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Tani Muu a Ta Materia Na Mama Na Mama Na Mtoto TANI MUU ATA MATERIAUS009834545B2 NA MAMA NA MAMA NA MTOTO (12 ) United States Patent ( 10 ) Patent No. : US 9 , 834 ,545 B2 Chen et al. ( 45 ) Date of Patent: Dec. 5 , 2017 ( 54 ) MODULATORS OF CHEMOKINE ( 58 ) Field of Classification Search RECEPTORS None See application file for complete search history. ( 71) Applicant : CHEMOCENTRYX , INC . , Mountain View , CA (US ) ( 56 ) References Cited (72 ) Inventors : Xi Chen , E . Palo Alto , CA (US ); Dean U . S . PATENT DOCUMENTS R . Dragoli , Los Altos, CA ( US ) ; Junfa 6 , 166 ,050 A 12 /2000 Lombardo et al. Fan , Palo Alto , CA (US ); Jaroslaw 2003 /0204085 A1 10 / 2003 Taveras et al. Kalisiak , Mountain View , CA (US ) ; 2004 / 0097547 AL 5 / 2004 Taveras et al . Antoni Krasinski, Sunnyvale , CA 2004 /0106794 Al 6 / 2004 Taveras et al. (US ) ; Manmohan Reddy Leleti, San 2004 /0147559 Al 7 / 2004 Taveras et al. 2004 /0209946 Al 10 / 2004 Yin et al . Jose , CA (US ) ; Venkat Mali, 2008 / 0261917 A1 10 / 2008 Willems et al . Cupertino , CA (US ) ; Jeffrey 2009 / 0306079 Al 12 / 2009 Taveras et al. McMahon , San Francisco , CA (US ) ; 2010 / 0029670 A1 2 /2010 Baettig et al . Rajinder Singh , Belmont, CA (US ) ; 2010 /0267712 Al 10 / 2010 Heemskerk et al . 2011 / 0086842 Al 4 / 2011 Stadtmueller et al. Hiroko Tanaka , Mountain View , CA 2011 / 0213029 Al 9 / 2011 Taveras et al. (US ) ; Ju Yang , Palo Alto , CA (US ) ; 2013 / 0231393 A1 9 / 2013 Aubert Chao Yu , Sunnyvale , CA (US ) ; Penglie 2014 /0296254 Al 10 / 2014 Musicki et al . Zhang , Foster City , CA (US ) 2014 / 0309208 A 10 / 2014 Musicki et al . 2015 /0087675 Al 3 /2015 Musicki et al . (73 ) Assignee : CHEMOCENTRYX , INC ., Mountain 2017 /0144996 Al 5 /2017 Chen et al . View , CA (US ) FOREIGN PATENT DOCUMENTS ( * ) Notice: Subject to any disclaimer, the term of this WO 01/ 64208 AL 9 / 2001 patent is extended or adjusted under 35 wo 01/ 92202 Al 12 / 2001 U . S . C . 154 (b ) by 0 days . WO 02 /057230 AL 7 / 2002 WO 02 / 067919 AL 9 / 2002 WO 02 / 076926 AL 10 / 2002 ( 21 ) Appl. No .: 15 / 353, 889 WO 02 / 083624 Al 10 / 2002 WO 03 /080053 AL 10 / 2003 ( 22 ) Filed : Nov . 17 , 2016 WO 2004 /011418 AL 2 /2004 wo 2005 /075447 AL 8 / 2005 (65 ) Prior Publication Data Wo 2006 /021544 AL 3 /2006 US 2017 /0144997 A1 May 25, 2017 ( Continued ) OTHER PUBLICATIONS Related U . S . Application Data Aki, Cynthia et al. , “ Diaminocyclobutenediones as potent and orally (60 ) Provisional application No . 62/ 257 , 389, filed on Nov. available CXCR2 receptor antagonists : SAR in the phenolic amide 19 , 2015 , provisional application No . 62/ 277 ,711 , region , " Bioorganic & Medicinal Chemistry Letters (available filed on Jan . 12 , 2016 . online May 18 , 2009 ) ; 19 :4446 - 4449 . (Continued ) (51 ) Int. Cl. C07D 405 / 14 ( 2006 . 01 ) Primary Examiner — Brian J Davis A61K 31 / 506 ( 2006 .01 ) ( 74 ) Attorney , Agent, or Firm — Mintz Levin Cohn Ferris A61K 31 /4155 ( 2006 .01 ) Glovsky and Popeo PC A61K 31 /4439 ( 2006 .01 ) A61K 31 / 454 ( 2006 .01 ) (57 ) ABSTRACT A61K 31 /341 ( 2006 .01 ) Compounds are provided as chemokine inhibitors having A61K 31 / 4035 ( 2006 .01 ) the structure : A61K 45 / 06 ( 2006 . 01 ) C07D 209 /46 (2006 .01 ) C07D 307 / 52 ( 2006 . 01 ) C07D 405 / 12 ( 2006 .01 ) RSa R56 A61K 31/ 4725 ( 2006 .01 ) (52 ) U . S . CI. 7 CPC .. .. .. .. C07D 405 / 14 (2013 .01 ) ; A61K 31 /341 N Jo ( 2013 .01 ) ; A61K 31/ 4035 ( 2013 .01 ) ; A61K ROS 31/ 4155 (2013 . 01 ) ; A61K 31 /4439 ( 2013 .01 ) ; A61K 31/ 454 (2013 . 01 ) ; A61K 31/ 4725 ROA ( 2013 .01 ) ; A61K 31/ 506 ( 2013 .01 ) ; A61K 45 / 06 ( 2013 .01 ) ; C07D 209 / 46 ( 2013 . 01 ) ; C07D 307 / 52 (2013 . 01 ) ; CO7D 405 / 12 ( 2013 .01 ) 33 Claims, 38 Drawing Sheets US 9 ,834 ,545 B2 Page 2 (56 ) References Cited Gunda, Shravan Kumar et al. , “ Structural investigations of CXCR2 receptor antagonists by COMFA , COMSIA and flexible docking FOREIGN PATENT DOCUMENTS studies , ” Acta Pharm ( Jul. 17 , 2012 ) ; 62 : 287 - 304 . Lai, Gaifa et al. , “ Synthesis and structure -activity relationships of wo 2008 /005570 AL 1 /2008 new disubstiuted phenyl -containing 3 , 4 -diamino - 3 - cyclobutene WO 2008 / 109178 A1 9 / 2008 WO 2008 / 109179 Al 9 / 2008 1 , 2 - diones as CXCR2 receptor antagonists , Bioorganic & wo 2008 / 148790 Al 12 / 2008 Medicinal Chemistry Letters (available online Feb . 10 , 2008 ) ; WO 2009 /005801 A1 1 / 2009 18: 1864 - 1868 . WO 2009 /005802 A1 1 / 2009 Liu , Shilan et al. , “ Design , synthesis , and evaluation of novel WO 2009 /012375 A2 1 / 2009 3 -amino - 4 -hydrazine -cyclobut - 3 -ene - 1 , 2 -diones as potent and WO 2009 /073683 A2 6 / 2009 WO 2009 / 156421 Al 12 / 2009 selective CXCR2 chemokine receptor antagonists, ” Bioorganic & WO 2010 / 0045303 A2 4 / 2010 Medicinal Chemistry Letters (available online Aug . 7 , 2009 ) ; WO 2010 /063802 Al 6 / 2010 19 : 5741 -5745 . WO 2010 /091543 A1 8 / 2010 WO 2010 / 131145 Al 11 / 2010 McCleland , Brent W . et al. , “ Comparison of N , N -diarylsquaramides WO 2010 / 131147 Al 11 / 2010 and N , N -diarylureas as antagonists of the CXCR2 chemokine WO 2012 /001076 A1 1 / 2012 receptor ,” Bioorganic & Medicinal Chemistry Letters (2007 ; avail W0 2012 /080456 A1 6 / 2012 WO 2012 /080457 A1 6 / 2012 able online Dec . 23 , 2006 ) ; 17 : 1713 - 1717 . WO 2013 /030803 Al 3 / 2013 Merritt , J . Robert et al . , “ Synthesis and structure -activity relation WO 2013 /061002 A1 5 / 2013 ships of 3 , 4 -diaminocyclobut - 3 -ene - 1 , 2 -dione CXCR2 wo 2013 /061004 A1 5 / 2013 antagonists ,” Bioorganic & Medicinal Chemistry Letters ( available WO 2013 / 061005 A1 5 / 2013 WO 2013 / 174947 AL 11 / 2013 online May 11 , 2006 ) ; 16 : 4107 -4110 . WO 2016 / 079049 Al 5 / 2016 Wijtmans, Maikel et al. , “ Therapeutic targeting of chemokine receptors by small molecules, " Drug Discovery Today : Technolo OTHER PUBLICATIONS gies (2012 ; http : // dx .doi . org / 10 . 1016 / j .ddtec .2012 .03 .004 ) ; 9 ( 4 ) : e229 -e236 . Asadollahi, Tahereh et al. , “ QSAR Models for CXCR2 Receptor Yu , Younong et al. , “ Synthesis and structure -activity relationships of Antagonists Based on the Genetic Algorithm for Data Preprocessing heteroaryl substituted - 3 , 4 - diamino - 3 - cyclobut- 3 - ene- 1 , 2 -dione Prior to Application of the PLS Linear Regression Method and CXCR2/ CXCR1 receptor antagonists , ” Bioorganic & Medicinal Design of the New Compounds Using In Silico Virtual Screening , " Molecules (Feb . 25 , 2011 ) ; 16 : 1928 - 1955 . Chemistry Letters ( available online Jan . 11, 2008 ); 18 : 1318 - 1322. Biju , Purakkattle et al. , “ 3 , 4 -Diamino - 2 , 5 - thiadiazole - 1 -oxides as Zhang , Shuang et al. , " Comparative Analysis of Pharmacophore potent CXCR2 / CXCR1 antagonists ,” Bioorganic & Medicinal Features and Quantitative Structure - Activity Relationships for Chemistry Letters ( 2008; available online Oct. 30 , 2007) ; 18 : 228 CD38 Covalent and Non -covalent Inhibitors , " Chemical Biology & 231 . Biju , Purakkattle et al ., “ Fluoroalkyl a side chain containing Drug Design (Dec . 2015 ; first published Jul. 14 , 2015 ) ; 86 ( 6 ) : 1411 3 , 4 - diamino - cyclobutenediones as potent and orally bioavailable 1424 . CXCR2 -CXCR1 dual antagonists , " Bioorganic & Medicinal Zhou , Yi et al. , “ Design , Synthesis and Biological Evaluation of Chemistry Letters (available online Jan . 15 , 2009 ) ; 19 : 1431 - 1433 . Noncovalent Inhibitors of Human CD38 NADase ,” ChemMedChem Biju , Purakkattle et al . , “ 3 , 4 - Diamino - 1 , 2 , 5 - thiadizole as potent and selective CXCR2 antagonists , ” Bioorganic & Medicinal Chemistry ( Feb . 6 , 2012 ) ; 7 ( 2 ) :223 -228 . Letters ( available online Jan . 15 , 2009 ) ; 19 : 1434 - 1437 . International Search Report and Written Opinion corresponding to Busch - Petersen , Jakob et al. , “ Phenol -containing antagonists of the PCT Application No . PCT/ US2016 /062417 dated Jan . 12 , 2017 , 12 CXCR2 receptor, ” Expert Opin . Ther. Patents ( published online pages May 26 , 2008 ) ; 18 ( 6 ) :629 -637 . International Search Report and Written Opinion corresponding to Chao , Jianhua et al. , “ C ( 4 ) -alkyl substituted furanyl cyclobutenediones as potent, orally bioavailable CXCR2 and PCT Application No. PCT/ US2016 /062427 dated Feb . 21 , 2017 ; 9 CXCR1 receptor antagonists ,” Bioorganic & Medicinal Chemistry pages . Letters ( available online Apr. 10 , 2007 ) ; 17: 3778 - 3783 . Barbosa , Maria Leticia de Castro et al ., “ Therapeutic approaches for Dwyer, Michael P . et al . , “ Discovery of 2 -Hydrozy - N , N - dimethyl tumor necrosis factor inhibition ,” Brazilian Journal of Pharmaceuti 3 - 12 - [ [ ( R ) - 1 - ( 5 -methylfuran - 2 - yl ) propyl) amino ] - 3 , 4 - dioxo cyclobut - 1 - enylamino )benzamide (SCH 527123 ) : A Potent, Orally cal Sciences ( Jul. / Sep . 2011; accepted for pub May 25, 2011 ) ; Bioavailable CXCR2/ CXCR1 Receptor Antagonist ,” J . Med . Chem . 47 : 427 -446 . ( Aug. 9 , 2006 ) ; 49 ( 26 ) : 7603 - 7606 . Nieuwenhuis , S . A . M . et al ., “ Structure of the Y , Tyrosine Radical Ebsworth , Karen et al ., " Chemokine Receptor Inhibition as a Novel in Photosystem II. Determination of the Orientation of the Phenoxyl Therapeutic Approach for Psoriasis ," Poster No . 521 Ring by Enantioselective Deuteration of the Methylene Group , " J . ChemoCentryx , Inc. , Mountain View , CA (May 12 , 2016 ) ; 2 pages. Am . Chem . Soc . ( Jan . 16 , 1998 ) ; 120: 829- 830 . U . S . Patent Dec . 5 , 2017 Sheet 1 of 38 US 9 ,834 , 545 B2 FIGURE 1A CCR6 IC50 CXCR2 IC50 O . 1 . 000 +to +uffin + ++ + ToCOHCOH 0 0 1 . 001 + + + * * * 1 .002 Nto + + + + + + -???
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