Substituted 1,2-ethylenediamines, Methods for Preparing Them and Uses Thereof

A compound of formula (I):

• wherein:
• A denotes aryl or heteroaryl, optionally substituted by one or more fluorine atoms;
• L each independently denotes hydrogen, fluorine, chlorine, bromine, iodine, hydroxy, carboxy, formyl, cyano, nitro, F3C, HF2C, FH2C, C1-6-alkyl, C2-6-alkenyl, C2-6-alkynyl, C1-6-alkyl-S, C1-6-alkyl-S—C1-3-alkyl, C3-7-cycloalkyl, C3-7-cycloalkenyl, C3-7-cycloalkyl-C1-6-alkyl, C3-7-cycloalkyl-C2-6-alkenyl, C3-7-cycloalkyl-C2-6-alkynyl, C3-7-cycloalkenyl-C1-6-alkyl, C3-7-cycloalkenyl-C2-6-alkenyl, C3-7-cycloalkenyl-C2-6-alkynyl, aryl, aryl-C1-6-alkyl, aryl-C2-6-alkenyl, aryl-C2-6-alkynyl, heterocyclyl, heterocyclyl-C1-6-alkyl, heterocyclyl-C2-6-alkenyl, heterocyclyl-C2-6-alkynyl, heteroaryl, heteroaryl-C1-6-alkyl, heteroaryl-C2-6-alkenyl, heteroaryl-C2-6-alkynyl, R15—O, R15—O—C1-3-alkyl, (R14)2N, (R14)2N—CO, R14—CO—(R14)N, (R14)2N—CO—(R14)N, R14—SO2—(R14)N, (R14)2N—SO2 or R14—SO2, wherein the above-mentioned groups are optionally substituted independently of one another by one or more groups selected from fluorine, chlorine, bromine, iodine, hydroxy, oxo, carboxy, formyl, cyano, nitro, F3C, HF2C, FH2C, hydroxy-C1-6-alkyl, C1-3-alkyl, C1-6-alkoxy, (R14)2N, (R14)2N—C1-3-alkyl, (R14)2N—CO and HOSO2—;
• i denotes 0, 1, 2 or 3;
• B denotes a C1-4-alkylene bridge, optionally substituted by one or more groups selected from fluorine, chlorine, bromine, iodine, hydroxy, oxo, carboxy, cyano, nitro, F3C, HF2C, FH2C, C1-4-alkyl, C1-6-alkyl-S—C1-3-alkyl, C3-7-cycloalkyl, C3-7-cycloalkyl-C1-3-alkyl, heterocyclyl, heterocyclyl-C1-3-alkyl, aryl, aryl-C1-3-alkyl, heteroaryl, heteroaryl-C1-3-alkyl, R15—O, (R14)2N—SO2, (R14)2N, (R14)2N—C1-3-alkyl, (R14)2N—CO, R14—SO2, R14—CO—(R14)N, R14—SO2(R14)N, (R14)2N—SO2, R14—CO— and R14—SO—, wherein
• two C1-4-alkyl groups bound to the same carbon atom of the C1-4-alkylene bridge may be joined together to form a C3-7-cycloalkyl group, and each of the the above-mentioned groups and the C3-7-cycloalkyl group formed from the C1-4-alkyl groups are optionally substituted independently of one another by one or more groups selected from fluorine, chlorine, bromine, iodine, hydroxy, oxo, carboxy, formyl, cyano, nitro, F3C, HF2C, FH2C, C1-3-alkyl, C1-3-alkoxy, R15—O—C1-3-alkyl, R14—CO(R14)N, R14—SO2(R14)N, (R14)2N, (R14)2N—C1-3-alkyl, (R14)2N—CO, (R14)2N—SO2— and HOSO2—, and
• wherein when B is a C3-4-alkylene bridge, the CH2 group of the C3-4-alkylene bridge, which is bound to the group A, may be replaced by —O—;
• R1 denotes hydrogen, C1-6-alkyl, C2-6-alkenyl, C2-6-alkynyl, C3-7-cycloalkyl, C3-7-cycloalkyl-C1-6-alkyl, C3-7-cycloalkyl-C2-6-alkenyl, C3-7-cycloalkyl-C2-6-alkynyl, C3-7-cycloalkenyl, C3-7-cycloalkenyl-C1-6-alkyl, C3-7-cycloalkenyl-C2-6-alkenyl, C3-7-cycloalkenyl-C2-6-alkynyl, aryl, aryl-C1-6-alkyl, aryl-C2-6-alkenyl, aryl-C2-6-alkynyl, heterocyclyl, heterocyclyl-C1-6-alkyl, heterocyclyl-C2-6-alkenyl, heterocyclyl-C2-6-alkynyl, heteroaryl, heteroaryl-C1-6-alkyl, heteroaryl-C2-6-alkenyl or heteroaryl-C2-6-alkynyl,
• wherein the above-mentioned groups are optionally substituted independently of one another by one or more groups selected from fluorine, chlorine, bromine, iodine, hydroxy, oxo, carboxy, formyl, cyano, nitro, F3C, HF2C, FH2C, C1-3-alkyl, C1-3-alkoxy, hydroxy-C1-6-alkyl, (R14)2N, (R14)2N—C1-3-alkyl, (R14)2N—CO— (R14)2N—SO2, R14—CO—(R14)N, R14—SO2—(R14)N and HOSO2—;
• X1, denotes nitrogen or C(R10);
• X2, X3, X4 each independently denotes nitrogen or C(R11),
• with the proviso that 0, 1, 2 or 3 of the groups X1, X2, X3 and X4 may be nitrogen;
• R2 denotes C1-6-alkyl, C2-6-alkenyl, C2-6-alkynyl, R15—O—C1-3-alkyl, C1-6-alkyl-S—C1-3-alkyl, C3-7-cycloalkyl, C3-7-cycloalkyl-C2-6-alkynyl, C3-7-cycloalkenyl, C3-7-cycloalkenyl-C1-6-alkyl, C3-7-cycloalkenyl-C2-6-alkenyl, C3-7-cycloalkenyl-C2-6-alkynyl, heterocyclyl, C3-7-cycloalkyl-C1-3-alkyl, heterocyclyl-C1-3-alkyl, C3-7-cycloalkyl-C2-3-alkenyl, heterocyclyl-C2-3-alkenyl, heterocyclyl-C2-3-alkynyl, aryl, heteroaryl, aryl-C1-3-alkyl, heteroaryl-C1-3-alkyl, aryl-C2-3-alkenyl, aryl-C2-3-alkynyl, heteroaryl-C2-3-alkenyl or heteroaryl-C2-3-alkynyl,
• wherein the above-mentioned groups are optionally substituted independently of one another by one or more groups selected from fluorine, chlorine, bromine, iodine, F3C, HF2C, FH2C, hydroxy, oxo, carboxy, formyl, cyano, nitro, (R14)2N, HOSO2—, C1-3-alkyl, C1-6-alkyl-S—C1-3-alkyl, (R14)2N—SO2—, R14—CO—(R14)N, R14—SO2—(R14)N, (R14)2N—C1-3-alkyl, (R14)2N—CO, R15—O and R15—O—C1-3-alkyl;
• R3, R4 each independently denotes hydrogen, C1-6-alkyl, fluorine, F3C, HF2C or FH2C;
• R5, R7 each independently denote hydrogen, C1-6-alkyl, C2-6-alkenyl, C2-6-alkynyl, C3-7-cycloalkyl, heterocyclyl, C3-7-cycloalkyl-C1-3-alkyl, C3-7-cycloalkyl-C2-6-alkynyl, heterocyclyl-C1-3-alkyl, C3-7-cycloalkyl-C2-4-alkenyl, heterocyclyl-C2-4-alkenyl, heterocyclyl-C2-4-alkynyl, C3-7-cycloalkenyl, C3-7-cycloalkenyl-C1-6-alkyl, C3-7-cycloalkenyl-C2-6-alkenyl, C3-7-cycloalkenyl-C2-6-alkynyl, aryl, heteroaryl, aryl-C1-3-alkyl, heteroaryl-C1-3-alkyl, aryl-C2-3-alkenyl, heteroaryl-C2-3-alkenyl, aryl-C2-3-alkynyl or heteroaryl-C2-3-alkynyl,
• wherein the above-mentioned groups are optionally substituted independently of one another by one or more groups selected from fluorine, chlorine, bromine, iodine, hydroxy, oxo, carboxy, formyl, cyano, nitro, C1-3-alkyl, R15—O, C1-3-alkyl-S, aryl, heteroaryl, heteroaryl-C1-3-alkyl, aryl-C1-6-alkyl, R14—CO—(R14)N, R14—SO2—(R14)N, (R14)2N—SO2—, (R14)2N, (R14)2N—C1-3-alkyl, (R14)2N—CO and HOSO2—;
• R6, R9 each independently denotes hydrogen, C1-6-alkyl, C1-6-alkoxy-C1-3-alkyl, C3-7-cycloalkyl, C3-7-cycloalkyl-C1-3-alkyl, C2-6-alkenyl, heterocyclyl-C1-3-alkyl, heteroaryl, heteroaryl-C1-3-alkyl or C2-6-alkynyl,
• wherein the above-mentioned groups are optionally substituted independently of one another by one or more groups selected from among fluorine, chlorine, bromine, iodine, cyano, C1-3-alkyl, C1-6-alkoxy- and (R14)2N;
• R8 denotes hydrogen, C1-6-alkyl, C2-6-alkenyl, C2-6-alkynyl, C3-7-cycloalkyl, C3-7-cycloalkyl-C1-3-alkyl, C3-7-cycloalkyl-C2-4-alkenyl, C3-7-cycloalkyl-C2-4-alkynyl, C3-7-cycloalkenyl, C3-7-cycloalkenyl-C1-6-alkyl, C3-7-cycloalkenyl-C2-6-alkenyl, C3-7-cycloalkenyl-C2-6-alkynyl, heterocyclyl, heterocyclyl-C1-3-alkyl, heterocyclyl-C2-4-alkenyl, heterocyclyl-C2-4-alkynyl, aryl, aryl-C1-3-alkyl, aryl-C2-4-alkenyl, aryl-C2-4-alkynyl, heteroaryl, heteroaryl-C1-3-alkyl, heteroaryl-C2-4-alkenyl or heteroaryl-C2-4-alkynyl,
• wherein the above-mentioned groups are optionally substituted independently of one another by one or more groups selected from fluorine, chlorine, bromine, iodine, hydroxy, oxo, carboxy, formyl, cyano, nitro, C1-3-alkyl, heterocyclyl, heterocyclyl-C1-3-alkyl, R15—O, R15—O—C1-3-alkyl, R15—S, R15—S—C1-3-alkyl, aryl, heteroaryl, heteroaryl-C1-3-alkyl, aryl-C1-6-alkyl, (R14)2N, (R14)2N—C1-3-alkyl, (R14)2N—CO, (R14)2N—CO—N(R14)—, (R14)2N—SO2— and HOSO2—;
• R10 denotes hydrogen, fluorine, chlorine, bromine, iodine, cyano, C1-6-alkyl, C2-6-alkenyl, C2-6-alkynyl, C3-7-cycloalkyl, C3-7-cycloalkyl-C1-6-alkyl, C3-7-cycloalkyl-C2-6-alkynyl, heterocyclyl, heterocyclyl-C1-6-alkyl, heterocyclyl-C2-6-alkenyl, heterocyclyl-C2-6-alkynyl, C3-7-cycloalkyl-C2-6-alkenyl, heterocyclyl-C2-4-alkenyl, C3-7-cycloalkenyl, C3-7-cycloalkenyl-C1-6-alkyl, C3-7-cycloalkenyl-C2-6-alkenyl, C3-7-cycloalkenyl-C2-6-alkynyl, aryl, aryl-C1-6-alkyl, heteroaryl, heteroaryl-C1-6-alkyl, aryl-C2-6-alkenyl, heteroaryl-C2-6-alkenyl, aryl-C2-6-alkynyl or heteroaryl-C2-6-alkynyl, R15—O, R15—O—C1-3-alkyl, R12—SO2—(R13)N or R12—CO—(R13)N
• wherein the above-mentioned groups are optionally substituted independently of one another by one or more groups selected from among fluorine, chlorine, bromine, iodine, hydroxy, oxo, carboxy, formyl, cyano, nitro, C1-6-alkyl, C2-6-alkenyl, C2-6-alkynyl, C1-6-alkyl-S, C1-6-alkyl-S—C1-3-alkyl, C3-7-cycloalkyl, C3-7-cycloalkyl-C1-6-alkyl, aryl, aryl-C1-6-alkyl, heterocyclyl, heterocyclyl-C1-6-alkyl, heteroaryl, heteroaryl-C1-6-alkyl, R15-0, R15—O—CO, R15—CO, R15—O—CO—(R14)N, (R14)2N—CO—O, R15—O—C1-3-alkyl, (R14)2N, (R14)2N—CO, R14—CO—(R14)N, (R14)2N—CO—(R14)N, (R14)2N—SO2—, (R14)2N—SO2—(R14)N, R14—SO2—, F3C, HF2C, FH2C, F3C—O, HF2C—O, FH2C—O and R14—SO2—(R14)N;
• R11 each independently denotes hydrogen, fluorine, chlorine, bromine, iodine, R15—O, (R14)2N or C1-3-alkyl,
• wherein the C1-3-alkyl group is optionally substituted by one or more fluorine atoms;
• R12 denotes C1-6-alkyl, C2-6-alkenyl, C2-6-alkynyl, C3-7-cycloalkyl-C2-6-alkenyl, aryl-C2-3-alkenyl, heteroaryl-C2-4-alkenyl, heterocyclyl-C2-4-alkenyl, aryl-C2-3-alkynyl, C3-7-cycloalkyl-C2-4-alkynyl, heterocyclyl-C2-4-alkynyl-heteroaryl-C2-3-alkynyl, C3-7-cycloalkyl, C3-7-cycloalkyl-C1-6-alkyl, heterocyclyl, heterocyclyl-C1-4-alkyl, C3-7-cycloalkenyl, C3-7-cycloalkenyl-C1-6-alkyl, C3-7-cycloalkenyl-C2-6-alkenyl, C3-7-cycloalkenyl-C2-6-alkynyl, aryl, aryl-C1-4-alkyl, heteroaryl, heteroaryl-C1-3-alkyl or (R14)2N,
• wherein the above-mentioned groups are optionally substituted independently of one another by one or more groups selected from among fluorine, chlorine, bromine, hydroxy, oxo, carboxy, formyl, cyano, nitro, C1-3-alkyl, heterocyclyl, heterocyclyl-C1-3-alkyl, R15—O, R15—O—C1-3-alkyl, R14—CO(R14)N, R14—SO2(R14)N, (R14)2N—SO2—, R14—SO2—, R14—SO, R14—S, (R14)2N, (R14)2N—C1-3-alkyl and (R14)2N—CO;
• R13 denotes hydrogen, C1-6-alkyl, C2-6-alkenyl, C2-6-alkynyl, C3-7-cycloalkyl, C3-7-cycloalkyl-C1-3-alkyl, aryl, aryl-C1-3-alkyl, heterocyclyl, heterocyclyl-C1-3-alkyl, heterocyclyl-C2-3-alkenyl, heterocyclyl-C2-3-alkynyl, heteroaryl, heteroaryl-C2-3-alkenyl, heteroaryl-C2-3-alkynyl or heteroaryl-C1-3-alkyl, wherein the above-mentioned groups are optionally substituted independently of one another by one or more groups selected from among fluorine, chlorine, bromine, hydroxy, oxo, carboxy, formyl, cyano, nitro, C1-3-alkyl, heterocyclyl, heterocyclyl-C1-3-alkyl, R15—O, R15—O—C1-3-alkyl, (R14)2N, (R14)2N—C1-3-alkyl and R14CO;
• or
• R12 and R13 together form a C2-6-alkylene bridge, so that with the inclusion of the nitrogen atom linked to R13 and the SO2— or CO group linked to R12, a heterocyclic ring is formed,
• wherein one or two CH2 groups of the C2-6-alkylene bridge may be replaced independently of one another by O, S, SO, SO2 or N(R14) in such a way that in each case two O or S atoms or an O and an S atom are not joined together directly, and
• the C atoms of the above-mentioned C2-6-alkylene bridge are optionally substituted by one or more groups selected from fluorine, chlorine, bromine, hydroxy, carboxy, formyl, cyano, F3C, HF2C, FH2C, C1-6-alkyl, C1-6-alkoxy, oxo and nitro;
• R14 each independently denotes hydrogen, C1-6-alkyl, C1-6-alkoxy-C1-3-alkyl, C3-6-cyclyoalkyl, C3-6-cyclyoalkyl-C1-3-alkyl, aryl or aryl-C1-3-alkyl, heterocyclyl, heterocyclyl-C1-3-alkyl, heteroaryl or heteroaryl-C1-3-alkyl, wherein
• two C1-6-alkyl groups bound to the same nitrogen atom together may form a C2-6-alkylene bridge, so that with the inclusion of the nitrogen atom bound to the groups R14 a heterocyclic ring is formed,
• wherein a CH2 group of the C2-6-alkylene bridge may be replaced by O, S or N(R14), and
• the above-mentioned groups and the heterocyclic ring are optionally substituted independently of one another by one or more groups selected from among fluorine, chlorine, bromine, iodine, hydroxy, oxo, carboxy, formyl, cyano, nitro, C1-3-alkyl, hydroxy-C1-3-alkyl, C1-3-alkoxy, (R15)2N—CO or (R15)2N, and
• R15 each independently denotes hydrogen, C1-6-alkyl, C2-6-alkenyl, C2-6-alkynyl, C3-7-cycloalkyl, C3-7-cyclyoalkyl-C1-3-alkyl, aryl, aryl-C1-3-alkyl, heterocyclyl, heterocyclyl-C1-3-alkyl, heteroaryl or heteroaryl-C1-3-alkyl, wherein the above-mentioned groups are optionally substituted independently of one another by one or more groups selected from fluorine, chlorine, bromine, iodine, hydroxy, oxo, carboxy, formyl, cyano, nitro, C1-3-alkyl- and C1-3-alkoxy;
• and tautomers, diastereomers, enantiomers, mixtures thereof and salts thereof.