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AR048834A1 - Compuestos derivados de piperidina o tropano; metodos para su preparacion; composiciones farmaceuticas que los contienen y su uso en la fabricacion de medicamentos para el tratamiento de enfermedades mediadas por quimioquinas (ccr5) - Google Patents

Compuestos derivados de piperidina o tropano; metodos para su preparacion; composiciones farmaceuticas que los contienen y su uso en la fabricacion de medicamentos para el tratamiento de enfermedades mediadas por quimioquinas (ccr5)

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Publication number
AR048834A1
AR048834A1 ARP050101605A ARP050101605A AR048834A1 AR 048834 A1 AR048834 A1 AR 048834A1 AR P050101605 A ARP050101605 A AR P050101605A AR P050101605 A ARP050101605 A AR P050101605A AR 048834 A1 AR048834 A1 AR 048834A1
Authority
AR
Argentina
Prior art keywords
alkyl
optionally substituted
alkoxy
cyano
nitro
Prior art date
Application number
ARP050101605A
Other languages
English (en)
Inventor
Alan Faull
Howard Tucker
Original Assignee
Astrazeneca Ab
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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=35197429&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=AR048834(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Priority claimed from SE0401057A external-priority patent/SE0401057D0/xx
Priority claimed from SE0500057A external-priority patent/SE0500057D0/sv
Application filed by Astrazeneca Ab filed Critical Astrazeneca Ab
Publication of AR048834A1 publication Critical patent/AR048834A1/es

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Abstract

Compuestos de formula (1), composiciones que los contienen, procesos para prepararlos y su uso en terapia médica (por ejemplo modulando la actividad del receptor CCR5 en un animal de sangre caliente. Reivindicacion 1: Un compuesto caracterizado porque responde a formula (1). donde: A está ausente o es (CH2)2; L es CH o N; M es NR1, O, S, S(O) o S(O)2; R1 es H, C1-6 alquilo [opcionalmente sustituido con fenilo {que a su vez está opcionalmente sustituido con halo, C1-4 alquilo, C1-4 alcoxi, ciano, nitro, CF3, OCF3, (C1-4 alquil)C(O)NH, S(O)2NH2, C1-4 alquiltio, S(O)(C1-4 alquilo) o S(O)2(C1-4alquilo)} o heteroarilo {que a su vez está opcionalmente sustituido con halo, C1-4 alquilo, C1-4 alcoxi, ciano, nitro, CF3, (C1-4 alquil)C(O)NH, S(O)2NH2, C1-4 alquiltio, S(O)(C1-4 alquilo) o S(O)2(C1-4 alquilo)}], fenilo {opcionalmente sustituido con halo, C1-4 alquilo, C1-4 alcoxi, ciano, nitro, CF3, OCF3, (C1-4 alquil)C(O)NH, S(O)2NH2, C1-4 alquiltio, S(O)(C1-4 alquilo) o S(O)2(C1-4 alquilo)}, heteroarilo {opcionalmente sustituido con halo, C1-4 alquilo, C1-4 alcoxi, ciano, nitro, CF3, (C1-4 alquil)C(O)NH, S(O)2NH2, C1-4 alquiltio, S(O)(C1-4 alquilo) o S(O)2(C1-4 alquilo)}, S(O)2R5, S(O)2NR6R7, C(O)R8, C(O)2(C1-6 alquilo) (como por ejemplo tert-butoxicarbonilo), C(O)2(fenil(C1-2 alquilo)) (como por ejemplo benciloxicarbonilo) o C(O)NHR11; R2 es fenilo (opcionalmente sustituido con halo, CN o C1-4 haloalquilo), tienilo o halotienilo; R3 es H o metilo; Rb es H o C1-3 alquilo; R4 es un heterociclo de 5 o 6 miembros con al menos un átomo de C, entre uno y cuatro átomos de C y, opcionalmente, un átomo de O o S, un C del anillo de dicho heterociclo R4 está opcionalmente sustituido con oxo, C1-6 alquilo [que está opcionalmente sustituido con halogeno, CN, OH, C1-4 alcoxi, S(C1-4 alquilo), S(O)(C1-4 alquilo), S(O)2(C1-4 alquilo) o heterociclilo {a su vez opcionalmente sustituido con C1-6 alquilo [que está opcionalmente sustituido con oxo, halogeno, OH, C1-4 alcoxi, OCF3, C(O)(C1-4 alcoxi), CN, C(O)NH2, C(O)NH(C1-4 alquilo), C(O)N(C1-4 alquil)2, NH2, NH(C1-4 alquilo) o N(C1-4 alquil)2], C(O)(C1-4 alquilo) [donde el alquilo está opcionalmente sustituido con C1-4 alcoxi o fluoro], bencilo [que está opcionalmente sustituido con halogeno, C1-4 alquilo, C1-4 alcoxi, CF3, OCF3, ciano, nitro, S(C1-4 alquilo), S(O)(C1-4 alquilo) o S(O)2(C1-4 alquilo)], C(O)(C1-4 alcoxi), C(O)NH2, C(O)NH(C1-4 alquilo), C(O)N(C1-4 alquil)2 o S(O)2(C1-4 alquilo) [donde el alquilo está opcionalmente sustituido con fluoro]}], C2-6 alquenilo, C3-6 cicloalquilo, CN, C(O)NH2, C(O)NH(fenil C1-2 alquilo), fenilo [que está opcionalmente sustituido con halogeno, C1-4 alquilo, C1-4 alcoxi, CF3, OCF3, ciano, nitro, S(C1-4 alquilo), S(O)(C1-4 alquilo) o S(O)2(C1-4 alquil)] o bencilo [que está opcionalmente sustituido con halogeno, C1-4 alquilo, C1-4 alcoxi, CF3, OCF3, ciano, nitro, S(C1-4 alquilo), S(O)(C1-4 alquilo) o S(O)2(C1-4 alquilo)]; cuando es posible, un N del anillo de dicho heterociclo R4 está opcionalmente sustituido con C1-6 alquilo [opcionalmente sustituido con oxo, halogeno, OH, C1-4 alcoxi, OCF3, NH2, NH(C1-4 alquilo), N(C1-4 alquil)2, S(C1-4 alquilo), S(O)(C1-4 alquilo), S(O)2(C1-4 alquilo), C(O)(C1-4 alcoxi), CONH2, CONH(C1-4 alquilo), CON(C1-4 alquil)2, ciano, arilo {opcionalmente sustituido con halogeno, C1-4 alquilo, C1-4 alcoxi, CF3, OCF3, ciano, nitro, S(C1-4 alquilo), S(O)(C1-4 alquilo) o S(O)2(C1-4 alquilo)}, heteroarilo {opcionalmente sustituido oxo, halogeno, C1-4 alquilo, C1-4 alcoxi, CF3, OCF3, ciano, nitro, S(C1-4 alquilo), S(O)(C1-4 alquilo) o S(O)2(C1-4 alquilo)}, heterociclilo {opcionalmente sustituido con C1-4 alquilo, arilo [opcionalmente sustituido con halogeno, C1-4 alquilo, C1-4 alcoxi, CF3, OCF3, ciano, nitro, S(C1-4 alquilo), S(O)(C1-4 alquilo) o S(O)2(C1-4 alquilo)], SO2NH(C1-4 alquilo), SO2N(C1-4 alquil)2, CONH(C1-4 alquilo), CON(C1-4 alquil)2, CO(C1-4 alquilo), CO(arilo) [opcionalmente sustituido con halogeno, C1-4 alquilo, C1-4 alcoxi, CF3, OCF3, ciano, nitro, S(C1-4 alquilo), S(O)(C1-4 alquilo) o S(O)2(C1-4 alquilo)], SO2(arilo) [opcionalmente sustituido con halogeno, C1-4 alquilo, C1-4 alcoxi, CF3, OCF3, ciano, nitro, S(C1-4 alquilo), S(O)(C1-4 alquilo) o S(O)2(C1-4 alquilo)]}], C3-6 cicloalquilo, CO(C1-4 alquilo) [opcionalmente sustituido con halogeno], CO(arilo) [opcionalmente sustituido con halogeno, C1-4 alquilo, C1-4 alcoxi, CF3, OCF3, ciano, nitro, S(C1-4 alquilo), S(O)(C1-4 alquilo) o S(O)2(C1-4 alquilo)], SO2(arilo) [opcionalmente sustituido con halogeno, C1-4 alquilo, C1-4 alcoxi, CF3, OCF3, ciano, nitro, S(C1-4 alquilo), S(O)(C1-4 alquilo) o S(O)2(C1-4 alquilo)], SO2(C1-4 alquilo) [opcionalmente sustituido con fluor], COO(C1-6 alquilo), arilo [opcionalmente sustituido con halogeno, C1-4 alquilo, C1-4 alcoxi, CF3, OCF3, ciano, nitro, S(C1-4 alquilo), S(O)(C1-4 alquilo) o S(O)2(C1-4 alquilo)], heteroarilo [opcionalmente sustituido con oxo, halogeno, C1-4 alquilo, C1-4 alcoxi, CF3, OCF3, ciano, nitro, S(C1-4 alquilo), S(O)(C1-4 alquilo) o S(O)2(C1-4 alquilo)], CONH(C1-4 alquilo), CONH(arilo) [opcionalmente sustituido con halogeno, C1-4 alquilo, C1-4 alcoxi, CF3, OCF3, ciano, nitro, S(C1-4 alquilo), S(O)(C1-4 alquilo) o S(O)2(C1-4 alquilo)], SO2NH(C1-4 alquilo) o SO2N(C1-4 alquil)2; con la condicion de que cuando un N del anillo de dicho heterociclo R4 está sustituido con un grupo alquilo, dicho alquilo no tiene un sustituyente oxo, halogeno, OH, C1-4 alcoxi, OCF3, NH2, NH(C1-4 alquilo), N(C1-4 alquil)2, S(C1-4 alquilo), S(O)(C1-4 alquilo) o S(O)2(C1-4 alquilo) sobre el C unido al N del anillo de dicho heterociclo R4; el heterociclo de 5 o 6 miembros R4 está opcionalmente fusionado a un anillo ciclohexano, piperidina, benceno, piridina, piridazina, pirimidina o pirazina; los átomos de C del anillo de dicho anillo ciclohexano, piperidina, benceno, piridina, piridazina, pirimidina o pirazina fusionado están opcionalmente sustituidos con halogeno, C1-4 alquilo, C1-4 alcoxi, CF3, OCF3, ciano, nitro, S(C1-4 alquilo), S(O)(C1-4 alquilo) o S(O)2(C1-4 alquilo); y el N de dicho anillo piperidina fusionado está opcionalmente sustituido con C1-4 alquilo [que está opcionalmente sustituido con oxo, halogeno, OH, C1-4 alcoxi, OCF3, C(O)(C1-4 alcoxi), CN, C(O)NH2, C(O)NH(C1-4 alquilo), C(O)N(C1-4alquil)2, NH2, NH(C1-4 alquilo) o N(C1-4 alquil)2], C(O)(C1-4 alquilo) [donde el alquilo está opcionalmente sustituido con C1-4 alcoxi o halogeno], bencilo [que está opcionalmente sustituido con halogeno, C1-4 alquilo C1-4 alcoxi, CF3, OCF3, ciano, nitro, S(C1-4 alquilo), S(O)(C1-4 alquilo) o S(O)2(C1-4 alquilo)],C(O)(C1-4 alcoxi), C(O)NH2, C(O)NH(C1-4 alquilo), C(O)N(C1-4 alquil)2 o S(O)2(C1-4 alquilo) [donde el alquilo está opcionalmente sustituido con fluoro]; R5 es C1-6 alquilo [opcionalmente sustituido con halo (como por ejemplo fluoro), C1-4 alcoxi, fenilo {que a su vez está opcionalmente sustituido con halo, C1-4 alquilo, C1-4 alcoxi, ciano, nitro, CF3, OCF3, (C1-4 alquil)C(O)NH, S(O)2NH2, C1-4 alquiltio, S(O)(C1-4 alquilo) o S(O)2(C1-4 alquilo)} o heteroarilo {que a su vez está opcionalmente sustituido con halo, C1-4 alquilo, C1-4 alcoxi, ciano, nitro, CF3, (C1-4 alquil)C(O)NH, S(O)2NH2, C1-4 alquiltio, S(O)(C1-4 alquilo) o S(O)2(C1-4 alquilo)}], C3-7 cicloalquilo (opcionalmente sustituido con halo o C1-6 alquilo), piranilo, fenilo {opcionalmente sustituido con halo, C1-4 alquilo, C1-4 alcoxi, ciano, nitro, CF3, OCF3, (C1-4 alquil)C(O)NH, S(O)2NH2, C1-4 alquiltio, S(O)(C1-4 alquilo) o S(O)2(C1-4 alquilo)}, heteroarilo {opcionalmente sustituido con halo, C1-4 alquilo, C1-4 alcoxi, ciano, nitro, CF3, (C1-4 alquil)C(O)NH, S(O)2NH2, C1-4 alquiltio, S(O)(C1-4 alquilo) o S(O)2(C1-4 alquilo)} o un anillo heterocíclico con N de 5 o 6 miembros {opcionalmente sustituido con S(O)2(C1-4 alquilo) o C(O)(C1-4 alquilo)}; R8 y R11 son, en forma independiente, H, C1- 6 alquilo [opcionalmente sustituido con halo (como por ejemplo fluoro), C1-4 alcoxi, fenilo {que a su vez está opcionalmente sustituido con halo, C1-4 alquilo, C1-4 alcoxi, ciano, nitro, CF3, OCF3, (C1-4 alquil)C(O)NH, S(O)2NH2, C1-4 alquiltio, S(O)(C1-4 alquilo) o S(O)2(C1-4 alquilo)} o heteroarilo {que a su vez está opcionalmente sustituido con halo, C1-4 alquilo, C1-4 alcoxi, ciano, nitro, CF3, (C1-4 alquil)C(O)NH, S(O)2NH2, C1-4 alquiltio, S(O)(C1-4 alquilo) o S(O)2(C1-4 alquilo)}], C3- 7 cicloalquilo (opcionalmente sustituido con halo o C1-6 alquilo), piranilo, fenilo { opcionalmente sustituido con halo, C1-4 alquilo, C1-4 alcoxi, ciano, nitro, CF3, OCF3, (C1-4 alquil)C(O)NH, S(O)2NH2, C1-4 alquiltio, S(O)(C1-4 alquilo) o S(O)2(C1- 4 alquilo)}, heteroarilo {opcionalmente sustituido con halo, C1-4 alquilo, C1-4 alcoxi, ciano, nitro, CF3, (C1-4 alquil)C(O)NH, S(O)2NH2, C1-4 alquiltio, S(O)(C1-4 alquilo) o S(O)2(C1-4 alquilo)} o un anillo heterocíclico con N de 5 o 6 miembros {opcionalmente sustituido con S(O)2(C1-4 alquilo) o C(O)(C1-4 alquilo)}; R6 y R7 son, en forma independiente, H o C1-4 alquilo; o R6 y R7 se unen para formar un anillo de 5 o 6 miembros que está opcionalmente sustituido con C1-4 alquilo o fenilo (donde el anillo fenilo está opcionalmente sustituido con halo, ciano, nitro, hidroxi, C1-4 alquilo, C1-4 alcoxi, S(O)mC1-4 alquilo, S(O)2NH2, S(O)2NH(C1-4 alquilo), S(O)2N(C1-4 alquil)2, NHS(O)2(C1-4 alquilo), NH2, NH(C1-4 alquilo), N(C1-4 alquil)2, NHC(O)NH2, C(O)NH2, C(O)NH(C1-4 alquilo), NHC(O)(C1-4 alquilo), CO2H, CO2(C1-4 alquilo), C(O)(C1-4 alquilo, CF3, CHF2, CH2F, CH2CF3 o OCF3); R9 y R10 son, en forma independiente, H o C1-6 alquilo; o una sal aceptable para uso farmacéutico de los mismos. Reivindicacion 11: Un proceso para preparar un compuesto de acuerdo con la reivindicacion 1, caracterizado porque comprende la aminacion reductiva de un compuesto de formula (2): con un compuesto de formula (3): en presencia de NaBH(OAc)3 (donde Ac es C(O)CH3) y ácido acético, en un solvente adecuado, a temperatura ambiente.
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