Novel indolyl alkyl amines, method of producing same, and their use as anorectic agents

#This invention relates to novel indolyl alkyl amines of the general formula ##SPC2##

#And their salts with organic or inorganic acids. In this formula I, A and A.sup.1 denote identical or different alkyl radicals which both together have a total of 3-8 C-atoms. R.sup.1 denotes hydrogen, a lower alkyl radical having up to 4 C-atoms or a possibly substituted benzyl or benzoyl radical. R.sup.2 and R.sup.3 may be the same or different and denote hydrogen, a halogen (more particularly chlorine, bromine or fluorine) or (possibly halogenated) lower alkyl radicals or (possibly etherified) hydroxy radicals. R.sup.4 denotes hydrogen, a lower alkyl radical, an acyl group or a (possibly substituted) benzyl radical or the cyano-ethyl group. The compounds represented by Formula I and their salts (in particular the 3-(2'-amino-2'-methylbutyl)-indole and the salts of same such as the hydrochloride salt) are useful as anorectic agents for a method of inhibiting or reducing appetite in mammals and human beings.

#The novel compounds of the invention are preferably prepared by reacting a gramine which is possibly substituted with R.sup.2 and/or R.sup.3 at the benzene ring, with a nitroparaffin, the nitro-group of which is fixed to a non-terminal C-atom, whereupon the 3-nitroalkyl indol which forms as intermediate is condensed with a compound of the formula R.sup.1 --X (where X denotes a radical liberated under condensation conditions, for example a halogen or an aryl-sulphonic acid radical), if desired, for the purposes of introducing a substituent R.sup.1 other than H into the ring nitrogen, and then the nitro-group is reduced to the amino-group, whereupon if required a radical R.sup.4 other than H is introduced into the amino-group. The resulting primary or secondary amines can then, if required, be converted to the corresponding salts by the action of organic or inorganic acid.

#A mixture of 34.8 g (200 mM) of gramine, 242.5 ml of 2-nitrobutane and 9 g of solid sodium hydroxide was heated to reflux temperature in a nitrogen atmosphere for 8 hours. The mixture was suction-filtered after cooling. The pH of the filtrate was adjusted to 4 with 10% acetic acid (80 ml) and the filtrate was washed with five times 180 ml of water. The organic phase was treated with activated charcoal and then dried with sodium sulphate. Evaporation yielded 43.4 g of residue having a melting point of 69.degree.-73.degree.C. This was chromatographed on 15 times the quantity of aluminium oxide activity III. Evaporation of the combined benzene eluates gave 36.6 g of product having a melting point of 76.5-78.5.degree.C. (yield: 79% of the theoretical), from which 3-(2'-methyl-2'-nitrobutyl)-indole was obtained by recrystallising from benzine to a constant melting point of 79.degree.-81.degree.C.

#Calculated for C.sub.13 H.sub.16 N.sub.2 O.sub.2 (232.3): 13.77% O.

#Found: C.sub.12.8 H.sub.15.4 N.sub.2 13.75% O.