AR038365A1 - Compuestos de benzamida, composiciones farmaceuticas que contienen los mismos para el tratamiento de enfermedades mediadas por p2x7 - Google Patents
Compuestos de benzamida, composiciones farmaceuticas que contienen los mismos para el tratamiento de enfermedades mediadas por p2x7Info
- Publication number
- AR038365A1 AR038365A1 ARP020104318A ARP020104318A AR038365A1 AR 038365 A1 AR038365 A1 AR 038365A1 AR P020104318 A ARP020104318 A AR P020104318A AR P020104318 A ARP020104318 A AR P020104318A AR 038365 A1 AR038365 A1 AR 038365A1
- Authority
- AR
- Argentina
- Prior art keywords
- alkyl
- cycloalkyl
- heterocyclyl
- heteroaryl
- cr11r12
- Prior art date
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- 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
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- C07D253/06—1,2,4-Triazines
- C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
- C07D253/07—1,2,4-Triazines having 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
- C07D253/075—Two hetero atoms, in positions 3 and 5
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- C07—ORGANIC CHEMISTRY
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- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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- C07D263/18—Oxygen atoms
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Abstract
Un compuesto de benzamida de fórmula (1) donde A es -(C=O)NH- ó -NH(C=O)-; X, Y, y Z son =(CR6)-, =(CR7)-, y =(CR8)-, o =N-, =(CR7)-, y =(CR8)-; o =(CR6)-, =N-, y =(CR8)-, o =(CR6)-, =(CR7)-, y =N-, o =N-, =(CR7)-, y =N-, o =(CR6)-, =N-, y =N-; R1 es un heterociclilo C1-10 ligado a N que contiene 1 a 6 heteroátomos seleccionados independientemente de -N=, -N<, -NH-, -O- y -S(O)n-; estando sustituido el citado heterociclilo C1-10 ligado a N con al menos un grupo oxo o siendo uno de los citados heteroátomos -S(O)n-, siendo n 1 o 2, pudiendo estar también el citado heterociclilo C1-10 ligado a N opcionalmente sustituido en cualquier átomo de C que pueda llevar sustituyentes adicionales con 1 a 3 grupos R9 por anillo, estando seleccionado independientemente cada R9 del grupo de sustituyentes constituido por H, halo-hidroxilo, -CN, alquilo C1-4 opcionalmente sustituido con 1 a 3 fluoro-, HO-alquilo(C1-4), alcoxi C1-4 opcionalmente sustituido con 1 a 3 fluoro-, HO2C-, alquil(C1-6)-O-(C=O)-, R4R5N(O2S)-, alquil (C1-4)-(O2S)-NH-, alquil (C1-4)-O2S-[alquil(C1-4)-N]-, R4R5N(C=O)-, R4R5N(CH2)t-, arilo C6-10, cicloalquilo C3-8, heteroarilo C1-10, heterociclilo C1-10, aril(C6-10)-O-, cicloalquil(C3-8)-O-,heteroaril(C1-10)-O- y heterociclil(C1-10)-O-, pudiendo estar opcionalmente sustituido también el citado heterociclilo C1-10 ligado a N, en cualquier átomo de N del anillo que pueda llevar un sustituyente adicional, con 1 a 2 grupos R10 por anillo, seleccionándose independientemente cada R10 del grupo de sustituyentes constituido por H, alquilo C1-4 opcionalmente sustituido con 1 a 3 fluoro-, HO-alquil(C1-4), alquil(C1-4)-(C=O)-, alquil(C1-4)-SO2-, arilo (C6-10), cicloalquilo (C3-8), heteroarilo C1-10 y heterociclilo C1-10, pudiendo estar opcionalmente sustituido cada uno de los arilo C6-10, cicloalquilo C3-8, heteroarilo C1-10 y heterociclilo C1-10 anteriormente citados en cualquier lugar de los citados sustituyentes R9 y R10, en cualquier átomo de C del anillo, con uno a tres restos por anillo seleccionados independientemente del grupo constituido por halo-, hidroxilo, amino, -CN, alquilo C1-4, alcoxi C1-4, -CF3, -CF3O-, alquil(C1-4)-NH-, [alquil (C1-4)]2-N-, alquil (C1-4)-S-, alquil(C1-4)-(S=O)-, alquil (C1-4)-(SO2)-, alquil (C1-4)-O-(C=O)-, formilo y alquil (C1-4)-(C=O)-, n es un número entero de 0 a 2; q es el número entero 1 o 2; s es un número entero de 1 a 3; t es un número entero de 0 a 3; R2 es Cl, Br, alquilo C1-4, -CF3 o -CN; R3 se selecciona del grupo constituido por alquilo C4-10, cicloalquil (C3-12)-(CR11R12)s-, aril(C6-10)-(CR11R12)q-(CH2)-, heterociclil(C1-10)-(CR11R12)s- y heteroaril (C1-10)-(CR11R12)s- estando opcionalmente sustituido el citado alquilo C4-10 con uno a tres sustituyentes seleccionados independientemente de halo, hidroxilo, -CN, alquilo C1-4, alcoxi C1-4, -CF3, CF3O-, alquil(C1-4)-S-,alquil (C1-4)-(S=O)-, alquil(C1-4)-(SO2)-, alquil(C1-4)-CO2-, formilo, alquil(C1-4)-(C=O)-, arilo(C6-10), cicloalquilo C3-8, heteroarilo C1-10, heterociclilo C1-10, aril (C6-10)-O-, cicloalquil(C3-8)-O-, heteroaril (C1-10)-O- y heterociclil(C1-10)-O-; conteniendo cada uno de los citados miembros del grupo R3 heterociclil (C1-10)-(CR11R12)s- y heteroaril (C1-10)-(CR11R12)s-, de 1 a 3 heteroátomos seleccionados independientemente de -O- y -S(O)n-, pudiendo estar opcionalmente sustituidos cada uno de los citados miembros del grupo R3 cicloalquil (C3-12)-(CR11R12)s-, aril (C6-10)-(CR11R12)q-(CH2)-, heterociclil (C1-10)-(CR11R12)s- y heteroaril (C1-10)-(CR11R12)s-, en cualquier átomo de C del anillo que pueda llevar un sustituyente adicional, con 1 a 4 sustituyentes por anillo seleccionados del grupo constituido por halo-, hidroxilo, -CN, alquilo(C1-4), alcoxi C1-4, -CF3, CF3O-, alquil(C1-4)-S-, alquil(C1-4)-(S=O)-, alquil(C1-4)-(SO2)-, alquil(C1-4)-O-(C=O)-, formilo, alquil(C1-4)-(C=O)-, arilo C6-10, [aril(C6-10)]2-CH-, cicloalquilo C3-8, heteroarilo C1-10, heterociclilo C1-10, aril(C6-10)-O-, bencil-O-, cicloalquil(C3-8)-O-, heteroaril(C1-10)-O- y heterociclil (C1-10)-O-, pudiendo estar también opcionalmente sustituidos los citados miembros del grupo R3 cicloalquil (C3-8)-(CR11R12)s-, y heterociclil (C1-10)-(CR11R12)s-, con oxo; pudiendo estar opcionalmente sustituidos cada uno de los arilo C6-10, cicloalquilo C3-8, heteroarilo C1-10 y heterociclilo C1-10 anteriormente citados, en cualquier lugar de los citados sustituyentes R3, en cualquier átomo de C del anillo con 1 a 3 restos por anillo, seleccionados independientemente del grupo constituido por halo-, hidroxilo, amino, -CN, alquilo C1-4, alcoxi C1-4, -CF3, CF3O-, alquil(C1-4)-NH-, [alquil(C1-4)]2-N-, alquil(C1-4)-S-, alquil(C1-4)-(S=O)-, alquil(C1-4)-(SO2)-, alquil (C1-4)-O-(C=O)-, formilo y alquil (C1-4)-(C=O)-; R4 y R5 se seleccionan cada uno independientemente del grupo constituido por H, alquilo C1-6, HO-alquilo C2-6, y cicloalquilo C3-8, o R4 y R5 pueden tomarse opcionalmente junto con el átomo de N al que están unidos para formar un heterociclo de 3 a 8 miembros; R6, R7 y R8 se seleccionan cada uno independientemente del grupo constituido por H, halógeno, ciano-, hidroxilo, alquilo C1-6 opcionalmente sustituido con 1 a 4 Cl-, o fluoro-, y alquil (C1-5)oxi opcionalmente sustituido con 1 a 4 Cl-, o fluoro-; R11 y R12 se seleccionan cada uno independientemente del grupo constituido por H, fluoro-, ciano-, hidroxilo, -CF3, CF3O-, alquilo C1-6, cicloalquilo C3-8, alquil(C1-6)oxi, cicloalquil(C3-8)oxi, fenilo, heteroarilo C1-10, y heterociclilo C1-10, pudiendo estar opcionalmente sustituidos los citados alquilo C1-6, cicloalquilo C3-8, alquil(C1-6)oxi, cicloalquil(C3-8)oxi, fenilo, heteroarilo C1-10 y heterociclilo C1-10 con 1 a 3 sustituyentes seleccionados independientemente de Cl-, fluoro-, ciano-, hidroxilo, -CF3, CF3O-, alquil(C1-4)-S-, alquil(C1-4)-(S=O)-, alquil(C1-4)-(SO2)-, alquil(C1-4)-O-(C=O)-, formilo o alquil (C1-4)-(C=O)-; con la condición de que cuando el citado R3 es cicloalquil (C3-12)-(CR11R12)s, R1 y R2 sean cada uno H y s sea uno o dos, entonces el citado cicloalquilo C3-12 debe ser distinto de adamantilo opcionalmente sustituido; o una sal o solvato farmacéuticamente aceptable del mismo y composiciones farmacéuticas que los contienen. Estos compuestos activos de la presente son potentes inhibidores de P2X7, y como tales son útiles en el tratamiento de la inflamación, osteoartritis, artritis reumatoide, cáncer, reperfusión o isquemia en la apoplejía o infarto de miocardio, enfermedades autoinmunes y otros trastornos.
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- 2002-11-04 WO PCT/IB2002/004613 patent/WO2003042191A1/en active Application Filing
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