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(12) United States Patent (10) Patent No.: US 9,603,826 B2 Soni (45) Date of Patent: Mar USOO96.03826B2 (12) United States Patent (10) Patent No.: US 9,603,826 B2 Soni (45) Date of Patent: Mar. 28, 2017 (54) METHODS OF REDUCING THE RISK OF A 5,618,558 A 4/1997 Horrobin et al. CARDOVASCULAREVENT IN A SUBJECT 5,656,667 A 8, 1997 Breivik et al. 5,698,594 A 12/1997 Breivik et al. ON STATIN THERAPY 5,760,081 A 6/1998 Leaf et al. 5,776,978 A 7/1998 Bruzzese (71) Applicant: Amarin Pharmaceuticals Ireland 5,792,795. A 8, 1998 Buser et al. Limited, Dublin (IE) 5,837,731 A 11/1998 Vaddadi 5,840,944 A 11/1998 Furihata et al. 5,886,037 A 3, 1999 Klor et al. (72) Inventor: Paresh Soni, Mystic, CT (US) 5,888,541 A 3, 1999 Horrobin et al. 5.948,818 A 9, 1999 Buser et al. (73) Assignee: AMARIN PHARMACEUTICALS 6,025,008 A 2/2000 Akahoshi IRELAND LIMITED, Dublin (IE) 6,069,168 A 5, 2000 Horrobin et al. 6,193.999 B1 2/2001 Gennadios (*) Notice: Subject to any disclaimer, the term of this 6,284,268 B1 9, 2001 Mishra et al. 6,313,330 B1 11/2001 Kiyohara et al. patent is extended or adjusted under 35 6,326,031 B1 12/2001 Hsia et al. U.S.C. 154(b) by 0 days. 6,326,355 B1 12/2001 Abbruzzese et al. 6,331,568 B1 12/2001 Horrobin (21) Appl. No.: 14/411,815 6,368,621 B1 4/2002 Engel et al. 6,384,077 B1 5, 2002 Peet (22) PCT Fed: Jun. 28, 2013 6.479,544 B1 1 1/2002 Horrobin 6,531,150 B1 3/2003 Sunohara et al. (86) PCT No.: PCT/US2013/048.559 (Continued) FOREIGN PATENT DOCUMENTS S 371 (c)(1), (2) Date: Dec. 29, 2014 CA 2628.305 5/2007 CA 2653787 12/2007 (87) PCT Pub. No.: WO2O14/OOSO13 (Continued) PCT Pub. Date: Jan. 3, 2014 OTHER PUBLICATIONS Prior Publication Data Ethyl eicosapentaenoic acid online), retrieved on Dec. 11, 2015 (65) Retrieved from the Internet, URL: http://en.wikipedia.org/wiki/ US 2015/O157592 A1 Jun. 11, 2015 Ethyl eicosapentaenoic acid. Ethyl icosapentate online), retrieved on Dec. 11, 2015 Retrieved from the Internet, URL: http://www.chemspider.com/Chemical Related U.S. Application Data Structure.4445394.html. A study of AMR101 to evaluate its ability to reduce cardiovascular (60) Provisional application No. 61/666.447, filed on Jun. events in high risk patients with hypertriglyceridemia and on statin 29, 2012. (REDUCE-IT). Available at: http://clinicaltrials.gov/show? NCTO 1492361. (51) Int. C. Aarsland, et al., “On the Effect of Peroximsomal beta-Oxidation and A6 IK 3L/232 (2006.01) Carnitine Palmitoyltransferase Activity by Eicosapentaenoic Aid in Live and Heart of Rats.” Lipids, 25:546-548, (1990). A 6LX 3L/397 (2006.01) Aas, V., et al., “Eicosapentaenoic acid (20:5 n-3) increases fatty acid A6 IK 45/06 (2006.01) and glucose uptake in cultured human skeletal muscle cells.” (52) U.S. C. Journal of Lipid Research, 47:366-374 (2006). CPC .......... A6 IK3I/232 (2013.01); A61K 3 1/397 Abbey, M., et al., “Effect of fish oil on lipoproteins, lecithin:cholesterol acyltransferase, and lipid transfer protein activ (2013.01); A61K 45/06 (2013.01) ity in humans' Arterioscler. Thromb. Vasc. Biol. 10:85-94 (1990). (58) Field of Classification Search Abela GS, Aziz K. Cholesterol crystals cause mechanical damage to CPC ..... A61K 31/232; A61K 45/06; A61K 3 1/397 biological membranes: a proposed mechanism of plaque rupture and See application file for complete search history. erosion leading to arterial thrombosis. Clin. Cardiol. 2005:28(9):413-420. References Cited Abelo A, Andersson TB, Antonsson M, et al. Stereoselective (56) metabolism of omeprazole by human cytochrome P450 enzymes. U.S. PATENT DOCUMENTS Drug Metab. Dispos. Aug. 28, 2000 (8): 966-72. (Continued) 4,377,526 A 3/1983 Fujita et al. 4,526,902 A 7, 1985 Rubin Primary Examiner — Kristin Vajda 4,920,098 A 4, 1990 Cotter et al. (74) Attorney, Agent, or Firm — Perkins Coie LLP 4,935,243 A 6, 1990 Borkan et al. 5,013,443 A 5/1991 Higashidate et al. (57) ABSTRACT 5,116,871 A 5, 1992 Horrobin et al. In various embodiments, the present invention provides 5,178,873 A 1/1993 Horrobin et al. methods of reducing the risk of a cardiovascular event in a 5, 198,468 A 3, 1993 Horrobin Subject on statin therapy and, in particular, a method of 5,215,630 A 6, 1993 Hata et al. reducing the risk of a cardiovascular event in a Subject on 5,252.333 A 10, 1993 Horrobin statin therapy having a fasting baseline triglyceride level of 5,343,389 A 8, 1994 OtvOS about 135 mg/dL to about 500 mg/dL, and administering to 5,457,130 A 10, 1995 Tisdale et al. the Subject a pharmaceutical composition comprising about 5,502,077 A 3, 1996 Breivik et al. 1 g to about 4 g of eicosapentaenoic acid ethyl ester or a 5,567,730 A 10/1996 Miyashita et al. derivative thereof. 5,589,508 A 12/1996 Schlotzer et al. 5,603,959 A 2f1997 Horrobin et al. 13 Claims, No Drawings US 9,603,826 B2 Page 2 (56) References Cited 2006/0172012 A1 8/2006 Finley et al. 2006/0189682 A1 8/2006 Payne et al. 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