AR090829A2 - Antagonistas del receptor de quimiocinas y metodos de uso de los mismos - Google Patents

Antagonistas del receptor de quimiocinas y metodos de uso de los mismos

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Publication number
AR090829A2
AR090829A2 ARP130101374A ARP130101374A AR090829A2 AR 090829 A2 AR090829 A2 AR 090829A2 AR P130101374 A ARP130101374 A AR P130101374A AR P130101374 A ARP130101374 A AR P130101374A AR 090829 A2 AR090829 A2 AR 090829A2
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Argentina
Prior art keywords
group
substituted
aromatic
aliphatic
aliphatic group
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ARP130101374A
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English (en)
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Millennium Pharm Inc
Kyowa Hakko Kogyo Kk
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Priority claimed from US09/989,086 external-priority patent/US20020169155A1/en
Application filed by Millennium Pharm Inc, Kyowa Hakko Kogyo Kk filed Critical Millennium Pharm Inc
Publication of AR090829A2 publication Critical patent/AR090829A2/es

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Abstract

Compuestos de citocina o quimiocina quimiotáctica con actividad antiinflamatoria, útiles en enfermedades como alergia, y enfermedades respiratorias como el asma. Reivindicación 1: Un compuesto caracterizado porque tiene la fórmula (1) o sal fisiológicamente aceptable del mismo, en donde: n es uno a cuatro; M es >NR² o >CR¹R²; R¹ es -H, -OH, -N₃, un halógeno, un grupo alifático, un grupo alifático sustituido, un grupo aminoalquilo, -O-(grupo alifático), -O-(grupo alifático sustituido), -SH, -S-(grupo alifático), -S-(grupo alifático sustituido), -OC(O)-(grupo alifático), -O-C(O)-(grupo alifático sustituido), -C(O)O-(grupo alifático), -C(O)O-(grupo alifático sustituido), -COOH, -CN, -CO-NR³R⁴, o -NR³R⁴; R² es -OH, un halógeno, un grupo acilo, un grupo acilo sustituido, -NR⁵R⁶, un grupo alifático, un grupo alifático sustituido, un grupo aromático, un grupo aromático sustituido, un grupo bencilo, un grupo bencilo sustituido, un grupo heterocíclico no aromático, un grupo heterocíclico no aromático sustituido, -O-(grupo aromático sustituido o no sustituido), -O-(grupo alifático sustituido o no sustituido), -C(O)-(grupo aromático sustituido o no sustituido) o -C(O)-(grupo alifático sustituido o no sustituido); R³, R⁴, R⁵ y R⁶ son independientemente -H, un grupo acilo, un grupo acilo sustituido, un grupo alifático, un grupo alifático sustituido, un grupo aromático, un grupo aromático sustituido, un grupo bencilo, un grupo bencilo sustituido, un grupo heterocíclico no aromático o un grupo heterocíclico no aromático sustituido; o R¹ y R², R³ y R⁴, o R⁵ y R⁶ tomados junto con el átomo al que están unidos, forman un anillo carbocíclico o heterocíclico no aromático sustituido o no sustituido; R⁷⁰ y R⁷¹ son independientemente -H, -OH, -N₃, un halógeno, un grupo alifático, un grupo alifático sustituido, un grupo aminoalquilo, -O-(grupo alifático), -O-(grupo alifático sustituido), -SH, -S-(grupo alifático), -S-(grupo alifático sustituido), -OC(O)-(grupo alifático), -O-C(O)-(grupo alifático sustituido), -C(O)O-(grupo alifático), -C(O)O-(grupo alifático sustituido), -COOH, -CN, -CO-NR³R⁴, -NR³R⁴, un grupo acilo, un grupo acilo sustituido, un grupo bencilo, un grupo bencilo sustituido, un grupo heterocíclico no aromático, un grupo heterocíclico no aromático sustituido, o -O-(grupo aromático sustituido o no sustituido); R⁷² y R⁷³ son independientemente -OH, -N₃, un halógeno, un grupo alifático, un grupo alifático sustituido, un grupo aminoalquilo, -O-(grupo alifático), -O-(grupo alifático sustituido), -SH, -S-(grupo alifático), -S-(grupo alifático sustituido), -O-C(O)-(grupo alifático), -O-C(O)-(grupo alifático sustituido), -C(O)O-(grupo alifático), -C(O)O-(grupo alifático sustituido), -COOH, -CN, -CO-NR³R⁴, -NR³R⁴, un grupo acilo, un grupo acilo sustituido, un grupo bencilo, un grupo bencilo sustituido, un grupo heterocíclico no aromático, un grupo heterocíclico no aromático sustituido, o -O-(grupo aromático sustituido o no sustituido); Z es un compuesto de fórmula (2); X¹ es -CH₂-O-, -O-CH₂-, -S-, -CH₂-, -CH₂-CH₂-, -CH₂-S-, -S-CH₂, -NRᶜ-CH₂-, -CH₂-NRᶜ-, -SO-CH₂-, -CH₂-SO-, -S(O)₂-CH₂-, -CH₂-S(O)₂-, -CH=CH-, -NRᶜ-CO-, un enlace, -O-, o -CO-NRᶜ-; Rᶜ es -H, un grupo alifático, un grupo alifático sustituido, un grupo aromático, un grupo aromático sustituido, un grupo bencilo o un grupo bencilo sustituido; Anillos A y B son independientemente no sustituidos o sustituidos; dicho grupo acilo es un carbonilo alifático, carbonilo aromático, sulfonilo alifático o sulfonilo aromático; dicho grupo alifático es un C₁₋₆ alquilo, alquenilo o alquinilo; dicho grupo aromático está seleccionado a partir de fenilo, 1-naftilo, 2-naftilo, 1-antracilo, 2-antracilo, N-imidazolilo, 2-imidazolilo, 4-imidazolilo, 5-imidazolilo, 2-tienilo, 3-tienilo, 2-furanilo, 3-furanilo, 2-pirrolilo, 3-pirrolilo, 2-piridilo, 3-piridilo, 4-piridilo, 2-pirimidilo, 4-pirimidilo, 5-pirimidilo, 3-piridazinilo, 4-piridazinilo, 3-pirazolilo, 4-pirazolilo, 5-pirazolilo, 2-pirazinilo, 2-tiazolilo, 4-tiazolilo, 5-tiazolilo, 5-tetrazolilo, 2-oxazolilo, 4-oxazolilo, 5-oxazolilo, tetrahidronaftilo, 2-benzotienilo, 3-benzotienilo, 2-benzofuranilo, 3-benzofuranilo, 2-indolilo, 3-indolilo, 2-quinolinilo, 3-quinolinilo, 2-benzotiazolilo, 2-benzooxazolilo, 2-benzimidazolilo, 1-isoquinolinilo, 3-quinolinilo, 1-isoindolilo, 3-isoindolilo, acridinilo, 3-benzisoxazolilo, benzociclopentilo, o benzociclohexilo; dicho grupo heterocíclico no aromático es un anillo no aromático de cinco a ocho miembros que contiene uno o más heteroátomos independientemente seleccionados a partir de nitrógeno, oxigeno o azufre; dicho grupo alifático sustituido está sustituido con uno o más sustituyentes seleccionados a partir de grupo oxo, grupo epoxi, anillo heterocíclico no aromático, grupo bencilo, grupo bencilo sustituido, grupo aromático o grupo aromático sustituido, grupo atractor de electrones, halo, azido, -CN, -CONR²⁴R²⁵, -NR²⁴R²⁵, -OS(O)₂NR²⁴R²⁵, -S(O)₂NR²⁴R²⁵, -SO₃H, guanidino, oxalo, -C(=NR⁶⁰)NR²¹R²², =NR⁶⁰, -(O)ᵘ-(CH₂)ₜ-C(O)OR²⁰, -(O)ᵘ-(CH₂)ₜ-OC(O)R²⁰, -(O)ᵘ-(CH₂)ₜ-C(O)-NR²¹R²², -(O)ᵘ-(CH₂)ₜ-NHC(O)OR²⁰, -Q-H, -Q-(grupo alifático), -Q-(grupo alifático sustituido), -Q-(arilo), -Q-(grupo aromático), -Q-(grupo aromático sustituido), -Q-(CH₂)ₚ-(grupo aromático sustituido o no sustituido), -Q-(grupo heterocíclico no aromático) o -Q-(CH₂)ₚ-(grupo heterocíclico no aromático); dicho anillo heterocíclico no aromático sustituido está sustituido con uno o más sustituyentes seleccionados a partir de =O, =S, grupo atractor de electrones, halo, azido, -CN, -CONR²⁴R²⁵, -NR²⁴R²⁵, -OS(O)₂NR²⁴R²⁵, -S(O)₂NR²⁴R²⁵, -SO₃H, guanidino, oxalo, -C(=NR⁶⁰)NR²¹R²², =NR⁶⁰, -(O)ᵘ-(CH₂)ₜ-C(O)OR²⁰, -(O)ᵘ-(CH₂)ₜ-OC(O)R²⁰, -(O)ᵘ-(CH₂)ₜ-C(O)NR²¹R²², -(O)ᵘ-(CH₂)ₜ-NHC(O)OR²⁰, -Q-H, -Q-(grupo alifático), -Q-(grupo alifático sustituido), -Q-(arilo), -Q-(grupo aromático), -Q-(grupo aromático sustituido), -Q-(CH₂)ₚ-(grupo aromático sustituido o no sustituido), -Q-(grupo heterocíclico no aromático) o -Q-(CH₂)ₚ-(grupo heterocíclico no aromático); dicho grupo aromático sustituido, grupo bencilo sustituido, el Anillo A cuando está sustituido y el Anillo B cuando está sustituido, están sustituidos con uno o más sustituyentes seleccionados a partir de grupo atractor de electrones, grupo alifático, grupo alifático sustituido, grupo aromático, grupo aromático sustituido, halo, azido, -CN, -CONR²⁴R²⁵, -NR²⁴R²⁵, -OS(O)₂NR²⁴R²⁵, -S(O)₂NR²⁴R²⁵, -SO₃H, guanidino, oxalo, -C(=NR⁶⁰)NR²¹R²², =NR⁶⁰, -(O)ᵘ-(CH₂)ₜ-C(O)OR²⁰, -(O)ᵘ-(CH₂)ₜ-OC(O)R²⁰, -(O)ᵘ-(CH₂)ₜ-C(O)NR²¹R²², -(O)ᵘ-(CH₂)ₜ-NHC(O)O-R²⁰, -Q-H, -Q-(grupo alifático), -Q-(grupo alifático sustituido), -Q-(arilo), -Q-(grupo aromático), -Q-(grupo aromático sustituido), -Q-(CH₂)ₚ-(grupo aromático sustituido o no sustituido), -Q-(grupo heterocíclico no aromático) o -Q-(CH₂)ₚ-(grupo heterocíclico no aromático); Q es -O-, -S-, -S(O)-, -S(O)₂-, -OS(O)₂-, -C(O)-, -OC(O)-, -C(O)O-, -C(O)C(O)-O-, -O-C(O)C(O)-, -NHC(O)-, -OC(O)NH-, -NH-C(O)-NH-, -S(O)₂NH-, -NHS(O)₂-, -C(NR²³)NHNH-, -NHNHC(NR²³)-, -NR²⁴C(O)- o -NR²⁴S(O)₂-; R²⁰, R²¹ y R²² son independientemente -H, un grupo alifático, un grupo aromático, un grupo heterocíclico no aromático, -NHC(O)-O-(grupo alifático), -NHC(O)-O-(grupo aromático) o -NHC(O)-O-(grupo heterocíclico no aromático) o R²¹ y R²², tomados junto con el átomo de nitrógeno al cual están unidos, puede formar un anillo heterocíclico no aromático sustituido o no sustituido; R²³ es -H, un grupo alifático, un grupo bencilo, un grupo arilo o grupo heterocíclico no aromático; R²⁴ y R²⁵ son independientemente -H, un grupo alifático, un grupo alifático sustituido, un grupo bencilo, un grupo arilo, grupo heterocíclico no aromático o R²⁴ y R²⁵ tomados junto con el átomo de nitrógeno al cual están unidos pueden formar un anillo heterocíclico no aromático sustituido o no sustituido; R⁶⁰ es un -H, -OH, -NH₂, un grupo aromático o un grupo aromático sustituido; t es cero a tres; u es cero o uno; y p es uno a cinco.
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