ES2562447T3 - Derivados de piridina - Google Patents
Derivados de piridina Download PDFInfo
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- ES2562447T3 ES2562447T3 ES09700450.1T ES09700450T ES2562447T3 ES 2562447 T3 ES2562447 T3 ES 2562447T3 ES 09700450 T ES09700450 T ES 09700450T ES 2562447 T3 ES2562447 T3 ES 2562447T3
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Abstract
Un compuesto de Fórmula X como se define a continuación:**Fórmula** en, forma libre o de sal, donde**Fórmula**
Description
- Ej.
- IC50 (µM)
- 1.3
- 0.023
- 1.6
- 0.029
- 1.10
- 0.057
- 1.15
- 0.190
- 1.23
- 0.214
- 2.1
- 0.017
- 2.2
- 0.030
- 2.12
- 0.209
- 2.17
- 0.236
- 2.23
- 0.016
- 2.24
- 0.014
- 2.26
- 0.012
- 2.28
- 0.052
- 2.30
- 0.008
- 2.31
- 0.004
- 2.62
- 0.235
- 2.69
- 0.028
- 2.70
- 0.089
- 2.71
- 0.074
- 2.72
- 0.042
- 2.80
- 0.039
- 2.81
- 0.028
- 2.82
- 0.036
- 2.83
- 0.059
- 2.84
- 0.020
- 2.85
- 0.074
- 2.86
- 0.092
- 2.87
- 0.139
- 2.88
- 0.022
- 2.89
- 0.017
9
donde T1, T2 y T3 son como se muestra a continuación, en la Tabla 1 y la Tabla 2. Siendo el método de preparación descrito en lo sucesivo.
TABLA 1
- Ej.
- T1 T2 T3 [M+H]+
- 1.1
-
imagen13 imagen14 imagen15 381 367 395
- 1.2
- 1.3
14
- Ej.
- Datos físicos
- 1.10
- 1H RMN (500 MHz, DMSO-d6) δ 10.86 (1H, Br), 8.91 (1H, d, 2.5 Hz), 8.67 (1H, dd, 1.8 Hz), 8.66 (1H, dd, 1.7 Hz), 8.40 (1H, d, 8.4 Hz), 8.11 (1H, ddd, 8.0, 2.0, 2.0 Hz), 7.95 (1H, ddd, 7.7, 7.7, 1.9 Hz), 7.85 (1H, d, 1.5 Hz), 7.63 (1H, d, 7.8 Hz), 7.55 (1H, ddd, 7.9 Hz, 4.8 Hz), 7.43 (1H, ddd, 7.5, 4.6, <0.5 Hz), 7.37 (1H, d, 8.1 Hz), 7.25 (1H, d, 2.4 Hz), 7.09 (1H, ddd, 7.3, 7.0, <0.5 Hz), 7.0 (1H, dd, 7.3 Hz, 7.3 Hz), 6.94 (1H, br t, 7 Hz), 6.85 (1H, d, 1Hz), 3.77 (2H, dt, 7.3, 7 Hz), 3.08 (2H, t, 7.3 Hz)
- 2.1
- 1H RMN (400 MHz, DMSO-d6) δ 8.99 (1H, d, 1.2 Hz), 8.93 (1H, d, 1.1 Hz), 8.66 (1H, dd, 4.7 Hz, 1.6 Hz), 8.40 (1H, dd, 7.9 Hz, 1.1 Hz), 8.37 (1H, dd, 1.2 Hz, 1.1 Hz), 7.95 (1H, m), 7.94 (2H, d, 8.1 Hz), 7.93 (1H, d, 1.5 Hz), 7.54 (2H, d, 8.1 Hz), 7.42 (1H, m), 6.91 (1H, d, 1.5Hz), 6.75 (1H, q, 4.8 Hz), 3.64-3.40 (4H, hombros anchos), 2.97 (3H, d, 4.8 Hz), 2.33 (4H, hombro ancho), 2.23 (3H, s)
- 2.2
- 1H RMN (400 MHz, DMSO-d6) δ 8.91 (1H, d, 1.72 Hz), 8.8 (1H, s), 8.67 (1H, d, 4.56 Hz), 8.41 (1H, d, 7.96 Hz), 8.23 (1H, m), 7.94 (2H, m), 7.73 (2H, d, 8.64 Hz), 7.43 (1H, m), 7.07 (2H, d, 8.68 Hz), 6.88 (1H, s), 6.75 (1H, m), 3.3-3.2 (8H, hombro ancho), 2.97 (3H, d, 4.68Hz), 2.26 (3H, s).
- 2.12
- 1H RMN (400 MHz, DMSO-d6) δ 8.93 (1H, d, 2.17 Hz), 8.88 (1H, d, 2.15 Hz), 8.68 (1H, dd, 7.9 Hz, 1.72 Hz), 8.4 (1H, dd, 1.2 Hz, 1.1 Hz), 8.27 (1H, m), 7.94 (1H, m), 7.9 (1H, d, 1.56 Hz), 7.43 (1H, m), 7.33 (1H, t), 7.0 (1H, d,2.32 Hz), 6.88 (2H, m), 6.78 (1H, m), 6.64 (1H, dd, 8, 2.48 Hz), 3.34 (4H, hombro ancho), 2.97 (3H, d, 4.8 Hz), 1.99 (4H, amplio).
- 2.23
- 1H RMN (400 MHz, DMSO-d6) δ 8.95 (1H, d, 2.16 Hz), 8.9 (1H, d, 2.12 Hz), 8.67 (1H, m), 8.41 (1H, d, 7.91 Hz), 8.31 (1H, m), 7.96 (1H, m), 7.92 (1H, m), 7.73 (2H, m), 7.48 (2H, m), 7.42 (1H, m), 6.9 (1H, d, 1.36 Hz), 6.75 (1H, m), 3.56 (2H, s), 2.97 (3H, d, 4.8 Hz), 2.55-2.20 (8H, hombros anchos), 2.15 (3H, s)
- 2.24
- 1H RMN (500 MHz, DMSO-d6) δ 8.95 (1H, d, 1.8 Hz), 8.89 (1H, d, 1.8 Hz), 8.66 (1H, m), 8.39 (1H, d, 8.0 Hz), 8.31 (1H, m), 7.95 (1H, m), 7.91 (1H, m), 7.8 (2H, d, 8.0 Hz), 7.44 (2H, d, 8.0 Hz), 7.42 (1H, m), 6.9 (1H, d, 1.0 Hz), 6.74 (1H, q, 4.8 Hz), 3.51 (2H, s), 2.96 (3H, d, 4.7 Hz), 2.59 (1H, septeto, 6.5 Hz), 2.55-2.20 (8H, hombros anchos), 0.95 (6H, d, 6.5 Hz)
- 2.26
- 1H RMN (400 MHz, DMSO-d6) δ 8.96 (1H, d, 2.16 Hz), 8.89 (1H, d, 2.12 Hz), 8.67 (1H, m), 8.41 (1H, d, 7.93 Hz), 8.31 (1H, m), 7.96 (1H, m), 7.92 (1H, m), 7.8 (2H, m), 7.46 (2H, m), 7.42 (1H, m), 6.9 (1H, d, 1.32 Hz), 6.75 (1H, m), 3.53 (2H, s), 2.97 (3H, d, 4.8 Hz), 2.55-2.20 (8H, hombros anchos), 2.17 (3H, s)
- 2.28
- 1H RMN (400 MHz, MeOD-d4) δ 8.94 (2H, dd), 8.48 (1H, t), 8.20 (1H, m), 7.91 (2H, m), 7.83 (2H, d, 1.32 Hz), 7.62 (2H, m), 7.31 (1H, d, 7.56 Hz), 6.88 (1H, d, 1.4 Hz), 3.82 (2H, br), 3.56 (2H, br), 3.06 (3H, s), 2.65 (3H, s), 2.36 (3H, s).
- 2.30
- 1H RMN (400 MHz, DMSO-d6) δ 9 (1H, d, 1.2 Hz), 8.95 (1H, d, 1.1 Hz), 8.66 (1H, dd, 4.7 Hz, 1.6 Hz), 8.40 (1H, dd, 7.9 Hz, 1.1 Hz), 8.37 (1H, dd, 1.2 Hz, 1.1 Hz), 7.95 (1H, m), 7.94 (2H, d, 8.1 Hz), 7.93 (1H, d, 1.5 Hz), 7.54 (2H, d, 8.1 Hz), 7.42 (1H, m), 7.08 (1H, d, 1.5Hz), 7.02 (1H, q, 4.8 Hz), 5.76 (1H, s), 3.64-3.40 (4H, hombros anchos), 3.63 (1H, amplio), 2.78 (4H, hombro ancho), 0.80 (2H, m), 0.54 (2H, m).
- 2.31
- 1H RMN (500 MHz, DMSO-d6) δ 8.96 (1H, d, 2.2 Hz), 8.91 (1H, d, 2.1 Hz), 8.67 (1h, dd, 5 Hz, 1.5 Hz), 8.36 (1H, dd, 7.9 Hz, <1 Hz), 8.37 (1h, m), 7.96 (1H, d, 1.5 Hz), 7.93 (1H, m), 7.80 (2h, d, 7.7 Hz), 7.45 (2H, d, 7.7 Hz), 7.45 (1H, m), 7.08 (1H, d, 2.5 Hz), 7.01 (1h, d, 1.5 Hz), 3.51 (2H, s), 2.73 (1H, m), 2.60 (1H, septeto, 6.4 Hz), 2.502.30 (8H, hombro ancho), 0.95 (6H, d, 6.4 Hz), 0.79 (2H, m), 0.53 (2H, m).
- 2.62
- 1H RMN (500 MHz, DMSO-d6) δ 8.96 (1H, d, 1.79 Hz), 8.9 (1H, d, 1.79 Hz), 8.66 (1H,d, 3.4 Hz), 8.36 (1H, d, 7.9 Hz), 8.32 (1H, br s), 7.96 (1H, s), 7.93 (1H, t, 7.72 Hz), 7.8 (2H, d, 7.95 Hz), 7.45 (2H, d, 7.82 Hz), 7.42 (1H, br t, 6.0 Hz), 7.08 (1H, s), 7.00 (1H, s), 3.61 (2H, br m), 2.73 (1H, m), 2.72 (1H, m), 2.68-2.29 (2H, m), 2.59-2.46 (2H, m), 2.09 (6H, s), 1.85-1.62 (2H, m), 0.79-0.53 (4H, m).
- 2.72
- 1H RMN (400 MHz, DMSO-d6) δ 8.96 (1H, d, 3.0 Hz), 8.87 (1H, d, 2.0 Hz), 8.66 (1H, d, 4.0 Hz), 8.32 (1H, s), 8.29 (1H, d, 3.0 Hz), 7.92 (2H, m), 7.81 (2H, d, 1.3 Hz), 7.44 (3H, m), 6.91 (1H, d, 1.0Hz), 6.23 (1H, s), 3.53 (2H, s), 3.31 (1H, m), 2.49 (8H, br), 0.98 (6H, s)
93
- Ej.
- Datos físicos
- 2.80
- 1H RMN (500 MHz, DMSO-d6) δ 8.99 (1H, d, 2.2 Hz), 8.98 (1H, d, 2.2 Hz), 8.71 (1H, m), 8.58 (1H, d, 1.7 Hz), 8.5 (1H, dd, 7.9 Hz), 8.42 (1H, dd, 2.2 Hz, 2.2 Hz), 8.1 (1H, d, 1.7 Hz), 7.99 (1H, ddd, 7.9, 7.9, 1.6 Hz), 7.82 (2H, d, 8.1 Hz), 7.48 (1H, m), 7.45 (2H, d, 8.1 Hz), 5.4 (1H, s), 3.5 (2H, s), 2.59 (1H, septeto, 6.4 Hz), 2.48-2.28 (8H, hombros anchos), 1.6 (6H, s), 0.95 (6H, d, 6.4 Hz).
- 2.81
- 1H RMN (400 MHz, DMSO-d6) δ 9 (1H, d, 2.2 Hz), 8.99 (1H, d, 2.2 Hz), 8.73 (1H, m), 8.59(1H, d, 1.7 Hz), 8.51 (1H, dd, 7.9 Hz), 8.43 (1H, dd, 2.2 Hz, 2.2 Hz), 8.1 (1H, d, 1.7 Hz), 7.99 (1H, ddd, 7.9, 7.9, 1.6 Hz), 7.82 (2H, d, 8.1 Hz), 7.48 (1H, m), 7.45 (2H, d, 8.1 Hz), 5.4 (1H, s), 3.5 (2H, s), 2.71 (4H, m), 2.32 (4H, m), 1.6 (6H, s).
- 2.82
- 1H RMN (400 MHz, DMSO-d6) δ 9.00 (2H, q), 8.74 (1H, d, 4.58 Hz), 8.59 (1H, s), 8.51 (1H, d, 7.92 Hz), 8.45 (1H, s), 8.12 (1H, s), 8.00 (1H, t), 7.84 (2H, d, 8.04 Hz), 7.47 (3H, m), 5.41 (1H, s), 3.52 (2H, s), 2.39 (8H, br), 1.62 (6H, s), 1.00 (9H, s).
- 2.83
- 1H RMN (400 MHz, DMSO-d6) δ 9.06 (2H, q), 8.74 (1H, d, 4.26 Hz), 8.61 (1H, s), 8.52 (1H, s), 8.50 (1H,s), 8.12 (1H, d, 1.27 Hz), 7.98 (3H, m), 7.57 (2H, d, 8.12 Hz), 7.50 (1H, m), 5.42 (1H, s), 3.67 (4H, br), 2.37 (4H br), 1.63 (6H, s).
- 2.84
- 1H RMN (400 MHz, DMS0-d6) δ 8.99 (1H, s), 8.81 (1H, d, 1.91 Hz), 8.74 (1H, m), 8.60 (1H, s), 8.55 (1H, s), 8.50 (1H, d, 7.93 Hz), 8.39 (1H, s), 8.17 (1H, s), 8.05 (1H, s), 8.00 (1H, t), 7.51 (1H, m), 4.45 (1H, m), 3.99 (2H, m), 3.51 (2H, m), 2.02 (4H, m), 1.62 (6H, s).
- 2.85
- 1H RMN (400 MHz, DMSO-d6) δ 9.01 (2H, q), 8.73 (1H, d, 4.29 Hz), 8.61 (1H, s), 8.52 (1H, d, 7.89 Hz), 8.44 (1H, s), 8.13 (1H, s), 8.00 (1H, t), 7.84 (2H, d), 7.47 (3H, m), 5.41 (1H, s), 3.56 (2H, s), 2.42 (8H, br), 1.62 (6H, s).
- 2.86
- 1H RMN (400 MHz, DMSO-d6) δ 8.95 (1H, d, 2.08 Hz), 8.8 (1H, d, 2.16 Hz), 8.74 (1H, m), 8.54 (1H, d, 1.64 Hz), 8.5 (1H, m), 8.44 (1H, m), 8.37 (1H, m), 8.13 (1H, d, 0.6 Hz), 8.05 (1H, d, 1.65 Hz), 7.98 (1H, m), 7.49 (1H, m), 5.4 (1H, s), 3.9 (3H, s), 1.6 (6H, s)
- 2.87
- 1H RMN (400 MHz, DMSO-d6) δ 9.06 (2H, q), 8.74 (1H, d, 3.96 Hz), 8.62 (1H, d, 1.57 Hz), 8.52 (2H, m), 8.13 (1H, d, 1.58), 7.99 (3H, m), 7.56 (2H, d, 8.19), 7.50 (1H, m), 5.42 (1H, s), 2.19 (4H, br), 1.63 (6H, s), 1.10 (6H, t), 0.94 (3H, br).
- 2.88
- 1H RMN (400 MHz, DMSO-d6) δ 8.98 (1H, d, 1.89 Hz), 8.80 (1H, m), 8.75 (1H, m), 8.54 (3H, m), 8.50 (1H, d, 7.89 Hz), 8.40 (1H, s), 8.17 (1H, s), 8.06 (1H, s), 8.01 (1H, t), 7.50 (1H, m), 5.41 (1H, s), 4.25 (1H, br), 3.09 (2H, br), 2.64 (2H, br), 2.02 (2H, br), 1,86 (2H, br), 1.62 (6H, s).
- 2.89
- 1H RMN (400 MHz, DMSQ-d6) δ 8.98 (1H, d, 2.01 Hz), 8.80 (1H, d, 2.12 Hz), 8.74 (1H, d, 3.95 Hz), 8.60 (1H, s), 8.55 (1H, s), 8.50 (1H, d, 1.55 Hz), 8.40 (1H, s), 8.16 (1H, s), 8.05 (1H, s), 8.01 (1H, t), 7.51 (1H, m), 5.41 (1H, s), 4.51 (1H, br m), 2.93 (2H, br d), 2.78 (1H, br m), 2.30 (2H, br t), 2.07 (2H, br), 1.94 (2H, br q), 1.61 (6H, s), 1.02 (6H, s).
- 2.90
- 1H RMN (400 MHz, DMSO-d6) δ 9.02 (1H, d, 2.08 Hz), 8.72 (1H, d, 4 Hz), 8.69 (1H, d, 1.92 Hz), 8.57 (1H, d, 1.42 Hz), 8.51 (1H, d, 7.93 Hz), 8.18 (1H, s), 8.09 (1H, s), 7.98 (1H, m), 7.49 (1H, m), 7.32 (3H, m), 5.38 (1H, s), 3.49 (2H, s), 2.60 (1H, septeto), 2.43 (8H, br), 2.30 (3H, s), 1.62 (6H, s), 0.97 (6H, d, 6.52 Hz).
- 2.91
- 1H RMN (400 MHz, DMSO-d6) δ 9.01 (2H, dd), 8.74 (1H, d, 4.08), 8.60 (1H, d, 1.31 Hz), 8.52 (1H, d, 7.93 Hz), 8.45 (1H, s), 8.11 (1H, s), 8.01 (1H, t), 7.84 (2H, d, 8.08 Hz), 7.48 (4H, m), 5.43 (1H, s), 3.51 (3H, m), 2.69 (6H, m), 1.62 (6H, s), 0.91 (3H, s).
- 2.92
- 1H RMN (400 MHz, DMSO-d6) δ 9.00 (2H, dd), 8.75 (1H, d, 3.94 Hz), 8.60 (1H, d, 1.48 Hz), 8.51 (1H, d, 7.91 Hz), 8.46 (1H, m), 8.12 (1H, d, 1.42 Hz), 8.01 (1H, t), 7.85 (2H, d, 7.7 Hz), 7.47 (3H, m), 5.41 (1H, s), 3.48 (2H, s), 2.78 (2H, br), 2.28 (2H, br), 2.09 (2H, br), 1.63 (6H, s), 1.07 (6H, s).
94
- Ej.
- Datos físicos
- 2.95
- 1H RMN (400 MHz, DMSO-d6) δ 9.01 (1H, d, 2.2 Hz), 8.98 (1H, d, 2.2 Hz), 8.72 (1H, m), 8.54 (1H, d, 1.6 Hz), 8.50 (1H, dd, 7.9, 1.2, 1.2 Hz), 8.30 (1H, dd, 2.2, 2.2 Hz), 7.99 (1H, ddd, 7.9, 7.9, 1.9 Hz), 7.91 (1H, d, 1.6 Hz), 7.83 (2H, d, 7.8 Hz), 7.48 (1h, ddd, 7.9, 4.8, 1.2 Hz), 7.45 (2H, d, 7.8 Hz), 3.52 (2H, s), 2.59 (1H, m), 2.55-2.3 (8H, hombro ancho), 1.48 (9H, s), 0.95 (6H, d, 6.2 Hz).
- 2.100
- 1H RMN (400 MHz, DMSO-d6) δ 8.96 (1H, d, 1.8 Hz), 8.89 (1H, d, 1.8 Hz), 8.66 (1H, m), 8.39 (1H, d, 8.0 Hz), 8.31 (1H, m), 7.96 (1H, m), 7.91 (1H, m), 7.81 (2H, d, 8.0 Hz), 7.46 (2H, d, 8.0 Hz), 7.42 (1H, m), 6.9 (1H, d, 1.0 Hz), 6.72 (1H, q, 4.8 Hz), 3.51 (2H, s), 2.60 (1H, septeto, 6.5 Hz), 2.55-2.20 (8H, hombros anchos), 0.95 (6H, d, 6.5 Hz)
- 2.102
- 1H RMN (400 MHz, DMSO-d6) δ 8.96 (1H, d, 1.8 Hz), 8.89 (1H, d, 1.8 Hz), 8.66 (1H, m), 8.39 (1H, d, 8.0 Hz), 8.31 (1H, m), 7.96 (1H, m), 7.91 (1H, m), 7.81 (2H, d, 8.0 Hz), 7.46 (2H, d, 8.0 Hz), 7.42 (1H, m), 6.9 (1H, d, 1.0 Hz), 6.72 (1H, q, 4.8 Hz), 3.51 (2H, s), 2.83 (4H, hombros anchos), 2.41 (4h, hombro ancho).
- 2.104
- 1H RMN (400 MHz, DMSO-d6) δ 8.91 (1H, d, 2.08 Hz), 8.7 (1H, s), 8.68 (1H, d, 3.96 Hz), 8.41 (1H, d, 8.3 Hz), 8.39 (1H, m), 8.25 (1H, m), 8.1 (1H, m), 7.94 (1H, t), 7.87 (1H, m), 7.43 (1H, m), 6.84 (1H, m), 6.74 (1H, q, 4.8 Hz), 3.9 (3H, s)
- 2.106
- 1H RMN (400 MHz, DMSO-d6) δ 9.00 (1H, d, 1.9 Hz), 8.9 (1H, d, 1,84 Hz), 8.65 (1H, d, 4.01 Hz), 8.45 (2H, m), 7.95 (4H, m), 7.55 (2H, d, 7.95 Hz), 7.45 (1H, m), 6.9 (1H, s), 6.7 (1H, s), 3.65 (4H, br), 2.5 (4H, br).
- 2.107
- 1H RMN (400 MHz, DMSO-d6) δ 8.5 (1H, d, 2.14 Hz), 8.0 (1H, d, 2.12 Hz), 8.65 (1H, d, 3.9 Hz), 8.4 (1H, d, 3.9 Hz), 8.3 (1H, d, 7.97 Hz), 7.95 (1H, m), 7.90 (1H, s), 7.80 (2H, d, 8.05 Hz), 7.45 (3H, m), 6.9 (1H, d, 1.36 Hz), 6.7 (1H, s), 3.5 (2H, br), 2.5 (4H, br), 2.4 (4H, br), 1.0 (9H, s).
- 2.111
- 1H RMN (400 MHz, DMSO-d6 δ 8.99 (1H, m), 8.96 (1H, s), 8.90 (1H, d, 2Hz), 8.81 (1H, m), 8.67 (1H, d, 8.51 Hz), 8.40 (1H, d, 7.93 Hz), 8.30 (1H, m), 7.95 (1H, t), 7.90 (1H, s), 7.78 (1H, br), 7.54 (1H, m), 7.43 (2H, m), 6.89 (1H, m), 6.80 (1H, t), 3.72 (2H, s), 3.45 (4H, br), 3.02 (2H, br), 2.40 (2H, br), 1.24 (12H, br)
- 2.114
- 1H RMN (400 MHz, DMSO-d6) δ 8.95 (1H, d, 8.13 Hz), 8.90 (1H, d, 8.04), 8.66 (1H, d, 3.94 Hz), 8.39 (1H, d, 7.94 Hz), 8.29 (1H, s), 7.96 (1H, t), 7.89 (1H, s), 7.71 (2H, m), 7.51 (1H, t), 7.41 (2H, m), 6.90 (1H, s), 6.78 (1H, t), 5.76 (1H, s), 3.57 (2H, s), 3.47 (2H, t), 2.60 (2H, br), 2.43 (8H, br), 1.24 (3H, t), 0.95 (6H, d).
- 2.116
- 1H RMN (400 MHz, DMSO-d6) δ 8.93 (1H, d, 2.16 Hz), 8.90 (1H, d, 2.12 Hz), 8.65 (1H, d, 5.61 Hz), 8.4 (1H, d, 7.93 Hz), 8.25 (1H, t), 7.95 (1H, t), 7.9 (1H, d, 1.36 Hz), 7.55 (2H, d, 5.75 Hz), 7.4 (1H, m), 7.25 (1H, s), 6.9 (1H, t), 6.75 (1H, t), 5.25 (2H, t), 4.55 (2H, d, 5.67 Hz), 3.45 (2H, q), 2.4 (3H, s), 1.25 (3H, t).
- 2.119
- 1H RMN (400 MHz, DMSO-d6) δ 8.95 (1H, m), 8.92 (1H, m), 8.68 (1H, m), 8.37 (1H, m), 8.32 (1H, s), 7.97 (2H, m), 7.75 (2H, m), 7.51 (1H, m), 7.40 (2H, m), 7.12 (1H, s), 7.02 (1H, s), 3.57 (2H, s), 2.75 (1H, s), 2.42 (8H, br), 0.98 (9H, s), 0.81 (2H, d, 4.88 Hz), 0.54 (2H, m).
- 2.120
- 1H RMN (400 MHz, DMSO-d6) δ 8.97 (1H, s), 8.91 (1H. s), 8.67 (1H, m), 8.36 (2H, d, 7.8 Hz), 7.96 (2H, m), 7.82 (2H, d, 7.76 Hz), 7.44 (3H, m), 7.10 (1H, s), 7.04 (1H, s), 3.52 (2H, s), 2.75 (1H, s), 2.41 (8H, br), 1.00 (9H, s), 0.80 (2H, d, 4.96 Hz), 0.53 (2H, m).
- 2.125
- 1H RMN (400 MHz, DMSO-d6) δ 8.95 (1H, d, 2Hz), 8.91 (1H, d, 2 Hz), 8.34 (1H, m), 7.81 (2H, d, 8.08 Hz), 7.45 (2H, d, 8.04 Hz), 7.29 (1H, s), 7.04 (1H, s), 6.94 (1H, d, 3.12 Hz), 6.85 (1H, s), 6.24 (1H, d, 2.28 Hz), 3.54 (2H, s), 2.63 (1H, br), 2.46 (8H, br), 2.36 (3H, s), 0.97 (1H, m), 0.76 (2H, m), 0.49 (2H, m).
- 2.133
- 1H RMN (400 MHz, DMSO-d6) δ 8.95 (1H, d, 2 Hz), 8.88 (1H, d, 2.3 Hz), 8.66 (1H, d, 4.04 Hz), 8.38 (1H, d, 8 Hz), 8.27 (1H, s), 7.94 (1H, t), 7.87 (1H, s), 7.73 (2H, m), 7.51 (1H, m), 7.42 (2H, m), 6.88 (1H, s), 6.63 (1H, d, 7.28 Hz), 4.24 (1H, m), 3.55 (2H, s), 2.41 (8H, br), 1.24 (6H, d, 6.44 Hz), 0.99 (9H, s).
- 2.134
- 1H RMN (400 MHz, DMSO-d6) δ 8.96 (1H, d, 2.04 Hz), 8.88 (1H, d, 1.96), 8.66 (1H, d, 2.80 Hz), 8.37 (1H, d, 7.88 Hz), 8.29 (1H, s), 7.95 (1H, t), 7.89 (1H, s), 7.81 (1H, d, 8.04 Hz), 7.44 (4H, m), 6.89 (1H, s), 6.62 (1H, d, 7.44 Hz), 4.24 (1H, m), 3.51 (2H, s), 2.40 (8H, br), 1.26 (6H, d, 6.40 Hz), 1.00 (9H, s).
95
Claims (1)
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imagen1 imagen2 imagen3 imagen4 imagen5 imagen6 imagen7 imagen8 imagen9 imagen10 imagen11 imagen12 imagen13 imagen14 imagen15 imagen16 imagen17 imagen18 imagen19 imagen20 imagen21 imagen22 imagen23 imagen24 imagen25 imagen26 imagen27 imagen28 imagen29 imagen30 imagen31 imagen32 imagen33 imagen34 imagen35 imagen36 imagen37 imagen38 imagen39 imagen40 imagen41 imagen42 imagen43 imagen44 imagen45 imagen46 imagen47 imagen48 imagen49 imagen50 imagen51 imagen52 imagen53
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EP08168207 | 2008-11-03 | ||
PCT/EP2009/050208 WO2009087212A2 (en) | 2008-01-11 | 2009-01-09 | Pyridine derivatives |
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CA (1) | CA2711803A1 (es) |
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EA (1) | EA201001127A1 (es) |
EC (1) | ECSP10010336A (es) |
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US20110086834A1 (en) * | 2008-06-26 | 2011-04-14 | Amgen Inc. | Alkynyl alcohols as kinase inhibitors |
MX2011012343A (es) * | 2009-05-19 | 2011-12-14 | Dow Agrosciences Llc | Compuestos y metodos para controlar hongos. |
EA201300080A1 (ru) | 2010-07-05 | 2013-06-28 | Мерк Патент Гмбх | Дипиридильные производные, пригодные для лечения заболеваний, индуцированных киназами |
WO2014060381A1 (de) | 2012-10-18 | 2014-04-24 | Bayer Cropscience Ag | Heterocyclische verbindungen als schädlingsbekämpfungsmittel |
US20150284380A1 (en) | 2012-10-31 | 2015-10-08 | Bayer Cropscience Ag | Novel heterocyclic compounds as pest control agents |
EA032458B1 (ru) | 2014-01-14 | 2019-05-31 | Милленниум Фармасьютикалз, Инк. | Гетероарилы и их применение |
EP3094326A4 (en) | 2014-01-14 | 2017-07-26 | Millennium Pharmaceuticals, Inc. | Heteroaryls and uses thereof |
EA201692140A1 (ru) | 2014-04-24 | 2017-04-28 | Новартис Аг | Производные аминопиридина в качестве ингибиторов фосфатидилинозитол 3-киназы |
ES2667424T3 (es) | 2014-04-24 | 2018-05-10 | Novartis Ag | Derivados de pirazina como inhibidores de fosfatidil-inositol-3-quinasa |
CA2945212A1 (en) | 2014-04-24 | 2015-10-29 | Novartis Ag | Amino pyrazine derivatives as phosphatidylinositol 3-kinase inhibitors |
KR20190017030A (ko) | 2016-06-13 | 2019-02-19 | 글락소스미스클라인 인털렉츄얼 프로퍼티 디벨로프먼트 리미티드 | Dnmt1의 억제제로서의 치환된 피리딘 |
US11666555B2 (en) * | 2017-05-17 | 2023-06-06 | Drexel University | RelA inhibitors for biofilm disruption |
US11919902B2 (en) | 2017-12-22 | 2024-03-05 | Hibercell, Inc. | Aryl-bipyridine amine derivatives as phosphatidylinositol phosphate kinase inhibitors |
KR20200128531A (ko) | 2018-01-29 | 2020-11-13 | 카풀루스 테라퓨틱스, 엘엘씨 | 6원 중심 고리를 포함하는 srebp 억제제 |
AU2021307559A1 (en) | 2020-07-15 | 2023-02-16 | Chiesi Farmaceutici S.P.A. | Pyridazinyl amino derivatives as ALK5 inhibitors |
EP4182322B1 (en) | 2020-07-15 | 2024-04-24 | Chiesi Farmaceutici S.p.A. | Pyrido oxazine derivatives as alk5 inhibitors |
CA3185108A1 (en) | 2020-07-15 | 2022-01-20 | Daniele PALA | Pyrido oxazine amino derivatives as alk5 inhibitors |
US20240116948A1 (en) | 2020-12-23 | 2024-04-11 | Chiesi Farmaceutici S.P.A. | Pyrido oxazine derivatives as alk5 inhibitors |
CN112707924A (zh) * | 2020-12-26 | 2021-04-27 | 蚌埠中实化学技术有限公司 | 一种4-胺甲基苯硼酸盐酸盐的合成方法 |
TW202328102A (zh) | 2021-09-21 | 2023-07-16 | 義大利商吉斯藥品公司 | 作為alk5抑制劑之嗒𠯤基胺基衍生物 |
KR102556500B1 (ko) * | 2021-11-19 | 2023-07-19 | 하나제약 주식회사 | 피롤 유도체 또는 이의 약학적 또는 식품학적으로 허용 가능한 염, 및 이를 유효성분으로 포함하는 위장 질환의 예방, 개선 또는 치료용 조성물 |
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US2909529A (en) | 1956-07-19 | 1959-10-20 | Merck Ag E | Process for preparing 3, 4-dihydro-1, 2-pyrano-(3, 4-c)-pyridone-(6) |
BE789099A (fr) | 1971-09-22 | 1973-03-21 | Boehringer Sohn Ingelheim | Nouveaux derives de la pyridine et procede pour les fabriquer |
JP4272338B2 (ja) * | 2000-09-22 | 2009-06-03 | バイエル アクチェンゲゼルシャフト | ピリジン誘導体 |
EP1539748A1 (en) | 2002-07-31 | 2005-06-15 | Smithkline Beecham Corporation | 2-phenylpyridin-4-yl derivatives as alk5 inhibitors |
US20040142978A1 (en) * | 2002-12-12 | 2004-07-22 | Pharmacia Corporation | Aminocyanopyridine inhibitors of mitogen activated protein kinase-activated protein kinase-2 |
RU2005119173A (ru) | 2002-12-20 | 2006-02-27 | Фармация Корпорейшн (Us) | Ациклические пиразольные соединения |
MY145822A (en) | 2004-08-13 | 2012-04-30 | Neurogen Corp | Substituted biaryl piperazinyl-pyridine analogues |
MX2008013430A (es) | 2006-04-19 | 2009-01-26 | Novartis Vaccines & Diagnostic | Compuestos de indazol y metodos para la inhibición de cdc7. |
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WO2007124545A1 (en) | 2006-04-28 | 2007-11-08 | Avexa Limited | Integrase inhibitors - 2 |
WO2007124544A1 (en) | 2006-04-28 | 2007-11-08 | Avexa Limited | Integrase inhibitors - 1 |
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EP2144877A1 (en) * | 2007-04-04 | 2010-01-20 | UCB Pharma, S.A. | Novel pyridine derivatives, processes for preparing them, pharmaceutical compositions thereof |
NZ581397A (en) | 2007-04-27 | 2012-02-24 | Astrazeneca Ab | Pyrimidine compounds for the inhibition of Eph receptors and for the treatment of cancer |
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2010
- 2010-06-02 ZA ZA2010/03929A patent/ZA201003929B/en unknown
- 2010-06-04 TN TN2010000255A patent/TN2010000255A1/fr unknown
- 2010-06-10 IL IL206276A patent/IL206276A0/en unknown
- 2010-06-10 CR CR11490A patent/CR11490A/es not_active Application Discontinuation
- 2010-06-29 MA MA32965A patent/MA31947B1/fr unknown
- 2010-07-09 EC EC2010010336A patent/ECSP10010336A/es unknown
Also Published As
Publication number | Publication date |
---|---|
EP2242742A2 (en) | 2010-10-27 |
JP5566909B2 (ja) | 2014-08-06 |
EP2242742B1 (en) | 2015-12-02 |
US8343966B2 (en) | 2013-01-01 |
US20090215776A1 (en) | 2009-08-27 |
CA2711803A1 (en) | 2009-07-16 |
PE20091316A1 (es) | 2009-09-24 |
TN2010000255A1 (en) | 2011-11-11 |
EA201001127A1 (ru) | 2011-02-28 |
CN101918362A (zh) | 2010-12-15 |
MX2010007606A (es) | 2010-08-23 |
AR070519A1 (es) | 2010-04-14 |
BRPI0907611A2 (pt) | 2015-07-21 |
ZA201003929B (en) | 2011-03-30 |
JP2011509277A (ja) | 2011-03-24 |
AU2009203681A1 (en) | 2009-07-16 |
KR20100101138A (ko) | 2010-09-16 |
CL2009000029A1 (es) | 2009-07-24 |
WO2009087212A2 (en) | 2009-07-16 |
AU2009203681B2 (en) | 2012-08-16 |
CR11490A (es) | 2010-08-11 |
IL206276A0 (en) | 2010-12-30 |
CN101918362B (zh) | 2013-11-27 |
WO2009087212A3 (en) | 2009-09-24 |
MA31947B1 (fr) | 2010-12-01 |
ECSP10010336A (es) | 2010-08-31 |
TW200938536A (en) | 2009-09-16 |
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