Patent TW-550256-B (TW)
Title: N-substituted indole-3-glyoxylamides having anti-asthmatic, antiallergic and immunosuppressant/immuno-modulating action
Inventor: LEBAUT GUILLAUME
IPC: A61P43/00
Filed: 1997-09-30
Granted: 2003-09-01
Abstract: The invention relates to novel N-substituted indole-3-glyoxylamides, to processes for their preparation and to their pharmaceutical use. The compounds have antiasthmatic, antiallergic and immunosuppressant/immunomodulating actions. N-substituted indol-3-glyoxylamides of the formula I and their acid addition salts, where the radicals R, R1, R2, R3, R4 and Z have the following meaning: R= hydrogen or (C1-C6)-alkyl, where the alkyl group can be mono-substituted by a phenyl ring, R1 can be a phenyl ring which is substituted by one, two or three substituted selected from the group consisting of (C1-C6)-alkyl, (C1-C6)-alkoxy, nitro, amino, and (C1-C6)-alkoxy-carbonylamino, and substituted by one carboxyl group or a carboxyl group esterified by (C1-C6)-alkanols, or is a pyridin structure of the formula II, 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, (C1-C6)-alkoxy, amino, halogen, trifluoromethyl and the ethoxy-carbonylamino radical (in which the alkyl group can have 1-4 C atoms), R1 can furthermore be a pyridylmethyl radical in which CH2 can be in the 2-, 3-, 4-position, furthermore are [sic] the 2-, 3-, and 4-quinolyl structure substituted by (C1-C6)-alkyl, R1 for the case where R is hydrogen or the benzyl group, can furthermore be the acid radical of a natural amino acid which is the alpha-histidyl radical, where the amino group of the amino acid can be present in an unprotected or protected from of an ester with C1-C6-alkanols, R1 can furthermore be the allylaminocarbonyl-2-methylprop-1-yl group, or 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 homopiperzine ring if R1 is an aminoalkylene group in which R7 is an alkyl radical, or a phenyl ring which can be mono-, di- or tri-substituted by (C1-C6)-alkyl, (C1-C6)-alkoxy, halogen or the nitro group, or is a benzhydyl group in which the phenyl ring can be mono-, di- or tri-substituted with halogen, R2 can be hydrogen or the (C1-C6)-alkyl group, where the alkyl group can be substituted by phenyl which for its part can be mono-, di- or tri-substituted by halogen, (C1-C6)-alkyl, 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-, 3- and 4-pyridyl structure, R2 is furthermore the aroyl radical, where the aryl moiety on which this radical is based is the phenyl ring which can be mono-, di- or tri-substituted by halogen, R3 and R4 can be identical and are hydrogen, hydroxyl, (C1-C6)-alkyl, (C1-C6)-alkoxy, halogen and benzyloxy, R3 and R4 can furthermore be the nitro group, the 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 has a ""straight-chain"" or ""branched"" alkyl moiety, and the designation ""halogen"" represents fluorine, chlorine, bromine or iodine.