N-phenyl-N-acetamidoglycinamides, their preparation and medicame

Details N-phenyl-N-acetamidoglycinamides, their preparation and medicame N-phenyl-N-acetamidoglycinamides, their preparation and medicame

1992-07-08

1995-01-17

Shah, Mukund J.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

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

5142275, 5142278, 5142305, 514249, 514278, 514326, 514330, 514331, 514340, 514561, 514576, 514597, 540543, 540596, 540607, 544 52, 544 59, 544 60, 544105, 544353, 546 16, 546 19, 546146, 546166, 546210, 546226, 546276, 5483355, 5483381, 548407, 548518, A61K 31415, A61K 3150, A61K 31505, A61K 3139, C07D23366, C07D27912, C07D26530, C07D24114

Patent

active

053825900

DESCRIPTION:

BRIEF SUMMARY
DESCRIPTION OF THE INVENTION

The present invention relates to compounds of formula ##STR2## their preparation and medicaments containing them.
In the formula (I) a phenyl radical (unsubstituted or substituted by one or more substituents chosen from halogen atoms and alkyl, alkoxy, alkylthio, nitro and amino radicals), substituted by an alkoxycarbonyl radical), (unsubstituted or substituted by one or more substituents chosen from halogen atoms and alkyl, alkoxy, alkylthio and dialkylamino radicals) or quinolyl radical, or attached, a saturated or unsaturated monocyclic or polycyclic heterocycle containing 4 to 9 carbon atoms and one or more heteroatoms (O,S,N) and which is unsubstituted or substituted by one or more alkyl, alkoxycarbonyl, dialkylcarbamoyl, phenyl or alkoxy radicals or, in combination with a carbon atom of the heterocycle, a monocyclic spiro ring having 4 or 5 members and which may contain one or more heteroatoms (O,S,N), more substituents chosen from halogen atoms and alkyl, alkoxy and alkylthio radicals), a naphthyl, indolyl or quinolyl radical or a phenylamino radical in which the phenyl ring is unsubstituted or substituted by one or more substituents chosen from halogen atoms and alkyl, alkoxy, alkylthio, hydroxyl, monohydroxyalkyl or polyhydroxyalkyl, nitro, amino, acyl, cyano, sulphamoyl, trifluoromethylsulphonamido, carbamoyl, benzoyl, carboxyl, alkoxycarbonyl, phenylhydroxymethyl, piperidino, hydroxyiminoalkyl, alkoxyiminoalkyl, alkylsulphinyl, hydroxyaminocarbonyl, alkoxyaminocarbonyl, 5-tetrazolyl, 5-tetrazolylalkyl, sulpho, --alk--O--CO--alk, --alk--O--alk, --alk--COOX, --O--alk--COOX, --alk'--COOX, --CH.dbd.CH--COOX, --CO--COOX, --alk--SO.sub.3 H, --CH.dbd.CH--alk', --C(.dbd.NOH)--COOX and --S--alk--COOX radicals, when R.sub.1 represents a hydrogen atom, R.sub.4 represents a naphthyl or indolyl radical or a phenylamino radical in which the phenyl ring is unsubstituted or substituted by an alkyl, alkoxy, alkylthio, nitro or hydroxyl radical or by one or two halogen atoms, R.sub.2 and R.sub.3 cannot form, with the nitrogen atom to which they are attached, a 1-pyrrolidinyl radical unsubstituted or substituted by an alkyl radical or R.sub.2 and R.sub.3 cannot represent alkyl radicals.
In the above definitions and those which will be given below, unless indicated to the contrary, the alkyl, alkylene and alkoxy radicals and moieties contain 1 to 4 carbon atoms in a straight or branched chain, the cycloalkyl moieties contain 3 to 6 carbon atoms and the acyl radicals contain 2 to 4 carbon atoms.
In formula (I), the halogen atoms are preferably chlorine, bromine or fluorine atoms.
When R.sub.2 and R.sub.3 form a heterocycle with the nitrogen atom to which they are attached, said heterocycle is preferably a piperidino (unsubstituted or substituted by at least one alkyl, phenyl, alkoxycarbonyl or dialkylcarbamoyl radical), 1-perhydroazepinyl, 1,2,3,6-tetrahydro-1-pyridyl, 1,2,3,4-tetrahydro-1-quinolyl, 1-pyrrolidinyl, 3,4-dihydro-1,4-2H-benzoxazin-4-yl, 3,4-dihydro-1,4-2H-benzothiazin-4-yl, N-alkyl-1,2,3,4-tetrahydro-1-quinoxalinyl, 1-perhydroquinolyl, 1,2,3,4-tetrahydro-2-isoquinolyl, 8-azaspiro[4,5]decan-8-yl, 8-aza-1,4-dioxaspiro[4,5]decan-8-yl, 2- or 3-phenyl-1-pyrrolidinyl, thiomorpholino (unsubstituted or substituted by at least one alkyl radical) or 1-indolinyl ring.
The compounds of formula (I) containing one or more asymmetric centers possess isomeric forms. The racemates and enantiomers of these compounds also form part of the invention.
The compounds of formula (I) for which R.sub.4 represents a phenylamino radical in which the phenyl ring is unsubstituted or substituted by one or more substituents chosen from halogen atoms and alkyl, alkoxy, alkylthio, nitro, acyl, cyano, sulphamoyl, benzoyl, alkoxycarbonyl, 5-tetrazolyl, 5-tetrazolylalkyl, trifluoromethylsulphonamido and --alk--O--alk radicals may be prepared by the action of an amino derivative of formula: ##STR3## in which R.sub.1, R.sub.2 and R.sub.3 have the same meanings as in formula (I), on an isocyanate of formula: or

REFERENCES:
patent: 4645678 (1987-02-01), Nofre et al.
Chem Abstr, vol. 113, No. 25, Dec. 17, 1990 "Synthesis of disulfides of N-(N-(2-mercaptobenzoyl)glycyl)-N-alkyl/aryl-glycine;" p. 784, #231990r.
Chem Abstr, vol. 93, No. 3, Jul. 21, 1980 "Synthesis of peptices containing 1,2,3,4-tetrahydroquinoline-2-carboxylic acid," pp. 740-741 #26769c.

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