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AR035851A1 - 3-cianoquinolinas, 3-ciano-1,6-naftiridinas y 3-ciano-1,7-naftiridinas como inhibidoras de proteina quinasas - Google Patents

3-cianoquinolinas, 3-ciano-1,6-naftiridinas y 3-ciano-1,7-naftiridinas como inhibidoras de proteina quinasas

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Publication number
AR035851A1
AR035851A1 ARP010101423A ARP010101423A AR035851A1 AR 035851 A1 AR035851 A1 AR 035851A1 AR P010101423 A ARP010101423 A AR P010101423A AR P010101423 A ARP010101423 A AR P010101423A AR 035851 A1 AR035851 A1 AR 035851A1
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AR
Argentina
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nhr5
r6oc
nhc
conh2
optionally substituted
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ARP010101423A
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Wyeth Corp
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Abstract

Estos compuestos resultan útiles como agentes antineoplásicos y en el tratamiento de la osteoporosis y la enfermedad poliquística renal. Reivindicación 1: Un compuesto de la Fórmula (1), en la cual X es -NH-, -NR5- -O- ó -S(O)m-; n es un entero de valor 0 ó 1; m es un entero de valor 0 a 2; q es un entero de valor 0 a 1; p es un entero de valor 2 a 5; s es un entero de valor 0 a 5; r es un entero de valor 0 a 5; J es halógeno; A es -(C(R9)2)r-, -C(O)-, -C(O)(C(R9)2)r-, -(C(R9)2)rRC(O)-, cicloalquilo o está ausente; T y Z son, cada uno independientemente, carbono o N, siempre que T y Z no sean simultáneamente N; R1 se selecciona entre: un anillo cicloalquilo C3-10 sustituido opcionalmente con uno o más grupos alquilo de 1 a 6 átomos seleccionados independientemente; arilo C6-12 sustituido opcionalmente con 1 a 4 sustituyentes que pueden ser iguales o diferentes, seleccionados independientemente entre los grupos -H, -J, -NO2, -NH2, -OH, -SH, -CN, -N3, -COOH, -CONH2, -NHC(O)NH2, -C(O)H, -CF3, -OCF3, -R5, -OR5, -NHR5, -Q, -S(O)mR5, -NHSO2R5, -R6OH, -R6OR5, -R6NH2, -R6NHR5, -R6Q, -R6SH, -R6S(O)mR5, -NHR7OH, -NHR7OR5, -N(R5)R7OH, -N(R5)R7OR5, -NHR7NH2, -NHR7NHR5, -NHR7Q, -N(R5)R7NH2, -N(R5)R7NR5, -N(R5)R7Q, -OR7OH, -OR7OR5, -OR7NH2, -OR7NHR5, -OR7Q, -OC(O)R5, -NHC(O)R5, -NHC(O)NHR5, -OR6C(O)R5, -NHR6C(O)R5, -C(O)R5, -C(O)NHR5, -C(O)Q, -R6C(O)H, -R6C(O)R5, -R6C(O)OH, -R6C(O)OR5, -R6C(O)NH2, -R6C(O)NHR5, -R6C(O)Q, -R6OC(O)R5, -R6OC(O)NH2, -R6OC(O)NHR5, -R6OC(O)Q e YR8 en el cual Y se selecciona independientemente entre -C(O)-, -C(O)O-, -OC(O)-, -C(O)NH-, -NHC(O)-, -NHSO2-, -SO2NH-, -C(OH)H-, -O(C(R9)2)q-, -S(O)m(C(R9)2)q-, -NH-(C(R9)2)q-, -NR10(C(R9)2)q-, -(C(R9)2)q-, -(C(R9)2)rO-, -(C(R9)2)q-S(O)m, -(C(R9)2)qNH-, -(C(R9)2)qNR10-, -CsC-, cis y trans -C=C- y cicloalquilo C3-10; un anillo heteroarilo de 5 ó 6 miembros que contenga de 1 a 4 heteroátomos o en particular 1 ó 2 heteroátomos que pueden ser iguales o diferentes, seleccionados entre N, O y S, en el cual el anillo heteroarilo puede estar opcionalmente sustituido con 1 a 4 sustituyentes que pueden ser iguales o diferentes seleccionados entre los grupos -H, -J, -NO2, -NH2, -OH, -SH, -CN, -N3, -COOH, -CONH2, -NHC(O)NH2, -C(O)H, -CF3, -OCF3, -R5, -OR5, -NHR5, -Q, -S(O)mR5, -NHSO2R5, -R6OH, -R6OR5, -R6NH2, -R6NHR5, -R6Q, -R6SH, -R6S(O)mR5, -NHR7OH, -NHR7OR5, -N(R5)R7OH, -N(R5)R7OR5, -NHR7NH2, -NHR7NHR5, -NHR7Q, -N(R5)R7NH2, -N(R5)R7NR5, -N(R5)R7Q, -OR7OH, -OR7OR5, -OR7NH2, -OR7NHR5, -OR7Q, -OC(O)R5, -NHC(O)R5, -NHC(O)NHR5, -OR6C(O)R5, -NHR6C(O)R5, -C(O)R5, -C(O)NHR5, -C(O)Q, -R6C(O)H, -R6C(O)R5, -R6C(O)OH, -R6C(O)OR5, -R6C(O)NH2, -R6C(O)NHR5, -R6C(O)Q, -R6OC(O)R5, -R6OC(O)NH2, -R6OC(O)NHR5, -R6OC(O)Q y YR8 en el cual Y se selecciona independientemente entre -C(O)-, -C(O)O-, -OC(O)-, -C(O)NH-, -NHC(O)-, -NHSO2-, -SO2NH-, -C(OH)H-, -O(C(R9)2)q-, -S(O)m(C(R9)2)q-, -NH-(C(R9)2)q-, -NR10(C(R9)2)q-, -(C(R9)2)q- -(C(R9)2)rO-, -(C(R9)2)q-S(O)m, -(C(R9)2)qNR10-, -CsC-, cis y trans -C=C- y cicloalquilo C3-10; un sistema de anillos heteroarilo bicíclico que posea entre 8 y 20 átomos que contenga de 1 a 4 heteroátomos, que pueden ser iguales o diferentes, seleccionados entre N, O y s, en el cual el sistema de anillos heteroarilo bicíclico puede estar opcionalmente sustituido con 1 a 4 sustituyentes que pueden ser iguales o diferentes seleccionados entre los grupos -H, -J, -NO2, -NH2, -OH, -SH, -CN, -N3, -COOH, -CONH2, -NHC(O)NH2, -C(O)H, -CF3, -OCF3, -R5, -OR5, -NHR5, -Q, -S(O)mR5, -NHSO2R5, -R6OH, -R6OR5, -R6NH2, -R6NHR5, -R6Q, -R6SH, -R6S(O)mR5, -NHR7OH, -NHR7OR5, -N(R5)R7OH, -N(R5)R7OR5, -NHR7NH2, -NHR7NHR5, -NHR7Q, -N(R5)R7NH2, -N(R5)R7NHR5, -N(R5)R7Q, -OR7OH, -OR7OR5, -OR7NH2, -OR7NHR5, -OR7Q, -OC(O)R5, -NHC(O)R5, -NHC(O)NHR5, -OR6C(O)R5, -NHR6C(O)R5, -C(O)R5, -C(O)NHR5, -C(O)Q, -R6C(O)H, -R6C(O)R5, -R6C(O)OH, -R6C(O)OR5, -R6C(O)NH2, -R6C(O)NHR5, -R6C(O)Q, -R6OC(O)R5, -R6OC(O)NH2, -R6OC(O)NHR5, -R6OC(O)Q y YR8 en el cual Y se selecciona independientemente entre -C(O)-, -C(O)O-, -OC(O)-, -C(O)NH-, -NHC(O)-, -NHSO2-, -SO2NH-, -C(OH)H-, -O(C(R9)2)q-, -S(O)m(C(R9)2)q-, -NH-(C(R9)2)q-, -NR10(C(R9)2)q-, -(C(R9)2)q- -(C(R9)2)rO-, -(C(R9)2)q-S(O)m, -(C(R9)2)qNR10-, -CsC-, cis y trans -C=C- y cicloalquilo C3-10; y un grupo de fórmula (2), en donde E es -NH-, -NR5-, -O-, -S(O)m-, -C(O)-, -CH2-, -CHR5- ó -CR5R5-; Q es -NR5R5 y además siempre que cada R5 se seleccione independientemente entre alquilo y alquenilo, R5R5 pude tomarse opcionalmente en forma conjunta con el átomo de nitrógeno al cual están unidos formando un anillo heterociclo de entre 3 y 8 átomos, conteniendo opcionalmente 1 ó 2 heteroátomos adicionales, que pueden ser iguales o diferentes, seleccionados entre N, O y S; R1a, R1b, R1c, R1d y R1e se seleccionan cada uno, independientemente entre -H, -J, -NO2, -NH2, -OH, -SH, -CN, -N3, -COOH, -CONH2, -NHC(O)NH2, -C(O)H, -CF3, -OCF3, -R5, -OR5, -NHR5, -Q, -S(O)mR5, -NHSO2R5, -R6OH, -R6OR5, -R6NH2, -R6NHR5, -R6Q, -R6SH, -R6S(O)mR5, -NHR7OH, -NHR7OR5, -N(R5)R7OH, -N(R5)R7OR5, -NHR7NH2, -NHR7NHR5, -NHR7Q, -N(R5)R7NH2, -N(R5)R7NR5, -N(R5)R7Q, -OR7OH, -OR7OR5, -OR7NH2, -OR7NHR5, -OR7Q, -OC(O)R5, -NHC(O)R5, -NHC(O)NHR5, -OR6C(O)R5, -NHR6C(O)R5, -C(O)R5, -C(O)NHR5, -C(O)Q, -R6C(O)H, -R6C(O)R5, -R6C(O)OH, -R6C(O)OR5, -R6C(O)NH2, -R6C(O)NHR5, -R6C(O)Q, -R6OC(O)R5, -R6OC(O)NH2, -R6OC(O)NHR5, arilo, -CH2-arilo, NH-arilo, -O-arilo, S(O)m-arilo, -OR11 y -R6OC(O)Q; R2a, R2b y R2c se seleccionan cada uno, independientemente entre -H, -arilo, -CH2-arilo, -NH-arilo, -O-arilo, -S(O)m-arilo, -J, -NO2, -OH, -SH, -CN, -N3, -COOH, -CONH2, -NHC(O)NH2, -C(O)H, -CF3, -OCF3, -R5, -OR5, -S(O)mR5, -NHSO2R5, -R11, -OR11, -R6OH, -R6OR5, -R6SH, -R6S(O)mR5, -OR7OH, -OR7OR5, -OC(O)R5, -NHC(O)R5, -NHC(O)NHR5, -OR6C(O)R5, -NHR6C(O)R5, -C(O)R5, -C(O)OR5, -C(O)NHR5, -C(O)Q, -R6C(O)H, -R6C(O)R5, -R6C(O)OH, -R6C(O)OR5, -R6C(O)NH2, -R6C(O)NHR5, -R6C(O)Q, -R6OC(O)R5, -R6OC(O)NH2, -R6OC(O)NHR5, -R6OC(O)Q, -G-(C(R9)2)p-R12, -(C(R9)2)q-R12, R18-CONH(CH2)r-, R18CsC-CONH(CH2)r-, N(R18)2C(O)O(CH2)r-, N(R18)2C(O)NH(CH2)r-, N(R18)2C(S)NH(CH2)r-, R18OC(O)NH(CH2)r-, C(R18)2=C(R18)CONH(CH2)r y -C(R18)2=C(R18)SO2NH(CH2)r-; G es -NH-, -NR10-, -O- ó -S(O)m-; R3 se selecciona entre: alquenilo C2-6, opcionalmente sustituido con uno o más entre -R10, -(C(R9)2)s-R12, -CHO, 1,3-dioxolano, -NO2, -CN, -CO2H, -CONH2, -CO2R10, -CONHR10, -COR10, -(C(R9)2)q-OH, -(C(R9)2)qOR10, -(C(R9)2)qNHR10, -(C(R9)2)qJ, -(C(R9)2)qNH2, -(C(R9)2)rH, -G(C(R9)2)pOR10, -G(C(R9)2)pR12 y -G(C(R9)2)pOH; alquinilo C2-6, sustituido opcionalmente con un o más entre -R10, -(C(R9)2)s-R12, -CHO, 1,3-dioxolano, -NO2, -CN, -CO2H, -CONH2, -CO2R10, -CONHR10, -COR10, -(C(R9)2)q-OH, -(C(R9)2)qOR10, -(C(R9)2)qNHR10, -(C(R9)2)qJ, -(C(R9)2)qNH2, -(C(R9)2)rH, -G(C(R9)2)pOR10, -G(C(R9)2)pR12 y -G(C(R9)2)pOH; arilo C6-12 sustituido opcionalmente con 1 a 4 sustituyentes que pueden ser iguales o diferentes, seleccionado entre -R10, -(C(R9)2)s-R12, -CHO, 1,3-dioxolano, -NO2, -CN, -CO2H, -CONH2, -CO2R10, -CONHR10, -COR10, -(C(R9)2)q-OH, -(C(R9)2)qOR10, -(C(R9)2)qNHR10, -(C(R9)2)qJ, -(C(R9)2)qNH2, -(C(R9)2)rH, -G(C(R9)2)pOR10, -G(C(R9)2)pR12 y -G(C(R9)2)pOH; un anillo heteroarilo de 5 ó 6 átomos que contenga 1 a 4 heteroátomos o en particular 1 ó 2 heteroátomos que pueden ser iguales o diferentes, seleccionados entre N, O y S, en donde el anillo heteroarilo puede estar opcionalmente sustituido con 1 a 4 sustituyentes que pueden ser iguales o diferentes, seleccionados entre -R10, -(C(R9)2)s-R12, -CHO, 1,3-dioxolano, -NO2, -CN, -CO2H, -CONH2, -CO2R10, -CONHR10, -COR10, -(C(R9)2)q-OH, -(C(R9)2)qOR10, -(C(R9)2)qNHR10, -(C(R9)2)qJ, -(C(R9)2)qNH2, -(C(R9)2)rH, -G(C(R9)2)pOR10, -G(C(R9)2)pR12 y -G(C(R9)2)pOH; un sistema de anillos heteroarilo bicíclico que posea entre 8 y 20 átomos que contenga de 1 a 4 heteroátomos, que pueden ser iguales o diferentes seleccionados entre N, O y S, en el cual el sistema de anillos heteroarilo bibíclico puede estar opcionalmente sustituido con 1 a 4 sustituyentes que pueden ser iguales o diferentes seleccionados entre -R10, -(C(R9)2)s-R12, -CHO, 1,3-dioxolano, -NO2, -CN, -CO2H, -CONH2, -CO2R10, -CONHR10, -COR10, -(C(R9)2)q-OH, -(C(R9)2)qOR10, -(C(R9)2)qNHR10, -(C(R9)2)qJ, -(C(R9)2)qNH2, -(C(R9)2)rH, -G(C(R9)2)pOR10, -G(C(R9)2)pR12 y -G(C(R9)2)pOH; R4 se selecciona entre -(C(R9)2)rH, opcionalmente sustituido con uno o más de entre -R10, -(C(R9)2)s-R12, -CHO, 1,3-dioxolano, -NO2, -CN, -CO2H, -CONH2, -CO2R10, -CONHR10, -COR10, -(C(R9)2)q-OH, -(C(R9)2)qOR10, -(C(R9)2)qNHR10, -(C(R9)2)qJ, -(C(R9)2)qNH2, -(C(R9)2)rH, -G(C(R9)2)pOR10, -G(C(R9)2)pR12 y -G(C(R9)2)pOH; alquenilo C2-6, opcionalmente sustituido con uno o más entre -R10, -(C(R9)2)s-R12, -CHO, 1,3-dioxolano, -NO2, -CN, -CO2H, -CONH2, -CO2R10, -CONHR10, -COR10, -(C(R9)2)q-OH, -(C(R9)2)qOR10, -(C(R9)2)qNHR10, -(C(R9)2)qJ, -(C(R9)2)qNH2, -(C(R9)2)rH, -G(C(R9)2)pOR10, -G(C(R9)2)pR12 y -G(C(R9)2)pOH; alquinilo C2-6, sustituido opcionalmente con uno o más entre -R10, -(C(R9)2)s-R12, -CHO, 1,3-dioxolano, -NO2, -CN, -CO2H, -CONH2, -CO2R10, -CONHR10, -COR10, -(C(R9)2)q-OH, -(C(R9)2)qOR10, -(C(R9)2)qNHR10, -(C(R9)2)qJ, -(C(R9)2)qNH2, -(C(R9)2)rH, -G(C(R9)2)pOR10, -G(C(R9)2)pR12 y -G(C(R9)2)pOH; arilo C6-12 sustituido opcionalmente con 1 a 4 sustituyentes que pueden ser iguales o diferentes, seleccionados entre -R10, -(C(R9)2)s-R12, -CHO, 1,3-dioxolano, -NO2, -CN, -CO2H, -CONH2, -CO2R10, -CONHR10, -COR10, -(C(R9)2)q-OH, -(C(R9)2)qOR10, -(C(R9)2)qNHR10, -(C(R9)2)qJ, -(C(R9)2)qNH2, -(C(R9)2)rH, -G(C(R9)2)pOR10, -G(C(R9)2)pR12 y -G(C(R9)2)pOH; un anillo heteroarilo de 5 ó 6 átomos que contenga 1 a 4 heteroátomos o en particular 1 ó 2 heteroátomos que pueden ser iguales o diferentes, seleccionados entre N, O y S, en donde el anillo heteroarilo puede estar opcionalmente sustituido con 1 a 4 sustituyentes que pueden ser iguales o diferentes, seleccionados entre -R10, -(C(R9)2)s-R12, -CHO, 1,3-dioxolano, -NO2, -CN, -CO2H, -CONH2, -CO2R10, -CONHR10, -COR10, -(C(R9)2)q-OH, -(C(R9)2)qOR10, -(C(R9)2)qNHR10, -(C(R9)2)qJ, -(C(R
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ATE371647T1 (de) 2007-09-15
BR0109650A (pt) 2003-04-22
DE60130200D1 (de) 2007-10-11
DE60130200T2 (de) 2008-03-13
MXPA02009439A (es) 2003-02-24
CN1419545A (zh) 2003-05-21
AU2001251063A1 (en) 2001-10-08
ES2291311T3 (es) 2008-03-01
CA2404662A1 (en) 2001-10-04
JP2003528857A (ja) 2003-09-30
WO2001072711A1 (en) 2001-10-04
DK1268431T3 (da) 2007-12-10
EP1268431A1 (en) 2003-01-02
EP1268431B1 (en) 2007-08-29

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