CA2656780C - Anti-viral pyrimidine nucleoside derivatives - Google Patents

Anti-viral pyrimidine nucleoside derivatives Download PDF

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Publication number
CA2656780C
CA2656780C CA 2656780 CA2656780A CA2656780C CA 2656780 C CA2656780 C CA 2656780C CA 2656780 CA2656780 CA 2656780 CA 2656780 A CA2656780 A CA 2656780A CA 2656780 C CA2656780 C CA 2656780C
Authority
CA
Canada
Prior art keywords
compound
valine
alkyl
treatment
amino acid
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 - Fee Related
Application number
CA 2656780
Other languages
English (en)
French (fr)
Other versions
CA2656780A1 (en
Inventor
Christopher Mcguigan
Jan Balzarini
Marco Migliore
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.)
Katholieke Universiteit Leuven
University College Cardiff Consultants Ltd
Original Assignee
Katholieke Universiteit Leuven
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 Katholieke Universiteit Leuven, University College Cardiff Consultants Ltd filed Critical Katholieke Universiteit Leuven
Publication of CA2656780A1 publication Critical patent/CA2656780A1/en
Application granted granted Critical
Publication of CA2656780C publication Critical patent/CA2656780C/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/70Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7042Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7052Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
    • A61K31/706Compounds 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
    • A61K31/7064Compounds 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
    • A61K31/7068Compounds 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/70Carbohydrates; Sugars; Derivatives thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12Antivirals
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D487/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02Heterocyclic 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
    • C07D487/04Ortho-condensed systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D491/00Heterocyclic 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
    • C07D491/02Heterocyclic 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
    • C07D491/04Ortho-condensed systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D495/00Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04Ortho-condensed systems
    • 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/70Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7042Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7052Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/70Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7042Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7052Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
    • A61K31/706Compounds 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/70Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7042Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7052Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
    • A61K31/706Compounds 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
    • A61K31/7064Compounds 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Molecular Biology (AREA)
  • Epidemiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Virology (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
CA 2656780 2006-05-09 2007-05-09 Anti-viral pyrimidine nucleoside derivatives Expired - Fee Related CA2656780C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GBGB0609178.9A GB0609178D0 (en) 2006-05-09 2006-05-09 Novel compounds
GB0609178.9 2006-05-09
PCT/GB2007/001677 WO2007129083A1 (en) 2006-05-09 2007-05-09 Anti-viral pyrimidine nucleoside derivatives

Publications (2)

Publication Number Publication Date
CA2656780A1 CA2656780A1 (en) 2007-11-15
CA2656780C true CA2656780C (en) 2015-04-28

Family

ID=36637171

Family Applications (1)

Application Number Title Priority Date Filing Date
CA 2656780 Expired - Fee Related CA2656780C (en) 2006-05-09 2007-05-09 Anti-viral pyrimidine nucleoside derivatives

Country Status (22)

Country Link
US (3) US8329664B2 (enExample)
EP (1) EP2016081B1 (enExample)
JP (1) JP5261374B2 (enExample)
KR (1) KR101447522B1 (enExample)
CN (1) CN101443332B (enExample)
AT (1) ATE506367T1 (enExample)
AU (1) AU2007246814B2 (enExample)
BR (1) BRPI0711354A2 (enExample)
CA (1) CA2656780C (enExample)
CY (1) CY1111711T1 (enExample)
DE (1) DE602007014030D1 (enExample)
DK (1) DK2016081T3 (enExample)
EA (1) EA015178B1 (enExample)
ES (1) ES2365057T3 (enExample)
GB (1) GB0609178D0 (enExample)
IL (1) IL194806A (enExample)
NZ (1) NZ573377A (enExample)
PL (1) PL2016081T3 (enExample)
PT (1) PT2016081E (enExample)
SI (1) SI2016081T1 (enExample)
TW (1) TWI385172B (enExample)
WO (1) WO2007129083A1 (enExample)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB0009486D0 (en) * 2000-04-17 2000-06-07 Univ Cardiff Chemical compounds
GB2452556A (en) * 2007-09-07 2009-03-11 Univ Leuven Kath Nucleoside analogues esterified at 3 and/or 5 positions by neutral non-polar amino acid, or oligopeptide thereof, for combating Varicella Zoster virus
US9260469B2 (en) * 2010-10-09 2016-02-16 Contravir Pharmaceuticals, Inc. Method of preparation of antiviral compounds and useful intermediates thereof
CN105037468A (zh) * 2010-10-09 2015-11-11 英希比泰克斯公司 制备抗病毒组合物的方法及其中间体的应用
MD4110C1 (ro) * 2010-10-21 2011-12-31 Валериу РУДИК Preparat antiherpetiс
KR101875997B1 (ko) * 2015-05-04 2018-07-06 엔 앤드 엔 파마세우티칼스 인크. 엔-메탄노카르바티미딘을 이용한 대상포진의 치료방법

Family Cites Families (18)

* 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
EP0346108A3 (en) 1988-06-09 1991-04-24 The Wellcome Foundation Limited Anti-infective nucleosides
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
GB9505025D0 (en) 1995-03-13 1995-05-03 Medical Res Council Chemical compounds
US6022876A (en) * 1996-11-15 2000-02-08 Yale University L-β-dioxolane uridine analogs and methods for treating and preventing Epstein-Barr virus infections
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
MXPA02000763A (es) 1999-07-22 2002-08-12 Newbiotics Inc Activacion terapeutica catalizada por enzima.
MXPA02000761A (es) 1999-07-22 2002-08-12 Newbiotics Inc Agentes terapeuticos anti-infecciosos catalizados por enzima.
CN1391486A (zh) 1999-07-22 2003-01-15 新生物公司 治疗对治疗有抗性的肿瘤的方法
GB0009486D0 (en) * 2000-04-17 2000-06-07 Univ Cardiff Chemical compounds
GB0011203D0 (en) * 2000-05-09 2000-06-28 Univ Cardiff Chemical compounds
MY141594A (en) * 2000-06-15 2010-05-14 Novirio Pharmaceuticals Ltd 3'-PRODRUGS OF 2'-DEOXY-ß-L-NUCLEOSIDES
US6875751B2 (en) 2000-06-15 2005-04-05 Idenix Pharmaceuticals, Inc. 3′-prodrugs of 2′-deoxy-β-L-nucleosides
CA2490191C (en) 2002-06-28 2010-08-03 Idenix (Cayman) Limited Modified 2' and 3' -nucleoside prodrugs for treating flaviviridae infections
EP1745573A4 (en) * 2003-03-20 2010-05-26 Microbiol Quimica Farmaceutica PROCESS FOR PREPARING 2-DEOXY-BETA-L-NUCLEOSIDES
US20050137141A1 (en) 2003-10-24 2005-06-23 John Hilfinger Prodrug composition
JP4856638B2 (ja) 2004-06-07 2012-01-18 アナディス・ファーマシューティカルズ・インコーポレイテッド 3−β−D−リボフラノシルチアゾロ[4,5−d]ピリミジンヌクレオシドおよびその使用

Also Published As

Publication number Publication date
EA200870505A1 (ru) 2009-04-28
IL194806A (en) 2015-08-31
CA2656780A1 (en) 2007-11-15
US20150072948A1 (en) 2015-03-12
SI2016081T1 (sl) 2011-09-30
DK2016081T3 (da) 2011-06-20
JP2009536188A (ja) 2009-10-08
US8859512B2 (en) 2014-10-14
EA015178B1 (ru) 2011-06-30
US20130096079A1 (en) 2013-04-18
DE602007014030D1 (de) 2011-06-01
IL194806A0 (en) 2009-09-22
PT2016081E (pt) 2011-06-28
CN101443332B (zh) 2011-11-09
KR20090042204A (ko) 2009-04-29
BRPI0711354A2 (pt) 2011-09-27
EP2016081A1 (en) 2009-01-21
PL2016081T3 (pl) 2011-12-30
US8329664B2 (en) 2012-12-11
TW200813066A (en) 2008-03-16
US20100222295A1 (en) 2010-09-02
NZ573377A (en) 2011-03-31
AU2007246814B2 (en) 2012-07-19
CY1111711T1 (el) 2015-10-07
JP5261374B2 (ja) 2013-08-14
ATE506367T1 (de) 2011-05-15
WO2007129083A1 (en) 2007-11-15
CN101443332A (zh) 2009-05-27
GB0609178D0 (en) 2006-06-21
US9427447B2 (en) 2016-08-30
EP2016081B1 (en) 2011-04-20
ES2365057T3 (es) 2011-09-21
AU2007246814A1 (en) 2007-11-15
TWI385172B (zh) 2013-02-11
KR101447522B1 (ko) 2014-10-06

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Effective date: 20190509