CA2527805C - Pyrimidine compounds having phosphonate groups as antiviral nucleotide analogs - Google Patents

Pyrimidine compounds having phosphonate groups as antiviral nucleotide analogs Download PDF

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Publication number
CA2527805C
CA2527805C CA2527805A CA2527805A CA2527805C CA 2527805 C CA2527805 C CA 2527805C CA 2527805 A CA2527805 A CA 2527805A CA 2527805 A CA2527805 A CA 2527805A CA 2527805 C CA2527805 C CA 2527805C
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CA
Canada
Prior art keywords
compound
formula
alkyl
independently
hydroxy
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
CA2527805A
Other languages
English (en)
French (fr)
Other versions
CA2527805A1 (en
Inventor
Jan Marie Rene Balzarini
Erik Desire Alice De Clercq
Dana Hockova
Antonin Holy
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.)
KU Leuven
Institute of Organic Chemistry and Biochemistry
Original Assignee
KU Leuven
Institute of Organic Chemistry and Biochemistry
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 KU Leuven, Institute of Organic Chemistry and Biochemistry filed Critical KU Leuven
Publication of CA2527805A1 publication Critical patent/CA2527805A1/en
Application granted granted Critical
Publication of CA2527805C publication Critical patent/CA2527805C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • 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
    • C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
    • C07F9/6509—Six-membered rings
    • C07F9/6512—Six-membered rings having the nitrogen atoms in positions 1 and 3
    • 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
    • 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
    • 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
    • A61P31/18—Antivirals for RNA viruses for HIV
    • 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

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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)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Molecular Biology (AREA)
  • Virology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Oncology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Communicable Diseases (AREA)
  • Biochemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Biotechnology (AREA)
  • AIDS & HIV (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
CA2527805A 2003-06-16 2004-06-16 Pyrimidine compounds having phosphonate groups as antiviral nucleotide analogs Expired - Lifetime CA2527805C (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US47889303P 2003-06-16 2003-06-16
US60/478,893(CON) 2003-06-16
US60/478,893 2003-06-16
PCT/CZ2004/000034 WO2004111064A1 (en) 2003-06-16 2004-06-16 Pyrimidine compounds having phosphonate groups as antiviral nucleotide analogs

Publications (2)

Publication Number Publication Date
CA2527805A1 CA2527805A1 (en) 2004-12-23
CA2527805C true CA2527805C (en) 2012-08-21

Family

ID=33551859

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2527805A Expired - Lifetime CA2527805C (en) 2003-06-16 2004-06-16 Pyrimidine compounds having phosphonate groups as antiviral nucleotide analogs

Country Status (15)

Country Link
US (2) US7115592B2 (enExample)
EP (1) EP1644389B1 (enExample)
JP (2) JP5280631B2 (enExample)
KR (1) KR101102815B1 (enExample)
CN (1) CN1805966B (enExample)
AT (1) ATE496056T1 (enExample)
AU (1) AU2004247305B2 (enExample)
CA (1) CA2527805C (enExample)
DE (1) DE602004031115D1 (enExample)
DK (1) DK1644389T3 (enExample)
EA (1) EA011948B1 (enExample)
IL (1) IL172015A (enExample)
NZ (1) NZ543864A (enExample)
SI (1) SI1644389T1 (enExample)
WO (1) WO2004111064A1 (enExample)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2006272521A1 (en) * 2005-07-27 2007-02-01 Gilead Sciences, Inc. Antiviral phosphonate conjugates for inhibition of HIV
FR2908133B1 (fr) * 2006-11-08 2012-12-14 Centre Nat Rech Scient Nouveaux analogues de nucleotides comme molecules precurseurs d'antiviraux
US9950062B2 (en) 2009-09-02 2018-04-24 Glaxosmithkline Biologicals Sa Compounds and compositions as TLR activity modulators
CN102939291B (zh) * 2010-04-14 2016-09-07 加利福尼亚大学董事会 用于病毒感染治疗的具有降低的毒性的膦酸酯
CN105998039A (zh) * 2010-08-31 2016-10-12 奇默里克斯公司 膦酸酯衍生物及其合成方法
JP2013538217A (ja) 2010-09-01 2013-10-10 ノバルティス アーゲー 不溶性金属塩への免疫増強物質の吸着
WO2012079035A1 (en) 2010-12-10 2012-06-14 Sigmapharm Laboratories, Llc Highly stable compositions of orally active nucleotide analogues or orally active nucleotide analogue prodrugs
CN103533954B (zh) 2011-03-02 2015-09-09 诺华股份有限公司 含较低剂量的抗原和/或佐剂的联合疫苗
CA2857490C (en) 2011-12-22 2020-03-31 Geron Corporation Guanine analogs as telomerase substrates and telomere length affectors
CA2866406A1 (en) 2012-03-08 2013-09-12 Novartis Ag Adjuvanted formulations of booster vaccines
CN107312039B (zh) * 2012-08-30 2019-06-25 江苏豪森药业集团有限公司 一种替诺福韦前药的制备方法
CN102796138B (zh) * 2012-09-07 2014-10-22 山东大学 (2-(3-甲硫基-1,2,4-噻二嗪)乙氧基)甲基膦酸酯类衍生物及其制备与应用
KR20150130355A (ko) 2013-03-15 2015-11-23 더 리전트 오브 더 유니버시티 오브 캘리포니아 비환식 뉴클레오사이드 포스포네이트 디에스테르
MX377983B (es) 2014-09-15 2025-03-04 Univ California Análogos de nucleótidos.
EP3875462A1 (en) 2015-09-15 2021-09-08 The Regents of The University of California Nucleotide analogs
KR20250052378A (ko) 2022-07-21 2025-04-18 안티바 바이오사이언시즈, 인크. Hpv 감염 및 hpv-유도 신생물의 치료를 위한 조성물 및 투여 형태

Family Cites Families (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CS233665B1 (en) 1983-01-06 1985-03-14 Antonin Holy Processing of isomere o-phosphonylmethylderivative of anantiomere racemic vicinal diene
US4740365A (en) 1984-04-09 1988-04-26 Toyo Boseki Kabushiki Kaisha Sustained-release preparation applicable to mucous membrane in oral cavity
CS263952B1 (en) 1985-04-25 1989-05-12 Holy Antonin Remedy with antiviral effect
CS263951B1 (en) 1985-04-25 1989-05-12 Antonin Holy 9-(phosponylmethoxyalkyl)adenines and method of their preparation
JPS63501194A (ja) * 1985-10-30 1988-05-12 プラネルト・イエンス 歯の残根から冠，ブリツジ等を除去するための装置
US5141752A (en) * 1986-05-09 1992-08-25 Alza Corporation Delayed drug delivery device
CS264222B1 (en) * 1986-07-18 1989-06-13 Holy Antonin N-phosphonylmethoxyalkylderivatives of bases of pytimidine and purine and method of use them
IL84477A (en) 1986-11-18 1995-12-08 Bristol Myers Squibb Co History of Phosphonomethoxyalkylene Purinopyrimidine and Pharmaceutical Preparations Containing Them
CA2001715C (en) 1988-11-14 1999-12-28 Muzammil M. Mansuri Carbocyclic nucleosides and nucleotides
US5098443A (en) * 1989-03-23 1992-03-24 University Of Miami Method of implanting intraocular and intraorbital implantable devices for the controlled release of pharmacological agents
CA2297294C (en) 1989-05-15 2005-11-08 Institute Of Organic Chemistry And Biochemistry Of The Academy Of Sciences Of The Czech Republic Phosphonomethoxymethylpurine/pyrimidine derivatives
MY104575A (en) 1989-12-22 1994-04-30 The Wellcome Foundation Ltd Therapeutic nucleosides.
US5302585A (en) * 1990-04-20 1994-04-12 Institute Of Organic Chemistry And Biochemistry Of The Academy Of Sciences Of The Czech Republic Use of chiral 2-(phosphonomethoxy)propyl guanines as antiviral agents
CZ285420B6 (cs) 1990-04-24 1999-08-11 Ústav Organické Chemie A Biochemie Avčr N-(3-Fluor-2-fosfonylmethoxypropyl)deriváty purinových a pyrimidinových heterocyklických bazí, způsoby jejich přípravy a použití
JPH05509307A (ja) * 1990-07-19 1993-12-22 ビーチャム・グループ・パブリック・リミテッド・カンパニー プリンの抗ウイルス性ホスホノ―アルケン誘導体
EP0468119A1 (en) 1990-07-24 1992-01-29 Merrell Dow Pharmaceuticals Inc. Novel carbocyclic analogs of certain nucleosides
DK0481214T3 (da) 1990-09-14 1999-02-22 Acad Of Science Czech Republic Prolægemidler af phosphonater
US5208221A (en) 1990-11-29 1993-05-04 Bristol-Myers Squibb Company Antiviral (phosphonomethoxy) methoxy purine/pyrimidine derivatives
US5378475A (en) 1991-02-21 1995-01-03 University Of Kentucky Research Foundation Sustained release drug delivery devices
CZ284678B6 (cs) * 1991-05-20 1999-01-13 Ústav Organické Chemie A Biochemie Avčr Di(2-propyl)estery 1-fluor-2-fosfonomethoxy-3-p -toluensulfonyloxypropanů, způsob jejich přípravy a použití
EP0630381B1 (en) 1991-10-11 1997-04-09 Institute Of Organic Chemistry And Biochemistry Of The Academy Of Sciences Of The Czech Republic Antiviral acyclic phosphonomethoxyalkyl substituted, alkenyl and alkynyl purine and pyrimidine derivatives
US6057305A (en) 1992-08-05 2000-05-02 Institute Of Organic Chemistry And Biochemistry Of The Academy Of Sciences Of The Czech Republic Antiretroviral enantiomeric nucleotide analogs
EP0618214A1 (en) 1993-04-01 1994-10-05 Merrell Dow Pharmaceuticals Inc. Unsaturated phosphonate derivatives of purines and pyrimidines
ATE486882T1 (de) 1993-09-17 2010-11-15 Gilead Sciences Inc Nukleotidanaloge
CN100409844C (zh) 1995-02-27 2008-08-13 吉里德科学公司 神经氨酸苷酶抑制剂
US5977061A (en) 1995-04-21 1999-11-02 Institute Of Organic Chemistry And Biochemistry Of The Academy Of Sciences Of The Czech Republic N6 - substituted nucleotide analagues and their use
WO1998004569A1 (en) 1996-07-26 1998-02-05 Gilead Sciences, Inc. Nucleotide analogs
BRPI0210746B8 (pt) * 2001-06-29 2021-05-25 Inst Of Organic Chemistry And Biochemistry Ascr derivados de 6-'2-(fosfonometóxi)alcóxi-pirimidina e seu método de preparação

Also Published As

Publication number Publication date
JP2006527702A (ja) 2006-12-07
EA011948B1 (ru) 2009-06-30
DK1644389T3 (da) 2011-05-09
CA2527805A1 (en) 2004-12-23
AU2004247305A1 (en) 2004-12-23
IL172015A (en) 2016-07-31
KR101102815B1 (ko) 2012-01-05
NZ543864A (en) 2009-10-30
CN1805966A (zh) 2006-07-19
ATE496056T1 (de) 2011-02-15
EP1644389B1 (en) 2011-01-19
CN1805966B (zh) 2013-03-13
DE602004031115D1 (de) 2011-03-03
US7115592B2 (en) 2006-10-03
EP1644389A1 (en) 2006-04-12
JP2012153731A (ja) 2012-08-16
KR20060041182A (ko) 2006-05-11
US20060241081A1 (en) 2006-10-26
US20050075318A1 (en) 2005-04-07
WO2004111064A1 (en) 2004-12-23
IL172015A0 (en) 2009-02-11
EA200600046A1 (ru) 2006-06-30
HK1088013A1 (en) 2006-10-27
AU2004247305B2 (en) 2010-02-18
SI1644389T1 (sl) 2011-06-30
JP5280631B2 (ja) 2013-09-04

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