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AR041190A1 - Composicion y actividad antiviral de derivados de piperazina azaindoloxoacetico sustituidas - Google Patents

Composicion y actividad antiviral de derivados de piperazina azaindoloxoacetico sustituidas

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Publication number
AR041190A1
AR041190A1 ARP030102835A ARP030102835A AR041190A1 AR 041190 A1 AR041190 A1 AR 041190A1 AR P030102835 A ARP030102835 A AR P030102835A AR P030102835 A ARP030102835 A AR P030102835A AR 041190 A1 AR041190 A1 AR 041190A1
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AR
Argentina
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group
alkyl
heteroaryl
aryl
heteroalicyclic
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ARP030102835A
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Bristol Myers Squibb Co
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First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=31714265&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=AR041190(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Bristol Myers Squibb Co filed Critical Bristol Myers Squibb Co
Publication of AR041190A1 publication Critical patent/AR041190A1/es

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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
    • A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
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    • C07D471/02—Heterocyclic 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
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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
    • A61K31/47—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
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/513—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim having oxo groups directly attached to the heterocyclic ring, e.g. cytosine
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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
    • A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
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    • 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
    • A61K31/536—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 ortho- or peri-condensed with carbocyclic ring systems
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    • A61K31/635—Compounds containing para-N-benzenesulfonyl-N-groups, e.g. sulfanilamide, p-nitrobenzenesulfonyl hydrazide having a heterocyclic ring, e.g. sulfadiazine
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    • A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
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    • A61K31/7068—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines having oxo groups directly attached to the pyrimidine ring, e.g. cytidine, cytidylic acid
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    • A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
    • A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
    • A61K31/7064—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines
    • A61K31/7068—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines having oxo groups directly attached to the pyrimidine ring, e.g. cytidine, cytidylic acid
    • A61K31/7072—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines having oxo groups directly attached to the pyrimidine ring, e.g. cytidine, cytidylic acid having two oxo groups directly attached to the pyrimidine ring, e.g. uridine, uridylic acid, thymidine, zidovudine
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    • A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
    • A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
    • A61K31/7064—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines
    • A61K31/7076—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines containing purines, e.g. adenosine, adenylic acid
    • A61K31/708—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines containing purines, e.g. adenosine, adenylic acid having oxo groups directly attached to the purine ring system, e.g. guanosine, guanylic acid
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    • C07D471/02—Heterocyclic 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
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    • C07D471/12—Heterocyclic 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 three hetero rings

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Abstract

La presente, provee compuestos que poseen propiedades farmacológicas y de bio-afectación, sus composiciones farmacéuticas y método de uso. En particular, la invención se refiere a derivados de azaindoloxoacetilpiperazina. Estos compuestos ejercen una actividad exclusiva, ya sea cuando se los usa solos o en combinación con otros antivirales, anti-infecciosos, inmunomoduladores o inhibidores de la entrada del VIH. Más específicamente, la presente se refiere al tratamiento del VIH y SIDA Reivindicación 1: Un compuesto de fórmula (1), que incluye sus sales farmacéuticamente aceptables, caracterizado porque: Q es seleccionado del grupo integrado por las estructuras (2), donde R1, R2, R3 y R4, son independientemente seleccionados del grupo integrado por hidrógeno, halógeno, ciano, nitro, COOR56, XR57, C(O)R7, C(O)NR55R56, B, D, y E siempre y cuando, al menos uno entre R1-R4 sea seleccionado entre B o E; donde la linea punteada representa un enlace carbono-carbono o no existe; m es 1 o 2; R5 es hidrógeno o (CH2)nCH3, -C(O)(CH2)nCH3, -C(O)O(CH2)nCH3s, -C(O)(CH2)nN(CH3)2 donde n es 0-5; R6 es O o no existe; A es seleccionado del grupo integrado por C1-6alcoxi, arilo y heteroarilo; donde dicho arilo es fenilo o naftilo; dicho heteroarilo seleccionado del grupo integrado por piridinilo, pirimidinilo, pirazinilo, triazinilo, furanilo, tienilo, pirrolilo, imidazolilo, tiazolilo, isotiazolilo, oxazolilo, isoxazolilo, quinolinilo, isoquinolinilo, benzofuranilo, benzotienilo, benzoimidazolilo y benzotiazolilo; y dicho arilo o heteroarilo es opcionalmente substituido con uno o dos miembros iguales o diferentes seleccionados del grupo integrado por amino, nitro, ciano, hidroxi, C1-6alcoxi, -C(O)NH2, C1-6alquilo, -NHC(O)CH3, halógeno y trifluorometilo; -W- es de fórmula (3), B es seleccionado del grupo integrado por -C(=NR46)(R47), C(O)NR40R41, arilo, heteroarilo, heteroalicíclico, S(O)2R8, C(O)R7, XR8a, alquilo C1-6NR40R41, alquilo C1-6COOR8b; donde dicho arilo, heteroarilo, y heteroalicíclico son opcionalmente substituidos con uno a tres halógenos iguales o diferentes o entre uno a tres substituyentes iguales o diferentes seleccionados del grupo F; donde arilo es naftilo o fenilo substituido; donde heteroarilo es un sistema mono o bicíclico que contiene entre 3 y 7 átomos anulares para un sistema monocíclico y hasta 12 átomos en un sistema bicíclico fusionado, que incluye entre 1 y 4 heteroátomos; donde heteroalicíclico es un anillo monocíclico de 3 a 7 miembros que puede contener entre 1 y 2 heteroátomos en el esqueleto del anillo y que puede fusionarse a un anillo de benceno o piridina; q es 0, 1, o 2; D es seleccionado del grupo integrado por alquilo C1-6 y alquenilo C2-6; donde dicho alquilo C1-6 y alquenilo C2-6 están opcionalmente substituidos con uno a tres halógenos iguales o diferentes o entre uno y tres substituyentes seleccionados del grupo integrado por C(O)NR55R56, hidroxi, ciano y XR57; E es seleccionado del grupo integrado por alquilo C1-6 y alquenilo C2-6; donde dicho alquilo C1-6 y alquenilo C2-6 están opcional e independientemente substituidos con un miembro seleccionado del grupo integrado por fenilo, heteroarilo, SMe, SPh, -C(O)NR56R57, C(O)R57, SO2alquilo C1-6 y SO2Ph; donde heteroarilo es un sistema monocíclico que contiene entre 3 y 7 átomos anulares, que incluye entre 1 y 4 heteroátomos; F es seleccionado del grupo integrado por alquilo, cicloalquilo, arilo, heteroarilo, heteroalicíclico, hidroxi, alcoxi C1-6, ariloxi, tioalcoxi C1-6, ciano, halógeno, nitro, -C(O)R57, bencilo, -NR42C(O)-alquilo C1-6, -NR42C(O)-cicloalquilo C3-6, -NR42C(O)-arilo, -NR42C(O)-heteroarilo, -NR42C(O)-heteroalicíclico, un anillo cíclico de N-lactama de 4, 5, o 6 miembros, -NR42S(O)2-alquilo C1-6, -NR42S(O)2-cicloalquilo C3-6, -NR42S(O)2-arilo, -NR42S(O)2-heteroarilo, -NR42S(O)2-heteroalicíclico, S(O)2alquilo C1-6, S(O)2arilo,-S(O)2NR42R43, NR42R43, alquilo C1-6C(O)NR42R43, C(O)NR42R43, NHC(O)NR42R43, OC(O)NR42R43, NHC(O)OR54, alquilo C1-6NR42R43, COOR54, y alquilo C1-6COOR54; donde dicho alquilo C1-6, cicloalquilo C3-7, arilo, heteroarilo, heteroalicíclico, alcoxi C1-6, y ariloxi, están opcionalmente substituidos con uno a nueve halógenos iguales o diferentes o entre uno y cinco substituyentes iguales o diferentes seleccionados del grupo G; donde arilo es fenilo; heteroarilo es un sistema monocíclico que contiene entre 3 y 7 átomos anulares, que incluye entre 1 y 4 heteroátomos; heteroalicíclico es seleccionado del grupo integrado por aziridina, azetidina, pirrolidina, piperazina, piperidina, tetrahidrofurano, tetrahidropirano, azepina, y morfolina; G es seleccionado del grupo integrado por alquilo C1-6, cicloalquilo C3-7, arilo, heteroarilo, heteroalicíclico, hidroxi, alcoxi C1-6, ariloxi, ciano, halógeno, nitro, -C(O)R57, bencilo, -NR48C(O)-alquilo C1-6, -NR48C(O)-cicloalquilo C3-6, -NR48C(-O)-arilo, -NR48C(O)-heteroarilo, -NR48C(O)-heteroalicíclico, un anillo cíclico de N-lactama de 4, 5, o 6 miembros, -NR48S(O)2-alquilo C1-6, -NR48S(O)2-cicloalquilo C3-6, -NR48S(O)2-arilo, -NR48S(O)2-heteroarilo, -NR48S(O)2-heteroalicíclico, sulfinilo, sulfonilo, sulfonamida, NR48R49, alquilo C1-6C(O)NR48R49, C(O)NR48R49, NHC(O)NR48R49, OC(O)NR48R49, NHC(O)OR54', alquilo C1-6NR48R49, COOR54, y alquilo COOR54; donde arilo es fenilo; heteroarilo es un sistema monocíclico que contiene entre 3 y 7 átomos anulares, que incluye entre 1 y 4 heteroátomos; heteroalicíclico es seleccionado del grupo integrado por aziridina, azetidina, pirrolidina, piperazina, piperidina, tetrahidrofurano, tetrahidropirano, azepina, y morfolina; R7 es seleccionado del grupo integrado por arilo, heteroarilo, heteroalicíclico; donde dicho arilo, heteroarilo, y heteroalicíclico son opcionalmente substituidos con uno a tres halógenos iguales o diferentes o entre uno a tres substituyentes iguales o diferentes seleccionados del grupo F; donde para R7, R8, R8a, R8b arilo es fenilo; heteroarilo es un sistema mono o bicíclico que contiene entre 3 y 7 átomos anulares para un sistema monocíclico y hasta 10 átomos en un sistema bicíclico, que incluye entre 1 y 4 heteroátomos; donde heteroalicíclico es seleccionado del grupo integrado por aziridina, azetidina, pirrolidina, piperazina, piperidina, tetrahidrofurano, tetrahidropirano, azepina, y morfolina; R8 es seleccionado del grupo integrado por hidrógeno, alquilo C1-6, cicloalquilo C3-7, alquenilo C2-6, cicloalquenilo C3-7, alquinilo C2-6, arilo, heteroarilo, y heteroalicíclico; donde dicho alquilo C1-6, cicloalquilo C3-7, alquenilo C2-6, cicloalquenilo C3-7, alquinilo C2-6, arilo, heteroarilo, y heteroalicíclico están opcionalmente substituidos con uno a seis halógenos iguales o diferentes o entre uno y cinco substituyentes iguales o diferentes seleccionado del grupo F; R8a es un miembro seleccionado del grupo integrado por arilo, heteroarilo, heteroalicíclico; donde cada miembro está opcional e independientemente substituido con uno a seis halógenos iguales o diferentes o entre uno y cinco substituyentes iguales o diferentes seleccionados del grupo F; R8b es seleccionado del grupo integrado por hidrógeno, alquilo C1-6 y fenilo; R9, R10, R11, R12, R13, R14, R15, R16, son independientemente seleccionados del grupo integrado por hidrógeno y alquilo; donde dicho alquilo está opcionalmente substituido con uno a tres halógenos iguales o diferentes; X es seleccionado del grupo integrado por NH o NCH3, O, y S; R40 y R41 son independientemente seleccionado del grupo integrado por (a) hidrógeno; (b) alquilo C1-6 o cicloalquilo C3-7 substituido con uno a tres halógenos iguales o diferentes o entre uno y dos substituyentes iguales o diferentes seleccionados del grupo F; y (c) alcoxi C1-6, arilo, heteroarilo o heteroalicíclico; o R40 y R41 tomados en conjunto con el nitrógeno al cual se unen forman un miembro seleccionado del grupo integrado por aziridina, azetidina, pirrolidina, piperazina, 4-NMe piperazina, piperidina, azepina, y morfolina; y donde dicho arilo, heteroarilo, y heteroalicíclico son opcionalmente substituidos con uno a tres halógenos iguales o diferentes o entre uno y dos substituyentes iguales o diferentes seleccionados del grupo F; donde para R40 y R41 arilo es fenilo; heteroarilo es un sistema monocíclico que contiene entre 3 y 6 átomos anulares, que incluye entre 1 y 4 heteroátomos; heteroalicíclico es seleccionado del grupo integrado por aziridina, azetidina, pirrolidina, piperazina, piperidina, tetrahidrofurano, tetrahidropirano, azepina, y morfolina; con la condición que cuando B sea C(O)NR40R41, al menos uno, R40 o R41 no sea seleccionado entre los grupos (a) o (b); R42 y R43 son independientemente seleccionado del grupo integrado por hidrógeno, alquilo C1-6, alilo, alcoxi C1-6, cicloalquilo C3-7, arilo, heteroarilo y heteroalicíclico; o R42 y R43 tomados en conjunto con el nitrógeno al cual se unen forman un miembro seleccionado del grupo integrado por aziridina, azetidina, pirrolidina, piperazina, 4-NMe piperazina, piperidina, azepina, y morfolina; y donde dicho alquilo C1-6, alcoxi C1-6, cicloalquilo C3-7, arilo, heteroarilo, y heteroalicíclico están opcionalmente substituidos con uno a tres halógenos iguales o diferentes o entre uno y dos substituyentes iguales o diferentes seleccionados del grupo G; donde para R42 y R43 arilo es fenilo; heteroarilo es un sistema monocíclico que contiene entre 3 y 6 átomos anulares, que incluye entre 1 y 4 heteroátomos; heteroalicíclico es un miembro seleccionado del grupo integrado por aziridina, azetidina, pirrolidina, piperazina, piperidina, tetrahidrofurano, tetrahidropirano, azepina, y morfolina; Ra y Rb son independientemente H, alquilo C1-6 o fenilo; R46 es seleccionado del grupo integrado por H, OR57, y NR55R56; R47 es seleccionado del grupo integrado por H, amino, halógeno, fenilo, y alquilo; R48 y R49 son independientemente seleccionado del grupo integrado por hidrógeno, alquilo y fenilo; R50 es seleccionado del grupo integrado por H, alquilo C1-6, cicloalquilo C3-6,
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