Bradykinin-B1 antagonists, process for their preparation and their use as medicaments

A compound of the formula

• in which
• R1 is a phenyl, naphthyl or heteroaryl group, a phenyl-C1-3-alkyl or C3-7-cycloalkyl group,
• R4 is a hydrogen atom or a C1-6-alkyl group,
• G is the group —(CH2)m—, in which m is the number 2 or 3 and in which one to three hydrogen atoms independently of one another may be replaced by C1-3-alkyl groups,
• Ar is a phenylene or heteroarylene group,
• Q is the group —(CH2)p—, in which p is the number 2 or 3 and in which one to three hydrogen atoms independently of one another may be replaced by C1-3-alkyl groups,
• A is a group, attached via a nitrogen atom to the sulphonyl group in formula (I), of the formulae (IIa) to (IIi)
• where the groups (IIa) to (IIi) are preferably attached to the sulphonyl group in formula (I) via the position marked *″,
• n is the number 2 or 3,
• o is the number 1, 2 or 3,
• R2 is a hydrogen atom, a C1-6alkyl, C2-5-alkenyl-methyl, C2-5-alkynyl-methyl, C3-7-cycloalkyl or a phenyl group and
• R3 is a hydrogen atom, a phenyl, C1-6-alkyl, C2-5-alkenyl-methyl, C2-5-alkynyl-methyl or C3-7-cycloalkyl group or a group —CH2—CF3, —CH2—CHF2 or —CH2—CH2F,
• where the phenyl and phenylene groups present in the definitions mentioned above may be mono-, di-, tri- or tetrasubstituted by fluorine, chlorine, bromine or iodine atoms, by C1-5-alkyl, trifluoromethyl, amino, C1-3-alkylamino, di-(C1-3-alkyl)-amino, di-(C1-3-alkyl)-amino-carbonylamino, nitro, cyano, C1-3-alkylcarbonyl, C1-3-alkylsulphonyl, aminocarbonyl, C1-3-alkylaminocarbonyl, di-(C1-3-alkyl)-aminocarbonyl, aminosulphonyl, C1-3-alkylaminosulphonyl, di-(C1-3-alkyl)-aminosulphonyl, C1-3-alkylcarbonylamino, carboxy-C1-3-alkyl, C1-3-alkyloxycarbonyl-C1-3-alkyl, phenyl, phenyloxy, hydroxyl, C1-4-alkyloxy, monofluoromethyloxy, difluoromethyloxy or trifluoromethyloxy groups or by N-pyrrolidinocarbonyl, N-pyrrolidinosulphonyl, N-piperidinocarbonyl or N-piperidinosulphonyl, where the methylene group present in the piperidine rings mentioned above may be replaced in the 4-position by O, S, SO, SO2, NH or N(C1-3-alkyl), and the substituents may be identical or different, except for substitution by two, three or four nitro groups,
• where the naphthyl groups present in the definitions mentioned above may be mono- or disubstituted by fluorine, chlorine, bromine or iodine atoms, by C1-3-alkyl, amino or di-(C1-3-alkyl)-amino groups and the substituents may be identical or different,
• where, unless indicated otherwise, a heteroaryl group mentioned above is a monocyclic 5-membered heteroaryl group attached via a carbon or nitrogen atom which
• contains an imino group which is optionally substituted by a C1-3-alkyl, phenyl or phenyl-C1-3-alkyl group, an oxygen or sulphur atom or
• an imino group which is optionally substituted by a C1-3-alkyl, phenyl, amino-C2-3-alkyl, C1-3-alkylamino-C2-3-alkyl or di-(C1-3-alkyl)-amino-C2-3-alkyl group, by a 4- to 7-membered cycloalkyleneimino-C1-3-alkyl or phenyl-C1-3-alkyl group or an oxygen atom or sulphur atom and additionally a nitrogen atom or
• an imino group which is optionally substituted by a C1-3-alkyl or phenyl-C1-3-alkyl group and two or three nitrogen atoms,
• or a monocyclic 6-membered heteroaryl group which contains one, two or three nitrogen atoms,
• or a bicyclic 9-membered heteroaryl group consisting of one of the 5-membered heteroaryl groups mentioned above which is fused to one of the 6-membered heteroaryl groups mentioned above via two adjacent carbon atoms or a carbon and an adjacent nitrogen atom forming a bicycle, where the 5-membered heteroaryl group may also be replaced by a cyclopentadienyl group or the 6-membered heteroaryl group may also be replaced by a phenyl ring,
• or a bicyclic 10-membered heteroaryl group which consists of a phenyl ring and one of the 6-membered heteroaryl groups mentioned above or of two of the 6-membered heteroaryl groups mentioned above which are in each case condensed via two adjacent carbon atoms forming a bicycle,
• where the mono- and bicyclic heteroaryl groups mentioned above may additionally be mono-, di- or trisubstituted in the carbon skeleton by fluorine, chlorine, bromine or iodine atoms or by C1-3-alkyl groups and where the substituents may be identical or different,
• and the term “heteroarylene group” mentioned above in the definitions is to be understood as meaning the mono- or bicyclic heteroaryl groups mentioned above which, however, are attached to the adjacent groups via two carbon atoms or via one carbon and one nitrogen atom,
• where the alkyl and alkoxy groups present in the definitions mentioned above which have more than two carbon atoms may, unless indicated otherwise, be straight-chain or branched, and
• where some or all of the hydrogen atoms of the methyl or ethyl groups present in the definitions mentioned above may be replaced by fluorine atoms,
• or a tautomer or a salt thereof.