CA3065682A1 - Synthesis of substantially diastereomerically pure phosphate protides - Google Patents

Synthesis of substantially diastereomerically pure phosphate protides Download PDF

Info

Publication number
CA3065682A1
CA3065682A1 CA3065682A CA3065682A CA3065682A1 CA 3065682 A1 CA3065682 A1 CA 3065682A1 CA 3065682 A CA3065682 A CA 3065682A CA 3065682 A CA3065682 A CA 3065682A CA 3065682 A1 CA3065682 A1 CA 3065682A1
Authority
CA
Canada
Prior art keywords
compound
formula
mixture
pure form
nuc
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.)
Pending
Application number
CA3065682A
Other languages
English (en)
French (fr)
Inventor
Hugh Griffith
Gordon Kennovin
Venkata Lakshmi Narasimha Rao Dammalapati
Mani Bushan Kotala
Original Assignee
Nucana PLC
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Nucana PLC filed Critical Nucana PLC
Publication of CA3065682A1 publication Critical patent/CA3065682A1/en
Pending legal-status Critical Current

Links

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
    • 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
    • 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
    • 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)
CA3065682A 2017-06-14 2018-06-14 Synthesis of substantially diastereomerically pure phosphate protides Pending CA3065682A1 (en)

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

Publications (1)

Publication Number Publication Date
CA3065682A1 true CA3065682A1 (en) 2018-12-20

Family

ID=59358400

Family Applications (2)

Application Number Title Priority Date Filing Date
CA3065682A Pending CA3065682A1 (en) 2017-06-14 2018-06-14 Synthesis of substantially diastereomerically pure phosphate protides
CA3064177A Pending CA3064177A1 (en) 2017-06-14 2018-06-14 Synthesis of 3'-deoxyadenosine-5'-0-[phenyl(benzyloxy-l-alaninyl)]phosphate (nuc-7738)

Family Applications After (1)

Application Number Title Priority Date Filing Date
CA3064177A Pending CA3064177A1 (en) 2017-06-14 2018-06-14 Synthesis of 3'-deoxyadenosine-5'-0-[phenyl(benzyloxy-l-alaninyl)]phosphate (nuc-7738)

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)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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

Also Published As

Publication number Publication date
EP3638685A1 (en) 2020-04-22
NZ800534A (en) 2026-03-27
IL271159B1 (en) 2023-06-01
BR112019026747A2 (pt) 2020-06-30
MX2019014914A (es) 2020-02-13
US20220402962A1 (en) 2022-12-22
SA519410795B1 (ar) 2023-11-19
KR20200016864A (ko) 2020-02-17
CN110785425A (zh) 2020-02-11
JP2020523381A (ja) 2020-08-06
MX2022003822A (es) 2022-05-25
US20200181186A1 (en) 2020-06-11
IL271159B2 (en) 2023-10-01
JP2023095954A (ja) 2023-07-06
IL302559B2 (en) 2024-09-01
NZ759692A (en) 2026-03-27
KR102920287B1 (ko) 2026-01-30
US20250171487A1 (en) 2025-05-29
IL271159A (en) 2020-01-30
IL312228B1 (en) 2025-02-01
MX2019014907A (es) 2020-02-13
JP7248209B2 (ja) 2023-03-29
CA3064177A1 (en) 2018-12-20
AU2018284131A1 (en) 2020-01-16
SG11201911543UA (en) 2020-01-30
JP7525687B2 (ja) 2024-07-30
CN110753697B (zh) 2023-10-13
GB201709471D0 (en) 2017-07-26
WO2018229495A1 (en) 2018-12-20
CN117486959A (zh) 2024-02-02
WO2018229493A3 (en) 2019-02-07
JP7279991B2 (ja) 2023-05-23
WO2018229493A2 (en) 2018-12-20
AU2022204691A1 (en) 2022-08-04
AU2018284131B2 (en) 2022-04-07
IL312228B2 (en) 2025-06-01
EP3638684A2 (en) 2020-04-22
JP2026034703A (ja) 2026-02-27
CN110753697A (zh) 2020-02-04
MX390901B (es) 2025-03-21
US11414452B2 (en) 2022-08-16
IL302559B1 (en) 2024-05-01
US12054511B2 (en) 2024-08-06
MX391332B (es) 2025-03-21
IL302559A (en) 2023-07-01
US20200181190A1 (en) 2020-06-11
CN110785425B (zh) 2023-11-21
PH12019502825A1 (en) 2020-10-26
EA201992873A1 (ru) 2020-05-19
AU2024200428B2 (en) 2025-10-16
JP2020523378A (ja) 2020-08-06
KR20240127483A (ko) 2024-08-22
JP2024138523A (ja) 2024-10-08
MA49379A (fr) 2020-04-22
KR102695300B1 (ko) 2024-08-16
AU2024200428A1 (en) 2024-02-08
CL2019003632A1 (es) 2020-08-14
AU2022204691B2 (en) 2023-11-23
IL312228A (en) 2024-06-01
US11897913B2 (en) 2024-02-13

Similar Documents

Publication Publication Date Title
AU2022204691B2 (en) Synthesis of substantially diastereomerically pure phosphate protides
AU2016367237B2 (en) Diastereoselective synthesis of phosphate derivatives and of the gemcitabine prodrug NUC-1031
EP3684780B1 (en) Floxuridine synthesis
AU2024200428C1 (en) Synthesis of substantially diastereomerically pure phosphate protides
EA050738B1 (ru) Получение фосфатных производных
EA043691B1 (ru) Получение фосфатных производных
EA047265B1 (ru) Получение фосфатных производных

Legal Events

Date Code Title Description
EEER Examination request

Effective date: 20230613

D15 Examination report completed

Free format text: ST27 STATUS EVENT CODE: A-2-2-D10-D15-D126 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: EXAMINER'S REPORT

Effective date: 20240722

B12 Application deemed to be withdrawn, abandoned or lapsed

Free format text: ST27 STATUS EVENT CODE: N-6-6-B10-B12-B303 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: DEEMED ABANDONED - FAILURE TO RESPOND TO AN EXAMINER'S REQUISITION

Effective date: 20241122

W00 Other event occurred

Free format text: ST27 STATUS EVENT CODE: A-2-2-W10-W00-W100 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: LETTER SENT

Effective date: 20251209

U13 Renewal or maintenance fee not paid

Free format text: ST27 STATUS EVENT CODE: N-2-6-U10-U13-U300 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: DEEMED ABANDONED - FAILURE TO RESPOND TO MAINTENANCE FEE NOTICE

Effective date: 20260209