4-(arylaminomethylene)-2,4-dihydro-3-pyrazolones

Details 4-(arylaminomethylene)-2,4-dihydro-3-pyrazolones 4-(arylaminomethylene)-2,4-dihydro-3-pyrazolones

C - Chemistry, Metallurgy

07

D

C07D 231/20 (2006.01) A61K 31/4152 (2006.01)

Patent

CA 2176649

The invention relates to 5-pyrazolinone derivatives of the general formula I: Image in which R1 is benzyl, alkoxybenzyl with 1-3 C atoms in the alkyl moiety, phenyl, phenyl which is substituted once to three times by amino, acyl, halogen, nitro, CN, AO-, carboxyl, sulphonyl, A-O-CO-, A-CO-NH-, A-CO-NA-, carbamoyl, N-alkylcarbamoyl, N,N-dialkylcarbamoyl (with 1-6 C atoms in the alkyl moiety), A-O-CO-NH-, A-O-CO-NA-, A-SO2-, SO2NR4R5 (R4 and R5 representing H or alkyl with 1-6 C atoms, or NR4R5 representing a 5- or 6-membered ring, optionally with other heteroatoms, which may be substituted by A), A-CO-NH-SO2-, A-CO-NA-SO2-, A-SO2-NH-, A-SO2-NA-, (A-SO2-) 2N-, tetrazolyl or phosphonyl; or pyridyl, R 2 is alkyl with 1-5 C atoms, alkoxycarbonylalkyl, hydroxyalkyl, hydroxycarbonylalkyl, R3 is straight-chain or branched alkyl with 1-5 C atoms, straight-chain or branched alkoxy with 1-5 C atoms, fluorine- or chlorine-substituted alkyl, A is straight-chain or branched alkyl with 1-6 C atoms, straight-chain or branched alkyl with 1-6 C atoms which is substituted by fluorine or chlorine, or a pharmaceutically acceptable salt thereof, with exclusion of 5-methyl-2-phenyl-4-(o- tolylaminomethylene)-2,4-dihydropyrazol-3-one. Part of the invention also comprises processes for the preparation of these compounds, but in particular their use as selective inhibitors of cGMP-specific phosphodiesterase (cGMP PDE) and thus as pharmaceutically active compounds.

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