AU2018284131B2 - Synthesis of substantially diastereomerically pure phosphate protides - Google Patents
Synthesis of substantially diastereomerically pure phosphate protides Download PDFInfo
- Publication number
- AU2018284131B2 AU2018284131B2 AU2018284131A AU2018284131A AU2018284131B2 AU 2018284131 B2 AU2018284131 B2 AU 2018284131B2 AU 2018284131 A AU2018284131 A AU 2018284131A AU 2018284131 A AU2018284131 A AU 2018284131A AU 2018284131 B2 AU2018284131 B2 AU 2018284131B2
- Authority
- AU
- Australia
- Prior art keywords
- compound
- diastereoisomer
- formula
- mixture
- formula ila
- 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.)
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/16—Purine radicals
- C07H19/20—Purine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
- C07H19/207—Purine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids the phosphoric or polyphosphoric acids being esterified by a further hydroxylic compound, e.g. flavine adenine dinucleotide or nicotinamide-adenine dinucleotide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/16—Purine radicals
- C07H19/20—Purine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/02—Phosphorylation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/06—Pyrimidine radicals
- C07H19/10—Pyrimidine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU2022204691A AU2022204691B2 (en) | 2017-06-14 | 2022-06-30 | Synthesis of substantially diastereomerically pure phosphate protides |
| AU2024200428A AU2024200428B2 (en) | 2017-06-14 | 2024-01-24 | Synthesis of substantially diastereomerically pure phosphate protides |
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/GB2018/051638 WO2018229493A2 (en) | 2017-06-14 | 2018-06-14 | Synthesis of phosphate derivatives |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2022204691A Division AU2022204691B2 (en) | 2017-06-14 | 2022-06-30 | Synthesis of substantially diastereomerically pure phosphate protides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2018284131A1 AU2018284131A1 (en) | 2020-01-16 |
| AU2018284131B2 true AU2018284131B2 (en) | 2022-04-07 |
Family
ID=59358400
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2018284131A Active AU2018284131B2 (en) | 2017-06-14 | 2018-06-14 | Synthesis of substantially diastereomerically pure phosphate protides |
| AU2022204691A Active AU2022204691B2 (en) | 2017-06-14 | 2022-06-30 | Synthesis of substantially diastereomerically pure phosphate protides |
| AU2024200428A Active AU2024200428B2 (en) | 2017-06-14 | 2024-01-24 | Synthesis of substantially diastereomerically pure phosphate protides |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2022204691A Active AU2022204691B2 (en) | 2017-06-14 | 2022-06-30 | Synthesis of substantially diastereomerically pure phosphate protides |
| AU2024200428A Active AU2024200428B2 (en) | 2017-06-14 | 2024-01-24 | Synthesis of substantially diastereomerically pure phosphate protides |
Country Status (18)
| Country | Link |
|---|---|
| US (4) | US11414452B2 (OSRAM) |
| EP (2) | EP3638684A2 (OSRAM) |
| JP (4) | JP7248209B2 (OSRAM) |
| KR (2) | KR102695300B1 (OSRAM) |
| CN (3) | CN110753697B (OSRAM) |
| AU (3) | AU2018284131B2 (OSRAM) |
| BR (1) | BR112019026747A2 (OSRAM) |
| CA (2) | CA3065682A1 (OSRAM) |
| CL (1) | CL2019003632A1 (OSRAM) |
| EA (1) | EA201992873A1 (OSRAM) |
| GB (1) | GB201709471D0 (OSRAM) |
| IL (3) | IL312228B2 (OSRAM) |
| MA (1) | MA49379A (OSRAM) |
| MX (3) | MX391332B (OSRAM) |
| PH (1) | PH12019502825A1 (OSRAM) |
| SA (1) | SA519410795B1 (OSRAM) |
| SG (1) | SG11201911543UA (OSRAM) |
| WO (2) | WO2018229493A2 (OSRAM) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HRP20160346T1 (hr) | 2011-03-01 | 2016-05-06 | Nucana Biomed Limited | Fosforoamidatni derivati 5-fluoro-2'-deoksiuridina za upotrebu u tretmanu raka |
| DK3119794T3 (en) | 2014-06-25 | 2018-01-22 | NuCana plc | FORMULA CONTAINING A GEMCITABIN PRODRUG |
| KR102548806B1 (ko) | 2014-11-28 | 2023-06-27 | 뉴카나 피엘씨 | 항암제로서 새로운 2' 및/또는 5' 아미노산 에스테르 포스포르아미데이트 3'-디옥시아데노신 유도체 |
| WO2017098252A1 (en) | 2015-12-11 | 2017-06-15 | Nucana Biomed Limited | 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 |
| EP4630433A1 (en) | 2022-12-07 | 2025-10-15 | NuCana plc | Synthesis of nucleoside derivative nuc-3373 |
Citations (4)
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| WO2016030335A1 (en) * | 2014-08-25 | 2016-03-03 | Medivir Ab | Dioxolane analogues of uridine for the treatment of cancer |
| WO2016083830A1 (en) * | 2014-11-28 | 2016-06-02 | Nucana Biomed Limited | 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 |
| WO2017207989A1 (en) * | 2016-06-01 | 2017-12-07 | Nucana Biomed Limited | Adenosine derivatives for use in the treatment of cancer |
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| 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 |
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| GB201609601D0 (en) | 2016-06-01 | 2016-07-13 | Nucana Biomed Ltd | Phosphoramidate 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 AU AU2018284131A patent/AU2018284131B2/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 BR BR112019026747-6A patent/BR112019026747A2/pt unknown
- 2018-06-14 JP JP2019569336A patent/JP7248209B2/ja active Active
- 2018-06-14 PH PH1/2019/502825A patent/PH12019502825A1/en unknown
- 2018-06-14 IL IL312228A patent/IL312228B2/en unknown
- 2018-06-14 CN CN201880039189.1A patent/CN110785425B/zh active Active
- 2018-06-14 KR KR1020197036989A patent/KR102695300B1/ko active Active
- 2018-06-14 US US16/623,263 patent/US11414452B2/en active Active
- 2018-06-14 IL IL302559A patent/IL302559B2/en unknown
- 2018-06-14 CA CA3064177A patent/CA3064177A1/en active Pending
- 2018-06-14 MX MX2019014907A patent/MX391332B/es unknown
- 2018-06-14 IL IL271159A patent/IL271159B2/en unknown
- 2018-06-14 KR KR1020247026745A patent/KR20240127483A/ko active Pending
- 2018-06-14 EA EA201992873A patent/EA201992873A1/ru unknown
- 2018-06-14 WO PCT/GB2018/051638 patent/WO2018229493A2/en not_active Ceased
- 2018-06-14 US US16/623,272 patent/US11897913B2/en active Active
- 2018-06-14 MX MX2019014914A patent/MX390901B/es unknown
- 2018-06-14 EP EP18735380.0A patent/EP3638684A2/en active Pending
- 2018-06-14 EP EP18735381.8A patent/EP3638685A1/en active Pending
- 2018-06-14 CN CN202311430904.3A patent/CN117486959A/zh active Pending
- 2018-06-14 JP JP2019569286A patent/JP7279991B2/ja active Active
- 2018-06-14 SG SG11201911543UA patent/SG11201911543UA/en unknown
- 2018-06-14 MA MA049379A patent/MA49379A/fr unknown
- 2018-06-14 WO PCT/GB2018/051641 patent/WO2018229495A1/en not_active Ceased
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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
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2022
- 2022-06-30 AU AU2022204691A patent/AU2022204691B2/en active Active
- 2022-08-15 US US17/888,312 patent/US12054511B2/en active Active
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2023
- 2023-05-02 JP JP2023076006A patent/JP7525687B2/ja active Active
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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
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016030335A1 (en) * | 2014-08-25 | 2016-03-03 | Medivir Ab | Dioxolane analogues of uridine for the treatment of cancer |
| WO2016083830A1 (en) * | 2014-11-28 | 2016-06-02 | Nucana Biomed Limited | 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 |
| WO2017207989A1 (en) * | 2016-06-01 | 2017-12-07 | Nucana Biomed Limited | Adenosine derivatives for use in the treatment of cancer |
Non-Patent Citations (4)
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| McGuigan, C. et al.; J. Med. Chem., 54, 7247-7258 (2011). DOI: 10.1021/jm200815w. * |
| Ross, B. S. et al.; J. Org. Chem., 76, 8311-8319 (2011). DOI:10.1021/jo201492m. * |
| Serpi, M. et al.; ChemistryOpen, 6, 424-436 (2017). DOI: 10.1002/open.201700019. * |
| Simmons, B. et al.; Org. Lett., 19, 2218-2221 (2017). DOI: 10.1021/acs.orglett.7b00469. * |
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| FGA | Letters patent sealed or granted (standard patent) |