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AR110592A1 - (aza)indol- y benzofuran-3-sulfanomidas - Google Patents

(aza)indol- y benzofuran-3-sulfanomidas

Info

Publication number
AR110592A1
AR110592A1 ARP170103687A ARP170103687A AR110592A1 AR 110592 A1 AR110592 A1 AR 110592A1 AR P170103687 A ARP170103687 A AR P170103687A AR P170103687 A ARP170103687 A AR P170103687A AR 110592 A1 AR110592 A1 AR 110592A1
Authority
AR
Argentina
Prior art keywords
alkoxy
substituted
unsubstituted
halogen
alkyl
Prior art date
Application number
ARP170103687A
Other languages
English (en)
Inventor
Anas Barr
LAUFENBERG Daniel VON
Sabrina Gollos
Lukas Schwach
Mario Funke
Vigneshwaran Namasivayam
Sanjay Bhattarai
Nader M Boshta
Laurent Provins
Jel Mercier
Marie Ledecq
Joerg Hockemeyer
Ali El-Tayeb
Michael Louis Robert Deligny
Ccile Pegurier
Christa E Mueller
Original Assignee
Ucb Pharma Gmbh
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 Ucb Pharma Gmbh filed Critical Ucb Pharma Gmbh
Publication of AR110592A1 publication Critical patent/AR110592A1/es

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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
    • A61K31/40—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
    • A61K31/403—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
    • A61K31/404—Indoles, e.g. pindolol
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    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/425—Thiazoles
    • A61K31/429—Thiazoles condensed with heterocyclic ring systems
    • A61K31/43—Compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula, e.g. penicillins, penems
    • A61K31/431—Compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula, e.g. penicillins, penems containing further heterocyclic rings, e.g. ticarcillin, azlocillin, oxacillin
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    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/433—Thidiazoles
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    • 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
    • A61K31/4353—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
    • A61K31/437—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 five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
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    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
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    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/90—Benzo [c, d] indoles; Hydrogenated benzo [c, d] indoles
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    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans 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 carbon atoms of the hetero ring
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    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring
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    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
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  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

Reivindicación 1: Un compuesto caracterizado porque tiene la fórmula (1), en donde X¹ es N o C(R⁷); X² es NH, S u O; X³ es N o C(R¹²); R² se selecciona de hidrógeno, fluoro, cloro, bromo, yodo y metoxi; R⁴ se selecciona de hidrógeno, metoxi y halógeno; R⁵ se selecciona de hidrógeno, halógeno, ciano, alquilo C₁₋₆, alcoxi C₁₋₆, alquilcarbonilo C₁₋₃, alcoxicarbonilo C₁₋₃, alquilsulfinilo C₁₋₃ y alquilsulfonilo C₁₋₃, en donde cada alquilo o alcoxi puede ser opcionalmente sustituido o más veces seleccionadas de halógeno, alcoxi C₁₋₃, alquinilo C₂₋₃, alquenilo C₂₋₃, ciano, azido, hidroxilo y alquilaminocarbonilo C₁₋₃, o R⁵ forma un anillo junto con R⁶ como se describe en la presente; R⁶ se selecciona de hidrógeno, hidroxi, halógeno, ciano, azido, nitro, alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, alcoxi C₁₋₆, cicloalquilo C₃₋₇, cicloalquenilo C₃₋₆, heterocicloalquilo C₃₋₇, heterocicloalquenilo C₃₋₇, fenilo, heteroarilo C₅₋₁₀, heterociclilo C₈₋₁₀, -ORˣ, -SRˣ, -SORˣ, SO₂Rˣ, -pentafluorosulfanilo, NRʸRᶻᶻ, -NRʸCORˣ, -NRʸCO₂Rˣ, -NRˣCONRʸRᶻ, -NRʸSORˣ, -NRʸSO₂Rˣ, -CORˣ, -CO₂Rˣ, -CONRʸRᶻ, en donde cada grupo alquilo, alquenilo, alquinilo, alcoxi, cicloalquilo, heterocicloalquilo, cicloalquenilo, fenilo, heteroarilo o heterociclilo en R⁶ puede ser no sustituido o sustituido con uno o más sustituyentes seleccionados de halógeno, hidroxi, oxo, ciano, azido, nitro, alquilo C₁₋₆, haloalquilo C₁₋₆, alcoxi C₁₋₆alquilo C₁₋₃, cicloalquilo C₃₋₇, heterocicloalquilo C₃₋₇, fenilo, heteroarilo C₅₋₁₀, ORˣ, -SRˣ, -SORˣ, SO₂Rˣ, -pentafluorosulfanilo, NRʸRᶻ, -NRʸCORˣ, -NRʸCO₂Rˣ, -CORˣ, -CO₂Rˣ, -CONRʸRᶻ, en donde Rˣ, Rʸ, Rᶻ y Rᶻᶻ se seleccionan independientemente de hidrógeno, alquilo C₁₋₆, haloalquilo C₁₋₆, cicloalquilo C₃₋₇, cicloalquenilo C₃₋₆, cicloalquilo C₃₋₇alquilo C₁₋₆, fenilo, fenilalquilo C₁₋₆, heterocicloalquilo C₃₋₇, heterocicloalquilo C₃₋₇alquilo C₁₋₆, heteroarilo C₅₋₆ o heteroarilalquilo C₁₋₆, grupos cualquiera de los cuales puede ser no sustituido o sustituido con uno o más sustituyentes, seleccionado de los descritos anteriormente, o Rʸ y Rᶻ, o Rʸ y Rᶻᶻ junto con el átomo de amino al que ambos están unidos pueden formar un heterociclo C₅₋₆ aromático o no aromático, no sustituido o sustituido, en donde Rᶻᶻ es diferente de hidrógeno, o (i) R⁶ forma junto con R⁷ y los átomos de carbono a los que están unidos un anillo aromático o no aromático de 5 ó 6 miembros que puede contener opcionalmente uno o más heteroátomos seleccionados de S, O y N, y en donde dicho anillo puede ser no sustituido o sustituido con uno o más sustituyentes seleccionados de halógeno, hidroxi, ciano, alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₇, cicloalquilo C₃₋₇alquilo C₁₋₃, heterocicloalquilo C₃₋₇alquilo C₁₋₃, y alcoxi C₁₋₆, en donde cada alquilo o alcoxi puede ser no sustituido o sustituido con uno o más sustituyentes seleccionados de halógeno, hidroxi y alcoxi C₁₋₃ no sustituido o fluorado, o (ii) R⁶ forma junto con R⁵ y los átomos de carbono a los que están unidos R⁶ y R⁵, un 1,3-dioxolano que puede ser no sustituido o sustituido con uno o dos sustituyentes seleccionados de fluoro y metilo, o hidroxi, ciano, haloalcoxi C₁₋₆ preferiblemente fluoroalcoxi C₁₋₃ y alcoxi C₁₋₆; R⁷ se selecciona de hidrógeno, halógeno, ciano, alquilo C₁₋₆, alcoxi C₁₋₆, alquinilo C₂₋₆, alquenilo C₂₋₆, alquilcarbonilo C₁₋₆, alcoxicarbonilo C₁₋₆, alquilsulfonilo C₁₋₆, alquilsulfinilo C₁₋₆, alquiltio C₁₋₆, cicloalquilo C₃₋₇, cicloalquiloxi C₃₋₇, heterocicloalquilo C₃₋₄, heterocicloalquiloxi C₃₋₇, fenilo, feniloxi, fenilsulfonilo, fenilsulfinilo, heteroarilo C₅₋₆, heteroariloxi C₅₋₆, heteroarilo C₅₋₆alquilo C₁₋₃, heteroarilo C₅₋₆alcoxi C₁₋₃, cicloalquilo C₃₋₆alquilo C₁₋₂, cicloalquilo C₃₋₆alcoxi C₁₋₃, heterocicloalquiloxi C₃₋₆, heterocicloalquilo C₃₋₆alquilo C₁₋₂, heterocicloalquilo-alquiloxi C₁₋₂, fenilalquilo C₁₋₂, fenilalcoxi C₁₋₂, en donde cada grupo en R⁷ puede ser no sustituido o sustituido con uno o más sustituyentes seleccionados de halógeno, hidroxi, ciano, haloalcoxi C₁₋₆, o R⁷ forma un anillo junto con R⁶ como se describe en este documento; R⁸ se selecciona de hidrógeno, alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, alcoxi C₁₋₆, ciano y halógeno, en donde cada alquilo o alcoxi puede ser no sustituido o sustituido con uno o más sustituyentes seleccionados de halógeno y C₁₋₃ alcoxi, o forma un sistema de anillo junto con R⁹, como se describe en el presente documento; R⁹ se selecciona de hidrógeno, halógeno, ciano, azido, alquilo C₁₋₆, alcoxi C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆ y halógeno, en donde cada alquilo o alcoxi puede ser no sustituido o sustituido con uno o más sustituyentes seleccionados de halógeno y alcoxi C₁₋₃, o R⁹ forma junto con R⁸ o R¹⁰ y los átomos de C a los que están unidos un anillo de 5 ó 6 miembros que puede ser opcionalmente sustituido adicionalmente y que puede contener uno o más heteroátomos formadores de anillo seleccionados de N, S, O y Se; en donde el anillo formado por R⁹ junto con R⁸ o R¹⁰ y el anillo al que están unidos se seleccionan de un sistema de anillo bicíclico seleccionado de (a) 2,1,3-benzotiadiazol, (b) 2,1,3-benzoselenadiazol, (c) 2,1,3-benzoxadiazol, (d) 1,3-benzotiazol, (e) 1,3-benzoxazol que puede ser no sustituido o puede estar parcialmente hidrogenado y no sustituido o sustituido con oxo, (f) 1,3-benzodioxol que puede ser no sustituido o sustituido con uno o dos sustituyentes seleccionados de fluoro y metilo, (g) benzotiofeno, que pueden ser no sustituido o puede estar parcialmente hidrogenado y no sustituido o sustituido con uno o dos sustituyentes seleccionados de oxo, metilo o fluoro, en donde el benzotiofeno se hidrogena parcialmente a 1,3-dihidro-2-benzotiofeno, que puede ser opcionalmente sustituido con dos oxos para formar 1,1-dioxido-2,3-dihidro-1-benzotiofeno, y que puede ser opcionalmente sustituido adicionalmente, (h) 1,3-dihidro-2-benzofurano que puede ser sustituido con oxo para formar 3-oxo-1,3-dihidrobenzofurano, que puede ser opcionalmente sustituido además con uno o más, y (i) 2,3-dihidro-1H-isoindol, que no está sustituido o está sustituido con oxo para dar 3-oxo-2,3-dihidro-1H-isoindol, que puede ser opcionalmente sustituido adicionalmente; R¹⁰ se selecciona de hidrógeno, halógeno, alquilo C₁₋₆, alcoxi C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, ciano, cianoalquilo C₁₋₆, cianoalquiloxi C₁₋₆, alquilcarbonilo C₁₋₆, alcoxicarbonilo C₁₋₆, alquilsulfonilo C₁₋₆, alquilsulfinilo C₁₋₆, alquiltio C₁₋₆, cicloalquilo C₃₋₆, cicloalquiloxi C₃₋₆, heterociclo C₃₋₆heterocicloalquilo C₃₋₆, amino, azido, pentafluorosulfanilo, nitro, alquilaminocarbonilo C₁₋₃, di-alquilaminocarbonilo C₁₋₃, alquilsulfinilo C₁₋₃ y alquilsulfonilo C₁₋₃, en donde cada alquilo, alquenilo, alquinilo o alcoxi puede ser no sustituido o sustituido con uno o más sustituyentes seleccionados de halógeno, alcoxi C₁₋₆, haloalcoxi C₁₋₆, hidroxialcoxi C₁₋₆, alquiltio C₁₋₆ opcionalmente halogenado, alquilcarbonilo C₁₋₃ opcionalmente halogenado, alquiloxicarbonilo C₁₋₃, opcionalmente halogenado, alquilsulfonilo C₁₋₃ opcionalmente halogenado, alquilsulfinilo C₁₋₃ opcionalmente halogenado, alquilaminocarbonilo C₁₋₃, di-alquilaminocarbonilo C₁₋₃, hidroxi, ciano, nitro, oxo, cicloalquilo C₃₋₆, cicloalcoxi C₃₋₆, heterocicloalquilo C₃₋₆, heterocicloalcoxi C₃₋₆, fenilo, feniloxi y heteroarilo C₅₋₆, en donde cualquier cicloalquilo C₃₋₆, heterocicloalquilo C₃₋₆, fenilo y heteroarilo puede ser no sustituido o sustituido con uno o más residuos seleccionados de halógeno, hidroxi, hidroximetilo, oxo, ciano, nitro, amino, opcionalmente halogenado o hidroxilado alquilo C₁₋₃, opcionalmente hidroxilado o halogenado, alcoxi C₁₋₃ opcionalmente hidroxilado o halogenado, alquilcarbonilo C₁₋₃ opcionalmente halogenado y alcoxicarbonilo C₁₋₃ opcionalmente halogenado, en donde el grupo amino puede ser sustituido con uno o dos grupos seleccionados de alquilo C₁₋₃, alquilsulfonilo C₁₋₃, alquilcarbonilo C₁₋₃, y alcoxicarbonilo C₁₋₃, o R¹⁰ forma un sistema de anillo junto con R⁹, como se describe en el presente documento; R¹¹ se selecciona de hidrógeno, halógeno, ciano, azido, alquilo C₁₋₆, alcoxi C₁₋₆, alquilcarbonilo C₁₋₆, alcoxicarbonilo C₁₋₆, alquilsulfonilo C₁₋₆, y alquilsulfinilo C₁₋₆, alquenilo C₂₋₆, y alquinilo C₂₋₆, en donde cada alquilo o alcoxi puede ser no sustituido o sustituido con uno o más sustituyentes seleccionados de halógeno y alcoxi C₁₋₃ halogenado o no sustituido; R¹², si está presente, se selecciona de hidrógeno, alquilo C₁₋₆, alcoxi C₁₋₆ y halógeno, en donde cada alquilo o alcoxi puede ser no sustituido o sustituido con uno o más sustituyentes seleccionados de halógeno y alcoxi C₁₋₃, halogenado o no sustituido; y sales, solvatos, isótopos y co-cristales farmacéuticamente aceptables del mismo.
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