Benzylamine derivatives, their preparation and their application

Details Benzylamine derivatives, their preparation and their application Benzylamine derivatives, their preparation and their application

1999-02-26

2000-05-09

Lambkin, Deborah C.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

514443, 549467, 549 49, A61K 3134, A61K 3138, C07D30778, C07D33352

Patent

active

060605081

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to benzylamine derivatives, their preparation and their application in therapeutics.
The compounds of the present invention correspond to the general formula (I) ##STR2## in which: A represents either a hydrogen atom, a hydroxyl, a C.sub.1-6 hydroxyalkyl group, a thiol, a C.sub.1-6 alkylsulphanyl group, an amino group, a C.sub.1-6 alkylamino group, a di(C.sub.1-6 alkyl)amino group, a C.sub.1-6 alkylhydroxylamine group, a C.sub.1-6 alkoxy group, a hydroxylamine group, an N,O-di(C.sub.1-6 alkyl)hydroxylamine group, an azido or a halogen such as fluorine, chlorine or bromine, C.sub.2-6 alkenyl group, a C.sub.1-6 fluoroalkyl group, a C.sub.1-2 perfluoroalkyl group, a C.sub.1-6 alkoxy group, a phenyl group or an oxo group, hydrogen atom, a halogen such as fluorine, chlorine or bromine, a cyano, a carboxamide, a linear or branched C.sub.1-6 alkyl group, a C.sub.2-6 alkenyl group, a C.sub.3-6 cycloalkyl group, a C.sub.1-6 alkoxycarbonyl group, a C.sub.1-6 hydroxyalkyl group, a C.sub.1-6 alkoxy group, a C.sub.1-6 alkoxyalkyl group, a C.sub.1-6 fluoroalkyl group or a C.sub.1-2 perfluoroalkyl group or R.sub.1 and R.sub.2, together with the double bond to which they are attached, form a C.sub.3 -C.sub.6 cycloalkenyl ring, a C.sub.4 -C.sub.6 cycloalk-diene-yl ring or a C.sub.5-6 aryl ring, hydrogen atom, a C.sub.1-6 alkyl group, a C.sub.2-6 alkenyl group, a C.sub.3-6 cycloalkyl group, a C.sub.3-6 cycloalkenyl group, a C.sub.1-6 fluoroalkyl group or a C.sub.1-2 perfluoroalkyl group or R.sub.3 and R.sub.4 together form a C.sub.2-6 alkylene group or a C.sub.2-6 alkenylene group, such as, for example, a --C.sub.2 H.sub.5 group, a --C.sub.3 H.sub.3 -- group or a --C.sub.4 H.sub.8 -- group, or R.sub.3 and R.sub.4, together with the nitrogen atom to which they are attached, form a saturated or unsaturated heterocyclic ring having 2 nitrogen atoms and from 3 to 6 carbon atoms, the available nitrogen atom optionally being substituted by a C.sub.1-4 alkyl group, such as, for example, a piperazyl ring or imidazolyl ring, or R.sub.3 and R.sub.4, together with the nitrogen atom to which they are attached, form a saturated or unsaturated heterocyclic ring having an O atom, a N atom and from 3 to 6 carbon atoms, such as, for example, a morpholinyl ring, and or bromine.
The compounds of general formula (I) can contain one or more asymmetric carbon atom. They can thus exist in the form of enantiomers or of diastereoisomers. These isomers and their mixtures, including racemic mixtures, form part of the invention. Suitable pharmaceutically acceptable acids include hydrochloric and fumaric acids.
The compounds of general formula (I) can exist in the form of a free base or of addition salts with pharmaceutically acceptable acids, which also form part of the invention.
The compounds of the invention can be prepared by processes illustrated in the following schemes.
The compounds of formula (I), in particular those in which A represents a hydroxyl group, can be prepared according to the process described in Scheme 1, set out below.
According to this process, an ethenyl derivative of formula IV can be reacted with an oxidizing agent, such as sodium periodate, osmium tetroxide or meta-chloroperbenzoic acid, in basic or acidic medium, so as to form a diol of formula III. The hydroxyl group geminal to the group B can be selectively protected by a protecting group P, in a way known to a person skilled in the art, for example by formation of a silyl ether, so as to obtain a compound of formula II. The hydroxyl group carried by the carbon alpha to the heterocycle of the compound thus obtained can then optionally be activated, in a way known to a person skilled in the art, so as to obtain a nucleofuge group, such as a mesyl or tosyl group or a bromine atom. The compound of formula (I) according to the invention can then be prepared from this compound by reacting the compound with an amine NMR.sub.3 R.sub.4, followed by deprotection by methods known to a person skilled in the art. The meanings of X, R.sub.1, R.sub.2, R.

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