Derivatives having expectorant activity, the procedure for their preparation and the pharmaceutical compositions which contain them

Claim 2

A compound having formula (I), ##STR19## where R represents the groups: guaiacolglycolyl, (4-methylguaiacol)glycolyl, m-cresolglycolyl, o-cresolglycolyl, p-cresolglycolyl, thymolglycolyl, carvacrolglycolyl and guaiacolcarbonyl and pharmaceutically acceptable salts of the same compound.

Claim 3

A compound, as per claim 1, wherein it is N-(2-amino-3,5-dibromobenzyl)-trans-4-amino-1-(guaiacolglycolyl)cyclohexane or one of its pharmaceutically acceptable salts.

Claim 4

A compound, as per claim 1, wherein it is N-(2-amino-3,5-dibromobenzyl)-trans-4-amino-1-(4-methyl-guaiacolglycolyl)cyclohexane or one of its pharmaceutically acceptable salts.

Claim 5

A compound, as per claim 1, wherein it is N-(2-amino-3,5-dibromobenzyl)-trans-4-amino-1-(m-cresolglycolyl)cyclohexane or one of its pharmaceutically acceptable salts.

Claim 6

A compound, as per claim 1, wherein it N-(2-amino-3,5-dibromobenzyl)-trans-4-amino-1-(o-cresolglycolyl)cyclohexane or one of its pharmaceutically acceptable salts.

Claim 7

A compound, as per claim 1, wherein it N-(2-amino-3,5-dibromobenzyl)-trans-4-amino-1-(p-cresolglycolyl)cyclohexane or one of its pharmaceutically acceptable salts.

Claim 8

A compound, as per claim 1, wherein it is N-(2-amino-3,5-dibromobenzyl)-trans-4-amino-1-(thymoglycolyl)cyclohexane or one of its pharmaceutically acceptable salts.

Claim 9

A compound, as per claim 1, wherein it is N-(2-amino-3,5-dibromobenzyl)-trans-4-amino-1-(carvacrolglycolyl)cyclohexane or one of its pharmaceutically acceptable salts.

Claim 10

A compound, as per one of the preceding claims from 1 to 8, wherein the said pharmaceutically acceptable salt is a salt with the acids; hydrochloric, hydrobromic, hydroiodic, phosphoric, sulphuric, maleic, citric, acetic, oxalic, succinic, benzoic, tartaric, fumaric, mandelic, ascorbic and malic.

Claim 11

A compound, as per one of the preceding claims from 2 to 8, wherein the said pharmaceutically acceptable salts is a hydrochloride.

Claim 12

A process for the preparation of a compound, as defined in claim 1, wherein trans-1-bromo-4-aminocyclohexane, having formula (II), ##STR20## is made to react with 2-amino-3,5-dibromobenzaldehyde, having formula (III), ##STR21## to obtain the aldiminic intermediate having formula (IV), ##STR22## which is reduced with hydrogen in the presence of Nickel-Raney to obtain N-(2-amino-3,5-dibromobenzyl)-trans-4-amino-1-bromo-cyclohexane, having formula (V) ##STR23## which is made to react with carboxylic acid having formula (VI), ROH (VI) where R is as defined in claim 1, in the presence of an alkaline carbonate and a catalyst, to obtain the corresponding formula (I) compound, as defined in claim 1, which, optionally, is salified.

Claim 13

A process, of claim 11, wherein the reaction between compounds (V) and (VI) is effected in N,N-dimethylformamide.

Claim 14

A process, as per one of the preceding claims 11 and 12, wherein the said alkaline carbonate is either sodium or potassium carbonate.

Claim 15

A process, as per one of the preceding claims 11 to 13, wherein the said catalyst is either sodium or potassium iodide.

Claim 16

A process, as per one of the preceding claims 11 to 14, wherein the formula (II) compound, as defined in claim 11, is obtained in the form of hydrochloride by reacting trans-4-aminocyclohexanol, which has formula (VII) ##STR24## with phthalic anhydride and then with phosphorus tribromide to obtain trans-1-bromocyclohexyl-4-phthalimide, having formula (XI), ##STR25## which is hydrolyzed with hydrochloric acid to obtain the formula (II) compound.

Claim 17

A pharmaceutical composition, wherein it contains, as active principle, an effective quantity of one or more of the compounds as per claim 1, just as they are or in combination with vehicles, diluents, solvents and/or pharmaceutically acceptable excipients.

Claim 18

A composition, of claim 16, wherein it is a capsule or pill, which releases the active principle at a normal or a progressively retarded rate, a syrup or emulsion, which is either ready-to-use or extemporaneous, containing from 45 to 135 mg of active principle per posological unit.

Claim 19

A composition, of claim 16, wherein it is a vial, which is ready-to-use or extemporaneous, for administration by injection, containing from 15 to 45 mg of active principle.

Claim 20

A composition, of claim 16, wherein it is suitable for administration by spraying.

Claim 21

A composition, of claim 19, wherein it contains from 15 to 30 mg of active principle per posological unit.

Claim 22

A composition, of claim 16, wherein it is suitable for rectal administration and contains from 15 to 90 mg of active principle per posological unit.