N-substituted indole-3glyoxylamides having anti-asthmatic, antiallergic and immunosuppressant/immuno-modulating action

N-substituted indol-3-glyoxylamides of the formula

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• and their acid addition salts, where the radicals R, R1, R2, R3, R4 and Z have the following meaning:
• R=hydrogen, (C1-C6)-alkyl, where the alkyl group can be mono- or polysubstituted by the phenyl ring. This phenyl ring, for its part, can be mono- or polysubstituted by halogen, (C1-C6)-alkyl, (C3-C7)-cycloalkyl, by carboxyl groups, carboxyl groups esterified with (C1-C6)-alkanols, trifluoromethyl groups, hydroxyl groups, methoxy groups, ethoxy groups, benzyloxy groups and by a benyl [sic] group which is mono- or polysubstituted in the phenyl moiety by (C1-C6)-alkyl groups halogen atoms or trifluoromethyl groups,
• R1 can be a phenyl ring which is mono- or polysubstituted by (C1-C6)-alkyl, (C1-C6)-alkoxy, hydroxyl, benzyloxy, nitro, amino, (C1-C6)-alkylamino, (C1-C6)-alkoxy-carbonylamino and by a carboxyl group or a carboxyl group esterified by (C1-C6)-alkanols, or is a pyridin structure of the formula II
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• where the pyridin structure is alternatively bonded to the ring carbon atoms 2, 3 and 4 and can be substituted by the substitutents R5 and R6. The radicals R5 and R6 can be identical or different and have the meaning (C1-C6)-alkyl, and also the meaning (C3-C7)-cycloalkyl, (C1-C6)-alkoxy, nitro, amino, hydroxyl, halogen and trifluoromethyl and are furthermore the ethoxy-carbonylamino radical and the group carboxy-alkyloxy in which the alkyl group can have 1-4 C atoms,
• R1 can furthermore be a 2- or 4-pyrimidinyl-heterocycle or a pyridylmethyl radical in which CH2 can be in the 2-, 3-, 4-position where the 2-pyrimidinyl ring can be mono- or polysubstituted by the methyl group, furthermore are [sic] the 2-, 3- and 4-quinolyl structure substituted by (C1-C6)-alkyl, halogen, the nitro group, the amino group and the (C1-C6)-alkylamino radical, or are [sic] a 2-, 3- and 4-quinolyl methyl group, where the ring carbons of the pyridylmethyl and quinolylmethyl radical can be substituted by (C1-C6)-alkyl, (C1-C6)-alkoxy, nitro, amino and (C1-C6)-alkoxy-carbonylamino,
• R1 for the case where R is hydrogen or the benzyl group, can furthermore be the acid radical of a natural or unnatural amino acid, e.g. the α-glycyl, the α-sarcosyl, the α-alanyl, the α-leucyl, the α-isoleucyl, the α-seryl, the α-phenylalanyl, the α-histidyl, the α-prolyl, the α-arginyl, the α-lysyl, the α-asparagyl and the α-glutamyl radical, where the amino groups of the respective amino acids can be present in unprotected or protected form and are possible protective groups for the amino function of the carbobenzoxy radical (Z radical) and the tert-butoxycarbonyl radical (BOC radical) and also the acetyl group. In the case of the asparagyl and glutamyl radical claimed for R1, the second, nonbonded carboxyl group is present as a free carboxyl group or in the form of an ester with C1-C6-alkanols, e.g. as the methyl, ethyl or as the tert-butyl ester. R1 can furthermore be the allylaminocarbonyl-2-methylprop-1-yl group. R and R1, together with the nitrogen atom to which they are bonded, can furthermore form a piperazine ring of the formula III or a homopiperazine ring if R1 is an aminoalkylene group in which
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• R7 is an alkyl radical, a phenyl ring which can be mono- or polysubstituted by (C1-C1)-alkyl, (C1-C6)-alkoxy, halogen, the nitro group, the amino function, by (C1-C6)-alkylamino, the benzhydryl group and the bis-p-fluorobenzylhydryl group,
• R2 can be hydrogen or the (C1-C6)-alkyl group, where the alkyl group can be mono- or polysubstituted by halogen and phenyl which for its part can be 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. The (C1-C6)-alkyl group counting as R2 can furthermore be substituted by the 2-quinolyl group and the 2-, 3- and 4-pyridyl structure, which in each case can both be mono- or polysubstituted by halogen, (C1-C4)-alkyl groups or (C1-C4)-alkoxy groups. R2 is furthermore the aroyl radical, where the aryl moiety on which this radical is based is the phenyl ring which can be mono- or polysubstituted by halogen, (C1-C6)-alkyl, (C3-C7)-cycloalkyl, carboxyl groups, carboxyl groups esterified by (C1-C6)-alkanols, trifluoromethyl groups, hydroxyl groups, methoxy groups, ethoxy groups or benzyloxy groups,
• R3 and R4 can be identical or different and are hydrogen, hydroxyl, (C1-C6)-alkyl, (C3-C7)-cyclo-alkyl, (C1-C6)-alkanoyl, (C1-C6)-alkoxy, halogen and benzyloxy. R3 and R4 can furthermore be the nitro group, the amino group, the (C1-C4)-mono- or dialkyl-substituted amino group, and the (C1-C3)-alkoxycarbonylamino function or the (C1-C3)-alkoxy-carbonylamino-(C1-C3)-alkyl function,
• Z is O or S,
• and where the designation alkyl, alkanol, alkoxy or alkylamino group for the radicals R, R1, R2, R3, R4, R5, R6 and R7 is normally to be understood as meaning “straight-chain” and “branched” alkyl groups, where “straight-chain alkyl groups” can be, for example, radicals such as methyl, ethyl, n-propyl, n-butyl, n-pentyl and n-hexyl and “branched alkyl groups” designate, for example, radicals such as isopropyl or tert-butyl. “Cycloalkyl” is to be understood as meaning radicals such as, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl, additionally the designation “halogen” represents fluorine, chlorine, bromine or iodine, and the designation “alkoxy group” represents radicals such as, for example, methoxy, ethoxy, propoxy, butoxy, isopropoxy, isobutoxy or pentoxy.