Patent ID: 6169096
Filing Date: 2001-01-02
Classification: A61P,C07D,Y02P

Abstract:
A compound of formula (I), ##STR28## a stereoisomeric form thereof, a pharmaceutically acceptable acid or base addition salt thereof, wherein the dotted line represents an optional bond; X is oxygen or sulfur; R.sup.1 is hydrogen, C.sub.1-12 alkyl, Ar.sup.1, Ar.sup.2 C.sub.1-6 alkyl, quinolinylC.sub.1-6 -alkyl, pyridylC.sub.1-6 alkyl, hydroxyC.sub.1-6 alkyl, C.sub.1-6 alkyloxyC.sub.1-6 alkyl, mono- or di(C.sub.1-6 alkyl)aminoC.sub.1-6 alkyl, aminoC.sub.1-6 alkyl, or a radical of formula --Alk.sup.1 --C(.dbd.O)--R.sup.9, --Alk.sup.1 --S(O)--R.sup.9 or --Alk.sup.1 --S(O).sub.2 --R.sup.9, wherein Alk.sup.1 is C.sub.1-6 alkanediyl, R.sup.9 is hydroxy, C.sub.1-6 alkyl, C.sub.1-6 alkyloxy, amino, C.sub.1-8 alkylamino or C.sub.1-8 alkylamino substituted with C.sub.1-6 alkyloxycarbonyl; R.sup.2, R.sup.3 and R.sup.16 each independently are hydrogen, hydroxy, halo, cyano, C.sub.1-6 alkyl, C.sub.1-6 alkyloxy, hydroxyC.sub.1-6 alkyloxy, C.sub.1-6 alkyloxyC.sub.1-6 alkyloxy, aminoC.sub.1-6 alkyloxy, mono- or di(C.sub.1-6 alkyl)aminoC.sub.1-6 alkyloxy, Ar.sup.1, Ar.sup.2 C.sub.1-6 alkyl, Ar.sup.2 oxy, Ar.sup.2 C.sub.1-6 alkyloxy, hydroxycarbonyl, C.sub.1-6 alkyloxycarbonyl, trihalomethyl, trihalomethoxy, C.sub.2-6 alkenyl, 4,4-dimethyloxazolyl; or when on adjacent positions R.sup.2 and R.sup.3 taken together may form a bivalent radical of formula --O--CH.sub.2 --O-- (a-1), --O--CH.sub.2 --CH.sub.2 --O-- (a-2), --O--CH.dbd.CH-- (a-3), --O--CH.sub.2 --CH.sub.2 -- (a-4), --O--CH.sub.2 --CH.sub.2 --CH.sub.2 -- (a-5), or --CH.dbd.CH--CH.dbd.CH-- (a-6); R.sup.4 is hydrogen or C.sub.1-6 alkyl; R.sup.5 is hydrogen; R.sup.6 and R.sup.7 each independently are hydrogen, halo, cyano, C.sub.1-6 alkyl, C.sub.1-6 alkyloxy, Ar.sup.2 oxy, trihalomethyl, C.sub.1-6 alkylthio, di(C.sub.1-6 alkyl)amino, or when on adjacent positions R.sup.6 and R.sup.7 taken together may form a bivalent radical of formula --O--CH.sub.2 --O-- (c-1), or --CH.dbd.CH--CH.dbd.CH-- (c-2); R.sup.8 is hydrogen, C.sub.1-6 alkyl, cyano, hydroxycarbonyl, C.sub.1-6 alkyloxycarbonyl, C.sub.1-6 alkylcarbonylC.sub.1-6 alkyl, cyanoC.sub.1-6 alkyl, C.sub.1-6 alkyloxycarbonylC.sub.1-6 alkyl, carboxyC.sub.1-6 alkyl, hydroxyC.sub.1-6 alkyl, aminoC.sub.1-6 alkyl, mono- or di(C.sub.1-6 alkyl)aminoC.sub.1-6 alkyl, imidazolyl, haloC.sub.1-6 alkyl, C.sub.1-6 alkyloxyC.sub.1-6 alkyl, aminocarbonylC.sub.1-6 alkyl, or a radical of formula --O--R.sup.10 (b-1), --S--R.sup.10 (b-2), --N--R.sup.11 R.sup.12 (b-3), wherein R.sup.10 is hydrogen, C.sub.1-6 alkyl, C.sub.1-6 alkylcarbonyl, Ar.sup.1, Ar.sup.2 C.sub.1-6 alkyl, C.sub.1-6 alkyloxycarbonylC.sub.1-6 alkyl, a radical or formula --Alk.sup.2 --OR.sup.13 or --Alk.sup.2 --NR.sup.14 R.sup.15 ; R.sup.11 is hydrogen, C.sub.1-12 alkyl, Ar.sup.1 or Ar.sup.2 C.sub.1-6 alkyl; R.sup.12 is hydrogen, C.sub.1-6 alkyl, C.sub.1-6 alkylcarbonyl, C.sub.1-6 alkyloxycarbonyl, C.sub.1-6 alkylaminocarbonyl, Ar.sup.1, Ar.sup.2 C.sub.1-6 alkyl, C.sub.1-6 alkylcarbonylC.sub.1-6 alkyl, a natural amino acid, Ar.sup.1 carbonyl, Ar.sup.2 C.sub.1-6 alkylcarbonyl, aminocarbonylcarbonyl, C.sub.1-6 alkyloxyC.sub.1-6 alkylcarbonyl, hydroxy, C.sub.1-6 alkyloxy, aminocarbonyl, di(C.sub.1-6 alkyl) aminoC.sub.1-6 alkylcarbonyl, amino, C.sub.1-6 alkylamino, C.sub.1-6 alkylcarbonylamino, or a radical of formula --Alk.sup.2 --OR.sup.13 or --Alk.sup.2 --NR.sup.14 R.sup.15 ; wherein Alk.sup.2 is C.sub.1-6 alkanediyl; R.sup.13 is hydrogen, C.sub.1-6 alkyl, C.sub.1-6 alkylcarbonyl, hydroxyC.sub.1-6 alkyl, Ar.sup.1 or Ar.sup.2 C.sub.1-6 alkyl; R.sup.14 is hydrogen, C.sub.1-6 alkyl, Ar.sup.1 or Ar.sup.2 C.sub.1-6 alkyl; R.sup.15 is hydrogen, C.sub.1-6 alkyl, C.sub.1-6 alkylcarbonyl, Ar.sup.1 or Ar.sup.2 C.sub.1-6 alkyl; R.sup.17 is hydrogen, halo, cyano, C.sub.1-6 alkyl, C.sub.1-6 alkyloxycarbonyl, Ar.sup.1 ; R.sup.18 is hydrogen, C.sub.1-6 alkyl, C.sub.1-6 alkyloxy or halo; R.sup.19 is hydrogen or C.sub.1-6 alkyl; Ar.sup.1 is phenyl or phenyl substituted with C.sub.1-6 alkyl, hydroxy, amino, C.sub.1-6 alkyloxy or halo; and Ar.sup.2 is phenyl or phenyl substituted with C.sub.1-6 alkyl, hydroxy, amino, C.sub.1-6 alkyloxy or halo.