AR090548A1 - Azaheterociclobencilaminas biciclicas como inhibidores de pi3k - Google Patents

Azaheterociclobencilaminas biciclicas como inhibidores de pi3k

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AR090548A1
AR090548A1 ARP130101033A ARP130101033A AR090548A1 AR 090548 A1 AR090548 A1 AR 090548A1 AR P130101033 A ARP130101033 A AR P130101033A AR P130101033 A ARP130101033 A AR P130101033A AR 090548 A1 AR090548 A1 AR 090548A1
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alkyl
independently selected
alkynyl
alkenyl
haloalkyl
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Incyte Corp
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    • C—CHEMISTRY; METALLURGY
    • 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
    • A61K31/495—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
    • A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
    • 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
    • A61K31/55—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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/06—Antipsoriatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
    • C07C53/15—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen containing halogen
    • C07C53/16—Halogenated acetic acids
    • C07C53/18—Halogenated acetic acids containing fluorine

Abstract

Modulan la actividad de las fosfoinositida 3-quinasas (PI3K) y son útiles en el tratamiento de enfermedades relacionadas con la actividad de PI3K, que incluye, por ejemplo, trastornos inflamatorios, trastornos con base inmunológica, cáncer y otras enfermedades. Reivindicación 1: Un compuesto de fórmula (1) o una sal farmacéuticamente aceptable de este, donde: V es C(=O), S(=O)₂, CH₂, CHR³ᶜ, y CR³ᶜR³ᶜ; T es C(=O), S(=O)₂, CH₂, CHR³ᵃ, y CR³ᵃR³ᵃ; Q es C(=O), S(=O)₂, (CH₂)ₙ, (CHR³ᵃ)ₙ, y (CR³ᵃR³ᵃ)ₙ; donde n es 0, 1, ó 2; U es O ó NR³ᵈ; siempre que cuando T es C(=O) o S(=O)₂, Q es (CH₂)ₙ,(CHR³ᵃ)ₙ, o -(CR³ᵃR³ᵃ)ₙ; y siempre que cuando Q es C(=O) o S(=O)₂, T es CH₂, CHR³ᵃ, o CR³ᵃR³ᵃ y U es NR³ᵈ; RA es H o alquilo C₁₋₃; Ar es un resto de formula (2), (3), (4) ó (5); X¹ es CH o N; Y¹ es CH o N; o alternativamente, RA y Ar, junto con el N al que están unidos, se combinan para formar un grupo funcional de fórmula (6); X es CR⁹ o N; W es CR⁷ o N; Y es CR⁸, CR⁸ᵃ, o N; Z es un enlace o C(=O); siempre que -W=Y-Z- es -CR⁷=CR⁸-, -N=CR⁸-, -CR⁷=CR⁸ᵃ-C(=O)-, -N=CR⁸ᵃ-C(=O)-, o -CR⁷=N-C(=O)-; R¹ es alquilo C₁₋₃; cada R³ᵃ se selecciona independientemente de alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, haloalquilo C₁₋₆, y Cy¹; donde dicho alquilo C₁₋₆, alquenilo C₂₋₆, y alquinilo C₂₋₆ está cada uno opcionalmente sustituido con 1, 2, ó 3 grupos R¹¹ seleccionados independientemente; R³ᵇ es H, Cy, -(alquileno C₁₋₃)-Cy, alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, haloalquilo C₁₋₆, C₍₌O₎Rᵇ, C(=O)NRᶜRᵈ, C(=O)ORᵃ, C(=NRᵉ)Rᵇ, C(=NRᵉ)NRᶜRᵈ, S(=O)₂Rᵇ, o S(=O)₂NRᶜRᵈ; donde dicho alquilo C₁₋₆, alquenilo C₂₋₆, y alquinilo C₂₋₆ está cada uno opcionalmente sustituido por 1, 2, 3, ó 4 grupos R¹³ᵇ seleccionados independientemente; cada R³ᶜ se selecciona independientemente de alquilo C₁₋₄, haloalquilo C₁₋₄, alcoxi C₁₋₄-alquilo C₁₋₄, y haloalcoxi C₁₋₄-alquilo C₁₋₄; R³ᵈ es H, alquilo C₁₋₄, haloalquilo C₁₋₄, alcoxi C₁₋₄-alquilo C₁₋₄, o haloalcoxi C₁₋₄-alquilo C₁₋₄; R⁴ es H, halo, OH, CN, alquilo C₁₋₄, haloalquilo C₁₋₄, alcoxi C₁₋₄, o haloalcoxi C₁₋₄; R⁵ es halo, OH, CN, alquilo C₁₋₄, haloalquilo C₁₋₄, alcoxi C₁₋₄, haloalcoxi C₁₋₄, o ciclopropilo; R⁶ es H, halo, OH, CN, alquilo C₁₋₄, haloalquilo C₁₋₄, alcoxi C₁₋₄, o haloalcoxi C₁₋₄; R⁷ es H o alquilo C₁₋₄; R⁸ es H, halo, -OH, -CN, alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, haloalquilo C₁₋₆, Cy², -(alquileno C₁₋₃)-Cy², ORᵃ², SRᵃ², C(=O)Rᵇ², C(=O)NRᶜ²Rᵈ², C(=O) ORᵃ², OC(=O)Rᵇ², OC(=O)NRᶜ²Rᵈ², NRᶜ²Rᵈ², NRᶜ²C(=O)Rᵇ², NRᶜ²C(=O)ORᵇ², NRᶜ²C(=O)NRᶜ²Rᵈ², C(=NRᵉ)Rᵇ², C(=NRᵉ)NRᶜ²Rᵈ², NRᶜ²C(=NRᵉ)NRᶜ²Rᵈ², NRᶜ²S(=O)Rᵇ², NRᶜ²S(=O)₂NRᶜ²Rᵈ², S(=O)Rᵇ², S(=O)₂Rᵇ², o S(=O)₂NRᶜ²Rᵈ²; donde dicho alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆ está cada uno opcionalmente sustituido por 1, 2, 3, ó 4 grupos R¹¹ seleccionados independientemente; R⁸ᵃ es H, halo, -CN, alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, haloalquilo C₁₋₆, Cy², -(alquileno C₁₋₃)-Cy², C(=O)Rᵇ², C(=O)NRᶜ²Rᵈ², C(=O)ORᵃ², NRᶜ²Rᵈ², NRᶜ²C(=O)Rᵇ², NRᶜ²C(=O)ORᵇ², NRᶜ²C(=O)NRᶜ²Rᵈ², NRᶜ²S(=O)Rᵇ², NRᶜ²S(=O)₂NRᶜ²Rᵈ², S(=O)Rᵇ², S(=O)₂Rᵇ², o S(=O)₂NRᶜ²Rᵈ²; donde dicho alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆ está cada uno opcionalmente sustituido por 1, 2, 3, ó 4 grupos R¹¹ seleccionados independientemente; R⁹ es H, halo, OH, CN, alquilo C₁₋₄, haloalquilo C₁₋₄, alcoxi C₁₋₄, o haloalcoxi C₁₋₄; R¹⁰ es H o alquilo C₁₋₄; cada R¹¹ se selecciona independientemente de halo, OH, NO₂, CN, alquilo C₁₋₃-, alquenilo C₂₋₃, alquinilo C₂₋₃, haloalquilo C₁₋₃, ciano-alquilo C₁₋₃, HO-alquilo C₁₋₃, alcoxi C₁₋₃-alquilo C₁₋₃, cicloalquilo C₃₋₇, alcoxi C₁₋₃, haloalcoxi C₁₋₃, amino, alquil C₁₋₃amino, di(alquil C₁₋₃)amino, tio, alquil C₁₋₃tio, alquil C₁₋₃sulfinilo, alquil C₁₋₃sulfonilo, carbamilo, alquil C₁₋₃carbamilo, di(alquil C₁₋₃)carbamilo, carboxi, alquil C₁₋₃carbonilo, alcoxi C₁₋₄carbonilo, alquil C₁₋₃carbonilamino, alquil C₁₋₃sulfonilamino, aminosulfonilo, alquil C₁₋₃aminosulfonilo, di(alquil C₁₋₃)aminosulfonilo, aminosulfonilamino, alquil C₁₋₃aminosulfonilamino, di(alquil C₁₋₃)aminosulfonilamino, aminocarbonilamino, alquil C₁₋₃aminocarbonilamino, y di(alquil C₁₋₃)aminocarbonilamino; cada R¹³ᵇ se selecciona independientemente de Cy¹, -(alquileno C₁₋₃)-Cy¹, halo, CN, NO₂, alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, haloalquilo C₁₋₆, ORᵃ¹, SRᵃ¹, C(=O)Rᵇ¹, C(=O)NRᶜ¹Rᵈ¹, C(=O)ORᵃ¹, OC(=O)Rᵇ¹, OC(=O)NRᶜ¹Rᵈ¹, NRᶜ¹Rᵈ¹, NRᶜ¹C(=O)Rᵇ¹, NRᶜ¹C(=O)ORᵇ¹, NRᶜ¹C(=O)NRᶜ¹Rᵈ¹, C(=NRᵉ)Rᵇ¹, C(=NRᵉ)NRᶜ¹Rᵈ¹, NRᶜ¹C(=NRᵉ)NRᶜ¹Rᵈ¹, NRᶜ¹S(=O)Rᵇ¹, NRᶜ¹S(=O)₂NRᶜ¹Rᵈ¹, S(=O)Rᵇ¹, S(=O)₂Rᵇ¹, S(=O)₂NRᶜ¹Rᵈ¹; donde dicho alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆ está cada uno opcionalmente sustituido con 1, 2, ó 3 grupos R¹¹ seleccionados independientemente; cada Cy se selecciona independientemente de cicloalquilo C₃₋₇, heterocicloalquilo de 4 - 10 miembros, fenilo, naftilo y heteroarilo de 5 - 10 miembros, donde dicho cicloalquilo C₃₋₇, heterocicloalquilo de 4 - 10 miembros, fenilo, naftilo y heteroarilo de 5 - 10 miembros están opcionalmente sustituidos con 1, 2, 3, ó 4 grupos R¹³ᵇ seleccionados independientemente; cada Rᵃ, Rᶜ, y Rᵈ se selecciona independientemente de H, alquilo C₁₋₆, haloalquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, y Cy; donde dicho alquilo C₁₋₆, alquenilo C₂₋₆, y alquinilo C₂₋₆ está cada uno opcionalmente sustituido con 1, 2, ó 3 grupos R¹³ᵇ seleccionados independientemente; cada Rᵇ se selecciona independientemente de alquilo C₁₋₆, haloalquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, y Cy; donde dicho alquilo C₁₋₆, alquenilo C₂₋₆, y alquinilo C₂₋₆ está cada uno opcionalmente sustituido con 1, 2, ó 3 grupos R¹³ᵇ seleccionados independientemente; o alternativamente, Rᶜ y Rᵈ junto con el átomo N al que están unidos forman un grupo heterocicloalquilo de 4-, 5-, 6- ó 7- miembros, que está opcionalmente sustituido con 1, 2, ó 3 grupos R¹³ᵇ seleccionados independientemente; cada Rᵉ se selecciona independientemente de H, CN, OH, alquilo C₁₋₄, y alcoxi C₁₋₄; cada Cy¹ se selecciona independientemente de cicloalquilo C₃₋₇, heterocicloalquilo de 4 - 7 miembros, fenilo y heteroarilo de 5 - 6 miembros, donde dicho cicloalquilo C₃₋₇, heterocicloalquilo de 4 - 7 miembros, fenilo y heteroarilo de 5 - 6 miembros están opcion
ARP130101033A 2012-04-02 2013-03-27 Azaheterociclobencilaminas biciclicas como inhibidores de pi3k AR090548A1 (es)

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