Substituted arylsulfonylaminomethylphosphonic acid derivatives, their preparation and their use in the treatment of type I and II diabetes mellitus

A compound of formula (I)

• wherein
• R denotes a group of formula
• wherein
• R1 denotes H, C1-6-alkyl-carbonyl-oxy-C1-3-alkyl or C1-6-alkoxy-carbonyl-oxy-C1-3-alkyl,
• R2 and R3 independently of one another denote H, halogen, C1-3-alkyl, C1-3-perfluoralkyl, C1-3-perfluoroalkoxy, C1-3-alkoxy, cyano, nitro or hydroxy
• and
• A denotes CH or N,
• and the heterocyclic group
• denotes a group of formula
• wherein the above-mentioned heterocycles of formula n (Ia), (Ib), (Ic), (Id), (If), (Ig), (Ih), (Ii), (Ik) and (Io) may optionally be substituted at the carbon atoms of the 5 ring in each case by a group selected from among C1-3-alkyl, cyano, C1-3-perfluoralkyl, C3-6-cycloalkyl, C1-3-alkyl-carbonyl, C1-3-Perfluoralkyl-carbonyl, carboxyl, amino-methyl, C1-3-alkyl-aminomethyl, di-(C1-3-alkyl)-aminomethyl, C1-3-alkyl-carboxyl, carboxy-C1-3-alkyl, aminocarbonyl, C1-3-alkyl-aminocarbonyl or di-(C1-3-alkyl)-aminocarbonyl and
• R4 denotes H, C1-6-alkyl, C1-6-alkyl-carbonyl, cyano, carboxyl, C1-6-alkoxy-carbonyl, phenylcarbonyl, 5-chloro-1H-indol-2-yl-carbonyl, aminocarbonyl, C1-6-alkyl-aminocarbonyl, di-(C1-6-alkyl)-aminocarbonyl, C3-6-cycloalkyl-aminocarbonyl, N—(C3-6-cycloalkyl)-N—(C1-6-alkyl)-aminocarbonyl, morpholin-4-yl-carbonyl, piperazin-1-yl-carbonyl, 4-(C1-3-alkyl)-piperazin-1-yl-carbonyl, aryl-amino-carbonyl, N-oxy-pyridylamino-carbonyl, aminocarbonyl-carbonyl, C1-3-alkylaminocarbonyl-carbonyl, di-(C1-3-alkyl)-aminocarbonyl-carbonyl, pyrrolidinylcarbonyl-carbonyl, piperidinyl-carbonyl-carbonyl, morpholinylcarbonyl-carbonyl, piperazinylcarbonyl-carbonyl, 4-methyl-piperazin-1-ylcarbonyl-carbonyl, C1-3-alkyl-sulphonyl or phenyl-sulphonyl,
• while the C1-6-alkyl group mentioned above in the definition of R4 may be substituted by phenyl or phenylsulphonyl,
• the C1-6-alkyl-carbonyl group mentioned above in the definition of R4 may be substituted in the alkyl moiety by di-(C1-3-alkyl)-amino, pyrrolidin-1-yl, piperidin-1-yl, morpholin-4-yl, piperazin-1-yl, 4-methyl-piperazin-1-yl or phenyl,
• the C1-6-alkyl-aminocarbonyl, di-(C1-6-alkyl)-aminocarbonyl and N—(C3-6-cycloalkyl)-N—(C1-6-alkyl)-aminocarbonyl groups mentioned above in the definition of R4 may each be substituted in the alkyl moiety by C1-3-alkyl-amino, di-(C1-3-alkyl)-amino, C3-6-cycloalkyl-amino, N—(C3-6-cycloalkyl)-N—(C1-6-alkyl)-amino, pyrrolidin-1-yl, piperidin-1-yl, morpholin-4-yl, piperazin-1-yl, 4-methyl-piperazin-1-yl or methylaminocarbonyl,
• the aryl moiety of the aryl-amino-carbonyl groups mentioned above in the definition of R4 is a 6-membered aromatic system which contains 0 to 3 nitrogen atoms and may be substituted by nitro,
• the C1-6-alkyl groups of the di-(C1-6-alkyl)-aminocarbonyl groups mentioned above in the definition of R4, together with the nitrogen atom to which they are bound, may form a saturated 4- to 7-membered ring system, which may be substituted by hydroxy, and
• the C1-3-alkyl-sulphonyl group mentioned above in the definition of R4 may be substituted by phenyl in the alkyl moiety,
• or the tautomers, stereoisomers, mixtures thereof and salts thereof.