Propenecarboxylic acid amidoxime derivatives, a process for the preparation thereof , and pharmaceutical compositions containing the same

A propenecarboxylic acid amidoxime derivative of the formula

• 20
• wherein
• R represents a C1-20 alkyl group, a phenyl group which latter is optionally substituted by 1-3 substituent(s)—wherein the substituent is a halo atom and/or a C1-2 alkyl group and/or a C1-2 alkoxy group and/or an amino group and/or a (C1-4 alkyl)amino group and/or a di(C1-4 alkyl)amino group and/or a (C1-4 alkanoyl)amino group—, furthermore a 5- or 6-membered saturated or unsaturated heterocyclic group containing one or two nitrogen atom(s) or a sulphur atom as the heteroatom and said heterocyclic group is optionally fused with one or more benzene ring(s) and/or one or more heterocyclic group(s), and
• R′ stands for a hydrogen atom, or
• R forms together with R′ a C5-7 cycloalkyl group optionally fused with a benzene ring,
• R4 and R5 represent, independently, a hydrogen atom, a C1-5 alkyl group, a C1-5 alkanoyl group or a phenyl group which latter is optionally substituted by 1-3 substituent(s)—wherein the substituent is a halo atom and/or a C1-2 alkyl group and/or a C1-2 alkoxy group—, or
• R4 and R5 form together with the adjacent nitrogen atom a 5- or 6-membered saturated or unsaturated heterocyclic group that may contain a further nitrogen atom and/or an oxygen atom and/or a sulphur atom as the heteroatom and can be fused with a benzene ring, and the heterocyclic group and/or the benzene ring may bear one or two substituent(s) wherein the substituent is a halo atom and/or a C1-2 alkyl group and/or a C1-2 alkoxy group,
• R1 and R2 stand for a hydrogen atom and
• R3 means a hydrogen atom, a hydroxy group or a C1-5 alkoxy group, or
• R1 forms together with R2 a carbonyl group or a thiocarbonyl group the carbon atom of which is bound to the oxygen atom adjacent to R1 and to the nitrogen atom adjacent to R2, and
• R3 represents a hydrogen atom, a halo atom, a hydroxy group, a C1-5 alkoxy group, a C1-5 alkylthio group, a C1-20 alkanoyl-oxy group, a C3-22 alkenoyloxy group containing one or more double bond(s), a methylsulfonyloxy group, a benzene-sulfonyloxy group or a toluenesulfonyloxy group, or
• R2 is a hydrogen atom and
• R1 forms together with R3 a valence bond between the oxygen atom adjacent to R1 and the carbon atom adjacent to R3, furthermore N-oxides and/or geometrical isomers and/or optical isomers and/or pharmaceutically suitable acid addition salts and/or quaternary derivatives thereof.