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)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562201546P | 2015-08-05 | 2015-08-05 | |
| US62/201,546 | 2015-08-05 | ||
| 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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2993615A1 true CA2993615A1 (en) | 2017-02-09 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2993615A Abandoned CA2993615A1 (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 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US9751863B2 (enExample) |
| EP (1) | EP3331866B1 (enExample) |
| JP (2) | JP6816106B2 (enExample) |
| CN (1) | CN108349933A (enExample) |
| AU (2) | AU2016303614A1 (enExample) |
| CA (1) | CA2993615A1 (enExample) |
| MX (1) | MX365590B (enExample) |
| WO (1) | WO2017024134A1 (enExample) |
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| EP3200800A1 (en) | 2014-09-29 | 2017-08-09 | 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 |
| EP3331866B1 (en) * | 2015-08-05 | 2023-07-26 | Les Laboratoires Servier | Methods of preparing a 6-heteroaryl-1,3,5-triazine-2,4-diol and a 6-heteroaryl-1,3,5-triazine-2,4-diamine |
| MX381582B (es) | 2015-10-15 | 2025-03-12 | Celgene Corp | Terapia de combinacion para el tratamiento de neoplasias malignas. |
| CA3001599A1 (en) | 2015-10-15 | 2017-04-20 | Agios Pharmaceuticals, Inc. | Combination therapy for treating malignancies |
| 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 |
| WO2017146795A1 (en) | 2016-02-26 | 2017-08-31 | Agios Pharmaceuticals, Inc. | Idh1 inhibitors for the treatment of haematological malignancies and solid tumours |
| JP2019529534A (ja) | 2016-09-07 | 2019-10-17 | セルジーン コーポレイション | 錠剤組成物 |
| EP3618828B1 (en) | 2017-05-05 | 2023-11-01 | Memorial Sloan Kettering Cancer Center | Methods of treatment of myeloproliferative neoplasm |
| US20220017489A1 (en) | 2018-11-02 | 2022-01-20 | Celgene Corporation | Solid dispersions for treatment of cancer |
| US20220017490A1 (en) | 2018-11-02 | 2022-01-20 | 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 |
| US12215094B2 (en) | 2018-11-02 | 2025-02-04 | 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 |
Family Cites Families (19)
| 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 |
| 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 |
| ATE130882T1 (de) | 1990-07-12 | 1995-12-15 | 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 |
| EP1187825A1 (en) | 1999-06-07 | 2002-03-20 | Shire Biochem Inc. | Thiophene integrin inhibitors |
| HUE029020T2 (en) | 2002-07-18 | 2017-02-28 | Janssen Pharmaceutica Nv | Substituted triazine kinase inhibitors |
| EP2152676B1 (en) | 2007-04-30 | 2013-04-03 | ProMetic BioSciences Inc. | "triazine derivatives, compositions containing such derivatives, and methods of treatment of cancer and autoimmune diseases using such derivatives" |
| GB0805477D0 (en) | 2008-03-26 | 2008-04-30 | Univ Nottingham | Pyrimidines triazines and their use as pharmaceutical agents |
| US20120238576A1 (en) | 2009-06-08 | 2012-09-20 | California Capital Equity, Llc | Triazine Derivatives and their Therapeutical Applications |
| LT2800743T (lt) * | 2012-01-06 | 2018-06-25 | Agios Pharmaceuticals, Inc. | Terapiškai aktyvūs junginiai ir jų panaudojimo būdai |
| 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 |
| ES2807582T3 (es) | 2013-07-11 | 2021-02-23 | Agios Pharmaceuticals Inc | Compuestos N,6-bis(aril o heteroaril)-1,3,5-triazina-2,4-diamina como inhibidores de mutantes IDH2 para el tratamiento del cáncer |
| WO2015003360A2 (en) * | 2013-07-11 | 2015-01-15 | Agios Pharmaceuticals, Inc. | Therapeutically active compounds and their methods of use |
| WO2015017821A2 (en) | 2013-08-02 | 2015-02-05 | Agios Pharmaceuticals, Inc. | Therapeutically active compounds and their methods of use |
| EP3200800A1 (en) | 2014-09-29 | 2017-08-09 | 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 |
| EP3331866B1 (en) * | 2015-08-05 | 2023-07-26 | Les Laboratoires Servier | Methods of preparing a 6-heteroaryl-1,3,5-triazine-2,4-diol and a 6-heteroaryl-1,3,5-triazine-2,4-diamine |
-
2016
- 2016-08-04 EP EP16751449.6A patent/EP3331866B1/en active Active
- 2016-08-04 WO PCT/US2016/045553 patent/WO2017024134A1/en not_active Ceased
- 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 MX MX2018001424A patent/MX365590B/es active IP Right Grant
- 2016-08-04 CN CN201680045391.6A patent/CN108349933A/zh active Pending
-
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 |
| AU2016303614A1 (en) | 2018-02-15 |
| AU2021200494A1 (en) | 2021-03-11 |
| US9751863B2 (en) | 2017-09-05 |
| EP3331866B1 (en) | 2023-07-26 |
| EP3331866A1 (en) | 2018-06-13 |
| JP2018528182A (ja) | 2018-09-27 |
| CN108349933A (zh) | 2018-07-31 |
| JP6816106B2 (ja) | 2021-01-20 |
| WO2017024134A1 (en) | 2017-02-09 |
| US20170037031A1 (en) | 2017-02-09 |
| JP2021063097A (ja) | 2021-04-22 |
| MX2018001424A (es) | 2018-08-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20221025 |