Patent ID: 6515015
Filing Date: 2003-02-04
Classification: A61K,C07D

Abstract:
A compound having the formula I or Ia: or a pharmaceutically acceptable salt thereof, wherein:A is a single or double bonded carbon or a single or double bond; R1 is selected from a group consisting of: H, C1-15 alkyl, C2-15 alkenyl, C2-15 alkynyl and C3-10 cycloalkyl, said alkyl, alkenyl, alkynyl, and cycloalkyl optionally substituted with 1 to 3 groups of Ra; R2 is selected from a group consisting of: H, C1-15 alkyl, C2-15 alkenyl, OR3, CO2alkyl, COalkyl, OH, â€”OC(O)R3, C2-15 alkynyl, C5-10 aryl, and C5-10 heteroaryl, wherein said heteroaryl is selected from the group consisting of tetrazole, benzothiophene, and benzofuran, said alkyl, alkenyl, alkynyl, aryl and heteroaryl optionally substituted with 1 to 3 groups of Ra; R3 is selected from a group consisting of: H, NHR1, NHacyl, C1-15 alkyl, C2-15 alkenyl, C1-15 alkoxy, CO2alkyl, OH, C2-15 alkynyl, C5-10 aryl, and C5-10 heteroaryl, wherein said heteroaryl is selected from the group consisting of tetrazole, benzothiophene, and benzofuran, said alkyl, alkenyl, alkynyl, aryl and heteroaryl optionally substituted with 1 to 3 groups of Ra; R4 is selected from the group consisting of: R2, â€”Dâ€”R5 and R5 is selected from the group consisting of: C5-10 aryl and C5-10 heteroaryl, wherein said heteroaryl is selected from the group consisting of tetrazole, benzothiophene, and benzofuran, said aryl and heteroaryl optionally substituted with 1 to 3 groups of Ra; W is â€”CR6R7â€”, or R8 is selected from the group consisting of CR6R7, O, NR6, and S(O)P; R6 and R7 are independently selected from the group consisting of H and C1-6 alkyl; B is a 5 membered heterocycle containing 1 double bond and 1 heteroatom selected from the group consisting of O and S, wherein said heterocycle and the aromatic ring to which it is fused represent benzothiophene or benzofuran, the heterocycle being optionally unsubstituted or substituted with 1 to 3 groups of Ra; D is selected from the group consisting of: O, S(O)p and NR1; X1 and X2 are independently selected from a group consisting of: H, OH, C1-15 alkyl, C2-15 alkenyl, C2-15 alkynyl, halo, OR3, C5-10 aryl, C5-10 aralkyl, C5-10 heteroaryl and C2-10 acyl, wherein said heteroaryl is selected from the group consisting of tetrazole, benzothiophene, and benzofuran, said alkyl, alkenyl, alkynyl, aryl and heteroaryl optionally substituted with 1 to 3 groups of Ra; Ra represents a member selected from the group consisting of: halo, aryl, heteroaryl, CF3, OCF3, CN, NO2, R3, OR3; SR3, S(O)R3, SO2R3, NR3R3, NR3COR3, NR3CO2R3, NR3CON(R3)2, NR3SO2R3, COR3, CO2R3, CON(R3)2, SO2N(R3)2, and OCON(R3)2, wherein said heteroaryl is selected from the group consisting of tetrazole, benzothiophene, and benzofuran and said aryl and heteroaryl are optionally substituted with 1 to 3 groups of halo or C1-6 alkyl; Y is selected from the group consisting of: S, â€”CH2â€”, CO, and O with the proviso that if A is a single or double bonded carbon or a single bond, Y is â€”CH2â€” or CO; Y2 is selected from the group consisting of: O, N(C1-15) alkyl, N(CO2)alkyl, Nâ€”Oalkyl, Nâ€”Oacyl and Nâ€”OH, with the proviso that if Y2 is O and R3 is CH3 then n is 2; Y1 is selected from the group consisting of: O, NH, S(O)p and CH2; Z is selected from the group consisting of: CO2R3, CONHSO2Me, CONH2 and 5-(1H-tetrazole); or (Zâ€”W)t or (Zâ€”W)v together with X1 can form a 5 or 6 membered ring, said ring being a carbocycle, optionally substituted with 1 to 3 groups of Ra; in the case where (Zâ€”W)t is used v is 0 or 1; in the case where (Zâ€”W)v is used t is 0 or 1; t and v are independently 0 or 1 such that t+v=1; n is 2-4; p is 0-2; and at least one heteroaryl substituent or the combination of B and the aromatic ring to which B is fused or the bicyclic structure on the left side of formula 1 or 1a is benzofuran.