GB1253709A — Thiadiazole derivatives

USPTO Abstract

1,253,709. Thiadiazoles. CHARLES E. FROSST & CO. 19 May, 1969 [22 May, 1968; 21 April, 1969], No. 25333/69. Heading C2C. Compounds of the general formula (R = H, Cl, Br, C 1-5 alkyl or alkoxy, C 2-5 alkenyl, C 3-6 cycloalkyl, Y-X-Z (Y = C 1-4 alkyl optionally substituted by Ph or Ph having one or more substituents selected from halogen atoms and OH, C 1-3 alkyl and alkoxy groups; Z= C 1-2 alkyl; X=O, S), R<SP>51</SP> HNCO (R<SP>51</SP> = C 1-5 alkyl), Ph or Ph-(C 1-4 alkyl) optionally having one or more substituents selected from halogen atoms and C 1-3 alkyl and alkoxy groups attached to the ring, NR<SP>7</SP>R<SP>8</SP> (R<SP>7</SP> = H, C 1-4 alkyl, C 2-4 hydroxyalkyl R<SP>8</SP> = H, C 1-4 alkyl, C 2-4 hydroxyalkyl, Ph or NR<SP>7</SP>R<SP>8</SP> = 3-7 membered ring optionally having one or more substituents selected from OH, C 1-5 alkyl, C 1-3 hydroxyalkyl or R<SP>7</SP> and R<SP>8</SP> are joined through an O, N or S atom to form a 5-6 membered ring together with the N atom to which they are attached, optionally C 1-3 alkyl substituted), 5-6 membered heterocyclic ring linked through a carbon atom and having O, N or S as the hetero atom; R<SP>1,2,4</SP>=H, C 1-3 alkyl; R<SP>3</SP>=H, PhCO, C 2- 4 alkanoyl; R<SP>5</SP>=H, C 1-5 alkyl, Ph C 1-3 alkyl or C 2-5 alkanoyl; R<SP>6</SP>=C 1-20 alkyl, C 2-6 alkenyl or alkynyl optionally having one or more substituents selected from halogen atoms, OH, carboxy, (C 1-3 alkoxy) carbonyl, C 1-4 alkoxy and alkylthio, di-(C 1-3 alkyl) amino, pyrrolidinyl, piperazinyl, piperidinyl, morpholino, thiazolidinyl, thiazinyl, 5-6 membered heterocyclic rings attached through a nuclear carbon atom and having O, N or S as the hetero atom, Ph and PhO optionally having 1-3 substituents selected from halogen atoms, OH and C 1-3 alkoxy groups, Ph optionally substituted by C 1-3 alkyl, pyrrolidinyl, piperidinyl, C 3-6 cycloalkyl optionally substituted by C 1-3 alkyl or 5-6 membered N or O-containing ring, 5-6 membered heterocyclic ring containing O, N or S as the hetero atom and attached through a nuclear carbon atom and optionally substituted by C 1-3 alkyl or 5-6 membered N or O-containing heterocyclic ring, or NR<SP>5</SP>R<SP>6</SP>=4-6 membered ring which may contain in addition to but not adjacent to the N atom one or two different hetero atoms selected from O, S, N and which may be substituted by one or more C 1-3 alkyl radicals) and their salts are prepared by the following routes: optionally followed by esterification. The above compounds are #-adrenergic blocking agents and may be administered in the form of pharmaceutical preparations containing them in association with a carrier.