Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1998-06-08
1999-07-13
Kight, John
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
549373, 548517, 546207, 546245, 514336, 514422, 514452, A01N 4332, A01N 4340, C07D31906, C07D40100
Patent
active
059227397
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to compounds of general formula (I) ##STR2## in which R.sub.1 represents a hydrogen atom or a (C.sub.1 -C.sub.4)alkyl, (C.sub.3 -C.sub.6)cycloalkylmethyl or phenyl(C.sub.1 -C.sub.3)alkyl group optionally substituted on the phenyl ring with one or more atoms or groups chosen from halogens and methyl, trifluoromethyl, methoxy and cyano groups, R.sub.2 represents a hydroxyl or (C.sub.1 -C.sub.4)alkoxy group or a group of general formula NR.sub.3 R.sub.4 in which R.sub.3 and R.sub.4, independently of each other, each represent a hydrogen atom, a linear or optionally branched (C.sub.1 -C.sub.4)alkyl group, a (C.sub.3 -C.sub.6)cycloalkyl group, a (C.sub.3 -C.sub.6)cycloalkylmethyl group, a phenyl group, a phenylmethyl group or a pyridyl group, or alternatively R.sub.3 and R.sub.4 form, together with the nitrogen atom which bears them, a pyrrolidine or piperidine ring, and n represents the number 1, 2 or 3.
The compounds of the invention may exist in the form of cis or trans stereoisomers or mixtures of such isomers; they may also exist in the form of free bases or addition salts with acids.
The preferred compounds are those of general formula (I) in which R.sub.1 represents a methyl, ethyl or phenylmethyl group optionally substituted on the phenyl ring, R.sub.2 represents an amino or (C.sub.1 -C.sub.4)alkylamino group and n is equal to 1; among the latter, the compound in whose formula R.sub.1 represents a phenylmethyl group and R.sub.2 represents an amino group is particularly advantageous.
The compounds according to the invention may be prepared by various processes.
According to a first variant, an amine of general formula (II) ##STR3## in which R.sub.1 represents a hydrogen atom or an alkyl group, may be reacted with an .omega.-halo alkanoate of general formula (III) ##STR4## in which Z represents a chlorine or bromine atom and n is as defined above; a compound of general formula (I) is thus obtained in which R.sub.1 represents a hydrogen atom or an alkyl group and R.sub.2 represents an ethoxy group. If so desired, the compound thus obtained may then be saponified to convert it into the corresponding acid, or alternatively it may be reacted with an amine of general formula HNR.sub.3 R.sub.4, in which R.sub.3 and R.sub.4 are as defined above, to convert it into amide. The conditions of these reactions are standard and are well known to those skilled in the art.
According to a second variant, the amides of general formula (I) in which R.sub.1 represents a hydrogen atom or an alkyl group may be obtained by reacting the amine of general formula (II) directly with an .omega.-halo alkanamide of general formula (IV) ##STR5## in which X represents a chlorine or bromine atom and R.sub.3, R.sub.4 and n are as defined above. The conditions of this reaction are well known to those skilled in the art.
According to a third variant, the amides of general formula (I) in which R.sub.1 represents a hydrogen atom or an alkyl group and n=2 may be obtained by reacting the amine of general formula (II) with a propenamide of general formula (V) ##STR6## in which R.sub.3 and R.sub.4 are as defined above. The conditions of this Michael reaction are well known.
Lastly, and according to a fourth variant, the compounds of general formula (I) in which R.sub.1 does not represent a hydrogen atom may be prepared by alkylation of the corresponding compound in whose formula R.sub.1 represents a hydrogen atom, in a polar aprotic solvent, for example acetonitrile, in the presence of a base, for example potassium carbonate.
The starting amines of general formula (II) in which R.sub.1 represents an alkyl group may be obtained by reduction of the corresponding alkanamides, described in Patent Application EP-461,958; the starting amines of general formula (II) in which R.sub.1 represents a hydrogen atom may be obtained by reaction of 2-(6-methoxynaphthalen-1-yl)propane-1,3-diol with 4,4-diethoxybutanamine, as described in the said patent application.
The starting compounds of general formulae (III), (IV) and (V) are c
REFERENCES:
patent: 5192797 (1993-03-01), Raizon et al.
Dargazanli Gihad
Evanno Yannick
Frost Jonathan
George Pascal
Lardenois Patrick
Kight John
Synthelabo
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