US007795436 B2 (12) United States Patent (10) Patent No.: US 7,795,436 B2 Chen et al. (45) Date of Patent: Sep. 14, 2010 (54) SUBSTITUTED TRICYCLIC 5,686,104 A 11, 1997 Mills et al. HETEROCYCLES AS SEROTONN 5,698,527 A 12, 1997 Kim RECEPTORAGONSTS AND ANTAGONSTS 5,712,396 A 1/1998 Magnin et al. 5,753,675 A 5/1998 Wattanasin (75) Inventors: Wenting Chen, Beijing (CN); Taekyu 5,770,615 A 6/1998 Cheng et al. Lee, Doylestown, PA (US) 5,776,983 A 7/1998 Washburn et al. 5.990,109 A 11/1999 Chen et al. (73) Assignee: Bristol-Myers Squibb Company, 6,043,265 A 3/2000 Murugesan et al. Princeton, NJ (US) 6,184,231 B1 2/2001 Hewawasam et al. 6,358,950 B1 3/2002 He et al. (*) Notice: Subject to any disclaimer, the term of this 6,362,180 B1 3/2002 Wilde et al. patent is extended or adjusted under 35 6,395,767 B2 5, 2002 Roblet al. U.S.C. 154(b) by 1056 days. (21) Appl. No.: 11/509,354 (Continued) (22) Filed: Aug. 24, 2006 FOREIGN PATENT DOCUMENTS (65) Prior Publication Data DE 19622 222 12/1997 US 2007/OO4.9613 A1 Mar. 1, 2007 Related U.S. Application Data (Continued) (60) Provisional application No. 60/710,954, filed on Aug. OTHER PUBLICATIONS 24, 2005. Caplus English abstract Fuller Ray, 1976.* (51) Int. Cl. (Continued) CO7D 22 I/O (2006.01) A63/4.375 (2006.01) Primary Examiner Rita J Desai (52) U.S. Cl. ......................................... 546/79:514/290 (74) Attorney, Agent, or Firm Terence J. Bogie (58) Field of Classification Search ................... 546/79; (57) ABSTRACT 514/290 See application file for complete search history. The present application describes compounds, including all (56) References Cited pharmaceutically acceptable salts, prodrugs, Solvates and Ste U.S. PATENT DOCUMENTS reoisomers thereof, according to Formula I, pharmaceutical compositions, comprising at least one compound according 3,462.443 A 8/1969 Paragamian 3,674,836 A 7, 1972 Creger to Formula I and optionally at least one additional therapeutic 3,678,058 A * 7/1972 Ebnother et al. ............ 546,111 agent and methods of treating various diseases, conditions 3,983,140 A 9, 1976 Endo et al. and disorders associated with modulation of serotonin recep 4,027,009 A 5, 1977 Grier et al. tors such as, for example: metabolic diseases, which includes 4,231,938 A 11/1980 Monaghan et al. but is not limited to obesity, diabetes, diabetic complications, 4,346,227 A 8, 1982 Terahara et al. atherosclerosis, impared glucose tolerance and dyslipidemia; 4,379,785 A 4/1983 Weyer et al. central nervous system diseases which includes but is not 4,448,784. 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