CA2268434C - Mycophenolic bisphosphonate derivatives and their preparation from tetraphosphonate bicyclic trisanhydrides - Google Patents

Mycophenolic bisphosphonate derivatives and their preparation from tetraphosphonate bicyclic trisanhydrides Download PDF

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Publication number
CA2268434C
CA2268434C CA002268434A CA2268434A CA2268434C CA 2268434 C CA2268434 C CA 2268434C CA 002268434 A CA002268434 A CA 002268434A CA 2268434 A CA2268434 A CA 2268434A CA 2268434 C CA2268434 C CA 2268434C
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Prior art keywords
phosphonate
methylenebis
ene
hydroxy
methoxy
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Expired - Fee Related
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CA002268434A
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English (en)
French (fr)
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CA2268434A1 (en
Inventor
Krzysztof W. Pankiewicz
Krystyna Lesiak
Kyoichi A. Watanabe
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Pharmasset Inc
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Priority to CA002575919A priority Critical patent/CA2575919A1/en
Publication of CA2268434A1 publication Critical patent/CA2268434A1/en
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Publication of CA2268434C publication Critical patent/CA2268434C/en
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    • 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
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
    • C07F9/32—Esters thereof
    • 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
    • C07H19/10—Pyrimidine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/02—Antineoplastic agents specific for leukemia
    • 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
    • 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
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/22—Amides of acids of phosphorus
    • C07F9/24—Esteramides
    • C07F9/2454—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/2479—Compounds containing the structure P(=X)n-N-acyl, P(=X)n-N-heteroatom, P(=X)n-N-CN (X = O, S, Se; n = 0, 1)
    • C07F9/2495—Compounds containing the structure P(=X)n-N-acyl, P(=X)n-N-heteroatom, P(=X)n-N-CN (X = O, S, Se; n = 0, 1) containing the structure P(=X)n-N-P (X = O, S, Se; n = 0, 1)
    • 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
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
    • C07F9/32—Esters thereof
    • C07F9/3205—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/3235—Esters of poly(thio)phosphinic acids
    • 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
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/40—Esters thereof
    • C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4025—Esters of poly(thio)phosphonic acids
    • 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
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/44—Amides thereof
    • C07F9/4403—Amides thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4423—Amides of poly (thio)phosphonic acids
    • 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
    • C07F9/657163—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 the ring phosphorus atom being bound to at least one carbon atom
    • C07F9/657172—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 the ring phosphorus atom being bound to at least one carbon atom the ring phosphorus atom and one oxygen atom being part of a (thio)phosphinic acid ester: (X = O, S)
    • 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
    • C07F9/657163—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 the ring phosphorus atom being bound to at least one carbon atom
    • C07F9/657181—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 the ring phosphorus atom being bound to at least one carbon atom the ring phosphorus atom and, at least, one ring oxygen atom being part of a (thio)phosphonic acid derivative
    • 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
    • C07F9/6581—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 nitrogen atoms with or without oxygen or sulfur atoms, as 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
    • C07H19/16—Purine radicals
    • C07H19/20—Purine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
    • 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
    • C07H19/207—Purine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids the phosphoric or polyphosphoric acids being esterified by a further hydroxylic compound, e.g. flavine adenine dinucleotide or nicotinamide-adenine dinucleotide

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • Genetics & Genomics (AREA)
  • Biotechnology (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Oncology (AREA)
  • Hematology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
CA002268434A 1996-10-09 1997-10-09 Mycophenolic bisphosphonate derivatives and their preparation from tetraphosphonate bicyclic trisanhydrides Expired - Fee Related CA2268434C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CA002575919A CA2575919A1 (en) 1996-10-09 1997-10-09 Tetraphosphonate bicyclic trisanhydrides

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US2815496P 1996-10-09 1996-10-09
US3836097P 1997-02-13 1997-02-13
US60/038,360 1997-02-13
US60/028,154 1997-02-13
PCT/US1997/018323 WO1998015563A1 (en) 1996-10-09 1997-10-09 Tetraphosphonate bicyclic trisanhydrides

Related Child Applications (1)

Application Number Title Priority Date Filing Date
CA002575919A Division CA2575919A1 (en) 1996-10-09 1997-10-09 Tetraphosphonate bicyclic trisanhydrides

Publications (2)

Publication Number Publication Date
CA2268434A1 CA2268434A1 (en) 1998-04-16
CA2268434C true CA2268434C (en) 2007-05-01

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CA002268434A Expired - Fee Related CA2268434C (en) 1996-10-09 1997-10-09 Mycophenolic bisphosphonate derivatives and their preparation from tetraphosphonate bicyclic trisanhydrides

Country Status (13)

Country Link
US (2) US6326490B1 (enExample)
EP (1) EP0934325B1 (enExample)
JP (1) JP4118958B2 (enExample)
KR (1) KR100560182B1 (enExample)
CN (1) CN1113888C (enExample)
AT (1) ATE271058T1 (enExample)
AU (1) AU4815197A (enExample)
BR (1) BR9712285A (enExample)
CA (1) CA2268434C (enExample)
DE (1) DE69729877T2 (enExample)
ES (1) ES2225958T3 (enExample)
PT (1) PT934325E (enExample)
WO (1) WO1998015563A1 (enExample)

Families Citing this family (41)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU4815197A (en) 1996-10-09 1998-05-05 Pharmasset, Ltd. Tetraphosphonate bicyclic trisanhydrides
EP0981534B1 (en) 1997-02-06 2006-05-03 Inspire Pharmaceuticals, Inc. Dinucleotides and their uses
US7223744B2 (en) 1997-02-10 2007-05-29 Inspire Pharmaceuticals, Inc. Pharmaceutical formulation comprising dinucleoside polyphosphates and salts thereof
US20040181078A1 (en) * 1997-10-10 2004-09-16 Pharmasset, Ltd. Tetraphosphonate bicyclic trisanhydrides
WO2001044260A2 (en) * 1999-12-17 2001-06-21 Ariad Pharmaceuticals, Inc. Novel purines
US7115589B2 (en) 1999-12-17 2006-10-03 Ariad Pharmaceuticals, Inc. Purine derivatives
US6787526B1 (en) 2000-05-26 2004-09-07 Idenix Pharmaceuticals, Inc. Methods of treating hepatitis delta virus infection with β-L-2′-deoxy-nucleosides
US6875751B2 (en) 2000-06-15 2005-04-05 Idenix Pharmaceuticals, Inc. 3′-prodrugs of 2′-deoxy-β-L-nucleosides
US6867199B2 (en) 2000-08-21 2005-03-15 Inspire Pharmaceuticals, Inc. Dinucleoside polyphosphate compositions and their therapeutic use
US6555675B2 (en) 2000-08-21 2003-04-29 Inspire Pharmaceuticals, Inc. Dinucleoside polyphosphate compositions and their therapuetic use as purinergic receptor agonists
JP2005502580A (ja) * 2000-12-15 2005-01-27 フアーマセツト・リミテツド フラビウィルス感染治療用抗ウィルス薬
US7452901B2 (en) 2003-04-25 2008-11-18 Gilead Sciences, Inc. Anti-cancer phosphonate analogs
WO2004096285A2 (en) 2003-04-25 2004-11-11 Gilead Sciences, Inc. Anti-infective phosphonate conjugates
SG182849A1 (en) 2003-04-25 2012-08-30 Gilead Sciences Inc Antiviral phosphonate analogs
US7427636B2 (en) 2003-04-25 2008-09-23 Gilead Sciences, Inc. Inosine monophosphate dehydrogenase inhibitory phosphonate compounds
US7432261B2 (en) 2003-04-25 2008-10-07 Gilead Sciences, Inc. Anti-inflammatory phosphonate compounds
US7470724B2 (en) 2003-04-25 2008-12-30 Gilead Sciences, Inc. Phosphonate compounds having immuno-modulatory activity
EP1620109A2 (en) 2003-04-25 2006-02-01 Gilead Sciences, Inc. Kinase inhibitor phosphonate conjugates
US7407965B2 (en) 2003-04-25 2008-08-05 Gilead Sciences, Inc. Phosphonate analogs for treating metabolic diseases
WO2005002626A2 (en) 2003-04-25 2005-01-13 Gilead Sciences, Inc. Therapeutic phosphonate compounds
RU2358979C2 (ru) 2003-05-30 2009-06-20 Фармассет, Инк. Модифицированные фторированные аналоги нуклеозида
WO2005044279A1 (en) 2003-10-24 2005-05-19 Gilead Sciences, Inc. Purine nucleoside phosphonate conjugates
US7432273B2 (en) 2003-10-24 2008-10-07 Gilead Sciences, Inc. Phosphonate analogs of antimetabolites
BRPI0417988A (pt) 2003-12-22 2007-04-27 Gilead Sciences Inc análogos de fosfonato antivirais
DE10361932A1 (de) * 2003-12-30 2005-07-28 Celanese Ventures Gmbh Protonenleitende Membran und deren Verwendung
DE10361832A1 (de) * 2003-12-30 2005-07-28 Celanese Ventures Gmbh Protonenleitende Membran und deren Verwendung
PT2258376T (pt) 2004-07-27 2019-05-31 Gilead Sciences Inc Análogos fosfonatados de compostos inibidores do vih
EP1933848A2 (en) * 2005-10-06 2008-06-25 Innate Pharma Phosphoantigen salts of organic bases and methods for their crystallization
US20090111774A1 (en) * 2007-06-01 2009-04-30 Luitpold Pharmaceuticals, Inc. Pmea lipid conjugates
CN104324044A (zh) * 2008-02-15 2015-02-04 微量医疗技术有限公司 制造核苷四磷酸类似物的方法
BRPI0915878A2 (pt) 2008-07-08 2015-11-03 Gilead Sciences Inc sais ou hidratos de compostos inibidores de hiv, seu uso e composição farmacêutica que os compreende
EP2447274B1 (en) 2008-10-24 2017-10-04 Ionis Pharmaceuticals, Inc. Oligomeric compounds and methods
WO2011139702A2 (en) 2010-04-28 2011-11-10 Isis Pharmaceuticals, Inc. Modified nucleosides and oligomeric compounds prepared therefrom
WO2011139695A2 (en) 2010-04-28 2011-11-10 Isis Pharmaceuticals, Inc. Modified 5' diphosphate nucleosides and oligomeric compounds prepared therefrom
WO2011139699A2 (en) 2010-04-28 2011-11-10 Isis Pharmaceuticals, Inc. 5' modified nucleosides and oligomeric compounds prepared therefrom
WO2014160200A1 (en) * 2013-03-13 2014-10-02 Dana-Farber Cancer Institute, Inc. Ras inhibitors and uses thereof
LT3399984T (lt) 2016-01-08 2023-11-10 Arcus Biosciences, Inc. 5'-nukleotidazės, ekto moduliatoriai ir jų panaudojimas
CN110022881B (zh) * 2016-11-18 2023-05-02 艾库斯生物科学有限公司 Cd73介导的免疫抑制的抑制剂
PT3661937T (pt) 2017-08-01 2021-09-24 Gilead Sciences Inc Formas cristalinas de ((s)-((((2r,5r)-5-(6-amino-9h-purin-9-il)-4-fluoro-2,5-dihidrofurano-2-il)oxi)metil)(fenoxi)fosforil)-l-alaninato de etil (gs-9131) para tratamento de infeções virais
WO2020210970A1 (en) * 2019-04-16 2020-10-22 Bioardis Llc Imidazotriazine derivatives as cd73 inhibitors
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Publication number Priority date Publication date Assignee Title
FI89365C (fi) * 1990-12-20 1993-09-27 Leiras Oy Foerfarande foer framstaellning av nya farmakologiskt anvaendbara metylenbisfosfonsyraderivat
US5569650A (en) * 1993-06-11 1996-10-29 Sloan-Kettering Institute For Cancer Research C-nucleoside isosters of analogs thereof and pharmaceutical compositions
DE4341161A1 (de) * 1993-12-02 1995-06-08 Michael Prof Dr Zeppezauer Membrangängiger Wirkstoff zur Störung der DNA-Biosynthese
FR2721931B1 (fr) * 1994-06-30 1996-08-02 Commissariat Energie Atomique Conjugues d'analogues de diphosphates ou triphosphates avec des enzymes ou des proteurs antigeniques et dosage immunologique utilisant de tels conjugues
AU4815197A (en) 1996-10-09 1998-05-05 Pharmasset, Ltd. Tetraphosphonate bicyclic trisanhydrides

Also Published As

Publication number Publication date
BR9712285A (pt) 2001-11-20
JP4118958B2 (ja) 2008-07-16
CA2268434A1 (en) 1998-04-16
EP0934325B1 (en) 2004-07-14
ATE271058T1 (de) 2004-07-15
EP0934325A1 (en) 1999-08-11
EP0934325A4 (en) 2000-08-16
ES2225958T3 (es) 2005-03-16
US20020161220A1 (en) 2002-10-31
WO1998015563A1 (en) 1998-04-16
CN1239964A (zh) 1999-12-29
KR100560182B1 (ko) 2006-03-13
KR20000049026A (ko) 2000-07-25
CN1113888C (zh) 2003-07-09
DE69729877T2 (de) 2005-07-14
US6326490B1 (en) 2001-12-04
PT934325E (pt) 2004-10-29
US6713623B2 (en) 2004-03-30
JP2001501952A (ja) 2001-02-13
AU4815197A (en) 1998-05-05
DE69729877D1 (de) 2004-08-19

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