CA2993615A1 - 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 - Google Patents
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 Download PDFInfo
- Publication number
- CA2993615A1 CA2993615A1 CA2993615A CA2993615A CA2993615A1 CA 2993615 A1 CA2993615 A1 CA 2993615A1 CA 2993615 A CA2993615 A CA 2993615A CA 2993615 A CA2993615 A CA 2993615A CA 2993615 A1 CA2993615 A1 CA 2993615A1
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- Canada
- Prior art keywords
- compound
- formula
- reacting
- give
- alkylene
- 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.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 64
- 150000001875 compounds Chemical class 0.000 claims abstract description 152
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 22
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 claims description 17
- 239000003153 chemical reaction reagent Substances 0.000 claims description 16
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 claims description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims description 12
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 11
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- 125000004452 carbocyclyl group Chemical group 0.000 description 7
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- AYABEJGGSWJVPN-UHFFFAOYSA-N methyl 6-(trifluoromethyl)pyridine-2-carboxylate Chemical compound COC(=O)C1=CC=CC(C(F)(F)F)=N1 AYABEJGGSWJVPN-UHFFFAOYSA-N 0.000 description 7
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
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| PCT/US2016/045553 WO2017024134A1 (en) | 2015-08-05 | 2016-08-04 | 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 |
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| CA2993615A1 true CA2993615A1 (en) | 2017-02-09 |
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| MX (1) | MX365590B (cg-RX-API-DMAC7.html) |
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| WO2016053850A1 (en) | 2014-09-29 | 2016-04-07 | Agios Pharmaceuticals, Inc. | Therapeutically active compounds and their methods of use |
| WO2016126798A1 (en) | 2015-02-04 | 2016-08-11 | Agios Pharmaceuticals, Inc. | Therapeutically active compounds and their methods of use |
| CN108349933A (zh) * | 2015-08-05 | 2018-07-31 | 安吉奥斯医药品有限公司 | 制备6-(芳基或杂芳基)-1,3,5-三嗪-2,4-二醇和6-(芳基或杂芳基)-1,3,5-三嗪-2,4-二胺的方法 |
| AU2016340098B2 (en) | 2015-10-15 | 2022-06-02 | Celgene Corporation | Combination therapy for treating malignancies |
| WO2017066599A1 (en) | 2015-10-15 | 2017-04-20 | Agios Pharmaceuticals, Inc. | Combination therapy for treating malignancies |
| ES2905915T3 (es) | 2015-12-04 | 2022-04-12 | Servier Lab | Procedimientos de tratamiento de neoplasias malignas |
| JP6930991B2 (ja) | 2016-02-26 | 2021-09-01 | セルジーン コーポレイション | 血液学的悪性腫瘍及び固形腫瘍の治療のためのｉｄｈ２阻害剤 |
| SG11201901873PA (en) | 2016-09-07 | 2019-03-28 | Celgene Corp | Tablet compositions |
| US11229653B2 (en) | 2017-05-05 | 2022-01-25 | Celgene Corporation | Methods of treatment of myeloproliferative neoplasm |
| US20220017489A1 (en) | 2018-11-02 | 2022-01-20 | Celgene Corporation | Solid dispersions for treatment of cancer |
| WO2020092906A1 (en) | 2018-11-02 | 2020-05-07 | Celgene Corporation | Co-crystals 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, compositions and methods of use thereof |
| 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 |
| WO2021097160A1 (en) | 2019-11-14 | 2021-05-20 | Celgene Corporation | Pediatric formulations for treatment of cancer |
| CN111592524B (zh) * | 2020-05-20 | 2023-11-17 | 温州市天聚万迅信息科技有限公司 | 恩西德尼的制备方法 |
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| US2390529A (en) | 1942-02-03 | 1945-12-11 | Ernst A H Friedheim | Hydrazino-1,3,5-triazino derivatives of substituted phenylarsenic compounds |
| JPS5170779A (ja) * | 1974-12-17 | 1976-06-18 | Nippon Shinyaku Co Ltd | Shinkinaguanamidoruino seiho |
| 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 |
| EP0466647B1 (de) | 1990-07-12 | 1995-11-29 | Ciba-Geigy Ag | Verfahren zur photochemischen und thermischen Stabilisierung von Polyamid-Fasermaterialien |
| JPH11158073A (ja) | 1997-09-26 | 1999-06-15 | Takeda Chem Ind Ltd | アデノシンａ３拮抗剤 |
| US6274620B1 (en) | 1999-06-07 | 2001-08-14 | Biochem Pharma Inc. | Thiophene integrin inhibitors |
| EP2256108B1 (en) | 2002-07-18 | 2016-03-23 | Janssen Pharmaceutica NV | Substituted triazine kinase inhibitors |
| CN101679321B (zh) | 2007-04-30 | 2012-10-03 | 普罗米蒂克生物科学公司 | 三嗪衍生物、含所述衍生物的组合物以及所述衍生物在制备用于治疗癌症和自身免疫性疾病药物中的应用 |
| GB0805477D0 (en) | 2008-03-26 | 2008-04-30 | Univ Nottingham | Pyrimidines triazines and their use as pharmaceutical agents |
| CN102573485B (zh) | 2009-06-08 | 2014-11-26 | 加利福尼亚资本权益有限责任公司 | 三嗪衍生物及其治疗应用 |
| SI2800743T1 (en) * | 2012-01-06 | 2018-08-31 | Agios Pharmaceuticals, Inc. | Therapeutically active compounds and methods for their use |
| CN104169260A (zh) | 2012-03-09 | 2014-11-26 | 卡尔那生物科学株式会社 | 新三嗪衍生物 |
| WO2015003360A2 (en) * | 2013-07-11 | 2015-01-15 | Agios Pharmaceuticals, Inc. | Therapeutically active compounds and their methods of use |
| NZ715738A (en) | 2013-07-11 | 2021-06-25 | 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 |
| EA030428B1 (ru) | 2013-08-02 | 2018-08-31 | Аджиос Фармасьютикалз, Инк. | Терапевтически активные соединения и способы их применения |
| WO2016053850A1 (en) | 2014-09-29 | 2016-04-07 | Agios Pharmaceuticals, Inc. | Therapeutically active compounds and their methods of use |
| WO2016126798A1 (en) | 2015-02-04 | 2016-08-11 | Agios Pharmaceuticals, Inc. | Therapeutically active compounds and their methods of use |
| CN108349933A (zh) * | 2015-08-05 | 2018-07-31 | 安吉奥斯医药品有限公司 | 制备6-(芳基或杂芳基)-1,3,5-三嗪-2,4-二醇和6-(芳基或杂芳基)-1,3,5-三嗪-2,4-二胺的方法 |
-
2016
- 2016-08-04 CN CN201680045391.6A patent/CN108349933A/zh active Pending
- 2016-08-04 MX MX2018001424A patent/MX365590B/es active IP Right Grant
- 2016-08-04 CA CA2993615A patent/CA2993615A1/en not_active Abandoned
- 2016-08-04 AU AU2016303614A patent/AU2016303614A1/en not_active Abandoned
- 2016-08-04 JP JP2018505739A patent/JP6816106B2/ja active Active
- 2016-08-04 US US15/229,011 patent/US9751863B2/en active Active
- 2016-08-04 WO PCT/US2016/045553 patent/WO2017024134A1/en not_active Ceased
- 2016-08-04 EP EP16751449.6A patent/EP3331866B1/en active Active
-
2020
- 2020-12-23 JP JP2020213670A patent/JP2021063097A/ja active Pending
-
2021
- 2021-01-27 AU AU2021200494A patent/AU2021200494A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| MX365590B (es) | 2019-06-07 |
| EP3331866B1 (en) | 2023-07-26 |
| WO2017024134A1 (en) | 2017-02-09 |
| MX2018001424A (es) | 2018-08-01 |
| JP6816106B2 (ja) | 2021-01-20 |
| JP2018528182A (ja) | 2018-09-27 |
| US20170037031A1 (en) | 2017-02-09 |
| JP2021063097A (ja) | 2021-04-22 |
| CN108349933A (zh) | 2018-07-31 |
| EP3331866A1 (en) | 2018-06-13 |
| US9751863B2 (en) | 2017-09-05 |
| AU2016303614A1 (en) | 2018-02-15 |
| AU2021200494A1 (en) | 2021-03-11 |
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| Date | Code | Title | Description |
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| FZDE | Discontinued |
Effective date: 20221025 |