Substituted indoles

A compound of the formula I

• 24
• in any stereoisomeric form, or a physiologically acceptable salt thereof, where
• one of the substituents R1, R2, R3 and R4 is a radical of the formula II
• 25
• in which D is —C(O)—, —S(O)— or —S(O)2—,
• R7 is hydrogen or —(C1-C4)-alkyl,
• R8 is R9 or the characteristic radical of an amino acid,
• R9 is 1. aryl, where aryl is unsubstituted or substituted,
• 2. heteroaryl having 5 to 14 ring members, where heteroaryl is unsubstituted or substituted,
• 3. heterocycle having 5 to 12 ring members, where heterocycle is unsubstituted or substituted, or
• 4. —(C1-C6)-alkyl, where alkyl is straight-chain or branched and is unsubstituted or mono-, di- or trisubstituted, independently of one another, by
• 4.1 aryl, where aryl is unsubstituted or substituted,
• 4.2 heteroaryl having 5 to 14 ring members, where heteroaryl is unsubstituted or substituted,
• 4.3 heterocycle having 5 to 12 ring members, where heterocycle is unsubstituted or substituted,
• 4.4 —O—R10,
• 4.5 ═O,
• 4.6 halogen,
• 4.7 —CN,
• 4.8 —CF3,
• 4.9 —S(O)x—R10, where x is the integer zero, 1 or 2,
• 4.10 —C(O)—O—R10,
• 4.11 —C(O)—N(R10)2,
• 4.12 —N(R10)2,
• 4.13 —(C3-C6)-cycloalkyl,
• 4.14 radical of the formula
• 26
• or
• 4.15 radical of the formula
• R10 is a) hydrogen,
• b) —(C1-C6)-alkyl, where alkyl is unsubstituted or mono- to trisubstituted, independently of one another, by
• 1. aryl,
• 2. heteroaryl having 5 to 14 ring members,
• 3. heterocycle having 5 to 12 ring members,
• 4. halogen,
• 5. —N-(C1-C6)n-alkyl, where n is the integer zero, 1 or 2 and alkyl is unsubstituted or mono-, di- or trisubstituted, independently of one another, by halogen or by —COOH, or
• 6. —COOH,
• c) aryl,
• d) heteroaryl having 5 to 14 ring members or
• e) heterocycle having 5 to 12 ring members and, in the case of (R10)2 R10, independently of one another, has the meaning of a) to e),
• Z is 1. aryl, where aryl is unsubstituted or substituted,
• 2. heteroaryl having 5 to 14 ring members, where heteroaryl is unsubstituted or substituted,
• 3. heterocycle having 5 to 12 ring members, where heterocycle is unsubstituted or substituted, or
• 4. —C(O)—R11, where
• R11 is 1. —O—R10 or
• 2. —N(R10)2, or
• R7 and R8 form, together with the nitrogen atom and carbon atom to which they are each bonded, a heterocyclic ring of the formula IIa,
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• in which D, Z and R are as defined in formula II,
• A is a nitrogen atom or the radical —CH2—,
• B is an oxygen atom, sulfur atom, nitrogen atom or the radical —CH2—,
• X is an oxygen atom, sulfur atom, nitrogen atom or the radical —CH2—,
• Y is absent or is an oxygen atom, sulfur atom, nitrogen atom or the radical —CH2—, or
• X and Y together form a phenyl, 1,2-diazine, 1,3-diazine or a 1,4-diazine radical,
• where the ring system formed by N, A, X, Y, B and the carbon atom contains not more than one oxygen atom, X is not an oxygen atom, sulfur or nitrogen atom if A is a nitrogen atom, contains not more than one sulfur atom, contains 1, 2, 3 or 4 nitrogen atoms and where an oxygen and sulfur atom do not occur at the same time, where the ring system formed by N, A, X, Y, B and the carbon atom is unsubstituted or mono- to trisubstituted, independently of one another, by —(C1-C8)-alkyl, unsubstituted or mono- to disubstituted by
• 1.1. —OH,
• 1.2. (C1-C8)-alkoxy,
• 1.3. halogen,
• 1.4. —NO2,
• 1.5. —NH2,
• 1.6. —CF3,
• 1.7. —OH,
• 1.8 methylenedioxy,
• 1.9 —C(O)—CH3,
• 1.10. —CH(O),
• 1.11. —CN,
• 1.12. —C(O)—OH,
• 1.13. —C(O)—NH2,
• 1.14. (C1-C4)-alkoxycarbonyl,
• 1.15. phenyl,
• 1.16. phenoxy,
• 1.17. benzyl,
• 1.18. benzyloxy or
• 1.19. tetrazolyl, or
• R8 and Z form, together with the carbon atoms to which they each are bonded, a heterocyclic ring of the formula IIc,
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• in which D, R and R are as defined in formula II,
• T is an oxygen atom, sulfur atom, nitrogen atom or the radical —CH2—,
• W is an oxygen atom, sulfur atom, nitrogen atom or the radical —CH2—,
• V is absent or is an oxygen atom, sulfur atom, nitrogen atom or the radical —CH2—, or
• T and V or V and W together form a phenyl, 1,2-diazine, 1,3-diazine or a 1,4-diazine radical, where the ring system formed by N, T, V, W and two carbon atoms contains not more than one oxygen atom, not more than one sulfur atom and 1, 2, 3 or 4 nitrogen atoms, where an oxygen atom and sulfur atom do not occur at the same time, and where the ring system formed by N, T, V, W and two carbon atoms is unsubstituted or mono- to trisubstituted, independently of one another, by the substituents defined above under 1.1. to 1.19., and the respective other substituents R1, R2, R3 and R4 independently of one another are
• 1. hydrogen,
• 2. halogen,
• 3. aryl, where aryl is unsubstituted or substituted,
• 4. heteroaryl having 5 to 14 ring members, where heteroaryl is unsubstituted or substituted,
• 5. heterocycle having 5 to 12 ring members, where heterocycle is unsubstituted or substituted,
• 6. —(C1-C6)-alkyl,
• 7. —CN,
• 8. —O—R10,
• 9. —N(R10)2,
• 10. —S(O)x—R10, where x is the integer zero, 1 or 2, or
• 11. —CF3,
• R5 is 1. hydrogen,
• 2. —OH or
• 3. ═O, and
• R6 is 1. aryl, where aryl is unsubstituted or substituted,
• 2. heteroaryl having 5 to 14 ring members, where heteroaryl is unsubstituted or mono- to trisubstituted, or
• 3. heterocycle having 5 to 12 ring members, where heterocycle is unsubstituted or mono-, di- or trisubstituted.