Urea derivatives, their preparation and medicinal products conta

Details Urea derivatives, their preparation and medicinal products conta Urea derivatives, their preparation and medicinal products conta

1992-09-11

1994-08-16

Dees, Jose' G.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Ester doai

560 34, 560 9, C07C22926, A61K 3113

Patent

active

053387600

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to compounds of formula ##STR2## to their preparation and to medicinal products containing them.
In the formula (I): --CO--R.sub.4 in which m is equal to 0, 1 or 2 and R.sub.4 represents hydroxyl, alkoxy or amino radical, alkylthio radical, and except where otherwise stated, the alkyl and alkoxy radicals contain 1 to 4 carbon atoms in a straight or branched chain.
In the formula (I), the halogen atoms are preferably chlorine, bromine or fluorine atoms.
The racemates and enantiomers of the compounds of formula (I) form part of the invention.
The compounds of formula (I) for which R.sub.2 represents a phenyl radical or a chain --(CH.sub.2).sub.m --CO--R.sub.4 in which m is equal to 0, 1 or 2 and R.sub.4 represents an alkoxy radical may be obtained by the action of an amine of formula: ##STR3## in which R.sub.1 has the same meanings as in the formula (I), on an acid of formula: ##STR4## in which n and R.sub.3 have the same meanings as in the formula (I) and R.sub.2 has the same meanings as above, or a reactive derivative of this acid.
When the acid is employed, the reaction is performed in the presence of a peptide-condensing agent such as a carbodiimide (e.g. dicyclohexylcarbodiimide ) or N,N'-carbonyldiimidazole in an inert solvent such as an ether (e.g. THF, dioxane), an amide (e.g. DMF) or a chlorinated solvent (e.g. methylene chloride, 1,2-dichloroethane, chloroform) at a temperature between 0.degree. C. and the refluxing temperature of the reaction mixture.
When a reactive derivative of the acid is employed, it is possible to react the anhydride, a mixed anhydride, an acid halide or an ester (which may be selected from the activated or unactivated esters of the acid).
The reaction is then performed either in an organic medium, optionally in the presence of an acceptor for acid such as a nitrogenous organic base (e.g. a trialkylamine, a pyridine, 1,8-diazabicyclo[5.4.0]undec-7-ene or 1,5-diazabicyclo[4.3.0]non-5-ene), in a solvent such as is mentioned above or a mixture of these solvents, at a temperature of between 0.degree. C. and the refluxing temperature of the reaction mixture, or in a two-phase aqueous-alcoholic medium in the presence of an alkali metal or alkaline-earth metal base (sodium hydroxide. potassium hydroxide) or alkali metal or alkaline-earth metal carbonate or bicarbonate at a temperature of between 0.degree. and 40.degree. C.
The amines of formula (II) may be obtained by the action of aniline on a derivative of formula: represents a halogen atom (preferably chlorine or bromine).
This reaction is preferably performed in an inert solvent such as acetonitrile, dimethylformamide or tetrahydrofuran, at the boiling point of the solvent.
The derivatives of the formula (IV) may be obtained by application or adaptation of the methods described in Beilstein 2,213 and 2,197.
The acids of formula (III) may be prepared by the action of a phenyl isocyanate of formula: ##STR5## in which R.sub.3 has the same meanings as in the formula (I), on a derivative of formula: ##STR6## in which n has the same meanings as in the formula (I) and R.sub.2 represents a phenyl radical or a chain --(CH.sub.2).sub.m --CO--R.sub.4 in which m is equal to 0, 1 or 2 and R.sub.4 represents an alkoxy radical.
This reaction is generally performed in an inert solvent such as tetrahydrofuran, dimethylformamide, a chlorinated solvent (e.g. chloroform, 1,2-dichloroethane ) or an aromatic solvent (e.g. benzene, toluene ), at a temperature between 10 .degree. C. and the boiling point of the solvent.
The isocyanates of formula (V) may be obtained by application or adaptation of the method described by R. Richter et al., The Chemistry of Cyanates and their thio derivatives, S. Patai, part 2, Wiley N.Y. (1977).
The derivatives of formula (V) for which R.sub.2 represents a chain --(CH.sub.2).sub.m --CO--R.sub.4 in which R.sub.4 represents an alkoxy radical may be obtained by application or adaptation of the method described by D. Coleman, J. Chem. Soc., 2294 (1951).
The compounds of formula ( I ) for whic

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