GB1211258A — Amines

USPTO Abstract

1,211,258. Amines. BOEHRINGER INGELHEIM G.m.b.H. 1 Feb., 1968 [1 Feb., 1967; 2 June, 1967; 19 July, 1967], No. 5295/68. Heading C2C. Racemic and optically active cis, trans and cis-trans compounds of the general Formula (I) (R 1,2 = H, halogen, Me, OMe, CF 3 , CN, OH or R 1+2 together with the adjacent ring = naphthalene, indane, tetrahydronaphthalene, benz-1,3-dioxole or benzodioxane ring system; R 3 = H, Me, Et, Ph optionally substituted by at least one methyl group; R 4 = H, Me, Et, Ph optionally substituted by halogen, Me, OMe; R 5 = H, C 1-3 alkyl, PhCH 2 optionally substituted by halogen and/or C 1-3 alkyl; R 6 = H, C 1-3 alkyl or -NR 5 R 6 = pyrrolidino, piperidino, morpholino or 5-6 membered ring containing a further nitrogen atom optionally N-substituted by Me, Et, Ph optionally substituted by at least one halogen and/or Me and/or Et; X = O, S, CH 2 provided that when X = O and R 1,2 = 7- and 8-Me, at least one of R 3-6 is not H and when X = S at least one of R 1-6 is not H) and their acid addition salts are prepared by (a) reacting a compound of the Formula (II) with a reducing agent whereby the ketonic oxyten atom is converted to an OH group with simultaneous introduction of R 3 , (b) alkylating or benzylating a compound of the Formula (I) in which R 5,6 = H, or (c) hydrolysing or hydrogenolysing a compound of the Formula (IV) (R<SP>1</SP> = protecting group), optionally followed in each case by salt formation and/or separation of the racemates of the cis and trans isomers and in the latter case by resolution. The above compounds are antidepressants and anticonvulsants, and may be administered in the form of pharmaceutical preparations containing them in association with a carrier.