Benzo-indolyl guanidine(s) - having salidiuretic and antihypertensive properties, prepd. from benzo-indolyl amine(s)

摘要

Benzo(c,d) indolyl-1-guanidine derivs. of formula (I) and their salts are new. In the formula R1 is in position 3 or 5 and is F, Cl, Br, -NHCOR3 or NR4R5; R2 is H, or -COR6; R3 is H, 1-4C alkyl or alkoxy, 3-7C cycloalkyl, 5-6 membered O, N, or S heterocycle, phenyl or phenyl 1-5C alkyl, the benzene rings in these last two substituents opt. being substd. by 1 or 2 F, Cl, Br, or 1-4C alkyl or alkoxy gps; R4 is H; R5 is 7-7C cycloalkyl, or R4 and R5 are independently H or 1-4C alkyl; R6 is selected from the same groups as R3; with the proviso that when R1 is halogen in the 5 position then R2 is not H or -COR'6 where R6 is 1-4C alkyl). Specific (I) is N-acetyl-N-(1,2,6,7,8,8a-hexahydro-5-propionamido-1-benzol c,d indolyl) guanidine methane sulphonate, m.pt. 184-186 degrees C (decomp). This was prepd. by mixing 15.3 g 1-amino-1,2,6,7,8,8a-hexahydro-5-propionamido-benzo c,d indole and 181 ml isopropanol and adding 14.2 g 1-acetyl-2-methyl iosthioruea methane sulphonate over 1 hour. The mixt. was heated at 30-35 degrees C and N2 passed to eliminate methane thiol. The prod. was recrystallised from methanol and isopropanol.