5-[1-(imidazol)methyl]-3,3-disubstituted-2(3h)furanone...

C - Chemistry – Metallurgy – 07 – D

Patent

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167/231, 167/237

C07D 405/06 (2006.01) A61K 31/415 (2006.01) A61K 31/435 (2006.01) C07D 405/14 (2006.01) C07D 409/14 (2006.01) C07D 471/04 (2006.01) C07D 487/04 (2006.01) C07D 521/00 (2006.01)

Patent

CA 2030396

Furanone compounds and compositions having anticholinergic activity are described. The compounds have the formula: Image wherein: the dashed line indicates either the 4,5-unsaturated or the 4,5-dihydrofuranone ring; R1 and R2 may be the same or different and are hydrogen, thienyl, furanyl, or cycloalkyl (C3-C6), benzyl, phenyl, substituted phenyl or substituted benzyl wherein the phenyl or benzyl group may be substituted with halogen, trifluoromethyl, lower alkyl, lower alkoxy or hydroxy; R3, R4 and R5 may be the same or different and are hydrogen, lower alkyl, lower alkyl substituted with a halogen, alkoxy, amino or carboxylic acid group, an alkyl or alkylene bridge between R4 and R5 or R3 and the ring N, trifluoromethyl, nitro, a cycloalkyl group containing 3 to 6 carbons, halogen, benzyl, phenyl, substituted phenyl or substituted benzyl, for which the substituents are the same as those set forth for R1 and R2 substituted benzyl or phenyl. R6 in the dihydrofuranone series is hydrogen or lower alkyl. Also described are the pharmaceutically acceptable quaternary alkyl and acid addition salts of such compounds. The compounds are particularly useful in the treatment of neurogenic bladder disorder and chronic obstructive pulmonary diseases.

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