Title:
HETEROARYL-CARBOXYLIC ACIDS AS HISTONE DEMETHYLASE INHIBITORS
Document Type and Number:
WIPO Patent Application WO/2017/207813
Kind Code:
A1
Abstract:
The invention relates to heteroaryl-carboxylic acids as described herein, useful as histone demethylase inhibitors. The invention also relates to pharmaceutical compositions comprising these compounds and to their use in therapy, including e.g., in the treatment of cancer.
Inventors:
ORTEGA MUÑOZ ALBERTO (ES)
SALAS SOLANA JORGE (ES)
CARCELLER GONZÁLEZ ELENA (ES)
SALAS SOLANA JORGE (ES)
CARCELLER GONZÁLEZ ELENA (ES)
Application Number:
PCT/EP2017/063585
Publication Date:
December 07, 2017
Filing Date:
June 02, 2017
Export Citation:
Assignee:
ORYZON GENOMICS SA (ES)
International Classes:
C07D401/14; A61K31/444; A61P35/00; C07D213/79; C07D403/04; C07D403/14; C07D413/14
Domestic Patent References:
| WO2010043866A2 | 2010-04-22 | |||
| WO2010043866A2 | 2010-04-22 |
Foreign References:
| US20160068507A1 | 2016-03-10 | |||
| US20160068507A1 | 2016-03-10 |
Other References:
DATABASE PubChem Compound [online] 21 March 2013 (2013-03-21), XP002772507, retrieved from NCBI Database accession no. 71080218
DATABASE PubChem Compound [online] 30 November 2012 (2012-11-30), XP002772508, retrieved from NCBI Database accession no. 67963602
SMITH M.B.: "March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure", 2013, WILEY
GREENE TW; WUTS PGM: "Greene's Protective Groups in Organic Synthesis", 2006, WILEY
BENEVOLENSKAYA E.V. ET AL., MOL CELL, vol. 18, no. 6, 2005, pages 623 - 635
CHICAS A. ET AL., PNAS, vol. 109, no. 23, 2012, pages 8971 - 8976
LIN W. ET AL., PNAS, vol. 108, no. 33, 2011, pages 13379 - 13386
SHARMA S.V. ET AL., CELL, vol. 141, no. 1, 2010, pages 69 - 80
VINOGRADOVA M. ET AL., NATURE CHEM BIO, 2016
HOU J. ET AL., AM J TRANSL RES, vol. 4, no. 3, 2012, pages 247 - 256
TENG Y.C. ET AL., CANCER RES, vol. 73, no. 15, 2013, pages 4711 - 4721
VIEIRA F.Q. ET AL., ENDOCR RELAT CANCER, vol. 21, no. 1, 2013, pages 51 - 61
LI H. ET AL., MOL CANCER RES, vol. 12, no. 4, 2014, pages 571 - 582
BANNELLI B. ET AL., CELL CYCLE, vol. 14, no. 21, 2015, pages 3418 - 3429
ZENG J. ET AL., GASTROENTEROLOGY, vol. 138, no. 3, 2010, pages 981 - 992
HIDALGO A. ET AL., BMC CANCER, vol. 5, 2005, pages 77
MAGGI E.C. ET AL., ONCOGENESIS, vol. 5, no. 8, 2016, pages e257
DE ROOIJ J.D. ET AL., LEUKEMIA, vol. 27, no. 12, 2013, pages 2280 - 2288
WONG P.P. ET AL., MOL CELL BIOL, vol. 32, no. 9, 2012, pages 1633 - 1644
WANG D. ET AL., J EXP CLIN CANCER RES, vol. 35, 2016, pages 37
WANG Z. ET AL., AM J CANCER RES, vol. 5, no. 1, 2014, pages 87 - 100
KANO Y. ET AL., MOL CLIN ONCOL, vol. 1, no. 4, 2013, pages 753 - 757
OHTA K. ET AL., INT J ONCOL, vol. 42, no. 4, 2013, pages 1212 - 1218
YAMAMOTO S. ET AL., CANCER CELL, vol. 25, no. 6, 2014, pages 762 - 777
BAMODU OA ET AL., BMC CANCER, vol. 16, no. 1, 2016, pages 160
YAMANE K. ET AL., MOL CELL, vol. 25, no. 6, 2007, pages 801 - 812
TUMBER A. ET AL., CELL CHEM BIOL., vol. 24, no. 3, 2017, pages 371 - 380
WANG D. ET AL., J EXP CLIN CANCER RES., vol. 35, 2016, pages 37
HALEY J.A. ET AL., FRONT ONCOL, vol. 4, 2014, pages 344
WANG L. ET AL., TUMOUR BIOL, vol. 36, no. 4, 2015, pages 2465 - 2472
HAYAMI S. ET AL., MOL CANCER, vol. 9, 2010, pages 59
XIANG Y. ET AL., PNAS, vol. 104, no. 49, 2007, pages 19226 - 19231
ROESCH A. ET AL., CANCER CELL, vol. 23, no. 6, 2013, pages 811 - 825
RADBERGER P. ET AL., INVEST OPHTHALMOL VIS SCI, vol. 53, no. 8, 2012, pages 4442 - 4449
PTASCHINSKI C. ET AL., PLOS PATHOG, vol. 11, no. 6, 2015, pages e1004978
AGUILAR-VALLES A. ET AL., BIOL PSYCHIATRY, vol. 76, no. 1, 2014, pages 57 - 65
JENSEN L.R. ET AL., AM J HUM GENET, vol. 76, no. 2, 2005, pages 227 - 236
SIMENSEN R.J. ET AL., GENET COUNS, vol. 23, no. 1, 2012, pages 31 - 40
VASHISHTHA M. ET AL., PNAS, vol. 110, 2013, pages E3027 - E3036
DALGLIESH G.L. ET AL., NATURE, vol. 463, no. 7279, 2010, pages 360 - 363
PATANI N. ET AL., ANTICANCER RES, vol. 31, no. 12, 2011, pages 4115 - 4125
STEIN J. ET AL., AM J PATHOL, vol. 184, no. 9, 2014, pages 2430 - 2437
XU L. ET AL., TECHNOL CANCER RES TREAT, 2016
WANG Q. ET AL., BIOCHEM BIOPHYS RES COMMUN, vol. 464, no. 2, 2015, pages 659 - 666
JI X. ET AL., BMC CANCER, vol. 15, 2015, pages 801
LIN N. ET AL., CANCER RES, vol. 76, no. 4, 2016, pages 831 - 843
WHETSTINE J.R. ET AL., CELL, vol. 125, no. 3, 2006, pages 467 - 481
PETERS A.H. ET AL., CELL, vol. 107, no. 3, 2001, pages 323 - 337
CLOOS, P.A. ET AL., NATURE, vol. 442, 2006, pages 307 - 311
ZHANG D. ET AL., MOL CELL BIOL, vol. 25, 2005, pages 6404 - 6414
BERRY W.L. ET AL., INT J ONCOL, vol. 41, 2012, pages 1701 - 1706
SHI L. ET AL., PROC NATL ACAD SCI USA., vol. 108, no. 18, 2011, pages 7541 - 7546
LIU G. ET AL., ONCOGENE, vol. 28, no. 50, 2009, pages 4491 - 4500
KIM T.D., CARCINOGENESIS, vol. 113, no. 4, 2012, pages 1368 - 1376
FU L. ET AL., CARCINOGENESIS, vol. 33, 2012, pages 1664 - 1673
BEYER S. ET AL., J BIOL CHEM., vol. 283, 2008, pages 36542 - 36552
YAMAMOTO S. ET AL., CARCINOGENESIS, vol. 34, no. 10, 2013, pages 2380 - 2388
MALLETTE F.A. ET AL., CELL REPORTS, vol. 2, 2012, pages 1233 - 1243
HU C.E. ET AL., BIOCHEM BIOPHYS RES COMMUN., vol. 449, no. 1, 2014, pages 1 - 7
TOYOKAWA G., CANCER PREV RES, vol. 4, no. 12, 2011, pages 2051 - 2061
LI W., BIOCHEM BIOPHYS RES COMMUN., vol. 416, no. 3-4, 2011, pages 372 - 378
LI S., ACTA BIOCHIM BIOPHYS SIN, vol. 47, no. 12, 2015, pages 997 - 1004
SHIN S., BIOCHEM BIOPHYS RES COMMUN, vol. 359, 2007, pages 742 - 746
WISSMANN M. ET AL., NAT CELL BIOL., vol. 9, no. 3, 2007, pages 347 - 353
DING X. ET AL., SCI SIGNAL., vol. 6, no. 273, 2013
YANG Z.Q. ET AL., JPN J CANCER RES., vol. 92, no. 4, 2001, pages 423 - 428
KNUUTILA, S. ET AL., AM. J. PATHOL., vol. 152, 1998, pages 1107 - 1123
RUI L. ET AL., CANCER CELL., vol. 18, no. 6, 2010, pages 590 - 605
CHEUNG N. ET AL., CANCER CELL., vol. 29, no. 1, 2016, pages 32 - 48
LOH,Y.H. ET AL., GENES DEV., vol. 21, 2007, pages 2545 - 2557
LIZCANO F. ET AL., GENET MOL BIOL, vol. 34, no. 1, 2011, pages 19 - 24
LIANG ET AL., SCI TRANSL MED., vol. 5, no. 167, 2013, pages 167ra5
CHANG ET AL., J VIROL., vol. 85, no. 7, 2011, pages 3283 - 3293
XIANG ET AL., CELL RES, vol. 17, no. 10, 2017, pages 850 - 857
SVOTELIS ET AL., EMBO J., vol. 30, no. 19, 2011, pages 3947 - 3961
RAMADOSS ET AL., J BIOL CHEM., vol. 287, no. 53, 2012, pages 44508 - 44517
PEREIRA ET AL., CELL CYCLE, vol. 11, no. 6, 2012, pages 1081 - 1089
MCLAUGHLIN-DRUBIN ET AL., PNAS, vol. 110, no. 40, 2013, pages 16175 - 16180
PARK ET AL., CANCER RES, vol. 76, no. 1, 2016, pages 161 - 170
SHEN ET AL., BMC CANCER, vol. 12, 2012, pages 470
XIA ET AL., ONCOTARGET, 2017
TANG ET AL., CANCER RES, vol. 76, no. 22, 2016, pages 6520 - 6532
SAKAKI ET AL., ANTICANCER RES, vol. 35, no. 12, 2015, pages 6607 - 6614
HASHIZUME ET AL., NAT MED, vol. 20, no. 12, 2014, pages 1394 - 1396
LIAU ET AL., CELL STEM CELL, vol. 20, no. 2, 2017, pages 233 - 246
CREGAN ET AL., INT J ONCOL., vol. 50, no. 3, 2017, pages 1044 - 1052
SHI ET AL., NAT COMMUN, vol. 5, 2014, pages 5425
WEI ET AL., LEUKEMIA, vol. 27, no. 11, 2013, pages 2177 - 2186
NTZIACHRISTOS ET AL., NATURE, vol. 514, no. 7523, 2014, pages 513 - 517
ANDERTON ET AL., ONCOGENE, vol. 30, no. 17, 2011, pages 2037 - 2043
MARTHUR, HAEMATOLOGICA, vol. 102, no. 2, 2017, pages 373 - 380
ROSSETTO ET AL., PLOS PATHOG., vol. 8, no. 5, 2012, pages e1002680
CHEN ET AL., SCI REP., vol. 6, 2016, pages 35974
MCLAUGHLIN-DRUBIN ET AL., PNAS, vol. 108, no. 5, 2011, pages 2130 - 2135
"Remington: The Science and Practice of Pharmacy", 2012, PHARMACEUTICAL PRESS
DATABASE PubChem Compound [online] 30 November 2012 (2012-11-30), XP002772508, retrieved from NCBI Database accession no. 67963602
SMITH M.B.: "March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure", 2013, WILEY
GREENE TW; WUTS PGM: "Greene's Protective Groups in Organic Synthesis", 2006, WILEY
BENEVOLENSKAYA E.V. ET AL., MOL CELL, vol. 18, no. 6, 2005, pages 623 - 635
CHICAS A. ET AL., PNAS, vol. 109, no. 23, 2012, pages 8971 - 8976
LIN W. ET AL., PNAS, vol. 108, no. 33, 2011, pages 13379 - 13386
SHARMA S.V. ET AL., CELL, vol. 141, no. 1, 2010, pages 69 - 80
VINOGRADOVA M. ET AL., NATURE CHEM BIO, 2016
HOU J. ET AL., AM J TRANSL RES, vol. 4, no. 3, 2012, pages 247 - 256
TENG Y.C. ET AL., CANCER RES, vol. 73, no. 15, 2013, pages 4711 - 4721
VIEIRA F.Q. ET AL., ENDOCR RELAT CANCER, vol. 21, no. 1, 2013, pages 51 - 61
LI H. ET AL., MOL CANCER RES, vol. 12, no. 4, 2014, pages 571 - 582
BANNELLI B. ET AL., CELL CYCLE, vol. 14, no. 21, 2015, pages 3418 - 3429
ZENG J. ET AL., GASTROENTEROLOGY, vol. 138, no. 3, 2010, pages 981 - 992
HIDALGO A. ET AL., BMC CANCER, vol. 5, 2005, pages 77
MAGGI E.C. ET AL., ONCOGENESIS, vol. 5, no. 8, 2016, pages e257
DE ROOIJ J.D. ET AL., LEUKEMIA, vol. 27, no. 12, 2013, pages 2280 - 2288
WONG P.P. ET AL., MOL CELL BIOL, vol. 32, no. 9, 2012, pages 1633 - 1644
WANG D. ET AL., J EXP CLIN CANCER RES, vol. 35, 2016, pages 37
WANG Z. ET AL., AM J CANCER RES, vol. 5, no. 1, 2014, pages 87 - 100
KANO Y. ET AL., MOL CLIN ONCOL, vol. 1, no. 4, 2013, pages 753 - 757
OHTA K. ET AL., INT J ONCOL, vol. 42, no. 4, 2013, pages 1212 - 1218
YAMAMOTO S. ET AL., CANCER CELL, vol. 25, no. 6, 2014, pages 762 - 777
BAMODU OA ET AL., BMC CANCER, vol. 16, no. 1, 2016, pages 160
YAMANE K. ET AL., MOL CELL, vol. 25, no. 6, 2007, pages 801 - 812
TUMBER A. ET AL., CELL CHEM BIOL., vol. 24, no. 3, 2017, pages 371 - 380
WANG D. ET AL., J EXP CLIN CANCER RES., vol. 35, 2016, pages 37
HALEY J.A. ET AL., FRONT ONCOL, vol. 4, 2014, pages 344
WANG L. ET AL., TUMOUR BIOL, vol. 36, no. 4, 2015, pages 2465 - 2472
HAYAMI S. ET AL., MOL CANCER, vol. 9, 2010, pages 59
XIANG Y. ET AL., PNAS, vol. 104, no. 49, 2007, pages 19226 - 19231
ROESCH A. ET AL., CANCER CELL, vol. 23, no. 6, 2013, pages 811 - 825
RADBERGER P. ET AL., INVEST OPHTHALMOL VIS SCI, vol. 53, no. 8, 2012, pages 4442 - 4449
PTASCHINSKI C. ET AL., PLOS PATHOG, vol. 11, no. 6, 2015, pages e1004978
AGUILAR-VALLES A. ET AL., BIOL PSYCHIATRY, vol. 76, no. 1, 2014, pages 57 - 65
JENSEN L.R. ET AL., AM J HUM GENET, vol. 76, no. 2, 2005, pages 227 - 236
SIMENSEN R.J. ET AL., GENET COUNS, vol. 23, no. 1, 2012, pages 31 - 40
VASHISHTHA M. ET AL., PNAS, vol. 110, 2013, pages E3027 - E3036
DALGLIESH G.L. ET AL., NATURE, vol. 463, no. 7279, 2010, pages 360 - 363
PATANI N. ET AL., ANTICANCER RES, vol. 31, no. 12, 2011, pages 4115 - 4125
STEIN J. ET AL., AM J PATHOL, vol. 184, no. 9, 2014, pages 2430 - 2437
XU L. ET AL., TECHNOL CANCER RES TREAT, 2016
WANG Q. ET AL., BIOCHEM BIOPHYS RES COMMUN, vol. 464, no. 2, 2015, pages 659 - 666
JI X. ET AL., BMC CANCER, vol. 15, 2015, pages 801
LIN N. ET AL., CANCER RES, vol. 76, no. 4, 2016, pages 831 - 843
WHETSTINE J.R. ET AL., CELL, vol. 125, no. 3, 2006, pages 467 - 481
PETERS A.H. ET AL., CELL, vol. 107, no. 3, 2001, pages 323 - 337
CLOOS, P.A. ET AL., NATURE, vol. 442, 2006, pages 307 - 311
ZHANG D. ET AL., MOL CELL BIOL, vol. 25, 2005, pages 6404 - 6414
BERRY W.L. ET AL., INT J ONCOL, vol. 41, 2012, pages 1701 - 1706
SHI L. ET AL., PROC NATL ACAD SCI USA., vol. 108, no. 18, 2011, pages 7541 - 7546
LIU G. ET AL., ONCOGENE, vol. 28, no. 50, 2009, pages 4491 - 4500
KIM T.D., CARCINOGENESIS, vol. 113, no. 4, 2012, pages 1368 - 1376
FU L. ET AL., CARCINOGENESIS, vol. 33, 2012, pages 1664 - 1673
BEYER S. ET AL., J BIOL CHEM., vol. 283, 2008, pages 36542 - 36552
YAMAMOTO S. ET AL., CARCINOGENESIS, vol. 34, no. 10, 2013, pages 2380 - 2388
MALLETTE F.A. ET AL., CELL REPORTS, vol. 2, 2012, pages 1233 - 1243
HU C.E. ET AL., BIOCHEM BIOPHYS RES COMMUN., vol. 449, no. 1, 2014, pages 1 - 7
TOYOKAWA G., CANCER PREV RES, vol. 4, no. 12, 2011, pages 2051 - 2061
LI W., BIOCHEM BIOPHYS RES COMMUN., vol. 416, no. 3-4, 2011, pages 372 - 378
LI S., ACTA BIOCHIM BIOPHYS SIN, vol. 47, no. 12, 2015, pages 997 - 1004
SHIN S., BIOCHEM BIOPHYS RES COMMUN, vol. 359, 2007, pages 742 - 746
WISSMANN M. ET AL., NAT CELL BIOL., vol. 9, no. 3, 2007, pages 347 - 353
DING X. ET AL., SCI SIGNAL., vol. 6, no. 273, 2013
YANG Z.Q. ET AL., JPN J CANCER RES., vol. 92, no. 4, 2001, pages 423 - 428
KNUUTILA, S. ET AL., AM. J. PATHOL., vol. 152, 1998, pages 1107 - 1123
RUI L. ET AL., CANCER CELL., vol. 18, no. 6, 2010, pages 590 - 605
CHEUNG N. ET AL., CANCER CELL., vol. 29, no. 1, 2016, pages 32 - 48
LOH,Y.H. ET AL., GENES DEV., vol. 21, 2007, pages 2545 - 2557
LIZCANO F. ET AL., GENET MOL BIOL, vol. 34, no. 1, 2011, pages 19 - 24
LIANG ET AL., SCI TRANSL MED., vol. 5, no. 167, 2013, pages 167ra5
CHANG ET AL., J VIROL., vol. 85, no. 7, 2011, pages 3283 - 3293
XIANG ET AL., CELL RES, vol. 17, no. 10, 2017, pages 850 - 857
SVOTELIS ET AL., EMBO J., vol. 30, no. 19, 2011, pages 3947 - 3961
RAMADOSS ET AL., J BIOL CHEM., vol. 287, no. 53, 2012, pages 44508 - 44517
PEREIRA ET AL., CELL CYCLE, vol. 11, no. 6, 2012, pages 1081 - 1089
MCLAUGHLIN-DRUBIN ET AL., PNAS, vol. 110, no. 40, 2013, pages 16175 - 16180
PARK ET AL., CANCER RES, vol. 76, no. 1, 2016, pages 161 - 170
SHEN ET AL., BMC CANCER, vol. 12, 2012, pages 470
XIA ET AL., ONCOTARGET, 2017
TANG ET AL., CANCER RES, vol. 76, no. 22, 2016, pages 6520 - 6532
SAKAKI ET AL., ANTICANCER RES, vol. 35, no. 12, 2015, pages 6607 - 6614
HASHIZUME ET AL., NAT MED, vol. 20, no. 12, 2014, pages 1394 - 1396
LIAU ET AL., CELL STEM CELL, vol. 20, no. 2, 2017, pages 233 - 246
CREGAN ET AL., INT J ONCOL., vol. 50, no. 3, 2017, pages 1044 - 1052
SHI ET AL., NAT COMMUN, vol. 5, 2014, pages 5425
WEI ET AL., LEUKEMIA, vol. 27, no. 11, 2013, pages 2177 - 2186
NTZIACHRISTOS ET AL., NATURE, vol. 514, no. 7523, 2014, pages 513 - 517
ANDERTON ET AL., ONCOGENE, vol. 30, no. 17, 2011, pages 2037 - 2043
MARTHUR, HAEMATOLOGICA, vol. 102, no. 2, 2017, pages 373 - 380
ROSSETTO ET AL., PLOS PATHOG., vol. 8, no. 5, 2012, pages e1002680
CHEN ET AL., SCI REP., vol. 6, 2016, pages 35974
MCLAUGHLIN-DRUBIN ET AL., PNAS, vol. 108, no. 5, 2011, pages 2130 - 2135
"Remington: The Science and Practice of Pharmacy", 2012, PHARMACEUTICAL PRESS
Attorney, Agent or Firm:
RIDDERBUSCH, OSWIN; VOSSIUS & PARTNER (DE)
Download PDF: