Preparation of benzothiazepines and analogs for the treatment and prophylaxis of respiratory syncytial virus infection.

Abstract

The invention is related to the prepn. of compds. I [R1-3 = independently H, halo, alkyl; R4 = H, alkyl; R5 = H, halo; R6 = H, OH, CO2H, alkylpiperazin-1-yl, etc.; R7 = H, alkyl, alkylaminocarbonyl, etc.; R8 = H, halo, alkoxy; R9 = H, alkyl, :O; R10 = H, :O; provided that R9 and R10 are not :O simultaneously; A = N, CH and derivs.; X = CH2, O, NH, CF2, S(O)0-2, etc.; Y = CH, N; Q = H, halo, alkyl], their pharmaceutically acceptable salts and stereoisomers useful as a medicament for the treatment of respiratory syncytial virus (RSV). Thus, monoamination of 2,4-dichloro-6-methylquinoline with 8-methoxy-2,3,4,5-tetrahydro-1,4-benzothiazepine (prepn. given), oxidn. of benzothiazepine and amination of the chloro intermediate with 3-(aminomethyl)-N,N-dibenzyloxetan-3-amine (prepn. given) gave II. I had an EC50 in the range of 0.0001 μM to about 0.1 μM were tested for their anti-RSV activity in a viral cytopathic effect assay and displayed an EC50 in the range of 0.0001 μM to about 10 μM. [on SciFinder(R)]