The present invention has as its aim aminoalkoxybenzofurans, the method of 
their preparation and their application in therapeutics. These compounds 
correspond more precisely to the formula: 
##STR7## 
in which the whole of the three parameters 
##STR8## 
takes on any one of the following values: 
##STR9## 
WHERE THE ALKYL GROUP COMPRISES 1 OR 2 CARBON ATOMS) IN WHICH CASE 
##STR10## 
represents a monoalkylamino group in which the alkyl group comprises 1 to 
3 carbon atoms, a dialkylamino group in which the alkyl groups comprise 1 
to 3 carbon atoms, a cycloalkylamino group comprising 5 or 6 carbon atoms 
or a heterocyclic radical, particularly pyrrolidino, piperidino, 
hexamethyleneimino, heptamethyleneimino, 4-methyl piperidino, 4-methyl 
piperazino and 1,2,5,6-tetrahydro pyridino; and 
##STR11## 
in which cases 
##STR12## 
represents a piperidino radical. 
The method of the invention consists: 
(A) IN TREATING 5-ACETAMINO 4,7-DIMETHOXY 6-HYDROXY BENZOFURAN OF FORMULA: 
##STR13## 
described in French Pat. No. 2,178,815, with a dilute hydrochloric acid 
solution to obtain the compound: 
##STR14## 
also described in French Pat. No. 2,178,815 which is condensed: 
on isocyanates of formula: 
EQU R'.sub.4 NCO (IV) 
in which R'.sub.4 represents a methyl or ethyl group, in chloroform at room 
temperature, or 
on dimethylcarbamoyl chloride of formula: 
##STR15## 
to reflux in chloroform or in toluene in an autoclave, to obtain compounds 
of formula: 
##STR16## 
in which the group 
##STR17## 
represents a methylamino, ethylamino or dimethylamino group, then in 
condensing the compounds of formula (VI): 
either with chlorated amines of formula: 
##STR18## 
in which 
##STR19## 
represents a dialkylamino group in which the alkyl groups comprise from 1 
to 3 carbon atoms, or a heterocyclic radical, particularly pyrrolidino, 
piperidino, hexamethyleneimino, heptamethyleneimino, 4-methyl piperidino, 
4-methyl piperazino and 1,2,5,6-tetrahydro pyridino; and m being equal to 
1 or 2, to reflux in acetone or in acetonitrile in the presence of 
potassium carbonate, which leads to compounds of formula: 
##STR20## 
in which the groups 
##STR21## 
have the same significance as in formulae (VI) and (VII) respectively, m 
being equal to 1 or 2; 
or with halogenated derivatives of formula: 
##STR22## 
in which m has the value 1 or 2 at 90.degree. C. in 50% aqueous soda, or 
halogenated derivatives of formulae: 
EQU Br -- CH.sub.2 -- (CH.sub.2).sub.m -- Cl (IX) 
or 
EQU Br -- CH.sub.2 -- (CH.sub.2).sub.m -- Br (X) 
in which m has the value of 1 or 2, to reflux in acetone or acetonitrile in 
the presence of potassium carbonate; and in reacting on the new compounds 
thus obtained of formula: 
##STR23## 
in which m has the value 1 or 2, and the group 
##STR24## 
has the same significance as in formula (VI), amines of formula: 
##STR25## 
in which the group 
##STR26## 
has the same significance as in formula (VII) and may moreover represent a 
monoalkylamino group in which the alkyl group comprises 1 to 3 carbon 
atoms and a cycloalkylamino group comprising 5 to 6 carbon atoms, in 
toluene in an autoclave at a temperature of 100.degree. to 110.degree. C. 
which leads to compounds of formula: 
##STR27## 
or, when 
##STR28## 
in formula (VI) represents a monomethylamino group, with chlorated amide 
of formula: 
##STR29## 
to reflux in acetone or acetonitrile in the presence of potassium 
carbonate to obtain the compound of formula: 
##STR30## 
which is then reduced with the lithium and aluminium hydride, to reflux in 
tetrahydrofuran, which leads to the compound of formula: 
##STR31## 
(b) or by reacting the compound of said formula (II): 
with a chlorated amine of formula: 
##STR32## 
to reflux in acetone or acetonitrile in the presence of potassium 
carbonate, or 
with any one of the halogenated derivatives of formulae: 
##STR33## 
in which m is equal to 1 or 2, in 50% aqueous soda in the case of the 
derivative of formula (VIII) and in acetone or acetonitrile in the 
presence of potassium carbonate in the other cases, and in condensing the 
compounds thus obtained of formula: 
##STR34## 
with amines of formula: 
##STR35## 
in which 
##STR36## 
has the same significance as in formula (VII) in toluene in an autoclave, 
which leads to obtaining compounds of formula: 
##STR37## 
in which m is equal to 1 or 2 and 
##STR38## 
has the same significance as in formula (XVI), which is treated with a 
diluted hydrochloric acid solution to obtain compounds of formula: 
##STR39## 
where m and 
##STR40## 
have the same significance as in formula (XVII), which are reacted: 
with said isocyanates of formula (IV), in toluene in an autoclave to obtain 
compounds of formula: 
##STR41## 
in which R'.sub.4 has the same significance as in formula (IV) and 
##STR42## 
has the same significance as in formula (XVIII), and m is equal to 1 or 2, 
or, 
when 
##STR43## 
represents a piperidino radical and m is equal to 1 or 2, with said 
dimethyl carbamoyl chloride of formula (V), to obtain the compound of 
formula: 
##STR44## 
this reaction being carried out in toluene at room temperature. 
The compound of formula: 
##STR45## 
prepared in accordance with the above method may then be reacted with 
N-methylpiperazine of formula: 
##STR46## 
to reflux in toluene which leads to the compound of formula: 
##STR47##