AR063680A1 - Derivados de pirazolo[1, 5-a]pirimidina, metodos e intermediario para su preparacion, composiciones farmaceuticas que los comprenden y su uso en la fabricacion de medicamentos para el tratamiento de enfermedades mediadas por la modulacion de mglur5. - Google Patents
Derivados de pirazolo[1, 5-a]pirimidina, metodos e intermediario para su preparacion, composiciones farmaceuticas que los comprenden y su uso en la fabricacion de medicamentos para el tratamiento de enfermedades mediadas por la modulacion de mglur5.Info
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- AR063680A1 AR063680A1 ARP070103437A ARP070103437A AR063680A1 AR 063680 A1 AR063680 A1 AR 063680A1 AR P070103437 A ARP070103437 A AR P070103437A AR P070103437 A ARP070103437 A AR P070103437A AR 063680 A1 AR063680 A1 AR 063680A1
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- Prior art keywords
- alkylaminocarbonyl
- alkylamino
- alkyl
- aryl
- heterocyclyl
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Abstract
Estos compuestos son potentes moduladores de mGluR5 y son útiles, por ejemplo, para el tratamiento de diversos trastornos neurológicos. Reivindicación 1: Un compuesto de pirazolo-pirimidina de fórmula (1) donde Y1, Y2 e Y3 independientemente son CR10, CR11, CR10R11, NR12, S o O, donde al menos uno de Y1, Y2 e Y3 denota CR10; o Y1 e Y2 juntos denotan un grupo R10C=N; R10C=CR11; R10R11C-C(=O) o R12N-(C=O); o Y2 e Y3 juntos denotan un grupo R10C=N; R10C=CR11; R10R11C-C(=O) o R12N-(C=O); R1 representa cloro o bromo; R2 representa hidrógeno, alquilo C1-6, cicloalquiIo C3-7 o trifluorometilo; R3 representa hidrógeno, alquilo C1-6, cicloaIquilo C3-7 o trifluorometilo; o R2 y R3, junto con el átomo de carbono del anillo, representan un grupo carbonilo; R4 representa hidrógeno, alquilo C1-6, cicloalquilo C3-7 o trifluorometilo; R5 representa hidrógeno, alquilo C1-6, cicloalquilo C3-7 o trifluorometilo; o R4 y R5, junto con el átomo de carbono del anillo, representan un grupo carbonilo; R6 representa hidrógeno, alquilo C1-6, cicloalquilo C3-7 o trifluorometilo; R7 representa hidrógeno, alquilo C1-6, cicloalquilo C3-7 o trifluorometilo; R6 y R7, junto con el átomo de carbono del anillo, representan un grupo carbonilo; R2 o R3, junto con R6 o R7, pueden formar un radical bivalente del tipo CH2-CH2 o CH2-O; R10 y R11 independientemente representan hidrógeno, halógeno, amino, hidroxi, nitro, ciano, trifluorometilo, trifluorometoxi, arilo, alquilo C1-6, cicloalquilo C3- 7, alquenilo C2-6, alquinilo C2-6, alcoxi C1-6, cicloalquiloxi C3-7, alqueniloxi C2-6, alquiniloxi C2-6, heteroarilo, heterociclilo, ariloxi, heteroariloxi, heterocicliloxi, alquilamino C1-6, di-alquilamino C1-6, cicloalquilamino C3-7, di- cicloalquilamino C3-7, alquil C1-6-cicloalquilamino C3-7, alquenilamino C2-6, alquinilamino C2-6, di-alquenilamino C2-6, di-alquinilamino C2-6, alquil C1-6-alquenilamino C2-6, alquil C1-6-alquinilamino C2-6, alquenil C2-6-cicloalquilamino C3-7, alquinil C2-6-cicloalquilamino C3-7, alquenil C2-6-alquinilamino C2-6, arilamino, diarilamino, aril-alquilamino C1-6, aril-alquenilamino C2-6, aril-alquinilamino C2-6, aril-cicloalquilamino C3-7, heteroarilamino, diheteroarilamino, heteroaril- alquilamino C1-6, heteroaril-alquenilamino C2-6, heteroaril-alquinilamino C2-6, heteroaril-cicloalquilamino C3-7, heteroarilarilamino, heterociclilamino, diheterociclilamino, heterociclilalquilamino C1-6, heterociclil-alquenilamino C2-6, heterociclil-alquinilamino C2-6, heterociclil-cicloalquilamino C3-7, heterociclilarilamino, heterociclilheteroarilamino, acil, aciloxi, acilamino, alcoxicarbonilo C1-6, cicloalcoxicarbonilo C3-7, alqueniloxicarbonilo C2-6, alquiniloxicarbonilo C2-6, ariloxicarbonilo, heteroariloxicarbonilo, heterocicliloxicarbonilo, aminocarbonilo, alquilamino-carbonilo C1-6, di-alquilaminocarbonilo C1-6, cicloalquilaminocarbonilo C3-7, di-cicloalquilaminocarbonilo C3-7, aIquil C1-6-cicloalquilaminocarbonilo C3- 7, alquenil-aminocarbonilo C2-6, alquinil-aminocarbonilo C2-6, di-alquenilaminocarbonilo C2-6, di-alquinilaminocarbonilo C2-6, alquil C1-6-alquenilaminocarbonilo C2-6, aIquil C1-6-alquinil-aminocarbonilo C2-6, alquenil C2-6- cicloalquilaminocarbonilo C3-7, alquinil C2-6-cicloalquilaminocarbonilo C3-7, alqueniI C2-6-alquinilaminocarbonilo C2-6, arilaminocarbonilo, diarilaminocarbonilo, aril-alquilaminocarbonilo C1-6, aril-alquenilaminocarbonilo C2-6, aril- alquinilaminocarbonilo C2-6, aril- cicloalquilaminocarbonilo C3-7, heteroarilaminocarbonilo, diheteroarilaminocarbonilo, heteroaril-alquilaminocarbonilo C1-6, heteroaril-alquenilaminocarbonilo C2-6, heteroaril-alquinilaminocarbonilo C2-6, heteroaril- cicloalquilaminocarbonilo C3-7, heteroarilarilaminocarbonilo, heterociclilaminocarbonilo, diheterociclilamino-carbonilo, heterociclil-alquilaminocarbonilo C1-6, heterociclil-alquenilamino-carbonilo C2-6, heterociclil-alquinilaminocarbonilo C2-6, heterociclil- cicloalquilaminocarbonilo C3-7, heterociclilarilaminocarbonilo, heterociclilheteroarilamino-carbonilo, alquilsulfinilo C1-6, cicloalquilsulfinilo C3-7, alquenilsulfinilo C2-6, alquinilsulfinilo C2-6, arilsulfinilo, heteroarilsulfinilo, heterociclilsulfinilo, alquilsulfonilo C1-6, cicloalquilsulfonilo C3-7, alquenilsulfonilo C2-6, alquinilsulfonilo C2-6, arilsulfonilo, heteroarilsulfonilo, heterociclilsulfonilo, alquilsulfonilamino C1-6 o arilsulfonilamino; y R12 representa hidrógeno, alquilo C1-6, cicloalquilo C3-7, alquenilo C2-6, alquinilo C2-6, acilo, arilo, heteroarilo, heterociclilo, alquilamino-carbonilo C1-6, di-alquilamino-carbonilo C1-6, alquilsulfonilo C1-6, arilsulfonilo o heteroarilsulfonilo; e isómeros ópticos, sales, hidratos, solvatos y polimorfos farmacéuticamente aceptables de dicho compuesto. Reivindicación 29: Un proceso para la síntesis de un compuesto seleccionado entre aquellos de fórmula (1) donde: Y1, Y2 e Y3 independientemente son CR10, CR11, CR10R11, NR12, S o O, donde al menos uno de Y1, Y2 e Y3 denota CR10; o Y1 e Y2 juntos denotan un grupo R10C=N; R10C=CR11; R10R11C-C(=O) o R12N-(C=O); o Y2 e Y3 juntos denotan un grupo R10C=N; R10C=CR11; R10R11C-C(=O) o R12N-(C=O); R1 representa cloro o bromo; R2 representa hidrógeno, alquilo C1-6, cicloalquiIo C3-7 o trifluorometilo; R3 representa hidrógeno, alquilo C1-6, cicloaIquilo C3-7 o trifluorometilo; o R2 y R3, junto con el átomo de carbono del anillo, representan un grupo carbonilo; R4 representa hidrógeno, alquilo C1-6, cicloalquilo C3-7 o trifluorometilo; R5 representa hidrógeno, alquilo C1-6, cicloalquilo C3-7 o trifluorometilo; o R4 y R5, junto con el átomo de carbono del anillo, representan un grupo carbonilo; R6 representa hidrógeno, alquilo C1-6, cicloalquilo C3-7 o trifluorometilo; R7 representa hidrógeno, alquilo C1-6, cicloalquilo C3-7 o trifluorometilo; R6 y R7, junto con el átomo de carbono del anillo, representan un grupo carbonilo; R2 o R3, junto con R6 o R7, pueden formar un radical bivalente del tipo CH2-CH2 o CH2-O; R10 y R11 independientemente representan hidrógeno, halógeno, amino, hidroxi, nitro, ciano, trifluorometilo, trifluorometoxi, arilo, alquilo C1-6, cicloalquilo C3- 7, alquenilo C2-6, alquinilo C2-6, alcoxi C1-6, cicloalquiloxi C3-7, alqueniloxi C2-6, alquiniloxi C2-6, heteroarilo, heterociclilo, ariloxi, heteroariloxi, heterocicliloxi, alquilamino C1-6, di-alquilamino C1-6, cicloalquilamino C3-7, di- cicloalquilamino C3-7, alquil C1-6-cicloalquilamino C3-7, alquenilamino C2-6, alquinilamino C2-6, di-alquenilamino C2-6, di-alquinilamino C2-6, alquil C1-6-alquenilamino C2-6, alquil C1-6-alquinilamino C2-6, alquenil C2-6-cicloalquilamino C3-7, alquinil C2-6-cicloalquilamino C3-7, alquenil C2-6-alquinilamino C2-6, arilamino, diarilamino, aril-alquilamino C1-6, aril-alquenilamino C2-6, aril-alquinilamino C2-6, aril-cicloalquilamino C3-7, heteroarilamino, diheteroarilamino, heteroaril- alquilamino C1-6, heteroaril-alquenilamino C2-6, heteroaril-alquinilamino C2-6, heteroaril-cicloalquilamino C3-7, heteroarilarilamino, heterociclilamino, diheterociclilamino, heterociclilalquilamino C1-6, heterociclil-alquenilamino C2-6, heterociclil-alquinilamino C2-6, heterociclil-cicloalquilamino C3-7, heterociclilarilamino, heterociclilheteroarilamino, acil, aciloxi, acilamino, alcoxicarbonilo C1-6, cicloalcoxicarbonilo C3-7, alqueniloxicarbonilo C2-6, alquiniloxicarbonilo C2-6, ariloxicarbonilo, heteroariloxicarbonilo, heterocicliloxicarbonilo, aminocarbonilo, alquilamino-carbonilo C1-6, di-alquilaminocarbonilo C1-6, cicloalquilaminocarbonilo C3-7, di-cicloalquilaminocarbonilo C3-7, aIquil C1-6-cicloalquilaminocarbonilo C3- 7, alquenil-aminocarbonilo C2-6, alquinil-aminocarbonilo C2-6, di-alquenilaminocarbonilo C2-6, di-alquinilaminocarbonilo C2-6, alquil C1-6-alquenilaminocarbonilo C2-6, aIquil C1-6-alquinil-aminocarbonilo C2-6, alquenil C2-6- cicloalquilaminocarbonilo C3-7, alquinil C2-6-cicloalquilaminocarbonilo C3-7, alqueniI C2-6-alquinilaminocarbonilo C2-6, arilaminocarbonilo, diarilaminocarbonilo, aril-alquilaminocarbonilo C1-6, aril-alquenilaminocarbonilo C2-6, aril- alquinilaminocarbonilo C2-6, aril- cicloalquilaminocarbonilo C3-7, heteroarilaminocarbonilo, diheteroarilaminocarbonilo, heteroaril-alquilaminocarbonilo C1-6, heteroaril-alquenilaminocarbonilo C2-6, heteroaril-alquinilaminocarbonilo C2-6, heteroaril- cicloalquilaminocarbonilo C3-7, heteroarilarilaminocarbonilo, heterociclilaminocarbonilo, diheterociclilamino-carbonilo, heterociclil-alquilaminocarbonilo C1-6, heterociclil-alquenilamino-carbonilo C2-6, heterociclil-alquinilaminocarbonilo C2-6, heterociclil- cicloalquilaminocarbonilo C3-7, heterociclilarilaminocarbonilo, heterociclilheteroarilamino-carbonilo, alquilsulfinilo C1-6, cicloalquilsulfinilo C3-7, alquenilsulfinilo C2-6, alquinilsulfinilo C2-6, arilsulfinilo, heteroarilsulfinilo, heterociclilsulfinilo, alquilsulfonilo C1-6, cicloalquilsulfonilo C3-7, alquenilsulfonilo C2-6, alquinilsulfonilo C2-6, arilsulfonilo, heteroarilsulfonilo, heterociclilsulfonilo, alquilsulfonilamino C1-6 o arilsulfonilamino; y R12 representa hidrógeno, alquilo C1-6, cicloalquilo C3-7, alquenilo C2-6, alquinilo C2-6, acilo, arilo, heteroarilo, heterociclilo, alquilamino-carbonilo C1-6, di-alquilamino-carbonilo C1-6, alquilsulfonilo C1-6, arilsulfonilo o heteroarilsulfonilo; e isómeros ópticos, sales, hidratos, solvatos y polimorfos farmacéuticamente aceptables de dicho compuesto, donde un compuesto de fórmula (2) se suspende en una mezcla de etanol y agua y se trata con ácido clorhídrico, seguido por la reacción con H2NNHCOOCH3, para proporcionar un compuesto de fórmula (3), el cual se hace reaccionar con un compuesto de fórmula (4) para proporcionar un compuesto de fórmula (5) el cual se hidroliza en condiciones ácidas para proporcionar un compuesto de fórmula (6) el cual se trata con una amina de fórmula (7) en presencia de un agente de condensación, para proporcionar un compuesto de fórmula (1), el cual se convierte, si así se desea, en una sal, hidrato, solvato o polimorfo farmacé
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2007
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- 2007-08-03 KR KR1020097002224A patent/KR20090047450A/ko not_active Application Discontinuation
- 2007-08-03 RU RU2009107688/04A patent/RU2009107688A/ru not_active Application Discontinuation
- 2007-08-03 AU AU2007280429A patent/AU2007280429A1/en not_active Abandoned
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- 2007-08-03 JP JP2009522284A patent/JP2010500288A/ja active Pending
- 2007-08-03 DE DE602007011773T patent/DE602007011773D1/de active Active
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- 2007-08-03 AR ARP070103438A patent/AR062209A1/es unknown
- 2007-08-03 EP EP07788196.9A patent/EP2054416B8/en active Active
- 2007-08-03 US US11/890,211 patent/US7947689B2/en not_active Expired - Fee Related
- 2007-08-03 MX MX2009000919A patent/MX2009000919A/es active IP Right Grant
- 2007-08-03 US US11/890,230 patent/US20080032998A1/en not_active Abandoned
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