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AR092809A1 - 3,5-diaminopirazol como inhibidor de quinasa - Google Patents

3,5-diaminopirazol como inhibidor de quinasa

Info

Publication number
AR092809A1
AR092809A1 ARP130100838A ARP130100838A AR092809A1 AR 092809 A1 AR092809 A1 AR 092809A1 AR P130100838 A ARP130100838 A AR P130100838A AR P130100838 A ARP130100838 A AR P130100838A AR 092809 A1 AR092809 A1 AR 092809A1
Authority
AR
Argentina
Prior art keywords
heterocyclyl
alkyl
heteroaryl
cycloalkyl
aryl
Prior art date
Application number
ARP130100838A
Other languages
English (en)
Original Assignee
Axikin Pharmaceuticals Inc
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 Axikin Pharmaceuticals Inc filed Critical Axikin Pharmaceuticals Inc
Publication of AR092809A1 publication Critical patent/AR092809A1/es

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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/415—1,2-Diazoles
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    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/415—1,2-Diazoles
    • A61K31/4155—1,2-Diazoles non condensed and containing further heterocyclic rings
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    • A61K31/415—1,2-Diazoles
    • A61K31/416—1,2-Diazoles condensed with carbocyclic ring systems, e.g. indazole
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Abstract

Útiles para modular la actividad de la quinasa regulada en EPOC, y composiciones farmacéuticas de aquellos. En la presente también se proveen métodos de uso para tratar, prevenir o aliviar uno o más síntomas de un trastorno, enfermedad o afección mediados por RC quinasa. Reivindicación 1: Un compuesto de la fórmula (1), o un estereoisómero, un enantiómero, una mezcla de enantiómeros, una mezcla de diastereómeros o una variante isotópica de aquel; o una sal, un solvato, un hidrato o un profármaco de aquel aceptables desde el punto de vista farmacéutico, en donde: R¹ es hidrógeno, alquilo C₁₋₆, alquenilo C₂₋₆ alquinilo C₂₋₆, cicloalquilo C₃₋₁₀, arilo C₆₋₁₄, heteroarilo o heterociclilo; R² es cicloalquilo C₃₋₁₀, arilo C₆₋₁₄, heteroarilo o heterociclilo; R³ es hidrógeno, alquilo C₁₋₆, alquenilo C₂₋₆ alquinilo C₂₋₆ cicloalquilo C₃₋₁₀, arilo C₆₋₁₄, heteroarilo, heterociclilo, -C(O)R¹ᵃ, -C(O)OR¹ᵃ, -C(O)NR¹ᵇR¹ᶜ, -C(NR¹ᵃ)NR¹ᵇR¹ᶜ, -S(O)R¹ᵃ, -S(O)₂R¹ᵃ, -S(O)NR¹ᵇR¹ᶜ o -S(O)₂NR¹ᵇR¹ᶜ; R⁴ es ciano, aminocarbonilo, C(O)N=CR⁴ᵃR⁴ᵇ o -C(O)NR⁴ᵃR⁴ᵇ; en donde: R⁴ᵃ es alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₁₀, arilo C₆₋₁₄, heteroarilo o heterociclilo; R⁴ᵇ es independientemente hidrógeno, alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₁₀, arilo C₆₋₁₄, heteroarilo heterociclilo, C(O)R¹ᵃ, -C(O)OR¹ᵃ, -C(O)NR¹ᵇR¹ᶜ, -C(NR¹ᵃ)NR¹ᵇR¹ᶜ, -S(O)R¹ᵃ, -S(O)₂R¹ᵃ, -S(O)NR¹ᵇR¹ᶜ o -S(O)₂NR¹ᵇR¹ᶜ; R⁵ es -N(R⁵ᵉ)CR⁵ᵃR⁵ᶜR⁵ᵈ; en donde: R⁵ᵃ es cicloalquilo C₃₋₁₀, arilo C₁₋₄, heteroarilo o heterociclilo; R⁵ᶜ y R⁵ᵈ son, cada uno independientemente, hidrógeno, halo, alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₁₀, arilo C₆₋₁₄, heteroarilo o heterociclilo; y R⁵ᵉ es hidrógeno, alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₁₀, arilo C₆₋₁₄, heteroarilo, heterociclilo, -C(O)R¹ᵃ, -C(O)OR¹ᵃ, -C(O)NR¹ᵇR¹ᶜ, -C(NR¹ᵃ)NR¹ᵇR¹ᶜ, -S(O)R¹ᵃ, -S(O)₂R¹ᵃ, -S(O)NR¹ᵇR¹ᶜ o -S(O)₂NR¹ᵇR¹ᶜ; y cada R¹ᵃ, R¹ᵇ, R¹ᶜ y R¹ᵈ es, independientemente, hidrógeno, alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₁₀, arilo C₆₋₁₄, heteroarilo o heterociclilo; o R¹ᵃ y R¹ᶜ, junto con lo átomos C y N a los que están unidos, forman un heterociclilo; o R¹ᵇ y R¹ᶜ, junto con el átomo N al que están unidos, forman un heterociclilo; en donde cada alquilo, alquenilo, alquinilo, cicloalquilo, arilo, heteroarilo y heterociclilo se sustituye opcionalmente con uno o más sustituyentes Q, en donde cada Q se selecciona independientemente de (a) oxo, ciano, halo, nitro y pentafluorosulfanilo; (b) alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆ cicloalquilo C₃₋₁₀, arilo C₆₋₁₄, aralquilo C₇₋₁₅, heteroarilo, heteroaralquilo, heterociclilo y heterociclil-alquilo C₁₋₆, cada uno de los cuales también se sustituye opcionalmente con uno o más, en una forma de realización 1, 2, 3 ó 4 sustituyentes Qᵃ; y (c) -B(Rᵃ)ORᵈ, -B(ORᵃ)ORᵈ, -C(O)Rᵃ, -C(O)ORᵃ, -C(O)NRᵇRᶜ, -C(NRᵃ)NRᵇRᶜ, -ORᵃ, -OC(O)Rᵃ, -OC(O)ORᵃ, -OC(O)NRᵇRᶜ, -OC(=NRᵃ)NRᵇRᶜ, -OS(O)Rᵃ, -OS(O)₂Rᵃ, -OS(O)NRᵇRᶜ, -OS(O)₂NRᵇRᶜ, -NRᵇRᶜ, -NRᵃC(O)Rᵈ, -NRᵃC(O)ORᵈ, -NRᵃC(O)NRᵇRᶜ, -NRᵃC(=NRᵈ)NRᵇRᶜ, -NRᵃS(O)Rᵈ, -NRᵃS(O)₂Rᵈ, -NRᵃS(O)NRᵇRᶜ, -NRᵃS(O)₂NRᵇRᶜ, -P(O)RᵃRᵈ, -P(O)(ORᵃ)Rᵈ, -P(O)(ORᵃ)(ORᵈ), -SRᵃ, -S(O)Rᵃ, -S(O)₂Rᵃ, -S(O)NRᵇRᶜ y -S(O)₂NRᵇRᶜ, en donde cada Rᵃ, Rᵇ, Rᶜ y Rᵈ es independientemente (i) hidrógeno; (ii) alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₁₀, arilo C₆₋₁₄, aralquilo, heteroarilo, heteroaralquilo, heterociclilo o heterociclil-alquilo C₁₋₆, cada uno opcionalmente sustituido con uno o más, en una forma de realización 1, 2, 3 ó 4 sustituyentes Qᵃ; o (iii) Rᵇ y Rᶜ, junto con el átomo N al que están unidos, forman un heterociclilo opcionalmente sustituido con uno o más, en una forma de realización, 1, 2, 3 ó 4 sustituyentes Qᵃ; en donde cada Qᵃ se selecciona independientemente del grupo que consiste en (a) oxo, ciano, halo, nitro y pentafluorosulfanilo; (b) alquilo C₁₋₆, alquenilo C₂₋₆ alquinilo C₂₋₆, cicloalquilo C₃₋₁₀, arilo C₆₋₁₄, aralquilo C₇₋₁₅, heteroarilo, heteroaralquilo, heterociclilo y heterociclil-alquilo C₁₋₆; y (c) -B(Rᵉ)ORᵍ, -B(ORᵉ)ORᵍ, -C(O)Rᵉ, -C(O)ORᵉ, -C(O)NRᶠRᵍ, -C(NRᵉ)NRᶠRᵍ, -ORᵉ, -OC(O)Rᵉ, -OC(O)ORᵉ, -OC(O)NRᶠRᵍ, -OC(=NRᵉ)NRᶠRᵍ, -OS(O)Rᵉ, -OS(O)₂Rᵉ, -OS(O)NRᶠRᵍ, -OS(O)₂NRᶠRᵍ, -NRᶠRᵍ, -NRᵉC(O)₂Rʰ, -NRᵉC(O)ORᶠ, -NRᵉC(O)NRᶠRᵍ, -NRᵉC(=NRʰ)NRᶠRᵍ, -NRᵉS(O)Rʰ, -NRᵉS(O)₂Rʰ, -NRᵉS(O)NRᶠRᵍ, -NRᵉS(O)₂RᶠRᵍ, -P(O)RᵉRʰ, -P(O)(ORᵉ)Rʰ, -P(O)(ORᵉ)(ORʰ), -SRᵉ, -S(O)Rᵉ, -S(O)₂Rᵉ, -SF₅, -S(O)NRᶠRᵍ y -S(O)₂NRᶠRᵍ; en donde cada Rᵉ, Rᶠ, Rᵍ y Rʰ es, independientemente (i) hidrógeno; (ii) alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₁₀, arilo C₆₋₁₄, aralquilo C₇₋₁₅, heteroarilo, heteroaralquilo, heterociclilo, o heterociclil-alquilo C₁₋₆; o (iii) Rᶠ y Rᵍ, junto con el átomo N al que están unidos, forman un heterociclilo.
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