Substituted propiolic acid amides and their use for producing drugs

A substituted propiolic acid amide of the formula I,

• in which
• a, b and c, mutually independently, in each case denote 0 or 1, wherein the sum of a, b and c is equal to 1, 2 or 3;
• A denotes one of the following residues
• Q and U respectively denote CR10 or N;
• R and V respectively denote CR11 or N;
• K and W respectively denote CR12 or N;
• P and T respectively denote O, S or NR13;
• with the proviso that compounds are excluded in which P denotes S, Q denotes N, R denotes CR11 and K denotes CR12 or N;
• R1 and R8, mutually independently, in each case denote H;
• —C(═O)—R28;
• —C(═O)—O—R29;
• —C(═O)—NH2;
• —C(═O)—NH—R30;
• —C(═O)—NR31R32;
• —S(═O)—R33;
• —S(═O)2—R34;
• unsubstituted or substituted alkyl, alkenyl or alkynyl;
• unsubstituted or substituted heteroalkyl, heteroalkenyl or heteroalkynyl;
• unsubstituted or substituted cycloalkyl or cycloalkenyl;
• unsubstituted or substituted heterocycloalkyl or heterocycloalkenyl;
• unsubstituted or substituted -(alkylene)-cycloalkyl, -(alkenylene)-cycloalkyl, -(alkynylene)-cycloalkyl, -(alkylene)-cycloalkenyl, -(alkenylene)-cycloalkenyl or -(alkynylene)-cycloalkenyl;
• unsubstituted or substituted -(heteroalkylene)-cycloalkyl, -(heteroalkenylene)-cycloalkyl, -(heteroalkylene)-cycloalkenyl or -(heteroalkenylene)- cycloalkenyl;
• unsubstituted or substituted -(alkylene)-heterocycloalkyl, -(alkenylene)-heterocycloalkyl, -(alkynylene)-heterocycloalkyl, -(alkylene)-heterocycloalkenyl, -(alkenylene)-heterocycloalkenyl or -(alkynylene)-heterocycloalkenyl;
• unsubstituted or substituted -(heteroalkylene)-heterocycloalkyl, -(heteroalkenylene)-heterocycloalkyl, -(heteroalkylene)-heterocycloalkenyl or -(heteroalkenylene)-heterocycloalkenyl;
• unsubstituted or substituted aryl;
• unsubstituted or substituted heteroaryl;
• unsubstituted or substituted -(alkylene)-aryl, -(alkenylene)-aryl, -(alkynylene)-aryl, -(heteroalkylene)-aryl or -(heteroalkenylene)-aryl;
• or unsubstituted or substituted -(alkylene)-heteroaryl, -(alkenylene)-heteroaryl, -(alkynylene)-heteroaryl, -(heteroalkylene)-heteroaryl or -(heteroalkenylene)-heteroaryl;
• R2, R3, R4, R5, R6, R7, R14, R15, R16, R17, R18, R19, R20, R21, R22, R23, R24, R25, R26 and R27, mutually independently, in each case denote H;
• F;
• Cl;
• Br;
• I;
• —NO2;
• —CN;
• —NH2;
• —OH;
• —SH;
• —C(═O)—OH;
• —C(═O)—H;
• —NH—C(═O)—H;
• —C(═O)—R28;
• —C(═O)—O—R29;
• —C(═O)—NH2;
• —C(═O)—NH—R30;
• —C(═O)—NR31R32;
• —S(═O)—R33;
• —S(═O)2—R34;
• —NH—R35;
• —NR36R37;
• —O—C(═O)—R38;
• —NH—C(═O)—R39;
• —NR40—C(═O)—R41;
• —O—R42, —S—R43;
• —NH—C(═O)—NH—R44;
• —NH—C(═S)—NH—R45;
• —NH—S(═O)2—R46;
• —NR47—S(═O)2—R48;
• unsubstituted or at least monosubstituted alkyl, alkenyl or alkynyl;
• unsubstituted or at least monosubstituted heteroalkyl, heteroalkenyl or heteroalkynyl;
• unsubstituted or at least monosubstituted cycloalkyl or cycloalkenyl;
• unsubstituted or at least monosubstituted heterocycloalkyl or heterocycloalkenyl;
• unsubstituted or at least monosubstituted -(alkylene)-cycloalkyl, -(alkenylene)-cycloalkyl, -(alkynylene)-cycloalkyl, -(alkylene)-cycloalkenyl, -(alkenylene)-cycloalkenyl or -(alkynylene)-cycloalkenyl;
• unsubstituted or at least monosubstituted -(heteroalkylene)-cycloalkyl, -(heteroalkenylene)-cycloalkyl, -(heteroalkylene)-cycloalkenyl or -(heteroalkenylene)-cycloalkenyl;
• unsubstituted or at least monosubstituted -(alkylene)-heterocycloalkyl, -(alkenylene)-heterocycloalkyl, -(alkynylene)-heterocycloalkyl, -(alkylene)-heterocycloalkenyl, -(alkenylene)-heterocycloalkenyl or -(alkynylene)-heterocycloalkenyl;
• unsubstituted or at least monosubstituted -(heteroalkylene)-heterocycloalkyl, -(heteroalkenylene)-heterocycloalkyl, -(heteroalkylene)-heterocycloalkenyl or -(heteroalkenylene)-heterocycloalkenyl;
• unsubstituted or at least monosubstituted aryl;
• unsubstituted or at least monosubstituted heteroaryl;
• unsubstituted or at least monosubstituted -(alkylene)-aryl, -(alkenylene)-aryl, -(alkynylene)-aryl, -(heteroalkylene)-aryl or -(heteroalkenylene)-aryl;
• or unsubstituted or at least monosubstituted -(alkylene)-heteroaryl, -(alkenylene)-heteroaryl, -(alkynylene)-heteroaryl, -(heteroalkylene)-heteroaryl or -(heteroalkenylene)-heteroaryl;
• or R2 and R3 or R4 and R5 or R6 and R7 or R14 and R15 or R16 and R17 or R18 and R19 or R20 and R21 or R22 and R23 or R24 and R25 or R26 and R27, mutually independently, jointly denote a residue selected from the group consisting of an oxo group (═O) and a thioxo group (═S);
• or R1 and R8 together with the —N—CR2R3—(CR4R5)b—(CR6R7)c group joining them together form a residue of the formula B,
• wherein d denotes 1, 2 or 3 and b denotes 0 or 1 and c denotes 0 or 1;
• or R1 and R2 together with the —N—CR3 group joining them together form a residue of the formula C,
• wherein e denotes 1, 2, 3 or 4 and, in this case, b denotes 0 or 1 and c denotes 0;
• or R1 and R4 together with the —N—CR2R3—CR5 group joining them together form a residue of the formula D,
• wherein f denotes 1, 2, 3 or 4, and, in this case, c denotes 0;
• or R1 and R6 together with the —N—CR2R3—CR4R5—CR7 group joining them together form a residue of the formula E,
• wherein g denotes 1, 2 or 3;
• or R6 and R8 together with the —N—CR7 group joining them together form a residue of the formula F
• wherein h denotes 1, 2, 3 or 4 and, in this case, b denotes 0 or 1 and a denotes 0;
• or R4 and R8 together with the —N—CR6R7—CR5 group joining them together form a residue of the formula G,
• wherein k denotes 1, 2, 3 or 4, and, in this case, a denotes 0;
• or R2 and R8 together with the —N—CR6R7—CR4R5—CR3 group joining them together form a residue of the formula H,
• wherein m denotes 1, 2 or 3;
• R9 denotes unsubstituted or substituted aryl or unsubstituted or substituted heteroaryl;
• R10, R11 and R12, mutually independently, in each case denote H;
• F;
• Cl;
• Br;
• I;
• —NO2;
• —CN;
• —NH2;
• —OH;
• —SH;
• —C(═O)—OH;
• —C(═O)—H;
• —NH—C(═O)—H;
• —C(═O)—R28;
• —C(═O)—O—R29;
• —C(═O)—NH2;
• —C(═O)—NH—R30;
• —C(═O)—NR31R32;
• —S(═O)—R33;
• —S(═O)2—R34;
• —NH—R35;
• —NR36R37;
• —O—C(═O)—R38;
• —NH—C(═O)—R39;
• —NR40—C(═O)—R41;
• —O—R42;
• —S—R43;
• —NH—C(═O)—NH—R44;
• —NH—C(═S)—NH—R45;
• —NH—S(═O)2—R46;
• —NR47—S(═O)2—R48;
• unsubstituted or at least monosubstituted alkyl, alkenyl or alkynyl;
• unsubstituted or at least monosubstituted heteroalkyl, heteroalkenyl or heteroalkynyl;
• unsubstituted or at least monosubstituted cycloalkyl or cycloalkenyl;
• unsubstituted or at least monosubstituted heterocycloalkyl or heterocycloalkenyl;
• unsubstituted or at least monosubstituted -(alkylene)-cycloalkyl, -(alkenylene)-cycloalkyl, -(alkynylene)-cycloalkyl, -(alkylene)-cycloalkenyl, -(alkenylene)-cycloalkenyl or -(alkynylene)-cycloalkenyl;
• unsubstituted or at least monosubstituted -(heteroalkylene)-cycloalkyl, -(heteroalkenylene)-cycloalkyl, -(heteroalkylene)-cycloalkenyl or -(heteroalkenylene)-cycloalkenyl;
• unsubstituted or at least monosubstituted -(alkylene)-heterocycloalkyl, -(alkenylene)-heterocycloalkyl, -(alkynylene)-heterocycloalkyl, -(alkylene)-heterocycloalkenyl, -(alkenylene)-heterocycloalkenyl or -(alkynylene)-heterocycloalkenyl;
• unsubstituted or at least monosubstituted -(heteroalkylene)-heterocycloalkyl, -(heteroalkenylene)-heterocycloalkyl, -(heteroalkylene)-heterocycloalkenyl or -(heteroalkenylene)-heterocycloalkenyl;
• unsubstituted or at least monosubstituted aryl;
• unsubstituted or at least monosubstituted heteroaryl;
• unsubstituted or at least monosubstituted -(alkylene)-aryl, -(alkenylene)-aryl, -(alkynylene)-aryl, -(heteroalkylene)-aryl or -(heteroalkenylene)-aryl;
• or unsubstituted or at least monosubstituted -(alkylene)-heteroaryl, -(alkenylene)-heteroaryl, -(alkynylene)-heteroaryl, -(heteroalkylene)-heteroaryl or -(heteroalkenylene)-heteroaryl;
• R13 denotes H;
• —C(═O)—OH;
• —C(═O)—H;
• —C(═O)—R28;
• —C(═O)—O—R29;
• —C(═O)—NH2;
• —C(═O)—NH—R30;
• —C(═O)—NR31R32;
• —S(═O)—R33;
• —S(═O)2—R34;
• unsubstituted or at least monosubstituted alkyl, alkenyl or alkynyl;
• unsubstituted or at least monosubstituted heteroalkyl, heteroalkenyl or heteroalkynyl;
• unsubstituted or at least monosubstituted cycloalkyl or cycloalkenyl;
• unsubstituted or at least monosubstituted heterocycloalkyl or heterocycloalkenyl;
• unsubstituted or at least monosubstituted -(alkylene)-cycloalkyl, -(alkenylene)-cycloalkyl, -(alkynylene)-cycloalkyl, -(alkylene)-cycloalkenyl, -(alkenylene)-cycloalkenyl or -(alkynylene)-cycloalkenyl;
• unsubstituted or at least monosubstituted -(heteroalkylene)-cycloalkyl, -(heteroalkenylene)-cycloalkyl, -(heteroalkylene)-cycloalkenyl or -(heteroalkenylene)-cycloalkenyl;
• unsubstituted or at least monosubstituted -(alkylene)-heterocycloalkyl, -(alkenylene)-heterocycloalkyl, -(alkynylene)-heterocycloalkyl, -(alkylene)-heterocycloalkenyl, -(alkenylene)-heterocycloalkenyl or -(alkynylene)-heterocycloalkenyl;
• unsubstituted or at least monosubstituted -(heteroalkylene)-heterocycloalkyl, -(heteroalkenylene)-heterocycloalkyl, -(heteroalkylene)-heterocycloalkenyl or -(heteroalkenylene)-heterocycloalkenyl;
• unsubstituted or at least monosubstituted aryl;
• unsubstituted or at least monosubstituted heteroaryl;
• unsubstituted or at least monosubstituted -(alkylene)-aryl, -(alkenylene)-aryl, -(alkynylene)-aryl, -(heteroalkylene)-aryl or -(heteroalkenylene)-aryl;
• or unsubstituted or at least monosubstituted -(alkylene)-heteroaryl, -(alkenylene)-heteroaryl, -(alkynylene)-heteroaryl, -(heteroalkylene)-heteroaryl or -(heteroalkenylene)-heteroaryl;
• and R28, R29, R30, R31, R32, R33, R34, R35, R36, R37, R38, R39, R40, R41, R42, R43, R44, R45, R46, R47 and R48, mutually independently, in each case denote unsubstituted or substituted alkyl, alkenyl or alkynyl;
• unsubstituted or substituted heteroalkyl, heteroalkenyl or heteroalkynyl;
• unsubstituted or substituted cycloalkyl or cycloalkenyl;
• unsubstituted or substituted heterocycloalkyl or heterocycloalkenyl;
• unsubstituted or substituted -(alkylene)-cycloalkyl, -(alkenylene)-cycloalkyl, -(alkynylene)-cycloalkyl, -(alkylene)-cycloalkenyl, -(alkenylene)-cycloalkenyl or -(alkynylene)-cycloalkenyl;
• unsubstituted or substituted -(heteroalkylene)-cycloalkyl, -(heteroalkenylene)-cycloalkyl, -(heteroalkylene)-cycloalkenyl or -(heteroalkenylene)-cycloalkenyl;
• unsubstituted or substituted -(alkylene)-heterocycloalkyl, -(alkenylene)-heterocycloalkyl, -(alkynylene)-heterocycloalkyl, -(alkylene)-heterocycloalkenyl, -(alkenylene)-heterocycloalkenyl or -(alkynylene)-heterocycloalkenyl;
• unsubstituted or substituted -(heteroalkylene)-heterocycloalkyl, -(heteroalkenylene)-heterocycloalkyl, -(heteroalkylene)-heterocycloalkenyl;
• or -(heteroalkenylene)-heterocycloalkenyl;
• unsubstituted or substituted aryl;
• unsubstituted or substituted heteroaryl;
• unsubstituted or substituted -(alkylene)-aryl, -(alkenylene)-aryl, -(alkynylene)-aryl, -(heteroalkylene)-aryl or -(heteroalkenylene)-aryl;
• or unsubstituted or substituted -(alkylene)-heteroaryl, -(alkenylene)-heteroaryl, -(alkynylene)-heteroaryl, -(heteroalkylene)-heteroaryl or -(heteroalkenylene)-heteroaryl;
• in each case optionally in the form of one of the pure stereoisomers thereof, in the form of one of the racemates thereof or in the form of a mixture of stereoisomers in any mixing ratio, or in each case in the form of a corresponding salt.