SE8206546L - (2,3)-Alkylenedioxy-benzamide derivs. - for use as anxiolytics, antidepressants and antiemetics - Google Patents

Abstract

of formula (I) and their acid -addn. salts, quat. ammonium salts, oxides and optical isomers are new. In (I), A is 1-3C alkylene opt. substd by 1-4C alkyl, 2-4C alkenyl or 1-4C hydroxyalkyl. R is H, 1-4C alkyl or -B-NR1R2; B is a direct bond or a 1-3C alkylene gp. opt. substd. by 1-4C alkyl or 2-4C alkenyl; R1 is H, 1-4C alkyl, 2-4C alkenyl, 2-4C alkynyl, substd. alkyl, or forms a heterocyclic ring with B, and R2 is H, 1-4C alkyl, 2-4C alkenyl or alkynyl, substd. alkyl, an opt. substd. heterocyclic gp., or a phenyl, adamantyl, cycloalkyl, bicycloalkyl or cycloalkenyl gp. bonded directly to the N atom or via an opt. substd. alkylene chain, or NR1R2 is a heterocycle opt. contg. other heteroatoms (including NR", where R" is H- 1-4C alkyl, 2-4C alkenyl or alkynyl, phenyl, benzyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkenylalkyl, adamantyl, bicycloalkyl or alkyl substd by OH, SH, acyl, thioacyl, alkoxy or alkylthio). R' is H, 1-4c alkyl, 2-4C alkenyl or alkynyl, adamantyl, pyrimidinyl, pyrazinyl, diazepinyl, quinuclidinyl, azabicycloalkyl, diazabicycloalkyl, bicycloalkyl, or opt. substd. phenyl or aralkyl, or R'+B forms an opt. substd. heterocycle contg. a single N atom, or R'+R1 forms an opt. substd. heterocycle contg. two heteroatoms, X is H, halogen, OH, 1-4C alkoxy, 1-4C alkyl, amino opt. mono- or disubstd. by 1-4C alkyl, acyl, aralkyl, furyl, pyranyl or alkoxycacarbonyl, or forms an A' chain with Y. Y is as defined for X or is NO2, 1-4C alkylsulphonyl, adamantyl-sulphonyl, cycloalkyl sulphonyl or SO2NR3R'; R3 and R4 are H, 1-4C alkyl, 2-4C alkenyl, 2-4C alkynyl, phenyl, benzyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkenylalkyl, bicycloalkyl, adamantyl, pyrimidinyl, pyrazinyl, or alkyl substd. by OH, SH, acyl, thioacyl, alkoxy or alkylthio, or NR3R4 is an opt. substd. heterocycle opt. congt. another heteroatom; or Y forms an A chain with X or Z. Z is as defined for X or is NO2, or forms an A chain with Y. A is a carbon chain opt. substd. or opt. interrupted by one or more opt. substd. heteroatoms. Cpds. (I) have anxiolytic, antidepressant and antiemetic activity with little or no cataleptic activity. A typical cpd. of N-(1-allyl-2-pyrrolidinylmethyl)-7-methylsulphamoyl-1, 4-benzodioxan-5-carboxamide. In an example, this is prepd. from 1,4-benzodioxan-5-carboxylic acid.

Claims (3)

Claims 1. Substituted 2,3-alkylene-bis (oxy) benzoic acids for use as intermediates in the preparation of therapeutically valuable, substituted 2,3-alkylene-bis- (oxy) -benzamides, characterized by the general formula: COOS ( V) 'X van i A represents an alkylene chain having 1-3 carbon atoms, preferably di. methylene, ethylene or propylene, X represents hydrogen, halogen, hydroxy, alkoxy having 1-4 carbon atoms, mainly damethoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy or t-butoxy, alkyl having 1-4 carbon atoms, mainly methyl, ethyl, propyl, isopropyl, butyl, isobutyl or t-butyl, nitro or acetamino, Y represents halogen, 111110.4 amino or acetamino, or Y represents sulfonyl mecol atoms, especially methylwilfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, butylsulfonyl, butylsulfonyl , or sulfamoyl, C 1 -C 4 alkylsulfamoyl, C 1 -C 4 dialkylsulfamoyl, adamantylsulfamoyl or cycloalkylsulfamoyl or are attached to X to form an azimido group, and represent hydrogen, halogen, nitro or acetamino, or are attached to Y to alt. azinido group, with the conditions, alt 1. nal, A represents methylene or ethylene and Z represents vate. X and Y joke simultaneously denote vale, 2. nal. X and 2 represent Irate and A represents methylene or ethylene, Y is different from a bromine atom, 3. when X and Z denote hydrogen atoms and A denotes a methylene group, Y joke denotes nitro, acetamino or amino, - when Y and Z denote hydrogen atoms and A denotes a methylene group, s joke denotes a methoxy group, s - when A denotes a methylene group and Z represents X and Y joke-like betec'methoxy.