5-Amidinoindoles as dual inhibitors of coagulation factors IXa and Xa

…, DA Pierson, KA Rossi, JM Luettgen, RM Knabb…

Index: Batt, Douglas G.; Qiao, Jennifer X.; Modi, Dilip P.; Houghton, Gregory C.; Pierson, Deborah A.; Rossi, Karen A.; Luettgen, Joseph M.; Knabb, Robert M.; Jadhav; Wexler, Ruth R. Bioorganic and Medicinal Chemistry Letters, 2004 , vol. 14, # 21 p. 5269 - 5273

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Citation Number: 27

Abstract

... a) Et 3 SiH, CF 3 COOH, rt; (b) (PhSeO) 2 O, indole, THF, 60 °C, 76% (2 steps); (c) for 5a: KN(TMS) 2 , THF, 0 °C; i-Pr 3 SiCl, to rt (75%); for 5b: NaH, DMF, 0 °C; MeI, to rt (99%); (d) LiN(TMS) 2 , THF, −78 °C; RBr or RI, to rt (30–80%); (e) Me 3 Al, R′NH 2 , CH 2 Cl 2 ; or LiOH, then DIC, pyridine/DMSO, R′NH 2 , 60–80%; (f) EtOH, HCl, rt; (g) NH 3 ... Compd, X, Y, Z a, W, fIXa K i , nM, fXa K i , nM, fIXa/fXa. ... Rep. Med. Chem., 36 (2001), p. 79 and references cited therein ...