Patent DE-19635522-A1 (DE)
Title: New pyrrolidone, imidazolone, furanone or thiophenone derivatives
Inventor: WEHNER VOLKMAR DR
IPC: C07D233/96
Filed: 1996-09-02
Abstract: 5-Membered azacyclic derivatives (I) and their salts are new. W = C(R16)-D-B-A-R1 (a), C=C(R16)-D-B-A-R1 (b) or a group of formula (c) or (d); the ring of formula (e) is saturated or partly or fully unsaturated, and optionally contains 1 or 2 N, O and/or S atoms and is optionally mono-, di- or trisubstituted by R16 or mono- or disubstituted by =Q; Y = CQ or CH2; Z = N(R0), Q or CH2; A = bond, 1-8C alkanediyl, CR2=NNR2, NR2CQNR2, QCQ'NR2, NR2S(O)nNR2, OS(O)nNR2, S(O)nNR2, 3-12 cycloalkanediyl, C triple bond C, NR2CO, CONR2, NR2CO-5-14C arylene, O, S(O)n, 5-14C arylene, CO, CO-5-14C arylene, NR2, NR2SO2, OCO, COO, N=CR2 CR2=N, CR2=CR3 or S(O)n-5-14C arylene (all optionally substituted by NR2 and/or by 1 or 2 1-8C alkanediyl); Q, Q' = O or S; B = bond, 1-8C alkanediyl, 5-10C arylene, 3-8C cycloalkanediyl, C triple bond C, NR2, CO, CONR2, NR2CO, NR2-CQ-NR2, OCO, COO, SO, SO2, SONR2, SO2NR2, NR2SO, NR2SO2, Q or CR2=CR3 (all optionally mono- or disubstitute d by 1-6C alkanediyl) or a divalent residue of a 5-6 membered saturated or unsaturated ring containing 1 or 2 N atoms (optionally mono- or disubstituted substituted by 1-6C alkyl or =Q); D, F = bond, 1-8C alkanediyl, 5-10C arylene, Q, NR2, CONR2, NR2CO, NR2CQNR2, OCO, COO, CQ, SO, SO2, SO2NR2, NR2SO, NR2SO2, CR2=CR3, C triple bond C, CR2=NNR2, N=CR2, CR2=N or CHOH (all optionally mono- or disubstituted by 1-8C alkanediyl, CR2=CR3 or 5-6C arylene); E = bond, 1-6C alkanediyl, 2-6C alkenediyl, 2-6C alkynediyl, phenylene, phenylene-1-3C alkanediyl or 1-3C alkanediyl-phenylene; G = CR4R5(CR6R7)p(CH2)qR10; L = C(R16) or N; R0 = H, 1-8C  alkyl (optionally substituted by 3-12C cycloalkyl or 5-14C aryl), 1-8C alkylcarbonyl, 3-12C cycloalkyl-carbonyl, (3-12C cycloalkyl- or 5-14C aryl-substituted) 1-6C alkylcarbonyl, 5-14C aryl-carbonyl, 3-12C cycloalkyl or 5-14C aryl (where all alkyl are optionally substituted by 1 or more F); R1 = NR2CR2(=NR2), C(=NR2)NR2R3, NR2C(=NR2)NR2R3, or a 4-14 membered mono- or polycyclic optionally aromatic ring (optionally containing 1-4 N, O and/or S and optionally substituted by R12-R15); R2, R3 = H. 1-10C alkyl (optionally substituted by 1 or more F), 3-12C cycloalkyl, 3-12C cycloalkyl-1-8C alkyl, 5-14C aryl, 5-14C aryl-1-8C alkyl, NH2; NR9OR8, R9OR8, R9COOR8, R9-5-14C aryl-R8, R9N(R8)2, R9-NR8-(1-8C hydroxyalkyl), R9CON(R8)2, R9NR8COR8, R9COR8, C(=NR8)N(R8)2; NR8C(=NR8)N(R8)2 or (1-18C alkyl)-COO-1-6C alkoxycarbonyl; R4-R7 = H, F, OH, 1-8C alkyl, 3-12C cycloalkyl, 3-12C cycloalkyl-1-8C alkyl, R9QR8, R9OCOR8, R9COOR8, R9-5-14C aryl-R8, R9N(R2)R8, R9N(R8)2, R9OCONR8R2, R9N(R2)S(O)nR8, R9NR2COQR8, R9NR2COR8, R9N(R2)CON(R2)R8, R9N(R2)S(O)nNR2R8, R9S(O)nR8, R9NR2COSR8, R9COR8, R9CONR2R8 or R9S(O)nNR2R8; R8 = H, 1-8C  alkyl (optionally substituted by 3-12C cycloalkyl or 5-14C aryl), 3-12C cycloalkyl or 5-14C aryl (where all alkyl are optionally substituted by 1 or more F); R9 = bond or 1-8C alkanediyl; R10 = CQR11, S(O)nR11, P(O)nR11 or a 4-8 membered saturated or unsaturated heterocycle containing 1-4 N, O and/or S atoms; R11 = OH, 1-8C alkoxy, 5-14C aryl-1-8C alkoxy, 5-14C aryloxy, 1-8C alkylcarbonyloxy-1-4C alkoxy, 5-14C aryl-1-8C alkylcarbonyloxy-1-4C alkoxy, NH2, mono- or di-1-8C alkylamino, 5-14C aryl-1-8C alkylamino, 1-8C dialkylaminocarbonylmethoxy, 5-14C aryl-1-8C dialkylaminocarbonylmethoxy, 5-14C arylamino or a D- or L-amino acid; R12-R15 = H, 1-10C alkyl (optionally substituted by one or more F), 3-12C cycloalkyl, 3-12C cycloalkyl-1-8C alkyl, 5-14C aryl, 5-14C aryl-1-8C alkyl, NH2, R9OR8, R9COOR8, R9N(R8)2, R9-5-14C aryl-R8; R9-NR2 (1-8C hydroxyalkyl), R9CON(R2)R8, R9N(R2)COR8, R9COR8, NR2C(=NR3)-NR2R3, C(=NR2)NR2R3 or Q; or 2 of R12-R15 which are adjacent form -OCH2O-, -OCH2CH2O- or -OC(CH3)2O-; R16 = H, 1-10C alkyl optionally substituted by 1 or more F, 3-12C cycloalkyl, 3-12C cycloalkyl-1-8C alkyl, 5-14C aryl, 5-14C aryl-1-8C alkyl, 2-20C alkenyl or 2-10C alkynyl; m = 1-6; n = 1 or 2; p, q = 0 or 1; with provisos