ES2552515T3 - Derivados de piridopirazina y su uso - Google Patents
Derivados de piridopirazina y su uso Download PDFInfo
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- ES2552515T3 ES2552515T3 ES12713705.7T ES12713705T ES2552515T3 ES 2552515 T3 ES2552515 T3 ES 2552515T3 ES 12713705 T ES12713705 T ES 12713705T ES 2552515 T3 ES2552515 T3 ES 2552515T3
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- alkyl
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- heteroaryl
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- heterocyclyl
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Abstract
Un compuesto de acuerdo con la fórmula general (I)**Fórmula** en la que los sustituyentes R1, R2, X tienen el siguiente significado: X es O R1 (I) arilo sustituido, en donde el grupo arilo puede estar sustituido con uno o más F, CI, Br, I, CF3, CN, NH2, NH-alquilo, NH-cicloalquilo, NH-heterociclilo, NH-arilo, NH-heteroarilo, NH-alquil-cicloalquilo, NH-alquil-heterociclilo, NH-alquil-arilo, NH-alquil-heteroarilo, NH-alquil-NH2, NH-alquil-OH, N(alquilo)2, NHC(O)-alquilo, NHC(O)-cicloalquilo, NHC(O)-heterociclilo, NHC(O)-arilo, NHC(O)-heteroarilo, NHC(O)-alquil-arilo, NHC(O)-alquil-heteroarilo, NHSO2-alquilo, NHSO2-cicloalquilo, NHSO2-heterociclilo, NHSO2-arilo, NHSO2-heteroarilo, NHSO2-alquil-arilo, NHSO2-alquil-heteroarilo, NO2, SH, S-alquilo, S-arilo, S-heteroarilo, OH, OCF3, O-alquilo, O-cicloalquilo, O-heterociclilo, O-arilo, O-heteroarilo, O-alquil-cicloalquilo, O-alquil-heterociclilo, O-alquil-arilo, O-alquil-heteroarilo, O-alquil-OH, O-(CH2)n-O, O-(-CH2-CH2-O-)n-CH2-CH2-OH, OC(O)-alquilo, OC(O)-cicloalquilo, OC(O)-heterociclilo, OC(O)-arilo, OC(O)-heteroarilo, OC(O)-alquil-arilo, OC(O)-alquil-heteroarilo, OC(O)-NH-alquilo, OSO3H, OSO2-alquilo, OSO2-cicloalquilo, OSO2-heterociclilo, OSO2-arilo, OSO2-heteroarilo, OSO2-alquil-arilo, OSO2-alquil-heteroarilo, OP(O)(OH)2, C(O)-alquilo, C(O)-arilo, C(O)-heteroarilo, O- CO2-alquilo, CO2H, CO2-alquilo, CO2-cicloalquilo, CO2-heterociclilo, CO2-arilo, CO2-heteroarilo, CO2-alquil-cicloalquilo, CO2-alquil-heterociclilo, CO2-alquil-arilo, CO2-alquil-heteroarilo, C(O)-NH2, C(O)NH-alquilo, C(O)NHcicloalquilo, C(O)NH-heterociclilo, C(O)NH-arilo, C(O)NH-heteroarilo, C(O)NH-alquil-cicloalquilo, C(O)NH-alquilheterociclilo, C(O)NH-alquil-arilo, C(O)NH-alquil-heteroarilo, C(O)N(alquilo)2, C(O)N(cicloalquilo)2, C(O)N(arilo)2, C(O)N(heteroarilo)2, SO-alquilo, SO-arilo, SO2-alquilo, SO2-heterociclilo; SO2-arilo, SO2NH2, SO2NH-alquilo, SO2NH-arilo, SO2NH-heteroarilo, SO2NH-alquil-arilo, SO3H, SO2O-alquilo, SO2O-arilo, SO2O-alquil-arilo, alquilo, cicloalquilo, heterociclilo, arilo o heteroarilo iguales o diferentes, n puede tener el valor 0, 1, 2 o 3 y los sustituyentes alquil-, cicloalquil-, heterociclil-, aril-, heteroaril-, alquil-cicloalquil-, alquil-heterociclil-, alquil-aril- y alquil-heteroarilo por su parte pueden estar a su vez sustituidos, (II) heteroarilo no sustituido o sustituido, en donde el grupo heteroarilo puede estar sustituido con uno o más F, CI, Br, I, CF3, CN, NH2, NH-alquilo, NH-cicloalquilo, NH-heterociclilo, NH-arilo, NH-heteroarilo, NH-alquil-cicloalquilo, NH-alquil-heterociclilo, NH-alquil-arilo, NH-alquil-heteroarilo, NH-alquil-NH2, NH-alquil-OH, N(alquilo)2, NHC(O)-alquilo, NHC(O)-cicloalquilo, NHC(O)-heterociclilo, NHC(O)-arilo, NHC(O)-heteroarilo, NHC(O)-alquil-arilo, NHC(O)-alquil-heteroarilo, NHSO2-alquilo, NHSO2-cicloalquilo, NHSO2-heterociclilo, NHSO2-arilo, NHSO2-heteroarilo, NHSO2-alquil-arilo, NHSO2-alquil-heteroarilo, NO2, SH, S-alquilo, S-arilo, S-heteroarilo, OH, OCF3, O-alquilo, O-cicloalquilo, O-arilo, O-heteroarilo, O-alquil-cicloalquilo, O-alquil-heterociclilo, O-alquil-arilo, O-alquil-heteroarilo, OC(O)-alquilo, OC(O)-cicloalquilo, OC(O)-heterociclilo, OC(O)-arilo, OC(O)-heteroarilo, OC(O)-alquil-arilo, OC(O)-alquil-heteroarilo, OSO3H, OSO2-alquilo, OSO2-cicloalquilo, OSO2-heterociclilo, OSO2-arilo, OSO2-heteroarilo, OSO2-alquil-arilo, OSO2-alquil-heteroarilo, OP(O)(OH)2, C(O)-alquilo, C(O)-arilo, C(O)-heteroarilo, CO2H, CO2-alquilo, CO2-cicloalquilo, CO2-heterociclilo, CO2-arilo, CO2-heteroarilo, CO2-alquil-cicloalquilo, CO2-alquil-heterociclilo, CO2-alquil-arilo, CO2-alquil-heteroarilo, C(O)-NH2, C(O)NH-alquilo, C(O)NH-cicloalquilo, C(O)NH-heterociclilo, C(O)NH-arilo, C(O)NH-heteroarilo, C(O)NH-alquil-cicloalquilo, C(O)NH-alquil-heterociclilo, C(O)NH-alquil-arilo, C(O)NH-alquil-heteroarilo, C(O)N(alquilo)2, C(O)N(cicloalquilo)2, C(O)N(arilo)2, C(O)N(heteroarilo)2, SO2NH2, SO2NH-alquilo, SO2NH-arilo, SO2NH-heteroarilo, SO2NH-alquil-arilo, S03H, SO2O-alquilo, SO2O-arilo, SO2O-alquil-arilo, alquilo, cicloalquilo, heterociclilo, alquil-cicloalquilo, alquil-heterociclilo, alquil-arilo, alquil-heteroarilo, arilo o heteroarilo iguales o diferentes, y los sustituyentes alquil-, cicloalquil-, heterociclil-, alquil-heterociclilo, alquil-arilo, alquil-cicloalquilo, alquil-heteroarilo, aril- y heteroarilo por su parte pueden estar a su vez sustituidos, y R2: (I) alquil-arilo no sustituido o sustituido, en donde el grupo alquil-arilo puede estar sustituido con uno o más F, CI, Br, I, CF3, CN, NH2, NH-alquilo, NH-cicloalquilo, NH-heterociclilo, NH-arilo, NH-heteroarilo, NH-alquil-cicloalquilo, NH-alquil-heterociclilo, NH-alquil-arilo, NH-alquil-heteroarilo, N(alquilo)2, NHC(O)-alquilo, NHC(O)-cicloalquilo, NHC(O)-heterociclilo, NHC(O)-arilo, NHC(O)-heteroarilo, NHC(O)-alquilarilo, NHC(O)-alquil-heteroarilo, NHSO2-alquilo, NHSO2-cicloalqui), NHSO2-heterociclilo, NHSO2-arilo, NHSO2-heteroarilo, NHSO2-alquil-arilo, NHSO2-alquil-heteroarilo, NO2, SH, S-alquilo, S-cicloalquilo, S-heterociclilo, S-arilo, S-heteroarilo, >=O, OH, OCF3, O-alquilo, O-cicloalquilo, O-heterociclilo, O-arilo, O-heteroarilo, O- alquil-cicloalquilo, O-alquil-heterociclilo, O-alquil-arilo, O-alquil-heteroarilo, OC(O)-alquilo, OC(O)-cicloalquilo, OC(O)-heterociclilo, OC(O)-arilo, OC(O)-heteroarilo, OC(O)-alquil-arilo, OC(O)-alquil-heteroarilo, OSO3H, OSO2-alquilo, OSO2-cicloalquilo, OSO2-heterociclilo, OSO2-arilo, OSO2-heteroarilo, OSO2-alquil-arilo, OSO2-alquil-heteroarilo, OP(O)(OH)2, C(O)-alquilo, C(O)-arilo, C(O)-heteroarilo, CO2H, CO2-alquilo, CO2-cicloalquilo, CO2-heterociclilo, CO2-arilo, CO2-heteroarilo, CO2-alquil-cicloalquilo, CO2-alquil-heterociclilo, CO2-alquil-arilo, CO2-alquil-heteroarilo, C(O)-NH2, C(O)NH-alquilo, C(O)NH-cicloalquilo, C(O)NH-heterociclilo, C(O)NH-arilo, C(O)NH-heteroarilo, C(O)NH-alquil-cicloalquilo, C(O)NH-alquil-heterociclilo, C(O)NH-alquil-arilo, C(O)NH-alquil-heteroarilo, C(O)N(alquilo)2, C(O)N(cicloalquilo)2, C(O)N(arilo)2, C(O)N(heteroarilo)2, SO-alquilo, SO-arilo, SO2-alquilo, SO2-arilo, SO2NH2, SO2NH-alquilo, SO2NH-arilo, SO2NH-heteroarilo, SO2NH-alquil-arilo, SO3H, SO2O-alquilo, SO2O-arilo, SO2O-alquil-arilo, alquilo, cicloalquilo, heterociclilo, arilo o heteroarilo iguales o diferentes, (II) alquil-heteroarilo no sustituido o sustituido, en donde el grupo alquil-heteroarilo puede estar sustituido con uno o más F, CI, Br, I, CF3, CN, NH2, NH-alquilo, NH-cicloalquilo, NH-heterociclilo, NH-arilo, NH-heteroarilo, NH-alquil-cicloalquilo, NH-alquil-heterociclilo, NH-alquil-arilo, NH-alquil-heteroarilo, N(alquilo)2, NHC(O)-alquilo, NHC(O)-cicloalquilo, NHC(O)-heterociclilo, NHC(O)-arilo, NHC(O)-heteroarilo, NHC(O)-alquil-arilo, NHC(O)-alquil-heteroarilo, NHSO2-alquilo, NHSO2-cicloalquilo, NHSO2-heterociclilo, NHSO2-arilo, NHSO2-heteroarilo, NHSO2-alquil-arilo, NHSO2-alquil-heteroarilo, NO2, SH, S-alquilo, S-cicloalquilo, S-heterociclilo, S-arilo, S-heteroarilo, OH, OCF3, O-alquilo, O-cicloalquilo, O-heterociclilo, O-arilo, O-heteroarilo, O-alquil-cicloalquilo, O-alquil-heterociclilo, O-alquil-arilo, O-alquil-heteroarilo, OC(O)-alquilo, OC(O)-cicloalquilo, OC(O)-heterociclilo, OC(O)-arilo, OC(O)-heteroarilo, OC(O)-alquil-arilo, OC(O)-alquil-heteroarilo, OSO3H, OSO2-alquilo, OSO2-cicloalquilo, OSO2-heterociclilo, OSO2-arilo, OSO2-heteroarilo, OSO2-alquil-arilo, OSO2-alquil-heteroarilo, OP(O)(OH)2, C(O)-alquilo, C(O)-arilo, C(O)-heteroarilo, CO2H, CO2-alquilo, CO2-cicloalquilo, CO2-heterociclilo, CO2-arilo, CO2-heteroarilo, CO2-alquil-cicloalquilo, CO2-alquil-heterociclilo, CO2-alquil-arilo, CO2-alquil-heteroarilo, C(O)-NH2, C(O)NH-alquilo, C(O)NH-cicloalquilo, C(O)NH-heterociclilo, C(O)NH-arilo, C(O)NH-heteroarilo, C(O)NH-alquil-cicloalquilo, C(O)NH-alquil-heterociclilo, C(O)NH-alquil-arilo, C(O)NH-alquil-heteroarilo, C(O)N(alquilo)2, C(O)N(cicloalquilo)2, C(O)N(arilo)2, C(O)N(heteroarilo)2, SO-alquilo, SO-arilo, SO2-alquilo, SO2-arilo, SO2NH2, SO2NH-alquilo, SO2NH-arilo, SO2NH-heteroarilo, SO2NH-alquil-arilo, SO3H, SO2O-alquilo, SO2O-arilo, SO2O-alquil-arilo, cicloalquilo, heterociclilo, arilo o heteroarilo iguales o diferentes; sus sales fisiológicamente tolerables, en forma de sus racematos, en forma de sus enantiómeros y/o diastereómeros puros o en forma de mezclas de estos enantiómeros y/o diastereómeros o en forma de sus tautómeros para su uso en el tratamiento o la prevención de estados fisiológicos y/o patofisiológicos en mamíferos mediados por la ruta de transducción de señal ras-Raf-Mek-Erk, en donde los estados fisiológicos y/o patofisiológicos se seleccionan entre el grupo que consiste en: "tumores malignos, tumores benignos, enfermedades inflamatorias, inflamaciones, dolor, enfermedades reumáticas, enfermedades artríticas, infecciones por VIH, enfermedades neurológicas o neurodegenerativas, reumatismo, artritis, SIDA, ARC (complejo relacionado con SIDA), sarcoma de Kaposi, tumores originados en el cerebro y/o en el sistema nervioso y/o en las meninges, demencia, enfermedad de Alzheimer, enfermedades hiperproliferativas, psoriasis, endometriosis, cicatrices, hiperplasia benigna de próstata (BPH), enfermedades del sistema inmune, enfermedades autoinmunes, enfermedades de inmunodeficiencia, tumor de colon, tumor gástrico, tumor intestinal, tumor pulmonar, tumor pancreático, tumor de ovario, tumor prostático, leucemia, melanoma, tumor hepático, tumor renal, tumor de cabeza, tumor de garganta, glioma, tumor de mama, cáncer uterino, cáncer endometrial, carcinoma cervico-uterino, tumor cerebral, adeno-acantoma, cáncer de la vejiga, tumor gástrico, tumor colorrectal, cáncer esofágico, tumor ginecológico, tumor de ovario, cáncer de la tiroides, linfoma, leucemia crónica, leucemia aguda, reestenosis, diabetes, nefropatía diabética, enfermedades fibróticas, fibrosis quística, nefroesclerosis maligna, síndrome de microangiopatía trombótica, rechazo de trasplante de órganos, glomerulopatía, enfermedades metabólicas, tumores sólidos/fijos, artritis
Description
Compuesto 97: 1-[3-(1-Metil-1H-pirazol-4-il)-pirido[2,3-b]pirazin-6-il]-3-(4-p-tolil-butil)-urea
Compuesto 100: 1-(4-Metil-4-fenil-pentil)-3-[3-(1-propil-1H-pirazol-4-il)-pirido[2,3-b]pirazin-6-il]-urea
Compuesto 101: 1-[3-(2,4-Dimetoxi-fenil)-pirido[2,3-b]pirazin-6-il]-3-(4-fenil-butil)-urea
Compuesto 103: 1-[3-(3,5-Dicloro-4-hidroxi-fenil)-pirido[2,3-b]pirazin-6-il]-3-(4-fenil-butil)-urea
Compuesto 104: 1-[3-(3-Hidroxi-fenil)-pirido[2,3-b]pirazin-6-il]-3-(4-fenil-butil)-urea
Compuesto 105: 1-(4-fenil-butil)-3-[3-(2H-pirazol-3-il)-pirido[2,3-b]pirazin-6-il]-urea
7
Compuesto 114: 1-[3-(1-Butil-1H-pirazol-4-il)-pirido[2,3-b]pirazin-6-il]-3-(4-fenil-butil)-urea
Compuesto 115: 1-[4-(4-Metoxi-fenil)-butil]-3-[3-(1-metil-1H-pirazol-4-il)-pirido[2,3-b]pirazin-6-il]-urea
Compuesto 116: 1-(4-fenil-butil)-3-[3-(piperidin-4-ilamino)-pirido[2,3-b]pirazin-6-il]-urea
Compuesto 117: 1-(4-fenil-butil)-3-{3-[(piridin-4-ilmetil)-amino]-pirido[2,3-b]pirazin-6-il}-urea
Compuesto 118: 1-[3-(4-Metoxi-fenil)-pirido[2,3-b]pirazin-6-il]-3-(4-fenil-butil)-urea
Compuesto 120: 1-(4-fenil-butil)-3-(3-o-tolil-pirido[2,3-b]pirazin-6-il)-urea
Compuesto 121: Éster etílico del ácido 3-{6-[3-(4-fenil-butil)-ureido]-pirido[2,3-b]pirazin-3-il}-benzoico
9
Evaluación
Los valores de % de inhibición por concentración de sustancia se calcularon mediante la siguiente fórmula a partir de los datos sin procesar determinados en el lector de placa Envision:
Se hicieron ocho determinaciones para cada control y dos para las muestras de sustancia. El 0 % de control contiene nada de ATP o nada de sustrato, el 100 % de control (quinasa completamente activa) contiene nada de sustancia de 10 ensayo. Los valores de CI50 se determinaron usando GraphPadPrism.
Los compuestos de la invención mostraron inhibición eficaz de Erk y/o PI3K con valores de CI50 de hasta 1 nM (véase la Tabla 1).
15 Tabla 1: resultados de ensayo para el ensayo de quinasa alfa de Erk2 (CI50 [µM] a ATP 10 µM)
- Compuesto
- Erk2
- 108
- 0,004
- 127
- 0,005
- 155
- 0,004
- 156
- 0,001
- 157
- 0,002
- 158
- 0,001
- 159
- 0,001
- 160
- 0,001
- 161
- 0,002
- 162
- 0,002
- 163
- 0,002
- 164
- 0,002
- 165
- 0,003
- 166
- 0,003
- 167
- 0,003
- 168
- 0,003
- 169
- 0,003
- 170
- 0,004
- 171
- 0,004
- 172
- 0,005
- 173
- 0,005
- 174
- 0,006
- 175
- 0,006
- 176
- 0,006
- 177
- 0,006
- 178
- 0,006
- 179
- 0,006
- 180
- 0,006
- 181
- 0,006
- 189
- 0,004
- 194
- 0,001
- 195
- 0,001
- 196
- 0,004
- 197
- 0,005
- 198
- 0,003
- 201
- 0,039
- 202
- 0,041
- 203
- 0,024
Ensayo celular: ensayo para el efecto antiproliferativo (ensayo XTT)
El principio de este ensayo se basa en la reducción intracelular del colorante tetrazolio XTT (ácido
20 3’-[1-(fenilaminocarbonil)-3,4-tetrazolio]-bis(4-metoxi-6-nitro)benzeno sulfónico sódico, Sigma) en un colorante formazán por deshidrogenasas mitocondriales. El colorante es el único formado por células metabólicamente activas y su intensidad fotométricamente medible es un indicador cuantitativo de la presencia de células vivas. La reducción de
57
Claims (1)
-
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
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161472245P | 2011-04-06 | 2011-04-06 | |
| EP11161248A EP2508184A1 (en) | 2011-04-06 | 2011-04-06 | Pyridopyrazine derivatives and their use |
| US201161472245P | 2011-04-06 | ||
| EP11161248 | 2011-04-06 | ||
| PCT/EP2012/056138 WO2012136691A1 (en) | 2011-04-06 | 2012-04-04 | Pyridopyrazine derivatives and their use |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2552515T3 true ES2552515T3 (es) | 2015-11-30 |
Family
ID=44350566
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| ES12713705.7T Active ES2552515T3 (es) | 2011-04-06 | 2012-04-04 | Derivados de piridopirazina y su uso |
Country Status (19)
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| US (2) | US8791118B2 (es) |
| EP (3) | EP2508184A1 (es) |
| JP (2) | JP2014510125A (es) |
| KR (2) | KR20140025443A (es) |
| CN (2) | CN103826636A (es) |
| AR (2) | AR085844A1 (es) |
| AU (2) | AU2012238681A1 (es) |
| BR (1) | BR112013025630A2 (es) |
| CA (2) | CA2832321A1 (es) |
| ES (1) | ES2552515T3 (es) |
| IL (2) | IL228433A0 (es) |
| MX (2) | MX2013011444A (es) |
| NZ (1) | NZ615578A (es) |
| PL (1) | PL2694067T3 (es) |
| RU (2) | RU2013146618A (es) |
| SG (2) | SG194097A1 (es) |
| TW (2) | TWI564299B (es) |
| WO (2) | WO2012136694A1 (es) |
| ZA (2) | ZA201306862B (es) |
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| WO2017033113A1 (en) | 2015-08-21 | 2017-03-02 | Acerta Pharma B.V. | Therapeutic combinations of a mek inhibitor and a btk inhibitor |
| AU2016353442A1 (en) * | 2015-11-13 | 2018-05-31 | Massachusetts Institute Of Technology | Methods and compositions for detecting and modulating cancer cells |
| BR112018012914B1 (pt) | 2015-12-22 | 2023-04-18 | SHY Therapeutics LLC | Composto, uso de um composto e composição farmacêutica |
| WO2017180817A1 (en) * | 2016-04-15 | 2017-10-19 | Musc Foundation For Research Development | Treatment of septicemia and ards with erk inhibitors |
| SG11201911929XA (en) | 2017-06-21 | 2020-01-30 | SHY Therapeutics LLC | Compounds that interact with the ras superfamily for the treatment of cancers, inflammatory diseases, rasopathies, and fibrotic disease |
| WO2018237383A1 (en) * | 2017-06-23 | 2018-12-27 | The Trustees Of Columbia University In The City Of New York | METHODS OF PREVENTING AND TREATING DISEASES CHARACTERIZED BY SYNAPTIC DYSFUNCTION AND NEURODEGENERATION, INCLUDING ALZHEIMER'S DISEASE |
| WO2019238933A1 (en) * | 2018-06-15 | 2019-12-19 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Use of pi3kc2b inhibitors for the preservation of vascular endothelial cell barrier integrity |
| CN112830897B (zh) * | 2019-11-22 | 2022-09-09 | 石家庄以岭药业股份有限公司 | 含脲基苯并咪唑类衍生物及其制备方法和应用 |
| WO2022147210A1 (en) * | 2020-12-31 | 2022-07-07 | Evrys Bio, Llc | Anti-tumor compositions and methods |
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| US3809695A (en) | 1967-04-19 | 1974-05-07 | Degussa | 2,6-dichloro-3-nitro-pyridine |
| EP0735025B1 (en) | 1995-03-28 | 1998-07-01 | Sumitomo Chemical Company Limited | Process for producing aminonitropyridines |
| UA71555C2 (en) | 1997-10-06 | 2004-12-15 | Zentaris Gmbh | Methods for modulating function of serine/threonine protein kinases by 5-azaquinoline derivatives |
| ES2154253T3 (es) | 1997-12-22 | 2012-01-27 | Bayer Healthcare Llc | Inhibición de la actividad de p38 cinasa usando ureas heterocíclicas sustituidas. |
| AU2002327627B2 (en) | 2001-09-14 | 2006-09-14 | Methylgene Inc. | Inhibitors of histone deacetylase |
| US20040023961A1 (en) | 2002-02-11 | 2004-02-05 | Bayer Corporation | Aryl ureas with raf kinase and angiogenisis inhibiting activity |
| EP1496981A2 (en) | 2002-04-08 | 2005-01-19 | Merck & Co., Inc. | Method of treating cancer |
| CA2480800C (en) | 2002-04-08 | 2008-09-23 | Mark T. Bilodeau | Inhibitors of akt activity |
| CA2480880C (en) | 2002-04-08 | 2011-03-22 | Merck & Co., Inc. | Inhibitors of akt activity |
| JP4903997B2 (ja) | 2002-07-02 | 2012-03-28 | サザン リサーチ インスティチュート | ＦｔｓＺの阻害剤およびそれらの用途 |
| DE10323345A1 (de) | 2003-05-23 | 2004-12-16 | Zentaris Gmbh | Neue Pyridopyrazine und deren Verwendung als Kinase-Inhibitoren |
| PT1636228E (pt) * | 2003-05-23 | 2009-02-02 | Aeterna Zentaris Gmbh | Novas piridopirazinas e sua utilização como moduladores de cinases |
| WO2005007099A2 (en) | 2003-07-10 | 2005-01-27 | Imclone Systems Incorporated | Pkb inhibitors as anti-tumor agents |
| AU2004297235A1 (en) | 2003-12-04 | 2005-06-23 | Vertex Pharmaceuticals Incorporated | Quinoxalines useful as inhibitors of protein kinases |
| GB0413953D0 (en) | 2004-06-22 | 2004-07-28 | Syngenta Participations Ag | Chemical compounds |
| EP1790342A1 (de) * | 2005-11-11 | 2007-05-30 | Zentaris GmbH | Pyridopyrazin-Derivate und deren Verwendung als Modulatoren der Signaltransduktionswege |
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| EP1785423A1 (de) * | 2005-11-11 | 2007-05-16 | Zentaris GmbH | Neue Pyridopyrazine und deren Verwendung als Modulatoren von Kinasen |
| US8217042B2 (en) | 2005-11-11 | 2012-07-10 | Zentaris Gmbh | Pyridopyrazines and their use as modulators of kinases |
| US7733554B2 (en) * | 2006-03-08 | 2010-06-08 | E Ink Corporation | Electro-optic displays, and materials and methods for production thereof |
| KR101097177B1 (ko) | 2006-07-06 | 2011-12-22 | 한국화학연구원 | 2-알킬레닐옥시-3-에티닐피리도［2,3-ｂ］피라진 유도체 |
| GB0614471D0 (en) | 2006-07-20 | 2006-08-30 | Syngenta Ltd | Herbicidal Compounds |
| US20100093738A1 (en) | 2006-10-06 | 2010-04-15 | Basf Se | Fungicidal Compounds and Fungicidal Compositions |
| EP1990342A1 (en) | 2007-05-10 | 2008-11-12 | AEterna Zentaris GmbH | Pyridopyrazine Derivatives, Process of Manufacturing and Uses thereof |
| EP2220503A1 (en) * | 2007-11-30 | 2010-08-25 | Schering Corporation | Braf biomarkers |
| AU2008337286B2 (en) | 2007-12-19 | 2014-08-07 | Cancer Research Technology Limited | Pyrido[2,3-b]pyrazine-8-substituted compounds and their use |
-
2011
- 2011-04-06 EP EP11161248A patent/EP2508184A1/en not_active Withdrawn
-
2012
- 2012-04-03 TW TW101111889A patent/TWI564299B/zh not_active IP Right Cessation
- 2012-04-03 TW TW101111888A patent/TW201302742A/zh unknown
- 2012-04-04 CN CN201280019613.9A patent/CN103826636A/zh active Pending
- 2012-04-04 KR KR1020137029386A patent/KR20140025443A/ko not_active Application Discontinuation
- 2012-04-04 AR ARP120101163A patent/AR085844A1/es unknown
- 2012-04-04 EP EP12713705.7A patent/EP2694067B1/en active Active
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