AU2016240117C1 - Novel compound of 4'-thionucleoside, as well as preparation method therefor, pharmaceutical composition thereof and application thereof - Google Patents

Novel compound of 4'-thionucleoside, as well as preparation method therefor, pharmaceutical composition thereof and application thereof Download PDF

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Publication number
AU2016240117C1
AU2016240117C1 AU2016240117A AU2016240117A AU2016240117C1 AU 2016240117 C1 AU2016240117 C1 AU 2016240117C1 AU 2016240117 A AU2016240117 A AU 2016240117A AU 2016240117 A AU2016240117 A AU 2016240117A AU 2016240117 C1 AU2016240117 C1 AU 2016240117C1
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AU
Australia
Prior art keywords
compound
pharmaceutical composition
group
tumor
compound according
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Ceased
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AU2016240117A
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English (en)
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AU2016240117B2 (en
AU2016240117A1 (en
Inventor
Hua Deng
Donghong Li
Shaohua Li
Wenjia LI
Gang Liu
Yan QING
Donghai SU
Jingyi Wang
Lichun WANG
Xunwei Wu
Hong Ye
Nan Yu
Hong Zeng
Mingliang ZHAO
Wei Zhong
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.)
Sichuan Kelun Biotech Biopharmaceutical Co Ltd
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Sichuan Kelun Biotech Biopharmaceutical Co Ltd
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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
    • C07H19/06—Pyrimidine radicals
    • C07H19/10—Pyrimidine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
    • 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
    • A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
    • A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
    • A61K31/7064—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines
    • A61K31/7068—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines having oxo groups directly attached to the pyrimidine ring, e.g. cytidine, cytidylic acid
    • 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
    • A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
    • A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
    • A61K31/7064—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines
    • A61K31/7076—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines containing purines, e.g. adenosine, adenylic acid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/02—Antineoplastic agents specific for leukemia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
    • C07F9/65586—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system at least one of the hetero rings does not contain nitrogen as ring hetero atom
    • 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
    • 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

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Biochemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Epidemiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oncology (AREA)
  • Hematology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Virology (AREA)
  • Communicable Diseases (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Saccharide Compounds (AREA)
AU2016240117A 2015-04-03 2016-03-28 Novel compound of 4'-thionucleoside, as well as preparation method therefor, pharmaceutical composition thereof and application thereof Ceased AU2016240117C1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CN201510157772 2015-04-03
CN201510157772.0 2015-04-03
PCT/CN2016/077519 WO2016155593A1 (zh) 2015-04-03 2016-03-28 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

Publications (3)

Publication Number Publication Date
AU2016240117A1 AU2016240117A1 (en) 2017-08-24
AU2016240117B2 AU2016240117B2 (en) 2020-08-06
AU2016240117C1 true AU2016240117C1 (en) 2020-11-26

Family

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AU2016240117A Ceased AU2016240117C1 (en) 2015-04-03 2016-03-28 Novel compound of 4'-thionucleoside, as well as preparation method therefor, pharmaceutical composition thereof and application thereof

Country Status (8)

Country Link
US (2) US10662214B2 (enExample)
EP (1) EP3279207B1 (enExample)
JP (1) JP6769000B2 (enExample)
CN (2) CN106661077B (enExample)
AU (1) AU2016240117C1 (enExample)
CA (1) CA2975990A1 (enExample)
EA (1) EA034375B1 (enExample)
WO (1) WO2016155593A1 (enExample)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101770246B1 (ko) 2012-03-28 2017-08-22 후지필름 가부시키가이샤 1-(2-디옥시-2-플루오로-4-티오-β-D-아라비노푸라노실)시토신의 염
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
RU2752172C2 (ru) 2016-08-31 2021-07-23 Фуджифилм Корпорэйшн Противоопухолевый агент, усилитель противоопухолевого действия и противоопухолевый набор
EP3560944A4 (en) * 2016-12-22 2020-08-26 Sichuan Kelun-Biotech Biopharmaceutical Co., Ltd. SOLID FORM OF 4'-THIO-2'-FLUORONUCLEOSIDE PHOSPHAMIDE COMPOUND, PROCESS FOR PREPARATION AND USE
CN110573521B (zh) * 2017-06-29 2023-04-21 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的制备方法和此制备方法中的中间体
US11266674B2 (en) * 2017-09-01 2022-03-08 Sichuan Kelun-Biotech Biopharmaceutical Co., Ltd. Pharmaceutical composition for tumor treatment or prevention, method, and use thereof
MX2018002611A (es) 2018-01-29 2019-07-30 Fujifilm Corp Agente antitumoral para cancer del tracto biliar y metodo para tratar cancer del tracto biliar.
US20210363170A1 (en) * 2018-04-19 2021-11-25 Southern Research Institute 4'-thio-nucleotide and -nucleoside prodrugs for the treatment of cancer
WO2020108343A1 (zh) * 2018-11-28 2020-06-04 四川科伦博泰生物医药股份有限公司 以4'-硫代核苷类化合物为活性成分的口服药物组合物、其制备方法及其用途
KR20220039748A (ko) * 2019-07-30 2022-03-29 주식회사 피노바이오 암 치료용 디뉴클레오티드 화합물 및 그의 의약 용도
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

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20140315850A1 (en) * 2011-07-19 2014-10-23 Nanjing Molecular Research, Inc. 2',3'-Dideoxy-2'-alpha-Fluoro-2'-beta-C-Methylnucleosides and Prodrugs Thereof
WO2014197578A1 (en) * 2013-06-05 2014-12-11 Idenix Pharmaceuticals, Inc. 1',4'-thio nucleosides for the treatment of hcv
AU2015337512A1 (en) * 2014-10-31 2017-05-18 Fujifilm Corporation Thionucleoside derivative or salt thereof, and pharmaceutical composition

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5128458A (en) 1990-04-20 1992-07-07 Southern Research Institute 2',3'-dideoxy-4'-thioribonucleosides as antiviral agents
JPH1087687A (ja) 1996-04-09 1998-04-07 Yamasa Shoyu Co Ltd ５−置換−１−（２−デオキシ−２−フルオロ−４−チオ−β−Ｄ−アラビノフラノシル）ウラシル
WO1997038001A1 (en) * 1996-04-09 1997-10-16 Yamasa Corporation 1-(2-DEOXY-2-FLUORO-4-THIO-β-D-ARABINOFURANOSYL)CYTOSINES
GB0317009D0 (en) * 2003-07-21 2003-08-27 Univ Cardiff Chemical compounds
WO2005027962A1 (en) 2003-09-18 2005-03-31 Isis Pharmaceuticals, Inc. 4’-thionucleosides and oligomeric compounds
WO2007056596A2 (en) * 2005-11-09 2007-05-18 Wayne State University Phosphoramidate derivatives of fau
GB201016855D0 (en) * 2010-10-06 2010-11-17 Nucana Biomed Ltd Chemical compounds
WO2014124430A1 (en) * 2013-02-11 2014-08-14 Emory University Nucleotide and nucleoside therapeutic compositions and uses related thereto
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

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20140315850A1 (en) * 2011-07-19 2014-10-23 Nanjing Molecular Research, Inc. 2',3'-Dideoxy-2'-alpha-Fluoro-2'-beta-C-Methylnucleosides and Prodrugs Thereof
WO2014197578A1 (en) * 2013-06-05 2014-12-11 Idenix Pharmaceuticals, Inc. 1',4'-thio nucleosides for the treatment of hcv
AU2015337512A1 (en) * 2014-10-31 2017-05-18 Fujifilm Corporation Thionucleoside derivative or salt thereof, and pharmaceutical composition

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
MAGDALENA SLUSARCZYK ET AL, Journal of Medicinal Chemistry, 2014, vol. 57, no. 4, pages 1531 - 1542 *
UGO PRADERE ET AL, "Synthesis of Nucleoside Phosphate and Phosphonate Prodrugs", CHEMICAL REVIEWS, (2014-09-24), vol. 114, no. 18, pages 9154 - 9218 *
VELANGUPARACHEL W, ET AL, "Syntheis, anti-HIV and cytostatic evaluation of 3'-deoxy-3'-fluorothymidine (FLT) pro-nucleotides", BIOROGANIC & MEDICINAL CHEMISTRY LETTERS, vol 24 (2014), pages 2240-2243 *
YOSHIMURA Y ET AL, "A novel synthesis of 2'-modified 2'-deoxy-4'-thiocytidines from D-glucose", JOURNAL OF ORGANIC CHEMISTRY,, vol. 62 (1997), no. 10, pages 3140 - 3152 *
YOSHIMURA YUICHI ET AL, "Synthesis and biological activities of 2'-deoxy-2'-fluoro-4'-thioarabinofuranosylpyrimidine and -purine nucleosides", BIOORGANIC & MEDICINAL CHEMISTRY, vol. 8 (2000), no. 7, pages 1545 - 1558 *
YUICHI YOSHIMURA ET AL, "An Alternative Synthesis of the Antineoplastic Nucleoside 4'-ThioFAC and Its Application to the Synthesis of 4'-ThioFAG and 4'-Thiocytarazid", JOC vol. 64 (1999), no. 21, pages 7912 - 7920, *

Also Published As

Publication number Publication date
US20200262860A1 (en) 2020-08-20
CN106661077B (zh) 2019-02-12
CN106661077A (zh) 2017-05-10
JP6769000B2 (ja) 2020-10-14
HK1243424A1 (en) 2018-07-13
CN109553651B (zh) 2021-08-06
EA201791535A1 (ru) 2018-01-31
WO2016155593A1 (zh) 2016-10-06
JP2018513832A (ja) 2018-05-31
AU2016240117B2 (en) 2020-08-06
EP3279207A1 (en) 2018-02-07
EP3279207B1 (en) 2024-01-24
US10662214B2 (en) 2020-05-26
EA034375B1 (ru) 2020-01-31
HK1232229A1 (zh) 2018-01-05
AU2016240117A1 (en) 2017-08-24
US20180079770A1 (en) 2018-03-22
CN109553651A (zh) 2019-04-02
CA2975990A1 (en) 2016-10-06
EP3279207A4 (en) 2018-11-14

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