Patent ID: 6107320
Filing Date: 2000-08-22
Classification: C07D

Abstract:
A compound of the formula: ##STR9## wherein: one of X and Y is N and the other is O;R.sup.1, R.sup.2 and R.sup.3 are each independently(a) hydrogen, except that R.sup.1 is other than hydrogen;(b) alkyl, alkenyl, alkynyl, alkoxy, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, aryl, aryloxy, aralkyl or aralkoxy, any of which may be substituted with Z.sup.1, Z.sup.2 and Z.sup.3 ;(c) halo;(d) hydroxyl;(e) cyano;(f) nitro;(g) --C(O)H or --C(O)R.sup.6 ;(h) --CO.sub.2 H or --CO.sub.2 R.sup.6 ;(i) --SH, --S(O).sub.n R.sup.6, --S(O).sub.m --OH, --S(O).sub.m --OR.sup.6, --O--S(O).sub.m --R.sup.6, --O--S(O).sub.m OH or --O--S(O).sub.m --OR.sup.6 ;(j) --Z.sup.4 --NR.sup.7 R.sup.8 ; or(k) --Z.sup.4 --N(R.sup.11)--Z.sup.5 --NR.sup.9 R.sup.10 ;wherein at least one of R.sup.1, R.sup.2 or R.sup.3 is phenyl or biphenyl which may be substituted with Z.sup.1, Z.sup.2 and Z.sup.3 ;R.sup.4 and R.sup.5 are each independently(a) hydrogen;(b) alkyl, alkenyl, alkynyl, alkoxy, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, aryl, aryloxy, aralkyl or aralkoxy, any of which may be substituted with Z.sup.1, Z.sup.2 and Z.sup.3 ;(c) halo;(d) hydroxyl;(e) cyano;(f) nitro;(g) --C(O)H or --C(O)R.sup.6 ;(h) --CO.sub.2 H or --CO.sub.2 R.sup.6 ;(i) --SH, --S(O).sub.n R.sup.6, --S(O).sub.m --OH, --S(O).sub.m --OR.sup.6, --O--S(O).sub.m --R.sup.6, --O--S(O).sub.m OH or --O--S(O).sub.m --OR.sup.6 ;(j) --Z.sup.4 --NR.sup.7 R.sup.8 ; or(k) --Z.sup.4 --N(R.sup.11)--Z.sup.5 --NR.sup.9 R.sup.10 ; or(l) R.sup.4 and R.sup.5 together are alkylene or alkenylene, either of which may be substituted with Z.sup.1, Z.sup.2 and Z.sup.3, completing a 4- to 8-membered saturated, unsaturated or aromatic ring together with the carbon atoms to which they are attached;R.sup.6 is alkyl, alkenyl, alkynyl, alkoxy, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, aryl or aralkyl, any of which may be substituted with Z.sup.1, Z.sup.2 and Z.sup.3 ;R.sup.7 is(a) hydrogen;(b) alkyl, alkenyl, alkynyl, alkoxy, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, aryl or aralkyl, any of which may be substituted with Z.sup.1, Z.sup.2 and Z.sup.3 ;(c) cyano;(d) hydroxyl;(e) --C(O)H or --C(O)R.sup.6 ;(f) --CO.sub.2 R.sup.6 ; or (g) --SH, --S(O).sub.n R.sup.6, --S(O).sub.m --OH, --S(O).sub.m --OR.sup.6, --O--S(O).sub.m --R.sup.6, --O--S(O).sub.m OH or --O--S(O).sub.m --OR.sup.6, except when Z.sup.4 is --S(O).sub.n --;R.sup.8 is(a) hydrogen;(b) --C(O)H or --C(O)R.sup.6, except when Z.sup.4 is --C(O)-- and R.sup.7 is --C(O)H, --C(O)R.sup.6 or --CO.sub.2 R.sup.6 ; or(c) alkyl, alkenyl, alkynyl, alkoxy, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, aryl or aralkyl, any of which may be substituted with Z.sup.1, Z.sup.2 and Z.sup.3 ; orR.sup.7 and R.sup.8 together are alkylene or alkenylene, either of which may be substituted with Z.sup.1, Z.sup.2 and Z.sup.3, completing a 3- to 8-membered saturated, unsaturated or aromatic ring together with the nitrogen atom to which they are attached;R.sup.9 is(a) hydrogen;(b) hydroxyl;(c) --C(O)H or --C(O)R.sup.6 ;(d) --CO.sub.2 R.sup.6 ;(e) --SH, --S(O).sub.n R.sup.6, --S(O).sub.m --OH, --S(O).sub.m --OR.sup.6, --O--S(O).sub.m --R.sup.6, --O--S(O).sub.m OH or --O--S(O).sub.m --OR.sup.6 ; or(f) alkyl, alkenyl, alkynyl, alkoxy, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, aryl or aralkyl, any of which may be substituted with Z.sup.1, Z.sup.2 and Z.sup.3 ;R.sup.10 is(a) hydrogen;(b) --C(O)H or --C(O)R.sup.6, except when Z.sup.5 is --C(O)-- and R.sup.9 is --C(O)H, --C(O)R.sup.6 or --CO.sub.2 R.sup.6 ; or(c) alkyl, alkenyl, alkynyl, alkoxy, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, aryl or aralkyl, any of which may be substituted with Z.sup.1, Z.sup.2 and Z.sup.3 ;R.sup.11 is(a) hydrogen;(b) hydroxyl;(c) --C(O)H, --C(O)R.sup.6 or CO.sub.2 R.sup.6 ; or(d) alkyl, alkenyl, alkynyl, alkoxy, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, aryl or aralkyl, any of which may be substituted with Z.sup.1, Z.sup.2 and Z.sup.3 ; or any two of R.sup.9, R.sup.10 and R.sup.11 together are alkylene or alkenylene, either of which may be substituted with Z.sup.1, Z.sup.2 and Z.sup.3, completing a 3- to 8-membered saturated, unsaturated or aromatic ring together with the atoms to which they are attached;Z.sup.1, Z.sup.2 and Z.sup.3 are each independently(a) hydrogen;(b) halo;(c) hydroxy;(d) alkyl;(e) alkenyl;(f) aralkyl;(g) alkoxy;(h) aryloxy;(i) aralkoxy;(j) --SH, --S(O).sub.n Z.sup.6, --S(O).sub.m --OH, --S(O).sub.m --OZ.sup.6, --O--S(O).sub.m --Z.sup.6, --O--S(O).sub.m OH or --O--S(O).sub.m --OZ.sup.6 ;(k) oxo;(l) nitro;(m) cyano;(n) --C(O)H or --C(O)Z.sup.6 ;(o) --CO.sub.2 H or --CO.sub.2 Z.sup.6 ;(p) --Z.sup.4 --NZ.sup.7 Z.sup.8 ;(q) --Z.sup.4 --N(Z.sup.11)--Z.sup.5 --Z.sup.6 ; or(r) --Z.sup.4 --N(Z.sup.11)--Z.sup.5 --NZ.sup.7 Z.sup.8 ;Z.sup.4 and Z.sup.5 are each independently(a) a single bond;(b) --Z.sup.9 --S(O).sub.n --Z.sup.10 --;(c) --Z.sup.9 --C(O)--Z.sup.10 --;(d) --Z.sup.9 --C(S)--Z.sup.10 --;(e) --Z.sup.9 --O--Z.sup.10 --;(f) --Z.sup.9 --S--Z.sup.10 --; or(g) --Z.sup.9 --O--C(O)--Z.sup.10 --;Z.sup.6, Z.sup.7 and Z.sup.8 are each independently hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, aryl or aralkyl, or Z.sup.7 and Z.sup.8 together are alkylene or alkenylene, completing a 3- to 8-membered saturated, unsaturated or aromatic ring together with the nitrogen atom to which they are attached;Z.sup.9 and Z.sup.10 are each independently a single bond, alkylene, alkenylene or alkynylene;Z.sup.11 is(a) hydrogen;(b) hydroxyl;(c) --C(O)H, --C(O)Z.sup.6 or CO.sub.2 Z.sup.6 ; or(d) alkyl, alkenyl, alkynyl, alkoxy, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, aryl or aralkyl;or any two of Z.sup.7, Z.sup.8 and Z.sup.11 together are alkylene or alkenylene, completing a 3- to 8-membered saturated, unsaturated or aromatic ring together with the atoms to which they are attached;m is 1 or 2; andn is 0, 1, or 2,or a pharmaceutically acceptable salt thereof.