Thienyl substituted acylguanidines as inhibitors of bone resorption and vitronectin receptor antagonists

A compound of the formula I

• 47
• in which
• A is a saturated or unsaturated bivalent (C1-C9)-alkylene residue or a bivalent (C3-C7)-cycloalkylene residue, wherein the alkylene residue and the cycloalkylene residue each is unsubstituted or is substituted by one or more residues from the series consisting of halogen, (C1-C6)-alkyl, (C1-C6)-alkoxy, (C6-C14)-aryl, (C5-C14)-aryl-(C1-C6)-alkyl-, (C5-C14)-heteroaryl, (C5-C14)-heteroaryl-(C1-C6)-alkyl-, (C3-C12)-cycloalkyl, (C3-C12)-cycloalkyl-(C1-C6)-alkyl- and oxo;
• B is hydrogen, —NH—CO—OR5, —NH—SO2R5, —NH—SO2—(C6-C14)-aryl, —NH—SO2—(C5-C14)-heteroaryl, —NH—CO—R5, —NH—CO—(C5-C14)-aryl, —NH—CO—(C5-C14)-heteroaryl, —NH—CO—NH—R5, —NH—CO—NH—(C6-C14)-aryl, —NH—CO—NH—(C5-C14)-heteroaryl, —NH—SO2—NH—R5, —NH—SO2NH—(C6-C14)-aryl or —NH—SO2—NH—(C5-C14)-heteroaryl;
• D is hydrogen, (C6-C14)-aryl, (C5-C14)-heteroaryl or R5;
• R1 and R2 independently of one another are hydrogen or (C1-C6)-alkyl which is unsubstituted or substituted by one or more residues R3,
• or R1 and R2 together are a saturated or unsaturated bivalent (C2-C9)-alkylene residue which is unsubstituted or is substituted by one or more residues from the series consisting of halogen, (C1-C6)-alkyl, (C1-C6)-alkoxy, (C6-C14)-aryl, (C6-C14)-aryl-(C1-C6)-alkyl-, (Cs-C14)-heteroaryl, (C5-C14)-heteroaryl-(C1-C6)-alkyl-, (C3-C12)-cycloalkyl, (C3-C12)-cycloalkyl-(C1-C6)-alkyl- and oxo, where a 5- to 7-membered saturated or unsaturated ring which is unsubstituted or is substituted by one or more residues R3 and which is a carbocyclic ring or a heterocyclic ring containing one or two ring nitrogen atoms, can be fused to a carbon-carbon bond in the (C2-C9)-alkylene residue;
• R3 is (C1-C8)-alkyl, (C1-C8)-alkoxy, (C5-C14)-aryl, (C5-C14)-aryl-(C1-C4)-alkyl-, halogen, trifluoromethyl, hydroxyl, nitro or amino;
• R4 is hydrogen, (C1-C6)-alkyl-CO—O—(C1-C4)-alkyl- or (C1-C6)-alkyl which is unsubstituted or is substituted by a residue from the series consisting of hydroxyl, (C1-C4)-alkoxy, (C1-C4)-alkyl-S(O)2—, —NR7R7a and —N+R7R7aR7b Q−, where R7, R7a and Rb independently of one another are-hydrogen, (C1-C6)-alkyl, (C5-C14)-aryl or (C5-C14)-aryl-(C1-C6)-alkyl- and Q− is a physiologically tolerable anion, or R4 is one of the residues
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• in which the bonds via which the residues are bonded, are indicated by dashed lines;
• R5 is (C1-C14)-alkyl, (C3-C12)-cycloalkyl, (C3-C12)-cycloalkyl-(C1-C6)-alkyl-, (C6-C14)-aryl-(C1-C6)-alkyl- or (C5-C14)-heteroaryl-(C1-C6)-alkyl-, where the (C1-C14)-alkyl residue is unsubstituted or substituted by one or more halogen atoms and where the aryl residue and the heteroaryl residue is unsubstituted or is substituted by one or more residues R3;
• R6 is hydrogen, (C1-C6)-alkyl-O—CO—, hydroxyl, (C1-C6)-alkyl-O—CO—O— or nitro;
• in all their stereoisomeric forms and mixtures thereof in all ratios, and their physiologically tolerable salts and their prodrugs.