BR122017014843B1 - métodos para preparar compostos úteis para tratamento de câncer - Google Patents
métodos para preparar compostos úteis para tratamento de câncer Download PDFInfo
- Publication number
- BR122017014843B1 BR122017014843B1 BR122017014843-5A BR122017014843A BR122017014843B1 BR 122017014843 B1 BR122017014843 B1 BR 122017014843B1 BR 122017014843 A BR122017014843 A BR 122017014843A BR 122017014843 B1 BR122017014843 B1 BR 122017014843B1
- Authority
- BR
- Brazil
- Prior art keywords
- alkyl
- alkylene
- optionally substituted
- phenyl
- triazine
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 331
- 238000000034 method Methods 0.000 title claims abstract description 125
- 206010028980 Neoplasm Diseases 0.000 title abstract description 71
- 201000011510 cancer Diseases 0.000 title abstract description 53
- 125000002947 alkylene group Chemical group 0.000 claims description 282
- -1 -C1- alkyl C4 Chemical group 0.000 claims description 245
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 225
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 215
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 168
- 239000000203 mixture Substances 0.000 claims description 157
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 113
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 99
- 229910052739 hydrogen Inorganic materials 0.000 claims description 93
- 239000001257 hydrogen Substances 0.000 claims description 92
- 125000000623 heterocyclic group Chemical group 0.000 claims description 86
- 125000000217 alkyl group Chemical group 0.000 claims description 78
- 125000001188 haloalkyl group Chemical group 0.000 claims description 67
- 238000006243 chemical reaction Methods 0.000 claims description 62
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 57
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 57
- 125000004076 pyridyl group Chemical group 0.000 claims description 57
- 125000003118 aryl group Chemical group 0.000 claims description 56
- 229910052731 fluorine Inorganic materials 0.000 claims description 56
- 125000001072 heteroaryl group Chemical group 0.000 claims description 55
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 53
- 239000000460 chlorine Substances 0.000 claims description 51
- 239000011737 fluorine Substances 0.000 claims description 50
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 47
- 229910052801 chlorine Inorganic materials 0.000 claims description 47
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 46
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 45
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 43
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 38
- 125000001424 substituent group Chemical group 0.000 claims description 37
- 229910052757 nitrogen Inorganic materials 0.000 claims description 35
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 32
- 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 27
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 26
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 25
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 23
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 22
- 125000001475 halogen functional group Chemical group 0.000 claims description 22
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 22
- 125000000304 alkynyl group Chemical group 0.000 claims description 20
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 18
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 17
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 16
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical group [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 16
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 14
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 14
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 14
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 13
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 11
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
- 229910052794 bromium Inorganic materials 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 8
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 8
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 8
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 8
- 229910019213 POCl3 Inorganic materials 0.000 claims description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 6
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims description 6
- 235000015320 potassium carbonate Nutrition 0.000 claims description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000002393 azetidinyl group Chemical group 0.000 claims description 5
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 5
- 125000002971 oxazolyl group Chemical group 0.000 claims description 5
- 229910052763 palladium Inorganic materials 0.000 claims description 5
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical group [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 5
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 5
- 125000000335 thiazolyl group Chemical group 0.000 claims description 5
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000002757 morpholinyl group Chemical group 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- 235000017550 sodium carbonate Nutrition 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims 4
- 150000004703 alkoxides Chemical class 0.000 claims 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Inorganic materials [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 claims 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 341
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 285
- 238000005160 1H NMR spectroscopy Methods 0.000 description 209
- 238000002360 preparation method Methods 0.000 description 125
- 125000005843 halogen group Chemical group 0.000 description 122
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 87
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 77
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 72
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 71
- 239000000243 solution Substances 0.000 description 66
- 239000000047 product Substances 0.000 description 65
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 58
- 230000035772 mutation Effects 0.000 description 55
- 238000010561 standard procedure Methods 0.000 description 55
- 150000002431 hydrogen Chemical class 0.000 description 48
- 239000011541 reaction mixture Substances 0.000 description 48
- 239000007832 Na2SO4 Substances 0.000 description 45
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 45
- 229910052938 sodium sulfate Inorganic materials 0.000 description 45
- 235000011152 sodium sulphate Nutrition 0.000 description 45
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 42
- 235000017168 chlorine Nutrition 0.000 description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 42
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 41
- 125000004432 carbon atom Chemical group C* 0.000 description 41
- 239000012044 organic layer Substances 0.000 description 40
- 235000002639 sodium chloride Nutrition 0.000 description 39
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- 230000002829 reductive effect Effects 0.000 description 37
- 150000003839 salts Chemical class 0.000 description 37
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 36
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- 238000011282 treatment Methods 0.000 description 35
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 21
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
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- 239000007858 starting material Substances 0.000 description 16
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 15
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- XJLXINKUBYWONI-DQQFMEOOSA-N [[(2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2s,3r,4s,5s)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate Chemical compound NC(=O)C1=CC=C[N+]([C@@H]2[C@H]([C@@H](O)[C@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-DQQFMEOOSA-N 0.000 description 13
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- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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| CNPCT/CN2013/079200 | 2013-07-11 | ||
| BR112016000561A BR112016000561B8 (pt) | 2013-07-11 | 2014-07-10 | Compostos terapeuticamente ativos, uso dos mesmos, composição farmacêutica e uso da mesma |
| PCT/CN2014/081957 WO2015003640A1 (en) | 2013-07-11 | 2014-07-10 | Therapeutically active compounds and their methods of use |
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Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CN104822373B (zh) | 2012-10-15 | 2018-08-28 | 安吉奥斯医药品有限公司 | 治疗性化合物和组合物 |
| AU2014287121B2 (en) | 2013-07-11 | 2018-11-15 | Agios Pharmaceuticals, Inc. | 2,4- or 4,6-diaminopyrimidine compounds as IDH2 mutants inhibitors for the treatment of cancer |
| US9579324B2 (en) | 2013-07-11 | 2017-02-28 | Agios Pharmaceuticals, Inc | Therapeutically active compounds and their methods of use |
| WO2015003355A2 (en) | 2013-07-11 | 2015-01-15 | Agios Pharmaceuticals, Inc. | Therapeutically active compounds and their methods of use |
| WO2015003360A2 (en) | 2013-07-11 | 2015-01-15 | Agios Pharmaceuticals, Inc. | Therapeutically active compounds and their methods of use |
| US20150031627A1 (en) | 2013-07-25 | 2015-01-29 | Agios Pharmaceuticals, Inc | Therapeutically active compounds and their methods of use |
| EA036325B1 (ru) | 2014-03-14 | 2020-10-27 | Аджиос Фармасьютикалз, Инк. | Фармацевтическая композиция на основе твердой дисперсии ингибитора idh1 |
| CN104672093B (zh) * | 2015-03-22 | 2016-04-13 | 成都塞恩斯医药科技有限公司 | 一种双环丙基甲胺的制备方法 |
| HUE056537T2 (hu) * | 2015-07-30 | 2022-02-28 | Chia Tai Tianqing Pharmaceutical Group Co Ltd | 1,3,5-triazinszármazék és annak alkalmazási módszere |
| US9751863B2 (en) * | 2015-08-05 | 2017-09-05 | Agios Pharmaceuticals, Inc. | Therapeutically active compounds and their methods of use |
| UA123401C2 (uk) | 2015-10-15 | 2021-03-31 | Аджиос Фармасьютікалз, Інк. | Комбінована терапія для лікування злоякісних пухлин |
| ES2897959T3 (es) | 2015-10-15 | 2022-03-03 | Servier Lab | Terapia de combinación para tratar neoplasias malignas |
| CA3002531C (en) | 2015-10-21 | 2020-08-18 | NeuForm Pharmaceuticals, Inc. | Deuterated compounds for treating hematologic malignancies, and compositions and methods thereof |
| WO2017140758A1 (en) | 2016-02-19 | 2017-08-24 | Debiopharm International S.A. | Derivatives of 2-amino-4-(2-oxazolidinon-3-yl)-pyrimidine fused with a five-membered heteroaromatic ring in 5,6-position which are useful for the treatment of various cancers |
| US10774064B2 (en) | 2016-06-02 | 2020-09-15 | Cadent Therapeutics, Inc. | Potassium channel modulators |
| US10961222B2 (en) | 2016-07-21 | 2021-03-30 | Nanjing Sanhome Pharmaceutical Co., Ltd. | Chemical compound of isocitrate dehydrogenase inhibitor, and application thereof |
| DK3490972T3 (da) * | 2016-07-28 | 2020-12-14 | Bayer Cropscience Ag | Fremgangsmåde til fremstilling af fluoralkylnitriler og de tilsvarende fluoralkyltetrazoler |
| CU24560B1 (es) | 2017-01-23 | 2021-12-08 | Cadent Therapeutics Inc | N-(4,4-difluorociclohexil)-2-(3-metil-1h-pirazol-1-il)-6-morfolinopirimidin-4-amina útil como modulador de canales de potasio |
| BR112019026435A2 (pt) | 2017-06-12 | 2020-07-14 | Agios Pharmaceuticals, Inc. | métodos de tratamento de tumores cerebrais usando terapia de combinação |
| CN119280245A (zh) * | 2017-06-12 | 2025-01-10 | 法国施维雅药厂 | 使用组合疗法治疗脑肿瘤的方法 |
| CN109265444B (zh) * | 2017-07-17 | 2022-03-11 | 南京圣和药业股份有限公司 | 取代的三嗪类idh抑制剂的光学异构体及其应用 |
| CN109467538A (zh) | 2017-09-07 | 2019-03-15 | 和记黄埔医药(上海)有限公司 | 环烯烃取代的杂芳环类化合物及其用途 |
| IL274123B2 (en) * | 2017-11-02 | 2024-01-01 | Agios Pharmaceuticals Inc | Cocrystals, pharmaceutical compositions thereof, and methods of treatment involving same |
| US10980788B2 (en) | 2018-06-08 | 2021-04-20 | Agios Pharmaceuticals, Inc. | Therapy for treating malignancies |
| AU2019366312B2 (en) | 2018-10-22 | 2025-04-24 | Novartis Ag | Crystalline forms of potassium channel modulators |
| CN114585359B (zh) | 2019-10-16 | 2025-08-12 | 凯莫森特里克斯股份有限公司 | 用于治疗pd-l1疾病的杂芳基联苯酰胺 |
| WO2022019289A1 (ja) | 2020-07-21 | 2022-01-27 | 第一三共株式会社 | テモゾロミドと変異型idh1酵素阻害剤の組み合わせ医薬 |
| US11865079B2 (en) * | 2021-02-12 | 2024-01-09 | Servier Pharmaceuticals Llc | Therapeutically active compounds and their methods of use |
| EP4291198A4 (en) * | 2021-02-12 | 2024-12-25 | Les Laboratoires Servier | THERAPEUTICALLY ACTIVE COMPOUNDS AND METHODS OF USE THEREOF |
| CN113461660B (zh) * | 2021-06-11 | 2022-08-02 | 浙江大学 | 2,4,6-三取代-1,3,5-均三嗪类化合物及制备和应用 |
| CN118355008A (zh) * | 2022-01-11 | 2024-07-16 | 正大天晴药业集团股份有限公司 | 一种1,3,5-三嗪衍生物的制备方法 |
| US20250051301A1 (en) * | 2022-03-15 | 2025-02-13 | Betta Pharmaceuticals Co., Ltd | Mutant idh1 and idh2 inhibitor and application thereof |
| CN114773320A (zh) * | 2022-05-29 | 2022-07-22 | 重庆医科大学 | 1,3,5-三嗪化合物及其制备方法和用途 |
| AU2023407344A1 (en) * | 2022-12-23 | 2025-07-31 | The Board Of Trustees Of The University Of Illinois | Foxm1 inhibitors and their use in treating cancers |
| WO2025168757A1 (en) | 2024-02-09 | 2025-08-14 | Les Laboratoires Servier | Process for the preparation of vorasidenib |
Family Cites Families (183)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2390529A (en) | 1942-02-03 | 1945-12-11 | Ernst A H Friedheim | Hydrazino-1,3,5-triazino derivatives of substituted phenylarsenic compounds |
| DE1252822B (enExample) * | 1963-02-15 | |||
| BE754242A (fr) * | 1970-07-15 | 1971-02-01 | Geigy Ag J R | Diamino-s-triazines et dinitro-s-triazines |
| US3867383A (en) * | 1971-03-29 | 1975-02-18 | Ciba Geigy Corp | Monoanthranilatoanilino-s-triazines |
| US3681332A (en) * | 1971-04-13 | 1972-08-01 | Lilly Industries Ltd | Dihalo-s-triazine compounds |
| BE793501A (fr) * | 1971-12-31 | 1973-06-29 | Ciba Geigy | Composes heterocycliques et produits phytopharmaceutiques qui en contiennent |
| CH606334A5 (enExample) * | 1974-06-21 | 1978-10-31 | Ciba Geigy Ag | |
| JPS5170779A (ja) * | 1974-12-17 | 1976-06-18 | Nippon Shinyaku Co Ltd | Shinkinaguanamidoruino seiho |
| DE2715984A1 (de) | 1977-04-09 | 1978-10-26 | Basf Ag | Farbstoffzubereitungen fuer cellulose und cellulosehaltiges textilmaterial |
| DE2737984A1 (de) | 1977-08-23 | 1979-03-08 | Lentia Gmbh | Verfahren zur herstellung von lagerstabilen und vergilbungsfrei einbrennbaren lackharzen |
| DE2928485A1 (de) | 1979-07-14 | 1981-01-29 | Bayer Ag | Verwendung von harnstoffderivaten als arzneimittel bei der behandlung von fettstoffwechselstoerungen |
| JPS5655302A (en) * | 1979-10-15 | 1981-05-15 | Hokko Chem Ind Co Ltd | Fungicide for agriculture and horticulture |
| DE3103110A1 (de) * | 1981-01-30 | 1982-08-26 | Basf Ag, 6700 Ludwigshafen | Triazingruppenhaltige verbindungen |
| JPS58186682A (ja) | 1982-04-27 | 1983-10-31 | 日本化薬株式会社 | セルロ−ス又はセルロ−ス含有繊維材料の染色法 |
| DE3512630A1 (de) | 1985-04-06 | 1986-10-23 | Hoechst Ag, 6230 Frankfurt | Verfahren zum faerben oder bedrucken von cellulosefasern oder cellulosemischfasern |
| US5041443A (en) | 1989-02-21 | 1991-08-20 | Dainippon Pharmaceutical Co., Ltd. | Medicament for treating cerebral insufficiency diseases, novel 2-(1-piperazinyl)-4-phenylcycloalkanopyrimidine derivatives, and process for the production thereof |
| DE69010232T2 (de) | 1989-03-03 | 1994-12-01 | Dainippon Pharmaceutical Co | 2-(1-Piperazinyl)-4-phenylcycloalkanpyridin-Derivate, Verfahren zu deren Herstellung und pharmazeutische Zusammensetzungen, die sie enthalten. |
| DE3922735A1 (de) * | 1989-07-11 | 1991-01-24 | Hoechst Ag | Aminopyrimidin-derivate, verfahren zu ihrer herstellung, sie enthaltende mittel und ihre verwendung als fungizide |
| JPH0499768A (ja) | 1990-08-17 | 1992-03-31 | Dainippon Pharmaceut Co Ltd | 4―(4―フェニルピリジン―2―イル)ピペラジン―1―オキシド誘導体 |
| JPH05140126A (ja) * | 1991-11-26 | 1993-06-08 | Hokko Chem Ind Co Ltd | トリアゾール誘導体および除草剤 |
| US5489591A (en) * | 1992-02-28 | 1996-02-06 | Zenyaku Kogyo Kabushiki Kaisha | S-triazine derivative and remedy for estrogen-dependent disease containing said derivative as effective component |
| US5441563A (en) | 1993-07-06 | 1995-08-15 | Armstrong World Industries, Inc. | Highly insoluble azole embossing inhibitor and the use thereof |
| IL115420A0 (en) | 1994-09-26 | 1995-12-31 | Zeneca Ltd | Aminoheterocyclic derivatives |
| IL117580A0 (en) | 1995-03-29 | 1996-07-23 | Merck & Co Inc | Inhibitors of farnesyl-protein transferase and pharmaceutical compositions containing them |
| JPH08311047A (ja) * | 1995-05-16 | 1996-11-26 | Nissan Chem Ind Ltd | シアノエチルメラミン誘導体およびその製造方法 |
| FR2735127B1 (fr) | 1995-06-09 | 1997-08-22 | Pf Medicament | Nouvelles piperazines heteroaromatiques utiles comme medicaments. |
| AU6015896A (en) | 1995-06-15 | 1997-01-15 | Nissan Chemical Industries Ltd. | Epoxy/acid anhydride composition |
| ES2100129B1 (es) | 1995-10-11 | 1998-02-16 | Medichem Sa | Nuevos compuestos aminopiridinicos policiclicos inhibidores de acetilcolinesterasa, procedimiento para su preparacion y su utilizacion. |
| AU1608397A (en) | 1996-02-02 | 1997-08-22 | Zeneca Limited | Heterocyclic compounds useful as pharmaceutical agents |
| GB9602166D0 (en) | 1996-02-02 | 1996-04-03 | Zeneca Ltd | Aminoheterocyclic derivatives |
| US5807876A (en) | 1996-04-23 | 1998-09-15 | Vertex Pharmaceuticals Incorporated | Inhibitors of IMPDH enzyme |
| JPH09291034A (ja) | 1996-02-27 | 1997-11-11 | Yoshitomi Pharmaceut Ind Ltd | 縮合ピリジン化合物およびその医薬としての用途 |
| US6262113B1 (en) | 1996-03-20 | 2001-07-17 | Smithkline Beecham Corporation | IL-8 receptor antagonists |
| US5834485A (en) | 1996-05-20 | 1998-11-10 | Chiroscience Limited | Quinoline sulfonamides and their therapeutic use |
| US5984882A (en) | 1996-08-19 | 1999-11-16 | Angiosonics Inc. | Methods for prevention and treatment of cancer and other proliferative diseases with ultrasonic energy |
| EP0945446A4 (en) | 1996-11-14 | 1999-12-08 | Nissan Chemical Ind Ltd | CYANOETHYLMELAMINE DERIVATIVES AND PROCESS FOR PRODUCING THE SAME |
| US6399358B1 (en) | 1997-03-31 | 2002-06-04 | Thomas Jefferson University | Human gene encoding human chondroitin 6-sulfotransferase |
| JPH11158073A (ja) * | 1997-09-26 | 1999-06-15 | Takeda Chem Ind Ltd | アデノシンa3拮抗剤 |
| CA2313776A1 (en) * | 1997-12-12 | 1999-06-24 | Abbott Laboratories | Triazine angiogenesis inhibitors |
| US7517880B2 (en) | 1997-12-22 | 2009-04-14 | Bayer Pharmaceuticals Corporation | Inhibition of p38 kinase using symmetrical and unsymmetrical diphenyl ureas |
| EP1042305B1 (en) | 1997-12-22 | 2005-06-08 | Bayer Pharmaceuticals Corp. | INHIBITION OF p38 KINASE USING SYMMETRICAL AND UNSYMMETRICAL DIPHENYL UREAS |
| AU9064598A (en) | 1998-07-10 | 2000-02-01 | Harald Groger | Precusors for pna-monomers |
| US6783965B1 (en) | 2000-02-10 | 2004-08-31 | Mountain View Pharmaceuticals, Inc. | Aggregate-free urate oxidase for preparation of non-immunogenic polymer conjugates |
| PT2158923E (pt) | 1998-08-06 | 2013-06-04 | Univ Duke | Conjugados de peg-urato oxidase e sua utilização |
| CA2348234A1 (en) * | 1998-10-29 | 2000-05-11 | Chunjian Liu | Compounds derived from an amine nucleus that are inhibitors of impdh enzyme |
| UY25842A1 (es) | 1998-12-16 | 2001-04-30 | Smithkline Beecham Corp | Antagonistas de receptores de il-8 |
| EP1187825A1 (en) | 1999-06-07 | 2002-03-20 | Shire Biochem Inc. | Thiophene integrin inhibitors |
| CA2382789A1 (en) | 1999-08-27 | 2001-03-08 | Sugen, Inc. | Phosphate mimics and methods of treatment using phosphatase inhibitors |
| BR0014076A (pt) | 1999-09-17 | 2002-10-15 | Millennium Pharm Inc | Benzamidas e inibidores correlatos do fator xa |
| HUP0203954A2 (hu) | 1999-09-17 | 2003-03-28 | Millennium Pharmaceuticals, Inc. | Xa faktor inhibitorok |
| JP4794793B2 (ja) | 1999-12-28 | 2011-10-19 | ファーマコペイア, インコーポレイテッド | N−ヘテロ環TNF−α発現阻害剤 |
| DK1259485T3 (da) | 2000-02-29 | 2006-04-10 | Millennium Pharm Inc | Benzamider og beslægtede inhibitorer for faktor Xa |
| EP1301484A2 (en) | 2000-07-20 | 2003-04-16 | Neurogen Corporation | Capsaicin receptor ligands |
| JP4113323B2 (ja) * | 2000-08-07 | 2008-07-09 | 富士フイルム株式会社 | アゾ色素及びそれを含むインクジェット記録用インク、並びにインクジェット記録方法 |
| US6525091B2 (en) | 2001-03-07 | 2003-02-25 | Telik, Inc. | Substituted diarylureas as stimulators for Fas-mediated apoptosis |
| AU2002256418A1 (en) | 2001-04-27 | 2002-11-11 | Vertex Pharmaceuticals Incorporated | Inhibitors of bace |
| US7144883B2 (en) | 2001-06-11 | 2006-12-05 | Biovitrum Ab | Bicyclic sulfonamide compounds |
| HUP0402352A2 (hu) | 2001-06-19 | 2005-02-28 | Bristol-Myers Squibb Co. | Foszfodiészteráz (PDE) 7 inhibitorként alkalmazható pirimidinszármazékok és ezeket tartalmazó gyógyszerkészítmények |
| WO2003016289A1 (en) * | 2001-08-17 | 2003-02-27 | Ciba Specialty Chemicals Holding Inc. | Triazine derivatives and their use as sunscreens |
| JP4753336B2 (ja) * | 2001-09-04 | 2011-08-24 | 日本化薬株式会社 | 新規アリル化合物及びその製法 |
| AU2002367153A1 (en) | 2001-12-21 | 2003-07-15 | Dow Global Technologies Inc. | Tertiary amine modified polyols and polyurethane products made therefrom |
| US6878196B2 (en) | 2002-01-15 | 2005-04-12 | Fuji Photo Film Co., Ltd. | Ink, ink jet recording method and azo compound |
| EP1485381B8 (en) | 2002-03-15 | 2010-05-12 | Vertex Pharmaceuticals Incorporated | Azolylaminoazine as inhibitors of protein kinases |
| TWI319387B (en) * | 2002-04-05 | 2010-01-11 | Astrazeneca Ab | Benzamide derivatives |
| US20040067234A1 (en) | 2002-07-11 | 2004-04-08 | Paz Einat | Isocitrate dehydrogenase and uses thereof |
| DK2256108T3 (en) | 2002-07-18 | 2016-04-11 | Janssen Pharmaceutica Nv | Substituted triazinkinaseinhibitorer |
| JP2004083610A (ja) * | 2002-08-22 | 2004-03-18 | Fuji Photo Film Co Ltd | インクセット、インクカートリッジ、記録方法、プリンター及び記録物 |
| JP2004107220A (ja) * | 2002-09-13 | 2004-04-08 | Mitsubishi Pharma Corp | TNF−α産生抑制剤 |
| TWI335913B (en) | 2002-11-15 | 2011-01-11 | Vertex Pharma | Diaminotriazoles useful as inhibitors of protein kinases |
| US7361691B2 (en) | 2002-12-02 | 2008-04-22 | Arqule, Inc. | Method of treating cancers using β-lapachone or analogs or derivatives thereof |
| WO2004058797A2 (en) | 2002-12-16 | 2004-07-15 | Medarex, Inc. | Human monoclonal antibodies against interleukin 8 (il-8) |
| US6979675B2 (en) | 2003-01-10 | 2005-12-27 | Threshold Pharmaceuticals, Inc. | Treatment of cancer with 2-deoxyglucose |
| US7358262B2 (en) | 2003-01-29 | 2008-04-15 | Whitehead Institute For Biomedical Research | Identification of genotype-selective anti-tumor agents |
| WO2004073619A2 (en) | 2003-02-14 | 2004-09-02 | Smithkline Beecham Corporation | Ccr8 antagonists |
| WO2004074438A2 (en) | 2003-02-14 | 2004-09-02 | Smithkline Beecham Corporation | Ccr8 antagonists |
| EP1618090A1 (en) | 2003-04-11 | 2006-01-25 | Novo Nordisk A/S | 11ß-HYDROXYSTEROID DEHYDROGENASE TYPE 1 ACTIVE COMPOUNDS |
| WO2004099163A1 (en) | 2003-05-05 | 2004-11-18 | New York University | Solid phase synthesis of biaryl triazine library by suzuki cross-coupling reaction |
| WO2005003103A2 (en) * | 2003-06-30 | 2005-01-13 | Astrazeneca Ab | 2, 4, 6-tri-substituted 6-membered heterocycles and their use in the treatment of neurodegenerative diseases |
| AR045731A1 (es) | 2003-08-06 | 2005-11-09 | Vertex Pharma | Compuestos de aminotriazol utiles como inhibidores de quinasas de proteinas |
| WO2005035507A2 (en) | 2003-10-10 | 2005-04-21 | Bayer Pharmaceuticals Corporation | 4-aminopyrimidine derivatives for treatment of hyperproliferative disorders |
| WO2005060956A1 (en) | 2003-12-12 | 2005-07-07 | University Of Maryland, Baltimore | IMMUNOMODULATORY COMPOUNDS THAT TARGET AND INHIBIT THE pY+3 BINDING SITE OF TYROSENE KINASE p56 LCK SH2 DOMAIN |
| BRPI0417213A (pt) | 2003-12-24 | 2007-02-06 | Scios Inc | tratamento de gliomas malìgnos com inibidores de tgf-beta |
| JP2005264016A (ja) * | 2004-03-19 | 2005-09-29 | Fuji Photo Film Co Ltd | インクジェット記録用インク、インクセット及びインクジェット記録方法 |
| US7335770B2 (en) | 2004-03-24 | 2008-02-26 | Reddy U5 Therapeutics, Inc. | Triazine compounds and their analogs, compositions, and methods |
| GB0412526D0 (en) | 2004-06-05 | 2004-07-14 | Leuven K U Res & Dev | Type 2 diabetes |
| MX2007003319A (es) | 2004-09-20 | 2007-06-05 | Xenon Pharmaceuticals Inc | Derivados heterociclicos y su uso como agentes terapeuticos. |
| WO2006034473A2 (en) | 2004-09-23 | 2006-03-30 | Reddy Us Therapeutics, Inc. | Novel pyrimidine compounds, process for their preparation and compositions containing them |
| WO2006038594A1 (ja) | 2004-10-04 | 2006-04-13 | Ono Pharmaceutical Co., Ltd. | N型カルシウムチャネル阻害薬 |
| EP1836188A1 (en) | 2004-12-30 | 2007-09-26 | Astex Therapeutics Limited | Pyrazole derivatives as that modulate the activity of cdk, gsk and aurora kinases |
| MX2007008924A (es) | 2005-01-25 | 2007-08-21 | Astrazeneca Ab | Compuestos quimicos. |
| CA2604545A1 (en) | 2005-04-11 | 2006-10-19 | Savient Pharmaceuticals, Inc. | A variant form of urate oxidase and use thereof |
| EP2687608B1 (en) | 2005-06-08 | 2017-02-08 | Millennium Pharmaceuticals, Inc. | Methods for the identification, assessment, and treatment of patients with cancer therapy |
| GB0513702D0 (en) | 2005-07-04 | 2005-08-10 | Sterix Ltd | Compound |
| WO2007023186A1 (en) | 2005-08-26 | 2007-03-01 | Laboratoires Serono S.A. | Pyrazine derivatives and use as pi3k inhibitors |
| US8133900B2 (en) | 2005-11-01 | 2012-03-13 | Targegen, Inc. | Use of bi-aryl meta-pyrimidine inhibitors of kinases |
| JP4753363B2 (ja) | 2005-12-28 | 2011-08-24 | 株式会社ジョイコシステムズ | 遊技媒体貸出装置用設定アダプタ、遊技媒体貸出装置用設定アダプタ付き接続ケーブルおよび遊技媒体貸出システム |
| WO2007095812A1 (en) | 2006-02-27 | 2007-08-30 | Shanghai Institute Of Materia Medica, Chinese Academy Of Sciences | Substituted [1,3,5] triazine compounds, their processes for preparation and uses thereof |
| TW200815426A (en) | 2006-06-28 | 2008-04-01 | Astrazeneca Ab | New pyridine analogues II 333 |
| US20100297673A1 (en) | 2006-09-20 | 2010-11-25 | Reddy Us Therapeutics | Methods and compositions for upregulation of peroxiredoxin activity |
| US7906555B2 (en) | 2006-10-26 | 2011-03-15 | Arizona Board Of Regents On Behalf Of The University Of Arizona | Aquaporin modulators and methods of using them for the treatment of edema and fluid imbalance |
| HUP0600810A3 (en) | 2006-10-27 | 2008-09-29 | Richter Gedeon Nyrt | New sulfonamide derivatives as bradykinin antagonists, process and intermediates for their preparation and pharmaceutical compositions containing them |
| PE20081229A1 (es) | 2006-12-01 | 2008-08-28 | Merck & Co Inc | Antagonistas de receptor de orexina de diazepam sustituido |
| WO2008070661A1 (en) | 2006-12-04 | 2008-06-12 | Neurocrine Biosciences, Inc. | Substituted pyrimidines as adenosine receptor antagonists |
| PT2101760E (pt) | 2006-12-08 | 2013-05-07 | Millennium Pharm Inc | Formulações de dose unitária e métodos de tratamento da trombose com um inibidor oral do fator xa |
| CN101583365B (zh) * | 2006-12-15 | 2012-09-26 | 阿布拉西斯生物科学公司 | 三嗪衍生物及其治疗应用 |
| BRPI0810921A2 (pt) | 2007-04-30 | 2014-10-29 | Prometic Biosciences Inc | Derivados de triazina, composições contendo tais derivados e métodos de tratamento de câncer e doenças autoimunes usando tais compostos |
| JP2010529193A (ja) | 2007-06-11 | 2010-08-26 | ミイカナ セラピューティクス インコーポレイテッド | 置換ピラゾール化合物 |
| PL2176231T3 (pl) | 2007-07-20 | 2017-04-28 | Nerviano Medical Sciences S.R.L. | Podstawione pochodne indazolu aktywne jako inhibitory kinazy |
| KR20100038108A (ko) | 2007-07-25 | 2010-04-12 | 브리스톨-마이어스 스큅 컴퍼니 | 트리아진 키나제 억제제 |
| TW200906818A (en) | 2007-07-31 | 2009-02-16 | Astrazeneca Ab | Chemical compounds |
| EA201070451A1 (ru) | 2007-10-10 | 2010-10-29 | Такеда Фармасьютикал Компани Лимитед | Амидные соединения |
| ES2445444T3 (es) | 2007-10-11 | 2014-03-03 | Glaxosmithkline Llc | Nuevos inhibidores de sEH y su uso |
| AU2008345225A1 (en) | 2007-12-21 | 2009-07-09 | University Of Rochester | Method for altering the lifespan of eukaryotic organisms |
| EP2231624A4 (en) * | 2007-12-21 | 2011-07-06 | Progenics Pharm Inc | TRIAZINE AND CORRESPONDING COMPOUNDS WITH ANTIVIRAL EFFECT, COMPOSITIONS AND METHOD THEREFOR |
| JP5277685B2 (ja) * | 2008-03-26 | 2013-08-28 | 富士ゼロックス株式会社 | 電子写真感光体、画像形成装置、プロセスカートリッジ及び画像形成方法 |
| GB0805477D0 (en) | 2008-03-26 | 2008-04-30 | Univ Nottingham | Pyrimidines triazines and their use as pharmaceutical agents |
| US20090281089A1 (en) | 2008-04-11 | 2009-11-12 | Genentech, Inc. | Pyridyl inhibitors of hedgehog signalling |
| CN101575408B (zh) | 2008-05-09 | 2013-10-30 | Mca技术有限公司 | 用作阻燃剂和光稳定剂的聚三嗪基化合物 |
| AU2009259026B2 (en) | 2008-06-11 | 2012-10-04 | Astrazeneca Ab | Tricyclic 2,4-diamin0-L,3,5-triazine derivatives useful for the treatment of cancer and myeloproliferative disorders |
| FR2932483A1 (fr) | 2008-06-13 | 2009-12-18 | Cytomics Systems | Composes utiles pour le traitement des cancers. |
| CN101307029B (zh) * | 2008-07-08 | 2011-04-13 | 浙江大学 | 2,4,6-三取代-1,3,5-三嗪类衍生物库及制备方法 |
| WO2010007756A1 (ja) | 2008-07-14 | 2010-01-21 | 塩野義製薬株式会社 | Ttk阻害作用を有するピリジン誘導体 |
| EP2326735B1 (en) | 2008-09-03 | 2016-11-16 | The Johns Hopkins University | Genetic alterations in isocitrate dehydrogenase and other genes in malignant glioma |
| US20100144722A1 (en) | 2008-09-03 | 2010-06-10 | Dr. Reddy's Laboratories Ltd. | Novel heterocyclic compounds as gata modulators |
| JP2010079130A (ja) * | 2008-09-29 | 2010-04-08 | Fuji Xerox Co Ltd | 電子写真感光体、プロセスカートリッジ、及び画像形成装置 |
| EP2370417A2 (en) | 2008-11-21 | 2011-10-05 | Millennium Pharmaceuticals, Inc. | Lactate salt of 4-[6-methoxy-7-(3-piperidin-1-yl-propoxy)quinazolin-4-yl]piperazine-1-carboxylic acid(4-isopropoxyphenyl)-amide and pharmaceutical compositions thereof for the treatment of cancer and other diseases or disorders |
| JP2010181540A (ja) * | 2009-02-04 | 2010-08-19 | Fuji Xerox Co Ltd | 電子写真感光体、プロセスカートリッジ、及び画像形成装置 |
| JP5263304B2 (ja) | 2009-02-06 | 2013-08-14 | 日本新薬株式会社 | アミノピラジン誘導体及び医薬 |
| CN108524505A (zh) | 2009-03-13 | 2018-09-14 | 安吉奥斯医药品有限公司 | 用于细胞增殖相关病症的方法和组合物 |
| PL2427441T3 (pl) | 2009-05-04 | 2017-06-30 | Agios Pharmaceuticals, Inc. | Aktywatory PKM2 do stosowania w leczeniu raka |
| WO2010130638A1 (en) | 2009-05-14 | 2010-11-18 | Evotec Ag | Sulfonamide compounds, pharmaceutical compositions and uses thereof |
| CA2764785C (en) | 2009-06-08 | 2015-10-27 | California Capital Equity, Llc | Triazine derivatives and their therapeutical applications |
| JP2012529513A (ja) | 2009-06-08 | 2012-11-22 | アブラクシス バイオサイエンス リミテッド ライアビリティー カンパニー | トリアジン誘導体類及びそれらの治療応用 |
| BRPI1011527A2 (pt) * | 2009-06-09 | 2016-07-26 | California Capital Equity Llc | derivados de triazina substituídos com ureidofenil e suas aplicações terapêuticas. |
| AU2010258974A1 (en) * | 2009-06-09 | 2012-01-12 | California Capital Equity, Llc | Pyridil-triazine inhibitors of hedgehog signaling |
| US8877924B2 (en) | 2009-06-09 | 2014-11-04 | NantBio Inc. | Benzyl substituted triazine derivatives and their therapeutical applications |
| PT2448582T (pt) | 2009-06-29 | 2017-07-10 | Agios Pharmaceuticals Inc | Compostos e composições terapêuticas |
| US20120197411A1 (en) | 2009-07-10 | 2012-08-02 | Milux Holding Sa | Knee joint device and method |
| WO2011025838A1 (en) * | 2009-08-25 | 2011-03-03 | Abraxis Bioscience, Llc | Combination therapy with nanoparticle compositions of taxane and hedgehog inhibitors |
| US20120157471A1 (en) | 2009-09-01 | 2012-06-21 | Pfizer Inc. | Benzimidazole derivatives |
| WO2011032169A2 (en) | 2009-09-14 | 2011-03-17 | Phusis Therapeutics Inc. | Pharmaceutical compositions and formulations including inhibitors of the pleckstrin homology domain and methods for using same |
| JP5473851B2 (ja) * | 2009-09-30 | 2014-04-16 | 富士フイルム株式会社 | 高分子フィルム、位相差フィルム、偏光板及び液晶表示装置 |
| US8652534B2 (en) | 2009-10-14 | 2014-02-18 | Berry Pharmaceuticals, LLC | Compositions and methods for treatment of mammalian skin |
| EP3561077B1 (en) | 2009-10-21 | 2022-12-21 | Les Laboratoires Servier | Methods for cell-proliferation-related disorders |
| EP2491030B1 (en) | 2009-10-22 | 2015-07-15 | Fibrotech Therapeutics PTY LTD | Fused ring analogues of anti-fibrotic agents |
| JP5967827B2 (ja) | 2009-12-09 | 2016-08-10 | アジオス ファーマシューティカルズ, インコーポレイテッド | Idh変異体をもつことを特徴とする癌治療用の治療的活性化合物 |
| NZ578968A (en) | 2010-02-10 | 2011-03-31 | Allans Sheetmetal And Engineering Services | Fuel feed system for a pellet fire |
| EP2553116A4 (en) | 2010-04-01 | 2013-10-23 | Agios Pharmaceuticals Inc | METHOD FOR IDENTIFYING A CANDIDATE COMPOUND |
| WO2011143160A2 (en) | 2010-05-10 | 2011-11-17 | The Johns Hopkins University | Metabolic inhibitor against tumors having an idh mutation |
| WO2012006506A1 (en) | 2010-07-09 | 2012-01-12 | Massachusetts Institute Of Technology | Metabolic gene, enzyme, and flux targets for cancer therapy |
| CN103097340B (zh) | 2010-07-16 | 2018-03-16 | 安吉奥斯医药品有限公司 | 治疗活性组合物及其使用方法 |
| PT2630146T (pt) | 2010-10-21 | 2020-07-20 | Medivation Tech Llc | Sal tosilato de (8s,9r)-5-fluoro-8-(4-fluorofenil)-9-(1-metil-1h-1,2,4-triazol-5-il)-8,9-di-hidro-2h-pirido[4,3,2-de]ftalazin-3(7h)-ona cristalino |
| AU2011336764B2 (en) * | 2010-11-29 | 2017-02-23 | Galleon Pharmaceuticals, Inc. | Novel compounds as respiratory stimulants for treatment of breathing control disorders or diseases |
| 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 |
| EP2691391A4 (en) | 2011-03-29 | 2014-09-10 | Broad Inst Inc | COMPOUNDS AND METHODS OF TREATING DISORDERS MEDIATED BY ISOCITRATE DEHYDROGENASE |
| WO2012151452A1 (en) | 2011-05-03 | 2012-11-08 | Agios Pharmaceuticals, Inc | Pyruvate kinase activators for use in therapy |
| TWI555737B (zh) | 2011-05-24 | 2016-11-01 | 拜耳知識產權公司 | 含有硫醯亞胺基團之4-芳基-n-苯基-1,3,5-三氮雜苯-2-胺 |
| 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 |
| 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 |
| US9199962B2 (en) * | 2011-07-07 | 2015-12-01 | Merck Patent Gmbh | Substituted azaheterocycles for the treatment of cancer |
| US10441577B2 (en) | 2011-07-08 | 2019-10-15 | Helmholtz Zentrum Fuer Infektionsforschung | Medicament for treatment of liver cancer |
| US9167820B2 (en) * | 2011-07-22 | 2015-10-27 | University Of Louisville Research Foundation, Inc. | Anti-biofilm compounds |
| MX342326B (es) * | 2011-09-27 | 2016-09-26 | Novartis Ag | 3-pirimidin-4-il-oxazolidin-2-onas como inhibidoras de idh mutante. |
| CN102659765B (zh) * | 2011-12-31 | 2014-09-10 | 沈阳药科大学 | 嘧啶及三嗪类化合物的制备方法和应用 |
| ES2675760T3 (es) | 2012-01-06 | 2018-07-12 | Agios Pharmaceuticals, Inc. | Compuestos terapéuticamente activos y métodos de uso de los mismos |
| US9474779B2 (en) | 2012-01-19 | 2016-10-25 | Agios Pharmaceuticals, Inc. | Therapeutically active compositions and their methods of use |
| ES2698625T3 (es) | 2012-01-19 | 2019-02-05 | Agios Pharmaceuticals Inc | Compuestos terapéuticamente activos y sus métodos de uso |
| EP2634259A1 (en) | 2012-03-01 | 2013-09-04 | Deutsches Krebsforschungszentrum | Means and methods for the determination of (D)-2-hydroxyglutarate (D2HG) |
| WO2013133367A1 (ja) | 2012-03-09 | 2013-09-12 | カルナバイオサイエンス株式会社 | 新規トリアジン誘導体 |
| WO2014015422A1 (en) | 2012-07-27 | 2014-01-30 | Ontario Institute For Cancer Research | Cellulose-based nanoparticles for drug delivery |
| CN104822373B (zh) | 2012-10-15 | 2018-08-28 | 安吉奥斯医药品有限公司 | 治疗性化合物和组合物 |
| EP2922828B1 (en) | 2012-11-21 | 2020-07-08 | PTC Therapeutics, Inc. | 4,6-diamino-pyrimidine derivatives as bmi-1 inhibitors for treating cancer |
| WO2015003360A2 (en) * | 2013-07-11 | 2015-01-15 | Agios Pharmaceuticals, Inc. | Therapeutically active compounds and their methods of use |
| WO2015003355A2 (en) | 2013-07-11 | 2015-01-15 | Agios Pharmaceuticals, Inc. | Therapeutically active compounds and their methods of use |
| KR102302091B1 (ko) | 2013-07-11 | 2021-09-16 | 아지오스 파마슈티컬스 아이엔씨. | 암 치료용의 idh2 돌연변이체 억제제로서의 n,6-비스(아릴 또는 헤테로아릴)-1,3,5-트리아진-2,4-디아민 화합물 |
| US9579324B2 (en) | 2013-07-11 | 2017-02-28 | Agios Pharmaceuticals, Inc | Therapeutically active compounds and their methods of use |
| AU2014287121B2 (en) | 2013-07-11 | 2018-11-15 | Agios Pharmaceuticals, Inc. | 2,4- or 4,6-diaminopyrimidine compounds as IDH2 mutants inhibitors for the treatment of cancer |
| US20150031627A1 (en) | 2013-07-25 | 2015-01-29 | Agios Pharmaceuticals, Inc | Therapeutically active compounds and their methods of use |
| ES2886211T3 (es) | 2013-08-02 | 2021-12-16 | Agios Pharmaceuticals Inc | Compuestos terapéuticamente activos y sus métodos de uso |
| WO2015018060A1 (en) | 2013-08-09 | 2015-02-12 | Agios Pharmaceuticals, Inc. | Crystalline forms of therapeutically active compounds and use thereof |
| ES2897959T3 (es) | 2015-10-15 | 2022-03-03 | Servier Lab | Terapia de combinación para tratar neoplasias malignas |
| US10961222B2 (en) | 2016-07-21 | 2021-03-30 | Nanjing Sanhome Pharmaceutical Co., Ltd. | Chemical compound of isocitrate dehydrogenase inhibitor, and application thereof |
| BR112019004356A2 (pt) | 2016-09-07 | 2019-05-28 | Celgene Corporation | composições de comprimido |
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