JP2014519518A5 - - Google Patents
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- JP2014519518A5 JP2014519518A5 JP2014515041A JP2014515041A JP2014519518A5 JP 2014519518 A5 JP2014519518 A5 JP 2014519518A5 JP 2014515041 A JP2014515041 A JP 2014515041A JP 2014515041 A JP2014515041 A JP 2014515041A JP 2014519518 A5 JP2014519518 A5 JP 2014519518A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- alkylene
- heteroaryl
- aryl
- optionally substituted
- 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
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- 125000000217 alkyl group Chemical group 0.000 claims description 101
- 125000002947 alkylene group Chemical group 0.000 claims description 82
- 150000001875 compounds Chemical class 0.000 claims description 44
- 125000003118 aryl group Chemical group 0.000 claims description 36
- -1 C 1 -C 6 alkyl Chemical group 0.000 claims description 35
- 125000001072 heteroaryl group Chemical group 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 29
- 125000000623 heterocyclic group Chemical group 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
- 229920006395 saturated elastomer Polymers 0.000 claims description 24
- 125000003342 alkenyl group Chemical group 0.000 claims description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
- 125000005843 halogen group Chemical group 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 16
- 125000000304 alkynyl group Chemical group 0.000 claims description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 125000005842 heteroatom Chemical group 0.000 claims description 13
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 239000001301 oxygen Substances 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 239000011593 sulfur Substances 0.000 claims description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 10
- 101001042041 Bos taurus Isocitrate dehydrogenase [NAD] subunit beta, mitochondrial Proteins 0.000 claims description 9
- 101000960234 Homo sapiens Isocitrate dehydrogenase [NADP] cytoplasmic Proteins 0.000 claims description 9
- 102100039905 Isocitrate dehydrogenase [NADP] cytoplasmic Human genes 0.000 claims description 9
- 125000001153 fluoro group Chemical group F* 0.000 claims description 9
- ASSKVPFEZFQQNQ-UHFFFAOYSA-N 2-benzoxazolinone Chemical compound C1=CC=C2OC(O)=NC2=C1 ASSKVPFEZFQQNQ-UHFFFAOYSA-N 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 150000002431 hydrogen Chemical group 0.000 claims description 8
- 125000001041 indolyl group Chemical group 0.000 claims description 8
- 230000035772 mutation Effects 0.000 claims description 8
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 206010028980 Neoplasm Diseases 0.000 claims description 6
- 125000001246 bromo group Chemical group Br* 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims description 5
- RSQUAQMIGSMNNE-UHFFFAOYSA-N 1-methyl-3h-indol-2-one Chemical compound C1=CC=C2N(C)C(=O)CC2=C1 RSQUAQMIGSMNNE-UHFFFAOYSA-N 0.000 claims description 4
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical compound OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 claims description 4
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 4
- 201000003793 Myelodysplastic syndrome Diseases 0.000 claims description 4
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
- 125000002619 bicyclic group Chemical group 0.000 claims description 4
- 201000011510 cancer Diseases 0.000 claims description 4
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 4
- 125000004980 cyclopropylene group Chemical group 0.000 claims description 4
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 4
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 claims description 4
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 4
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- 125000004193 piperazinyl group Chemical group 0.000 claims description 4
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 4
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 4
- 229940124597 therapeutic agent Drugs 0.000 claims description 4
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims description 3
- YJRMHIKEMDTYDR-UHFFFAOYSA-N 2-methylisoquinolin-1-one Chemical compound C1=CC=C2C(=O)N(C)C=CC2=C1 YJRMHIKEMDTYDR-UHFFFAOYSA-N 0.000 claims description 3
- 201000007224 Myeloproliferative neoplasm Diseases 0.000 claims description 3
- 208000006990 cholangiocarcinoma Diseases 0.000 claims description 3
- 125000005054 dihydropyrrolyl group Chemical group [H]C1=C([H])C([H])([H])C([H])([H])N1* 0.000 claims description 3
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 3
- 125000005493 quinolyl group Chemical group 0.000 claims description 3
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims description 2
- 208000005243 Chondrosarcoma Diseases 0.000 claims description 2
- 206010009944 Colon cancer Diseases 0.000 claims description 2
- 108090000790 Enzymes Proteins 0.000 claims description 2
- 102000004190 Enzymes Human genes 0.000 claims description 2
- 208000032612 Glial tumor Diseases 0.000 claims description 2
- 206010018338 Glioma Diseases 0.000 claims description 2
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims description 2
- 206010039491 Sarcoma Diseases 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 208000029742 colonic neoplasm Diseases 0.000 claims description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 208000005017 glioblastoma Diseases 0.000 claims description 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 2
- 201000001441 melanoma Diseases 0.000 claims description 2
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 2
- 125000003566 oxetanyl group Chemical group 0.000 claims description 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 7
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 3
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 2
- MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 claims 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 2
- KPGXRSRHYNQIFN-UHFFFAOYSA-L 2-oxoglutarate(2-) Chemical compound [O-]C(=O)CCC(=O)C([O-])=O KPGXRSRHYNQIFN-UHFFFAOYSA-L 0.000 claims 1
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 125000001288 lysyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 150000002926 oxygen Chemical class 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 description 11
- 125000003709 fluoroalkyl group Chemical group 0.000 description 4
- 239000000203 mixture Substances 0.000 description 3
- 206010004593 Bile duct cancer Diseases 0.000 description 2
- 125000004450 alkenylene group Chemical group 0.000 description 2
- 208000026900 bile duct neoplasm Diseases 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- HWXBTNAVRSUOJR-UHFFFAOYSA-N 2-hydroxyglutaric acid Chemical compound OC(=O)C(O)CCC(O)=O HWXBTNAVRSUOJR-UHFFFAOYSA-N 0.000 description 1
- KPGXRSRHYNQIFN-UHFFFAOYSA-N 2-oxoglutaric acid Chemical compound OC(=O)CCC(=O)C(O)=O KPGXRSRHYNQIFN-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002632 imidazolidinyl group Chemical group 0.000 description 1
- 230000002071 myeloproliferative effect Effects 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000009826 neoplastic cell growth Effects 0.000 description 1
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 description 1
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2011101721691A CN102827073A (zh) | 2011-06-17 | 2011-06-17 | 治疗活性组合物和它们的使用方法 |
| CN201110172169.1 | 2011-06-17 | ||
| US201161509071P | 2011-07-18 | 2011-07-18 | |
| US61/509,071 | 2011-07-18 | ||
| US201261584210P | 2012-01-06 | 2012-01-06 | |
| US61/584,210 | 2012-01-06 | ||
| PCT/CN2012/000841 WO2012171337A1 (en) | 2011-06-17 | 2012-06-18 | Therapeutically active compositions and their methods of use |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016251072A Division JP2017057221A (ja) | 2011-06-17 | 2016-12-26 | 治療活性組成物およびそれらの使用方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014519518A JP2014519518A (ja) | 2014-08-14 |
| JP2014519518A5 true JP2014519518A5 (enExample) | 2015-08-13 |
| JP6152098B2 JP6152098B2 (ja) | 2017-06-21 |
Family
ID=47330415
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014515041A Expired - Fee Related JP6152098B2 (ja) | 2011-06-17 | 2012-06-18 | 治療活性組成物およびそれらの使用方法 |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US20140213580A1 (enExample) |
| EP (1) | EP2721019B1 (enExample) |
| JP (1) | JP6152098B2 (enExample) |
| CN (1) | CN102827073A (enExample) |
| AR (1) | AR086977A1 (enExample) |
| AU (1) | AU2012269648B2 (enExample) |
| CA (1) | CA2839675C (enExample) |
| ES (1) | ES2694160T3 (enExample) |
| MX (1) | MX345928B (enExample) |
| TW (1) | TWI628165B (enExample) |
| WO (1) | WO2012171337A1 (enExample) |
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| PE20120693A1 (es) | 2009-06-29 | 2012-07-04 | Agios Pharmaceuticals Inc | Compuestos heterociclos como moduladores de la piruvato cinasa m2 (pkm2) |
| WO2012057262A1 (ja) * | 2010-10-28 | 2012-05-03 | 日本新薬株式会社 | ピリジン誘導体及び医薬 |
| CN102827170A (zh) | 2011-06-17 | 2012-12-19 | 安吉奥斯医药品有限公司 | 治疗活性组合物和它们的使用方法 |
| CN102827073A (zh) | 2011-06-17 | 2012-12-19 | 安吉奥斯医药品有限公司 | 治疗活性组合物和它们的使用方法 |
| MX342326B (es) | 2011-09-27 | 2016-09-26 | Novartis Ag | 3-pirimidin-4-il-oxazolidin-2-onas como inhibidoras de idh mutante. |
| SMT201800334T1 (it) | 2012-01-06 | 2018-09-13 | Agios Pharmaceuticals Inc | Composti terapeuticamente attivi e loro metodi di utilizzo |
| US9474779B2 (en) | 2012-01-19 | 2016-10-25 | Agios Pharmaceuticals, Inc. | Therapeutically active compositions and their methods of use |
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| JP6888101B2 (ja) | 2017-01-18 | 2021-06-16 | アレイ バイオファーマ インコーポレイテッド | ＲＥＴキナーゼ阻害剤としての置換ピラゾロ［１，５−ａ］ピラジン化合物 |
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