US 20140288017A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2014/0288017 A1 Jorgensen et al. (43) Pub. Date: Sep. 25, 2014

(54) CATECHOLDIETHERS AS POTENT A 6LX3 L/505 (2006.01) ANT-HIV AGENTS C07D 25L/42 (2006.01) A613 L/53 (2006.01) (71) Applicant: YALE UNIVERSITY, New Haven, CT C07D 213/69 (2006.01) (US) A613 L/442 (2006.01) C07D 487/04 (2006.01) (72) Inventors: William L. Jorgensen, Deep River, CT A 6LX3 L/5025 (2006.01) (US); Karen S. Anderson, Guilford, CT C07D 213/57 (2006.01) (US) (52) U.S. Cl. CPC ...... C07C 255/54 (2013.01); C07D 213/57 (21) Appl. No.: 14/348,952 (2013.01); A61 K3I/4409 (2013.01); A61 K 45/06 (2013.01); C07D 239/54 (2013.01); (22) PCT Filed: Oct. 12, 2012 A61 K3I/513 (2013.01); C07D 239/553 (2013.01); A61 K3I/5377 (2013.01); A61 K (86). PCT No.: PCT/US2O12/059886 3I/277 (2013.01); A61 K3I/536 (2013.01); S371 (c)(1), A6IK3I/505 (2013.01); C07D 251/42 (2), (4) Date: Apr. 1, 2014 (2013.01); A61K3I/53 (2013.01); C07D 213/69 (2013.01); A61 K3I/4412 (2013.01): Related U.S. Application Data C07D 487/04 (2013.01); A61K3I/5025 (60) Provisional application No. 61/546,285, filed on Oct. (2013.01) 12, 2011. USPC ...... 514/27: 546/330; 514/357: 544/314: 514/274; 54.4/313; 54.4/123: 514/235.8; Publication Classification 558/424; 514/520; 514/230.5: 514/272: 514/275; 544/211: 514/245; 546/296; 514/348; (51) Int. Cl. 544/236; 514/248: 514/120 C07C 255/54 (2006.01) A6 IK3I/4409 (2006.01) (57) ABSTRACT A6 IK 45/06 (2006.01) C07D 239/54 (2006.01) The present invention is directed to novel catechol diether A6 IK3I/53 (2006.01) compounds, pharmaceutical compositions therefrom and C07D 239/553 (2006.01) methods for inhibiting reverse transcriptase and treating HIV A 6LX3/5377 (2006.01) , especially included drug resistant strains of HIV 1 A 6LX3L/277 (2006.01) and 2 and/or secondary disease states and/or conditions A6 IK3I/536 (2006.01) which occur as a consequence of HIV . Patent Application Publication Sep. 25, 2014 Sheet 1 of 11 US 2014/0288017 A1

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