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AR077173A1 - Compuestos heterociclicos antivirales - Google Patents

Compuestos heterociclicos antivirales

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Publication number
AR077173A1
AR077173A1 ARP100102180A ARP100102180A AR077173A1 AR 077173 A1 AR077173 A1 AR 077173A1 AR P100102180 A ARP100102180 A AR P100102180A AR P100102180 A ARP100102180 A AR P100102180A AR 077173 A1 AR077173 A1 AR 077173A1
Authority
AR
Argentina
Prior art keywords
alkyl
hydrogen
alkoxy
oxo
halogen
Prior art date
Application number
ARP100102180A
Other languages
English (en)
Inventor
Elbert Chin
Jim Li
Alfred Sui-Ting Lui
Kristen Lynn Mccaleb
Ryan Craig Schoenfeld
Francisco Xavier Talamas
Vicente Fidalgo Javier De
Original Assignee
Hoffmann La Roche
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 Hoffmann La Roche filed Critical Hoffmann La Roche
Publication of AR077173A1 publication Critical patent/AR077173A1/es

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D239/08—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms directly attached in position 2
    • C07D239/10—Oxygen or sulfur atoms
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/44—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/30—Oxygen or sulfur atoms
    • C07D233/32—One oxygen atom
    • C07D233/34—Ethylene-urea
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
    • C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D237/14—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/34—One oxygen atom
    • C07D239/36—One oxygen atom as doubly bound oxygen atom or as unsubstituted hydroxy radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D241/18—Oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D249/12—Oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
    • C07D275/04—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D275/06—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems with hetero atoms directly attached to the ring sulfur atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/15—Six-membered rings
    • C07D285/16—Thiadiazines; Hydrogenated thiadiazines

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Virology (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • General Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Veterinary Medicine (AREA)
  • Molecular Biology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
  • Hydrogenated Pyridines (AREA)

Abstract

Estos compuestos son inhibidores de la polimerasa NS5B del virus de la hepatitis C. Se describen también composiciones y su uso para tratar una infeccion del HCV y para inhibir la replicacion del HCV. Reivindicacion 1: Un compuesto de la formula 1: en la que R1 es (i) un resto heterocíclico elegido entre el grupo formado por el 2-oxo-tetrahidro-pirimidin-1-ilo, 2-oxo-imidazolin-1-ilo, 2, 6-dioxo-tetrahidro-pirimidin-1-ilo, 2,5-oxo-imidazolin-l-ilo, 2-oxo-piperidin-1-ilo, 2-oxo-pirrolidin-1-ilo, 1,1-dioxo-1lambda6-isotiazolidin-2-ilo y 1,1-dioxo-1lambda6-[1,2,6]tiadiazinan-2-ilo, dicho heterociclo está opcionalmente sustituido por uno o dos sustituyentes elegidos con independencia entre alquilo C1-6, o (ii) un resto heteroarilo elegido entre el grupo formado por 2-oxo-2(H)-piridin-1-ilo, 6-oxo-6H-piridazin-1-ilo, 6-oxo-6H-pirimidin-1-ilo, 2-oxo-2H-pirazin-1-ilo y 5-oxo-1,5-dihidro-[1,2,4]triazol-4-ilo, dicho resto heteroarilo está opcionalmente sustituido con independencia por uno o dos sustituyentes halogeno o alquilo C1-3; R2 es (a) -CR2a=CR2aAr, (b) -(C(R2b)2)nAr, (c) -X[C(R6)2]pNRaRb, en el que X es O o NR7, R7 es hidrogeno o alquilo C1-4, R6 es con independencia de cada aparicion hidrogeno, alquilo C1-3 o dos restos R6 en un mismo átomo de carbono son alquileno C2-5 o dos R6 restos en diferentes átomos de carbono son alquileno C1-4, (d) 1-oxo-1H-isocromen-7-ilo o 2H-isoquinolin-1-ona que pueden opcionalmente sustituidos por NRaRb, o, (e) benzooxazol-2-ilo o benzotiazol-2-ilo que pueden estar opcionalmente sustituidos por NRaRb; R2a es con independencia de cada aparicion hidrogeno, alquilo C1-3, ciano, carboxilo o halogeno; R2b es con independencia de cada aparicion hidrogeno o alquilo C1-3, ciano, carboxilo, hidroxialquilo C1-3 o (alcoxi C1-3) -alquilo C1-3; R3 es hidrogeno, alcoxi C1-6, alquilo C1-6, haloalquilo C1-6, haloalcoxi C1-6 o halogeno o R3 y R4a juntos son CH2-O o (CH2)2 y junto con los átomos a los que están unidos forman un 2,3-dihidrobenzofurano o un indano; Ar es (a) arilo o naftilo, o (b) heteroarilo, dichos arilo o heteroarilo están opcionalmente sustituidos con independencia de una a tres veces por sustituyentes elegidos entre el grupo formado por hidroxi, alcoxi C1-6, alquilo C1-6, hidroxialquilo C1-6, (alcoxi C1-3) -alquilo C1-6, halogeno, (CH2)nNRaRb, ciano, (alcoxi C1-6) -carbonilo, carbamoilo, N-alquilcarbamoílo, N,N-dialquilcarbamoílo, (CH2)nCO2H, SO2NH2, alquilsulfinilo C1-6 y alquilsulfonilo C1-6; Ra y Rb son con independencia hidrogeno, alquilo C1-6, haloalquilo C1-6, acilo C1-6, alquilsulfonilo C1-6, haloalquilsulfonilo C1-6, cicloalquilsulfonilo C3-7, (cicloalquil C3-7)-alquilsulfonilo C1-3, (alcoxi C1-6)-alquilsulfonilo C1-6, -SO2-NRcRd, (alquil C1-3) carbamoilo o di(alquil C1-3)- carbamoilo; Rc y Rd son (i) con independencia hidrogeno, alquilo C1-3 o (CH2)2-6NReRf o (ii) junto con el nitrogeno al que están unidos forman un (CH2)2X5(CH2)2, en el que X5 es O o NRi y Ri es hidrogeno, alquilo C1-3, acilo C1-3 o alquilsulfonilo C1-3; Re y Rf son con independencia de cada aparicion hidrogeno o alquilo C1-3; R4 es hidrogeno, alquilo C1-6, haloalquilo C1-6, cicloalquilo C3-5, halogeno, alcoxi C1-6, haloalcoxi C1-3 o CR4aR4bR4c, en el que: (i) R4a, R4b y R4c se eligen con independencia entre alquilo C1-3, alcoxi C1-2, fluoralquilo C1-2, hidroxi-alquilo C1-3, ciano o hidroxi; o (ii) tomados juntos, R4a y R4b juntos son alquileno C2-4 y R4c es hidrogeno, alquilo C1-3, alcoxi C1-2, halogeno, hidroxialquilo C1-3, ciano o fluoralquilo C1-2, o R4a y R4b junto con el átomo de carbono al que están unidos forman un 3-oxetanilo o tetrahidrofuran-2-ilo; o, (iii) o R5 o R3 y R4a juntos son CH2-O o (CH2)2 y junto con los átomos a los que están unidos forman un 2,3-dihidro-benzofurano o un indano y R4b y R4C son alquilo C1-3; R5 es hidrogeno o halogeno o R5 y R4a juntos son CH2-O o (CH)2 y junto con los átomos a los que están unidos forman un 2,3-dihidrobenzofurano o un indano; n con independencia de cada aparicion es un numero de cero a tres; o una sal farmacéuticamente aceptable del mismo. Reivindicacion 20: Un compuesto de la formula 2 en la que: R3 es hidrogeno, alcoxi C1-6, alquilo C1-6, haloalquilo C1-6, haloalcoxi C6 o halogeno, o R3 y R4a juntos son CH2-O o (CH2)2 y junto con los átomos a los que están unidos forman un 2,3-dihidrobenzofurano o un indano; Ar es (a) arilo o (b) heteroarilo, dichos arilo o heteroarilo están opcionalmente sustituidos con independencia de una a tres veces por sustituyentes elegidos entre el grupo formado por hidroxi, alcoxi C1-6, alquilo C1-6, hidroxialquilo C1-6, (alcoxi C1-3) -alquilo C1-6, halogeno, (CH2)NRaRb, ciano, (alcoxi C1-6)-carbonilo, carbamoilo, N-alquilcarbamoílo, N-dialquilcarbamoílo, (CH2)nCO2H, SO2NH2, alquilsulfinilo C1-6 y alquilsulfonilo C1-6; Ra y Rb son con independencia hidrogeno, alquilo C1-6, haloalquilo C1-6, acilo C1-6, alquilsulfonilo C1-6, haloalquilsulfonilo C1-6, cicloalquilsulfonilo C3-7, (cicloalquil C3-7)-alquil-sulfonilo C1-3, (alcoxi C1-6) -alquilsulfonilo C1-6, -SO2-NRcRd, (alquil C1-3) carbamoilo o di (alquil C1-3) -carbamoilo; Rc y Rd son (i) con independencia hidrogeno, alquilo C1-3 o (CH2)2-6NReRf o (ii) junto con el nitrogeno al que están unidos forman (CH2)2X5(CH2)2, en el que X5 es O o NRi y Ri es hidrogeno, alquilo C1-3 acilo C1-3 o alquilsulfonilo C1-3; Re y Rf son con independencia de cada aparicion hidrogeno o alquilo C1-3; R4a y R4b (i) juntos son alquileno C2 y R4c es fluoralquilo C1-2 (ii) o R5 o R3 y R4a juntos son CH2-O o (CH2)2 y junto con los átomos a los que están unidos forman un 2,3-dihidro-benzofurano o un indano y R4b y R4c son alquilo C1-3 R5 es hidrogeno o R5 y R4a juntos son CH2-O o (CH2)2 y junto con los átomos a los que están unidos forman un 2,3-dihidrobenzofurano o un indano; n con independencia de cada aparicion es un numero de cero a tres; o una sal farmacéuticamente aceptable del mismo.
ARP100102180A 2009-06-24 2010-06-22 Compuestos heterociclicos antivirales AR077173A1 (es)

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Country Status (13)

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US (1) US8158631B2 (es)
EP (1) EP2445875A2 (es)
JP (1) JP2012530751A (es)
CN (1) CN102803212A (es)
AR (1) AR077173A1 (es)
AU (1) AU2010264802A1 (es)
BR (1) BRPI1011744A2 (es)
CA (1) CA2762675A1 (es)
IL (1) IL216338A0 (es)
MX (1) MX2011012541A (es)
SG (1) SG176976A1 (es)
TW (1) TW201103545A (es)
WO (1) WO2010149598A2 (es)

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WO2010149598A2 (en) 2010-12-29
IL216338A0 (en) 2012-01-31
AU2010264802A1 (en) 2012-01-19
US8158631B2 (en) 2012-04-17
JP2012530751A (ja) 2012-12-06
EP2445875A2 (en) 2012-05-02
TW201103545A (en) 2011-02-01
WO2010149598A3 (en) 2011-05-19
US20100330032A1 (en) 2010-12-30
CA2762675A1 (en) 2010-12-29
CN102803212A (zh) 2012-11-28
SG176976A1 (en) 2012-02-28

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