US 2010O3.31307A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2010/0331307 A1 Salituro et al. (43) Pub. Date: Dec. 30, 2010 (54) THERAPEUTIC COMPOUNDS AND Publication Classification COMPOSITIONS (51) Int. Cl. (76) Inventors: Francesco G. Salituro, A 6LX 3/553 (2006.01) Marlborough, MA (US); Jeffrey O. A6IP35/00 (2006.01) Saunders, Concord, MA (US); A 6LX 3L/2197 (2006.01) Shunqi Yan, Irvine, CA (US) C07D 40/12 (2006.01) C07D 417/4 (2006.01) Correspondence Address: C07D 405/4 (2006.01) LANDO & ANASTASI, LLP C07D 40/4 (2006.01) ONE MAINSTREET, SUITE 1100 CAMBRIDGE, MA 02142 (US) (52) U.S. Cl. ............... 514/210.21; 514/218: 514/253.06; (21) Appl. No.: 12/826,630 540/575:544/363 Filed: Jun. 29, 2010 (22) (57) ABSTRACT Related U.S. Application Data Compounds and compositions comprising compounds that (60) Provisional application No. 61/221,430, filed on Jun. modulate pyruvate kinase M2 (PKM2) are described herein. 29, 2009, provisional application No. 61/292,360, Also described herein are methods of using the compounds filed on Jan. 5, 2010. that modulate PKM2 in the treatment of cancer. Patent Application Publication Dec. 30, 2010 Sheet 1 of 70 US 2010/0331307 A1 Figure 1 Compound ACso Patent Application Publication Dec. 30, 2010 Sheet 2 of 70 US 2010/0331307 A1 Figure 1 Compound ACso MeO a. N ) C CSS B O F N S CC F C O MeO Ol s 9 OMe N C C5.S. B O C a OMe N^ S N O B O Cl OWe O s 9 OEt N CO S B O C OMe N1 RéaS -4. O A N 3. 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