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

Composicion y actividad antiviral de derivados de piperazina azaindoloxoacetico sustituidas

Info

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
Authority
AR
Argentina
Prior art keywords
group
alkyl
heteroaryl
aryl
heteroalicyclic
Prior art date
Application number
ARP030102835A
Other languages
English (en)
Original Assignee
Bristol Myers Squibb Co
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
Family has litigation
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

Links

Classifications

    • 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
    • A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—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
    • 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
    • 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
    • A61K31/41—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
    • A61K31/427—Thiazoles not condensed and containing further 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
    • A61K31/435—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
    • A61K31/4402—Non condensed pyridines; Hydrogenated derivatives thereof only substituted in position 2, e.g. pheniramine, bisacodyl
    • 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
    • A61K31/435—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
    • 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
    • A61K31/435—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
    • 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
    • A61K31/513—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim having oxo groups directly attached to the heterocyclic ring, e.g. cytosine
    • 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
    • A61K31/52—Purines, e.g. adenine
    • 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
    • A61K31/535—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
    • 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
    • A61K31/63—Compounds containing para-N-benzenesulfonyl-N-groups, e.g. sulfanilamide, p-nitrobenzenesulfonyl hydrazide
    • A61K31/635—Compounds containing para-N-benzenesulfonyl-N-groups, e.g. sulfanilamide, p-nitrobenzenesulfonyl hydrazide having a heterocyclic ring, e.g. sulfadiazine
    • 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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • 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
    • A61K31/7068—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
    • 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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • 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
    • A61K31/7068—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
    • 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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A61P31/18—Antivirals for RNA viruses for HIV
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—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
    • 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
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—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
    • 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

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Epidemiology (AREA)
  • Organic Chemistry (AREA)
  • Molecular Biology (AREA)
  • Communicable Diseases (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oncology (AREA)
  • Virology (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • AIDS & HIV (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

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,
ARP030102835A 2002-08-07 2003-08-07 Composicion y actividad antiviral de derivados de piperazina azaindoloxoacetico sustituidas AR041190A1 (es)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US10/214,982 US20030207910A1 (en) 2001-02-02 2002-08-07 Composition and antiviral activity of substituted azaindoleoxoacetic piperazine derivatives

Publications (1)

Publication Number Publication Date
AR041190A1 true AR041190A1 (es) 2005-05-04

Family

ID=31714265

Family Applications (1)

Application Number Title Priority Date Filing Date
ARP030102835A AR041190A1 (es) 2002-08-07 2003-08-07 Composicion y actividad antiviral de derivados de piperazina azaindoloxoacetico sustituidas

Country Status (31)

Country Link
US (1) US20030207910A1 (es)
EP (4) EP2497770B1 (es)
KR (1) KR101045154B1 (es)
CN (2) CN101229164B (es)
AR (1) AR041190A1 (es)
AU (2) AU2003261367B2 (es)
BR (1) BRPI0313286B8 (es)
CA (1) CA2494832C (es)
CY (3) CY1113413T1 (es)
DK (3) DK2801576T3 (es)
ES (4) ES2560844T3 (es)
GE (1) GEP20084284B (es)
HK (4) HK1174037A1 (es)
HR (1) HRP20050123B8 (es)
HU (1) HUE027396T2 (es)
IL (1) IL166512A (es)
IS (1) IS2919B (es)
MX (1) MXPA05001441A (es)
MY (1) MY146549A (es)
NO (1) NO331591B1 (es)
NZ (1) NZ537930A (es)
PE (1) PE20040772A1 (es)
PL (1) PL219566B1 (es)
PT (3) PT2497770E (es)
RS (1) RS53428B (es)
RU (1) RU2325389C2 (es)
SI (3) SI2801576T1 (es)
TW (1) TWI328452B (es)
UA (1) UA82199C2 (es)
WO (1) WO2004014380A1 (es)
ZA (1) ZA200501018B (es)

Families Citing this family (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB0307834D0 (en) * 2003-04-04 2003-05-14 Ta Contrast Ab Composition
US20050075364A1 (en) * 2003-07-01 2005-04-07 Kap-Sun Yeung Indole, azaindole and related heterocyclic N-substituted piperazine derivatives
US20050124623A1 (en) * 2003-11-26 2005-06-09 Bender John A. Diazaindole-dicarbonyl-piperazinyl antiviral agents
US7745625B2 (en) 2004-03-15 2010-06-29 Bristol-Myers Squibb Company Prodrugs of piperazine and substituted piperidine antiviral agents
US20050215544A1 (en) * 2004-03-24 2005-09-29 Pin-Fang Lin Methods of treating HIV infection
US7776863B2 (en) * 2004-03-24 2010-08-17 Bristol-Myers Squibb Company Methods of treating HIV infection
DE602005010698D1 (de) 2004-06-09 2008-12-11 Glaxo Group Ltd Pyrrolopyridinderivate
US20060100209A1 (en) * 2004-11-09 2006-05-11 Chong-Hui Gu Formulations of 1-(4-benzoyl-piperazin-1-yl)-2-[4-methoxy-7-(3-methyl-[1,2,4]triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-ethane-1,2-dione
US20060100432A1 (en) * 2004-11-09 2006-05-11 Matiskella John D Crystalline materials of 1-(4-benzoyl-piperazin-1-yl)-2-[4-methoxy-7-(3-methyl-[1,2,4]triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-ethane-1,2-dione
US7183284B2 (en) * 2004-12-29 2007-02-27 Bristol-Myers Squibb Company Aminium salts of 1,2,3-triazoles as prodrugs of drugs including antiviral agents
US7601715B2 (en) 2005-06-22 2009-10-13 Bristol-Myers Squibb Company Process for preparing triazole substituted azaindoleoxoacetic piperazine derivatives and novel salt forms produced therein
US7598380B2 (en) * 2005-08-03 2009-10-06 Bristol-Myers Squibb Company Method of preparation of azaindole derivatives
US7851476B2 (en) * 2005-12-14 2010-12-14 Bristol-Myers Squibb Company Crystalline forms of 1-benzoyl-4-[2-[4-methoxy-7-(3-methyl-1H-1,2,4-triazol-1-YL)-1-[(phosphonooxy)methyl]-1H-pyrrolo[2,3-C]pyridin-3-YL]-1,2-dioxoethyl]-piperazine
US7807671B2 (en) 2006-04-25 2010-10-05 Bristol-Myers Squibb Company Diketo-piperazine and piperidine derivatives as antiviral agents
US7504399B2 (en) * 2006-06-08 2009-03-17 Bristol-Meyers Squibb Company Piperazine enamines as antiviral agents
US8318941B2 (en) * 2006-07-06 2012-11-27 Bristol-Myers Squibb Company Pyridone/hydroxypyridine 11-beta hydroxysteroid dehydrogenase type I inhibitors
EP2346508B1 (en) 2008-09-26 2016-08-24 Intellikine, LLC Heterocyclic kinase inhibitors
GB0910667D0 (en) * 2009-06-19 2009-08-05 Glaxo Wellcome Mfg Pte Ltd Novel compounds
WO2012019003A1 (en) * 2010-08-06 2012-02-09 Bristol-Myers Squibb Company Substituted indole and azaindole oxoacetyl piperazinamide derivatives
ES2585396T3 (es) * 2010-12-02 2016-10-05 VIIV Healthcare UK (No.5) Limited Alquilamidas como inhibidores de la unión del VIH
CN102718692B (zh) * 2012-07-03 2014-01-08 苏州和健医药科技有限公司 一种7位甲基-5位氧取代吲哚化合物的制备方法
WO2016004272A1 (en) 2014-07-02 2016-01-07 Pharmacyclics Llc Inhibitors of bruton's tyrosine kinase
EP3194387B1 (en) * 2014-09-17 2019-07-31 Celgene Quanticel Research, Inc. Histone demethylase inhibitors
CA2983927A1 (en) 2015-05-06 2016-11-10 The Regents Of The University Of California K-ras modulators
EP4340839A1 (fr) * 2021-05-21 2024-03-27 Centre National de la Recherche Scientifique (CNRS) Nouveaux derives azaindole en tant qu'agents antiviraux

Family Cites Families (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2761201A (en) 1952-05-02 1956-09-04 Griffin Wheel Co Renewing molds
US3830602A (en) 1973-03-14 1974-08-20 Commercial Shearing Rotary pumps and motors
US5023265A (en) * 1990-06-01 1991-06-11 Schering Corporation Substituted 1-H-pyrrolopyridine-3-carboxamides
IL99843A0 (en) 1990-11-01 1992-08-18 Merck & Co Inc Synergistic combination of hiv reverse transcriptase inhibitors
US5811432A (en) 1990-11-09 1998-09-22 Pfizer Inc Azaoxindole derivatives
JP3119485B2 (ja) 1991-07-03 2000-12-18 ファルマシア・アンド・アップジョン・カンパニー 抗−エイズ薬としての置換インドール類
US5124327A (en) * 1991-09-06 1992-06-23 Merck & Co., Inc. HIV reverse transcriptase
WO1993005020A1 (en) 1991-09-06 1993-03-18 Merck & Co., Inc. Indoles as inhibitors of hiv reverse transcriptase
US5413999A (en) 1991-11-08 1995-05-09 Merck & Co., Inc. HIV protease inhibitors useful for the treatment of AIDS
IT1265057B1 (it) 1993-08-05 1996-10-28 Dompe Spa Tropil 7-azaindolil-3-carbossiamidi
US5424329A (en) * 1993-08-18 1995-06-13 Warner-Lambert Company Indole-2-carboxamides as inhibitors of cell adhesion
GB9420521D0 (en) 1994-10-12 1994-11-30 Smithkline Beecham Plc Novel compounds
IL146309A0 (en) 1999-05-21 2002-07-25 Scios Inc Indole-type derivatives as inhibitors of p38 kinase
US6469006B1 (en) 1999-06-15 2002-10-22 Bristol-Myers Squibb Company Antiviral indoleoxoacetyl piperazine derivatives
US6476034B2 (en) 2000-02-22 2002-11-05 Bristol-Myers Squibb Company Antiviral azaindole derivatives
US20020061892A1 (en) 2000-02-22 2002-05-23 Tao Wang Antiviral azaindole derivatives
ES2250422T3 (es) 2000-07-10 2006-04-16 Bristol-Myers Squibb Company Composicion y actividad antiviral de derivados de piperazina indoloxoaceticos sustituidos.
US6403211B1 (en) 2000-07-18 2002-06-11 3M Innovative Properties Company Liquid crystal polymer for flexible circuits
EE05424B1 (et) * 2001-02-02 2011-06-15 Bristol-Myers Squibb Company Asendatud asaindooloksoatseetpiperasiini derivaadid, neid sisaldav ravimpreparaat ning nende kasutamine ravis
AU2003217604A1 (en) * 2002-02-23 2003-09-09 Bristol-Myers Squibb Company Method of treating hiv infection by preventing interaction of cd4 and gp120

Also Published As

Publication number Publication date
PT2497770E (pt) 2014-07-18
CY1117217T1 (el) 2017-04-05
EP2801576B1 (en) 2015-12-09
CY1113413T1 (el) 2016-06-22
HK1220181A1 (zh) 2017-04-28
UA82199C2 (uk) 2008-03-25
CN1688311A (zh) 2005-10-26
JP2006504669A (ja) 2006-02-09
HUE027396T2 (en) 2016-09-28
US20030207910A1 (en) 2003-11-06
RU2325389C2 (ru) 2008-05-27
EP2975038A1 (en) 2016-01-20
TW200410696A (en) 2004-07-01
KR20060021811A (ko) 2006-03-08
CN101229164A (zh) 2008-07-30
CA2494832A1 (en) 2004-02-19
EP1549313B9 (en) 2012-11-21
HRP20050123B8 (hr) 2015-04-10
BRPI0313286A8 (pt) 2018-05-08
DK2801576T3 (en) 2016-03-07
CY1115580T1 (el) 2017-01-04
PT1549313E (pt) 2012-09-05
ES2481044T3 (es) 2014-07-29
ES2560844T3 (es) 2016-02-23
WO2004014380A1 (en) 2004-02-19
KR101045154B1 (ko) 2011-07-04
BRPI0313286B8 (pt) 2021-05-25
IL166512A0 (en) 2006-01-15
BRPI0313286A2 (pt) 2005-07-05
IS2919B (is) 2015-01-15
RS53428B (en) 2014-12-31
SI2497770T1 (sl) 2014-11-28
NO20050514L (no) 2005-03-18
PT2801576E (pt) 2016-03-03
PL375360A1 (en) 2005-11-28
AU2003261367B2 (en) 2009-03-12
EP2801576A1 (en) 2014-11-12
DK2497770T3 (da) 2014-07-28
HRP20050123A2 (en) 2006-02-28
CN101229164B (zh) 2013-01-02
AU2009202361A1 (en) 2009-07-02
EP1549313A1 (en) 2005-07-06
MXPA05001441A (es) 2005-06-06
BRPI0313286B1 (pt) 2019-02-05
TWI328452B (en) 2010-08-11
EP1549313B1 (en) 2012-06-27
DK1549313T3 (da) 2012-10-01
PE20040772A1 (es) 2004-11-20
NO331591B1 (no) 2012-01-30
HK1202530A1 (en) 2015-10-02
IL166512A (en) 2014-12-31
EP2497770B1 (en) 2014-05-14
ES2388919T3 (es) 2012-10-19
ES2641893T3 (es) 2017-11-14
ZA200501018B (en) 2006-09-27
RS20050108A (en) 2007-09-21
AU2009202361B2 (en) 2011-10-13
IS7682A (is) 2005-02-01
CN100379421C (zh) 2008-04-09
NZ537930A (en) 2008-01-31
JP4430539B2 (ja) 2010-03-10
PL219566B1 (pl) 2015-05-29
EP2497770A1 (en) 2012-09-12
EP2975038B1 (en) 2017-07-12
EP1549313A4 (en) 2010-08-04
SI1549313T1 (sl) 2013-01-31
MY146549A (en) 2012-08-15
GEP20084284B (en) 2008-01-10
HK1174037A1 (en) 2013-05-31
RU2005106350A (ru) 2005-11-20
HRP20050123B1 (hr) 2014-04-25
AU2003261367A1 (en) 2004-02-25
HK1072731A1 (en) 2005-09-09
SI2801576T1 (sl) 2016-03-31
CA2494832C (en) 2012-07-10

Similar Documents

Publication Publication Date Title
AR041190A1 (es) Composicion y actividad antiviral de derivados de piperazina azaindoloxoacetico sustituidas
AR046920A1 (es) Hidroxamatos conectados a acilurea y conectado a sulfonilurea
AR060658A1 (es) Derivados de diceto-piperazina y piperidina como agentes antivirales
AR064345A1 (es) Derivados de 8-oxoadenina
EA200501617A1 (ru) Новые гетероциклические соединения, применяемые для лечения нарушений аллергической или воспалительной природы: способы синтеза и содержащие их фармацевтические составы
AR057979A1 (es) PIRAZOLPIRIMIDINAS COMO INHIBIDORAS DE PROTEíNA QUINASA. COMPOSICIONES FARMACEUTICAS.
HUP0401784A2 (hu) Heterobiciklikus szerkezetû virális polimeráz inhibitorok, eljárás az elõállításukra, köztitermékek és ezeket tartalmazó gyógyszerkészítmények
AR057989A1 (es) Derivados de indol-2-il-amida 1,5-sustituida. procesos de obtencion y composiciones farmaceuticas
AR055878A1 (es) Derivados de ciclopropanocarboxamida
NO20063470L (no) Tetrazolforbindelser og deres anvendelse av metabotrofe glutamatreseptorantagonister
AR025884A1 (es) Compuestos de amina ciclica, su produccion y su uso
AR061651A1 (es) Analogos de piridina ii
AR055801A1 (es) Derivados de piperazina azaindoloxoacetica sustituida, forma cristalina del derivado 1,2,3-triazol, procesos de preparacion de los mismos y composiciones farmaceuticas que los contienen
AR056883A1 (es) Derivados de 7-azaindol-2 carboxamida, un proceso para la preparacion de los mismos, composiciones farmaceuticas que los contienen y su uso en la fabricacion de un medicamento para el tratamiento de enfermedades asociadas con la modulacion de receptores de h3
AR058287A1 (es) Derivados de isoquinolina y composicion farmaceutica
AR037534A1 (es) Derivado de adamantano, su uso en la fabricacion de un medicamento para usar en terapia, composicion farmaceutica, proceso para la preparacion de dicho compuesto y dicha composicion y compuestos intermediarios
AR049398A1 (es) Derivados de sulfamato y sulfamida; una composicion farmaceutica que los contiene y su uso en la preparacion de un medicamento util para el tratamiento de la epilepsia y trastornos relacionados.
MD3820873T2 (ro) Degradanți selectivi ai receptorului estrogen
AR053195A1 (es) Compuestos inhibidores de dipeptidil peptidasa-iv metodos para preparar los mismos y composiciones farmaceuticas que los contienen como un agente activo
AR038172A1 (es) Compuesto de ciclohexano y ciclohexeno, su uso para preparar una composicion farmaceutica, dicha composicion farmaceutica, procedimiento para preparar el compuesto y compuestos intermediarios en dicho procedimiento
HUP0100950A2 (hu) Ciklusos aminovegyületek, alkalmazásuk gyógyászati készítmények előállítására és a vegyületeket tartalmazó gyógyászati készítmények
AR058404A1 (es) Derivados diamina como inhibidores de leucotrieno a4 hidrolasa
AR041672A1 (es) Compuesto biciclico de benzamida, composicion farmaceutica que lo comprende, su uso para la fabricacion de un medicamento y procedimiento para prepararlo
AR048042A1 (es) Inhibidores no nucleosidos de transcriptasa inversa y composiciones farmaceuticas
PE20001303A1 (es) Derivados de la 4-aroilpiperidina como antagonistas del receptor ccr-3

Legal Events

Date Code Title Description
FG Grant, registration