AR093403A1 - COMPUESTOS DE PIRIDILO SUSTITUIDOS CON ALQUILAMIDA UTILES COMO MODULADORES DE LAS RESPUESTAS DE IL-12, IL23 Y/O INFa - Google Patents

COMPUESTOS DE PIRIDILO SUSTITUIDOS CON ALQUILAMIDA UTILES COMO MODULADORES DE LAS RESPUESTAS DE IL-12, IL23 Y/O INFa

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Publication number
AR093403A1
AR093403A1 ARP130104094A ARP130104094A AR093403A1 AR 093403 A1 AR093403 A1 AR 093403A1 AR P130104094 A ARP130104094 A AR P130104094A AR P130104094 A ARP130104094 A AR P130104094A AR 093403 A1 AR093403 A1 AR 093403A1
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Argentina
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substituted
alkyl
heteroatoms selected
carbon atoms
membered
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ARP130104094A
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English (en)
Inventor
Zhang Yanlei
S Weinstein David
S Tokarski John
Lin Shuqun
M Moslin Ryan
T Wrobleski Stephen
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Bristol Myers Squibb Co
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Publication of AR093403A1 publication Critical patent/AR093403A1/es

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    • 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
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • 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
    • A61P37/00—Drugs for immunological or allergic disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • 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
    • 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C07D213/82—Amides; Imides in position 3
    • 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
    • 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
    • C07D401/14—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 three or more hetero rings
    • 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
    • C07D405/14—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 three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems

Abstract

Modulación de IL-12, IL-23 y/o IFNa que actúan en Tyk-2 para generar la inhibición de la transducción de señal. Reivindicación 1: Un compuesto caracterizado porque tiene la fórmula (1), o un estereoisómero o una sal de aquel aceptable desde el punto de vista farmacéutico, en donde R¹ es alquilo C₁₋₃ opcionalmente sustituido con 0 - 7 R¹ᵃ; R¹ᵃ es, en cada caso, independientemente hidrógeno, deuterio, F, Cl, Br, CF₃ o CN; R² es un heterociclo de 5 - 14 miembros que contiene 1 - 4 heteroátomos seleccionados de N, O y S, sustituido con 0 - 4 R²ᵃ; R²ᵃ es, en cada caso, independientemente hidrógeno, =O, halo, OCF₃, CN, NO₂, -(CH₂)ʳORᵇ, -(CH₂)ʳSRᵇ, -(CH₂)ʳC(O)Rᵇ, -(CH₂)ʳC(O)ORᵇ, -(CH₂)ʳOC(O)Rᵇ, -(CH₂)ʳNR¹¹R¹¹, -(CH₂)ʳC(O)NR¹¹R¹¹, -(CH₂)ʳNRᵇC(O)Rᶜ, -(CH₂)ʳNRᵇC(O)ORᶜ, -NRᵇC(O)NR¹¹R¹¹, -S(O)ₚNR¹¹R¹¹, -NRᵇS(O)ₚRᶜ, -S(O)ₚRᶜ, alquilo C₁₋₆ sustituido con 0 - 3 Rᵃ, haloalquilo C₁₋₆, alquenilo C₂₋₆ sustituido con 0 - 3 Rᵃ, alquinilo C₂₋₆ sustituido con 0 - 3 Rᵃ, -(CH₂)ʳ-carbociclo de 3 - 14 miembros sustituido con 0 - 1 Rᵃ, -(CH₂)ʳ-heteroarilo de 5 - 7 miembros que comprende átomos de carbono y 1 - 4 heteroátomos seleccionados de N, O y S(O)ₚ, sustituido con 0 - 2 Rᵃ; y -(CH₂)ʳ-heterociclo de 5 - 7 miembros que comprende átomos de carbono o 1 - 4 heteroátomos seleccionados de N, O y S(O)ₚ, sustituido con 0 - 2 Rᵃ; R³ es cicloalquilo C₃₋₁₀ sustituido con 0 - 3 R³ᵃ, arilo C₆₋₁₀ sustituido con 0 - 3 R³ᵃ, un heterociclo de 5 - 10 miembros que contiene 1 - 4 heteroátomos seleccionados de N, O y S, sustituido con 0 - 3 R³ᵃ, o un heteroarilo de 5 - 10 miembros que contiene 1 - 4 heteroátomos seleccionados de N, O y S, sustituido con 0 - 3 R³ᵃ; R³ᵃ es, en cada caso, independientemente hidrógeno, =O, halo, OCF₃, OCHF₂, CF₃, CHF₂, CN, NO₂, -(CH₂)ʳORᵇ, -(CH₂)ʳSRᵇ, -(CH₂)ʳC(O)Rᵇ, -(CH₂)ʳC(O)ORᵇ, -(CH₂)ʳOC(O)Rᵇ, -(CH₂)ʳNR¹¹R¹¹, -(CH₂)ʳC(O)NR¹¹R¹¹, -(CH₂)ʳNRᵇC(O)Rᶜ, -(CH₂)ʳNRᵇC(O)ORᶜ, -NRᵇC(O)NR¹¹R¹¹, -S(O)ₚNR¹¹R¹¹, -NRᵇS(O)ₚRᶜ, -S(O)ₚRᶜ, alquilo C₁₋₆ sustituido con 0 - 3 Rᵃ, alquenilo C₂₋₆ sustituido con 0 - 3 Rᵃ, alquinilo C₂₋₆ sustituido con 0 - 3 Rᵃ, haloalquilo C₁₋₆, -(CH₂)ʳ-carbociclo de 3 - 14 miembros sustituido con 0 - 3 Rᵃ, -(CH₂)ʳ-heteroarilo de 5 - 7 miembros que comprende átomos de carbono y 1 - 4 heteroátomos seleccionados de N, S u O sustituido con 0 - 3 Rᵃ, o -(CH₂)ʳ-heterociclo de 5 - 10 miembros que comprende átomos de carbono y 1 - 4 heteroátomos seleccionados de N, O y S(O)ₚ, sustituido con 0 - 3 Rᵃ; o dos R³ᵃ, junto con los átomos a los que están unidos, se combinan para formar un anillo fusionado, en donde el anillo se selecciona de fenilo y un heteroarilo o heterociclo de 5 - 7 miembros cada uno de los cuales comprende átomos de carbono y 1 - 4 heteroátomos seleccionados de N, S u O; R⁴ y R⁵ son independientemente hidrógeno, alquilo C₁₋₄ sustituido con 0 - 1 Rᶠ, (CH₂)ʳ-fenilo sustituido con 0 - 3 Rᵈ o -(CH₂)-heterociclo de 5 - 7 miembros que comprende átomos de carbono y 1 - 4 heteroátomos seleccionados de N, O y S(O)ₚ; R¹¹ es, en cada caso, independientemente hidrógeno, alquilo C₁₋₆ sustituido con 0 - 3 Rᶠ, CF₃, a cicloalquilo C₃₋₁₀ sustituido con 0 - 3 Rᶠ, (CH)ʳ-fenilo sustituido con 0 - 3 Rᵈ o -(CH₂)ʳ-heterociclo de 5 - 7 miembros que comprende átomos de carbono y 1 - 4 heteroátomos seleccionados de N, O y S(O)ₚ, sustituido con 0 - 3 Rᵈ; Rᵃ es, en cada caso, independientemente hidrógeno, =O, F, Cl, Br, OCF₃, CF₃, CHF₂, CN, NO₂, -(CH₂)ʳORᵇ, -(CH₂)ʳSRᵇ, -(CH₂)ʳC(O)Rᵇ, -(CH₂)ʳC(O)ORᵇ, -(CH₂)ʳOC(O)Rᵇ, -(CH₂)ʳNR¹¹R¹¹, -(CH₂)ʳC(O)NR¹¹R¹¹, -(CH₂)ʳNRᵇC(O)Rᶜ, -(CH₂)ʳNRᵇC(O)ORᶜ, -NRᵇC(O)NR¹¹R¹¹, -S(O)ₚNR¹¹R¹¹, -NRᵇS(O)ₚRᶜ, -S(O)Rᶜ, -S(O)₂Rᶜ, alquilo C₁₋₆ sustituido con 0 - 3 Rᶠ, haloalquilo C₁₋₆, alquenilo C₂₋₆ sustituido con 0 - 3 Rᵃ, alquinilo C₂₋₆ sustituido con 0 - 3 Rᵃ, -(CH₂)ʳ-carbociclo de 3 - 14 miembros, -(CH₂)ʳ-heteroarilo de 5 - 7 miembros que comprende átomos de carbono y 1 - 4 heteroátomos seleccionados de N, O y S(O)ₚ sustituido con 0 - 3 Rᶠ; o -(CH₂)ʳ-heterociclo de 5 - 7 miembros que comprende átomos de carbono y 1 - 4 heteroátomos seleccionados de N, O y S(O)ₚ sustituido con 0 - 3 Rᶠ; de manera alternativa, dos Rᵃ en átomos de carbono adyacentes o en el mismo átomo de carbono forman un acetal cíclico de la fórmula -O-(CH₂)ₙ-O- u -O-CF₂-O-, en donde n se selecciona de 1 ó 2; Rᵇ es hidrógeno, alquilo C₁₋₆ sustituido con 0 - 3 Rᵈ, haloalquilo C₁₋₆, cicloalquilo C₃₋₆ sustituido con 0 - 2 Rᵈ, o -(CH₂)ʳ-heterociclo de 5 - 7 miembros que comprende átomos de carbono y 1 - 4 heteroátomos seleccionados de N, O y S(O)ₚ sustituido con 0 - 3 Rᶠ o (CH₂)ʳ-fenilo sustituido con 0 - 3 Rᵈ; Rᶜ es alquilo C₁₋₆ sustituido con 0 - 3 Rᶠ, (CH₂)ʳ-cicloalquilo C₃₋₆ sustituido con 0 - 3 Rᶠ, (CH₂)ʳ-fenilo sustituido con 0 - 3 Rᶠ; o Rᵈ es, en cada caso, independientemente hidrógeno, F, Cl, Br, OCF₃, CF₃, CN, NO₂, -ORᵉ, -(CH₂)ʳC(O)Rᶜ, -NRᵉRᵉ, -NRᵉC(O)ORᶜ, alquilo C₁₋₆ o (CH₂)ʳ-fenilo sustituido con 0 - 3 Rᶠ; Rᵉ se selecciona de hidrógeno, alquilo C₁₋₆, cicloalquilo C₃₋₆ o (CH₂)ʳ-fenilo sustituido con 0 - 3 Rᶠ; Rᶠ es, en cada caso, independientemente hidrógeno, halo, CN, NH₂, NH(alquilo C₁₋₆), N(alquilo C₁₋₆)₂, OH, cicloalquilo C₃₋₆, CF₃, O(alquilo C₁₋₆), fenilo; o Rᶠ es, en cada caso, independientemente un -(CH₂)ʳ-heteroarilo de 5 - 10 miembros opcionalmente sustituido que comprende átomos de carbono y 1 - 4 heteroátomos seleccionados de N, O y S(O) o cicloalquilo C₃₋₆, cada grupo opcionalmente sustituido con halo, CN, CF₃, alquilo C₁₋₆ ó O(alquilo C₁₋₆); p es 0, 1 ó 2; y r es 0, 1, 2, 3 ó 4; siempre que el compuesto de la fórmula (1) no sea un compuesto del grupo de fórmulas (2).
ARP130104094A 2012-11-08 2013-11-07 COMPUESTOS DE PIRIDILO SUSTITUIDOS CON ALQUILAMIDA UTILES COMO MODULADORES DE LAS RESPUESTAS DE IL-12, IL23 Y/O INFa AR093403A1 (es)

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US (1) US9315494B2 (es)
EP (1) EP2922841B8 (es)
JP (1) JP6259463B2 (es)
KR (1) KR102233252B1 (es)
CN (1) CN104781252B (es)
AR (1) AR093403A1 (es)
AU (1) AU2013341185B2 (es)
BR (1) BR112015010244A8 (es)
CA (1) CA2890929A1 (es)
EA (1) EA028526B1 (es)
IL (1) IL238554A0 (es)
MX (1) MX2015005272A (es)
SG (1) SG11201503396UA (es)
TW (1) TWI620737B (es)
WO (1) WO2014074660A1 (es)

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CA2890929A1 (en) 2014-05-15
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EP2922841B8 (en) 2017-08-02
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