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AR087355A1 - Derivados de piridin-2(1h)-ona como inhibidores de jak - Google Patents

Derivados de piridin-2(1h)-ona como inhibidores de jak

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Publication number
AR087355A1
AR087355A1 ARP120102737A ARP120102737A AR087355A1 AR 087355 A1 AR087355 A1 AR 087355A1 AR P120102737 A ARP120102737 A AR P120102737A AR P120102737 A ARP120102737 A AR P120102737A AR 087355 A1 AR087355 A1 AR 087355A1
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AR
Argentina
Prior art keywords
group
cycloalkyl
linear
hydroxyalkyl
haloalkyl
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ARP120102737A
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English (en)
Inventor
Paul Robert Eastwood
Taa Jordi Bach
Santacana Lluis Miquel Pages
Original Assignee
Almirall Sa
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Application filed by Almirall Sa filed Critical Almirall Sa
Publication of AR087355A1 publication Critical patent/AR087355A1/es

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    • 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
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
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    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
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Abstract

Se describen un procedimiento para su preparación, composiciones farmacéuticas que los comprenden y su uso en terapia como inhibidores de quinasas Janus (JAK).Reivindicación 1: Un compuesto de fórmula (1), o una sal farmacéuticamente aceptable, o solvato, o N-óxido, o estereoisómero o derivado deuterado del mismo, en donde: m es 0, 1, 2 ó 3; cada uno de X e Y independientemente representa un átomo de nitrógeno o un grupo -CR6, en donde al menos uno de X e Y representa un grupo -CR6; cada uno de A y B representa independientemente un átomo de nitrógeno o un grupo -CR7, en donde al menos uno de A y B representa un grupo -CR7; D representa un átomo de nitrógeno o un grupo -CR5, en donde cuando uno de A y B representa un átomo de nitrógeno, D representa un grupo -CR5; W representa un grupo enlazador seleccionado de un grupo -NR8-, un grupo -(CR9R10)-, -O- o -S-; R1 representa un átomo de hidrógeno, un grupo alquilo lineal o ramificado C1-6, un grupo haloalquilo C1-4, un grupo hidroxialquilo C1-4, un grupo alcoxi C1-4, un grupo cicloalquilo C3-10, un grupo cicloalquenilo C3-10, un grupo arilo monocíclico o bicíclico C6-14, un grupo heteroarilo de 5 a 14 miembros que contiene al menos un heteroátomo seleccionado de O, S y N, o un grupo heterocíclico de 5 a 14 miembros que contiene al menos un heteroátomo seleccionado de O, S y N, en donde los grupos cicloalquilo, cicloalquenilo, arilo, heteroarilo y heterociclilo están no sustituidos o sustituidos con uno o más sustituyentes seleccionados de un átomo de halógeno, un grupo ciano, un grupo alquilo lineal o ramificado C1-6, un grupo haloalquilo C1-4, un grupo hidroxialquilo C1-4, un grupo alquilsulfonilo C1-4, un grupo cicloalquilo C3-7, un grupo fenilo, un grupo piridilo, un grupo pirimidinilo o un grupo piperidilo; cada uno de R2 y R7 independientemente representa un átomo de hidrógeno, un átomo de halógeno, un grupo ciano, un grupo alquilo lineal o ramificado C1-6, un grupo haloalquilo C1-4, un grupo hidroxialquilo C1-4, un grupo cicloalquilo C3-10, un grupo cicloalquenilo C3-10, un grupo arilo monocíclico o bicíclico C6-14, un grupo heteroarilo de 5 a 14 miembros que contiene al menos un heteroátomo seleccionado de O, S y N, un grupo heterocíclico de 5 a 14 miembros que contiene al menos un heteroátomo seleccionado de O, S y N, o un grupo bicíclico que es un grupo monocíclico arilo C6-9 o heteroarilo de 5 a 9 miembros condensado con un grupo cicloalquilo o heterocíclico de 5 a 9 miembros, donde dicho grupo heteroarilo o heterocíclico contiene al menos un heteroátomo seleccionado de O, S y N, en donde los grupos cicloalquilo, cicloalquenilo, arilo, heteroarilo y heterociclilo, y el grupo bicíclico que es un grupo monocíclico arilo C6-9 o heteroarilo de 5 a 9 miembros condensado con un grupo cicloalquilo o heterocíclico de 5 a 9 miembros, están no sustituidos o sustituidos con uno o más sustituyentes seleccionados de un átomo de halógeno; un grupo ciano; un grupo alquilo lineal o ramificado C1-6 un grupo haloalquilo C1-4 un grupo hidroxialquilo C1-4 un grupo cicloalquilo C3-7 un grupo arilo monocíclico o bicíclico C6-14 un grupo heteroarilo de 5 a 14 miembros que contiene al menos un heteroátomo seleccionado de O, S y N; un grupo heterocíclico de 5 a 14 miembros que contiene al menos un heteroátomo seleccionado de O, S y N; un grupo -(CH2)1-3CN; un grupo -(CH2)nOR11; un grupo -NR11R12; un grupo -NR11C(O)-(CH2)n-R12; un grupo -NR11C(O)-(CH2)n-NR12R13; un grupo -C(O)-(CH2)1-3-CN; un grupo -C(O)-(CH2)n-R11; un grupo -(CH2)n’-C(O)-(CH2)n-NR11R12; un grupo -(CH2)n’-S(O)2(CH2)nR11; un grupo -(CH2)n’-S(O)2(CH2)nNR11R12; un grupo -NR11S(O)2(CH2)nR12 o un grupo -NR11S(O)2(CH2)nNR12R13; en donde cada n’ y n son 0, 1 ó 2; en donde dicho grupo arilo monocíclico o bicíclico C6-14 está no sustituido o sustituido adicionalmente con uno o más grupos carboxilo; cada uno de R3 y R4 independientemente representa un átomo de hidrógeno, un grupo haloalquilo C1-4, un grupo hidroxialquilo C1-4 o un grupo alquilo lineal o ramificado C1-6, donde dicho grupo alquilo está no sustituido o sustituido con uno o más sustituyentes seleccionados de un grupo alcoxi C1-4, un grupo ciano, un grupo cicloalquilo C3-7, un grupo fenilo, un grupo piridilo, un grupo pirimidinilo o un grupo piperidilo; cada uno de R5 y R6 independientemente representa un átomo de hidrógeno, un átomo de halógeno, un grupo ciano, un grupo alquilo lineal o ramificado C1-6, un grupo haloalquilo C1-4, un grupo hidroxialquilo C1-4, un grupo cicloalquilo C3-10, un grupo cicloalquenilo C3-10, un grupo arilo monocíclico o bicíclico C6-14, un grupo heteroarilo de 5 a 14 miembros que contiene al menos un heteroátomo seleccionado de O, S y N, o un grupo heterocíclico de 5 a 14 miembros que contiene al menos un heteroátomo seleccionado de O, S y N, un grupo -(CH2)nOR11; un grupo -NR11R12; un grupo -NR11C(O)-(CH2)n-R12; un grupo -NR11C(O)-(CH2)n-NR12R13; un grupo -C(O)-(CH2)1-3-CN; un grupo -C(O)-(CH2)n-R11; un grupo -C(O)-(CH2)n-NR11R12; un grupo -S(O)2(CH2)nR11; un grupo -S(O)2(CH2)nNR11R12; un grupo -NR11S(O)2(CH2)nR12 o un grupo -NR11S(O)2(CH2)nNR12R13; en donde cada n es 0, 1 o 2; en donde los grupos cicloalquilo, cicloalquenilo, arilo, heteroarilo, y heterociclilo están no sustituidos o sustituidos con uno o más sustituyentes seleccionados de un átomo de halógeno, un grupo ciano, un grupo alquilo lineal o ramificado C1-6, un grupo haloalquilo C1-4, un grupo hidroxialquilo C1-4, un grupo cicloalquilo C3-7, un grupo fenilo, un grupo piridilo, un grupo pirimidinilo, un grupo piperidilo, o un grupo -C(O)-(CH2)n-NR11R12; en donde n es 0, 1 ó 2; cada uno de R8, R9 y R10 independientemente representa un átomo de hidrógeno, un grupo haloalquilo C1-4, un grupo hidroxialquilo C1-4 o un grupo alquilo lineal o ramificado C1-6, donde dicho grupo alquilo está no sustituido o sustituido con uno o más sustituyentes seleccionados de un grupo alcoxi C1-4, un grupo ciano, un grupo cicloalquilo C3-7, un grupo fenilo, un grupo piridilo, un grupo pirimidinilo o un grupo piperidilo; R11, R12 y R13 representan independientemente cada uno un átomo de hidrógeno; un grupo haloalquilo C1-4 un grupo hidroxialquilo C1-4 un grupo heterocíclico de 5 a 9 miembros que contiene uno, dos o tres heteroátomos seleccionados de O, S y N, en donde el grupo heterocíclico está no sustituido o sustituido por uno o más sustituyentes seleccionados de un átomo de halógeno, un grupo hidroxilo, un grupo alquilo C1-4 lineal o ramificado, un grupo haloalquilo C1-4 o un grupo hidroxialquilo C1-4, o un grupo alquilo C1-6 lineal o ramificado, en donde el grupo alquilo está no sustituido o sustituido por uno o más sustituyentes seleccionados de un grupo alcoxi C1-4, un grupo ciano, un grupo cicloalquilo C3-7, un grupo fenilo, un grupo piridilo, un grupo pirimidinilo o un grupo piperidilo; en donde el compuesto de fórmula (1) es distinto que: a) 3-[[5-cloro-2-[[2,5-dimetil-4-(piperidin-4-il)fenil]amino]pirimidin-4-il]amino]piridin-2(1H)-ona; y b) 2-[7-[[5-cloro-4-[(2-oxo-1,2-dihidropiridin-3-il)amino]pirimidin-2-il]amino]-8-metoxi-1,2,4,5-tetrahidrobenzo[d]azepin-3-il]-N,N-dimetilacetamida.
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