ES438257A2 - Process for preparing alkanolamine derivative and its acid addition salt - Google Patents

Abstract

Improvements introduced in the object of the main patent No. 421,538, filed on December 15, 1973, by PROCEDURE FOR THE OBTAINING OF ALCANOLAMINE DERIVATIVES, of general formula: r-Och2.chOh.ch2nh-a-nh-x-y-r1 where A is an alkylene radical with 2 to 12 carbon atoms; X signifies the carbonyl radical - (- CO-) or sulfonyl (-SO2-); Y means a direct bond, or an alkylene, oxyalkylene, or alkylenoxy radical each having up to 6 carbon atoms, or the imino radical (-NH-), or an alkylimino, iminoalkylene, iminoalkylenoxy, or iminoalkylenecarbonyloxy radical each having up to 6 carbon atoms carbon, or (except when R1 signifies a hydrogen atom) the oxygen atom; and where: (a) R represents a heterocyclic radical or an aryl radical of the formula: **(See formula)** and R1 represents a heterocyclic radical or an aryl radical of the formula: **(See formula)** cycloalkyl, alkenyl, alkynyl, alkoxy, alkylthio, cycloalkoxy, alkenyloxy, alkynyloxy or alkanoyl, each with up to 6 carbon atoms, or an aryl, aryloxy or dialkylamino radical, each with up to 12 carbon atoms; or wherein R12 and R13 together and/or R12 and R13 together form the radical trimethylene, tetramethylene, 1-oxotetramethylene, propenylene, but-2-enylene or butal-1,3-dienylene so that, together with 2 carbon atoms Adjacent to the benzene ring, they respectively form the indanyl radical, 5,6,7,8-tetrahydronaphthyl, 5-oxo-5,6,7,8-tetrahydronaphthyl, indenyl, 5,8-dihydronaphthyl or naphthyl; R4 represents a hydrogen atom or an amide radical of the formula: **(See formula)** where Q represents a direct bond or an alkylene or alkenylene radical each having up to 6 carbon atoms; Q1 represents an alkylene radical of up to 6 carbon atoms; R15 represents the hydrogen atom or an alkyl radical of up to 6 carbon atoms; R16 represents the hydrogen atom or an alkenyl, cycloalkyl, hydroxyalkyl or alkoxyalkyl radical, each with up to 6 carbon atoms, or an alkyl, aryl, aralkyl or aralkenyl radical, each with up to 10 carbon atoms; and R14 represents an amide radical as defined for R4; or (b) R represents a heterocyclic radical and R1 represents the hydrogen atom or an alkyl, haloalkyl, alkenyl or cycloalkyl radical, each having up to 10 carbon atoms, or an aryl radical of the formula: **(See formula)** wherein R12 and R13, the same or different, are defined as above; or its acid addition salts; characterized in that they comprise bringing together, by chemical synthesis, the following five radicals: (i) an aryloxy radical of the formula: R-O- where R has the meanings previously expressed; (ii) an oxygenated radical with 3 carbon atoms of the formula: **(See formula)** wherein R5 signifies hydrogen or a protecting group; (iii) an imino radical of formula -NR6-, wherein R6 represents hydrogen or a protecting group; (iv) a radical of the formula: -A - NR7. - where A has the above meaning and R7 signifies hydrogen or a protecting group; and (v) a radical of formula: - X - Y - R1 where R1, X and Y have the meanings previously expressed; after which if one or more of the substituents R5, R6 and R7 signify a protecting group, the protecting group or groups are removed; after which a racemic alkanolamine derivative can be resolved into its optically active anantiomorphs; and after which an alkanolamine derivative in the form of the free base can be converted into an acid addition salt thereof, by reaction with an acid. (Machine-translation by Google Translate, not legally binding)