Pyrazol-5-ones

C - Chemistry – Metallurgy – 07 – D

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C07D 231/20 (2006.01) C07D 231/24 (2006.01) C07D 231/52 (2006.01)

Patent

CA 1048513

PYRAZOL-5-ONES Abstract of the Disclosure 1-Substituted pyrazol-5-ones of the formula Image and pharmaceutically acceptable, nontoxic salts thereof, wherein R is hydrogen or amino; R1 is hydrogen, alkyl, alkenyl, unsubstituted or sub- stituted aryl or unsubstituted or substituted aralkyl; X is a) ethylene, ethylene wherein 1 hydrogen atom on one of the carbon atoms is substituted by alkyl of 1 to 4 carbon atoms, ethylene wherein 1 hydro- gen atom on each of the two carbon atoms is sub- stituted by alkyl of 1 to 4 carbon atoms or said ethylene which is linked to R2 via an oxygen or sulphur atom; b) propenyl, propenyl wherein 1 hydrogen atom on one, two or three of the carbon atoms is substituted by alkyl of 1 to 4 carbon atoms, said propenyl being linked to the N1 atom of the pyrazol ring via its methylene moiety; or c) methylene; provided that when X is methylene, R1 is not hydrogen if R is amino; -1- R2 is aryl unsubstituted or substituted by: a) 1 or 2 of the same or different substituents selected from the group consisting of halogen, trifluoromethyl, alkyl of 1 to 8 carbon atoms, alkenyl of 2 to 8 carbon atoms and lower alkoxy; b) cycloalkyl of 5, 6 or 7 carbon atoms or cyclo- alkenyl of 5, 6 or 7 carbon atoms; c) alkylamino, dialkylamino, cyano, trifluoromethoxy, nitro, carbamoyl, alkylcarbamoyl, dialkylcarbamoyl, or said carbamoyl wherein the nitrogen atom is a member of a heterocyclic ring, sulphamyl, alkyl- sulphamyl, dialkylsulphamyl, or said sulphamyl wherein the nitrogen is a member of a heterocyclic ring, or -SOn-alkyl wheeein n is 0, 1 or 2; d) alkylamino, dialkylamino, cyano, trifluoromethoxy, nitro, carbamoyl, alkylcarbamoyl, dialkylcarbamoyl, or said carbamoyl wherein the nitrogen atom is a member of a heterocyclic ring, sulphamyl, alkyl- sulphamyl, dialkylsulphamyl or said sulphamyl wherein the nitrogen is a member of heterocyclic ring, or -SOn-alkyl whereln n is 0, 1 or 2, and 1 or 2 of the same or different substituents selected from the group consisting of alkyl, alkenyl, alkoxy, halogen, and trifluoromethyl; or e) a fused, saturated or unsaturated 5-, 6-, or 7- membered ring or said ring containing 1 or 2 oxygen or sulphur atoms; are useful for their diuretic, saluretic, antihypertensive and antithrombotic effects. -2-

197658

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