Title:
TETRAHYDROBENZOFURODIAZEPINONE COMPOUNDS AND PHARMACEUTICAL APPLICATIONS THEREOF
Document Type and Number:
WIPO Patent Application WO/2022/075240
Kind Code:
A1
Abstract:
The present invention provides compounds that have a Pim-1 inhibitory activity. The present invention provides, inter alia, compounds with formula [I] and their pharmaceutically acceptable salts, pharmaceutical compositions containing the same, and pharmaceutical applications thereof. (The symbols in the formula are as defined in the Description.)
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Inventors:
INOUE MASAFUMI (JP)
OGOSHI YOSUKE (JP)
FURUKAWA TAKAYUKI (JP)
MACHIDA TAKUYA (JP)
MITANI IKUO (JP)
HARADA KAZUHITO (JP)
NAKAGAWA YUICHI (JP)
YAMAOKA NOBUTAKA (JP)
OGOSHI YOSUKE (JP)
FURUKAWA TAKAYUKI (JP)
MACHIDA TAKUYA (JP)
MITANI IKUO (JP)
HARADA KAZUHITO (JP)
NAKAGAWA YUICHI (JP)
YAMAOKA NOBUTAKA (JP)
Application Number:
PCT/JP2021/036553
Publication Date:
April 14, 2022
Filing Date:
October 04, 2021
Export Citation:
Assignee:
JAPAN TOBACCO INC (JP)
International Classes:
C07D491/048; A61K31/551; A61P9/12; A61P11/00; A61P17/06; A61P35/00; A61P43/00; C07D491/107; C07D519/00
Domestic Patent References:
| WO2002014324A2 | 2002-02-21 | |||
| WO2009086264A1 | 2009-07-09 |
Other References:
AMY LEW TSUHAKO; DAVID S. BROWN; ELENA S. KOLTUN; NAING AAY; ARLYN ARCALAS; VICKY CHAN; HONGWANG DU; STEFAN ENGST; MAURIZIO FRANZI: "The design, synthesis, and biological evaluation of PIM kinase inhibitors", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, ELSEVIER, AMSTERDAM, NL, vol. 22, no. 11, AMSTERDAM, NL , pages 3732 - 3738, XP028423353, ISSN: 0960-894X, DOI: 10.1016/j.bmcl.2012.04.025
LI WEI, WAN XIAOBO, ZENG FANQI, XIE YUTING, WANG YANLI, ZHANG WEI, LI LI, HUANG NIU: "More than just a GPCR ligand: structure-based discovery of thioridazine derivatives as Pim-1 kinase inhibitors", MEDCHEMCOMM, ROYAL SOCIETY OF CHEMISTRY, UNITED KINGDOM, vol. 5, no. 4, 1 January 2014 (2014-01-01), United Kingdom , pages 507 - 511, XP055919716, ISSN: 2040-2503, DOI: 10.1039/C4MD00030G
LAURENT BRAULTCHRISTELLE GASSERFRANZ BRACHERKILIAN HUBERSTEFAN KNAPPJUERG SCHWALLERL: "PIM serine/threonine kinases in the pathogenesis and therapy of hematologic malignancies and solid cancers", HAEMATOLOGICA, vol. 95, no. 6, June 2010 (2010-06-01), pages 1004 - 15
PATRIZIA MONDELLOSALVATORE CUZZOCREAMICHAEL MIAN: "Pim kinases in hematological malignancies: where are we now and where are we going?", J HEMATOL ONCOL., vol. 7, no. 95, 10 December 2014 (2014-12-10)
SE'BASTIEN RENARD, ROXANE PAULIN, SANDRA BREUILS-BONNET, SERGE SIMARD, PHILIPPE PIBAROT, SE'BASTIEN BONNET, AND STEEVE PROVENCHER: "A new biomarker in pulmonary arterial hypertension", PULM CIRC., vol. 3, no. 1, January 2013 (2013-01-01), pages 74 - 81
ROXANE PAULIN, MSC; AUDREY COURBOULIN,MSC; JOLYANE MELOCHE, BSC; VINCENT MAINGUY, MSC; ERIC DUMAS DE LA ROQUE, MD; NEHME' SAKSOUK,: "PhD:Signal Transducers and Activators of Transcription-3/Pim1 Axis Plays a Critical Role in the Pathogenesis of Human Pulmonary Arterial Hypertension", CIRCULATION, vol. 123, no. 11, 22 March 2011 (2011-03-22), pages 1205 - 15
RICHARD ZANGJOCELYN HOLASHMATTHEW T.: "Burger:Pan-PIM Kinase Inhibition Provides a Novel Therapy for Treating Hematologic Cancers", CLIN CANCER RES., vol. 20, no. 7, 1 April 2014 (2014-04-01), pages 1834 - 45, XP055139356, DOI: 10.1158/1078-0432.CCR-13-2062
YONG-HAI PENGJIAN-JUN LIFANG-WEI XIEJIAN-FANG CHENYING-HAO YUXUE-NONG OUYANGHOUJIE LIANG: "Expression of pim-1 in Tumors, Tumor Stroma and Tumor-Adjacent Mucosa Co-Determines the Prognosis of Colon Cancer Patients", PLOS ONE, vol. 8, no. 10, 7 October 2013 (2013-10-07), pages e76693
JIANWEI XUGUANGBING XIONGZHE CAOHUA HUANGTIANXIAO WANGLEI YOULI ZHOULIANFANG ZHENGYA HUTAIPING ZHANG: "PIM-1 contributes to the malignancy of pancreatic cancer and displays diagnostic and prognostic value", J EXP CLIN CANCER RES., vol. 35, no. 1, 5 September 2016 (2016-09-05), pages 133
T L CIBULLT D JONESL LIJ N EBLEL ANN BALDRIDGES R MALOTTY LUOL CHENG: "Overexpression of Pim-1 during progression of prostatic adenocarcinoma", J CLIN PATHOL., vol. 59, no. 3, March 2006 (2006-03-01), pages 285 - 8
SHENGJIE GUOXIAOPENG MAOJUNXING CHENBIN HUANGCHU JINZHENBO XUSHAOPENG QIU: "Overexpression of Pim-1 in bladder cancer", J EXP CLIN CANCER RES., vol. 29, 11 December 2010 (2010-12-11), pages 161, XP021091191, DOI: 10.1186/1756-9966-29-161
YUNFEI LIAOYONG FENGJACSON SHENYAN GAOGREGORY COTEEDWIN CHOYDAVID HARMONHENRY MANKINFRANCIS HORNICEKZHENFENG DUAN: "Clinical and biological significance of PIM1 kinase in osteosarcoma", J ORTHOP RES., vol. 34, no. 7, July 2016 (2016-07-01), pages 1185 - 94
HORIUCHI DCAMARDA RZHOU AYYAU CMOMCILOVIC 0BALAKRISHNAN SCORELLA ANEYOB HKESSENBROCK KLAWSON DA: "PIM1 kinase inhibition as a targeted therapy against triple-negative breast tumors with elevated MYC expression", NAT MED., vol. 22, no. 11, November 2016 (2016-11-01), pages 1321 - 1329, XP055683797, DOI: 10.1038/nm.4213
ULRIKE WEIRAUCHNADINE BECKMANNMAREN THOMASARNOLD GRUNWELLERKILIAN HUBERFRANZ BRACHERROLAND K. HARTMANNACHIM AIGNER: "Functional Role and Therapeutic Potential of the Pim-1 Kinase in Colon Carcinoma", NEOPLASIA, vol. 15, no. 7, July 2013 (2013-07-01), pages 783 - 94
PERERA GKAINALI CSEMENOVA EHUNDHAUSEN CBARINAGA GKASSEN DWILLIAMS AEMIRZA MMBALAZS MWANG X: "Integrative biology approach identifies cytokine targeting strategies for psoriasis", SCI TRANSL MED., vol. 6, no. 223, 12 February 2014 (2014-02-12), pages 223ra22
HUI CHENGCHONGMEI HUANGXIAOQIAU XUXIAOXIA HUSHENGLAN GONGGUSHENG TANGXIANIMN SONGWEIPING ZHANGJIANMIN WANGLI CHEN: "PIM-1 mRNA expression is a potential prognostic biomarker in acute myeloid leukemia", J TRANSL MED., vol. 15, 2017, pages 179
RUI-FANG FANYING LUZHI-GANG FANGXIAO-YAN GUOYU-XIN CHENYI-CHUAN XUYA-MEI LEIKE-FANG LIUDONG-JUN LINLING-LING LIU: "PIM-1 kinase inhibitor SMI-4a exerts antitumor effects in chronic myeloid leukemia cells by enhancing the activity of glycogen synthase kinase 3β", MOL MED REP., vol. 16, no. 4, October 2017 (2017-10-01), pages 4603 - 4612
HOLLY KOBLISHYUN-LONG LINIU SHINLESILE HALLQIAN WANGKATHY WANGMARYANNE COVEINGTONCINDY MARANDOKEVIN BOWMANJASON BOER: "Preclinical characterization of INCB053914, a novel pan-PIM Kinase inhibitor, alone and in combination with anticancer agents, in models of hematologic malignancies", PLOS ONE, vol. 13, no. 6, 21 June 2018 (2018-06-21), pages e0199108
GARY W. REUTHER: "The pan-PIM inhibitor INCB053914 displays potent synergy in combination with ruxolitinib in models of MPN", BLOOD ADV., vol. 3, no. 22, 26 November 2019 (2019-11-26), pages 3503 - 3514
RONG FU MD, PHDYONG XIA MD, PHDMEIRONG LI BSRENXIANG MAO MDCHAOHUAN GUO MDMIANJING ZHOU MDHECHANG TAN MD, PHDMEILING LIU BSSHUANG : "Pim-1 as a Therapeutic Target in Lupus Nephritis", ARTHRITIS RHEUMATOL ., vol. 71, no. 8, August 2019 (2019-08-01), pages 1308 - 1318
BERGE ET AL., J. PHARM. SCI., vol. 66, 1977, pages 1 - 19
STAHL ET AL.: "Handbook of Pharmaceutical Salt: Properties, Selection, and Use", 2002, WILEY-VCH
PAULEKUHN ET AL., J. MED. CHEM., vol. 50, 2007, pages 6665 - 6672
"NCBI", Database accession no. NM_002648.3
LI WEI, WAN XIAOBO, ZENG FANQI, XIE YUTING, WANG YANLI, ZHANG WEI, LI LI, HUANG NIU: "More than just a GPCR ligand: structure-based discovery of thioridazine derivatives as Pim-1 kinase inhibitors", MEDCHEMCOMM, ROYAL SOCIETY OF CHEMISTRY, UNITED KINGDOM, vol. 5, no. 4, 1 January 2014 (2014-01-01), United Kingdom , pages 507 - 511, XP055919716, ISSN: 2040-2503, DOI: 10.1039/C4MD00030G
LAURENT BRAULTCHRISTELLE GASSERFRANZ BRACHERKILIAN HUBERSTEFAN KNAPPJUERG SCHWALLERL: "PIM serine/threonine kinases in the pathogenesis and therapy of hematologic malignancies and solid cancers", HAEMATOLOGICA, vol. 95, no. 6, June 2010 (2010-06-01), pages 1004 - 15
PATRIZIA MONDELLOSALVATORE CUZZOCREAMICHAEL MIAN: "Pim kinases in hematological malignancies: where are we now and where are we going?", J HEMATOL ONCOL., vol. 7, no. 95, 10 December 2014 (2014-12-10)
SE'BASTIEN RENARD, ROXANE PAULIN, SANDRA BREUILS-BONNET, SERGE SIMARD, PHILIPPE PIBAROT, SE'BASTIEN BONNET, AND STEEVE PROVENCHER: "A new biomarker in pulmonary arterial hypertension", PULM CIRC., vol. 3, no. 1, January 2013 (2013-01-01), pages 74 - 81
ROXANE PAULIN, MSC; AUDREY COURBOULIN,MSC; JOLYANE MELOCHE, BSC; VINCENT MAINGUY, MSC; ERIC DUMAS DE LA ROQUE, MD; NEHME' SAKSOUK,: "PhD:Signal Transducers and Activators of Transcription-3/Pim1 Axis Plays a Critical Role in the Pathogenesis of Human Pulmonary Arterial Hypertension", CIRCULATION, vol. 123, no. 11, 22 March 2011 (2011-03-22), pages 1205 - 15
RICHARD ZANGJOCELYN HOLASHMATTHEW T.: "Burger:Pan-PIM Kinase Inhibition Provides a Novel Therapy for Treating Hematologic Cancers", CLIN CANCER RES., vol. 20, no. 7, 1 April 2014 (2014-04-01), pages 1834 - 45, XP055139356, DOI: 10.1158/1078-0432.CCR-13-2062
YONG-HAI PENGJIAN-JUN LIFANG-WEI XIEJIAN-FANG CHENYING-HAO YUXUE-NONG OUYANGHOUJIE LIANG: "Expression of pim-1 in Tumors, Tumor Stroma and Tumor-Adjacent Mucosa Co-Determines the Prognosis of Colon Cancer Patients", PLOS ONE, vol. 8, no. 10, 7 October 2013 (2013-10-07), pages e76693
JIANWEI XUGUANGBING XIONGZHE CAOHUA HUANGTIANXIAO WANGLEI YOULI ZHOULIANFANG ZHENGYA HUTAIPING ZHANG: "PIM-1 contributes to the malignancy of pancreatic cancer and displays diagnostic and prognostic value", J EXP CLIN CANCER RES., vol. 35, no. 1, 5 September 2016 (2016-09-05), pages 133
T L CIBULLT D JONESL LIJ N EBLEL ANN BALDRIDGES R MALOTTY LUOL CHENG: "Overexpression of Pim-1 during progression of prostatic adenocarcinoma", J CLIN PATHOL., vol. 59, no. 3, March 2006 (2006-03-01), pages 285 - 8
SHENGJIE GUOXIAOPENG MAOJUNXING CHENBIN HUANGCHU JINZHENBO XUSHAOPENG QIU: "Overexpression of Pim-1 in bladder cancer", J EXP CLIN CANCER RES., vol. 29, 11 December 2010 (2010-12-11), pages 161, XP021091191, DOI: 10.1186/1756-9966-29-161
YUNFEI LIAOYONG FENGJACSON SHENYAN GAOGREGORY COTEEDWIN CHOYDAVID HARMONHENRY MANKINFRANCIS HORNICEKZHENFENG DUAN: "Clinical and biological significance of PIM1 kinase in osteosarcoma", J ORTHOP RES., vol. 34, no. 7, July 2016 (2016-07-01), pages 1185 - 94
HORIUCHI DCAMARDA RZHOU AYYAU CMOMCILOVIC 0BALAKRISHNAN SCORELLA ANEYOB HKESSENBROCK KLAWSON DA: "PIM1 kinase inhibition as a targeted therapy against triple-negative breast tumors with elevated MYC expression", NAT MED., vol. 22, no. 11, November 2016 (2016-11-01), pages 1321 - 1329, XP055683797, DOI: 10.1038/nm.4213
ULRIKE WEIRAUCHNADINE BECKMANNMAREN THOMASARNOLD GRUNWELLERKILIAN HUBERFRANZ BRACHERROLAND K. HARTMANNACHIM AIGNER: "Functional Role and Therapeutic Potential of the Pim-1 Kinase in Colon Carcinoma", NEOPLASIA, vol. 15, no. 7, July 2013 (2013-07-01), pages 783 - 94
PERERA GKAINALI CSEMENOVA EHUNDHAUSEN CBARINAGA GKASSEN DWILLIAMS AEMIRZA MMBALAZS MWANG X: "Integrative biology approach identifies cytokine targeting strategies for psoriasis", SCI TRANSL MED., vol. 6, no. 223, 12 February 2014 (2014-02-12), pages 223ra22
HUI CHENGCHONGMEI HUANGXIAOQIAU XUXIAOXIA HUSHENGLAN GONGGUSHENG TANGXIANIMN SONGWEIPING ZHANGJIANMIN WANGLI CHEN: "PIM-1 mRNA expression is a potential prognostic biomarker in acute myeloid leukemia", J TRANSL MED., vol. 15, 2017, pages 179
RUI-FANG FANYING LUZHI-GANG FANGXIAO-YAN GUOYU-XIN CHENYI-CHUAN XUYA-MEI LEIKE-FANG LIUDONG-JUN LINLING-LING LIU: "PIM-1 kinase inhibitor SMI-4a exerts antitumor effects in chronic myeloid leukemia cells by enhancing the activity of glycogen synthase kinase 3β", MOL MED REP., vol. 16, no. 4, October 2017 (2017-10-01), pages 4603 - 4612
HOLLY KOBLISHYUN-LONG LINIU SHINLESILE HALLQIAN WANGKATHY WANGMARYANNE COVEINGTONCINDY MARANDOKEVIN BOWMANJASON BOER: "Preclinical characterization of INCB053914, a novel pan-PIM Kinase inhibitor, alone and in combination with anticancer agents, in models of hematologic malignancies", PLOS ONE, vol. 13, no. 6, 21 June 2018 (2018-06-21), pages e0199108
GARY W. REUTHER: "The pan-PIM inhibitor INCB053914 displays potent synergy in combination with ruxolitinib in models of MPN", BLOOD ADV., vol. 3, no. 22, 26 November 2019 (2019-11-26), pages 3503 - 3514
RONG FU MD, PHDYONG XIA MD, PHDMEIRONG LI BSRENXIANG MAO MDCHAOHUAN GUO MDMIANJING ZHOU MDHECHANG TAN MD, PHDMEILING LIU BSSHUANG : "Pim-1 as a Therapeutic Target in Lupus Nephritis", ARTHRITIS RHEUMATOL ., vol. 71, no. 8, August 2019 (2019-08-01), pages 1308 - 1318
BERGE ET AL., J. PHARM. SCI., vol. 66, 1977, pages 1 - 19
STAHL ET AL.: "Handbook of Pharmaceutical Salt: Properties, Selection, and Use", 2002, WILEY-VCH
PAULEKUHN ET AL., J. MED. CHEM., vol. 50, 2007, pages 6665 - 6672
"NCBI", Database accession no. NM_002648.3
Attorney, Agent or Firm:
TAKASHIMA, Hajime (JP)
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