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AR106018A1 - Compuestos de arilo, heteroarilo y heterocíclicos para el tratamiento de trastornos médicos - Google Patents

Compuestos de arilo, heteroarilo y heterocíclicos para el tratamiento de trastornos médicos

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Publication number
AR106018A1
AR106018A1 ARP160102593A ARP160102593A AR106018A1 AR 106018 A1 AR106018 A1 AR 106018A1 AR P160102593 A ARP160102593 A AR P160102593A AR P160102593 A ARP160102593 A AR P160102593A AR 106018 A1 AR106018 A1 AR 106018A1
Authority
AR
Argentina
Prior art keywords
4alkyl
independently selected
6alkyl
halogen
cyano
Prior art date
Application number
ARP160102593A
Other languages
English (en)
Inventor
Allan Wiles Jason
S Phadke Avinash
Deshpande Milind
Agarwal Atul
Wang Xiangzhu
Chen Dawei
Hashimoto Akihiro
Pais Godwin
Rao GADHACHANDA Venkat
Wang Qiuping
Original Assignee
Achillion 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 Achillion Pharmaceuticals Inc filed Critical Achillion Pharmaceuticals Inc
Publication of AR106018A1 publication Critical patent/AR106018A1/es

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Abstract

La presente se relaciona con compuestos de la fórmula (1) o sales farmacéuticamente aceptables de los mismos, donde: Q¹ es C(R¹R¹’); Q² es C(R²R²’); Q³ es C(R³R³’); X¹ es N y X² es CH; R¹, R¹’, R², R²’, R³ y R³’ se seleccionan independientemente entre hidrógeno, halógeno, hidroxilo, nitro, ciano, amino, C₁₋₆alquilo, C₂₋₆alquenilo, C₁₋₆alcoxi, C₂₋₆alquinilo, C₂₋₆alcanoilo, C₁₋₆tioalquilo, -C(O)OR⁹, -OC(O)R⁹, -NR⁹C(O)R¹⁰, -C(O)NR⁹R¹⁰, -OC(O)NR⁹R¹⁰, -NR⁹C(O)OR¹⁰, C₁₋₂haloalquilo, y C₁₋₂haloalcoxi; R⁹ y R¹⁰ se seleccionan independientemente, cada vez que aparecen, entre hidrógeno, C₁₋₆alquilo, (C₃₋₇cicloalquil)C₀₋₄alquilo, -C₀₋₄alquil(C₃₋₇cicloalquilo), y -O-C₀₋₄alquil(C₃₋₇cicloalquilo); o R¹ y R² se toman juntos para formar un anillo carbocíclico de 3 miembros; o R² y R³ se toman juntos para formar un anillo carbocíclico de 3 a 6 miembros; A es un grupo seleccionado entre los compuestos de fórmula (3) y (4); R⁵ y R⁶ se seleccionan independientemente entre -CHO, -C(O)NH₂, -C(O)NH(CH₃), C₂₋₆alcanoilo, hidrógeno, hidroxilo, halógeno, ciano, nitro, -COOH, -SO₂NH₂, vinilo, C₁₋₆alquilo, C₂₋₆alquenilo, C₁₋₆alcoxi, -C₀₋₄alquil(C₃₋₇cicloalquilo), -C(O)C₀₋₄alquil(C₃₋₇cicloalquilo), -P(O)(OR⁹)₂, -OC(O)R⁹, -C(O)OR⁹, -C(O)N(CH₂CH₂R⁹)(R¹⁰), -NR⁹C(O)R¹⁰, fenilo, y heteroarilo de 5 a 6 miembros; R⁸ y R⁸’ se seleccionan independientemente entre hidrógeno, halógeno, hidroxilo, C₁₋₆alquilo, -C₀₋₄alquil(C₃₋₇cicloalquilo), C₁₋₆alcoxi, y (C₁₋₄alquilamino)C₀₋₂alquilo; o R⁸ y R⁸’ se toman juntos para formar un grupo oxo; o R⁸ y R⁸’ se pueden tomar junto con el átomo de carbono al cual están unidos para formar un anillo carbocíclico de 3 miembros; X¹¹ es N o CR¹¹; X¹² es CR¹²; X¹³ es CR¹³; X¹⁴ es N o CR¹⁴; uno de R¹² y R¹³ se selecciona entre R³¹, y el otro de R¹² y R¹³ se selecciona entre R³²; R³¹ se selecciona entre hidrógeno, halógeno, hidroxilo, nitro, ciano, amino, -COOH, C₁₋₂haloalquilo, C₁₋₂haloalcoxi, C₁₋₆alquilo, -C₀₋₄alquil(C₃₋₇cicloalquilo), C₂₋₆alquenilo, C₂₋₆alcanoilo, C₁₋₆alcoxi, C₂₋₆alqueniloxi, -C(O)OR⁹, C₁₋₆tioalquilo, -C₀₋₄alquilo-NR⁹R¹⁰, -C(O)NR⁹R¹⁰, -SO₂R⁹, -SO₂NR⁹R¹⁰, -OC(O)R⁹, y -C(NR⁹)NR⁹R¹⁰, en donde cada R³¹ distinto de hidrógeno, halógeno, hidroxilo, nitro, ciano, C₁₋₂haloalquilo, y C₁₋₂haloalcoxi no está sustituido o está sustituido con uno o más sustituyentes seleccionados independientemente entre halógeno, hidroxilo, nitro, ciano, amino, -COOH, -CONH₂, C₁₋₂haloalquilo, y C₁₋₂haloalcoxi, y cada R³¹ también está sustituido opcionalmente con un sustituyente seleccionado entre fenilo y heterociclo de 4 a 7 miembros que contiene 1, 2 ó 3 heteroátomos independientemente seleccionados entre N, O y S; en donde el fenilo o heterociclo de 4 a 7 miembros no está sustituido o está sustituido con uno o más sustituyentes seleccionados independientemente entre halógeno, hidroxilo, nitro, ciano, C₁₋₆alquilo, C₂₋₆alquenilo, C₂₋₆alcanoilo, C₁₋₆alcoxi, (mono y di-C₁₋₆alquilamino)C₀₋₄alquilo, C₁₋₆alquiléster, -(C₀₋₄alquil)(C₃₋₇cicloalquilo), C₁₋₂haloalquilo, y C₁₋₂haloalcoxi; R³² se selecciona entre: (i) un arilo seleccionado entre el grupo que consiste en fenilo y naftilo; o (ii) un heterociclo de 5 a 6 miembros saturado o insaturado que tiene 1, 2 ó 3 heteroátomos independientemente seleccionado entre N, O ó S, en donde el heterociclo es unido a través de un átomo de carbono en el anillo heterocíclico a un átomo de carbono del anillo A; o (iii) un heteroarilo seleccionado entre el grupo que consiste en piridinilo, pirimidinilo, pirazolilo, pirazinilo, furilo, tienilo, isoxazolilo, tiazolilo, oxadiazolilo, oxazolilo, isotiazol, quinolinilo, isoquinolinilo, benzofuranilo, cinolinilo, indolizinilo, flalazinilo, piridazinilo, triazinilo, pteridinilo, tiadiazolilo, furazanilo, benzofurazanilo, benzotiofenilo, benzotiazolilo, benzooxazolilo, quinazolinilo, quinoxalinilo, naftiridinilo, tetrahidrofuranilo y furopiridilo; en donde cada R³² puede estar opcionalmente sustituido con uno o más sustituyentes seleccionados entre halógeno, hidroxilo, amino, ciano, -CHO, -COOH, -CONH₂, C₁₋₆alquilo, C₂₋₆alquenilo, C₂₋₆alquinilo, -C₁₋₆alcoxi, C₂₋₆alcanoilo, C₁₋₆alquiléster, (mono y di-C₁₋₆alquilamino)C₀₋₂alquilo, C₁₋₂haloalquilo, hidroxi-C₁₋₆alquilo, éster, carbamato, urea, sulfonamida, -C₁₋₆alquil(heterociclo), C₁₋₆alquil(heteroarilo), -C₁₋₆alquil(C₃₋₇cicloalquilo), O-C₁₋₆alquil(C₃₋₇cicloalquilo), B(OH)₂, fosfato, fosfonato y C₁₋₂haloalcoxi; R¹¹ y R¹⁴ se seleccionan independientemente, cada vez que aparecen, entre hidrógeno, halógeno, hidroxilo, nitro, ciano, -O(PO)(OR⁹)₂, -(PO)(OR⁹)₂, C₁₋₆alquilo, C₂₋₆alquenilo, C₂₋₆alquinilo, C₂₋₆alcanoilo, C₁₋₆alcoxi, C₁₋₆tioalquilo, -C₀₋₄alquil(mono y di-C₁₋₆alquilamino), -C₀₋₄alquil(C₃₋₇cicloalquilo), -C₀₋₄alcoxi(C₃₋₇cicloalquilo), C₁₋₂haloalquilo, y C₁₋₂haloalcoxi; R²¹ y R²² se seleccionan independientemente, cada vez que aparecen, entre hidrógeno, hidroxilo, ciano, amino, C₁₋₆alquilo, C₁₋₆haloalquilo, C₁₋₆alcoxi, (C₃₋₇cicloalquil)C₀₋₄alquilo, (fenil)C₀₋₄alquilo, -C₁₋₄alquil-OC(O)OC₁₋₆alquilo, -C₁₋₄alquil-OC(O)C₁₋₆alquilo, -C₁₋₄alquil-C(O)OC₁₋₆alquilo, (heterocicloalquilo de 4 a 7 miembros)C₀₋₄alquilo que tiene 1, 2 ó 3 heteroátomos independientemente seleccionados entre N, O y S, y (heterociclo aromático o insaturado de 5 o 6 miembros)C₀₋₄alquilo que tiene 1, 2 ó 3 heteroátomos independientemente seleccionados entre N, O y S; R²³ se selecciona independientemente, cada vez que aparece, entre C₁₋₆alquilo, C₁₋₆haloalquilo, (aril)C₀₋₄alquilo, (C₃₋₇cicloalquil)C₀₋₄alquilo, (fenil)C₀₋₄alquilo, (heterocicloalquilo de 4 a 7 miembros)C₀₋₄alquilo que tiene 1, 2 ó 3 heteroátomos independientemente seleccionados entre N, O y S, y (heterociclo aromático o insaturado de 5 ó 6 miembros)C₀₋₄alquilo que tiene 1, 2 ó 3 heteroátomos independientemente seleccionados entre N, O y S; R²⁴ y R²⁵ se toman junto con el átomo de nitrógeno al cual están unidos para formar un grupo heterocicloalquilo monocíclico de 4 a 7 miembros, o un grupo heterocíclico bicíclico de 6 a 10 miembros que tiene anillos fusionados, espiro o en puente; L es un compuesto de fórmula (4); R¹⁷ es hidrógeno, C₁₋₆alquilo, o -C₀₋₄alquil(C₃₋₇cicloalquilo); R¹⁸ y R¹⁸’ se seleccionan independientemente entre hidrógeno, halógeno, hidroximetilo, y metilo; m es 0, 1, 2 ó 3; B es un grupo carbocíclico monocíclico o bicíclico; un grupo carbocíclico-oxi monocíclico o bicíclico; un grupo heterocíclico monocíclico, bicíclico o tricíclico que tiene 1, 2, 3, ó 4 heteroátomos independientemente seleccionados entre N, O y S, y entre 4 a 7 átomos en el anillo por anillo; C₂₋₆alquenilo; C₂₋₆alquinilo; -(C₀₋₄alquil)(arilo); -(C₀₋₄alquil)(heteroarilo); o -(C₀₋₄alquil)(bifenilo), y B no está sustituido o está sustituido con uno o más sustituyentes seleccionados independientemente entre R³³ y R³⁴, y 0 ó 1 sustituyente seleccionado entre R³⁵ y R³⁶; R³³ se selecciona independientemente entre halógeno, hidroxilo, -COOH, ciano, C₁₋₆alquilo, C₂₋₆alcanoilo, C₁₋₆alcoxi, -C₀₋₄alquilo-NR⁹R¹⁰, -SO₂R⁹, C₁₋₂haloalquilo, y C₁₋₂haloalcoxi; R³⁴ se selecciona independientemente entre nitro, C₁₋₆alquenilo, C₂₋₆alquinilo, C₁₋₆tioalquilo, -JC₃₋₇cicloalquilo, -B(OH)₂, -JC(O)NR⁹R²³, -JOSO₂OR²¹, -C(O)(CH₂)₁₋₄S(O)R²¹, -O(CH₂)₁₋₄S(O)NR²¹R²², -JOP(O)(OR²¹)(OR²²), -JP(O)(OR²¹)(OR²²), -JOP(O)(OR²¹)R²², -JP(O)(OR²¹)R²², -JOP(O)R²¹R²², -JP(O)R²¹R²², -JSP(O)(OR²¹)(OR²²), -JSP(O)(OR²¹)(R²²), -JSP(O)(R²¹)(R²²), -JNR⁹P(O)(NHR²¹)(NHR²²), -JNR⁹P(O)(OR²¹)(NHR²²), -JNR⁹P(O)(OR²¹)(OR²²), -JC(S)R²¹, -JNR²¹SO₂R²², -JNR⁹S(O)NR¹⁰R²², -JNR⁹SO₂NR¹⁰R²², -JSO₂NR⁹COR²², -JSO₂NR⁹CONR²¹R²², JNR²¹SO₂R²², -JC(O)NR²¹SO₂R²², -JC(NH₂)NR²², -JC(NH₂)NR⁹S(O)₂R²², -JOC(O)NR²¹R²², -JNR²¹C(O)OR²², -JNR²¹OC(O)R²², -(CH₂)₁₋₄C₍O₎NR²¹R²², -JC(O)NR²⁴R²⁵, -JNR⁹C(O)R²¹, -JC(O)R²¹, -JNR⁹C(O)NR¹⁰R²², -CCR²¹, -(CH₂)₁₋₄OC(O)R²¹, y -JC(O)OR²³; en donde cada R³⁴ puede no estar sustituido o estar sustituido con uno o más sustituyentes seleccionados independientemente entre halógeno, hidroxilo, nitro, ciano, amino, oxo, -B(OH)₂, -Si(CH₃)₃, -COOH, -CONH₂, -P(O)(OH)₂, C₁₋₆alquilo, -C₀₋₄alquil(C₃₋₇cicloalquilo), C₁₋₆alcoxi, -C₀₋₂alquil(mono y di-C₁₋₄alquilamino), C₁₋₆alquiléster, C₁₋₄alquilamino, C₁₋₄hidroxiloalquilo, C₁₋₂haloalquilo, y C₁₋₂haloalcoxi; R³⁵ se selecciona independientemente entre naftilo, naftiloxi, indanilo, (heterocicloalquilo de 4 a 7 miembros)C₀₋₄alquilo que contiene 1 ó 2 heteroátomos seleccionados entre N, O y S, y heterociclo bicíclico que contiene 1, 2 ó 3 heteroátomos independientemente seleccionados entre N, O y S, y que contiene 4 a 7 átomos en cada anillo; en donde cada R³⁵ no está sustituido o está sustituido con uno o más sustituyentes seleccionados independientemente entre halógeno, hidroxilo, nitro, ciano, C₁₋₆alquilo, C₂₋₆alquenilo, C₂₋₆alcanoilo, C₁₋₆alcoxi, (mono y di-C₁₋₆alquilamino)C₀₋₄alquilo, C₁₋₆alquiléster, -C₀₋₄alquil(C₃₋₇cicloalquilo), -SO₂R⁹, C₁₋₂haloalquilo, y C₁₋₂haloalcoxi; R³⁶ se selecciona independientemente entre tetrazolilo, (fenil)C₀₋₂alquilo, (fenil)C₁₋₂alcoxi, fenoxi, y heteroarilo de 5 ó 6 miembros que contiene 1, 2 ó 3 heteroátomos independientemente seleccionados entre N, O, B y S, en donde cada R³⁶ no está sustituido o está sustituido con uno o más sustituyentes seleccionados independientemente entre halógeno, hidroxilo, nitro, ciano, C₁₋₆alquilo, C₂₋₆alquenilo, C₂₋₆alcanoilo, C₁₋₆alcoxi, (mono- y di-C₁₋₆alquilamino)C₀₋₄alquilo, C₁₋₆alquiléster, -C₀₋₄alquil(C₃₋₇cicloalquilo), -SO₂R⁹, -OSi(CH₃)₂C(CH₃)₃, -Si(CH₃)₂C(CH₃)₃, C₁₋₂haloalquilo, -S(O)₂R²¹, y C₁₋₂haloalcoxi; y J se selecciona independientemente, cada vez que aparece, entre un enlace covalente, C₁₋₄alquileno, -OC₁₋₄alquileno, C₂₋₄alquenileno, y C₂₋₄alquinileno.
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