Process for producing antifungal pyridazinone derivatives...

Details Process for producing antifungal pyridazinone derivatives... Process for producing antifungal pyridazinone derivatives...

C - Chemistry, Metallurgy

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D

260/264.7

C07D 237/02 (2006.01) A01N 43/58 (2006.01) C07C 45/46 (2006.01) C07C 45/63 (2006.01) C07C 51/347 (2006.01) C07C 51/363 (2006.01) C07C 59/88 (2006.01) C07D 237/04 (2006.01) C07D 237/14 (2006.01) C07D 401/12 (2006.01)

Patent

CA 1199327

ABSTRACT Process for producing antifungal pyridazinone derivatives and certain novel compounds produced by such a process Compounds of formula (I): Image (I) [wherein R1 and R3 represent hydrogen or halogen atoms, R2 represents a hydrogen or halogen atom or a lower alkyl or alkoxy group (provided R1, R2 and R3 are not simultaneously hydrogen), Image represents a single or double carbon-carbon bond and, where it is a single bond, R4 represents a group of formula -SR5 (wherein R5 represents an optionally substituted alkyl, phenyl, aralkyl or pyridyl group or a lower alkenyl group) and, where it is a double bond, R4 represents hydrogen] can be prepared by reacting a compound of formula (II): Image (II) with a compound of formula R6H [where R6 represents a group -SR5, a group -SR7 (where R7 represents a group of formula or and Y Image Image represents oxygen or sulphur, R8 and R9 represent lower alkoxy groups and R10 represents a lower alkoxy, lower alkyl or phenyl group), a methoxy group or a halogen atom] to give a compound of formula (IV): Image (IV) or, where R6 represents a methoxy group, a methyl ester thereof; reacting this compound with hydrazine to give a compound of formula (V): Image (V) or (VI): Image (VI) and, if necessary, treating the compound of formula (V) with an acid or a base to produce the compound of formula (VI). All of the compounds of formula (I) are valuable antifungal agents and compounds of formula (V) where R6 represents a group of formula -SR5 are novel compounds.

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