CA2870722C - Compositions and methods for inhibiting viral polymerase - Google Patents

Compositions and methods for inhibiting viral polymerase Download PDF

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Publication number
CA2870722C
CA2870722C CA2870722A CA2870722A CA2870722C CA 2870722 C CA2870722 C CA 2870722C CA 2870722 A CA2870722 A CA 2870722A CA 2870722 A CA2870722 A CA 2870722A CA 2870722 C CA2870722 C CA 2870722C
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virus
compound
tert
amino
group
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CA2870722A1 (en
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Pravin L. Kotian
Yarlagadda S. Babu
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Biocryst Pharmaceuticals Inc
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    • 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
    • A61K31/13—Amines
    • A61K31/14—Quaternary ammonium compounds, e.g. edrophonium, choline
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/10—Dispersions; Emulsions
    • A61K9/12—Aerosols; Foams
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/20—Pills, tablets, discs, rods
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • 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
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • 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
    • A61P31/14—Antivirals for RNA viruses
    • A61P31/16—Antivirals for RNA viruses for influenza or rhinoviruses
    • 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
    • A61P31/20—Antivirals for DNA viruses
    • 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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/056—Ortho-condensed systems with two or more oxygen atoms as ring hetero atoms in the oxygen-containing ring
    • 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
    • C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
    • C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
    • 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
    • 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
    • C07H19/213—Purine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids containing cyclic phosphate
    • 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
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

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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)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Virology (AREA)
  • Molecular Biology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Engineering & Computer Science (AREA)
  • Biotechnology (AREA)
  • Biochemistry (AREA)
  • Dispersion Chemistry (AREA)
  • Genetics & Genomics (AREA)
  • Nutrition Science (AREA)
  • Physiology (AREA)
  • Dermatology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pulmonology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
CA2870722A 2012-04-18 2013-04-17 Compositions and methods for inhibiting viral polymerase Active CA2870722C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201261625994P 2012-04-18 2012-04-18
US61/625,994 2012-04-18
PCT/US2013/036945 WO2013158746A1 (en) 2012-04-18 2013-04-17 Compositions and methods for inhibiting viral polymerase

Publications (2)

Publication Number Publication Date
CA2870722A1 CA2870722A1 (en) 2013-10-24
CA2870722C true CA2870722C (en) 2020-05-12

Family

ID=49384030

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2870722A Active CA2870722C (en) 2012-04-18 2013-04-17 Compositions and methods for inhibiting viral polymerase

Country Status (14)

Country Link
US (2) US9580428B2 (OSRAM)
EP (1) EP2838535B1 (OSRAM)
JP (2) JP2015514772A (OSRAM)
KR (3) KR102156819B1 (OSRAM)
CN (1) CN104379146B (OSRAM)
AR (1) AR090699A1 (OSRAM)
AU (1) AU2013249344B2 (OSRAM)
BR (1) BR112014025909B1 (OSRAM)
CA (1) CA2870722C (OSRAM)
IL (1) IL235123A (OSRAM)
MX (1) MX363270B (OSRAM)
RU (1) RU2654482C2 (OSRAM)
TW (1) TWI664180B (OSRAM)
WO (1) WO2013158746A1 (OSRAM)

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WO2014078778A2 (en) * 2012-11-16 2014-05-22 Biocryst Pharmaceuticals, Inc. Antiviral azasugar-containing nucleosides
CN103864791B (zh) * 2014-03-18 2016-01-27 福建天泉药业股份有限公司 一种恩替卡韦衍生物及其制备方法
CN104513249B (zh) * 2014-12-26 2016-08-31 苏州明锐医药科技有限公司 抗埃博拉病毒药物bcx4430的制备方法
CA2973152A1 (en) * 2015-01-07 2016-07-14 Euro-Celtique S.A. Process for manufacture of forodesine
TWI874791B (zh) * 2020-02-18 2025-03-01 美商基利科學股份有限公司 抗病毒化合物
WO2021207386A1 (en) * 2020-04-07 2021-10-14 Biocryst Pharmaceuticals, Inc. Methods, compositions, and dosing regimens for treatment of sars-cov-2 infections
US20230285434A1 (en) * 2020-04-14 2023-09-14 Oyagen, Inc. Method for treating arenaviridae infections
CN111704619B (zh) * 2020-07-30 2021-10-19 四川大学 一种Forodesine的制备方法
US12274700B1 (en) 2020-10-30 2025-04-15 Accencio LLC Methods of treating symptoms of coronavirus infection with RNA polymerase inhibitors
CA3098164A1 (en) * 2020-11-05 2022-05-05 Eurofins Cdmo Alphora Inc. Process for preparation of advanced intermediate for eribulin synthesys
WO2023022216A1 (ja) 2021-08-20 2023-02-23 塩野義製薬株式会社 ウイルス増殖抑制作用を有するヌクレオシド誘導体及びそれらのプロドラッグ
CN113666941B (zh) * 2021-09-01 2023-03-10 浙江珲达生物科技有限公司 一种2,3-O-异亚丙基-D-核糖酸-γ-内酯的重结晶方法
US12552827B2 (en) 2022-01-21 2026-02-17 Biocryst Pharmaceuticals, Inc. Synthesis of an antiviral azasugar triphosphate
CN116693541A (zh) * 2023-06-15 2023-09-05 安徽大学 一种4-氯-5h-吡咯并[3,2-d]嘧啶的合成方法
CN118359621B (zh) * 2024-04-16 2025-05-16 上海陶术生物科技股份有限公司 加利司伟及加利司伟中间体的制备方法和相应的加利司伟中间体
CN118359623B (zh) * 2024-04-16 2025-06-27 上海陶术生物科技股份有限公司 一种呋咯地辛的合成方法、中间体及应用
CN118359622B (zh) * 2024-04-16 2025-08-26 上海陶术生物科技股份有限公司 加利司伟中间体的制备方法

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Also Published As

Publication number Publication date
AU2013249344A1 (en) 2014-11-27
KR102156819B1 (ko) 2020-09-16
MX363270B (es) 2019-03-19
EP2838535A1 (en) 2015-02-25
IL235123A (en) 2017-09-28
MX2014012525A (es) 2015-01-15
RU2014145857A (ru) 2016-06-10
TW201345912A (zh) 2013-11-16
HK1206627A1 (en) 2016-01-15
CA2870722A1 (en) 2013-10-24
JP2018111692A (ja) 2018-07-19
EP2838535B1 (en) 2019-03-06
BR112014025909B1 (pt) 2021-09-14
US9580428B2 (en) 2017-02-28
KR20200070428A (ko) 2020-06-17
AU2013249344B2 (en) 2018-06-07
KR20150002844A (ko) 2015-01-07
US20170128454A1 (en) 2017-05-11
RU2654482C2 (ru) 2018-05-21
EP2838535A4 (en) 2015-09-09
AR090699A1 (es) 2014-12-03
KR20210011517A (ko) 2021-02-01
KR102409853B1 (ko) 2022-06-15
JP2015514772A (ja) 2015-05-21
BR112014025909A2 (OSRAM) 2017-06-20
US20150191472A1 (en) 2015-07-09
CN104379146B (zh) 2018-07-10
TWI664180B (zh) 2019-07-01
CN104379146A (zh) 2015-02-25
JP6559266B2 (ja) 2019-08-14
WO2013158746A1 (en) 2013-10-24

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