AR044517A1 - INDOLIN AND INDOLINE DERIVATIVES REPLACED - Google Patents

INDOLIN AND INDOLINE DERIVATIVES REPLACED

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Publication number
AR044517A1
AR044517A1 ARP040101392A ARP040101392A AR044517A1 AR 044517 A1 AR044517 A1 AR 044517A1 AR P040101392 A ARP040101392 A AR P040101392A AR P040101392 A ARP040101392 A AR P040101392A AR 044517 A1 AR044517 A1 AR 044517A1
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AR
Argentina
Prior art keywords
alkyl
cycloalkyl
ilo
cyano
halo
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ARP040101392A
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Spanish (es)
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Lundbeck & Co As H
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Publication of AR044517A1 publication Critical patent/AR044517A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
    • 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
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
    • A61K31/404—Indoles, e.g. pindolol
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • 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
    • C07D405/06—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 carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • 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
    • C07D413/06—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 carbon chain containing only aliphatic carbon atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Indole Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Composición farmacéutica y usos. Reivindicación 1: Un derivado de indol o indolina de la fórmula general (1) en el cual la línea punteada representa un enlace opcional; R1 y R1' se seleccionan en forma independiente del grupo formado por hidrógeno,alqu(en/in)ilo C1-6, cicloalqu(en)ilo C3-8, cicloalqu(en)il C3-8-alqu(en/in)ilo C1-6, hidroxi-alqu(en/in)ilo C1-6, hidroxi-cicloalqu(en)ilo C3-8, hidroxi-cicloalqu(en)il C3-8-alqu(en/in)ilo C1-6, halo-alqu(en/in)ilo C1-6, halo- cicloalqu(en)ilo C3-8, halo-cicloalqu(en)il C3-8-alqu(en/in)ilo C1-6, ciano-alqu(en/in)ilo C1-6, ciano-cicloalqu(en)ilo C3-8 y ciano-cicloalqu(en)il C3-8-alqu(en/in)ilo C1-6; o R1 y R1' junto con el átomo de carbono al cual están unidos forman un anillo saturado o insaturado de 3-8 miembros que contiene en forma opcional 1 o 2 heteroátomos; s es 0 ó 1; U es O, NR11, S, SO2, SO2NR11, CO-O o CO-NR11; en los cuales R11 se selecciona del grupo formado por hidrógeno, alqu(en/in)ilo C1-6, cicloalqu(en)ilo C3-8, cicloalqu(en)il C3-8-alqu(en/in)ilo C1-6; o R2 y R11 junto con el átomo de nitrógeno al cual están unidos forman un anillo saturado o insaturado de 4-8 miembros que contiene, en forma opcional 1, 2 o 3 heteroátomos adicionales; R2 se selecciona del grupo formado por hidrógeno, alqu(en/in)ilo C1-6, cicloalqu(en)ilo C3-8, cicloalqu(en)il C3-8-alqu(en/in)ilo C1-6, Ar, Ar-alqu(en/in)ilo C1-6, Ar-cicloalqu(en)ilo C3-8, Ar-cicloalqu(en)il C3-8-alqu(en/in)ilo C1-6, acilo, hidroxi-alqu(en/in)ilo C1-6, hidroxi-cicloalqu(en)ilo C3-8, hidroxi-cicloalqu(en)il C3-8-alqu(en/in)ilo C1-6, halógeno, halo-alqu(en/in)ilo C1-6, halo-cicloalqu(en)ilo C3-8, halo-C3-8cicloalqu(en)il C3-8-alqu(en/in)ilo C1-6, ciano, ciano- alqu(en/in)ilo C1-6, ciano-cicloalqu(en)ilo C3-8, ciano-cicloalqu(en)il C3-8-alqu(en/in)ilo C1-6, -NO2, NR10R10'-alqu(en/in)ilo C1-6, NR10R10'-cicloalqu(en)ilo C3-8 y NR10R10'-cicloalqu(en)il C3-8-alqu(en/in)ilo C1-6; en los cuales R10 y R10 se seleccionan en forma independiente del grupo formado por hidrógeno, alqu(en/in)ilo C1-6, cicloalqu(en)ilo C3-8, cicloalqu(en)il C3-8-alqu(en/in)ilo C1-6, hidroxi-alqu(en/in)ilo C1-6, hidroxi-cicloalqu(en)ilo C3-8, hidroxi-cicloalqu(en)il C3-8- alqu(en/in)ilo C1-6, halo-alqu(en/in)ilo C1-6, halo-cicloalqu(en)ilo C3-8, halo-cicloalqu(en)il C3-8-alqu(en/in)ilo C1-6, ciano-alqu(en/in)ilo C1-6, ciano-cicloalqu(en)ilo C3-8 y ciano-cicloalqu(en)il C3-8-alqu(en/in)ilo C1-6, o R10 y R10' junto con el átomo de nitrógeno al cual están unidos forman un anillo de 4-8 miembros saturado o insaturado que contiene en forma opcional 1, 2 o 3 heteroátomos adicionales; con la salvedad de que cuando R2 es NO2, halógeno o ciano entonces s es 0; y con la salvedad de que cuando es un átomo de hidrógeno o acilo y s es 1 entonces U es NR11, O ó S; en los cuales los grupo -(U)s-R2 está ligado a la posición 4 o 6 del indol o indolina; q es 0 o 1; Z es O ó S; X es CO o SO2; con la salvedad de que q es 0 cuando X es SO2; R3 se selecciona del grupo formado por alqu(en/in)ilo C1-6, cicloalqu(en)ilo C3-8, heterocicloalqu(en)ilo, cicloalqu(en)il C3-8-alqu(en/in)ilo C1-6, alqu(en/in)il C1-6-cicloalqu(en)ilo C3-8, alqu(en/in)il C1-6- heterocicloalqu(en)ilo, Ar, Ar-alqu(en/in)ilo C1-6, Ar-cicloalqu(en)ilo C3-8, Ar-heterocicloalqu(en)ilo, Ar-cicloalqu(en)il C3-8-alqu(en/in)ilo C1-6, Ar-alqu(en/in)il C1-6-cicloalqu(en)ilo C3-8, Ar-alqu(en/in)il C1-6-heterocicloalqu(en)ilo, alqu(en/in)iloxi C1-6-alqu(en/in)ilo C1-6, cicloalqu(en)iloxi C3-8-alqu(en/in)ilo C1-6, alqu(en/in)iloxi C1-6-cicloalqu(en)ilo C3-8, alqu(en/in)iloxi C1-6-heterocicloalqu(en)ilo C1-6, Ar-oxi-alqu(en/in)ilo C1-6, Ar-alqu(en/in)iloxi C1-6- alqu(en/in)ilo C1-6, alqu(en/in)iloxi C1-6-carbonil-alqu(en/in)ilo C1-6, cicloalqu(en)iloxi C3-8-carbonil-alqu(en/in)ilo C1-6, cicloalqu(en)il C3-8-alqu(en/in)iloxi C1-6-carbonil-alqu(en/in)ilo C1-6, hidroxi-alqu(en/in)ilo C1-6, hidroxi- cicloalqu(en)ilo C3-8, hidroxi-heterocicloalqu(en)ilo, hidroxi-cicloalqu(en)il C3-8-alqu(en/in)ilo C1-6, hidroxi-alqu(en/in)il C1-6-cicloalqu(en)ilo C3-8, hidroxi-alqu(en/in)il C1-6-heterocicloalqu(en)ilo, halo-alqu(en/in)ilo C1-6, halo- cicloalqu(en)ilo C3-8, halo-heterocicloalqu(en)ilo, halo-cicloalqu(en)il C3-8-alqu(en/in)ilo C1-6, haloalqu(en/in)il C1-6-cicloalqu(en)ilo C3-8, halo-alqu(en/in)il C1-6-heterocicloalqu(en)ilo, halo-alqu(en/in)il C1-6-Ar, halo-cicloalqu(en)il C3-8- Ar, halo-cicloalqu(en)il C3-8-alqu(en/in)il C1-6-Ar, halo-alqu(en/in)il C1-6-cicloalqu(en)il C3-8-Ar, ciano-alqu(en/in)ilo C1-6, ciano-cicloalqu(en)ilo C3-8, ciano-heterocicloalqu(en)ilo, ciano-cicloalqu(en)il C3-8-alqu(en/in)ilo C1-6, ciano- alqu(en/in)il C1-6-cicloalqu(en)ilo C3-8, ciano-alqu(en/in)il C1-6-heterocicloalqu(en)ilo, acil-alqu(en/in)ilo C1-6, acil-cicloalqu(en)ilo C3-8, acil-heterocicloalqu(en)ilo, acil-cicloalqu(en)il C3-8-alqu(en/in)ilo C1-6, acil-alqu(en/in)il C1-6- cicloalqu(en)ilo C3-8, acil-alqu(en/in)il C1-6-heterocicloalqu(en)ilo y NR12R12'-alqu(en/in)ilo C1-6, substituido en forma opcional, NR12R12'-cicloalqu(en)ilo C3-8 substituido en forma opcional, NR12R12'-cicloalqu(en)il C3-8-alqu(en/in)ilo C1-6 substituido en forma opcional; en los cuales R12 y R12' se seleccionan en forma independiente del grupo formado por hidrógeno, alqu(en/in)ilo C1-6, cicloalqu(en)ilo C3-8, cicloalqu(en)il C3-8-alqu(en/in)ilo C1-6, Ar, Ar-alqu(en/in)ilo C1-6, Ar- cicloalqu(en)ilo C3-8, Ar-cicloalqu(en)il C3-8-alqu(en/in)ilo C1-6, hidroxi-alqu(en/in)ilo C1-6, hidroxi-cicloalqu(en)ilo C3-8, hidroxi-cicloalqu(en)il C3-8-alqu(en/in)ilo C1-6, halo-alqu(en/in)ilo C1-6, halo-cicloalqu(en)ilo C3-8, halo- cicloalqu(en)il C3-8-alqu(en/in)ilo C1-6, ciano-alqu(en/in)ilo C1-6, ciano-cicloalqu(en)ilo C3-8 y ciano-cicloalqu(en)il C3-8-alqu(en/in)ilo C1-6, o R12 y R12' junto con el átomo de nitrógeno al cual están unidos forman un anillo saturado o insaturado de 4-8 miembros que contiene 1, 2 o 3 heteroátomos adicionales; con la salvedad de que cuando R3 es NR12R12' entonces q es 0; e Y representa un grupo de fórmulas (2), (3), (4), (5), (6), (7) y (8) en los cuales la línea representa un enlace que une el grupo representado por Y al átomo de carbono; W es O ó S;T es N, NH u O; L es N, C o CH; a es 0, 1, 2 ó 3; b es 0, 1, 2, 3 ó 4; c es 0 ó 1; d es 0, 1, 2 ó 3; e es 0, 1 ó 2; f es 0, 1, 2, 3, 4 ó 5; g es 0, 1, 2, 3 ó 4; h es 0, 1, 2 ó 3; j es 0, 1, 2 ó 3; con la salvedad de que cuando T es un átomo de nitrógeno entonces j es 0, 1, 2 ó 3; y cuando T es NH o un átomo de oxígeno entonces j es 0, 1 ó 2; k es 0, 1, 2, 3 ó 4; y cada R5 se selecciona en forma independiente del grupo formado por un alqu(en/in)ilo C1-6, cicloalqu(en)ilo C3-8, cicloalqu(en)il C3-8-alqu(en/in)ilo C1-6, Ar, Ar-alqu(en/in)ilo C1-6 , Ar-tio, Ar-oxi, acilo, alqu(en/in)iloxi C1-6, cicloalqu(en)iloxi C3-8, cicloalqu(en)il C3-8-alqu(en/in)iloxi C1-6, halógeno, halo-alqu(en/in)ilo C1-6, halo-cicloalqu(en)ilo C3-8, halo-cicloalqu(en)il C3-8-alqu(en/in)ilo C1-6, -CO-NR6R6', ciano, ciano-alqu(en/in)ilo C1-6, ciano-cicloalqu(en)ilo C3-8, ciano-cicloalqu(en)il C3-8-alqu(en/in)ilo C1-6, -NR7R7', -S-R8 y -SO2R8, o dos R5 adyacentes junto con el grupo aromático al cual están unidos forman un anillo de 4-8 miembros que contiene, en forma opcional, uno o dos heteroátomos; R6 y R6' se seleccionan en forma independiente del grupo formado por hidrógeno, alqu(en/in)ilo C1-6, cicloalqu(en)ilo C3-8, cicloalqu(en)il C3-8-alqu(en/in)ilo C1-6 y Ar; R7 y R7' se seleccionan en forma independiente del grupo formado por hidrógeno, alqu(en/in)ilo C1-6, cicloalqu(en)ilo C3-8, cicloalqu(en)il C3-8- alqu(en/in)ilo C1-6, Ar y acilo; y R8 se selecciona del grupo formado por hidrógeno, alqu(en/in)ilo C1-6, cicloalqu(en)ilo C3-8, cicloalqu(en)il C3-8-alqu(en/in)ilo C1-6, Ar y -NR9R9'; en los cuales R9 y R9' se seleccionan en forma independiente del grupo formado por hidrógeno, alqu(en/in)ilo C1-6, cicloalqu(en)ilo C3-8 y cicloalqu(en)il C3-8-alqu(en/in)ilo C1-6; con la salvedad de que cuando R8 es -NR9R9' entonces R5 no es -S-R8; o sus sales; con la salvedad de que el compuesto de fórmula (1) no sea: N-[1-(fenilmetil)-1H-indol-5-il]-metansulfonamida; N-[1-[(4-fluorofenil)metil]-1H-indol-5-il]-metansulfonamida; N-[2,3-dihidro-1-(fenilmetil)-1H-indol-5-il]-metansulfonamida; N-[1-(fenilmetil)-1H-indol-5-il]-N'-4-quinolinil-urea; N-[1- (fenilmetil)-1H-indol-5-il]-N'-4-quinolinil-urea; o 1-(1-bencil-5-indolinil)-3-fenil-urea; o sus sales.Pharmaceutical composition and uses. Claim 1: An indole or indoline derivative of the general formula (1) in which the dotted line represents an optional bond; R1 and R1 'are independently selected from the group consisting of hydrogen, alkyl (en / in) C1-6 yl, cycloalkyl (en) C3-8yl, cycloalkyl (en) and C3-8-alkyl (en / in) C1-6 yl, hydroxy-alkyl (en / in) C1-6 yl, hydroxy-cycloalkyl (en) C3-8yl, hydroxy-cycloalkyl (en) and C3-8-alkyl (en / in) C1-6yl , halo-alkyl (en / in) C1-6 yl, halo-cycloalkyl (en) C3-8 yl, halo-cycloalkyl (en) yl C3-8-alkyl (en / in) C1-6yl, cyano-alkyl (en / in) C1-6 yl, cyano-cycloalk (en) C3-8 yl, and cyano-cycloalkyl (en) yl C3-8-alkyl (en / in) C1-6 yl; or R1 and R1 'together with the carbon atom to which they are attached form a saturated or unsaturated 3-8 membered ring that optionally contains 1 or 2 heteroatoms; s is 0 or 1; U is O, NR11, S, SO2, SO2NR11, CO-O or CO-NR11; in which R 11 is selected from the group consisting of hydrogen, C 1-6 alkyl (en / in), C 3-8 cycloalkyl, C 3-8 cycloalkyl (en) and C 3-8 alkyl (en / in) C 1-10 6; or R2 and R11 together with the nitrogen atom to which they are attached form a saturated or unsaturated 4-8 membered ring which optionally contains 1, 2 or 3 additional heteroatoms; R2 is selected from the group consisting of hydrogen, alkyl (en / in) C1-6 yl, cycloalkyl (en) C3-8yl, cycloalkyl (en) and C3-8 -alkyl (en / in) C1-6yl, Ar , Ar-alk (en / in) C1-6 yl, Ar-cycloalkyl (en) C3-8 yl, Ar-cycloalkyl (en) and C3-8-alkyl (en / in) C1-6 yl, acyl, hydroxy -alk (en / in) C1-6 yl, hydroxy-cycloalkyl (en) C3-8 yl, hydroxy-cycloalkyl (en) yl C3-8-alkyl (en / in) C1-6yl, halogen, halo-alkyl (en / in) ilo C1-6, halo-cycloalkyl (en) ilo C3-8, halo-C3-8cycloalkyl (en) yl C3-8-alkyl (en / in) ilo C1-6, cyano, cyano-alkyl (en / in) ilo C1-6, cyano-cycloalk (en) ilo C3-8, cyano-cycloalk (en) yl C3-8-alky (in / in) ilo C1-6, -NO2, NR10R10'-alky (en / in) C1-6, NR10R10'-cycloalkyl (en) C3-8yl and NR10R10'-cycloalkyl (en) and C3-8-alkyl (en / in) C1-6yl; in which R10 and R10 are independently selected from the group consisting of hydrogen, C1-6 alkyl (en / in) C3-8 cycloalkyl (C3-8yl), C3-8alkyl (en) and C3-8alkyl (en / in) C1-6 yl, hydroxy-alkyl (en / in) C1-6 yl, hydroxy-cycloalkyl (en) C3-8 yl, hydroxy-cycloalkyl (en) and C3-8-alkyl (en / in) C1-yl -6, halo-alkyl (en / in) ilo C1-6, halo-cycloalkyl (en) ilo C3-8, halo-cycloalkyl (en) yl C3-8-alkyl (en / in) ilo C1-6, cyano -alk (en / in) ilo C1-6, cyano-cycloalk (en) ilo C3-8 and cyano-cycloalk (en) yl C3-8-alkyl (en / in) ilo C1-6, or R10 and R10 ' together with the nitrogen atom to which they are attached they form a saturated or unsaturated 4-8 membered ring that optionally contains 1, 2 or 3 additional heteroatoms; with the proviso that when R2 is NO2, halogen or cyano then s is 0; and with the proviso that when it is a hydrogen or acyl atom and s is 1 then U is NR11, O or S; in which the group - (U) s-R2 is linked to the 4 or 6 position of the indole or indoline; q is 0 or 1; Z is O or S; X is CO or SO2; with the proviso that q is 0 when X is SO2; R3 is selected from the group consisting of alkyl (en / in) C1-6 yl, cycloalkyl (en) C3-8yl, heterocycloalkyl (en) yl, cycloalkyl (en) and C3-8-alkyl (en / in) C1-yl -6, alky (en / in) il C1-6-cycloalk (en) yl C3-8, alky (en / in) il C1-6- heterocycloalkyl (en) ilo, Ar, Ar-alk (en / in) C1-6 yl, Ar-cycloalkyl (en) C3-8 yl, Ar-heterocycloalkyl (en) ilo, Ar-cycloalkyl (en) and C3-8-alkyl (en / in) C1-6yl, Ar-alkyl ( en / in) C1-6-cycloalkyl (en) yl C3-8, Ar-alkyl (en / in) and C1-6-heterocycloalkyl (en) ilo, alky (in / in) C1-6-alkyloxy ( en / in) C1-6 yl, cycloalk (en) C3-8-yloxy-al (en / in) C1-6-yl, alky (en / in) C1-6-yloxy-en-yl C3-8, alky (en / in) C1-6-yloxy-heterocycloalk (en) C1-6-yl, Ar-oxy-alkyl (en / in) C1-6-yl, Ar-alkyl (en / in) C1-6-alkyloxy / in) C1-6 yl, alky (in / in) C1-6-carbonyl-alkylo (en / in) C1-6 yl, cycloalkyl (en) C3-8-yloxy-alkylo (en / in) yl C1-6, cycloalkyl (en) yl C3-8-alkyl (en / in) yloxy C1-6-carbonyl-alkyl (en / in) yl C1-6, hydroxy-alkyl (en / in) yl C1-6, hydroxy-cycloalkyl (en) C3-8 yl, hydroxy-heterocycloalkyl (en) yl, hydroxy-cycloalkyl (en) C3-8-alkyl (en / in) C1-6 yl, hydroxy-alkyl (en / in) and C1-6-cycloalkyl (en) C3-8 yl, hydroxy-alkyl (en / in) il C1-6-heterocycloalkyl (en) ilo, halo-alkyl (en / in) ilo C1-6, halocycloalkyl (en) ilo C3-8, halo-heterocycloalkyl (en) ilo, halo-cycloalkyl (en) il C3 -8-alky (en / in) ilo C1-6, haloalk (en / in) il C1-6-cycloalk (en) ilo C3-8, halo-alkyla (en / in) il C1-6-heterocycloalqu (en ) ilo, halo-alkyl (en / in) il C1-6-Ar, halo-cycloalkyl (en) il C3-8- Ar, halo-cycloalkyl (en) and C3-8-alkyl (en / in) il C1 -6-Ar, halo-alkyl (en / in) il C1-6-cycloalk (en) yl C3-8-Ar, cyano-alkyl (en / in) ilo C1-6, cyano-cycloalk (en) ilo C3 -8, cyano-heterocycloalk (en) ilo, cyano-cycloalk (en) yl C3-8-alkyl (en / in) yl C1-6, cyano-alky (en / in) il C1-6-cycloalk (en) C3-8 yl, cyano-alkyl (en / in) yl C1-6-heterocycloalkyl (en) ilo, acyl-alkyl (en / in) C1-6yl, acyl-cycloalkyl (en) Cyl- C3-8, acyl- heterocycloalkyl (en) yl, acyl-cycloalkyl (en) yl C3-8-alkyl (en / in) yl C1-6, acyl-alkyl (en / in) yl C1-6- cycloalkyl (en) yl C3-8, acyl-alkyl (en / in) yl C1-6-heterocycloalkyl (en) yl and NR12R12'-alkyl (en / in) yl C 1-6, optionally substituted, NR12R12'-cycloalkyl (en) C3-8 yl optionally substituted, NR12R12'-cycloalkyl (en) and C3-8-alkyl (en / in) C1-6yl substituted optional; in which R12 and R12 'are independently selected from the group consisting of hydrogen, C1-6 alkyl (en / in) C3-8 cycloalkyl (C3-8yl), C3-8 -alkyl (en) / in) ilo C1-6, Ar, Ar-alkyl (en / in) ilo C1-6, Arcycloalkyl (en) ilo C3-8, Ar-cycloalkyl (en) and C3-8-alkyl (en / in ) C1-6-yl, hydroxy-alkyl (en / in) C1-6-yl, hydroxy-cycloalkyl (en) C3-8yl, hydroxy-cycloalkyl (en) and C3-8 -alkyl (en / in) C1- 6, halo-alkyl (en / in) C1-6 yl, halo-cycloalkyl (en) C3-8-yl, halo-C3-8 -alkyl (en / in) C1-6-yl, cyano- C1-6 alkyl (en / in) C1-6, cyano-cycloalkyl (en) C3-8yl and cyano-cycloalkyl (en) and C3-8 -alkyl (en / in) C1-6yl, or R12 and R12 'together with the nitrogen atom to which they are attached they form a saturated or unsaturated 4-8-membered ring containing 1, 2 or 3 additional heteroatoms; with the proviso that when R3 is NR12R12 'then q is 0; and Y represents a group of formulas (2), (3), (4), (5), (6), (7) and (8) in which the line represents a link linking the group represented by Y to carbon atom; W is O or S; T is N, NH or O; L is N, C or CH; a is 0, 1, 2 or 3; b is 0, 1, 2, 3 or 4; c is 0 or 1; d is 0, 1, 2 or 3; e is 0, 1 or 2; f is 0, 1, 2, 3, 4 or 5; g is 0, 1, 2, 3 or 4; h is 0, 1, 2 or 3; j is 0, 1, 2 or 3; with the proviso that when T is a nitrogen atom then j is 0, 1, 2 or 3; and when T is NH or an oxygen atom then j is 0, 1 or 2; k is 0, 1, 2, 3 or 4; and each R5 is independently selected from the group consisting of a C1-6 alkyl (en / in) C3-8 cycloalkyl (C3-8yl), C3-8ylcycloalkyl (en / yl) C1-Cyl -6, Ar, Ar-alkyl (en / in) C1-6 yl, Ar-thio, Ar-oxy, acyl, alkyl (en / in) C1-6 yloxy, cycloalkyl (en) C3-8 yloxy, cycloalk ( en) C3-8-alkyl (en / in) C1-6 yloxy, halogen, halo-alkyl (en / in) C1-6 yl, halo-C3-8 cycloalkyl, halo-cycloalkyl (en) C3-8-alkyl (en / in) ilo C1-6, -CO-NR6R6 ', cyano, cyano-alkyl (en / in) ilo C1-6, cyano-cycloalkyl (en) ilo C3-8, cyano- cycloalkyl (en) yl C3-8-alkyl (en / in) C1-6, -NR7R7 ', -S-R8 and -SO2R8, or two adjacent R5 together with the aromatic group to which they are attached form a ring of 4 -8 members containing, optionally, one or two heteroatoms; R6 and R6 'are independently selected from the group consisting of hydrogen, alkyl (en / in) C1-6 yl, cycloalkyl (en) C3-8yl, cycloalkyl (en) and C3-8-alkyl (en / in) C1-6 yl and Ar; R7 and R7 'are independently selected from the group consisting of hydrogen, alkyl (en / in) C1-6 yl, cycloalkyl (en) C3-8yl, cycloalkyl (en) and C3-8-alk (en / in) C1-6 yl, Ar and acyl; and R8 is selected from the group consisting of hydrogen, alkyl (en / in) C1-6 yl, cycloalkyl (en) C3-8yl, cycloalkyl (en) and C3-8-alkyl (en / in) C1-6yl, Ar and -NR9R9 '; in which R9 and R9 'are independently selected from the group consisting of hydrogen, C1-6 alkyl (en / in) C3-8 cycloalkyl (C3-8yl) and C3-8 -alkyl (en) / in) C1-6 yl; with the proviso that when R8 is -NR9R9 'then R5 is not -S-R8; or its salts; with the proviso that the compound of formula (1) is not: N- [1- (phenylmethyl) -1H-indole-5-yl] -methanesulfonamide; N- [1 - [(4-fluorophenyl) methyl] -1H-indole-5-yl] -methanesulfonamide; N- [2,3-dihydro-1- (phenylmethyl) -1H-indol-5-yl] -methanesulfonamide; N- [1- (phenylmethyl) -1H-indol-5-yl] -N'-4-quinolinyl-urea; N- [1- (phenylmethyl) -1H-indol-5-yl] -N'-4-quinolinyl-urea; or 1- (1-benzyl-5-indolinyl) -3-phenyl-urea; or its salts.

ARP040101392A 2003-04-25 2004-04-23 INDOLIN AND INDOLINE DERIVATIVES REPLACED AR044517A1 (en)

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