JP2020515645A5 - - Google Patents
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- Publication number
- JP2020515645A5 JP2020515645A5 JP2020503253A JP2020503253A JP2020515645A5 JP 2020515645 A5 JP2020515645 A5 JP 2020515645A5 JP 2020503253 A JP2020503253 A JP 2020503253A JP 2020503253 A JP2020503253 A JP 2020503253A JP 2020515645 A5 JP2020515645 A5 JP 2020515645A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- amino
- phenyl
- pyridine
- carboxylic acid
- 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.)
- Granted
Links
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 42
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 claims 26
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 18
- -1 ethoxy, cyclopropylmethoxy, methoxymethyl Chemical group 0.000 claims 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 201000011510 cancer Diseases 0.000 claims 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 2
- NKEJIEXGYADMFB-IBGZPJMESA-N 3-[[(1R)-6-(4-ethoxy-N-methylanilino)-1,2,3,4-tetrahydronaphthalen-1-yl]methylamino]pyridine-4-carboxylic acid Chemical compound C(C)OC1=CC=C(C=C1)N(C=1C=C2CCC[C@H](C2=CC=1)CNC=1C=NC=CC=1C(=O)O)C NKEJIEXGYADMFB-IBGZPJMESA-N 0.000 claims 1
- PGKAQFZWUJVTHU-IBGZPJMESA-N 3-[[(1R)-6-(N,4-dimethylanilino)-1,2,3,4-tetrahydronaphthalen-1-yl]methylamino]pyridine-4-carboxylic acid Chemical compound CN(C=1C=C2CCC[C@H](C2=CC=1)CNC=1C=NC=CC=1C(=O)O)C1=CC=C(C=C1)C PGKAQFZWUJVTHU-IBGZPJMESA-N 0.000 claims 1
- XSMABFRQESMONQ-SFHVURJKSA-N 3-[[(1R)-6-(N-methylanilino)-1,2,3,4-tetrahydronaphthalen-1-yl]methylamino]pyridine-4-carboxylic acid Chemical compound CN(C=1C=C2CCC[C@H](C2=CC=1)CNC=1C=NC=CC=1C(=O)O)C1=CC=CC=C1 XSMABFRQESMONQ-SFHVURJKSA-N 0.000 claims 1
- VSPGQTYJHFYEBS-NRFANRHFSA-N 3-[[(1R)-6-[4-(cyclopropylmethoxy)-N-methylanilino]-1,2,3,4-tetrahydronaphthalen-1-yl]methylamino]pyridine-4-carboxylic acid Chemical compound C1(CC1)COC1=CC=C(C=C1)N(C=1C=C2CCC[C@H](C2=CC=1)CNC=1C=NC=CC=1C(=O)O)C VSPGQTYJHFYEBS-NRFANRHFSA-N 0.000 claims 1
- SSBNZTLLEJJQLB-KRWDZBQOSA-N 3-[[(1R)-6-[4-(difluoromethoxy)-N-methylanilino]-1,2,3,4-tetrahydronaphthalen-1-yl]methylamino]pyridine-4-carboxylic acid Chemical compound FC(OC1=CC=C(C=C1)N(C=1C=C2CCC[C@H](C2=CC=1)CNC=1C=NC=CC=1C(=O)O)C)F SSBNZTLLEJJQLB-KRWDZBQOSA-N 0.000 claims 1
- MOXLRSVBIMTHOC-IBGZPJMESA-N 3-[[(1R)-6-[4-(dimethylamino)-N-methylanilino]-1,2,3,4-tetrahydronaphthalen-1-yl]methylamino]pyridine-4-carboxylic acid Chemical compound CN(C1=CC=C(C=C1)N(C=1C=C2CCC[C@H](C2=CC=1)CNC=1C=NC=CC=1C(=O)O)C)C MOXLRSVBIMTHOC-IBGZPJMESA-N 0.000 claims 1
- KMPDJTNJCUCIDZ-FQEVSTJZSA-N 3-[[(1R)-6-[4-(methoxymethyl)-N-methylanilino]-1,2,3,4-tetrahydronaphthalen-1-yl]methylamino]pyridine-4-carboxylic acid Chemical compound COCC1=CC=C(C=C1)N(C=1C=C2CCC[C@H](C2=CC=1)CNC=1C=NC=CC=1C(=O)O)C KMPDJTNJCUCIDZ-FQEVSTJZSA-N 0.000 claims 1
- XASPFQFJTSXHEL-KRWDZBQOSA-N 3-[[(1R)-6-[methyl(pyridin-2-yl)amino]-1,2,3,4-tetrahydronaphthalen-1-yl]methylamino]pyridine-4-carboxylic acid Chemical compound CN(C=1C=C2CCC[C@H](C2=CC=1)CNC=1C=NC=CC=1C(=O)O)C1=NC=CC=C1 XASPFQFJTSXHEL-KRWDZBQOSA-N 0.000 claims 1
- YBGXCOXIQBWINS-IBGZPJMESA-N 3-[[(4R)-7-(4-cyclopropyl-N-methylanilino)-3,4-dihydro-2H-chromen-4-yl]methylamino]pyridine-4-carboxylic acid Chemical compound C1(CC1)C1=CC=C(C=C1)N(C1=CC2=C([C@@H](CCO2)CNC=2C=NC=CC=2C(=O)O)C=C1)C YBGXCOXIQBWINS-IBGZPJMESA-N 0.000 claims 1
- RBVPIXLZUBCYPJ-SFHVURJKSA-N 3-[[(4R)-7-(4-ethyl-N-methylanilino)-3,4-dihydro-2H-chromen-4-yl]methylamino]pyridine-4-carboxylic acid Chemical compound C(C)C1=CC=C(C=C1)N(C1=CC2=C([C@@H](CCO2)CNC=2C=NC=CC=2C(=O)O)C=C1)C RBVPIXLZUBCYPJ-SFHVURJKSA-N 0.000 claims 1
- NGWSPOACPNNXIY-KRWDZBQOSA-N 3-[[(4R)-7-(N,4-dimethylanilino)-3,4-dihydro-2H-chromen-4-yl]methylamino]pyridine-4-carboxylic acid Chemical compound CN(C1=CC2=C([C@@H](CCO2)CNC=2C=NC=CC=2C(=O)O)C=C1)C1=CC=C(C=C1)C NGWSPOACPNNXIY-KRWDZBQOSA-N 0.000 claims 1
- AAHQMDZQWCCAAA-KRWDZBQOSA-N 3-[[(4R)-7-(N-ethylanilino)-3,4-dihydro-2H-chromen-4-yl]methylamino]pyridine-4-carboxylic acid Chemical compound C(C)N(C1=CC2=C([C@@H](CCO2)CNC=2C=NC=CC=2C(=O)O)C=C1)C1=CC=CC=C1 AAHQMDZQWCCAAA-KRWDZBQOSA-N 0.000 claims 1
- MMTXZUYOXAFOAK-HNNXBMFYSA-N 3-[[(4R)-7-[4-(difluoromethoxy)-N-methylanilino]-3,4-dihydro-2H-chromen-4-yl]methylamino]pyridine-4-carboxylic acid Chemical compound FC(OC1=CC=C(C=C1)N(C1=CC2=C([C@@H](CCO2)CNC=2C=NC=CC=2C(=O)O)C=C1)C)F MMTXZUYOXAFOAK-HNNXBMFYSA-N 0.000 claims 1
- NHVGUSAWBMEIPC-NRFANRHFSA-N 3-[[(4R)-7-[N-methyl-4-(oxan-4-yl)anilino]-3,4-dihydro-2H-chromen-4-yl]methylamino]pyridine-4-carboxylic acid Chemical compound CN(C1=CC2=C([C@@H](CCO2)CNC=2C=NC=CC=2C(=O)O)C=C1)C1=CC=C(C=C1)C1CCOCC1 NHVGUSAWBMEIPC-NRFANRHFSA-N 0.000 claims 1
- RGJVLNLBHVELQL-INIZCTEOSA-N 3-[[(4R)-7-[methyl-(5-methylpyridin-2-yl)amino]-3,4-dihydro-2H-chromen-4-yl]methylamino]pyridine-4-carboxylic acid Chemical compound CN(C1=CC2=C([C@@H](CCO2)CNC=2C=NC=CC=2C(=O)O)C=C1)C1=NC=C(C=C1)C RGJVLNLBHVELQL-INIZCTEOSA-N 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- 101000615488 Homo sapiens Methyl-CpG-binding domain protein 2 Proteins 0.000 claims 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims 1
- 239000004472 Lysine Substances 0.000 claims 1
- 102100021299 Methyl-CpG-binding domain protein 2 Human genes 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000002393 azetidinyl group Chemical group 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 1
- 150000003222 pyridines Chemical class 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762478785P | 2017-03-30 | 2017-03-30 | |
| US62/478,785 | 2017-03-30 | ||
| US201762513875P | 2017-06-01 | 2017-06-01 | |
| US62/513,875 | 2017-06-01 | ||
| PCT/US2018/024624 WO2018183370A2 (en) | 2017-03-30 | 2018-03-27 | Kdm4 inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2020515645A JP2020515645A (ja) | 2020-05-28 |
| JP2020515645A5 true JP2020515645A5 (enExample) | 2021-05-06 |
| JP7442439B2 JP7442439B2 (ja) | 2024-03-04 |
Family
ID=63678220
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020503253A Active JP7442439B2 (ja) | 2017-03-30 | 2018-03-27 | Ｋｄｍ４阻害剤 |
Country Status (6)
| Country | Link |
|---|---|
| US (3) | US20200039938A1 (enExample) |
| EP (1) | EP3600301B1 (enExample) |
| JP (1) | JP7442439B2 (enExample) |
| ES (1) | ES2991090T3 (enExample) |
| TW (1) | TWI814723B (enExample) |
| WO (1) | WO2018183370A2 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SG11201610813TA (en) * | 2014-06-25 | 2017-01-27 | Quanticel Pharmaceuticals Inc | Histone demethylase inhibitors |
| CN113876953B (zh) * | 2020-07-02 | 2022-12-09 | 中国科学院上海营养与健康研究所 | 新型细胞衰老干预靶点及其在化疗抗癌中的靶向应用 |
| EP4319748A4 (en) * | 2021-04-09 | 2025-02-26 | Tachyon Therapeutics, Inc. | TREATMENT OF CANCER WITH KDM4 INHIBITORS |
| US20250129056A1 (en) * | 2021-08-18 | 2025-04-24 | Celgene Corporation | Process for preparing histone demethylase inhibitors |
| US20250134874A1 (en) * | 2021-12-23 | 2025-05-01 | Tachyon Therapeutics, Inc. | Pharmaceutical formulations comprising 3-({[(4r)-7-{methyl[4-(propan-2-yl)phenyl]amino}-3,4-dihydro-2h-1-benzopyran-4-yl]methyl}amino)pyridine-4-carboxylic acid |
| CA3268325A1 (en) * | 2022-09-21 | 2024-03-28 | Celgene Corp | CRYSTALLINE FORMS OF L-LYSINE SALT OF 3-({[(4R)-7-{METHYL[4-(PROPAN-2-YL)PHENYL]AMINO}-3,4-DIHYDRO-2H-1-BENZOPYRAN-4-YL]METHYL}AMINO)PYRIDINE-4-CARBOXYLIC ACID AS A HISTONE DEMETHYLASE INHIBITOR |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3773919A (en) | 1969-10-23 | 1973-11-20 | Du Pont | Polylactide-drug mixtures |
| US20140163041A1 (en) * | 2011-02-08 | 2014-06-12 | Oryzon Genomics S.A. | Lysine demethylase inhibitors for myeloproliferative or lymphoproliferative diseases or disorders |
| ES2718495T3 (es) * | 2012-12-21 | 2019-07-02 | Celgene Quanticel Res Inc | Inhibidores de la histona desmetilasa |
| EA035727B1 (ru) | 2013-10-18 | 2020-07-31 | Селджен Квонтисел Рисёрч, Инк. | Ингибиторы бромодомена |
| US9890434B2 (en) * | 2014-03-19 | 2018-02-13 | National Tsing Hua University | Method for identifying compound for inhibiting an activity of a histone lysine demethylase |
| AR099890A1 (es) * | 2014-03-31 | 2016-08-24 | Epitherapeutics Aps | Inhibidores de histona demetilasas |
| SG11201609033TA (en) | 2014-05-01 | 2016-11-29 | Celgene Quanticel Res Inc | Inhibitors of lysine specific demethylase-1 |
| SG11201610813TA (en) * | 2014-06-25 | 2017-01-27 | Quanticel Pharmaceuticals Inc | Histone demethylase inhibitors |
| US10059687B2 (en) * | 2015-12-28 | 2018-08-28 | Celgene Quanticel Research, Inc. | Histone demethylase inhibitors |
-
2018
- 2018-03-27 US US16/498,714 patent/US20200039938A1/en not_active Abandoned
- 2018-03-27 ES ES18774276T patent/ES2991090T3/es active Active
- 2018-03-27 WO PCT/US2018/024624 patent/WO2018183370A2/en not_active Ceased
- 2018-03-27 US US15/936,811 patent/US20180290977A1/en not_active Abandoned
- 2018-03-27 EP EP18774276.2A patent/EP3600301B1/en active Active
- 2018-03-27 JP JP2020503253A patent/JP7442439B2/ja active Active
- 2018-03-29 TW TW107110863A patent/TWI814723B/zh active
-
2022
- 2022-05-20 US US17/749,233 patent/US20240076271A1/en active Pending
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