Imino compounds, process for their preparation and their use as victronectin antagonists

A compound of formula (1),

• R.sup.1 --Y--A--B--D--E--F--G (1),
• in which:
• A is a direct bond, (C.sub.1 -C.sub.8)-alkanediyl, --NR.sup.2 --N.dbd.CR.sup.2 --, --NR.sup.2 --C(O)--NR.sup.2 --, --NR.sup.2 --C(O)O--, --NR.sup.2 --C(O)S--, --NR.sup.2 --C(S)--NR.sup.2 --, --NR.sup.2 --C(S)--O--, --NR.sup.2 --C(S)--S--, --NR.sup.2 --S(O).sub.n n--NR.sup.2, --NR.sup.2 --S(O).sub.n --O--, --NR.sup.2 --S(O).sub.n --, (C.sub.3 --C.sub.12)-cycloalkanediyl, --C.tbd.C--, --NR.sup.2 --C(O)--, --C(O)--NR.sup.2 --, --(C.sub.5 --C.sub.14)-arylene-C(O)--NR.sup.2 --, --O--, --S(O).sub.n --, --(C.sub.5 -C.sub.14)-arylene-, --CO--, --(C.sub.5 -C.sub.14)-arylene-CO--, NR.sup.2 --, --SO.sub.2 --NR.sup.2 --, --CO.sub.2 --, --N.dbd.CR.sup.2 --, --R.sup.2 C.dbd.N--, --CR.sup.2 .dbd.CR.sup.3 --, --(C.sub.5 -C.sub.14)-arylene-S(O).sub.n --, wherein each case is unsubstituted or mono- or disubstituted by (C.sub.1 -C.sub.8)-alkanediyl;
• B is a direct bond, (C.sub.1 -C.sub.8)-alkanediyl, --CR.sup.2 .dbd.CR.sup.3 -- or --C.tbd.C--, wherein each case is unsubstituted or mono- or disubstituted by (C.sub.1 -C.sub.8)-alkanediyl, or a divalent radical of a 5- or 6-membered saturated or unsaturated ring, which contains from 0 to 2 nitrogen atom and is unsubstituted or mono-or disubstituted by (C.sub.1 -C.sub.6)-alkyl or doubly bonded oxygen or sulfur;
• D is a direct bond, (C.sub.1 -C.sub.8)-alkanediyl, or --O--, --NR.sup.2 --, --CO--NR.sup.2 --, --NR.sup.2 --CO--, --NR.sup.2 --C(O)--NR.sup.2 --, --NR.sup.2 --C(S)--NR.sup.2 --, --OC(O)--, --C(O)O--, --CO--, --CS--, --S(O)--, --S(O).sub.2 --S(O).sub.2 --NR.sup.2 --, --NR.sup.2 --S(O)--, --NR.sup.2 --S(O).sub.2 --, --S--, --CR.sup.2 .dbd.CR.sup.3 --, --C.dbd.--C--, --NR.sup.2 --N.dbd.CR.sup.2 --, --N.dbd.CR.sup.2 --, --R.sup.2 C.dbd.N-- or --CH(OH)--, wherein each case is unsubstituted or mono- or disubstituted by (C.sub.1 -C.sub.8)-alkanediyl;
• E is a 6-membered aromatic ring system, which contains from 0 to 4 nitrogen atoms and is unsubstituted or substituted by 1-4 identical or different radicals selected from the group consisting of R.sup.2, R.sup.3, fluorine, Cl, Br, I, NO.sub.2 and OH;
• F is selected from the group consisting of the same constituents as defined for D and is the same or different than D;
• G is ##STR29## Y is a direct bond or --NR.sup.2 --;
• R.sup.1 is --C(.dbd.NR.sup.2)--NR.sup.2 --, R.sup.2 R.sup.3 N--C(.dbd.NR.sup.2)--, R.sup.2 R.sup.3 N--C(.dbd.NR.sup.2)--NR.sup.2 --, or a 4-10-membered mono- or polycyclic aromatic or nonaromatic ring system, substituted with from 0 to 4 heteroatoms selected from the group consisting of N, O and S and is unsubstituted or monosubstituted or polysubstituted by substituents selected from the group consisting of R.sup.12, R.sup.13, R.sup.14 and R.sup.15 ;
• R.sup.2, R.sup.3 independently of one another are H, (C.sub.1 -C.sub.10)-alkyl, which is unsubstituted or mono- or polysubstituted by fluorine, (C.sub.3 -C.sub.12)-cyclo-alkyl, (C.sub.3 -C.sub.12)-cycloalkyl-(C.sub.1 -C.sub.8)-alkanediyl, (C.sub.5 -C.sub.14)-aryl, (C.sub.5 -C.sub.14)-aryl-(C.sub.1 -C.sub.8)-alkanediyl, H.sub.2 N, (R.sup.8 O)R.sup.8 NR.sup.9, R.sup.8 OR.sup.9, R.sup.8 OC(O)R.sup.9, R.sup.8 --(C.sub.1 -C.sub.14)-arylene-R.sup.9, R.sup.8 R.sup.8 NR.sup.9, HO--(C.sub.1 -C.sub.8)-alkanediyl-NR.sup.8 R.sup.9, R.sup.8 R.sup.8 NC(O)R.sup.9, R.sup.8 C(O)NR.sup.8 R.sup.9, R.sup.8 C(O)R.sup.9, R.sup.8 R.sup.8 N--C(.dbd.NR.sup.8)--, R.sup.8 R.sup.8 N--C(.dbd.NR.sup.8)--NR.sup.8 -- or (C.sub.1 -C18)-alkylcarbonyloxy-(C.sub.1 -C.sub.6)-alkanediyloxycarbonyl;
• R.sup.4, R.sup.5, R.sup.6, R.sup.7 independently of one another are H, fluorine, OH, (C.sub.1 -C.sub.8)-alkyl, (C.sub.3 -C.sub.12)-cycloalkyl, (C.sub.3 -C.sub.12)-cycloalkyl-(C.sub.1 -C.sub.8)-alkanediyl, or R.sup.8 OR.sup.9, R.sup.8 SR.sup.9, R.sup.8 CO.sub.2 R.sup.9, R.sup.8 OC(O)R.sup.9, R.sup.8 --(C.sub.5 -C.sub.14)-arylene-R.sup.9, R.sup.8 N(R.sup.2)R.sup.9, R.sup.8 R.sup.8 NR.sup.9, R.sup.8 N(R.sup.2)C(O)OR.sup.9, R.sup.8 S(O).sub.n N(R.sup.2)R.sup.9, R.sup.8 OC(O)N(R.sup.2)R.sup.9, R.sup.8 C(O)N(R.sup.2)R.sup.9, R.sup.8 N(R.sup.2)C(O)N(R.sup.2)R.sup.9, R.sup.8 N(R.sup.2)S(O).sub.n N(R.sup.2)R.sup.9, R.sup.8 S(O).sub.n R.sup.9, R.sup.8 SC(O)N(R.sup.2)R.sup.9, R.sup.8 C(O)R.sup.9, R.sup.8 N(.sup.2)C(O)R.sup.9, or R.sup.8 N(R.sup.2)S(O).sub.n R.sup.9 ;
• R.sup.8 is H, (C.sub.1 -C.sub.8)-alkyl, (C.sub.3 -C.sub.12)-cycloalkyl, (C.sub.3 -C.sub.12)-cycloalkyl-(C.sub.1 -C.sub.8)-alkanediyl, (C.sub.5 -C.sub.14)-aryl, or (C.sub.5 -C.sub.14)-aryl-(C.sub.1 -C.sub.8)-alkanediyl, wherein alkyl or cycloalkyl or alkanediyl is unsubstituted or mono- or polysubstituted by fluorine;
• R.sup.9 is a direct bond or (C,-C.sub.8)-alkanediyl;
• R.sup.10 is C(O)R.sup.11, C(S)R.sup.11, S(O).sub.n R.sup.11, P(O)(R.sup.11).sub.n or a four- to eight-membered, saturated or unsaturated heterocycle which contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of:
• N, O and S;
• R.sup.11 is OH, (C.sub.1 -C.sub.8)-alkoxy, (C.sub.5 -C.sub.14)-aryl-(C.sub.1 -C.sub.8)-alkanediyloxy, (C.sub.5 -C.sub.14)aryloxy, (C.sub.1 -C.sub.8)-alkylcarbonyloxy-(C.sub.1 -C.sub.4)-alkanediyloxy, (C.sub.5 -C.sub.14)-aryl-(C.sub.1 -C.sub.8)-alkanediylcarbonyloxy-(C.sub.1 -C.sub.6)-alkanediyloxy, NH.sub.2, mono- or di-(C.sub.1 -C.sub.8 -alkyl)-amino, (C.sub.5 -C.sub.14)-aryl-(C.sub.1 -C.sub.8)-alkanediylamino, (C.sub.1 -C.sub.8)-dialkylaminocarbonylmethylenoxy, (C.sub.5 -C.sub.14)-aryl-(C.sub.1 -C.sub.8)-dialkylaminocarbonylmethylenoxy or (C.sub.5 -C.sub.14)-arylamino or a radical of an L- or D-amino acid;
• R.sup.12, R.sup.13, R.sup.14, R.sup.15 independently of one another are H, (C.sub.1 -C.sub.10)-alkyl, wherein each case is unsubstituted or mono- or polysubstituted by fluorine, (C.sub.3 -C.sub.12)-cycloalkyl, (C.sub.3 --C.sub.12)-cycloalkyl-(C.sub.1 -C.sub.8)-alkanediyl, (C.sub.5 -C.sub.14)-aryl, (C.sub.5 -C.sub.14)-aryl-(C.sub.1 -C.sub.8)-alkanediyl, H.sub.2 N, (R.sup.8 O)R.sup.8 NR.sup.9, R.sup.8 OR.sup.9, R.sup.8 OC(O)R.sup.9, R.sup.8 R.sup.8 NR.sup.9, R.sup.8 --(C.sub.5 -C.sub.14)-arylene-R.sup.9, HO--(C.sub.1 -C.sub.8)-alkanediyl-N(R.sup.2)R.sup.9, R.sup.8 N(R.sup.2)C(O)R.sup.9, R.sup.8 C(O)N(R.sup.2)R.sup.9, R.sup.8 C(O)R.sup.9, R.sup.2 R.sup.3 N--C(.dbd.NR.sup.2)--NR.sup.2 --, R.sup.2 R.sup.3 N--C(.dbd.NR.sup.2)--, .dbd.O, or .dbd.S;
• n is 1 or 2;
• p, q independently of one another are 0 or 1;
• in all their stereoisomeric forms or mixtures thereof in any ratio;
• or their physiologically tolerable salts;
• wherein at least one of the groups A, D or F is --NR.sup.2 --N.dbd.CR.sup.2 --, --N.dbd.CR.sup.2 -- or --R.sup.2 C.dbd.N--.