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1
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0004195999
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Lippincott, Williams and Wilkins, Philadelphia (Chapter 1)
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Colman R.W., Clowes A.W., George J.N., Hirsh J., and Marder V.J. Hemostasis and Thrombosis: Basic Principles and Clinical Practice (2001), Lippincott, Williams and Wilkins, Philadelphia (Chapter 1)
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(2001)
Hemostasis and Thrombosis: Basic Principles and Clinical Practice
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Colman, R.W.1
Clowes, A.W.2
George, J.N.3
Hirsh, J.4
Marder, V.J.5
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2
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0033591756
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and references therein
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Pass M., Abu-Rabie S., Baxter A., Conroy R., Coote S.J., Craven A.P., Finch H., Hindley S., Kelly H.A., Lowdon A.W., McDonald E., Mitchell W.L., Pegg N.A., Procopiou P.A., Ramsden N.G., Thomas R., Walker D.A., Watson N.S., Jhoti H., Mooney C.J., Tang C.-M., Thomas P.J., Parry S., and Patel C. Bioorg. Med. Chem. Lett. 9 (1999) 1657 and references therein
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(1999)
Bioorg. Med. Chem. Lett.
, vol.9
, pp. 1657
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Pass, M.1
Abu-Rabie, S.2
Baxter, A.3
Conroy, R.4
Coote, S.J.5
Craven, A.P.6
Finch, H.7
Hindley, S.8
Kelly, H.A.9
Lowdon, A.W.10
McDonald, E.11
Mitchell, W.L.12
Pegg, N.A.13
Procopiou, P.A.14
Ramsden, N.G.15
Thomas, R.16
Walker, D.A.17
Watson, N.S.18
Jhoti, H.19
Mooney, C.J.20
Tang, C.-M.21
Thomas, P.J.22
Parry, S.23
Patel, C.24
more..
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8
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33746578467
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Ewing, W. R.; Becker, M. R.; Pauls, H. W.; Cheney, D. L.; Mason, J. S.; Spada, A. P.; Choi-Sledeski, Y. M. WO 9640679 A1, 1996.
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9
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0033539050
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Ewing W.R., Becker M.R., Manetta V.E., Davis R.S., Pauls H.W., Mason H., Choi-Sledeski Y.M., Green D., Cha D., Spada A.P., Cheney D.L., Mason J.S., Maignan S., Guilloteau J.-P., Brown K., Colussi D., Bentley R., Bostwick J., Kasiewski C.J., Morgan S.R., Leadley R.J., Dunwiddie C.T., Perrone M.H., and Chu V. J. Med. Chem. 42 (1999) 3557
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(1999)
J. Med. Chem.
, vol.42
, pp. 3557
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Ewing, W.R.1
Becker, M.R.2
Manetta, V.E.3
Davis, R.S.4
Pauls, H.W.5
Mason, H.6
Choi-Sledeski, Y.M.7
Green, D.8
Cha, D.9
Spada, A.P.10
Cheney, D.L.11
Mason, J.S.12
Maignan, S.13
Guilloteau, J.-P.14
Brown, K.15
Colussi, D.16
Bentley, R.17
Bostwick, J.18
Kasiewski, C.J.19
Morgan, S.R.20
Leadley, R.J.21
Dunwiddie, C.T.22
Perrone, M.H.23
Chu, V.24
more..
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10
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33746558613
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fXa inhibitory activities were determined using N-α-Z-d-Arg-Gly-Arg-p-nitroanilide as chromogenic substrate; details are described in Ref. 11.
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11
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33746504511
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Anticoagulant activities were determined in the prothrombin time (PT) assay; details (test 2) are described in Ref. 11
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12
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0033000366
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Macdonald S.J.F., Clarke G.D.E., Dowle M.D., Harrison L.A., Hodgson S.T., Inglis G.G.A., Johnson M.R., Shah P., Upton R.J., and Walls S.B. J. Org. Chem. 64 (1999) 5166
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(1999)
J. Org. Chem.
, vol.64
, pp. 5166
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-
Macdonald, S.J.F.1
Clarke, G.D.E.2
Dowle, M.D.3
Harrison, L.A.4
Hodgson, S.T.5
Inglis, G.G.A.6
Johnson, M.R.7
Shah, P.8
Upton, R.J.9
Walls, S.B.10
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13
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33746565964
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note
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Compounds 13a and 13b were prepared as racemates from the corresponding diastereomeric intermediates 16 which were separated by chromatography; the relative stereochemistry of the diastereomers 13a and 13b have not been determined.
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14
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0019963407
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2-Azido-4-iodobutanoate was derived from the 4-bromo derivative by reaction with sodium iodide in acetone; 2-azido-4-bromobutanoate was prepared from the 2,4-dibromo derivative (Ref. 9b) by the method reported for the corresponding methyl ester
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2-Azido-4-iodobutanoate was derived from the 4-bromo derivative by reaction with sodium iodide in acetone; 2-azido-4-bromobutanoate was prepared from the 2,4-dibromo derivative (Ref. 9b) by the method reported for the corresponding methyl ester. J. Org. Chem. 47 (1982) 1319
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(1982)
J. Org. Chem.
, vol.47
, pp. 1319
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-
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16
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33746562355
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note
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Compounds 21-22 were derived by deprotection of the corresponding Boc-protected derivatives by treatment with TFA in DCM. Compound 23 was prepared as a 1:1 mixture of two diastereomers by the route outlined in Scheme 2 utilising the tert-butyl ester of l-alanine.
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17
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33746492243
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Chan, C.; Hamblin, J. N.; Kelly, H. A.; King, N. P.; Mason, A. M.; Patel, V. K.; Senger, S.; Shah, G. P.; Watson, N. S.; Weston, H. E.; Whitworth, C.; Young, R. J. WO 02100886 A1, 2002.
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18
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33746490010
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Chan, C.; Hamblin, J. N.; Kelly, H. A.; King, N. P.; Mason, A. M.; Patel, V. K.; Senger, S.; Shah, G. P.; Watson, N. S.; Weston, H. E.; Whitworth, C.; Young, R. J. WO 02100830 A1, 2002.
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19
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0034929926
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Valko K., Du C.M., Bevan C., Reynolds D.P., and Abraham M.H. Curr. Med. Chem. 8 (2001) 1137
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(2001)
Curr. Med. Chem.
, vol.8
, pp. 1137
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Valko, K.1
Du, C.M.2
Bevan, C.3
Reynolds, D.P.4
Abraham, M.H.5
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20
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33746504510
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note
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Compound 21 shows good selectivity over other trypsin-like serine proteases tested, including thrombin.
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21
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33746497337
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Chan, C. et al. J. Med. Chem., manuscript in preparation.
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22
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33746572742
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Senger, S. et al. Bioorg. Med. Chem. Lett., manuscript in preparation.
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23
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0034710722
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free of 0.242. Coordinates are deposited in the protein data bank with code 2cji.
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free of 0.242. Coordinates are deposited in the protein data bank with code 2cji.
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(2000)
J. Med. Chem.
, vol.43
, pp. 3226
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Maignan, S.1
Guilloteau, J.-P.2
Pouzieux, S.3
Choi-Sledeski, S.4
Becker, M.R.5
Klein, S.I.6
Ewing, W.R.7
Pauls, H.W.8
Spada, A.P.9
Mikol, V.10
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24
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0037468474
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Similar findings have been reported recently for other series of fXa inhibitors
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Similar findings have been reported recently for other series of fXa inhibitors. Choi-Sledeski Y.M., Kearney R., Poli G., Pauls H., Gardner C., Gong Y., Becker M., Davis R., Spada A., Liang G., Chu V., Brown K., Collussi D., Leadley Jr. R., Rebello S., Moxey P., Morgan S., Bentley R., Kasiewski C., Maignan S., Guilloteau J.-P., and Mikol V. J. Med. Chem. 46 (2003) 681
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(2003)
J. Med. Chem.
, vol.46
, pp. 681
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Choi-Sledeski, Y.M.1
Kearney, R.2
Poli, G.3
Pauls, H.4
Gardner, C.5
Gong, Y.6
Becker, M.7
Davis, R.8
Spada, A.9
Liang, G.10
Chu, V.11
Brown, K.12
Collussi, D.13
Leadley Jr., R.14
Rebello, S.15
Moxey, P.16
Morgan, S.17
Bentley, R.18
Kasiewski, C.19
Maignan, S.20
Guilloteau, J.-P.21
Mikol, V.22
more..
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25
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11144357441
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Jia Z.J., Su T., Zuckett J.F., Wu Y., Goldman E.A., Li W., Zhang P., Clizbe L.A., Song Y., Bauer S.M., Huang W., Woolfrey J., Sinha U., Arfsten A.E., Hutchaleelaha A., Hollenbach S.J., Lambing J.L., Scarborough R.M., and Zhu B.-Y. Bioorg. Med. Chem. Lett. 14 (2004) 2073
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(2004)
Bioorg. Med. Chem. Lett.
, vol.14
, pp. 2073
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-
Jia, Z.J.1
Su, T.2
Zuckett, J.F.3
Wu, Y.4
Goldman, E.A.5
Li, W.6
Zhang, P.7
Clizbe, L.A.8
Song, Y.9
Bauer, S.M.10
Huang, W.11
Woolfrey, J.12
Sinha, U.13
Arfsten, A.E.14
Hutchaleelaha, A.15
Hollenbach, S.J.16
Lambing, J.L.17
Scarborough, R.M.18
Zhu, B.-Y.19
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26
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24944536065
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Roehrig S., Straub A., Pohlmann J., Lampe T., Pernerstorfer J., Schlemmer K.-H., Reinemer P., and Perzborn E. J. Med. Chem. 48 (2005) 5900
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(2005)
J. Med. Chem.
, vol.48
, pp. 5900
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Roehrig, S.1
Straub, A.2
Pohlmann, J.3
Lampe, T.4
Pernerstorfer, J.5
Schlemmer, K.-H.6
Reinemer, P.7
Perzborn, E.8
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27
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33746487389
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note
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Compound 24 was administered iv (1 mg/kg) as a slow bolus over 5 min and po (1 mg/kg) via gavage to female Beagle dogs. The dosing vehicle was a 5:95% (v/v) mixture of DMSO and 50:50 PEG-200:sterile water.
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