N-phenylglycinamide CCK antagonists and pharmaceutical compositi

Details N-phenylglycinamide CCK antagonists and pharmaceutical compositi N-phenylglycinamide CCK antagonists and pharmaceutical compositi

1992-10-08

1995-12-12

Higel, Floyd D.

Organic compounds -- part of the class 532-570 series

Organic compounds

Chalcogen in the nitrogen containing substituent

544 585, 546168, 546194, 548253, 5483341, 548545, 560 9, 560 21, 560 22, 560 34, 560 39, 560 41, C07K 506, A61K 31325, C07C22900, C07C20500

Patent

active

054751063

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to N-phenylglycinamide derivatives of formula: ##STR2## to their preparation and to medicinal products containing them. In the formula (I), phenyl radical (optionally substituted with one or more substituents selected from halogen atoms and alkyl, alkoxy, alkylthio, nitro and amino radicals), least one alkyl radical), cycloalkylalkyloxy, phenylalkyloxy, polyfluoroalkyloxy or cinnamyloxy radical or a radical --NR.sub.5 R.sub.6, substituted with one or more substituents selected from halogen atoms and alkyl, alkoxy, alkylthio, carboxyl, hydroxyl, mono- or polyhydroxyalkyl, nitro, amino, acyl, cyano, sulphamoyl, carbamoyl, benzoyl, trifluoromethylsulphonamido, 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), phenyl (optionally substituted with one or more substituents selected from halogen atoms and alkyl, alkoxy and alkylthio radicals), naphthyl, indolyl or quinolyl radicals, substituents selected from halogen atoms, alkyl, alkoxy, hydroxyl, polyfluoroalkyl, nitro, alkylthio, alkoxycarbonyl, carboxyl, acylamino, methylenedioxy, polyfluoroalkoxy, trifluoromethylthio, phenoxy, phenyl, benzyl and phenylamino radicals and a radical --CO--NR.sub.5 R.sub.6, hydrogen atom or an alkyl, phenyl (optionally substituted with one or more substituents selected from halogen atoms and alkyl, alkoxy and alkylthio radicals), indanyl, cycloalkylalkyl, cycloalkyl or phenylalkyl radicals, or alternatively R.sub.5 and R.sub.6, together with the nitrogen atom to which they are attached, form a saturated or unsaturated mono- or polycyclic heterocycle containing 4 to 9 carbon atoms and one or more hetero atoms (O, N, S) and optionally substituted with one or more alkyl, alkoxy, alkoxycarbonyl, dialkylcarbamoyl or phenyl radicals or, in combination with a carbon atom of the heterocycle, optionally substituted with a 4- or 5-membered spiromonocyclic ring-system optionally containing one or more hetero atoms (O, S, N),
In the foregoing definitions and those which will be mentioned below, except where otherwise stated, the alkyl, alkylene and alkoxy radicals and alkyl, alkylene and alkoxy portions contain 1 to 4 carbon atoms in a straight or branched chain, cycloalkyl radicals and portions contain 3 to 6 carbon atoms and the acyl radicals contain 2 to 4 carbon atoms.
In the formula (I), the halogen atoms are preferably chlorine, bromine and fluorine atoms.
When R.sub.5 and R.sub.6, together with the nitrogen atom to which they are attached, form a heterocycle, the latter is preferably a piperidino ring (optionally substituted with at least one alkyl, phenyl, alkoxycarbonyl or dialkylcarbamoyl radical) or a perhydro-1-azepinyl, 1-indolinyl, 1,2,3,6-tetrahydro-1pyridyl, 1,2,3,4-tetrahydro-l-quinolyl, 1-pyrrolidinyl, 3,4-dihydro-2H-1,4-benzoxazin-4-yl, 3,4-dihydro-2H-1,4-benzothiazin-4-yl, N-alkyl-1,2,3,4-tetrahydro-1-quinoxalinyl, perhydro-1-quinolyl, 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 or thiomorpholino (optionally substituted with at least one alkyl radical) ring-system.
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.3 represents a phenylamino radical (in which the phenyl ring is optionally substituted with one or more substituents selected from halogen atoms and alkyl, alkoxy, alkylthio, nitro, acyl, cyano, sulphamoyl, benzoyl, alkoxycarbonyl, --alk--O--alk, 5-tetrazolyl and 5-tetrazolylalkyl radicals) may be obtained by the action of an isocyanate of formula: one or more substituents selected from halogen atoms and a

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