Patent ID: 6083949
Filing Date: 2000-07-04
Classification: C07D

Abstract:
A compound represented by formula I: ##STR100## or a pharmaceutically acceptable salt thereof, wherein: AR represents an aromatic group containing 6-10 atoms;X and X' each independently represent --(CH.sub.2).sub.m --Y--(CH.sub.2).sub.n --, wherein m and n represent integers within the range of from 0-4, such that the sum of m and n is from 0-6; Y represents a member selected from the group consisting of: a direct bond; O; S(O).sub.y, with y equal to 0, 1 or 2; NR.sup.q ', with R.sup.q ' as defined below; C(O); OC(O); C(O)O; SO.sub.x NR.sup.q ' with x equal to 1 or 2 and R.sup.q ' as defined below; NR.sup.q 'SO.sub.x ; C(O)NR.sup.q ' and NR.sup.q 'C(O); ##STR101## represents a piperazinyl group; R.sup.x represents H, C.sub.1-6 alkyl(R.sup.q).sub.3, OC.sub.1-6 alkyl(R.sup.q).sub.3 or C(O)C.sub.1-6 alkyl(R.sup.q).sub.3 ;each R and R"" independently represents a member selected from the group consisting of: halo; hydroxy; C.sub.1-6 alkyl(R.sup.q).sub.3 ; OC.sub.1-6 alkyl(R.sup.q).sub.3 ; C.sub.3-8 cycloalkyl(R.sup.q).sub.3 ; CN; CONH.sub.2 ; CONHC.sub.1-6 alkyl(R.sup.q).sub.3 ; CON(C.sub.1-6 alkyl(R.sup.q).sub.3).sub.2 ; NH.sub.2 ; NHC.sub.1-6 alkyl(R.sup.q).sub.3 ; N(C.sub.1-6 alkyl(R.sup.q).sub.3).sub.2 ; CO.sub.2 H; CO.sub.2 C.sub.1-6 alkyl(R.sup.q).sub.3 ; C(O)C.sub.1-6 alkyl(R.sup.q).sub.3 ; aryl(R.sup.q).sub.3 ; heteroaryl(R.sup.q).sub.3 ; CF.sub.3 ; SH; NO.sub.2 ; SO.sub.y C.sub.1-6 alkyl(R.sup.q).sub.3, with y as defined above; SO.sub.2 NH.sub.2 ; SO.sub.2 NHC.sub.1-6 alkyl(R.sup.q).sub.3 ; SO.sub.2 N (C.sub.1-6 alkyl(R.sup.q).sub.3).sub.2 ; NHSO.sub.2 Cl.sub.1-6 alkyl(R.sup.q).sub.3, NHSO.sub.2 aryl(R.sup.q).sub.3, NHS.sub.2 heteroary (R.sup.q).sub.3, N(R.sup.q ')C(O)C.sub.1-6 alkyl(R.sup.q).sub.3 ; NR.sup.q 'C(O)NH(C.sub.1-6 alkyl(R.sup.q).sub.3); C.sub.2-4 alkenyl(R.sup.q).sub.2-3 and C.sub.2-4 alkynyl(R.sup.q)1-3;each R' independently represents a member selected from the group consisting of: hydroxy; C.sub.1-6 alkyl(R.sup.q).sub.3 ; C.sub.3-8 cycloalkyl(R.sup.q).sub.3 ; OC.sub.1-6 alkyl(R.sup.q).sub.3 ; OC.sub.3-8 cycloalkyl(R.sup.q).sub.3 ; heterocyclyl(R.sup.q).sub.3 ; CN; NH(R.sup.q ""); NHC.sub.1-6 alkyl(R.sup.q).sub.3 ; N(C.sub.1-6 alkyl(R.sup.q).sub.3).sub.2 ; NHC.sub.3-8 cycloalkyl(R.sup.q).sub.3 ; N(C.sub.3-8 cycloalkyl(R.sup.q).sub.3).sub.2 ; CF.sub.3 ; SH; NO.sub.2 ; C.sub.2-4 alkenyl(R.sup.q).sub.2-3, aryl(R.sup.q).sub.3, heteroaryl(R.sup.q).sub.3 ; C.sub.2-4 alkynyl(R.sup.q) --OC(O) C.sub.3-8 cycloalkyl(R.sup.q).sub.3 ; SO.sub.2 NH.sub.2 ; SO.sub.2 NHC.sub.1-6 alkyl(R.sup.q).sub.3 ; SO.sub.2 N(C.sub.1-6 alkyl(R.sup.q).sub.3).sub.2 ; NHSO.sub.2 C.sub.1-6 alkyl(R.sup.q).sub.3, NHSO.sub.2 aryl(R.sup.q).sub.3, NHSO.sub.2 heteroary(R.sup.q).sub.3, --OC(O) heterocyclyl(R.sup.q).sub.3 ; N(R.sub.q ')C(O)C.sub.1-6 alkyl(R.sup.q).sub.3 ; NR.sup.q 'C(O)NH(C.sub.1-6 alkyl (R.sup.q).sub.3); --OC(O)C.sub.1-6 alkyl(R.sup.q).sub.3 ; --OC(O)aryl(R.sup.q).sub.3, --OC(O) heteroaryl(R.sup.q).sub.3 ; --C(.dbd.NR.sup.q ') NH.sub.2 ; --C(.dbd.N.sup.q ')NHC.sub.1-6 alkyl(R.sup.q).sub.3, --C(.dbd.N.sup.q ')N(C.sub.1-6 alkyl(R.sup.q).sub.3).sub.2 ; CONH.sub.2 ; CONHC.sub.1-6 alkyl(R.sup.q).sub.3 ; CON(C.sub.1-6 alkyl(R.sup.q).sub.3).sub.2 ; CONHC.sub.3-8 cycloalkyl(R.sup.q).sub.3 ; CON(C.sub.3-8 cycloalkyl(R.sup.q).sub.3).sub.2 ; CO.sub.2 H; CO.sub.2 C.sub.1-6 alkyl(R.sup.q).sub.3 ; C(O)C.sub.1-6 alkyl(R.sup.q).sub.3 ; CO.sub.2 C.sub.3-8 cycloalkyl(R.sup.q).sub.3 ; C(O)C.sub.3-8 cycloalkyl(R.sup.q).sub.3 ; --[C(O)(CH.sub.2).sub.j --CR.sup.5 R.sup.6 --(CH.sub.2).sub.k --NR.sup.7 ]p-R.sup.8 ; --C(O)C.sub.3-8 cycloalkyl(R.sup.q).sub.3 ; --C(O)heterocyclyl(R.sup.q).sub.3 ; --CON[C.sub.1-6 alkyl(R.sup.q).sub.3 ][C.sub.3-8 cycloalkyl(R.sup.q).sub.3 ; --C(O)aryl(R.sup.q).sub.3, --C(O)heteroaryl(R.sup.q).sub.3 ; ##STR102## j and k independently represent integers of from 0-3; R.sup.5 and R.sup.6 are independently H, aryl, C.sub.1-6 alkyl(R.sup.q).sub.3, or CR.sup.5 R.sup.6 in combination represents a 3, 4, 5 or 6 membered cycloalkyl or heterocyclyl group, an aryl group or a heteroaryl group;p represents 1, 2 or 3, with the proviso that when p represents 1, CR.sup.5 R.sup.6 represents a 3, 4, 5 or 6 membered cycloalkyl group or a heterocyclyl group, an aryl group or a heteroaryl group, and at least one of j and k is 1, 2 or 3;R.sup.7 and R.sup.8 are independently H, C.sub.1-6 alkyl or aryl;R.sup.9 represents H, a negative charge balanced by a positively charged group or a protecting group;R.sup.q represents a member selected from the group consisting of: R.sup.q '; CN; CO.sub.2 H; CO.sub.2 C.sub.1-4 alkyl; C(O)C.sub.1-4 alkyl ; NH(R.sup.q ""); aryl(R.sup.a).sub.3 ; heteroaryl(R.sup.a).sub.3 ; NHC.sub.1-4 alkyl; N(C.sub.1-4 alkyl).sub.2 ; CONH.sub.2 ; SH; S(O).sub.y C.sub.1-6 alkyl(R.sup.a).sub.3 ; C(O)NHC.sub.1-6 alkyl(R.sup.a).sub.3 ; C(O)N(C.sub.1-6 alkyl(R.sup.a).sub.3).sub.2 ; NHC(NH)NH.sub.2 ; -heteroalkyl(R.sup.a).sub.3 ; --NHC(O)NH.sub.2 ; ##STR103## independently represent mono or bicyclic ring systems, non-aromatic or partially aromatic, containing from 5-10 ring atoms, 1-4 of which are N and 0-1 of which are O or S(O).sub.y, with y equal to 0, 1 or 2, optionally containing 1-2 carbonyl groups;each R.sup.a independently represents a member selected from the group consisting of: H, C.sub.1-6 alkyl, OC.sub.1-6 alkyl, aralkyl, substituted aralkyl, heteroaralkyl, substituted heteroaralkyl, aralkoxy, substituted aralkoxy, halo, hydroxy, CN, CONH.sub.2, CONHC.sub.1-6 alkyl, CON(C.sub.1-6 alkyl).sub.2, CO.sub.2 H, CO.sub.2 C.sub.1-6 alkyl, C(O)C.sub.1-6 alkyl, phenyl, CF.sub.3, SH, NO.sub.2, SO.sub.y C.sub.1-6 alkyl, with y as defined above; SO.sub.2 NH.sub.2, SO.sub.2 NHC.sub.1-6 alkyl, NHSO.sub.2 (substituted aryl), NHSO.sub.2 (substituted heteroaryl), NHSO.sub.2 C.sub.1-6 alkyl, NHSO.sub.2 aryl, NHSO.sub.2 heteroaryl, NH.sub.2, NHC.sub.1-6 alkyl, N(C.sub.1-6 alkyl).sub.2, NHC(O)C.sub.1-6 alkyl, NHC(O)NH(C.sub.1-6 alkyl), C.sub.2-4 alkenyl and C.sub.2-4 alkynyl;R.sup.q ' represents H, OH, C.sub.1-4 alkyl, --OC.sub.1-4 alkyl, aryl or C(O)C.sub.1-4 alkyl, andR.sup.q "" represents H, OH or OC.sub.1-4 alkyl.