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AR072824A1 - Derivados de piridina con accion antivirica - Google Patents

Derivados de piridina con accion antivirica

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Publication number
AR072824A1
AR072824A1 ARP090102751A ARP090102751A AR072824A1 AR 072824 A1 AR072824 A1 AR 072824A1 AR P090102751 A ARP090102751 A AR P090102751A AR P090102751 A ARP090102751 A AR P090102751A AR 072824 A1 AR072824 A1 AR 072824A1
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AR
Argentina
Prior art keywords
alkyl
alkoxy
hydrogen
amino
optionally substituted
Prior art date
Application number
ARP090102751A
Other languages
English (en)
Inventor
Eric Brian Sjogren
David Scott Carter
Francisco Xavier Talamas
Kenneth Albert Brameld
Elbert Chin
Vicente Fidalgo Javier De
Ryan Craig Schoenfeld
Jim Li
Original Assignee
Hoffmann La Roche
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Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche
Publication of AR072824A1 publication Critical patent/AR072824A1/es

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • 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
    • 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
    • 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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • 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
    • C07D405/10—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 linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Virology (AREA)
  • Engineering & Computer Science (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Molecular Biology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Son inhibidores de la polimerasa NS5b del virus de la hepatitis C (HCV). Se describen también composiciones y métodos para tratar una infeccion de HCV y para inhibir la replicacion del HCV. Reivindicacion 1: Un compuesto de formula (1) en la que R1 es hidrogeno, alquilo C1-6, haloalquilo C1-6, halogeno, hidroxi, alcoxi C1-6, haloalcoxi C1-6, ciano, NRaRb, carboxi, (alcoxi C1-3)carbonilo, carboxamido, amino-alquilo C1-3, (acilamino C1-3)-alquilo C1-3, hidroxialcoxi C1-6; R2 se elige entre el grupo formado por: (a) -[C(R8)2]p-Ar1, (b) -[C(R8)2]p-OAr1, (c) -(CH2)mC(=O)X, (d) -NR7C(=O)Ar4, (e) -alquilo C1-6, (f) -haloalquilo C1-6, (g) alcoxi C1-6, (h) haloalcoxi C1-6, (i) hidroxialquilo C1-6, (j) hidroxi, (k) halogeno, (l) hidrogeno, (m) fenoxisulfonilo, (n) -O(CH2)mAr1, (o) -[C(R8)2]p-NReRf, (p) (E)- o (Z)-R10C=CR10Ar1, (q) -CsCAr1, en los que R8 con independencia de su aparicion es hidrogeno, carboxilo, (alcoxi C1-3)carbonilo, carboxamido, hidroxialquilo C1-3, alquilo C1-3, -(CH2)rNRgRh o ciano, R10 con independencia de su aparicion es hidrogeno, alquilo C1-6, hidroxialquilo C1-6, ciano, (alcoxi C1-3)carbonilo, carboxamido o (alcoxi C1-3)-alquilo C1-6, p es un numero de cero a cuatro y r es un numero de 1 a 3; Ar1 es fenilo, naftilo, piridinilo, pirimidinilo, pirazinilo, piridazinilo, quinolinilo, opcionalmente sustituidos con independencia de una a tres veces por sustituyentes elegidos entre el grupo formado por (a) hidroxi, (b) alcoxi C1-6, (c) alquilo C1-6, (d) hidroxialquilo C1-10, del que uno o dos átomos de carbono pueden haberse remplazado opcionalmente por oxígeno, con la condicion de que los átomos reemplazantes no formen un enlace oxígeno-oxígeno, (e) (alcoxi C1-3)-alquilo C1-6, (f) halogeno, (g) ciano, (h) (alcoxi C1-6)carbonilo, (i) alquilsulfonilo C1-6, (j) X1(CH2)1-6CO2H, (k) (acilamino C1-3)alquilo C1-6, (l) (CH2)nNRaRb, (m) (CH2)nCONRaRb, (n) -O(CH2)nCO-NRaRb, (o) X2(CH2)2-6nRgRh, (p) X1-hidroxialquilo C1-6, (q) haloalquilo C1-6 o (r) carboxilo; Ra y Rb son (i) con independencia de su aparicion (a) hidrogeno, (b) alquilo C1-6, (c) haloalquilo C1-3, (d) acilo C1-6, (e) alquilsulfonilo C1-6, (f) haloalquilsulfonilo C1-6, (g) cicloalquilsulfonilo C3-7, (h) (cicloalquil C3-7)-alquilsulfonilo C1-3, (i) (alcoxi C1-6)-alquilsulfonilo C1-6, (j) (CH2)1-3NRgRh, (k) SO2(CH2)1-6NRgRh, en los que Rg y Rh tienen los significados definidos antes, (l) sulfamoilo, (m) (alquil C1-3)-sulfamoilo, (n) di(alquil C1-3)-sulfamoilo, (o) carbamoilo, (p) (alquil C1-3)carbamoilo, (q) di(alquil C1-3)-carbamoilo, (r) benzoílo, dicho benzoílo está opcionalmente sustituido con independencia por uno o dos restos elegidos entre el grupo formado por amino, halogeno, alquilo C1-6 o (alquil C1-3)sulfonilamido, (s) carboxi(alquil C1-6)sulfonilo, (t) hidroxialquilsulfonilo, o (ii) Ra y Rb junto con el átomo de nitrogeno al que están unidos forman (a) una amina cíclica opcionalmente sustituida, (b) (CH2)2-3OC(O), o (c) 2-oxo-oxazolidina; Re y Rf si (i) se toman con independencia se eligen entre (a) hidrogeno, (b) alquilo C1-3, (c) cicloalquilo C4-7, (d) (cicloalquil C3-7)carbonilo, (e) fenilo, dichos restos cicloalquilo y fenilo están opcionalmente sustituidos de una a tres veces por restos elegidos entre (alquil C1-3)sulfonilamido, alquilo C1-3, alcoxi C1-3 o halogeno, o si (ii) se toman junto con el nitrogeno al que están unidos forman una amina cíclica sustituida con independencia de una a tres veces por restos elegidos entre (alquil C1-3)sulfonilamido, alquilo C1-3, alcoxi C1-3, o halogeno; X es OH, alcoxi C1-6, NRcRd o Ar3; Ar3 es fenilo opcionalmente sustituido de una a tres veces por restos elegidos entre el grupo formado por: (a) halogeno, (b) hidroxi, (c) hidroxialquilo C1-3, (d) amino, (e) amino-alquilo C1-3, (f) alquilamino C1-3, (g) alquilamino C1-3-alquilo C1-3, (h) di(alquil C1-3)-amino, (i) di(alquil C1-3)-amino-alquilo C1-3, (j) carboxamido, (k) alquilsulfonilamido C1-6, (l) (alquilsulfonilamido C1-6)-alquilo C1-3, (m) NR7-(alquil C1-3)-alquilsulfonamido C1-6, (n) alquilo C1-6, (o) (alcoxi C1-6)carbonilo y (p) carboxilo; Rc y Rd son (i) con independencia de su aparicion; (a) hidrogeno, (b) Ar2, (c) Ar2-alquilo C1-6, (d) cicloalquilo C3-6 opcionalmente sustituido por di(alquil C1-3)-amino, alquilsulfonamido C1-6 o hidroxialquilo C1-3, (e) (alquil C1-6)-cicloalquilo C3-7, (f) (alcoxi C1-3)-alquilo C1-3, (q) piridinilo o piridinil-alquilo C1-6, dicho piridinilo está opcionalmente sustituido por amino, alquilamino C1-3, (dialquil C1-3)amino, alquilsulfonilamido C1-6, sulfamoilo, (alquil C1-3)-sulfamoilo, di(alquil C1-3)-sulfamoilo, (h) tienilo opcionalmente sustituido por alquilo C1-3, (i) heterociclilo o heterociclil-alquilo C1-6, dicho grupo heterociclilo es la pirrolidina o piperidina, dicho grupo heterociclilo está opcionalmente sustituido por alquilo C1-3 u oxo, (j) (alquil C1-3)-imidazol-4-ilo o (k) (CH2)2-4NRgRh; o (ii) Rc y Rd junto con el nitrogeno al que están unidos forman un pirrolidinilo o piperidinilo, ambos están opcionalmente sustituidos por alquilo C1-3, hidroxi o hidroxi-alquilo C1-3; Ar2 es fenilo opcionalmente sustituido de una a tres veces por restos elegidos con independencia entre el grupo formado por (a) alquilo C1-3, (b) amino, (c) amino-alquilo C1-3, (d) alquilamino C1-3, (e) (alquilamino C1-3)-alquilo C1-3, (f) di(alquil C1-3)-amino, (g) OCH2CONRgRh, (h) (alquil C1-3)sulfonilamido, (i) (alquilsulfonamido C1-3)-alquilo C1-3, (j) N-(alquil C1-3)-alquilsulfonamido C1-6, (k) hidroxialquilo C1-3 y (l) hidroxi; Ar4 es fenilo, piridinilo, pirazinilo, piridazinilo o pirimidinilo, cada uno de ellos está opcionalmente sustituido de una a tres veces por restos elegidos con independencia de su aparicion entre el grupo formado por: (a) amino, (b) alquilamino C1-3, (c) di(alquil C1-3)-amino, (d) haloalquilamino C1-3, (e) alquilsulfonilamido C1-6, (f) sulfamoilo, (g) (alquil C1-3)-sulfamoilo, (h) di(alquil C1-3)-sulfamoilo, (i) (alquil-sulfonilamido C1-6)-alquilo C1-3, (j) NR7-(alquil C1-3)-alquil-sulfonamido C1-6, (k) halogeno, (l) alquilo C1-3, (m) alcoxi C1-3, (n) acilamino C1-6, (o) hidroxi, (p) (CH2)nCONRaRb, (q) -O(CH2)nCONRaRb, (r) -O(CH2)nNRiRj en el que Ri y Rj son con independencia hidrogeno o alquilo C1-3, (s) -NRi(CH2)nORj que Ri y Rj son con independencia hidrogeno o alquilo C1-3, (t) haloalquilo C1-3, (u) (alcoxi C1-3)-alcoxi C1-6, (v) cicloalquilamina C3-6; R3 es hidrogeno, alquilo C1-6, haloalquilo C1-6, alcoxi C1-6, haloalcoxi C1-6, (alcoxi C1-3)-alcoxi C1-6, halogeno, O(CH2)2-6X3 en el que X3 es OH o N(R7)2; o R3 y R4a juntos forman un CH2-O y junto con los átomos a los que están unidos forman un 2,3-dihidrobenzofurano o un indano; R4a, R4b y R4c, (a) si se toman con independencia se eligen con independencia entre (i) alquilo C1-3, (ii) alcoxi C1-2, (iii) fluoroalquilo C1-2, (iv) hidroxialquilo C1-3, (v) hidroxi, (vi) CO2H, (vii) (alcoxi C1-6)-carbonilo, (viii) ciano o (ix) N(R7)2 o (b) si se toman juntos, (i) R4a y R4b juntos son metileno C2-4 y R4c es hidrogeno, alquilo C1-3, hidroxialquilo C1-3, alcoxi C1-2, halogeno, ciano o fluoroalquilo C1-2 o (ii) R4a y R4b junto con el carbono al que están unidos forman un 3-oxetanilo; R4c es hidrogeno, alquilo C1-3, o (c) o bien (i) R5 y R4a o bien (ii) 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, o (d) R4a, R4b, R4c junto con el carbono al que están unidos forman un ciclopropilo, trifluorometilo o 2,2,2-trifluoroetilo; R5 es hidrogeno, halogeno, alquilo C1-6, hidroxi o R5 y R4a juntos forman un CH2-O y junto con los átomos a los que están unidos forman un 2,3-dihidrobenzofurano o un indano; R6 es (a) halogeno, (b) alquilo C1-6 del que uno o dos átomos de carbono no adyacentes pueden haberse reemplazado por oxígeno, (c) haloalquilo C1-3, (d) alcoxi C1-3, (e) X1-hidroxi-alquilo C2-6 del que uno o dos átomos de carbono no adyacentes pueden haberse reemplazado por oxígeno, (f) ciano-alquilo C1-3, (g) X1(CH2)1-6CO2H o (h) X1(CH2)2-6NRgRh; R7 con independencia de su aparicion es hidrogeno o alquilo C1-3; R9 es hidrogeno, CH2OH, CH(Me)OH, CH(Me)OR9a o CH2OR9a, en los que R9a es (a) CO(CH2)sCO2H en el que s es un numero de uno a cuatro, (b) C(O)CHR9bNHR9c en el que R9b es hidrogeno, metilo, isopropilo, isobutilo, sec-butilo, fenilo o 4-hidroxi-fenilo y R9c es hidrogeno o (alcoxi C1-6)carbonilo, o R9b y R9c juntos forman un (CH2)3, (c) -P(O)(OH)2 o (d) COR11 en el que R11 es alquilo C1-6, piperidin-4-il-metilo o un arilo opcionalmente sustituido; X1 es O, NR7 o un enlace; X2 es O o NR7; Rg y Rh son con independencia hidrogeno o alquilo C1-6 o Rg y Rh junto con el nitrogeno al que están unidos forman una amina cíclica opcionalmente sustituida; m es un numero de cero a tres; n con independencia de su aparicion es un numero de cero a dos; o las sales farmacéuticamente aceptables del mismo.
ARP090102751A 2008-07-23 2009-07-20 Derivados de piridina con accion antivirica AR072824A1 (es)

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US8284708P 2008-07-23 2008-07-23
US20792509P 2009-02-17 2009-02-17
US17983709P 2009-05-20 2009-05-20

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US (1) US8273773B2 (es)
EP (1) EP2307372B1 (es)
JP (1) JP2011528686A (es)
KR (1) KR20110033291A (es)
CN (1) CN102099335A (es)
AR (1) AR072824A1 (es)
AT (1) ATE555096T1 (es)
AU (1) AU2009273327A1 (es)
BR (1) BRPI0916233A2 (es)
CA (1) CA2730517A1 (es)
CL (1) CL2011000136A1 (es)
ES (1) ES2383273T3 (es)
IL (1) IL209696A0 (es)
MX (1) MX2011000656A (es)
PE (1) PE20110409A1 (es)
TW (1) TW201008922A (es)
WO (1) WO2010010017A1 (es)
ZA (1) ZA201009183B (es)

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