JP2020523381A5 - - Google Patents
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- Publication number
- JP2020523381A5 JP2020523381A5 JP2019569336A JP2019569336A JP2020523381A5 JP 2020523381 A5 JP2020523381 A5 JP 2020523381A5 JP 2019569336 A JP2019569336 A JP 2019569336A JP 2019569336 A JP2019569336 A JP 2019569336A JP 2020523381 A5 JP2020523381 A5 JP 2020523381A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- protecting group
- nuc
- group
- 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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- 238000000034 method Methods 0.000 claims 19
- 150000001875 compounds Chemical class 0.000 claims 15
- 125000006239 protecting group Chemical group 0.000 claims 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- -1 for example Chemical group 0.000 claims 3
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims 3
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 2
- KQLDDLUWUFBQHP-UHFFFAOYSA-N Cordycepin Natural products C1=NC=2C(N)=NC=NC=2N1C1OCC(CO)C1O KQLDDLUWUFBQHP-UHFFFAOYSA-N 0.000 claims 1
- OFEZSBMBBKLLBJ-BAJZRUMYSA-N cordycepin Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)C[C@H]1O OFEZSBMBBKLLBJ-BAJZRUMYSA-N 0.000 claims 1
- OFEZSBMBBKLLBJ-UHFFFAOYSA-N cordycepine Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(CO)CC1O OFEZSBMBBKLLBJ-UHFFFAOYSA-N 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 150000004678 hydrides Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB1709471.5A GB201709471D0 (en) | 2017-06-14 | 2017-06-14 | Diastereoselective synthesis of hosphate derivatives |
| GB1709471.5 | 2017-06-14 | ||
| PCT/GB2018/051641 WO2018229495A1 (en) | 2017-06-14 | 2018-06-14 | Synthesis of 3'-deoxyadenosine-5'-0-[phenyl(benzyloxy-l-alaninyl)]phosphate (nuc-7738) |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2020523381A JP2020523381A (ja) | 2020-08-06 |
| JP2020523381A5 true JP2020523381A5 (https=) | 2021-07-26 |
| JP7248209B2 JP7248209B2 (ja) | 2023-03-29 |
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 After (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| 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 |
Country Status (19)
| Country | Link |
|---|---|
| US (4) | US11897913B2 (https=) |
| EP (2) | EP3638685A1 (https=) |
| JP (5) | JP7248209B2 (https=) |
| KR (2) | KR102920287B1 (https=) |
| CN (3) | CN110785425B (https=) |
| AU (2) | AU2018284131B2 (https=) |
| BR (1) | BR112019026747A2 (https=) |
| CA (2) | CA3065682A1 (https=) |
| CL (1) | CL2019003632A1 (https=) |
| EA (1) | EA201992873A1 (https=) |
| GB (1) | GB201709471D0 (https=) |
| IL (3) | IL271159B2 (https=) |
| MA (1) | MA49379A (https=) |
| MX (3) | MX390901B (https=) |
| NZ (2) | NZ759692A (https=) |
| PH (1) | PH12019502825A1 (https=) |
| SA (1) | SA519410795B1 (https=) |
| SG (1) | SG11201911543UA (https=) |
| WO (2) | WO2018229493A2 (https=) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HUE029022T2 (en) | 2011-03-01 | 2017-02-28 | Nucana Biomed Ltd | Phosphoramidate derivatives of 5-fluoro-2'-deoxyuridine for use in the treatment of cancer |
| JP6855248B2 (ja) | 2014-06-25 | 2021-04-07 | ヌカナ ピーエルシー | ゲムシタビン−プロドラッグを含む製剤 |
| IL291927A (en) | 2014-11-28 | 2022-06-01 | NuCana plc | Oligonucleotides containing modified nucleosides |
| HRP20211812T1 (hr) | 2015-12-11 | 2022-03-04 | NuCana plc | Dijastereoselektivna sinteza derivata fosfata i prolijeka gemcitabina 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 |
| AU2023268725A1 (en) | 2022-05-12 | 2024-12-12 | NuCana plc | Cancer treatment with nuc-7738 |
| JP2025539267A (ja) | 2022-12-07 | 2025-12-04 | ニューカナ パブリック リミテッド カンパニー | ヌクレオシド誘導体ｎｕｃ－３３７３の合成 |
Family Cites Families (59)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE279248C (https=) | ||||
| 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 |
| US7462605B2 (en) | 1998-01-23 | 2008-12-09 | Celmed Oncology (Usa), Inc. | Phosphoramidate compounds and methods of use |
| CA2317505C (en) | 1998-01-23 | 2011-01-04 | Newbiotics, Inc. | Enzyme catalyzed therapeutic agents |
| 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 |
| CA2589935A1 (en) | 2004-12-09 | 2006-06-15 | Regents Of The University Of Minnesota | Nucleosides with antiviral and anticancer activity |
| GB0505781D0 (en) * | 2005-03-21 | 2005-04-27 | Univ Cardiff | Chemical compounds |
| WO2007020193A2 (en) | 2005-08-15 | 2007-02-22 | F. Hoffmann-La Roche Ag | Antiviral phosphoramidates of 4 ' -substituted pronucleotides |
| GB0623493D0 (en) | 2006-11-24 | 2007-01-03 | Univ Cardiff | Chemical compounds |
| US20080261913A1 (en) * | 2006-12-28 | 2008-10-23 | Idenix Pharmaceuticals, Inc. | Compounds and pharmaceutical compositions for the treatment of liver disorders |
| 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 |
| SG172921A1 (en) | 2009-01-09 | 2011-08-29 | Univ Cardiff | Phosphoramidate derivatives of guanosine nucleoside compounds for treatment of viral infections |
| AU2010226466A1 (en) | 2009-03-20 | 2011-10-20 | Alios Biopharma, Inc. | Substituted nucleoside and nucleotide analogs |
| TWI598358B (zh) | 2009-05-20 | 2017-09-11 | 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 |
| PT2609923T (pt) | 2010-03-31 | 2017-08-30 | Gilead Pharmasset Llc | Processo para a cristalização de 2-(((s)- (perfluorofenoxi)(fenoxi)fosforil)amino)propanoato de (s)-isopropilo |
| UY33312A (es) | 2010-03-31 | 2011-10-31 | Pharmasset Inc | Fosforamidato de nucleosido de purina |
| KR101995598B1 (ko) | 2010-07-19 | 2019-07-02 | 길리애드 사이언시즈, 인코포레이티드 | 부분입체 이성질성으로 순수한 포스포라미데이트 전구약물의 제조 방법 |
| US20120070411A1 (en) | 2010-09-22 | 2012-03-22 | Alios Biopharma, Inc. | Substituted nucleotide analogs |
| BR112013005872A2 (pt) | 2010-09-22 | 2019-09-24 | Alios Biopharma Inc | compostos, composição farmacêutica e respectivos usos |
| AU2011336632B2 (en) | 2010-11-30 | 2015-09-03 | Gilead Pharmasset Llc | Compounds |
| AU2011349278C1 (en) | 2010-12-22 | 2017-01-19 | Alios Biopharma, Inc. | Cyclic nucleotide analogs |
| HUE029022T2 (en) | 2011-03-01 | 2017-02-28 | Nucana Biomed Ltd | Phosphoramidate derivatives of 5-fluoro-2'-deoxyuridine for use in the treatment of cancer |
| EP2890704B1 (en) | 2012-08-31 | 2018-02-28 | Novartis AG | 2'-ethynyl nucleoside derivatives for treatment of viral infections |
| SG11201503750YA (en) | 2012-11-16 | 2015-06-29 | Univ Cardiff | Process for preparing nucleoside prodrugs |
| HK1224229A1 (zh) | 2013-06-26 | 2017-08-18 | Alios Biopharma, Inc. | 取代的核苷，核苷酸及其类似物 |
| SI3043803T1 (sl) | 2013-09-11 | 2022-09-30 | Emory University | Nukleotidne in nukleozidne sestave in njihova uporaba |
| EP3055319A4 (en) | 2013-10-11 | 2018-01-10 | Alios Biopharma, Inc. | Substituted nucleosides, nucleotides and analogs thereof |
| RU2016125213A (ru) | 2013-11-27 | 2017-12-29 | АЙДЕНИКС ФАРМАСЬЮТИКАЛЗ ЭлЭлСи | Нуклеотиды для лечения рака печени |
| CZ307789B6 (cs) * | 2014-04-15 | 2019-05-09 | Zentiva, K.S. | Způsob výroby biologicky účinných fosforamidátových léčiv |
| WO2015161137A1 (en) | 2014-04-16 | 2015-10-22 | Idenix Pharmaceuticals, Inc. | 3'-substituted methyl or alkynyl nucleosides for the treatment of hcv |
| JP6855248B2 (ja) | 2014-06-25 | 2021-04-07 | ヌカナ ピーエルシー | ゲムシタビン−プロドラッグを含む製剤 |
| HRP20230584T1 (hr) | 2014-06-25 | 2023-09-15 | NuCana plc | Prolijekovi gemcitabina |
| WO2016012781A1 (en) | 2014-07-22 | 2016-01-28 | Nucana Biomed Limited | Process for the preparation of gemcitabine-[phenyl(benzoxy-l-alaninyl)] phosphate |
| SG10202001117YA (en) * | 2014-08-25 | 2020-04-29 | Medivir Ab | 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 |
| IL291927A (en) | 2014-11-28 | 2022-06-01 | NuCana plc | Oligonucleotides containing modified nucleosides |
| 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 |
| EP3415149A1 (en) | 2015-05-14 | 2018-12-19 | NuCana plc | Cancer treatments |
| CN106539810B (zh) | 2015-09-16 | 2021-03-09 | 济南高合医疗科技有限公司 | 一种富集了nuc-1031单一异构体的组合物及其制备方法和用途 |
| 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 |
| 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 |
| PH12018500691B1 (en) | 2015-10-05 | 2022-08-10 | NuCana plc | Combination therapy |
| US10745435B2 (en) * | 2015-11-16 | 2020-08-18 | Cerecor, Inc. | Nucleic acid prodrugs |
| HRP20211812T1 (hr) | 2015-12-11 | 2022-03-04 | NuCana plc | Dijastereoselektivna sinteza derivata fosfata i prolijeka gemcitabina nuc-1031 |
| GB201522764D0 (en) | 2015-12-23 | 2016-02-03 | Nucana Biomed Ltd | Formulations of phosphate derivatives |
| MA51576A (fr) | 2015-12-23 | 2020-11-18 | NuCana plc | Polythérapie |
| GB201609601D0 (en) | 2016-06-01 | 2016-07-13 | Nucana Biomed Ltd | Phosphoramidate compounds |
| GB201609602D0 (en) | 2016-06-01 | 2016-07-13 | Nucuna Biomed Ltd | Chemical compounds |
| 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 |
| 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 NZ NZ759692A patent/NZ759692A/en unknown
- 2018-06-14 WO PCT/GB2018/051638 patent/WO2018229493A2/en not_active Ceased
- 2018-06-14 CN CN201880039189.1A patent/CN110785425B/zh active Active
- 2018-06-14 SG SG11201911543UA patent/SG11201911543UA/en unknown
- 2018-06-14 PH PH1/2019/502825A patent/PH12019502825A1/en unknown
- 2018-06-14 MA MA049379A patent/MA49379A/fr unknown
- 2018-06-14 IL IL271159A patent/IL271159B2/en unknown
- 2018-06-14 KR KR1020247026745A patent/KR102920287B1/ko active Active
- 2018-06-14 CA CA3065682A patent/CA3065682A1/en active Pending
- 2018-06-14 WO PCT/GB2018/051641 patent/WO2018229495A1/en not_active Ceased
- 2018-06-14 US US16/623,272 patent/US11897913B2/en active Active
- 2018-06-14 KR KR1020197036989A patent/KR102695300B1/ko active Active
- 2018-06-14 CN CN202311430904.3A patent/CN117486959A/zh active Pending
- 2018-06-14 IL IL302559A patent/IL302559B2/en unknown
- 2018-06-14 IL IL312228A patent/IL312228B2/en unknown
- 2018-06-14 AU AU2018284131A patent/AU2018284131B2/en active Active
- 2018-06-14 EA EA201992873A patent/EA201992873A1/ru unknown
- 2018-06-14 MX MX2019014914A patent/MX390901B/es unknown
- 2018-06-14 MX MX2019014907A patent/MX391332B/es unknown
- 2018-06-14 NZ NZ800534A patent/NZ800534A/en unknown
- 2018-06-14 CN CN201880039747.4A patent/CN110753697B/zh active Active
- 2018-06-14 CA CA3064177A patent/CA3064177A1/en active Pending
- 2018-06-14 BR BR112019026747-6A patent/BR112019026747A2/pt unknown
- 2018-06-14 US US16/623,263 patent/US11414452B2/en active Active
- 2018-06-14 JP JP2019569336A patent/JP7248209B2/ja active Active
- 2018-06-14 JP JP2019569286A patent/JP7279991B2/ja active Active
- 2018-06-14 EP EP18735381.8A patent/EP3638685A1/en active Pending
- 2018-06-14 EP EP18735380.0A patent/EP3638684A2/en active Pending
-
2019
- 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
- 2024-06-20 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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