Title:
PIM2 INHIBITOR
Document Type and Number:
WIPO Patent Application WO/2022/163843
Kind Code:
A1
Abstract:
Provided are a compound having high PIM2 inhibitory activity, and a PIM2 inhibitor and a pharmaceutical composition that contain the compound. This PIM2 inhibitor contains a compound represented by formula (1) (in the formula, A is a benzene ring optionally having one or more substituents; when the benzene ring has two substituents mutually located at the ortho position, the two substituents may form a ring together with the carbon atoms of the benzene ring to which the substituents bond; X11-X13 each independently represent an oxygen atom or a sulfur atom, and at least one of X12 and X13 represents a sulfur atom) or a pharmacologically acceptable salt thereof.
Inventors:
TERAMACHI JUMPEI (JP)
NAKAO MICHIYASU (JP)
SANO SHIGEKI (JP)
ABE MASAHIRO (JP)
HARADA TAKESHI (JP)
FUJII HIDEKI (JP)
MURAKAMI KEIJI (JP)
NAKAO MICHIYASU (JP)
SANO SHIGEKI (JP)
ABE MASAHIRO (JP)
HARADA TAKESHI (JP)
FUJII HIDEKI (JP)
MURAKAMI KEIJI (JP)
Application Number:
PCT/JP2022/003446
Publication Date:
August 04, 2022
Filing Date:
January 28, 2022
Export Citation:
Assignee:
UNIV TOKUSHIMA (JP)
International Classes:
A61K31/421; A61K31/426; A61P35/00; A61P43/00; C07D263/46; C07D277/36
Foreign References:
| JP2008515955A | 2008-05-15 | |||
| JPH05331148A | 1993-12-14 |
Other References:
HOLIEN TORIL; VåTSVEEN THEA KRISTIN; HELLA HANNE; WAAGE ANDERS; SUNDAN ANDERS: "Addiction to c-MYC in multiple myeloma", BLOOD, AMERICAN SOCIETY OF HEMATOLOGY, US, vol. 120, no. 12, 20 September 2012 (2012-09-20), US , pages 2450 - 2453, XP086693836, ISSN: 0006-4971, DOI: 10.1182/blood-2011-08-371567
HOMMA KAZUKI; ODA TSUKASA; MURAKAMI YUKI; WATANABE SAKI; ISHIHARA REI; KURODA YUKO; MASUDA KEI KIMURA; MASUDA YUTA; KASAMATSU TETS: "Long Noncoding RNA PVT1 and MYC Are Co-Regulated By Bromodomain Protein BRD4 in Multiple Myeloma and Associated with Disease Progression", BLOOD, AMERICAN SOCIETY OF HEMATOLOGY, US, vol. 130, 8 December 2017 (2017-12-08), US , pages 4397, XP086632413, ISSN: 0006-4971, DOI: 10.1182/blood.V130.Suppl_1.4397.4397
ZHOU ZHUANLI; NI JIAYUN; LI JINGYAO; HUO CHUANBING; MIAO NAIJUN; YIN FAN; CHENG QIAN; XU DAN; XIE HONGYAN; CHEN PANPAN; ZHENG PEIQ: "RIG-I aggravates interstitial fibrosis via c-Myc-mediated fibroblast activation in UUO mice", JOURNAL OF MOLECULAR MEDICINE, SPRINGER BERLIN HEIDELBERG, BERLIN/HEIDELBERG, vol. 98, no. 4, 8 February 2020 (2020-02-08), Berlin/Heidelberg, pages 527 - 540, XP037111952, ISSN: 0946-2716, DOI: 10.1007/s00109-020-01879-x
L. ASTUDILLO, T. G. DA SILVA, Z. WANG, X. HAN, K. JIN, J. VANWYE, X. ZHU, K. WEAVER, T. OASHI, P. E. M. LOPES, D. ORTON, L. R. NEI: "The Small Molecule IMR-1 Inhibits the Notch Transcriptional Activation Complex to Suppress Tumorigenesis", CANCER RESEARCH, AMERICAN ASSOCIATION FOR CANCER RESEARCH, US, vol. 76, no. 12, 15 June 2016 (2016-06-15), US , pages 3593 - 3603, XP055320374, ISSN: 0008-5472, DOI: 10.1158/0008-5472.CAN-16-0061
ABDALLAH S. O., HAMMOUDA H. A., ALI F. A.: "8801-252: Heterodiene synthesis: syntheses of fused thiopyrano[2,3-d]thiazole, [1]benzopyrano[3',4':4,5]thiopyrano[2,3-d]thiazole and thiazolo[3,4-c]triazine derivatives", CHEMINFORM, vol. 19, no. 1, 5 January 1988 (1988-01-05), pages 130 - 131, XP009538645, ISSN: 0931-7597, DOI: 10.1002/chin.198801252
V'YUNOV K. A., GINAK A. I., SOCHILIN E. G.: "7945-217: Study of the reactivity and tautomerism of azolidines. XXV. Alkylation of salts of 5-benzylidenethiorhodanines", CHEMISCHER INFORMATIONSDIENST, vol. 10, no. 45, 6 November 1979 (1979-11-06), pages 98, XP009538646, ISSN: 0009-2975, DOI: 10.1002/chin.197945217
DONG XUECHANG, HAN YONG, HU QIUFEN, CHEN JING, YANG GUANGYU: "Simultaneous determination of palladium, platinum and rhodium by on-line column enrichment and HPLC with 2,4-dihydroxybenzylidenethiorhodanine as pre-column derivatization reagent", JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, SOCIEDADE BRASILEIRA DE QUíMICA, SAO PAULO, BR, vol. 17, no. 1, 1 January 2006 (2006-01-01), Sao Paulo, BR , pages 189 - 193, XP055954613, ISSN: 0103-5053, DOI: 10.1590/S0103-50532006000100027
SHIRO FUJII; SHINGEN NAKAMURA; ASUKA ODA; HIROKAZU MIKI; HIROFUMI TENSHIN; JUMPEI TERAMACHI; MASAHIRO HIASA; ARIUNZAYA BAT‐E: "Unique anti‐myeloma activity by thiazolidine‐2,4‐dione compounds with Pim inhibiting activity", BRITISH JOURNAL OF HAEMATOLOGY, JOHN WILEY, HOBOKEN, USA, vol. 180, no. 2, 12 January 2018 (2018-01-12), Hoboken, USA, pages 246 - 258, XP071121672, ISSN: 0007-1048, DOI: 10.1111/bjh.15033
LESYK, R. ; ZIMENKOVSKY, B. ; ATAMANYUK, D. ; JENSEN, F. ; KIEC-KONONOWICZ, K. ; GZELLA, A.: "Anticancer thiopyrano[2,3-d][1,3]thiazol-2-ones with norbornane moiety. Synthesis, cytotoxicity, physico-chemical properties, and computational studies", BIOORGANIC & MEDICINAL CHEMISTRY, ELSEVIER, AMSTERDAM, NL, vol. 14, no. 15, 1 August 2006 (2006-08-01), AMSTERDAM, NL, pages 5230 - 5240, XP027992789, ISSN: 0968-0896
HOMMA KAZUKI; ODA TSUKASA; MURAKAMI YUKI; WATANABE SAKI; ISHIHARA REI; KURODA YUKO; MASUDA KEI KIMURA; MASUDA YUTA; KASAMATSU TETS: "Long Noncoding RNA PVT1 and MYC Are Co-Regulated By Bromodomain Protein BRD4 in Multiple Myeloma and Associated with Disease Progression", BLOOD, AMERICAN SOCIETY OF HEMATOLOGY, US, vol. 130, 8 December 2017 (2017-12-08), US , pages 4397, XP086632413, ISSN: 0006-4971, DOI: 10.1182/blood.V130.Suppl_1.4397.4397
ZHOU ZHUANLI; NI JIAYUN; LI JINGYAO; HUO CHUANBING; MIAO NAIJUN; YIN FAN; CHENG QIAN; XU DAN; XIE HONGYAN; CHEN PANPAN; ZHENG PEIQ: "RIG-I aggravates interstitial fibrosis via c-Myc-mediated fibroblast activation in UUO mice", JOURNAL OF MOLECULAR MEDICINE, SPRINGER BERLIN HEIDELBERG, BERLIN/HEIDELBERG, vol. 98, no. 4, 8 February 2020 (2020-02-08), Berlin/Heidelberg, pages 527 - 540, XP037111952, ISSN: 0946-2716, DOI: 10.1007/s00109-020-01879-x
L. ASTUDILLO, T. G. DA SILVA, Z. WANG, X. HAN, K. JIN, J. VANWYE, X. ZHU, K. WEAVER, T. OASHI, P. E. M. LOPES, D. ORTON, L. R. NEI: "The Small Molecule IMR-1 Inhibits the Notch Transcriptional Activation Complex to Suppress Tumorigenesis", CANCER RESEARCH, AMERICAN ASSOCIATION FOR CANCER RESEARCH, US, vol. 76, no. 12, 15 June 2016 (2016-06-15), US , pages 3593 - 3603, XP055320374, ISSN: 0008-5472, DOI: 10.1158/0008-5472.CAN-16-0061
ABDALLAH S. O., HAMMOUDA H. A., ALI F. A.: "8801-252: Heterodiene synthesis: syntheses of fused thiopyrano[2,3-d]thiazole, [1]benzopyrano[3',4':4,5]thiopyrano[2,3-d]thiazole and thiazolo[3,4-c]triazine derivatives", CHEMINFORM, vol. 19, no. 1, 5 January 1988 (1988-01-05), pages 130 - 131, XP009538645, ISSN: 0931-7597, DOI: 10.1002/chin.198801252
V'YUNOV K. A., GINAK A. I., SOCHILIN E. G.: "7945-217: Study of the reactivity and tautomerism of azolidines. XXV. Alkylation of salts of 5-benzylidenethiorhodanines", CHEMISCHER INFORMATIONSDIENST, vol. 10, no. 45, 6 November 1979 (1979-11-06), pages 98, XP009538646, ISSN: 0009-2975, DOI: 10.1002/chin.197945217
DONG XUECHANG, HAN YONG, HU QIUFEN, CHEN JING, YANG GUANGYU: "Simultaneous determination of palladium, platinum and rhodium by on-line column enrichment and HPLC with 2,4-dihydroxybenzylidenethiorhodanine as pre-column derivatization reagent", JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, SOCIEDADE BRASILEIRA DE QUíMICA, SAO PAULO, BR, vol. 17, no. 1, 1 January 2006 (2006-01-01), Sao Paulo, BR , pages 189 - 193, XP055954613, ISSN: 0103-5053, DOI: 10.1590/S0103-50532006000100027
SHIRO FUJII; SHINGEN NAKAMURA; ASUKA ODA; HIROKAZU MIKI; HIROFUMI TENSHIN; JUMPEI TERAMACHI; MASAHIRO HIASA; ARIUNZAYA BAT‐E: "Unique anti‐myeloma activity by thiazolidine‐2,4‐dione compounds with Pim inhibiting activity", BRITISH JOURNAL OF HAEMATOLOGY, JOHN WILEY, HOBOKEN, USA, vol. 180, no. 2, 12 January 2018 (2018-01-12), Hoboken, USA, pages 246 - 258, XP071121672, ISSN: 0007-1048, DOI: 10.1111/bjh.15033
LESYK, R. ; ZIMENKOVSKY, B. ; ATAMANYUK, D. ; JENSEN, F. ; KIEC-KONONOWICZ, K. ; GZELLA, A.: "Anticancer thiopyrano[2,3-d][1,3]thiazol-2-ones with norbornane moiety. Synthesis, cytotoxicity, physico-chemical properties, and computational studies", BIOORGANIC & MEDICINAL CHEMISTRY, ELSEVIER, AMSTERDAM, NL, vol. 14, no. 15, 1 August 2006 (2006-08-01), AMSTERDAM, NL, pages 5230 - 5240, XP027992789, ISSN: 0968-0896
Attorney, Agent or Firm:
SAEGUSA & PARTNERS (JP)
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