Process of producing 3,5-di-tert-butyl-4-...

C - Chemistry – Metallurgy – 07 – D

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C07D 233/54 (2006.01) A61K 31/415 (2006.01) C07D 233/64 (2006.01) C07D 233/66 (2006.01) C07D 263/30 (2006.01) C07D 263/32 (2006.01) C07D 277/20 (2006.01) C07D 277/22 (2006.01)

Patent

CA 1187088

ABSTRACT A method of producing a 3,5-di-tert-butyl-4-hydroxyphenyl- substituted heterocyclic compound represented by formula I Image wherein one of R1, R2, and R3 represents a 3,5-di-tert-butyl-4- hydroxyphenyl group Image and others represent a hydrogen atom, a lower alkyl group, a lower aralkyl group, an aryl group, a lower alkoxy-substituted aryl group, or the group shown by -O-Z, Image , or -NH-Z (wherein Z represents a hydrogen atom, a lower alkyl group, a carboxy lower alkyl group, a lower alkoxycarbonyl lower alkyl group, a lower aralkyl group, or a aryl group and n represents 0, 1, or 2) and A represents an oxy- gen atom, a sulfur atom, an imino group, a lower alkylimino group, or a 3,5-di-tert-butyl-4-hydroxyphenacylimino group Image Image or a salt thereof which comprises reacting the compound repre- sented by formula II Image II and the ?-halocarbonyl compound represented by formula III Image III ABSTRACT: wherein R1, R2, R3, and A have the same significance as defined concerning formula I; A' represents an oxygen atom, a sulfur atom, an imino group, or a lower alkylimino group; and X repre- sents a halogen atom; and then, if desired, oxidizing, alkylat- ing or desulfurizing the product thus obtained. The compounds of this invention have an anti-inflammatory, an antipyretic, an analgesic, an anti-arthritic activity, and an immuno regulatory activity. Hence, they are particularly useful as an antirheumatic.

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