Process for the preparation of therapeutically useful...

C - Chemistry – Metallurgy – 07 – D

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C07D 295/16 (2006.01) C07C 275/34 (2006.01) C07D 211/46 (2006.01) C07D 211/52 (2006.01) C07D 211/70 (2006.01) C07D 215/06 (2006.01) C07D 215/08 (2006.01) C07D 215/42 (2006.01) C07D 215/44 (2006.01) C07D 217/06 (2006.01) C07D 261/02 (2006.01) C07D 265/30 (2006.01) C07D 265/36 (2006.01) C07D 295/088 (2006.01) C07D 295/13 (2006.01) C07D 295/15 (2006.01) C07D 295/185 (2006.01) C07D 295/205 (2006.01) C07D 295/215 (2006.01) C07D 295/24 (2006.01) C07D 295/26 (2006.01) C07D 295/28 (2006.01) C07D 307/14 (2006.01) C0

Patent

CA 1104132

ABSTRACT OF THE DISCLOSURE The disclosure describes derivatives of 3,4,5-tri- methoxybenzene, their preparation as well as their therapeutical use, in particular as tranquillisers, myorelaxants and anti- convulsants. They are compounds of the formula I Image (I) wherein each of m and n, which may be the same or different, represents 0, 1 or 2, X represents an oxygen atom or an imine group of formula NR3 (wherein R3 represent; a hydrogen atom or a benzyl or morpholinoethyl group), Y represents cne of the divalent groups CO, CONH, COO or SO2, and NR1R2 represents a dimethylamino, diethylamino, dipropyl- amino, dibutylamino, allylamino, isobutenylamino, cyclopentylamino, cyclohexylamino, cycloheptylamino, cyclooctylamino, N-methyl N-cyclopentylamino, N-methyl N-cyclohexylamino, N-allyl N-cyclohexylamino, adamantyl- amino, diethoxyethylamino, dimethylaminoethylamino, dimethylaminopropylamino, N-methyl N-dimethylamino- propyl-amino, benzylamino, 3,4,5-trimethoxybenzylamino, phenethylamino, p-chlorophenethylamino, tetrahydrofur- furylamino, tetrahydropyranyl-methylamino, pyrrolidino, isoxazolidinyl, piperidino, 4-hydroxypiperidino, 4-p-chlorophenyl-4-hydroxypiperidino, homopiperidino, 1,2,3,6-tetrahydropyridyl, morpholino, 2-methyl- morpholino, 2,6-dimethylmorpholino, 2-morpholino- ethylamino, thiamorpholino, piperazino, 4-methylpipera- zino, 4-(?-m-chlorophenyl-benzyl)-piperazino, 4-(3,4,5- trimethoxyphenylaminocarbonyl)-piperazino, 4-(3,4,5- trimethoxyphenylaminocarbonylmethyl)-piperazino, 4- phenylpiperazino, 4-m-trifluoromethylphenyl-piperazino, 4-piperidino carbonylmethyl-piperazino, 1,2,3,4- tetrahydroquinolyl, 1,2,3,4-tetrahydroisoquinolyl, (7-chloro-4-quinolyl)-amino, 1,2,3,4-tetrahydro- benzoxazinyl or 1,2,3,4-tetrahydro-6-chloro-benzoxazinyl group, as well as their pharmaceutically acceptable acid addition salts. The compounds of the formula I may be obtained from known compounds according to the following general scheme: Image In these formulae A represents a -N=C=O, NH2, OH or -NH-(CH2)m- CO-hal group, B represents H, NH2, OH, hal-CO- or hal-SO2-, hal being a halogen, preferably chlorine atom, and NR1R2, m and n have the same meanings aq in formula I.

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