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AR056191A1 - Anillo de nucleosidos de siete miembros como inhibidores de la replica viral, metodos para su sintesis, composiciones farmaceuticas que los contienen y su uso en el tratamiento de infecciones con virus de la familia flaviviridae - Google Patents

Anillo de nucleosidos de siete miembros como inhibidores de la replica viral, metodos para su sintesis, composiciones farmaceuticas que los contienen y su uso en el tratamiento de infecciones con virus de la familia flaviviridae

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Publication number
AR056191A1
AR056191A1 ARP060103671A ARP060103671A AR056191A1 AR 056191 A1 AR056191 A1 AR 056191A1 AR P060103671 A ARP060103671 A AR P060103671A AR P060103671 A ARP060103671 A AR P060103671A AR 056191 A1 AR056191 A1 AR 056191A1
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AR
Argentina
Prior art keywords
alkyl
alkynyl
alkenyl
acyl
halo
Prior art date
Application number
ARP060103671A
Other languages
English (en)
Inventor
Richard Storer
Gilles Gosselin
David Dukhan
Original Assignee
Idenix Phatmaceuticals Inc
Centre Nat Rech Scient
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 Idenix Phatmaceuticals Inc, Centre Nat Rech Scient filed Critical Idenix Phatmaceuticals Inc
Publication of AR056191A1 publication Critical patent/AR056191A1/es

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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
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
    • C07F9/65586—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system at least one of the hetero rings does not contain nitrogen as ring hetero atom
    • 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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D473/00—Heterocyclic compounds containing purine ring systems
    • 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
    • C07F9/6503—Five-membered rings
    • C07F9/6506—Five-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
    • 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
    • C07H19/14—Pyrrolo-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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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Virology (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Compuestos análogos de nucleosido que inhiben la réplica del RNA viral dependiente del RNA, composiciones que comprenden estos compuestos y la utilizacion de estos compuestos para el tratamiento de infeccion viral, especialmente la hepatitis C, en un huésped infectado. Reivindicacion 1: Un compuesto de la formula estructural general (1) en donde X es O, S, SO2, N-R, CH-R, o C-RR; R es H; alquilo C1-4, alquenilo C2-4, o alquinilo C2-4, cada uno de los cuales se podría substituir opcionalmente; CN, N3, halo, OH, CONH2, NH2, o amidino; R1 es OH, monofosfato, difosfato, trifosfato, fosfonato, fosforilo, un derivado de fosfonato, acilo, hidrogeno, alquilo, O-acilo, O-alquilo, O-arilo, O-alcoxialquilo, O-ariloxialquilo, O- alquilo substituido, O-alquenilo substituido, O-alquinilo substituido, alquilsulfonilo, arilsulfonilo, alquenilsulfonilo, aralquilsulfonilo, un residuo aminoácido, o cualquier substituto divisible que proporcione OH in vivo; R2, R3, R4 y R5 cada uno independientemente es H, OH, SH, NH2, halo, alquilcarbonilo C1-10, monofosfato, difosfato, trifosfato, fosforilo tal como fosfato, fosfonato, fosfinato, fosfonoamidato, carbamato, fosforotioato, fosforoditioato, carbonilo, tiocarbonilo, aminoacilo, amidina, NO2, CN, N3, sulfonilo, sulfoxido, sulfato, sulfonato, sulfamoilo, sulfonamida, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, acilo, haloalquilo, haloalquenilo, haloalquinilo, ciclopropilo, O-alquilo, O-alquenilo; O-alquinilo; O-acilo; S- alquilo; S-alquenilo; S-alquinilo; S-acilo; NH-alquilo; N(alquilo)2; NH(alquenilo); N(alquenilo)2; NH(alquinilo); N(alquinilo)2; NH(acilo); N(acilo)2; CONH2; COOH; CONH-alquilo; CON(alquilo)2; COSH2; COSH-alquilo; COS(alquilo)2; alquilo C1-6-O- alquilo C1-6; alquilo C1-6-O-alquenilo; alquilo C1-6-O-alquinilo; alquilo C1-6-S-alquilo; alquilo C1-6-S-alquenilo; alquilo C1-6-S-alquinilo; CH2CN; o CH2N3; y cada uno de R1', R2', R3', R4', R5' y W independientemente es H, OH, alquilcarbonilo C1- 10, fosforilo, fosfonato, fosfinato, fosfonoamidato, Cl, F, Br, I, CN, NO2, N3, NH2, acilamino, amida, amidina, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, carbonilo, tiocarbonilo, acilo, haloalquilo, haloalquenilo, haloalquinilo, ciclopropilo, sulfonilo, sulfoxido, sulfato, sulfonato, sulfamoilo, sulfonamida, alquilo C1-6-O-alquilo C1-6, alquilo C1-6-O-alquenilo, alquilo C1-6-O-alquinilo, alquilo C1-6-S-alquilo, alquilo C1-6-S-alquenilo, alquilo C1-6-S-alquinilo, CONH2, COOR, CH2CN, o CH2N3; y cada R2, R3, R4 y R5 y su correspondiente R' puede formar una mitad espiro; cada R2 + R3, R3 + R4, o R4 + R5 independientemente se podría unir para formar un anillo de 3-6 miembros que opcionalmente tenga 1-3 heteroátomos; cada R2' + R3', R3' + R4', o R4' + R5' independientemente se podría unir para formar un anillo de 3-6 miembros que opcionalmente tenga 1-3 heteroátomos; con la prevision de que al menos dos de R2, R3, R4, R5 y W deben ser OH; y con la prevision adicional de que W sea OH solo cuando X sea CH-R o C-R-R; y con la prevision adicional de que cualquier R1, R2, R3, R4 o R5 sea OH o NH2, luego su R1', R2', R3', R4' o R5' correspondiente no podría ser también OH o NH2; la base se selecciona del grupo (2) , caracterizado porque, cada ocurrencia de A, L y T independientemente es CH, N, C-alquilo, O o S dependiendo de la valencia correcta; o C-halo, C-alquilo C1-6, C-alquenilo C2-6, C-alquinilo C2-6, alquilamino C2-6, C-CF3, C-OH, C-NH2, C-NO2, C-CN, C- N3, C-COOR, o C-CONH2; D es CH, C-CN, C-NO2, N, C-alquilo C1-6, C-CONH2, C-CONH-alquilo C1-6, C-CON(alquilo C1-6)(alquilo C1-6), C-NH2, C-alcoxi, C-OH, C-alquilamino, C-C(=NH)NH2, C-COOH, C-COO-alquilo, C-CSNH2, C-CSNH-alquilo, C-CSN(alquilo)2, C- di(alquilo C1-6)amino, C-halo, C-heterociclo, en donde cualquier alquilo se substituye opcionalmente por uno a tres substitutos seleccionados del grupo que consiste de alcoxi, hidroxilo, carboxi, halo y amino, y en donde el heterociclo es un anillo de 5- a 6- miembros que tiene uno a tres heteroátomos; E es N o C-halo, C-alquilo C1-6, C-alquenilo C2-6, C-alquinilo C2-6, alquilamino C1-6, C-CF3, C-OH, C-NH2, C-NO2, C-CN, C-N3, C-COOR, o C-CONH2; Z es O o S; R6, R7, R8 y R9, es cada uno independientemente H, OH, SH, NH2, NO2, CN, N3, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, alquilamino C1-6, di(alquilo C1-6)amino, cicloalquilamino C3-6, cicloalquilo C3-6, halo, alcoxi C1-6, carboxi, alcoxicarbonilo C1-6, alquiltio C1-6, alquilsulfonilo C1-6, (alquilo C1-6)0-2 aminometilo, o CF3; R10 y R11 cada uno independientemente es H, OH, SH, NH2, halo, alquilcarbonilo C1-10, monofosfato, difosfato, trifosfato, fosforilo tal como fosfato, fosfonato, fosfinato, fosfonoamidato, carbamato, fosforotioato, fosforoditioato, carbonilo, tiocarbonilo, aminoacilo, amidina, NO2, CN, N3, sulfonilo, sulfoxido, sulfato, sulfonato, sulfamoilo, sulfonamida, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, acilo, haloalquilo, haloalquenilo, haloalquinilo, ciclopropilo, CONH2, COOH, CONH-alquilo, CON(alquilo)2, COSH2, COSH-alquilo, COS(alquilo)2, alquilo C1-6-O-alquilo C1-6, alquilo C1-6-O-alquenilo, alquilo C1-6-O-alquinilo, alquilo C1-6-S-alquilo, alquilo C1-6-S-alquenilo, alquilo C1- 6-S-alquinilo, CH2CN, o CH2N3; Q1 y Q2 cada uno independientemente es N, N-R, O, S, SO, SO2, CH-R o C-R-R, dependiendo de la valencia apropiada requerida; la línea de puntos indica la presencia de un enlace simple o doble; o una sal farmacéuticamente aceptable o prodroga, o una forma estereo-isomérica o tautomérica de estos.
ARP060103671A 2005-08-23 2006-08-23 Anillo de nucleosidos de siete miembros como inhibidores de la replica viral, metodos para su sintesis, composiciones farmaceuticas que los contienen y su uso en el tratamiento de infecciones con virus de la familia flaviviridae AR056191A1 (es)

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DE10238722A1 (de) 2002-08-23 2004-03-11 Bayer Ag Selektive Phosphodiesterase 9A-Inhibitoren als Arzneimittel zur Verbesserung kognitiver Prozesse
WO2008025160A1 (en) * 2006-08-31 2008-03-06 Mcgill University Oxepane nucleosides and oligonucleotides, uses thereof and methods of making the same
CN101730699A (zh) 2007-03-21 2010-06-09 百时美施贵宝公司 可用于治疗增殖性、变应性、自身免疫性和炎症性疾病的稠合杂环化合物
EP2217602B1 (en) 2007-11-30 2018-08-29 Boehringer Ingelheim International GmbH 1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one derivatives and their use as pde9a modulators for the treatment of cns disorders
UA105362C2 (en) 2008-04-02 2014-05-12 Бьорингер Ингельхайм Интернациональ Гмбх 1-heterocyclyl-1, 5-dihydro-pyrazolo [3, 4-d] pyrimidin-4-one derivatives and their use as pde9a modulators
EP2334684B1 (en) 2008-09-08 2017-08-02 Boehringer Ingelheim International GmbH Pyrazolopyrimidines and their use for the treatment of cns disorders
TWI491610B (zh) 2008-10-09 2015-07-11 必治妥美雅史谷比公司 作為激酶抑制劑之咪唑并嗒腈
BRPI1011533A2 (pt) 2009-03-31 2016-03-29 Boehringer Ingelheim Int derivados de 1-heterocicil-1 5- diidro-pirazolo [3,4--d] pirimidin-4-ona e seu uso como moduladores de pde9a.
CA2778949C (en) 2009-10-30 2018-02-27 Janssen Pharmaceutica Nv Imidazo[1,2-b]pyridazine derivatives and their use as pde10 inhibitors
EA021568B1 (ru) 2009-12-23 2015-07-30 Такеда Фармасьютикал Компани Лимитед Конденсированные гетероароматические пирролидиноны как ингибиторы syk
AR080754A1 (es) 2010-03-09 2012-05-09 Janssen Pharmaceutica Nv Derivados de imidazo (1,2-a) pirazina y su uso como inhibidores de pde10
SG187081A1 (en) 2010-08-12 2013-03-28 Boehringer Ingelheim Int 6-cycloalkyl-1, 5-dihydro-pyrazolo [3, 4-d] pyrimidin-4-one derivatives and their use as pde9a inhibitors
US8809345B2 (en) 2011-02-15 2014-08-19 Boehringer Ingelheim International Gmbh 6-cycloalkyl-pyrazolopyrimidinones for the treatment of CNS disorders
US9056873B2 (en) 2011-06-22 2015-06-16 Takeda Pharmaceutical Company Limited Substituted 6-aza-isoindolin-1-one derivatives
CN103619846B (zh) 2011-06-27 2016-08-17 詹森药业有限公司 1-芳基-4-甲基-[1,2,4]三唑[4,3-a]喹喔啉衍生物
ES2855575T3 (es) 2012-06-26 2021-09-23 Janssen Pharmaceutica Nv Combinaciones que comprenden compuestos de 4-metil-[1,2,4]triazolo[4,3-a]quinoxalina como inhibidores de PDE2 e inhibidores de PDE10 para su uso en el tratamiento de trastornos neurológicos o metabólicos
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MY164523A (en) * 2000-05-23 2017-12-29 Univ Degli Studi Cagliari Methods and compositions for treating hepatitis c virus
IL153020A0 (en) * 2000-05-26 2003-06-24 Idenix Cayman Ltd Methods and compositions for treating flaviviruses and pestiviruses
CA2489552A1 (en) * 2002-06-28 2004-01-08 Idenix (Cayman) Limited 2'-c-methyl-3'-o-l-valine ester ribofuranosyl cytidine for treatment of flaviviridae infections
US7608600B2 (en) * 2002-06-28 2009-10-27 Idenix Pharmaceuticals, Inc. Modified 2′ and 3′-nucleoside prodrugs for treating Flaviviridae infections

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