CA3097003A1 - 4'-thio-nucleotide and -nucleoside prodrugs for the treatment of cancer - Google Patents

4'-thio-nucleotide and -nucleoside prodrugs for the treatment of cancer Download PDF

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Publication number
CA3097003A1
CA3097003A1 CA3097003A CA3097003A CA3097003A1 CA 3097003 A1 CA3097003 A1 CA 3097003A1 CA 3097003 A CA3097003 A CA 3097003A CA 3097003 A CA3097003 A CA 3097003A CA 3097003 A1 CA3097003 A1 CA 3097003A1
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CA
Canada
Prior art keywords
alkyl
compound
present
further aspect
cancer
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
CA3097003A
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English (en)
French (fr)
Inventor
Omar MOUKHA-CHAFIQ
Corinne E. Augelli-Szafran
Mark J. Suto
Doo Young Jung
Hyunyong Cho
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Southern Research Institute
Original Assignee
Pinotbio Inc
Southern Research Institute
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 Pinotbio Inc, Southern Research Institute filed Critical Pinotbio Inc
Publication of CA3097003A1 publication Critical patent/CA3097003A1/en
Pending legal-status Critical Current

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    • 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
    • C07H19/12—Triazine radicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • 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
    • 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
    • C07H19/073—Pyrimidine radicals with 2-deoxyribosyl as the saccharide radical
    • 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
    • C07H19/06—Pyrimidine radicals
    • C07H19/10—Pyrimidine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
    • C07H19/11—Pyrimidine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids containing cyclic phosphate
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H21/00—Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids
    • C07H21/02—Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids with ribosyl as saccharide radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H21/00—Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids
    • C07H21/04—Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids with deoxyribosyl as saccharide radical

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
CA3097003A 2018-04-19 2019-04-18 4'-thio-nucleotide and -nucleoside prodrugs for the treatment of cancer Pending CA3097003A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201862660208P 2018-04-19 2018-04-19
US62/660,208 2018-04-19
PCT/US2019/028168 WO2019204637A1 (en) 2018-04-19 2019-04-18 4'-thio-nucleotide and -nucleoside prodrugs for the treatment of cancer

Publications (1)

Publication Number Publication Date
CA3097003A1 true CA3097003A1 (en) 2019-10-24

Family

ID=68239059

Family Applications (1)

Application Number Title Priority Date Filing Date
CA3097003A Pending CA3097003A1 (en) 2018-04-19 2019-04-18 4'-thio-nucleotide and -nucleoside prodrugs for the treatment of cancer

Country Status (8)

Country Link
US (1) US20210363170A1 (enExample)
EP (2) EP4209498A1 (enExample)
JP (1) JP7419259B2 (enExample)
KR (1) KR102810546B1 (enExample)
CN (1) CN112513061B (enExample)
AU (2) AU2019256465B2 (enExample)
CA (1) CA3097003A1 (enExample)
WO (1) WO2019204637A1 (enExample)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11447472B2 (en) 2020-07-23 2022-09-20 Pinotbio, Inc. Polymorophs of 5-aza-4′-thio-2′-deoxycytidine

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113993521A (zh) 2019-06-05 2022-01-28 南方研究院 基于噻拉滨和噻拉滨前药的治疗
AU2021260964A1 (en) 2020-04-23 2022-12-01 Pinotbio, Inc. Composition for treating blood cancer using 4'-thio-5-aza-2'-deoxycytidine and uses thereof
CN111393314A (zh) * 2020-04-30 2020-07-10 安徽红杉生物医药科技有限公司 2-烷基-2-氨基丙酸酯盐酸盐的制备方法
WO2022031150A1 (ko) * 2020-08-07 2022-02-10 주식회사 피노바이오 데옥시사이티딘계 항암제 및 실릴 에테르 함유 링커를 포함하는 접합체 및 이의 용도
CN114685558A (zh) * 2020-12-28 2022-07-01 尚科生物医药（上海）有限公司 一种瑞德西韦中间体的制备方法
KR102891437B1 (ko) * 2021-08-02 2025-11-26 주식회사 피노바이오 잘 설계된 다중 표적 억제제로 선정된 4'-티오-5-아자-2'-디옥시사이티딘의 의약 용도

Family Cites Families (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6020322A (en) * 1993-11-09 2000-02-01 Pro-Neuron, Inc. Acyl deoxyribonucleoside derivatives and uses thereof
US5591722A (en) * 1989-09-15 1997-01-07 Southern Research Institute 2'-deoxy-4'-thioribonucleosides and their antiviral activity
NZ509405A (en) * 1998-07-23 2004-10-29 Southern Res Inst Preparation of 1-(4-thio-thioarabinofuranosyl) cytosine derivatives and their use as anticancer agents and DNA replication inhibitors
IL144032A0 (en) 1999-01-13 2002-04-21 Genentech Inc Serine protease inhibitors
US20060127990A1 (en) * 2002-08-22 2006-06-15 Geneticlab Co., Ltd 4'-thionucleotide
MX2010003261A (es) * 2007-09-26 2010-08-18 Sinai School Medicine Analogos de azacitidina y usos de los mismos.
US20110218170A1 (en) * 2010-03-02 2011-09-08 Southern Research Institute Use of 2'-deoxy-4'-thiocytidine and its analogues as dna hypomethylating anticancer agents
US9156874B2 (en) * 2011-01-03 2015-10-13 Nanjing Molecular Research, Inc. Double-liver-targeting phosphoramidate and phosphonoamidate prodrugs
HRP20190572T1 (hr) * 2012-08-13 2019-05-17 Fujifilm Corporation POSREDNIK ZA SINTEZU 1-(2-DEOKSI-2 FLUORO-4-TIO-beta-D-ARABINOFURANOZIL) CITOZINA, POSREDNIK ZA SINTEZU TIONUKLEOZIDA, I METODE ZA PROIZVODNJU OVIH POSREDNIKA
TWI678373B (zh) 2014-10-31 2019-12-01 日商富士軟片股份有限公司 硫代核苷衍生物或其鹽及醫藥組合物
CN106661077B (zh) 2015-04-03 2019-02-12 四川科伦博泰生物医药股份有限公司 4’-硫代核苷的新型化合物及其制备方法、药物组合物和应用
US20160312261A1 (en) * 2015-04-24 2016-10-27 Plasmia Biotech, S.L. Enzymatic production of cytosinic nucleoside analogues
EP3303361A1 (en) * 2015-05-27 2018-04-11 Idenix Pharmaceuticals LLC Nucleotides for the treatment of cancer
JP7425734B2 (ja) 2018-02-01 2024-01-31 ザ ユナイテッド ステイツ オブ アメリカ， アズ リプレゼンテッド バイ ザ セクレタリー， デパートメント オブ ヘルス アンド ヒューマン サービシーズ ２’－デオキシヌクレオシドを製造するための立体選択的合成およびプロセス
AU2021260964A1 (en) * 2020-04-23 2022-12-01 Pinotbio, Inc. Composition for treating blood cancer using 4'-thio-5-aza-2'-deoxycytidine and uses thereof

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11447472B2 (en) 2020-07-23 2022-09-20 Pinotbio, Inc. Polymorophs of 5-aza-4′-thio-2′-deoxycytidine

Also Published As

Publication number Publication date
CN112513061A (zh) 2021-03-16
AU2024278376A1 (en) 2025-01-09
AU2019256465B2 (en) 2024-10-03
JP7419259B2 (ja) 2024-01-22
KR20210005638A (ko) 2021-01-14
CN112513061B (zh) 2025-01-24
KR102810546B1 (ko) 2025-05-20
WO2019204637A1 (en) 2019-10-24
EP3781584A1 (en) 2021-02-24
AU2019256465A1 (en) 2020-11-26
US20210363170A1 (en) 2021-11-25
EP4209498A1 (en) 2023-07-12
JP2021522197A (ja) 2021-08-30
EP3781584A4 (en) 2022-05-11

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