JP2014513134A5 - - Google Patents
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- Publication number
- JP2014513134A5 JP2014513134A5 JP2014509459A JP2014509459A JP2014513134A5 JP 2014513134 A5 JP2014513134 A5 JP 2014513134A5 JP 2014509459 A JP2014509459 A JP 2014509459A JP 2014509459 A JP2014509459 A JP 2014509459A JP 2014513134 A5 JP2014513134 A5 JP 2014513134A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- formula
- pharmaceutically acceptable
- compound
- piperazinyl
- 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
- 150000001875 compounds Chemical class 0.000 claims description 31
- 150000003839 salts Chemical class 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 26
- -1 carbocycle Chemical group 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 150000001721 carbon Chemical group 0.000 claims description 8
- 125000001188 haloalkyl group Chemical group 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
- 210000004369 blood Anatomy 0.000 claims description 7
- 239000008280 blood Substances 0.000 claims description 7
- 239000003937 drug carrier Substances 0.000 claims description 7
- 210000003743 erythrocyte Anatomy 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- XOHUEYCVLUUEJJ-UHFFFAOYSA-I 2,3-Diphosphoglycerate Chemical compound [O-]P(=O)([O-])OC(C(=O)[O-])COP([O-])([O-])=O XOHUEYCVLUUEJJ-UHFFFAOYSA-I 0.000 claims description 2
- WTQLCJQZNSECQT-UHFFFAOYSA-N 2-oxo-n-[4-(4-phenylpiperazine-1-carbonyl)phenyl]-1,3-dihydrobenzimidazole-5-sulfonamide Chemical compound C=1C=C(NS(=O)(=O)C=2C=C3NC(=O)NC3=CC=2)C=CC=1C(=O)N(CC1)CCN1C1=CC=CC=C1 WTQLCJQZNSECQT-UHFFFAOYSA-N 0.000 claims description 2
- GJUZEPDVPURTJO-UHFFFAOYSA-N 2-oxo-n-[4-(4-pyridin-2-ylpiperazine-1-carbonyl)phenyl]-1,3-dihydrobenzimidazole-5-sulfonamide Chemical compound C=1C=C(NS(=O)(=O)C=2C=C3NC(=O)NC3=CC=2)C=CC=1C(=O)N(CC1)CCN1C1=CC=CC=N1 GJUZEPDVPURTJO-UHFFFAOYSA-N 0.000 claims description 2
- BFTCRVGGPSHTOJ-UHFFFAOYSA-N 2-oxo-n-[4-[4-(2,2,2-trifluoroethyl)piperazine-1-carbonyl]phenyl]-1,3-dihydrobenzimidazole-5-sulfonamide Chemical compound C1CN(CC(F)(F)F)CCN1C(=O)C(C=C1)=CC=C1NS(=O)(=O)C1=CC=C(NC(=O)N2)C2=C1 BFTCRVGGPSHTOJ-UHFFFAOYSA-N 0.000 claims description 2
- XLIKYSFZVYNBAP-UHFFFAOYSA-N 2-oxo-n-[4-[4-(thiophen-3-ylmethyl)piperazine-1-carbonyl]phenyl]-1,3-dihydrobenzimidazole-5-sulfonamide Chemical compound C=1C=C(NS(=O)(=O)C=2C=C3NC(=O)NC3=CC=2)C=CC=1C(=O)N(CC1)CCN1CC=1C=CSC=1 XLIKYSFZVYNBAP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000002837 carbocyclic group Chemical group 0.000 claims description 2
- 210000004027 cell Anatomy 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
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([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
- TXMXKWSHRLLINA-UHFFFAOYSA-N ethyl 4-[4-[(2-oxo-1,3-dihydrobenzimidazol-5-yl)sulfonylamino]benzoyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1C(=O)C(C=C1)=CC=C1NS(=O)(=O)C1=CC=C(NC(=O)N2)C2=C1 TXMXKWSHRLLINA-UHFFFAOYSA-N 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims description 2
- 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 claims description 2
- 125000004499 isoxazol-5-yl group Chemical group O1N=CC=C1* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- RUZLIIJDZBWWSA-INIZCTEOSA-N methyl 2-[[(1s)-1-(7-methyl-2-morpholin-4-yl-4-oxopyrido[1,2-a]pyrimidin-9-yl)ethyl]amino]benzoate Chemical group COC(=O)C1=CC=CC=C1N[C@@H](C)C1=CC(C)=CN2C(=O)C=C(N3CCOCC3)N=C12 RUZLIIJDZBWWSA-INIZCTEOSA-N 0.000 claims description 2
- ZEZRSVCSJSRGLO-UHFFFAOYSA-N n-[3-(3,5-dimethoxyanilino)quinoxalin-2-yl]-4-(4-methylpiperazine-1-carbonyl)benzenesulfonamide Chemical compound COC1=CC(OC)=CC(NC=2C(=NC3=CC=CC=C3N=2)NS(=O)(=O)C=2C=CC(=CC=2)C(=O)N2CCN(C)CC2)=C1 ZEZRSVCSJSRGLO-UHFFFAOYSA-N 0.000 claims description 2
- SDPWIXFRKBOJHH-UHFFFAOYSA-N n-[4-(4-acetylpiperazine-1-carbonyl)phenyl]-2-oxo-1,3-dihydrobenzimidazole-5-sulfonamide Chemical compound C1CN(C(=O)C)CCN1C(=O)C(C=C1)=CC=C1NS(=O)(=O)C1=CC=C(NC(=O)N2)C2=C1 SDPWIXFRKBOJHH-UHFFFAOYSA-N 0.000 claims description 2
- PKNOUYFGJZBGIQ-UHFFFAOYSA-N n-[4-[4-(2,3-dimethylphenyl)piperazine-1-carbonyl]phenyl]-2-oxo-1,3-dihydrobenzimidazole-5-sulfonamide Chemical compound CC1=CC=CC(N2CCN(CC2)C(=O)C=2C=CC(NS(=O)(=O)C=3C=C4NC(=O)NC4=CC=3)=CC=2)=C1C PKNOUYFGJZBGIQ-UHFFFAOYSA-N 0.000 claims description 2
- YOTDGZDZJATVAS-UHFFFAOYSA-N n-[4-[4-(2-ethoxyphenyl)piperazine-1-carbonyl]phenyl]-2-oxo-1,3-dihydrobenzimidazole-5-sulfonamide Chemical compound CCOC1=CC=CC=C1N1CCN(C(=O)C=2C=CC(NS(=O)(=O)C=3C=C4NC(=O)NC4=CC=3)=CC=2)CC1 YOTDGZDZJATVAS-UHFFFAOYSA-N 0.000 claims description 2
- QUTMWIBWVVIQIV-UHFFFAOYSA-N n-[4-[4-(2-hydroxyphenyl)piperazine-1-carbonyl]phenyl]-2-oxo-1,3-dihydrobenzimidazole-5-sulfonamide Chemical compound OC1=CC=CC=C1N1CCN(C(=O)C=2C=CC(NS(=O)(=O)C=3C=C4NC(=O)NC4=CC=3)=CC=2)CC1 QUTMWIBWVVIQIV-UHFFFAOYSA-N 0.000 claims description 2
- GHZZESYKWCBRJB-UHFFFAOYSA-N n-[4-[4-(4-fluorophenyl)piperazine-1-carbonyl]phenyl]-2-oxo-1,3-dihydrobenzimidazole-5-sulfonamide Chemical compound C1=CC(F)=CC=C1N1CCN(C(=O)C=2C=CC(NS(=O)(=O)C=3C=C4NC(=O)NC4=CC=3)=CC=2)CC1 GHZZESYKWCBRJB-UHFFFAOYSA-N 0.000 claims description 2
- SLNRYAYGMZMYHV-UHFFFAOYSA-N n-[4-[4-(4-nitrophenyl)piperazine-1-carbonyl]phenyl]-2-oxo-1,3-dihydrobenzimidazole-5-sulfonamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1N1CCN(C(=O)C=2C=CC(NS(=O)(=O)C=3C=C4NC(=O)NC4=CC=3)=CC=2)CC1 SLNRYAYGMZMYHV-UHFFFAOYSA-N 0.000 claims description 2
- MERGJCWMDMBTNS-UHFFFAOYSA-N n-[4-[4-(furan-2-ylmethyl)piperazine-1-carbonyl]phenyl]-2-oxo-1,3-dihydrobenzimidazole-5-sulfonamide Chemical compound C=1C=C(NS(=O)(=O)C=2C=C3NC(=O)NC3=CC=2)C=CC=1C(=O)N(CC1)CCN1CC1=CC=CO1 MERGJCWMDMBTNS-UHFFFAOYSA-N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000003145 oxazol-4-yl group Chemical group O1C=NC(=C1)* 0.000 claims description 2
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 2
- 208000007056 sickle cell anemia Diseases 0.000 claims description 2
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 claims description 2
- 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 claims description 2
- 208000007475 hemolytic anemia Diseases 0.000 claims 1
- 238000000338 in vitro Methods 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 206010018910 Haemolysis Diseases 0.000 description 1
- 208000007502 anemia Diseases 0.000 description 1
- 230000008588 hemolysis Effects 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161482166P | 2011-05-03 | 2011-05-03 | |
| US61/482,166 | 2011-05-03 | ||
| PCT/US2012/036413 WO2012151452A1 (en) | 2011-05-03 | 2012-05-03 | Pyruvate kinase activators for use in therapy |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016173166A Division JP6267299B2 (ja) | 2011-05-03 | 2016-09-05 | ピルビン酸キナーゼアクチベーターの使用方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014513134A JP2014513134A (ja) | 2014-05-29 |
| JP2014513134A5 true JP2014513134A5 (enExample) | 2015-06-25 |
| JP6267112B2 JP6267112B2 (ja) | 2018-01-24 |
Family
ID=46085224
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014509459A Expired - Fee Related JP6267112B2 (ja) | 2011-05-03 | 2012-05-03 | ピルビン酸キナーゼアクチベーターの使用方法 |
| JP2016173166A Expired - Fee Related JP6267299B2 (ja) | 2011-05-03 | 2016-09-05 | ピルビン酸キナーゼアクチベーターの使用方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016173166A Expired - Fee Related JP6267299B2 (ja) | 2011-05-03 | 2016-09-05 | ピルビン酸キナーゼアクチベーターの使用方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US9404081B2 (enExample) |
| EP (1) | EP2704720B1 (enExample) |
| JP (2) | JP6267112B2 (enExample) |
| CN (1) | CN103608016A (enExample) |
| AU (1) | AU2012250690B2 (enExample) |
| CA (1) | CA2834692A1 (enExample) |
| ES (1) | ES2746558T3 (enExample) |
| WO (1) | WO2012151452A1 (enExample) |
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| EP2406389B1 (en) | 2009-03-13 | 2019-05-08 | Agios Pharmaceuticals, Inc. | Methods and compositions for cell-proliferation-related disorders |
| CA2758071C (en) | 2009-04-06 | 2018-01-09 | Agios Pharmaceuticals, Inc. | Pyruvate kinase m2 modulators, therapeutic compositions and related methods of use |
| TWI691493B (zh) | 2009-06-29 | 2020-04-21 | 美商阿吉歐斯製藥公司 | 治療化合物及組成物 |
| WO2011050210A1 (en) | 2009-10-21 | 2011-04-28 | Agios Pharmaceuticals, Inc. | Methods and compositions for cell-proliferation-related disorders |
| WO2012088314A1 (en) | 2010-12-21 | 2012-06-28 | Agios Pharmaceuticals, Inc. | Bicyclic pkm2 activators |
| TWI549947B (zh) * | 2010-12-29 | 2016-09-21 | 阿吉歐斯製藥公司 | 治療化合物及組成物 |
| SMT202400081T1 (it) | 2011-05-03 | 2024-03-13 | Agios Pharmaceuticals Inc | Attivatori della piruvato chinasi per uso in terapia |
| ES2746558T3 (es) | 2011-05-03 | 2020-03-06 | Agios Pharmaceuticals Inc | Activadores de piruvato cinasa R para uso en terapia |
| 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 |
| US9474779B2 (en) | 2012-01-19 | 2016-10-25 | Agios Pharmaceuticals, Inc. | Therapeutically active compositions and their methods of use |
| PT2968316T (pt) | 2013-03-13 | 2019-10-29 | Forma Therapeutics Inc | Derivados de 2-hidroxi-1-{4-[(4-fenilfenil)carbonil]piperazin-1-il}etano-1-ona e compostos relacionados como inibidores da sintase de ácidos gordos (fasn) para o tratamento do cancro |
| WO2014139144A1 (en) * | 2013-03-15 | 2014-09-18 | Agios Pharmaceuticals, Inc. | Therapeutic compounds and compositions |
| WO2015003355A2 (en) | 2013-07-11 | 2015-01-15 | Agios Pharmaceuticals, Inc. | Therapeutically active compounds and their methods of use |
| US10376510B2 (en) | 2013-07-11 | 2019-08-13 | Agios Pharmaceuticals, Inc. | 2,4- or 4,6-diaminopyrimidine compounds as IDH2 mutants inhibitors for the treatment of cancer |
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| UA121211C2 (uk) | 2014-03-14 | 2020-04-27 | Аджіос Фармасьютикалз, Інк. | Фармацевтична композиція, що містить тверду дисперсію, та спосіб лікування гострої мієлогенної/мієлоїдної лейкемії (гмл) |
| FR3030516B1 (fr) * | 2014-12-19 | 2019-12-27 | Galderma Research & Development | Derives sulfonamides bicycles en tant qu'agonistes inverses du recepteur gamma orphelin associe aux retinoides ror gamma (t) |
| PL3307271T3 (pl) * | 2015-06-11 | 2024-02-05 | Agios Pharmaceuticals, Inc. | Sposoby stosowania aktywatorów kinazy pirogronianowej |
| MX386735B (es) | 2015-10-15 | 2025-03-19 | Servier Lab | Terapia de combinacion para tratar tumores malignos. |
| ES2981538T3 (es) | 2015-10-15 | 2024-10-09 | Servier Lab | Terapia de combinación que comprende ivosidenib, citarabina y daunorrubicina o idarrubicina para el tratamiento de leucemia mielógena aguda |
| SMT201900517T1 (it) | 2017-03-20 | 2019-11-13 | Forma Therapeutics Inc | Composizioni di pirrolopirrolo come attivatori di piruvato chinasi (pkr) |
| RS64221B1 (sr) | 2017-08-15 | 2023-06-30 | Agios Pharmaceuticals Inc | Modulatori piruvat kinaze i njihova upotreba |
| US10980788B2 (en) | 2018-06-08 | 2021-04-20 | Agios Pharmaceuticals, Inc. | Therapy for treating malignancies |
| US11001588B2 (en) | 2018-09-19 | 2021-05-11 | Forma Therapeutics, Inc. | Activating pyruvate kinase R and mutants thereof |
| CN113166060B (zh) | 2018-09-19 | 2024-01-09 | 诺沃挪第克健康护理股份公司 | 用丙酮酸激酶激活化合物治疗镰状细胞病 |
| TWI767148B (zh) | 2018-10-10 | 2022-06-11 | 美商弗瑪治療公司 | 抑制脂肪酸合成酶(fasn) |
| CN113382633A (zh) | 2018-10-29 | 2021-09-10 | 福马治疗股份有限公司 | (4-(2-氟-4-(1-甲基-1H-苯并[d]咪唑-5-基)苯甲酰基)哌嗪-1-基)(1-羟基环丙基)甲酮的固体形式 |
| US20220127267A1 (en) * | 2019-02-13 | 2022-04-28 | Agios Pharmaceuticals, Inc. | Thieno[3,2-b] pyrrole[3,2-d]pyridazinone derivatives and their use as pkm2 derivatives for the treatment of cancer, obesity and diabetes related disorders |
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| CN111892599B (zh) * | 2020-08-14 | 2023-01-13 | 黄芳 | 一种2,5-二氮杂双环[2.2.2]辛烷-2-羧酸叔丁酯的合成方法 |
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| EP4147700A1 (en) * | 2021-09-08 | 2023-03-15 | LQT Therapeutics Inc. | N-(4-(azaindazol-6-yl)-phenyl)-sulfonamides for use in the treatment of sickle cell disease |
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| TWI691493B (zh) | 2009-06-29 | 2020-04-21 | 美商阿吉歐斯製藥公司 | 治療化合物及組成物 |
| US20120189670A1 (en) | 2009-09-14 | 2012-07-26 | Kirkpatrick D Lynn | Pharmaceutical compositions and formulations including inhibitors of the pleckstrin homology domain and methods for using same |
| CN105153188B (zh) | 2009-10-22 | 2018-06-01 | 法博太科制药有限公司 | 抗纤维化剂的稠环类似物 |
| KR20130044382A (ko) * | 2010-03-01 | 2013-05-02 | 마이렉시스 인코포레이티드 | 화합물 및 그의 치료 용도 |
| FR2967674B1 (fr) * | 2010-11-23 | 2012-12-14 | Pf Medicament | Derives d'heteroarylsulfonamides, leur preparation et leur application en therapeutique humaine |
| TWI549947B (zh) | 2010-12-29 | 2016-09-21 | 阿吉歐斯製藥公司 | 治療化合物及組成物 |
| SMT202400081T1 (it) * | 2011-05-03 | 2024-03-13 | Agios Pharmaceuticals Inc | Attivatori della piruvato chinasi per uso in terapia |
| ES2746558T3 (es) * | 2011-05-03 | 2020-03-06 | Agios Pharmaceuticals Inc | Activadores de piruvato cinasa R para uso en terapia |
-
2012
- 2012-05-03 ES ES12721111T patent/ES2746558T3/es active Active
- 2012-05-03 CA CA2834692A patent/CA2834692A1/en not_active Abandoned
- 2012-05-03 US US14/115,292 patent/US9404081B2/en not_active Expired - Fee Related
- 2012-05-03 AU AU2012250690A patent/AU2012250690B2/en not_active Ceased
- 2012-05-03 CN CN201280028693.4A patent/CN103608016A/zh active Pending
- 2012-05-03 EP EP12721111.8A patent/EP2704720B1/en active Active
- 2012-05-03 JP JP2014509459A patent/JP6267112B2/ja not_active Expired - Fee Related
- 2012-05-03 WO PCT/US2012/036413 patent/WO2012151452A1/en not_active Ceased
-
2016
- 2016-09-05 JP JP2016173166A patent/JP6267299B2/ja not_active Expired - Fee Related
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