5-imidazolidinones and thiohydantoin compounds

C - Chemistry – Metallurgy – 07 – D

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260/315.05, 260/

C07D 233/32 (2006.01) C07D 233/86 (2006.01)

Patent

CA 1122989

ABSTRACT OF THE DISCLOSURE Compounds of the formula (I): Image (I) wherein: Y is -CH2CH2-, -CH-CH- or -C=C- n is 1 to 5; R1 is hydrogen, or CO2R1 represents an ester group in which the R1 moiety contains from 1 to 12 carbon atoms; R2 is hydrogen, C1-4 alkyl, trifluoromethyl, or phenyl; R3 is hydroxy or protected hydroxy: R5 is hydrogen, C1-6 alkyl, phenyl or phenyl C1-6 alkyl, any of which phenyl moieties may be substituted by one or more halogen, trifluoromethyl, C1-6 alkyl, C1-6 alkoxy or nitro groups; and X is CH2 and R4 is C1-9 alkyl, C3-8 cycloalkyl-C1-6 alkyl, phenyl-C1-6 alkyl or naphthy1-C1-6 alkyl, any of which groups may have one acyclic carbon-carbon bond interrupted by an oxygen atom; hydrogen, C3-8 cycloalkyl, phenyl or naphthyl, any of which phenyl of naphthyl moieties in R4 may be substituted by one or more halogen, tri- fluoromethyl, C1-6 alkyl, hydroxy, C1-6 alkoxy or nitro groups; or R2 and R4 taken with the carbon atom to which they are joined represent a C5-8 cycloalkyl group; or X is CS and R4 is C1-9 alkyl, C3-8 cycloalkyl-C1-6 alkyl, phenyl-C1-6 alkyl or naphthyl-C1-6 alkyl, having one acyclic carbon-carbon bond interrupted by an oxygen atom, and in which any phenyl or naphthyl moieties may be substituted by one or more halogen, trifluoromethyl, C1-6 alkyl, hydroxy, C1-6 alkoxy or nitro groups; and salts thereof; having similar pharmacological activity to natural prostaglandins, processes for their prepara- tion, intermediates useful in those processes and pharmaceutical compositions containing compounds of the formula (I).

324464

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