GB1112601A - 9,10-dihydro-4h-benzo[4,5] cyclohepta [1,2-b] thiophene derivatives and their production - Google Patents

Abstract

The invention comprises compounds of the formula <FORM:1112601/C2/1> and acid addition salts thereof, in which (i) R1 is H or CH3, R2 is H, R3 is C1- 4 alkyl and R14 is C1- 4 alkyl; or (ii) R1 is H or CH3, R2 is H and R3 and R14 with the nitrogen atom form a piperidino, pyrrolidino or 4-(C1- 4 alkyl)-piperazino radical; or (iii) R1 with R3 forms a -(CH2)2- or -(CH2)3 - radical, R2 is H and R14 is H or C1- 4 alkyl; or (iv) R1 and R3 together form a -(CH2)3- or -(CH2)4-radical and R14 is H or C1- 4 alkyl; X and Y are hydrogen atoms or together form a second bond and in the case where X and Y are hydrogen R14 may also be a group -COOR5, in which R5 is a C1- 4 alkyl or C7- 10 aralkyl group; and comprises also processes for preparing these compounds by (a) for the preparation of compounds wherein X and Y are hydrogen, heating the corresponding compound wherein X and Y together form a second bond or X represents OH and Y represents H with hydrogen iodide and red phosphorus, or (b) for the preparation of compounds wherein R14 is H or COOR5, reacting a compound wherein R14 is CH3 with a chloroformic ester Cl.COOR5 and if desired, hydrolysing the resulting compound wherein R14 is COOR5. Compounds of the above formula wherein X and Y together form a second bond are made by reacting 9,10-di-hydro - 4H - benzo - [4,5] - cyclohepta - [1,2-b]-thiopen-4-one with a Grignard compound of the formula Hal-Mg-CH2.CHR1.CHR2.NR3R4 to give an intermediate product of the above formula wherein X is OH and Y is H which is then treated to split off water, e.g. with hydrogen chloride and glacial acetic acid. Pharmaceutical preparations having pharmacodynamic properties comprise the above compounds of the invention and a carrier, preferably in a form adapted to the enteral or parenteral administration of 15-300 mg. per day.