A polymer containing a carboxyl group, a preparation method and an application thereof, a supported catalyst and a preparation method thereof and preparation methods of a penem antibiotic intermediate are disclosed. The polymer is prepared by polymerizing three monomers with different structures. The carboxyl group-containing polymer is a cross-linked polymer, and a polymer chain contains a large number of benzene rings, which can improve the rigidity and hardness of the polymer, thus effectively improving the mechanical properties of the polymer. Meanwhile, in the polymer, the carboxyl group is used as a main functional group, and is used as a carrier to prepare, by means of a coordination reaction between the carboxyl group and a heavy metal, a supported metal catalyst which has better connection stability between the metal and the polymer. The above two factors can improve the stability of the supported metal catalyst, such that the catalyst can be recycled without losing the catalytic activity. Meanwhile, loss of a heavy metal active ingredient and production cost can be reduced.

The present invention relates to preparing carbapenem intermediates that are useful to produce Ertapenem, Meropenem and Doripenem; and provides an effective process for recovering ertapenem compounds.

The present invention relates to preparing carbapenem intermediates that are useful to produce Ertapenem, Meropenem and Doripenem; and provides an effective process for recovering ertapenem compounds.

The present invention provides a process for efficiently producing a 1β-methylcarbapenem compound for oral administration. The process, which is for producing a 1β-methylcarbapenem compound represented by general formula (2), is characterized by reacting a β-lactam compound represented by general formula (1) as a starting material with a thiol compound (R₃-SH) in the presence of a base and optionally eliminating the protective group R₁. In the formulae (1) and (2), R₁ denotes a hydrogen atom, a trimethylsilyl group or a triethylsilyl group; R₂ denotes an alkyl group having 1 to 10 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms; R₃ denotes an organic group; and R₄ denotes hydrogen, a trimethylsilyl group or a triethylsilyl group.

A process for the preparation of carbapenem antibiotics, which is free from the two disadvantages: (1) use of column chromatography and (2) recovery of a difficulty soluble salt and by which the objective compounds can be efficiently prepared in a short period. Specifically, a process for the preparation of compounds represented by the general formula (IV), salts thereof, or hydrates of both, characterized by reacting a compound represented by the general formula (I) with a compound represented by the general formula (II): X-H (wherein X is a member selected from the group consisting of substituents represented by the formulae (X-1) to (X-8)) to thereby obtain a compound represented by the general formula (III) or salt thereof, converting the compound (III) or salt thereof into a compound represented by the general formula (IV) or a salt thereof through the removal of the protecting group (R3), and purifying the compound (IV) or salt thereof by crystallization.

A process for the preparation of a carbapenem-type antibacterial agent of formula (4) having a 1-alkylpyrrolidine structure or a salt thereof, a useful synthetic intermediate of formula (1) or a salt thereof, and a process for the preparation thereof: [wherein R¹ represents a C₁-C₃ alkyl group, R² and R³ each independently represents a hydrogen atom or the like].