Heteroaryl-substituted 1,3-dihydroindol-2-one derivatives and medicaments containing Them

A compound of the formula (II)

• in which
• B is selected from the group consisting of thiophene, furan, pyrrole, pyridine, quinoline, tetrahydroquinoline, isoquinoline, tetrahydroisoquinoline, benzothiophene, benzofuran, dihydrobenzofuran, indole, dihydroisoindole,
• an aromatic heteromonocyclic and an aromatic or partially aromatic heterobicyclic ring,
• where the heterocycles are 5- or 6-membered rings and comprise 2 to 4 heteroatoms selected from the group consisting of N, O and S, and up to 2 oxo groups, and
• B may be substituted by the radicals R21, R22 and/or R23,
• R21, R22 and R23 at each occurrence are selected independently of one another from the group consisting of hydrogen, chlorine, bromine, iodine, fluorine, CN, CF3, OCF3, NO2, OH, O—C1-C4-alkyl, O-phenyl, O—C1-C4-alkylen-phenyl, phenyl, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, NH2, NH(C1-C4-alkyl) and N(C1-C4-alkyl)2, morpholin-4-yl, pyrrolidin-1-yl, piperidin-1-yl, 4-piperazin-1-yl, 4-(C1-C4-alkyl)-piperazin-1-yl,
• R3 and R4 are selected independently of one another from the group consisting of hydrogen, chlorine, bromine, iodine, fluorine, CN, CF3, OCF3, NO2, OH, O—C1-C4-alkyl, O-phenyl, O—C1-C4-alkylen-phenyl, phenyl, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, NH2, NH(C1-C4-alkyl) and N(C1-C4-alkyl)2, or
• R3 and R4 are connected to give —CH═CH—CH═CH—, —(CH2)4— or —(CH2)3—,
• R5 is a radical (W)—(X)—(Y)-Z, where
• W is selected from the group consisting of C1-C4-alkylen, C2-C4-alkenylen, C2-C4-alkynylen, O, O—(C1-C4-alkylen), S, S—(C1-C4-alkylen), NR54, NR54—(C1-C4-alkylen) and a bond,
• X is selected from the group consisting of CO, CO—O, SO2, NR54, NR54—CO, NR54—SO2, CO—NR58 and a bond,
• Y is C1-C6-alkylen, C2-C6-alkenylen, C2-C6-alkynylen, or a bond,
• Z is selected from the group consisting of hydrogen, E, O—R52, NR51R52, S—R52, where
• E is an unsaturated, saturated or partially unsaturated mono-, bi- or tricyclic ring having a maximum of 14 carbon atoms and 0 to 5 nitrogen atoms, 0 to 2 oxygen atoms and/or 0 to 2 sulfur atoms, said ring may comprise up to two oxo groups, and may be substituted by radicals R55, R56, R57 and/or up to three radicals R53 and,
• R51 at each occurrence is independently selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, phenyl and C1-C4-alkylen-phenyl, where the phenyl ring may be substituted by up to two radicals R53,
• R52 at each occurrence is independently selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, E and C1-C4-alkylen-E,
• R53 at each occurrence is independently selected from the group consisting of hydrogen, chlorine, bromine, iodine, fluorine, CN, CF3, OCF3, NO2, OH, O—C1-C4-alkyl, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, NH2, NH(C1-C4-alkyl) and N(C1-C4-alkyl)2,
• R54 at each occurrence is independently selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, phenyl and C1-C4-alkylen-phenyl, where the phenyl ring may be substituted by up to two radicals R59,
• R55 at each occurrence is independently selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, phenyl, C1-C4-alkylen-phenyl, where the ring may be substituted by up to two radicals R60, and OH, O—C1-C4-alkyl, O-phenyl, O—C1-C4-alkylen-phenyl, NH2, NH(C1-C4-alkyl) and N(C1-C4-alkyl)2,
• R56 is a group Q1-Q2-Q3, where
• Q1 is selected from the group consisting of a bond, C1-C4-alkylen, C2-C4-alkenylen, C2-C4-alkynylen, C1-C4-alkylen-N(C1-C4-alkyl), N(C1-C4-alkyl), C1-C4-alkylen-NH, NH, N(C1-C4-alkyl)-C1-C4-alkylen, NH—C1-C4-alkylen, O, C1-C4-alkylen-O, O—C1-C4-alkylen, CO—NH, CO—N(C1-C4-alkyl), NH—CO, N(C1-C4-alkyl)-CO, CO, SO2, SO, S, O, SO2—NH, SO2—N(C1-C4-alkyl), NH—SO2, N(C1-C4-alkyl)-SO2, O—CO—NH, O—CO—N(C1-C4-alkyl), NH—CO—O, N(C1-C4-alkyl)-CO—O, N(C1-C4-alkyl)-CO—N(C1-C4-alkyl), NH—CO—N(C1-C4-alkyl), N(C1-C4-alkyl)-CO—NH, and NH—CO—NH,
• Q2 is selected from the group consisting of C1-C4-alkylen, C2-C4-alkenylen, C2-C4-alkynylen, and a bond,
• Q3 is a hydrogen or an unsaturated, saturated or partially unsaturated mono-, bi- or tricyclic ring having a maximum of 14 carbon atoms and 0 to 5 nitrogen atoms, 0 to 2 oxygen atoms and/or 0 to 2 sulfur atoms, which may comprise up to two oxo groups and may be substituted by the radicals R63, R64 and/or R65,
• R57 at each occurrence is independently selected from the group consisting of hydrogen, C1-C6-alkyl, phenyl, C1-C4-alkylen-phenyl, COOH, CO—O—C1-C4-alkyl, CONH2, CO—NH—C1-C4-alkyl, CO—N(C1-C4-alkyl)2, CO—C1-C4-alkyl, CH2—NH2, CH2—NH—C1-C4-alkyl and CH2—N(C1-C4-alkyl)2,
• R58 at each occurrence is independently selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, phenyl and C1-C4-alkylen-phenyl, where the phenyl ring may be substituted by up to two radicals R62,
• R59, R60 and R62 at each occurrence are selected independently of one another from the group consisting of hydrogen, chlorine, bromine, iodine, fluorine, CN, CF3, OCF3, NO2, OH, O—C1-C4-alkyl, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, NH2, NH(C1-C4-alkyl) and N(C1-C4-alkyl)2,
• R63, R64 and R65 at each occurrence are independently selected of one another from the group consisting of hydrogen, chlorine, bromine, iodine, fluorine, CN, CF3, OCF3, NO2, OH, O—C1-C4-alkyl, O-phenyl, O—C1-C4-alkylen-phenyl, phenyl, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, NH2, NH(C1-C4-alkyl) and N(C1-C4-alkyl)2,
• R6 and R7 at each occurrence are selected independently of one another from the group consisting of hydrogen, chlorine, bromine, iodine, fluorine, CN, CF3, OCF3, NO2, OH, O—C1-C4-alkyl, O-phenyl, O—C1-C4-alkylen-phenyl, phenyl, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, NH2, NH(C1-C4-alkyl) and N(C1-C4-alkyl)2,
• and their tautomeric forms, enantiomeric and diastereomeric forms, and prodrugs thereof.

A compound of the formula (III),

• in which
• D is an aromatic heteromonocyclic, or an aromatic or partially aromatic heterobicyclic ring,
• where the heterocycles are 5- or 6-membered rings and comprise up to 4 heteroatoms selected from the group consisting of N, O and S, and up to 2 oxo groups,
• and D may be substituted by radicals R21, R22 and/or R23,
• G is an aromatic heteromonocyclic, aromatic or partially aromatic heterobicyclic ring,
• where the heterocycles are 5- or 6-membered rings and comprise up to 4 heteroatoms selected from the group consisting of N, O and S, and up to 2 oxo groups and
• G may be substituted by radicals R71, R72 and/or R73,
• R21, R22, R23, R71, R72 and R73 at each occurrence are selected independently of one another from the group consisting of hydrogen, chlorine, bromine, iodine, fluorine, CN, CF3, OCF3, NO2, OH, O—C1-C4-alkyl, O-phenyl, O—C1-C4-alkylen-phenyl, phenyl, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, NH2, NH(C1-C4-alkyl) and N(C1-C4-alkyl)2, morpholin-4-yl, pyrrolidin-1-yl, piperidin-1-yl, 4-piperazin-1-yl, 4-(C1-C4-alkyl)-piperazin-1-yl,
• R3 and R4 at each occurrence are selected independently of one another from the group consisting of hydrogen, chlorine, bromine, iodine, fluorine, CN, CF3, OCF3, NO2, OH, O—C1-C4-alkyl, O-phenyl, O—C1-C4-alkylen-phenyl, phenyl, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, NH2, NH(C1-C4-alkyl) and N(C1-C4-alkyl)2, or
• R3 and R4 are connected to give —CH═CH—CH═CH—, —(CH2)4— or —(CH2)3—,
• R5 is a radical (W)—(X)—(Y)-Z, where
• W is selected from the group consisting of C1-C4-alkylen, C2-C4-alkenylen, C2-C4-alkynylen, O, O—(C1-C4-alkylen), S, S—(C1-C4-alkylen), NR54, NR54—(C1-C4-alkylen) and a bond,
• X is selected from the group consisting of CO, CO—O, SO2, NR54, NR54—CO, NR54—SO2, CO—NR58 and a bond,
• Y is C1-C6-alkylen, C2-C6-alkenylen, C2-C6-alkynylen, or a bond,
• Z is selected from the group consisting of hydrogen, E, O—R52, NR51R52, S—R52, where
• E is an unsaturated, saturated or partially unsaturated mono-, bi- or tricyclic ring having a maximum of 14 carbon atoms and 0 to 5 nitrogen atoms, 0 to 2 oxygen atoms and/or 0 to 2 sulfur atoms, which may comprise up to two oxo groups, and E may be substituted by radicals R55, R56, R57 and/or up to three radicals R53, R51 at each occurrence is independently selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, phenyl and C1-C4-alkylen-phenyl, where the phenyl ring may be substituted by up to two radicals R53,
• R52 at each occurrence is independently selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, E and C1-C4-alkylen-E,
• R53 at each occurrence is independently selected from the group consisting of hydrogen, chlorine, bromine, iodine, fluorine, CN, CF3, OCF3, NO2, OH, O—C1-C4-alkyl, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, NH2, NH(C1-C4-alkyl) and N(C1-C4-alkyl)2,
• R54 at each occurrence is independently selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, phenyl and C1-C4-alkylen-phenyl, where the phenyl ring may be substituted by up to two radicals R59,
• R55 at each occurrence is independently selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, phenyl, C1-C4-alkylen-phenyl, where the ring may be substituted by up to two radicals R60, and OH, O—C1-C4-alkyl, O-phenyl, O—C1-C4-alkylen-phenyl, NH2, NH(C1-C4-alkyl) and N(C1-C4-alkyl)2,
• R56 is a group Q1-Q2-Q3, where
• Q1 is selected from the group consisting of a bond, C1-C4-alkylen, C2-C4-alkenylen, C2-C4-alkynylen, C1-C4-alkylen-N(C1-C4-alkyl), N(C1-C4-alkyl), C1-C4-alkylen-NH, NH, N(C1-C4-alkyl)-C1-C4-alkylen, NH—C1-C4-alkylen, O, C1-C4-alkylen-O, O—C1-C4-alkylen, CO—NH, CO—N(C1-C4-alkyl), NH—CO, N(C1-C4-alkyl)-CO, CO, SO2, SO, S, O, SO2—NH, SO2—N(C1-C4-alkyl), NH—SO2, N(C1-C4-alkyl)-SO2, O—CO—NH, O—CO—N(C1-C4-alkyl), NH—CO—O, N(C1-C4-alkyl)-CO—O, N(C1-C4-alkyl)-CO—N(C1-C4-alkyl), NH—CO—N(C1-C4-alkyl), N(C1-C4-alkyl)-CO—NH, and NH—CO—NH,
• Q2 is selected from the group consisting of C1-C4-alkylen, C2-C4-alkenylen, C2-C4-alkynylen, and a bond,
• Q3 is a hydrogen or an unsaturated, saturated or partially unsaturated mono-, bi- or tricyclic ring having a maximum of 14 carbon atoms and 0 to 5 nitrogen atoms, 0 to 2 oxygen atoms and/or 0 to 2 sulfur atoms, which may comprise up to two oxo groups and may be substituted by the radicals R63, R64 and/or R65,
• R57 at each occurrence is independently selected from the group consisting of hydrogen, C1-C6-alkyl, phenyl, C1-C4-alkylen-phenyl, COOH, CO—O—C1-C4-alkyl, CONH2, CO—NH—C1-C4-alkyl, CO—N(C1-C4-alkyl)2, CO—C1-C4-alkyl, CH2—NH2, CH2—NH—C1-C4-alkyl and CH2—N(C1-C4-alkyl)2,
• R58 at each occurrence is independently selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, phenyl and C1-C4-alkylen-phenyl, where the phenyl ring may be substituted by up to two radicals R62,
• R59, R60 and R62 at each occurrence are selected independently of one another from the group consisting of hydrogen, chlorine, bromine, iodine, fluorine, CN, CF3, OCF3, NO2, OH, O—C1-C4-alkyl, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, NH2, NH(C1-C4-alkyl) and N(C1-C4-alkyl)2,
• R63, R64 and R65 at each occurrence are selected independently of one another from the group consisting of hydrogen, chlorine, bromine, iodine, fluorine, CN, CF3, OCF3, NO2, OH, O—C1-C4-alkyl, O-phenyl, O—C1-C4-alkylen-phenyl, phenyl, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, NH2, NH(C1-C4-alkyl) and N(C1-C4-alkyl)2,
• and their tautomeric forms, enantiomeric and diastereomeric forms, and prodrugs thereof.