N-phenyl-n-alkoxycarbonylalkyl glycinamides, their preparation a

Details N-phenyl-n-alkoxycarbonylalkyl glycinamides, their preparation a N-phenyl-n-alkoxycarbonylalkyl glycinamides, their preparation a

1992-06-25

1994-12-20

Richter, Johann

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Ester doai

560 9, 560 21, 560 34, 560 39, 560 41, A61K 31325, C07C20500, C07C22900

Patent

active

053746562

DESCRIPTION:

BRIEF SUMMARY
DESCRIPTION OF THE INVENTION

The present invention relates to compounds of formula: ##STR2## their preparation and the medicaments containing them.
In formula (I), a phenyl radical which is unsubstituted or substituted by one or more substituents chosen from halogen atoms and alkyl, alkoxy, nitro, amino and alkylthio radicals, a cycloalkyl radical which is unsubstituted or substituted by one or more alkyl radicals, more substituents chosen from alkyl, alkoxy and alkylthio radicals and halogen atoms), a naphthyl, indolyl, quinolyl or phenylamino radical (in which the phenyl ring is optionally substituted by one or more substituents chosen from halogen atoms and alkyl, alkoxy and alkylthio radicals) or a quinolylamino radical, and alkyl or phenyl radical, R.sub.3 represents a naphthyl, indolyl or phenylamino radical, optionally substituted by an alkyl, alkoxy or alkylthio radical or by one or two halogen atoms, and m is 0, R.sub.2 is not an alkyl radical containing 1 to 4 carbon atoms or a cycloalkyl radical.
In the definitions above and in those which will be given below, unless indicated to the contrary, the alkyl and alkoxy radicals and the alkyl and alkoxy portions contain 1 to 4 carbon atoms in a straight or branched chain and the cycloalkyl radicals contain 3 to 6 carbon atoms.
In formula (I), the halogen atoms are preferably chlorine, bromine or fluorine atoms.
The compounds of formula (I) containing one or more centers of asymmetry have isomeric forms. The racemates and the enantiomers of these compounds also form part of the invention.
The compounds of formula (I) for which R.sub.3 represents a phenylamino radical in which the phenyl ring is optionally substituted may be prepared by the action of an acid of formula: ##STR3## in which m, R.sub.1 and R.sub.2 have the same meanings as in formula (I).
This reaction generally takes place in an inert solvent, such as a chlorinated solvent (chloroform, dichloromethane or 1,2-dichloroethane for example), by means of thionyl chloride, at the boiling point of the solvent.
The acids of formula (II) may be obtained by the action of a phenyl isocyanate in which the phenyl ring is optionally substituted by one or more substituents chosen from halogen atoms and alkyl, alkoxy and alkylthio radicals, on a derivative of formula:
This reaction generally takes place in an aqueous medium, in the presence of an alkaline agent, such as an alkali metal bicarbonate, at a temperature of between 15 and 30.degree. C.
The amines of formula (III) for which m is 0 may be obtained by the action of aniline on a derivative of formula: represents a halogen atom (preferably chlorine or bromine).
This reaction preferably takes place in an inert solvent, such as acetonitrile, dimethylformamide or tetrahydrofuran, at the boiling point of the solvent.
The derivatives of formula (V) for which R.sub.1 represents an alkyl, alkoxycarbonyl or substituted phenyl radical may be obtained by halogenation of a derivative of formula: meanings as in formula (I) and m is 0.
This halogenation takes place by means of a halogenating agent such as N-bromosuccinimide, N-chlorosuccinimide or bromine, if appropriate in the presence of azobisisobutyronitrile, or acetamide, in an inert solvent, such as a chlorinated solvent (chloroform or carbon tetrachloride for example), at a temperature between 20.degree. C. and the boiling point of the solvent.
The derivatives of formula (VI) may be obtained by the action of an alcohol of formula: formula: reactive derivative of this acid, such as a halide.
When the acid is used, the reaction is carried out in the presence of an acid such as sulphuric acid, at the boiling point of the reaction medium.
When a halide is used, the reaction is carried out in the presence of a tertiary amine, such as triethylamine or N,N-dimethylaniline, at a temperature close to 20.degree. C.
The derivatives of formula (VIII) for which R.sub.1 represents an alkoxycarbonyl radical may be obtained by application or adaptation of the method described in Acta Chem. Scand., B29, 687 (1975).
The de

REFERENCES:
Chemical Abstracts Service, CA114(17):164819x (1994).
Peptides, Structure and Function, Proceedings of the Ninth American Peptide Symposium, 1985, Pierce Chemical Company.
Chem. Abs., vol. 105, 1986, p. 801, abstract 173038h.
Chem. Abs., vol. 113, 1990, T. Lu, et al., "Synthesis of disulfides of N-(N-(2-mercaptobenzoyl)glycl)-N-alkyl/aryl-glycine", p. 784, abstract 231990r.

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