JP2020523378A5 - - Google Patents
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- Publication number
- JP2020523378A5 JP2020523378A5 JP2019569286A JP2019569286A JP2020523378A5 JP 2020523378 A5 JP2020523378 A5 JP 2020523378A5 JP 2019569286 A JP2019569286 A JP 2019569286A JP 2019569286 A JP2019569286 A JP 2019569286A JP 2020523378 A5 JP2020523378 A5 JP 2020523378A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- iia
- compound
- diastereomer
- mixture
- 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
- 238000000034 method Methods 0.000 claims 16
- 150000001875 compounds Chemical class 0.000 claims 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 12
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 8
- 239000000203 mixture Substances 0.000 claims 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- 125000006239 protecting group Chemical group 0.000 claims 3
- 239000004215 Carbon black (E152) Substances 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- BIOWRMNRHMERIO-ZVAHOJSLSA-N benzyl (2s)-2-[[[(2r,3s,5r)-5-(5-fluoro-2,4-dioxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy-naphthalen-1-yloxyphosphoryl]amino]propanoate Chemical compound N1([C@@H]2O[C@@H]([C@H](C2)O)COP(=O)(N[C@@H](C)C(=O)OCC=2C=CC=CC=2)OC=2C3=CC=CC=C3C=CC=2)C=C(F)C(=O)NC1=O BIOWRMNRHMERIO-ZVAHOJSLSA-N 0.000 claims 2
- 125000006575 electron-withdrawing group Chemical group 0.000 claims 2
- 229930195733 hydrocarbon Natural products 0.000 claims 2
- 150000002430 hydrocarbons Chemical class 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 238000003756 stirring Methods 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- QUXHCILOWRXCEO-UHFFFAOYSA-M magnesium;butane;chloride Chemical compound [Mg+2].[Cl-].CCC[CH2-] QUXHCILOWRXCEO-UHFFFAOYSA-M 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 239000003495 polar organic solvent Substances 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 claims 1
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2023076006A JP7525687B2 (ja) | 2017-06-14 | 2023-05-02 | ホスフェート誘導体の合成 |
| JP2024114519A JP2024138523A (ja) | 2017-06-14 | 2024-07-18 | ホスフェート誘導体の合成 |
| JP2025266864A JP2026034703A (ja) | 2017-06-14 | 2025-12-19 | ホスフェート誘導体の合成 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1709471.5 | 2017-06-14 | ||
| GBGB1709471.5A GB201709471D0 (en) | 2017-06-14 | 2017-06-14 | Diastereoselective synthesis of hosphate derivatives |
| PCT/GB2018/051638 WO2018229493A2 (en) | 2017-06-14 | 2018-06-14 | Synthesis of phosphate derivatives |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2023076006A Division JP7525687B2 (ja) | 2017-06-14 | 2023-05-02 | ホスフェート誘導体の合成 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2020523378A JP2020523378A (ja) | 2020-08-06 |
| JP2020523378A5 true JP2020523378A5 (enExample) | 2021-07-26 |
| JP7279991B2 JP7279991B2 (ja) | 2023-05-23 |
Family
ID=59358400
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019569336A Active JP7248209B2 (ja) | 2017-06-14 | 2018-06-14 | ３’－デオキシアデノシン－５’－ｏ－［フェニル（ベンジルオシキ－ｌ－アラニニル）］ホスフェート（ｎｕｃ－７７３８）の合成 |
| JP2019569286A Active JP7279991B2 (ja) | 2017-06-14 | 2018-06-14 | ホスフェート誘導体の合成 |
| JP2023076006A Active JP7525687B2 (ja) | 2017-06-14 | 2023-05-02 | ホスフェート誘導体の合成 |
| JP2024114519A Pending JP2024138523A (ja) | 2017-06-14 | 2024-07-18 | ホスフェート誘導体の合成 |
| JP2025266864A Pending JP2026034703A (ja) | 2017-06-14 | 2025-12-19 | ホスフェート誘導体の合成 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019569336A Active JP7248209B2 (ja) | 2017-06-14 | 2018-06-14 | ３’－デオキシアデノシン－５’－ｏ－［フェニル（ベンジルオシキ－ｌ－アラニニル）］ホスフェート（ｎｕｃ－７７３８）の合成 |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2023076006A Active JP7525687B2 (ja) | 2017-06-14 | 2023-05-02 | ホスフェート誘導体の合成 |
| JP2024114519A Pending JP2024138523A (ja) | 2017-06-14 | 2024-07-18 | ホスフェート誘導体の合成 |
| JP2025266864A Pending JP2026034703A (ja) | 2017-06-14 | 2025-12-19 | ホスフェート誘導体の合成 |
Country Status (21)
| Country | Link |
|---|---|
| US (4) | US11897913B2 (enExample) |
| EP (3) | EP3638684B1 (enExample) |
| JP (5) | JP7248209B2 (enExample) |
| KR (2) | KR102695300B1 (enExample) |
| CN (3) | CN117486959A (enExample) |
| AU (3) | AU2018284131B2 (enExample) |
| BR (1) | BR112019026747A2 (enExample) |
| CA (2) | CA3065682A1 (enExample) |
| CL (1) | CL2019003632A1 (enExample) |
| EA (1) | EA201992873A1 (enExample) |
| ES (1) | ES3075652T3 (enExample) |
| GB (1) | GB201709471D0 (enExample) |
| IL (3) | IL302559B2 (enExample) |
| MA (1) | MA49379A (enExample) |
| MX (3) | MX390901B (enExample) |
| NZ (2) | NZ759692A (enExample) |
| PH (1) | PH12019502825A1 (enExample) |
| SA (1) | SA519410795B1 (enExample) |
| SG (1) | SG11201911543UA (enExample) |
| WO (2) | WO2018229493A2 (enExample) |
| ZA (1) | ZA201908054B (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2569185T3 (es) | 2011-03-01 | 2016-05-09 | Nucana Biomed Limited | Derivados de fosforamidato de 5-fluoro-2'-desoxiuridina para uso en el tratamiento del cáncer |
| EA033046B1 (ru) | 2014-06-25 | 2019-08-30 | НУКАНА ПиЭлСи | Состав, содержащий пролекарство гемцитабина |
| HRP20191461T1 (hr) | 2014-11-28 | 2019-11-15 | NuCana plc | Novi 2' i/ili 5' derivati 3'-deoksi adenozina supstituirani aminokiselinskim esterom fosforamidata, kao antikancerogenog spoja |
| CA3007347C (en) | 2015-12-11 | 2020-08-04 | NuCana plc | Diastereoselective synthesis of phosphate derivatives and of the gemcitabine prodrug nuc-1031 |
| GB201522764D0 (en) | 2015-12-23 | 2016-02-03 | Nucana Biomed Ltd | Formulations of phosphate derivatives |
| GB201609600D0 (en) | 2016-06-01 | 2016-07-13 | Nucuna Biomed Ltd | Cancer treatments |
| GB201709471D0 (en) | 2017-06-14 | 2017-07-26 | Nucana Biomed Ltd | Diastereoselective synthesis of hosphate derivatives |
| GB201715011D0 (en) | 2017-09-18 | 2017-11-01 | Nucana Biomed Ltd | Floxuridine synthesis |
| CN112409421A (zh) * | 2020-12-01 | 2021-02-26 | 上海兆维科技发展有限公司 | 一种3’-磷酸酯核苷的制备方法 |
| KR20250012582A (ko) | 2022-05-12 | 2025-01-24 | 뉴카나 피엘씨 | 암 치료 |
| CN120584123A (zh) | 2022-12-07 | 2025-09-02 | 努卡那有限公司 | 核苷衍生物nuc-3373的合成 |
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| DE279248C (enExample) | ||||
| US3792039A (en) | 1971-12-27 | 1974-02-12 | Miles Lab | Poly 2'-fluoro-2'-deoxyuridylic acid |
| US4500707A (en) * | 1980-02-29 | 1985-02-19 | University Patents, Inc. | Nucleosides useful in the preparation of polynucleotides |
| US4357324A (en) | 1981-02-24 | 1982-11-02 | The United States Of America As Represented By The Department Of Health And Human Services | Prodrug derivatives of 9β-D-arabinofuranosyl-2-fluoroadenine |
| US4668777A (en) * | 1981-03-27 | 1987-05-26 | University Patents, Inc. | Phosphoramidite nucleoside compounds |
| ES2172303T3 (es) | 1998-01-23 | 2002-09-16 | Newbiotics Inc | Agentes terapeuticos obtenidos por catalisis enzimatica. |
| US7462605B2 (en) | 1998-01-23 | 2008-12-09 | Celmed Oncology (Usa), Inc. | Phosphoramidate compounds and methods of use |
| US6683061B1 (en) | 1999-07-22 | 2004-01-27 | Newbiotics, Inc. | Enzyme catalyzed therapeutic activation |
| GB0317009D0 (en) | 2003-07-21 | 2003-08-27 | Univ Cardiff | Chemical compounds |
| EP1827460A4 (en) | 2004-12-09 | 2012-03-14 | Univ Minnesota | NUCLEOSIDE WITH ANTIVIRAL AND ANTI-CANCER EFFECT |
| GB0505781D0 (en) | 2005-03-21 | 2005-04-27 | Univ Cardiff | Chemical compounds |
| CN101287472B (zh) | 2005-08-15 | 2011-10-12 | 弗·哈夫曼-拉罗切有限公司 | 抗病毒的4'-取代前核苷酸的氨基磷酸酯类化合物 |
| GB0623493D0 (en) | 2006-11-24 | 2007-01-03 | Univ Cardiff | Chemical compounds |
| US7951789B2 (en) * | 2006-12-28 | 2011-05-31 | Idenix Pharmaceuticals, Inc. | Compounds and pharmaceutical compositions for the treatment of viral infections |
| US7964580B2 (en) | 2007-03-30 | 2011-06-21 | Pharmasset, Inc. | Nucleoside phosphoramidate prodrugs |
| US20090206007A1 (en) | 2008-02-20 | 2009-08-20 | Air Products And Chemicals, Inc. | Process and apparatus for upgrading coal using supercritical water |
| BRPI1004575A2 (pt) | 2009-01-09 | 2016-04-05 | Inhibitex Inc | composto, composição farmacêutica, método de tratamento de infecções virais, método de separação dos diaestereômeros de fósforo |
| WO2010108140A1 (en) | 2009-03-20 | 2010-09-23 | Alios Biopharma, Inc. | Substituted nucleoside and nucleotide analogs |
| TWI576352B (zh) | 2009-05-20 | 2017-04-01 | 基利法瑪席特有限責任公司 | 核苷磷醯胺 |
| US8618076B2 (en) | 2009-05-20 | 2013-12-31 | Gilead Pharmasset Llc | Nucleoside phosphoramidates |
| AP2012006535A0 (en) | 2010-03-31 | 2012-10-31 | Gilead Pharmasset Llc | Stereoselective synthesis of phosphorous containing actives |
| TW201136945A (en) | 2010-03-31 | 2011-11-01 | Pharmasset Inc | Purine nucleoside phosphoramidate |
| EA025311B1 (ru) | 2010-07-19 | 2016-12-30 | Гайлид Сайэнсиз, Инк. | Способы получения диастереомерно чистых фосфорамидатных пролекарств |
| WO2012040127A1 (en) | 2010-09-22 | 2012-03-29 | Alios Biopharma, Inc. | Substituted nucleotide analogs |
| US20120070411A1 (en) | 2010-09-22 | 2012-03-22 | Alios Biopharma, Inc. | Substituted nucleotide analogs |
| ES2716158T3 (es) | 2010-11-30 | 2019-06-10 | Gilead Pharmasset Llc | 2'-spiro-nucleótidos para el tratamiento de hepatitis C |
| US8772474B2 (en) | 2010-12-22 | 2014-07-08 | Alios Biopharma, Inc. | Cyclic nucleotide analogs |
| ES2569185T3 (es) | 2011-03-01 | 2016-05-09 | Nucana Biomed Limited | Derivados de fosforamidato de 5-fluoro-2'-desoxiuridina para uso en el tratamiento del cáncer |
| US9556216B2 (en) * | 2012-08-31 | 2017-01-31 | Novartis Ag | 2′-Ethynyl nucleoside derivatives for treatment of viral infections |
| AU2013346515B2 (en) | 2012-11-16 | 2017-05-25 | NuCana plc | Process for preparing nucleoside prodrugs |
| ES2952714T3 (es) | 2013-06-26 | 2023-11-03 | Janssen Pharmaceuticals Inc | Nucleósidos sustituidos, nucleótidos y análogos de los mismos |
| TW201542581A (zh) | 2013-09-11 | 2015-11-16 | 艾默理大學 | 核苷酸與核苷治療組成物及其相關用途 |
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| CZ307789B6 (cs) | 2014-04-15 | 2019-05-09 | Zentiva, K.S. | Způsob výroby biologicky účinných fosforamidátových léčiv |
| EP3131914B1 (en) * | 2014-04-16 | 2023-05-10 | Idenix Pharmaceuticals LLC | 3'-substituted methyl or alkynyl nucleosides for the treatment of hcv |
| EA033046B1 (ru) | 2014-06-25 | 2019-08-30 | НУКАНА ПиЭлСи | Состав, содержащий пролекарство гемцитабина |
| RS60968B1 (sr) | 2014-06-25 | 2020-11-30 | NuCana plc | Prolekovi gemcitabina |
| US9834577B2 (en) | 2014-07-22 | 2017-12-05 | Laurus Labs Limited | Process for the preparation of gemcitabine-[phenyl(benzoxy-L-alaninyl)] phosphate |
| EP3572410B1 (en) * | 2014-08-25 | 2022-07-20 | Medivir Aktiebolag | Dioxolane analogues of uridine for the treatment of cancer |
| GB201417644D0 (en) | 2014-10-06 | 2014-11-19 | Nucana Biomed Ltd | Method of separating phosphate diastereoisomers |
| CN105646629A (zh) | 2014-11-25 | 2016-06-08 | 广州市恒诺康医药科技有限公司 | L-核苷类化合物及其应用 |
| HRP20191461T1 (hr) | 2014-11-28 | 2019-11-15 | NuCana plc | Novi 2' i/ili 5' derivati 3'-deoksi adenozina supstituirani aminokiselinskim esterom fosforamidata, kao antikancerogenog spoja |
| WO2016098123A2 (en) * | 2014-12-16 | 2016-06-23 | Laurus Labs Private Ltd | A recycling process for preparing (s)-2-[(substituted-phenoxy)-phenoxy- phosphorylamino] propionic acid isopropyl ester diastereomers |
| WO2016145142A1 (en) | 2015-03-10 | 2016-09-15 | Emory University | Nucleotide and nucleoside therapeutics compositions and uses related thereto |
| CN107835687A (zh) | 2015-05-14 | 2018-03-23 | 努卡那有限公司 | 癌症治疗 |
| CN106543252A (zh) | 2015-09-16 | 2017-03-29 | 博瑞生物医药（苏州）股份有限公司 | 核苷氨基磷酸酯类前药的制备方法及其中间体 |
| CN106478753A (zh) | 2015-09-16 | 2017-03-08 | 博瑞生物医药（苏州）股份有限公司 | 一种nuc‑1031单一异构体的制备方法和用途 |
| CN106543220A (zh) * | 2015-09-16 | 2017-03-29 | 博瑞生物医药（苏州）股份有限公司 | 氨基磷酸酯化合物及其制备方法和晶体 |
| PH12018500691B1 (en) | 2015-10-05 | 2022-08-10 | NuCana plc | Combination therapy |
| EP3377512A4 (en) | 2015-11-16 | 2019-09-18 | Ichorion Therapeutics, Inc. | Nucleic Acid PRODRUGS |
| CA3007347C (en) * | 2015-12-11 | 2020-08-04 | NuCana plc | Diastereoselective synthesis of phosphate derivatives and of the gemcitabine prodrug nuc-1031 |
| GB201522764D0 (en) | 2015-12-23 | 2016-02-03 | Nucana Biomed Ltd | Formulations of phosphate derivatives |
| SI3393478T1 (sl) | 2015-12-23 | 2020-07-31 | NuCana plc | Kombinacijska terapija |
| GB201609600D0 (en) | 2016-06-01 | 2016-07-13 | Nucuna Biomed Ltd | Cancer treatments |
| GB201609602D0 (en) * | 2016-06-01 | 2016-07-13 | Nucuna Biomed Ltd | Chemical compounds |
| GB201609601D0 (en) | 2016-06-01 | 2016-07-13 | Nucana Biomed Ltd | Phosphoramidate compounds |
| GB201709471D0 (en) | 2017-06-14 | 2017-07-26 | Nucana Biomed Ltd | Diastereoselective synthesis of hosphate derivatives |
| GB201713916D0 (en) | 2017-08-30 | 2017-10-11 | Nucana Biomed Ltd | Treatment regimens |
-
2017
- 2017-06-14 GB GBGB1709471.5A patent/GB201709471D0/en not_active Ceased
-
2018
- 2018-06-14 JP JP2019569336A patent/JP7248209B2/ja active Active
- 2018-06-14 MA MA049379A patent/MA49379A/fr unknown
- 2018-06-14 IL IL302559A patent/IL302559B2/en unknown
- 2018-06-14 MX MX2019014914A patent/MX390901B/es unknown
- 2018-06-14 WO PCT/GB2018/051638 patent/WO2018229493A2/en not_active Ceased
- 2018-06-14 CN CN202311430904.3A patent/CN117486959A/zh active Pending
- 2018-06-14 IL IL271159A patent/IL271159B2/en unknown
- 2018-06-14 NZ NZ759692A patent/NZ759692A/en unknown
- 2018-06-14 EA EA201992873A patent/EA201992873A1/ru unknown
- 2018-06-14 CN CN201880039189.1A patent/CN110785425B/zh active Active
- 2018-06-14 PH PH1/2019/502825A patent/PH12019502825A1/en unknown
- 2018-06-14 SG SG11201911543UA patent/SG11201911543UA/en unknown
- 2018-06-14 KR KR1020197036989A patent/KR102695300B1/ko active Active
- 2018-06-14 CA CA3065682A patent/CA3065682A1/en active Pending
- 2018-06-14 CN CN201880039747.4A patent/CN110753697B/zh active Active
- 2018-06-14 NZ NZ800534A patent/NZ800534A/en unknown
- 2018-06-14 CA CA3064177A patent/CA3064177A1/en active Pending
- 2018-06-14 KR KR1020247026745A patent/KR102920287B1/ko active Active
- 2018-06-14 EP EP18735380.0A patent/EP3638684B1/en active Active
- 2018-06-14 US US16/623,272 patent/US11897913B2/en active Active
- 2018-06-14 IL IL312228A patent/IL312228B2/en unknown
- 2018-06-14 EP EP26186784.0A patent/EP4786476A2/en active Pending
- 2018-06-14 JP JP2019569286A patent/JP7279991B2/ja active Active
- 2018-06-14 ES ES18735380T patent/ES3075652T3/es active Active
- 2018-06-14 MX MX2019014907A patent/MX391332B/es unknown
- 2018-06-14 BR BR112019026747-6A patent/BR112019026747A2/pt unknown
- 2018-06-14 AU AU2018284131A patent/AU2018284131B2/en active Active
- 2018-06-14 US US16/623,263 patent/US11414452B2/en active Active
- 2018-06-14 EP EP18735381.8A patent/EP3638685A1/en active Pending
- 2018-06-14 WO PCT/GB2018/051641 patent/WO2018229495A1/en not_active Ceased
-
2019
- 2019-12-04 ZA ZA2019/08054A patent/ZA201908054B/en unknown
- 2019-12-10 MX MX2022003822A patent/MX2022003822A/es unknown
- 2019-12-11 CL CL2019003632A patent/CL2019003632A1/es unknown
- 2019-12-12 SA SA519410795A patent/SA519410795B1/ar unknown
-
2022
- 2022-06-30 AU AU2022204691A patent/AU2022204691B2/en active Active
- 2022-08-15 US US17/888,312 patent/US12054511B2/en active Active
-
2023
- 2023-05-02 JP JP2023076006A patent/JP7525687B2/ja active Active
-
2024
- 2024-01-24 AU AU2024200428A patent/AU2024200428C1/en active Active
- 2024-06-20 US US18/749,420 patent/US20250171487A1/en active Pending
- 2024-07-18 JP JP2024114519A patent/JP2024138523A/ja active Pending
-
2025
- 2025-12-19 JP JP2025266864A patent/JP2026034703A/ja active Pending
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