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( 12 ) United States Patent US009963446B2 (12 ) United States Patent ( 10 ) Patent No. : US 9 ,963 , 446 B2 Burch et al. ( 45) Date of Patent: * May 8 , 2018 ( 54 ) OXEPAN - 2 - YL - PYRAZOL - 4 - YL 6 ,395 , 916 B1 5 /2002 Buchwald et al . HETEROCYCLYL - CARBOXAMIDE 6 , 946, 560 B2 9 / 2005 Buchwald et al. 7 , 026 , 498 B2 4 /2006 Buchwald et al . COMPOUNDS AND METHODS OF USE 7 , 223 , 879 B2 5 / 2007 Buchwald et al . 7 ,247 , 731 B2 7 / 2007 Buchwald et al . ( 71 ) Applicant: Genentech , Inc. , South San Francisco , 7 , 329, 758 B1 2 / 2008 Grubbs et al. CA (US ) 7 ,560 , 582 B2 . 7 / 2009 Buchwald et al. 7 , 858 ,784 B2 12 / 2010 Buchwald et al . (72 ) Inventors : Jason Burch , Pointe - Claire (CA ) ; 8 , 318 ,723 B2 * 11/ 2012 Mao CO7D 213/ 74 Huifen Chen , Burlingame, CA (US ) ; 514 /217 . 05 9 , 328 , 106 B2 * 5 / 2016 Burch .. .. .. .. .. .. .. C07D 417 / 14 Xiaojing Wang, Foster City , CA (US ) 2012 / 0225062 A1 9 / 2012 Burger et al . ( 73 ) Assignee: Genentech , Inc. , South San Francisco , 2013 /0079321 A1 3 /2013 Hodges et al . CA (US ) FOREIGN PATENT DOCUMENTS ( * ) Notice : Subject to any disclaimer, the term of this Wo 1996 /015111 Al 5 / 1996 patent is extended or adjusted under 35 WO 2007 / 044515 AL 4 / 2007 U . S .C . 154 ( b ) by 0 days . days . WO 2007 /099326 AL 9 /2007 WO 2011 / 124580 A 10 / 2011 This patent is subject to a terminal dis wo 2012 /004217 AL 1 / 2012 claimer . ( Continued ) (21 ) Appl. No. : 15 /266 , 243 OTHER PUBLICATIONS International Search Report issued in International Application No . ( 22) Filed : Sep . 15 , 2016 PCT/ EP2015 / 055596 , dated May 27, 2015 , in 4 pages. Written Opinion of the International Searching Authority issued in (65 ) Prior Publication Data International Application No. PCT/ EP2015 /055596 , dated May 27 , US 2017 /0001997 A1 Jan . 5 , 2017 2015 , in 7 pages. ( Author Not Identified ) Beilsteins Handbuch Der Organischen Related U . S . Application Data Chemie ( Table of Contents , total in 8 pages ), Prager et al ., 4th edition , Berlin : Julius Springer, vol. 2 ( 1920 ) . (63 ) Continuation of application No . (Author Not Identified ) Chiral Liquid Chromatography ( Table of PCT/ EP2015 / 055596 , filed on Mar. 18 , 2015 . Contents , total in 9 pages ), W . J . Lough , Glasgow : Blackie Academic & Professional ( 1989 ) . Provisional application No . 61 / 954 ,752 , filed on Mar. (Author Not Identified ) Comprehensive Heterocyclic Chemistry II (60 ) ( Table of Contents , in 4 pages ) , Katritzky et al ., Oxford , 18 , 2014 . UK :Elsevier Science Ltd . , vol. 3 ( 1996 ) . ( Author Not Identified ) Drug Stereochemistry : Analytical Methods (51 ) Int . CI. and Pharmacology ( Table of Contents only , in 5 pages ) , Irving W . C07D 417 / 14 ( 2006 .01 ) Wainer , Second edition , New York :Marcel Dekker , Inc . ( 1993 ) . A61K 31/ 427 ( 2006 . 01 ) (Continued ) A61K 31 /4439 ( 2006 .01 ) A61K 31 /4709 ( 2006 . 01 ) Primary Examiner — Yevgeny Valenrod A61K 31/ 497 ( 2006 .01 ) (74 ) Attorney , Agent, or Firm — Brian L . Buckwalter A61K 31/ 4985 ( 2006 . 01 ) (57 ) ABSTRACT A61K 31 /06 ( 2006 .01 ) Oxepan - 2 - yl pyrazol- 4 - yl- heterocyclyl - carboxamide com CO7D 487 /04 ( 2006 . 01 ) pounds of Formula 1 , including stereoisomers , geometric isomers , tautomers , and pharmaceutically acceptable salts A61K 45 / 06 ( 2006 . 01) thereof, wherein X is thiazolyl, pyrazinyl , pyridinyl, or (52 ) U . S . CI. pyrimidinyl, are useful for inhibiting Pim kinase , and for CPC . .. .. .. C07 417 / 14 (2013 .01 ) ; A61K 31 /427 treating disorders such as cancer mediated by Pim kinase . ( 2013 .01 ) ; A61K 31 /4439 ( 2013 . 01 ) ; A61K Methods of using compounds of Formula I for in vitro , in 31/ 4709 ( 2013 .01 ) ; A61K 31/ 497 ( 2013 .01 ) ; situ , and in vivo diagnosis , prevention or treatment of such A61K 31/ 4985 ( 2013 .01 ) ; A61K 45 / 06 disorders in mammalian cells , or associated pathological (2013 .01 ); C07D 487/ 04 ( 2013 .01 ) conditions, are disclosed . (58 ) Field of Classification Search CPC . .. .. .. .. .. A61K 31/ 427 ; A61K 31 /4439 ; A61K 31/ 4709 ; A61K 31 /497 ; A61K 31 / 4985 ; A61K 45 /06 ; CO7D 417 / 14 ; C07D 487 / 04 USPC . .. .. .. .. .. .. .. .. 514 / 249 RI See application file for complete search history . ( 56 ) References Cited U . S . PATENT DOCUMENTS NH 3 ,773 , 919 A 11/ 1973 Boswell et al . 07x 6 , 111, 121 A 8 / 2000 Grubbs et al. 6 , 307 ,087 B1 10 / 2001 Buchwald et al. 21 Claims, 6 Drawing Sheets US 9 , 963 ,446 B2 Page 2 References Cited De Bruin et al ., “ Anti -HERG Activity and the Risk of Drug - Induced ( 56 ) Arrhythmias and Sudden Death ” , European Heart Journal, 26 :590 597 (2005 ) . FOREIGN PATENT DOCUMENTS Dhanasekaran et al ., “ Delineation of prognostic biomarkers in wo 2013 /045461 AL 4 / 2013 prostate cancer ” , Nature , 412 (6849 ) :822 - 826 ( Aug . 23 , 2001 ) . WO 2014 / 048939 AL 4 / 2014 Eliel et al. , Stereochemistry of Organic Compounds, “ 7 - 3 . Chemical Separation of Enantiomers Via Diastereomers ” , New York : John Wiley & Sons, Inc. , 322 -381 ( 1994 ) . OTHER PUBLICATIONS Ellwood - Yen et al ., “ Myc -driven murine prostate cancer shares (Author Not Identified ) Remington ' s Pharmaceutical Sciences molecular features with human prostate tumors ” , Cancer Cell, ( Table of Contents , total in 4 pages) , Osol et al. , 16th edition , 4 ( 3 ) : 223 - 238 (Sep . 2003 ) . Easton , Pennsylvania :Mack Publishing Company ( 1980 ) . Emmons et al. , The Chemistry of Heterocyclic Compounds, A ( Author Not Identified ) Remington ' s Pharmaceutical Sciences Series of Monographs ( Table of Contents , total in 14 pages ) , ( Table of Contents , total in 6 pages ), Osol et al. , 15th edition , Weissberger, New York , NY, USA : Interscience Publishers , Inc ., vol. Easton , PA :Mack Publishing Company ( 1975 ) . 19 ( 1964 ) . ( Author Not Identified ) , “ International Union of Pure and Applied Ferroni et al . , " Cyclic Guanidines : Synthesis and Antiplatelet Activ Chemistry ” , Journal of The American Chemical Society , 82 : 5566 ity of 4 ,6 , 7 , 8 - Tetrahydro - 1H - imidazo [ 1 , 2 - a ]pyrazolo [ 3 , 4 5572 ( 1960 ) . d ]pyrimidin - 7 -ones and 1 , 4 , 6 , 7 , 8 , 9 -Hexahydropyrazolo Adam et al. , “ Targeting PIM Kinases Impairs Survival of [ 3 ', 4 ": 4 , 5 ]pyrimido [ 2 , 1 - c ] [ 1 , 2 , 4 ] triazin - 7 - ones ” , Arzneim . - Forsch ./ Hematopoietic Cells Transformed by Kinase Inhibitor - Sensitive and Drug Res , 40 :1328 - 1331 (1990 ) . Kinase Inhibitor -Resistant Forms of Fms- Like Tyrosine Kinase 3 Fox et al . , “ The Serine / Threonine Kinase Pim - 2 is a Transcription and BCR /ABL ” , Cancer Res , 66 ( 7 ) : 3828 - 3835 ( Apr. 2006 ) . ally Regulated Apoptotic Inhibitor” , Genes & Development , Aho et al ., “ Expression of Human pim Family Genes is Selectively 17 : 1841 - 1854 (2003 ) . up - regulated by Cytokines Promoting T Helper Type 1 , but not T Fujii et al. , " Aberrant Expression of Serine / Threonine Kinase Pim - 3 Helper Type 2 , Cell Differentiation ” , Immunology , 116 : 82 - 88 in Hepatocellular Carcinoma Development and its Role in the ( 2005 ) . Proliferation of Human Hepatoma Cell Lines ” , International Journal Aho et al ., “ Pim - 1 Kinase Promotes Inactivation of the Pro of Cancer, 114 :209 - 218 (2005 ) . Apoptotic Bad Protein by Phosphorylating it on the Ser112 Gate Green et al. , Protective Groups in Organic Synthesis ( Table of keeper Site ” , FEBS Letters, 571: 43 -49 ( 2004 ) . Contents only , in 4 pages ), Second edition , New York : John Wiley & Aksoy et al ., “ Self -Renewal of Murine Embryonic Stem Cells is Sons , Inc . ( 1991 ) . Supported by the Serine / Threonine Kinases Pim - 1 and Pim - 3 ” , Greene et al. Protective Groups in Organic Syntheis ( Table of Stem Cells, 25 :2996 -3004 ( 2007 ) . Contents , in 4 pages) , 3rd edition , New York , NY, USA : John Wiley Allen et al . , " Pim - 2 Transgene Induces Lymphoid Tumors , Exhib & Sons , Inc . ( 1999 ) . iting Potent Synergy with c -myc ” , Oncogene, 15 : 1133 - 1141 ( 1997 ) . Greenstein et al. , “ Characterization of the MM . 1 Human Multiple Amson et al. , “ The Human Protooncogene Product p33pim is Myeloma (MM ) Cell Liness : A Model System to Elucidate the Expressed During Fetal Hematopoiesis and in Diverse Leukemias” , Characteristics , Behavior, and Signaling of Steroid -Sensitive and Proc . Natl . Acad . Sci . USA , 86 : 8857 -8861 ( 1989 ) . Resistant MM Cells” , Experimental Hematology , 31 : 271 - 282 Bachmann et al. , “ The Oncogenic Serine / Threonine Kinase Pim - 1 Directly Phosphorylates and Activates the G2 / M Specific ( 2003 ) . Phosphatase Cdc25C ” , The International Journal of Biochemistry & Hammerman et al. , “ Pim and Akt oncogenes are independent Cell Biology 38 :430 -443 ( 2006 ) . regulators of hematopoietic cell growth and survival” , Blood , Barnes et al . , The Chemistry of Heterocyclic Compounds, A Series 105 ( 11 ) : 4477 -4483 ( 2005 ) . of Monographs ( Table of Contents, total in 8 pages ) , Weissberger , Hedley et al. , “ The Genetic Basis of Long QT and Short QT New York , NY, USA : Interscience Publishers , Inc. , vol. 14 ( 1960 ) . Syndromes : A Mutation Update ” , Human Mutation , 30 ( 11 ) : 1486 Billingsley et al . , “ Pallaium - Catalyzed Borylation of Aryl Chlo 1511 (2009 ) . rides: Scope , Applications, and Computational Studies ” , Hirano et al ., “ Roles of STAT3 in Mediating the Cell Growth , Angewandte Chemie Int. Ed , . 46 :5359 - 5363 (2007 ) . Differentiation and Survival Signals Relayed Through the IL - 6 Biscoe et al. , “ A New Class of Easily Activated Palladium Family of Cytokine Receptors ”
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