CA2764827C - Phosphonates synthons for the synthesis of phosphonates derivatives showing better bioavailability - Google Patents

Phosphonates synthons for the synthesis of phosphonates derivatives showing better bioavailability Download PDF

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Publication number
CA2764827C
CA2764827C CA2764827A CA2764827A CA2764827C CA 2764827 C CA2764827 C CA 2764827C CA 2764827 A CA2764827 A CA 2764827A CA 2764827 A CA2764827 A CA 2764827A CA 2764827 C CA2764827 C CA 2764827C
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CA
Canada
Prior art keywords
group
formula
branched
straight
alkyl group
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
CA2764827A
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English (en)
French (fr)
Other versions
CA2764827A1 (en
Inventor
Luigi A. Agrofoglio
Vincent Roy
Ugo Pradere
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.)
Centre National de la Recherche Scientifique
University of Orléans
Original Assignee
Centre National de la Recherche Scientifique
University of Orléans
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Publication of CA2764827A1 publication Critical patent/CA2764827A1/en
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Publication of CA2764827C publication Critical patent/CA2764827C/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

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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
    • C07F9/28—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
    • C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4075—Esters with hydroxyalkyl compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • 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
    • C07F9/28—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
    • C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
    • 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
    • C07F9/4015—Esters of acyclic unsaturated 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
    • C07F9/645—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
    • 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
    • C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
    • C07F9/65616—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings containing the ring system having three or more than three double bonds between ring members or between ring members and non-ring members, e.g. purine or analogs

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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)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
CA2764827A 2009-06-18 2010-06-17 Phosphonates synthons for the synthesis of phosphonates derivatives showing better bioavailability Expired - Fee Related CA2764827C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP09305562A EP2270021A1 (en) 2009-06-18 2009-06-18 Phosphonates synthons for the synthesis of phosphonates derivatives showing better bioavailability
EP09305562.2 2009-06-18
PCT/EP2010/058567 WO2010146127A1 (en) 2009-06-18 2010-06-17 Phosphonates synthons for the synthesis of phosphonates derivatives showing better bioavailability

Publications (2)

Publication Number Publication Date
CA2764827A1 CA2764827A1 (en) 2010-12-23
CA2764827C true CA2764827C (en) 2018-08-21

Family

ID=41171101

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2764827A Expired - Fee Related CA2764827C (en) 2009-06-18 2010-06-17 Phosphonates synthons for the synthesis of phosphonates derivatives showing better bioavailability

Country Status (6)

Country Link
US (1) US8785629B2 (enExample)
EP (2) EP2270021A1 (enExample)
JP (1) JP2012530113A (enExample)
CA (1) CA2764827C (enExample)
ES (1) ES2601849T3 (enExample)
WO (1) WO2010146127A1 (enExample)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012034719A1 (en) * 2010-09-14 2012-03-22 Centre National De La Recherche Scientifique Novel antiviral acyclic nucleoside phosphonates
JPWO2021177339A1 (enExample) * 2020-03-04 2021-09-10
WO2023288045A2 (en) * 2021-07-15 2023-01-19 Alnylam Pharmaceuticals, Inc. Simple chemical approaches to introduce 2,6-diaminopurine and 2-aminoadenine conjugates into oligonucleotides

Family Cites Families (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL6814978A (enExample) 1967-10-30 1969-05-02
BR6914868D0 (pt) * 1969-01-23 1973-03-20 & Co Inc Merck Processos quimicos
JPS6069089A (ja) 1983-09-26 1985-04-19 Nissan Chem Ind Ltd ジヒドロピリジン−５−ホスホネ−ト誘導体およびその製造法
ES2083580T3 (es) * 1990-06-13 1996-04-16 Arnold Glazier Profarmacos de fosforo.
EP0521622B1 (en) 1991-07-03 1997-08-13 PHARMACIA & UPJOHN COMPANY Pyrazolopyrimidine and pyrimidinyl bisphosphonic esters as anti-inflammatories
ZA941088B (en) * 1993-02-19 1995-09-27 Symphar Sa Substituted ketophosphonates the processes for their preparation and pharmaceutical compositions containing them
DE4343599A1 (de) 1993-12-21 1995-06-22 Bayer Ag Verwendung von Phosphonsäureestern zur Behandlung von Hirnleistungsstörungen und Depressionen
US5635449A (en) * 1995-04-07 1997-06-03 American Cyanamid Company Arylthioalkyl- and arylthioalkenylphosphonic acids and derivatives thereof useful as herbicidal agents
IT1281498B1 (it) * 1995-06-07 1998-02-18 Sardinian Antiviral Research C Pirazolo - derivati ad attivita' antitumorale, processo per la loro preparazione e composizioni farmaceutiche che li contengono , e
JP4129993B2 (ja) * 1996-01-16 2008-08-06 ブリストル―マイヤーズ・スクイブ・カンパニー ミクロソーム・トリグリセリド転移プロテインの立体配座制限芳香族抑制剤および方法
IT1290444B1 (it) 1997-03-27 1998-12-03 Boehringer Mannheim Italia Coniugati di bis-fosfonati con funzionalita' alchilanti aventi attivita' antitumorale
US6716825B2 (en) * 1999-12-03 2004-04-06 The Regents Of The University Of California Phosphonate compounds
TW200408645A (en) 2002-04-26 2004-06-01 Gilead Sciences Inc Non nucleoside reverse transcriptase inhibitors
AU2003299029A1 (en) 2002-09-19 2004-04-08 Ilex Oncology Research, Sarl Substituted phosphonate compounds having bone anabolic activity
AU2003301439A1 (en) * 2002-10-16 2004-05-04 Gilead Sciences, Inc. Pre-organized tricyclic integrase inhibitor compounds
JP2010535701A (ja) * 2003-04-25 2010-11-25 ギリアード サイエンシーズ， インコーポレイテッド 抗癌ホスホネートアナログ
EP2428516A1 (en) 2003-11-19 2012-03-14 Metabasis Therapeutics, Inc. Novel phosphorus-containing thyromimetics
US20080261923A1 (en) * 2004-08-04 2008-10-23 Etzkorn Felicia A Alkene Mimics
WO2008096002A1 (en) 2007-02-08 2008-08-14 Tibotec Pharmaceuticals Ltd. Hcv inhibiting macrocyclic phosphonates and amidophosphates

Also Published As

Publication number Publication date
US20120142897A1 (en) 2012-06-07
EP2443130B1 (en) 2016-08-03
ES2601849T3 (es) 2017-02-16
CA2764827A1 (en) 2010-12-23
EP2270021A1 (en) 2011-01-05
EP2443130A1 (en) 2012-04-25
US8785629B2 (en) 2014-07-22
WO2010146127A1 (en) 2010-12-23
JP2012530113A (ja) 2012-11-29

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Effective date: 20150520

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Effective date: 20220301

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