ES2625378T3 - Derivado de sulfonamida que tiene actividad antagonista del receptor de PGD2 - Google Patents
Derivado de sulfonamida que tiene actividad antagonista del receptor de PGD2 Download PDFInfo
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- ES2625378T3 ES2625378T3 ES06810485.0T ES06810485T ES2625378T3 ES 2625378 T3 ES2625378 T3 ES 2625378T3 ES 06810485 T ES06810485 T ES 06810485T ES 2625378 T3 ES2625378 T3 ES 2625378T3
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Abstract
Un compuesto de fórmula general:**Fórmula** o una sal farmacéuticamente aceptable del mismo
Description
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A una solución en TH (20 mL) del compuesto (45) (5,0 g, 14,29 mmoles) obtenido en el paso 1, se le agregó ácido clorhídrico 2N (15 mL) y se agitó a 70°C durante 2 horas. Después de enfriarse a temperatura ambiente, la mezcla de reacción se extrajo con acetato de etilo, la capa orgánica se lavó con salmuera saturada y el disolvente se evaporó al vacío. Al residuo resultante se le agregó acetonitrilo (15 mL) y la solución se usó en el siguiente paso.
Una solución de trifenilfosfina (7,45 g, 28,40 mmoles) y hexacloroetano (6,72 g, 28,40 mmoles) en acetonitrilo se agitó durante 30 minutos, y a esta se le agregó una solución del residuo obtenido en acetonitrilo (15 mL) y piridina (4,6 mL, 56,80 mmoles); la mezcla se agitó a temperatura ambiente durante 30 minutos. Después se agitó a 60°C durante una hora. A la solución de reacción se le agregó agua y la solución de reacción se extrajo con acetato de etilo. La capa orgánica se lavó con agua y solución acuosa al 10% de ácido cítrico y el disolvente se evaporó al vacío. El residuo se purificó por cromatografía de columna en gel de sílice (acetato de etilo /hexano = 1/4) para dar el producto (46) (3,35 g, 83% de rendimiento).
Paso 3
Una solución del compuesto (46) (200 mg, 0.70 mmoles) obtenido en el paso 2, el compuesto (13) (239 mg, 0.84 mmoles) obtenido en el paso 2 del ejemplo 3, tetraacetato de plomo (3,1 mg, 0,014 mmoles), butildiadamantilfosfina (10,0 mg, 0,028 mmoles) y t-butóxido de sodio (94,2 mg, 0,98 mmoles) en tolueno (2 mL), se agitó a 110°C bajo una atmósfera de nitrógeno durante 15 horas. Después de enfriarse a temperatura ambiente, la solución de reacción se extrajo con cloroformo y a la capa orgánica se le agregó ácido cítrico (147 mg, 0.70 mmoles); la capa orgánica se lavó con agua y salmuera saturada. El disolvente se evaporó al vacío y se cristalizó de acetato de etilo -hexano para dar el producto (47) (331 mg, 89% de rendimiento).
Paso 4
Una solución del compuesto (47) (100 mg, 0,187 mmoles) obtenido en el paso 3 y paladio al 10% en carbón (30 mg), en THF (15 mL) – MeOH (15 mL), se agitó bajo una atmósfera de hidrógeno durante 2 horas. Después de filtrar, el filtrado se concentró al vacío para dar el producto (48) (81,3 mg, 98% de rendimiento) como un sólido blanco.
Paso 5
Una solución del compuesto (48) (200 mg, 0,45 mmoles) obtenido en el paso 4, carbonato de potasio (93 mg, 0.67 mmoles), yoduro de potasio (15 mmoles) y bromoacetato de metilo (0,064 mL, 0.68 mmoles) en DMF(1,6 mL), se agitó a 90°C durante una hora. Después de enfriarse a 0°C, se le agregó ácido clorhídrico 2N (0,23 mL), MeOH(5,0 mL) y agua (5,0 mL). El cristal obtenido se recogió por filtración para dar el producto III-74 (212 mg, 91% de rendimiento) como un cristal blanco.
Paso 6
Una solución del compuesto III-74 (65 mg, 0,126 mmoles) obtenido en el paso 5 y solución acuosa 4N de hidróxido de sodio (80 μL, 0,315 mmoles) en DMF(1 mL), se agitó durante la noche. Después se le agregó ácido clorhídrico 2N (315 μL) y se agitó; se le agregó agua (20. mL) y se agitó a 0°C durante 30 minutos. El precipitado cristalino se recogió por filtración para dar el producto II-74 (50.6 mg, 80% de rendimiento) como un cristal blanco.
1 H-RMN (CDCl3 ) δ ppm: 1,37 (d, 6H, J = 6,0 Hz), 3,16 (t, 4H), 3,42 (t, 4H), 4,63 (m, 1H), 4,77 (s, 2H), 6,40 (d, 1H, J = 2,7 Hz), 6,62 (dd, 1H, J = 9,0 Hz, 2,4 Hz), 6,98 (d, 2H, J = 3,0 Hz), 7,27 (d, 1H), 7,67-7,72 (m, 3H), 7,79 (d, 1H, J = 3,0 Hz).
Las propiedades físicas del compuesto de la invención se muestran en las tablas de más abajo.
Ejemplo de prueba 1 actividad inhibitoria DP in vitro
1) Preparación de plaquetas y método de prueba de AMPc
Se extrajeron 30 mL de sangre periférica de un voluntario sano utilizando una jeringa que contenía una novena parte de citrato de sodio al 3,8%. Después de centrifugar a 180g durante 10 minutos a temperatura ambiente, el sobrenadante se recogió y se usó como plasma rico en plaquetas (PRP). El PRP resultante se lavó con amortiguador de lavado y se centrifugó tres veces (plaquetas lavadas: PL), y las plaquetas se contaron por medio de un contador de microcelda. Las PL se añadieron a una placa en una cantidad de 1,5 x 108 /prueba y la placa se trató con 3-isobutil-1-metilxantina (IBMX;
0.5 mM) durante 5 minutos. Se inició una reacción añadiendo 100 nM de PGD2, 5 minutos después de la adición de un
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compuesto de prueba. La reacción se terminó con la adición de ácido clorhídrico 1N después de 2 minutos y las células se destruyeron usando triton X-100 al 12%. La cantidad de AMPc en el sobrenadante se determinó por medio de fluorescencia transitoria homogénea (HTRF).
2) Prueba de unión de receptor
Las PL preparadas se homogeneizaron y se recogió una fracción de membrana por centrifugación de alta velocidad. Se añadió a la placa el compuesto de la presente invención y también [3H]-PGD2. A la membrana de plaqueta se le agregó una concentración de proteína de 2 mg/mL y se mezcló en la placa, y se puso sobre hielo durante 2 horas. La solución de reacción se transfirió a un filtro de adsorción baja de proteína y se lavó ocho veces con una solución de lavado usando un cosechador de células. Después del lavado final, se retiró bastante agua y se le añadió escintilador. La actividad inhibitoria de DP se investigó midiendo [3H] usando Micro Beta.
Las concentraciones 50% inhibitorias de DP (CI50) en la prueba de AMPc y los valores de Ki en la prueba de unión de receptor se muestran a continuación.
3) Prueba de agonista y antagonista de prostanoide
Se evaluó la actividad agonista y antagonista de los compuestos de la presente invención contra receptores prostanoides, basándose en el flujo de calcio intracelular o la producción de AMPc como indicador, usando células HEK 293 que expresan EP1, EP2, EP3, EP4, FP, TP e IP humanas, respectivamente. Ningún compuesto mostró actividad agonista contra cada prostanoide. Por otra parte, en cada compuesto se encontró una actividad antagonista (CI50) veinte veces más potente en comparación con la CI50 de la prueba de AMPc con PL.
- Comp. No.
- CI50 (M) Ki (M)
- II-74
- 0.52 0,24
Ejemplo de prueba 2
Prueba usando el modelo de asma OVA de rata
Ratas pardas Noruegas (PN) se sensibilizaron por administración ip. de 0,1 mg/mL de ovoalbúmina (OVA) y 1 mg de gel de hidróxido de aluminio. Se preparó un aerosol de una solución de OVA al 1% con un nebulizador ultrasónico (NE-U17), y después de 12, 19, 26 y 33 días de la sensibilización tres ratas se sometieron a inhalación del aerosol durante 30 minutos en una cámara de exposición. Una hora antes de la cuarta exposición del antígeno, los compuestos de la presente invención se administraron en una dosis de 10 mg/kg por vía oral una vez al día durante tres días consecutivamente. En un grupo de control se administró 0.5% de metilcelulosa en lugar del compuesto de la presente invención.
Tres días después de la cuarta exposición al antígeno se inyectó en la vena yugular de las ratas, bajo anestesia de pentobarbital (80 mg/kg ip.), acetilcolina (3,9, 7,8, 15,6, 31,3, 62,5, 125, 250 y 500 μg/kg), sucesivamente desde una dosis baja a intervalos de 5 minutos, y de inmediato se midió la reacción contráctil de las vías respiratorias (aumento de la presión de insuflación), por medio de un método modificado de Konnzett y Rössler. Se calculó el porcentaje de inhibición de la hipersensibilidad de las vías respiratorias contra el grupo de control basándose en el área bajo la curva (ABC) obtenida de la curva de dosis-respuesta de acetilcolina.
Después de terminar la medición del aumento de hipersensibilidad de las vías respiratorias, los alvéolos bronquiales de las ratas se lavaron tres veces con 5 mL de solución salina. El número total de células en los lavados se contó por medio de un hemacitómetro bajo microscopio óptico y se calculó el porcentaje de inhibición de infiltración de las células inflamatorias contra el grupo de control. Además, se midió la mucina en el fluido de lavado de las vías respiratorias por medio del método ELISA, usando jacalina, una lectina de unión de mucina, y se calculó el porcentaje de inhibición de la secreción de moco contra el grupo de control.
Los resultados se muestran más abajo.
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25
30
Cuadro 62
- Comp. No.
- Dosis (mg/kg) Porcentaje de inhibición (%)
- Hipersensibilidad de vías respiratorias
- Infiltración de células inflamatorias Secreción de moco
- II-74
- 10 111 65 92
Ejemplo de prueba 3
Prueba de modelo de congestión nasal de conejillo de indias
A continuación se muestran métodos para medir la resistencia de las vías nasales y para evaluar la actividad de anticongestión nasal usando conejillos de indias.
Se preparó un aerosol de una solución de ovoalbúmina (OVA) al 1% con un nebulizador ultrasónico; conejillos de indias Hartley machos se sensibilizaron dos veces por inhalación del aerosol durante 10 minutos con un intervalo de una semana, y se inició una reacción 7 días después por exposición al antígeno. La tráquea del conejillo de indias se cortó bajo anestesia con pentobarbital (30 mg/kg, vía oral) y se acoplaron cánulas en partes de la cavidad nasal y el pulmón, respectivamente. En la parte del pulmón se conectó un ventilador que suministraba 4 mL de aire a una velocidad de 60 veces/min. La respiración espontánea del conejillo de indias se detuvo administrando galamina (2 mg/kg, iv.) y usando un ventilador se suministraron 4 mL de aire a una velocidad de 70 veces/min al pico de la nariz, a través de la cánula de la parte lado nasal. La presión de aire necesaria para suministrar el aire se midió por medio de un transductor acoplado en la rama lateral y se usó como indicador de resistencia de la cavidad nasal. La exposición al antígeno se realizó generando el aerosol de solución de OVA al 3% entre el ventilador y la cánula de cavidad nasal durante tres minutos. Los compuestos de la presente invención se administraron por vía intravenosa 10 minutos antes de la exposición al antígeno. La resistencia de la cavidad nasal se midió continuamente durante un periodo de 0 a 30 minutos, y basándose en el ABC de los 30 minutos se obtuvo el porcentaje de inhibición contra el vehículo, que se registró como la resistencia de la cavidad nasal (cm de H2O) en el eje longitudinal y el tiempo (de 0 a 30 min) en el eje de la abscisa.
Ejemplos de formulación
Los siguientes ejemplos de formulación 1-8 solo son para fines ilustrativos y no tienen la intención de limitar al alcance de la presente invención. El término “ingrediente activo” significa los compuestos de la presente invención, sales o
- hidratos farmacéuticamente aceptables de los mismos.
- Ejemplo de formulación 1
- Se prepara una cápsula de gelatina dura con los siguientes ingredientes:
- Cantidad (mg/cápsula)
- Ingrediente activo
- 250
- Almidón (seco)
- 200
- Estearato de magnesio
- 10
- Total
- 460 mg
- Ejemplo de formulación 2
- Se prepara una tableta con los siguientes ingredientes:
- Cantidad (mg/tableta)
- Ingrediente activo Celulosa (microcristalina) Dióxido de silicio (fumante) Acido esteárico
- 250 400 10 5
- Total
- 665 mg
Los ingredientes anteriores de mezclan y la mezcla se comprime para obtener una tableta con un peso de 665 mg/tableta.
9
Ejemplo de formulación 7
Se prepara una suspensión que contiene 50 mg de un ingrediente activo, de la siguiente manera:
Ingrediente activo 50 mg Carboximetilcelulosa de sodio 50 mg Jarabe 1,25 ml Solución de ácido benzoico 0,10 ml Saborizante c.s. Pigmento c.s. Total (agregando agua purificada) 5 ml
El ingrediente activo se tamiza a través de una malla No. 45 US y se mezcla con la carboximetilcelulosa de sodio y el 5 jarabe para obtener una pasta suave. La solución de ácido benzoico y el saborizante se diluyen con una parte de agua y se añaden a la pasta y se agita. Se agrega la cantidad necesaria de agua para obtener la suspensión objetivo.
Ejemplo de formulación 8
Se prepara una formulación para inyección iv, de la siguiente manera:
Ingrediente activo 100 mg Glicérido de ácido graso saturado 1000 ml
10 Usualmente la solución que contiene el ingrediente activo anterior se inyecta por vía intravenosa a un paciente, a una velocidad de 1 ml/min.
Aplicación industrial
Se encontró que un derivado de sulfonamida novedoso tiene actividad antagonista del receptor DP y es eficaz en el tratamiento de enfermedades alérgicas.
15
11
Claims (1)
-
imagen1
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JP2006062617 | 2006-03-08 | ||
PCT/JP2006/318917 WO2007037187A1 (ja) | 2005-09-27 | 2006-09-25 | Pgd2受容体アンタゴニスト活性を有するスルホンアミド誘導体 |
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ES06810485.0T Active ES2625378T3 (es) | 2005-09-27 | 2006-09-25 | Derivado de sulfonamida que tiene actividad antagonista del receptor de PGD2 |
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EP (3) | EP2407459A1 (es) |
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AU (1) | AU2006296004B2 (es) |
BR (1) | BRPI0616574A2 (es) |
CA (1) | CA2621310C (es) |
ES (1) | ES2625378T3 (es) |
IL (1) | IL189906A (es) |
NO (1) | NO20081970L (es) |
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2006
- 2006-09-25 EP EP11008295A patent/EP2407459A1/en not_active Withdrawn
- 2006-09-25 BR BRPI0616574-5A patent/BRPI0616574A2/pt not_active IP Right Cessation
- 2006-09-25 US US11/992,602 patent/US8993763B2/en active Active
- 2006-09-25 AU AU2006296004A patent/AU2006296004B2/en not_active Ceased
- 2006-09-25 RU RU2008116708/04A patent/RU2405770C2/ru not_active IP Right Cessation
- 2006-09-25 CA CA2621310A patent/CA2621310C/en not_active Expired - Fee Related
- 2006-09-25 WO PCT/JP2006/318917 patent/WO2007037187A1/ja active Application Filing
- 2006-09-25 EP EP11008294A patent/EP2407453A1/en not_active Withdrawn
- 2006-09-25 KR KR1020087007310A patent/KR101289995B1/ko not_active IP Right Cessation
- 2006-09-25 ES ES06810485.0T patent/ES2625378T3/es active Active
- 2006-09-25 EP EP06810485.0A patent/EP1939175B1/en active Active
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- 2006-09-26 TW TW095135455A patent/TWI325861B/zh not_active IP Right Cessation
- 2006-09-26 TW TW099105796A patent/TWI445695B/zh not_active IP Right Cessation
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2008
- 2008-03-03 IL IL189906A patent/IL189906A/en not_active IP Right Cessation
- 2008-04-25 NO NO20081970A patent/NO20081970L/no not_active Application Discontinuation
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