JP2020523381A5 - - Google Patents
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- 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 |
|---|---|---|---|
| GB1709471.5 | 2017-06-14 | ||
| GBGB1709471.5A GB201709471D0 (en) | 2017-06-14 | 2017-06-14 | Diastereoselective synthesis of hosphate derivatives |
| 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 (enExample) | 2021-07-26 |
| JP7248209B2 JP7248209B2 (ja) | 2023-03-29 |
Family
ID=59358400
Family Applications (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 |
| 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 |
| 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 |
Family Applications Before (1)
| 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 |
Family Applications After (2)
| 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 |
Country Status (18)
| Country | Link |
|---|---|
| US (4) | US11414452B2 (enExample) |
| EP (2) | EP3638685A1 (enExample) |
| JP (4) | JP7279991B2 (enExample) |
| KR (2) | KR20240127483A (enExample) |
| CN (3) | CN110785425B (enExample) |
| AU (3) | AU2018284131B2 (enExample) |
| BR (1) | BR112019026747A2 (enExample) |
| CA (2) | CA3064177A1 (enExample) |
| CL (1) | CL2019003632A1 (enExample) |
| EA (1) | EA201992873A1 (enExample) |
| GB (1) | GB201709471D0 (enExample) |
| IL (3) | IL302559B2 (enExample) |
| MA (1) | MA49379A (enExample) |
| MX (3) | MX391332B (enExample) |
| PH (1) | PH12019502825A1 (enExample) |
| SA (1) | SA519410795B1 (enExample) |
| SG (1) | SG11201911543UA (enExample) |
| WO (2) | WO2018229495A1 (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SI2681227T1 (sl) | 2011-03-01 | 2016-04-29 | Nucana Biomed Limited | Fosforamidatni derivati 5-fluoro-2'-deoksiuridina za uporabo pri zdravljenju raka |
| EA033046B1 (ru) | 2014-06-25 | 2019-08-30 | НУКАНА ПиЭлСи | Состав, содержащий пролекарство гемцитабина |
| EP3683225A1 (en) | 2014-11-28 | 2020-07-22 | Nucana PLC | New 2' and/or 5' amino-acid ester phosphoramidate 3'-deoxy adenosine derivatives as anti-cancer compounds |
| SG11201804774YA (en) | 2015-12-11 | 2018-07-30 | 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 |
| CN119546313A (zh) | 2022-05-12 | 2025-02-28 | 努卡那有限公司 | 使用nuc-7738的癌症治疗 |
| WO2024121527A1 (en) | 2022-12-07 | 2024-06-13 | NuCana plc | Synthesis of nucleoside derivative nuc-3373 |
Family Cites Families (59)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US7462605B2 (en) | 1998-01-23 | 2008-12-09 | Celmed Oncology (Usa), Inc. | Phosphoramidate compounds and methods of use |
| IL137164A0 (en) | 1998-01-23 | 2001-07-24 | 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 |
| 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 |
| CA2618335C (en) | 2005-08-15 | 2015-03-31 | F.Hoffmann-La Roche Ag | Antiviral phosphoramidates of 4'-substituted pronucleotides |
| 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 |
| JP2012514657A (ja) | 2009-01-09 | 2012-06-28 | ユニバーシテイ・カレツジ・オブ・カーデイフ・コンサルタンツ・リミテツド | ウィルス感染を治療するためのグアノシンヌクレオシド化合物のホスホルアミダート誘導体 |
| EP2623104A1 (en) | 2009-03-20 | 2013-08-07 | 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 |
| JP2013527145A (ja) | 2010-03-31 | 2013-06-27 | ギリード・ファーマセット・エルエルシー | リン含有活性化剤の立体選択的合成 |
| TW201136945A (en) | 2010-03-31 | 2011-11-01 | Pharmasset Inc | Purine nucleoside phosphoramidate |
| NZ606141A (en) | 2010-07-19 | 2015-03-27 | Gilead Sciences Inc | Methods for the preparation of diasteromerically pure phosphoramidate prodrugs |
| WO2012040126A1 (en) | 2010-09-22 | 2012-03-29 | Alios Biopharma, Inc. | Substituted nucleotide analogs |
| CA2810928A1 (en) | 2010-09-22 | 2012-03-29 | Alios Biopharma, Inc. | Substituted nucleotide analogs |
| PT3042910T (pt) | 2010-11-30 | 2019-04-16 | Gilead Pharmasset Llc | 2'-espiro-nucleósidos para utilização na terapia da hepatite c |
| AU2011349278C1 (en) | 2010-12-22 | 2017-01-19 | Alios Biopharma, Inc. | Cyclic nucleotide analogs |
| SI2681227T1 (sl) | 2011-03-01 | 2016-04-29 | Nucana Biomed Limited | Fosforamidatni derivati 5-fluoro-2'-deoksiuridina za uporabo pri zdravljenju raka |
| EP2890704B1 (en) * | 2012-08-31 | 2018-02-28 | Novartis AG | 2'-ethynyl nucleoside derivatives for treatment of viral infections |
| CN104903339A (zh) | 2012-11-16 | 2015-09-09 | 卡迪夫大学学院顾问有限公司 | 用于制备核苷前体药物的方法 |
| US9815864B2 (en) | 2013-06-26 | 2017-11-14 | Alios Biopharma, Inc. | Substituted nucleosides, nucleotides and analogs thereof |
| PL3043803T3 (pl) | 2013-09-11 | 2022-11-07 | Emory University | Kompozycje nukleotydowe i nukleozydowe oraz ich zastosowanie |
| EP3055319A4 (en) | 2013-10-11 | 2018-01-10 | Alios Biopharma, Inc. | Substituted nucleosides, nucleotides and analogs thereof |
| WO2015081133A2 (en) | 2013-11-27 | 2015-06-04 | Idenix Pharmaceuticals, Inc. | Nucleotides for the treatment of liver cancer |
| 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 |
| PL3160978T3 (pl) | 2014-06-25 | 2020-11-30 | NuCana plc | Proleki gemcytabiny |
| EA033046B1 (ru) | 2014-06-25 | 2019-08-30 | НУКАНА ПиЭлСи | Состав, содержащий пролекарство гемцитабина |
| JP6646663B2 (ja) | 2014-07-22 | 2020-02-14 | ニューカナ バイオメッド リミテッドＮｕｃａｎａ Ｂｉｏｍｅｄ Ｌｉｍｉｔｅｄ | ゲムシタビン−［フェニル（ベンゾキシ−ｌ−アラニニル）］ホスフェートの製造方法リン酸誘導体を製造する方法 |
| CN111269264A (zh) * | 2014-08-25 | 2020-06-12 | 美迪维尔公司 | 用于治疗癌症的尿苷的二氧戊环类似物 |
| 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 |
| EP3683225A1 (en) | 2014-11-28 | 2020-07-22 | Nucana PLC | New 2' and/or 5' amino-acid ester phosphoramidate 3'-deoxy adenosine derivatives as anti-cancer compounds |
| 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 |
| KR20180021697A (ko) | 2015-05-14 | 2018-03-05 | 뉴카나 피엘씨 | 암 치료 |
| 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 |
| 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 |
| CN112156102B (zh) | 2015-09-16 | 2023-10-03 | 济南高合医疗科技有限公司 | 一种nuc-1031单一异构体的晶型及其制备方法 |
| WO2017060661A1 (en) | 2015-10-05 | 2017-04-13 | Nucana Biomed Limited | Combination therapy |
| CN108431016A (zh) * | 2015-11-16 | 2018-08-21 | 艾可瑞恩治疗公司 | 核酸前体药物 |
| SG11201804774YA (en) | 2015-12-11 | 2018-07-30 | NuCana plc | Diastereoselective synthesis of phosphate derivatives and of the gemcitabine prodrug nuc-1031 |
| CA3008749C (en) | 2015-12-23 | 2024-01-02 | NuCana plc | Treatment of ovarian cancer or biliary tract cancer with a combination of gemcitabine-(phenyl-benzoxy-l-alaninyl)]-phosphate and cisplatin |
| GB201522764D0 (en) | 2015-12-23 | 2016-02-03 | Nucana Biomed Ltd | Formulations of phosphate derivatives |
| 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 |
| 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 CA CA3064177A patent/CA3064177A1/en active Pending
- 2018-06-14 KR KR1020247026745A patent/KR20240127483A/ko active Pending
- 2018-06-14 WO PCT/GB2018/051641 patent/WO2018229495A1/en not_active Ceased
- 2018-06-14 EP EP18735381.8A patent/EP3638685A1/en active Pending
- 2018-06-14 JP JP2019569286A patent/JP7279991B2/ja active Active
- 2018-06-14 CN CN201880039189.1A patent/CN110785425B/zh active Active
- 2018-06-14 AU AU2018284131A patent/AU2018284131B2/en active Active
- 2018-06-14 BR BR112019026747-6A patent/BR112019026747A2/pt unknown
- 2018-06-14 PH PH1/2019/502825A patent/PH12019502825A1/en unknown
- 2018-06-14 EA EA201992873A patent/EA201992873A1/ru unknown
- 2018-06-14 IL IL302559A patent/IL302559B2/en unknown
- 2018-06-14 CN CN202311430904.3A patent/CN117486959A/zh active Pending
- 2018-06-14 US US16/623,263 patent/US11414452B2/en active Active
- 2018-06-14 MX MX2019014907A patent/MX391332B/es unknown
- 2018-06-14 MA MA049379A patent/MA49379A/fr unknown
- 2018-06-14 MX MX2019014914A patent/MX390901B/es unknown
- 2018-06-14 US US16/623,272 patent/US11897913B2/en 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 JP JP2019569336A patent/JP7248209B2/ja active Active
- 2018-06-14 WO PCT/GB2018/051638 patent/WO2018229493A2/en not_active Ceased
- 2018-06-14 IL IL312228A patent/IL312228B2/en unknown
- 2018-06-14 EP EP18735380.0A patent/EP3638684A2/en active Pending
- 2018-06-14 IL IL271159A patent/IL271159B2/en unknown
- 2018-06-14 SG SG11201911543UA patent/SG11201911543UA/en unknown
- 2018-06-14 KR KR1020197036989A patent/KR102695300B1/ko active Active
-
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
- 2024-01-24 AU AU2024200428A patent/AU2024200428B2/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
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