CA2288147C - Anti-viral pyrimidine nucleoside analogues - Google Patents

Anti-viral pyrimidine nucleoside analogues Download PDF

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Publication number
CA2288147C
CA2288147C CA002288147A CA2288147A CA2288147C CA 2288147 C CA2288147 C CA 2288147C CA 002288147 A CA002288147 A CA 002288147A CA 2288147 A CA2288147 A CA 2288147A CA 2288147 C CA2288147 C CA 2288147C
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CA
Canada
Prior art keywords
group
alkyl
halogens
compound according
aryl
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.)
Expired - Lifetime
Application number
CA002288147A
Other languages
English (en)
French (fr)
Other versions
CA2288147A1 (en
Inventor
Christopher Mcguigan
Christopher Yarnold
Garry Jones
Jan Balzarini
Erik De Clercq
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.)
Rega Foundation
University College Cardiff Consultants Ltd
Original Assignee
Rega Foundation
University College Cardiff Consultants Ltd
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 Rega Foundation, University College Cardiff Consultants Ltd filed Critical Rega Foundation
Publication of CA2288147A1 publication Critical patent/CA2288147A1/en
Application granted granted Critical
Publication of CA2288147C publication Critical patent/CA2288147C/en
Anticipated expiration legal-status Critical
Expired - Lifetime 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
    • C07H19/06—Pyrimidine radicals
    • 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
    • A61P31/20—Antivirals for DNA viruses
    • A61P31/22—Antivirals for DNA viruses for herpes viruses
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biotechnology (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Genetics & Genomics (AREA)
  • Virology (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
CA002288147A 1997-04-28 1998-04-27 Anti-viral pyrimidine nucleoside analogues Expired - Lifetime CA2288147C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GBGB9708611.0A GB9708611D0 (en) 1997-04-28 1997-04-28 Chemical compounds
GB9708611.0 1997-04-28
PCT/GB1998/001222 WO1998049177A1 (en) 1997-04-28 1998-04-27 Anti-viral pyrimidine nucleoside analogues

Publications (2)

Publication Number Publication Date
CA2288147A1 CA2288147A1 (en) 1998-11-05
CA2288147C true CA2288147C (en) 2008-03-11

Family

ID=10811493

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002288147A Expired - Lifetime CA2288147C (en) 1997-04-28 1998-04-27 Anti-viral pyrimidine nucleoside analogues

Country Status (13)

Country Link
US (1) US6573247B1 (https=)
EP (1) EP0980377B1 (https=)
JP (1) JP4514242B2 (https=)
AT (1) ATE221543T1 (https=)
AU (1) AU737902B2 (https=)
CA (1) CA2288147C (https=)
DE (1) DE69806919T2 (https=)
DK (1) DK0980377T3 (https=)
ES (1) ES2181208T3 (https=)
GB (1) GB9708611D0 (https=)
NZ (1) NZ500881A (https=)
PT (1) PT980377E (https=)
WO (1) WO1998049177A1 (https=)

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GB9708611D0 (en) * 1997-04-28 1997-06-18 Univ Cardiff Chemical compounds
GB9716231D0 (en) 1997-07-31 1997-10-08 Amersham Int Ltd Base analogues
ATE413881T1 (de) 1997-08-08 2008-11-15 Celmed Oncology Usa Inc Verfahren und zubereitungen um resistenz gegen biologische oder chemische therapien zu überwinden
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
AU774492B2 (en) 1999-07-22 2004-07-01 Celmed Oncology (Usa) Inc. Methods for treating therapy-resistant tumors
US6683061B1 (en) 1999-07-22 2004-01-27 Newbiotics, Inc. Enzyme catalyzed therapeutic activation
GB0009486D0 (en) * 2000-04-17 2000-06-07 Univ Cardiff Chemical compounds
GB0011203D0 (en) * 2000-05-09 2000-06-28 Univ Cardiff Chemical compounds
AU2003225701A1 (en) * 2002-03-08 2003-09-22 Glen Research Corporation Fluorescent nitrogenous base and nucleosides incorporating same
HUE033832T2 (en) 2002-11-15 2018-01-29 Idenix Pharmaceuticals Llc 2'-methyl nucleosides in combination with interferon and Flaviviridae mutation
GB0609178D0 (en) 2006-05-09 2006-06-21 Univ Cardiff Novel compounds
US20080261913A1 (en) 2006-12-28 2008-10-23 Idenix Pharmaceuticals, Inc. Compounds and pharmaceutical compositions for the treatment of liver disorders
EA201270566A1 (ru) * 2009-10-16 2012-11-30 Риб-Экс Фармасьютикалз, Инк. Противомикробные соединения и способы их получения и применения
NZ599290A (en) 2009-10-16 2014-10-31 Melinta Therapeutics Inc Antimicrobial compounds and methods of making and using the same
MX2012004341A (es) 2009-10-16 2012-10-05 Rib X Pharmaceuticals Inc Compuestos antimicrobianos y metodos para fabricar y utilizar los mismos.
GB201016855D0 (en) * 2010-10-06 2010-11-17 Nucana Biomed Ltd Chemical compounds
EP2691409B1 (en) 2011-03-31 2018-02-21 Idenix Pharmaceuticals LLC. Compounds and pharmaceutical compositions for the treatment of viral infections
MY173518A (en) 2011-04-15 2020-01-30 Melinta Therapeutics Inc Antimicrobial compounds and methods of making and using the same
GB201111779D0 (en) 2011-07-08 2011-08-24 Univ Cardiff Chemical compounds
TW201329096A (zh) 2011-09-12 2013-07-16 Idenix Pharmaceuticals Inc 經取代羰氧基甲基磷酸醯胺化合物及用於治療病毒感染之藥學組成物
US8507460B2 (en) 2011-10-14 2013-08-13 Idenix Pharmaceuticals, Inc. Substituted 3′,5′-cyclic phosphates of purine nucleotide compounds and pharmaceutical compositions for the treatment of viral infections
WO2013177188A1 (en) 2012-05-22 2013-11-28 Idenix Pharmaceuticals, Inc. 3',5'-cyclic phosphoramidate prodrugs for hcv infection
US9296778B2 (en) 2012-05-22 2016-03-29 Idenix Pharmaceuticals, Inc. 3′,5′-cyclic phosphate prodrugs for HCV infection
CA2873315A1 (en) 2012-05-22 2013-11-28 Idenix Pharamaceuticals, Inc. D-amino acid compounds for liver disease
SG11201407336PA (en) 2012-05-25 2015-03-30 Janssen Sciences Ireland Uc Uracyl spirooxetane nucleosides
WO2014052638A1 (en) 2012-09-27 2014-04-03 Idenix Pharmaceuticals, Inc. Esters and malonates of sate prodrugs
KR102001280B1 (ko) 2012-10-08 2019-07-17 아이데닉스 파마슈티칼스 엘엘씨 Hcv 감염에 대한 2'-클로로 뉴클레오시드 유사체
WO2014066239A1 (en) 2012-10-22 2014-05-01 Idenix Pharmaceuticals, Inc. 2',4'-bridged nucleosides for hcv infection
EP2935304A1 (en) 2012-12-19 2015-10-28 IDENIX Pharmaceuticals, Inc. 4'-fluoro nucleosides for the treatment of hcv
US9309275B2 (en) 2013-03-04 2016-04-12 Idenix Pharmaceuticals Llc 3′-deoxy nucleosides for the treatment of HCV
US9339541B2 (en) 2013-03-04 2016-05-17 Merck Sharp & Dohme Corp. Thiophosphate nucleosides for the treatment of HCV
WO2014160484A1 (en) 2013-03-13 2014-10-02 Idenix Pharmaceuticals, Inc. Amino acid phosphoramidate pronucleotides of 2'-cyano, azido and amino nucleosides for the treatment of hcv
EP2981542B1 (en) 2013-04-01 2021-09-15 Idenix Pharmaceuticals LLC 2',4'-fluoro nucleosides for the treatment of hcv
US10005779B2 (en) 2013-06-05 2018-06-26 Idenix Pharmaceuticals Llc 1′,4′-thio nucleosides for the treatment of HCV
WO2015017713A1 (en) 2013-08-01 2015-02-05 Idenix Pharmaceuticals, Inc. D-amino acid phosphoramidate pronucleotides of halogeno pyrimidine compounds for liver disease
CA2923214A1 (en) 2013-09-09 2015-03-12 Melinta Therapeutics, Inc. Antimicrobial compounds and methods of making and using the same
EP3038623A4 (en) 2013-09-09 2017-04-19 Melinta Therapeutics, Inc. Antimicrobial compounds and methods of making and using the same
WO2015161137A1 (en) 2014-04-16 2015-10-22 Idenix Pharmaceuticals, Inc. 3'-substituted methyl or alkynyl nucleosides for the treatment of hcv
HK1249758A1 (zh) 2015-03-11 2018-11-09 Melinta Therapeutics, Inc. 抗微生物化合物及其制备和使用方法
US11098047B2 (en) 2016-05-06 2021-08-24 BioVersys AG Antimicrobials and methods of making and using same
US12606863B2 (en) 2021-05-13 2026-04-21 Promega Corporation Bioluminescent detection of DNA synthesis
US20260062437A1 (en) * 2022-08-26 2026-03-05 Regents Of The University Of Minnesota Antiviral compounds

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS62255499A (ja) * 1986-04-28 1987-11-07 Teijin Ltd 螢光性ヌクレオシド又はヌクレオチド
US5047519A (en) * 1986-07-02 1991-09-10 E. I. Du Pont De Nemours And Company Alkynylamino-nucleotides
GB9109186D0 (en) * 1991-04-29 1991-06-19 Wellcome Found Preparation of thionucleosides
YU43193A (sh) * 1992-06-22 1997-01-08 Eli Lilly And Company 2'-deoksi-2',2'-difluoro(4-supstituisani)pirimidinski nukleozidi antivirusnog i antikancerogenog dejstva i međuproizvodi
JPH06192285A (ja) * 1992-12-25 1994-07-12 Yamasa Shoyu Co Ltd １−（β−Ｄ−エリスロ−ペントフラン−２−ウロシル）ピリミジン誘導体の製造法
DE4321978A1 (de) * 1993-07-01 1995-01-12 Boehringer Mannheim Gmbh Liponucleotide von Desoxynucleosiden, deren Herstellung sowie deren Verwendung als antivirale Arzneimittel
GB9505025D0 (en) * 1995-03-13 1995-05-03 Medical Res Council Chemical compounds
GB9708611D0 (en) * 1997-04-28 1997-06-18 Univ Cardiff Chemical compounds
GB9716231D0 (en) * 1997-07-31 1997-10-08 Amersham Int Ltd Base analogues
JP2003527317A (ja) * 1999-07-22 2003-09-16 ニューバイオティックス インコーポレイテッド 酵素触媒抗感染性治療剤
CN1390227A (zh) * 1999-07-22 2003-01-08 新生物生物公司 酶催化的治疗活化
AU774492B2 (en) * 1999-07-22 2004-07-01 Celmed Oncology (Usa) Inc. Methods for treating therapy-resistant tumors

Also Published As

Publication number Publication date
EP0980377A1 (en) 2000-02-23
JP4514242B2 (ja) 2010-07-28
WO1998049177A8 (en) 2000-01-13
DK0980377T3 (da) 2002-11-18
ES2181208T3 (es) 2003-02-16
GB9708611D0 (en) 1997-06-18
WO1998049177A1 (en) 1998-11-05
CA2288147A1 (en) 1998-11-05
EP0980377B1 (en) 2002-07-31
JP2001522369A (ja) 2001-11-13
ATE221543T1 (de) 2002-08-15
US6573247B1 (en) 2003-06-03
NZ500881A (en) 2001-11-30
DE69806919D1 (de) 2002-09-05
AU737902B2 (en) 2001-09-06
DE69806919T2 (de) 2003-02-27
PT980377E (pt) 2002-12-31
AU7219398A (en) 1998-11-24

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Effective date: 20180427