AR088925A1 - Derivados de 3-cianaril-1h-pirrolo[2,3-b]piridina - Google Patents

Derivados de 3-cianaril-1h-pirrolo[2,3-b]piridina

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Publication number
AR088925A1
AR088925A1 ARP120104361A ARP120104361A AR088925A1 AR 088925 A1 AR088925 A1 AR 088925A1 AR P120104361 A ARP120104361 A AR P120104361A AR P120104361 A ARP120104361 A AR P120104361A AR 088925 A1 AR088925 A1 AR 088925A1
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Argentina
Prior art keywords
phet1
hal
nhcoo
nhconh
atoms
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ARP120104361A
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English (en)
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Dr Dipl-Chem Dorsch Dieter
Dr Hoelzemann Guenter
Dr Eggenweiler Hans
Michael-Dr Czodrowski Paul
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Merck Patent Ges Mit Beschränkter Haftung
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Publication of AR088925A1 publication Critical patent/AR088925A1/es

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    • C07DHETEROCYCLIC COMPOUNDS
    • C07D471/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04Ortho-condensed systems
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435Heterocyclic 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
    • A61K31/4353Heterocyclic 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
    • A61K31/437Heterocyclic 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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    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495Heterocyclic 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
    • A61K31/496Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
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    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/535Heterocyclic 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
    • A61K31/53751,4-Oxazines, e.g. morpholine
    • A61K31/53771,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
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    • A61K45/00Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
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  • General Health & Medical Sciences (AREA)
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  • Life Sciences & Earth Sciences (AREA)
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Abstract

Los compuestos de la fórmula (1) en donde X es CH o N; R¹ es H, A o Cyc; R² es O[C(R⁶)₂]ₙHet¹, NR⁶[C(R⁶)₂]ₙHet¹, O[C(R⁶)₂]ₙCyc o NR⁶[C(R⁶)₂]ₙCyc; R³ es H, Hal, A, OR⁶, N(R⁶)₂, O[C(R⁶)₂]ₘN(R⁶)₂, O[C(R⁶)₂]ₙHet², NR⁶[C(R⁶)₂]ₘN(R⁶)₂, NR⁶[C(R⁶)₂]ₙHet², Ar o Het²; R⁴ es H u OR⁶; R⁵ es H u OR⁶; R⁶ es H o alquilo C₁₋₆ no ramificado o ramificado, en donde 1 - 7 átomos de H pueden estar reemplazados por F; Het¹ es dihidropirrolilo, pirrolidinilo, azetidinilo, oxetanilo, tetrahidroimidazolilo, dihidropirazolilo, tetrahidropirazolilo, tetrahidrofuranilo, dihidropiridilo, tetrahidropiridilo, piperidinilo, morfolinilo, hexahidropiridazinilo, hexahidropirimidinilo, [1,3]dioxolanilo, tetrahidropiranilo o piperazinilo no sustituido o monosustituido con Hal, CN, OH, OA, COOA, CONH₂, S(O)ₙA, S(O)ₙAr, COA, A u =O; Het² es dihidropirrolilo, pirrolidinilo, azetidinilo, tetrahidroimidazolilo, tetrahidrofuranilo, dihidropirazolilo, tetrahidropirazolilo, dihidropiridilo, tetrahidropiridilo, dihidropiranilo, tetrahidropiranilo, piperidinilo, morfolinilo, hexahidropiridazinilo, hexahidropirimidinilo, [1,3]dioxolanilo, piperazinilo, furilo, tienilo, pirrolilo, imidazolilo, pirazolilo, oxazolilo, isoxazolilo, tiazolilo, triazolilo, tetrazolilo, piridilo, pirimidilo, piridazinilo, indolilo, isoindolilo, bencimidazolilo, indazolilo, quinolilo, 1,3-benzodioxolilo, benzotiofenilo, benzofuranilo, imidazopiridilo o furo[3,2-b]piridilo no sustituido o mono- o disustituido con Hal, A, [C(R⁶)₂]ₚOR⁶, [C(R⁶)₂]ₚN(R⁶)₂, [C(R⁶)₂]ₚHet¹, NO₂, CN, [C(R⁶)₂]ₚCOOR⁶, CON(R⁶)₂, NR⁶COA, NR⁶SO₂A, SO₂N(R⁶)₂, S(O)ₙA, COHet¹, O[C(R⁶)₂]ₚN(R⁶)₂, O[C(R⁶)₂]ₚHet¹, NHCOOA, NHCON(R⁶)₂, NHCOO[C(R⁶)₂]ₚN(R⁶)₂, NHCOO[C(R⁶)₂]ₚHet¹, NHCONH[C(R⁶)₂]ₚN(R⁶)₂, NHCONH[C(R⁶)₂]ₚHet¹, OCONH[C(R⁶)₂]ₚN(R⁶)₂, OCONH[C(R⁶)₂]ₚHet¹, CHO, COA, =S, =NR⁶ y/u =O; Ar es fenilo o naftilo no sustituido o mono-, disustituido o trisustituido con Hal, A, [C(R⁶)₂]ₚOR⁶, [C(R⁶)₂]ₚN(R⁶)₂, [C(R⁶)₂]ₚHet¹, NO₂, CN, [C(R⁶)₂]ₚCOOR⁶, CON(R⁶)₂, NR⁶COA, NR⁶SO₂A, SO₂N(R⁶)₂, S(O)ₙA, COHet¹, O[C(R⁶)₂]ₚN(R⁶)₂, O[C(R⁶)₂]ₚHet¹, NHCOOA, NHCON(R⁶)₂, NHCOO[C(R⁶)₂]ₚN(R⁶)₂, NHCOO[C(R⁶)₂]ₚHet¹, NHCONH[C(R⁶)₂]ₚN(R⁶)₂, NHCONH[C(R⁶)₂]ₚHet¹, OCONH[C(R⁶)₂]ₚN(R⁶)₂, OCO-H[C(R⁶)₂]ₚHet¹, CHO y/o COA; A es alquilo C₁₋₁₀ no ramificado o ramificado, en donde uno o dos grupos CH y/o CH₂ no adyacentes pueden estar reemplazados por átomos de N, O y/o S y/o también 1 - 7 átomos de H pueden estar reemplazados por F y/o Cl; Cyc es alquilo cíclico no sustituido o monosustituido con CN o sustituido con A con 3, 4, 5, 6 o 7 átomos de C; Hal es F, Cl, Br o I; m es 1, 2 ó 3; n es 0, 1 ó 2; p es 0, 1, 2, 3 ó 4; así como sus sales, tautómeros y estereoisómeros farmacéuticamente aceptables, incluyendo sus mezclas en todas las proporciones. Son inhibidores de TBK1 e IKKe y se pueden usar, por ejemplo, para el tratamiento de cáncer y enfermedades inflamatorias.
ARP120104361A 2011-11-22 2012-11-21 Derivados de 3-cianaril-1h-pirrolo[2,3-b]piridina AR088925A1 (es)

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DE102011119127A DE102011119127A1 (de) 2011-11-22 2011-11-22 3-Cyanaryl-1H-pyrrolo[2.3-b]pyridin-Derivate

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US (1) US9102675B2 (es)
EP (1) EP2794602B1 (es)
JP (1) JP6096797B2 (es)
CN (1) CN103946223B (es)
AR (1) AR088925A1 (es)
AU (1) AU2012342891B2 (es)
CA (1) CA2856357C (es)
DE (1) DE102011119127A1 (es)
ES (1) ES2661256T3 (es)
IL (1) IL232717B (es)
WO (1) WO2013075785A1 (es)

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GB201702947D0 (en) 2017-02-23 2017-04-12 Domainex Ltd Novel compounds
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CA2856357C (en) 2019-10-01
US9102675B2 (en) 2015-08-11
IL232717A0 (en) 2014-08-03
DE102011119127A1 (de) 2013-05-23
CN103946223A (zh) 2014-07-23
US20140323481A1 (en) 2014-10-30
IL232717B (en) 2018-08-30
WO2013075785A1 (de) 2013-05-30
CA2856357A1 (en) 2013-05-30
CN103946223B (zh) 2017-01-18
EP2794602A1 (de) 2014-10-29
JP6096797B2 (ja) 2017-03-15
ES2661256T3 (es) 2018-03-28
AU2012342891A1 (en) 2014-07-03
AU2012342891B2 (en) 2016-10-13
AU2012342891A8 (en) 2014-07-31
JP2014534246A (ja) 2014-12-18

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