| 摘要 |
Prepn. of 2-R14-A-S-3-R2OOC -6-R1-6-R8-carbapenem derivs. of formula (I) and quat. ammonium and acceptable salts comprises reaction of intermediate (IV) with a thiol HS-A-R14 X(-) (VII) in inert solvent in the presence of a base to give protected carbapenem (I), followed by removal of carboxy-protecting gp. to give unprotected (I). (Where R8 = H; R1 = H, 1-10C alkyl, 2-10C alkenyl, 2-10C alkynyl, 3-6C cycloalkyl, 3-6C cycloalkyl-1-6C alkyl, phenyl, phenyl-1-6C alkyl, phenyl-2-6C alkenyl, phenyl-2-6C-alkynyl, heterocyclyl or heterocyclyl-1-6C-alkyl (where heterocyclic gps. are opt. unsatd. e.g. heteroaryl and contain 1-4 heteroatoms from N, O and S). The gps. are opt. substd. by one or more from 1-6C alkyl (opt. substd. by amino, halo, hydroxy or carboxy), halo, -OR3, -OOCNR3R4, -CONR3R4, -NR3R4, -C(=NR3)-NR3R4, -SO2NR3R4, -NHCONR3R4, R3-CO-NR4-, R3-COO-, =O, -COOR3, -SR3, -SO-R9, -CN, -N3, -O-SO3-R3, -O-SO2-R3, -NR3-SO2-R4, -NR3-C(=NR4)-R3, -NR3-COOR4 or -NO2; R3, R4 independently = H, 1-10C alkyl, 2-10C alkenyl, 2-10C alkynyl, 3-6C cycloalkyl, 3-6C cycloalkyl-1-6C-alkyl, 1-6C-alkyl-3-6C-cycloalkyl-, phenyl, phenyl-1-6C alkyl, phenyl-2-6C alkenyl, phenyl-2-6C alkynyl, heterocyclyl or heterocyclyl-1-6C alkyl (where the heterocyclic gps. are opt. unsatd. and contain 1-4 heteroatoms chosen from N, O and S) or R3 and R4 with the N atom form a 5-6 membered heterocyclic; R9 = R3, except it may not be H or R1 and R8 together = opt. hydroxy substd. 2-10C alkylidene; A = cyclopentylene, cyclohexylene or 2-6C alkylene, opt. substd. by one or more 1-4C alkyl; R2 = H, an anionic charge or easily removable carboxy protecting gp., with the condition that when R2 = H or protecting gp. a centre-anion is opt. present; R14 = an opt. aromatic, opt. polycyclic N-heterocyclic, in which the N is a quat. and joined to A; R2' = an easily removable protecting gp.; X(-) = a centre-anion and L = a readily removable gp.
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