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2
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53549109444
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For examples of benzimidazole-based IGF1R kinase inhibitors see:
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For examples of benzimidazole-based IGF1R kinase inhibitors see:. Velaparthi U., Wittman M., Liu P., Carboni J.M., Lee F.Y., Attar R., Balimane P., Clarke W., Sinz M.W., Hurlburt W., Patel K., Discenza L., Kim S., Gottardis M., Greer A., Li A., Saulnier M., Yang Z., Zimmermann K., Trainor G., and Vyas D. J. Med. Chem. 51 (2008) 5897
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Balimane, P.7
Clarke, W.8
Sinz, M.W.9
Hurlburt, W.10
Patel, K.11
Discenza, L.12
Kim, S.13
Gottardis, M.14
Greer, A.15
Li, A.16
Saulnier, M.17
Yang, Z.18
Zimmermann, K.19
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Vyas, D.21
more..
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34548552538
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Hubbard R.D., Bamaung N.Y., Palazzo F., Zhang Q., Kovar P., Osterling D.J., Hu X., Wilsbacher J.L., Johnson E.F., Bouska J., Wang J., Bell R.L., Davidsen S.K., and Sheppard G.S. Bioorg. Med. Chem. Lett. 17 (2007) 5406
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Kovar, P.5
Osterling, D.J.6
Hu, X.7
Wilsbacher, J.L.8
Johnson, E.F.9
Bouska, J.10
Wang, J.11
Bell, R.L.12
Davidsen, S.K.13
Sheppard, G.S.14
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Hirashima S., Suzuki T., Ishida T., Noji S., Yata S., Ando I., Komatsu M., Ikeda S., and Hashimoto H. J. Med. Chem. 49 (2006) 4721
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Ando, I.6
Komatsu, M.7
Ikeda, S.8
Hashimoto, H.9
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6
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33847403132
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Lansing T.J., McConnell R.T., Duckett D.R., Spehar G.M., Knick V.B., Hassler D.F., Noro N., Furuta M., Emmitte K.A., Gilmer T.M., Mook Jr. R.A., and Cheung M. Mol. Cancer Ther. 6 (2007) 450
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Hassler, D.F.6
Noro, N.7
Furuta, M.8
Emmitte, K.A.9
Gilmer, T.M.10
Mook Jr., R.A.11
Cheung, M.12
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7
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51549109898
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For the synthesis of ester and amide substrates 1 see: (a) Hornberger, K. R.; Badiang, J. G.; Salovich, J. M.; Kuntz, K. W.; Emmitte, K. A.; Cheung, M. Tetrahedron Lett. 2008, 49, 6348. (b) Kuntz, K.; Emmitte, K. A.; Rheault, T. R.; Smith, S.; Hornberger, K.; Dickson, H.; Cheung, M. PCT Int. Appl. WO2007143456, 2007.
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For the synthesis of ester and amide substrates 1 see: (a) Hornberger, K. R.; Badiang, J. G.; Salovich, J. M.; Kuntz, K. W.; Emmitte, K. A.; Cheung, M. Tetrahedron Lett. 2008, 49, 6348. (b) Kuntz, K.; Emmitte, K. A.; Rheault, T. R.; Smith, S.; Hornberger, K.; Dickson, H.; Cheung, M. PCT Int. Appl. WO2007143456, 2007.
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8
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10744227006
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Bilodeau M.T., Cunningham A.M., Koester T.J., Ciecko P.A., Coll K.E., Huckle W.R., Hungate R.W., Kendall R.L., McFall R.C., Mao X., Rutledge R.Z., and Thomas K.A. Bioorg. Med. Chem. Lett. 13 (2003) 2485
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Bilodeau, M.T.1
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Coll, K.E.5
Huckle, W.R.6
Hungate, R.W.7
Kendall, R.L.8
McFall, R.C.9
Mao, X.10
Rutledge, R.Z.11
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9
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59649084728
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Liu, H.; Pan, W.; Xu, Y.-J. PCT Int. Appl. WO2005042496, 2005.
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Liu, H.; Pan, W.; Xu, Y.-J. PCT Int. Appl. WO2005042496, 2005.
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10
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59649094189
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For an example where the reactivity of the coupling partners is reversed see: Bonjouklian, R.; Dally, R. D.; De Dios, A.; Del Prado Catalina, M. F.; Dominguez-Fernandez, C.; Jaramillo Aguado, C.; Lopez de Uralde-Garmendia, B.; Montero Salgado, C.; Shepherd, T. A. PCT Int. Appl. WO2005080380, 2005.
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For an example where the reactivity of the coupling partners is reversed see: Bonjouklian, R.; Dally, R. D.; De Dios, A.; Del Prado Catalina, M. F.; Dominguez-Fernandez, C.; Jaramillo Aguado, C.; Lopez de Uralde-Garmendia, B.; Montero Salgado, C.; Shepherd, T. A. PCT Int. Appl. WO2005080380, 2005.
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11
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59649101444
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note
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Ishiyama, T.; Chen, H. 4,4,4′,4′,5,5,5′,5′-Octamethyl-2,2′-bi-1,3,2-dioxaborolane. e-EROS Encyclopedia of Reagents for Organic Synthesis, 2001.
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12
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33646497228
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For examples of microwave-assisted boronate ester formation see:
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For examples of microwave-assisted boronate ester formation see:. DiMauro E.F., and Vitullo J.R. J. Org. Chem. 71 (2006) 3959
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J. Org. Chem.
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DiMauro, E.F.1
Vitullo, J.R.2
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13
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15944416437
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De Borggraeve W.M., Appukkuttan P., Azzam R., Dehaen W., Compernolle F., Van der Eycken E., and Hoornaert G. Synlett (2005) 777
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Synlett
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De Borggraeve, W.M.1
Appukkuttan, P.2
Azzam, R.3
Dehaen, W.4
Compernolle, F.5
Van der Eycken, E.6
Hoornaert, G.7
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16
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59649083529
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note
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The LC-MS data included in Table 1 were obtained using LC-MS systems calibrated on a daily basis with a system-suitability seven-component test mix to ensure fit for purpose (identity and purity).
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17
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59649102290
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note
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In addition to unreacted 1, the following by-products were also routinely observed: X = H, 2-12% by LC-MS; unreacted boronic acid, 7-11% by LC-MS; and dimers formed from homocoupling of 1, 0-6% by LC-MS.
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19
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9644262708
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For examples of pyrazole and imidazole moieties functioning as Pd ligands in Suzuki-Miyaura reactions see:
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For examples of pyrazole and imidazole moieties functioning as Pd ligands in Suzuki-Miyaura reactions see:. Mukherjee A., and Sarkar A. Tetrahedron Lett. 45 (2004) 9525
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Tetrahedron Lett.
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Mukherjee, A.1
Sarkar, A.2
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