2,3-substituted indole compounds as anti-inflammatory and analgesic agents

A compound of the following formula:

• or the pharmaceutically acceptable salts thereof wherein
• Z is OH, C1-6 alkoxy, —NR2R3 or a group of the formula (II) or (III):
• wherein r is 1, 2, 3 or 4, Y is a direct bond, O, S or NR4, and W is OH or —NR2R3;
• Q is selected from the following:
• (a) phenyl optionally substituted with one, two or three substituents independently selected from
• (a-1) halo, C1-4 alkyl, halo-substituted C1-4 alkyl, OH, C1-4 alkoxy, halo-substituted C1-4 alkoxy, C1-4 alkylthio, NO2, NH2, di-(C1-4 alkyl)amino, C1-4 alkylamino, CN, HO—(C1-4)alkyl, C1-4 alkoxy-C1-4 alkyl, C1-4 alkylsulfonyl, aminosulfonyl, —NH2S(O)2NR2R3, acetyl, —COOH, —C(O)O—C1-4 alkyl, C1-4 alkylsulfonylamino and C3-7 cycloalkyl,
• (a-2) aryl or —O—(CH2)n-aryl, and the aryl or aryl moiety being optionally substituted with one, two or three substituents independently selected from halo, C1-4 alkyl, halo-substituted C1-4 alkyl, OH, C1-4 alkoxy, halo-substituted C1-4 alkoxy, C1-4 alkylthio, NO2, NH2, di-(C1-4 alkyl)amino, C1-4 alkylamino and CN,
• (a-3) 5-membered monocyclic aromatic group optionally substituted with one, two or three substituents independently selected from halo, C1-4 alkyl, halo-substituted C1-4 alkyl, OH, C1-4 alkoxy, halo-substituted C1-4 alkoxy, C1-4 alkylthio, NO2, NH2, di-(C1-4 alkyl)amino, C1-4 alkylamino and CN,
• (a-4) 6-membered monocyclic aromatic group optionally substituted with one, two or three substituents independently selected from halo, C1-4 alkyl, halo-substituted C1-4 alkyl, OH, C1-4 alkoxy, halo-substituted C1-4 alkoxy, C1-4 alkylthio, NO2, NH2, di-(C1-4 alkyl)amino, C1-4 alkylamino and CN,
• (b) a 6-membered monocyclic aromatic group containing one, two, three or four nitrogen atom(s), and said monocyclic aromatic group being optionally substituted with one, two or three substituents independently selected from the above group (a-1), (a-2), (a-3) and (a-4),
• (c) a 5-membered monocyclic aromatic group containing one heteroatom selected from O, S and N and optionally containing one, two or three nitrogen atom(s) in addition to said heteroatom, and said monocyclic aromatic group being optionally substituted with one, two or three substituents independently selected from the above group (a-1), (a-2), (a-3) and (a-4);
• (d) C3-7 cycloalkyl optionally substituted with one or two substituents independently selected from OH, C1-4 alkyl, halo and halo-substituted C1-4 alkyl;
• and
• (e) a benzo-fuzed heterocycle optionally substituted with one, two or three substituents independently selected from the group (a-1);
• R1 is hydrogen, C1-4 alkyl or halo;
• R2 and R3 are independently H, OH, C1-4 alkoxy, C1-4 alkyl or C1-4 alkyl substituted with halo, OH, C1-4 alkoxy, NH2 or CN;
• R4 is hydrogen or C1-4 alkyl;
• X is independently selected from halo, C1-4 alkyl, halo-substituted C1-4 alkyl, OH, C1-4 alkoxy, halo-substituted C1-4 alkoxy, C1-4 alkylthio, NO2, NH2, di-(C1-4 alkyl)amino, C1-4 alkylamino, CN, HO—(C1-4)alkyl, C1-4 alkoxy-C1-4 alkyl, C1-4 alkylsulfonyl, aminosulfonyl, —NH2S(O)2NR2NR3, acetyl, —COOH, —C(O)O—C1-4 alkyl, C1-4 alkylsulfonylamino and C3-7 cycloalkyl;
• and
• n is 0, 1, 2, 3 or 4.