Indoline derivatives substituted in the 6-position, their preparation and their use as medicaments

A compound of the formula

• in which
• X is an oxygen atom,
• R1 is a hydrogen atom,
• R2 is a fluorine, chlorine or bromine atom or a cyano group,
• R3 is a phenyl group which is substituted
• by a carboxy-C1-4-alkoxy, C1-4-alkoxy-carbonyl-C1-3-alkoxy, aminocarbonyl-C1-3-alkyl, (C1-2-alkylamino)-carbonyl-C1-3-alkyl, di-(C1-2-alkyl)-aminocarbonyl-C1-3-alkyl, (C1-2-alkyl-carbonyl)-amino-C1-3-alkyl, or C1-3-alkyl-piperazin-1-yl-carbonyl-C1-3-alkyl group,
• R4 is a phenyl group which is monosubstituted
• by a C1-3-alkyl group which is terminally substituted by di-(C1-2-alkyl)-amino-, imidazol-1-yl, pyrrolidin-1-yl,
• or
• by a group of the formula
• in which
• R7 is a C1-2-alkyl, C1-2-alkyl-carbonyl, or C1-3-alkylsulphonyl group and
• R8 is ω-[di-(C1-2-alkyl)-amino]C2-3-alkyl, or
• a (C1-3-alkyl)-carbonyl group which is terminally substituted by a di-(C1-2-alkyl)-amino, piperazin-1-yl or 4-(C1-3-alkyl)-piperazin-1-yl group,
• where all dialkylamino groups present in the radical R4 may also be present in quaternized form, where the counterion is preferably selected from the group consisting of iodide, chloride, bromide, methylsulphonate, para-toluenesulphonate and trifluoroacetate,
• R5 is a hydrogen atom and
• R6 is a hydrogen atom,
• where the abovementioned alkyl groups include linear and branched alkyl groups in which additionally one to 3 hydrogen atoms may be replaced by fluorine atoms,
• where additionally a carboxyl, amino or imino group present may be substituted by an in vivo cleavable radical or may be present in the form of a prodrug radical,
• or a salt thereof.