Patent ID: 6344467
Filing Date: 2002-02-05
Classification: A61P,C07D

Abstract:
An N-substituted indol-3-glyoxylamide of formula I or an acid addition salt thereof, wherein the radicals R, R1, R2, R3, R4 and Z have the following meanings:R represents (1) hydrogen, or (2) (C1-C6)-alkyl, wherein the alkyl group is optionally mono- or polysubstituted by a phenyl ring, which ring is optionally mono- or polysubstituted by halogen, (C1-C6)-alkyl, (C3-C7)-cycloalkyl, carboxyl groups, carboxyl groups esterified with (C1-C6)-alkanols, trifluoromethyl groups, hydroxyl groups, methoxy groups, ethoxy groups, benzyloxy groups and benzyl groups which are optionally mono- or polysubstituted on the phenyl moiety by (C1-C6) alkyl groups, halogen atoms or trifluoromethyl groups; R1 represents (1) a phenyl ring which is mono- or polysubstituted by (C1-C6)-alkyl, (C1-C6)-alkoxy, hydroxyl, benzyloxy, nitro, amino, (C1-C6)-alkylamino, (C1-C6)-alkoxycarbonylamino and by a carboxyl group or a carboxyl group esterified by a (C1-C6)-alkanol; (2) a 2- or 4-pyrimidinyl-heterocycle or a pyridylmethyl radical in which CH2 is in the 2-, 3- or 4-position, wherein the 2-pyrimidinyl ring is optionally mono- or polysubstituted by a methyl group; (3) a 2-, 3- or 4-quinolyl structure substituted by (C1-C6)-alkyl, halogen, a nitro group, an amino group or a (C1-C6)-alkylamino radical; (4) a 2-, 3- or 4-quinolyl methyl group, wherein the ring carbons of the pyridylmethyl and quinolylmethyl radicals are optionally substituted by (C1-C6)-alkyl, (C1-C6)-alkoxy, nitro, amino and (C1-C6)-alkoxy-carbonylamino; (5) if R represents hydrogen or a benzyl group, R1 can represent the acid radical of a natural amino acid, or sarcosine wherein the amino group of said natural amino acid or sarcosine is present in protected or unprotected form wherein if R1 represents an asparagyl or a glutamyl radical having a second nonbonded carboxyl group, said nonbonded carboxyl group is present as a free carboxyl group or in the form of an ester with C1-C6-alkanols; (6) an allylaminocarbonyl-2-methylprop-1-yl group; or R1 and R, together with the nitrogen atom to which they are bonded, form a piperizine ring of formula III â€ƒor a homopiperazine ring if R1 represents an aminoalkylene group, in which R7 represents an alkyl radical, a phenyl ring which is optionally mono- or polysubstituted by (C1-C6)-alkyl, (C1-C6)-alkoxy, halogen, a nitro group, an amino function, (C1-C6)-alkylamino, benzhydryl group or bis-p-fluorobenzylhydryl group; R2 represents (1) hydrogen; (2) a (C1-C6)-alkyl group, said alkyl group being optionally mono- or polysubstituted by halogen or a phenyl ring, which ring is optionally mono- or polysubstituted by halogen, (C1-C6)-alkyl, (C3-C7)-cycloalkyl, carboxyl groups, carboxyl groups esterified with (C1-C6)-alkanols, trifluoromethyl groups, hydroxyl groups, methoxy groups, ethoxy groups, or benzyloxy groups; or by a 2-quinolyl group or a 2-,3- or 4-pyridyl structure which are optionally mono- or polysubstituted by halogen, (C1-C4)-alkyl groups or (C1-C4)-alkoxy groups; (3) an aroyl radical, wherein the aroyl moiety on which the radical is based is a phenyl ring which is optionally mono- or polysubstituted by halogen, (C1-C6)-alkyl, (C3-C7)-cycloalkyl, carboxyl groups, carboxyl groups esterified with (C1-C6)-alkanols, trifluoromethyl groups, hydroxyl groups, methoxy groups, ethoxy groups, or benzyloxy groups; R3 and R4, which are identical or different, represent hydrogen, hydroxyl, (C1-C6)-alkyl, (C3-C7)-cycloalkyl, (C1-C6)-alkanoyl, (C1-C6)-alkoxy, halogen, benzoxy, a nitro group, an amino group, a (C1-C4)-mono- or dialkyl substituted amino group, a (C1-C3)-alkoxycarbonylamino function or a (C1-C3)-alkoxycarbonylamino-(C1-C3)-alkyl function; and z represents O; wherein alkyl, alkanol, alkoxy and alkylamino groups may be straight chained or branched.