,273,995 A 12/1993 Roth Frost, P.H. et al., Rationale for use of nonihighidensity lipo 5,280,126 A 1/1994 Butler et al. protein cholestrol rather than lowidensity lipoprotein cho 5,354,772 A 10/1994 Kathawala lesterol as a tool for lipoprotein cholestrol screening and 5,378,729 A 1/1995 Kohn etal. assessment ofrisk and therapy, Am. J. Cardiol. 81: 26Bi3lB 5,969,156 A * 10/1999 Briggs et al. .............. .. 548/537 6,087,511 A 7/2000 Lin et al. (1 998). 6,121,461 A 9/2000 McKenzie etal. Havel, R]. et al., The role of nonihighalensity lipoprotein 6,274,740 B1 8/2001 Lin et al. cholesterol in evaluation and treatment of lipid disorders. J. 6,605,729 B1 8/2003 Byrn et al. Clin. Endocrinology and Metabolism 85: 2105*2108 7,144,915 B2 * 12/2006 Byrn et al. ................ .. 514/423 (2000). 2006/0241169 A1 * 10/2006 Park ........................