Patent GB-1380243-A (GB)
Title: Thienobenzazepines processes for their preparation and compositions incorporating them
IPC: C07D495/04
Filed: 1972-03-01
Abstract: 1380243 4-Aminoalkyl-4H-thieno-[3,2-b][f] benzazepines ROUSSEL-UCLAF 1 March 1972 [1 March 1971] 9654/72 Heading C2C Novel 4 - aminoalkyl - 4H - thieno - [3,2-b] [f]benzazepines of the general formula wherein each of R<SP>1</SP> and R<SP>2</SP> (at the 5-, 6-, 7- or 8- position), is a hydrogen or halogen atom or a trifluoromethyl, optionally substituted alkoxy, alkylthio, alkyl, optionally substituted sulphamoyl, dialkylamino or acylamino group; A is C 2-5  alkylene group; B is a hydrogen atom or an alkyl or aralkyl group; C is an alkyl or aralkyl group; or B and C together form a C 2-6  alkylene group, optionally interrupted by one or two heteroatoms; R (at the 2- or 3-position), is a hydrogen atom or alkyl group; Y is a hydrogen atom or a hydroxyl, alkoxy, alkylthio or acyloxy group; Z is a hydrogen atom or an alkyl, alkoxy or alkylthio group; Z<SP>1</SP> is a hydrogen atom or alkyl group ; X is a hydrogen atom; or Y and Z together form a ketonic oxygen function or a C 2-4  alkylenedioxy, alkylenedithio or alkylenethiooxy group; or Y and X together form an additional C-C bond between the atoms to which they are attached, and acid addition salts thereof are prepared (a) by reaction of the corresponding compound in which -A-NBC is replaced by a hydrogen atom with an aminoalkyl halide of the general formula wherein hal is a chlorine, bromine or iodine atom, in the presence of a basic agent; (b) when Y and Z together form a ketonic oxygen function, by acid hydrolysis of the corresponding compound in which each of Y and Z is an alkoxy or alkylthio group or Y and Z together form an alkylenedioxy, alkylenedithio or alkylene thiooxy group; (c) when Y is a hydroxyl group and Z is a hydrogen atom, by reduction of the corresponding compound in which Y and Z together form a ketonic oxygen function; (d) when Y and X together form an additional C-C bond between the atoms to which they are attached, by dehydration of the corresponding compound in which Y is a hydroxyl group with an acid; (e) when each of Y and Z is a hydrogen atom, by reduction of the corresponding compound in which Y and Z together form a ketonic oxygen function; (f) when Y is a hydroxyl group and Z is an alkyl group, by reaction of the corresponding compound in which Y and Z together form a ketonic oxygen function with an appropriate organometallic reagent; (g) when Y is a hydrogen atom, by hydrogenolysis of the corresponding compound wherein Y is a hydroxyl group; (h) when Z<SP>1</SP> is an alkyl group, by alkylation of the corresponding compound in which Z<SP>1</SP> is a hydrogen atom; and (i) when B is a hydrogen atom and C is an alkyl group, by reaction of the corresponding compound in which each of B and C is an alkyl group, with an alkyl haloformate and alkaline hydrolysis of the resulting N-alkyl-N- carbalkoxy-amino derivative; followed optionally by salification of the product. Pharmaceutical compositions having antidepressant activity comprise, as active ingredient, a 4-aminoalkyl-4H-thieno[3,2-b][f]benzazepines of the first general formula above or an acid addition salt thereof, together with a suitable pharmaceutical vehicle.