JP2016523977A5 - - Google Patents
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- Publication number
- JP2016523977A5 JP2016523977A5 JP2016525491A JP2016525491A JP2016523977A5 JP 2016523977 A5 JP2016523977 A5 JP 2016523977A5 JP 2016525491 A JP2016525491 A JP 2016525491A JP 2016525491 A JP2016525491 A JP 2016525491A JP 2016523977 A5 JP2016523977 A5 JP 2016523977A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- pyridin
- ring
- fluorophenyl
- fluoro
- 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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- -1 -cyclopropyl-OH Chemical group 0.000 claims 88
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 9
- 150000001875 compounds Chemical class 0.000 claims 7
- 239000008194 pharmaceutical composition Substances 0.000 claims 7
- 230000035772 mutation Effects 0.000 claims 5
- 206010028980 Neoplasm Diseases 0.000 claims 4
- 201000011510 cancer Diseases 0.000 claims 4
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 3
- 101000599886 Homo sapiens Isocitrate dehydrogenase [NADP], mitochondrial Proteins 0.000 claims 3
- 102100037845 Isocitrate dehydrogenase [NADP], mitochondrial Human genes 0.000 claims 3
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 201000003793 Myelodysplastic syndrome Diseases 0.000 claims 2
- 201000007224 Myeloproliferative neoplasm Diseases 0.000 claims 2
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 102200116484 rs121913502 Human genes 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 229940124597 therapeutic agent Drugs 0.000 claims 2
- 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 claims 2
- 125000006017 1-propenyl group Chemical group 0.000 claims 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 1
- HWXBTNAVRSUOJR-UHFFFAOYSA-N 2-hydroxyglutaric acid Chemical compound OC(=O)C(O)CCC(O)=O HWXBTNAVRSUOJR-UHFFFAOYSA-N 0.000 claims 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 1
- ZCHCHJQEWYIJDQ-UHFFFAOYSA-N 2-methyl-1,3-oxazole Chemical compound CC1=NC=CO1 ZCHCHJQEWYIJDQ-UHFFFAOYSA-N 0.000 claims 1
- SNJKHBIYYOBZOB-UHFFFAOYSA-N 2-n-phenyl-6-pyridin-2-yl-1,3,5-triazine-2,4-diamine Chemical compound N=1C(C=2N=CC=CC=2)=NC(N)=NC=1NC1=CC=CC=C1 SNJKHBIYYOBZOB-UHFFFAOYSA-N 0.000 claims 1
- KPGXRSRHYNQIFN-UHFFFAOYSA-N 2-oxoglutaric acid Chemical compound OC(=O)CCC(=O)C(O)=O KPGXRSRHYNQIFN-UHFFFAOYSA-N 0.000 claims 1
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims 1
- GASCNUBLHQPAMW-UHFFFAOYSA-N 3-[[4-[4-amino-6-(3-chloroanilino)-1,3,5-triazin-2-yl]pyridin-2-yl]amino]propan-1-ol Chemical compound N=1C(C=2C=C(NCCCO)N=CC=2)=NC(N)=NC=1NC1=CC=CC(Cl)=C1 GASCNUBLHQPAMW-UHFFFAOYSA-N 0.000 claims 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 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
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- WNDZCMWLOVCQCX-UHFFFAOYSA-N 4-(3-chlorophenyl)-6-(2-chloropyridin-4-yl)-1H-1,3,5-triazine-2,4-diamine Chemical compound ClC=1C=C(C=CC=1)C1(NC(=NC(=N1)N)C1=CC(=NC=C1)Cl)N WNDZCMWLOVCQCX-UHFFFAOYSA-N 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- VVMOQUNIQBUIAF-UHFFFAOYSA-N 4-pyridin-2-yl-6-pyridin-3-yl-1H-1,3,5-triazine-2,4-diamine Chemical compound N1=C(C=CC=C1)C1(NC(=NC(=N1)N)C=1C=NC=CC=1)N VVMOQUNIQBUIAF-UHFFFAOYSA-N 0.000 claims 1
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 1
- ZXCCTEXFQSKWGV-UHFFFAOYSA-N 6-(2-methoxypyridin-3-yl)-2-n-(4-methylphenyl)-1,3,5-triazine-2,4-diamine Chemical compound COC1=NC=CC=C1C1=NC(N)=NC(NC=2C=CC(C)=CC=2)=N1 ZXCCTEXFQSKWGV-UHFFFAOYSA-N 0.000 claims 1
- OXJGETFIDLHUNV-UHFFFAOYSA-N 6-(6-methoxypyridin-3-yl)-2-n-(4-methylphenyl)-1,3,5-triazine-2,4-diamine Chemical compound C1=NC(OC)=CC=C1C1=NC(N)=NC(NC=2C=CC(C)=CC=2)=N1 OXJGETFIDLHUNV-UHFFFAOYSA-N 0.000 claims 1
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims 1
- HEIWIFCGAFDAQU-UHFFFAOYSA-N Cc1nccc(n1)-c1nc(N)nc(Nc2cc(NC(=O)Nc3ccc(Cl)c(c3)C(F)(F)F)ccc2C)n1 Chemical compound Cc1nccc(n1)-c1nc(N)nc(Nc2cc(NC(=O)Nc3ccc(Cl)c(c3)C(F)(F)F)ccc2C)n1 HEIWIFCGAFDAQU-UHFFFAOYSA-N 0.000 claims 1
- 208000005243 Chondrosarcoma Diseases 0.000 claims 1
- 102000004190 Enzymes Human genes 0.000 claims 1
- 108090000790 Enzymes Proteins 0.000 claims 1
- 208000032612 Glial tumor Diseases 0.000 claims 1
- 206010018338 Glioma Diseases 0.000 claims 1
- 206010039491 Sarcoma Diseases 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 208000006990 cholangiocarcinoma Diseases 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 230000001419 dependent effect Effects 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 208000005017 glioblastoma Diseases 0.000 claims 1
- 125000004498 isoxazol-4-yl group Chemical group O1N=CC(=C1)* 0.000 claims 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims 1
- 125000003145 oxazol-4-yl group Chemical group O1C=NC(=C1)* 0.000 claims 1
- UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical compound CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 claims 1
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 1
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims 1
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims 1
- 230000002792 vascular Effects 0.000 claims 1
- DNWCRFXHXMDIHP-UHFFFAOYSA-N Nc1nc(NC2CCCCCCCC2)nc(C2CCCCCCCC2)n1 Chemical compound Nc1nc(NC2CCCCCCCC2)nc(C2CCCCCCCC2)n1 DNWCRFXHXMDIHP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361845352P | 2013-07-11 | 2013-07-11 | |
| US61/845,352 | 2013-07-11 | ||
| PCT/US2014/046204 WO2015006592A1 (en) | 2013-07-11 | 2014-07-10 | N,6-bis(aryl or heteroaryl)-1,3,5-triazine-2,4-diamine compounds as idh2 mutants inhibitors for the treatment of cancer |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016523977A JP2016523977A (ja) | 2016-08-12 |
| JP2016523977A5 true JP2016523977A5 (https=) | 2017-01-19 |
| JP6471155B2 JP6471155B2 (ja) | 2019-02-13 |
Family
ID=51261261
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016525491A Active JP6471155B2 (ja) | 2013-07-11 | 2014-07-10 | 癌の治療のためのｉｄｈ２変異体阻害剤としてのｎ，６−ビス（アリール又はヘテロアリール）−１，３，５−トリアジン−２，４−ジアミン化合物 |
Country Status (24)
| Country | Link |
|---|---|
| US (2) | US9724350B2 (https=) |
| EP (1) | EP3019490B1 (https=) |
| JP (1) | JP6471155B2 (https=) |
| KR (1) | KR102302091B1 (https=) |
| CN (1) | CN105492435B (https=) |
| AU (1) | AU2014287122B9 (https=) |
| BR (1) | BR112016000489A8 (https=) |
| CA (1) | CA2917592A1 (https=) |
| CL (1) | CL2016000045A1 (https=) |
| CR (1) | CR20160022A (https=) |
| EA (1) | EA032070B1 (https=) |
| ES (1) | ES2807582T3 (https=) |
| IL (1) | IL243522B (https=) |
| MX (1) | MX375030B (https=) |
| MY (1) | MY185687A (https=) |
| NI (1) | NI201600007A (https=) |
| NZ (1) | NZ715738A (https=) |
| PE (1) | PE20160744A1 (https=) |
| PH (1) | PH12016500055B1 (https=) |
| SA (1) | SA516370386B1 (https=) |
| SG (1) | SG11201600058XA (https=) |
| UA (1) | UA119242C2 (https=) |
| WO (1) | WO2015006592A1 (https=) |
| ZA (1) | ZA201600210B (https=) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
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| 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 |
| CN105593215B (zh) | 2013-07-11 | 2019-01-15 | 安吉奥斯医药品有限公司 | 用于治疗癌症的作为idh2突变体抑制剂的2,4-或4,6-二氨基嘧啶化合物 |
| MY185687A (en) * | 2013-07-11 | 2021-05-30 | Agios Pharmaceuticals Inc | N,6-bis(aryl or heteroaryl)-1,3,5-triazine-2,4-diamine 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 |
| TWI666208B (zh) | 2013-08-02 | 2019-07-21 | 美商阿吉斯藥品有限公司 | 治療活性化合物及其使用方法（三） |
| AU2015324158A1 (en) | 2014-09-29 | 2017-04-13 | Agios Pharmaceuticals, Inc. | Therapeutically active compounds and their methods of use |
| CN107531675A (zh) | 2015-02-04 | 2018-01-02 | 安吉奥斯医药品有限公司 | 治疗活性化合物及其使用方法 |
| CA2993615A1 (en) | 2015-08-05 | 2017-02-09 | Agios Pharmaceuticals, Inc. | Methods of preparing 6-(aryl or heteroaryl)-1,3,5-triazine-2,4-diols and 6-(aryl or heteroaryl)-1,3,5-triazine-2,4-diamines |
| US10695352B2 (en) * | 2015-10-15 | 2020-06-30 | Celgene Corporation | Combination therapy for treating malignancies |
| CN108366980A (zh) | 2015-10-15 | 2018-08-03 | 安吉奥斯医药品有限公司 | 用于治疗恶性肿瘤的组合疗法 |
| IL298663A (en) | 2015-12-04 | 2023-01-01 | Agios Pharmaceuticals Inc | Methods for treating acute myeloid leukemia characterized by the presence of a mutant allele of idh2 and the absence of a mutant allele of nras |
| 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 |
| ES2912909T3 (es) | 2016-02-26 | 2022-05-30 | Celgene Corp | Enasidenib para su uso en el tratamiento de la leucemia mieloide aguda recidivante o refractaria |
| CN107382840B (zh) * | 2016-05-16 | 2020-09-01 | 四川大学 | 吡啶类化合物及其作为idh功能变异突变体抑制剂类药物的用途 |
| CN107556366B (zh) * | 2016-06-30 | 2025-02-07 | 上海海和药物研究开发股份有限公司 | 具有突变型异柠檬酸脱氢酶抑制活性的化合物、其制备方法及用途 |
| CN109890806B (zh) | 2016-07-21 | 2022-04-26 | 南京圣和药业股份有限公司 | 作为异柠檬酸脱氢酶抑制剂的化合物及其应用 |
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| MX392941B (es) | 2016-09-07 | 2025-03-24 | Celgene Corp | Composiciones para comprimidos. |
| WO2018204787A1 (en) | 2017-05-05 | 2018-11-08 | Memorial Sloan Kettering Cancer Center | Methods of treatment of myeloproliferative neoplasm |
| EP4201399A3 (en) | 2017-06-30 | 2023-08-09 | Celgene Corporation | Compositions and methods of use of 2-(4-chlorophenyl)-n-((2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-5-yl) methyl) -2,2-difluoroacetamide |
| 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 |
| CN110054617A (zh) * | 2018-01-19 | 2019-07-26 | 南京圣和药业股份有限公司 | 三嗪类化合物、其制备方法及用途 |
| WO2020092894A1 (en) | 2018-11-02 | 2020-05-07 | Celgene Corporation | Solid forms of 2-methyl-1-[(4-[6-(trifluoromethyl) pyridin-2-yl]-6-{[2-(trifluoromethyl)pyridin-4-yl]amino}-1,3,5-triazin-2-yl) amino]propan-2-ol |
| CN111662242B (zh) * | 2019-03-08 | 2023-10-24 | 中国药科大学 | 杂环类idh突变体抑制剂、其制备方法及用途 |
| CN111087408B (zh) * | 2020-01-03 | 2021-04-02 | 浙江大学 | 一种大环结构的idh2突变体抑制剂及其医药用途 |
| CN112250639B (zh) * | 2020-11-19 | 2022-05-24 | 浙江工业大学 | 一种杂环取代的芳胺类化合物及其制备方法和应用 |
| CN112592958B (zh) * | 2020-12-07 | 2022-11-01 | 山东大学第二医院 | 利用fad依赖型d-2-羟基戊二酸脱氢酶和刃天青检测d-2-羟基戊二酸的方法 |
| CN112645893A (zh) * | 2020-12-28 | 2021-04-13 | 营口昌成新材料科技有限公司 | 一种二卤代均三嗪的合成方法 |
| CN115536637B (zh) * | 2022-10-24 | 2025-03-18 | 陕西中医药大学 | 一种均三嗪类衍生物及其合成方法与用途 |
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