Substituted heterocyclic carboxamide esters, their preparation and their use as pharmaceuticals

A compound of the formula I ##STR12## in which Q is O, S, NR' or a bond,

• X is O or S,
• Y is CR.sup.3,
• m is 0 or 1,
• A is (C.sub.1 -C.sub.3)-alkylene which is optionally substituted once by halogen, cyano, trifluoromethyl, (C.sub.1 -C.sub.6)-alkyl, (C.sub.1 -C.sub.6)-hydroxyalkyl, (C.sub.1 -C.sub.6)-alkoxy or --O--[CH.sub.2 ].sub.x --C.sub.f H.sub.(2f+1-g) F.sub.g or alternatively,
• A is --CH R.sup.5 --, where R.sup.5 differs from said substituent recited above for A and is a substituent of the .alpha.-carbon atom of an .alpha.-amino acid, said .alpha.-amino acid being a natural L-amino acid or its D-isomer,
• B is CO.sub.2 G or a carboxyl radical,
• G is the radical of an alcohol G--OH, in which G is selected from:
• a (C.sub.1 -C.sub.20)-alkyl radical, a (C.sub.3 -C.sub.8) cycloalkyl radical, a (C.sub.2 -C.sub.20)-alkenyl radical, a (C.sub.3 -C.sub.8) cycloalkenyl radical, a retinyl radical, a (C.sub.2 -C.sub.20)-alkynyl radical, a (C.sub.4 -C.sub.20)-alkenynyl radical, where the alkenyl, cycloalkenyl, alkynyl, and alkenynyl radicals in each case contain one or more multiple bonds, a (C.sub.6 -C.sub.16)-carbocyclic aryl radical, a (C.sub.7 -C.sub.16)-carbocyclic aralkyl radical, a heteroaryl radical, and a heteroaralkyl radical, wherein said heteroaryl radical or said heteroaryl moiety of said heteroaralkyl radical contains 5 or 6 ring atoms,
• wherein the above radicals defined for G are substituted by one or more substituents selected from hydroxyl, halogen, cyano, trifluoromethyl, nitro, carboxyl, (C.sub.1 -C.sub.12)-alkyl, (C.sub.3 -C.sub.8)-cycloalkyl, (C.sub.5 -C.sub.8)-cycloalkenyl, (C.sub.6 -C.sub.12)-aryl, (C.sub.7 -C.sub.16)-aralkyl, (C.sub.2 -C.sub.12)-alkenyl, (C.sub.2 -C.sub.12)-alkynyl, (C.sub.1 -C.sub.12)-alkoxy, (C.sub.1 -C.sub.12)-alkoxy-(C.sub.1 -C.sub.12)alkyl, (C.sub.1 -C.sub.12)-alkoxy-(C.sub.1 -C.sub.12)alkoxy, (C.sub.6 -C.sub.12)-aryloxy, (C.sub.7 -C.sub.16)-aralkyloxy, (C.sub.1 -C.sub.8)-hydroxyalkyl, --O--[CH.sub.2- ].sub.x --C.sub.f H.sub.(2f+1-g) (F.sub.g, --OCF.sub.2 Cl, --OCF.sub.2 --CHFCl,
• (C.sub.1 -C.sub.12)-alkylcarbonyl, (C.sub.3 -C.sub.8)-cycloalkylcarbonyl, (C.sub.6 -C.sub.12)-arylcarbonyl, (C.sub.7 -C.sub.16)-aralkylcarbonyl, cinnamoyl, (C.sub.2 -C.sub.12)-alkenylcarbonyl, (C.sub.2 -C.sub.12)-alkynylcarbonyl,
• (C.sub.1 -C.sub.12)-alkoxycarbonyl, (C.sub.1 -C.sub.12)-alkoxy-(C.sub.1 -C.sub.12)-alkoxycarbonyl, (C.sub.6 -C.sub.12)-aryloxycarbonyl, (C.sub.7 -C.sub.16)-aralkoxycarbonyl, (C.sub.3 -C.sub.8)-cycloalkoxycarbonyl, (C.sub.2 -C.sub.12)-alkenyloxycarbonyl, (C.sub.2 -C.sub.12)-alkynyloxycarbonyl, acyloxy, (C.sub.1 -C.sub.12)-alkoxycarbonyloxy, (C.sub.1 -C.sub.12)-alkoxy-(C.sub.1 -C.sub.12)-alkoxycarbonyloxy, (C.sub.6 -C.sub.12)-aryloxycarbonyloxy, (C.sub.7 -C.sub.16) aralkyloxycarbonyloxy, (C.sub.3 -C.sub.8)-cycloalkoxycarbonyloxy, (C.sub.2 -C.sub.12)-alkenyloxycarbonyloxy, (C.sub.2 -C.sub.12)-alkynyloxycarbonyloxy,
• carbamoyl, N-(C.sub.1 -C.sub.12)-alkylcarbamoyl, N,N-di(C.sub.1 -C.sub.12)-alkylcarbamoyl, N-(C.sub.3 -C.sub.8)-cycloalkyl-carbamoyl, N-(C.sub.6 -C.sub.16)-arylcarbamoyl, N-(C.sub.7 -C.sub.16)-aralkylcarbamoyl, N-(C.sub.1 -C.sub.10)-alkyl-N-(C.sub.6 -C.sub.16)arylcarbamoyl, N-(C.sub.1 -C.sub.10)-alkyl-N-(C.sub.7 -C.sub.16)-aralkylcarbamoyl, N-((C.sub.1 -C.sub.10)-alkoxy-(C.sub.1 -C.sub.10)alkyl)-carbamoyl, N-((C.sub.6 -C.sub.12)-aryloxy-(C.sub.1 -C.sub.10)alkyl)carbamoyl, N-((C.sub.7 -C.sub.16)-aralkyloxy-(C.sub.1 -C.sub.10)alkyl)carbamoyl, N-(C.sub.1 -C.sub.10)-alkyl-N-((C.sub.1 -C.sub.10)-alkoxy-(C.sub.1 -C.sub.10)-alkyl)carbamoyl, N-(C.sub.1 -C.sub.10)-alkyl-N-((C.sub.6 -C.sub.16)-aryloxy-(C.sub.1 -C.sub.10)-alkyl)carbamoyl, N-(C.sub.1 -C.sub.10)-alkyl-N-((C.sub.7 -C.sub.16)aralkyloxy-(C.sub.1 -C.sub.10)alkyl)carbamoyl,
• carbamoyloxy, N-(C.sub.1 -C.sub.12)-alkylcarbamoyloxy, N,N-di-(C.sub.1 -C.sub.12)-alkylcarbamoyloxy, N-(C.sub.3 -C.sub.8)-cycloalkylcarbamoyloxy, N-(C.sub.6 -C.sub.12)-arylcarbamoyloxy, N-(C.sub.7 -C.sub.16)-aralkylcarbamoyloxy, N-(C.sub.1 -C.sub.10)-alkyl-N-(C.sub.6 -C.sub.12)arylcarbamoyloxy, N(C.sub.1 -C.sub.10)-alkyl-N-(C.sub.7 -C.sub.16)-aralkylcarbamoyloxy, N-((C.sub.1 -C.sub.10)alkyl)carbamoyloxy, N-((C.sub.6 -C.sub.12)-aryloxy-(C.sub.1 -C.sub.10)alkyl)carbamoyloxy, N-((C.sub.7 -C.sub.16)-aralkyloxy-(C.sub.1 -C.sub.10)alkyl)carbamoyloxy, N-(C.sub.1 -C.sub.10)-alkyl-N-((C.sub.1 -C.sub.10)-alkoxy-(C.sub.1 -C.sub.10)-alkyl)carbamoyloxy, N-(C.sub.1 -C.sub.10)-alkyl-N-((C.sub.6 -C.sub.12)-aryloxy-(C.sub.1 -C.sub.10)-alkyl)carbamoyloxy, N-(C.sub.1 -C.sub.10)-alkyl-N-((C.sub.7 -C.sub.16)-aralkyloxy-(C.sub.1 -C.sub.10)alkyl)carbamoyloxy,
• amino, (C.sub.1 -C.sub.12)-alkylamino, di-(C.sub.1 -C.sub.12)alkylamino, (C.sub.3 -C.sub.8)-cycloalkylamino, (C.sub.2 -C.sub.12)-alkenylamino, (C.sub.2 -C.sub.12)-alkynylamino, N-(C.sub.6 -C.sub.12)-arylamino, N-(C.sub.7 -C.sub.11)-aralkylamino, N-alkyl-aralkylamino, N-alkyl-arylamino, (C.sub.1 -C.sub.12)-alkoxyamino, (C.sub.1 -C.sub.12)-alkoxy-N-(C.sub.1 -C.sub.10)-alkylamino,
• (C.sub.1 -C.sub.12)-alkylcarbonylamino, (C.sub.3 -C.sub.8)-cycloalkylcarbonyl-amino, (C.sub.6 -C.sub.12) arylcarbonylamino, (C.sub.7 -C.sub.16)-aralkylcarbonylamino, (C.sub.1 -C.sub.12)-alkylcarbonyl-N-(C.sub.1 -C.sub.10)-alkylamino, (C.sub.3 -C.sub.8)-cycloalkylcarbonyl-N-(C.sub.1 -C.sub.10)-alkylamino, (C.sub.6 -C.sub.12)-arylcarbonyl-N-(C.sub.1 -C.sub.10)alkylamino, (C.sub.7 -C.sub.11)-aralkylcarbonyl-N-(C.sub.1 -C.sub.10)-alkylamino,
• (C.sub.1 -C.sub.12)-alkylcarbonylamino-(C.sub.1 -C.sub.8)-alkyl, (C.sub.3 -C.sub.8)-cycloalkylcarbonylamino-(C.sub.1 -C.sub.8)alkyl, (C.sub.6 -C.sub.12)-arylcarbonylamino-(C.sub.1 -C.sub.8)-alkyl, (C.sub.7 -C.sub.12)-aralkylcarbonylamino(C.sub.1 -C.sub.8)-alkyl, amino-(C.sub.1 -C.sub.10)-alkyl, N-(C.sub.1 -C.sub.10) alkylamino-(C.sub.1 -C.sub.10)alkyl, N,N-di(C.sub.1 -C.sub.10)-alkylamino-(C.sub.1 -C.sub.10)alkyl, (C.sub.3 -C.sub.8)cycloalkylamino-(C.sub.1 -C.sub.10)alkyl,
• (C.sub.1 -C.sub.12)-alkylmercapto, (C.sub.1 -C.sub.12)-alkylsulfinyl, (C.sub.1 -C.sub.12)-alkylsulfonyl, (C.sub.6 -C.sub.16)-arylmercapto, (C.sub.6 -C.sub.16)-arylsulfinyl, (C.sub.6 -C.sub.12)-arylsulfonyl, (C.sub.7 -C.sub.16)-aralkylmercapto, (C.sub.7 -C.sub.16)-aralkylsulfinyl, (C.sub.7 -C.sub.16)-aralkylsulfonyl,
• sulfamoyl, N-(C.sub.1 -C.sub.10)-alkylsulfamoyl, N,N-di(C.sub.1 -C.sub.10)-alkylsulfamoyl, (C.sub.3 -C.sub.8)-cycloalkylsulfamoyl, N-(C.sub.6 -C.sub.12)-alkylsulfamoyl, N-(C.sub.7 -C.sub.16)-aralkylsulfamoyl, N-(C.sub.1 -C.sub.10)-alkyl-N-(C.sub.6 -C.sub.12)-arylsulfamoyl, N-(C.sub.1 -C.sub.10)-alkyl-N-(C.sub.7 -C.sub.16)-aralkylsulfamoyl, (C.sub.1 -C.sub.10)-alkyl-sulfonamido, N-((C.sub.1 -C.sub.10)alkyl)-(C.sub.1 -C.sub.10)alkylsulfonamido, (C.sub.7 -C.sub.16)-aralkylsulfonamido and N-((C.sub.1 -C.sub.10)-alkyl-(C.sub.7 -C.sub.16)-aralkylsulfonamido,
• wherein the radicals which are aryl or which contain an aryl moiety may be substituted on the aryl by from 1 to 5 identical or different radicals selected from:
• hydroxyl, halogen, cyano, trifluoromethyl, nitro, carboxyl, (C.sub.1 -C.sub.12)-alkyl, (C.sub.3 -C.sub.8)-cycloalkyl, (C.sub.6 -C.sub.12)-aryl, (C.sub.7 -C.sub.16)-aralkyl, (C.sub.1 -C.sub.12)-alkoxy, (C.sub.1 -C.sub.12)-alkoxy-(C.sub.1 -C.sub.12)alkyl,(C.sub.1 -C.sub.12)-alkoxy-(C.sub.1 C.sub.12)alkoxy, (C.sub.6 -C.sub.12)-aryloxy, (C.sub.7 -C.sub.16)-aralkyloxy, (C.sub.1 -C.sub.8)-hydroxyalkyl,
• (C.sub.1 -C.sub.12)-alkylcarbonyl, (C.sub.3 -C.sub.8)-cycloalkyl-carbonyl, (C.sub.6 -C.sub.12)-arylcarbonyl, (C.sub.7 -C.sub.16) aralkylcarbonyl,
• (C.sub.1 -C.sub.12)-alkoxycarbonyl, (C.sub.1 -C.sub.12)-alkoxy-(C.sub.1 -C.sub.12)-alkoxycarbonyl, (C.sub.6 -C.sub.12)-aryloxycarbonyl, (C.sub.7 -C.sub.16)-aralkoxycarbonyl, (C.sub.3 -C.sub.8)-cycloalkoxycarbonyl, (C.sub.2 -C.sub.12)-alkenyloxycarbonyl, (C.sub.2 -C.sub.12)-alkynyloxycarbonyl,
• (C.sub.1 -C.sub.12)-alkylcarbonyloxy, (C.sub.3 -C.sub.8)-cycloalkylcarbonyloxy, (C.sub.6 -C.sub.12)-arylcarbonyloxy, (C.sub.7 -C.sub.16)-aralkylcarbonyloxy, cinnamoyloxy, (C.sub.2 -C.sub.12)-alkenylcarbonyloxy, (C.sub.2 -C.sub.12)-alkynylcarbonyloxy,
• (C.sub.1 -C.sub.12)-alkoxycarbonyloxy, (C.sub.1 -C.sub.12)-alkoxy-(C.sub.1 -C.sub.12)-alkoxycarbonyloxy, (C.sub.6 -C.sub.12)-aryloxycarbonyloxy, (C.sub.7 -C.sub.16)-aralkyloxycarbonyloxy, (C.sub.3 -C.sub.8)-cycloalkoxycarbonyloxy, (C.sub.2 -C.sub.12)-alkenyloxycarbonyloxy, (C.sub.2 -C.sub.12)-alkynyloxycarbonyloxy,
• carbamoyl, N-(C.sub.1 -C.sub.12)-alkylcarbamoyl, N,N-di(C.sub.1 -C.sub.12)alkylcarbamoyl, N-(C.sub.3 -C.sub.8)-cycloalkylcarbamoyl, N-(C.sub.6 -C.sub.12)-arylcarbamoyl, N-(C.sub.7 -C.sub.16)-aralkylcarbamoyl, N-(C.sub.1 -C.sub.10)-alkyl-N-(C.sub.6 -C.sub.12)-arylcarbamoyl, N-(C.sub.1 -C.sub.10)-alkyl-N-(C.sub.7 -C.sub.16)-aralkylcarbamoyl, N-((C.sub.1 -C.sub.10)-alkoxy-(C.sub.1 -C.sub.10)alkyl)carbamoyl, N-((C.sub.6 -C.sub.12)-aryloxy-(C.sub.1 -C.sub.10)alkyl)carbamoyl, N-((C.sub.7 -C.sub.16)-aralkyloxy-(C.sub.1 -C.sub.10)alkyl)carbamoyl,
• N-(C.sub.1 -C.sub.10)-alkyl-N-((C.sub.1 -C.sub.10)-alkoxy-(C.sub.1 -C.sub.10)-alkyl)carbamoyl, N-(C.sub.1 -C.sub.10)-alkyl-N-((C.sub.6 -C.sub.12)-aryloxy-(C.sub.1 -C.sub.10)-alkyl)carbamoyl, N-(C.sub.1 -C.sub.10)-alkyl-N-((C.sub.7 -C.sub.16)aralkyloxy-(C.sub.1 -C.sub.10)alkyl)carbamoyl,
• carbamoyloxy, N-(C.sub.1 -C.sub.12)-alkylcarbamoyloxy, N,N-di-(C.sub.1 -C.sub.12)-alkylcarbamoyloxy, N-(C.sub.3 -C.sub.8)-cycloalkylcarbamoyloxy, N-(C.sub.6 -C.sub.12)-arylcarbamoyloxy, N-(C.sub.7 -C.sub.16)-aralkylcarbamoyloxy, N-(C.sub.1 -C.sub.10)-alkyl-N-(C.sub.6 -C.sub.12)-arylcarbamoyloxy, N(C.sub.1 -C.sub.10)-alkyl-N-(C.sub.7 -C.sub.16)-aralkylcarbamoyloxy, N-((C.sub.1 -C.sub.10)alkyl)carbamoyloxy, N-((C.sub.6 -C.sub.12)-aryloxy-(C.sub.1 -C.sub.10)alkyl)-carbamoyloxy, N-((C.sub.7 -C.sub.16)-aralkyloxy-(C.sub.1 -C.sub.10)alkyl)carbamoyloxy, N-(C.sub.1 -C.sub.10)-alkyl-N-((C.sub.1 -C.sub.10)-alkoxy-(C.sub.1 -C.sub.10)-alkyl)carbamoyloxy, N-(C.sub.1 -C.sub.10)-alkyl-N-((C.sub.6 -C.sub.12)-aryloxy-(C.sub.1 -C.sub.10)-alkyl)carbamoyloxy, N-(C.sub.1 -C.sub.10)-alkyl-N-((C.sub.7 -C.sub.16)-aralkyloxy-(C.sub.1 -C.sub.10)alkyl)carbamoyloxy,
• amino, (C.sub.1 -C.sub.12)-alkylamino, di-(C.sub.1 -C.sub.12)alkylamino, (C.sub.3 -C.sub.8)-cycloalkylamino, (C.sub.3 -C.sub.12)-alkenylamino, (C.sub.3 -C.sub.12)-alkynylamino, N-(C.sub.6 -C.sub.12)-arylamino, N-(C.sub.7 -C.sub.11)-aralkylamino, N-alkylaralkylamino, N-alkyl-arylamino, (C.sub.1 -C.sub.12)-alkoxyamino, (C.sub.1 -C.sub.12)-alkoxy-N-(C.sub.1 -C.sub.10)-alkylamino,
• (C.sub.1 -C.sub.12)-alkylcarbonylamino, (C.sub.3 -C.sub.8)-cycloalkylcarbonylamino, (C.sub.6 -C.sub.12)-arylcarbonylamino, (C.sub.7 -C.sub.16)-alkylcarbonylamino, (C.sub.1 -C.sub.12)-alkylcarbonyl-N-(C.sub.1 -C.sub.10)-alkylamino, (C.sub.3 -C.sub.8)-cycloalkylcarbonyl-N-(C.sub.1 -C.sub.10)-alkylamino, (C.sub.6 -C.sub.12)-arylcarbonyl-N-(C.sub.1 -C.sub.10)alkylamino, (C.sub.7 -C.sub.11)-aralkylcarbonyl-N-(C.sub.1 -C.sub.10)-alkylamino,
• (C.sub.1 -C.sub.12)-alkylcarbonylamino-(C.sub.1 -C.sub.8)-alkyl, (C.sub.3 -C.sub.8)-cycloalkylcarbonylamino-(C.sub.1 -C.sub.8)alkyl, (C.sub.6 -C.sub.12)-arylcarbonylamino-(C.sub.1 -C.sub.8)-alkyl, (C.sub.7 -C.sub.16)-aralkylcarbonylamino-(C.sub.1 -C.sub.8)-alkyl, amino-(C.sub.1 -C.sub.10)-alkyl, N-(C.sub.1 -C.sub.10)alkylamino-(C.sub.1 -C.sub.10)alkyl, N,N-di(C.sub.1 -C.sub.10)-alkylamino-(C.sub.1 -C.sub.10)alkyl, (C.sub.3 -C.sub.8)-cycloalkylamino-(C.sub.1 -C.sub.10)alkyl,
• (C.sub.1 -C.sub.12)-alkylmercapto, (C.sub.1 -C.sub.12)-alkylsulfinyl, (C.sub.1 -C.sub.12)-alkylsulfonyl, (C.sub.6 -C.sub.12)-arylmercapto, (C.sub.6 -C.sub.12)-arylsulfinyl, (C.sub.6 -C.sub.12)-arylsulfonyl, (C.sub.7 -C.sub.16)-aralkylmercapto, (C.sub.7 -C.sub.16)-aralkylsulfinyl and (C.sub.7 -C.sub.16)-aralkylsulfonyl,
• R.sup.1 and R.sup.3 are identical or different and are hydrogen, halogen, (C.sub.1 -C.sub.20)-alkyl, (C.sub.2 -C.sub.20)-alkenyl, (C.sub.1 -C.sub.12)-alkoxy, --O--[CH.sub.2 ].sub.x --C.sub.f H.sub.(2f+1-g) Hal.sub.g, (C.sub.1 -C.sub.12)-alkoxy-(C.sub.1 -C.sub.12)-alkyl, (C.sub.1 -C.sub.8)-alkoxy-(C.sub.1 -C.sub.12)-alkoxy, (C.sub.1 -C.sub.12)-alkoxy-(C.sub.1 -C.sub.8)-alkoxy-(C.sub.2 -C.sub.6)-alkyl, (C.sub.7 -C.sub.11)-aralkyloxy, (C.sub.3 -C.sub.8)-cycloalkyl, (C.sub.3 -C.sub.6)-cycloalkyl-(C.sub.1 -C.sub.8)-alkyl, (C.sub.3 -C.sub.8)-cycloalkyloxy, (C.sub.3 -C.sub.8)-cycloalkyl-(C.sub.1 -C.sub.8)-alkoxy, (C.sub.3 -C.sub.8)-cycloalkyloxy-(C.sub.1 -C.sub.8)-alkyl, (C.sub.3 -C.sub.8)-cycloalkyloxy-(C.sub.1 -C.sub.8)-alkoxy, (C.sub.3 -C.sub.8)cycloalkyl-(C.sub.1 -C.sub.6)-alkyl-(C.sub.1 -C.sub.6)-alkoxy, (C.sub.3 -C.sub.8)-cycloalkyl-(C.sub.1 -C.sub.6)-alkoxy-(C.sub.1 -C.sub.6)-alkyl, (C.sub.3 -C.sub.8)-cycloalkoxy-(C.sub.1 -C.sub.6)-alkoxy-(C.sub.1 -C.sub.6)-alkyl, NR.sup.Y R.sup.Z, (C.sub.1 -C.sub.8)-alkylmercapto, (C.sub.1 -C.sub.8)-alkylsulfinyl, (C.sub.1 -C.sub.8)-alkysulfonyl, (C.sub.6 -C.sub.12)-arylmercapto, (C.sub.6 -C.sub.12)-arylsulfinyl, (C.sub.6 -C.sub.12)-arylsulfonyl, (C.sub.7 -C.sub.12)-aralkylmercapto, (C.sub.7 -C.sub.12)-aralkylsulfinyl, (C.sub.7 -C.sub.11)-aralkylsulfonyl, substituted (C.sub.6 -C.sub.12)-aryloxy-(C.sub.1 -C.sub.6)-alkyl, (C.sub.7 -C.sub.11)-aralkyloxy-(C.sub.1 -C.sub.6)-alkyl, (C.sub.6 -C.sub.12)-aryloxy-(C.sub.1 -C.sub.6)-alkoxy-(C.sub.1 -C.sub.6)-alkyl, (C.sub.7 -C.sub.11)-aralkyloxy-(C.sub.1 -C.sub.6)-alkoxy-(C.sub.1 -C.sub.6)-alkyl, (C.sub.6 -C.sub.12)-aryloxy, (C.sub.7 -C.sub.11)-aralkyloxy, (C.sub.6 -C.sub.12)-aryloxy-(C.sub.6 -C.sub.12)-alkoxy or (C.sub.7 -C.sub.11)-aralkoxy-(C.sub.1 -C.sub.6)-alkoxy,
• where the radicals which are aryl or which contain an aryl moiety may be substituted on the aryl by from 1 to 5 identical or different substituents selected from halogen, cyano, nitro, trifluoromethyl, (C.sub.1 -C.sub.12)-alkyl, (C.sub.2 -C.sub.12)-alkenyl, (C.sub.1 -C.sub.6)-hydroxyalkyl, (C.sub.1 -C.sub.12 -alkoxy, (C.sub.2 -C.sub.12)-alkenyloxy, --O--[CH.sub.2 ].sub.x --C.sub.f H.sub.(2f+1-g) F.sub.g, --OCF.sub.2 Cl, --O--CF.sub.2 --CHFCl, C.sub.1 -C.sub.6)-alkylmercapto, (C.sub.1 -C.sub.6)-alkylsulfinyl, (C.sub.1 -C.sub.6)-alkylsulfonyl, (C.sub.1 -C.sub.6)-alkylcarbonyl, carbamoyl, N-(C.sub.1 -C.sub.4)-alkylcarbamoyl, N,N-di-(C.sub.1 -C.sub.4)-alkylcarbamoyl, (C.sub.1 -C.sub.6)-alkylcarbonyloxy, (C.sub.3 -C.sub.8)-cycloalkylcarbamoyl, phenyl, benzyl, phenoxy, benzyloxy, NR.sup.Y R.sup.Z, phenylmercapto, phenylsulfonyl, phenylsulfinyl, sulfamoyl, N-(C.sub.1 -C.sub.4)-alkylsulfamoyl or N,N-di-(C.sub.1 -C.sub.4)-alkylsulfamoyl, or
• alternatively, in the case where said radicals which are aryl or which contain an aryl moiety are substituted on the aryl by up to 3 of said radicals recited as aryl substitutents above, then two adjacent carbon atoms of an aralkyloxy radical recited in the definition of R.sup.1 and R.sup.3 together carry at least one chain selected from --[CH.sub.2 ].sub.n -- and --CH.dbd.CH--CH.dbd.CH--, where a CH.sub.2 group of the chain is optionally replaced by O, S, SO, SO.sub.2 or NR.sup.Y, or
• alternatively R.sup.3 is as defined above and R.sup.1 and R.sup.2 can form a chain --[CH.sub.2 ].sub.o -, where o is 3, 4, or 5, or
• alternatively R.sup.1 is as defined above and R.sup.2 and R.sup.3 can form a chain --[CH.sub.2 ].sub.o - where o is 3, 4, or 5, or
• alternatively R.sup.1 and R.sup.2 or R.sup.2 and R.sup.3 together with the carbon atoms to which they are attached form a carbocyclic 6-membered ring of either formula Ia or Ib ##STR13## wherein Q and R.sup.4 are as defined above for formula (I) and R.sup.11 to R.sup.18 are independently as defined above for R.sup.1 and R.sup.3
• R.sup.2 is hydrogen, (C.sub.1 -C.sub.20)-alkyl, (C.sub.2 -C.sub.20)-alkenyl, (C.sub.2 -C.sub.20)-alkenyloxy, (C.sub.2 -C.sub.20)-alkynyloxy, retinyloxy, (C.sub.1 -C.sub.20)-alkoxy-(C.sub.1 -C.sub.3)-alkyl, (C.sub.1 -C.sub.20)-alkoxy-(C.sub. -C.sub.3)-alkyl, (C.sub.2 -C.sub.20)-alkenyloxy-(C.sub.1 -C.sub.3)-alkyl, retinyloxy-(C.sub.1 -C.sub.3)-alkyl, (C.sub.2 -C.sub.20)-alkynyloxy-(C.sub.1 -C.sub.3)-alkyl, (C.sub.1 -C.sub.20)-alkoxy, halogen, cyano, trifluoromethyl, (C.sub.1 -C.sub.16)-hydroxyalkyl, (C.sub.1 -C.sub.20)-alkylcarbonyl, (C.sub.7 -C.sub.12)-aralkylcarbonyl, (C.sub.6 -C.sub.12)arylcarbonyl, --O--[CH.sub.2 ].sub.x C.sub.f H.sub.(2f+1-g) F.sub.g, NR.sup.y R.sup.z, C.sub.1 -C.sub.10)-alkylmercapto, (C.sub.1 -C.sub.10)-alkylsulfinyl, (C.sub.1 -C.sub.10)-alkylsulfonyl, (C.sub.6 -C.sub.12)-arylmercapto, (C.sub.6 -C.sub.12)-arylsulfinyl, (C.sub.6 -C.sub.12)-arylsulfonyl, (C.sub.7 -C.sub.12)-aralkylmercapto, (C.sub.7 -C.sub.12)-aralkylsulfinyl, (C.sub.7 -C.sub.12)-aralkylsulfonyl, (C.sub.6 -C.sub.12)-aryloxy, (C.sub.7 -C.sub.16)-aralkyloxy, carboxyl, (C.sub.1 -C.sub.20)-alkoxycarbonyl, (C.sub.1 -C.sub.12)-alkoxy-(C.sub.1 -C.sub.12)-alkoxycarbonyl, (C.sub.6 -C.sub.12)-aryloxycarbonyl, (C.sub.7 -C.sub.16)-aralkoxycarbonyl, (C.sub.3 -C.sub.8)-cycloalkoxycarbonyl, (C.sub.2 -C.sub.20)-alkenyloxycarbonyl, retinyl-oxycarbonyl, (C.sub.2 -C.sub.20)-alkynyloxycarbonyl, (C.sub.3 -C.sub.8)-cycloalkyl-(C.sub.1 -C.sub.6)-alkoxycarbonyl, (C.sub.3 -C.sub.8)-cycloalkoxy-(C.sub.1 -C.sub.6)-alkoxycarbonyl, (C.sub.6 -C.sub.12)-aryloxy-(C.sub.1 -C.sub.6)-alkoxycarbonyl, (C.sub.7 -C.sub.16)-aralkoxy-(C.sub.1 -C.sub.6)-alkoxycarbonyl,
• carbamoyl, N-(C.sub.1 -C.sub.12)-alkylcarbamoyl, N,N-di-(C.sub.1 -C.sub.12)-alkylcarbamoyl, N-(C.sub.3 -C.sub.8)-cycloalkylcarbamoyl-N,N-dicyclo(C.sub.3 -C.sub.8)-alkylcarbamoyl, N-(C.sub.1 -C.sub.10)-alkyl-N-(C.sub.3 -C.sub.8)-cycloalkylcarbamoyl, N-((C.sub.3 -C.sub.8)-cycloalkyl-(C.sub.1 -C.sub.6)-alkyl)carbamoyl, N-(C.sub.1 -C.sub.6)-alkyl-N-((C.sub.3 -C.sub.8)-cycloalkyl-(C.sub.1 -C.sub.6)-alkyl)carbamoyl, N-(+)-dehydroabietylcarbamoyl, N-(C.sub.1 -C.sub.6)alkyl-N-(+)-dehydroabietylcarbamoyl, N-(C.sub.6 -C.sub.12)-arylcarbamoyl, N-(C.sub.7 -C.sub.16)-aralkylcarbamoyl, N-(C.sub.1 -C.sub.10)-alkyl-N-(C.sub.6 -C.sub.16)-arylcarbamoyl, N-(C.sub.1 -C.sub.10)-alkyl-N-(C.sub.7 -C.sub.12 -aralkylcarbamoyl, N-((C.sub.1 -C.sub.12)-alkoxy-(C.sub.1 -C.sub.10)-alkyl)carbamoyl, N-((C.sub.6 -C.sub.16)-aryloxy-(C.sub.1 -C.sub.10)-alkyl)carbamoyl,
• N-(C.sub.7 -C.sub.16)-aralkyloxy-(C.sub.1 -C.sub.10)-alkyl)carbamoyl, N-(C.sub.1 -C.sub.10)-alkyl-N-(C.sub.1 -C.sub.10)-alkoxy-(C.sub.1 -C.sub.10)-alkyl)carbamoyl, N-(C.sub.1 -C.sub.10)-alkyl-N-((C.sub.6 -C.sub.12)-aryloxy-(C.sub.1 -C.sub.10)-alkyl)carbamoyl, N-(C.sub.1 -C.sub.10)-alkyl-N-((C.sub.7 -C.sub.16)-aralkyloxy-(C.sub.1 -C.sub.10)-alkyl)-carbamoyl, or CON(CH.sub.2).sub.h, in which a CH.sub.2 group can be replaced by O, S, N-(C.sub.1 -C.sub.8)-alkylimino, N-(C.sub.3 -C.sub.8)-cycloalkylimino, N-(C.sub.3 -C.sub.8)-cycloalkyl-(C.sub.1 -C.sub.4)-alkylimino, N-(C.sub.6 -C.sub.12)-arylimino, N-(C.sub.7 -C.sub.16)-aralkylimino or N-(C.sub.1 -C.sub.4)-alkoxy-(C.sub.1 -C.sub.6)-alkylimino,
• wherein the aryl moieties and aryl radicals defined herein for R.sup.2 may be substituted in the manner defined for R.sup.1 and R.sup.3,
• R.sup.4, if Q is a bond, is chlorine or,
• if Q is O, S, or NR', is a (C.sub.1 -C.sub.10)-alkyl radical, a (C.sub.2 -C.sub.10)-alkenyl radical, a (C.sub.2 -C.sub.10)-alkynyl radical, wherein said alkenyl or alkynyl radical contains one or two C--C multiple bonds, an unsubstituted fluoroalkyl radical of the formula --[CH.sub.2 ].sub.x --C.sub.f H.sub.(2f+1-g) F.sub.g, a (C.sub.1 -C.sub.8)-alkoxy-(C.sub.1 -C.sub.6)-alkyl radical, a (C.sub.1 -C.sub.6)-alkoxy-(C.sub.1 -C.sub.4)-alkoxy-(C.sub.1 -C.sub.4)-alkyl radical or a radical of the formula Z,
• --[CH.sub.2 ].sub.v --[O].sub.w --[CH.sub.2 ].sub.t --E (Z),
• where E is a heteroaryl radical, a (C.sub.3 -C.sub.8)-cycloalkyl radical, or a phenyl radical of the formula F ##STR14## wherein v is 0, 1, 2, 3, 4, 5 or 6, w is 0 or 1, and t is 0, 1, 2 or 3, with the restriction that v is not 0 if w is 1, and
• R.sup.6, R.sup.7, R.sup.8, R.sup.9 and R.sup.10 are identical or different and are selected from hydrogen, halogen, cyano, nitro, trifluoromethyl, (C.sub.1 -C.sub.6)-alkyl, (C.sub.3 -C.sub.8)-cycloalkyl, (C.sub.1 -C.sub.6)-alkoxy, --O--[CH.sub.2. ].sub.x --C.sub.f H.sub.(2f+1-g) F.sub.g, --OCF.sub.2 Cl, --O--CF.sub.2 CHFCl, (C.sub.1 -C.sub.6)-alkylmercapto, (C.sub.1 -C.sub.6)-hydroxyalkyl, (C.sub.1 -C.sub.6)-alkoxy-(C.sub.1 -C.sub.6)-alkoxy, (C.sub.1 -C.sub.6)-alkoxy-(C.sub.1 -C.sub.6)-alkyl, (C.sub.1 -C.sub.6)-alkylsulfinyl, (C.sub.1 -C.sub.6)-alkylsulfonyl, (C.sub.1 -C.sub.6)-alkylcarbonyl, (C.sub.1 -C.sub.8 -alkoxycarbonyl, carbamoyl, N-(C.sub.1 -C.sub.8)-alkylcarbamoyl, N,N-di-(C.sub.1 -C.sub.8)-alkylcarbamoyl, (C.sub.7 -C.sub.11)-aralkylcarbamoyl optionally substituted by fluorine, chlorine, bromine, trifluoromethyl or (C.sub.1 -C.sub.6)-alkoxy, N-(C.sub.3 -C.sub.8)-cycloalkylcarbamoyl, N-(C.sub.3 -C.sub.8)-cycloalkyl-(C.sub.1 -C.sub.4)-alkylcarbamoyl, (C.sub.1 -C.sub.6)-alkylcarbonyloxy, phenyl, benzyl, phenoxy, benzyloxy, NR.sup.Y R.sup.Z, phenylmercapto, phenylsulfonyl, phenylsulfinyl, sulfamoyl, N-(C.sub.1 -C.sub.8)-alkylsulfamoyl or N, N-di-(C.sub.1 -C.sub.8)-alkylsulfamoyl, or
• alternatively R.sup.6 and R.sup.7, R.sup.7 and R.sup.8, R.sup.8 and R.sup.9, or R.sup.9 and R.sup.10 together are a chain selected from --[CH.sub.2- ].sub.n - and --CH.dbd.CH--CH.dbd.CH--, where a CH.sub.2 group of the chain is optionally replaced by O, S, SO, SO.sub.2 or NR.sup.Y, and
• if E is said heteroaryl radical, said radical can carry 1, 2 or 3 substituents selected from those defined herein for R.sup.6 -R.sup.10 or
• if E is said cycloalkyl radical, said radical can carry one substituent selected from those defined herein for R.sup.6 -R.sup.10, or
• alternatively, R.sup.4 is R", provided Q has the meaning of NR', where R' and R" are identical or different and are hydrogen, (C.sub.6 -C.sub.12)-aryl, C.sub.7 -C.sub.11)-aralkyl, (C.sub.1 -C.sub.8)-alkyl, (C.sub.1 -C.sub.8)-alkoxy-(C.sub.1 -C.sub.8)-alkyl, (C.sub.7 -C.sub.12)-aralkoxy-(C.sub.1 -C.sub.8)-alkyl, (C.sub.6 -C.sub.12)-aryloxy-(C.sub.1 -C.sub.8)-alkyl, (C.sub.1 -C.sub.10)-alkylcarbonyl, optionally substituted (C.sub.7 -C.sub.16)-aralkylcarbonyl or optionally substituted C.sub.6 -C.sub.12)-arylcarbonyl, or R' and R" together are --[CH.sub.2 ].sub.h, in which a CH.sub.2 group can be replaced by O, S, N-acylimino or N-(C.sub.1 -C.sub.10)-alkoxycarbonylimino or
• alternatively, R.sup.2 is as defined above, and at least one of R.sup.1 and R.sup.3, which are identical or different, is selected from a radical of the formula (D)
• OZ (D),
• wherein Z is as defined above for R.sup.4, and if one of R.sup.1 and R.sup.3 is not (D), said one is as defined above, or
• alternatively R.sup.2 is as defined above and R.sup.1 and R.sup.3 are identical or different and are selected from a radical of the formula Z, wherein Z is as defined above for R.sup.4,
• R.sup.Y and R.sup.Z are identical or different and are hydrogen, (C.sub.6 -C.sub.12)-aryl, (C.sub.1 -C.sub.10)-alkyl, (C.sub.3 --C.sub.10)-cycloalkyl, (C.sub.1 -C.sub.8)-alkoxy-(C.sub.1 -C.sub.8)-alkyl, (C.sub.7 -C.sub.12)-aralkoxy-(C.sub.1 -C.sub.8)-alkyl, (C.sub.6 -C.sub.12)-aryloxy-(C.sub.1 -C.sub.8)-alkyl, (C.sub.1 -C.sub.10)-alkylcarbonyl, optionally substituted (C.sub.7 -C.sub.16)-aralkylcarbonyl or optionally substituted (C.sub.6 -C.sub.12)-arylcarbonyl, or alternatively R.sup.Y and R.sup.Z are together --[CH.sub.2 ].sub.h -, in which a CH.sub.2 group can be replaced by O, S, N-(C.sub.1 -C.sub.4)-alkylcarbonylimino or N-(C.sub.1 -C.sub.4)-alkoxycarbonylimino,
• f is 1 to 8,
• g is 0 or 1 to (2f+1),
• h is 3 to 6,
• x is 0 to 3, and
• n is 3 or 4,
• or a physiologically active salt thereof,
• with the proviso that 3-benzyloxypyridine-2-carboxylic acid (L-threonyl methyl ester) amide, 3-benzyloxy-pyridine-2-carboxylic acid (L-threonyl (Fmoc-Phg) tert-butyl ester) amide, 3-benzyloxy-pyridine-2-carboxylic acid (L-threonyl tertbutyl ester) amide, 3-benzyloxypyridine-2-carboxylic acid (D-allothreonyl methyl ester) amide, 3-benzyloxy-pyridine-2-carboxylic acid (glycyl ethyl ester) amide, 3-benzyloxypyridine-2-carboxylic acid (L-threonyl) amide, 3-benzyloxypyridine-2-carboxylic acid, and 3-benzyloxypyridine-2-carboxylic acid ((Fmoc-Phg) L-threonyl) amide hydrochloride are excluded.