Patent ID: 6063928
Filing Date: 2000-05-16
Classification: C07D

Abstract:
A method to produce a compound of the following chemical formula I: ##STR6## and the pharmaceutically acceptable salts thereof, wherein Ar.sup.1 is a heterocyclic moiety which is selected from the group consisting of imidazolyl, pyrrolyl, pyrazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, indolyl, indazolyl and benzimidazolyl, which is bonded to X.sup.1 through a ring nitrogen atom, and which may be optionally substituted with one or two substituents selected from halo, hydroxy, cyano, amino, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 alkylthio, C.sub.1-4 halo-substituted alkyl, C.sub.1-4 halo-substituted alkoxy, C.sub.1-4 alkylamino and di(C.sub.1-4) alkylamino;X.sup.1 is a direct bond or C.sub.1-4 alkylene;Ar.sup.2 is phenylene optionally substituted with one or two substituents selected from halo, hydroxy, cyano, amino, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 alkylthio, C.sub.1-4 halo-substituted alkyl and C.sub.1-4 halo-substituted alkoxy;X.sup.2 is --A--X-- or --X--A-- wherein A is a direct bond or C.sub.1-4 alkylene and X is oxy, thio, sulfinyl or sulfonyl;Ar.sup.3 is phenylene, pyridylene, thienylene, furylene, oxazolylene or thiazolylene optionally substituted with one or two substituents selected from halo, hydroxy, cyano, amino, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 alkylthio, C.sub.1-4 halo-substituted alkyl, C.sub.1-4 halo-substituted alkoxy, C.sub.1-4 alkylamino and di(C.sub.1-4) alkylamino;R.sup.1 and R.sup.2 are each C.sub.1-4 alkyl, or together they form a group of formula --D.sup.1 --Z--D.sup.2 -- which together with the carbon atom to which it is attached defines a ring having 3 to 8 atoms, wherein D.sup.1 and D.sup.2 are C.sub.1-4 alkylene and Z is a direct bond or oxy, thio, sulfinyl, sulfonyl, or vinylene, and D.sup.1 and D.sup.2 may be substituted by C.sub.1-3 alkyl; andY is CONR.sup.3 R.sup.4, CN, C(R.sup.3).dbd.N--OR.sup.4, COOR.sup.3, COR.sup.3 or CSNR.sup.3 R.sup.4, wherein R.sup.3 and R.sup.4 are each H or C.sub.1-4 alkyl; comprising reacting a compound of the formula (II) with a compound of the formula (III): ##STR7## or, reacting a compound of the formula (IV) with a compound of the formula (V): ##STR8## wherein Ar.sup.1, Ar.sup.2, Ar.sup.3, R.sup.1, R.sup.2, A, X, X.sup.1, and Y are defined as above; and Q is a displaceable group, in a reaction-inert solvent.