Amido substituted naphthalenes and intermediates thereof

C - Chemistry – Metallurgy – 07 – C

Patent

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167/268, 260/472

C07C 59/84 (2006.01) C07C 59/90 (2006.01) C07C 69/738 (2006.01) C07C 259/06 (2006.01)

Patent

CA 1284336

ABSTRACT Amido substituted naphthalene compounds of the formula: Image where: R1 may be C1-12 alkyl, C3-12 branched-chain alkyl, C2-6 alkenyl, C3-6 alkynyl, or an aralkyl wherein the alkyl group is C1-3 unsubstituted or substituted with C1 2 alkyl or hydroxyalkyl, wherein the alkyl group is C1-6; R2 may be H, C1-10 alkyl, C3-10 branched-chain alkyl, C5-7 cycloalkyl, phenyl or phenyl substituted by C1-3 alkyl or C1-3 alkoxy; R3 may be H or C1-3 alkyl; and (CH2)n may be a straight- or branched- alkyl chain of 0-5 carbons. Intermediates of the compound of formula I having the formula: Image I I where R1 and (CH2)n are as defined above. R1 may also be H and R4 may be H or C1-3 alkyl with the proviso that when (CH2)n is an alkyl chain of 0-2 carbons, R1 is not C1-2 alkyl. The compounds of formula I or II are useful as anti-inflammatory agents. The compounds inhibit the cyclooxygenase pathway and may additionally inhibit the lipoxygenase pathway. In particular the amido substituted naphthalenes are pharmacologically active in alleviating inflammation, asthma, hyper- sensitivity, myocardial ischemia, dermatological conditions such as psoriasis, and dermatitis and gastrointestinal inflammatory conditions such as inflammatory bowel syndromes. Processes of preparing these compounds, compositions containing same and medical treatments using them are also disclosed.

537498

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