CA2885719C - Oligonucleotide and artificial nucleoside having guanidine bridge - Google Patents

Oligonucleotide and artificial nucleoside having guanidine bridge Download PDF

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Publication number
CA2885719C
CA2885719C CA2885719A CA2885719A CA2885719C CA 2885719 C CA2885719 C CA 2885719C CA 2885719 A CA2885719 A CA 2885719A CA 2885719 A CA2885719 A CA 2885719A CA 2885719 C CA2885719 C CA 2885719C
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Prior art keywords
group
amino
compound
nucleic acid
dihydropyrimidine
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CA2885719A
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English (en)
French (fr)
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CA2885719A1 (en
Inventor
Satoshi Obika
Yutaro KOTOBUKI
Reiko WAKI
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University of Osaka NUC
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Osaka University NUC
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/06Pyrimidine radicals
    • C07H19/10Pyrimidine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/06Pyrimidine radicals
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/16Purine radicals
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H21/00Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H21/00Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids
    • C07H21/02Compounds 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H21/00Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids
    • C07H21/04Compounds 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H23/00Compounds containing boron, silicon or a metal, e.g. chelates or vitamin B12
    • CCHEMISTRY; METALLURGY
    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12NMICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N15/00Mutation or genetic engineering; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification; Use of hosts therefor
    • YGENERAL 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
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00Technologies relating to chemical industry
    • Y02P20/50Improvements relating to the production of bulk chemicals
    • Y02P20/55Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Genetics & Genomics (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Zoology (AREA)
  • General Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Wood Science & Technology (AREA)
  • Biomedical Technology (AREA)
  • Biophysics (AREA)
  • Plant Pathology (AREA)
  • Microbiology (AREA)
  • Physics & Mathematics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
CA2885719A 2012-09-21 2013-09-19 Oligonucleotide and artificial nucleoside having guanidine bridge Active CA2885719C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
JP2012208906 2012-09-21
JP2012-208906 2012-09-21
JP2013022360 2013-02-07
JP2013-022360 2013-02-07
PCT/JP2013/075370 WO2014046212A1 (ja) 2012-09-21 2013-09-19 グアニジン架橋を有する人工ヌクレオシドおよびオリゴヌクレオチド

Publications (2)

Publication Number Publication Date
CA2885719A1 CA2885719A1 (en) 2014-03-27
CA2885719C true CA2885719C (en) 2017-07-11

Family

ID=50341516

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2885719A Active CA2885719C (en) 2012-09-21 2013-09-19 Oligonucleotide and artificial nucleoside having guanidine bridge

Country Status (9)

Country Link
US (1) US10377789B2 (enExample)
EP (1) EP2899197B1 (enExample)
JP (1) JP6048982B2 (enExample)
KR (1) KR101707437B1 (enExample)
CN (1) CN104768964B (enExample)
CA (1) CA2885719C (enExample)
ES (1) ES2622716T3 (enExample)
IN (1) IN2015DN02238A (enExample)
WO (1) WO2014046212A1 (enExample)

Families Citing this family (28)

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JP6292631B2 (ja) 2013-02-18 2018-03-14 塩野義製薬株式会社 含窒素複素環構造を有するヌクレオシド及びヌクレオチド
TW201718618A (zh) * 2015-09-18 2017-06-01 田邊三菱製藥股份有限公司 架橋型核酸GuNA,其製造方法,及中間體化合物
JP6569920B2 (ja) * 2016-01-07 2019-09-04 国立大学法人大阪大学 α−シヌクレイン発現抑制剤
JP7095893B2 (ja) 2017-02-21 2022-07-05 国立大学法人大阪大学 アンチセンスオリゴ核酸
WO2018155451A1 (ja) 2017-02-21 2018-08-30 国立大学法人大阪大学 核酸化合物およびオリゴヌクレオチド
WO2019009298A1 (ja) * 2017-07-05 2019-01-10 国立大学法人大阪大学 α-シヌクレイン発現抑制剤
WO2019045075A1 (ja) 2017-08-31 2019-03-07 田辺三菱製薬株式会社 Il-33アンタゴニストを含む子宮内膜症治療剤
CA3099778A1 (en) * 2018-05-10 2019-11-14 Nippon Shinyaku Co., Ltd. Method for preparing oligonucleic acid compound
WO2020027227A1 (ja) 2018-07-31 2020-02-06 国立大学法人大阪大学 オリゴヌクレオチドを含有する小細胞肺癌治療薬
JP7396577B2 (ja) 2018-09-05 2023-12-12 国立大学法人大阪大学 Arl4cを標的分子とするアンチセンスオリゴヌクレオチド、及び当該アンチセンスオリゴヌクレオチドを使用した核酸医薬
MX2021005537A (es) 2018-11-12 2021-09-10 Mitsubishi Tanabe Pharma Corp Ácido nucleico alna artificial reticulado.
EP3950006A4 (en) 2019-03-29 2024-06-12 Mitsubishi Tanabe Pharma Corporation Compound, method and pharmaceutical composition for dux4 expression adjustment
CN113646007B (zh) 2019-03-29 2024-08-23 希森美康株式会社 新人工核酸、其制造方法及用途
WO2020243490A2 (en) 2019-05-31 2020-12-03 Aligos Therapeutics, Inc. Modified gapmer oligonucleotides and methods of use
BR112021025497A2 (pt) * 2019-06-20 2022-02-01 Hoffmann La Roche Oligonucleotídeos, processo para a preparação de um oligonucleotídeo, uso do oligonucleotídeo, método para a determinação da biodistribuição e farmacocinética de um oligonucleotídeo no tecido ou fluido corporal
US20230227824A1 (en) 2020-05-12 2023-07-20 Mitsubishi Tanabe Pharma Corporation Compound, method and pharmaceutical composition for regulating expression of ataxin 3
EP4219517A4 (en) 2020-09-25 2024-09-25 Riken Genesis Co., Ltd. NOVEL ARTIFICIAL NUCLEIC ACID, METHOD FOR PRODUCING THE SAME AND USE THEREOF
CN116507727A (zh) 2020-11-06 2023-07-28 住友制药株式会社 Rps25基因的表达和/或功能调节剂
US20240148775A1 (en) 2021-02-25 2024-05-09 Osaka University Oligonucleotide for inducing n-exon skipping during rest mrna precursor processing
JP2024105742A (ja) * 2021-05-26 2024-08-07 ルクサナバイオテク株式会社 心疾患治療薬
AU2022279820A1 (en) 2021-05-28 2023-12-14 Sumitomo Pharma Co., Ltd. Antisense nucleic acid
CN113552198B (zh) * 2021-05-31 2024-03-26 武汉维尔博生物科技有限公司 一种基于高响应葡萄糖适配体的电化学传感器及其制备方法
EP4389893A4 (en) 2021-08-21 2025-09-10 Takeda Pharmaceuticals Co PEPTIDE-DRUG CONJUGATE BINDING HUMAN TRANSFERRIN RECEPTOR
WO2023093960A1 (en) * 2021-11-26 2023-06-01 Syddansk Universitet Modified peptide-oligonucleotide conjugate
WO2023127857A1 (ja) 2021-12-27 2023-07-06 株式会社理研ジェネシス 新規人工核酸、その製造方法及び用途
WO2023177808A1 (en) * 2022-03-17 2023-09-21 Aligos Therapeutics, Inc. Modified gapmer oligomers and methods of use thereof
CN120187739A (zh) 2022-11-10 2025-06-20 璐库萨那生物技术株式会社 桥联部具有胍基结构的修饰核苷和使用其的寡核苷酸的制造方法
US20250368996A1 (en) 2024-05-14 2025-12-04 Aligos Therapeutics, Inc. Modified antisense oligonucleotides for treating hepatitis b virus

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4458066A (en) * 1980-02-29 1984-07-03 University Patents, Inc. Process for preparing polynucleotides
US4500707A (en) * 1980-02-29 1985-02-19 University Patents, Inc. Nucleosides useful in the preparation of polynucleotides
US5132418A (en) * 1980-02-29 1992-07-21 University Patents, Inc. Process for preparing polynucleotides
US4668777A (en) * 1981-03-27 1987-05-26 University Patents, Inc. Phosphoramidite nucleoside compounds
US4973679A (en) * 1981-03-27 1990-11-27 University Patents, Inc. Process for oligonucleo tide synthesis using phosphormidite intermediates
US5696253A (en) * 1994-06-30 1997-12-09 The Regents Of The University Of California Polynucleoside chain with 3'→5' guanidyl linkages
JP3756313B2 (ja) 1997-03-07 2006-03-15 武 今西 新規ビシクロヌクレオシド及びオリゴヌクレオチド類縁体
JP4151751B2 (ja) * 1999-07-22 2008-09-17 第一三共株式会社 新規ビシクロヌクレオシド類縁体
EP2354148B1 (en) 2002-02-13 2013-09-04 Takeshi Imanishi Nucleoside analogues and oligonucleotide derivative comprising nucleotide analogue thereof
JP4731324B2 (ja) 2003-08-28 2011-07-20 武 今西 N−o結合性架橋構造型新規人工核酸
WO2007026824A1 (ja) * 2005-08-31 2007-03-08 Osaka University オリゴヌクレオチド類縁体
US8541562B2 (en) 2009-10-29 2013-09-24 Osaka University Bridged artificial nucleoside and nucleotide
US9206216B2 (en) * 2010-04-21 2015-12-08 Pierce Biotechnology, Inc. Modified nucleotides methods and kits
US8536323B2 (en) * 2010-04-21 2013-09-17 Pierce Biotechnology, Inc. Modified nucleotides

Also Published As

Publication number Publication date
KR101707437B1 (ko) 2017-02-16
US10377789B2 (en) 2019-08-13
EP2899197B1 (en) 2017-03-22
CN104768964A (zh) 2015-07-08
JP6048982B2 (ja) 2016-12-21
CN104768964B (zh) 2017-03-29
KR20150056647A (ko) 2015-05-26
US20150266917A1 (en) 2015-09-24
ES2622716T3 (es) 2017-07-07
IN2015DN02238A (enExample) 2015-08-21
CA2885719A1 (en) 2014-03-27
EP2899197A4 (en) 2016-03-09
JPWO2014046212A1 (ja) 2016-08-18
EP2899197A1 (en) 2015-07-29
WO2014046212A1 (ja) 2014-03-27

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