Title:
SUBSTITUENT-INCLUDING UREA COMPOUND
Document Type and Number:
WIPO Patent Application WO/2020/153433
Kind Code:
A1
Abstract:
The present invention addresses the problem of providing a compound that is useful as an active ingredient for preventing and treating inflammatory diseases and that has a specific chemical structure having an effect of activating SIRT6. The present invention pertains to a compound represented by formula (1), or a pharmaceutically acceptable salt thereof (each symbol in formula (1) is identical to that defined in the description).
Inventors:
KAWAI JUNYA (JP)
IWAMOTO OSAMU (JP)
UMEZAKI YUMA (JP)
NAKAJIMA KATSUYOSHI (JP)
TSURUOKA HIROYUKI (JP)
SAITO KEIJI (JP)
KURIKAWA NOBUYA (JP)
NISHIHAMA NATSUMI (JP)
TANAKA SHINJI (JP)
OGITANI MOMOKO (JP)
HONDA TOMOHIRO (JP)
SAITOH WATARU (JP)
SONEDA TSUYOSHI (JP)
OHKAWA NOBUYUKI (JP)
IWAMOTO OSAMU (JP)
UMEZAKI YUMA (JP)
NAKAJIMA KATSUYOSHI (JP)
TSURUOKA HIROYUKI (JP)
SAITO KEIJI (JP)
KURIKAWA NOBUYA (JP)
NISHIHAMA NATSUMI (JP)
TANAKA SHINJI (JP)
OGITANI MOMOKO (JP)
HONDA TOMOHIRO (JP)
SAITOH WATARU (JP)
SONEDA TSUYOSHI (JP)
OHKAWA NOBUYUKI (JP)
Application Number:
PCT/JP2020/002351
Publication Date:
July 30, 2020
Filing Date:
January 23, 2020
Export Citation:
Assignee:
DAIICHI SANKYO CO LTD (JP)
International Classes:
A61P1/00; A61K31/437; A61K31/5386; A61P1/02; A61P1/04; A61P1/16; A61P1/18; A61P3/10; A61P9/04; A61P9/10; A61P11/00; A61P11/02; A61P11/04; A61P11/06; A61P11/08; A61P17/00; A61P17/02; A61P17/04; A61P17/06; A61P17/08; A61P17/14; A61P19/02; A61P25/00; A61P25/02; A61P27/02; A61P27/16; A61P29/00; A61P37/02; A61P37/08; A61P43/00; C07D513/04; C07D513/08; C07D513/18
Domestic Patent References:
| WO2010024258A1 | 2010-03-04 | |||
| WO2010125799A1 | 2010-11-04 | |||
| WO2014113191A1 | 2014-07-24 | |||
| WO2010024258A1 | 2010-03-04 | |||
| WO2010125799A1 | 2010-11-04 | |||
| WO2013134226A1 | 2013-09-12 | |||
| WO2016025669A1 | 2016-02-18 | |||
| WO2016207785A1 | 2016-12-29 | |||
| WO2018037223A1 | 2018-03-01 | |||
| WO2009037296A1 | 2009-03-26 | |||
| WO2013150416A1 | 2013-10-10 | |||
| WO2011106114A1 | 2011-09-01 | |||
| WO2012082689A1 | 2012-06-21 |
Foreign References:
| US4289524A | 1981-09-15 | |||
| JP2015097508A | 2015-05-28 | |||
| JP2015038046A | 2015-02-26 | |||
| JP2019010252A | 2019-01-24 |
Other References:
DATABASE CAS [online] 17 May 2015 (2015-05-17), ANONYMOUS: "/1 -(C) FILE REGISTRY RN -1706365-47-0 REGISTRY ED -Entered STN: 17 May 2015 CN -Thiazolo[5,4-c]pyridine-5(4H)-acetamide, 2-[[(cyclopentylamino)carbonyl]amino]-6,7-dihydro-N-(1-methylethyl)- (CA INDEX NAME)", XP055727961, retrieved from STN Database accession no. 1706365-47-0
DATABASE CAS [online] 15 May 2015 (2015-05-15), retrieved from STN Database accession no. 1705447-81-9
WEIJIE YOU, DANTE ROTILI, TIE-MEI LI, CHRISTIAN KAMBACH, MARAT MELESHIN, MIKE SCHUTKOWSKI,KATRIN F. CHUA, ANTONELLO MAI, CLEMENS S: "Structural Basis of Sirtuin 6 Activation by Synthetic Small Molecules", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, vol. 56, no. 4, 19 December 2016 (2016-12-19), pages 1007 - 1011, XP055727167, ISSN: 1433-7851, DOI: 10.1002/anie.201610082
IMAI SGUARENTE L: "Ten years of NAD-dependent SIR2 family deacetylases: implications for metabolic diseases", TRENDS PHARMACOL SCI., vol. 31, no. 5, 2010, pages 212 - 220, XP027032564
GUARENTE L.: "Calorie restriction and sirtuins revisited", GENES DEV., vol. 27, no. 19, 2013, pages 2072 - 2085
MICHISHITA EPARK JYBURNESKIS JM ET AL.: "Evolutionarily conserved and nonconserved cellular localizations and functions of human SIRT proteins", MOL BIOL CELL, vol. 16, no. 10, 2005, pages 4623 - 4635, XP002430110, DOI: 10.1091/mbc.E05-01-0033
MICHISHITA EMCCORD RABERBER E ET AL.: "SIRT6 is a histone H3 lysine 9 deacetylase that modulates telomeric chromatin", NATURE, vol. 452, no. 7186, 2008, pages 492 - 496, XP002623499, DOI: 10.1038/nature06736
MICHISHITA EMCCORD RABOXER LD ET AL.: "Cell cycle-dependent deacetylation of telomeric histone H3 lysine K56 by human SIRT6", CELL CYCLE, vol. 8, no. 16, 2009, pages 2664 - 2666
MOSTOSLAVSKY RCHUA KFLOMBARD DB ET AL.: "Genomic instability and aging-like phenotype in the absence of mammalian SIRT6", CELL, vol. 124, no. 2, 2006, pages 315 - 329, XP002430108, DOI: 10.1016/j.cell.2005.11.044
KAWAHARA TLMICHISHITA EADLER AS ET AL.: "SIRT6 links histone H3 lysine 9 deacetylation to NF-kappaB-dependent gene expression and organismal lifespan", CELL, vol. 136, no. 1, 2009, pages 62 - 74
KANFI YNAIMAN SAMIR G ET AL.: "The sirtuin SIRT6 regulates lifespan in male mice", NATURE, vol. 483, no. 7388, 2012, pages 218 - 221
MCCORD RAMICHISHITA EHONG T ET AL.: "SIRT6 stabilizes DNA-dependent protein kinase at chromatin for DNA double-strand break repair", AGING, vol. 1, no. 1, 2009, pages 109 - 121
KIM HSXIAO CWANG RH ET AL.: "Hepatic-specific disruption of SIRT6 in mice results in fatty liver formation due to enhanced glycolysis and triglyceride synthesis", CELL METAB, vol. 12, no. 3, 2010, pages 224 - 236
KANFI YPESHTI VGIL R ET AL.: "SIRT6 protects against pathological damage caused by diet-induced obesity", AGING CELL, vol. 9, no. 2, 2010, pages 162 - 173, XP055081662, DOI: 10.1111/j.1474-9726.2009.00544.x
STOHR RMAVILIO MMARINO A ET AL.: "ITCH modulates SIRT6 and SREBP2 to influence lipid metabolism and atherosclerosis in ApoE null mice", SCI REP., vol. 5, 17 March 2015 (2015-03-17), pages 9023
MINAGAWA SARAYA JNUMATA T ET AL.: "Accelerated epithelial cell senescence in IPF and the inhibitory role of SIRT6 in TGF-(3-induced senescence of human bronchial epithelial cells.", AM J PHYSIOL LUNG CELL MOL PHYSIOL., vol. 300, no. 3, 2011, pages L391 - 401
SUNDARESAN NRVASUDEVAN PZHONG L ET AL.: "The sirtuin SIRT6 blocks IGF-Akt signaling and development of cardiac hypertrophy by targeting c-Jun", NAT MED, vol. 18, no. 11, 2012, pages 1643 - 1650
PROG. MED., VOL., vol. 5, 1985, pages 2157 - 2161
SYNTHETIC COMMUNICATIONS, vol. 39, no. 11, 2009, pages 2053 - 2057
CHEMISTRY - A EUROPEAN JOURNAL, vol. 23, no. 50, 2017, pages 12363 - 12371
See also references of EP 3915558A4
DATABASE CAS [online] 15 May 2015 (2015-05-15), retrieved from STN Database accession no. 1705447-81-9
WEIJIE YOU, DANTE ROTILI, TIE-MEI LI, CHRISTIAN KAMBACH, MARAT MELESHIN, MIKE SCHUTKOWSKI,KATRIN F. CHUA, ANTONELLO MAI, CLEMENS S: "Structural Basis of Sirtuin 6 Activation by Synthetic Small Molecules", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, vol. 56, no. 4, 19 December 2016 (2016-12-19), pages 1007 - 1011, XP055727167, ISSN: 1433-7851, DOI: 10.1002/anie.201610082
IMAI SGUARENTE L: "Ten years of NAD-dependent SIR2 family deacetylases: implications for metabolic diseases", TRENDS PHARMACOL SCI., vol. 31, no. 5, 2010, pages 212 - 220, XP027032564
GUARENTE L.: "Calorie restriction and sirtuins revisited", GENES DEV., vol. 27, no. 19, 2013, pages 2072 - 2085
MICHISHITA EPARK JYBURNESKIS JM ET AL.: "Evolutionarily conserved and nonconserved cellular localizations and functions of human SIRT proteins", MOL BIOL CELL, vol. 16, no. 10, 2005, pages 4623 - 4635, XP002430110, DOI: 10.1091/mbc.E05-01-0033
MICHISHITA EMCCORD RABERBER E ET AL.: "SIRT6 is a histone H3 lysine 9 deacetylase that modulates telomeric chromatin", NATURE, vol. 452, no. 7186, 2008, pages 492 - 496, XP002623499, DOI: 10.1038/nature06736
MICHISHITA EMCCORD RABOXER LD ET AL.: "Cell cycle-dependent deacetylation of telomeric histone H3 lysine K56 by human SIRT6", CELL CYCLE, vol. 8, no. 16, 2009, pages 2664 - 2666
MOSTOSLAVSKY RCHUA KFLOMBARD DB ET AL.: "Genomic instability and aging-like phenotype in the absence of mammalian SIRT6", CELL, vol. 124, no. 2, 2006, pages 315 - 329, XP002430108, DOI: 10.1016/j.cell.2005.11.044
KAWAHARA TLMICHISHITA EADLER AS ET AL.: "SIRT6 links histone H3 lysine 9 deacetylation to NF-kappaB-dependent gene expression and organismal lifespan", CELL, vol. 136, no. 1, 2009, pages 62 - 74
KANFI YNAIMAN SAMIR G ET AL.: "The sirtuin SIRT6 regulates lifespan in male mice", NATURE, vol. 483, no. 7388, 2012, pages 218 - 221
MCCORD RAMICHISHITA EHONG T ET AL.: "SIRT6 stabilizes DNA-dependent protein kinase at chromatin for DNA double-strand break repair", AGING, vol. 1, no. 1, 2009, pages 109 - 121
KIM HSXIAO CWANG RH ET AL.: "Hepatic-specific disruption of SIRT6 in mice results in fatty liver formation due to enhanced glycolysis and triglyceride synthesis", CELL METAB, vol. 12, no. 3, 2010, pages 224 - 236
KANFI YPESHTI VGIL R ET AL.: "SIRT6 protects against pathological damage caused by diet-induced obesity", AGING CELL, vol. 9, no. 2, 2010, pages 162 - 173, XP055081662, DOI: 10.1111/j.1474-9726.2009.00544.x
STOHR RMAVILIO MMARINO A ET AL.: "ITCH modulates SIRT6 and SREBP2 to influence lipid metabolism and atherosclerosis in ApoE null mice", SCI REP., vol. 5, 17 March 2015 (2015-03-17), pages 9023
MINAGAWA SARAYA JNUMATA T ET AL.: "Accelerated epithelial cell senescence in IPF and the inhibitory role of SIRT6 in TGF-(3-induced senescence of human bronchial epithelial cells.", AM J PHYSIOL LUNG CELL MOL PHYSIOL., vol. 300, no. 3, 2011, pages L391 - 401
SUNDARESAN NRVASUDEVAN PZHONG L ET AL.: "The sirtuin SIRT6 blocks IGF-Akt signaling and development of cardiac hypertrophy by targeting c-Jun", NAT MED, vol. 18, no. 11, 2012, pages 1643 - 1650
PROG. MED., VOL., vol. 5, 1985, pages 2157 - 2161
SYNTHETIC COMMUNICATIONS, vol. 39, no. 11, 2009, pages 2053 - 2057
CHEMISTRY - A EUROPEAN JOURNAL, vol. 23, no. 50, 2017, pages 12363 - 12371
See also references of EP 3915558A4
Attorney, Agent or Firm:
EIKOH PATENT FIRM, P.C. (JP)
Download PDF: