AR043648A1 - Derivados de bencenosulfonamida - Google Patents

Derivados de bencenosulfonamida

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Publication number
AR043648A1
AR043648A1 ARP040100901A ARP040100901A AR043648A1 AR 043648 A1 AR043648 A1 AR 043648A1 AR P040100901 A ARP040100901 A AR P040100901A AR P040100901 A ARP040100901 A AR P040100901A AR 043648 A1 AR043648 A1 AR 043648A1
Authority
AR
Argentina
Prior art keywords
alkyl
amino
optionally substituted
hydroxy
mono
Prior art date
Application number
ARP040100901A
Other languages
English (en)
Original Assignee
Bayer Healthcare Ag
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 Bayer Healthcare Ag filed Critical Bayer Healthcare Ag
Publication of AR043648A1 publication Critical patent/AR043648A1/es

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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • 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
    • A61K31/439—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 the ring forming part of a bridged ring system, e.g. quinuclidine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/02—Nasal agents, e.g. decongestants
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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    • C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
    • C07C311/29—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
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    • C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/37—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
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    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
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    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/36—Oxygen or sulfur atoms
    • C07D207/40—2,5-Pyrrolidine-diones
    • C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
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    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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Abstract

Los derivados de bencenosulfonamida tienen actividad antagonista de CCR3 (receptor de quimioquina de tipo CC), y pueden utilizarse para la profilaxis y el tratamiento de enfermedades asociadas a la actividad CCR3, en particular para el tratamiento de asma, dermatitis atópica, rinitis alérgica y otros trastornos inflamatorios/inmunológicos. Reivindicación 1: Un derivado de bencenosulfonamida de fórmula (1), su forma tautomérica o estereoisomérica, o una sal del mismo, en la que: X representa O o S; R1 representa hidrógeno, halógeno, hidroxi, nitro, ciano, alcoxi(C1-6) carbonilo, amino, alquil(C1-6) amino, di(alquil (C1-6))amino, alcanoilo C1-6, fenilo, alquilo C1-6 opcionalmente sustituido con mono-, di- o trihalógeno, o alcoxi C1-6 opcionalmente sustituido con mono-, di- o trihalógeno; R2 representa hidrógeno, halógeno, hidroxi, nitro, ciano, alcoxi(C1-6) carbonilo, amino, alquil(C1-6) amino, di(alquil (C1-6))amino, alcanoilo C1-6, fenilo, alquilo C1-6 opcionalmente sustituido con mono-, di- o trihalógeno o alcoxi C1-6 opcionalmente sustituido con mono-, di- o trihalógeno; R3 representa hidrógeno, halógeno, hidroxi, nitro, ciano, amino, carboxi, tetrazolilo, alcoxi C1-6, alcoxi(C1-6) carbonilo, alcanoilo C1-6, alcanoil(C1-6) amino, alquilo C1-6 opcionalmente sustituido con mono-, di- o trihalógeno o hidroxi; R4 es un resto de grupo de fórmula (2), en las que: R40 representa alquilo C1-6 sustituido con pirrolidinilo o piperidinilo, estando dichos pirrolidinilo o piperidinilo opcionalmente sustituidos con mono- o dioxi, 7-oxa-biciclo[4.1.0]hept-3-ilo que tiene opcionalmente 1 ó 2 sustituyentes seleccionados del grupo constituido por amino, (alquil C1-6)amino y di(alquil (C1-6))amino, o un anillo heterocíclico saturado de 5 a 8 miembros que contiene 1 ó 2 heteroátomos seleccionados del grupo constituido por N y O y que tiene opcionalmente de 1 a 3 sustituyentes seleccionados del grupo constituido por hidroxi, amino, oxo y alquilo C1-6; R41 representa hidrógeno, alquilo C1-5 opcionalmente sustituido con amino, alquil(C1-6) amino, di(alquil (C1-6))amino, o 2,5-dioxopirrolidin-1-ilo o un cicloalquilo C5-8 opcionalmente sustituido con hidroxi; o R40 y R41 pueden formar, junto con el átomo de N adyacente, un anillo heterocíclico saturado de 5 a 8 miembros opcionalmente interrumpido por O; R42 representa alquileno C1-6 opcionalmente sustituido con hidroxi o carboxi, o un cicloalquilo C5-8 sustituido con al menos un hidroxi y además opcionalmente con 1 ó 2 sustituyentes seleccionados del grupo constituido por hidroxi, amino, oxo y alquilo C1-6; o R41 y R42 pueden formar, junto con el átomo de N adyacente, un anillo heterocíclico saturado de 5 a 8 miembros opcionalmente interrumpido por NH o O, estando dicho anillo heterocíclico saturado de 5 a 8 miembros sustituido con mono- o dioxo, con al la condición de que cuando R41 es hidrógeno, alquilo C1-6 opcionalmente sustituido con amino, alquil(C1-6) amino o di(alquil (C1-6))amino, R42 es alquileno C16 sustituido con hidroxi o alquileno C1-6 sustituido con carboxi; R43 representa hidrógeno o alquilo C1-6 opcionalmente sustituido con hidroxi o carboxi; R44 representa hidrógeno o alquilo C1-6 opcionalmente sustituido con hidroxi o carboxi, con la condición de que cuando R41 y R42 forman, junto con el átomo de N adyacente, un anillo heterocíclico saturado de 5 a 8 miembros sustituido por mono- o dioxo, R44 representa alquilo C1-6 sustituido con hidroxi o alquilo C1-6 sustituido con carboxi, R45, R47, R49 y R50 representan independientemente hidrógeno o alquilo C1-6; R46 y R48 representan independientemente alquileno C1-6 opcionalmente sustituido con hidroxi o carboxi; n representa un número entero seleccionado de 1 a 3; m representa un número entero seleccionado de 0 a 3; R51 representa hidrógeno, alquilo C1-6, o un anillo saturado de 3 a 8 miembros opcionalmente interrumpido por NH o O; R52 representa hidrógeno, alcoxi(C1-6) carbonilo, o alquilo C1-6 sustituido con carboxi, amino, (alquil C1-6)amino, di(alquil (C1-6))amino, N-(alquil C1-6)sulfonilamino, N-(alcanoil C1-6)amino, alcoxi(C1-6) carbonilo, tetrazolilo, triazolilo, indolinilo, isoindolinilo, indolilo, isoindolilo, pirrolidinilo opcionalmente sustituido con mono- o dioxo, o piperidinilo opcionalmente sustituido con mono- o dioxo, con la condición de que cuando R51 y R52 son hidrógeno al mismo tiempo, R3 sea tetrazolilo o alcanoilo C1-6, o cuando R51 es hidrógeno o alquilo C1-6, R52 sea distinto de hidrógeno; R61 y R62 representan independientemente hidrógeno o alquilo C1-6 opcionalmente sustituido con hidroxi, carboxi, fenilo o mono-, di- o trihalógeno; R71 representa hidrógeno o alquilo C1-6 opcionalmente sustituido con amino, hidroxi, carboxi, pirrolidinilo o piperidinilo, estando dichos pirrolidinilo y piperidinilo opcionalmente sustituidos con mono- o dioxo; R72 representa hidrógeno, carboxi, alcanoilo C1-6, amino, (alquil C1-6)amino, di(alquil (C1-6))amino, N-(alquil C1-6)aminocarbonilo, alquilo C1-6 opcionalmente sustituido con hidroxi, carboxi o mono-, di- o trihalógeno, alcoxi C1-6 opcionalmente sustituido con mono-, di- o trihalógeno, pirrolidinilo o piperidinilo, estando dichos pirrolidinilo y piperidinilo opcionalmente sustituidos con mono- o dioxo; Z1 representa -[CH2]p-, en la que p representa el número entero 1 ó 2; R81 representa hidrógeno, alcoxi(C1-6) carbonilo, o alquilo C1-6 sustituido con pirrolidinilo o piperidinilo, estando dichos pirrolidinilo y piperidinilo opcionalmente sustituidos con mono- o dioxo; R82 representa hidrógeno, hidroxi, carboxi o alquilo C1-6 sustituido con hidroxi, amino o carboxi, R83 representa hidrógeno, hidroxi, carboxi o alquilo C1-6 sustituido con hidroxi, amino o carboxi, con la condición de que cuando R81 es hidrógeno, R82 o R83 sea distinto de hidrógeno; Z2 representa -[CH2]q-, en la que q representa un número entero seleccionado de 0 a 3; R91 representa hidrógeno o alquilo C1-6 opcionalmente sustituido con fenilo; R111 representa hidrógeno, carboxi, alcoxi(C1-6) carbonilo, alcanoilo C1-6, N-(alquil C1-6)aminocarbonilo, alcoxi C1-6 opcionalmente sustituido con mono-, di- o trihalógeno, o alquilo C1-6 opcionalmente sustituido con hidroxi, mono-, di- o trihalógeno, amino, (alquil C1-6)amino, di(alquil (C1-6))amino, N-(alquil C1-6)sulfonilamino, N-(alcanoil C1-6)amino, alcoxi(C1-6)carbonilo, tetrazolilo, triazolilo, indolinilo, isoindolinilo, indolilo, isoindolilo, pirrolidinilo o piperidinilo, estando dichos pirrolidinilo o piperidinilo opcionalmente sustituidos con mono- o dioxo; Anillo A representa un anillo heterocíclico saturado de 3 a 8 miembros en el que el átomo de nitrógeno NA es el único heteroátomo; Anillo B representa un anillo heterocíclico saturado de 3 a 8 miembros en el que el átomo de nitrógeno NB es el único heteroátomo; los anillos C y D forman conjuntamente un anillo diazabicíclico de 7 a 15 miembros; y Anillo E representa un anillo heterocíclico saturado de 5 a 8 miembros en el que el átomo de nitrógeno NE es el único heteroátomo.
ARP040100901A 2003-03-24 2004-03-18 Derivados de bencenosulfonamida AR043648A1 (es)

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