DEXTROROTATORY ISOMER OF N-PHENOXYPHENYLCYCLOPENTENE-N-HYDROXY- -UREA AND PHARMACEUTICAL COMPOSITION INHIBITING 5-LIPOXYGENASE ACTIVITY Russian patent published in 1999 - IPC

Abstract RU 2125987 C1

FIELD: organic chemistry, pharmacy, biochemistry. SUBSTANCE: invention relates to new derivatives of cyclopentenylhydroxyurea that are dextrorotatory isomers of the general formula (I) and their pharmaceutically acceptable salts where R1 - hydrogen, fluorine or chlorine; R2 - hydrogen or methyl, and pharmaceutical compositions based on compounds said. Compounds of the formula (I) are synthesized by multistep method: method involves conversion of 1-bromo-3- -(4-fluorophenoxy)benzene to 3-(4-fluorophenoxy)-benzaldehyde that is converted to 1-[3-(4-fluorophenoxy)phenyl]-1,4-pentane- -dione which is converted then to the corresponding 2-cyclo- -pentene-1-one and then to its oxime; from the latter N-[3- -[3-(4-fluorophenoxyphenyl)] -2-cyclopentene-1-yl] -N-hydroxyl- -amine is synthesized which interacts with trimethylsilyliso- -cyanate and forms the corresponding N-hydroxyurea. From obtained racemate dextrorotatory enantiomer is obtained. Other dextrorotatory isomers of N-phenoxyphenylcyclopentene-N- -hydroxyurea are obtained similarly. A pharmaceutical composition has a compound of the formula (I) as an active component and a carrier. Thus, compounds of the formula (I) can be used for prophylaxis, treatment or relief of inflammatory diseases, allergy and cardiovascular diseases in mammals and as an active component in pharmaceutical compositions for treatment of patients with these states. Synthesized compounds inhibit activity of enzyme 5-lipoxygenase. EFFECT: improved method of synthesis, enhanced effectiveness of compounds. 4 cl, 1 tbl, 4 ex

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RU 2 125 987 C1

Authors

Akijosi Kavai

Rodni V.Stivens

Dates

1999-02-10Published

1994-08-15Filed