GB1282336A - Thiaxanthene derivatives and their preparation - Google Patents

Abstract

1282336 Quinuclidine derivatives SOC GENERALE DE RECHERCHES ET D'APPLICATIONS SCIENTIFIQUES 19 April 1971 [25 March 1970] 14594/70 Heading C2C The invention comprises compounds of formula and their acid addition and quaternary ammonium salts, wherein R is H, halogen, C 1-4 alkyl, C 1-4 alkoxy, CF 3 or dialkylsulphamyl; A is S, SO or SO 2 ; the quinuclidine ring is substituted in the 2- or 3-position; x is 1 or 2 when the quinuclidine ring is 2-substituted and 0 or 1 when it is 3- substituted; and the broken line represents an optional bond, the ring-attached CH 2 group (x = 1 or 2) then becoming = CH-. In examples, 9 - (3-quinuclidylmethyl)thiaxanthenes, prepared by reacting a 9-M-thiaxanthene (II : M=Na or Li) with 3-chloromethylquinuclidine, are oxidized to the 10-oxides, which are converted with Ac 2 O to the 9-(3-quinuclidylmethylene)thiaxanthenes-also prepared by dehydrating 9-(3- quinuclidylhydroxymethyl)thiaxanthene (III) with POCl 3 /pyridine; 9-(3-quinuclidyl)thiaxanthenes are prepared by reacting II with 3-phenylsulphonyloxyquinuclidine; and III is prepared by LiAlH 4 reduction of 9-(3-quinuclidylcarbonyl)- thiaxanthene. Therapeutic compositions for oral, parenteral, topical or rectal administration comprise compounds of the above formula, said to be active on the central and peripheral nervous systems and in particular to have antihistaminic, anticholinergic, neuroleptic, tranquillizing and antidepressant activity.