Leukotriene antagonists

C - Chemistry – Metallurgy – 07 – C

Patent

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167/233, 167/246

C07C 59/90 (2006.01) A61K 31/41 (2006.01) C07D 257/04 (2006.01)

Patent

CA 1327588

(1) ABSTRACT This invention provides benzene derivatives of the Formula I Image I wherein: R1 is hydrogen, C1-C6 alkyl, C3-C8 phenyl-substituted-(C1-C3 alkyl), phenyl, or phenyl substituted with a halo, C1-C4 alkyl, or C1-C4 alkoxy functionality; R2 is C1-C10 alkyl, C2-C6 alkenyl, benzyl or 2-phenylethyl; R3 is hydrogen, bromo, chloro, C1-C3 alkyl, nitro, or -NRR; Z is -O-, -NR- , or Image ; p is 0, 1 or 2; each A is a bond or a straight or branched chain C1-C10 alkylidene, C5-C10 cyclic alkylidene, or C2-C4 alkenylidene group; Q is -?- or -CHOH-; Y is -?-, -CHOH, -O-, or a bond, or -A-Q-A-Y-, when taken together with two adjacent carbon atoms of the phenyl ring to which A is attached, is Image , where E is a bond, -CH2-, -S-, or -O-; and R4 is -COR9, 5-tetrazolyl, 3-(1,2,5-thiadiazolyl), 2-thioxo-4-thiazolidinonyl, or -CN; where each R is hydrogen or C1-C3 alkyl; each R5 and R6 is independently hydrogen, C1-C3 alkyl, phenyl, or benzyl; each R7 and R8 is independently hydrogen, C1-C3 alkoxy, halo, amino, hydroxy, or C1-C3 alkyl; and R9 is hydroxy or C1-C4 alkoxy; provided that (a) all three A groups may not be a bond at the same time; and (b) when Y is a group other than a bond, the A group between Q and Y may not be a bond; and pharmaceutically acceptable salts thereof. These compounds are selective leukotriene antagonists that are useful in the treatment of conditions characterized by an excessive release of leukotrienes, as for example, asthma.

563379

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