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AR040074A1 - Tiazolidinonas, su preparacion y su uso como medicamentos, e intermediarios para la preparacion de dichos compuestos - Google Patents

Tiazolidinonas, su preparacion y su uso como medicamentos, e intermediarios para la preparacion de dichos compuestos

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Publication number
AR040074A1
AR040074A1 ARP030101572A ARP030101572A AR040074A1 AR 040074 A1 AR040074 A1 AR 040074A1 AR P030101572 A ARP030101572 A AR P030101572A AR P030101572 A ARP030101572 A AR P030101572A AR 040074 A1 AR040074 A1 AR 040074A1
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AR
Argentina
Prior art keywords
alkyl
alkylene
cycloalkyl
group
aryl
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Application number
ARP030101572A
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English (en)
Inventor
Eis Knut Dr
Buchmann Bernd Dr
Briem Hans Dr
Gerhard Siemeister
Boemer Ulf Dr
Schawede Wolfgang Dr
Schulze Volker Dr
Original Assignee
Schering Ag
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Publication of AR040074A1 publication Critical patent/AR040074A1/es

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    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
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    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
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    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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 to ring carbon atoms
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    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/68—Benzothiazoles 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
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    • C07D417/06—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 carbon chain containing only aliphatic carbon atoms
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    • 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
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    • C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
    • C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
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Abstract

Tiazolidonas de la fórmula general (1), preparación de un medicamento en base al compuesto y su uso como inhibidores de la cinasa tipo polo (PLK) para el tratamiento de diversas enfermedades; así como productos intermediarios para preparar las tiazolidonas. Estos compuestos son inhibidores de la cinasa tipo polo (PLK) y se aplican en el tratamiento de ciertas enfermedades, especialmente las tumorales. Reivindicación 1: Compuestos de la fórmula general (1) donde: X e Y son iguales o diferentes y son hidrógeno, arilo, ciano, cicloalquilo C3-6 o el grupo -COOR4, -CONR15-(CH2)n-R25, -COOR25, -CONR15R16 o -COR13; R1, R11, R12, R15, R16, R19 y R20 son iguales o diferentes y son hidrógeno, alquilo C1-10, alquenilo C2-10, alquinilo C2-10, (COOR14)-(CH2)n-, cicloalquil (C3-6)-alquileno (C1-4), cicloalquilo C3-6, fenilsulfonilo, fenil-cicloalquilo C3-6, alcanoilo C1-10, alcoxi(C1-6)-alquileno(C1-6), alcoxicarbonil(C1-4)-alquileno(C1-4), hidroxi-alquileno C1-4, alquil (C1-6)-O-Si(fenil)2-alquilo (C1-6), o el grupo COOR14, -COR13, -SO2R18, -(CH2)n-NR15R16 o -(CH2)n-C(CH3)q-(CH2)nNR15R16 o -NR11R12, o un grupo del resto de fórmulas (2), o son, arilo, heteroarilo, heterociclilo, aril-alquileno (C1-4), heteroaril-alquileno C1-4, ariloxi-alquileno C1-4, heteroariloxi-alquileno C1-4 o aril-alquilenoxi(C1-4)-alquileno(C1-4) opcionalmente mono o polisustituido, igual o diferente, por alquilo C1-6, alquenilo C2-6, alquinilo C2-6, cicloalquilo C3-6, cicloalquiloxi C3-6, fenilo, ciano, halógeno, hidroxi, alcoxi C1-4, fenoxi, benciloxi, alquilsulfanilo C1-4, bencilsulfanilo, fenilsulfanilo, dimetilamino, acetilamino, trifluorometilo, trifluorometoxi, trifluorometilsulfanilo, acetilo, -CO-alquilo C1-6, 1-iminoetilo o nitro, o alquilo C1-10 mono o polisustituido por flúor; R2 y R3 son iguales o diferentes y son hidrógeno, alquilo C1-6, hidroxi-alquileno C1-6, ciclohexilo C3-6 o el grupo -COOR14, -CONR15R16, -COR13, -SO2R18, -NR11R12, -(CH2)n-A, o un resto de fórmula (3) y (4), o arilo, heteroarilo o heterociclilo opcionalmente mono o polisustituido, igual o diferente, por alquilo C1-6, cicloalquilo C3-6, halo-alquilo C1-6, halo-alcoxi C1-6, halógeno, ciano, hidroxi-alquileno C1-6, hidroxi-alquilenoxi C1-6, arilo, heteroarilo, heterociclilo, alquil(C1-6)-COOR8 o por el grupo -OR10, -COR13, -COOR14, -NR11R12, -NR11-CO-NR11R12, -NR11-CO-R13, -NR11-SO2-R13, -(CH2)n-CO-NR15R16, -SR10 o -SO2R18; R4, R8, R9, R10, R13, R14, R17 y R18 son iguales o diferentes y son hidrógeno, alquilo C1-10, hidroxi-alquilenoxi(C1-6)-alquileno(C1-6), alcoxi(C1-6)-CO-alquileno(C1-6), -(CH2)n-CO-NR15R16, alquenilo C2-10, alquinilo C2-10, cicloalquil (C3-6)-alquileno(C1-4), halo-alquilo C1-6, hidroxi-alquileno C1-6, (COOR14)-(CH2)n-, hidroxi-(CH2)n-O-(CH2)n, cicloalquilo C3-6, alcanoilo C1-10, o el grupo -NR11R12, -(CH2)n-CO-R25, -(CH2)n-NR15R16, COOR14-(CH2)n- o -COR13, o arilo, heteroarilo, heterociclilo, aril-alquileno C1-4, heteroaril-alquileno C14, ariloxi-alquileno C1-4, heteroariloxi-alquileno C1-4 o aril-alquilenoxi(C1-4)-alquileno(C1-4) opcionalmente mono o polisustituido, igual o diferente, por alquilo C1-6, alquenilo C2-6, cicloalquilo C3-6, cicloalquiloxi C3-6, fenilo, ciano, halógeno, hidroxi-alquilo C1-6, alcoxi C1-4, fenoxi, benciloxi, alquilsulfanilo C1-4, bencilsulfanilo, fenilsulfanilo, dimetilamino, acetil-amino, trifluorometilo, trifluorometoxi, trifluorometilsulfanilo, acetilo, -CO-alquilo C1-6, 1-iminoetilo o nitro, o alquilo C1-10 mono o polisustituido por flúor o el grupo -NR11R12, -COR13, -SO2R18, -(CH2)n-NR15R16, -(CH2)n-C(CH3)q-(CH2)nR15R16 o un grupo de resto de fórmula (2), o R2 y R3, R11 y R12, R15 y R16 y R19 y R20 forman cada uno, independientemente entre sí, un anillo de 3 a 10 miembros, que puede contener opcionalmente uno o varios átomos de nitrógeno, oxígeno o azufre; o R3 es hidrógeno y R2 es el grupo -(L-M), donde L es un grupo -C(O)-, -S(O)2-, -C(O)N(R7)-, -S(O)2 n(R7)-, -C(S)N(R7)-, C(S)N(R7)C(O)O-, -C(O)O- o -C(O)S- y M es hidrógeno, alquilo C1-10, alquenilo C2-10, alquinilo C2-10, cicloalquil(C3-6)-alquileno(C1-4), cicloalquilo C3-6, fenil-cicloalquilo C3-6, alcanoilo C1-10, alcoxi(C1-4)-alquileno(C1-4), alcoxicarbonil(C1-4)-alquileno(C1-4), hidroxialquileno C1-10, o arilo, heteroarilo, heterociclilo, aril-alquileno C1-4, heteroaril-alquileno C1-4, ariloxi-alquileno C1-4, heteroariloxi-alquileno C1-4 o aril-alquilenoxi(C1-4)-alquileno(C1-4) opcionalmente mono o polisustituido, igual o diferente, por alquilo C1-4, alquenilo C2-6, cicloalquilo C3-6, cicloalquiloxi C3-6, fenilo, ciano, halógeno, fenoxi, benciloxi, halo-alcoxi C1-4, halo-alquilo C1-6, nitro, alquil C1-6-COOR8, alquenil C2-6-COOR8, alquinil C2-6-COOR8, alquil C1-6-OR9, alquenil C2-6-OR9, alquinil C1-6-OR9 o por el grupo -OR10, -NR11R12, -COR13, -COOR14, -CONR15R16, -SR17, -SO2R18, SO2NR19R20 o -C(NH)(NH2), o un alquilo C1-10 mono o polisustituido por flúor; y R7 es hidrógeno, alquilo C1-10, alquenilo C2-10, alquinilo C2-10, cicloalquilo C3-6, (cicloalquil C3-6)-alquileno C1-4, aril-alquileno C1-4; A es arilo, heteroarilo o heterociclilo opcionalmente sustituido; R22 es hidrógeno, hidroxi-alquilo C1-6, o es el grupo -OR10, -NR11R12, -COR13, -CONR15R16, -SO2R18, -NR15-(C=S)-NR16-(CH2)n-R24, -NR15-(C=O)-NR16-(CH2)n-R24; R23 es hidrógeno o alquilo C1-6; R24 es hidrógeno, fenilo, alcoxi C1-6 o el grupo -(CH2)n-COO-alquilo C1-6; R25 el grupo -OR10 o alquenilo C2-6, fenilo, piridilo, imidazolilo, morfolinilo, piperidinilo, cicloalquilo C3-6 o un restos de fórmula (5) opcionalmente mono o polisustituido, igual o diferente, por halógeno, alquilo C1-6, hidroxi-alquilo C1-6 o por el grupo -OR10 o -COOR14; o m, p, k son cada uno, independientemente entre sí 0 ó 1; n es 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 ó 10; q es 1 ó 2, así como los estereoisómeros, las mezclas de los estereoisómeros y las sales de los mismos.
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