Substituted cyslopentane and cyclopentene compounds useful as neuraminidase inhibitorsCompounds represented by formulae (I, II or III), wherein U is CH, O, or S; Z is -C(R2)(R3), -CH-N(R2)(R3), C(R3)[(CH2)nR2], CH-C(R3)(R8)(CH2)nR2, C[(CH2)nR2]-[CH(R3)(R8)], C[(R3)][CH[(CH2)nR2](R8)]; R1 is H, (CH2)nOH, (CH2)nNH2, (CH2)nNR10R11, (CH2)nOR11, (CH2)nSR11, or (CH2)n halogen; R9 is (CH2)nCO2H, (CH2)nSO3H, (CH2)nPO3H2, (CH2)nNO2, CH(SCH3)3, esters thereof, or salts thereof.Compound shown in the following formula and pharmacy acceptable salt thereof: wherein u is ch, o or s;z is-c (r 2) (r 3) ,-ch-n (r 2) (r 3), c (r 3) [(ch 2) nr 2], ch-c (r 3) (r 8) (ch 2) nr 2, c[(ch 2) nr 2]-[ch (r 3) (r 8)], c[(r 3)] [ch[(ch 2) nr 2] (r 8)]; r 1be h, (ch 2) noh, (ch 2) nnh 2, (ch 2) nnr 10r 11, (ch 2) nor 11, (ch 2) nsr 11or (ch 2) the n halogen; r 9be (ch 2) nco 2h, (ch 2) nso 3h, (ch 2) npo 3h 2, (ch 2) nno 2, ch (sch 3) 3, its ester or salt; or r 1r 9representative=o together, or r 2be h, nhc (o) r 5, nhc (s) r 5, nhso 2r 5, c (o) nhr 5, so 2nhr 5, ch 2s (o) r 5, or ch 2so 2r 5r 3and r 8the h that respectively does for oneself, (ch 2) nc (o) r 10, (ch 2) nco 2r 10, (ch 2) mor 10, ch (or 10) ch (r 10) m, c (o) n (r 10) m, c (o) n (or 10) r 10, (ch 2) nn (r 10) m, ch (r 10) m, (ch 2) n (r 10) m, ch 2ch (or 10) ch 2or 10, ch (or 10) ch (or 10) ch 2or 10, ch 2or 10, ch (or 10) ch 2nhr 10, ch 2ch (or 10) ch 2nhr 10, ch (or 10) ch (or 10) ch 2nhr 10, c (=nr 10) n (r 10) m, nhr 10, nhc (=nr 10) n (r 10) m, (ch 2) m-x-w-y, ch 2ch (x-w-y) ch 2or 10, ch (x-w-y) ch (or 10) ch 2or 10, ch (x-w-y) ch 2(or 10), ch (or 10) ch (x-w-y) ch 2or 10, ch (or 10) ch 2(x-w-y), ch 2ch (x-w-y) ch 2nhr 10, ch (x-w-y) ch (or 10) ch 2nhr 10, ch (x-w-y) ch 2(nhr 10), ch (or 10) ch (x-w-y) ch 2nhr 10or ch (nhr 10) ch 2(x-w-y); condition is r 2, r 3and r 8in at least one is not h; r 4be h, (ch 2) noh, (ch 2) nor 11, (ch 2) noc (o) r 11, (ch 2) nnhc (nr 11) nhr 11, (ch 2) nnr 10r 11, (ch 2) nnh 2, (ch 2) nc (=nh) (nh 2), (ch 2) nnhc (=nr 11) nh 2, (ch 2) nnhc (=nr 7) nh 2, (ch 2) ncn, (ch 2) nn 3, c (=nh) nh 2, c (nr 7) nh 2or c (nr 11) nh 2r 5be h, low alkyl group, cycloalkyl, the alkyl that halogen replaces, aryl, substituted aryl or cf 3r 7be h, (ch 2) noh, (ch 2) ncn, (ch 2) nnh 2or (ch 2) nno 2r 10be h, low alkyl group, low-grade alkenyl, branched-chain alkyl, cycloalkyl, (ch 2) the n aromatic base, (ch 2) the n substituted aromatic base, or when m be 2, two r 10base can interconnect and form the heterocycle that n replaces, or other five yuan or hexa-member heterocycle; r 11be low alkyl group, branched-chain alkyl, (ch 2) the m aromatic base, so 2r 10, c (o) r 10, or (o) or 10r 12and r 13be h, (ch 2) noh, (ch 2) nh 2, (ch 2) nnr 10r 11, (ch 2) nor 11, (ch 2) nf, (ch 2) noc (o) r 11, (ch 2) nnhc (o) r 11or x-w-y; m is 1 or 2;n is 0-4;p is 0 or 1;x is o, s, ch 2or nh; w is the spacer of the chain formation of 1-100 atom, also can randomly comprise the carbon and/or the nitrogen-atoms of replacement, can randomly comprise sauerstoffatom or sulphur atom; andy is h, oh, sh, nh 2, ch=o, ch=ch 2, co 2h, conhnh 2, or a kind of protection form of these functional end-groups.
뉴라미니다아제 감염저해 물질로서 유용한 치환된시클로펜탄 및 시클로펜틴 화합물발명의 요약본 발명의 관점은 다음의 구조식; (Ⅰ) (Ⅱ) (Ⅲ)으로 묘사되는 화합물이다.여기서, U는 CH, O 또는 S; Z는 -C(R2)(R3), -CH-N(R2)(R3), C(R3)[(CH3)nR2], CH-C(R3)(R8)(CH2)nR2, C[(CH2)NR2]-[CH(R3)(R8)], C[(R3)][CH(CH2)nR2](R8)]; R1는 H, (CH2)nOH, (CH2)nNH2, (CH2)nNR10R11, (CH2)nNR11, (CH2)nSR11 또는 (CH2)n할로겐; R9는 (CH2)nCO2H, (CH2)nSO2H, (CH2)nPO3H2, (CH2)nNO2, CH2(SCH3)3, 그것의 에스테르 또는 그것의 염.하기의 구조식으로 표현되는 화합물: [이미지] 여기서, U는 CH, O 또는 S; Z는 -C(R2)(R3), -CH-N(R2)(R3), C(R3)[(CH2)nR2], CH-C(R3)(R8)(CH2)nR2, C[(CH)2nR2]-[CH(R3)(R8)], C[(R3)]{CH(CH2)NR2](R8)]; R1은 H, (CH2)nOH, (CH2)nNH, (CH2)nNR10R11, (CH2)nOR11, (CH2)nSR11, 또는 (CH2)n 할로겐 R9는 (CH2)nCO2H, (CH2)nSO2H, (CH2)nPO3H2, (CH2)nNO2, CH2(SCH3)3, 그 에스테르 또는 그 염; 또는 R1, R9는 =O 또는 [이미지]로 표현되고 R2는 H, NHC(O)R5, NHC(S)R5, NHSO2R5, C(0)NHR5, SO2NHR5, CH2S(O)R5 또는 CH2SO2R5 R3 및 R8은 각각 H, (CH2)nC(O)R10,(CH2)nCO2R10,(CH2)mOR10, CH(OR10)CH(R10)m, C(O)N(R10)m, C(O)N(OR10)R10, (CH2)nN(R10)m, CH(R10)m, (CH2)n(R10)m, CH2CH(0R10)CH20R10, CH(0R10)CH(0R10)CH20R10, CH20R10, CH(0R10)CH2NHR10, CH2CH(0R10)CH2NHR10, CH(0R10)CH(0R10)CH2NHR10, C(=NR10)N(R10)m, NHR10, NHC(=NR10)N(R10)m, (CH2)m-X-W-Y,CH2CH(X-W-Y)CH2OR10, CH(X-W-Y)CH(OR10)CH2OR10, CH(X-W-Y)CH2(OR10), CH(OR10)CH(X-W-Y)CH2OR10, CH(OR10)CH2(X-W-Y), CH2CH(X-W-Y)CH2NHR10, CH(X-W-Y)CH(OR10)CH2NHR10,CH(X-W-Y)CH2(NHR10), CH(OR10)CH(X-W-Y)CH2NHR10, 또는 CH(NHR10)CH2(X-W-Y); R1,R2,R3,중 적어도 어느 하나는 H가 아닌 것으로 제공되며; R4는 H, (CH2)nOH, (CH2)nOR11, (CH2)nOC(O)R11, (CH2)nNHC(NR11)NHR11, (CH2)nNR10R11, (CH2)nNH2, (CH2)nC(=NH)(NH2), (CH2)nNHC(=NR11)NH2, (CH2)nNHC(=NR7)NH2, (CH2)nCN, (CH2)nN3, C(=NH)NH3, C(=NH)NH2, C(NR7)NH2 또는 C(NR11)NH2; R5는 H, 저급 알킬, 시클로 알킬, 할로겐으로 치환된 알킬, 아릴, 치환된 아릴 또는 CF3; R7은 H, (CH2)nOH, (CH2)nCN, (CH2)nNH2 또는 (CH2)nNO2; R10은 저급 알킬, 저급 알킬렌, 가지모양(branched) 알킬, 시클로 알킬, (CH2)n 방향족, (CH2)n 치환된 방향족 또는 m은 2일 때, R10의 기(group)들은 서로 연결되어 N 치환된 헤테로시클릭 환, 또는 다른 5나 6 원환의 헤테로시클릭 환; R11은 저급 알킬, 가지모양(branched) 알킬, (CH2)m 방향족, SO2R10, C(O)R10 또는 C(O)OR10; R12 및 R13은 H, (CH2)nOH, (CH2)nNH2, (CH2)nOR11, (CH2)nF, (CH2)nF, (CH2)nOC(O)R11, (CH2)nNHC(O)R11 또는 X-W-Y; m은 1 또는 2; n은 0 - 4; p는 0 또는 1; X는 O, S, CH2 또는 NH; W는 1 내지 100 원자의 사슬로 이루어진 공간군(spacer group), 임의적으로 또한 치환된 탄소 및/또는 질소 원자 또는 임의적으로 산소 또는 황 원자; 및 Y는 H, OH, SH, NH2, CH=O, CH=CH2, CO2H, CONHNH2 또는 이들 끝에 기능성의 보호기; 및 약물학적으로 수용가능한 염.