Benzimidazole derivatives and pharmaceutical compositions comprising these compounds
AssigneeNeuroSearch A/S
InventorsLene Teuber, Frank Watjen
Life of this patent
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Abstract
The present invention relates to novel 1-phenylbenzimidazole derivatives having particular alkoxycarbonyl substituents in the 5-position of the benz ring and having particular cyclic substituents in the meta-position of the phenyl ring, as well as to pharmaceutical compositions containing these compounds and to methods of treatment therewith. The compounds of the invention are useful in the treatment of central nervous system diseases and disorders, which are responsive to modulation of GABAA receptor complex, and in particular for inducing and maintaining anaesthesia, sedation, and muscle relaxation, as well as for combating febrile convulsions in children. The compounds of the invention may also be used by veterinarians.
Claims12
A benzimidazole derivative represented by Formula I,
- or a pharmaceutically acceptable salt thereof,
- wherein:
- R′ represents a group of the formula -(alk)q-R1, in which (alk) represents alkyl, alkenyl, or alkynyl, q is 0 or 1, and R1 represents a group of the formula —CO2R2, wherein R2 represents hydroxy-alkyl, alkoxy-alkyl, or thioalkoxy-alkyl;
- and
- R″ represents a group of the formula
- in which formula “o” is 0 or 1, “n” is 0, 1, or 2, X represents N or CR, Y represents O, NR11, or CHR11, wherein R11 represents hydrogen, alkyl, hydroxyalkyl, alkoxy-alkyl, carboxyl, or acyl, or a group of the formula -(alkyl)p-CN, -(alkyl)p-aryl, -(alkyl)p-O-aryl, -(alkyl)p-O-aralkyl, -(alkyl)p-“Heterocycle”, -(alkyl)p-CO2-“Heterocycle”, or -(alkyl-CO2)p-(alkyl)t-COR5, wherein p, s, and t independently of each another is 0 or 1, “Heterocycle” represents a mono- or polycyclic heterocyclic group, which heterocyclic group is optionally substituted one or more times with substituents selected from the group consisting of halogen, alkyl, hydroxy, oxo, cyano, hydroxy-alkyl, alkoxy—alkyl, carboxyl, and acyl, R5 represents hydroxy, alkoxy, hydroxy-alkoxy, alkoxy—alkoxy, thioalkoxy-alkoxy, aryl, or aralkyl, or a group of the formula —NR6R7 or -O-alkyl-NR6R7, in which formulas R6 and R7 independently of each another represent hydrogen, alkyl, cycloalkyl, or a mono- or polycyclic heterocyclic group, which heterocyclic group is optionally substituted one or more times with substituents selected from the group consisting of alkyl and acyl, or R6 and R7 together with the nitrogen to which they are attached form a mono- or polycyclic heterocyclic group, which heterocyclic group is optionally substituted one or more times with substituents selected from the group consisting of alkyl and acyl, and R14 and R15 independently of each another represent hydrogen, alkyl, hydroxy-alkyl, alkoxy-alkyl, carboxyl, or acyl.
Dependencies are inferred from the claim text.