Patent ID: 6252084
Filing Date: 2001-06-26
Classification: C07D,C07F

Abstract:
A 1H-indole-3-acetamide represented by the formula (III), or a pharmaceutically acceptable salt or prodrug derivative thereof; ##STR70##whereinX is oxygen or sulfur;R.sub.21 is --(CH.sub.2).sub.n --(R.sub.80), or --(NH)--(R.sub.80), where n is 1 to 8, and R.sub.80 is aryl or aryl substituted by C.sub.1 -C.sub.10 alkyl, C.sub.2 -C.sub.10 alkenyl, C.sub.2 -C.sub.10 alkynyl, C.sub.1 -C.sub.10 haloalkyl, C.sub.4 -C.sub.12 cycloalkyl, C.sub.1 -C.sub.10 hydroxyalkyl, carboxyl, halo, --CN, --CHO, --OH, --SH, C.sub.1 -C.sub.10 alkylthio, C.sub.1 -C.sub.10 alkoxyl, carboxyl, amino, or hydroxyamino;R.sub.22 is hydrogen, halo, C.sub.1 -C.sub.3 alkyl, ethenyl, cyclopropyl, C.sub.1 -C.sub.2 alkylthio, C.sub.1 -C.sub.2 alkoxy, --CHO, --CN;each R.sub.23 is independently hydrogen, halo, or methyl;R.sub.24 and R.sub.25 are each independently selected from (a) and (b) where;(a) is hydrogen, halo, alkyl, or alkoxy, and;(b) is a group having the formula: ##STR71##with the proviso that at least one of R.sub.24 and R.sub.25 must be selected from (b), and where:R.sub.84 and R.sub.85 are each independently selected from hydrogen, C.sub.1 -C.sub.10 alkyl, hydroxy, or R.sub.84 and R.sub.85 taken together are .dbd.O;p is 1 to 5,Z is a bond, --O--, --N(C.sub.1 -C.sub.10 alkyl)--, --NH--, or --S--; andQ is --CON(R.sub.82 R.sub.83), -5-tetrazolyl, --SO.sub.3 H, ##STR72##where n is 1 to 8, R.sub.86 is independently selected from hydrogen, a metal, or C.sub.1 -C.sub.10 alkyl, and R.sub.99 is selected from hydrogen or C.sub.1 -C.sub.10 alkyl;R.sub.26, and R.sub.27 are each independently hydrogen, C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.10 alkenyl, C.sub.1 -C.sub.10 alkynyl, C.sub.3 -C.sub.8 cycloalkyl, aryl, aralkyl, or the adjacent hydrocarbyl groups in the groups R.sub.26 and R.sub.27 combine with the ring carbon atoms to which they are attached to form a 5 or 6 membered substituted or unsubstituted carbocyclic ring; or C.sub.1 -C.sub.10 haloalkyl, C.sub.1 -C.sub.10 alkoxy, C.sub.1 -C.sub.10 haloalkoxy, C.sub.4 -C.sub.8 cycloalkoxy, phenoxy, halo, hydroxy, carboxyl, --SH, --CN, C.sub.1 -C.sub.10 alkylthio, arylthio, thioacetal, --C(O)O(C.sub.1 -C.sub.10 alkyl), hydrazide, hydrazino, hydrazido, --NH.sub.2, --NO.sub.2, --NR.sub.82 R.sub.83, and --C(O)NR.sub.82 R.sub.83, where, R82 and R.sub.83 are independently hydrogen, C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.10 hydroxyalkyl, or taken together with N, R.sub.82 and R.sub.83 form a 5 to 8 membered heterocyclic ring; or a group having the formula: ##STR73##where,R.sub.84 and R.sub.85 are each independently selected from hydrogen, C.sub.1 -C.sub.10 alkyl, hydroxy, or R.sub.84 and R.sub.85 taken together are .dbd.O;p is 1 to 5,Z is a bond, --O--, --N(C.sub.1 -C.sub.10 alkyl)--, --NH--, or --S--; andQ is --CON(R.sub.82 R.sub.83), -5-tetrazolyl, --SO.sub.3 H, ##STR74##where n is 1 to 8, R.sub.86 is independently selected from hydrogen, a metal, or C.sub.1 -C.sub.10 alkyl, and R.sub.99 is selected from hydrogen or C.sub.1 -C.sub.10 alkyl.