JP2016509047A5 - - Google Patents
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- JP2016509047A5 JP2016509047A5 JP2015558495A JP2015558495A JP2016509047A5 JP 2016509047 A5 JP2016509047 A5 JP 2016509047A5 JP 2015558495 A JP2015558495 A JP 2015558495A JP 2015558495 A JP2015558495 A JP 2015558495A JP 2016509047 A5 JP2016509047 A5 JP 2016509047A5
- Authority
- JP
- Japan
- Prior art keywords
- cycloalkyl
- alkyl
- heteroaryl
- aryl
- alkynyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 125000000217 alkyl group Chemical group 0.000 claims description 225
- 125000000304 alkynyl group Chemical group 0.000 claims description 175
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 171
- 125000003342 alkenyl group Chemical group 0.000 claims description 162
- 125000001072 heteroaryl group Chemical group 0.000 claims description 145
- 125000000623 heterocyclic group Chemical group 0.000 claims description 145
- 125000003118 aryl group Chemical group 0.000 claims description 141
- 229910052799 carbon Inorganic materials 0.000 claims description 95
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 81
- 229910052739 hydrogen Inorganic materials 0.000 claims description 81
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 74
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 64
- 150000001875 compounds Chemical class 0.000 claims description 56
- 125000003545 alkoxy group Chemical group 0.000 claims description 45
- 125000004043 oxo group Chemical group O=* 0.000 claims description 42
- 229910052736 halogen Inorganic materials 0.000 claims description 36
- 150000002367 halogens Chemical class 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 35
- -1 heterocyclylene Chemical group 0.000 claims description 34
- 125000002947 alkylene group Chemical group 0.000 claims description 29
- 125000004104 aryloxy group Chemical group 0.000 claims description 27
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 27
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 27
- 239000000651 prodrug Substances 0.000 claims description 25
- 229940002612 prodrug Drugs 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 25
- 239000012453 solvate Substances 0.000 claims description 25
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 23
- 125000004419 alkynylene group Chemical group 0.000 claims description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 18
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 18
- 125000004450 alkenylene group Chemical group 0.000 claims description 18
- 125000000732 arylene group Chemical group 0.000 claims description 18
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 18
- 125000005549 heteroarylene group Chemical group 0.000 claims description 18
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 18
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 17
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 17
- 125000004122 cyclic group Chemical group 0.000 claims description 16
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 14
- 125000003003 spiro group Chemical group 0.000 claims description 11
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 238000006467 substitution reaction Methods 0.000 claims description 9
- 230000001419 dependent effect Effects 0.000 claims description 7
- 201000010099 disease Diseases 0.000 claims description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims description 2
- 229940072107 ascorbate Drugs 0.000 claims description 2
- 235000010323 ascorbic acid Nutrition 0.000 claims description 2
- 239000011668 ascorbic acid Substances 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 7
- 125000006586 (C3-C10) cycloalkylene group Chemical group 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 description 3
- 239000003814 drug Substances 0.000 description 2
- 0 **N(*)Cc1nccc(*)c1 Chemical compound **N(*)Cc1nccc(*)c1 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
Applications Claiming Priority (15)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361770067P | 2013-02-27 | 2013-02-27 | |
| US201361770065P | 2013-02-27 | 2013-02-27 | |
| US201361770058P | 2013-02-27 | 2013-02-27 | |
| DKPA201370114 | 2013-02-27 | ||
| DKPA201370114 | 2013-02-27 | ||
| DKPA201370113 | 2013-02-27 | ||
| US61/770,067 | 2013-02-27 | ||
| DKPA201370115 | 2013-02-27 | ||
| US61/770,058 | 2013-02-27 | ||
| US61/770,065 | 2013-02-27 | ||
| DKPA201370113 | 2013-02-27 | ||
| DKPA201370115 | 2013-02-27 | ||
| US201461931126P | 2014-01-24 | 2014-01-24 | |
| US61/931,126 | 2014-01-24 | ||
| PCT/EP2014/053674 WO2014131777A1 (en) | 2013-02-27 | 2014-02-26 | Inhibitors of histone demethylases |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018082444A Division JP2018127486A (ja) | 2013-02-27 | 2018-04-23 | ヒストン脱メチル化酵素の阻害剤 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016509047A JP2016509047A (ja) | 2016-03-24 |
| JP2016509047A5 true JP2016509047A5 (cg-RX-API-DMAC10.html) | 2017-03-30 |
| JP6514117B2 JP6514117B2 (ja) | 2019-05-15 |
Family
ID=51427545
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015558495A Active JP6514117B2 (ja) | 2013-02-27 | 2014-02-26 | ヒストン脱メチル化酵素の阻害剤 |
| JP2018082444A Withdrawn JP2018127486A (ja) | 2013-02-27 | 2018-04-23 | ヒストン脱メチル化酵素の阻害剤 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018082444A Withdrawn JP2018127486A (ja) | 2013-02-27 | 2018-04-23 | ヒストン脱メチル化酵素の阻害剤 |
Country Status (23)
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2014
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