AR093364A1 - Imidazo[1,2-a]piridincarboxamidas aminosustituidas y su uso - Google Patents

Imidazo[1,2-a]piridincarboxamidas aminosustituidas y su uso

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Publication number
AR093364A1
AR093364A1 ARP130104043A ARP130104043A AR093364A1 AR 093364 A1 AR093364 A1 AR 093364A1 AR P130104043 A ARP130104043 A AR P130104043A AR P130104043 A ARP130104043 A AR P130104043A AR 093364 A1 AR093364 A1 AR 093364A1
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AR
Argentina
Prior art keywords
alkyl
substituted
alkoxy
group
trifluoromethyl
Prior art date
Application number
ARP130104043A
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English (en)
Inventor
Dr Vakalopoulos Alexandros
Dr Follmann Markus
Dr Hartung Ingo
Dr Buchgraber Philipp
Dr Jautelat Rolf
Dr Hafeld Jorma
Lindner Niels
Dr Gromov Alexey
Dr Wunder Frank
Prof Dr Stasch Johannes
Peter - Dr Redlich Gorden
Min Dr Li Volkhart
Maria Jian - Dr Becker-Pelster Eva
Dr Knorr Andreas
Original Assignee
Bayer Pharma AG
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Priority claimed from US13/789,655 external-priority patent/US9126998B2/en
Application filed by Bayer Pharma AG filed Critical Bayer Pharma AG
Publication of AR093364A1 publication Critical patent/AR093364A1/es

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Abstract

La presente se refiere a imidazo[1,2-a]piridin-3-carboxamidas sustituidas, a procedimientos para su preparación, a su uso solas o en combinaciones para el tratamiento y/o la prevención de enfermedades, así como a su uso para la preparación de medicamentos para el tratamiento y/o la prevención de enfermedades, en especial para el tratamiento y/o la prevención de enfermedades cardiovasculares. Reivindicación 1: Compuesto de la fórmula (1), en donde A representa CH₂, CD₂ o CH(CH₃); R¹ representa alquilo C₄₋₆, cicloalquilo C₃₋₇ o fenilo, en donde alquilo C₄₋₆ puede estar sustituido hasta seis veces con flúor, en donde cicloalquilo C₃₋₇ puede estar sustituido con 1 a 4 sustituyentes seleccionados, de modo independiente entre si del grupo de flúor, trifluorometilo y alquilo C₁₋₄, y en donde fenilo puede estar sustituido con 1 a 4 sustituyentes seleccionados, de modo independiente entre sí, del grupo de halógeno, ciano, monofluorometilo, difluorometilo, trifluorometilo, alquil C₁₋₄, cicloalquilo C₃₋₆, alcoxi C₁₋₄, difluorometoxi y trifluorometoxi; R² representa hidrógeno, alquilo C₁₋₄, ciclopropilo, monofluorometilo, difluorometilo o trifluorometilo; R³ representa un grupo de la fórmula (2) ó (3) en donde * representa el sitio de unión con el grupo carbonilo; L¹A representa un enlace o alcan C₁₋₄-diílo, en donde alcan C₁₋₄-diílo puede estar sustituido con 1 a 3 sustituyentes seleccionados, de modo independiente entre sí del grupo de flúor, trifluorometilo, alquilo C₁₋₄, cicloalquilo C₃₋₇, hidroxi y alcoxi C₁₋₄; L¹B representa un enlace o alcan C₁₋₄-diílo; L¹C representa un enlace o alcan C₁₋₄-diilo, en donde alcan C₁₋₄-diílo puede estar sustituido con 1 a 3 sustituyentes seleccionados, de modo independiente entre sí, del grupo de flúor, trifluorometilo, alquilo C₁₋₄, cicloalquilo C₃₋₇, hidroxi y alcoxi C₁₋₄; R⁷ representa hidrógeno, alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₇, ciano, heteroalquilo de 5 a 10 miembros, naftilo o fenilo, en donde alquilo C₁₋₆ puede estar sustituido con 1 a 3 sustituyentes seleccionados, de modo independiente entre sí, del grupo de flúor, trifluorometilo, difluorometoxi, trifluorometoxi, hidroxi, alcoxi C₁₋₄, alcoxi C₁₋₄-carbonilo, alquil C₁₋₄-sulfonilo, fenilo, fenoxi y benciloxi, en donde fenilo, fenoxi y benciloxi, a su vez, pueden estar sustituidos con 1 a 3 sustituyentes halógeno o alcoxi C₁₋₄, en donde cicloalquilo C₃₋₇ puede estar sustituido con 1 ó 2 sustituyentes seleccionados, de modo independiente entre sí, del grupo de flúor, trifluorometilo, alquilo C₁₋₄ y alcoxi C₁₋₄, y en donde fenilo y heteroarilo de 5 a 10 miembros pueden estar sustituidos con 1 a 3 sustituyentes seleccionados, de modo independiente entre sí, del grupo de halógeno, ciano, nitro, difluorometilo, trifluorometilo, difluorometoxi, trifluorometoxi, -NH(CO)CH₃, alquilo C₁₋₄, cicloalquilo C₁₋₄, alquenilo C₁₋₄, alquil C₁₋₄-sulfonilo, alcoxi C₁₋₄-carbonil y alcoxi C₁₋₄, en donde alcoxi C₁₋₄ puede estar sustituido con hidroxi, y en donde el fenilo puede estar sustituido en 2 átomos de carbono adyacentes con un puente de difluorometilendioxi; R⁸ representa hidrógeno o alquilo C₁₋₄, o R⁷ y R⁸ junto con el átomo de carbono al que están unidos, forman un carbociclo de 3 a 7 miembros o un heterociclo de 4 a 7 miembros, en donde el carbociclo de 3 a 7 miembros o el heterociclo de 4 a 7 miembros, a su vez, pueden estar sustituidos con 1 ó 2 sustituyentes seleccionados, de modo independiente entre sí, del grupo de flúor y alquilo C₁₋₄; R⁹ representa hidrógeno, ciano, alquilo C₁₋₆, alquenil C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₇, heteroarilo de 5 a 10 miembros o fenilo, en donde alquilo C₁₋₆ puede estar sustituido con 1 a 3 sustituyentes seleccionados, de modo independiente entre sí, del grupo de flúor, difluorometilo, trifluorometilo, difluorometoxi, trifluorometoxi, hidroxi, ciano, alcoxi C₁₋₄, alcoxi C₁₋₄-carbonilo, alquil C₁₋₄-sulfonilo, heteroarilo de 5 ó 6 miembros, fenilo, fenoxi y benciloxi, en donde fenilo, fenoxi y benciloxi, a su vez, pueden estar sustituidos con 1 a 3 sustituyentes halógeno o alcoxi C₁₋₄, en donde heteroarilo de 5 ó 6 miembros puede estar benzocondensado o sustituido con un heteroarilo de 5 ó 6 miembros, en donde heteroarilo de 5 ó 6 miembros puede estar sustituido con alquilo C₁₋₄ o trifluorometilo, en donde cicloalquilo C₃₋₇ puede estar sustituido con 1 ó 2 sustituyentes seleccionados, de modo independiente entre sí, del grupo de flúor, trifluorometilo, alquilo C₁₋₄ y alcoxi C₁₋₄, y en donde fenilo y heteroarilo de 5 a 10 miembros pueden estar sustituidos con 1 a 3 sustituyentes seleccionados, de modo independiente entre sí, del grupo de halógeno, ciano, difluorometilo, trifluorometilo, difluorometoxi, trifluorometoxi, alquilo C₁₋₄, cicloalquilo C₁₋₄, alcoxi C₁₋₄, alcoxi C₁₋₄-carbonilo y alquil C₁₋₄-sulfonilo, en donde alcoxi C₁₋₄ puede estar sustituido con hidroxi, y en donde puede estar sustituido en 2 átomos de carbono adyacentes del fenilo con un puente de difluorometilendioxi; R¹⁰ representa hidrógeno o alquilo C₁₋₄, o R⁹ y R¹⁰ junto con el átomo de carbono al que están unidos, forman un carbociclo de 3 a 7 miembros o un heterociclo de 4 a 7 miembros, en donde el carbociclo de 3 a 7 miembros o el heterociclo de 4 a 7 miembros, a su vez, pueden estar sustituidos con 1 ó 2 sustituyentes seleccionados, de modo independiente entre sí, del grupo de flúor, bencilo y alquilo C₁₋₄, siempre que los radicales R⁷ y R⁹ no representen al mismo tiempo fenilo, o R⁷ y R⁹ junto con los átomos de carbono a los que están unidos, así como el grupo L¹B forman un carbociclo de 3 a 7 miembros o un heterociclo de 4 a 7 miembros, en donde el carbociclo de 3 a 7 miembros puede estar sustituido con 1 ó 2 sustituyentes seleccionados, de modo independiente entre sí, del grupo de alquilo C₁₋₄, flúor, hidroxi y alcoxi C₁₋₄, siempre que, al mismo tiempo, no más que uno de los pares de radicales R⁷ y R⁸, R⁹ y R¹⁰ o bien R⁷ y R⁹ forme un carbo- o heterociclo; R¹¹ representa hidrógeno o alquilo C₁₋₄, en donde alquilo C₁₋₄ puede estar sustituido con 1 a 3 sustituyentes seleccionados, de modo independiente entre sí, del grupo de flúor, trifluorometilo, hidroxi y alcoxi C₁₋₄; R¹² representa hidrógeno, alquilo C₁₋₆, cicloalquil C₃₋₇, fenilo o bencilo, en donde alquilo C₁₋₆ puede estar sustituido con 1 a 3 sustituyentes seleccionados, de modo independiente entre sí, del grupo de flúor, trifluorometilo, hidroxi, alcoxi C₁₋₄ y fenoxi, y en donde fenilo y bencilo pueden estar sustituidos con 1 a 3 sustituyentes seleccionados, de modo independiente entre sí, del grupo de halógeno y trifluorometilo, o R¹¹ y R¹² junto con el átomo de nitrógeno al que están unidos, forman un aza-heterociclo de 4 a 7 miembros, en donde el aza-heterociclo de 4 a 7 miembros puede estar sustituido con 1 ó 2 sustituyentes seleccionados, de modo independiente entre sí, del grupo de flúor, trifluorometilo, alquilo C₁₋₄, cicloalquil C₃₋₇, hidroxi, alcoxi C₁₋₄ y heterociclilo de 4 a 7 miembros; y L² representa un enlace o alcan C₁₋₄-diílo; R¹³ representa un aza-heterociclilo de 5 a 9 miembros, unido a través de un átomo de carbono del anillo, en donde el aza-heterociclilo de 5 a 9 miembros puede estar sustituido con 1 a 5 sustituyentes seleccionados, de modo independiente, del grupo de flúor, trifluorometilo, alquilo C₁₋₄, cicloalquilo C₃₋₇ y bencilo, y en donde el aza-heterociclilo de 5 a 9 miembros puede estar fusionado con un anillo fenilo que, a su vez, puede estar sustituido con 1 ó 2 sustituyentes seleccionados de halógeno, alquilo C₁₋₄, alcoxi C₁₋₄ y trifluorometilo, o representa adamantilo; R⁴ representa hidrógeno; R⁵ representa hidrógeno, halógeno, ciano, monofluorometilo, difluorometilo, trifluorometilo, alquilo C₁₋₄, cicloalquilo C₃₋₇, alquenil C₂₋₄, alquinilo C₂₋₄, difluorometoxi, trifluorometoxi, alcoxi C₁₋₄, amino, heterociclilo de 4 a 7 miembros o heteroarilo de 5 ó 6 miembros; R⁶ representa hidrógeno, ciano o halógeno; así como sus N-óxidos, sales, solvatos, sales de los N-óxidos y solvatos de los N-óxidos y sales.
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