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DK2794628T3 - 4'-azido-3'-fluor-substituerede nukleosidderivater som inhibitorer af hcv-rna-replikation - Google Patents

4'-azido-3'-fluor-substituerede nukleosidderivater som inhibitorer af hcv-rna-replikation Download PDF

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Publication number
DK2794628T3
DK2794628T3 DK12808791.3T DK12808791T DK2794628T3 DK 2794628 T3 DK2794628 T3 DK 2794628T3 DK 12808791 T DK12808791 T DK 12808791T DK 2794628 T3 DK2794628 T3 DK 2794628T3
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compound
azido
fluoro
furan
pyrimidin
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DK12808791.3T
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Mark Smith
Francisco Xavier Talamas
Jing Zhang
Zhuming Zhang
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Riboscience Llc
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    • 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
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
    • A61K31/706—Compounds 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
    • A61K31/7064—Compounds 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
    • A61K31/7068—Compounds 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
    • 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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
    • A61K31/706—Compounds 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
    • A61K31/7064—Compounds 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
    • A61K31/7068—Compounds 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
    • A61K31/7072—Compounds 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 having two oxo groups directly attached to the pyrimidine ring, e.g. uridine, uridylic acid, thymidine, zidovudine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
    • 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
    • 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
    • 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

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  • Communicable Diseases (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)

Claims (14)

  1. ^-AZIDO-S’-FLUOR-SUBSTITUEREDE NUKLEOS1DDERSVATER SOM INHIBITORER AF HCV-RNA-REPLIKATION
    1. Forbindelse med formlen I
    hvor: R1 er H, Ci-7-haloalkyi eller aryl, hvor aryl er phenyl eller naphthyl, valgfrit substitueret med ét eller flere C-i-7-alkyl, C2-7-alkenyl, C2-7-alkynyi, Ci-7-alkoxy, halogen, C1-7 halogenalkyl, -N(R1a)2, acylamlno, -S02N(R1a)2, -COR1b, -S02(R1c), - NHS02(R1c), nitro eller cyano; hvert R1a uafhængigt af hinanden er H eller Ci~7~alkyl; hvert R1b uafhængigt af hinanden er -OR1a eller -N(R1a)2; hvert R1c er Ci-7-aikyi; R2a og R2b uafhængigt af hinanden er H eller Cw-alkyl; R3 er Ci-7-alkyi, phenyl eller phenyi-Ci-?-a!kyl; R4 er H, Ci-y-alkyl, eller R2b og R4 tilsammen danner (CH2X3; R5 er H, C(=0)R1c, C(=0)R1b, P(=0)(OR1)(OR1a) eller P(=0)(0R1)(NR4R7); og R6 er
    eller et farmakologisk acceptabelt salt deraf,
  2. 2. Forbindelse ifølge krav 1, hvor R4 er H.
  3. 3. Forbindelse ifølge krav 2, hvor R1 er naphthyl eller phenyl.
  4. 4. Forbindelse ifølge krav 3, hvor R2a er H.
  5. 5. Forbindelse ifølge krav 4, hvor R2b er methyl.
  6. 6. Forbindelse ifølge krav 5, hvor R3 er isopropyl, ethyl eller benzyl.
  7. 7. Forbindelse ifølge krav 6, hvor R5 er H.
  8. 8. Forbindelse ifølge krav 6, hvor R5 er C(=0)R1c.
  9. 9. Forbindelse ifølge krav 8, hvor R1c er ethyl.
  10. 10. Forbindelse ifølge krav 7, hvor R6 er
  11. 11. Forbindelse ifølge krav 7, hvor R6 er
  12. 12. Forbindelse ifølge krav 1, hvor forbindelsen er valgt fra gruppen bestående af: (S)-2-{[(2R,3S,4S,5R)-2-azido-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-y!)-3-fiuor-4- hydroxy-tetrahydro-furan-2-ylmethoxy]-phenoxy-phosphorylamino}-prop!onsyre- isopropylester; (S)-2-{[(2Rl3S!4S!5R)-2-azido-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-fluor-4- hydroxy-tetrahydro-furan-2-ylmethoxy]-phenoxy-phosphory!amino}-propionsyre- ethylester; (S)-2-[[(2R,3S,4S,5R)-2-azido-5-(2,4-dioxo-3)4-dihydro-2/-/-pyrim!din-1-yl)-3-fluor-4- hydroxy-tetrahydro-furan-2-ylmethoxy]-(naphthaien-1-yloxy)-phosphorylamino]- proplonsyre-ethylester; (S)-2-[[(2R,3S,4S,5R)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-2-azido-3-fluor-4- hydroxy-tetrahydro-furan-2-ylmethoxy]-(naphthalen-1-yioxy)-phosphory!amino]- propionsyre-isopropylester; (S)-2-[[(2R,3S,4S,5R)-5-(4-amino-2-oxo-2W-pyrimidin-1-yl)-2-azido-3-fluor-4- hydroxy-tetrahydro-furan-2-ylmethoxy]-(naphthalen-1-yloxy)-phosphorylam!no]- propionsyre-benzylester; (S)-2-[[(2R,3S,4S,5R)-5-(4-amino-2-oxo-2/-/-pyrimidin-1-yl)-2-azido-3-fluor-4- hydroxy-tetrahydro-furan-2-ylmethoxy]-(naphthalen-1-yloxy)-phcsphorylamino]- propionsyre-ethylester; (S)-2-{[(2R,3S,4S,5R)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-2-azido-3-fluor-4- hydroxy-ietrabydro-furan-2-ylmethoxy]-phenoxy-phosphoryiamino}-propionsyre- isopropylester; (S)-2-{[(2R,3S,4S,5R)-5-{4-amino-2-oxo-2H-pyr!midin-1-yi)-2-azido-3-f]uor-4- hydroxy-telrahydro-furan-2-yimethoxy]-hydroxy-pbosphorylamino}-prQpionsyre- isopropylester; og (S)~2-[[(2R,3S,4S,5R)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-2-azido-3-fluor~4- propionyloxy-tetrahydro-furan-2~y!methoxy]-(naphihalen-1-yloxy)-phosphorylamino3- propionsyre-isopropylester,
  13. 13, Forbindelse ifølge et hvilket som helst af kravene 1-12 til anvendelse ved behandling eller profylakse af hepatitis C-virus-(HCV)-infektion.
  14. 14. Farmaceutisk sammensætning, der omfatter en forbindelse ifølge et hvilket som helst af kravene 1-12 og terapeutisk inerte bærere.
DK12808791.3T 2011-12-20 2012-12-17 4'-azido-3'-fluor-substituerede nukleosidderivater som inhibitorer af hcv-rna-replikation DK2794628T3 (da)

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US201161577712P 2011-12-20 2011-12-20
PCT/EP2012/075688 WO2013092447A1 (en) 2011-12-20 2012-12-17 4'-azido, 3'-fluoro substituted nucleoside derivatives as inhibitors of hcv rna replication

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CA2869317C (en) 2016-05-17
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AU2012357986B2 (en) 2017-02-02
LT2794628T (lt) 2017-07-10
CN104011060A (zh) 2014-08-27
PH12014501283A1 (en) 2014-09-08
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NZ625844A (en) 2016-08-26
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UA110428C2 (uk) 2015-12-25
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