ES2654847T3 - Compuestos de benzoxazol y benzotiazol sustituidos en 6-O y métodos para inhibir la señalización CSF-1R - Google Patents
Compuestos de benzoxazol y benzotiazol sustituidos en 6-O y métodos para inhibir la señalización CSF-1R Download PDFInfo
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- ES2654847T3 ES2654847T3 ES07797244.6T ES07797244T ES2654847T3 ES 2654847 T3 ES2654847 T3 ES 2654847T3 ES 07797244 T ES07797244 T ES 07797244T ES 2654847 T3 ES2654847 T3 ES 2654847T3
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Abstract
Un compuesto seleccionado de entre el grupo que consiste en**Tabla** o un estereoisómero, tautómero, solvato, u óxido, o sal derivada del mismo farmacéuticamente aceptable.
Description
Esquema 4 de referencia
En el esquema 4 de referencia, 3-(2-piperidin-1-il-etil)-fenilamina es un ejemplo de una amina que puede ser usada para formar un compuesto de los Ejemplos o Ejemplos de referencia. 3-(2-piperidin-1-il-etil)-fenilamina es formada por la sulfonación de 2-(3-nitrofenil)-etanol, luego introducción de amina en el 2-(3-nitrofenil)etil éster de ácido metanosulfónico resultante, y a continuación reducción de la 1-[2-(3-nitrofenil)-etil]-piperidina resultante.
Esquema 5 de referencia
En el esquema 5 de referencia, con ciclohexilmetanamina se introduce amina en 4-(2-(metilsulfinil)benzo[d]oxazol
10 6-iloxi)-N-metilpiridin-2-carboxamida. La 4-(2-(ciclohexilmetilamino)benzo[d]oxazol-6-iloxi)-N-metilpiridin-2carboxamida resultante es entonces hidrolizada para formar ácido 4-[2-(ciclohexilmetil-amino)-benzooxazol-6-iloxi]piridin-2-carboxílico. El ácido 4-[2-(ciclohexilmetil-amino)-benzooxazol-6-iloxi]-piridin-2-carboxílico reacciona entonces con hexafluorofosfato de benzotriazol-1-iloxitris(dimetilamino)-fosfonio, tert-butil carbazato, y trietil amina para formar 4-(2-(ciclohexilmetilamino) benzo[d]oxazol-6-iloxi)piridin-2-carbohidrazida. La 4-(2
15 (ciclohexilmetilamino)benzo[d]oxazol-6-iloxi)piridin-2-carbohidrazida reacciona entonces con trimetil ortoformiato para formar un compuesto de los Ejemplos o Ejemplos de referencia.
Esquema 6 de referencia
18
Tabla 3
- Comp.
- Prep Ej. Estructura Nombre (M+H)+, Tr (min.)
- 7
-
201
imagen41 4-(2-((1R,2R)-2hidroxiciclohexilamino)benzo[d]oxazol6-iloxi)-N-metilpicolinamida 383, 1.96
- 10
-
171
imagen42 4-(2-((1R,2R)-2hidroxiciclohexilamino)benzo[d]tiazol-6iloxi)-N,Ndimetilpicolinamida 413.1, 1.87
- 11
- 171 N-ciclopropil-4-(2-((1R,2R)-2hidroxiciclohexilamino)benzo[d]tiazol-6iloxi)picolinamida 425.2, 2.13
- 12
-
171
imagen43 4-(2-((1R,2R)-2hidroxiciclohexilamino)benzo[d]tiazol-6iloxi)-N-(tetrahidro-2H-piran-4il)picolinamida 469.2, 2.09
- 13
-
171
imagen44 4-(2-((1R,2R)-2hidroxiciclohexilamino)benzo[d]tiazol-6iloxi)-N-(1-metilpiperidin-4il)picolinamida 482.2, 1.85
- 14
- 171 4-(2-((1R,2R)-2hidroxiciclohexilamino)benzo[d]tiazol-6iloxi)-N-(1-metilpiperidin-3il)picolinamida 482.2, 1.87
- 15
-
171
imagen45 N-(2-acetamidoetil)-4-(2-((1R,2R)-2hidroxiciclohexilamino)benzo[d]tiazol6-iloxi)picolinamida 470.2, 1.86
- 16
-
171
imagen46 4-(2-((1R,2R)-2hidroxiciclohexilamino)benzo[d]tiazol6-iloxi)-N-(2-(pirrolidin-1il)etil)picolinamida 482.2, 1.84
- 17
-
171
imagen47 4-(2-((1R,2R)-2hidroxiciclohexilamino)benzo[d]tiazol6-iloxi)-N-((tetrahidrofuran-2il)metil)picolinamida 469.2, 2.16
- 18
-
171
imagen48 4-(2-((1R,2R)-2hidroxiciclohexilamino)benzo[d]tiazol6-iloxi)-N-((tetrahidro-2H-piran-4il)metil)picolinamida 483.2, 2.12
40
- (cont.)
- Comp.
- Prep Ej. Estructura Nombre (M+H)+, Tr (min.)
- 19
-
171
imagen49 4-(2-((1R,2R)-2hidroxiciclohexilamino)benzo[d]tiazol6-iloxi)-N-((1-metilpiperidin-4il)metil)picolinamida 496.2, 1.84
- 20
-
171
imagen50 N-(((S)-1-etilpirrolidin-2-il)metil)-4-(2((1R,2R)-2hidroxiciclohexilamino)benzo[d]tiazol6-iloxi)picolinamida 496.2, 1.88
- 47
-
171
imagen51 N-etil-4-(2-((1R,2R)-2hidroxiciclohexilamino)benzo[d]tiazol6-iloxi)picolinamida 413.2, 2.09
- 48
-
171
imagen52 4-(2-((1R,2R)-2hidroxiciclohexilamino)benzo[d]tiazol6-iloxi)-N-(2,2,2trifluoroetil)picolinamida 467.1, 2.37
- 49
-
171
imagen53 4-(2-((1R,2R)-2hidroxiciclohexilamino)benzo[d]tiazol6-iloxi)-N-propilpicolinamida 427.1, 2.25
- 50
-
171
imagen54 N-(ciclopropilmetil)-4-(2-((1R,2R)-2hidroxiciclohexilamino)benzo[d]tiazol6-iloxi)picolinamida 439.2, 2.32
- 51
-
171
imagen55 4-(2-((1R,2R)-2hidroxiciclohexilamino)benzo[d]tiazol6-iloxi)-N-isopropilpicolinamida 427.2, 2.24
- 125
-
162
imagen56 4-(2-((1r,4r)-4hidroxiciclohexilamino)benzo[d]tiazol6-iloxi)-N-metilpicolinamida 399.1, 1.83
- 155
-
175
imagen57 (1R,2R)-2-(6-(2-(1-metil-1H-imidazol2-il)piridin-4-iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 422.1, 1.83
41
- (cont.)
- Comp.
- Prep Ej. Estructura Nombre (M+H)+, Tr (min.)
- 156
-
175
imagen58 (1R,2R)-2-(6-(2-(pirazin-2-il)piridin-4iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 420.1, 1.91
- 157
-
175
imagen59 (1R,2R)-2-(6-(2-(tiazol-5-il)piridin-4iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 425.0, 2.05
- 158
-
175
imagen60 (1R,2R)-2-(6-(2-(1-metil-1H-imidazol5-il)piridin-4-iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 422.1, 1.84
- 159
-
175
imagen61 (1R,2R)-2-(6-(2-(tiazol-4-il)piridin-4iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 425.0, 1.85
- 160
-
175
imagen62 (1R,2R)-2-(6-(2-(tiazol-2-il)piridin-4iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 425.0, 2.28
- 161
-
188
imagen63 (1R,2R)-2-(6-(2-(1,2,3,6tetrahidropiridin-4-il)piridin-4iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 423.1, 1.38
- 162
- 177 (1R,2R)-2-(6-(2-(5-etil-4-metil-1Himidazol-2-il)piridin-4iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 450.1, 1.82
- 164
- 174 (1R,2R)-2-(6-(6’-(4-metilpiperazin-1-il)2,3’-bipiridin-4-iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 517.2, 1.75
42
- (cont.)
- Comp.
- Prep Ej. Estructura Nombre (M+H)+, Tr (min.)
- 165
- 174 (1R,2R)-2-(6-(6’-morfolino-2,3’-bipiridin4-iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 504.1, 1.93
- 166
- 174 (1R,2R)-2-(6-(2-(3(morfolinometil)fenil)piridina-4iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 517.1, 1.78
- 167
- 174 (1R,2R)-2-(6-(2-ciclohexenilpiridin-4iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 422.1, 2.07
- 168
- 174 (1R,2R)-2-(6-(2-(4(morfolinometil)fenil)p yridin-4iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 517.2, 1.76
- 169
- 174 (1R,2R)-2-(6-(2-ciclopropilpiridin-4iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 382.1, 1.84
- 170
- 174 (1R,2R)-2-(6-(6’-metoxi-2,3’-bipiridin-4iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 449.1, 1.98
- 171
- 174 (1R,2R)-2-(6-(2’-fluoro-2,4’-bipiridin-4iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 437.1, 2.22
- 172
- 174 (1R,2R)-2-(6-(3’-fluoro-2’-morfolino-2,4’bipiridin-4-iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 522.2, 2.17
- 173
- 174 (1R,2R)-2-(6-(6’-fluoro-2,3’-bipiridin-4iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 437.1, 2.04
43
- (cont.)
- Comp.
- Prep Ej. Estructura Nombre (M+H)+, Tr (min.)
- 174
- 183 (1R,2R)-2-(6-(2-(piperidin-1-il)piridin-4iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 425.1, 1.98
- 175
- 183 (1R,2R)-2-(6-(2-morfolinopiridin-4iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 427.1, 1.80
- 176
- 183 (1R,2R)-2-(6-(2-(4-metilpiperazin-1il)piridin-4-iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 440.1, 1.66
- 177
- 183 N-((R)-1-(4-(2-((1R,2R)-2hidroxiciclohexilamino)benzo[d]tiazol-6iloxi)piridin-2-il)pirrolidin-3-il)acetamida 468.1, 1.78
- 178
- 183 N-((S)-1-(4-(2-((1R,2R)-2hidroxiciclohexilamino)benzo[d]tiazol-6iloxi)piridin-2-il)pirrolidin-3-il)acetamida 468.1, 1.77
- 179
- 183 4-(4-(2-((1R,2R)-2hidroxiciclohexilamino)benzo[d]tiazol-6iloxi)piridin-2-il)piperazin-2-one 440.1, 1.70
- 180
- 175 (1R,2R)-2-(6-(2,2’-bipiridin-4iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 419.0, 1.87
- 181
- 175 (1R,2R)-2-(6-(2-(1-metil-3(trifluorometil)-1H-pirazol-5-il)piridin-4iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 490.1, 2.60
44
- (cont.)
- Comp.
- Prep Ej. Estructura Nombre (M+H)+, Tr (min.)
- 182
- 174 (1R,2R)-2-(6-(2-(1-(2-morfolinoetil)-1Hpirazol-4-il)piridin-4-iloxi)benzo[d]tiazol2-ilamino)ciclohexanol 521.1, 1.71
- 184
- 192 (1R,2R)-2-(6-(6,7-dimetoxiquinolin-4iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 452.1, 2.00
- 185
- 176 (1R,2R)-2-(6-(2-(1-etil-1H-pirazol-4il)piridin-4-iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 436.0, 1.89
- 186
- 176 (1R,2R)-2-(6-(2-(1-(2-(dietilamino)etil)1H-pirazol-4-il)piridin-4iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 507.1, 1.75
- 187
- 176 (1R,2R)-2-(6-(2-(1-(2,2-difluoroetil)-1Hpirazol-4-il)piridin-4-iloxi)benzo[d]tiazol2-ilamino)ciclohexanol 472.0, 1.90
- 188
- 179 (1R,2R)-2-(6-(3-(1H-pirazol-4-il)piridin4-iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 408.1, 1.70
- 189
- 179 (1R,2R)-2-(6-(3-(1-metil-1H-pirazol-4il)piridin-4-iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 422.1, 1.79
45
- (cont.)
- Comp.
- Prep Ej. Estructura Nombre (M+H)+, Tr (min.)
- 190
- 179 (1R,2R)-2-(6-(3,3’-bipiridin-4iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 419.1, 1.66
- 191
- 179 (1R,2R)-2-(6-(3-(1-metil-1H-pirazol-5il)piridin-4-iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 422.1, 1.83
- 192
- 179 (1R,2R)-2-(6-(3,4’-bipiridin-4iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 419.1, 1.61
- 193
- 179 (1R,2R)-2-(6-(6’-amino-3,3’-bipiridin-4iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 434.1, 1.60
- 194
- 179 (1R,2R)-2-(6-(6’-(4-metilpiperazin-1-il)3,3’-bipiridin-4-iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 517.2, 1.64
- 195
- 179 (1R,2R)-2-(6-(3-ciclopropilpiridin-4iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 382.1, 1.97
- 196
- 174 (1R,2R)-2-(6-(2-(2-morfolinopirimidin-5il)piridin-4-iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 505.1, 2.03
46
- (cont.)
- Comp.
- Prep Ej. Estructura Nombre (M+H)+, Tr (min.)
- 197
- 174 (1R,2R)-2-(6-(2-(4-(4-metilpiperazin-1il)fenil)piridin-4-iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 516.2, 1.85
- 200
- 177 (1R,2R)-2-(6-(2-(4-(trifluorometil)-1Himidazol-2-il)piridin-4iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 476.1, 2.35
- 203
- 192 (1R,2R)-2-(6-(2-metilpiridin-4iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 356.1, 1.73
- 209
- 192 (1R,2R)-2-(6-(3-fluoropiridin-4iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 360.1, 1.83
- 224
- 178 (1R,2R)-2-(6-(3-bromopiridin-4iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 420.1/42 2.0, 1.81
- 225
- 173 (1R,2R)-2-(6-(2-chloropiridin-4iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 376.1, 2.13
- 226
- 173 4-(2-((1R,2R)-2hidroxiciclohexilamino)benzo[d]tiazol-6iloxi)picolinonitrile 367.1, 2.03
- 231
- 177 (1R,2R)-2-(6-(2-(4-metil-1H-imidazol-2il)piridin-4-iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 422.1, 1.88
47
- (cont.)
- Comp.
- Prep Ej. Estructura Nombre (M+H)+, Tr (min.)
- 232
- 177 (1R,2R)-2-(6-(2-(4,5-dimetil-1Himidazol-2-il)piridin-4iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 436.1, 1.93
- 258
- 177 (1R,2R)-2-(6-(2-(4,5,6,7-tetrahidro-1Hbenzo[d]imidazol-2-il)piridin-4iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 462.2, 2.03
- 259
- 176 (1R,2R)-2-(6-(2-(1-(2-fluoroetil)-1Hpirazol-4-il)piridin-4-iloxi)benzo[d]tiazol2-ilamino)ciclohexanol 454.2, 1.89
- 260
- 176 (1R,2R)-2-(6-(2-(1-(2-metoxietil)-1Hpirazol-4-il)piridin-4-iloxi)benzo[d]tiazol2-ilamino)ciclohexanol 466.2, 1.89
- 261
- 174 (1R,2R)-2-(6-(6’-amino-2,3’-bipiridin-4iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 434.2, 1.78
- 262
- 187 (1R,2R)-2-(6-(2-(1H-imidazol-1-il)piridin4-iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 408.2, 1.85
- 265
- 174 (1R,2R)-2-(6-(2-(1-metil-1H-pirazol-5il)piridin-4-iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 422.1, 1.93
- 266
- 177 (1R,2R)-2-(6-(2-(4,5-dietil-1H-imidazol2-il)piridin-4-iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 464.2, 2.10
48
- (cont.)
- Comp.
- Prep Ej. Estructura Nombre (M+H)+, Tr (min.)
- 267
- 177 (1R,2R)-2-(6-(2-(5-metil-4-propil-1Himidazol-2-il)piridin-4iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 464.2, 2.10
- 280
- 174 (1R,2R)-2-(6-(2,4’-bipiridin-4iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 419.0, 1.68
- 281
- 174 (1R,2R)-2-(6-(2-(1-propil-1H-pirazol-4il)piridin-4-iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 450.0, 2.02
- 282
- 174 (1R,2R)-2-(6-(6’-amino-5’(trifluorometil)-2,3’-bipiridin-4iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 502.0, 2.02
- 283
- 174 (1R,2R)-2-(6-(2-(1,3,5-trimetil-1Hpirazol-4-il)piridin-4-iloxi)benzo[d]tiazol2-ilamino)ciclohexanol 450.0, 1.86
- 284
- 174 (1R,2R)-2-(6-(2-(1H-pirrolo[2,3-b]piridin5-il)piridin-4-iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 458.0, 1.91
- 285
- 174 (1R,2R)-2-(6-(2-(pirimidin-5-il)piridin-4iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 420.1, 1.90
- 286
- 174 (1R,2R)-2-(6-(2-(2(dimetilamino)pirimidin-5-il)piridin-4iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 463.1, 1.96
49
- (cont.)
- Comp.
- Prep Ej. Estructura Nombre (M+H)+, Tr (min.)
- 287
- 174 4-(2-((1R,2R)-2hidroxiciclohexilamino)benzo[d]tiazol-6iloxi)-2,3’-bipiridine-6’-carbonitrile 444.0, 2.18
- 288
- 174 (1R,2R)-2-(6-(2-(4-fluorofenil)piridin-4iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 436.0, 2.06
- 291
- 195 4-(2-((1R,2R)-2hidroxiciclohexilamino)benzo[d]tiazol-6iloxi)-N-metilnicotinamida 399.1, 1.72
- 293
- 162 4-(2-(3hidroxiciclohexilamino)benzo[d]tiazol-6iloxi)-N-metilpicolinamida 399.1, 1.76
- 320
- 162 4-(2-((1S,2S)-2hidroxiciclopentilamino)benzo[d]tiazol6-iloxi)-N-metilpicolinamida 385.1, 1.74
- 322
- 162 4-(2-((1S,2R)-2hidroxiciclopentilamino)benzo[d]tiazol6-iloxi)-N-metilpicolinamida 385.1, 1.75
- 324
- 162 4-(2-((1R,2R)-2hidroxiciclopentilamino)benzo[d]tiazol6-iloxi)-N-metilpicolinamida 385.1, 1.75
- 344
- 174 (1R,2R)-2-(6-(2-(1-metil-1H-pirazol-4il)piridin-4-iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 422.2, 1.68
- 345
- 174 (1R,2R)-2-(6-(2,3’-bipiridin-4iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 419.1, 1.69
50
- (cont.)
- Comp.
- Prep Ej. Estructura Nombre (M+H)+, Tr (min.)
- 346
- 174 (1R,2R)-2-(6-(2-(2-aminopirimidin-5il)piridin-4-iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 435.2, 1.61
- 359
- 174 (1R,2R)-2-(6-(2-(1-isobutil-1H-pirazol-4il)piridin-4-iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 464.4, 1.95
- 360
- 174 (1R,2R)-2-(6-(2-(1H-pirazol-4-il)piridin4-iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 408.1, 1.63
- 368
- 170 (1R,2R)-2-(6-(2-(metilamino)piridin-4iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 371.1, 1.79
- 369
- 170 (1R,2R)-2-(6-(2-(etilamino)piridin-4iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 385.1, 1.74
- 371
- 175 (1R,2R)-2-(6-(2-(furan-2-il)piridin-4iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 408.1, 1.94
- 372
- 175 (1R,2R)-2-(6-(2-(oxazol-2-il)piridin-4iloxi)benzo[d]tiazol-2ilamino)ciclohexanol 409.1, 1.98
- 376
- 195 4-(7-bromo-2-((1R,2R)-2hidroxiciclohexilamino)benzo[d]tiazol-6iloxi)-Nmetilpicolinamida 479, 2.37
- 377
- 196 4-(2-((1R,2R)-2-hidroxiciclohexilamino)7-metilbenzo[d]tiazol-6-iloxi)-Nmetilpicolinamida 413, 2.09
- 378
- 197 4-(7-chloro-2-((1R,2R)-2hidroxiciclohexilamino)benzo[d]tiazol-6iloxi)-Nmetilpicolinamida 433, 2.33
51
muestras desconocidas a partir de la curva estándar y expresarse en U/L de Trap5b. La sensibilidad analítica del ensayo es 0.1 U/L y la variación dentro del ensayo y entre los ensayos está por debajo de 10%. Se encontró que los niveles de Trap5b tenían buena correlación con el promedio de puntaje osteolítico (evaluado por rayos x).
Mientras se han descrito en detalle varias realizaciones preferidas de la invención y variaciones de las mismas,
5 otras modificaciones y métodos de uso serán fácilmente evidentes para aquellos expertos en la técnica. De acuerdo con ello, debería entenderse que pueden hacerse diferentes aplicaciones, modificaciones y sustituciones de equivalentes, sin apartarse del espíritu de la invención o del alcance las reivindicaciones.
Las actividades de inhibición porcentuales de los compuestos de las tablas 2 y 3, cuando se prueban a aproximadamente 1µM en el ensayo indicado, como se describe en los Ejemplos biológicos, son mostrados
10 respectivamente en las tablas 5, 6, y 7. Se contempla que los compuestos que tienen una inhibición de 0 % a 1µM exhibirán actividades inhibitorias a una concentración mayor. Un "N/D" indica que el compuesto no fue probado en el ensayo particular.
Tabla 5. Actividades de los compuestos de la tabla 2
- Comp.
- PDGFRβ CSF-1R cKit M-NFS-60 CP pCSF1R
- 52
- 50 100 12 56 71
- 137
- 98 100 45 100 98
- 157
- 20 100 20 100 99
15 Tabla 6. Actividades de los compuestos de la tabla 3
- Comp.
- PDGFRβ CSF-1R cKit M-NFS-60 CP pCSF1R
- 7
- 9 100 12 35 N/D
- 10
- 9 67 0 N/D N/D
- 11
- 60 100 0 69 92
- 12
- 1 95 0 N/D N/D
- 13
- 0 93 9 N/D N/D
- 14
- 0 96 3 N/D N/D
- 15
- 7 99 15 4 N/D
- 16
- 9 99 12 30 N/D
- 17
- 12 99 19 23 N/D
- 18
- 23 99 80 22 N/D
- 19
- 0 96 8 23 N/D
- 20
- 0 76 0 N/D N/D
- 47
- 4 100 0 55 83
- 48
- 16 99 14 26
- 49
- 12 100 21 33 77
- 50
- 14 99 13 18 N/D
- 51
- 0 95 10 N/D N/D
- 125
- 9 99 2 17 N/D
- 155
- 18 99 34 0 N/D
- 156
- 3 100 36 33 N/D
- 157
- 17 100 43 42 N/D
56
- Cont.
- Comp.
- PDGFRβ CSF-1R cKit M-NFS-60 CP pCSF1R
- 158
- 1 99 27 0 N/D
- 159
- 23 100 29 98 96
- 160
- 19 100 95 30 N/D
- 161
- 26 54 20 N/D N/D
- 162
- 30 100 20 100 99
- 164
- 87 100 79 100 100
- 165
- 83 100 83 100 98
- 166
- 0 100 13 49 78
- 167
- 0 100 16 24 N/D
- 168
- 43 100 40 100 99
- 169
- 0 75 12 N/D N/D
- 170
- 23 100 28 100 96
- 171
- 18 100 25 96 95
- 172
- 18 100 22 100 97
- 173
- 8 100 18 52 81
- 174
- 3 86 18 N/D N/D
- 175
- 1 100 11 17 N/D
- 176
- 0 63 12 N/D N/D
- 177
- 0 67 15 N/D N/D
- 178
- -3 82 17 N/D N/D
- 179
- 16 98 10 27 N/D
- 180
- 12 100 23 96 93
- 181
- 17 72 27 N/D N/D
- 182
- 4 100 16 100 98
- 184
- 84 100 45 100 95
- 185
- 29 100 32 100 94
- 186
- 14 100 13 100 99
- 187
- 25 100 32 100 98
- 188
- 35 100 55 38 N/D
- 189
- 23 100 31 26 N/D
- 190
- 19 98 22 5 N/D
- 191
- 15 45 19 N/D N/D
- 192
- 22 99 56 14 N/D
- 193
- 15 95 27 0 N/D
- 194
- 16 77 20 N/D N/D
- 195
- 25 81 90 N/D N/D
- 196
- 23 100 29 100 98
57
- Cont.
- Comp.
- PDGFRβ CSF-1R cKit M-NFS-60 CP pCSF1R
- 197
- 89 100 93 100 98
- 200
- 19 100 29 69 83
- 203
- 15 98 22 20 N/D
- 209
- 1 100 17 36 N/D
- 224
- 0 100 26 33 N/D
- 225
- 0 90 21 N/D N/D
- 226
- 0 80 20 N/D N/D
- 231
- 49 100 9 100 99
- 232
- 64 100 34 100 99
- 258
- 62 100 44 100 99
- 259
- 6 100 24 100 98
- 260
- 0 100 25 100 98
- 261
- 30 100 25 100 98
- 262
- 3 100 20 46 48
- 265
- 12 100 9 32 N/D
- 266
- 21 100 18 100 94
- 267
- 26 100 16 100 96
- 280
- 22 100 11 100 65
- 281
- 36 100 22 100 96
- 282
- 7 99 23 22 N/D
- 283
- 20 99 38 0 N/D
- 284
- 53 100 61 100 N/D
- 285
- 8 99 33 0 N/D
- 286
- 0 100 23 71 94
- 287
- 20 100 57 35 N/D
- 288
- 24 100 78 70 N/D
- 291
- 0 48 4 N/D N/D
- 293
- 0 100 22 67 82
- 320
- 20 100 16 25 N/D
- 322
- 11 99 18 21 N/D
- 324
- 19 99 21 15 N/D
- 344
- 65 100 45 100 95
- 345
- 13 100 19 97 93
- 346
- 0 100 13 67 84
- 359
- 19 100 31 95 93
- 360
- 16 100 29 100 98
- 368
- 8 100 24 12 N/D
58
Claims (1)
-
imagen1 imagen2 imagen3 imagen4 imagen5 imagen6 imagen7 imagen8 imagen9 imagen10 imagen11 imagen12 imagen13 imagen14
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