Benzodiazepine derivatives useful in treating a respiratory syncytial virus infection

Abstract

Benzodiazepine derivatives of formula (Ie) wherein one Rand Ris a benzodiazepinyl-containing group of formula (II) in which Ris H or halo; the other of Rand Ris a group Z selected from H, C-Ccycloalkyl, halo, —NHR, benzyl, phenyl, 4- to 10-membered heterocyclyl and 4- to 10-membered heteroaryl, wherein phenyl, heterocyclyl and heteroaryl are unsubstituted or substituted by one or two substituents selected from 4- to 10-membered heterocyclyl which is unsubstituted or substituted by OR, and from C-Calkyl, C-Chydroxyalkyl, C-Chaloalkyl, C-Ccycloalkyl, halo, —OR, —(CH)OR, —NR, —(CH)NR, —NHR″, —SONR, —SOR, —SR, nitro, —COR, —CN, —CONR, —NHCOR, —CHNRRand —NRR, in which each R is independently H or C-Calkyl, R″ is C-Ccycloalkyl and m is 1 or 2; Ris selected from phenyl and 4- to 10-membered heteroaryl wherein phenyl and heteroaryl are unsubstituted or substituted by halo; Rand Rare each independently H or C-Calkyl; or Rand Rform, together with the N atom to which they are attached, either (a) a morpholine ring which is optionally bridged by a —CH— group linking two ring carbon atoms that are positioned para to each other, or (b) a spiro group of the following formula (b): and ring A is a ring of one of the following structural formulae (I-1), (I-2) and (I-3): and ring A is a ring of one of the following structural formulae (I-1), (I-2) and (I-3): in which Y is selected from O, S, SOand NR, wherein R is as defined above, and each of Rto Ris independently H, C-Calkyl, C-Chydroxyalkyl, C-Ccycloalkyl, halo, —OR, —CHOR, —NR, —CHNRR, —NRCOOR, —CHOR, —SONR, —SOR, —CHSOR, nitro, —COR, —CN, —CONRor —NHCOR, in which R and m are as defined above and Rand Rare each independently H, C-Calkyl, benzyl, 4- to 10-membered heterocyclyl or Rand Rform, together with the N atom to which they are attached, a 4- to 10-membered heteroaryl which is unsubstituted or a 4- to 10-membered heterocyclyl which is unsubstituted or substituted with C-Calkyl or halo, or any two of Rto Rthat bond to the same carbon atom form a spiro ring selected from a C-Ccycloalkyl spiro ring and a spiro oxetane ring of the following structure: (Formula A) and the pharmaceutically acceptable salts thereof are inhibitors of RSV and can therefore be used to treat or prevent an RSV infection.