Phenylethanolamine therapeutic agents

Claim 2

Compounds of the general formula ##STR16## or physiologically acceptable salts thereof, in which R 1 is a halogen atom or a group NR 2 R 3 ; R 2 and R 3 , which may be the same or different, are hydrogen or (C 1 -C 6 ) straight or branched chain alkyl; or R 2 may be hydrogen and R 3 may be group R 4 CO or R 4 SO 2 where R 4 is hydrogen or alkyl (C 1-4 ); R 5 is hydrogen or one or more halogen atoms or hydroxy or alkoxy (C 1-4 ) groups; and X is CH 2 , O or a group NR 6 where R 6 is hydrogen or alkyl (C 1-4 ).

Claim 3

Compounds as claimed in claim 1 in which R 1 is chlorine, fluorine, amino, alkyl (C 1-4 ) amino, or dialkyl (C 1-4 ) amino.

Claim 4

Compounds as claimed in claim 1 in which R 5 is hydrogen or halogen.

Claim 5

Compounds as claimed in claim 3 in which R 5 is para-fluoro.

Claim 6

Compounds as claimed in claim 1 in which X is --CH 2 --.

Claim 7

A compound as claimed in claim 1 which is 2-fluoro-5-[1-hydroxy-2[[3-(4-fluorophenyl)-1-methylpropyl]-amino]ethyl]benzenesulphonamide.

Claim 8

A compound as claimed in claim 1 which is 2-fluoro-5-[1-hydroxy-2-[(1-methyl-3-phenylpropyl)amino]ethyl]benzenesulphonamide.

Claim 9

A compound as claimed in claim 1 which is 2-dimethylamino-5-[1-hydroxy-2-[(1-methyl-3-phenylpropyl)amino]ethyl]benzenesulphonamide.

Claim 10

A compound as claimed in claim 1 which is 2-amino-5-[1-hydroxy-2-[(1-methyl-3-phenylpropyl)amino]ethyl] benzenesulphonamide.

Claim 11

A compound as claimed in claim 1 which is 5-[1-hydroxy-2-[(1-methyl-3-phenylpropyl)amino]ethyl]-2-methylaminobenzenesulphonamide.

Claim 12

A compound as claimed in claim 1 which is 2-(butylmethylamino)-5-[1-hydroxy-2-[(1-methyl-3-phenylpropyl)amino]ethyl]benzenesulphonamide.

Claim 13

A compound as claimed in claim 1 which is 2-fluoro-5-[1-hydroxy-2-[[3-(3-fluorophenyl)-1-methylpropyl]amino]ethyl]benzenesulphonamide.

Claim 14

A compound as claimed in claim 1 which is 2-(ethylmethylamino)-5-[1-hydroxy-2-[(1-methyl-3-phenylpropyl)amino]amino]ethyl]benzenesulphonamide.

Claim 15

A process for the preparation of compounds as claimed in claim 1 which comprises; a. reducing compounds of the general formula: ##STR17## in which R 1 has the meaning given in claim 1 and R 7 represents a group R of the formula: ##STR18## in which X and R 5 have the meanings given in claim 1 and R 8 represents hydrogen or benzyl, with subsequent conversion of the group R 8 when this is benzyl to hydrogen; or b. reductively alkylating a compound of the formula: ##STR19## or the corresponding alcohol thereof in which R 1 has the meaning given in claim 1, and R 7 represents benzyl and R 8 represents hydrogen or benzyl with a ketone of the formula: ##STR20## in which R 5 and X have the meaning given in claim 1; or c. condensing an amine of the formula: ##STR21## in which R 1 has the meaning given in claim 1 and R 7 and R 8 are both hydrogen, with a ketone of the formula ##STR22## in which R 5 and X have the meanings given in claim 1 and reducing the resulting condensation product; d. condensing a glyoxal of the formula ##STR23## in which R 1 has the meaning given in claim 1, with an amine of the formula RNH 2 , in which R has the meaning given in (a) above to provide an intermediate azomethine of the formula: ##STR24## which is then reduced; or e. reacting a halohydrin of the formula (XIV) or an epoxide of formula (XV): ##STR25## in which R 1 has the meaning given in claim 1 and Hal represents halogen, with an amine of the formula RNH 2 in which R has the meaning given in (a) above; the desired product in all cases being isolated in the free base or in the form of a physiologically acceptable salt thereof.

Claim 16

A process as claimed in claim 14(a) in which reduction is effected by a non-catalytic reduction procedure and subsequent debenzylation is effected by catalytic hydrogenolysis.