Patent ID: 6689784
Filing Date: 2004-02-10
Classification: A61P,C07D

Abstract:
A compound of formula I: wherein:Z is oxygen or sulfur; R1 is hydrogen, â€”CHN2, â€”R, â€”CH2OR, â€”CH2SR, or â€”CH2Y; R is a C1-12 aliphatic, aryl, aralkyl, heterocyclyl, or heterocyclylalkyl ring, wherein each of these groups is optionally substituted, and wherein said heterocyclic ring is a three to nine membered saturated or unsaturated mono-, bi-, or tri-heterocyclic ring system wherein each ring contains up to three heteroatoms selected from O, N, or S; Y is an electronegative leaving group selected from F, Cl, Br, I, arylsulfonyloxy, alkylsulfonyloxy, trifluoromethanesulfonyloxy, ORâ€², SRâ€², â€”OC&boxH;O(Râ€²), or â€”OPO(R6)(R7); wherein Râ€² is an aliphatic group, an aryl group, an aralkyl group, a carbocyclic group, an alkyl carbocyclic group, a heterocyclic group, or an alkyl heterocyclic group; wherein R6 and R7 are independently selected from R or OR; R2 is: i) CO2H, or an ester, or an amide thereof; or R2 is an isostere of said CO2H; or ii) CH2CO2H, or an ester, or an amide thereof; or R2 is an isostere of said CH2CO2H; R3 is selected from H, a side chain of a natural &agr;-amino acid, or a substituted or unsubstituted group having a molecular weight up to about 140 Daltons selected from aliphatic, aryl, aralkyl, heterocyclyl or heterocyclylalkyl ring wherein said heterocyclyl or heterocyclylalkyl ring is a three to nine membered saturated or unsaturated mono-, bi-, or tri-heterocyclic ring system wherein each ring contains up to three heteroatoms selected from O, N, or S; and R4 and R5 taken together with the intervening nitrogen form a substituted or unsubstituted carbazolyl or indolyl ring; wherein said carbazolyl or indolyl ring is optionally substituted with one or more groups independently selected from halogen, â€”R9, â€”OR9, â€”OH, â€”SH, â€”SR9, protected OH (such as acyloxy), phenyl (Ph), substituted Ph, â€”OPh, substituted â€”OPh, â€”NO2, â€”CN, â€”NH2, â€”NHR9, â€”N(R9)2, â€”NHCOR9, â€”NHCONHR9, â€”NHCON(R9)2, â€”NR9COR9, â€”NHCO2R9, â€”CO2R9, â€”CO2H, â€”COR9, â€”CONHR9, â€”CON(R9)2, â€”S(O)2R9, â€”SONH2, â€”S(O)R9, â€”SO2NHR9, or â€”NHS(O)2R9; wherein each R9 is independently selected from an aliphatic group or a substituted aliphatic group; wherein the optional substituents on said C1-12 aliphatic group or aryl, aralkyl, heterocyclyl, or heterocyclylalkyl ring is independently selected from, from halogen, â€”R11, â€”OR11, â€”OH, â€”SH, â€”SR11, acyloxy, substituted or unsubstituted Ph or OPh, â€”NO2, â€”CN, â€”NH2, â€”NHR11, â€”N(R11)2, â€”NHCOR11, â€”NHCONHR11, â€”NHCON(R11)2, â€”NR11COR11, â€”NHCO2R11, â€”CO2R11, â€”CO2H, â€”COR11, â€”CONHR11, â€”CON(R11)2, â€”S(O)2R11, â€”SONH2, â€”S(O)R11, â€”SO2NHR11, â€”NHS(O)2R11, &boxH;O, &boxH;S, &boxH;NNHR11, &boxH;NNR112, &boxH;Nâ€”OR11, &boxH;NNHCOR11, &boxH;NNHCO2R11, &boxH;NNHSO2R11, or &boxH;NR11; and wherein each R11 is independently selected from a C1-12 aliphatic group or a substituted C1-12 aliphatic group.