AR090259A1 - Inhibidores de benzodioxano de la produccion de leucotrieno para terapia de combinacion - Google Patents

Inhibidores de benzodioxano de la produccion de leucotrieno para terapia de combinacion

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Publication number
AR090259A1
AR090259A1 ARP130100729A ARP130100729A AR090259A1 AR 090259 A1 AR090259 A1 AR 090259A1 AR P130100729 A ARP130100729 A AR P130100729A AR P130100729 A ARP130100729 A AR P130100729A AR 090259 A1 AR090259 A1 AR 090259A1
Authority
AR
Argentina
Prior art keywords
dihydro
benzodioxin
benzyl
alkyl
members
Prior art date
Application number
ARP130100729A
Other languages
English (en)
Inventor
Anders Bylock Lars
Original Assignee
Boehringer Ingelheim Int
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 Boehringer Ingelheim Int filed Critical Boehringer Ingelheim Int
Publication of AR090259A1 publication Critical patent/AR090259A1/es

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    • A—HUMAN NECESSITIES
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    • 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
    • A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
    • A61K31/553—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having at least one nitrogen and one oxygen as ring hetero atoms, e.g. loxapine, staurosporine
    • 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
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • 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
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/357—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having two or more oxygen atoms in the same ring, e.g. crown ethers, guanadrel
    • A—HUMAN NECESSITIES
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    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/365—Lactones
    • A61K31/366—Lactones having six-membered rings, e.g. delta-lactones
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    • A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
    • A61K31/381—Heterocyclic compounds having sulfur as a ring hetero atom having five-membered rings
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    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/397—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having four-membered rings, e.g. azetidine
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    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/4025—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil not condensed and containing further heterocyclic rings, e.g. cromakalim
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    • A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
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    • A61K31/407—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with other heterocyclic ring systems, e.g. ketorolac, physostigmine
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    • A61K31/436—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a six-membered ring having oxygen as a ring hetero atom, e.g. rapamycin
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    • A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/4365—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system having sulfur as a ring hetero atom, e.g. ticlopidine
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    • A61K31/438—The ring being spiro-condensed with carbocyclic or heterocyclic ring systems
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    • 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
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    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
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    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
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Abstract

Reivindicación 1: Una combinación caracterizada porque comprende un compuesto de la fórmula (1) o una sal de este aceptable desde el punto de vista farmacéutico, en donde: X es N o CH; n es un entero de 0 a 3; R¹ se selecciona de halo, -OH, -CN, -alquilo C₁₋₆, -O-alquilo C₁₋₆ y -cicloalquilo C₃₋₆; R² y R³ se seleccionan, cada uno, independientemente de -H y -alquilo C₁₋₆; en donde R²y R³ pueden unirse para formar un anillo de 3 a 6 miembros que comprende, opcionalmente, de 1 a 3 heteroátomos, opcionalmente también sustituido con 1 a 3 grupos seleccionados de halo, -OH, (=O), -alquilo C₁₋₆, -O-alquilo C₁₋₆, -C(O)OH, -C(O)alquilo C₁₋₆ y -C(O)NH₂; A es un grupo de la fórmula -NR⁴R⁵, en donde R⁴ y R⁵ se seleccionan, cada uno, independientemente de -H, -alquilo C₁₋₆, -cicloalquilo C₃₋₆, -heterocicloalquilo (de 4 a 14 miembros), -arilo C₆₋₁₀ y -heteroarilo (de 5 a 11 miembros); en donde cada uno de los anteriores -alquilo C₁₋₆, -cicloalquilo C₃₋₆, -heterocicloalquilo (de 4 a 14 miembros), -arilo C₆₋₁₀ y heteroarilo -(de 5 a 11 miembros) de dichos grupos R⁴ y R⁵ se sustituye de manera opcional e independiente con 1 a 3 grupos R⁶; en donde dos grupos R⁶, cuando se ligan al mismo átomo de carbono de dicho -alquilo C₁₋₆, pueden unirse para formar un anillo de 3 a 6 miembros que comprende, opcionalmente, de 1 a 3 heteroátomos, opcionalmente también sustituido con 1 a 3 grupos seleccionados de halo, -OH, (=O), -alquilo C₁₋₆, -O-alquilo C₁₋₆, -C(O)OH, -C(O)alquilo C₁₋₆ y -C(O)NH₂; A es un anillo N-heterocíclico (de 4 a 14 miembros) de la fórmula (2) en donde el anillo B es: (c) un radical monocíclico no aromático de 4 - 8 miembros; o (d) un radical bicíclico en puente, un radical spirocíclico o un radical bicíclico fusionado de 6 a 11 miembros, en donde cada radical bicíclico en puente, radical spirocíclico y radical bicíclico fusionado de 6 a 11 miembros comprende al menos un anillo N-heterocíclico no aromático que se une al átomo de carbono 1 del compuesto de la fórmula (1); en donde cada radical bicíclico en puente, radical spirocíclico y radical bicíclico fusionado de 6 a 11 miembros puede comprender opcionalmente un anillo aromático; en donde dicho anillo B también puede comprender de 1 a 3 heteroátomos adicionales del anillo seleccionados independientemente de N, O y S; en donde dicho anillo B también se puede sustituir opcionalmente con 1 a 3 grupos seleccionados de halo, -OH, (=O), -C(O)OH, -C(O)O-alquilo C₁₋₆ y -alquilo C₁₋₆; y en donde L está ausente o es un ligador seleccionado de -alquileno C₁₋₆; cada R⁶ se selecciona independientemente de halo, -OR⁷, -CF₃, -CN, -alquilo C₁₋₆, -O-alquilo C₁₋₆, -C(O)R⁷, -C(O)₂R⁷, -C(O)N(R⁷)₂, -N(R⁷)₂, -NHC(O)R⁷, -NHC(O)N(R⁷)₂, -S(O)₂R⁷, -NH-S(O)₂-R⁷, -cicloalquilo C₃₋₆, heterocicloalquilo (de 4 a 14 miembros), -arilo C₆₋₁₀ y heteroarilo (de 5 a 11 miembros); en donde cada uno de -alquilo C₁₋₆, -O-alquilo C₁₋₆, -cicloalquilo C₃₋₆, heterocicloalquilo (de 4 a 14 miembros), -arilo C₆₋₁₀ y heteroarilo (de 5 a 11 miembros) del grupo R⁶ se sustituye opcionalmente, cuando fuese posible, con 1 a 3 grupos seleccionados de halo, -OH, -CF₃, -CN, (=O), -alquilo C₁₋₆, -C(O)O-H, -C(O)O-alquilo C₁₋₆, -NH₂, -NH-alquilo C₁₋₆, -N(alquilo C₁₋₆)₂, -S(O)₂alquilo C₁₋₆, -cicloalquilo C₃₋₆, heterocicloalquilo (de 4 a 14 miembros), -arilo C₆₋₁₀ y heteroarilo (de 5 a 11 miembros); y cada R⁷ se selecciona independientemente de -H, -alquilo C₁₋₆, -alquil C₁₋₆-OH, -alquil C₁₋₆-O-alquilo C₁₋₆, -O-alquilo C₁₋₆, -cicloalquilo C₃₋₆, -cicloalquil C₃₋₆-OH, heterocicloalquilo (de 4 a 14 miembros), -arilo C₆₋₁₀ y heteroarilo (de 5 a 11 miembros); en donde cada uno de los grupos R⁷ se sustituye opcionalmente, cuando fuese posible, con un grupo seleccionado de -OH, -NH-alquilo C₁₋₆, -NHC(O)alquilo C₁₋₆, -C(O)NH₂, -S(O)₂alquilo C₁₋₆ y heterocicloalquilo (de 4 a 14 miembros); en donde el grupo heterocicloalquilo (de 4 a 14 miembros) se sustituye opcionalmente, cuando fuese posible, con un grupo (=O); y uno o más agentes activos adicionales. Reivindicación 2: La combinación de la reivindicación 1, caracterizada porque el compuesto de la fórmula (1) se selecciona del grupo que consiste en: 1-[4-(2,3-dihidro-1,4-benzodioxin-2-il)bencil]pirrolidina, 4-[4-(2,3-dihidro-1,4-benzodioxin-2-il)bencil]morfolina, 1-[4-(2,3-dihidro-1,4-benzodioxin-2-il)bencil]-4,4-dimetilpiperidina, 8-[4-(2,3-dihidro-1,4-benzodioxin-2-il)bencil]-2,8-diazaspiro[4.5]decan-1-ona, 1-[4-(2,3-dihidro-1,4-benzodioxin-2-il)bencil]-4-fluoropiperidina, (1s,4s)-7-[4-(2,3-dihidro-1,4-benzodioxin-2-il)bencil]-7-azabiciclo[2.2.1]heptano, 1,1-dióxido de 4-[4-(2,3-dihidro-1,4-benzodioxin-2-il)bencil]tiomorfolina, 1-{4-[(2S)-2,3-dihidro-1,4-benzodioxin-2-il]bencil}-N,N-dimetilpiperidin-4-carboxamida, (3S)-1-[4-(2,3-dihidro-1,4-benzodioxin-2-il)bencil]pirrolidin-3-ol, 1-({1-[4-(2,3-dihidro-1,4-benzodioxin-2-il)bencil]piperidin-3-il}metil)pirrolidin-2-ona, 1-{4-[4-(2,3-dihidro-1,4-benzodioxin-2-il)bencil]piperazin-1-il}etanona, 2-{[4-(2,3-dihidro-1,4-benzodioxin-2-il)bencil]amino}-1-(pirrolidin-1-il)etanona, N-{4-[(2S)-2,3-dihidro-1,4-benzodioxin-2-il]bencil}-N-metil-1-(metilsulfonil)piperidin-4-amina, 1-{4-[{4-[(2S)-2,3-dihidro-1,4-benzodioxin-2-il]bencil}(metil)amino]piperidin-1-il}etanona, 3-[4-(pirrolidin-1-ilmetil)fenil]-2,3-dihidro[1,4]dioxino[2,3-b]piridina, 7-[4-(2,3-dihidro-1,4-benzodioxin-2-il)bencil]-5,6,7,8-tetrahidro[1,2,4]triazolo[4,3-a]pirazina, 3-{4-[(1,1-dioxidotiomorfolin-4-il)metil]fenil}-2,3-dihidro[1,4]dioxino[2,3-b]piridina, 3-[4-(morfolin-4-ilmetil)fenil]-2,3-dihidro[1,4]dioxino[2,3-b]piridina, ácido (3R)-1-{4-[(2S)-2,3-dihidro-1,4-benzodioxin-2-il]bencil}piperidin-3-carboxílico, ácido (3S)-1-{4-[(2S)-2,3-dihidro-1,4-benzodioxin-2-il]bencil}piperidin-3-carboxílico, 1-(1-{4-[(2S)-2,3-dihidro-1,4-benzodioxin-2-il]bencil}piperidin-4-il)-2,2,2-trifluoroetanol, 2-(1-{4-[(2S)-2,3-dihidro-1,4-benzodioxin-2-il]bencil}piperidin-4-il)-1,1,1,3,3,3-hexafluoropropan-2-ol, N-[4-(2,3-dihidro-1,4-benzodioxin-2-il)bencil]-2-metilpropan-2-amina, (2R)-N-[4-(2,3-dihidro-1,4-benzodioxin-2-il)bencil]butan-2-amina, 1-[4-(2,3-dihidro-1,4-benzodioxin-2-il)bencil]-N-metilpiperidin-4-carboxamida, ácido 4-{1-[4-(2,3-dihidro-1,4-benzodioxin-2-il)bencil]piperidin-4-il}butanoico, {1-[4-(2,3-dihidro-1,4-benzodioxin-2-il)bencil]piperidin-4-il}metanol, 2-{1-[4-(2,3-dihidro-1,4-benzodioxin-2-il)bencil]piperidin-4-il}propan-2-oI, 3-{1-[4(2,3-dihidro-1,4-benzodioxin-2-il)bencil]piperidin-4-il}propan-1-oI, 1-[4-(2,3-dihidro-1,4-benzodioxin-2-il)bencil]-4-metil-1,4-diazepan, 1-{4-[4-(2,3-dihidro-1,4-benzodioxin-2-il)bencil]-1,4-diazepan-1-il}etanona, 4-[4-(2,3-dihidro-1,4-benzodioxin-2-il)bencil]-1,4-oxazepan, N-[4-(2,3-dihidro-1,4-benzodioxin-2-il)bencil]-2-metoxi-N-metiletanamina, (3R)-1-[4-(2,3-dihidro-1,4-benzodioxin-2-il)bencil]pirrolidin-3-oI, 8-[4-(2,3-dihidro-1,4-benzodioxin-2-il)bencil]-1,3,8-triazaspiro[4.5]decan-2,4-diona, 1-[4-(2,3-dihidro-1,4-benzodioxin-2-il)bencil]-3-metoxiazetidina, {1-[4-(2,3-dihidro-1,4-benzodioxin-2-il)bencil]piperidin-4-il}(morfolin-4-il)metanona 2-{1-[4-(2,3-dihidro-1,4-benzodioxin-2-il)bencil]piperidin-4-il}-N,N-dimetilacetamida, 1-[4-(2,3-dihidro-1,4-benzodioxin-2-il)bencil]-4-(metilsulfonil)piperidina, 1-[4-(2,3-dihidro-1,4-benzodioxin-2-il)bencil]azepan, N-[4-(2,3-dihidro-1,4-benzodioxin-2-il)bencil]ciclopentanamina, N-[4-(2,3-dihidro-1,4-benzodioxin-2-il)bencil]-N-metil-2(piridin-2-il)etanamina, 1-ciclopropil-N-[4-(2,3-dihidro-1,4-benzodioxin-2-il)bencil]metanamina, 1-[4-(2,3-dihidro-1,4-benzodioxin-2-il)bencil]-4-fenilpiperidin-4-ol, N-[4-(2,3-dihidro-1,4-benzodioxin-2-il)bencil]-N-etiletanamina, 1-[4-(2,3-dihidro-1,4-benzodioxin-2-il)bencil]azetidin-3-carbonitrilo, 1-[4-(2,3-dihidro-1,4-benzodioxin-2-il)bencil]-3-metoxipirrolidina N-{1-[4-(2,3-dihidro-1,4-benzodioxin-2-il)bencil]piperidin-4-il}metansulfonamida, N-[4-(2,3-dihidro-1,4-benzodioxin-2-il)bencil]-2-metil-1-(pirrolidin-1-il)propan-2-amina, 1-({1-[4-(2,3-dihidro-1,4-benzodioxin-2-il)bencil]piperidin-4-il}metil)pirrolidin-2-ona, 1-[4-(2,3-dihidro-1,4-benzodioxin-2-il)bencil]-N,N-dimetilpiperidin-4-carboxamida, 1-[4-(2,3-dihidro-1,4-benzodioxin-2-il)bencil]-N-(2-hidroxietiI)piperidin-4-carboxamida, 1-{1-[4-(2,3-dihidro-1,4-benzodioxin-2-il)bencil]piperidin-4-il}urea, 1-[4-(2,3-dihidro-1,4-benzodioxin-2-il)fenil]-N-(piridin-3-ilmetil)metanamina, 1-[4-(2,3-dihidro-1,4-benzodioxin-2-il)fenil]-N-[(1-metil-1H-imidazol-4-il)metil]metanamina, ácido 2-{4-[(2S)-2,3-dihidro-1,4-benzodioxin-2-il]bencil}-1,2,3,4-tetrahidroisoquinolin-4-carboxílico, ácido (1R,3S)-3-({4-[(2S)-2,3-dihidro-1,4-benzodioxin-2-il]bencil}amino)ciclopentancarboxilico, ácido 3-({4-[(2S)-2,3-dihidro-1,4-benzodioxin-2-il]bencil}amino)-4,4,dimetilpentanoico, ácido 1-({4-[(2S)-2,3-dihidro
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