Patent ID: 6274607
Filing Date: 2001-08-14
Classification: A61P,C07D

Abstract:
A compound of formula I: ##STR9##or a pharmaceutically acceptable salt, ester, or solvate thereof, wherein:A and B are taken together with the nitrogen and carbon atoms to which they are respectively attached to form a thiazolyl ring containing any combination of CH.sub.2, S, SO, or SO.sub.2 ;X is either O or S;Y is a direct bond to Z, a C.sub.1 -C.sub.6 straight or branched chain alkyl, or a C.sub.2 -C.sub.6 straight or branched chain alkenyl, wherein any of the carbon atoms of said alkyl or alkenyl are optionally substituted in one or more positions with amino, halo, haloalkyl, thiocarbonyl, ester, thioester, alkoxy, alkenoxy, cyano, nitro, imino, alkylamino, aminoalkyl, sulfhydryl, thioalkyl, sulfonyl, oxygen to form a carbonyl, or wherein any of the carbon atoms of said alkyl or alkenyl are optionally replaced with O, NH, NR.sub.2, S, SO, or SO.sub.2, wherein R.sub.2 is selected from the group consisting of hydrogen, (C.sub.1 -C.sub.6)-straight or branched chain alkyl, (C.sub.3 -C.sub.6)-straight or branched chain alkenyl or alkynyl, and (C.sub.1 -C.sub.4) bridging alkyl wherein said bridging alkyl forms a heterocyclic ring starting with the nitrogen of NR.sub.1 and ending with one of the carbon atoms of said alkyl or alkenyl chain, and wherein said heterocyclic ring is optionally fused to an Ar group;Z is a direct bond, or a C.sub.1 -C.sub.6 straight or branched chain alkyl, or a C.sub.2 -C.sub.6 straight or branched chain alkenyl, wherein any of the carbon atoms of said alkyl or alkenyl are optionally substituted in one or more positions with amino, halo, haloalkyl, thiocarbonyl, ester, thioester, alkoxy, alkenoxy, cyano, nitro, imino, alkylamino, aminoalkyl, sulfhydryl, thioalkyl, sulfonyl, oxygen to form a carbonyl, or wherein any of the carbon atoms of said alkyl or alkenyl are optionally replaced with O, NH, NR.sub.2, S, SO, or SO.sub.2, wherein R.sub.2 is selected from the group consisting of hydrogen, (C.sub.1 -C.sub.6)-straight or branched chain alkyl, (C.sub.3 -C.sub.6)-straight or branched chain alkenyl or alkynyl, and (C.sub.1 -C.sub.4) bridging alkyl wherein said bridging alkyl forms a heterocyclic ring starting with the nitrogen of NR.sub.1 and ending with one of the carbon atoms of said alkyl or alkenyl chain, and wherein said heterocyclic ring is optionally fused to an Ar group;C and D are independently:hydrogen, Ar, C.sub.1 -C.sub.6 straight or branched chain alkyl, or C.sub.2 -C.sub.6 straight or branched chain alkenyl, wherein any of the carbon atoms of said alkyl or alkenyl are optionally substituted in one or more position(s) with C.sub.3 -C.sub.9 cycloalkyl, C.sub.5 -C.sub.7 cycloalkenyl, hydroxyl, carbonyl oxygen, or Ar, wherein said alkyl, alkenyl, cycloalkyl or cycloalkenyl groups are optionally substituted with C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl, hydroxy, amino, halo, haloalkyl, thiocarbonyl, ester, thioester, alkoxy, alkenoxy, cyano, nitro, imino, alkylamino, aminoalkyl, sulfhydryl, thioalkyl, sulfonyl, wherein any of the carbon atoms of said alkyl or alkenyl are optionally substituted in one or more positions with oxygen to form a carbonyl, or wherein any of the carbon atoms of said alkyl or alkenyl are optionally replaced with O, NH, NR.sub.2, S, SO, or SO.sub.2, wherein R.sub.2 is selected from the group consisting of hydrogen, (C.sub.1 -C.sub.6)-straight or branched chain alkyl, (C.sub.3 -C.sub.6)-straight or branched chain alkenyl or alkynyl, and (C.sub.1 -C.sub.4) bridging alkyl wherein said bridging alkyl forms a heterocyclic ring starting with the nitrogen of NR.sub.1 and ending with one of the carbon atoms of said alkyl or alkenyl chain, and wherein said heterocyclic ring is optionally fused to an Ar group;wherein Ar is an aryl or heteroaryl moiety which is substituted or unsubstituted;W is oxygen or sulfur;U is either O or N, wherein when U is O, then R.sub.1 is a lone pair of electrons and R.sub.2 is selected from the group consisting of:Ar as defined above, C.sub.3 -C.sub.9 cycloalkyl, C.sub.1 -C.sub.6 straight or branched chain alkyl or alkenyl, or C.sub.1 -C.sub.6 straight or branched chain alkyl or alkenyl substituted in one or more positions with Ar, amino, halo, haloalkyl, hydroxy, trifluoromethyl, C.sub.1 -C.sub.6 straight or branched chain alkyl, C.sub.2 -C.sub.6 straight or branched chain alkenyl, carbonyl, thiocarbonyl, ester, thioester, alkoxy, alkenoxy, cyano, nitro, imino, alkylamino, aminoalkyl, sulfhydryl, thioalkyl, sulfonyl, substituted alkyl or alkenyl wherein any of the carbon atoms of the alkyl or alkenyl are optionally replaced with S, SO, SO.sub.2, O, or NR.sub.2 wherein R.sub.2 is selected from the group consisting of hydrogen, (C.sub.1 -C.sub.6)-straight or branched chain alkyl, (C.sub.3 -C.sub.6)-straight or branched chain alkenyl or alkynyl, and (C.sub.1 -C.sub.4) bridging alkyl wherein said bridging alkyl forms a heterocyclic ring starting with the nitrogen of NR.sub.1 and ending with one of the carbon atoms of said alkyl or alkenyl chain, and wherein said heterocyclic ring is optionally fused to an Ar group or C.sub.3 -C.sub.9 cycloalkyl;and when U is N, R.sub.1 and R.sub.2 are selected independently from the group consisting of:hydrogen, Ar as defined above, C.sub.3 -C.sub.9 cycloalkyl, C.sub.1 -C.sub.6 straight or branched chain alkyl or alkenyl, or C.sub.1 -C.sub.6 straight or branched chain alkyl or alkenyl substituted in one or more positions with Ar, amino, halo, haloalkyl, hydroxy, trifluoromethyl, C.sub.1 -C.sub.6 straight or branched chain alkyl, C.sub.2 -C.sub.6 straight or branched chain alkenyl, carbonyl, thiocarbonyl, ester, thioester, alkoxy, alkenoxy, cyano, nitro, imino, alkylamino, aminoalkyl, sulfhydryl, thioalkyl, sulfonyl, substituted alkyl or alkenyl wherein any of the carbon atoms of the alkyl or alkenyl are optionally replaced with S, SO, SO.sub.2, O, or NR.sub.2 wherein R.sub.2 is selected from the group consisting of hydrogen, C.sub.1 -C.sub.6)-straight or branched chain alkyl, (C.sub.3 -C.sub.6)-straight or branched chain alkenyl or alkynyl, and (C.sub.1 -C.sub.4) bridging alkyl wherein said bridging alkyl forms a heterocyclic ring starting with the nitrogen of NR.sub.1 and ending with one of the carbon atoms of said alkyl or alkenyl chain, and wherein said heterocyclic ring is optionally fused to an Ar group or C.sub.3 -C.sub.9 cycloalkyl;or R.sub.1 and R.sub.2 may be taken together to form a heterocyclic ring.