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Tha T the Lulluloitti THA T THEUS009796668B2 LULLULOITTI (12 ) United States Patent ( 10 ) Patent No. : US 9 ,796 ,668 B2 Anderson et al . ( 45 ) Date of Patent: Oct . 24 , 2017 ( 54 ) NATURAL PRODUCT ANALOGS (58 ) Field of Classification Search INCLUDING AN ANTI- INFLAMMATORY CPC . .. .. C07C 255 /46 ; C07C 2101 / 16 ; C07J CYANOENONE PHARMACORE AND 41 /0094 ; C07J 41 /0055 ; C07J 53 /001 ; METHODS OF USE C07J 71 /0005 ; C07J 21 /003 USPC .. .. .. 558 /426 ; 514 /520 See application file for complete search history . (71 ) Applicant: REATA PHARMACEUTICALS , INC ., Irving , TX (US ) ( 56 ) References Cited U . S . PATENT DOCUMENTS ( 72 ) Inventors : Eric Anderson , Southlake , TX (US ) ; 3 ,013 ,010 A 2 / 1957 Cardenas 2 , 875 , 201 A 2 / 1959 Johns Gary L . Bolton , Ann Arbor, MI (US ) ; 4 , 395 ,423 A 7 / 1983 Neumann Deborah A . Ferguson , Branchburg , NJ 4 , 808 ,614 A 2 / 1989 Hertel (US ) ; Xin Jiang , Coppell, TX (US ) ; 5 ,002 , 939 A 3 / 1991 Streber Robert M . Kral, Jr ., Grapevine, TX 5 ,013 , 649 A 5 / 1991 Wang et al. (US ) ; Patrick M . O ' Brien , 5 ,064 , 823 A 11/ 1991 Lee et al. 5 ,401 , 838 A 3 / 1995 Chou Stockbridge , MI (US ) ; Melean Visnick , 5 ,426 , 183 A 6 / 1995 Kjell Irving , TX (US ) 5 , 464 ,826 A 11/ 1995 Grindey 5 , 521, 294 A 5 / 1996 Wildfeuer (73 ) Assignee : REATA PHARMACEUTICALS , 5 , 597 , 124 A 1 / 1997 Kessel INC . , Irving , TX (US ) 5 ,603 ,958 A 2 / 1997 Morein et al . 5 ,606 , 048 A 2 / 1997 Chou et al . 5 ,629 , 295 A 5 / 1997 Deninno et al . ( * ) Notice : Subject to any disclaimer , the term of this 5 , 972 , 703 A 10 / 1999 Long et al. patent is extended or adjusted under 35 6 ,025 , 395 A 2 / 2000 Breitner et al. U . S . C . 154 ( b ) by 0 days. 6 ,303 , 569 B1 10 / 2001 Greenwald et al. 6 ,326 ,507 B1 12 / 2001 Gribble et al . (21 ) Appl. No. : 14 / 950, 557 ( Continued ) ( 22 ) Filed : Nov . 24 , 2015 FOREIGN PATENT DOCUMENTS (65 ) Prior Publication Data CN 1687021 A 10 / 2005 CN 102070697 5 / 2010 US 2016 /0145200 A1 May 26 , 2016 ( Continued ) Related U . S . Application Data OTHER PUBLICATIONS (60 ) Division of application No . 13 / 552, 530 , filed on Jul. “ CDDO in treating patients with metastatic or unresectable solid 18 , 2012 , now Pat . No . 9 , 233 , 998 , which is a tumors or lymphoma, " www . clinicaltrials . gov / ct2 / show / continuation of application No. 12 /426 , 889 , filed on NCT00352040 ? term = CDDO & rank = 1 , Dec . 14 , 2008 . Apr. 20 , 2009 , now Pat. No. 8 , 258 , 329 . ( Continued ) Primary Examiner - Barbara P Badio ( 60 ) Provisional application No . 61/ 046 , 363 , filed on Apr. (74 ) Attorney, Agent , or Firm — Parker Highlander PLLC 18 , 2008 . (57 ) ABSTRACT (51 ) Int. Ci. This invention provides novel compounds comprising the A61K 31 /277 ( 2006 .01 ) following anti - inflammatory pharmacore : C07C 255 / 46 ( 2006 .01 ) CO7D 311 / 74 ( 2006 .01 ) C070 317 / 26 ( 2006 .01 ) CO7D 493 / 10 ( 2006 . 01 ) CO7F 7 / 18 ( 2006 .01 ) 2 C07 ) 21/ 00 ( 2006 . 01 ) C07J 41/ 00 ( 2006 . 01 ) mun C07 ) 53/ 00 ( 2006 .01 ) Ri R2 C07 ) 71 /00 ( 2006 .01 ) (52 ) U . S . CI. ??? . .. C07C 255 /46 ( 2013 . 01 ) ; C070 311/ 74 wherein X , R , and R , are defined herein . Also provided are (2013 . 01 ) ; C070 317 / 26 ( 2013 .01 ) ; C07D pharmaceutical compositions, kits and articles of manufac 493 / 10 ( 2013 .01 ) ; C07F 7 / 1856 (2013 .01 ) ; ture comprising such compounds, methods and intermedi C07 ) 21 /003 ( 2013 .01 ) ; C07J 41 /0055 ates useful for making the compounds , and methods ofusing (2013 . 01 ) ; C07J 41/ 0094 ( 2013 .01 ) ; C07 ) the compounds and compositions. 53/ 001 ( 2013 .01 ) ; C07J 71 /0005 ( 2013 .01 ) ; C07C 2601/ 16 ( 2017 .05 ) 7 Claims, 24 Drawing Sheets US 9 , 796 ,668 B2 Page 2 (56 ) References Cited 2009 / 0060873 A1 3 /2009 Sporn et al. 2009 / 0093447 Al 4 / 2009 Konopleva et al. U . S . PATENT DOCUMENTS 2009 / 0326063 Al 12 /2009 Sporn et al. 2010 / 0041904 Al 2 / 2010 Jiang et al . 6 , 369 , 101 B1 4 / 2002 Carlson 2010 /0048887 Al 2 / 2010 Anderson et al . 6 ,485 ,756 B1 11 / 2002 Aust et al. 2010 / 0048892 Al 2 /2010 Anderson et al. 6 , 552 , 075 B2 4 / 2003 Gribble et al. 2010 / 0048911 A1 2 / 2010 Jiang et al. 6 ,642 , 217 B2 11/ 2003 Krasutsky et al . 2010 / 0056777 Al 3 / 2010 Anderson et al . 6 ,649 ,654 B1 11/ 2003 Karin et al . 2010 / 0261930 A1 10 / 2010 Honda et al. 6 ,689 ,787 B1 2 / 2004 McKearn et al. 2011 / 0009363 AL 1 / 2011 Honda et al. 6 , 951 , 847 B2 10 / 2005 Gibson et al. 2011/ 0196007 Al 8 / 2011 Honda et al . 6 . 974 . 801 B2 12 / 2005 Honda et al . 2011/ 0245206 Al 10 / 2011 Jiang et al. 6 , 991 , 814 B2 1 / 2006 Ray et al. 2011 / 0245233 A 10 / 2011 Anderson et al . 7 , 053, 119 B2 5 / 2006 Karin et al. 2011/ 0281955 A1 11/ 2011 Meyer et al. 7 ,144 , 875 B2 12 / 2006 Gibson et al . 2012 / 0022156 Al 1 / 2012 Zhang et al. 7 ,176 , 237 B2 2 / 2007 Honda et al. 2012 / 0071684 Al 3 / 2012 Walling et al . 7 , 265 , 096 B2 9 / 2007 Gallop et al. 2012 /0101149 A1 4 / 2012 Honda et al. 7 ,288 , 568 B2 10 / 2007 Gribble et al . 2012 /02 14814 Al 8 / 2012 Anderson et al. 7 ,399 , 606 B2 7 / 2008 Karin et al . 2012 / 0220652 Al 8 / 2012 Sporn et al . 7 , 410 , 958 B2 8 / 2008 Krasutsky et al . 2012 /0238767 Al 9 / 2012 Jiang et al . 7 , 435 , 755 B2 10 /2008 Konopleva et al. 2012 /0245374 A1 9 / 2012 Anderson et al. 7 ,678 ,830 B2 3 / 2010 Honda et al. 2012 /0252776 A1 10 / 2012 Anderson et al. 7 , 795 ,305 B2 . 9 / 2010 Konopleva et al. 2012 / 0283450 A111 / 2012 Anderson et al. 7 , 863 ,327 B2 1 / 2011 Gribble et al . 2013 /0237721 AL 9 /2013 Gribble et al. 7 , 915 , 402 B2 3 / 2011 Anderson et al . 2013 / 0274480 A 10 /2013 Honda et al . 7 , 943 , 778 B2 5 / 2011 Jiang et al. 2013 /0317007 AL 11/ 2013 Anderson et al . 8 , 034 , 955 B2 10 /2011 Gribble et al . 2013/ 0324599 Al 12 / 2013 Anderson et al. 8 , 067 , 394 B2 11 / 2011 Honda et al . 2013 / 0345276 A112 / 2013 Sporn et al . 8 , 067 , 465 B2 11/ 2011 Honda et al. 2014 / 0066408 A1 3 / 2014 Jiang et al . 8 , 071 , 632 B2 12 /2011 Jiang et al . 2014 /0073700 A1 3 / 2014 Wagner et al . 8 , 088 ,824 B2 1 / 2012 Walling et al . 2014 / 0088163 A1 3 /2014 Jiang et al. 8 , 124 , 656 B2 2 / 2012 Anderson et al . 2014 /0088188 A1 3 /2014 Jiang et al. 8 , 124 , 799 B2 2 / 2012 Anderson et al . 2014 /0100227 Al 4 / 2014 Bender et al . 8 , 129 , 429 B2 3 /2012 Sporn et al . 2014 /0179928 Al 6 / 2014 Anderson et al . 8 , 258, 329 B2 9 / 2012 Anderson et al. 2014 /0275618 A1 9 / 2014 Gribble et al . 8 ,299 , 046 B2 10 / 2012 Sporn et al. 2015 /0080465 A1 3 / 2015 Chin et al. 8 , 309 ,601 B2 11/ 2012 Walling et al . 2015 /0148384 A1 5 / 2015 Anderson et al. 8 , 314 , 137 B2 11/ 2012 Honda et al . 2015 /0152071 Al 6 / 2015 Jiang et al. 8 , 338 ,618 B2 12/ 2012 Jiang et al. 2015 / 0259377 AL 9 /2015 Anderson et al . 8 ,394 , 967 B2 3 / 2013 Jiang et al. 2015 / 0376121 Al 12 /2015 Anderson et al . 8 , 440, 820 B2 5 / 2013 Anderson et al . 2016 / 0130220 Al 5 /2016 Anderson et al . 8 , 440 , 854 B2 5 / 2013 Anderson et al . 2016 /0145200 A15 /2016 Anderson et al . 8 , 455 , 544 B2 6 / 2013 Sporn et al. 8 , 586 , 775 B2 11/ 2013 Gribble et al . 8 , 747 , 901 B2 6 / 2014 Zhang et al . 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