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AR100886A1 - 3-amino-1,5,6,7-tetrahidro-4h-indol-4-onas - Google Patents

3-amino-1,5,6,7-tetrahidro-4h-indol-4-onas

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Publication number
AR100886A1
AR100886A1 ARP150101931A ARP150101931A AR100886A1 AR 100886 A1 AR100886 A1 AR 100886A1 AR P150101931 A ARP150101931 A AR P150101931A AR P150101931 A ARP150101931 A AR P150101931A AR 100886 A1 AR100886 A1 AR 100886A1
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AR
Argentina
Prior art keywords
alkyl
independently
case
optionally substituted
phenyl
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ARP150101931A
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English (en)
Inventor
Dr Graubaum Heinz
Dr Blint Jozsef
Dr Sonnenschein Helmut
Dr Tempel Rene
Dr Lienau Philip
Dr Holton Simon
Dr Bone Wilhelm
Dr Siemeister Gerhard
Dr Schulze Volker
Dr Eis Knut
Dr Brfacker Lars
Dr Hitchcock Marion
Dr Briem Hans
Dr Graham Keith
Original Assignee
Bayer Pharma AG
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Publication of AR100886A1 publication Critical patent/AR100886A1/es

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    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • 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
    • A61K31/4353—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
    • A61K31/436—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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    • A61K31/437—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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    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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    • 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
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
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    • 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
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
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    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/472—Non-condensed isoquinolines, e.g. papaverine
    • A61K31/4725—Non-condensed isoquinolines, e.g. papaverine containing further heterocyclic rings
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    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/50—Pyridazines; Hydrogenated pyridazines
    • A61K31/501—Pyridazines; Hydrogenated pyridazines not condensed and containing further heterocyclic rings
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    • A61K31/00—Medicinal preparations containing organic active ingredients
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    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/5375—1,4-Oxazines, e.g. morpholine
    • A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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    • C07D—HETEROCYCLIC COMPOUNDS
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    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
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    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
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Abstract

Son inhibidores de la quinasa Bub1, procesos para su producción y su uso como compuestos farmacéuticos. Reivindicación 1: Un compuesto caracterizado porque es de fórmula (1) en donde: R¹ representa hidrógeno, C₁₋₄-alquilo, C₁₋₄-haloalquilo, C₃₋₆-cicloalquilo, o fenilo, donde dicho fenilo está opcionalmente sustituido, una o más veces, en forma independiente en cada caso, con R³, donde dicho C₃₋₆-cicloalquilo está opcionalmente sustituido, una o más veces, en forma independiente en cada caso, con halógeno; y R² representa hidrógeno, C₁₋₄-alquilo o C₁₋₄-haloalquilo; o R¹ y R² junto con el átomo de carbono al cual se encuentran unidos forman un anillo cicloalquilo de entre 3 y 7 miembros; y el anillo A representa un grupo seleccionado entre el grupo de fórmulas (2), donde * indica el punto de unión de dicho grupo con el resto de la molécula y dicho grupo está opcionalmente sustituido, una o más veces, en forma independiente en cada caso, con R³; y G¹ representa O, S, o NR²¹; G², G³ representan, en forma independiente entre sí, CR²¹ o N; R³ representa hidrógeno, halógeno, hidroxi, amino, nitro, ciano, C₁₋₄-alquilo, C₃₋₆-cicloalquilo, C₂₋₄-alquenilo, C₂₋₄-alquinilo, C₁₋₄-alcoxi, C₁₋₄-alcoxi-C₁₋₄-alquilo, C₁₋₄-haloalquilo, C₁₋₄-haloalcoxi, C₁₋₄-alquil-C(O)-, R¹⁸-O-C(O)-, R⁷R⁸N-C(O)-, C₁₋₄-alquil-C(O)-NH-, R⁷R⁸N-, R⁷R⁸N-SO₂-, o un grupo seleccionado entre el grupo de fórmulas (3), donde * indica el punto de unión de dicho grupo con el resto de la molécula; donde dichos grupos C₁₋₄-alquilo, C₁₋₄-alcoxi, C₁₋₄-haloalquilo o C₁₋₄-haloalcoxi están opcionalmente sustituidos con uno o dos grupos hidroxi; y G⁴ representa O, S, o NR²¹; G⁵, G⁶ representan, en forma independiente entre sí, CR²¹ o N; R⁶ representa, en forma independiente en cada caso, halógeno, hidroxi, amino, nitro, ciano, C₁₋₄-alquilo, C₁₋₄-alcoxi, C₁₋₄-alcoxi-C₁₋₄-alquilo, C₁₋₄-haloalquilo o C₁₋₄-haloalcoxi; y el anillo B representa un grupo seleccionado entre el grupo de fórmulas (4), donde * indica el punto de unión de dicho grupo con el resto de la molécula; y X representa CR⁴ o N; e Y representa CR⁴ o N, donde cuando uno de X e Y representa N, el otro representa CR⁴; y R⁴ representa, en forma independiente en cada caso, hidrógeno, halógeno, hidroxi, ciano, C₁₋₄-alquilo, C₃₋₄-cicloalquilo, C₁₋₄-alcoxi, C₁₋₄-alquil-S-, C₁₋₄-alquil-SO-, C₁₋₄-alquil-SO₂-, R⁹R¹⁰N-, R¹¹-C(O)-(NR⁷)-, (R¹¹-C(O)-)(R¹²-C(O)-)N-, R⁹R¹⁰N-C(O)-(NR⁷)-, R⁹R¹⁰N-C(S)-(NR⁷)-, R¹⁸-O-C(O)-(NR⁷)-, R⁹R¹⁰N-SO₂- o C₁₋₄-alquil-SO₂-NH-, donde dicho C₁₋₄-alquilo está opcionalmente sustituido, una o más veces, en forma independiente en cada caso, con un sustituyente seleccionado entre hidroxi y halógeno; y donde dicho C₁₋₄-alcoxi está opcionalmente sustituido, una o más veces, en forma independiente en cada caso, con un sustituyente seleccionado entre hidroxi, halógeno, C₁₋₄-alcoxi, C₃₋₆-cicloalquilo y fenilo, donde dicho fenilo está opcionalmente sustituido, una o más veces, en forma independiente en cada caso, con R³; y donde dicho C₃₋₄-cicloalquilo está opcionalmente sustituido, una o más veces, en forma independiente en cada caso, con halógeno; R⁵ representa, en forma independiente en cada caso, halógeno, hidroxi, amino, nitro, ciano, C₁₋₄-alquilo, C₃₋₆-cicloalquilo, C₁₋₄-alcoxi, C₁₋₄-haloalquilo, C₁₋₄-haloalcoxi o fenil-C₁₋₄-alquilo, donde dicho grupo fenilo está opcionalmente sustituido, una o más veces, en forma independiente en cada caso, con un sustituyente seleccionado entre halógeno, hidroxi, C₁₋₃-alquilo, C₁₋₃-haloalquilo y C₁₋₃-alcoxi; donde dicho grupo C₃₋₆-cicloalquilo está opcionalmente sustituido, una o más veces, en forma independiente en cada caso, con halógeno; y J representa hidrógeno o hidroxi; y E representa hidrógeno, C₁₋₄-alquilo, C₁₋₄-alcoxi-C₂₋₄-alquilo, R¹⁷ᵃR¹⁷ᵇR¹⁷ᶜSi-O-C₂₋₄-alquilo, C₁₋₄-alquil-SO₂-C₁₋₄-alquilo, R¹⁸-O-C(O)-C₁₋₄-alquilo, R⁷R⁸N-C₂₋₄-alquilo, R⁷R⁸N-C(O)-C₁₋₄-alquilo o fenil-C₁₋₄-alquilo, donde dicho C₁₋₄-alquilo está opcionalmente sustituido, una o más veces, en forma independiente en cada caso, con un sustituyente seleccionado entre hidroxi y halógeno; y donde dicho grupo fenilo está opcionalmente sustituido, una o más veces, en forma independiente en cada caso, con R⁵; Q representa O ó N-OR¹⁶; R⁷, R⁸ representan, en forma independiente entre sí, hidrógeno, C₁₋₄-alquilo o tert-butil-O-C(O)-; y R⁹, R¹⁰ representan, en forma independiente entre sí, hidrógeno, C₁₋₄-alquilo, C₃₋₆-cicloalquilo, C₁₋₄-haloalquilo, fenilo o heteroarilo, donde dicho grupo fenilo o heteroarilo está opcionalmente sustituido, una o más veces, en forma independiente en cada caso, con R⁵; y donde dicho C₁₋₄-alquilo está opcionalmente sustituido, una o más veces, en forma independiente en cada caso, con un sustituyente seleccionado entre hidroxi, C₁₋₄-alcoxi, C₁₋₄-alquil-S-, C₃₋₆-cicloalquilo, heterocicloalquilo de entre 4 y 6 miembros, fenilo, heteroarilo y R¹⁸-O-C(O)-, donde dicho C₃₋₆-cicloalquilo o heterocicloalquilo de entre 4 y 6 miembros está opcionalmente sustituido, una o más veces, en forma independiente en cada caso, con un sustituyente seleccionado entre halógeno, C₁₋₄-alquilo y tert-butil-O-C(O)-, donde dicho grupo fenilo o heteroarilo está opcionalmente sustituido, una o más veces, en forma independiente en cada caso, con R⁵; o R⁹ y R¹⁰ junto con el átomo de nitrógeno al cual están unidos forman un anillo heterocíclico de entre 3 y 7 miembros que contiene nitrógeno, que contiene opcionalmente un heteroátomo adicional seleccionado entre O, NH o S, y que puede estar sustituido opcionalmente, una o más veces, en forma independiente en cada caso, con R⁵; y R¹¹, R¹² representan, en forma independiente entre sí, C₁₋₄-alquilo, C₂₋₄-alquenilo, C₂₋₄-alquinilo, C₃₋₆-cicloalquilo, heterocicloalquilo de entre 4 y 6 miembros, fenilo, heteroarilo, o R¹³-(C₁₋₄-alquil)-O-CH₂-, donde dicho C₁₋₄-alquilo está opcionalmente sustituido, una o más veces, en forma independiente en cada caso, con un sustituyente seleccionado entre halógeno, hidroxi, ciano, C₁₋₄-alcoxi, R⁷R⁸N-, R¹⁴, R¹⁵-O-, y fenilo opcionalmente sustituido, una o más veces, en forma independiente en cada caso, con R⁵, y donde dicho C₃₋₆-cicloalquilo está opcionalmente sustituido, una o más veces, en forma independiente en cada caso, con un sustituyente seleccionado entre halógeno, ciano, C₁₋₄-alquilo, C₁₋₄-haloalquilo y fenilo opcionalmente sustituido, una o más veces, en forma independiente en cada caso, con R⁵, y donde dicho heterocicloalquilo de entre 4 y 6 miembros está opcionalmente sustituido, una o más veces, en forma independiente en cada caso, con un sustituyente seleccionado entre hidroxi, C₁₋₄-alquilo, C₁₋₄-alcoxi, R⁷R⁸N- y R¹⁸-O-C(O)-, y donde dicho fenilo o heteroarilo está opcionalmente sustituido, una o más veces, en forma independiente en cada caso, con R⁵; R¹³ representa C₃₋₄-alquilo ramificado, C₁₋₄-haloalquilo, C₂₋₄-alquenilo, C₂₋₄-alquinilo, C₃₋₆-cicloalquilo, heterocicloalquilo de entre 4 y 6 miembros, fenilo o heteroarilo, donde dicho fenilo o heteroarilo está opcionalmente sustituido, una o más veces, en forma independiente en cada caso, con R⁵; R¹⁴ representa C₁₋₄-alquil-S-, C₁₋₄-alquil-SO₂-, C₃₋₆-cicloalquilo, heterocicloalquilo de entre 4 y 6 miembros, fenilo o heteroarilo, donde dicho fenilo o heteroarilo está opcionalmente sustituido, una o más veces, en forma independiente en cada caso, con R⁵; R¹⁵ representa fenilo o heteroarilo, donde dicho fenilo o heteroarilo está opcionalmente sustituido, una o más veces, en forma independiente en cada caso, con R⁵; y R¹⁶ representa hidrógeno, C₁₋₆-alquilo, fenilo o C₁₋₄-alquil-C(O)-, donde dicho grupo fenilo está opcionalmente sustituido, una o más veces, en forma independiente en cada caso, con R⁵; R¹⁷ᵃ, R¹⁷ᵇ, R¹⁷ᶜ, representan, en forma independiente entre sí, C₁₋₄-alquilo; R¹⁸ representa hidrógeno o C₁₋₆-alquilo; R²¹ representa hidrógeno, C₁₋₄-alquilo, C₁₋₄-haloalquilo, o C₁₋₆-cicloalquilo opcionalmente sustituido, una o más veces, en forma independiente en cada caso, con halógeno; R²² representa hidrógeno, halógeno, C₁₋₄-alquilo, C₁₋₄-haloalquilo, o C₁₋₆-cicloalquilo opcionalmente sustituido, una o más veces, en forma independiente en cada caso, con halógeno; m representa 0, 1 ó 2; n representa 0, 1, 2 ó 3; o un N-óxido, una sal, un tautómero o un estereoisómero de dicho compuesto, o una sal de dicho N-óxido, tautómero o estereoisómero.
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