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AR038928A1 - Benzimidazol sulfonamidas sustituidas, como inhibidores de amplio espectro de la proteasa del vih - Google Patents

Benzimidazol sulfonamidas sustituidas, como inhibidores de amplio espectro de la proteasa del vih

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Publication number
AR038928A1
AR038928A1 ARP030100829A ARP030100829A AR038928A1 AR 038928 A1 AR038928 A1 AR 038928A1 AR P030100829 A ARP030100829 A AR P030100829A AR P030100829 A ARP030100829 A AR P030100829A AR 038928 A1 AR038928 A1 AR 038928A1
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Argentina
Prior art keywords
alkyl
het1
het2
aryl
cycloalkyl
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ARP030100829A
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English (en)
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Tibotec Pharm Ltd
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Publication of AR038928A1 publication Critical patent/AR038928A1/es

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—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
    • 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
    • C07D401/12—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 linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D235/08—Radicals containing only hydrogen and carbon atoms
    • 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
    • A61K31/415—1,2-Diazoles
    • 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
    • A61P31/14—Antivirals for RNA viruses
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
    • C07D235/30—Nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
    • C07D235/30—Nitrogen atoms not forming part of a nitro radical
    • C07D235/32—Benzimidazole-2-carbamic acids, unsubstituted or substituted; Esters thereof; Thio-analogues thereof
    • C—CHEMISTRY; METALLURGY
    • 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
    • C07D405/02—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 two hetero rings
    • C07D405/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/04—Ortho-condensed systems

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

Abstract

Se reivindica compuestos, composición farmacéutica, método y uso. Reivindicación 1: Un compuesto que tiene la fórmula (1), o su N-óxido, sal, forma estereoisomérica, mezcla racémica, pro-droga, éster o metabolito del mismo, en la cual fórmula (1): R1 es hidrógeno, alquilo (C1-6), alquenilo (C2-6), arilalquilo (C1-6), aril-alquenilo (C2-6), cicloalquilo (C3-7), cicloalquilo(C3-7)-alquilo(C1-6), arilo, Het1, Het1-alquilo (C1-6), Het2, Het2-alquilo(C1-6); R1 también puede ser un radical de la fórmula (2), en la cual: R9, R10a y R10b son, cada uno de ellos e independientemente entre sí, hidrógeno, alquilo(C1-4)-alcoxicarbonilo, carboxilo, aminocarbonilo, mono- ó di-(alquilo C1-4)-aminocarbonilo, cicloalquilo (C3-7), alquenilo (C2-6), alquinilo (C2-6) ó alquilo (C1-4) opcionalmente sustituido por arilo, Het1, Het2, cicloalquilo (C3-7), alquilo(C1-4)-oxicarbonilo, carboxilo, aminocarbonilo, mono ó di(alquilo C1-4)aminocarbonilo, aminosulfonilo, alquilo(C1-4)S(O)t, hidroxi, ciano, halógeno u opcionalmente amino mono- o di-sustituido, siendo los sustituyentes seleccionados entre el grupo que consiste en: alquilo (C1-4), arilo, arilalquilo (C1-4), cicloalquilo (C3-7), cicloalquilo(C3-7)-alquilo(C1-4)alquilo, Het1, Het2, Het1-alquilo (C1-4) y Het2-alquilo (C1-4); en lo cual, R9, R10a y los átomos de carbono a los cuales están unidos, opcionalmente forman un radical cicloalquilo (C3-7); R11a es hidrógeno, alquenilo (C2-6), alquinilo (C2-6), cicloalquilo (C3-7), arilo, amino carbonilo opcionalmente mono o di- sustituido, amino-alquilo (C1-4)carboniloxi opcionalmente mono- o di-sustituido, ariloxicarbonilo, Het1-oxicarbonilo, Het2-oxicarbonilo, ariloxicarbonil-alquilo (C1-4), aril-alquilo (C1-4)oxicarbonilo, alquilo (C1-4)carbonilo, cicloalquilo(C3-7)carbonilo, cicloalquilo(C3-7)-alquilo(C1-4)oxicarbonilo, cicloalquilo(C3-7)alquilcarboniloxi, carboxil-alquilo (C1-4)carboniloxi, alquilo(C1-4)carboniloxi, arilalquilo(C1-4)carboniloxi, arilacarboniloxi, ariloxicarboniloxi, Het1-carbonilo, Het1-carboniloxi, Het1-alquilo(C1-4)xicarboniloxi, Het2-carboniloxi, Het2-alquil(C1-4)carboniloxi, Het2-alquilo(C1-4)carboniloxi ó alquilo (C1-4) opcionalmente sustituido por arilo, ariloxi, Het2 ó hidroxi, estando los sustituyentes opcionales en los grupos amino, cada uno de ellos e independientemente entre sí, seleccionados entre el grupo que consiste en:alquilo (C1-4), arilo, arilalquilo (C1-4), cicloalquilo (C3-7), cicloalquilo (C3-7)-alquilo (C1-4), Het1, Het2, Het1-alquilo (C1-4) y Het1-alquilo (C1-4); con lo cual R11a puede estar opcionalmente ligado al resto de la molécula por intermedios de un grupo sulfonilo; R11b es hidrógeno, cicloalquilo (C3-7), alquenilo (C2-6), alquinilo (C2-6), arilo, Het1, Het2 ó alquilo (C1-4) opcionalmente sustituido por halógeno, hidroxi, alquilo(C1-4)S(=O)t, arilo, cicloalquilo (C3-7),Het1, Het2, amino opcionalmente mono- o di- sustituido siendo los sustituyentes seleccionados entre el grupo que consiste en: alquilo (C1-4), arilo, arilo, aril-alquilo (C1-4), cicloalquilo (C3-7), cicloalquilo(C3-7)-alquilo(C1-4), Het1, Het2, Het1-alquilo (C1-4), y Het2-alquilo (C1-4); cada uno de los t, independientemente de los demás, vale 0, 1 R2 es hidrógeno ó alquilo (C1-6); L es -C(=O)-, -O-C(=O)-, -NR8-C(=O)-, -O-alcanodiilo(C1-6)-C(=O)-, -NR8-alcanodiilo(C1-6)-C(=O)-, -S(=O)2-, -O-S(=O)-2, -NR8-alcanodiilo(C1-6)-S(=O)2, con la cual sea el grupo C(=O) sea el grupo S(=O)2 está fijado a la parte NR2, con la cual sea la parte alconodiilo (C1-6) está opcionalmente sustituido por hidroxi, arilo, Het1 ó Het2; R3 es alquilo (C1-6), arilo, cicloalquilo (C3-7), cicloalquilo (C3-7)-alquilo(C1-4), ó arilalquilo (C1-4) opcionalmente sustituido por alquilo (C1-4), halógeno, nitro, ciano, poli halo alquilo (C1-4), hidroxi, alquilo (C1-4)oxi, mercapto ó alquilo (C1-4)tio; R4 es hidrógeno, alquilo (C1-4)oxicarbonilo, carboxilo, amino, carbonilo, mono- ó di-(alquilo C1-4)amino carbonilo, cicloalquilo (C3-7), alquenilo (C2-6), alquinilo (C2-6) ó alquilo (C1-4) opcionalmente sustituido por arilo, Het1, Het2, cicloalquilo (C3-7), alquilo(C1-4)oxicarbonilo, carboxilo, amino, carbonilo, mono- ó di-(alquiloC1-4)amino carbonilo, amino sulfonilo, alquilo(C1-4)S(=O)t, hidroxi, ciano, halógeno o amino mono- ó di- sustituido, siendo los sustituyentes seleccionados entre el grupo que consiste en: alquilo (C1-4), arilo, arilalquilo (C1-4), cicloalquilo (C3-7), cicloalquilo(C3-7)-alquilo(C1-4), Het1, Het2, Het1-alquilo (C1-4) y Het2-alquilo (C1-4); o R4 también puede ser -X-R7, en lo cual: X es -O- ó -N(R7)-Y-; Y es -C(=O)-, S(=O)2-, -O-C(=O)-, -NR8-C(=O)-, -C(=O)-C(=O)-, -O-S(=O)2- ó -Nt8(=O)2-; R5 es hidrógeno, hidroxi, alquilo (C1-6), Het1-alquilo (C1-6), Het2-alquilo (C1-6) amino-alquilo (C1-6), pudiendo el grupo amino estar opcionalmente mono- ó di- sustituido por alquilo (C1-4); R6 es hidrógeno, alquilo (C1-6)oxi, Het1, Het1-oxi, Het2, Het2-oxi, arilo, ariloxi, ariloxi-alquilo (C1-4), alquilo(C1-4)oxiarilo, alquilo (C1-4)oxi Het1, alquilo(C1-4)oxi Het2, alquilo(C1-4)oxicarbonilamino, amino(C1-4)amino, amino ó amino-alquilo(C1-4)oxi, y en el caso en que A no es alcanodiilo (C1-6), entonces R6 puede ser también alquilo (C1-6), Het1-alquilo (C1-4), Het1-oxi-alquilo (C1-4), Het2-alquilo (C1-4), Het2-oxi-alquilo (C1-4), ariloalquilo (C1-4), ariloxoxialquilo (C1-4) ó aminoalquilo (C1-4); pudiendo cada uno de los grupos amino estar mono- ó di- sustituido por alquilo (C1-4); R5 y -A-R6 tomados conjuntamente con el átomo de nitrógeno al cual están ligados, pueden también formar Het1 ó Het2; R7 es hidrógeno, arilo, cicloalquilo (C3-7), Het1, Het2, alquenilo (C2-6), alquinilo (C2-6), ó alquilo (C1-4) opcionalmente sustituido con arilo, Het1, Het2, cicloalquilo (C3-7), alquilo (C1-4)oxi carbonilo, carboxilo, aminocarbonilo, mono- ó di-(alquiloC1-4)aminocarbonilo, aminosulfonilo, alquilo(C1-4)S(=O)t, hidroxi, ciano, halógeno o amino opcionalmente mono- ó di- sustituido estando los sustituyentes seleccionados entre el grupo que consiste en: alquilo (C1-4), arilo arilalquilo (C1-4), cicloalquilo (C3-7), cicloalquilo(C3-7)-alquilo(C1-4), Het1, Het2, Het1 (C1-4) y Het2 (C1-4); R8 es hidrógeno, alquilo (C1-6), alquenil (C2-6), arilalquilo (C1-6), cicloalquilo (C3-7), cicloalquilo (C3-7)alquilo C(1-6), arilo, Het1, Het1 alquilo(C1-6), Het2 alquilo (C1-6) R12 es hidrógeno, -NH2, -alquilo (C1-6) ó -alquilo (C1-6)-W-R14, estando dicho alquilo (C1-6) opcionalmente sustituido por halógeno, hidroxi, arilo, heteroarilo, Het1, Het2, ó amino, estando dicho amino opcionalmente mono- ó di- sustituido por alquilo (C1-4) ; ó R12 también puede ser -(R5)(AR6), y A es alcanodiilo (C1-6), -C(=O)-, -C(=O)2-, alcanodiilo(C1-6)-C(O)-, alcanodiilo(C1-6)-C-(=S)-, ó alcanodiilo(C1-6)-S(=O)2-; en lo cual, si A es alcanodiilo(C1-6)-C(=O)-, alcanodiilo(C1-6)-C(=S)-, ó alcanodiilo(C1-6)-S(=O)2-, la parte NR5 está fijada a la parte alcanodiilo (C1-6); W es oxi,, carbonilo, oxicarboniolo, carboniloxi, oxicarboniloxi, amino, aminocarbonilo, carbonilamino ó azufre; R13 es hidrógeno, alquilo (C1-6), opcionalmente sustituido por arilo, Het1, Het2, hidroxi, halógeno, amino, pudiendo el grupo amino estar opcionalmente mono- ó di- sustituido por alquilo (C1-4); R14 es alquilo (C1-4), arilo, Het1 ó Het2.
ARP030100829A 2002-03-12 2003-03-11 Benzimidazol sulfonamidas sustituidas, como inhibidores de amplio espectro de la proteasa del vih AR038928A1 (es)

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US (2) US20050171175A1 (es)
EP (1) EP1485358B1 (es)
JP (1) JP4557552B2 (es)
KR (3) KR20040093119A (es)
CN (2) CN1653053A (es)
AP (1) AP2111A (es)
AR (1) AR038928A1 (es)
AT (1) ATE497494T1 (es)
AU (1) AU2003219159B2 (es)
BR (1) BR0303373A (es)
CA (1) CA2479012C (es)
DE (1) DE60335939D1 (es)
DK (1) DK1485358T3 (es)
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HR (1) HRP20040936B1 (es)
IL (1) IL163960A0 (es)
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AU2003219159B2 (en) 2009-09-03
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