MXPA01000611A - Novel carbapenem derivatives - Google Patents

Abstract

Novel compounds having a broad antibacterial activity over gram-positive and gram-negative bacteria, in particular, a potent antibacterial effect on&bgr;-lactamase producing bacteria, MRSA, tolerant Pseudomonas aeruginosa, DRSP, Enterococcus and Haemophilus influenzae and an extremely high stability to DHP-1.These compounds are those represented by general formula (I), pharmaceutically acceptable salts thereof and esters of the carboxylic acid at the 3-position of the carbapenem ring thereof.

Description

BACKGROUND OF THE INVENTION FIELD OF THE INVENTION The present invention relates to a carbapenem compound having an excellent antimicrobial activity and a broad range of antimicrobial spectrum, and which can be administered not only by injection but also orally. More particularly, the present invention relates to a novel carbapenem derivative having a substituted imidazo [5, 1-b] thiazole group or a salt thereof. BACKGROUND OF THE ART Derivatives of carbapenem, by virtue of a potent antibacterial activity against an amymix, are t ..;. of bacteria, have been studied deeply as a highly useful β-lactam agent, and imipenem, panipenem and meropenem have been clinically employed. Both imipenem and panipenem, however, are used as a mixture due to instability against renal dehydropeptidase-1 ("DHP-1") in the case of imipenem and to reduce nephrotoxicity in the case of panipenem. Meropenem that has recently been commercialized has a methyl group in the lß position in such a way that it has an increased stability in relation to DHP-1 and can therefore be used alone. However, there remains a need for a drug that has a greater stability in relation to DHP-1. In addition, effective drugs for methicillin-resistant Staphylococcus aureus ("MRSA"), penicillin-resistant Streptococcus pneumoneae ("PRSP"), resistant Pseudomonas aeruginosa and resistant enterococci that have recently become severe problems as well as influenza have also been requested. . Some of the present inventors have previously reported the carbapenem derivatives having an imidazo [5, 1-b] thiazolium-6-ylmethyl group of novel heteroaromatic ring at the 2-position on the carbapenem ring in O96 / 028455 and the carbapenem derivatives having an imidazo [5, 1-b] thiazole group through a pyrrolidinylthio group in the 2-position of the carbapenem ring in W98 / 023623 and, in addition, the carbapenem derivatives having an imidazo group [5, 1-b] thiazole directly at position 2 of the carbapenem ring in O98 / 032760. In addition, WO96 / 011932 and O96 / 034868 and Japanese Patent Publication No. 273876/1992 disclose the carbapenem derivatives wherein a carbon atom in the heteroaromatic ring is attached at the 2-position of the carbapenem ring. However, no specific data on antimicrobial activities or the effectiveness of these derivatives have been described. Neither bicyclic heteroaromatic rings nor carbapenem rings having an imidazo [5, 1-b] thiazole group have been described. SUMMARY OF THE INVENTION The present inventors have now found that novel carbapenem derivatives having a imidazo [5,1-b] thiazole group substituted at the 2-position on the carbapenem ring have potent antimicrobial activities against bacteria producing β- lactamase, MRSA, resistant Pseudomonas aeruginosa, PRSP, enterococci, and influenza, and high stabilities in relation to DHP-1. The present invention is based on such findings. Accordingly, the object of the present invention is to provide novel compounds having a wide range of anti-gram-positive and anti-gram-negative microbial activities, especially high antimicrobial activities against microorganisms including β-lactamase-producing bacteria, MRSA, enterococci, PRSP , influenza, and high stabilities in relation to DHP-1. According to the present invention, there is provided a compound represented by the formula (I), or a pharmacologically acceptable salt thereof or an ester at the 3-position in the carbapenem ring thereof: (I) where R represents a hydrogen atom or a methyl group, R2, R3, R4, and R5, any of them represents the union with the 2-position in the carbapenem ring, and the other three may be the same or different, and represent respectively a hydrogen atom, a halogen atom, a nitro group, a cyano group, a lower alkyl group which may be substituted, a lower cycloalkyl group which may be substituted, a lower alkylthio group, an arylthio group, an C2-4 alkenyl group which may be substituted, a formyl group, a lower alkylcarbonyl group which may be substituted, a lower alkoxycarbonyl group, a lower alkylsulfonyl group, an arisulfonyl group which. may be substituted, an aminosulfonyl group, a lower N-alkylsulfonyl group, a lower N-alkoxy-N-lower alkylsulfonyl group, a lower alkylsulfinyl group, an arylsulfinyl group, an aminosulfinyl group, an arylcarbonyl group, an aryl group which may be substituted, a carbamoyl group, a lower N-alkylcarbamoyl group, a lower N, N-di-alkylaminocarbonyl group, a lower alkoxyiminomethyl group, a hydroxyiminomethyl group, or an aromatic heterocyclic ring of five or six .. members having one or more heteroatoms selected from nitrogen, oxygen and sulfur atoms, and R represents a hydrogen atom or a group that may be hydrolyzed in organisms. DETAILED DESCRIPTION OF THE INVENTION Definition As used herein, the term "lower alkyl" or "lower alkoxy" as a group or part of a group means a straight-chain or branched-chain alkyl or alkyloxy having from 1 to 6 carbon atoms. carbon, preferably from 1 to 4 carbon atoms. Examples of the lower alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, i-butyl, s-butyl, t-butyl, n-pentyl, n-hexyl, and the like. In addition, lower alkoxy includes, by way of example, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, and the like. The term "lower cycloalkyl" means monocyclic alkyl having from 3 to 6 carbon atoms. In addition, the term "aryl" means an aromatic ring and an aromatic polycyclic hydrocarbon ring, preferably phenyl or naphthyl. The term "halogen" here means fluorine, chlorine, bromine or iodine. Compound In formula (I), any of R2, R3, R4, and R5 represents the bond with position 2 of the carbapenem ring. The remaining three groups, which may be the same or different, represent respectively a hydrogen atom, a halogen atom, a nitro group, a cyano group, a lower alkyl group which may be substituted, a lower -cycloalkyl group which may be substituted , a lower alkylthio group, an arylthio group, a C-4 alkenyl group which may be substituted, a formyl group, a lower alkylcarbonyl group which may be substituted, a lower alkoxycarbonyl group, a lower alkylsulfonyl group, an arylsulfonyl group which may be substituted, to be substituted, an aminosulfonyl group, a lower alkylaminosulfonyl group, a lower N, N-di-alkylaminosulfonyl group, an N-lower alkoxy-N-lower alkylsulfonyl group, a lower alkylsulfinyl group, an arylsulfinyl group, an aminosulfinyl group, a group arylcarbonyl, an aryl group that may be substituted, a carbamoyl group, a lower N-alkylcarbamoyl group, a N, N-di-alkylaminocarbonyl group or lower, a lower alkoxyiminomethyl group, a hydroxyiminomethyl group, or a five or six membered aromatic heterocyclic ring having one or more heteroatoms selected from nitrogen, oxygen and sulfur atoms. In accordance with the preferred embodiment of the present invention, the three remaining groups, which may be the same or different, respectively represent a hydrogen atom, a halogen atom, a cyano group, a lower alkyl group which may be substituted, an a lower cycloalkyl group which may be substituted, a lower alkylthio group, an arylthio group, a C 1 - alkenyl group which may be substituted, a formyl group, a lower alkylcarbonyl group which may be substituted, a lower alkylsulfonyl group, an arylsulfonyl group which may be substituted, an aminosulfonyl group, a lower N-alkylaminosulfonyl group which may be substituted, a lower N-di-alkylaminosulfonyl group which may be substituted, a lower alkylsulfinyl group, a group arylcarbonyl, an aryl group which may be substituted, a lower alkoxyiminomethyl group, a hydroxyiminomethyl group, or a five or six membered aromatic heterocyclic ring having one or more heteroatoms selected from nitrogen, oxygen and sulfur atoms. More preferably, the three remaining groups represent a hydrogen atom, a halogen atom, a cyano group, a lower alkyl group (in which one or more hydrogen atoms in the alkyl group may be substituted by selected groups within the group consisting of a halogen atom, a hydroxy group, an amino group, a formylamino group, a lower alkylcarbonylamino group, a carbamoyl group, and a lower alkylsulfonylamino group), a lower cycloalkyl group which may be substituted by carbamoyl, a group lower alkylthio, an arylthio group, a C 2-4 alkenyl group (where one or several hydrogen atoms in the alkenyl group may be substituted by a lower alkylcarbonyl group or a lower alkoxycarbonyl group), a formyl group, a lower alkylcarbonyl group (wherein one or more hydrogen atoms in the alkyl group may be substituted by groups selected from the group consisting of of a halogen atom, a hydroxy group, an amino group, a lower alkylcarbonylamino group, a lower N, N-di-alkylaminocarbonyl group, a (N-lower alkylamino) sulfonyl group, a (N, N-di-alkylamino group lower) sulfonyl, and a lower alkylsulfonylamino group), a lower alkylsulfonyl group, an arylsulfonyl group (in which one or more hydrogen atoms may be substituted by a lower alkyl group), an aminosulfonyl group, a lower N-alkylaminosulfonyl group (in where one or several hydrogen atoms in the alkyl group may be substituted by groups selected from the group consisting of a lower alkoxy group, a hydrogen atom, and an aryl group (wherein one or more hydrogen atoms in the aryl group) they may be substituted by an amino group), a lower N, N-di-alkylaminosulfonyl group, a lower alkylsulfinyl group, an arylcarbonyl group, an aryl group which may be substituted by a or lower alkylcarbonyl, a lower alkoxyiminomethyl group, a hydroxyiminomethyl group, or a five or six membered aromatic heterocyclic ring having one or more heteroatoms (nitrogen, oxygen or sulfur atom). In R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.5 and R.sub.3 which represent lower alkyl, one or more hydrogen atoms in the lower alkyl may be substituted by halogen, nitro, cyano, lower cycloalkyl, lower alkylthio, lower alkoxy, hydroxy, amino, N- lower alkylamino, formyl, lower alkylcarbonyl, arylcarbonyl, carboxyl, lower alkoxycarbonyl, formylamino, lower alkylcarbonylamino, carbamoyl, N-lower alkylcarbamoyl, N, N-di-lower alkylaminocarbonyl, aminosulfonyl, (N-lower alkylamino) sulfonyl, (N, N -di-lower alkylamino) sulfonyl, (N, -alkylamino) -sulfonylamino, aminosulfonylamino, (N, -di-lower alkylamino) sulfonylamino, lower alkylsulfonyl, and aryl. In accordance with the preferred embodiment of the present invention, the substituent preferably includes halogen, hydroxy, amino, formylamino, lower alkylcarbonyl, carbamoyl as well as lower alkylsulfonylamino. The substituted alkyl includes, for example, aminomethyl, hydroxymethyl, 2-hydroxyethyl, carbamoylmethyl, 2-carbamoylethyl, 2-fluoroethyl, cyclopropylmethyl, 2- (N-methylcarbamoyl) ethyl, N, N-dimethylcarbamoylmethyl, 2- (N, N- dimethylcarbamoyl) ethyl, 2-aminosulfonylaminoethyl, aminosulfonylaminomethyl, 2- (aminosulfonylamino) ethyl, methoxymethyl, ethoxycarbonylmethyl, formylaminomethyl, methoxyiminomethyl, hydroxyiminomethyl, and benzyl. In R2, R3, R4, and R5 representing lower cycloalkyl, one or more hydrogen atoms in the cycloalkyl can be substituted by a group selected from the group consisting of lower alkyl, halogen, nitro, cyano, lower alkylthio, lower alkoxy , hydroxy, amino, N-lower alkylamino, formyl, lower alkylcarbonyl, arylcarbonyl, carboxyl, lower alkoxycarbonyl, formylamino, lower alkylcarbonylamino, carbamoyl, N-lower alkylcarbamoyl, N, N-di-lower alkylaminocarbonyl, aminosulfonyl, (N-lower alkylamino ) sulfonyl, (N, N-di-lower alkylamino) sulfonyl, (N-lower alkylamino) sulfonylamino, aminosulfonylamino, (N, N-di-lower alkylamino) sulfonylamino, and aryl, more preferably carbamoyl. In addition, in R2, R3, R4, and R5 representing alkenyl, one or more hydrogen atoms in the alkenyl may be substituted, and the substituent includes for example a group selected from the group consisting of lower alkyl, halogen, nitro, cyano, lower cycloalkyl, lower alkylthio, lower alkoxy, hydroxy, amino, N-lower alkylamino, formyl, lower alkylcarbonyl, arylcarbonyl, carboxyl, lower alkoxycarbonyl, formylamino, lower alkylcarbonylamino, carbamoyl, N-lower alkylcarbamoyl, N, N-di- lower alkylaminocarbonyl, aminosulfonyl (N-lower alkylamino) sulfonyl, (N, N-di-lower alkylamino) sulfonyl, (N-lower alkylamino) "sulfonylamino, aminosulfonylamino, (N, N-di-lower alkylamino) sulfonylamino, and aryl, more preferably lower alkylcarbonyl and lower alkoxycarbonyl In R 2, R 3, R 4, and R 5 representing lower alkylcarbonyl, one or more hydrogen atoms in the group may be substituted, and the substituent includes for example a group selected from the group consisting of halogen, nitro, cyano, lower cycloalkyl, lower alkylthio, lower alkoxy, hydroxy, amino, N-lower alkylamino, formyl, lower alkylcarbonyl, arylcarbonyl, carboxyl, lower alkoxycarbonyl, formylamino, lower alkylcarbonylamino, carbamoyl, lower N-alkylcarbamoyl, N, N-di-lower alkylaminocarbonyl, aminosulfonyl, (N-lower alkylamino) sulfonyl, (N, N-di-lower alkylamino) sulfonyl, (N-lower alkylamino) sulfonylamino, aminosulfonylamino, (N, N-dialkylamino) sulfonylamino), lower alkylsulfonylate, and aryl, more preferably halogen, hydroxy, amino, lower alkylcarbonylamino, N, N-dialkylaminocarbonyl lower, (N-lower alkylamino) sulfonyl, aminosulfonylamino, (N, N-dialkylamino lower) sulfonylamino, and lower alkylsulfonylamino. In R2, R3, R4, and R5 representing arisulphonyl, one or more hydrogen atoms in the group may be substituted and the substituent includes for example a group selected from the group consisting of lower alkyl, halogen, nitro, cyano, cycloalkyl lower, lower alkylthio, lower alkoxy, hydroxy, amino, N-lower alkylamino, formyl, lower alkylcarbonyl, arylcarbonyl, carboxyl, lower alkoxycarbonyl, formylamino, lower alkylcarbonylamino, carbamoyl, N-lower alkylcarbamoyl, N, N-di-lower alkylaminocarbonyl, aminosulfonyl, (N-lower alkylamino) sulfonyl, (N, N-di-lower alkylamino) sulfonyl, (N-lower alkylamino) sulfonylamino, aminosulfonylamino, and (N, N-di-lower alkylamino) sulfonylamino, more preferably lower alkyl . Further, in R2, R3, R4, and R5 representing lower N-alkylaminosulfonyl, one or more hydrogen atoms in the group may be substituted, and the substituent includes for example a group selected from the group consisting of halogen, nitro, cyano, lower cycloalkyl, lower alkylthio, lower alkoxy, hydroxy, amino, N-lower alkylamino, formyl, lower alkylcarbonyl, arylcarbonyl, carboxyl, lower alkoxycarbonyl-, formylamino, lower alkylcarbonylamino, carbamoyl, N-lower alkylcarbamoyl, N, N-dialkylaminocarbonyl lower, aminosulfonyl, (N-lower alkylamino) sulfonyl, (N, N-di-lower alkylamino) sulfonyl, (N-lower alkylamino) sulfonylamino, aminosulfonylamino, "(N, N-dialkylamino) sulfonylamino, and aryl (wherein one or more hydrogen atoms in the aryl may be substituted, and the substituent includes for example a group selected from the group consisting of lower alkyl, halogen, nitro, no, lower cycloalkyl, lower alkylthio, lower alkoxy, hydroxy, amino, N-lower alkylamino, formyl, lower alkylcarbonyl, arylcarbonyl, carboxyl, lower alkoxycarbonyl, formylamino, lower alkylcarbonylamino, carbamoyl, N-lower alkylcarbamoyl, N, N-di- lower alkylaminocarbonyl, aminosulfonyl, (N-lower alkylamino) sulfonyl, (N, N-di-lower alkylamino) sulfonyl, (N-lower alkylamino) sulfonylamino, aminosulfonylamino, and (N, N-di-lower alkylamino) sulfonylamino), with more preferred are lower alkoxy, hydroxy, and aryl (which may be substituted by amino). In addition, in R2, R3, R4, and R5 representing lower N-dialkylaminosulfonyl, one or more hydrogen atoms in the group may be substituted, and the substituent includes for example a group selected from the group consisting of halogen, nitro, cyano, lower cycloalkyl, lower alkylthio, lower alkoxy, hydroxy, amino, N-lower alkylamino, formyl, lower alkylcarbonyl, arylcarbonyl, carboxyl, lower alkoxycarbonyl, formylamino, lower alkylcarbonylamino, carbamoyl, N-lower alkylcarbamoyl, N, N-dialkylaminocarbonyl lower , aminosulfonyl, (N-lower alkylamino) sulfonyl, (N, N-di-lower alkylamino) sulfonyl, (N-lower alkylamino) sulfonylamino, aminosulfonylamino, (N, N-dialkylamino) -sulfonylamino, and aryl.

In addition, in R2, R3, R4, and R5 representing aryl, one or more hydrogen atoms in the group may be substituted, and the substituent includes for example a group selected from the group consisting of lower alkyl, halogen, nitro, cyano, lower cycloalkyl, lower alkylthio, lower alkoxy, hydroxy, amino, N-lower alkylamino, formyl, lower alkylcarbonyl, arylcarbonyl, Carboxyl, lower alkoxycarbonyl, formylamino, lower alkylcarbonylamino, carbamoyl, N-lower alkylcarbamoyl, N, N-dialkylaminocarbonyl lower, aminosulfonyl, (N-alkylated lower ino) sulfonyl, (N, N-lower dialkylamino) sulfonyl, (N lower alkylamino) sulfonylamino, aminosulfonylamino, and (N, N-diacylamino lower) sulfonylamino, more preferably lower alkylcarbonyl. Examples of aromatic heterocyclic ring five or six members having one or more atoms selected from nitrogen, oxygen and sulfur represented by R2, R3, R4 and R5 heteroatoms include thiazolyl, imidazolyl, oxazolyl, pyridyl, pyrrolyl, pyrazinyl, and pyrimidinyl, more preferably thiazolyl. In these groups, one or more hydrogen atoms may be substituted, and the substituent includes, for example, lower alkyl, halogen, lower alkoxy, hydroxy, and amino. R represents a group that can be hydrolyzed in organisms, preferably an ester residue. Examples of the group include alkyl C? _10, a group arylcarbonyloxy-lower alkyl, an aryl-lower alkyloxy-alkylcarbonyloxy group-lower alkyl, lower alkylcarbonyloxy-lower alkyl, cycloalkylcarbonyloxy bottom-lower alkyl, lower cycloalkyl-lower alkylcarbonyloxy-lower alkyl, • lower alkyl lower-lower lower alkyl-lower diciclohexilmetilcarboniloxi-alkyl, adamantilcarboniloxi-lower alkyl, alkyloxycarbonyloxy, cycloalkyloxycarbonyloxy, (lower cycloalkyloxycarbonyloxy) (lower cycloalkyl) methyl, lower cycloalkyl-alkyloxycarbonyloxy-lower alkyl, adamantiloxicarboniloxi-lower alkyl, Z- indanyloxycarbonyloxy -lower alkyl, aryl-_ alkyloxycarbonyloxy alkyl 2-oxo-5-lower-alkyl lower, aryloxycarbonyloxy lower alkyl wherein the aromatic ring may be substituted, 5-indaniloxicarboniloxi- lower alkyl wherein the aromatic ring may be substituted, lower-1, 3-dioxolen-4-ylmethyl, 3-phthalidyl wherein the aromatic ring may be substituted, or 2- (3-phthalidylidene) ethyl wherein the aromatic ring may be substituted. According to another preferred embodiment of the invention, R preferably represents C: - o alkyl. arylcarbonyloxy-lower alkyl, aryl-lower alkyloxy-lower alkylcarbonyloxy-lower alkyl, lower cycloalkyl-lower alkylcarbonyloxy-lower alkyl, dicyclohexylmethylcarbonyloxy-lower alkyl, adamantylcarbonyloxy-lower alkyl, (cycloalkyloxycarbonyloxy) lower (cycloalkyl) methyl, cycloalkylethoxycarbonyloxy lower alkyl group bottom, adamantyloxycarbonyloxy-lower alkyl, 2-indanyloxycarbonyloxy-lower alkyl, aryloxy-lower alkyloxycarbonyloxy-lower alkyl, aryloxycarbonyloxy-lower alkyl wherein the aromatic ring may be substituted, or 5-indanyloxycarbonyloxy-lower alkyl. One or more hydrogen atoms in the alkyl group, the lower cycloalkyl group, or the aryl group in the above groups may be substituted. According to another preferred embodiment of the present invention, R represents benzoyloxymethyl, 1- (benzoyloxy) ethyl, 1- (2-methylbenzoyloxy) ethyl, 4-t-butylbenzoyloxymethyl, 2,4,6-trimethylbenzoyloxymethyl, 4- (N, N-di-n-propylaminosulfonyl) benzoyloxymethyl, 1- [4- (N, N-di-n-propylaminosulfonyl) benzoyloxymethyl] ethyl, 2-naphthylcarbonyloxymethyl, 1-adamantylcarbonyloxymethyl, 1- (1-adamantylcarbonyloxy) ethyl, cyclohexyl (cyclohexyloxycarbonyloxy) methyl, (IR, 2S, 5R) - (1) -methyloxycarbonyloxymethyl, (SS, 2R, 5R) - (d) -methyloxycarbonyloxymethyl , 1- [(cyclohexylethoxy) carbonyloxy] ethyl, 2-adamantyloxycarbonyloxymethyl, 1- (2-phenyl-1-ethyloxycarbsynyloxy) ethyl, 1- (4-methylphenoxycarbonyloxy) ethyl, 1- (2-methylphenoxycarbonyloxy) ethyl, 1- (2 -ethylphenoxycarbonyloxy) ethyl, 1- [2- (2-propyl) phenoxycarbonyloxy] ethyl, 1- (2,4-dimethylphenoxycarbonyloxy) ethyl, 1- (2,5-dimethylphenoxycarbonyloxy) ethyl, 1- (3,5-dimethylphenoxycarbonyloxy) ethyl, 1- (2,3-, 5-trimethylphenoxycarbonyloxy) ethyl, 1- (2,6-dimethylphenoxycarbonyloxy) methyl, 2-methyl-1- (phenoxycarbonyloxy) -1-propyl, 1- (2-methoxyphenoxycarbonyloxy) ethyl, - (1-naphthoxycarbonyloxy) ethyl, (indan-5-yl) oxycarbonyloxymethyl, 1- ((indan-5-yl) oxycarbonyloxy) ethyl, and 1- ((indan-5-yl) oxycarbonyloxy) -1-propyl. Examples of substituents on 2-indanyloxycarbonyloxy-lower alkyl, 5-indanyloxycarbonyloxy-lower alkyl, 2-oxo-5-lower alkyl-1,3-dioxolen-4-ylmethyl, 3-phthalidyl, and 2- (3-phthalidylidene) ethyl) include lower alkyl, halogen, nitro, cyano, lower cycloalkyl, lower alkylthio, lower alkoxy, hydroxy, amino, N-lower alkylamino, formyl, lower alkylcarbonyl, arylcarbonyl, carboxyl, lower alkoxycarbonyl, formylamino, lower alkylcarbonylamino, carbamoyl, N - lower alkylcarbamoyl, N, N-dialkylaminocarbonyl lower, aminosulfonyl, (N-lower alkylamino) sulfonyl, (N, N-dialkylamino lower) sulfonyl, (N-lower alkylamino) sulfonylamino, aminosulfonylamino, (N, N-dialkylamino lower) sulfonylamino , and aryl, more preferably lower alkoxy, hydroxy, formylamino, and carbamoyl. One or more hydrogen atoms in the alkyl group of "lower alkylcarbonyloxy-lower alkyl, lower alkyloxycarbonyloxy-lower alkyl, and 2-oxo-5-lower alkyl-1,3-dioxolen-4-ylmethyl represented by R may be substituted, and substituents include, for example, halogen, nitro, cyano, lower cycloalkyl, lower alkylthio, lower alkoxy, hydroxy, amino, N-lower alkylamino, formyl, lower alkylcarbonyl, arylcarbonyl, carboxyl, lower alkoxycarbonyl, formylamino, lower alkylcarbonylamino, carbamoyl , N-lower alkylcarbamoyl, N, N-dialkylaminocarbonyl lower, aminosulfonyl, (N-lower alkylamino) sulfonyl, (N, N-dialkylamino lower) sulfonyl, (N-lower alkylamino) sulfonylamino, aminosulfonylamino, (N, N-dialkylamino lower ) sulfonylamino, lower alkylsulfonylamino, and aryl, more preferably lower alkoxy, lower cycloalkyl, and aryl.One or more hydrogen atoms in the arylcarbon aryl group Boniloxy lower alkylAryl-lower alkyloxy-alkylaminocarbonyloxy-lower alkyl, arilalquiloxicarboniloxi-lower alkyl, aryloxycarbonyloxy-lower alkyl represented by R may be substituted, and the substituents include for example lower alkyl, halogen, nitro, cyano, lower cycloalkyl, lower alkylthio , lower alkoxy, hydroxy, amino, N-lower alkylamino, formyl, alkylcarbonyl "lower, arylcarbonyl, carboxyl, lower alkoxycarbonyl, ._ formylamino, lower alkylcarbonylamino, carbamoyl, N-lower alkylcarbamoyl, N, N-dialkylaminocarbonyl lower, aminosulfonyl, ( N-lower alkylamino) sulfonyl, (N, N-di-lower alkylamino) sulfonyl, (N-lower alkylamino) sulfonylamino, aminosulfonylamino, (N, N-dialkylamino _ lower) sulfonylamino, and aryl, more preferably lower alkyl, lower alkoxy, lower cycloalkyl, and aryl, one or more hydrogen atoms in the cycloalkyl group of lower cycloalkylcarbonyloxy lower lower lower alkyl-lower lower alkyl-lower lower alkyl-or-alkyl, cycloalkyl lower-alkylcarbonyloxy, cycloalkyl lower-alkylcarbonyloxy, cycloalkyloxycarbonyloxy, (lower cycloalkyloxycarbonyloxy) (lower cycloalkyl) methyl, and cycloalkyl lower-alkyloxycarbonyloxy-lower alkyl represented by R may be substituted, and substituents include, for example, lower alkyl, halogen, nitro, cyano, lower cycloalkyl, lower alkylthio, lower alkoxy, hydroxy, amino, N-lower alkylamino, formyl, lower alkylcarbonyl, arylcarbonyl, carboxyl, lower alkoxycarbonyl , formylamino, lower alkylcarbonylamino, carbamoyl, N-lower alkylcarbamoyl, N, N-dialkylaminocarbonyl lower, aminosulfonyl, (N-lower alkylamino) sulfonyl, (N, N-di-lower alkylamino) sulfonyl, (N-lower alkylamino) sulfonylamino, aminosulfonylamino, (N, N-dialkylamino lower) sulfonylamino, and aryl, with ma and preferably lower alkyl, lower alkoxy, and lower cycloalkyl. Preferred compounds of the formula (I) according to the present invention include the compounds in which R1 represents a hydrogen atom or a methyl group, R2, R3, R4, and R5, one of them represents the union in the position 2 in the carbapenem ring, and the other three may be the same or different, and represent respectively a hydrogen atom, a halogen atom, a cyano group, a lower alkyl group which may be substituted, a lower cycloalkyl group which may be substituted, a lower alkylthio group, an arylthio group, a C 2-4 alkenyl group which may be substituted, a formyl group, a lower alkylcarbonyl group which may be substituted, a lower alkylsulfonyl group, an aryisulfonyl group which may be substituted, a group aminosulfonyl, a lower N-alkylaminosulfonyl group, a lower N, N-dialkylaminosulfonyl group, a lower alkylsulfinyl group, an arylcarbonyl group, an aryl group which a substituted lower alkoxyiminium group, an inomethyl hydroxyl group, or a five or six membered aromatic heterocyclic ring having one or more heteroatoms selected from nitrogen, oxygen, and sulfur atoms. Preferred compounds according to formula (I) according to the present invention include those compounds in which R 2 represents the bond in the 2-position in the carbepenem ring. Among the compounds of the formula (I) wherein R 2 represents the bond at the 2-position on the carbapenem ring, preferred compounds include the compounds in which R 1 represents hydrogen or methyl, R 3, R 4, and R 5, which may be same or different, and represent respectively a hydrogen atom, a cyano group, a lower alkyl group in which one or more hydrogen atoms in the alkyl group may be substituted by groups selected from the group consisting of a halogen atom, a hydroxy group, an amino group, a formylamino group, a lower alkylcarbonylamino group, a carbamoyl group, and a lower alkylsulfonylamino group, a lower cycloalkyl group which may be substituted by a carbamoyl group, a lower alkylthio group, an arylthio group , a C2-C alkenyl group in which one or several hydrogen atoms in the alkenyl group can be substituted by a lower alkylcarbonyl group or a lower alkoxycarbonyl group, a formyl group, a lower alkylcarbonyl group in which one or several hydrogen atoms in the alkyl group they may be substituted by groups selected from the group consisting of a halogen atom, a hydroxy group, an amino group, a lower alkoxycarbonylamino group, a lower N, N-dialkylaminocarbonyl group, a group (lower N-alkylamino ) sulfonyl, a (N, N-dialkylamino) sulfonyl group and a lower alkylsulfonylamino group, a lower alkylsulfonyl group, a or arisulphonyl in which one or more hydrogen atoms in the aryl group may be substituted by a lower alkyl group, an aminosulfonyl group, a lower N-alkylaminosulfonyl group in which one or more hydrogen atoms in the alkyl group may be substituted by groups selected from the group consisting of a lower alkoxy group, a hydrogen atom, and an aryl group (wherein one or more hydrogen atoms in the alkyl group may be substituted by an amino group), a group N, N -dialkylaminosulfonyl lower a lower alkylsulfinyl group, an arylcarbonyl group, an aryl group which may be substituted by a lower alkylcarbonyl group, a lower alkoxyiminomethyl group, a hydroxyiminomethyl group, or a five or six membered aromatic heterocyclic ring having one or more heteroatoms selected from nitrogen, oxygen and sulfur atoms. Among the compounds, the most preferred compounds include the compounds in which R 1 represents methyl, R 3, R 4, and R 5, which may be the same or different, respectively represent a hydrogen atom, a lower alkyl group which may be substituted by selected groups within the group consisting of a halogen atom, a hydroxy group, an amino group, a formylamino group, a lower alkylcarbonylamino group, a carbamoyl group, a lower alkylsulfonylamino group and an aryl group, a lower alkylthio group, an arylthio group, a lower alkylcarbonyl group which may be substituted by groups selected from the group consisting of a halogen atom, a hydroxy group, an amino group, a lower alkylcarbonylamino group, a lower N, N-dialkylaminocarbonyl group, a group (N-alkylamino) lower) sulfonyl, a lower (N, N-dialkylamino) sulfonyl group, and a lower alkylsulfonylamino group, an lower alkylsulfonyl group or, an arylsulfonyl group which may be substituted by a lower alkyl group, an aminosulfonyl group, a lower N-alkylaminosulfonyl group which may be substituted by groups selected from the group consisting of a lower alkoxy group, a hydrogen atom, a group aryl (which may be substituted by an amino group), a lower N, N-dialkylaminosulfonyl group, a lower alkylsulfinyl group, a hydroxyiminomethyl group, or a five or six membered aromatic heterocyclic ring having one or more heteroatoms selected from among atoms of nitrogen, oxygen and sulfur. Other preferred compounds include the compounds in which R1 represents methyl, R2 represents the bond at the 2-position in the carbapenem ring R3 and R4. they represent a hydrogen atom, R3 represents a lower alkylthio group or a lower alkylsulfonyl group, and R represents a hydrogen atom or a group that may be hydrolyzed in organisms. Among these compounds, the most preferred compounds include those compounds in which R 5 represents methylthio or methylsulfonyl. Other preferred compounds include those compounds in which R 1 represents methyl, R 2 represents the bond at the 2-position on the carbapenem ring, R 3 and R 4 represent a hydrogen atom, R 5 represents a lower alkylcarbonyl group (wherein one or more hydrogen atoms in the alkyl group may be substituted by selected groups within of the group consisting of a halogen atom, a hydroxy group, an amino group, a lower alkylcarbonylamino group, a lower N, N-dialkylaminocarbonyl group, a (N-lower alkylamino) sulfonyl group, a (N, N-dialkylamino group lower) sulfonyl, and a lower alkylsulfonylamino group), a lower alkyl group substituted by a lower alkylcarbonylamino group, a lower N, N-di-alkylaminosulfonyl group, or a lower alkylsulfinyl group. Other preferred compounds include the compounds in which R1 represents methyl, R2 represents the bond at the 2-position in the carbapenem ring, R3 and R4 represent a hydrogen atom, R5 represents a lower alkyl group substituted by a lower alkylcarbonylamino group, the in which R1 represents methyl, R9 represents the bond at the 2-position in the carbapenem ring, R3 and R4 represent a hydrogen atom, R5 represents a lower N, N-di-alkylaminosulfonyl group, those in which R1 represents methyl , R 2 represents the bond in position 2 in the ring of carbapenem, R 3 and R 4 represent a hydrogen atom, R 5 represents a group N, N-dimethylaminosulfonyl, the compounds in which R 1 represents methyl, R 2 represents the bond in the 2-position in the carbapenem ring, R3 represents a hydrogen atom, R4 represents a lower alkyl group, R5 represents a lower alkylcarbonyl group which may be substituted gone by a hydroxyl group, the compounds in which R1 represents methyl, R2 represents the bond in the 2-position in the carbapenem ring, R3 represents a hydrogen atom, R4 represents a lower alkyl group, and R5 represents a lower alkylsulfonyl group compounds in which R1 represents methyl, R2 represents the bond at the position kZ on the carbapenem ring, R3 represents a hydrogen atom, R4 represents methyl, and R5 represents methylsulfonyl, the compounds in which R1 represents methyl, R2 represents the bond in the 2-position in the carbapenem ring, R3 and R4 represent a hydrogen atom, and R5 represents a lower alkylsulfinyl group), the compounds in which R1 represents methyl, R2 represents the bond in the 2-position in the ring of carbapenem, R3 and R4 represent a hydrogen atom, and R5 represents a methylsulfinyl group. Other preferred compounds include those compounds in which R.sup.1 represents a hydrogen atom or a methyl group, R.sup.2, R.sup.3, R.sup.4, and R.sup.5, except that which represents the bond in the 2-position in the carbapenem ring, which may be the same or different, represent respectively a hydrogen atom, a lower alkyl group which may be substituted, an arylthio group, a C 2-4 alkenyl group which may be substituted, a lower alkylcarbonyl group which may be substituted, an aryisulfonyl group which may be substituted, substituted, a lower N-alkylaminosulfonyl group which may be substituted, a lower N, N-di-alkylaminosulfonyl group which may be substituted, a lower N-lower alkoxy-N-lower alkylsulfonyl group, a lower alkylsulfinyl group, an aryisulfonyl group, an aminosulphinyl group or a five or six membered aromatic heterocyclic ring having one or more heteroatoms selected from the group consisting of nit atoms nitrogen, oxygen and sulfur, the compounds in which R1 represents methyl, R2, R3, R4, and R5, except that which represents at the junction at position 2 in the carbapenem ring, which may be the same or different, respectively represent a hydrogen atom, a lower alkyl group in which one or more hydrogen atoms in the alkyl group may be substituted by groups selected from the group consisting of a halogen atom, a hydroxy group, an amino group, a lower N-alkylamino group, a formylamino group, a lower alkylcarbonylamino group, a carbamoyl group, and a lower alkylsulfonylamino group, an arylthio group, a lower alkylcarbonyl group, in which or several atoms of hydrogen in the alkyl group may be substituted by groups selected from the group consisting of a halogen atom, a hydroxy group, an amino group, a lower alkylcarbonylamino group, a lower N, N-dialkylaminocarbonyl group, a group (N- lower) alkylsulfonyl group, a (N, N-lower dialkylamino) sulfonyl, and an alkylsulfonylamino group lower a ariisulfonilo group substituted by a group alquilaminc lower alkyl group, an N-alkylaminosulfonyl bottom in which one or more hydrogen atoms in the alkyl group can be substituted by groups selected from the group consisting of a lower alkoxy group, a hydrogen atom, and an aryl group (which can be to be substituted by an amino group), an N, N-dialkylaminosulfonyl, a lower alkylsulfinyl group, or a heterocyclic ring aromatic five- or six-membered ring having one or more atoms selected from nitrogen heteroatoms, _ oxygen and sulfur , and the compounds in which _R1 represents a hydrogen atom or a methyl group, R2, R3, R4, and R5, except that which represents the bond at position 2 in the carbapenem ring, which may be the same or different , respectively represent a hydrogen atom, a lower alkyl group, in which one or more hydrogen atoms in the alkyl group can be substituted by groups selected from the group consisting of a halogen atom, a nitro group, a cyan group , a lower cycloalkyl group, a lower alkylthio group, a lower alkoxy group, a hydroxy group, an amino group, a lower N-alkylamino group, a formyl group, an alkylcarbonyl group i nferior, an arylcarbonyl group, a carboxyl group, a lower alkoxycarbonyl group, a formylamino group, a lower alkylcarbonylamino group, a carbamoyl group, a lower-alkylcarbamoyl N, an N, N-di-alkylaminocarbonyl lower, an aminosulfonyl group group, a group (N-lower alkylamino) sulfonyl group, a (N, N-di-lower alkylamino) sulfonyl, a sulfonylamino group, N-lower alkylamino), an aminosulfonylamino group, a sulfonylamino group (N, N-di-lower alkylamino), an alkylsulfonylamino group lower and an aryl group, or an arylthio group. According to the preferred embodiment of the present invention, R preferably represents Ci-io alkyl which may be substituted, arylcarbonyloxy-lower alkyl which may be substituted, an aryl-lower alkoxy-lower alkylcarbonyloxy-lower alkyl group which may be substituted, cycloalkylcarbonyloxy-lower alkyl group which may be substituted, diciclohexilmetilcarboniloxi-alkyl which may be substituted, adamantilcarboniloxi-lower alkyl that may be substituted, lower (lower cycloalkyloxycarbonyloxy) (lower cycloalkyl) methyl which may be substituted, lower cycloalkyl-lower ethoxycarbonyloxy-alkyl may be substituted, adamantyloxycarbonyloxy-lower alkyl which may be substituted, 2-indanyloxycarbonyloxy-lower alkyl which may be substituted, aryl-lower alkyloxycarbonyl-lower alkyl which may be substituted, or 5-inynyloxycarbonyloxy-lower alkyl which may be substituted. According to another preferred embodiment of the present invention, R preferably represents C alkyl -? 0, arilcarbpniloxi-lower alkyl, aryl-lower alkoxy-alkylcarbonyloxy group-lower alkyl, lower cycloalkyl-lower alkylcarbonyloxy-lower alkyl, diciclohexilmetilcarboniloxi- lower alkyl, adamantylcarbonyloxy-lower alkyl, (lower cycloalkyloxycarbonyloxy) (lower cycloalkyl) methyl, lower cycloalkylethoxycarbonyloxy-lower alkyl, adamantyloxycarbonyloxy-lower alkyl, 2-indanyloxycarbonyloxy-lower alkyl, aryl-lower alkyloxycarbonyl-lower alkyl, aryloxycarbonyloxy-lower alkyl wherein the aromatic ring may be substituted, or 5-innyloxycarbonyloxy-lower alkyl. Among them, R preferably represents C? _ Or alkyl, arylcarbonyloxy-lower alkyl, aryl-lower alkyloxy-lower alkylcarbonyloxy-lower alkyl, lower cycloalkylcarbonyloxy-lower alkyl, lower cycloalkyl-lower alkylcarbonyloxy-lower alkyl, dicyclohexylmethylcarbonyloxy-lower alkyl, adamanty-carbonyloxy group -lower alkyl, lower alkylcarbonyloxy-lower alkyl, lower cycloalkyloxycarbonyloxy-lower alkyl, (lower cycloalkyloxycarbonyloxy) (lower cycloalkyl) methyl, lower cycloalkyl-lower alkyloxycarbonyloxy-lower alkyl, adamantyloxycarbhenyloxy-lower alkyl, 2-indanyloxycarbonyloxy-lower alkyl wherein the ring Aromatic may be substituted, lower aryl-alkyloxycarbonyloxy-lower alkyl, aryloxycarbonyloxy-lower alkyl 5-indanyloxycarbonyloxy-lower alkyl wherein the aromatic ring may be substituted. The compound represented by the formula (I) according to the present invention can exist as a salt, and the preferred salt is a pharmacologically acceptable salt. Said salt includes, for example, inorganic salts such as lithium, sodium, potassium, calcium or magnesium salts, an ammonium salt, salts with organic such as triethylamine or diisopropylethylamine, salts with mineral acids such as hydrochloric acid, sulfuric acid, phosphoric acid, or nitric acid, or salts with organic acids such as acetic acid, carbonic acid, citric acid, malic acid, oxalic acid, or methanesulfonic acid, preferably an internal sai, or a sodium or potassium salt. Carbapenem derivatives represented by the formula (I) according to the present invention include, but are not limited to: 1. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2 - (7-propionylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate sodium 2. (1S, 5R, 6S) -6- ((lR) -l -hydroxyethyl) -l-methyl-2- (7-propionylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of pivaloyloxymethyl 3. (1S, 5R, 6 S) -6- ((lR) -l-hydroxyethyl) -2- (7-hydroxyiminomethylimidazo [5, lb] thiazol-2-yl) -1-methyl-1-carbapene-2-em-3-carboxylate sodium (a geometric isomer derived from an initial compound such as a low polarity oxime isomer) 4. (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methoxyiminomethylimidazo [5, 1-b ] thiazol-3-yl) -l-carbapen-2-em-3-carboxylate sodium (a geometric isomer derived from an initial compound as a low polarity oxime isomer) . (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methoxyiminomethylimidazo [5, 1-b] thiazol-3-yl) -l-carbapen-2-em-3-carboxylate from pivaloyloxymethyl (a geometric isomer derived from an initial compound as a low polarity oxime isomer) 6. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7- Sodium pivaloylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate 7. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) - p-L-methyl-2- (7-pivaloylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of pivaloyloxymethyl 8. (5R, 6S) -2- (7- acetyl-3-methylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate sodium 9. (5R, 6S) -2- (7-Acetyl-3-methylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxy-ethyl) -l-carbapen-2- pivaloyloxymethyl-3-carboxylate 10. (SS, 5R, 6S) -2- [7- (2-formylaminopropionyl) imidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1 -hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate sodium (a high polarity isomer) 11. (1S, 5R, 6S) -2- [7- (2-formylaminopropionyl) imidazo [ 5,1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate sodium (a low polarity isomer) 12 (1S, 5R, 6S) -β- ((lR) -l-hydroxyethyl) -2- (7-isobutyrylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em- 3-sodium carboxylate 13. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-isobutyryl idazo [5, 1-b] thiazol-2-yl) -l- pivaloyloxymethyl methyl-l-carbapen-2-em-3-carboxylate 14. (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-propionylimidazo [5, 1-b] thiazole- Sodium 3-yl) -l-carbapen-2-em-3-carboxylate 15. (5R, 6S) -2- (7-acetylimidazo [5, 1-b] thiazol-2-yl) -6- (( 1R) -I-hydroxyethyl) -l-carbapen-2-em-3-carboxylic acid sodium 16. (5R, 6S) -2- (7-acetylimidazo [5, 1-b] thiazol-2-yl) -6 - ((1R) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate of pivaloyloxymethyl 17. (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (Sodium 7-isobutyrylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate 18. (5R, 6S) -6- ((lR) -l-hydroxyethyl) -2- (7-isobutyrylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of pivaloyloxymethyl 19. (S, 5R, 6S) -2- (7-acetyl -5-methylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylic acid sodium 20. (1S, 5R, 6S) -2- (7-acetyl-5-methylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate of pivaloyloxymethyl 21. (SS, 5R, 6S) -2- (7-acetyl-3-methylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em -3-sodium carboxylate 22. (SS, 5R, 6S) -2- (7-acetyl-3-methylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxy -ethyl) -l-methyl-l-carbapen-2-em-3-carboxylate of pivaloyloxymethyl 23. (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, Sodium 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate 24. (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo Sodium [5, 1-b] thiazol-3-yl) -l-carbapen-2-em-3-carboxylate 25. (S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-3-yl) -l-methyl-1-carbapene-2-em-3-carboxylate sodium 26. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfinil imidazq [5, 1-b] thiazol-2-yl) -1-methyl-1-carbapene-2-em-3-carboxylic acid sodium (a mixture of diastereomers) 27. (5R, 6S) -6- (( IR) -1-hydroxyethyl) -2- (7-propionylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid sodium 28. (5R, 6S) -6 - ((IR) -1-hydroxyethyl) -2- (7-propionylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of pivaloyloxymethyl 29. (5R, 6S ) -2- (7-Acetylimidazo [5, 1-b] thiazol-3-yl) -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate of pivaloyloxymethyl 30. ( ÍS, 5R, 6S) -2- (7-ethanesulfonylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em -3-sodium carboxylate 31. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-N-methylsulfamoylimidazo [5, 1-b] thiazole-2 -yl) -l-carbapen-2-em-3-carboxylic acid sodium 32. (5R, 6S) -β- ((IR) -1-hydroxyethyl) -2- (7-N-t-ethyl-sulphamoylimidazo [5, lb ] thiazol-2-yl) -i-carbapen-2-em-3-carboxylic acid sodium 33. (5R, 6S) -2- (7-acetyl-5-methylimidaz [5, lb] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate sodium 34. (5R, 6S) -2- (7-ethansulfonylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate from sodium . (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-p-toluenesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen- Sodium 2-em-3-carboxylate 36. (5R, 6S) -2- (7-hydroxyacetylimidazo [5, lb] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-carbapen -2-em-3-carboxylate sodium. 37. (ΔS, 5R, 6S) -2- (7-benzoylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-1-carbapen-2- sodium em-3-carboxylate 38. (5R, 6S) -2- (7-hydroxyacetylimidazo [5, 1-b] thiazol-3-yl) -6- ((IR) -1-hydroxyethyl) -l-carbapen -2-em-3-carboxylate sodium 39. (5R, 6S) -2- (7-benzoylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate from sodium 40. (1S, 5R, 6S) -2- [7- [N- (4-aminobenzyl) sulfamoyl] imidazo [5, 1-b] thiazol-2-yl] -6- ((IR) -1- sodium hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate 41. (1S, 5R, 6S) -2- (7-Fluoroimidazo [5, 1-b] thiazol-2-yl) - 6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate sodium 42. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- [7- [N- (2-hydroxyethyl) -N-methylsulfamoyl] imidazo [5, 1-b] thiazole-2- il) -1-methyl-l-carbapen-2-em-3-carboxylic acid sodium 43. (1S, 5R, 6S) -2- (7-acetylaminoacetylimidazo [5, 1-b] thiazol-2-yl) - 6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylic acid sodium 44. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonyl-5-methylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylic acid sodium 45. (IS, 5R, 6S ) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfinyl-5-methylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em- 3-sodium carboxylate (a mixture of diastereomers) 46. (SS, 5R, 6S) -2- (7-acetylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1- hydroxy-ethyl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 1- (ethoxycarbonyloxy) ester (a mixture of diastereomers) 47. (SS, 5R, 6S) -2- (7-acetylimidazo [ 5, 1-b] thiazol-2-yl) -6- ((IR) - 1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 1- (isopropoxycarbonyloxy) ethyl ester (a mixture of diastereomers) 48. (1S, 5R, 6S) -2- (7-acetylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2- em-3-carboxylate 1- (cyclohexyloxycarbonyloxy) ethyl (a [lagoon]) 49. (SS, 5R, 6S) -2- (7-acetylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1 -hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylic acid cyclohexyloxycarbonyloxymethyl ester 50 ((S, 5R, 6S) -2- (7-acetylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate 3-phthalidyl (a mixture of diastereomers) 51. (IS, 5R, 6S) -2- (7-Acetylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 1- (acetoxy) ethyl) (a mixture of diastereomers) 52. (1S, 5R, 6S) -2- (7-acetylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) - L-Methyl-l-carbapen-2-em-3-carboxylic acid (5-methyl-2-oxo-l, 3-dioxolen-4-yl) methyl 53. (1S, 5R, 6S) -2- (7 -N-acetylaminomethylimidazo- [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylic acid sodium 54. (1S, 5R, 6S) -2- (7-N-acetylaminomethylimidazo [5, lb] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-ca pivaloyloxymethyl rbapen-2-em-3-carboxylate 55. (1S, 5R, 6S) -2- (7-N-acetylaminomethylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) - 1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 1- (acetoxy) ethyl ester (a mixture of diastereomers) 56. (1S, 5R, 6S) -2- (7-N- acetylaminomethylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 1- (cyclohexyloxycarbonyloxy) ethyl ester ( a mixture of diastereomers) 57. (SS, 5R, 6S) -2- (7-N-acetylaminomethylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l -methyl-l-carbapen-2-em-3-carboxylate 3-phthalidyl (a mixture of diastereomers) 58. (1S, 5R, 6S) -2- (7-N-Acetylaminomethylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-1-carbapen- 2-em-3-carboxylate of (5-methyl-2-oxo-l), 3-dioxoien-4-yl) methyl 59. (1S, 5R, 6S) -2- (7-N-acetylaminomethylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1 -hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 1- [(cyclohexyl ethoxy) carbonyloxy] ethyl ester (a mixture of diastereomers) 60. (IS, 5R, 6S) -2- (7 -N-Acetylaminomethylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate of (IR, 2S , 5R) - (1) -methyloxycarbonyloxymethyl 61. (SS, 5R, 6S) -2- (7-N-acetylaminomethylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1- hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 1- (cyclohexyloxycarbonyloxy) -n-propyl ester (a mixture of diastereomers) 62. (lS, 5R, 6S) -6- ((IR) Sodium-1-hydroxyethyl) -2- (7- methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapene-2-em-3-carboxylate 63. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7- methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate of pivaloyloxymethyl 64. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7- metansu l-phenyl-imidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 1- (acetoxy) ethyl ester (a mixture of diastereomers) 65. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7- methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate of 1- (cyclohexyloxycarbonyloxy) ethyl (a mixture of diastereomers) 66. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7- methanesulfonylimidazo [5, 1-b] thiazole- 2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate 3-phthalidyl (a mixture of -diastereomers) 67. (SS, 5R, 6S) -6- ((IR) -1- hydroxyethyl) -2- (7-methanesulfonyl-imidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate of (5-methyl-2-oxo- 1, 3-dioxolen-4-yl) methyl 68. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazole-2- il) -l-methyl-l-carbapen-2-em-3-carboxylic acid 1- [(cyclohexylmethoxy) carbonyloxy] ethyl ester (a mixture of diastereomers) 69. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonyl-imidazo [5, 1-b] t iazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate of (1-methylcyclohexan-1-yl) carbonyloxymethyl 70. (1S, 5R, 6S) -6- ((IR) -J.-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, lb] thiazol-2-yl) -1-methyl-1-carbapen-2-em -3-carboxylic acid 1- (cyclohexyloxycarbonyloxy) -n-propyl ester (a mixture of diastereomers) 71. (SS, 5R, 6S) -2- (7-hydroxyacetylimidazo [5, 1-b] thiazol-2-yl) - 6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylic acid sodium 72. (SS, 5R, 6S) -2- (7-hydroxyacetylimidazo [5, 1-] b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate of pivaloyloxymethyl 73. (1S, 5R, 6S) -2- (7-hydroxyacetylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 1- (acetoxy) ethyl) (a mixture of diastereomers) 74. (SS, 5R, 6S) -2- (7-hydroxyacetylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) - l-methyl-l-carbapen-2-em-3-carboxylic acid 1- (cyclohexyloxycarbonyloxy) ethyl ester (a mixture of diastereomers) 75. (1S, 5R, 6S) -2- (7-hydroxyacetylimidazo [5, 1-b] ] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl- 3-phthalidyl l-carbapen-2-em-3-carboxylate (a mixture of diastereomers) 76. (1S, 5R, 6S) -2- (7-hydroxyacetylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 5- (methyl-2-oxo-l, 3-dioxolen-4-yl) methyl ester (SS, 5R, 6S) -2- (7-hydroxyacetylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2 -em-3-carboxylate of Q.-methylcyclohexan-1-yl) carbonyloxymethyl 78. (SS, 5R, 6S) -2- (7-hydroxyacetylimidazo [5, 1-b] thiazol-2-yl) -6- ( (IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 1- [(cyclohexylmethoxy) carbonyloxy] ethyl ester (a mixture of diastereomers) 79. (1S, 5R, 6S) - 2- (7-hydroxyacetylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate from 1 (cyclohexyloxycarbonyloxy) -n-propyl (a mixture of diastereomers 80. (SS, 5R, 6S) -2- [7- (N, N-dimethylcarbamoyl) -acetylimidazo [5, 1-b] thiazol-2-yl) - 6- ((IR) -1-hydroxyethyl) -1-methyl-l-carbapen-2-em-3- Sodium carboxylate 81. (1S, 5R, 6S) -2- [7- (N, N-dimethylcarbamoyl) acetylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl ) -l-methyl-l-carbapen-2-em-3-carboxylate of pivaloyloxymethyl 82. (SS, 5R, 6S) -2- [7- (N, N-dimethylcarbamoyl) acetylimidazo [5, 1-b] thiazole -2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate of (1-methylcyclohexan-1-yl) carbonyloxymethyl 83. (SS, 5R , 6S) -2- [7- (N, N-dimethylcarbamoyl) acetylimidazo [5,1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen -2- Em-3-carboxylic acid 1- (cyclohexyloxycarbonyloxy) ethyl ester (a mixture of diastereomers) 84. (1S, 5R, 6S) -2- [7- (N, N-dimethylcarbamoyl) acetylimidazo [5, 1-b] ] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate 3-phthalidyl (a mixture of diastereomers) 85. (SS, 5R, 6S) -2- [7- (N, N-dimethylcarbamoyl) acetylimidazo- [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-1 -carbapen-2-em-3-carboxylate (5-methyl-2-oxo-l, 3-dioxolen-4-yl) methyl 86. (1S, 5R, 6S) -2- [7- (N, N-dimethylcarbamoyl) acetylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl -l-carbapen-2-em-3-carboxylic acid 1- [(cyclohexylmethoxy) carbonyloxy] ethyl ester (a mixture of diastereomers) 87. (1S, 5R, 6S) -2- [7- (N, N-dimethylcarbamoyl) acetylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 1- (cyclohexylcarbonyloxy) - n-propyl (a mixture of diastereomers) 88. (SS, 5R, 6S) -2- [7- (N, -dimethylsulfamoyl) imidazo [5, 1-b] thiazol-2-yl) -6- ((IR Sodium 1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate 89. (SS, 5R, 6S) -2- [7- (N, N-dimethylsulfamoyl) imidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxy-pivaloyloxymethyl 90. (1S, 5R, 6S) -2- [7- (N, N-dimethylsulfamoyl) imidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3 - (1-methylcyclohexan-1-yl) carbonyloxymethylcarboxylate 91. (SS, 5R, 6S) -2- [7- (N, -dimethylsulfamoyl) imidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 1- (cyclohexyloxycarbonyloxy) ethyl ester (a mixture of diastereomers) 92. (SS, 5R, 6S) -2- [7- (N, N-dimethylsulfamoyl) imidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) 3-phthalidyl-l-methyl-l-carbapen-2-em-3-carboxylate (a mixture of diastereomers) 93. (1S, 5R, 6S) -2- [7- (N, N-dimethylsulfamoyl) imidazo [ 5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate of (5-methyl-2-oxo- 1, 3-dioxolen-4-yl) methyl 94. (SS, 5R, 6S) -2- [7- (N, N-dimethylsulfamoyl) imidazo [5, 1-b] thiazol-2-yl] - 6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 1- [(cyclohexylmethoxy) carbonyloxy] ethyl ester (a mixture of diastereomers) 95. (SS, 5R, 6S) -2- [7- (N, N-dimethylsulfamoyl) imidazo [5, 1-b] thiazol-2-yl] -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen- 2-em-3-carboxylic acid 1- (cyclohexyloxycarbonyloxy) n-propyl ester (a mixture of diastereomers) 96. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methoxycarbonylimidazo [5, 1-b] thiazol-2-yl) -1-methyl-l-carbapen-2-em-3-carboxylic acid sodium 97. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- [7- (N-methoxy-N-methylsulfamoyl) imidazo [5, 1-b] thiazol-2-yl] Sodium-1-methyl-l-carbapen-2-em-3-carboxylate 98. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-trifluoroacetylimidazole) [5, 1-b] thiazol-2-yl] -l-carbapen-2-em-3-carboxylic acid sodium 99. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l Sodium methyl-2- (7-sulfamoylimidazo [5, 1-b] thiazol-2-yl] -l-carbapen-2-em-3-carboxylate 100. (1S, 5R, 6S) -6- (( lR) -l-hydroxyethyl) -2- [7- (2- (E) -methoxycarbonylvinyl) imidazo [5, 1-b] thiazol-2-yl] -1-methyl-l-carbapen-2-em-3 sodium carboxylate 101. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- [7- (2- (Z) -methoxycarbonylvinyl) imidazo [5, 1-b] thiazole- 2-yl] -1-methyl-l-carbapen-2-em-3-carboxylate sodium 102. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- [7- (thiazol-4-yl) imidazo [5, 1-b] thiazol-2-yl] -l-carb sodium apen-2-em-3-carboxylate 103.. (1S, 5R, 6S) -2- (7-hydroxyacetyl-5-methylimidazo [5, 1-b] thiazol-2-yl] -6- ((IR) -1-hydroxyethyl) -l-methyl-l- sodium carbapen-2-em-3-carboxylate 104. (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonyl-5-ethylimidazo [5, 1-b] thiazole- 2-yl] -l-carbapen-2-em-3-carboxylic acid 105. (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfinyl-5-methylimidazo [5 , 1-b] thiazol-2-yl] -l-carbapen-2-em-3-carboxylate 106. (5R, 6S) -2- (7-hydroxyacetyl-5-methylimidazo [5, 1-b] thiazol-2-yl] -6- ((IR) -1-hydroxy-ethyl) -l-carbapen-2-em-3-carboxylate sodium 107. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonyl-5-methylimidazo [5, 1-b] thiazol-2-yl] -l-methyl-l-carbapen-2-em-3-carboxylate of pivaloyloxymethyl 108. ( 1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylaminoacetylimidazo [5, 1-b] thiazol-2-yl] -1-methyl-l-carbapen-2-em Sodium -3-carboxylate 109. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (5-methyl-7-methylthioimidazo [5, lb] thiazole-2 -il] -l-carbapen- Sodium 2-em-3-carboxylate 110. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- [7- (methanesulfonylaminomethyl) imidazo [5, 1-b] thiazole-2 sodium-1-methyl-l-carbapen-2-em-3-carboxylate 111. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- ( Sodium 7- ethylthioimidazo [5, lb] thiazol-2-yl] -l-carbapen-2-em-3-carboxylate 112. (5R, 6S) -2- (7-dimethylaminosulfonyl-imidazo [5, 1-b] ] thiazol-2-yl] -6- ((IR) -1-hydroxy-ethyl) -l-carbapen-2-em-3-carboxylic acid sodium 113. (5R, 6S) -2- (7-aminosulfonylimidazo [ 5, 1-b] thiazo? -2-yl) -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate sodium 114. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- [7- ((E) -3-oxo-1-buten-1-yl) imidazo [5, Sodium 1-b] thiazol-2-yl] -l-carbapen-2-em-3-carboxylate 115. (1S, 5R, 6S) -2- (7-formyl-5-methylimidazo [5, 1-b] ] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylic acid sodium 116. (5R, 6S) -6- ((lR ) -l-hydroxyethyl) 2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate sodium 117. (5R, 6S) -6- ( (IR) -1-hydroxyethyl) -2- (7-methansulfinylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid sodium (a mixture of diastereomers) 118. (5R, 6S) -2- [7- (N, N-dimethylaminosulfonylamino) acetylimidazo [5, 1-b] thiazol-2-yl] -6- ((IR) -1-hydroxyethyl) -l-carbapen-2 sodium em-3-carboxylate 119. (1S, 5R, 6S) -2- [7- (N, N-dimethylaminosulfonylamino) acetylimidazo [5, lb] thiazol-2-yl] -6- ((IR) - Sodium 1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate 120. (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (5-methyl-7 -methylthioimidazo [5, 1-b] thiazol-2-yl] sodium l-carbapen-2-em-3-carboxylate 121. (SS, 5R, 6S) -2- (7-aminoacetylimidazo [5, lb] thiazol-2-yl] -6- ((IR) -1 sodium-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate 122. (SS, 5R, 6S) -2- (7-aminomethylimidazo [5, 1-b] thiazol-2-yl] -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylic acid sodium 123. (SS, 5R, 6S) -2- [7- (2-aminoethanesulfonylamino) acetylimidazo [5, lb] thiazol-2-yl] -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate sodium 124. (5R, 6S) - 2- [7- (2-aminoethanesulfonylamino) acetylimidazo [5, 1-b] thiazol-2-yl] -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate sodium 125. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (5-methanesulfonylimidazo [5, lb] thiazol-2-yl) -l-methyl-l-carbapen-2- sodium em-3-carboxylate 126. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (5-methylthioimidazo [5, 1-b] thiazole-2- il) -l-carbapen-2-em-3-carboxylic acid sodium 127. (1S, 5R, 6S) -2- [5,7-bis (methylthio) imidazo [5, 1-b] thiazol-2-yl) ] -6- ((IR) -1-hid sodium roxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate 128. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7 sodium phenylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate 129. (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2 - (sodium 7-methylthioimidazo [5, 1-b] thiazol-3-yl) -l-carbapen-2-em-3-carboxylate 130. (5R, 6S) -6- ((IR) -1-hydroxyethyl ) -2- (7-phenylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate sodium 131. (SS, 5R, 6S) -6- ((IR ) -1- hydroxyethyl) -l-methyl-2- (3-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate, sodium 132. (1S, 5R , 6S) -2- (7-ethylthioimidazo- [5, 1-b] thiazol-2-i1) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3 sodium carboxylate 133. (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (3-methylthioimidazo [5, 1-b] thiazol-2-yl) -carbapen-2-em- 3-sodium carboxylate 134. (5R, 6S) -2- (7-ethylthioimidazo [5, lb] thiazol-2-yl) -6- ((1R) -1-hydroxyethyl) -l-carbapen-2-em Sodium carboxylate 135. (5R, 6S) -6- ((I R) -1-hydroxyethyl) -2- (3-methyl-7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate sodium 136. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfinyl-5-ethylthioimidazo [5, 1-b] thiazol-2-yl) -l-methyl-1-carbapen-2 sodium-3-carboxylate (a mixture of diastereomers) 137. (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (3-hydroxymethyl-7-? r_ethylthi__ > imidazo [5, l ~ b] tia¿.ol-2- ~ ii. -I-Cd.rbapen-2-em-3-carboxylate sodium 138. (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (3-phenylimidazo [5, 1-b] thiazole -2-yl) -l-carbapen-2-em-3-carboxylate sodium 139. (5R, 6S) -2- (7-aminoacetylimidazo [5, lb] thiazol-2-yl) -6- ((IR Sodium-1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate 140. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (5-methanesulfinylimidazo [5, 1-b] thiazol-2-yl] -l-methyl-l-carbapen-2- sodium em-3-carboxylate (a mixture of diastereomers) 141. (SS, 5R, 6S) -2- (5,7-dimethanesulfinyl-imidazo [5, 1-b] thiazol-2-yl] -6 - ((lR) -1-hydroxy-ethyl) -l-methyl- sodium l-carbapen-2-em-3-carboxylate (a mixture of diastereomers) 142. (1S.5R, 6S) -β- ((IR) -1-hydroxyethyl) -2- (5-methanesulfinyl-7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl] -l-methyl-l-carbapen-2 sodium em-3-carboxylate (a mixture of diastereomers) 143. (SS, 5R, 6S) -2- [5,7-bis (methanesulfonyl) imidazo [5, 1-b] thiazol-2-yl] -6 - ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate sodium 144. (5R, 6S) -2- (3-aminomethylimidazo [5, lb] thiazole-2 -yl) -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylic acid sodium 145. (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2 - (3-hydroxymethylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid sodium 146. (5R, 6S) -2- [5,7-bis (methylthio ) -imidazo [5, 1-b] thiazol-2-yl] -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate sodium 147. (SS.5R, 6S) -2- (5-acetyl-7-methylthioimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l- sodium carbapen-2-em-3-carboxylate 148. (1S, 5R, 6S) -2- [3, 7-bis (methylthio) -imidazo [5, 1-b] thiazol-2-yl] -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylic acid sodium 149. (SS, 5R, 6S) -2- (5-acetyl-7-methanesulfonimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate sodium 150. (SS, 5R, 6S) - 2- (5-bromo-7-methylthioimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3 sodium carboxylate 151. (5R, 6S) -2- (5-acetyl-7-methylthioimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-carbapen -2-Sodium 3-carboxylate 152. (SS, 5R, 6S) -2- (5-cyano-7-methylthioimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) Sodium 1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate 153. (5R, 6S) -2- [3,7- bis (methylthio) imidazo [5, lb] thiazole- 2-yl] -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate or sodium 154. (SS, 5R, 6S) -2- (5-Chloro-7-methylthioimidazo [5, 1-b] thiazol-2-yl] -6- ((IR) -1-hydroxyethyl) -l-methyl-l- sodium carbapen-2-em-3-carboxylate 155. (5R, 6S) -2- (5-cyano-7-methylthioimidazo [5, 1-b] thiazol-2-yl] -6- ((IR) - Sodium 1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate 156. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-? Aethyl-2- [7- (1-propyl) thioimidazo [5, 1-b] thiazol-2-yl] sodium l-carbapen-2-em-3-carboxylate 157. (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7- (1-propyl) thioimidazo [5, 1- b] thiazol-2-yl] -l-carbapen-2-em-3-carboxylate sodium 158. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-isopropylthioimidazo [5, 1-b] thiazol-2-yl] -l-methyl-l-carbapen-2-em-3-carboxylic acid sodium 159. (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-isopropylthioimidazo [5, 1-b] thiazol-2-yl] -l-carbapen-2-em-3-carboxylic acid sodium 160. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonyl-5-methylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 1-methylcyclohexylcarbonyloxymethyl ester 161 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonyl-5-methylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-1 -carbapen-2-em-3-carboxylic acid 1- (cyclohexyloxyparabanyloxy) ethyl ester (a mixture of diastereomers) 162. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7- m 5-methylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylic acid cyclohexyloxycarbonyloxymethyl ester (5S, 5R, 6S) -6- (( IR) -1-hydroxyethyl) -2- (7-methansul fonyl-5-methyl-imidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate of 3-phthalidyl (a mixture of diastereomers) 164. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonyl-5-methylimidazo [5, 1-b] thiazol-2-yl] -l-methyl-1 -carbapen-2-em-3-carboxylic acid 5-methyl-2-oxo-l, 3-dioxolen-4-ylmethyl 165. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) - 2- (7-methanesulfonyl-5-methylimidazo [5, 1-b] thiazol-2-yl] -l-methyl-l-carbapen-2-em-3-, carboxylate of (Z) -2- (3- phthalidilidene) ethyl 166. (SS, 5R, 6S) -2- (7-acetyl-5-methylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l -methyl-l-carbapen-2-em-3-carboxylic acid 1- (ethoxycarbonyloxy) ethyl ester (a mixture of diastereomers) 167. (SS, 5R, 6S) -2- (7-acetyl-5-methylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 1- (cyclohexyloxycarbonyloxy) ethyl ester (a mixture of diastereomers ) 168. (1S, 5R, 6S) -2- (7-Acetyl-5-methylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl Cyclohexyloxycarbonyloxymethyl-l-carbapen-2-em-3-carboxylate 169. '(1S, 5R, 6S) -2- (7-acetyl-5-methylimidazo [5, 1-b] thiazole -2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate 3-phthalidyl (a mixture of diastereomers) 170. (SS, 5R, 6S) -2- (7-acetyl-5-methylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l- 5-methyl-2-oxo-l, 3-dioxolen-4-ylmethyl carbapen-2-em-3-carboxylate 171. (SS, 5R, 6S) -2- (7-acetyl-5-methylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate of (cyclopentyloxycarbonylcximeyl 172. (1S, 5R, 6S ) -2- (7-Acetylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate from 1- (pivaloyloxy) ethyl (a mixture of diastereomers) 173. (1S, 5R, 6S) -2- (7-acetylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1 -hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 1-methylcyclohexylcarbonyloxymethyl ester 174. (1S.5R, 6S) -2- (7-acetylimidazo [5, 1-b] thiazole-2-) il) -6-. { (IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylic acid cyclohexycarbonyloxymethyl 175. (SS, 5R, 6S) -2- (7-acetylimidazo [5, 1-b] thiazole -2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 1- (cyclohexylcarbonyloxy) ethyl ester (a mixture of diastereomers) 176. (1S 5R, 6S) -2- (7-acetylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3 hexanoyloxymethylcarboxylate 177. (1S, 5R, 6S) -2- (7-acetylimidazo [5, 1-b] t? azol-2-yl) -6- ((IR) -1-hydroxyethyl) -l- methyl-l-carbapen-2-em-3-carboxylate from 2-Ethylbutyryloxymethyl 178. (1S, 5R, 6S) -2- (7-Acetylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-1 Cyclopentyloxycarbonyloxymethylcarbapene-2-ene-3-carboxylate 179. (1S, 5R, 6S) -2- (7-acetylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1 -hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 1- (3-pentyloxycarbonyloxy) ethyl ester (a mixture of diastereomers) 180. (1S, 5R, 6S) -2- (7-acetylimidazole) [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate from 3-pentyloxycarbonyloxymethyl 181. (1S, 5R, 6S) -2- (7-acetylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-1 Cyclohexylmethoxycarbonyloxymethylcarbapene-2-ene-3-carboxylate 182. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7- v. methanesulfonylimidazo [5, 1-b] ] thiazol-2-yl] -l-methyl-l-carbapen-2-em-3-carboxylic acid 1- (isobutyryloxy) ethyl ester (a mixture of diastereomers) 183. (1S, 5R, 6S) -6- (( IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 1- (pivaloyloxy) ethyl ester (a mixture of diastereomers) 1.84 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, lb] thiazol-2-yl) -l- methyl-l-carbapen-2-em-3-carboxylic acid hexanoyloxy ethyl 185. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonyl-imidazo [5,1] -b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate of cyclohexylcarbonyloxymethyl 186. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2 - (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) Cyclohexylacetoxymethyl-l-methyl-l-carbapen-2-em-3-carboxylate 187. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonyl-imidazo [5 , Dicyclohexylacetoxymethyl, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-ene-3-carboxylate 188. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (1- (1-methylcyclohexylcarbonyloxy) ethyl (a mixture of diastereomers) -2- (7-methanesulfonylimidazo [5, lb] thiazol-2-yl) -1-methyl-1-carbapen-2-em-3-carboxylate 189 (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonyl-imidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen -2-em-3-carboxylate of .1-adamantylcarbonyloxymethyl 190. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonyl-imidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 1- (1-adamantylcarbonyloxy) ethyl ester (a mixture of diastereomers) 191. (1S, 5R, 6S) -6- ( (IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 1- (benzoyloxy) ester ethyl (a mixture of diastereomers os) 192. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonyl-imidazo [5, 1-b] thiazol-2-yl) -l-methyl- 4- (2-propyl) benzoyloxymethyl l-carbapen-2-em-3-carboxylate 193. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonyl-imidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 4-n-butylbenzoyloxymethyl ester 194. (1S, 5R, 6S) -6- ((IR ) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl] -l-methyl-l-carbapen-2-em-3-carboxylic acid 4-phenylbenzoyloxymethyl ester 195. ( ÍS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonyl-imidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2 4-butylbenzoyloxymethyl-ene-3-carboxylate 196. (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonyl-imidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2- 1- (4-t-butylbenzoyloxy) ethyl em- 3-carboxylate (a mixture of diastereomers) 197. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7 -methansulfonyl-imidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 2,4,6-trimethylbenzoyloxymethyl 198. (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonyl-imidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate 1- (2-propyloxycarbonyloxy) ethyl (a mixture of diastereomers) 199 .. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonyl-imidazo [5,1] -b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 1- (2-butyloxycarbonyloxy) ethyl ester (a mixture of diastereomers) 200. (1S, 5R, 6S) - 6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonyl-imidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate from 1- (3-pentyloxycarbonyloxy) ethyl (a mixture of diastereomers) 201. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonyl-imidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3 1- (1-butyloxycarbonyloxy) ethyl carboxylate (a mixture of diastereomers) 202. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonyl-imidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 4-heptyloxycarbonyloxymethyl ester 203. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl ) -2- (7-methanesulfonyl-imidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 1- (4-heptyloxycarbonyloxy) ethyl ester (a mixture of diastereomers) 204. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonyl-imidazo [5, 1-b] thiazol-2-yl) -l- methyl 1- l-carbapen-2-em-3-carboxylic acid 1- (1-pentyloxycarbonyloxy) ethyl ester (a mixture of diastereomers) 205. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) - 2- (7-Methanesulfonylimidazo [5, lb] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 1- (4-methyl-1-pentyloxycarbonyloxy) ethyl ester (a mixture of diastereomers) 206. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonyl-imidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate of 5-nonyloxycarbonyloxymethyl 207. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonyl-imidazo [5, 1-b] thiazol-2-yl) -l- methyl (l-carbapen-2-em-3-carboxylic acid 1- (5-nonyloxycarbonyloxy) ethyl ester (a mixture of diastereomers) 208. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) - 2- (2, 2-dimethyl-l-propyloxycarbonyloxy) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl] -l-metii-l-carbapen-2-em-3-carboxylic acid ethyl ester (a mixture of diastereomers) 209. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl] -l-methyl-l-carbapen-2- 3- (3, 3-dimethyl-2-butyloxycarbonyloxy) ethyl em- 3-carboxylate (a mixture of diastereomers) 210. (SS, 5R, 6S) -6- ((IR) -l-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -1-methyl-l-carbapen-2-em-3-carboxylic acid cyclohexylmethoxycarbonyloxymethyl ester 211. (SS, 5R, 6S) -6- ((IR ) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 1- (cyclohexylmethoxycarbonyloxy) -1 -propyl (a mixture of diastereomers) 212. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) - 1-Methyl-l-carbapen-2-em-3-carboxylic acid 1- (dicyclohexylmethoxycarbonyloxy) ethyl ester (a mixture of diastereomers) 213. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) - 2- (7-methanesulfonyl-imidazo [5, lb] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylic acid cyclohexyloxycarbonyloxymethyl ester 214. (SS, 5R, 6S) -6- ( (IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, lb] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 1- (cyclohexyloxycarbonyloxy-2-) methyl-1-propyl (a mixture of diastereomers) 21J (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl ) -l-methyl-l-carbapen-2-em-3-carboxylic acid cyclohexyl (cyclohexyloxycarbonyloxy) methyl ester (a mixture of diastereomers) 216. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -I-methyl-l-carbapen-2-em-3-carboxylate of (IR, 2S, 5R) - (1) -methyloxycarbonyloxymethyl 217. (1S, 5R, 6SV6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, lb] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate of 1- ((IR, 2S, 5R) - (1) -methyloxycarbonyloxy) -ethyl (a mixture of diastereomers) 218. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate of (SS, 2R, 5S) - (d) -methyloxycarbonyloxymethyl 219. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2 emulsified 3-carboxylate of (SS, 2E, 5R) -isoxy-ethyloxycarbonyloxymethyl 220. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2- (S, 2S, 5R) -neomethyloxycarbonyloxymethyl-3-carboxylate 221. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2- 3,3,5,5-tetramethylcyclohexyloxycarbonyloxymethyl ether-3-carboxylate 222. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methansuifonii-imidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 2-adamantyloxycarbonyloxymethyl ester 223. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl ) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylic acid of 1- ((indan-2-yl) oxycarbonyloxy) ethyl (a mixture of diastereomers) 224.- (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methanesulfonylimidazo [5, 1-b] thiazole-2 -l) -l-carbapen-2-em-3-carboxylic acid 1- (2-methylphenoxycarbonyloxy) ethyl ester (a mixture of diastereomers) 225. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl ) -l-methyl-2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl] -l-carbapen-2-em-3- carboxylic acid 1- (2-ethylphenoxycarbonyloxy) ethyl ester (a mixture of diastereomers) 226. (SS, 5R, 6S) -6- ((IR) -1 -hydroxyethyl) -l-methyl-2- (7- ethansulfonylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 1- (3-methylphenoxycarbonyloxy) ethyl ester (a mixture of diastereomers) 227. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) - 1- (4-methylphenoxycarbonyloxy) ethyl l-carbapen-2-em-3-carboxylate (a mixture of diastereomers) 228. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l- Methyl-2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 1- (2,6-dimethylphenoxycarbonyloxy) ethyl ester (a mixture of diastereomers) 229. (1S, 5R, 6S) -6- ((IRL-l-hydroxyethyl) -l-methyl-2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl] -l-carbapen-2-em-3-carboxylic acid 1- (2,4-dimethylphenoxycarbonyloxy) ethyl ester (a mixture of diastereomers) 230. (1S, 5R, 6S) - 6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methanesulfonylimidazo [5, lb.] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate from 1 (3,5-dimethylphenoxycarbonyloxy) ethyl (a mixture of diastereomers) 231. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazole -2-) -l-methyl-l-carbapen-2-em-3-carboxylic acid 1- (2,, 6-trimethylphenoxycarbonyloxy) ethyl ester (a mixture of diastereomers) 232. (1S, 5R, 6S) -6 - ((IR) -1-hydroxyethyl) -2- (7- ethansulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate from 1- ( 4-t-butylphenoxycarbonyloxy) ethyl (a mixture of diastereomers) 233. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methanesulfonylimidazo [5, lb] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of (indan-5-yl) oxycarbonyloxymethyl 234. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2 - (7-methanesulfonylimid azo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 1- ((Indan-5-yl) oxycarbonyloxy) ethyl ester (a mixture of diastereomers) 235. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-ethanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-1-carbapen- 2-Em-3-carboxylic acid 1- ((Indan-5-yl) oxycarbonyloxy) -1-propyl ester (a mixture of diastereomers) 236. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl ) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylic acid ethyl ester 237. (1S, 5R, 6S) -6 - ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 2-propyl ester 238. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-1-carbapen- 2-Em-3-carboxylic acid 1-decyl 239. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonyl-imidazo [5, 1-b] thiazole- 2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate of (Z) -2- (3-phtalidylene) ethyl 240. (SS, 5R, 6S) -6- ((IR) - 1-hydr oxyethyl) -l-methyl-2- (7-methylthioimidazo- [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid acetoxymethyl ester 241. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo- [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of 1- (acetoxy) ethyl (a mixture of diastereomers) 242. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo- [5, 1-] b] thiazol-2-yl] -l-carbapen-2-em-3-carboxylic acid 1- (isobutyryloxy) ethyl ester (a mixture of diastereomers) 243. (1S, 5R, 6S) -6- ((IR) - 1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo- [5, 1-b] thiazol-2-yl] -l-carbapen-2-em-3-carboxylate of pivaloyloxymethyl 244. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo- [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3 1- (pivaloyloxy) ethyl carboxylate (a mixture of diastereomers) 245. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo- [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 2-ethylbutyryloxymethyl ester 246. (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate 1- (2-ethylbutyryloxy) ethyl (a mixture of diastereomers) 247. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid cyclohexylcarbonyloxymethyl ester 248. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl- 2- (7-Methylthio-imidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 1- (cyclohexylcarbonyloxy) ethyl ester (a mixture of diastereomers) 249. (1S , 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthio-imidazo [5, 1-b] thiazol-2-yl] -l-carbapen-2- dicyclohexylacetoxymethyl ether-3-carboxylate 250. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthio-imidazo [5, 1-b] thiazole- 2-yl] -l-carbapen-2-em-3-carboxylic acid 1-adamantylcarbonyloxymethyl 251. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7 -methylthio-imidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of 1- (1-ad) amylcarbonyloxy) ethyl (a mixture of diastereomers) 252. (1S.5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3 3-phthalidyl carboxylate (a mixture of diastereomers) 253. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo- [5, 1-b ] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid benzoyloxymethyl 254. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- ( 7-Methylthioimidazo- [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 1- (benzoyloxy) ethyl ester (a mixture of diastereomers) 255. (1S, 5R, 6S ) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo- [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of 2-methylbenzoyloxymethyl 256. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthio-imidazo [5, 1-b] thiazol-2-yl ) -l-carbapen-2-em-3-carboxylic acid 1- (2-methylbenzoyloxy) ethyl ester (a mixture of diastereomers) 257. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-ethylthioi idazo- [5, 1-b] thiazol-2-yl) -l-carbapen- 4-Methylbenzoyloxymethyl 2-em-3-carboxylate 258. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthia-imidazo [5, 1-] b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate from 4- (2-propyl) benzoyloxymethyl 259. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthio-imidazo [5, 1-b] thiazole -2-yl) -l-carbapen-2-em-3-carboxylic acid 2,4-dimethylbenzoyloxymethyl 260. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2 - (2,4-trimethylbenzoyloxymethyl 2,61 (1S, 5R, 6S) -6- (7-methylthio-imidazo [5, l-bltiazol-2-yl) -l-carbapen-2-em-3-carboxylate] ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthio-imidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate from 1 (benzyloxyacetoxy) ethyl (a mixture of diastereomers) 262. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthio-imidazo [5, 1-b ] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 1- (ethoxycarbonyloxy) ethyl ester (a mixture of diastereomers) 263. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthio-imidazo [5, 1-b] thiazol-2-yl) -l-carbapen- 2-propyloxycarbonyloxymethyl 2-em-3-carboxylate 264. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthio-imidazo [5, 1-] b) thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 1- (2-propyloxycarbonyloxy) ethyl ester (a mixture of diastereomers) 265. (SS, 5R, 6S) -6- ((IR 1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 1- (2-propyloxycarboxy? i.sub.oxi) -1-propyl (a mixture of diastereomers) 266. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b ] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 2-methyl-1- (2-propyloxycarbonyloxy) -1-propyl a mixture of diastereomers) 267. (SS, 5R, 6S) - 6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthio-imidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate from 1- (1-propyloxycarbonyloxy) ethyl (a mixture of diastereomers) 268. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthio-imidazo [5 3-pentyloxycarbonyloxymethyl, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate 269. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l -methyl-2- (7-methylthio-imidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 1- (3-pentyloxycarbonyloxy) ethyl ester (a mixture of diastereomers 270. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthio-imidazo [5, 1-b] thiazol-2-yl) -l -carbapen-2-em-3-carboxylic acid 1- (1-butyloxycarbonyloxy) ester (a mixture of diastereomers) 271. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthio-imidazo [5, 1-b] thiazol-2-yl) -l-carbapen- 4-heptyloxycarbonyloxymethyl 2-em-3-carboxylate 272. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthio-i idazo [5,1] -b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 1- (4-heptyloxycarbonyloxy) ethyl ester (a mixture of diastereomers) 273. (1S, 5R, 6S) -6- (( IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 1- (3-methyl) -l-butyloxycarbonyloxy) ethyl (a mixture of diastereomers) 274. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5,1] -b] thiazole-2-ii? i-carbapen-2-em-3-carboxylate 1- (1-pentyloxycarbonyloxy) ethyl (a mixture of diastereomers) 275. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5,1] -b] thiazol-2-yl] -l-carbapen-2-em-3-carboxylic acid 1- (4-methyl-1-pentyloxycarbonyloxy) ethyl ester (a mixture of diastereomers) 276. (SS, 5R, 6S) - 6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthiO-i idazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of 5-nonyloxycarbonyloxymethyl 277. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7- ethylthioimidazo [5, 1-b] thiazol-2-yl) - 1- [3- (2,4-dimethyl) pentoxycarbonyloxy) ethyl l-carbapen-2-em-3-carboxylate (a mixture of diastereomers) 278. (SS, 5R, 6S) -6- ((IR) - 1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, lb] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of 1- (2, 2-dimethyl-l-propyloxycarbonyloxy) ethyl (a mixture of diastereomers) 279. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5 , 1-b] thiazol-2-yl] -l-carbapen-2-em-3-carboxylic acid 1- (3, 3-dimethyl-2-butyloxycarbonyloxy) ethyl ester (a mixture of diastereomers) 280. (SS, 5R , 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3 1- (2-cyclohexyl-l-ethyloxycarbonyloxy) ethyl carboxylate (a mixture of diastereomers) 281. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7 5- (2-phenyl-1-ethyloxycarbonyloxy) ethyl (a mixture of diastereomers) -methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate 282. (IS , 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2- cyclohexyloxycarbonyloxymethyl ether-3-carboxylate 283. (S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazole-2 -yl) -l-carbapen-2-em-3-carboxylate 1- (cyclohexyloxycarbonyloxy) ethyl (a mixture of diastereomers) 284. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b ] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 1- (cyclohexyloxycarbonyloxy) -1-propyl ester (a mixture of diastereomers) 285. (1S, 5R, 6S) -6- ((IR 1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 1- (cyclohexyloxycarbonyloxy) -2 methyl-1-propyl (a mixture of diastereomers) 286. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-] b] thiazol-2-yl] -l-carbapen-2-em-3-carboxylic acid cyclohexyl (cyclohexyloxycarbonyloxy) ethyl ester (a mixture of diastereomers) 287. (1S, 5R, 6S) -6- ((IR) -1 -hydroxyethyl) -l-methyl-2- (7-methylthio-imidazo [5, 1-b] thiazol-2-yl] -l-carbapen-2-em-3-carboxylate from 2-adamantyloxycarbonyloxymethyl 288. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl] -l Phenoxycarbonyloxymethylcarbapene-2-ene-3-carboxylate 289. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5,1] -b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 1- (phenoxycarbonyloxy) ethyl ester (a mixture of diastereomers) 290. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthio-imidazo [5, 1-b] thiazol-2-yl) -l-carbapen- 2-Em-3-carboxylic acid 1- (phenoxycarbonyloxy) -1-propyl ester (a mixture of diastereomers) 291. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2 - (7- (2-methylthioimidazo [5, 1-b] thiazol-2-yl] -l-carbapen-2-em-3-carboxylic acid 1- (2-methylphenoxycarbonyloxy) ethyl ester (a mixture of diastereomers) 292. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7- ethylthioimidazo [5, 1-b] thiazol-2-yl] -l-carbapen-2-em-3 1- (2-ethylphenoxycarbonyloxy) ethyl carboxylate (a mixture of diastereomers) 293. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-ethylthioimidazo [ 5, lb] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 1- (2-methoxyphenoxycarbonyloxy) ethyl ester (a mixture of diastereomers) 294. (SS, 5R, 6S) -6- { (IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate from 1- ( 3-methylphenoxycarbonyloxy) ethyl (a mixture of diastereomers) 295. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen- 2-Em-3-carboxylic acid 1- (3-methoxyphenoxycarbonyloxy) ethyl ester (a mixture of diastereomers) 296. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-Methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 1- (4-methylphenoxycarbonyloxy) ethyl ester (a mixture of diastereomers) 297. (1S, 5R , 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl] -l-carbapen-2-em-3 1- (4-ethylphenoxycarbonyloxy) ethyl carboxylate (a mixture of diastereomers) 298. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5 , 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 1- (4-methoxyphenoxycarbonyloxy) ethyl ester (a mixture of diastereomers) 299. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl] -l-carbapen-2-em-3-carboxylate of 1- (2, 6-dimethylphenoxycarbonyloxy) ethyl (a mixture of diast eryomers) 300. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l- carbapen-2-em-3-carboxylic acid 1- (2,4-dimethylphenoxycarbonyloxy) ethyl ester (a mixture of diastereomers) 301. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l- Methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 1- (2,5-dimethylphenoxycarbonyloxy) ethyl ester (a mixture of diastereomers) 302. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen- 2-Em-3-carboxylic acid 1- [2-methyl-5- (2-propyl) phenoxycarbonyloxy] -ethyl ester (a mixture of diastereomers) 303. (1S, 5R, 6S) -6- ((IR) -1 -hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 1- (3,5-dimethylphenoxycarbonyloxy) ethyl ester (a mixture of diastereomers) 304. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl ) -l-carbapen-2-em-3-carboxylate 1- (2, 4, 6-trime) tylphenoxycarbonyloxy) ethyl (a mixture of diastereomers) 305. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazole- 2-yl] -l-carbapen-2-em-3-carboxylic acid 1- ((Indan-5-yl) oxycarbonyloxy) ethyl ester (a mixture of diastereomers) 306. (SS, 5R, 6S) -6- (( IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of 1- ((Indan- 5-yl) oxycarbonyloxy) -1-propyl (a mixture of diastereomers) 307. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-ethylthioimidazo [5 , 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 1-heptyl 308. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l -methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl] -l-carbapen-2-em-3-carboxylic acid 5-methyl-2-oxo-l, 3-dioxolen-4-methylmethion 309. (1S, 5R, 6S ) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate from (Z) -2- (3-phthallylidene) ethyl 310. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b ] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 1- (1,1-dimethyl-l-butyloxycarbonyloxy) ethyl ester (a mixture of diastereomers) 311. (1S, 5R, 6S) - 6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl] -l-carbapen-2-em-3-carboxylate from 1 (3, 3-dimethyl-l-butyloxycarbonyloxy) ethyl (a mixture of diastereomers) 312. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methyl) [1, 2-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 1- (2-methoxybenzoyloxy) ethyl ester (a mixture of diastereomers) 313. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthio-imidazo [5, 1-b] thiazol-2-yl) -l-carbapen- 3, 5-dimethylbenzoyloxymethyl 2-em-3-carboxylate 314. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 1- [2- (2-propyl) phenoxycarbonyloxy] ethyl ester (a mixture of diastereomers) 315. (1S, 5R, 6S ) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7- ethylthioimidazo [5, lb] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of (2) , 2-dimethyl-1-propyloxycarbonyloxy) methyl 316. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-ethylthioimidazo [5, 1-b ] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 1- (2-ethyl-1-butyloxycarbonyloxy) ethyl ester (a mixture of diastereomers) 317. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of 1- (3 -methyl-l-butyloxycarbonyloxy) -1-propyl (a mixture of diastereomers) 318. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) L-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 1- (2,6-dimethylphenoxycarbonyloxy) 319. ( 1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em -3-carboxylic acid 1- (2, 3, 5-trimethylphenoxycarbonyloxy) ethyl ester (a mixture of diastereomers) 320. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2 2-Naphthylcarbonyloxymethyl-7-methylthio-imidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate 321. (SS, 5R, 6S) -6- (( IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthio-imidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate from 2,5-dimethylbenzoyloxymethyl 322. (SS, 5R, 6S) -2- [7- (N, N-dimethylaminosulfonyl) imidazo [5, 1-b] thiazol-2-yl] -6- ((IR) -1 -hydroxyethyl) -1,3-methyl-l-carbapen-2-em-3-carboxylic acid cyclohexyloxycarbonyloxymethyl ester 323. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- ( 2-Methyl-1- (phenoxycarbonyloxy) -1-propyl 7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate (a mixture of diastereomers) 324. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2- 1- (1-naphthoxycarbonyloxy) ethyl em- 3-carboxylate (a mixture of diastereomers) 325. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7 [1- (2- (1-propyl) phenoxycarbonyloxy] ethyl] ethyl (a mixture of diastereomers) 326. (Methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid ( ÍS, 5R, 6S) -2- (7-acetylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em -3-carboxylic acid (2-ethylphenoxycarbonyloxy) ethyl ester (a mixture of e diastereomers) 327. (1S, 5R, 6S) -2- [7- (N, N-dimethylaminosulfonyl) imidazo [5, 1-b] thiazol-2-yl] -6- ((IR) -1-hydroxyethyl ) -l-methyl-l-carbapen-2-em-3-carboxylic acid (2-ethylphenoxycarbonyloxy) ethyl ester (a mixture of diastereomers) 328. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl ) -l-methyl-2- (7-methylsulfinyl-imidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of pivaloyloxymethyl (a mixture of diastereomers) 329. ( ÍS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em -3-carboxylic acid 1- (2-benzyloxycarbonyloxy) ethyl ester (a mixture of diastereomers) 330. (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-) Methylthioimidazo [5, 1-b] thiazol-2-yl] -l-carbapen-2-em-3-carboxylic acid 1- (2-methyl-1-propyloxycarbonyloxy) ethyl ester (a mixture of diastereomers) 331. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3 -carboxylate of 4- (N, N-di-n-propylaminosulfonyl) benzoyloxymethyl 332. (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen -2- Em-3-carboxylate of 1- [4- (N, N-di-n-propylaminosulfonyl) benzoyl-oxy] ethyl (a mixture of diastereomers) Preparation of the compounds The compounds according to the present invention can be prepared through several methods. The preferred preparation methods appear below. Process 1 The compound of the formula (I) wherein R is hydrogen can be prepared according to the following reaction scheme.

(I) (II) c the additive (V) vulnerability (I) where R1, R2, R3, R4 and R5 have the same meanings as defined in formula (I), R6 represents hydrogen or a hydroxyl protecting group such as for example t-butyldimethylsilyl, trimethylsilyl, triethylsilyl, 4- Nitrobenzyloxycarbonyl, 4-methoxybenzyloxycarbonyl, R7 represents a carboxyl protecting group such as for example 4-nitrobenzyl, 4-methoxybenzyl, diphenylmethyl, t-butyldimethylsilyl, R8 represents lower alkyl, preferably n-butyl and methyl, R9, R10, R11, and R12 have the same meaning as R1, R2, R3, R4 and R5 or represent a protected group thereof wherein a functional group such as for example hydroxyl, amino, carboxyl and hydroxyimino is protected by a conventional protection group. The compound of the formula (II) can be prepared by the usual method, and the tin compound of the formula (IV) can be prepared by a method described below. In the first step, the compound of the formula (II) can be converted to the compound of the formula (III) by the following method. The compound (III) can be prepared by reacting the compound of the formula (II) with one (1) equivalent or an excess amount of anhydrous trifluoromethanesulfonic acid in the presence of an organic base, preferably diisopropylethylamine in an amount of one (1) ) equivalent or an excess amount of anhydrous trifluoromethanesulfonic acid in an inert solvent such as acetonitrile, tetrahydrofuran, dichloromethane, and toluene, and the mixed solvent thereof at a temperature of -50 ° C to + 50 ° C for a period of time from 10 minutes to 24 hours, and then subjecting the reaction mixture to a usual purification procedure. In the second step, the Compound of the formula (III) can be converted to the compound of the formula (V) by the following method. The compound of the formula (V) can be prepared by the reaction of the compound of the formula (III) with one (1) equivalent or an excess amount of the compound of the formula (V) in the presence of 0.001 - 1 equivalent of a palladium catalyst such as tetrakis (triphenylphosphine) palladium (0), tris (dibenzylidene ketone) -dipaladium (0), or an adduct of tris (dibenzylideneacetone) dipalladium (0) -chloroform, 0.001-1 equivalent of a phosphine ligand such as for example triphenylphosphine, tri-2-furylphosphine or tri-2-thienylphosphine, tris (2,4,6-trimethoxyphenyl) phosphine, and 1-10 equivalents of an additive such as for example zinc chloride, lithium chloride, or cesium fluoride alone or in combination in an inert solvent such as, for example, tetrahydrofuran, dimethoxyethane, dioxane , acetonitrile, acetone, ethanol, dimethylsulfoxide, sulfolane, N, -dimethylformamide, N, N-dimethylacetamide, N -methylpyrrolidinone, or a hexamethylphosphoric triamide, or a mixed solvent thereof at a temperature of 0 ° C to 100 ° C for a period of 10 minutes to 7 days, and after by subjecting the reaction mixture to an ordinary after-treatment. In the third step, the protecting groups R6 'and R7 or the protective groups on R9, R10, R11, and R12 in the compound of the formula (V) can be removed by the deprotection reaction in one step or in several steps according to the types of protecting groups to obtain the compound of the formula (I) according to the present invention. The deprotection reactions, which depend on the types of the protecting groups R7 and R8 and the protecting groups on R9, R10, and R11 and R12 employed, can be carried out according to usual methods generally known in the art. When one or both of the protective groups can be removed in the acidic condition, a mineral acid, such as for example hydrochloric acid, an organic acid such as for example oxalic acid, acetic acid or citric acid, or an acid of Lewis such as for example aluminum chloride can be used. When the protective groups are removed in reducing condition, a catalytic reduction is used with several catalysts, or a metal reduction agent such as zinc or iron. When R6 is a silyl protecting group such as for example a t-butyldimethylsilyl group, a trimethylsilyl group or a triethylsilyl group, it can be easily removed with the use of a fluorine ion reagent such as for example tetrabutylammonium fluoride. When Rs is an allyloxycarbonyl group and R is an allyl group, the protecting groups can be easily removed with the use of various palladium complexes such as tetrakis (triphenylphosphine) palladium (0). Process (2) The compound of the formula (V) in which at least one of R9, R10, R11 and R12 is a lower alkylthio can be converted to the compound of the formula (V) in which the lower alkylthio group is converted to lower alkylsulfonyl or lower alkylsulfinyl according to the following reaction.

(V) (V) where R1 has the same meaning as defined in the formula. (I), R6, R7, R9, R10, Ru and R12 have the same meanings as defined in formula (V) in procedure (1) above, R13, R14, R15 and R16 have the same meanings as R9, R10, R and R > 12, provided that at least one of R ', R 10, R. 11 and R. 1-represents lower alkylthio and at least one of R 13, R 14, R 15 and R 16 represents lower alkylsulfonyl or lower alkylsulfinyl. The compound of the formula (V) can be converted into the compound of the formula (V) by reacting the compound of the formula (V) with one (1) equivalent or an excess amount of an oxygenation agent (e.g. , OXO'WL DuPont, -cloroperbenzeoico acid) in an inert solvent such as THF, dioxane, dichloromethane, chloroform or water, or a mixed solvent thereof at a temperature of - 50 ° C to + 100 ° C for a period of 10 minutes to 7 days, and then subjecting the reaction mixture to the usual purification procedure. The compound of the formula (V) can be converted to the compound of the formula (I) in the same manner as in the third step of the process (1). The compound of the formula (I) obtained in this way can be isolated and purified by crystallization or by chromatography with a non-ionic macroalta porous resin, gel filtration with Sephadex or the like, or reverse phase silica gel column chromatography. .

Process (3) The compounds of the formula (I) wherein R represents a hydrolysable ester in organisms can be prepared by the conversion of the compounds represented by the formula (I) wherein R is hydrogen in the ester derivatives. wherein R 1, R 2, R 3, R 4 and R 5 have the same meanings as defined in formula (I), R 17 represents C 1 - 0 alkyl, arylcarbonyloxy-lower alkyl group, aryl-lower alkyloxy-lower alkylcarbonyloxy-alkyl group "lower alkylcarbonyloxy-lower alkyl., cycloalkylcarbonyloxy-lower alkyl, cycloalkyl lower-alkylcarbonyloxy-lower alkyl, diciclohexilmetilcarboniloxi-lower alkyl, adamantilcarboniloxi-lower alkyl, alkyloxycarbonyloxy-lower alkyl, cycloalkyloxycarbonyloxy-lower alkyl, (lower cycloalkyloxycarbonyloxy ) (lower cycloalkyl) methyl, lower cycloalkyl-alkyloxycarbonyloxy-lower alkyl, adamantiloxicarboniloxi-lower alkyl, 2-indanyloxycarbonyloxy-lower alkyl wherein the aromatic ring may be substituted, aryl-alkyloxycarbonyloxy-lower alkyl, lower aryloxycarbonyloxy-alkyl where the aromatic ring can be substituted, lower 5-indanyloxycarbonyloxy-alkyl wherein the aromatic ring may be substituted, 2-oxo-5-lower alkyl-1, 3-dioxolen-4-ylmethyl, 3-phthalidyl in which the aromatic ring may be substituted, or 2- (3-phthalidylidene) ethyl wherein the aromatic ring may be substituted, X represents a leaving group such as Cl, Br, I, -OS02CF3, -OS02CH3, or -OS02PhCH3. The compound of the formula (I ') can be prepared by reacting the compound of the formula (I) with an alkyl halide R17-X in the presence of one (1) equivalent or an excess amount of a base at a temperature of -70 ° C to + 50 ° C, preferably from -30 ° C to + 20 ° C, for a period of 10 minutes to 20 hours. The base that can be used in the reaction includes, for example, organic bases such as diisopropylethylamine, diazabicyclo [2, 2, 2] undecene and 2, 6-lutidine, and inorganic bases such as sodium hydroxide, potassium hydroxide, hydrogencarbonate sodium, potassium hydrogen carbonate, sodium carbonate, potassium carbonate and cesium carbonate. The alkyl halide R17-X includes, for example, pivaloyloxymethyl iodide, 1- (pivaloyloxy) ethyl iodide, isobutyryloxymethyl iodide, 1- (isobutyryloxy) ethyl iodide.Iodide acetoxymethyl iodide, 1- (acetoxy) ethyl iodide, (1-methylcyclohexan-l-yl) carbonyloxymethyl iodide benzoyloxymethyl iodide 1- (benzoyloxy) ethyl iodide, 1- (2-methylbenzoyloxy) ethyl, iodide 4-t-butilbenzoiloximetilo iodide 2, 4, 6-trimethylbenzoyloxymethyl iodide, 4- (N, N-di-n-propylaminosulphonyl) benzoyloxymethyl iodide 1- [4- (N, N-di-n -propylaminosulfonyl) benzoyloxy] ethyl iodide, 2-naftilcarboniloximetilo .de iodide 1-adamantilcarboniloximetilo iodide 1- (1-adamantilcarboniloxi) ethyl iodide, cyclohexyloxycarbonyloxymethyl iodide, 1- (cyclohexyloxycarbonyloxy) ethyl iodide, 1- (cyclohexyloxycarbonyloxy ) -1-propyl, 1- [(cyclohexylmethoxy) carbonyloxy] ethyl iodide, 1- [(cyclohexylethoxy) carbonyloxy] ethyl iodide, 1- (ethoxycarbonyloxy) ethyl iodide, l - [(2-methylcyclohexan-1) iodide -yl) oxycarbonyloxy] ethyl, cyclopentyloxycarbonyloxymethyl iodide, 1- (isopropyloxycarbonyloxy) ethyl iodide, (IR, 2S) iodide , 5R) - (1) -metiloxicarboniloximetilo iodide (IS, 2R, 5S) - (d) -metiloxicarboniloximetilo iodide 2-adamantiloxicarboniloximetilo iodide 1- (2-phenyl-l-ethyloxycarbonyloxy) ethyl iodide, feniloxicarboniloximetilo , 1- (phenyloxycarbonyloxy) ethyl iodide, 1- (4-methylphenoxycarbonyloxy) ethyl iodide, 1- (2-methylphenoxycarbonyloxy) ethyl iodide, 1- (2-ethylphenoxycarbonyloxy) ethyl iodide, 1- (2-iodide - (2-propyl) phenoxycarbonyloxy] ethyl iodide, 1- (2, -dimetilfenoxicarboniloxi) ethyl iodide, 1- (2, 5-dimetilfenoxicarboniloxi) ethyl iodide, 1- (3, 5-dimetilfenoxicarboniloxi) ethyl iodide 1- (2, 3, 5-trimethylphenoxycarbonyloxy.) Ethyl, 1- (2,6-dimethylphenoxycarbonyloxy) methyl iodide, 2-methyl-1- (phenoxycarbonyloxy) -1-propyl iodide, 1- (2-iodide methoxyphenoxycarbonyloxy) ethyl, 1- (1-naphthoxycarbonyloxy) ethyl iodide, (indan-5-yl) oxycarbonyloxymethyl iodide, 1- ((indan-5-yl) oxycarbonyloxy) ethyl iodide, 1- (unsaturated 5-il) oxycarbonyloxy) -1-propyl, (5-methyl-2-oxo-l, 3-dioxolen-4-yl) methyl bromide, 3-phthalidyl bromide, 4- (Z) -2- (3-phthalidylidene bromide ethyl) The inert solvent which can be used in the reaction includes N, N-dimethylformamide, N, N-dimethylacetamide, N, N-diethylformamide, N, N-diethylacetamide, N-methylpyrrolidinone, N, N-dimethylimidazolidinone, dimethylsulfoxide, sulfolane, acetonitrile, acetone, ethyl acetate, tetrahydrofuran, 1,4-dioxane, diethyl ether, anisole, dichloromethane, 1,2-dichloroethane, chloroform, toluene, benzene, hexamethylphosphoric triamide, methanol, and ethanol. The compound (I ') obtained in this way can be isolated and purified by precipitation, crystallization, gel filtration with Sephadex, or silica gel chromatography. Process (4) The compound of the formula (IV) used in the reaction described above can be prepared by the following method: (VI) (IV) wherein R9, R10, R11 and R12, any of them is M or R93SN, and the other three, which may be the same or different, have the same meanings as R2, R3, R4 and R5, or they represent a protected group thereof wherein a functional group such as hydroxyl, amino, carboxyl, and hydroxyimino is protected by a conventional protecting group, R8 represents lower alkyl, preferably N-butyl or methyl, M represents Li, MgCl, MgBr or Mgl, and Z represents Cl, Br, I or -0S02CF3. The compound of the formula (VI) used can be prepared according to the method described in WO98 / 023623. The compound of the formula (VI) can be converted to the compound of the formula (IV) by the following method. The compound of the formula (IV) can be prepared by reacting the compound of the formula (VI) in an inert solvent such as tetrahydrofuran, diethyl ether, 1,4-dioxane, anisole, dimethoxyethane, dichloromethane or toluene alone or in combination of them with R93SNZ in a ratio of one (1) equivalent or an excess amount of the compound of the formula (VI) at a temperature of -100 ° C to + 50 ° C for a period of 15 minutes to 24 hours, and then submitting to usual after-treatment.

The compound of the formula (IV) obtained in this way can be isolated and purified by crystallization or by chromatography with a non-ionic macro-porous resin, gel filtration with Sephadex or the like, or reverse phase silica gel column chromatography. . Use of the compound / pharmaceutical composition The compound according to the present invention has broad and strong antimicrobial activities against gram-positive bacteria and against gram-negative bacteria, and has strong antimicrobial activities against MRSA, PRSP, enterococci, influenza and bacteria that produce ß -lactamase too. In addition, it has a low toxicity and is stable in relation to DHP-1. Thus, the compound according to the present invention can be used for the treatment of infections caused by various pathogenic bacteria in animals, including humans. The compound of the formula (I) wherein R represents a hydrolysable group in organisms may be beneficial especially when administered orally due to its excellent oral absorption property. The pharmaceutical composition comprising the compound according to the present invention and a pharmacologically acceptable salt and ester thereof as the effective ingredient can be administered orally or parenterally via the routes of administration including intravenous injection, intramuscular injection, or administration subcutaneous, rectal or percutaneous to humans and other animals. Thus, the pharmaceutical composition comprising the compound according to the present invention as an effective ingredient can be formed into appropriate administration forms according to the routes of administration, and can be prepared specifically primarily in any of the preparation forms including injections such as injection intravenous and intramuscular injection, preparations for oral administration such as capsules, tablets, granules, powders, pills, particles, lozenges, preparations for rectal administration and fatty suppositories. These preparations can be carried out by customary methods with the excipients, fillers, agglomerating agents, humidifiers, disintegrants, surfactants, lubricants, dispersants, buffers, storage agents, dissolving aids, preservatives, flavorings, analgesic agents, agents of stabilization and the like usually employed. Such non-toxic additives that can be used include, for example, lactose, fructose, glucose, starch, gelatin, magnesium carbonate, synthetic magnesium silicate, talc, magnesium stearate, methyl cellulose or a salt thereof, gum arabic, polyethylene glycol, syrup, petrolatum, glycerol, ethanol, propylene glycol, citric acid, sodium chloride, sodium sulfite, sodium phosphate, and the like. The dosage amount is appropriately determined taking into account the route of administration, the age, sex and condition of a patient, and the preparation can be administered for the treatment of infections usually in an amount of about 25 mg - 2000 mg, preferably of 50 mg to 1000 mg per day per adult in one or several portions. EXAMPLES The following examples and preparations further illustrate the present invention but are not intended to limit it. Preparation 1 7-propionyl-3- (tri-n-butylstannyl) imidazo [5, 1-b] -thiazole and 7-propionyl-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole a) 7-propionylimidazo [5, 1-b] -thiazole Aluminum chloride (16.0 g) was added to a solution of 12.1 ml of propionyl chloride in 100 ml of carbon disulfide. A solution of 2.48 g of imidazo [5, 1-b] thiazole in 100 ml of dichloromethane was added dropwise, the mixture was stirred at room temperature for 18 hours, propionyl chloride (12.1 ml) was further added, and 16.0 g of aluminum chloride, followed by stirring for 24 hours, the reaction solution was poured into 100 g of ice, dichloromethane (200 ml) was added, sodium carbonate (100 g) and sodium sulfate (100 g) were added. ) in this order to the mixture with stirring The insoluble particles were removed by filtration and washed with dichloromethane The filtrate was concentrated under reduced pressure Ethyl acetate (10 ml) was added to the concentrate The crystals formed in this way were collected The filtrate was purified by silica gel column chromatography (dichloromethane: ethyl acetate = 1: 1), and then combined with the collected crystals to obtain 2.49 g of 7-propionylimidazo [5, 1-b] - thiazole NMR (CDC13) d: 1.26 (3H, t, J = 7.4 Hz), 3.07 (2H, q, J = 7.4 Hz), 7.10 (1H, d, J = 4.2 Hz), 7.54 (1H, d, J = 4.2 Hz), 8.00 (1H, s) b) 7-propionyl-3- (tri-n-butylstannyl) imidazo [5, 1-b] -thiazole and 7-propionyl-2- (tri-n-butylstannyl) imidazo [5, 1-b] -thiazole A solution of 1.0 N / THF litiumbis (trimethylsilyl) amide (6.17 ml) was added to 60 ml of THF. A solution of 2.12 ml of tri-n-butylstannyl chloride in 24 ml of THF and a solution of 1.11 g of 7-propionylimidazo [5, 1-b] -thiazole in 24 ml of THF were added dropwise. This order, in an argon atmosphere at a temperature of -73 ° C to the mixture, was stirred at the same temperature for one hour, and a solution of 1.0 N / THF litiumbis (trimethylsilyl) amide was added dropwise. (6.17 ml) There the mixture was stirred at the same temperature for 2 hours, a solution of ammonium chloride (50 ml) was added to the reaction solution, followed by extraction with ethyl acetate. a saline solution, dried over anhydrous magnesium sulfate, and filtered.The solvent was removed by distillation under reduced pressure.The residue was purified by column chromatography on silica gel (hexane: ethyl acetate = 2: 1). the two main components, the fraction that had been eluted earlier, was collected to give 234 mg of 7-propionyl-3- (tri-n-butylstannyl) imidazo [5, 1-b] -thiazole. NMR (CDC13) d: 0.91 (9H, m), 1.30 (15H, m), 1.60 (6H,), 3.07 (2H, q, J = 7.4 Hz), 6.88 (1H, s), 7.88 (1H,, s) Of the two main components, the fraction that had been eluted subsequently was collected to provide the 234 mg of 7-propionyl-2- (tri-n-butylstannyl) imidazo [5, 1-b] -thiazole. NMR (CDCI3) d: 0.91 (9H, t, J = 7.1 Hz), 1.18 (6H, m), 1.26 (3H, t, J = 7.4 Hz), 1.35 (6H, m), 3.05 (2H, q, J = 7.4 Hz), 7.27 (1H, s), 7.93 (1H, s) Preparation 2 7- (4-Nitrobenzyloxyiminomethyl) -2- (tri-n-butylstannyl) imidazo [5, 1-b] -thiazole (a geometric isomer derived from an initial compound as a low polarity oxime isomer) a) 7-formylimidazo [5, 1-b] -thiazole.

DMF (15.48 ml) was added 80 ml of dichloromethane. A solution of 18.32 ml of phosphorus oxychloride in 80 ml of dichloromethane was added dropwise under ice-cooling. The reaction was allowed to proceed at room temperature for 30 minutes. A solution of imidazo [5, 1-b] thiazole in 40 ml of dichloromethane was added there dropwise. The mixture was heated under reflux for 2.5 hours. The reaction solution was poured on ice. The reaction solution was adjusted to a pH of 9.8 by the addition of a 5 N aqueous solution of sodium hydroxide, followed by extraction 5 times with 200 ml of dichloromethane. The extract was dried in anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by silica gel column chromatography (diluting with dichloromethane: ethyl acetate = 5: 1, ethyl acetate alone, and then dichloromethane: methanol = 10: 1) to give 2.37 g of 7-formylimidazo [5 , 1-b] -thiazole. NMR (CDC13) d: 7.17 (1H, d, J = 4.1 Hz), 7.60 (1H, d, J = 4.1 Hz), 8.07 (1H, s), 9.93 (1H, s) b) 7-hydroxyiminomethylimidazo [5 , 1-b] -thiazole (a geometric isomer of low polarity) 7-formylimidazo [5, 1-b] -thiazole (249 mg) was suspended in 10 ml of ethanol. Hydroxylamine hydrochloride (137 mg) and 2.0 ml of a 1 N aqueous sodium hydroxide solution were added under cooling with ice to the suspension. The mixture was stirred at the same temperature for 1.5 hours, and then stirred at room temperature for 3 hours. The reaction solution was concentrated under reduced pressure until the volume of the reaction solution was reduced to about half the original volume. The concentrate was adjusted to a pH of 12 by the addition of a potassium carbonate solution, followed by extraction three times with dichloromethane. The extract was dried in anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane: ethyl acetate = 1: 2). Of the two major components, the fraction that had been eluted earlier was collected to provide 160 mg of 7-hydroxyiminomethylimidazo [5, 1-b] -thiazole (a geometric isomer of low polarity). NMR (CDC13) d: 7.40 (1H, d, J = 4.1 Hz), 7.98 (1H, d, J = 4.1 Hz), 8.09 (1H, s), 8.27 (1H, s) c) 7-hydroxyiminomethyl-2 - (tri-n-butylstannyl) imidazo [5, 1-b] -thiazole (a geometric isomer derived from an initial compound as a low polarity oxime isomer) 7-hydroxyiminomethylimidazo [5, 1-b] - thiazole (a geometric isomer of low polarity) (8321 mg) in 25 ml of THF and 5 ml of hexylphosphoramide (HMPA). A solution of n-butyllithium / n-hexane 1.55 N (7.67 ml) was added dropwise under an argon atmosphere at a temperature of -70 ° C to the solution. The mixture was stirred at the same temperature for 40 minutes. Tri-n-butylstannyl chloride (1.84 ml) was added. The mixture was stirred for 1.5 hours while the temperature was raised to -40 ° C. A solution of ammonium chloride was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with a saline solution, dried over anhydrous magnesium sulfate and filtered. The solvent was removed by distillation under reduced pressure. The residue was purified by silica gel column chromatography (hexane: ethyl acetate = 3: lal: 1) to provide 6.80 mg of 7-hydroxyiminomethyl-2- (tri-n-butylstannyl) imidazo [5, 1-b ] -thiazole (a geometric isomer derived from an initial compound such as a low polarity oxime isomer). NMR (CDC13) d: 0.91 (9H, t, J = 7.4 Hz), 1.17 (6H, m), 1.35 (6H, m), 1.58 (6H, m), 7.23 (1H, s), 7.98 (1H, s), 8.30 (1H, S) d) "7- (4-nitrobenzyloxyiminomethyl) -2- (tri-n-butylstannyl) imidazo [5, 1-b] -thiazole (a geometric isomer derived from an initial compound as a low polarity oxime isomer) 4-Nitrobenzyl bromide (671 mg) and 290 mg of t-butoxypotassium in an argon atmosphere were added to a solution of 1.18 g of 7-hydroxyiminomethyl-2- (tri-n-butylstannyl) imidazo [5, 1-b] -thiazole (a geometric isomer derived from an initial compound as a low polarity oxime isomer) in 25 ml of DMF at a temperature of -40 ° C. The mixture was stirred at the same temperature for one hour . Ethyl acetate was added to the reaction solution. The mixture was washed three times with a saline solution, and dried with anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane: ethyl acetate = 5: 1) to give 169 mg of the title compound. NMR (CDC13) d: 0.92 (9H, m), 1.17 (6H, m), 1.35 (6H,), 1.59 (6H, m), 5.27 (2H, s), 7.21 (1H, s), 7.60 (2H , d, J = 8.9 Hz), 7.96 (1H, s), 8.22 (2H, d, J = 8.9 Hz), 8.32 (1H, s) Preparation 3 7-methoxyiminomethyl-3- (tri-n-butylstannyl) imidazo [5, 1-b] -thiazole (a stereoisomer derived from an initial compound as a low polarity oxime isomer) a) 7-methoxyiminomethylimidazo [5, 1-b] -thiazole (a low polarity stereoisomer) was suspended. -formylimidazo [5, 1-b] -thiazole (249 mg) in 10 ml of ethanol. O-Methylhydroxyamine hydrochloride (219 mg) and 2.67 ml of and a 1 N aqueous solution of sodium hydroxide were added to the suspension. The mixture was stirred at room temperature for 20 hours. The solution of the reaction was concentrated. Water (50 ml) was added to the concentrate, followed by dichloromethane extraction. The extract was dried in anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography on silica gel (dichloromethane: ethyl acetate = 1: 1). Of the two major components, the fraction that had been eluted earlier was collected to provide 164 mg of 7-methoxyiminomethylimidazo [5, 1-b] -thiazole (a geometric isomer of low polarity). NMR (CDC1) d: 3.96 (3H, s), 7.01 (1H, d, J = 4.1 Hz), 7.48 (1H, d, J = 4.1 Hz), 8.02 (1H, s), 8.24 (1H, s) b) 7-methoxyiminomethyl-3- (tri-n-butylstannyl) imidazo [5, 1-b] -thiazole (a stereoisomer derived from an initial compound as a low polarity oxime isomer) 7-methoxyiminomethylimidazo was dissolved [ 5, 1-b] -thiazole (a geometric isomer of low polarity) (1.47 g) in 454 ml of THF. A solution of n-butyllithium / n-hexane 1.55 N (6.27 ml) was added dropwise under an argon atmosphere at -70 ° C. The mixture was stirred at the same temperature for one hour. Tri-n-butylstannyl chloride (2.77 ml) was added to the reaction mixture. The mixture was stirred for two hours while the temperature was raised to -55 ° C. A solution of ammonium chloride was added to the reaction solution. The mixture was extracted with ethyl acetate. The organic layer was washed with a saline solution, dried over anhydrous magnesium sulfate, and filtered. The solvent was removed by distillation under reduced pressure. The residue was purified by silica gel column chromatography (hexane: ethyl acetate = 5: 1 to 3: 1). The title compound (1.68 mg) was obtained from the fraction of Rf = 0.7 (hexane: ethyl acetate = 3: 1). NMR (CDC13) d: 0.90 (8H, t, J = 7.4 Hz), 1.24 (6H, 'm), 1.35 (6H, m), 1.55 (6H, m), 3.96 (3H, s), 6.81 (1H , s), 7.92 (1H, s), 8.25 (1H, s) Preparation 4 7-pivaloyl-3- (tri-n-butylstannyl) imidazo [5, 1-b] -thiazole a) 7-pivaloylimidazo [5, 1-b] -thiazole Aluminum chloride (6.0 g) was added to a solution of 6.1 ml of pivaloyl chloride in 50 ml of carbon disulfide. The mixture was stirred. A solution of 1.2 g of imidazo [5, 1-b] -thiazole in 20 ml of dichloromethane was added, and the mixture was stirred at room temperature for 48 hours. Dichloromethane (200 ml) was added to the reaction mixture. The mixture was washed with water and a saturated aqueous solution of sodium hydrogencarbonate in this order, and then dried over anhydrous magnesium sulfate. The solvent was removed by distillation. The residue was purified by silica gel column chromatography (hexane: ethyl acetate = 1: 2) to give 0.92 g of 7-pivaloylimidazo [5., 1-b] -thiazole. NMR (CDC13) d: 1.39 (9H, s), 6.73 (1H, d, J = 4.3 Hz), 7.32 (1H, d, J = 4.3 Hz), 7.92 (1H, s) b) 7-pivaloyl-2 - (tri-n-butylstannyl) imidazo [5, 1-b] -thiazole A solution of n-butyllithium / n-hexane 1.6 N (2.9 ml) was added to a solution of 0.92 g of 7-pivaloylimidazo [5, 1 - b] -thiazole in 20 ml of dry THF in an argon atmosphere at a temperature of -50 ° C. The mixture was stirred at a temperature of -50 ° C. The mixture was stirred at that temperature for 20 minutes. Tri-n-butylstannyl chloride (1.3 ml) was added, followed by stirring for 20 minutes. A saturated aqueous solution of ammonium chloride was added to the reaction mixture. Acetate was added there _ ethyl. The mixture was washed with water and a saturated saline solution in this order. The organic layer was dried in anhydrous magnesium sulfate. The solvent was removed by distillation. The residue was purified by column chromatography on silica gel (hexane: ethyl acetate = 1: 3) to give 0.82 g of the title compound. NMR (CDCI3) d: 0.92 (9H, t, J = 7.2 Hz), 1.13 (6H, t, J = 8.4 Hz), 1.30-1.40 (15H, m), 1.52-1.62 (6H, m), 7.08 ( 1H, s), 7.88 (1H, s) Preparation 5 7-Acetyl-3-methyl-2- (tri-n-butylstannyl) imidazo [5, 1-b] -thiazole a) 7-acetyl-3-methylimidazo [ 5, 1-b] -thiazole Aluminum chloride (16.0 g) was added to a solution of 10.0 ml of acetyl chloride in 100 ml of carbon disulfide at room temperature. The mixture was stirred for 30 minutes. A solution of 2.76 g of 3-methyloxy [5, 1-b] thiazole in 40 ml of dichloromethane was added dropwise there over a period of 15 minutes with stirring. The mixture was further stirred for 6 hours. The reaction solution was added to a mixture of 200 ml of dichloromethane with 100 g of ice with complete stirring. After dissolution of the ice, 40 g of sodium carbonate and 50 g of sodium sulfate were added, in this order, with complete stirring. The mixture was stirred under cooling with ice for 30 minutes. After standing, the organic layer was separated by decantation. The gum residue was extracted with dichloromethane (100 ml, 5 times), and then combined with the organic layer. The combined organic layer was dried over anhydrous magnesium sulfate, and concentrated to dryness under reduced pressure. Ethyl acetate (10 ml) was added to the concentrate. The resulting solid was triturated with 10 ml of ethyl acetate, collected by filtration, and washed with a minor amount of ethyl acetate. The washed product was dried under reduced pressure to provide 2.92 g of 7-acetyl-3-methylimidazo [5, 1-b] -thiazole. NMR (CDC13) d: 2.51 (3H, d, J = 1.3 Hz), 2.61 (3H, s), 7.66 (1H, q, J = 1.3 Hz), 7.88 (1H, s) b) 7-acetyl-3 -methyl-2- (tri-n-butylstannyl) imidazo [5, 1-b] -thiazole A 1.0 N solution of lithium (trimethylsilyl) amide / n-hexane (2.2 ml) was added dropwise to a solution of 0.360 g of 7-acetyl-3-methylimidazo [5, 1-b] -thiazole in THF (20 ml) at a temperature of -70 ° C. The mixture was stirred for 15 minutes. A 1.6 N solution of n-butyllithium / n-hexane (2.8 ml) was added dropwise to the reaction solution at the same temperature. The mixture was stirred for one hour. A solution was added dropwise (4 ml) of 0.846 g of tri-n-butylstannyl in THF to the reaction solution. The mixture was stirred at a temperature of -40 ° C for 30 minutes. The reaction solution was added under cooling with ice to a mixed ether solution (50 ml) and 0.2 N phosphate buffer (pH 7) (50 ml) with complete stirring. The organic layer was separated, washed with 0.2 N phosphate buffer (pH 7) (30 ml), and dried over anhydrous magnesium sulfate. The solvent was removed by distillation. The residue was subjected to separation and purification by flash column chromatography on silica gel (ethyl acetate) to provide 0.752 g of the title compound. NMR (CDC13) d: 0.90 (9H, t, J = 7.3 Hz), 1.10 to 1.43 (12H, m), 1.50 to 1.62 (6H, m), 2.46 (3H, s), 2.60 (3H, s), 7.80 (1H, s) Preparation 6 7- (2-formylamino) propionyl-2- (tri-n-butylstannyl) imidazo [5,1- b] -thiazole a) 7-acetylimidazo [5, 1-b] -thiazole In the same manner as preparation 9-a), 5.09 g of 7-acetylimidazo [5, 1-b] -thiazole was obtained from 4.97 g of imidazo [5, 1-b] -thiazole. NMR (CDC13) d: 2.62 (3H, s), 7.10 (1H, d, J - 4.1 Hz), 7.55 (1H, d, J = 4.1 Hz), 8.00 (1H, s) MS (TS): 167 ( M ++ H) b) 7-azidoacetylimidazo [5, 1-b] -thiazole A 1.0 N solution of lithium (trimethylsilyl) amide / n-hexane (5.8 ml) a solution of 0.83 g of 7-acetylimidazole was added. [5, 1-b] -thiazole in 20 ml of dry THF and 5 ml of HMPA in an argon atmosphere at a temperature of -50 ° C. The mixture was stirred for 30 minutes, and trimethylsilyl chloride (0.76 ml) was added. ) and at a temperature of -20 ° C. The mixture was stirred for 30 minutes., - a solution of 1.07 g of N-bromosuccinimide in 20 ml of dry THF was added thereto at a temperature of 0 ° C. The mixture was stirred at room temperature for 2 hours. Ethyl acetate was added to the reaction mixture. The mixture was washed with water and a saturated saline solution, in this order, and dried in anhydrous magnesium sulfate. DMF (10 ml) was added. The solvent was concentrated. Sodium azide (0.39 g) was added to a solution of the reaction mixture in 10 ml of DMF. The mixture was stirred at room temperature for 12 hours. Ethyl acetate was added to the reaction mixture. The mixture was washed with water and a saturated saline solution, in this order, and dried in anhydrous magnesium sulfate. The solvent was removed by distillation. The residue was purified by column chromatography on silica gel (ethyl acetate) to give 0.44 of 7-azidoacetylimidazo [5, 1-b] -thiazole. NMR (CDC13) d: 4.62 (2H, s), 7.17 (1H, d, J = 3.6 Hz), 7.60 (1H, d, J = 3.6 Hz), 8.03 (1H, s) c) 7-formylaminoacetylimidazo [5 , 1-b] -thiazole A solution of 10% methanol hydrochloric acid (1 ml) and 120 mg of 10% Pd-C were added to a solution of 0.44 g of 7-azidoacetylimidazo [5, 1-b] -thiazole in 50 ml of methanol and 50 ml of THF. The atmosphere in the reactor was replaced with hydrogen. The system was stirred at room temperature for 2 hours. The reaction mixture was filtered. The solvent was removed by distillation, 10 ml of DMF, 0.39 g of 4-nitrophenyl formate and 0.66 ml of triethylamine were added to the residue, and the mixture was stirred at room temperature for 10 minutes. The mixture was washed with water and a saturated saline solution, in this order, and then dried over anhydrous magnesium sulfate.The solvent was removed by distillation.The residue was purified by column chromatography on silica gel (dichloromethane: ethanol = 10: 1) to provide 0.24 of 7-formylaminoacetylimidazo [5, 1-b] -thiazole, NMR (DMSO-de) d: 4.56 (2H, d, J = 5.8 Hz), 7.54 (1H, d, J = 5.0 Hz), 8.11 (1H, d, J = 5.0 Hz), 8.15 (1H, s), 8.33 (1H, s), 8.37 (1H, s) d) 7- (2-formylaminopropionyl) imidazo [5, 1 -b] -thiazole Sodium hydride (31 mg) was added to a solution of 0.24 g of 7-formylaminoacetylimidazo [5, 1-b] -thiazole in 4 ml of DMF.The mixture was stirred at a temperature of 60 ° C. for 30 minutes, and cooled to room temperature. Then, 176 mg of methyl iodide was added. The mixture was stirred for 1 hour. Dichloromethane was added to. the reaction mixture. The mixture was washed with water and a saturated saline solution, in this order, and dried in anhydrous magnesium sulfate. The solvent was removed by distillation. The residue was purified by column chromatography on silica gel (dichloromethane: methanol = 20: 1) to provide 0.12 g of 7- (2-formylaminopropionyl) imidazo [5, 1-b] -thiazole. NMR (CDC13) d: 1.61 (3H, d, J = 7.0 Hz), 5.60-5.70 (1H, m), 6.85 (1H, s), 7.16 (1H, d, J = 4.1 Hz), 7.60 (1H, d, J = 4.1 Hz), 8.02 (1H, s), 8.27 (1H, s) e) 7- (2-formylamino) propionyl-2- (tri-n-butylstannyl) imidazo [5, 1-b] - thiazole Substantially in the same manner as preparation 4-b), 96 mg of the title compound were obtained from 0.12 g of 7- (2-formylaminopropionyl) imidazo [5, 1-b] -thiazole. NMR (CDC13) d: 0.85-0.95 (9H, m), 1.15-1.25 (6H,), 1.25-1.45 (2H, m), 1.50-1.65 (9H, m), 5.60-5.70 (1H, m), 6.95 (1H, s), 7.32 (1H, s), 7.95 (1H, s), 8.26 (1H, s) Preparation 7 7-isobutyryl-2- (tri-n-butylstannyl) imidazo [5, 1-b] -thiazole a) 7-isobutyrylimidazo [5, 1-b] -thiazole Aluminum chloride (16.2 g) was added to a solution of 15.0 ml of isobutyryl chloride in 100 ml of carbon disulfide. A solution of 40 ml of dichloromethane in 2.50 g of imidazo [5, 1-b] thiazole was added dropwise to the mixture. The mixture was stirred at room temperature for 20 hours. Dichloromethane (100 ml) was added to the reaction solution. Water (60 ml) was added dropwise with stirring. The organic layer was then separated. Dichloromethane (200 ml) and 100 g of sodium carbonate were added to the aqueous layer. The mixture was stirred. The insoluble particles were removed by filtration, and washed with dichloromethane. The filtrate was combined with the organic layer. The combined organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica (dichloromethane: ethyl acetate = 1: 1) to provide 2.75 g of 7-isobutyrylimidazo [5, 1-b] -thiazole. NMR (CDC13) d: 1.26 (6H, d, J = 6.9 Hz), 3.73 (1H, m), 7.09 (1H, d, J = 4.1 Hz), 7.54 (1H, d, J = 4.1 Hz), 8.00 (1H, s) b) 7-isobutyryl-2- (tri-n-butylstannyl) imidazo [5, 1-b] -thiazole A 1.0 N solution of lithium (trimethylsilyl) amide / THF (12 ml) was added at 60 ml of THF. Tri- n-butylstannyl chloride (2.36 ml) and a solution of 1.18 g of 7-isobutyrylimidazo [5, 1-b] -thiazole in 18 ml of THF were added dropwise under an argon atmosphere at a temperature of - 68 ° C. The mixture was stirred at the same temperature for one hour. Ethyl acetate (450 ml) was added to the reaction solution, and the mixture was washed with 200 ml of saline. The organic layer was dried over anhydrous magnesium sulfate, and then filtered. The solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography on silica gel (hexane: ethyl acetate = 3: 2) to provide 1.55 g of the title compound. NMR (CDCl 3) d: "0.86 (9H, t, J = 7.3 Hz), 1.13 (6H, m), 1.21 (6H, d, J = 6.9 Hz), 1.30 (6H, m), 1.53 (6H, m ), 3.69 (1H, m), 7.28 (1H, s), 7.92 (1H, s) Preparation 8 7-Acetyl-3- (tri-n-butylstannyl) imidazo [5, 1-b] -thiazole and 7- acetyl-2- (tri-n-butylstannyl) imidazo [5, 1-b] -thiazole In the same manner as in Example 9-b), a reaction was allowed to be carried out using 10.5 g of 7-acetylimidazo [5]. , 1-b] -thiazole as starting compound The purification was carried out by column chromatography on silica gel (hexane: ethyl acetate = 1: 1) .From two main components, the fraction that had been eluted earlier was collected to provide 1.36 g of 7-acetyl-3- (tri-n-butylstannyl) imidazo [5, 1-b] -thiazole, NMR (CDC13) d: 0.90 (9H, t, J = 7.4 Hz), 1.31 (12H ,), 1.56 (6H, m), 2.62 (3H, s), 6.90 (1H, s), 7.89 (1H, s) MS (ESI): 457 (M ++ H) Of the two main components, the fraction that had been eluted subsequently was collected for prop Order 19.5 g of 7-acetyl-2- (tri-n-butylstannyl) imidazo [5, 1-b] -thiazole. _ NMR (CDCI3) d: 0.91 (9H, t, J = 7.2 Hz), 1.19 (6H, m), 1.35 (6H, m), 1.58 (6H, m), 2.61 (3H, s), 7.28 (1H , s), 7.94 (1H, s) MS (ESI): 457 (M ++ H) Preparation 9 7-Acetyl-5-methyl-2- (tri-n-butylstannyl) imidazo [5, 1-b] - thiazole a) 7-acetyl-5-methylimidazo [5, 1-b] -thiazole Aluminum chloride (6.96 g) was added to a solution of 4.33 ml of acetyl chloride in 40 ml of carbon disulfide. A solution of 1.20 g of 5-methylimidazo [5, 1-b] -thiazole in 40 ml of dichloromethane was added dropwise. The mixture was stirred at room temperature for 24 hours. The reaction solution was poured into 40 g of ice. Dichloromethane (100 ml) was added. Sodium carbonate (32 g) was added to the mixture with stirring. The insoluble particles were removed by filtration, and washed with dichloromethane. The filtrate was concentrated under reduced pressure. Ethyl acetate (20 ml) was added. The resulting crystal was collected by filtration. The filtrate was purified by column chromatography on silica gel (dichloromethane: methanol = 20: 1). The purification product was combined with the crystal collected above to provide 1.45 g of 7-acetyl-5-methylimidazo [5, l ~ b) -thiazole, NMR (CDC13) d: 2.58 (3H, s), 2.65 (3H, s), 7.06 (1H, d, J = 4.2 Hz), 7.37 (1H, d, J = 4.2 Hz) b) 7-Acetyl-5-methyl-2- (tri-n-butylstannyl) imidazo [5, 1-b] -thiazole A 1.0 N solution of lithium (trimethylsilyl) amide / THF (3.75 ml) was added dropwise to a solution of 613 mg of 7-acetyl-5-methylimidazo [5, 1-b] -thiazole in 34 ml of THF in an argon atmosphere at a temperature of -73 ° C. The mixture was stirred at the same temperature for 50 minutes. minutes A 1.59 N solution of n-butyllithium / n-hexane (4.71 ml) was added dropwise there. The mixture was stirred at the same temperature for 50 minutes. Tri- n-butylstannyl chloride (1.16 ml) was added dropwise. The mixture was further stirred at the same temperature for 40 minutes. A solution of ammonium chloride was added to the reaction solution, followed by extraction with ethyl acetate and washing with a saline solution. The extract was dried over anhydrous magnesium sulfate and then filtered. The solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography on silica gel (hexane: ethyl acetate = 1: 1) to provide 1.40 g of the title compound. NMR (CDC13) d: 0.91 (9H, t, J = 7.4 Hz), 1.18 (6H, m), 1.35 (6H, mf, 1.58 (6H, m), 2.57 (3H, s), 2.64 (3H, s ), 7.06 (1H, s) Preparation 10 7-methanesulfonyl-2- (tri-n-butylstannyl) imidazo [5, 1-b] -thiazole A solution 1.6 N n-butyllithium / n-hexane (2.8 ml) was added to a solution of 404 mg of 7-methanesulfonylimidazo [5, 1-b] -thiazole in 20 ml of dry THF under an argon atmosphere at a temperature -40 ° C. The mixture was stirred at the same temperature for 30 minutes. Tri-n-butylstannyl chloride (0.6 ml) was added. A saturated aqueous solution of ammonium chloride was added to the reaction solution. Ethyl acetate was then added. The mixture was washed with water and saturated saline in this order. The organic layer was dried over anhydrous magnesium sulfate. The solvent was removed by distillation. The residue was purified by column chromatography on silica gel (hexane: ethyl acetate = 2: 1) to give 251 mg of the title compound. NMR (CDCI3) d: 0.85-0.95 (9H, m), 1.25-1.33 (6H, m), 1.25-1.40 (6H, m), 1.52-1.64 (6H, m), 3.20 (3H, s), 7.26 (1H, s), 7.99 (1H, s) Preparation 11 7-methanesulfonyl-3- (tri-n-butylstannyl) imidazo [5, 1-b] -thiazole a) 7-methanesulfonylimidazo [5, 1-b] - thiazole Substantially identical to example 12-a), 0.94 g of 7-methanesulfonylimidazo [5, 1-b] -thiazole was obtained from 2.50 g of 7-iodoimidazo [5, 1-b] -thiazole and 0.81 ml of methanesulfonyl chloride. NMR (CDCl 3) d: 3.20 (3H, s), 7.09 (1H, d, J = 4.2 Hz), 7.61 (1H, d, J = 4.2 Hz), 8.10 (1H, s) b) 7-methanesulfonyl-3 - (tri-n-butylstannyl) imidazo [5, 1-b] -thiazole A 1.6 N solution of n-butyllithium / n-hexane (0.7 ml) was added to a solution of 202 mg of 7-methanesulfonylimidazo [5, 1 -b] -thiazole in 20 ml of anhydrous THF in an argon atmosphere at a temperature of -70 ° C. The mixture was stirred at the same temperature for 30 minutes. Tri-n-butylstannyl chloride (0.3 ml) was added there. A saturated aqueous solution of ammonium chloride was added to the reaction mixture. Ethyl acetate was then added. The mixture was washed with water and a saturated saline solution in this order. The organic layer was dried in anhydrous magnesium sulfate. The solvent was removed by distillation. The residue was purified by column chromatography on silica gel (hexane: ethyl acetate = 2: 1) to provide 110 mg of the title compound. NMR (CDC13) d: 0.85-0.95 (9H, m), 1.25-1.40 (12H, m), 1.50-1.60 (6H, m), 3.20 (3H, s), 6.81 (1H, s), 7.95 (1H , s) Preparation 12 7-methylthio-2- (tri-n-butylstannyl) imidazo [5, 1-b] -thiazole a) 7-methylthioimidazo [5, 1-b] -thiazole A 1 N solution of ethylmagnesium bromide / THF (1.4 ml) was added under cooling with ice to a solution of 0.31 g of 7-iodoimidazo [5, 1-b] -thiazole in 3 ml of anhydrous THF under an argon atmosphere. The mixture was stirred at the same temperature for one hour. Methyl methantiolsulfonate (0.15 ml) was added. The mixture was stirred at room temperature for 12 hours, a saturated aqueous solution of ammonium chloride was added to the reaction solution, ethyl acetate was added thereto, the mixture was washed with a dilute aqueous sodium thiosulfate solution. and saturated saline solution in this order.The organic layer was dried over anhydrous magnesium sulfate.The solvent was removed by distillation.The residue was purified by silica gel column chromatography (ethyl acetate) to give 0.15 g of 7- methylthioimidazo [5, 1-b] thiazole, NMR (CDC1) d: 2.41 (3H, s), 6.86 (1H, d, J = 4.2 Hz), 7.39 (1H, d, J = 4.2 Hz), 8.00 (1H , s) b) 7-methylthio-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole Substantially in the same manner as in preparation 4-b), 1.50 g of the title compound was obtained from 0.79 g of 7-methylthioimidazo [5, 1-b] thiazole. NMR (CDCI3) d: 0.92 (9H, t, J = 7.2 Hz), 1.15 (6H, t, J = 8.4 Hz), 1.30 - 1.40 (6H, m), 1.55 - 1.65 (6H, m), 2.40 ( 3H, s), 7.13 (1H, s), 7.94 (1H, s) Preparation 13 7- ethanesulfonylimidazo-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole a) 7-ethanesulfonylimidazo [5, 1-b] thiazole A solution of 725 g of 7-ethanesulfonylimidazo [5, 1-b] thiazole in 35 ml of THF was cooled in an argon atmosphere at a temperature of -70 ° C. It was added dropwise to the At the same temperature a 1 N solution of lithium (trimethylsilyl) amide / THF (3.9 ml). The mixture was stirred for 30 minutes. Then 0.25 ml of methyl iodide was added. The mixture was stirred at the same temperature for 70 minutes. A saturated aqueous solution of sodium chloride was added, followed by extraction four times with ethyl acetate. The extract was dried in anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was chromatographed on silica gel (ethyl acetate: methanol = 9: 1) to give 0.79 g of 7-ethanesulfonylimidazo [5, 1-b] thiazole. NMR (CDC13) d: 1.34 (3H, t, J = 7.4 Hz), 3.33 (2H, q, J = 7.4 Hz), 7.07 (1H, d, J = 4.3 Hz), 7.55 (1H, s), 8.08 (1H, s) b) 7- ethanesulfonyl-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole A solution of 669 mg of 7- ethanesulfonylimidazo-2- (tri-n- butylstannyl) imidazo [5, 1-b] thiazole in 30 ml of THF was cooled to a temperature of -40 ° C in an argon atmosphere. A 1.6 N solution of butyllithium / n-hexane (4.3 ml) was added dropwise at the same temperature. The mixture was stirred for 15 minutes. Tri-n-butylstannyl chloride (0.88 ml) was added, followed by stirring at the same temperature for 10 minutes. A saturated aqueous solution of ammonium chloride was added. The mixture was extracted twice with ethyl acetate. The extract was dried in anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography on silica gel (hexane: ethyl acetate = 1: 1). The title compound (1.54 g) was obtained from the fraction of Rf = 0.2. NMR (CDCl 3) d: 0.92 (9H, t, J = 7.1 Hz), 1.22 (6H, m), 1.38 (9H,), 1.58 (6H, m), 3.31 (2H, q, J = 7.4 Hz), 7.26 (1H, s), 8.00 (1H, s) Preparation 14 7- (N-methylsulfamoyl) -2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole a) 7- (N-methylsulfamoyl) imidazo [5, 1-b] thiazole Substantially in the same manner as in Example 25-b), 0.34 g of 7- (N-methylsulfamoyl) imidazo [5, 1-b] thiazole was obtained from 0.36 g of 7- chlorosulfonylimidazo [5, 1-b] thiazole and 10 ml of a 2 N solution of methylamine / THF. NMR (CDC13) d: 2.71 (3H, d, J = 5.4 Hz), 4.76-4.85 (1H, m), 7.04 (1H, d, J = 4.1 Hz), 7.53 (1H, d, J = 4.1 Hz) , 8.06 (1H, s) b) 7- (N-methylsulfamoyl) -2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole A 1.6 N solution of n-butyllithium / n-hexane was added ( 1.6 ml) to a solution of 0.26 g of 7- (N-methylsulfamoyl) imidazo [5, 1-b] thiazole in 8 ml of dry THF and 4 ml of HMPA in an argon atmosphere at a temperature of -50 ° C. The mixture was stirred at the same temperature for 30 minutes. Tri-n-butylstannyl chloride (0.34 ml) was added. The mixture was stirred for 30 minutes, a solution of 1.6 N of n-butyllithium / n-hexane (0.8 ml) was added, the mixture was stirred for 30 minutes, and tri-n-butylstannyl chloride (0.2 ml) was added. ), followed by stirring at the same temperature for 30 minutes, a saturated aqueous solution of ammonium chloride was added, then ethyl acetate was added, followed by washing with water and saturated saline in that order. Anhydrous magnesium sulfate The solvent was removed by distillation The residue was purified by column chromatography on silica gel (hexane: ethyl acetate = 1: 2) to give 0.39 g of the title compound. NMR (CDC13) d: 0.92 (9H, t, J = 7.2 Hz), 1.18 (6H, t, J = 8.5 Hz), 1.30 - 1.40 (6H, m), 1.53 - 1.60 (6H, m), 2.71 (3H, d, J = 5.4 Hz), 4.65-4.72 (1H, m), 7.24 (1H, s), 7.98 (1H, s) Preparation 15 7-p-Toluenesulfonyl-2- (tri-n-butylstannyl) imidazo [5, 1-b ] thiazole ) 7- p-Toluenesulfonylimidazo [5, 1-b] thiazole A solution of 23.9 g of p-toluenesulfonyl chloride in 100 ml of dichloromethane was cooled to ice temperature under an argon atmosphere. Aluminum chloride (15.3 g) was added. The mixture was stirred for 10 minutes. A solution of 3.15 g of imidazo [5, 1-b] thiazole in 25 ml of dichloromethane was added dropwise. The mixture was stirred for 22 hours. Dichloromethane (200 ml), 70 ml of water, 75 g of a sodium carbonate powder were added, followed by extraction The extract was dried over anhydrous magnesium sulfate The solvent was removed by distillation under reduced pressure to provide 995 mg of 7-toluenesulfonylimidazo [5, 1-b] thiazole.

NMR (CDCl 3) d: 0.92 (3H, s), 7.40 (2H, d, J = 8.3 Hz), 7.46 (1H, d, J = 4.1 Hz), 7.76 (2H, d, J = 8.3 Hz) 8.03 ( 1H, d, J = 4.1 Hz), 8.34 (1H, s) b) 7-p-toluenesulfonyl-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole A solution of 669 mg of 7- p-Toluenesulfonylimidazo [5, 1-b] thiazole in 65 ml of THF was cooled to a temperature of -60 ° C under an argon atmosphere. A 1.6 N solution of n-butylithium / n-hexane (2.5 ml) was added dropwise at the same temperature. The mixture was stirred for 20 minutes. A solution of 1.25 g of tri-n-butylstannyl chloride in 10 ml of THF was added, and the mixture was stirred at the same temperature for 40 minutes. A half-saturated aqueous solution of ammonium chloride (150 ml) was added, followed by extraction with 250 ml of ethyl acetate. The extract was dried in anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography on silica gel (hexane: ethyl acetate = 1: 1). The title compound (590 mg) was obtained from the fraction of Rf = 0.4.

NMR (CDCl 3) d: 0.92 (9H, t, J = 7.3 Hz), 1.83 (6H, m), 1.35 (6H, m), 1.56 (6H, m), 2.39 (3H, s), 7.20 (1H, s), 7.29 (2H, d, J = 8.4 Hz), 7.91 (1H, s), 7.97 (2H, d, J = 8.4 Hz) Preparation 16 7-t-Butylmethylsilyloxyacetyl-3- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole and 7-t-butyldimethylsilyloxyacetyl-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole a) 7-acetoxyacetylimidazo [5, 1-b] thiazole was dissolved. - acetylimidazo [5, 1-b] thiazole (2.49 g) in a solution of 150 ml of THF and 30 ml of HMPA. A 1.0 N solution of lithium (trimethylsilyl) amide THF (18 ml) was added dropwise to the solution under an argon atmosphere at a temperature of -70 ° C. The mixture was stirred at the same temperature for 30 minutes. Trimethylsilyl chloride (2.28 ml) was added dropwise. The mixture was stirred at the same temperature for 30 minutes. A solution of 3.21 g of N-bromosuccinimide in 90 ml of THF was added dropwise. The mixture was stirred for 2 hours while the temperature was raised to room temperature. Ethyl acetate (400 ml) was added to the reaction solution. The mixture was washed twice with saline, dried over anhydrous magnesium sulfate, and filtered. The solvent was removed by distillation under reduced pressure. The residue was dissolved in 120 ml of DMF. Sodium acetate (1.48 g) was added to the solution. The mixture was stirred at room temperature for 14 hours and then at a temperature of 60 ° C for 4 hours. The reaction solution was concentrated under reduced pressure until the amount of the solution was half. A saline solution (200 ml) was added to the concentrate, followed by extraction twice with 300 ml of ethyl acetate. The organic layers were combined together, washed three times with saline, dried over anhydrous magnesium sulfate, and filtered. The solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography on silica gel (eluting with dichloromethane: ethyl acetate = 1: 1 and then with ethyl acetate) to provide 2.11 g of 7- acetoxyacetylimidazo [5, 1-b] thiazole. NMR (CDC1) d: 2.24 (3H, s), 5.44 (2H, s), 7.13 (1H, d, J = 4.1 Hz), 7.57 (1H, d, J = 4.1 Hz), 8.00 (1H, s) b) 7- hydroxyacetylimidazo [5, 1-b] thiazole. 7-acetoxyacetylimidazo [5, 1-b] thiazole (24.6 mg) was dissolved in 2 ml of ethanol and 0.5 ml of water. Potassium carbonate (17.3 mg) was added under cooling with ice to the solution. The mixture was stirred for 45 minutes. Methanol was removed by distillation under reduced pressure. Water (10 ml) was added to the residue followed by extraction five times by dichloromethane. The extract was dried over anhydrous magnesium sulfate, and then filtered. The solvent was removed by low pressure distillation to provide 18.8 mg of 7- hydroxyacetylimidazo [5, 1-b] thiazole. • NMR (CDCI3) d: 3.55 (1H, t, J = 4.7 Hz), 4.92 (2H, d, J = 4.7 Hz), 7.16 (lH / d, J = 4.1 Hz), 7.60 (1H, d, J = 4.1 Hz), 8.03 (1H, s) c) 7-Butyldimethylsilyloxyacetylimidazo [5, 1-b] thiazole 7-Hydroxyacetylimidazo [5, 1-b] thiazole (1.42 g) was dissolved in 10 ml of DMF. Imidazole (847 mg) and 1.77 g of t-butyldimethylsilyl chloride were added to the solution under an argon atmosphere. The mixture was stirred at room temperature for 24 hours. A saline solution was added to the reaction solution, followed by extraction twice with ethyl acetate. The organic layers were combined together, washed with saline, dried in anhydrous magnesium sulfate, and then filtered. The solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography on silica gel (hexane: ethyl acetate = 1: 1) to provide 2.19 g of 7-butyldimethylsilyloxyacetylimidazo [5, 1-b] thiazole. NMR (CDC13) d: 0.16 (6H, s), 0.97 (9H, s), 5.10 (2H, s), 7.11 (1H, d, J = 4.2 Hz), 7.55 (1H, d, J = 4.2 Hz) , 7.98 (1H, s) d) 7-butyldimethylsilyloxyacetylimidazo-3- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole and 7-butyldimethylsilyloxyacetylimidazo-3- (tri-n-butylstannyl) imidazo [5, 1 -b] thiazole Tri-n-butylstannyl chloride (2.97 ml) and 16.0 ml of a 1.0 N solution of lithium (trimethylsilyl) amide / THF were added dropwise in this order to a solution of 2.37 g of 7-butyldimethylsilyloxyacetylimidazo [ 5, 1-b] thiazole in 80 ml of THF in an argon atmosphere at a temperature of -73 ° C. The mixture was stirred at the same temperature for 30 minutes. A solution of ammonium chloride was added to the reaction solution followed by extraction with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and then filtered. The solvent was removed by distillation under reduced pressure. The residue was purified by silica gel column chromatography (hexane: ethyl acetate = 5: 1 to 2: 1) of the two main components, the fraction that had been eluted earlier was collected to provide 2.84 mg of 7- butyldimethylsilyloxyacetylimidazo-3- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole. NMR (CDC13) d: 0.16 (6H, s), 0.92 (9H, t, J = 7.1 Hz), 0.97 (9H, s), 1.31 (12H, m), 1.60 (6H, m), 5.10 (2H, s), 6.88 (1H, s), 7.85 (1H, s) Of the two main components, the fraction that had been eluded subsequently was collected to provide 3.51 g of 7-butyldimethylsilyloxyacetylimidazo-3- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole. NMR (CDCl 3) d: 0.15 (6H, s), 0.91 (9H, t, J = 7.2 Hz), 0.96 (9H, s), 1.18 (6H, m), 1.35 (6H, m), 1.56 (6H, m), 5.08 (2H, s), 7.27 (1H, s), 7.91 (1H, s) Preparation 17 7- benzoyl-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole a) 7 - benzoylimidazo [5, 1-b] thiazole Aluminum chloride (5.33 g) was added to a solution of 4.64 ml of benizoyl chloride in 50 ml of carbon disulfide.

A solution of 1.24 g of imidazo [5,1-b] thiazole in 50 ml of dichloromethane there was added dropwise. The mixture was stirred at room temperature for 2 h. The reaction solution was poured into 50 g of ice. Dichloromethane (100 ml) was added thereto. Sodium carbonate (16.7 g) and 16.7 g of sodium sulfate were added in this order to the mixture with stirring. The insoluble particles were removed by filtration through Celite, and then washed with dichloromethane. The filtrate was concentrated under reduced pressure. The mixture was purified by column chromatography on silica gel (hexane: ethyl acetate = 5: 1 to dichloromethane: ethyl acetate: 2: 1) to provide 1.39 mg of 7- benzoylimidazo [5, 1-b] thiazyl. NMR (CDC13) d: 7.16 (1H, d, J = 4.1 Hz, 7.54 (3H, m), 7.60 (1H, d, J = 4.1 Hz), 8.09 (1H, s), 8.54 (2H, m) In the same manner as in preparation 16-d), 2.59 g of the title compound was obtained from 1.39 g of 7-benzoylimidazo [5, 1-b] thiazole. NMR (CDCl 3) d: 0.92 (9H, t, J = 7.2 Hz, 1.21 (6H, m), 1.36 (6H, m), 7.34 (1H, s), 7.53 (3H, m), 8.03 (1H, s) ), 8.51 (2H, m) Preparation 18 7- (4-Nitrobenzylsulfamoyl) -2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole a) 7- (4-nitrobenzylsulfamoyl) imidazo [5, 1-b] thiazole 4-nitrobenzylamine (1.24 g) and 2 ml of diisopropylethylamine were added to a solution of 0.95 g of 7-chlorosulfonylimidazo [5, 1-b] thiazole in 20 ml of DMF. The mixture was stirred at room temperature for 12 hours. Ethyl acetate was added to the reaction mixture. The mixture was washed with water and saturated saline in this order. The organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated, and the resulting powder was collected by filtration to provide 1.07 g of 7- (4-nitrobenzylsulfamoyl) imidazo [5, 1-b] thiazole. NMR (DMSO-De) d: 4.18 (2H, s), 7.36 (1H, d, J = 4.2 Hz), 7.47 (1H, d, J = 12.0 Hz), 7.95 (1H, d, J = 4.2 Hz) , 8.07 (1H, d, J = 4.2 Hz), 8.30 (1H, s), 8.44 (1H, s) b) 7- (4-nitrobenzylsulfamoyl) -2- (tri-n-butylstannyl) imidazo [5, 1 -b] thiazole A 1.0 N solution of lithium (trimethylsilyl) amide / n-hexane (4.8 ml) was added to a solution of 0.68 g of 7- (4-nitrobenzylsulfamoyl) imidazo [5, 1-b] thiazole in 20 ml of THF and 4 ml of HMPA in an argon atmosphere at a temperature of -40 ° C. The mixture was stirred at the same temperature for 30 minutes. Tri-n-butylstannyl chloride (0.57 ml) was added there. The mixture was stirred at the same temperature for 30 minutes. A saturated aqueous solution of ammonium chloride was added thereto. Ethyl acetate was then added. The mixture was then washed with water and a saturated saline solution in this order. The organic layer was dried over anhydrous magnesium sulfate. The solvent was removed by distillation. The residue was purified by column chromatography on silica gel (hexane: ethyl acetate = 1: 1) to give 0.78 g of the title compound. NMR (CDC13) d: 0.92 (9H, t, J = 7.2 Hz), 1.19 (6H, t, J = 8.4 Hz), 1.30 - 1.40 (6H, m), 4.33 (2H, t, J = 6.4 Hz) , 6.25 (2H, d, J = 6.4 Hz), 7.17 (1H, s), 7.49 (2H, d, J = 11.0 Hz), 7.90 (1H, s), 8.07 (2H, d, J = 11.0 Hz) Preparation 19 7-Fluoro-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole a) 7-Fluoroimidazo [5, 1-b] thiazole N-Fluoro-N '- (chloromethyl) triethylene diaminebis was added (tetrafluoroborane) (11 ~ g) to a solution of 2.0 g of imidazo [5, 1-b] thiazole in 90 ml of 1,2-dichloroethane under an argon atmosphere. The mixture was stirred at room temperature for 6 hours. A saturated aqueous sodium hydrogencarbonate solution was added there, followed by extraction with dichloromethane and washing with saturated saline solution. The extract was dried over anhydrous magnesium sulfate and then filtered. The solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography on silica gel (dichloromethane: ethyl acetate = 40: 1) to give 457 mg of 7-fluoroimidazo [5, 1-b] thiazole.

NMR (CDCl 3) d: 6.80 (1H, t, J = 4.2 Hz), 7.32 (1H, dd, J. = 4.2 Hz, J2 = 1.7 Hz), 7.59 (1H, s) b) 7-fluoro-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole. A 1.0 N solution of lithium (trimethylsilyl) amide / THF (3.2 ml) and 0.75 ml of tri-n-butylstannyl chloride was added in this order to a solution of 7-fluoroimidazo [5, 1-b] thiazole in dry THF under an argon atmosphere at -78 ° C. The mixture was stirred at the same temperature for 10 minutes. Water was added, followed by extraction with ethyl acetate and washing with a saturated saline solution. The extract was dried over anhydrous magnesium sulfate and then filtered. The solvent was removed by distillation under reduced pressure. The residue was purified by silica gel column chromatography (hexane: ethyl acetate = 40: 1) to provide 820 mg of the title compound. NMR (CDCl 3) d: 0.94 (9H, t, J = 7.4 Hz), 1.15 (6H, m), 1.35 (6H, m), 1.57 (6H, m), 7.04 (1H, d, J = 1.7 Hz) 7.51 (1H, s) Preparation 20 7- [N- (2-hydroxyethyl) -N-methyl] sulfamoyl-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole a) 7- [ N- (2-hydroxyethyl) -N-methyl] sulfamoylimidazo- [5, 1-b] thiazole Substantially in the same manner as in Example 27-a), 1.11 g of 7- [N- (2-hydroxyethyl ) -N-methyl] sulfamoylimidazo- [5, 1-b] thiazole from 1.05 g of 7-chlorosulfonylimidazo [5, 1-b] thiazole and 0.46 g of N-methylethanolamine. NMR (CDC13) d: 2.88 (3H, s), 3.57 (2H, t, J = 4.5 Hz), 3.80 -3.90 (2H, m), 4.35 (1H, m), 4.30-4.40 (1H, m), 7.07 (1H, d, J = 4.2 Hz), 7.55 (1H, d, J = 4.2 Hz), 8.05 (1H, s) b) 7- [N- (2-t-butyldimethylsilyloxyethyl) -N-methyl] sulfamoylimidazole - [5, 1-b] thiazole t-Butyldimethylsilyl chloride (0.33 g) and 0.16 g of imidazole were added to a solution of 0.52 g of 7- [N- (2-hydroxyethyl) -N-methyl] sulfamoylimidazo- [ 5, 1-b] thiazole in 20 ml of dichloromethane. The mixture was stirred at room temperature for 30 minutes. Ethyl acetate was added to the reaction mixture. The mixture was washed with water and a saturated saline solution in this order. The organic layer was dried over anhydrous magnesium sulfate. The solvent was removed by distillation. The residue was purified by column chromatography on silica gel (hexane: ethyl acetate = 1: 1) to provide 0.87 g of 7- [N- (2-t-butyldimethylsilyloxyethyl) -N-methyl] sulfamoylimidazo- [5, 1-b] thiazole NMR (CDCI3) d: 0.05 (3H, s), 0.06 (3H, s), 0.88 (9H, s), 2.99 (3H, s), 3.33 (2H, t, J = 5.8 Hz) , 3.84 (2H, t, J = 5.8 Hz), 7.02 (1H, d, J = 4.1 Hz), 7.53 (1H, d, J = 4.1 Hz), 8.03 (1H, s) c) 7- [N- (2-t-butyldimethylsilyloxyethyl) -N-methyl] sulfamoyl-2- (tri-n-butylstannyl) imidazo- [5, 1-b] thiazole Substantially in the same manner as in example 4-b), 0.54 was obtained g of the title compound from 0.45 g of 7- [N- (2-t-butyldimethylsilyloxyethyl) -N-methyl] sulfamoylimidazo- [5, 1-b] thiazole. NMR (CDC13) d: 0.06 (6H, s), 0.85 - 0.95 (21H, m), 1.15-1.21 (6H, m), 1.30 - 1.40 (6H, m), 1.55 - 1.65 (6H, m), 2.99 (3H, s), 3.32 (2H, t, J = 6.0 Hz), 3.83 (2H, t, J = 6.0 Hz), 7.24 (1H, s), 7.96 (1H, s) Preparation 21 7- acetylaminoacetyl-2 - (tri-n-butylstannyl) imidazo [5, 1-b] thiazole a) 7- acetylaminoacetylimidazo [5, 1-b] thiazole A solution of (17 ml) of 10% hydrochloric acid in methanol and 800 mg of 10 % Pd-C were added to a solution of 1.78 g of 7- azidaacetylimidazo [5, 1-b] thiazole in 85 ml of methanol and 85 ml of THF. The atmosphere in the reactor was replaced by hydrogen. The system was stirred at room temperature for 58 hours. The catalyst was removed by filtration through Celite and washed with methanol. The solvent was removed by distillation. The residue was dissolved in 50 ml of DMF. Pyridine (3.43 ml) and 1.22 acetic anhydride were added to the solution under cooling with ice. The mixture was stirred at the same temperature _ for 2 hours. Dichloromethane and a saline solution were added to the reaction solution. The mixture was adjusted to a pH of 10 by the addition of potassium carbonate. The organic layer was separated. The aqueous layer was further extracted 5 times with dichloromethane. The organic layers were combined together, dried in anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (dichloromethane: methanol 40: 1 to 20: 1) to provide 397 mg of 7- acetylaminoacetylimidazo [5, 1-b] thiazole. NMR (CDC13) d: 2.10 (3H, s), 4.82 (2H, d, J = 4.7 Hz), 6.50 (1H, br), 7.14 (1H, d, J = 4.1 Hz), 7.58 (1H, d, J = 4.1 Hz), 8.01 (1H, s) b) 7- acetylaminoacetyl-2-vri-n-butylstannyl) imidazo [5, 1-b] thiazole 7-Acetylaminoacetylimidazo [5, 1-b] thiazole was dissolved (397 mg) in 40 ml of THF and 8 ml of HMPA. Tri- n-butylstannyl chloride (0.76 ml) and 7.1 ml of a 1 N solution of lithium (trimethylsilyl) amide / THF were added dropwise in this order in an argon atmosphere at a temperature of -73 ° C. The mixture was stirred at the same temperature for 1 hour. A solution of ammonium chloride was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed twice with saline, dried over anhydrous magnesium sulfate, and then filtered. The solvent removed by distillation under reduced pressure. The residue was purified by column chromatography on silica gel (eluting with ethyl acetate and then with dichloromethane: methanol 20: 1) to give 152 mg of the title compound. NMR (CDC1) d: 0.91 (9H, t, J = 7.2 Hz), 1.20 (6H, m), 1.35 (6H, m), 1.56 (6H, m), 2.09 (3H, s), 4.79 (2H, d, J = 4.5 Hz), 6.58 (1H, br), 7.31 (1H, s), 7.96 (1H, s) Preparation 22 5-methyl-7-methylthio-3- (tri-n-butylstannyl) imidazo [5 , 1-b] thiazole and 5-methyl-7-methylthio-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole a) 7-iodo-5-methylimidazo [5, 1-b] thiazole 5-Methylimidazo [5, 1-b] thiazole (6.90 g) was dissolved in 500 ml of dichloromethane. N-iodosuccinamide (10.6 g) was added to the solution. The mixture was stirred at room temperature for 24 hours. N-iodosuccinamide (1.06 g) was added thereto followed by stirring for an additional 1 hour. The reaction solution was washed with an aqueous solution of sodium thiosulfate and a saline solution, in this order, dried over anhydrous magnesium sulfate, and then filtered. The solvent removed by distillation under reduced pressure. The residue was dissolved in 200 ml of dichloromethane and 100 ml of ethyl acetate. Silica gel (30 g) was added to the solution. The mixture was stirred. The silica gel was removed by filtration. The filtrate was washed with 200 ml of a mixed solution of dichloromethane: ethyl acetate 2: 1. The filtrate was concentrated under reduced pressure to provide 13.08 g of 7-iodo-5-methylimidazo [5, 1-b] thiazole. NMR (CDC13) d: 2.58 (3H, s), 6.83 (1H, d, J = 4.2 Hz), 7.29 (1H, d, J = 4.2 Hz) b) 5-methyl-7-methylthioimidazo [5, 1- b] thiazole Substantially in the same manner as in example 12-a), 3.56 of 5-methyl-7-methylthioimidazo [5, 1-b] thiazole was obtained from 5.28 g of 7-iodo-5-methylthioimidazo [ 5, 1-b] thiazole. NMR (CDCI3) d: 2.40 (3H, s), 2.56 (3H, s), 6.81 (1H, d, J = 4.2 Hz), 7.20 (1H, d, J = 4.2 Hz) c) 5-methyl-7 -methylthio-3- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole and 5-methyl-L-7-methylthio-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole was dissolved 5-methyl-7-methylthioimidazo [5, 1-b] thiazole (3.34 g) in 150 ml of THF. A 1.59 solution of N-butyllithium / n-hexane (22.8 ml) was added dropwise to the solution under an argon atmosphere at a temperature of -73 ° C. The mixture was stirred at the same temperature for 40 minutes. Tri-n-butylstannyl chloride (6.39 ml) was added thereto, followed by stirring at the same temperature for 1 hour. A solution of ammonium chloride was added to the reaction solution. The mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and then filtered. The solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography on silica gel (hexane: ethyl acetate = 2: 1 to 1: 1). Of the two main components, the fraction that had been eluted before was collected to provide 598 mg of 5-methyl-7-methylthio-3- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole. NMR (CDC13) d: 0.92 (9H, t, J = 7.3 Hz), 1.15 (6H, m), 1.35 (6H, m), 1.57 (6H, m), 2.39 (3H, s), 2.56 (3H, s), 6.92 (1H, S) Of the two main components, the fraction that had been eluded was then collected to provide 6.04 g of 5-methyl-7-methylthio-3- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole NMR (CDCl 3) d: 0.92 (9H, t, J = 7.3 Hz), 1.15 (6H, m), 1.35 (6H, m), 1.57 (6H,), 2.39 (3H, s), 2.56 (3H, s), '6.92 (1H, s) Preparation 23 7- N-Acetylaminomethyl-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole a) 7-N-acetylaminomethylimidazo [5, 1-b] thiazole Hydrazine monohydrate (0.34 ml) was added to a solution of 0.63 g of 7-phthalimidomethylimidazo [5, 1-b] thiazole in 15 ml of ethanol. The mixture was heated under reflux for 1 hour. The system was cooled to room temperature. The insoluble particles were removed by filtration. The solvent was removed by distillation. DMF (10 ml), 2 ml of pyridine and 1 ml of acetic anhydride were added to the residue. The mixture was stirred at room temperature for 30 minutes. Methanol (5 ml) was added there. The solvent was removed by distillation. The residue was purified by column chromatography on silica gel (dichloromethane: methanol = 20: 1) to provide 0.41 g of 7-N-acetylaminomethylimidazo [5, 1-b] thiazole. NMR (CDC13) d: 2.02 (3H, s), 4.49 (2H, d, J = 5.5 Hz), 6.25 (1H, s), 6.83 (2H, d, J = 4.2 Hz), 7.37 (2H, d, J = 4.2 Hz), 7.93 (1H, s) b) 7- N-acetylaminomethyl-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole A 1.6_N solution of n-butyllithium / n-hexane (2.5 ml) to a solution of 0.24 g of 7- N-acetylaminomethylimidazo [5, 1-b] thiazole in 10 ml of dry THF and 2 ml of HMPA in an argon atmosphere at a temperature of -50 ° C. The mixture was stirred at the same temperature for 30 minutes. Added "tri-n-butylstannyl chloride (0.36 ml) there, followed by stirring for 30 minutes, a saturated aqueous solution of ammonium chloride was added thereto, then ethyl acetate was added, followed by washing with water and saline. The organic layer was dried over anhydrous magnesium sulfate, the solvent was removed by distillation, and the residue was purified by silica gel column chromatography (dichloromethane: methanol = 50: 1) to give 0.42. g of the title compound: NMR (CDC13) d: 0.91 (9H, t, J = 7.3 Hz), 1.14 (6H, t, J = 8.4 Hz), 1.30 - 1.40 (6H, m), 1.50 - 1.60 (6H , m), 2.02 (3H, s), 4.48 (2H, d, J = 5.3 Hz), 6.10 (1H, s), 7.12 (1H, s), 7.88 (1H, s) Preparation 24 7-N, N -dimethylcarbamoylacetyl-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole a) 7- [(2-N, N-dimethylcarbamoylacetyl-l-hydroxy) ethyl] imidazo [5, 1-b] thiazole Dimethylacetamide (0.97 ml) was added to 10 ml of a 1.0 N solution of litiumbis (tr imethylsilyl) amide / THF to the solution under an argon atmosphere at a temperature of -70 ° C. The mixture was stirred at the same temperature for 30 minutes. A solution of 1.52 g of 7-formiimidazo [5, 1-b] thiazole in 40 ml of dry THF was added there. The mixture was stirred at the same temperature for 30 minutes. A saturated aqueous solution of ammonium chloride was added thereto. Ethyl acetate was then added, followed by washing with water and saturated saline in this order. The organic layer was dried over anhydrous magnesium sulfate. The solvent was removed by distillation. The residue was purified by column chromatography on silica gel (dichloromethane: methanol = 20: 1) to provide 1.04 g of 7 - [(2-N, N-dimethylcarbamoylacetyl-1-hydroxy) ethyl] imidazo [5, 1-] b] thiazole NMR (CDC13) d: 2.80 (1H, m), 2.97 (3H, s), 3.03 - 3.10 (1H, m), 5.06 (1H, t, J = 3.6 Hz), 5.27 - 5.35 (1H, m), 6.81 (1H, d, J = 4.1 Hz), 7.35 (1H, d, J = 4.1 Hz), 7.92 (1H, s) b) 7-N, N-dimethylcarbamoylacetylimidazo [5, 1-b] thiazole Manganese dioxide (2.84 g) was added to a solution of 1.04 g of 7- [(2-N), N-dimethylcarbamoylacetyl-l-hydroxy) ethyl] imidazo [5, 1-b] thiazole in 30 ml of dichloromethane. The mixture was stirred at room temperature for 12 hours. Manganese dioxide was removed by filtration. The solvent was removed by distillation. The residue was purified by column chromatography on silica gel (dichloromethane: methanol = 20: 1) to provide 0.98 g of 7-N, N-dimethylcarbamoylacetylimidazo [5, 1-b] thiazole. NMR (CDCl 3) d: 3.01 (3H, s), 3.09 (3H, s), 4.18 (2H, s), 7.11 (1H, d, J = 4.1, Hz), 7.56 (1H, d, J = 4.1 Hz ), 8.00 (1H, s) c) 7-N, N-dimethylcarbamoylacetyl-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole A 1.0 N solution of lithium (trimethylsilyl) amide / THF was added (2.1 ml) to a solution of 0.24 g of 7-N, N-dimethylcarbamoylacetimidazo [5, 1-b] thiazole in 5 ml of dry THF under argon at a temperature of -50 ° C. The mixture was stirred at the same temperature for 30 minutes. Tri-n-butylstannyl chloride (0.29 ml) was added thereto. The mixture was stirred for 30 minutes. A saturated aqueous solution of ammonium chloride was added thereto. Ethyl acetate was then added, followed by washing with water and saturated saline in this order. The organic layer was dried over anhydrous magnesium sulfate. The solvent was removed by distillation. The residue was purified by column chromatography on silica gel (dichloromethane: methanol = 20: 1) to provide 0.29 g of the title compound. NMR (CDC13) d: 0.91 (9H, t, J = 7.1 Hz), 1.18 (3H, t, J = 8.3 Hz), 1.30 - 1.40 (6H, m), 1.53 - 1.65 (6H, m), 3.00 ( 3H, s), 3.07 (3H, s), 4.18 (2H, s), 7.27 (1H, s), 7.94 (1H, s) Preparation 25 7-N, N-dimethylsulfamoyl-2- (tri-n-butylstannyl ) imidazo [5,1-b] thiazole a) 7-chlorosulfonylimidazo [5, 1-b] thiazole A solution of chlorosulfuric acid in 20 ml of carbon tetrachloride was added under cooling with ice to a solution of 11.18 g of imidazo [ 5, 1-b] thiazole in 200 ml of carbon tetrachloride. The reaction mixture was heated under reflux for 6 hours. Water was added there with cooling with ice to finish the reaction. The mixture was extracted with dichloromethane. The organic layers were combined together. The combined organic layers were washed with a dilute aqueous solution of sodium hydroxide and a saturated saline solution in this order and then dried over anhydrous magnesium sulfate. The solvent was removed by distillation. Isopropyl ether was added to the residue. The resulting powder was collected by filtration to provide 4.01 g 7-chlorosulfonylimidazo [5, 1-b] thiazole. NMR (CDCls) d: 7.19 (1H, d, J = 4.1, Hz), 7.65 (1H, d, J = 4.1 Hz), 8.12 (1H, s) b) 7-N, N-dimethylsulfamoylimidazo [5, 1 -b] thiazole A solution of 2 N THF (6 ml) of dimethylamine was added while cooling with ice to a solution of 1.11 g of 7- chlorosulfonylimidazo [5, 1-b] thiazole in 20 ml of THF. Mix was stirred at room temperature for 30 minutes. Dichloromethane was added there, followed by washing with water and a saturated saline solution in this order. The organic layer was dried over anhydrous magnesium sulfate. The solvent was removed by distillation. Ethyl acetate was added to the residue. The resulting powder was collected by filtration to provide 1.10 g of 7-N, N-dimethylsulfamoylimidazo [5 ~, 1-b] thiazole. NMR (CDCl 3) d: 2.87 (6H, s), 7.03 (1H, d, J = 4.2, Hz), 7.54 (1H, d, J = 4.2 Hz), 8.05 (1H, s) c) 7- N, N-dimethylsulfamoyl-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole Substantially from the same mamary as in preparation 4-b), 1.11 g of the title compound was obtained from 1.22. g of 7-N, N-dimethylsulfamoylimidazo [5, 1-b] thiazole. NMR (CDC13) d: 0.92 (9H, t, J = 7.2 Hz), 1.15 - 1.22 (6H, m), 1.30 - 1.40 (6H, m), 1.56 - 1.63 (6H, m), 2.86 (6H, s ), 7.26 (1H, s), 7.97 (1H, s) Preparation 26 2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole-7-carboxylic acid a) imidazo [5, 1-] b] thiazole-7-carboxylic acid A 0.95 N solution of ethylmagnesium bromide / THF (12.6 ml) was added dropwise to a solution (50 ml) of 2,501 g of 7-iodoimidazo [5, 1-b] thiazole in THF at a temperature of -70 ° C. The mixture was stirred for .30 minutes. Carbon dioxide (which had been emitted from 5 g of dry ice and passed through a calcium chloride tube) was introduced into the reaction solution at the same temperature for a period of 40 minutes. The reaction solution was allowed to stand at a temperature of -20 ° C overnight and then an ice cold mixed solution composed of an aqueous solution (100 ml) of sodium hydroxide (0.41 g) and ether (200 ml) was added. ) with agitation. The mixture was stirred for 1 hour. The organic layer was separated and concentrated under the reduced pressure by a minor amount and the remaining organic solvent was removed by distillation.

The residue was adjusted to a pH of 3.5 by the addition of 2N hydrochloric acid with ice cooling. The resulting precipitate was washed with a minor amount of cold water, and then dried under reduced pressure to provide 1,407 g of imidazo [5, 1-b] thiazole-7-carboxylic acid. NMR (DMSO-Dβ) d: 7.44 (1H, d, J = 4.1 Hz), 8.03 (1H, d, J = 4.1 Hz), 8.29 (1H, s) b) imidazo [5, 1-b] thiazole- Methyl 7-carboxylate Imidazo [5, 1-b] thiazole-7-carboxylic acid (0.680 g) was suspended in 30 ml of water. Potassium carbonate (0.279 g) was added to the suspension. The mixture was stirred to prepare a homogeneous solution which was then lyophilized to provide a potassium salt. DMF (25 ml) was added to the potassium salt. The mixture was cooled with ice. Methyl iodide (0.633 g) was added, followed by stirring for 18 hours with ice cooling. DMF was removed from the reaction solution by distillation under reduced pressure. Dichloromethane (100 ml) and 100 ml of a 155 aqueous solution of sodium chloride were added to the residue for dissolution. The organic layer was separated. The aqueous layer was extracted with dichloromethane (50 ml, twice). The organic layers were combined together, dried in anhydrous magnesium sulfate, and then concentrated to a volume of 50 ml under reduced pressure. Ethyl acetate (50 ml) was then added to the concentrate, followed by concentration to a volume of 20 ml. The concentrate was allowed to stand at a temperature of 0 ° C for 3 hours. The resulting crystal was collected by filtration, washed with a lower amount of cold ethyl acetate, and then dried under reduced pressure to provide 0.644 g of methyl imidazo [5, 1-b] thiazole-7-carboxylate. NMR (CDC13) d: 3.96 (3H, s), 7.06 (1H, d, J = 4.2, Hz), 7.55 (1H, d, J = 4.2 Hz), 8.02 (1H, s) c) 2- (tri -n-butylstannyl) methyl imidazo [5, 1-b] thiazole-7-carboxylate A solution (5 ml) of 0716 g of tri-n-butylstannyl chloride in THF was added to a solution (20 ml) of 0.364 g of methyl imidazo [5, 1-b] thiazole-7-carboxylate in THF at a temperature of -70 ° C. A 1.0 N solution of lithium (trimethylsilyl) amide / n-hexane (4.4 ml) drop was added to drop and at a temperature of -70 ° C. the mixture was stirred at a temperature of -50 ° C for 30 minutes. The reaction solution was added to an ice-cooled mixed solution composed of 50 ml of a 0.2 N phosphate buffer (pH 7) and 50 ml of dichloromethane with stirring. The organic layer was separated, and then dried over anhydrous magnesium sulfate. The solvent was removed by distillation.

The residue was subjected to separation and purification by flash column chromatography on silica gel (hexane: ethyl acetate = 1: 1) to provide 0.395 g of the title compound. NMR (CDC13) d: 0.92 (9H, t, J = 7.3 Hz), 1.42 - 1.52 (6H, m), 3.94 (3H, s), 7.26 (3H, s), 7.95 (1H, s) Preparation 27 7 - (N-methoxy-N-methylsulfamoyl) -2- (tri-n-butyl-stanyl) imidazo [5, 1-b] thiazole a) 7- (N-methoxy-N-methylsulfamoyl) imidazo [5, 1- b] thiazole N, O-dimethylhydroxylamine hydrochloride (0.23 g) and 0.56 ml of triethylamine were added to a solution of 0.44 g of 7-chlorosulfonylimidazo [5, 1-b] thiazole in 5 ml of DMF. The mixture was stirred at room temperature for 1 hour. Ethyl acetate was added there, followed by washing with water and saturated saline, in this order. The organic layer was dried over anhydrous magnesium sulfate. The solvent was removed by distillation. The residue was purified by column chromatography on silica gel (hexane: ethyl acetate = 1: 2) to give 0.44 g of 7- (N-methoxy-N-methylsulfamoyl) imidazo [5, 1-b] thiazole NMR ( CDCI3) d: 3.05 (H, s), 3/83 (3H, s), 7.07 (1H, d, J = 4.2 Hz), 7.58 (1H, d, J = 4.2 Hz), 8.09 (1H, s) b) 7- (N-methoxy-N-methylsulfamoyl) -2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole A 1.0 N solution of lithium (trimethylsilyl) amide / THF (2.0 ml) was added to a solution of 0.44 g of 7- (N-methoxy-N-methylsulfamoyl) imidazo [5, 1-b] thiazole in 9 ml of dry THF in an argon atmosphere at a temperature of -40 ° C. The mixture was stirred at the same temperature for 30 minutes. Tri-n-butylstannyl chloride (0.58 ml) was added there. The mixture was stirred for 30 minutes. In addition, a 1.0 N solution of lithium (trimethylsilyl) amide / THF (2.5 ml) was then added, followed by stirring for 30 minutes. Tri-n-butylstannyl chloride (0.1 ml) was added there. The mixture was stirred at the same temperature for 30 minutes. An aqueous saturated saline solution of ammonium chloride was added thereto, and the ethyl acetate was then added, followed by washing with water, and saturated saline, in this order. The organic layer was dried over anhydrous magnesium sulfate. The solvent was removed by distillation. The residue was purified by column chromatography on silica gel (hexane: ethyl acetate = 1: 2) to give 0.39 g of the title compound. NMR (CDC13) d: 0.92 (9H, t, J = 7.2 Hz), 1.16 - 1.25 (6H, m), 1.35 - 1.45 (6H, m), 1.55 - 1.65 (6H, m), 3.05 (3H, s ), 3.84 (3H, s), 7.26 (1H, s), 8.00 (1H, s) Preparation 28 7-trifluoroacetyl-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole a) 7- trifluoroacetylimidazo [5, 1-b] thiazole A 1 N solution of ethylmagnesium bromide / THF (10 ml) was added to a solution 2.50 g of 7-iodoimidazo [5, 1-b] thiazole in 10 ml dry THF in an atmosphere of argon at a temperature of -50 ° C. The mixture was stirred at the same temperature for 1 hour. Trifluoroacetic anhydride (1.53 ml) was added, followed by stirring at the same temperature for 10 minutes. A saturated aqueous solution of ammonium chloride was added to the reaction mixture. Ethyl acetate was then added, followed by washing with a dilute aqueous solution of sodium thiosulfate and a saturated saline solution in this order. The organic layer was dried over anhydrous magnesium sulfate. The solvent was removed by distillation. The residue was purified by column chromatography on silica gel (hexane: ethyl acetate = 1: 1) to provide 0.64 g of 7-trifluoroacetylimidazo [5,1-b] thiazole. NMR (CDC13) d: 7.25 (1H, d, J = 4.1 Hz), 7.68 (1H, d, J = 4.1 Hz), 8.13 (1H, s) b) 7-trifluoroacetyl-2- (tri-n-butyl) -stannyl) imidazo [5,1-b] thiazole A 1.0 N solution of lithium (trimethylsilyl) amide / THF (2.0 ml) was added to a solution of 0.34 g of 7-trifluoroacetylimidazo [5]., 1-b] thiazole and 0.48 ml tri-n-butylstannyl chloride in 16 ml of dry THF in an argon atmosphere at a temperature of -40 ° C. The mixture was stirred at the same temperature for 30 minutes. There was added an aqueous saline solution saturated with ammonium chloride. Ethyl acetate was then added, followed by washing with water, and saturated saline, in this order. The organic layer was dried over anhydrous magnesium sulfate. The solvent was removed by distillation. The residue was purified by column chromatography on silica gel (hexane: ethyl acetate = 4: 1) to give 0.14 g of the title compound. NMR (CDC13) d: 0.92 (9H, t, J = 7.4 Hz), 1.20 - 1.40 (12H, m), 1.55 - 1.70 (6H, m), 7.38 (1H, s), 8.05 (1H, s) Preparation 29 7- (t-butyldimethylsilylsulfamoyl) -2- (tri-n-butyl-stanyl) imidazo [5, 1-b] thiazole a) 7-sulfamoylimidazo [5, 1-b] thiazole A 2N ammonia solution was added / Ethanol (4 ml) of 0.44 g of 7-chlorosulfonylimidazo [5, 1-b] in 10 ml of THF. The mixture was stirred at room temperature for 12 hours. The reaction mixture was concentrated. The residue was purified by column chromatography on silica gel (dichloromethane: methanol = 10: 1) to provide 0.34 g of 7-sulfamoylimidazo [5, 1-b] thiazole. NMR (CDCl 3) d: 7.33 (2H, s), 7.38 (1H, d, J = 4.1 Hz), 8.00 (1H, d, J = 4.1 Hz), 7.32 (1H, s) b) 7- (t- butyldimethylsilylsulfamoyl) imidazo [5, 1-b] thiazole t-butyldimethylsilyl chloride (0.30 g) and 0.33 ml of triethylamine were added to a solution of 0.20 g of 7-sulfamoylimidazo [5, 1-b] thiazole in 5 ml of DMF . The mixture was stirred at room temperature for 1 hour. Ethyl acetate was added to the reaction mixture, followed by washing with water and saturated saline in this order. The organic layer was dried over anhydrous magnesium sulfate. The solvent was removed by distillation. The residue was purified by column chromatography on silica gel (hexane: ethyl acetate = 1: 1) to provide 0.34 g of 7- (t-butyldimethylsilylsulfamoyl) imidazo [5, 1-b] thiazole. NMR (CDC13) d: 0.24 (6H, s), 0.82 (9H, s), 4.54 (1H, s), 7.00 (1H, d, J = 4.2 Hz), 7.50 (1H, d, J = 4.2 Hz) , 8.02 (1H, s) 'c) 7- (t-butyldimethylsilylsulfamoyl) -2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole Substantially in the same manner as in preparation 28-b), 0.73 g of the title compound was obtained from 0.52 g of 7- (t-butyldimethylsilylsulfamoyl) imidazo [5, 1-b] thiazole and 0.53 ml of tri-n-butylstannyl chloride. NMR (CDCl 3) d: 0.24 (6H, s), 0.88 - 096 (21H, s), 1.18 (6H, t, J = 8.4 Hz), 1.30 - 1.40 (6H, s), 1.55 - 1.65 (6H, m ), 4.52 (1H, s), 7.21 (1H, s), 7.94 (1H, s) Preparation 30 7- (2-methoxycarbonylvinyl) -2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole (a mixture of geometric isomers) a) 7- (2-methoxycarbonylvinyl) imidazo [5, 1-b] thiazole (a mixture of geometric isomers) Methyl triphenylphosphoranylidenacetate (500 mg) was added to a solution of 150 mg of 7- formylimidazo [5, 1-b) thiazole in 15 ml of methanol. The mixture was stirred at room temperature for 15 minutes. Ethyl acetate was added there. The mixture was washed with water, dried over anhydrous magnesium sulfate, and filtered. The solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography on silica gel (chloroform: methanol = 20: 1) to provide 228 mg of 7- (2-methoxycarbonylvinyl) imidazo [5, 1-b] thiazole (a mixture of geometric isomers) NMR (CDC13) d: 3.80 (3H, s), 6.17 (1H, d, J = 15.8 Hz), 7.01 (1H, d, J = 4.1 Hz), 7.50 (1H, d, J = 4.1 Hz), 7.77 ( 1H, d, J = 15.8 Hz), 8.05 (1H, s) NMR (CDCI3) d: 3.81 (3H, s), 5.82 (1H, d, J = 12.4 Hz), 7.03 (1H, d, J = 4.1 Hz), 7.13 (1H, d, J = 12.4 Hz), 7.50 (1H, d, J = 4.1 Hz), 8.06 (1H, s) b) 7- (2-methoxycarbonylvinyl) -2- (tri-n- butylstannyl) imidazo [5, 1-b] thiazole (a mixture of geometric isomers) tri-n-butylstannyl chloride (250 μl) and 2.1 ml of a 1.0 N solution of lithium (trimethylsilyl) amide / THF were added in this Order a solution of 7- (2-methoxycarbonylvinyl) imidazo [5, 1-b] thiazole (a mixture of geometric isomers) in dry THF under an argon atmosphere at a temperature of -78 ° C. The mixture was stirred at the same temperature for 15 minutes. Water was added there. The mixture was extracted with ethyl acetate, followed by washing with a saturated saline solution. The extract was dried over anhydrous magnesium sulfate and then filtered. The solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography on silica gel (hexane: ethyl acetate = 4: 1) to provide 408 mg of the title compound. NMR (CDC13) d: 0.92 (9H, t, J = 7.4 Hz), 1.18 (6H, m), 1.36 (6H, m), 1.58 (6H, s), 3.78 (3H, s), 6.13 (1H, d, J = 15.8 Hz), 7.23 (1H, s), 7.77 (1H, d, J = 15.8 Hz), 7.98 (1H, s) NMR (CDCI3) d: 0.92 (9H, t, J = 7.4 Hz) , 1.18 (6H, m), 1.36 (6H, m), 1.58 (6H, s), 3.82 (3H, s), 5.77 (1H, d, J = 12.4 Hz), 7.10 (1H, d, J = 12.4 Hz), 7.25 (1H, s), 8.01 (1H, s) Preparation 31 7- (thiazol-4-yl) -2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole a) 7- Chloroacetylimidazo [5, 1-b] thiazole Chloroacetyl chloride (5.97 ml) was added to a solution of 12. 5 g of aluminum chloride in 40 ml of 1,2-dichloroethane. The mixture was stirred at room temperature for 20 minutes. A solution of 1.93 g of imidazo [5,1-b] thiazole in 20 ml of 1,2-dichloroethane was added there. The mixture was heated under reflux for 2 hours. Water was added, followed by extraction with dichloromethane. The organic layers were combined together. The combined organic layers were washed with a dilute aqueous solution of sodium hydroxide and a saturated saline solution, in this order, the solvent was removed, by distillation. Ether was added Isopropyl to the residue The resulting powder was collected by filtration to obtain the title compound: NMR (CDCl 3) d: 4.83 (2H, s), 7.16 (1H, d, J = 4.1 Hz), 7.60 (1H, d, J = 4.1 Hz), 8.02 (1H, s) b) 7- (thiazol-4-yl) imidazo [5, 1-b] thiazole Diphosphorus pentasulfide (846 mg) was added to 8.4 ml of formamide. stirred at room temperature overnight 7. 7-Chloroacetylimidazo [5, 1-b] thiazole (2.32 g) was added to the reaction solution, the mixture was stirred at room temperature for 15 hours, water (20 ml) and 10 ml. The dichloromethane was added thereto The mixture was adjusted to a pH of 8.8 by the gradual addition of a sodium hydrogencarbonate powder The extraction was carried out 6 times with 50 ml of dichloromethane The organic layer was dried in anhydrous magnesium sulfate The solvent was removed by distillation under reduced pressure.The residue was purified by column chromatography on silica gel (hexane: ethyl acetate). ilo = 1: 2) to provide 172 g of 7- (thiazol-4-yl) imidazo [5, 1-b] thiazole. NMR (CDCI3) d: 6.93 (1H, d, J = 4.2 Hz), 7.46 (1H, d, J = 4.2 Hz), 7.60 (1H, d, J = 2.1 Hz), 8.05 (1H, s), 8.87 (1H, d, J = 2.1 Hz) MS (El): 207 (M +) c) 7- (thiazol-4-yl) -2- (tri-n-butylstannyl) imidazo [5, lb] thiazole A solution of 1.01 g of 7- (thiazol-4-yl) imidazo [5, 1-b] thiazole in 45 ml of THF was cooled to a temperature of -70 ° C under an argon atmosphere. Tri-n-butylstannyl chloride (1.58 ml) was added. A 1 N solution of lithium (trimethylsilyl) amide / THF (11.2 ml) was added dropwise at the same temperature. The mixture was stirred for 30 minutes. The temperature of the mixture was raised to a temperature of -30 ° C for a period of 1 hour. A saturated aqueous solution of sodium chloride was added, followed by extraction twice with ethyl acetate. The extract was dried in anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography on silica gel (hexane: ethyl acetate = 1: 1). The title compound (294 mg) was obtained from the fraction of Rf = 0.5. NMR (CDC13) d: 0.92 (9H, t, J = 7.4 Hz), 1.20 (6H, m), 1.37 (-6H, m), 1.58 (6H, m), 7.22 (1H, s), 7.59 (1H , d, J = 2.2 Hz), 8.00 (1H, s), 8.87 (1H, d, J = 2.2 Hz) Preparation 32 7-t-Butyldimethylsilyloxyacetyl-5-methyl-2- (tri-n-butylstannyl) imidazo [ 5, 1-b] thiazole a) 7-acetoxyacetyl-5-methylimidazo [5, 1-b] thiazole In the same manner as in preparation 16-a), 734 mg of 7-acetoxyacetyl-5-methylimidazo [ 5, 1-b] thiazole from 821 mg of 7-acetyl-5-methylimidazo [5, 1-b] thiazole. NMR (CDC13) d: 2.23 (3H, s), 2.63 (3H, s), 5.40 (2H, s), 7.08"(1H, d, J = 4.1 Hz), 7.39 (1H, d, J = 4.1 Hz ) b) 7-hydroxyacetyl-5-methylimidazo [5, 1-b] thiazole In the same manner as in preparation 16-b), 704 mg of 7-hydroxyacetyl-5-methylimidazo [5, 1-b] was obtained thiazole from 872 mg of 7-acetoxyacetyl-5-methylimidazo [5, 1-b] thiazole, NMR (CDCl 3) d: 2.56 (3H, s), 4.63 (2H, s), 7.49 (1H, d, J = 3.7 Hz), 8.05 (1H, d, J = 3.7 Hz) c) 7-t-butyldimethylsilyloxyacetylimidazo [5, 1-b] thiazole In the same manner as in preparation 16-c), 699 mg of 7 -t-butyldimethylsilyloxyacetylimidazo [5, 1-b] thiazole from 508 mg of 7-hydroxyacetyl-5-methylimidazo [5, 1-b] thiazole, NMR (CDCl 3) d: 0.15 (6H, s), 0.96 (9H, s), 2.63 (3H, s), 5.04 (2H, s), 7.05 (1H, d, J = 4.1 Hz), 7.36 (1H, d, J = 4.1 Hz) _ - d) 7-t-butyldimethylsilyloxyacetyl -5-methyl-2- (tri-n-butyl-stanyl) imidazo [5, 1-b] thiazole 7-t-Butyldimethylsilyloxy? Acetyl? M? Dazo [5, 1-b] thiazole (49.5 mg) was dissolved in 2 ml of THF and 0.4 ml of HMPA. Tri-n-butylstannyl chloride (0.059 ml) and 0.319 ml of a 1.0 N solution of lithium (trimethylsilyl) amide / THF were added dropwise in this order to the solution in an argon atmosphere at a temperature of -73 ° C. C. The mixture was stirred at the same temperature for 1 hour. A 1.0 N solution of lithium (trimethylsilyl) amide / THF (0.160 ml) was added dropwise there. The mixture was stirred at the same temperature for an additional 40 minutes. A solution of ammonium chloride was added to the reaction solution, followed by extraction with ethyl acetate and washing three times with a saline solution. The extract was dried over anhydrous magnesium sulfate, and then filtered. The solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography on silica gel (hexane: ethyl acetate = 5: 1) to provide 66.9 mg of the title compound. NMR (CDClo) d: 0.15 (6H, s), 0.91 (9H, t, J = 7.4 Hz), 0.96 (9H, s), 1.18 (6H, m), 1.35 (6H, m), 1.58 (6H, m), 2.62 (3H, s), 5.03 (2H, s), 7.06 (1H, s) Preparation 33 7-methanesulfonylaminoacetyl-2- (tri-n-butyl-stanyl) imidazo [5, 1-b] thiazole a 7-methanesulfonylaminoacetylimidazo [5, 1-b] thiazole- 2N hydrochloric acid (4.88 ml) and 336 mg of 10% Pd-C were added to a solution of 673 mg of 7-azidaacetylimidazo [5, 1-b] thiazole in 16 ml of water and 20 ml of THF. The atmosphere in the reactor was replaced by hydrogen. The system was stirred at room temperature for 2 hours. The catalyst was removed by filtration through Celite and washed with water. THF was removed by distillation under reduced pressure. A 1 N aqueous solution of hydroxide (12.8 ml) was added there, followed by extraction nine times with dichloromethane. The organic layers were combined together, dried in anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The residue was dissolved in 20 ml of dichloromethane. N, -diisopropylethylamine (0.849 ml) and 0.377 ml of methanesulfonyl chloride were added to the solution. The mixture was stirred at room temperature for 1 hour. An aqueous sodium hydrogencarbonate solution was added to the reaction solution, followed by extraction three times with dichloromethane. The organic layers were combined together, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (dichloromethane: methanol 30: 1) to provide 397 mg of 7-methanesulfonylaminoacetylimidazo [5, 1-b] thiazole. NMR (DMSO-De) d: 2.98 (3H, s), 4.51 (2H, d, J = 5.7 Hz), 7.36 (1H, t, J = 5.7 Hz), 7.55 (1H, d, J = 4.2 Hz) , 8.12 (1H, d, J = 4.2 Hz), 8.37 (1H, s) b) 7-methanesulfonylaminoacetyl-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole 7-methanesulfonylaminoacetylimidazo [5] was dissolved. , 1-b] thiazole (46.2 mg) in 2 ml of THF and 0.4 ml of HMPA. Tri-n-butylstannyl chloride (0.076 ml) and 0.713 ml of a 1.0 N solution of lithium (trimethylsilyl) amide / THF were added dropwise in this order to the solution in an argon atmosphere at a temperature of -70 ° C. C. The mixture was stirred at the same temperature for 1.5 hours. A 1.59 N solution of n-butyllithium / n-hexane (0.146 ml) was added dropwise there. The mixture was stirred at the same temperature for 1 hour. A 1.59 N solution of n-butyllithium / n-hexane (0.146 ml) and 0.76 ml of tri-γ-butylstannyl chloride were added dropwise there. The mixture was stirred at the same temperature for 45 minutes. A solution of ammonium chloride was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed twice with saline, dried over anhydrous magnesium sulfate, and filtered. The solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography on silica gel (hexane: ethyl acetate = 1: 1) to provide 37.5 mg of the title compound. NMR (CDC13) d: 0.92 (9H, t, J = 7.4 Hz), 1.20 (6H, m), .1.35 (6H, m), 1.60 (6H, m), 3.00 (3H, s), 4.69 (2H , d, J = 5.0 Hz), 5.44 (1H, br), 7.32 (1H, s), 7.96 (? H. s) Preparation 34 7-methanesulfonylaminomethyl-2- (tri-n-butylstannyl) imidazo [5, 1 - b] thiazole a) 7- (methanesulfonylaminomethyl) imidazo [5, 1-b] thiazole Triethylamine (0.18 ml) and 0.75 ml methanesulfonyl chloride were added in this order with ice cooling to a solution of 134 mg of aminomethylimidazo [5, 1-b] thiazole and 2.5 ml of dry dichloromethane. In this state, the system was stirred for 2 hours while the temperature was gradually raised to room temperature. The reaction solution was diluted with 20 ml of dichloromethane, followed by washing with a saturated saline solution. The aqueous layer was extracted with 10 ml of dichloromethane. The organic layers were combined together, dried in anhydrous magnesium sulfate, and filtered, the solvent was removed by distillation. The oil obtained in this way was purified by using Sephadex LH-20 (dichloromethane: methanol = 1: 1) to provide 130 mg of 7- (methanesulfonylaminomethyl) imidazo [5, 1-b] thiazole as a yellow solid Clear. NMR (CDC13) d: 2.91 (3H, s), 4.43 (2H, d, J = 6.0 Hz), 5.26 (1H, br.t), 6.87 (1H, d, J * = 4.2 Hz), 7.40 (1H , d, J = 4.2 Hz), 7.99 (1H, s) MS (TSP): m / z = 232 (M ++ H) b) 7-methanesulfonylaminomethyl-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole A solution of 231 mg of 7- (methanesulfonylaminomethyl) imidazo [5, 1-b] thiazole dissolved in a mixed solution composed of 10 ml of dry THF and 1 ml of dry HMPA was cooled to a temperature of - 50 ° C with shaking. A 1.6 N solution of n-butyllithium / n-hexane (2.0 ml) was added dropwise to the mixed solution in an argon atmosphere at a temperature of -51 ° C to -49 ° C over a period of 15 minutes. The mixture was stirred at the same temperature for 15 minutes. In addition, 0.34 ml of tri-n-butylstannyl chloride was added dropwise there at a temperature of -50 ° C to -48 ° C for a period of 10 minutes. The mixture was stirred at a temperature of -50 ° C to -40 ° C for 140 minutes. Tri-n-butylstannyl chloride (0.07 ml) was further added to the reaction solution at a temperature of -42 ° C. The mixture was stirred for 30 minutes. A 0.38 M phosphate buffer (pH 6.0) (15 ml) was added. The mixed solution was extracted with 30 ml of ethyl acetate. The organic layer was washed with a 0.8 M phosphate buffer (pH 6.0) and saturated saline in this order, and then dried in anhydrous sodium sulfate. The anhydrous magnesium sulfate was removed by filtration. The solvent was removed by distillation. The brown oil obtained from subtracting form was purified by column chromatography on silica gel (eluting with dichloromethane: ethyl acetate = 1: 1 and then with ethyl acetate alone) to provide 160 mg of the title compound as a yellow crystal. NMR (CDCl 3) d: 0.92 (9H, t, J = 7.2 Hz), 1.05-1.20 (6H, m), 1. 25 - 1.40 (6H, m), 1.45 - 1.70 (6H, m), 2.91 (3H, s), 4.41 (2H, d, J = 5.8 Hz), 5.03 (1H, br.t), 7.14 (1H, s), 7.92 (1H, MS (FAB *): m / z = (M + + H), 520 (M * -2 + H) Preparation 35 7- (N, N-dimethylaminosulfonylamino) acetyl-2- (tri-n-butylstannyl) ) imidazo [5, 1-b] thiazole a) 7- (N, N-dimethylaminosulfonylamino) acetyl-imidazo [5,1-b] thiazole 7-Azidaacetylimidazo [5, 1-b] thiazole (207 mg) was dissolved in 6 ml of THF, 4.5 ml of water and 3 ml of 1 N aqueous hydrochloric clay. 10% Pd-C (103 mg) was added to the solution. The air in the reactor was replaced by hydrogen. The system was then stirred at room temperature for 17 hours. The catalyst was removed by filtration through Celite, followed by washing with water. The filtrate was concentrated to half the amount. A 1N aqueous solution of sodium hydroxide (4 ml) was added to the filtrate. The mixture was extracted six times with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was dissolved in 5 ml of dichloromethane. N, N-diisopropyleethylamine (0.783 ml) and 0.322 ml of N, N-dimethylaminosulfonyl chloride were added to the solution. The mixture was stirred at room temperature for 7 hours. An aqueous hydrogencarbonate solution of. Sodium was added to the reaction solution. The mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane: methanol = 30: 1) to provide 167 mg of 7- (N, N-dimethylaminosulfonylamino) acetyl-imidazo [5, 1-b] thiazole. NMR (CDC13) d: 2.83 (6H, s), 4.59 (2H, d, J = 4.9 Hz), 5.45 (1H, br.s), 7.17 (1H, d, J = 4.1 Hz), 7.62 (1H, d, J = 4.1 Hz), 8.03 (1H, s) b) 7- (N, N-dimethylaminosulfonylamino) acetyl-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole Tri-n Chloride -butylsynyl (0.962 ml) and 8.42 ml of 1.0 N lithium (trimethylsilyl) amide / THF were added sequentially at a temperature of -73 ° C under an argon atmosphere to a solution of 485 mg of 7- (N, N-dimethylaminosulfonylamino ) acetyl-imidazo [5, 1-b] thiazole in 18 ml of THF. The mixture was stirred at the same temperature for 30 minutes. An aqueous solution of ammonium chloride was added to the reaction solution. The mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and then filtered. The solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography on silica gel (hexane: ethyl acetate = 1: 1) to provide 427 mg of the title compound. NMR (CDC13) d: 0.92 (9H, t, J = 7.3 Hz), 1.15 - 1.25 (6H, m), 1.3 - 1.45 (6H,), 1.5 - 1.7 (6H, m), 2.83 (6H, s), 4.58 (2H, d, J = 4.7 Hz), 5.47 (1H, br.s), 7.31 (1H, s), 7.95 (1H, s) Preparation 36 7- [2- (4-nitrobenzyloxycarbonyl) aminoethane -sulfonylamino] acetyl-2- (tri-n-butylstannyl) imidazo [5, lb] -thiazole a) 7- [2- (4-nitrobenzyloxycarbonyl) aminoethanesulfonylamino] acetyl -.- imidazo [5, 1-b] thiazole ~ - ~ 7-Azidaacetylimidazo [5, 1-b] thiazole (685 mg) was dissolved in 20 ml of THF, 15 ml of water and LO ml of 1 N aqueous hydrochloric acid. 10% Pd-C (341 mg) was added. to the solution. The air in the reactor was replaced by hydrogen. The system was then stirred at room temperature for 2 hours. The catalyst was removed by filtration through Celite, followed by washing with water. The filtrate was concentrated to half the amount. A 1N aqueous solution of sodium hydroxide (13 ml) was added to the filtrate. The mixture was extracted six times with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was dissolved in 10. ml of dichloromethane. N, N-diisopropylenetylamine (0.865 ml) and 1.60 g of 2- (4-nitrobenzyloxycarbonyl) chloride aminoethanesulfonyl were added to the solution with ice cooling. The mixture was stirred at the same temperature for 1 hour. An aqueous solution of sodium hydrogencarbonate was added to the reaction solution. The mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography on silica gel (dichloromethane: methanol = 30: 1) to provide 808 mg of 7- [2- (4-nitrobenzyloxycarbonyl) aminoethanesulfonylamino] acatyl-imidazo [5, 1-b] thiazole. NMR (CDC13) d: 3.25 - 3._3_5 (2H, m), 3.7 - 3.8 (2H, m), 4.69 (2H, d, J = 5.0 Hz), 5.20 (2H, s), 5.49 (1H, br .s), 5.75 (1H, br.s), 7.17 (1H, d, J = 4.2 Hz), 7.50 (2H, d, J = 8.7 Hz), 7.60 (1H, d, J = 4.2 Hz), 8.02 (1H, s), 8.19 (2H, d, J = 8.7 Hz) b) 7- [2- (4-Nitrobenzyloxycarbonyl) aminoethane-sulfonylamino] acetyl-2- (tri-n-butylstannyl) imidazo [5, 1- b] thiazole Tri-n-butylstannyl chloride (0.83 ml) and 7.3 ml of 1.0 N lithium (trimethylsilyl) amide / THF were added sequentially at a temperature of -73 ° C under an argon atmosphere to a solution of 682 mg of 7- [2- (4-Nitrobenzyloxycarbonyl) aminoethanesulfonylamino] acetyl-imidazo [5, 1-b] thiazole in 16 ml of THF and 3 ml of HMPA. The mixture was stirred at the same temperature for 30 minutes. An aqueous solution of ammonium chloride was added to the reaction solution. The mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and then filtered. The solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography on silica gel (hexane: ethyl acetate = 1: 1-1: 2) to give 327 mg of the title compound. NMR (CDC13) d: 0.91 (9H, t, J = 7.3 Hz), 1.15 - 1.25 (6H, m), 1.25 - 1.4 (6H, m), 1.5 - 1.65 (6H, m), 3.25 - 3.35 (2H , m), 3.7 - 3.8 (2H, m), 4.68 (2H, d, J = 5.1 Hz), 5.19 (2H, s), 5.60 (1H, br.s), 5.85 (1H, br.s), 7.32 (1H, s), 7.49 (2H, d, J = 8.8 Hz), 7.96 (1H, s), 8.18 (2H, d, J = 8.8 Hz) Preparation 37 7-phenylthio-2- (tri-n-) butylstanyl) imidazo [5, 1-b] thiazole a) 7-phenylthioimidazo [5, 1-b] thiazole A 1 N solution of ethylmagnesium bromide / THF (3.46 ml) was added under an argon atmosphere at a temperature with cooling with ice to a solution of 840 mg of 7-iodoimidazo [5, 1-b] thiazole in 20 ml of dry THF. The mixture was stirred at the same temperature for 1 hour. Phenylbenzothiol sulfonate (939 mg) was added, and the mixture was stirred at the same temperature for 1 hour. A saturated aqueous solution of ammonium chloride was added to the reaction mixture. Ethyl acetate was added there. The mixture was washed with a dilute aqueous solution of sodium thiosulfate and a saturated saline solution, in this order. The organic layer was dried over anhydrous magnesium sulfate. The solvent was removed by distillation. The residue was purified by column chromatography on silica gel (hexane: ethyl acetate = 1: 1) to provide 385 mg of 7-phenylthioimidazo [5, 1-b] thiazole. NMR (CDC13) d: 6.90 (1H, d, J = 4.3 Hz), 7.1 - 7.2 (1H, m), 7.2 - 7.25 (5H, m), 7.45 (1H, d, J = 4.3 Hz), 8.09 ( 1H, s) b) 7-phenylthio-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole. A 1.59 N n-butyllithium / n-hexane solution (0.189 ml) was added dropwise to a well. temperature of -73 ° C in an argon atmosphere to a solution of 66.5 mg of 7-phenylthioimidazo [5, 1-b] thiazole in 3 ml of THF. Subsequently, 0.098 ml of tri-n-butylstannyl chloride was added to the mixture. The mixture was stirred at the same temperature for 15 minutes. The temperature of the system was raised to -40 ° C. A 1.0 N solution of lithium (trimethylsilyl) amide / THF (0.11 ml) was added thereto. The mixture was stirred for 1 hour. An aqueous solution of ammonium chloride was added to the reaction solution. The mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and then filtered. The solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography on silica gel (hexane: ethyl acetate = 5: 1) to provide 115 mg of the title compound. NMR (CDC13) d: 0.91 (9H, t, J = 7.2 Hz), 1.1 - 1.2 (6H,), 1.3 - 1.4 (6H, m), 1.5 - 1.7 (6H, m), 7.05 - 7.15 (1H, m), 7.15 - 7.25 (6H, m), 8.03 (1H, s) Preparation 38 7-ethylthio-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole a) Ethylene-ethylene sulfonate Disulfide was dissolved of diethyl (3.69 ml) in 450 ml of dichloromethane. 3-Chloroperbenzoic acid (19.43 g) was added with ice cooling to the solution. The mixture was stirred at room temperature for 3 hours. The insoluble particles were removed by filtration. The filtrate was washed with an aqueous solution of sodium thiosulfate, an aqueous solution of sodium hydrogencarbonate, a saline solution, in this order, dried in anhydrous magnesium sulfate and then filtered. The solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography on silica gel (hexane: ethyl acetate = 5.: 1) to provide 2.05 g of ethylethanediol NMR (CDCl 3) d: 1.44 (3H, t, J = 7.4 Hz), 1.48 (3H, t, J = 7.4 Hz), 3.16 (2H, q, J = 7.4 Hz), 3.33 (2H, q, J = 7.4 Hz) b) 7-ethylthio-2- (tri-n-butylstannyl) Imidazo [5, 1-b] thiazole A 1 N solution of ethylmagnesium bromide / THF (8.52 ml) was added under an argon atmosphere at a temperature with ice-cooling to a solution of 2.07 g of 7-iodoimidazo [5, 1-b] thiazole in 40 ml of THF dry. The mixture was stirred at the same temperature for 1 hour. Ethylethyantiol sulfonate (1527 g) was added, and the mixture was stirred at room temperature for 30 minutes. A saturated aqueous solution of ammonium chloride was added to the reaction mixture. Ethyl acetate was then added there followed by washing with a dilute aqueous sodium thiosulfate and a saturated saline solution, in this order. The organic layer was dried over anhydrous magnesium sulfate. The solvent was removed by distillation. The residue was purified by column chromatography on silica gel (dichloromethane: ethyl acetate = 1: 1) to provide 1064 g of 7-ethylthioimidazo [5, 1-b] thiazole. NMR (CDC1) d: 1.26 (3H, t, J = 7.4 Hz), 2.83 (3H, q, J = 7.4 Hz), 6.87 (1H, d, J = 4.2 Hz), 7.40 (1H, d, J = 4.2 Hz), 8.01 (1H, s) c) 7-ethylthio-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole In the same manner as in preparation 37-b), 2.34 of the title compound was obtained from 1.10 g of 7-ethylthioimidazo [5, 1-b] thiazole. NMR (CDCI3) d: 0.92 (9H, t, J = 7.4 Hz), 1.1 - 1.2 (6H, m), 1.27 (3H, t, J = 7.3 Hz), 1.3 - 1.4 (6H, m), 1.5 - 1.65 (6H,), 2.82 (2H, q, J = 7.3 Hz), 7.14 (1H, s), 7.95 (1H, s) Preparation 39 3-methyl-7-methylthio-2- (tri-n-butylstannyl) imidazo '[5,1-b] thiazole a) 7-iodo-3-methylthioimidazo [5, 1-b] thiazole In the same manner as in preparation 22-a), 525 mg of 7-iodo-3 was obtained -methylthioimidazo [5, 1-b] thiazole from 505 mg of 3-methyl-7-methylthioimidazo [5, 1-b] thiazole. NMR (CDC13) d: 2.40 (3H, s), 6.46 (1H, s), 7.84 (1H, s) b) 3-methyl-7-methylthioimidazo [5, 1-b] thiazole In the same manner as in the Preparation 12-a), 1.88 g of 3-metii-7-methylthioimidazo [5, 1-b] thiazole was obtained from 3.0 g of 7-iodo-3-methylthioimidazo [5, 1-b] thiazole. NMR (CDCl 3) d: 2.40 (3H, s), 2.43 (3H, s), 6.44 (1H, s), 7.89 (1H, s) c) 3-methyl-7-methylthio-2- (tri-n-) butylstannyl) imidazo [5,1-b] thiazole In the same manner as in preparation 4-b), 4.70 g of the title compound was obtained from 2.15 g of 3-methyl-7-methylthioimidazo [5, 1- b] thiazole Preparation 40 3-t-butyldimethylsilyloxymethyl-7-methyl-thio-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole a) 3-t-butyldimethylsilyloxymethyl-7-methyl-iodoimidazo [5 , 1-b] thiazole In the same manner as in preparation 22-a), 3.21 g of 3-t-butyldimethylsilyloxymethyl-7-iodoimidazo- [5, 1-b] thiazole was obtained from 3.26 g of 3- t-butyldimethylsilyloxymethylimidazo- [5, 1-b] thiazole. NMR (CDC13) d: 0.10 (6H, s), 0.90 (9H, s), 4.75 (2H, s), 6.66 (1H, s), 7.98 (1H, s) b) 3-t-butyldimethylsilyloxymethyl-7 methyl-thioimidazo [5,1-b] thiazole In the same manner as in preparation 12-a), 1.06 g of 3-t-butyldimethylsilyloxymethyl-7-methylthioimidazo [5, 1-b] thiazole was obtained from 1.70 g of 3-t-butyldimethylsilyloxymethyl-7-iodoimidazo [5, 1-b] thiazole. NMR (CDCl 3) d: 0.11 (6H, s), 0.91 (9H, s), 2.44 (3H, s), 4.76 (2H, s), 6.64 (1H, s), 8.02 (1H, s) c) 3 -t-butyldimethylsilyloxymethyl-7-methylthio-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole In the same manner as in preparation 4-b), 1.77 g of the title compound was obtained from of 1.06 g of 3-t-butyldimethylsilyloxymethyl-7-methylthioimidazo [5, 1-b] thiazole. NMR (CDCI3) d: 0.14 (6H, s), 0.91 (9H, t, J = 7.4 Hz), 0.92 (9H, s), 1.1-1.2 (6H, m), 1.3-1.4 (6H, m), 1.5 - 1.65 (6H, m), 2.43 (3H, s), 4.66 (2H, s), 7.99 (1H, s) Preparation 41 3-Azidamethyl-2- (tri-n-butylstannyl) imidazo [5, 1- b] thiazole a) 3-azidamethylimidazo [5, 1-b] thiazole diphenylphosphoryl azide (0.259 ml) and 0.157 ml of 1,8-diazabicyclo [5, 4, 0] -7-undecene were added to a suspension of 154 mg of 3-hydroxymethylimidazo [5, 1-B] thiazole in 2 ml of toluene. The mixture was stirred at room temperature for 30 hours. A saline solution was added to the reaction mixture, and the mixture was extracted twice with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The solvent was removed by distillation. The residue was purified by column chromatography on silica gel (dichloromethane: methanol = 30: 1) to give 156 mg of 3-azidamethylimidazo [5, 1-b] thiazole. NMR (CBC13; d: 4.49 (2H, s), 6.82 (1H, s), 7.15 (1H, s), 8.02 (1H, s) b) 3-azidamethyl-2- (tri-n-butylstannyl) imidazo [5, 1- b] thiazole In the same manner as in preparation 16-d), 59.3 g of the title compound was obtained from 69.3 mg of 3-azidamethylimidazo [5, 1-b] thiazole. NMR (CDC13) d: 0.92 (9H, t, J = 7.3 Hz), 1.15 - 1.25 (6H, m), 1.25 - 1.4 (6H, m) ", 1.5 - 1.65 (6H, m), 4.41 (2H, s), 7.07 (1H, s), 7.96 (1H, s) Preparation 42 In the same manner as in preparation 4-b), 3.92 g of the title compound was obtained from 2.68 g of 3-t-butyldimethylsilyloxymethylimidazo [5, 1-b] -thiazole.

NMR (CDCI3) d: 0.15 (6H, s), 0.91 (9H, t, J = 7.4 Hz), 0.93 (9H, s), 1.1-1.2 (6H, m), 1.3-1.4 (6H, m), 1.5 - 1.65 (6H, m), 4.68 (2H, s), 7.02 (1H, s), 8.02 (1H, s) Preparation 43 3, 7-Bis (methylthio) -2- (tri-n-butylstannyl) imidazo [5,1-b] thiazole a) 7-methylthio-2-trimethylsilylimidazo- [5,1-b] thiazole A solution of 1.59 N of n-bityllithium / n-hexane (9.91 ml) was added dropwise in an Argon atmosphere at a temperature of -50 ° C to a solution of 2.55 g of 7-methylthioimidazo- [5, 1-b] thiazole in 100 ml of THF. The mixture was stirred at the same temperature for 25 minutes. Trimethylsilyl chloride (2.08 ml) was added there, and the mixture was stirred for 30 minutes. The temperature of the i = Leiua was elevated to -30 ° C. A 1.59 N solution of n-bityllithium / n-hexane (5.72 ml) was added dropwise there, and the mixture was stirred at the same temperature for 30 minutes . An aqueous solution of ammonium chloride was added to the reaction solution. The mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and then filtered. The solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography on silica gel (hexane: ethyl acetate = 1: 2) to provide 2.58 g of 7-methylthio-2-triethylsilylimidazo- [5, 1-b] thiazole. NMR (CDCl 3) d: 0.34 (9H, s), 2.42 (3H, s), 7.27 (1H, s), 7.93 (1H, s) b) 3, 7-Bis (methylthio) -2-trimethylsilyl-imidazo [ 5, 1-b] thiazole A solution of 1.59 N of n-bityllithium / n-hexane (7.38 ml) was added under an argon atmosphere at a temperature of -65 ° C to a solution of 2.58 g of 7-methylthio- 2-trimethylsilylimidazo [5, 1-b] thiazole in 40 ml of THF. The mixture was stirred at the same temperature for 20 minutes. Methylmethantiol sulfonate (1.32 ml) was added thereto, and the mixture was stirred at -30 ° C for 30 minutes. An aqueous solution of ammonium chloride was added to the reaction solution. The mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and then filtered. The solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography on silica gel (hexane: ethyl acetate = 1: 1) to provide 1.88 g of 3,7-Bis (methylthio) -2-trimethylsilylimidazo [5, 1-b] thiazole NMR ( CDC13) d: 0.42 (9H, s), 2.39 (3H, s), 2.42 (3H, s), 8.02 (1H, s) c) 3, 7-Bis (methylthio) imidazo [5, 1-b] thiazole A solution of 1.88 g of 3,7-Bis (methylthio) -2-trimethylsilylimidazo [5, 1-b] thiazole in 50 ml of THF was cooled with ice. A 1 N solution of tetra-n-butylammonium fluoride / THF (8.16 ml) in the argon atmosphere was added to the solution. The mixture was stirred at the same temperature for 1 hour. A salt solution was added there, and the mixture was extracted twice with ethyl acetate. The organic layer was washed with saline, then dried over anhydrous magnesium sulfate, and then filtered. The solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography on silica gel (hexane: ethyl acetate = 1: 1) to provide 1.30 g of 3,7-Bis (methylthio) imidazo [5, 1-b] thiazole. NMR (CDC13) d: 2.44 (3H, s), 2.49 (3H, s), 6.82 (1H, s), 8.04 (1H, s) d) 3, 7-Bis (methylthio) -2- (tri-n) -butylstanil) imidazo [5,1-b] thiazole In the same manner as in preparation 4-b), 2.10 g of the title compound was obtained from 1.30 g of 3,7-Bis (methylthio) imidazo [5]. , 1-b] thiazole. 0.92 (9H, t, J = 7.3 Hz), 0.93 (9H, s), 1.2 - 1.3 (6H, m), 1.3 - 1.4 (6H, m), 1.5 - 1.6 (6H, m), 2.37 (3H, s), 2.43 (3H, s), 7.99 (1H, s) Preparation 44 7- (1-propyl) thio-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole a) 1-propantiosulfonate of 1-propyl In the same manner as in preparation 38-a), 666 mg of 1-propyl-1-propionyl sulfonate was obtained from 1.57 ml of dipropyl disulfide. 1.04 (3H, t, J = 7.4 Hz), 1.09 (3H, t J = 7.4 Hz), 1.7 - 1.85 (2H, m), 1.9 - 2.05 (2H, m), 3.05 - 3.15 (2H, s), 3.25-3.35 (2H, s) b) 7- (1-propyl) thioimidazo [5, 1-b] thiazole In the same manner as in preparation 38-b), 1.74 g of 7- (1-propyl) was obtained thioimidazo [5, 1-b] thiazole from 3. 33 g of 1-propyl 1-propantiosulfonate 0.99 (3H, t, J = 7.4 Hz), 1.55 - 1.7 (2H,), 2.75 - 2.85 (2H,), 6.86 (1H, d, J = 4.2 Hz), 7.39 (1H, d, J = 4.2 Hz), 8. 00 (1H, s) c) 7- (1-propyl) thio-2- (tri-n-butylstannyl) imidazo [5,1-b] thiazole In the same manner as in preparation 37-b), 1. 84 g of the title compound from 882 mg of 7- (1-prpyl) thioimidazo [5, 1-b] thiazole. 0.92 (9H, t, J = 7.4_Hz), 0.99 (3H, t, J = 7.4 Hz), 1.1 - 1.2 (6H, m), 1.3 - 1.4 (6H, m), 1.5 - 1.7 (8H,), 2.7 - 2.8 (2H, m), 7.13 (1H, s), 7.94 (1H, s) Preparation 45 7-isopropylthio -2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole a) 7-isopropylthioimidazo [5, 1-b] thiazole. A 0. 69 N solution of isopropylmagnesium bromide / THF (9.13 ml) was added. in an argon atmosphere under cooling with ice to a solution of 1.50 g of 7-iodoimidazo [5, 1-b] thiazole in 30 ml of dry THF. The mixture was then stirred at the same temperature for 20 minutes, sulfur (211 mg) was added there and the mixture was heated under reflux for 1 hour. A saturated aqueous solution of ammonium chloride was added to the reaction mixture. The. The mixture was extracted twice with ethyl acetate, followed by washing with an aqueous solution of sodium thiosulfate and a saturated saline solution, in this order. The organic layer was dried over anhydrous magnesium sulfate. The solvent was removed by distillation. The residue was purified by column chromatography on silica gel (hexane: ethyl acetate = 1: 2) to provide 8.33 mg of 7-isopropylthioi idazo [5, 1-b] thiazole. 1.28 (6H, d, J = 6.7 Hz), 3.28 (1H, sept, J = 6.7 Hz), 6.87 (1H, d, J = 4.2 Hz), 7.40 (1H, d, J = 4.2 Hz), 8.02 ( 1H, s) b) 7-isopropylthio-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole In the same manner as in preparation 4-b), 1.38 g of the title compound was obtained from 1.02 g of 7-isopropylthioimidazo [5, 1-b] thiazole. 0.92 (9H, t, J = 7.3 Hz), 1.28 (6H, d, J = 6.8 Hz), 1.3 - 1.4 (6H,), 1.5 - 1.65 (6H, m), 3.26 3.28 (1H, sept, J = 6.8 Hz), 7.14 (1H, S), 7.95 (1H, s) Preparation 46 5-Methylthio-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole a) 5-methylthioimidazo [5 , 1-b] thiazole Substantially in the same manner as in preparation 12-a), 1. 03 g of 5-methylthioimidazo [5, 1-b] thiazole was obtained from 2.07 g of 5-iodoimidazo [5,1]. -b] thiazole. NMR (CDC13) d: 2.52 (3H, s), 6.84 (1H, d, J = 4.2 Hz), 7.13 (1H, s), 7.42 (1H, d, J = 4.2 Hz) b) 5-methylthio-2 - (tri-n-butylstannyl) imidazo [5, 1-b] thiazole In the same manner as in preparation 4-b), 2.40 g of the title compound was obtained from 1.03 g of 5-methylthioimidazo [5, lb] thiazole. 0.92 (9H, t, J = 7.2 Hz), 1.16 (6H, m), 1.30 - 1.40 (6H, m), 1.55 - 1.64 (6H, m), 2.51 (3H, s), 7.07 (1H, s) , 7.15 (1H, s) Preparation 47 5, 7-Bis (methylthio) -2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole a) 5,7-bis (methylthio) imidazo- [5 , 1-b] thiazole A 1 N solution of ethylmagnes * io / THF bromide (4.2 ml) was added under an argon atmosphere with ice cooling to a solution of 0.77 * g of 5,7-diiodoimidazo [5, 1]. -b] thiazole in 6 ml and dry THF. The mixture was stirred at the same temperature for 1 hour. Methylmethantiol sulfonate (0.46 ml) was added there. The mixture was stirred at room temperature for 2 hours. A saturated aqueous solution of ammonium chloride was added to the reaction mixture. Ethyl acetate was then added there, followed by washing with a dilute aqueous solution of sodium thiosulfate and a saturated saline solution, in this order. The organic layer was dried over anhydrous magnesium sulfate. The solvent was removed by distillation. The residue was purified by column chromatography on silica gel (ethyl acetate: hexane = 1: 2) to provide 0.27 g of 5,7-bis (methylthio) imidazo- [5, 1-b] thiazole. NMR (CDC13) d: 2.43 (3H, s), 2.55 (3H, s), 6.86 (1H, d, J = 4.4 Hz), 7.'38 (1H, d, J = 4.4 Hz) b) 5, 7-Bis (methylthio) -2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole In the same manner as in preparation 4-b), 2.31 g of the title compound was obtained from 1.66 g of 5,7-bis (methylthio) imidazo- [5, 1-b] thiazole 0.92 (9H, t, J = 7.2 Hz), 1.17 (6H,), 1.31 - 1.41 (6H,), 1.55 - 1.64 (6H, m), 2.42 (3H, s), 2.54 (3H, s), 7.12 (1H, s) Preparation 48 3-Methylthio-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole a) 2- (trimethylsilyl) imidazo- [5, 1-b] thiazole. drop a solution of 1.6 N of n-bityllithium / n-hexane (16.7 ml) in an argon atmosphere at a temperature of -50 ° C to a solution of 3.17 g of imidazo- [5, 1-b] thiazole in 120 ml of dry THF. The mixture was stirred at the same temperature for 30 minutes. Tri-ethylsilyl chloride (3.54 ml) was added there, and the mixture was stirred for 20 minutes. A 1.6 N solution of n-bityllithium / n-hexane (8.0 ml) was added thereto, and the mixture was stirred at the same temperature for 20 minutes. A saturated aqueous solution of ammonium chloride was added to the reaction mixture. Ethyl acetate was added there, followed by washing with water and saturated saline, in this order. The organic layer was dried in anhydrous magnesium sulfate. The solvent was removed by distillation. The residue was purified by column chromatography on silica gel (ethyl acetate to provide 4.53 g of 2- (trimethylsilyl) imidazo- [5, 1-b] thiazole, NMR (CDC13) d: 0.34 (9H, s), 7.04 (1H, s), 7.29 (1H, s) ), 7.94 (1H, s) b) 3-methylthio-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole A 1.6 N solution of n-bitillithium / n-hexane was added (15.3 ml) in an argon atmosphere at a temperature of -55 ° C to a solution of 4.40 g of 2- (trimethylsilyl) imidazo- [5,1-b] thiazole in 70 ml of dry THF. The mixture was stirred at the same temperature for 30 minutes. Methylmethantiol sulfonate (2.75 ml) was added there. The temperature of the system was brought to -5 ° C during a period of 2 hours. A saturated aqueous solution of ammonium chloride was added to the reaction mixture. Ethyl acetate was then added there, followed by washing with water and a saturated saline solution, in this order. The organic layer was dried over anhydrous magnesium sulfate. The solvent was removed by distillation. The residue was purified by column chromatography on silica gel (ethyl acetate) to provide 3.87 g of 3-methylthio-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole.

NMR (CDCl 3) d: 0.41 (9H, s), 2.39 (3H, s), 7.10 (1H, s), 8.04 (1H, s) c) 3-methylthioimidazo [5, 1-b] thiazole A solution was added 1 N of tetra-n-butylammonium fluoride / THF (20.0 ml) in an argon atmosphere, at room temperature, to a solution of 3-methylthio-2- (trimethylsilyl) imidazo [5, 1-b] -thiazole in 70 ml of dry THF. The mixture was stirred at the same temperature for 15 minutes. A half-saturated salt solution was added to the reaction mixture. Ethyl acetate was then added, followed by washing with a semi-saturated salt solution. The organic layer was dried over anhydrous magnesium sulfate. The solvent was removed by distillation. The residue was purified by column chromatography on silica gel (ethyl acetate) to provide 2.62 g of 3-methylthioimidazo [5, 1-b] thiazole.

NMR (CDCl 3) d: 2.49 (3H, s), 6.80 (1H, s), 7.14- (1H, s), 8.05 (1H, s) d) 3-methylthio-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole Substantially in the same manner as in preparation 4-b), 5.44 g of the title compound was obtained from 2. 62 g of 3-methylthioimidazo [5, 1-b] thiazole. 0.92 (9H, t, J = 7.3 Hz), 1.24 (6H, m), 1.30 - 1.40 (6H,), 1. 54 - 1.63 (6H, m), 2.37 (3H, s), 7.14 (1H, s), 8.01 (1H, s) Preparation 48 5-Acetyl-7-methylthio-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole a) 5-iodo-7-methylthioimidazo- [5, 1-b] thiazole N- was added iodosuccinimide (3.08) with ice-cooling to a solution of 2.28 g of 7-methylthioimidazo- [5, 1-b] thiazole in dichloromethane. The mixture was stirred at room temperature for 7 hours. Saturated saline was added to the reaction mixture, followed by separation. The organic layer was washed with a dilute aqueous solution of sodium thiosulfate and a saturated saline solution, in this order, and then dried over anhydrous magnesium sulfate.

The solvent was removed by distillation. The residue was purified by column chromatography on silica gel (ethyl acetate: dicyclohexan 1: 1) to provide 3. 78 g of 5-iodo-7-methylthioimidazo- [5, 1-b] thiazole NMR (CDC13) d: 2.42 (3H, s), 6.93 (1H, d, J = 4.4 Hz), 7.25 (1H, d, J = 4.4 Hz) b) 5-acetyl-7-methylthioimidazo [5, 1-b] thiazole A 1 N solution of ethylmagnesium bromide / THF (4.78 ml) was added under an argon atmosphere at a temperature of -40 ° C to a solution of 963 mg of 5-iodo-7-methylthioimidazo- [5, 1-b] thiazole in 30 ml of dry THF. The mixture was stirred at the same temperature for 30 minutes. Acetyl chloride (0.35 ml) was added thereto. The temperature of the system was raised to -5 ° C for a period of 2 hours. A saturated aqueous solution of ammonium chloride was added to the reaction mixture. Ethyl acetate was then added there, followed by washing with a dilute aqueous solution of sodium thiosulfate and a saturated saline solution, in this order. The organic layer was dried over anhydrous magnesium sulfate. The solvent was removed by distillation. The residue was purified by column chromatography on silica gel (dichloromethane: ethyl acetate: hexane 2: 1: 1) to provide 384 mg of 5-acetyl-7-methylthioimidazo [5, 1-b] thiazole. NMR (CDC13) d: 2.52 (3H, s), 2.67 (3H, s), 7.10 (1H, d, J = 4. 2 Hz), 8.46 (1H, d, J = 4.2 Hz) c) 5-acetyl-7-methylthio-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole Substantially in the same manner as in Preparation 5-b), 283 mg of the title compound was obtained from 378 mg of 5-acetyl-7-methylthioimidazo [5, 1-b] thiazole. 0.92 (9H, t, J = 7.3 Hz), 1.19 (6H, m), 1.33 - 1.44 (6H, m), 1. 55 - 1.64 (6H, m), 2.52 (3H, s), 2.66 (3H, s), 8.23 (1H, s) Preparation 48 5-Cyano-7-methylthio-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole a) 5-cyano-7-methylthioimidazo- [5, 1-b] thiazole 1 N was added of ethylmagnesium bromide / THF (2.0 ml) in an argon atmosphere at a temperature of -40 ° C to a solution of 405 mg of 5-iodo-methylthioimidazo- [5, 1-b] thiazole in 12 ml of THF. The mixture was stirred at the same temperature for 30 minutes. P-Toluenesulfonyl cyanide (372 mg) was added thereto. The temperature of the system was raised to -5 ° C for a period of 1 hour. A saturated aqueous solution of ammonium chloride was added to the reaction mixture. Ethyl acetate was added there, followed by washing with a saturated saline solution. The organic layer was dried over anhydrous magnesium sulfate. The solvent was removed by distillation. The residue was purified by column chromatography on silica gel (dichloromethane: ethyl acetate: hexane = 3: 1: 1) to give 131 mg of 5-cyano-7-methylthioimidazo- [5, 1-b] thiazole. NMR (CDC13) d: 2.52 (3H, s), 2.67 (3H, s), 7.10 (1H, d, J = 4.2 Hz), 8.46 (1H, d, J = 4.2 Hz) b) 5-cyano-7 -methylthio-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole Substantially in the same manner as in preparation 4-b), 262 mg of the title compound was obtained from 253 mg of sodium -cyano-7-methylthioimidazo- [5, 1-b] thiazole. NMR (CDCI3) d: 0.93 (9H, t, J = 7.3 Hz), 1.23 (6H, m), 1.31 -1.41 (6H, m), 1.52 - 1.62 (6H, m), 2.50 (3H, s), 7.37 (1H, s) Preparation 48 7- (4-Nitrobenzyloxycarbonylamino-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole a) 7- (4-nitrobenzyloxycarbonylamino) acetyl imidazo- [5,1] -b] thiazole 7-Azidaacetylimidazo [5, 1-b] thiazole (1.71 g) was dissolved in 60 ml of THF. Water (30 ml), 24.8 ml of 1 N hydrochloric acid, and 850 mg of 10% Pd-C were added to the solution. The reaction was allowed to proceed under a hydrogen atmosphere at room temperature for 1 hour. After finishing the reaction, the catalyst was removed by filtration through Celite, followed by washing with a 50% aqueous THF solution. A 1 N aqueous solution of sodium hydrogen (34.7 ml) and 2.14 g of 4-nitrobenzyl chlorocarbonate were added with ice cooling to the filtrate. The mixture was allowed to react at the same temperature for 1 hour. The resulting precipitate was collected by filtration, washed with an aqueous solution of 50% THF (20 ml) and ethyl acetate (20 ml) in this order, and then dried under reduced pressure to provide 2.59 g of 7- (4-Nitrobenzyloxycarbonylamino) acetylimidazo- [5, 1-b] thiazole. NMR (DMSO-D6) d: 4.47 (2H, d), 5.52 (2H, s), 7.53 (1H, d), 7.65 (2H, d). 8.10 (1H, d), 8.26 (2H, d), '8.35 (1H, s) b) 7- (4-Nitrobenzyloxycarbonylamino-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole was discontinued 7- (4-Nitrobenzyloxycarbonylamino) acetylimidazo- [5, 1-b] thiazole (2.52 g) in 50 ml of anhydrous THF The suspension was cooled in an argon atmosphere at a temperature of -70 ° C. tri-n-butylstannyl (3 ml) was added to the suspension, then a solution (31.5 ml) of 1 N lithium (trimethylsilyl) amide in THF was added dropwise over a period of 20 minutes. same temperature for 1 hour The reaction solution was poured into a mixed solution composed of 250 ml of ethyl acetate and 150 ml of a 15% saline solution.The organic layer was washed with a saline solution at 151, and then dried in anhydrous magnesium sulfate The solvent was removed by distillation The residue was purified by column chromatography on silica gel (ethyl acetate: dichloromethane = 1: 10) to provide 1.41 g of the title compound. NMR (CDC13) d: 0.92 (9H, t), 1.21 (6H, m), 1.38 (6H, m), 1.58 (611,), 4.77 (2H, d), 5.26 (2H, s), 5.88 (1H,), 7.30 (1H, s) , 7.54 (2H, d), 7.95 (1H, s), 8.22 (2H, d) Preparation 52 _ 7- (4-Nitrobenzyloxycarbonylamino) methyl-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole a) 7- (4-nitrobenzyloxycarbonylamino) methylimidazo- [5, 1-b] thiazole 7-Aminomethylimidazo [5, 1-b] thiazole (1.53 g) was dissolved in 50 ml of THF and Water (30 ml). A 1 N aqueous solution of sodium hydroxide (12. ml) and 2.59 g of 4-nitrobenzyl chlorocarbonate were added with ice cooling to the solution. The mixture was allowed to continue at the same temperature for 30 minutes. The reaction solution was extracted with 200 ml of ethyl acetate, followed by washing with 15% saline. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to about 20 ml. The resulting crystal was collected by filtration, washed with 20 ml of ethyl acetate and dried under reduced pressure to provide 2.26 g of 7- (4-nitrobenzyloxycarbonylamino) methylimidazo- [5, 1-b] thiazole. NMR (DMSO-D6) d: 4.23 (2H, d), 5.21 (2H, s), 7.14 (1H, d), 7.62 (2H, d), 7.81 (1H, d), 7.96 (1H, m), 8.10 (1H, s), 8.24 (2H, d) b) 7- (4-Nitrobenzyloxycarbonylamino) methyl-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole The title compound (772 mg) was obtained from 1.59 g of 7- (4-nitrobenzyloxycarbonylamino) methyl-imidazo [5, 1-b] thiazole in the same manner as in preparation 51-b), except that a mixed solution of anhydrous THF was used. HMPA as a reaction solvent. NMR (CDC13) d: 0.91 (9H, t), 1.15 (6H, m), 1.35 (6H, m), 1.58 (6H, m), 4.47 (2H, d), 5.22 (2H, s), 5.42 ( 1H, m), 7.12 (1H, s), 7.52 (2H, d), 7.89 (1H, s), 8.20 (2H, d) Preparation 53 3-pheny1-2- (tri-n-butylstannyl) imidazo [5 , 1-b] thiazole In the same manner as in preparation 4-b), 1.09 g of the title compound was obtained from 600 mg of 3-phenyl-imidazo [5, 1-b] thiazole.

NMR (CDCl 3) d: 0.85 (9H, t), 0.92 (6H, m), 1.25 (6H, m), 1.40 (6H, m), 7.06 (1H, s), 7.50 (5H, s), 7.77 ( 1H, s) Preparation 54 7- ((E) -3-oxo-l-buten-l-yl) -2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole a) 7- (( E) -3-oxo-l-buten-l-yl) imidazo [5, 1-b] thiazole 7-formyl-imidazo [5, 1-b] thiazole was dissolved in 15 ml of methanol. Methyl acetate (500 mg) was added to the solution (triphenylphosphoranilidene). The mixture was stirred at room temperature for 15 minutes. The reaction solution was concentrated under reduced pressure. The concentrate was purified by chromatography on silica gel to provide 208 mg of 7- ((E) -3-oxo-l-buten i il) imidazo [5, 1-b] thiazole. NMR (CDC13) d: 2.39 (3H, s), 6.43 (1H, dd, J = 16.3 Hz), 7.04 (1H, d, J = 4.1 Hz), 7.52 (1H, d, J = 16.3 Hz), 8.09 (1H, s) b) 7- ((E) -3-oxo-l-buten-l-yl) -2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole In the same way as in preparation 4-b), 408 mg of the title compound was obtained from 208 mg of 7- ((EV3-oxo-1-buten-1-yl) imidazo [5, 1-b] thiazole.

NMR (CDCl 3) d: 0.94 (9H, t, J = 7.3 Hz), 1.15 - 1.40 (12H, m), 1.55 - 1.65 (6H, m), 2.37 (3H, s), 6.38 (1H, d, J = 16.1 Hz), 7.25 (1H, s), 7.65 (1H, d, J = 16.1 Hz), 8.02 (1H, s) Preparation 55 7- (t-butyldimethylsilyloxy) methyl-5-methyl-2- (tri- n-butylstannyl) imidazo [5, 1-b] thiazole a) 7-formyl-5-methylimidazo [5, 1-b] thiazole DMF (8 ml) was added to 40 ml of dichloromethane. The mixture was cooled in an argon atmosphere at a temperature of 0 ° C. A solution of 9 ml of phosphorus oxychloride in 40 ml of dichloromethane was added dropwise. In addition, a solution of 1.2 g of 5-methylimidazo [5, 1-b] thiazole in 20 ml of dichloromethane was added dropwise. The mixture was heated under reflux for 5 hours. The reaction solution was poured into ice water, and then the pH was adjusted to 10 by the addition of an aqueous sodium hydroxide solution. The mixture was extracted with dichloromethane. The extract was blunted in magnesium sulfate. The solvent was then concentrated under reduced pressure. The residue was purified by chromatography on silica gel to provide 1.5 g of 7-formyl-5-methylimidazo [5, 1-b] thiazole. NMR (CDC13) d: 2.26 (3H, s), 7.13 (1H, d, J = 4.1 Hz), 7.42 s). 6.38 (1H, d, J = 4.1), 9.84 (1H, s) b) '7- (t-butyldimethylsilyloxy) methyl-5-methylimidazo [5, 1-b] thiazole 7-formyl-5-methylimidazo [ 5, 1-b] thiazole (1.5 g) in 20 ml of methanol. Borosodium hydride (210 mg) was added to the solution. The mixture was stirred at a temperature of 0 ° C for 40 minutes. A saturated solution of sodium hydrogencarbonate was added. The mixture was extracted with dichloromethane. The extract was dried over magnesium sulfate, and then concentrated under reduced pressure. The residue was dissolved in DMF. Imidazole (900 mg) and 1.8 g of t-butyldimethylsilyl chloride were added in an argon atmosphere to the solution. The mixture was stirred at room temperature for 16 hours. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate, followed by washing with a saturated saline solution. The extract was dried in magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by chromatography on silica gel to give 2.18 of 7- (t-butyldimethylsilyloxy) methyl-5-methylamidazo [5.1 L] NMR (CDC13) d: 0.13 (6H, s), 0.98 (9H, s), 2.54 (3H, s), 4.84 (2H, s), 6.73 (1H, d, J = 4.4 Hz), 7.16 (1H, d, J = 4.4 Hz), 7.27 (1H, s) c) 7- (t-butyldimethylsilyloxy) methyl-5-methyl-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole so that in preparation 4-b), 1.2 g of the title compound was obtained from 980 mg of 7- (t-butyldimethylsilyloxy) methyl-5-methylimidazo [5, 1-b] thiazole. NMR (CDCl 3) d: 0.13 (6H, s), 0.93 (9H, t, J = 7.3 Hz), 0.97 (9H, s), 1.13 (6H, s), 1.36 (6H, s), 1.58 (6H, s), 2.53 (3H, s), 4.82 (2H, s), 6.88 (1H, s), 7.27 (1H, s) Example 1 (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-propionylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3 sodium carboxylate a) (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-propionylimidazo [5, 1-b] thiazol-2-yl) -l -carbapen-2-em-3-carboxylate of 4-nitrobenzyl N, N-diisopropylethylamine (0.392 ml) and 0.252 ml of trifluoromethanesulfonic anhydride were added dropwise in this order to a solution of 543 mg of (IR, 3R, 5R , 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2-oxo-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl in 15 ml of dry acetonitrile in an argon atmosphere at a temperature of -30 ° C. The mixture was stirred at this temperature for 30 minutes. Ethyl acetate (150 ml) was added. The mixture was then washed with a semi-saturated saline solution, a mixed solution (pH 1.1) composed of semi-saturated saline solution and an aqueous solution of 1 N hydrochloric acid, a mixed solution (pH 8.9) composed of a semi-saturated saline solution and an aqueous solution saturated with sodium hydrogencarbonate and a semi-saturated salt solution, in this order. The mixture was then dried in anhydrous magnesium sulfate and filtered. The solvent was removed by distillation under reduced pressure. The residue was dissolved in 8 ml of dry N-methylpyrrolidinone. Tri-2-furylphosphine (42 mg), 409 mg of zinc chloride, 42 mg of tris (dibenzylidene ketone) dipalladium (0) and 844 mg of 7- propionyl-2- (tri-n-butylstannyl) imidazo [5, 1 -b] thiazole were added to the solution. The mixture was stirred under an argon atmosphere at a temperature of 50 ° C for 1.5 hours. Ethyl acetate (100 ml) and 50 ml of a semi-saturated aqueous solution of sodium hydrogencarbonate were added to the reaction, followed by stirring. The insoluble particles were removed by filtration. The organic layer was separated from the filtrate, washed three times with 100 ml of a semi-saturated salt solution, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was • purified by column chromatography on silica gel (dichloromethane: methanol = 30: 1 to 20: 1) to provide 454 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-. Propionylimidazo [5, 1-b] thiazol-2-yl) -l- carbapen-2-em-3-carboxylic acid 4-nitrobenzyl ester. NMR (CDC13) d: 1.26 (3H, t, J = 7.4 Hz), 1.30 (3H, d, J = 7.4 Hz), 1.60 (3H, d, J = 6.3 Hz), 3.06 (2H, q, J ' = 7.4 Hz), 3.39 (1H, dd, J? = 6.4 Hz, J _. = 2.8 Hz), 3.52 (1H, m), 4.33 (1H, m), 4.41 (1H, dd, J? = 9.8 Hz, J2 = 2.8 Hz), 5.28 (1H, d, J = 13.5 Hz), 5.52 (1H, d, J = 13.5 Hz), 7.68 (2H, d, J = 8.9 Hz), 8.00 (1H, s), 8.24 (2H, d, J = 8.9 Hz), 8.51 (1H, s) b) (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-propionylimidazo [ 5, lb] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid sodium (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-propionylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl (350 mg) was dissolved in 20 ml of THF and 20 ml of a buffer of sodium phosphate 1/15 M (pH 6.6). 10% Pd-C (350 mg) was added to the solution. The atmosphere in the reactor was replaced by hydrogen and the system was stirred at room temperature for 1.5 hours. The catalyst was removed by filtration through Celite, followed by washing with water. The filtrate was adjusted to a pH of 7.0 by the addition of an aqueous solution of sodium hydrogen carbonate and washing with ethyl acetate. The aqueous layer was purified by column chromatography on Diaion HP-20 (10% aqueous methanol) to provide 198 mg of the title compound. NMR (DaO) d (HOD = 4.80 PPM): 1.18 (3H, t, J = 7.5 Hz), 1.25 (3H, d, J = 7.1 Hz), 1.33 (3H, d.J = 6.3 Hz), 2.93 ( 2H, q, J = 7.5 Hz), 3.53 (1H, m), 3.64 (1H, m), 4.31 (2H, m), 8.04 (1H, s), 8.17 (1H, s) Example 2 (1S, 5R , 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-propionylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3 pivaloyloxymethyl carboxylate It was dissolved (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-propionylimidazo [5, 1-b] thiazol-2-yl) -l -carbapene-2-em-3-carboxylate sodium (75.8 mg) in 7 ml of DMF. Sodium hydrogen carbonate (4.9 mg) and 0.038 ml of pivaloyloxymethyl iodide were added to the solution under an argon atmosphere at a temperature of -30 ° C. The mixture was stirred for 1.5 hours. Ethyl acetate (50 ml) was added to the reaction solution. The mixture was washed three times with 30 ml of a semi-saturated salt solution. The organic layer was dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated to 5 ml under reduced pressure. The residue was purified by column chromatography on silica gel (dichloromethane: methanol = 30: 1) to provide 62.3 mg of the title compound. NMR (CDC13) d: 1.20 (9H, s), 1.26 (3H, t, J = 7.4 Hz), 1.28 (3H, d, J = 7.2 Hz), 1.37 (3H, d, J = 6.3 Hz), 3.07 (2H, q, J = 7.4 Hz), 3.35 (1H, dd, J? = 6.6 Hz, J2 = 2.8 Hz), 3.50 (1H, m), 4.30 (1H, m), 4.39 (1H, dd "J_ = 9.6 Hz, J2 = 2.8 Hz), 5.87 (1H, d, J = 5.6 Hz), 5.99 (1H, d, J = 5.6 Hz), 8.03 (1H, s), 8.51 (1H, s) Example 3 ( ÍS, 5R, 6S) -6- ((lR) -l-hydroxyethyl) -2- (7-hydroxyiminomethylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate sodium (a geometric isomer derived from an initial compound such as a low polarity oxime isomer) a) (SS, 5R, 6S) -6- (lR) -l-hydroxyethyl) -l-methyl-2- [7- 4-Nitrobenzyloxyiminomethyl) imidazo [5, 1-b] thiazol-2-yl) -1-carbapen-2-em-3-carboxylate of 4-nitrobenzyl (a geometric isomer derived from an initial compound as an isomer of oxime) low polarity) In the same manner as in Example la), 77.3 mg of (ΔS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- [7- (4-Nitrobenzyloxyiminomethyl) imidazo [5, 1 -b] thiazol-2-yl] -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl (a geometric isomer derived from an initial compound as a low polarity oxime isomer) from 86 mg of ( IR, 3R, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2-oxo-l-carbapenam-3-carboxylate of 4-nitrobenzyl and 169 mg of 7- (4-nitrobenzyloxyiminomethyl) ) -2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole (a geometric isomer derived from an initial compound as a low polarity oxime isomer). NMR (DMSO-Dg) d: 1.20 (6H, m), 3.42 (1H, m), 3.70 (1H,), 4.03 (1H, m), 4.34 (1H, m), 5.26 (2H, s), 5.39 (1H, d, -J = 13.5 Hz), 5.53 (1H, d, J = 13.5 Hz), 7.71 (4H, m), 8.22 (4H,), 8.32 (2H, s), 8.50 (1H, s) b) (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-hydroxyiminomethylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen- Sodium 2-em-3-carboxylate (a geometric isomer derived from an initial compound as a low polarity oxime isomer) The title compound (2.4 mg) was obtained from 77. 3 g of (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- [7- (4-nitrobenzyloxyiminomethyl) imidazo [5, 1-b] thiazol-2-yl] -1-carbapen-2- 4-Nitrobenzyl em-3-carboxylate (a geometric isomer derived from an initial compound as a low polarity oxime isomer) in the same manner as in Example 1-b), except that the purification was carried out by column chromatography in Diaion HP-20 (10% aqueous methanol) and Cosmosil 40C18-PREP (aqueous methanol so at 20%). NMR (D20) d (HOD = 4.80 PPM): 1.22 (3H, d, J = 6.6 Hz), 1.31 (3H, d.J = 6.3 Hz), 3.50 (2H, m), 4.28 (2H, m), 7.84 (1H, s), 8.04 (1H, s), 8.17 (1H, s) Example 4 (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methoxyiminomethylimidazo [5,1] -b] thiazol-3-yl) -l-carbapen-2-em-3-carboxylate sodium (a geometric isomer derived from an initial compound as a low polarity oxime isomer) a) (5R, 6S) -6 - ((lR) -l-hydroxyethyl) -2- (7-methoxyiminomethylimidazo [5, 1-b] thiazol-3-yl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl (a geometric isomer) derived from an initial compound as a low polarity oxime isomer) In the same manner as in Example la), 357 mg of (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- were obtained (7-methoxyiminomethylimidazo [5, 1-b] thiazol-3-yl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl (a geometric isomer derived from an initial compound as a low polarity oxime isomer) ) from 522 mg of (3R, 5R, 6S) -6- ((IR) -1-hydroxy ethyl) -2-oxo-l-carbapenam-3-carboxylate of 4-nitrobenzyl and 846 mg of 7-methoxyiminomethyl-3- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole (a geometric isomer derived from an initial compound such as a low polarity oxime isomer). NMR (CDC13) d: 1.40 (3H, d, J = 6.3 Hz), 3.39 (3H, m), 3.96 (3H, s), 4.32 (1H, m), 4.45 (1H, m), 5.17 (1H, d, J = 13.3 Hz), 5.32 (1H, d, J = 13.3 Hz), 7.15 (1H, s), 7.37 (2H, d, J = 8.5 Hz), 7.74 (1H, s), 8.15 (1H, s), 8.15 (2H, d, J = 8.5 Hz) b) (5R, 6S) -6- ((lR) -l-hydroxyethyl) -2- (7- methoxyiminomethylimidazo [5, 1-b] thiazole-3 -yl) -l-carbapen-2-em-3-carboxylate sodium (a geometric isomer derived from an initial compound as a low polarity oxime isomer) The title of the compound (93.9 ug) was obtained from 287 mg of (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methoxy: iminomethylimidazo [5, 1-b] thiazol-3-yl) -l-carbapen-2-em-3 4-Nitrobenzyl carboxylate (a geometric isomer derived from an initial compound as a low polarity oxime isomer) in the same manner as in Example 1-b), except that the purification was carried out by column chromatography in Diaion HP-20 (10% aqueous methanol) and Cosmosil 40C18-PREP (10% aqueous methanol). NMR (D20) d (HOD = 4.80 PPM): 1.32 (3H, d, J = 6.3 Hz), 3.21 (1H, m), 3.48 (1H, m), 3.60 (1H, m), 3.94 (3H, s ), 4.28 (1H,), 4.39 (1H, m), 7.20 (1H, s), 7.94 (1H, s), 8.22 (1H, s) Example 5 (5R, 6S) -6- ((IR) - 1-hydroxyethyl) -l-methyl-2- (7-methoxyiminomethylimidazo [5, 1-b] thiazol-3-yl) -l-carbapen-2-em-3-carboxylate of pivaloyloxymethyl (a geometric isomer derived from a compound initial as a low polarity oxime isomer) In the same manner as in Example 2, 22.6 g of the title compound was obtained from 40.0 mg of (5R, 6S) -6- ((IR) -1-hydroxyethyl ) -2- (7-methoxyiminomethylimidazo [5, 1-b] thiazol-3-yl) -l-carbapen-2-em-3-carboxylate sodium (a geometric isomer derived from an initial compound as an isomer of oxime) low polarity). NMR (CDC1) d: 1.19 (9H, s), 1.38 (3H, d, J = 6.3 Hz), 3.37 (3H,), 3.96 (3H, s), 4.30 (1H, _t_), 4.42, 1H, m), 5.78 (1H, d, J = 5.6 Hz), 5.88 (1H, d, J = 5.6 Hz), 7.25 (1H, s), 7.79 (1H, s), 8.21 (1H, s) Example 6 (1S, 5R, 6S) -6- ( (IR) -1-hydroxyethyl) -l-methyl-2- (7-pivaloylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid sodium a) (IS , 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-pivaloylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2- 4-nitrobenzyl em-3-carboxylate Substantially in the same manner as in Example la), 487 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -1-methyl- were obtained 2- (7-pivaloylimidazo [5, 1-b] thiazol-2-? L) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl from (IR 3R, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2-oxo-l-carbapenam-2-em-3-carboxylate and 460 mg of 7-pivaloyl-2- (tri-n-butylstannyl) imidazo [5, lb] thiazole. NMR (DMSO-Ds) d: 1.22 (3H, t, J = 7.4 Hz), 1.30 (12H, m), 3.38 - 3.43 (1H, m), 3.60 - 3.70 (1H, m), 3.95 - 4.05 (1H , m), 4.27 - 4.32 (1H,), 5.38 (1H, d, J = 13.5 Hz), 5.50 (1H, d, J = 13.5 Hz), 7.71 (2H, d, J = 8.9 Hz), 8.20 - 8.30 (3H, m), 8.35 (1H, s) b) (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-pivaloylimidazo [5, 1- sodium bia thiazol-2-yl) -l-carbapen-2-em-3-carboxylate The title compound (99 mg) was obtained from 487 mg of (IS, 5R, 6S) -6- (( IR) -1-hydroxyethyl) -l-methyl-2- (7-pivaloylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 4-nitrobenzyl ester of substantially the same way as in Example 1-b), except that the purification was carried out using Cosmosil 40C18-PREP (aqueous acetonitrile 10%) NMR (D20) d (HOD = 4.80 PPM): 1.24 (3H, d, J = 7.1 Hz), 1.28 - 1.32 (12H, m), 3.46 - 4.54 (2H, m), 4.23 - 4.32 (2H, m), 7.81 (1H, s), 8.02 (1H, s) Example 7 (ÍS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-pivaloylimide) [5, 1-b] thiazol-3-yl) -l-carbapen-2-em-3-pivaloyloxymethyl carboxylate Substantially in the same manner as in Example 2, the title compound (31 mg) was obtained from from 40 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-pivaloylimidazo [5, 1-b] thiazol-3-yl) -l -carbapen-2-em-3-carboxylate sodium. NMR (CDC13) d: 1.22 (9H, s), 1.28 (3H, d, J = 7.3 Hz), 1.35 -1.40 (12H, m), 3.31 (1H, dd, J_ = 6.7 Hz, J2 = 2.8 Hz) , 3.10 -3.56 (1H, m), 5.88 (1H, d, J = 5.6 Hz), 5.98 (1H, d, J = 5.6 Hz), 7.89 (1H, s), 8.25 (1H, s) Example 8 ( 5R, 6S) -2- (7- (-acetyl-3-methylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -i-ca? Ba? ~ 2-em ~ 3-carboxylic acid sodium a) (5R, 6S) -2- (7-acetyl-3-methylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1 -hydroxyethyl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl In the same manner as in Example la), 303 mg of (5R, 6S) -2- (7-acetyl-3- was obtained methylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl from 453 mg of (3R) , 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2-oxo-l-carbapenam-2-em-3-carboxylate of 4-nitrobenzyl and 745 mg of 7-acetyl-3-methyl-2 - (tri-n-butylstannyl) imidazo [5, 1-b] thiazole. NMR (CDCI3) d: 1.40 (3H, d, J = 6.3 Hz), 2.27 (3H, s), 2.61 (3H, s), 3.21 (1H, dd, J_ = 18.5 Hz, J; = 9.4 Hz), 3.23 (1H, dd, J? = 18.5 Hz, J2 = 9.5 Hz), 3.38 (1H, dd, J? = 6.4 Hz, J2 = 3.0 Hz), 4.26 - 4.41 (1H, m) , 4.42 (1H, td, J? = 9.5 Hz, J- = 3.0 Hz), 5.23 (1H, d, J = 13.5 Hz), 5.41 (1H, d, J = 13.5 Hz), 7.55 (2H, dm, J = 8.8 Hz), 7.82 (1H, s), 8.16 (2H, dm, J = 8.8 Hz) b) (5R, 6S) -2- (7-acetyl-3-methylimidazo [5, 1-b] thiazole -2-yl) -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate sodium In the same manner as in example 1-b), the title compound (125 mg) was obtained from 303 mg of (5R, 6S) -2- (7 - (- acetyl-3-methylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1 -hydroxyethyl) -l-carbapen-2-em-3-carboxylic acid 4-nitrobenzyl, NMR (D20) d (HOD = 4.80 PPM): 1.30 (3H, d, J = 6.5 Hz), 2.35 (3H, s) , 2.54 (3H, s), 3.14 (1H, dd, üi = 17.3 Hz, Jc = 9.9 Hz.i, 3.33 (1H, dd, J? = 17.3 Hz, J2 = 8.4 Hz), 3.57 (1H, dd, J? = 5.8 -Hz, J2 = 3.1 Hz), 4.27 (1H, qd, J? = 6.5 Hz, J2 = 5.8 Hz), 4.36 (1H, ddd, J? = 9.9 Hz, J2 = 8.4 Hz, J3 = 3.1 Hz), 8.19 (1H, s) Example 9 (5R, 6S) -2- (7-aceti l-3-Methylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate of pivaloyloxymethyl In the same manner as in Example 2, the title compound (19 mg) was obtained from 35 mg of (5R, 6S) -2- (7-acetyl-3-methylimidazo [5, 1-b] thiazol-2-yl) - 6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate sodium. NMR (CDC13) d: 1.10 (9H, s), 1.37 (3H, d, J = 6.3 Hz), 1.99 (1H, broad), 2.37 (1H, s), 2.61 (1H, s), 3.20 (1H, dd, Jx = 18.5 Hz, J2 = 7.5 Hz), 3.22 (1H, dd, J? = 18.5 Hz, J: = 7.5 Hz), 3.35 (1H, dd, J? = 6.5 Hz, J2 = 3.0 Hz), 4.33 - 4.35 (1H, m), 4.39 (1H, td, J? = 9.5 Hz, J2 = 3.0 Hz), 5.78 (1H, d, J = 5.5 Hz), 5.88 (1H, d, J = 5.5 Hz) 7.90 (1H, s) Example 10 (1S, 5R, 6S) -2- [7- (2-formylaminopropionyl) imidazo [5, 1-b] thiazol-2-yl] -6- ((IR) -1 sodium hydroxyethyl) -l-methyl-carbapen-2-em-3-carboxylate (a high polarity isomer) Substantially in the same manner as in Example la), 68 mg of a crude product of (IS, 5R, 6S) -2- [7- (2-formylaminopropionyl) imidazo [5, lb] thiazol-2-yl] -6- ((1R) -1-hydroxyethyl) -l-methyl-carbapen-2-em- 3-Nitrobenzyl 3-carboxylate (a mixture of diastereomers) from 91 mg of (IR, 3R, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2-oxo-l -carbapenam-3-carboxylate of 4-nitrobenzyl and 96 mg of 7- (2-formylaminopropionyl) -2- (t ri-n-butylstannyl) imidazo [5,1-b] thiazole. The title compound (3.2 mg) was obtained from this crude product substantially in the same manner as in Example 6-b). NMR (D20) d (HOD = 4.80 PPM): 1.23 (3H, d, J = 7.1 Hz), 1.32 (3H, d, J = 6.3 Hz), 1.50 (3H, d, J = 7.4 Hz), 3.52 (1H, dd, J? = 6.1 Hz, J2 = 2.1 Hz), 3.55 - 3.65 (1H, m), 4.22 - 4.35 (2H m), 5.35 (1H, q, J = 7.4 Hz), 8.00 (1H, s), 8.12 (2H, m) Example 11 (IS, 5R, 6S) -2- [7- (2-formylaminopropionyl) imidazo [5, 1-b] thiazol-2-yl] -6- ((IR) Sodium-1-hydroxyethyl) -l-methyl-carbapen-2-em-3-carboxylate (a low polarity isomer) Substantially in the same manner as in Example la), the title compound (3.4 mg) was obtained from 68 mg of the crude product of (SS, 5R, 6S) -2- [7- (2-formylaminopropionyl) imidazo [5, 1-b] thiazol-2-yl] -6- ((IR) -1 -hydroxyethyl) -l-methyl-carbapen-2-em-3-carboxylate of 4-nitrobenzyl (a mixture of diastereomers) prepared in example 10. NMR (D20) d (HOD = 4.80 PPM): 1.23 (3H, d , J = 7.1 Hz), 1.32 (3H, d, J = 6.3 Hz), 1.47 (3H, d, J = 7.4 Hz), 3.50 (1H, dd, Jx = €. 0 Hz, J2 = 2.4 Hz), 3.55 - 3.65 (1H, m), 4.23 - 4.35 (2H, m), 5.32 (1 H, d, J = 7.4 Hz), 8.03 (1H, s), 8.13 (1H, s), 8.18 (1H, s) Example 12 (1S, 5R, 6S) -6- ((lR) -l-hydroxyethyl ) -2- (7-isobutyrylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid sodium a) (S, 5R, 6S) -6- ((IR ) -1-hydroxyethyl) -2- (7-isobutyrylimidazo [5, 1-b] thiazol-2-yl) '-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl In the same manner as in the example la), 440 mg of (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-isobutyrylimidazo [5, 1-b] thiazol-2-yl) -l were obtained -carbapen-2-em-3-carboxylate of 4-nitrobenzyl from 725 mg of (IR, 3R, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2-oxo-l-carbapenam-3-carboxylate of 4-nitrobenzyl and 96 mg of 7-isobutyryl-2- ( tri-n-butylstannyl) imidazo [5, 1-b] thiazole. NMR (CDC13) d: 1.13 (6H, d, J = 6.6 Hz), 1.20 (3H, d, J = 7.4 Hz), 1.29 (3H, d, J = 6.0 Hz), 3.30 (1H, m), 3.46 (1H, m), 3.58 (1H,), 4.19 (1H, m), 4.36 (1H, dd, J? = 9.6 Hz, J2 = 2.7 Hz), 5.15 (1H, d, J = 13.7 Hz), 5.39 (1H, d, J = 13.7 Hz), 7.54 (2H, d, J = 8.6 Hz), 7.98 (1H, s), 8.05 (2H, d, J = 8.6 Hz), 8.37 (1H, s) b) (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-isobutyrylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3 sodium carboxylate The title compound (133 mg) was obtained from 400 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-isobutyrylimidazo [5, 1-] b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl in the same manner as example 1-b), except that the purification was carried out by column chromatography on Diaion HP- 20 (10% aqueous methanol) and Cosmosil 40C18-PREP (10% aqueous methanol). NMR (D20) d (HOD = 4.80 PPM): 1.18 (9H, m), 1.32 (3H, d, J = 6.5 Hz), 3.44 (1H, m), 3.49 (1H, dd, J? = 6.3 Hz, J2 = 2.7 Hz), 3.57 (1H, m), 4.27 '(1H, m), 4.32 (1H, dd, Jx = 9.2 Hz, J2 = 2.7 Hz), 7.94 (1H, s), 8.07 (1H, s Example 13 (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-isobutyrylimidazo [5, 1-b] thiazol-3-yl) -l-carbapen-2-em Pivaloyloxymethyl carboxylate In the same manner as in Example 2, 48 mg of the title compound was obtained from 52 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) - 2- (7-Isobutyrylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate sodium. NMR (CDC13) d: 1.17 (9H, s), 1.26 (9H, m), 1.35 (3H, d, J = 6.3 Hz), 3.35 (1H, dd, J? = 6.6 Hz, J2 = 2.8 Hz), 3.49 (1H, m), 3.70 (1H, m), 4.28 (1H, m), 4.39 (1H, dd, J? = 9.8 Hz, J2 = 2.8 Hz), 5.85 (1H, d, J = 5.6 Hz) , 5.97 (1H, d, J = 5.6 Hz), 8.05 (1H, s), 8.49 (1H, s) Example 14 (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7 sodium -propionylimidazo [5, 1-b] thiazol-3-yl) -l-carbapen-2-em-3-carboxylate a) (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2 - (7-propionylimidazo [5, 1-b] thiazol-3-yl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl In the same manner as in Example la), 51.8 mg of (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-propionylimidazo [5, 1-b] thiazol-3-yl) -l-carbapen-2-em-3-carboxylate from 4-Nitrobenzyl from 168 mg of (3R, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2-oxo-l-carbapenam-3-carboxylate of 4-nitrobenzyl and 272 mg of 7- propionyl-3- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole. NMR (CDC13) d: 1.24 (3H, t, J = 7.4 Hz), 1.41 (3H, d, J = 6.3 Hz), 3.03 (2H, q, J = 7.4 Hz), 3.39 (3H, m), 4.33 (1H, m), 4.47 (1H, m), 5.22 (1H, d, J = 13.6 Hz), 5.38 (1H, d, J = 13.6 Hz), 7.22 (1H, s), 7.49 (2H, d, J = 8.8 Hz), 7.64 (1H, s), 8.18 (2H, d, J = 8.8 Hz) b) (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-propionylimidazo Sodium [5, 1-b] thiazol-3-yl) -l-carbapen-2-em-3-carboxylate The same as in Example 1-b), the title compound (17.4) was obtained from of 51.8 mg of (5R, 6S) -6 - ((lR) -1-hydroxyethyl) -2- (7-propionylimidazo [5, 1-b] thiazol-3-yl) -1-carbapen-2-em- 4-Nitrobenzyl 3-carboxylate. NMR (D20) d (HOD = 4.80 PPM): 1.19 (3H, t, J = 7.4 Hz), 1.33 (3H, d, J = 6.2 Hz), 2.97 (2H, q, J = 7.4 Hz), 3.25 (1H, dd, J? = 17.4 Hz, J2 = 10.0 Hz), 3.50 (1H, dd, J? = 17.4 Hz, J2 = 8.7 Hz), 3.62 (1H, dd, J? = 5.9 Hz, J2 = 2.8 Hz), 4.30 (1H, m), 4.42 (1H,), 7.30 (1H, s), 7.92 (1H, s) Example 15 ( 5R, 6S) -2- (7-acetylimidazo [5, 1-b] thiazol-2-yl) 6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate sodium b ) (5R, 6S) -2- (7-Acetylimidazo [5, lb] thiazol-2-yl) 6- ((1R) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl In the same manner as in Example la), 0.79 g of (5R, 6S) -2- (7-acetylimidazo [5, 1-b] thiazol-2-yl) 6- ((IR) -1- was obtained. hydroxyethyl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl from 2.68 g of (3R, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2-oxo-l-carbapenam -3-carboxylic acid 4-nitrobenzyl ester and 3.86 g of 7-acetyl-2_- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole. NMR (CDCl 3) d: 1.37 (3H, t, J = 6.4 Hz), 2.61 (3H, s), 3.30 -3.42 (3H, m), 4.21 (1H, m), 4.35 (1H, m), 5.35 ( 1H, d, J = 13.5 Hz), 5.54 (1H, d, J = 14.1 Hz), 7.68 (2H, d, J = 14.1 Hz), 7.71 (2H, d, J = 8.8 Hz), 8.05 (1H, s), 8.24 (2H, d, J = 8.8 Hz), 8.39 (1H, s) MS (TSP): 497 (M ++ H) b) (5R, 6S) -2- (7-acetylimidazo [5, 1-b] thiazol-2-yl) 6- ((1R) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate sodium In the same manner as in example 1-b), 157 mg of the title compound from 368 mg of (5R, 6S) -2- (7-acetylimidazo [5, 1-b] thiazol-2-yl) 6- ((IR) -1-hydroxyethyl) -1 -carbapen-2-em-3-carboxylate of 4-nitrobenzyl. NMR (D20) d (HOD = 4.80 PPM): 1.31 (3H, d, J = 6.4 Hz), 2.49 (3H, s), 3.30 (2H,), 3.51 (1H, dd, J? = 5.8 Hz, J2 = 3.0 Hz), 4.25 (2H,), 7.85 (1H, s), 8.11 (lH, _s) Example 16 (5R, 6S) -2- (7-acetylimidazo [5, 1-b] thiazol-2-yl) ) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate of pivaloyloxymethyl In the same manner as in Example 2, 18.6 g of the title compound were obtained from 22..0 mg of (5R, 6S) -2- (7-acetylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -1-carbapen- Sodium 2-em-3-carboxylate and 0.014 ml of pivaloyloxymethyl iodide. NMR (CDCl 3) d: 1.17 (9H, s), 1.31 (3H, d, J = 6.3 Hz), 2.55 (3H, s), 3.22 - 3.32 (3H, m), 4.19 - 4.31 (2H, m), 5.83 (1H, d, J = 5.6 Hz), 5.95 (1H, d, J = 5.6 Hz), 7.95 (1H, s), 8.46 (1H, s), MS (TSP): 497 (M ++ H) Example 17 (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-isobutyrylimidazo [5, 1-b] ] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid sodium a) (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-isobutyrylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl In the same manner as in Example la), 360 mg of (5R, 6S) -6- were obtained ((IR) -1-hydroxyethyl) -2- (7-isobutyrylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl from 350 mg of (3R, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2-oxo-l-carbapenam-3-carboxylate of 4-nitrobenzyl and 450 mg of 7-isobutyryl-2- (tri-n) -butyl ethanyl) imidazo [5, 1-b] thiazole. NMR (CDC13) d: 1.21 (6H, d, J = 6.9 Hz), 1.36 (3H, d, J = 6.2 Hz), 3.35 (3H, m), 3.64 (1H, m), 4.32 (2H, m) , 5.23 (1H, d, J = 13.8 Hz), 5.45 (1H, d, J = 13.8 Hz), 7.60 (2H, d, J = 8.8 Hz), 7.98 (1H, s), 8.11 (2H, d, J = 8.8 Hz), 8.25 (1H, s) 'b) (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-isobutyrylimidazo [5, 1-b] thiazole-2- il) -l-carbapen-2-em-3-carboxylate sodium The title compound (178 mg) was obtained from 350 mg of (5R, 6S) -6- ((IR) -1-hydroxyethyl) - 2- (7-isobutyrylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 4-nitrobenzyl ester in the same manner as in "example 1-b), except purification was carried out by column chromatography on Diaion HP-20 (10% aqueous methanol) and Cosmosil 40C18-PREP (10% aqueous methanol), NMR (D20) d (HOD = 4.80 PPM): 1.16 (6H, m), 1.31 (3H, d, J = 6.5 Hz), 3.24 (2H, m), 3.42 (2H, m), 4.25 (2H, m), 7.75 (1H, s), 8.01 (1H, s) Example 18 (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-isobutyrylimidazole [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of pivaloyloxymethyl In the same manner as in Example 2, the title compound (60.8 mg) was obtained from 62 mg of (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-isobutyrylimidazo [5, 1-b] thiazole- 2-yl) -l-carbapen-2-em-3-carboxylate sodium. NMR (CDC13) d: 1.22 (9H, s), 1.26 (6H, d, J = 6.9 Hz), 1.37 (3H, d, J = 6.3 Hz), 3.34 (3H, m), 3.70 (1H, m) , 4.31 (2H, m), 5.89 (1H, d, J = 5.6 Hz), 6.01 (1H, d, J = 5.6 Hz), 8.04 (1H, s), 8.54 (1H, s) Example 19 (1S, 5R, 6S) -2- (7-acetyl-5-methylimidazo [5, lb] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em Sodium -3-carboxylate a) (SS, 5R, 6S) -2- (7-acetyl-5-methylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl ) -l-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl In the same manner as in Example la), 301 mg of (1S, 5R, 6S) -2- (7 -acetyl-5-methylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate from 4- Nitrobenzyl from 455 mg of (IR, 3R, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2-oxo-l-carbapenam-3-carboxylate of 4-nitrobenzyl and 707 mg of 7- acetyl-5-methyl-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole. NMR (CDC13) d: 1.30 (3H, d, J = 7.4 Hz), 1.40 (3H, d, J = 6.2 Hz), 2.58 (3H, s), 2.66 (3H, s), 3.38 (1H, dd, J_ = 6.5 Hz, J2 = 2.9 Hz), 3.51 (1H,), 4.32 (1H, m), 4.40 (1H, dd, J? = 9.5 Hz, J2 = 2.9 Hz), 5.28 (1H, d, J = 13.5 Hz), 5.54 (1H, d, J = 13.5 Hz), 7.68 (2H, d, J = 8.8 Hz), 8.24 (2H, d, J = 8.8 Hz), 8.38 (1H, s) b) (1S , _ 5R, 6S) -2- (7-acetyl-5-methylimidazo [5, lb] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2 Sodium-3-carboxylate In the same manner as in Example 1-b), the title compound (109 mg) was obtained from 155 mg of (IS, 5R, 6S) -2- (7- acetyl-5-methylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl . NMR (D20) d (HOD = 4.80 PPM): 1.17 (3H, d, J = 7.1 Hz), 1.33 (3H, d, J = 6.3 Hz), 2.38 (3H, s), 2.46 (3H, s), 3.46 (1H, m), 3.54 (1H, m), 4.29 (2H, m), 7.69 (1H, s) Example 20 (ls, 5R, 6S) -2- (7-acetyl-5-methylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate of pivaloyloxymethyl In the same manner as in example 2, the title compound (37.2 mg) was obtained from 49.1 mg of (1S, 5R, 6S) -2- (7-acetyl-5-methylimidazo [5, 1-b] thiazol-2-yl) -6-. { (IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate sodium. NMR (CDC13) d: 1.20 (9H, s), 1.28 (3H, d, J = 7.1 Hz), 1.37 (3H, d, J = 6.3 Hz), 2.58 (3H, s), 2.70 (3H, m) , 3.35 (1H, dd, J? = 6.6 Hz, J2 = 2.8 Hz), 3.49 (1H, m), 4.29 (1H, m), 4.38 (1H, dd, J? = 9.8 Hz, J2 = 2.8 Hz), 5.86 (1H, d, J = 5.6 Hz), 6.00 (1H, d, J = 5.6 Hz), 8.35 (1H, s) Example 21. (ls, 5R, 6S) -2- (7 -acetyl-3-met? limidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxy? sodium a) (ls, 5R, 6S) -2- (7-acetyl-3-methylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l -methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl In the same manner as in Example la), 237 mg of (Is, 5R, 6S) -2- (7-acetyl-3 was obtained -methylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 4-nitrobenzyl ester from 343 mg of (IR, 3R, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2-oxo-l-carbapenam-3-carboxylate 4-nitrobenzyl and 533 mg of 7- acetyl-3-methyl- * 2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole. NMR (CDC13) d: 1.19 (3H, d, J = 7.2 Hz), 1.39 (3H, d, J = 6.3 Hz), 2.28 (3H, s), 2.62 (3H, s), 3.44 (2H, m) , 4.33 (1H, m), 4.48 (1H, dd, J? = 10.2 Hz, J2 = 3.2 Hz), 5.20 (1H, d, J = 13.5 Hz), 5.40 (1H, d, J = 13.5 Hz), 7.53 (2H, d, J = 8.9 Hz), 7.82 (1H, s), 8.16 (2H, d, J = 8.9 Hz) b) (SS, 5R, 6S) -2- (7-acetyl-3-methylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate sodium In the same manner as in the . Example 1-b), 130 mg compound of the title was obtained from 237 mg of (SS, 5R, 6S) -2- (7-acetyl-3-methylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl. NMR (D20) d (HOD = 4.80 PPM): 1.16 (3H, d, J = 7.1 Hz), 1.30 (3H, d, J = 6.3 Hz) / 2.37 (3H, s), 2.53 (3H, s), 3.37 (1H, m), 3.56 (1H, dd, J_ = 5.8 Hz, J2 = 2.9 Hz), 8.20 (1H, s) 'Example 22 (ls, 5R, 6S) -2- (7-acetyl-3- methylimidazo [5, lb] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate of pivaloyloxymethyl In the same manner as in the example 2, was obtained from the title compound (41.2 mg) from 48.4 mg of (SS, 5R, 6S) -2- (7-acetyl-3-methylimidazo [5, 1-b] thiazol-2-yl) - 6- ((IR) -1-hydroxyethyl) -l-methyl-l-metcarbapen-2-em-3-carboxylate _. of sodium. NMR (CDCl 3) d: 1.08 (9H, s), 1.18 (3H, d, J = 7.4 Hz), 1.37 (3H, d, J = 6.3 Hz), 2.39 (3H, s), 2.61 (3H, s), 3.42 (2H, m), 4.30 (1H,), 4.46 (1H, dd, J? = 10.1 Hz, J2 = 3.0 Hz), 5.73 (1H, d, J = 5.56 Hz), 5.88 (1H, d, J = 5.5 Hz), 7.93 (1H, s) Example 23 (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2 - (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid sodium a) (5R, 6S) -6- ((IR) -1-hydroxyethyl ) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl Substantially in the same manner as in example la), obtained 453 mg of (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em- 3-Nitrobenzyl 3-carboxylate from 209 mg of (3R, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2-oxo-l-carbapenam-3-carboxylate of 4-nitrobenzyl and 251 mg of 7-methanesulfonyl-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole. NMR (CDCI3) d: 1.36 (3H, d, J = 6.3 Hz), 3.22 (3H, s), 3.32 (2H, dd, J? = 7.0 Hz, J2 = 3.1 Hz), 3.36 - 3.40 (1H, m), 4.20 -4.28 (1H, m), 4.30 - 4.38 (1H,), 5.34 (1H, d, J = 13.5 Hz), 5.52 (1H, d, J = 13.5 Hz), 7.70 (2H, d, J = 8.9 Hz), 8.13 (1H, s), 8.26 (2H, d, J = 8.9 Hz), 8.30 (1H, s) b) (5R, 6S) -6- ((lR) -l-hydroxyethyl) -2- (7- methanesulfoni i sodium limidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate The title compound (69.7 mg) was obtained from 282 mg of (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl substantially from the same way as in example 1-b), except that the purification was carried out using Cosmosil 40C18-PREP (5% aqueous methanol). NMR (D20) d (HOD = 4.80 PPM): 1.30 (3H, d, J = 6.3 Hz), 3.29 (3H, s), 3.29 - 3.36 (2H, m), 3.50 - 3.55 (1H,), 4.25 - 4.35 (2H, m), 7.90 (1H, s), 8.25 (1H, s) Example 24 (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5,1] -b] thiazol-3-yl) -l-carbapen-2-em-3-carboxylic acid sodium a) (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [ 5, 1-b] thiazol-3-yl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl Substantially in the same manner as in Example la), 84 mg of (5R, 6S) were obtained -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-3-yl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl from of 87 mg of (3R, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2-oxo-l-carbapenam-3-carboxylate of 4-nitrobenzyl and 110 mg of 7-methanesulfonyl-3- ( tri-n-butylstannyl) imidazo [5, 1-b] thiazole.

NMR _ (CDCl 3) d: 1.40 (3 H, d, J = 6.3 Hz), 3.20 (3 H, s), 3.35 -3.45 (3 H, m), 4.25 - 4.33 (1 H, m), 4.45 - 4.52 (1 H , d, J = 13.5 H), 5.38 (1H, d, J = 13.5 Hz), 7.20 (1H, s), 7.54 (2H, d, J = 8.8 Hz), 7.80 (1H, s), 8.20 (2H , d, J = 8.8 Hz) b) (5R, 6S) -6- ((lR) -l-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-3-yl) -l- sodium carbapen-2-em-3-carboxylate Substantially in the same manner the title compound (30.1 mg) was obtained from 84 mg of (5R, 6S) -6- ((IR) -1-hydroxyethyl) - 2- (7-methanesulfonylimidazo [5, 1-b] thiazol-3-yl) -1-carbapen-2-em-3-carboxylate of 4-nitrobenzyl, except that the purification was carried out using Cosmosil 40C18-PREP (5% aqueous methanol). NMR (D2O d (HOD = 4.80 PPM): 1.30 (3H, d, J = 6.3 Hz), 3.22 (1H, dd, J? = 17.3 Hz, J2 = 9.7 HzV 3.30 (3H, s), 3.48 (1H, dd, J? = 17.3 Hz, J2 = 8.2 Hz), 3.59 - 3.62 (1H, m), 4.23 - 4.30 (1H, m), 4.35 - 4.43 (1H, m), 7.25 (1H, s), 8.05 ( 1H, s) Example 25 (SS, 5R, 6S) -6- ((1R) -l-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-bl thiazol-3-yl] -l-methyl-1 sodium carbapene-2-em-3-carboxylate a) (ls, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] ] thiazol-3-yl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl Substantially in the same manner as in Example la), 817 mg of (1S, 5R, 6S) -6- were obtained ((IR) -1-hydroxyethyl) -2- (7-methylthioimidazo [5, 1-b] thiazol-3-yl) -l-carbapen-2-em-3-carboxylic acid 4-nitrobenzyl from 797 mg of (IR, 3R, 5R, 6S) -6- ((lR) -l-hydroxyethyl) -l-methyl-2-oxo-l-carbapenam-3-carboxylate of 4-nitrobenzyl and 919 mg of 7- methylthio- 3- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole. NMR (DMSO-D6) d: 1.06 (3H, d, J = 7.2 Hz), 1.17 (3H, d, J = 6.3 Hz), 3.32 (3H, s), 3.53 - 3.57 (1H, m), 3.63 - 3.70 (1H, m), 4.00 - 4.08 (1H, m), 4.41 (1H, dd, J? = 10.3 Hz, J2 = 3.1 Hz), 7.40 (1H, s), 7.45 (2H, d, J = 8.3 Hz), 8.15 (2H, d, J = 8.3 Hz), 8.19 (1H, s) b) (1S, 5R, 6S) -6- ((lR) -l-hydroxyethyl) -2- (7- methanesulfonylimidazo [ 5, 1-b] thiazol-3-yl) -l-methyl-l-carbapen-2'-em-3-carboxylate of 4-nitrobenzyl OXONE (manufactured by Du pont (El) of Nemours &Co. ) (123 mg) with ice cooling to a solution of 51.4 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methylthioimidazo [5, 1-b] thiazole -2-yl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl in a mixture of 0.5 ml of THF with 0.5 ml of water, followed by stirring at the same temperature for 40 minutes. Then a saturated aqueous solution of sodium hydrogencarbonate was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate. The solvent was removed by distillation. The residue was purified by column chromatography on silica gel (dichloromethane: methanol 20: 1) to provide 23.5 mg of (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7- methanesulfonylimidazo [5, 1-b] thiazol-3-yl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 4-nitrobenzyl NMR (CDC13) d: 1.20 (3H, d, J = 7.3 Hz ), 1.39 (3H, d, J = 6.3 Hz), 3.20 (3H, s), 3.50 (1H, dd, J? = 6.0 Hz, Jz = 3.2 Hz), 3.58 - 3.68 (1H, m), 4.30 - 4.40 (1H, m), 4.56 (1H, dd, Jx = 10.7 Hz, J2 = 3.2 Hz), 5.18 (1H, d, J = 13.5 Hz), 5.37 (1H, d, J = 13.5 Hz), 7.13 ( 1H, s), 7.49 (2H, d, J = 8.6 Hz), 7.82 (1H, s), 8.20 (2H, d, J = 8.6 Hz) c) (ÍS, 5R, 6S) -6- ((lR ) -l-hydroxyethyl) -2, - (7-methanesulfonylimidazo [5, 1-b] thiazol-3-yl) -l-methyl-l-carbapen-2-em-3-carboxylate sodium The title compound ( 29.8 mg) was obtained from 62.4 mg of (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-ethanesulfonylimidazo [5, 1-b] thiazol-3-yl) 4-nitrobenzyl-l-methyl-l-carbapen-2-em-3-carboxylate of substantially the same same as in Example 1-b) except that the purification was carried out using Cosmosil 40C18-PREP (5% aqueous methanol). NMR (D20) d (HOD = 4.80 PPM): 1.15 (3H, d, J = 7.0 Hz), 1.31 (3H, d, J = 6.3 Hz), 3.31 (3H, s), 3.51 - 3.65 (2H, m ), 4.25 -4.35 (1H, m), 4.43 (1H, d, J = 10.4 Hz), 7.30 (1H, s), 8.16 (1H), s) Example 26 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methansulfinylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-1 sodium-carbapen-2-em-3-carboxylate (a mixture of diastereomers) a) (Is, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo) [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl Substantially in the same manner as in example la), 453 mg of (IS, 5R , 6S) -6- ((IR) -1-hydroxyethyl) -1-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-3-yl) -l-carbapen-2-em-3- 4-Nitrobenzyl carboxylate from 399 mg of (IR, 3R, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2-oxo-l-carbapenam-3-carboxylate of 4-nitrobenzyl. -nitrobenzyl and 442 mg of 7-methylthio-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole. NMR (CDC13) d: 1.30 (3H, d, J = 7.4 Hz), 1.40 (3H, d, J = 6.3 Hz), 2.42 (3H, s), 3.36 (1H, dd, Jx = 6.3 Hz, J2 = 2.5 Hz), 3.40 - 3.50 (1H, m), 4.29 - 4.35 (1H, m), 4.38 (1H, dd, J? = 9.4 Hz, J2 = 2.8 Hz), 5.27 (1H, d, J = 13.5 Hz ), 5.52 (1H, d, J = 13.5 Hz), 7.68 (2H, d, J = 8.5 Hz), 8.07 (1H, s), 8.23 (2H, d, J = 8.5 Hz), 8.44 (1H, s) ) b) (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfinylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen -2-Em-3-carboxylate of 4-nitrobenzyl (a mixture of diastereomers) In the same manner as in Example 25-b), 61 mg of (1S, 5R, 6S) -6- ((IR) was obtained -1-hydroxyethyl) -2- (7- methansulfinylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl (a mixture of diastereomers ) employing 190 mg (SS, 5R, 6S) -6- ((IR) -1- hydroxyethyl) -2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -1- carbapen-2- 4-nitrobenzyl em-3-carboxylate and 227 mg of OXONE (manufactured by Du pont (El) of Nemours &; Co.) NMR (CDC13) d: 1.38, 129 (3H, d, J = 7.4 Hz), 1.39 (3H, d, J = 6.3 Hz), 3.35 - 3.39 (1H,), 3.40 - 3.50 (1H, m ), 4.25 - 4.35 (1H, m), 4.38 - 4.40 (1H, m), 5.27 (1H, d, J = 13.5 Hz), 5.52 (1H, d, J = 13.5 Hz), 7.68 (2H, d, J = 8.5 Hz), 8.07 (1H, s), 8.23 (2H, d, J = 8.5 Hz), 8.44 (1H, s) c) (SS, 5R, 6S) -6- ((lR) -l- hydroxyethyl) -2- (7-methanesulfinylimidazo [5, lb] thiazole -2-ii) - 1-methyl-1-carbapene-2-emper-3-carboxylate sodium (a mixture of diastereomers) The title compound ( 23.8 mg) was obtained from 61 mg of (ÍS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-3-yl) -l-Methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl in substantially the same manner as in Example 1-b), except that the -purification was carried out using Cosmosil 40C18-PREP (aqueous methanol 5%) . NMR (D20) d (HOD = 4.80 PPM): 1.21 (3H, d, J = 7.2 Hz), 1.31 (3H, d, J = 6.3 Hz), 3.06 (3H, d), 3.45 - 3.60 (2H, m ), 7.94, 7.96 (1H, s), 8.21, 8.22 (1H, s) Example 27 (5R, _6S) -6- ((IR) -1-hydroxyethyl) -2- (7-propionylimidazo [5, 1- b) thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid sodium a) (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-propionylimidazo [5 , 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl In the same manner as in Example la), 362 mg of (5R, 6S) -6 were obtained - ((IR) -1-hydroxyethyl) -2- (7-propionylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl from 522 mg of (3R, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2-oxo-l-carbapenam-3-carboxylate of 4-nitrobenzyl and 844 mg of 7-propionyl-2- (tri- n-butylstannyl) imidazo [5, 1-b] thiazole. NMR (-DMSO-Dβ) d: 1.10. (3H, L, J = 7.5 Hz), 1.17 (3H, d, J = 6.2 Hz), 2.91 (2H, q, J = 7.5 Hz), 3.49 (3H,), 4.01 (1H, m), 4.26 ( 1H, m), 5.43 (1H, d, _.J = 13.9 Hz), 5.56 (1H, d, J = 13.9 Hz), 7.77 (2H, d, J = 8.8 Hz), 8.24 (1H, d, J = 8.8 Hz), 8.32 (1H, s), 8.47 (1H, s) b) (5R, 6S) -6- ((lR) -l-hydroxyethyl) -2- (7-propionylimidazo [5, 1-b ] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate sodium In the same manner as in "Example 1-b), 91.2 mg of the title compound was obtained from 162 mg (5R) , 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-propionylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate from 4- Nitrobenzyl NMR (D20) d (HOD = 4.80 PPM): 1.11 (3H, t, J = 6.9 Hz), 1.32 (3H, d, J = 6.3 Hz), 2.77 (2H, q, J = 6.9 Hz), 3.20 (2H, m), 3.48 1H, dd, J = 5.7 Hz, J2 = 2.5 Hz), 4.25 (2H, m), 7.65 (1H, s), 7.93 (1H, s) Example 28 (5R, 6S) - 6- ((IR) -1-hydroxyethyl) -2- (7-propionylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of pivaloyloxymethyl In the same way as in the ej In Example 2, 28.6 of the title compound was obtained from 50.2 mg of (5R, 6S) -6 - ((lR) -1-hydroxyethyl) -2- (7-propionylimidazo [5, lb] thiazol-2-yl. ) -1-carbapen-2-em-3-carboxylate sodium. NMR (CDC13) d: 1.22 (9H, s), 1.26 (3H, t, J = 7.4 Hz), 1.38 (3H, d, J = 6.3 Hz), 3.06 (1H, q, J = 7.4 Hz), 3.32 (3H, m), 4. 30 - 4.40 (1H, m), 4.56 (1H, dd, 3.2 Hz), 4. 31 (2H, m), 5.90 (1H, d, J = 5.6 Hz), 6.02 (1H, d, J = 5.6 Hz), 8.02 (1H, s), 8.55 (1H, s) _ Example 29 (5R, 6S) -2- (7-Acetylimidazo [5, lb] thiazol-3-yl) -6- ((1R) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate of pivaloyloxymethyl a) (5R , 6S) -2- (7-acetylimidazo [5, 1-b] thiazol-3-yl) -6- ((1R) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate from 4- Nitrobenzyl In the same manner as in Example la), 312 mg of (5R, 6S) -2- (7-acetylimidazo [5, 1-b] thiazol-3-yl) -6- ((IR) - 1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl from 396 mg of (3R, 5R, 6S) -6- ((IR) -1- hydroxyethyl) -2-oxo- l-carbapenam-3-carboxylate of 4-nitrobenzyl and 621 mg of 7-acetyl-3- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole. NMR (CDC13) d: 1.40 (3H, d, J = 6.3 Hz), 2.58 83H, s), 3.42 (3H, m), 4.33 (1H, m), 4.48 (1H, m), 5.20 (1H , d, J = 13.5 Hz), 5.37 (1H, d, J = 13.5 Hz), 7.22 (1H, s), 7.47 (2H, d, J = 8.6 Hz), 7.67 (1H, s), 8.17 (2H , d, J = 8.6 Hz) b) (5R, 6S) -2- (7-acetylimidazo [5, lb] thiazol-3-yl) -6- ((1R) -1-hydroxyethyl) -l-carbapen- Sodium 2-em-3-carboxylate From the same rubber as in Example 1-b), 109 mg of (5R, 6S) -2- (7-acetylimidazo [5, lb] thiazol-3-yl) was obtained. -6- ((1R) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylic acid sodium from 216 mg of (5R, 6S) -2- (7-acetylimidazo [5, 1-b] ] thiazol-3-yl) -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate of .4-nitrobenzyl. NMR (D20) d (HOD = 4.80 PPM): 1.32 (3H, d, J = 6.3 Hz), 2.50 (3H, s), 3.23 (1H, dd, J? = 17.1 Hz, J2 = 9.9 Hz), 3.48 (1H, dd, J? = 17.1 Hz, J2 = 8.5 Hz), 3.60 (1H, dd, J: = 5.8 Hz, J2 = 2.7 Hz), 4.28 (1H, m), 4.41 (1H, m), 7.27 (1H, s), 7.83 (1H, s) c) (5R, 6S) -2- (7-acetylimidazo [5, lb] thiazol-3-yl) -6- ((1R) -1-hydroxyethyl) - pivaloyloxymethyl l-carbapen-2-em-3-carboxylate In the same manner as in Example 2, 61.3 mg of the title compound was obtained from 69.4 mg of (5R, 6S) -2- (7-acetylimidazo [ 5, lb] thiazol-3-yl) -6- ((IR) -1-hydroxyethyl) -1- carbapene-2-em-3-carboxylic acid sodium NMR (CDCI3) d: 1.19 (9H, s), 1.39 (3H, d, J = 6.2 Hz), 2.61 (3H, m), 4.30 (1H, m), 4.44 (1H,), 5.77 (1H, d, J = 5.6 Hz), 5.89 (1H, d, J = 5.6 Hz), 7.26 (1H, s), 7.73 (1H, s) Example 30 (SS, 5R, 6S) -2- (7-ethanesulfonylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylic acid sodium a) (SS, 5R, 6S) -2- (7-ethanesulfonylimidazo [5, 1-b] thiazol-2-yl) - 6- ( (IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl In the same manner as in example la), 765 mg of (13, 5R, 6S was obtained ) -2- (7-ethanesulfonylimidazo [5, 1-b] riazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate from 4-nitrobenzyl from 262 mg of (IR, 3R, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2-oxo-l-carbapenam-3-carboxylate of 4-nitrobenzyl and 413 mg of 7-ethanesulfonyl-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole. NMR (CDCI3) d: 1.31 (3H, t, J = 7.4 Hz), 1.34 (3H, d, J = 7.4"Hz), 1.39 (3H, d, J = 6.3 H), 3.31 (2H, q, J = 7.4 Hz), 3.38 (1H, dd, J? = 6.6 Hz, J2 = 2.7 Hz), 3.50 (1H, m), 4.31 (1H, m), 4.40 (1H, dd, J? = 9.6 Hz, J2 = 2.7 Hz), 5.27 (1H, d, J = 13.7 z), 5.51 (1H, d, J = 13.7 Hz), 7.67 (2H, d, J = 8.8 Hz), 8.08 (1H, s), 8.22 ( 2H, d, J = 8.8 Hz), 8.42 (1H, s) b) (Is, 5R, 6S) -2- (7-ethanesulfonylimidazo [5, 1-b] thiazol-2-yl) -6 (( IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate sodium In the same manner as in Example 1-b), 13.9 mg of the title compound was obtained from 232 mg of (SS, 5R, 6S) -2- (7-ethanesulfonylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1- hydroxyethyl) -l-methyl-1-carbapen- 4-Nitrobenzyl 2-em-3-carboxylate NMR (D20) d (HOD = 4.80 PPM): 1.22 (3H, t, J = 7.4 Hz), 1.25 (3H, d, J = 7.4 H)), 1.31 (3H, d, J = 6.3 Hz), 3.37 (2H, q, J = 7.4 Hz), 3.48 (1H, m), 3.56 (1H, m), 4.23-4.30 (2H, m), 7.97 (1H, s), 8.19 (1H, s) Example 31 (1S, 5R, 6S) -6 - ((IR) -1-hydroxyethi) -1-met? I- - methylsulfamoylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid a) (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl -2- (7-N-methylsulfamoylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl Substantially in the same manner as in example la), 307 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -1-methyl-2- (7-N-methylsulfamoylimidazo [5, 1-b] thiazol-2-yl were obtained ) -1-carbapen-2-em-3-carboxylic acid 4-nitrobenzyl from 362 mg of (IR, 3R, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2 -oxo-l-carbapenam-3-carboxylate of 4-nitrobenzyl and 327 mg of 7-N-methylsulfamoyl-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole.

NMR (DMSO-Ds) d: 1.18 (3H, d, J = 6.1 Hz), 1.22 (3H, d, J = 7. 2 Hz), 2.43 (3H, d, J = 5.1 Hz), 3.42 (1H, dd, J? = 5.7 Hz, J2 = 2.8 Hz), 3.70 - 3.76 (1H, m), 4.00 - 4.06 (1H, m), 4.43 (1H, dd, J? = 9.9 Hz, J2 = 2.8 Hz), 5.16 (1H, d, J = 5.0 Hz), 5.39 (1H, d, J = 13.6 Hz), 5.53 (1H, d, J = 13.6 Hz), 7.50 (1H, q, J = 5.1 Hz), 7.73 (2H, d, J = 8.5 Hz), 8.22 (2H, d, J = 8.5 Hz), 8.38 (1H, s), 8.53 (1H, s) b) (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-N) sodium methylsulfamoylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate Substantially in the same manner as in Example 1-b), the title compound was obtained ( 182 mg) from 307 mg of (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-N-methylsulfamoylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen- 2-em-3-carboxylate of 4-nitrobenzyl, except that the purification was carried out using Cosmosil 40C18-PREP (5% aqueous methanol). NMR (D20) d (HOD = 4.80 PPM): 1.26 (3H, d, J = 7.4 Hz), 1.32 (3H, d, J = 6.3 Hz), 2.60 (3H, s), 3.52 - 3.56 (1H, m ), 3.60 -3.70 (1H, m), 4.25-4.35 (2H, m), 8.05 (1H, s), 8.26 (1H, s) Example 32 (5R, 6S) -6- ((IR) -1- hydroxyethyl) -2- (7-N-methylsulfamoylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid sodium a) (5R, 6S) -6- (( IR) -1-hydroxyethyl) -2- (7-N-methylsulfamoylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl Substantially in the same way in Example la), 104 mg of (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-N-methylsulfamoylimidazo [5, 1-b] thiazol-2-yl was obtained ) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl from 139 mg of (3R, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2-oxo-l-carbapenam 3-Nitrobenzyl carboxylate and 164 mg of 7-N-methylsulfamoyl-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole. NMR (DMSO-D6) d: 1.16 (3 H, d, J = 6.3 Hz), 2.41 (3 H, d, J = 4.9 Hz), 3.43 - 3.55 (3 H, m), 3.96 - 4.05 (1 H, m), 4.20 -4.30 (1H, m) 5.18 (1H, d, J = 13.8 Hz), 5.56 (1H, d, J = 13.8 Hz), 7.51 (1H, q, J = 4.9 Hz), 7.76 (2H, d, J = 8.4 Hz), 8.25 (2H, d, J = 8.4 Hz), 8.39 (1H, s), 8.44 (1H, s) b) (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-N-methylsulfamoylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate sodium The title compound (54.3 mg) was obtained from 100 mg of (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-N-methylsulfamoylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em- 3-Nitrobenzyl 3-carboxylate in substantially the same manner as in Example 1-b), except that the purification was carried out using Cosmosil 40C18-PREP (5% aqueous methanol). NMR (D20) d (HOD = 4.80 PPM): 1.30 (3H, d, J = 6.3), 2.50 (3H, s), 3.30 - 3.40 (2H, m), 3.51 - 3.55 (1H, m), 4.23 - 4.35 (2H,), 7.90 (1H, s), 8.24 (1H, s) Example 33 (5R, 6S) -2- (7-acetyl-5-methylimidazo [5, 1-b] thiazol-2-yl) 6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylic acid sodium a) (5R, 6S) -2- (7-acetyl-5-methylimidazo [5, 1-b] thiazol-2-yl) 6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl In the same manner as in Example la), 380 mg of (5R , 6S) -2- (7-acetyl-5-methylimidazo [5, 1-b] thiazol-2-yl) 6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl from 480 of (3R, 5R, 6S) -6- ((1R) -1-hydroxyethyl) -2-oxo-l-carbapenam-3-carboxylate of 4-nitrobenzyl and 776 mg of 7-acetyl -5-methyl-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole. NMR (CDC13) d: 1.40 (3H, d, J = 6.3 Hz), 2.58 (3H, s), 2.66 (3H, m), 3.36 (3H, m), 4.35 (2H, m), 5.32 (1H, d, J = 13.3 Hz), 5.56 (1H, d, J = 13.3 Hz), 7.70 (2H, d, J = 8.9 Hz), 8.25 (2H, d, J = 8.9 Hz), 8.30 (1H, s) b) (5R, 6S) -2- (7-acetyl-5-methylimidazo [5, 1-b] thiazol-2-yl) 6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate sodium In the same manner as in Example 1-b), 110 mg of the title compound was obtained from 173 mg of (5R, 6S) -2- (7-Acetyl-5-methylimidazo [5, 1-b] thiazol-2-yl) 6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3 Nitrobenzyl 4-carboxylate NMR (D20) d (HOD = 4.80 PPM): 1.32 (3H, d, J = 6.3 Hz), 2.35 (3H, s), 2.36 (3H, s), 3.11 (2H, m), 3.48 (1H, dd, J_ = 5.3 Hz, J2 = 2.6 Hz), 4.23 (2H, m), 7.40 (1H, s) Example 34 (5R, 6S) -2- (7-ethansulfonylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate from sodium a) (5R, 6S) -2- (7-ethanesulfonylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3 4-Nitrobenzylcarboxylate In the same manner as in Example la), 74.2 mg of (5R, 6S) -2- (7-ethanesulfonylimidazo [5, 1-b] thiazol-2-yl) -6- was obtained. ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl from 253 mg of (3R, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2-Oxo-l-carbapenam-3-carboxylate of 4-nitrobenzyl and 396 mg of 7-ethanesulfonyl-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole. NMR (CDC13) d: 1.20 (3H, t, J = 7.0 Hz), 1.39 (3H, d, J = 6.2 Hz), 3.26 - 3.40 (4H, m), 3.48 (2H, q, J = 7.0 Hz) , 4.32 (1H, m), 5.29 (1H, d, J = 13.7 z), 5.52 (1H, d, J = 13.7 Hz), 7.68 (2H, d, J = 8.8 Hz), 7.85 (1H, s) , 8.15 (1H, s), 8.21 (2H, d, J = 8.9 Hz) b) (ls, 5R, 6S) -2- (7-ethanesulfonylimidazo [5, 1-b] thiazol-2-yl) -6 - ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate sodium In the same manner as in Example 1-b), 10.5 mg of the title compound was obtained from 74.2 mg of (SS, 5R, 6S) -2- (7-ethanesulfonylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-1 -carbapen-2-em-3-carboxylate of 4-nitrobenzyl. NMR (D20) d (HOD = 4.80 PPM): 1.24 (3H, t, J = 7.4 Hz), 1.30 (3H, d, J = 6.6 H)), 3.27 (2H, m), 3.39 (2H, q, J = 7.4 Hz), 3.50 (1H, m) 4.25 (2H, m), 7.84 (1H, s), 8.20 (1H, s) Example 35 (SS, 5R, 6S) -6- ((IR) - 1-hydroxyethyl) -l-methyl-2- (7-p-toluenesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid sodium a) (S, 5R , 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-p-toluenesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em- 4-Nitrobenzyl 3-carboxylate In the same manner as in Example la), 176 mg of (ÍS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- ( 7-p-Toluenesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 4-nitrobenzyl ester from 350 mg of (IR, 3R, 5R, 6S) - 6- ((IR) -1-hydroxyethyl) -l-methyl-2-oxo-l-carbapenam-3-carboxylate of 4-nitrobenzyl and 590 mg of 7-p-toluenesulfonyl-2- (tri-n-butylstannyl) imidazo [ 5, 1-b] thiazole. NMR (CDC13) d: 1.29 (3H, t, J = 7.0 Hz), 1.39 (3H, d, J = 6.3 Hz), 2.40 (3H, s), 3.37 (1H, dd, J? = 6.6 Hz, J2 = 2.8 Hz), 3.52 (1H, m), 4.30 (1H, m), 4.40 (1H, dd, J_ = 9.6 Hz, J2 = 2.8 Hz), 5.26 (1H, d, J = 13.7 z), 5.50 ( 1H, d, J = 13.7 Hz), 7.29 (2H, d, J = 8.4 Hz), 7.29 (2H, d, J = 8.4 Hz), 7.66 (2H, d, J = 8.9 Hz), 7.91 (2H, d, J = 8.4 Hz), 7.99 (1H, s), 8.20 (2H, d, J = 8. 9 Hz), 8.35 (1H, s) MS (TSP): 623 (M ++ H) b) (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-p-to'-transsulfonylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate sodium In the same manner as in example 1-b), 53.0 mg of the title compound from 176 mg of (IS, 5R, 6S) -2- (7-p-toluenesulfonylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1 -hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl. NMR (D20) d (HOD = 4.80 PPM): 1.17 (3H, t, J = 7.1 Hz), 1.31 (3H, d, J = 6.3 H)), 2.34 (3H, s), 3.47 (2H, m), 4.25 (2H, m), 7.35 (2H, d, J = 8.3 Hz), 7.77 (2H, d) , J = 8.3 Hz), 7.94 (1H, s), 8.12 (1H, s) Example 36 (5R, 6S) -2- (7-hydroxyacetylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl ) -l-carbapen-2-em-3-carboxylic acid sodium a) (5R, 6S) -2- (7-butyldimethylsilyloxyacetylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) - 1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl In the same manner as in Example la), 255 mg of (5R, 6S) -2- (7-butyldimethylsilyloxyacetylimidazo [5 , 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl from 325 mg of (3R, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2-oxo-l-carbapenam-3-carboxylate of 4-nitrobenzyl and 655 mg of 7-butyldimethylsilyloxyacetyl-2- (tri-n-butylstannyl) imidazo [5 , 1-b] thiazole. NMR (CDC1) d: 0.15 (6H, s), 0.96 (9H, s), 1.41 (3H, d, J = 6.3 Hz), 3.35 (3H, m), 4.34 (2H, m), 5.08 (2H, s), 5.31 (1H, d, J = 13.4 z), 5.53 (1H, d, J = 13.4 Hz), 7.69 (2H, d, J = 8.9 Hz), 7.97 (1H, s), 8.23 (2H, d, J = 8.9 Hz), 8.42 (1H, s) b) (5R, 6S) -2- (7-hydroxyacetylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-carbapen-2 4-Nitrobenzyl-ene-3-carboxylate Acetic acid (0.345 ml) and 2.04 ml of a solution of 1 M tetrafluoromethyl fluoride / THF were added to a solution of 255 mg of (5R, 6S) -2 - (7-Butyldimethylsilyloxyacetylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl in 8 ml of THF The mixture was stirred at room temperature for 3 hours. A saline solution was added to the reaction solution. The mixture was adjusted to a pH of 8.1 by the addition of a saturated solution of sodium hydrogencarbonate and extracted twice with ethyl acetate. The organic layers were combined, washed twice with a saline solution, and dried in anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. Diethyl ether (5 ml) was added to the residue. The insoluble part was collected by filtration to provide 196 mg of (5R, 6S) -2- (7-hydroxyacetyl idazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl. NMR (CDC13) d: 1.17 (3H, d, J = 6.5 Hz), 3.50 (3H, m), 4.01 (1H, m), 4.27 (1H, m), 4.69 (2H, s), 5.44 (1H, d, J = 13.8 Hz), 5.58 (1H, d, J = 13.8 Hz), 7.77 (2H, d, J = 8.9 Hz), 8.25 (2H, d J = 8.9 Hz), 8.34 (1H, s), 8.50 (1H, s) c) (5R, 6S) -2- (7-hydroxyacetylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -l-hydroxyethyl) -l-carbapen-2-em-3-carboxylate sodium In the same manner as in Example 1-b), 95.9 mg of the title compound was obtained from 196 mg of (5R, 6S) -2- (7-hydroxyacetylimidazo [5, 1-b] thiazole-2- il) -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl NMR (D20) d (HOD = 4.80 PPM): 1.33 (3H, d, J = 6.1 H)), 3.24 (3H, m), 3.50 (1H, m), 4.27 (2H, m), 4.77 (2H, s), 7.75 (1H, S), 8.02 (1H, s) Example 37 (ÍS, 5R, 6S) - 2- (7-benzoylimidazo [5, lb] thiazol-2-yl) -6- ((1R) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate sodium a) ( ÍS, 5R, 6S) -2- (7-benzoylimidazo [5, lb] thiazol-2-yl) -6- ((IR) -l-hydroxyethyl) -l-methyl-l-carbapen-2-em-3 4-Nitrobenzylcarboxylate In the same manner as in Example la), 288 mg of (SS, 5R, 6S) -2- (7-benzoylimidazo [5, 1-b] thiazol-2-yl) - were obtained 6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate 4-nitrobenzyl from 543 mg of (IR, 3R, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2-oxo-l-carbapenam-3-carboxylate of 4-nitrobenzyl and 931 mg of 7-benzoyl-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole. NMR (CDC13) d: 1.19 (3H, d, J = 6.2 Hz), 1.25 (3H, d, J = 7.1 Hz), 3.45 (1H, dd, J? = 5.7 Hz, J2 = 2.7 Hz), 3.77 ( 1H, m), 4.04 (1H, m), 4.37 (ÍH ", dd, J? = 10.1 Hz, J2 = 2.7 Hz), 5.41 (1H, d, J = 14.0 z), 5.55 (1H, d, J = 14.0 Hz), 7.58 (3H, m), 7.75 (2H, d, J = 8.8 Hz), 8.22 (2H, d, J = 8.8 Hz), 8.44 (1H, s), 8.49 (2H, m), 8.62 (1H, s) b) (SS, 5R, 6S) -2- (7-benzoylimidazo [5, lb] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl- sodium l-carbapen-2-em-3-carboxylate The title compound (120 mg) was obtained from 440 mg of (IS, 5R, 6S) -2- (7-benzoylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl in the same manner as in Example 1-b), except that the purification was carried out by column chromatography on Diaion HP-20 (30% aqueous methanol) and Cosmosil 40C18-PREP (30% aqueous methanol) . NMR (D20) d (HOD = 4.80 PPM): 1.10 (3H, d, J = 7.1 Hz), 1.32 (3H, d, J = 6.3 Hz), 3.44 (2H,), 4.23 (2H, m), 7.42 (2H, m), 7.57 (1H,), 7.87 (3H, m), 8.01 (1H, s) Example 38 (5R, 6S) -2- (7-hydroxyacetylimidazo [5, 1-b] thiazole-3) il) -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylic acid sodium a) (5R, 6S) -2- (7-butyldimethylsilyloxyacetylimidazo [5, 1-b] thiazole -3-yl) -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl In the same manner as in Example la), 167 mg of ( 5R, 6S) -2- (7- butyldimethylsilyloxyacetylimidazo [5, 1-b] thiazol-3-yl) -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate of 4 -nitrobenzyl from 293 mg of (3R, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2-oxo-l-carbapenam-3-carboxylate of 4-nitrobenzyl and 655 mg of 7-butyldimethylsilyloxyacetyl -3- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole. NMR (CDC13) d: 0.15 (6H, s), 0.96 (9H, s), 1.40 (3H, d, J = 6.3 Hz), 3.41 (3H, m), 4.31 (1H, m), 4.48 (1H, m), 5.05 (2H, s), 5.21 (1H, d, J = 13.5 z), 5.38 (1H, d, J = 13.5 Hz), 7.24 (1H, s), 7.50 (2H, d, J = 8.9 Hz), 7.66 (1H, s), 8.18 (2H, d, J = 8.9 Hz) b) (5R, 6S) -2- (7-hydroxyacetylimidazo [5, 1-bJ thiazol-3-yl) -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl In the same manner as in example 36-b), 56.5 mg of (5R, 6S) -2 were obtained - (7-hydroxyacetylimidazo [5, 1-b] thiazol-3-yl) -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl from 167 mg (5R, 6S) -2- (7-Butyldimethylsilyloxyacetylimidazo [5, 1-b] thiazol-3-yl) -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3 4-nitrobenzyl carboxylate NMR (CDC1) d: 1.41 (3H, d, J = 6.3 Hz), 3.40 (3H, m), 4.34 (1H, m), 4.48 (1H,), 4.88 (2H, s), 5.22 (1H, d, J = 13.4 Hz), 5.39 (1H, d, J = 13.4 Hz), 7.52 (2H, d, J = 8.6 Hz), 7.67 (1H, s), 8.20 (3H, m) c) (SS, 5R, V 6S) -2- (7-benzoylimidazo [5, 1-b] thiazol-3-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen -2-em-3-carboxylate sodium The title compound (27.7 mg) was obtained from 56.5 mg of (5R, 6S) -2- (7-hydroxyacetylimidazo [5, 1-b] thiazol-3-yl) ) -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl in the same manner as in Example 1-b), except that the purification was carried out by chromatography in column in Diaion HÉ-20 (10% aqueous methanol) and Cosmosil 40C18-PREP (5% aqueous methanol). NMR (D20) d (HOD = 4.80 PPM): 1.31 (3H, d, J = 6.5 Hz), 3.23 (1H, dd, J? = 17.5 Hz, J2 = 10.1 Hz), 3.48 (1H, dd, J? = 17.5 Hz, J2 = 8.8 Hz), 3.60 (1H, dd, J? = 5.8 Hz, J2 = 2.9 Hz), 4.28 (1H, m), 4.40 (1H, m), 4.89 (2H, s), 7.31 (1H , s), 7.93 (1H, s) Example 39 (5R, 6S) -2- (7-benzoylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) - sodium l-carbapen-2-em-3-carboxylate a) (5R, 6S) -2- (7-benzoylimidazo [5, lb] thiazol-2-yl) -6- ((1R) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl In the same manner as in Example la), 574 mg of (5R, 6S) -2- (7-benzoylimidazo [5, 1-b] were obtained ] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl from 522 mg of (3R, 5R, 6S) -6 - ((IR) -1-hydroxyethyl) -2-oxo-l-carbapenam-3-carboxylate of 4-nitrobenzyl and 931 mg of 7-benzoyl-2- (tri-n-butylstannyl) imidazo [5, 1-b ] thiazole NMR (CDC13) d: 1.41 (3H, d, J = 6.4 Hz), 3.37 (3H,), 4.25 (2H, m), 5.33 (1H, d, J = 13.5 Hz), 5.56 (1H, d, J = 13.5 Hz), 7.54 (3H, m), 7.71 (2H, q, J = 8.8 Hz), 8.08 (1H, s), 8.25 (2H, d, J = 8.8 Hz), 8.52 (1H, s), 8.54 (2H, m) b) (5R, 6S) -2- (7-benzoylimidazo [5, lb] thiazol-2-yl) -6- ((1R) -1-hydroxyethyl) -l-carbapen-2- sodium em-3-carboxylate The title compound (178 mg) was obtained from 504 mg of (5R, 6S) -2- (7-benzoylimidazo [5, 1-b] thiazol-2-yl) -6 - ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl in the same manner as in example 1-b), except that the purification was carried out by column chromatography in Diaion HP-20 (30% aqueous methanol) and Cosmosil 40C18-PREP (20% aqueous methanol). NMR (D20) d (HOD = 4.80 PPM): 1.26 (3H, d, J = 6.3 Hz), 2.90 (2H, m), 3.25 (1H, dd, Jx = 5.8 Hz, J: = 2.8 Hz), 4.00 (1H, m), 4.17 (1H, m), 7.38 (2H, m), 7.53 (2H, m), 7.83 (3H, m) Example 40 (SS, 5R, 6S) -2- [7- [N - (4-aminobenzyl) sulfamoyl] imidazo [5, 1-b] thiazol-2-yl] -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylic acid sodium a) (SS, 5R, 6S) -2- [7- [N- (4-aminobenzyl) sulfamoyl] imidazo [5, 1-b] thiazol-2-yl] -6- ((IR) -1-hydroxyethyl) - 4-Nitrobenzyl l-carbapen-2-em-3-carboxylate Substantially in the same manner as in Example la), 337 mg of (IS, 5R, 6S) -2- [7- [N- (4 -aminobenzyl) sulfamoyl] imidazo [5, 1-b] thiazol-2-yl] -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl from 507 mg of (IR, 3R, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl and 392 mg of 7- N- (4-Nitrobenzyl) sulfamoyl-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole. NMR (DMS0-D6) d: 1.15 - 1.22 (6H, m), 3.41 - 3.44 (1H, m), 3.65 - 3.74 (1H, m), 4.00 - 4.05 (1H, m), 4.17 (2H, d, J = 6.3 Hz), 4.30 - 4.36 (1H, m), 5.17 (1H, d, J = 5.1 Hz), 5.40 (1H, d, J = 13.5 Hz), 5.53 (1H, d, J = 13.5 Hz) , 7.45 (2H, d, J = 8.6 Hz), 7.74 (2H, d, J = 8.6 Hz), 8.03 (2H, d, J = 8.8 Hz), 8.22 (2H, d, J = 8.8 Hz), 8.29 (1H, s), 8.43 (1H, s), 8.50 (1H, t, J = 6.3 Hz) (SS, 5R, 6S) -2- [7- [N- (4-aminobenzyl) sulfamoyl] imidazo [5 , 1-b] thiazol-2-yl] -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate sodium Substantially in the same manner as in example 1-b) , 165 mg of the title compound was obtained from 337 mg of (1S, 5R, 6S) -2- [7- [N- (4-aminobenzyl) sulfamoyl] imidazo [5, 1-b] thiazole-2- il] -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl, except that the purification was performed using Cosmosil 40C18-PREP (5% aqueous methanol) NMR (D20) d (HOD = 4.80 PPM): 1.26 (3H, d, J = 7.3 Hz), 1.32 (3H, d, J = 6.4 Hz), 3.52 - 3.64 (2H, m), 4.10 (2H, s), 4.25 - 4.35 (2H, m), 6.46 (2H, d, J = 8.5 Hz), 6.86 ( 2H, d, J = 8. 6 Hz), 7.90 (1H, s), 7.96 (1H, s) Example 41 (1S, 5R, 6S) -2- (7-fluoroimidazo [5, lb] thiazol-2-yl) -6- (IR) Sodium 1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate a) (SS, 5R, 6S) -2- (7-fluoroimidazo [5, 1-b] thiazole-2-) il) -6- (IR) - 1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl In the same way as example la), 40 mg of (SS, 5R, 6S) -2- (7-fluoroimidazo [5, lb] thiazol-2-yl) -6- (lR) -1-hydroxyethyl) -l-methyl-1-carbapen was obtained -2-Em-3-carboxylate of 4-nitrobenzyl from 320 mg of (IR, 3R, 5R, 6S) -6- (IR) -1-hydroxyethyl) -l-methyl-2-oxo-carbapenam-3 -carboxylate and 400 mg of 7-fluoro-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole. NMR (CDC13) d: 1.31 (3H, d, J = 7.4 Hz), 1.39 (3H, d, J = 6.3 Hz), 3.39 (1H, dd, Jx = 6.4 Hz, J2 = 2.8 Hz), 3.46 (1H , m), 4.27 (1H, m), 4.40 (1H, dd, J_ = 9.7 Hz, J2 = 2.8 Hz), 5.27 (1H, d, J = 13.6 Hz), 5.51 (3H, d, J = 13.6 Hz ), 7.62 (1H, s), 7.68 (2H, d, J = 8.9 Hz), 8.21 (1H, s), 8.26 (2H, d, J = 8.9 Hz) b) (SS, 5R, 6S) -2- (7-fluoroimidazo [5, lb] sodium thiazol-2-yl) -6- (IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate In the same way as Example 1-b), 3.8 mg of the title compound from 40 mg of (SS, 5R, 6S) -2- (7-fluoroimidazo [5, 1-b] thiazol-2-yl) -6- (IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl. NMR (D20) d (HOD = 4.80 PPM): 1.24 (3H, d, J = 7.4 Hz), 1.32 (3H, d, J = 6.3 Hz), 3.51 (1H, dd, Jx = 6.3 Hz, J2 = 2.7 Hz), 3.53 (1H, m), 4.27 (1H,), 4.30 (1H, dd, Jx = 9.2 Hz, J2 = 2.7 Hz), 7.22 (1H, s), 7.72 (1H, s), 7.79 (1H, d, J = 1.9 Hz) Example 42 (SS, 5R, 6S) -6- ((IR) - 1-hydroxyethyl) -2- [7- [N- (2-hydroxyethyl) -N-methylsulfamoyl] imidazo [5, 1-b] -thiazol-2-yl] -l-methyl-1-carbapen-2-em -3-sodium carboxylate a) (SS, 5R, 6S) -2- [7- [N- (2-t-butyldimethylsilyloxyethyl) -N-ethylsulfamoyl] imidazo [5, 1-b] thiazole -2-yl) -6- (IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl In a manner substantially similar to that presented in example la), 273 mg of ( ÍS, 5R, 6S) -2- [7- [N- (2-t-butyldimethylsilyloxyethyl) -N-methylsulfamoyl] imidazo [5, 1-b] thiazole -2-yl) -6- (IR) -1- hydroxyethyl) -1-methyl-l- carbapen-2-em-3-carboxylate of 4-nitrobenzyl from 217 mg of (IR, 3R, 5R, 6S) -6- ((IR) -1-hydroxyethyl) - l-Methyl-2-oxo-l-carbapenam-3-carboxylate of 4-nitrobenzyl and 362 mg of 7- [N- (2-t-butyl dimethyl Icyloxyethyl) -N-methylsulfanyl] -2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole. NMR (CDC13) d: 0.07 (6H, s), 0.89 (9H, s), 1.32 (3H, d, J = 7.2 Hz), 1.41 (3H, d, J = 6.2 Hz), 2.99 (3H, s) , 3.33 (2H, t, J = 6.1 Hz), 3.38 (1H, dd, J? = 6.4 Hz, J2 = 3.3 Hz), 3.45- 3.53 (1H, m), 3.84 (1H, t, J = 6.1 Hz ), 4.30 - 4.37 (1H, m), 4.40 (1H, dd, J? = 9.6 Hz, J2 = 3.3 Hz), 5.30 (1H, d, J = 8.5 Hz), 5.54 (1H, d, J = 8.5 Hz), 7.69 (2H, d, J = 8.5 Hz), 8.05 (1H, s), 8.26 (2H, d, J = 8.5 Hz), 8.46 (1H, s) b) (ÍS, 5R, 6S) - 6- ((1R) -l-hydroxyethyl) -2- [7- [N- (2-hydroxyethyl) -N-methyl-sulfamoyl] imidazo [5, 1-b] -thiazole -2-yl] -l- methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl Acetic acid (0.36 ml) and 2.0 ml of a solution of tetra-n-butylammonium 1 M / THF were added with ice cooling to a solution of 273 mg of (SS, 5R, 6S) -2- [7- [N- (2-t-butyldimethylsilyloxyethyl) -N-methylsulfamoyl] imidazo [5,1-b] -thiazole -2-yl] -l-methyl- 4-Nitrobenzyl l-carbapen-2-em-3-carboxylate in 8 ml of THF. The mixture was stirred at room temperature for 6 hours. The reaction mixture was added to a dilute aqueous solution of sodium hydrogencarbonate, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate. The solvent was removed by distillation. The residue was purified by column chromatography on silica gel (dichloromethane: methanol = 10: 1) to give 175 mg of (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- [7 - [N- (2-hydroxyethyl) -N-methyl-sulfamoyl] imidazo [5,1-b] -thiazol-2-yl] -l-methyl-l-carbapen-2-em-3-carboxylate from 4- nitrobenzyl. NMR (CDC13) d: 1.30 (3H, d, J = 7.2 Hz), 1.39 (3H, d, J = 6.3 Hz), 2.87 (3H, s), 3.38 (1H, dd, J_ = 6.6 Hz, J2 = 2.7 Hz), 3.48 - 3.53 (1H, m), 3.54 (2H, t, J = 4.8 Hz), 3.82 (2H, t, J = 4.8 Hz), 4.27 - 4.37 (1H, m), 4.40 (1H, dd, J_ = 9.7 Hz, J2 = 2.7 Hz), 5.28 (1H, d, J = 13.7 Hz), 5.52 (1H, d, J = 13.7 Hz), 7.67 (2H, d, J = 8.8 Hz), 8.05 (1H, s), 8.23 (2H, d, J = 8.8 Hz), 8.42 (1H, s) c) (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- [7 - [N- (2-hydroxyethyl) -N-methylsulfamoyl] imidazo [5, 1-b] -thiazol-2-yl] -l-methyl-1-carbapen-2-em-3-carboxylate sodium The compound of the title (90.9 mg) was obtained from 175 mg of (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- [7- [N- (2-hydroxyethyl) -N-methylsulfamoyl ] imidazo [5, 1-b] -thiazol-2-yl] -l-methyl-1-carbapen-2-em-3-carboxylate of 4-nitrobenzyl in substantially the same manner as in Example 1-b), except that the purification was carried out with Cosmosil 40C18-PREP (2.5% aqueous methanol). NMR (D20) d (HOD = 4.80 PPM): 1.24 (3H, d, J = 7.2 Hz), 1.31 (3H7 d, J = 6.3 Hz), 2.83 (3H, m), 3.27 (2H, t J = 4.9 Hz), 3.51 (1H, m), 3.56 - 3.67 (1H ,), 3.72 (2H, t, J = 4.9 Hz), 4.23 - 4.35 (2H, m), 8.04 (1H, s), 8.22 (1H, s) Example 43 (SS, 5R, 6S) -2- ( 7-Acetylaminoacetylimidazo [5, 1-b] -thiazol-2-yl] -6- ((IR) -1-hydroxyethyl) -1-methyl-1-carbapen-2-em-3-carboxylic acid sodium ) (SS, 5R, 6S) -2- (7-acetylaminoacetylimidazo [5, 1-b] -thiazole -2-yl] -6- ((IR) -1-hydroxyethyl) -1- methyl-1-carbapen- 2-Em-3-carboxylate of 4-nitrobenzyl In the same manner as in Example la) 23.8 mg of (IS, 5R, 6S) -2- (7-acetylaminoacetylimidazo [5, 1-b] -thiazole - 2-yl] -6- ((IR) -1-hydroxyethyl) -1-methyl-1-carbapen-2-em-3-carboxylic acid 4-nitrobenzyl from 123 mg of (IR, 3R, 5R, 6S ) -6- ((IR) -1-hydroxyethyl) -l-methyl-2-oxo-carbapenam-3-carboxylate of 4-nitrobenzyl and 207 mg of 7-acetylaminoacetyl-2- (tri-n-butylstannyl) imidazo [ 5, 1-b] thiazole, NMR (CDC13) d: 1.30 (3H, d, J = 7.1 Hz), 1.40 (3H, d, J = 6.2 Hz), 2.10 (3H, s), 3.39 (1H, dd, J? = 6.7 Hz, J2 = 2.9 Hz), 3.52 (1H, m), 4.32 (1H, m), 4.42 (1H , dd, J? = 9.8 Hz, J2 = 2.9 Hz), 4.79 (2H, d, J = 4.7 Hz), 5.28 (1H, d, J = 13.4 Hz), 5.52 (1H, d, J = 13.4 Hz) , 6.51 (1H, br), 7.68 (2H, d, J = 8.5 Hz), 8.01 (1H, s), 8.24 (2H, d, J = 8.5 Hz), 8.46 (1H, s) c) (SS, 5R, 6S) -2- (7-acetylaminoacetylimidazo [5, 1-b] -thiazole -2-yl] -6- ((lR) -l-hydroxyethyl) -1-methyl-1-carbapen-2-em- 3-sodium carboxylate The title compound (9.0 mg) was obtained from 23.8 mg of (SS, 5R, 6S) -2- (7-acetylaminoacetylimidazo [5, 1-b] -thiazole -2-yl] - 6- ((IR) -1-hydroxyethyl) -1-methyl-1-carbapen-2-em-3-carboxylate of 4-nitrobenzyl in the same manner as in example 1-b), except that the purification was effected by column chromatography on Diaion HP-20 (10 aqueous methanol) and Cosmosil 40C18-PREP (5% aqueous methanol). NMR (D20) d (HOD = 4.80 PPM): 1.23 (3H, d, J = 6.9 Hz), 1.33 (3H, d, J = 6.3 Hz), 2.14 (3H, s), 3.52 (2H, m), 4.29 (2H, m), 4.49 (1H, d J = 18.9 Hz), 4.63 (1H, d, J = 18.9 Hz), 7.92 (1H, s), 8.07 (1H, s) Example 44 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonyl) -5-methylimidazo [5, 1-b] -thiazol-2-yl] -l-methyl-1-carbapen-2 sodium a-3-carboxylate a) (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (5-methyl-7-ethylthioimidazo [5, 1-b ] - thiazol-2-yl] -l-methyl-1-carbapen-2-em-3-carboxylate of 4-nitrobenzyl In the same manner as in Example la), 1.41 g of (ΔS, 5R, 6S were obtained ) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (5-methyl-7-methylthioimidazo [5, 1-b] -thiazole-2-yl] -l-methyl-1-carbapen -2-em-3-carboxylate of 4-nitrobenzyl from 1.81 g of (IR, 3R, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2-oxo-l- carbapenam-3-carboxylic acid 4-nitrobenzyl ester and 2.84 g of 5-methyl-7-methylthio-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole, NMR (CDC13) d: 1.31 (3H, d , J = 7.3 Hz), 1.40 (3H, d, J = 6.3 Hz), 2.40 (3H, s), 2.58 83H, s), 3.36 (1H, dd, 6.6 Hz, J2 = 3.0 Hz), 3.46 (1H , m), 4.34 (2H, m), 5.27 (1H, d, J = 13.7 Hz), 5.54 (1H, d, J = 13.7 Hz), 7.68 (2H, d, J = 8.9 Hz), 8.16 (1H, s), 8.25 (2H, d, J = 8.9 Hz) b) (ÍS, 5R, 6S) -6- ((lR) -l-hydroxyethyl) -2- (7-methanesulfonyl) -5-methylimidazo [5, 1-b] -thiazol-2-yl] -l-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl It was dissolved (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (5-methyl-7-methylthioimidazo [5, 1-b] -thiazol-2-yl] -l-methyl-1-carbapen-2-em-3-carboxylate of 4-nitrobenzyl (315 mg) in 6 ml of THF and 6 ml of water. To the solution were added 368 mg of OXONE (manufactured by Du pont (E.l) of Nemours &; Co.) with cooling with ice. The mixture was stirred at the same temperature for 1.5 hours. An aqueous solution of sodium hydrogencarbonate was added, followed by extraction with dichloromethane. The extract was dried in anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography on silica gel (dichloromethane: methanol: 20: 1 to 10: 1). Of the two main components, the fraction that had previously eluded was concentrated under reduced pressure to provide 145 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonyl) -5-Methylimidazo [5, 1-b] -thiazol-2-yl] -l-methyl-1-carbapen-2-em-3-carboxylate of 4-nitrobenzyl. NMR (CDC13) d: 1.30 (3H, d, J = 7.4 Hz), 1.40 (3H, d, J = 6.4 Hz), 2.64 (3H, s), 3.19 (3H, s), 3.38 (1H, dd, J? = 6.7 Hz, J2 = 2.9 Hz), 3.48 (1H, m), 4.32 (1H, m), 4.40 (1H, dd, J? = 9.7 Hz, J2 = 2.9 Hz), 5.28 (1H, d, J = 14.0 Hz), 5.54 (1H, d, J = 14.0 Hz), 7.69 (2H, d, J = 8.5 Hz), 8.25 (2H, d, J = 8.5 Hz), 8.32 (1H, s) c) (SS, 5R, 6S) -6- ((1R) -l-hydroxyethyl) -2- (7-methanesulfonyl) -5-methylimidazo [5, 1-b] -thiazol-2-yl] -l-methyl- sodium l-carbapen-2-em-3-carboxylate In the same manner as in example 1-b), 104 mg of the title compound was obtained from 172 mg of (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonyl) -5-methylimidazo [5, 1-b] -thiazol-2-yl] -l-methyl-1-carbapen-2-em-3 4-nitrobenzyl carboxylate. NMR (D20) d (HOD = 4.80 PPM): 1.22 (3H, d, J = 7.2 Hz), 1.32 (3H, d, J = 6.2 Hz), 2.57 (3H, s), 3.25 (3H, s), 3.50 (1H, m), 3.61 (1H,), 4.29 (1H, m), 7.84 (1H, s) Example 45 (ÍS, 5R, 6S) -6- ((lR) -l-hydroxyethyl) -2- (7-Methansulfinyl) -5-methylimidazo [5, 1-b] -thiazol-2-yl] -l-methyl-1-carbapen-2-em-3-carboxylic acid sodium (a mixture of diastereomers) a) ( ÍS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfinyl) -5-methylimidazo [5, 1-b] -thiazole -2-yl] -l-methyl-1 -carbapen-2-em-3-carboxylate of 4-nitrobenzyl (a mixture of diastereomers) Of the two main components, the fraction that had been subsequently eluted in column chromatography on silica gel in example 44-b) was concentrated under reduced pressure to provide 139 g of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfinyl) -5-methylimidazo [5, 1-b] -thiazole -2-yl] -l-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl (a mixture of diastereomers) NMR (CDC13) d: 1.29 (3H, m) , 1.39 (3H, d, J = 6.4 Hz), 2.62 (3H, s), 2.92, 2.94 (total 3H, each s), 3.36 (1H, m), 3.45 (1H, m), 4.32 (2H, m), 5.28 (1H, d, J = 13.4 Hz), 5.54 (1H, d, J = 13.4 Hz), 7.68 (2H, d, J = 8.8 Hz), 8.25 (2H, d, J = 8.8 Hz), 8.31 (1H, s) b) (SS, 5R, 6S) -6- ((lR) -l-hydroxyethyl) -2- (7-methanesulfinyl) -5-methylimidazo [5, 1-b] - sodium thiazol-2-yl] -l-methyl-l-carbapen-2-em-3-carboxylate (a mixture of diastereomers) In the same manner as example 1-b), 127 mg of the title compound were obtained from 204 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfinyl) -5-methylimidazo [5, 1-b] -thiazole -2-il ] -l-methyl-1-carbapen-2-em-3-carboxylate of 4-nitrobenzyl (a mixture of diastereomers). NMR (D20) d (HOD = 4.80 PPM): 1.23 (3H, d, J = 6.9 Hz), 1.32 (3H, d, J = 6.3 Hz), 2.56 (3H, s), 3.03 (3H, s), 3.50 (1H, m), 3.59 (1H, m), 4.29 (2H, m), 7.82, 7.85 (total 1H, each s) Example 46 (SS, 5R, 6S) -2- (7-acetylimidazo [5, lb] thiazol-2-yl) -6- ((1R) -1-hydroxy-ethyl) -1-methyl-1-carbapen-2-em-3-carboxylic acid 1- (ethoxycarbonyloxy) ethyl ester (a mixture of diastereomers ) a) (1S, 5R, 6S) -2- (7-acetylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -1- methyl-1-carbapen -2-em-3-carboxylate of 4-nitrobenzyl In the same manner as in Example la), 5.93 g of (SS, 5R, 6S) -2- (7-acetylimidazo [5, 1-b] thiazole were obtained. -2-yl) -6- ((IR) -1-hydroxyethyl) -1-methyl-1-carbapen-2-em-3-carboxylate of 4-nitrobenzyl from 5.80 g of (IR, 3R, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -1- methyl-1-carbapen-2-em-3-carboxylate of 4-nitrobenzyl and 8.80 g of 7-acetyl-2- (tri-n-butylstannyl) ) imidao [5, 1-b] thiazole. NMR (CDC13) d: 1.31 (3H, d, J = 7.4 Hz), 1.40 (3H, d, J = 6.2 Hz), 2.61 (3H, s), 3.40 (1H, dd, J_ = 6.6 Hz, J2 = 2.9 Hz), 3.52 (1H,), 4.32 (1H, m), 4.42 (1H, dd, J_ = 9.7 Hz, Jz = 2.9 Hz), 5.27 (1H, d, J = 13.5 Hz), 5.52 (1H, d, J = 13.5 Hz), 7.67 (2H, d, J = 8.5 Hz), 8.01 (1H, s), 8.22 (2H, d, J = 8.5 Hz), 8.50 (1H, s) c) (SS, 5R, 6S) -2- (7-acetylimidazo [5, lb] thiazol-2-yl) -6- ((IR) -1-hydroxy-ethyl) -1-methyl-1-carbapen-2-em-3 sodium carboxylate In the same manner as in Example 1-b), 954 mg of (SS, 5R, 6S) -2- (7-acetylimidazo [5, 1-b] thiazol-2-yl) - were obtained 6- ((IR) -1-hydroxy-ethyl) -1-methyl-1-carbapen-2-em-3-carboxylic acid sodium from '1.53 g of (IS, 5R, 6S) -2- (7 -acetylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxy-ethyl) -1-methyl-1-carbapen-2-em-3-carboxylate of 4-nitrobenzyl. NMR (D20) d (HOD = 4.80 PPM): 1.20 (3H, d, J = 7.2 Hz), 1.33 (3H, d, J = 6.4 Hz), 2.45 (3H, s), 3.50 (1H, dd, J? = 6.1 Hz, J2 = 2.5 Hz), 3.57 (1H, m), 4.28 (1H, m), 4.33 (1H, dd, J? = 9.3 Hz, J2 = 2.5 Hz), 7.92 (1H, s), 8.05 (1H, s) c) (SS, 5R, 6S) -2- (7-acetylimidazo [5, lb] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -1-methyl-1-carbapen-2-em-3-carboxylic acid 1- (ethoxycarbonyloxy) ethyl ester (a mixture of diastereomers) ( ÍS, 5R, 6S) -2- (7-acetylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -1-methyl-1-carbapen-2-em -3-sodium carboxylate (71.9 mg) was dissolved in 2.0 ml of DMF. 1- (ethoxycarbonyloxy) ethyl iodide (66.3 mg) was added to the solution in an argon atmosphere at a temperature of -20 ° C. The rocking was stirred for 2 hours while the temperature was raised to -10 ° C. He added ethyl acetate (20 ml) to the reaction solution. The mixture was extracted twice, followed by washing twice with 10 ml of a semi-saturated saline solution. The organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a volume of 2 ml. The residue was purified by column chromatography on silica gel (chloroform: methanol = 15: 1) and Sephadex LH-20 (dichloromethane: methanol = 1: 1) in this order to provide 57.4 of the title compound. NMR (CDC1) d: 1.28 (3H, d, J = 7.2 Hz), 1.32 - 1.41 (6H, m), 1.60, 1.65 (total 3H, each d, J = 5.4 H), 2.62 (3H, s), 3.34 (1H, m), 3.49 (1H, m), 4.21 (1H, m) 4.29 (1H, m), 4.39 (1H, m), 6.94 (1H,), 8.02 (1H, s), 8.61, 8.63 (total 1H, each s) MS (TSP): 492 (M ++ H) Example 47 (IS, 5R, 6S) -2- (7-acetylimidazo [5, lb] thiazole-2 -yl) -6- ((1R) -1-hydroxyethyl) -l-methyl-? - Carbapene-2-em-3-carboxylic acid 1- (isopropoxycarbonyloxy) ethyl ester (a mixture of diastereomers) In the same manner as in Example 46, 41.7 mg of the title compound was obtained from 54.8 mg of (IS, 5R, 6S) -2- (7- acetylimidazo [5, 1-b] thiazole -2-yl) -6- (( IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate sodium and 100.0 mg of iodide 1- (isopropoxycarbonyloxy) ethyl NMR (CDCI3) d: 1.25-1.40 (12H, m) , 1.59, 1.66 (total 3H, each d, J = 5.4 H), 2.62 (3H, s), 3.34 (1H, m), 3.49 (1H, m), 4.29 (1H, m), 4.38 (1H, m ), 4.90 (1H, m), 6.93 (1H, m), 8.03 (1H, m), 8.03 (1H, s), 8.43 (1H, s), 8.63, 8.64 (total 1H, each s) MS (TSP) ): 506 (M + + H) Example 48 (SS, 5R, 6S) -2- (7-acetylimidazo [5, lb] thiazol-2-yl) -6- ((1R) -1-hydroxyethyl) -1 - methyl-l-carbapen-2-em-3-carboxylate of 1- (cycloexyloxycarbonyloxy) et ilo (a mixture of diastereomers) In the same manner as in example 46, 59.4 mg of the title compound were obtained from 58.1 mg of (ΔS, 5R, 6S) -2- (7- acetylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -1- methyl-1-carbapene-2-em-3-carboxylate of sodium and 65.2 mg of 1- (cycloexyloxycarbonyloxy) ethyl iodide NMR (CDC13) d: 1.28 (3H, m), 1.38 (3H, m), 1.25-1.82 (8H,), 1.59, 1.65 (total 3H, each d, J = 5.4 H), 1.85 - 2.02 (2H, m), 2.62 (3H, s), 3.32 (1H, m), 3.48 (1H, m), 4.29 (1H,), 4.38 (1H, m), 4.65 (1H, m), 6.95 (1H , m), 8.01, 8.02 (total 1H, each s) 8.61, 8.63 (total 1H, each s) MS (TSP): 546 (M ++ H) Example 49 (ÍS, 5R, 6S) -2- (7-acetylimidazo [5, lb] thiazol-2-yl) -6- ((1R) -1-hydroxyethyl) -1-methyl-l-carbapen-2-em-3-carboxylic acid cycloexyloxycarbonyloxymethyl ester In the same manner as in example 46, 68.7 mg were obtained of the title compound from 56.4 mg of (IS, 5R, 6S) -2- (7- acetylimidazo [5, 1-b] thiazole -2-yl) -6- ((IR) -1-hydroxyethyl) - 1- sodium methyl-l-carbapen-2-em-3-carboxylate and 60.5 mg of cycloexyloxycarbonyloxymethyl iodide NMR (CDCI3) d: 1.28 (3H, d, J = 7.1 Hz), 1.37 (3H, d, J = 6.2 Hz), 1.25 - 1.55 (6H, m), 1.68, 1.78 (2H, m), 1.83 - 1.96 (2H, m), 2.62 (3H, s), 3.35 (1H, dd, J _. = 6.6 Hz, J2 = 2.7 Hz), 3.50 (1H, m), 4.30 (1H, m), 4.39 (1H, dd, J_ = 9.7 Hz, J2 = 2.7 Hz), 4.64 (1H, m), 5.87, 5.96 (2H, ABq, J = 5.8 Hz), 8.04 (1H, s), 8.57 (1H, s) MS (TSP): 532 (M ++ H) Example 50 (1S, 5R, 6S) -2- (7-acetylimidazo [ 5, 1-b] thiazol-2-yl) -6- ((1R) -1-hydroxyethyl) -1- methyl-1-carbapen 3-Ftalidyl-2-em-3-carboxylate (a mixture of diastereomers) In the same manner as in Example 46, 39.7 mg of the title compound was obtained from 56.2 mg of (1S, 5R, 6S) - 2- (7- acetylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -1-methyl-1-carbapen-2-em-3-carboxylate sodium and 60.3 mg of 3-phthalidyl bromide. NMR (CDC13) d: 1.12 (3H, m), 1.22 (3H, m), 2.46 (3H, s), 3.42 (1H, m), 3.75 (1H, m), 3.97 (1H, m), 4.30 ( 1H, m), 5.10, 5.12 (total 1H, each s), 7.65 (1H, s), 7.74 (1H, m), 7.83 (1H, m), 7.93 (1H, m) 8.33, 8.56 (total 1H, each s) 8.39, 8.60 (total 1H, each s) MS (TSP): 508 (M ++ H) Example 51 (IS, 5R, 6S) -2- (7-acetylimidazo [5, 1-b] thiazole -2-yl) -6- ((IR) -1-hydroxyethyl) -1- methyl-l-carbapen-2-em-3-carboxylic acid 1- (acetoxy) ethyl ester (a mixture of diastereomers) In the same way that in Example 46, 79.3 mg of the title compound was obtained from 93.1 mg of (IS, 5R, 6S) -2- (7- acetylimidazo [5, 1-b] thiazole -2-yl) -6- ((IR) -1-hydroxyethyl) -1-methyl-l-carbapen-2-em-3-carboxylic acid sodium and 118.0 mg of 1- (acetoxy) ethyl iodide NMR (CDC13) d: 1.20 (3H, d , J = 7.2 Hz), 1.31 (3H, m), 1.49, 1.54 (total 3H, each J = 5.5 Hz), 1.99, 2.07 (total 3H, each s), 2.55 (3H, * s), 3.28 (1H ,), 3.42 (1H, m) 4.22 (1H, m), 4.31 (1H, m), 6.98 (1H, m), 7. 95, 7.96 (total 1H, each s), 8.53, 8.54 (total 1H, each s) MS (TSP): 462 (M ++ H) Example 52 (IS, 5R, 6S) -2- (7-acetylimidazo [ 5, lb] thiazol-2-yl) -6- ((1R) -1-hydroxyethyl) -1-methyl-1-carbapen-2-em-3-carboxylate of (5-methyl-2-oxo-1, 3-dioxolen-4-yl) methyl. In the same manner as in Example 46, 94.1 mg of the title compound was obtained from 84.6 mg of (SS, 5R, 6S) -2- (7- acetylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -1-methyl-1-carbapen-2-em-3-carboxylate sodium and 81.3 mg of (5-methyl) bromide -2-oxo-l, 3-dioxolen-4-yl) methyl NMR (CDCI3) d: 1.28 (3H, d, J = 7.2 Hz), 1.37 (3H, d, J = 6.3 Hz), 2.22 (3H, m), 2.61 (3H, s), 3.45 (1H, dd, J_ = 6.5 Hz, J2 = 2.8 Hz), 3.54 (1H, m), 4.29 (1H, m), 4.39 (1H, dd, Jx = 9.8 Hz, J2 = 2.8 Hz), 5.01, 5.09 (2H, ABq, J = 13.8 Hz), 8.05 (1H, s), 8.40 (1H, s) MS (TSP): 488 (M ++ H) Example 53 ( ÍS, 5R, 6S) -2- (7-N-acetylaminomethylimidazo- [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -1-methyl-1-carbapen- 2-em-3-c sodium arboxylate a) (SS, 5R, 6S) -2- (7-N-acetylaminomethylimidazo- [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -1- methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl Substantially in the same manner as in example la), 1.11 g of (SS, 5R, 6S) -2- (7-N-acetylaminomethylimidazo- [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -1 were obtained. 4-Nitrobenzyl methyl-1-carbapen-2-em-3-carboxylate from 0.91 g of (IR, 3R, 5R, 6S) -6- (1R) -1-hydroxyethyl) -l-methyl-2 -oxo-carbapenam-3-carboxylate and 1.09 mg of 7-N-acetylaminomethyl-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole. NMR (DMS0-D6) d: 1.15-1.20 (6H, m), 1.86 (3H, s), 3.41 (1H, dd, J? = 6.0 Hz, J2 = 2.7 Hz), 3.07 - 3.17 (1H, m) , 3.62 (1H, dd, J? = 8.8 Hz, J2 = 2.7 Hz), 4.00 - 4.05 (1H, m), 4.16 (2H, d, J = 5.8 Hz), 5.13 (1H, d, J = 4.9 Hz ), 5.39 (1H, d, J = 13.8 Hz), 5.48 (1H, d, J = 13.8 Hz), 7.71 (2H, d, J = 8.5 Hz), 8.22 (2H, d, J = 8.5 Hz), 8.21 (1H, s), 8.36 (1H, s), 8.43 (2H, d, J = 5.8 Hz) b) (SS, 5R, 6S) -2- (7-N-acetylaminomethylimidazo- [5, 1-b ] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -1-methyl-1-carbapen-2-em-3-carboxylate sodium The title compound (0.52 mg) was obtained from 175 mg of (1S, 5R, 6S) -2- (7-N-acetylaminomethylimidazo- [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -1-methyl- 4-Nitrobenzyl l-carbapen-2-em-3-carboxylate in substantially the same manner as in Example 1-b), except that the purification was carried out with Cosmosil 40C18-PREP (5% aqueous methanol), NMR ( D20) d (HOD = 4.80 PPM): 1.22 (3H, d, J = 7.1 Hz), 1.31 (3H, d, J = 6.3 Hz), 2.08 (3H, s), 4.37 (2H, s), 7.82 (1H, s), 8.04 (1H, s) Example 54 (IS, 5R, 6S) -2- (7-N-acetylaminomethylimidazo- [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -1-methyl-l-carbapen-2-em-3-carboxylate of pivaloyloxymethyl Substantially in the same manner as in Example 2, 75 mg of the title compound was obtained from 81 mg of (IS, 5R, 6S) -2- (7-N-acetylaminomethylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -1-methyl-l-carbapen-2-em-3-carboxylic acid sodium NMR (CDC13) d: 1.21 (9H, s), 1.26 (3H, d, J = 7.4 Hz ), 1.36 (3H, d, J = 6.3 Hz), 3.02 (3H, s), 3.32 (1H, d, J_ = 6.6 Hz, J2 = 2.8 Hz), 3.40 - 3.50 (1H, m), 4.25 - 4.35 (2H, m), 4.39 -4.56 (2H, m), 5.87 (1H, d, J = 5.6 Hz), 5.98 (1H, d, J = 5.6 Hz), 6.30 (1H, s), 7.98 ( 1H, s), 8.35 (1H, s) Example 55 (SS, 5R, 6S) -2- (7-N-Acetylaminomethylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) - 1-hydroxyethyl) -1- methyl-1-carbapen-2-em-3-carboxylic acid 1- (acetoxy) ethyl ester (a mixture of diastere meros) In the same manner as in example 46, 14.4 mg of the title compound was obtained from 45.2 mg of (IS, 5R, 6S) -2- (7- acetylaminomethylimidazo [5, 1-b] thiazole -2-yl) -6- ((IR) -1-hydroxyethyl) -1-methyl-1-carbapen-2-em-3-carboxylic acid sodium ester and 90.8 mg of 1- (acetoxy) ethyl iodide NMR (CDC13) d: 1.26 (3H,), 1.37 (1H, m), 1.56, 1.61 (total 3H, each J = 5.5 Hz), 2.02 (3H, s), 2.06, 2.14 (total 3H, each s), 2.10 (1H, s), 3.32 (1H, m), 3.42 (1H, m) 4.26 - 4.35 (2H,), 4.40 -4.35 (2H, m), 6.25 (1H, m), 7.03 (1H, m) , 7.96, 7.97 (total 1H, each s), 8.43, 8.44 (total 1H, each s) MS (TSP): 491 (M ++ H) Example 56 (ÍS, 5R, 6S) -2- (7- acetylaminomethylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -1-methyl-1-carbapen-2-em-3-carboxylic acid 1- (cyclohexyloxycarbonyloxy) ethyl ester (a mixture of diastereomers) In the same manner as in Example 46, 46.5 mg of the title compound was obtained from 45.1 mg of (1S, 5R, 6S) -2- (7- 'acetylamin ometilimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -1-methyl-1-carbapen-2-em-3-carboxylate sodium and 63.0 mg of iodide of (cyclohexyloxycarbonyloxy) ethyl NMR (CDC13) d: 1.26 (3H,), 1.37 (3H, m), 1.38-2.00 (11H,), 1.59, 1.65 (total 3H, each J = 5.5 Hz), 2.03 (3H, s) ), 3.33 (1H, m), 3.42 (1H, m) 4.26 - 4.38 (2H, m), 4.40 -4.55 (2H, m), 4.65 (1H, m), 6.22 (1H, br.s) , 6.94 (1H, m), 7.95, 1H, s), 8.43, 8.44 (total 1H, each s) MS (TSP): 575 (MX-H) Example 57 (ÍS, 5R, 6S) -2- (7 -acetylaminomethylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -1-methyl-l-carbapen-2-em-3-carboxylate of 3-phthalidyl (a mixture of diastereomers) In the same way as in example 46, 27.7 mg of the title compound were obtained from 33.2 mg of (SS, 5R, 6S) -2- (7- acetylaminomethylimidazo [5, 1-b] thiazole -2-yl) -6- ((IR ) -1-hydroxyethyl) -1-methyl-1-carbapen-2-em-3-carboxylate sodium and 33.8 mg of 3-phthalidyl bromide. NMR (CDCl 3) d: 1.26-1.46 (6H, m), 1.70 (1H, m), 2.03 (3H, m), 3.33 (1H, m), 3.48 (1H, m), 4.15-4.35 (2H, m ), 4.38 - 4.68 (2H, m), 6.22 (1H, m), 7.45, 7.46 (total 1H, each s), ".64 -7.81 (3H, s), 7.91 - 7.98 (1H, m), 8.16 8.49 (total 1H, each s) MS (TSP): 537 (M ++ H) Example 58 (IS, 5R, 6S) -2- (7-acetylaminomethylimidazo [5, 1-b] thiazol-2-yl) - 6- ((IR) -1-hydroxyethyl) -1- methyl-1-carbapen-2-em-3-carboxylic acid (5-methyl-2-oxo-l, 3-dioxolen-4-yl) ethyl ester in the same manner as in Example 46, 25.0 mg of the title compound was obtained from 41.7 mg of (IS, 5R, 6S) -2- (7- acetylaminomethylimidazo [5, 1-b] thiazole -2-il) -6- ((IR) -1-hydroxyethyl) -1- methyl-1-carbapen-2-em-3-carboxylate sodium and 40.0 mg of (5-methyl-2-oxo-l, 3-dioxolen bromide -4-yl) methyl NMR (CDC13) d: 1.27 (3H, d, J = 7.1 Hz), 1.36 (3H, d, J = 6.2 Hz), 1.80 (1H, br.s), 2.03 (3H, s ), 2.21 (3H, s), 3.33 (1H, dd, J? = 6.5 Hz, J2 = 2.9 Hz), 3.47 (1H, m), 4.25 - 4.55 (2H, m), 5.01, 5.07 (2H , Abq, J = 14.0 Hz), 6.32 (1H, m), 7.98 (1H, s), 8.20 (1H, s) MS (TSP): 517 (M ++ H) Example 59 (1S, 5R, 6S) -2- (7-N-Acetylaminomethylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate of 1- [(cyclohexylmethoxy) carbonyloxy] ethyl (a mixture of diastereomers) In the same manner as in Example 46, 12.8 mg of the title compound was obtained from 24.3 mg (IS, 5R, 6S) -2- ( Sodium 7-N-acetylaminomethyl) -1-methyl-l-carbapen-2-em-3-carboxylate and 71.0 mg of 1- [(cyclohexylmethoxy) carbonyloxy] ethyl iodide. NMR (CDCI3) d: 0.92-1.05 (3H, m), 1.16-1.25 (2H,), 1.26 (3H,), 1.37 (3H, m), 1.60-1.78 (9H, m), 2.03 (3H, s), 3.31 (1H,), 3.43 (1H, m), 3.93-4.05 (2H, m), 4.25-4.35 (2H, m), 4.40-4.56 (2H, m), 6.20 (1H, m), 6.92 (1H, ), 7.96 (1H, s), 8.44, 8.45 (total 1H, each s) MS (TSP): 589 (M ++ H) Example 60 (IR, 2S, 5R) -2- (7-N-acetylaminomethylimidazo [ 5, 1.b] thiazol-2-yl) -6- (IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate of (IR, 2S, 5R) - (1 ) -methyloxycarbonyloxymethyl In the same manner as in Example 46, 38.1 mg of the title compound was obtained from 33.3 mg of (SS, 5R, 6S) -2- (7-N-acetylaminomethylimidazo [5, 1-b] thiazol-2-yl) -6- ((lr) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate sodium and 39.8 mg of iodide (IR, 2S, 5R) - (1) -methyloxycarbonyloxymethyl. NMR (CDCI3) d: 0.77 (3H, d, J = 7.6 Hz), 0.89 (3H, d, J = 7.1 Hz), 0.95-1.15 (2H, m), 1.26 (3H, d, J = 7.2 Hz) , 1.36 (3H, d, J = 6.1 Hz), 1.37-1.52 (2H, m), 1.64-1.72 (2H, m), 1.80-2.10 (3H, m), 2.03 (3H, s), 3.32 (1H , dd, Jj. = 6.6 Hz, J2 = 2.8 Hz), 3.44 (1H, m), 4.25-4.35 (2H, m), 4.45-4.60 (3H,), 5.91, 5.94 (2H, ABq, J = 5.5 Hz), 6.41 (1H, m), 7.97 (1H, s), 8.40 (1H, s) MS (TSP): 617 (M ++ H) Example 61 (1S, 5R, 6S) -2- (7- N-Acetylaminomethylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 1- (cyclohexyloxycarbonyloxy) -n-propyl (a mixture of diastereomers) In the same manner as in example 46, 15.9 mg of the title compound was obtained from 30.4 rr.g of (ΔS, 5R, 6S) -2- (7-N -acetylaminomethylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylic acid and 33.3 mg of iodide of 1- (cyclohexyloxycarbonyloxy) -n-propyl NMR (CDC13) d: 0.99, 1.07 (total 3H, each t, J = 7.7 Hz), 1.25 (3H, m), 1.36 (3H, m), 1.30-1.80 (8H, m), 1.85-2.05 (4H, m), 2.03 (3H, s), 3.31 (1H , m), 3.43 (1H,), 4.26-4.35 (1H, m), 4.45-4.50 (1H, m), 4.56-4.72 (1H, m), 6.27 (1H, m), 6.80 (1H, m) , 7.94, 7.95 (total 1H, each s), 8.45, 8.47 (total 1H, each s) MS (TSP): 589 (M ++ H) Example 62 (ÍS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylic acid sodium a) (1S, 5R, 6S) -6- ((LR-1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate of 4-Nitrobenzyl in substantially the same manner as in Example la), 123 mg of (IS, 5R, 6S) -6- ((1R-1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5,1- b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl from 109 mg of (IR, 3R5R, 6S) -6- ((IR) -1 -hydroxyethyl) -l-methyl-2-oxo-l-carbapenam-3-carboxylate of 4-nitrobenzyl and 141 mg of 7-methanesulfonyl-2- (tri-n-butyl) stanil) imidazo [5, ab] thiazole NMR (CDC13) d: 1.30 (3H, d, J = 7.2 Hz), 1.37 (3H, d, J = 6.3 Hz), 3.21 (3H, s), 3.36 (1H, dd, J_ = 6.9 Hz, J2 = 2.8 Hz), 3.45-3.55 (1H, m), 4.20-4.30 (1H, m), 4.39 (1H, dd, J_ = 9. 6 Hz, J2 = 2.8 Hz), 5.30 (1H, d, J = 13.5 Hz), 5.52 (1H, d, J = 13.5 Hz), 7.69 (2H, d, J = 8.9 Hz), 8.10 (1H, s), 8.24 (2H, d, J = 8.9 Hz), 8.43 (1H, s) b) (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1- sodium biathial-2-yl) -1-methyl-l-carbapen-2-em-3-carboxylate The title compound (83.4 mg) was obtained from 123 mg of (IS, 5R, 6S) - 6- ((IR) -1-hydroethyl) -2- (7-methanesulfonylimidazo [5, 1-b] -2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl , except that the purification was carried out using Cosmosil 40C18-PREP (5% aqueous methanol). NMR (D20) d: (HOD = 4.80 ppm): 1.25 (3H, d, J = 7.0 Hz), 1.32 (3H, d, J = 6.3 Hz), 3.30 (3H, s), 3.52-3.55 (1H, m), 3.55-3.66 (1H, m), 4.24-4.35 (2H,), 8.03 (1H, s), 8.28 (1H, Example 63 (1S, 5R, 6S) -6- ((IR) -1 -hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate of pivaloyloxymethyl in substantially the same manner as in the example 2, 68.5 mg of the title compound were obtained from 54.7 mg of, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonyl-imidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2- sodium em-3-carboxylate. NMR (CDC13) d: 1.21 (9H, s), 1.28 (3H, d, J = 7.3 Hz), 1.34 (3H, d, J = 6.3 Hz), 3.23 (3H, s), 3.40 (1H, dd, Ji = 5.8 Hz, J2 = 2.7 Hz), 3.50-3.61 (1H, m), 4.23-4.31 (1H, m), 4.40 (1H, dd, Ji = 9.7 Hz, J2 = 2.7 Hz), 5.87 (1H, d, J = 5.7 Hz), 5.98 (1H, d, J = 5.7 Hz), 8.25 (1H, s), 8.51 (1H, s). Example 64 (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b.] Thiazol-2-yl) -l-methyl-l- 1- (acetoxy) ethyl carbapen-2-em-3-carboxylate (a mixture of diastereomers) In the same manner as in Example 46, 22.2 mg of the title compound was obtained from 55.8 mg of (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-carboxylate sodium and 50.0 mg of 1- (acetoxy) ethyl iodide NMR (CDCl 3) d: 1.21 (3H, d, J = 7.4 Hz), 1.30 (3H, m), 1.50, 1. 54 (total 3H, each d, J = 5.5 Hz), 2.02, 2.10 (total 3H, each s), 3.28 (1H, m), 3.40 (1H, m), 4.22 (1H, m), 4.30 (1H, ), 6.95 (1H, m), 8.03, 8.04 (total 1H, each s), 8.48 (1H, s). MS (TSP): 498 (M + + H) Example 65 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazole-2 1-cyclohexyloxycarbonyloxy) ethyl ester (a mixture of diastereoisomers) In the same manner as in Example 46, 19.0 mg of the compound of the title from 24.8 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl sodium l-carbapen-2-em-3-carboxylate and 52.9 mg of 1- (cyclohexyloxycarbonyloxy) ethyl iodide, NMR (CDCl 3) d: 1.20 (3H, d, J = 7.2 Hz), 1.30 (3H, m )> 1.35-1.70 (8H, m), 1.52, 1.58 (total 3H, each d, J = 5.4 Hz), 1. 80-2.00 (2H, m), 3.15 (3H, s), 3.27 (1H, m), 3.38 (1H, m), 4. 20 (1H, m), 4.28 (1H, m), 4.58 (1H,), 6.87 (1H, m), 8.01 (1H, s), 8.49, 8.50 (total 1H, each s) MS (TSP): 582 (MAH) Example 66 (ÍS, 5R, 6S) -6- ((IR) -i-hydroxyethyl) -2- ( 7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-e-3-phthalidylcarboxylate (a mixture of diastereomers) In the same manner as in example 46, 23.5 mg of the title compound were obtained from 27.6 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2 sodium em-3-carboxylate and 30.0 mg of 3-phthalidyl bromide. NMR (CDC13) d: 1.29 83H, m), 1.32 (3h, m), 2.10 (lh, br.s), 3.21, 3.22 (total 1H, each s), 3.36 (1H,), 3.50 (1H, m ), 4.24 (1H, m), 4.38 (1H, m), 7.44.7.45 (total 1H, each s), 7.63-7.80 (3H, m), 7.81, 7.91 (total 1H, each s), 8.07, 8.12 (total 1H, each s), 8.32, 8.60 (total 1H, each s) MS (TSP): 544 (M ++ H) Example 67 (ÍS, 5R, 6S) -6- ((IR) -1-hydroxyethyl ) -2- (7-methanesulfonylimidazo [5, lb.] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate of (5-methyl-2-oxo-l, 3 -dioxolen-4-yl) methyl. In the same manner as in Example 46, 17.9 mg of the title compound was obtained from (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2 - (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -1-methyl-l-carbapen-2-em-3-carboxylate sodium and 34.0 mg of (5-methyl-2-oxo) bromide -l, 3-dioxolen-4-yl) methyl. NMR (CDCI3) d: 1.29 (3H, d, J = 7.4 Hz), 1.37 (3h, d, J = 6.3 Hz), 2.22 (3H, s), 3.23 (3H, s), 3.36 (1H, dd, J_ = 6.5 Hz, J2 = 2.8 Hz), 3.49 (1H, m), 4.29 (1H, m), 4.38 (1H, dd, J_ = 9.6 Hz, J2 = 2.8 Hz), 5.02, 5.09 (2H, ABq, J = 14.0 Hz), 8. 12 (1H, s), 8.34 (1H, s) MS (TSP): 524 (M ++ H) Example 68 (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- ( 7-Methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 1- [(cyclohexylmethoxy) carbonyloxy] ethyl ester (a mixture of diastereomers) In the same manner as in Example 46, 28.6 mg of the title compound were obtained from 32.2 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2 sodium carboxylate and 52.5 mg of 1- [(cyclohexylmethoxy) carbonyloxy] ethyl iodide. NMR (CDC13) d: 0.86-1.06 (3H,), 1.10-1.55 (3H, m), 1.27 (3H, d, J = 7.1 Hz), 1.37 (3H,, 1.60 (3H, d, J = 5.5 Hz), 1. 58 (3H, d, J = 5.5 Hz), 1.60-1.81 (8H, m), 3.21 (3H, s), 3.45 (1H,), 3.92-4.05 (2H, m), 4.28 (1H, m), 4.35 (1H, m), 6. 93 (1H, m), 8.08, 8.09 (total 3H, each s), 8.56, 8.57 (total 3H, each s) MS (TSP): 596 (M ++ H) Example 69 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, ib] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate of (1-methylcyclohexan-1-yl-carbonyloxymethyl) In the same manner as in Example 46, 28.6 mg of the Title compound from (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -1-methyl- sodium l-carbapen-2-em-3-carboxylate and 45.0 mg iodide (1-methylcyclohexan-1-yl) carbonyloxymethyl NMR (CDC13) d: 1.15 (3H, s), 1.27 (3H, d, J = 7.2 Hz), 1.37 (3H, d, J = 6.3 Hz), 1.28-1.70 (8H, m), 1.96-2.05 (1H,), 3.22 (3H, s), 3.35 (1H, dd, J_ = 9.8 Hz, J2 = 2.8 Hz ), 5.91, 5.97 (2H, ABq, J = 5.6 Hz), 8.11 (1H, s), 8.46 (1H, s) MS (TSP): 566 (MVH) Example 70 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 1- (cyclohexyloxycarbonyloxy) -n-propyl (mixture of diastereomers) In the same manner as in Example 46, 17.2 mg of the title compound was obtained from 25.0 mg of (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2 - (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylic acid sodium and 36.0 mg of 1- (cyclohexyloxycarbonyloxy) -n- iodide propyl. NMR (CDCI3) d: 1.02, 1.09 (total 3H, each t, J = 7.4 Hz), 1.20-2.05 (11H, m), 1.27 (3H,), 1.36 (3H, m), 3.22 (3H, s) , 3.34 (1H, m), 3.48 (1H, m), 4.29 (1H, m), 4.36 (1H, m), 4.65 (1H, m), 6.80 (1H, m), 8.07 (1H, s), 8.59, 8.60 (total 1H, each s) MS (TSP): 596 (M ++ H) Example 71 (1S, 5R, 6S) -2- (7-hydroxyacetylimidazo [5, 1-b] thiazol-2-yl) ) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylic acid sodium a) (SS, 5R, 6S) -2- (7-t-butyldimethylsilyloxyacetylimidazo [ 5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl In the same manner as in example la) 397 mg of (SS, 5R, 6S) -2- (7-t-butyldimethylsilyloxyacetylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) were obtained -l-Methyl-l-carbapen-2-em-3-carboxylic acid 4-nitrobenzyl from 567 mg of (IR, 3R, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l- Methyl-2-oxo-l-carbapenam-3-carboxylate of 4-nitrobenzyl and 1.10 g of 7-t-butyldimethylsilyloxyacetyl-2- (tri) -n-butylstannyl) -imidazo [5, 1-b] thiazole. NMR (CDC13) d: 0.15 (6H, s), 0.96 (9H, s), 1.30 (3H, d, J = 7.4 Hz), 1.40 (3H, d, J = 6.3 Hz), 3.38 (1H, m) , 3.50 (1H, m), 4.32 (1H, m), 4.40 (1H, dd, Jx = 9.5 Hz, J2 = 2.9 Hz), 5.08 (2H, s), 5.28 (1H, d, J = 14.1 Hz) , 5.52 (1H, d, J = 14.1 Hz), 7.68 (2H, d, J = 8.8 Hz), 7.98 (1H, s), 8.25 (2H, d, J = 8.8 Hz), 8.51 (1H, s) b) (SS, 5R, 6S) -2- (7-hydroxyacetylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-1-carbapen- 2-em-3-carboxylate of 4-nitrobenzyl From the same handle as in example 36-b), 193 mg of (1S, 5R, 6S) -2- (7-hydroxyacetylimidazo [5, 1-b] were obtained thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl from 397 mg of (IS, 5R, 6S ) -2- (7-t-Butyldimethylsilyloxyacetylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3 4-nitrobenzyl NMR (CDC13) d carboxylate: 1.32 (3H, d, J = 7.2 Hz), 1.40 (3H, d, J = 6.3 Hz), 3.40 (1H, dd, Jx = 6.3 Hz, J2 = 2.8 Hz ) , 3 .51 (2H, m), 4.33 (1H, m), 4.42 (1H, 'dd, Ji = 9.6 Hz, J2 = 2.8 Hz), 4.91 (2H, d, J = 4.4 Hz), 5.28 (1H, d , J = 13.7 Hz), 5.53 (1H, d, J = 13.7 Hz), 7.68 (2H, d, J = 8.8 Hz), 8.02 (1H, s), 8.24 (2H, d, J = 8.8 Hz), 8.51 (1H, s) c) (SS, 5R, 6S) -2- (7-hydroxyacetylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l- sodium methyl-l-carbapen-2-em-3-carboxylate In the same manner as in Example 1-b), 259 mg of the title compound was obtained from 407 mg of (1S, 5R, 6S) - 2- (7-hydroxyacetylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate from 4- Nitrobenzyl NMR (D20) d: (HOD = 4.08 ppm): 1.20 (3H, d, J = 6.7 Hz), 1.33 (3H, d, J = 6.3 Hz), 3.50 (2H, m), 4.75 (2H, m ), 7.88 (1H, s), 8.02 (1H, s) Example 72 (SS, 5R, 6S) -2- (7-hydroxyacetylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR Pivaloyloxymethyl) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate In the same manner as in Example 2, 56.2 were obtained mg of the title compound from 60.4 mg of (IS, 5R, 6S) -2- (7-hydroxyacetylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate sodium.

NMR (CDC13): 1.20 (9H, s), 1.30 (3H, d, J = 7.4 Hz), 1.38 (3H, d, J = 6.2 Hz), 3.36 (1H, dd, Ji = 6.7 Hz, J2 = 2.9 Hz), 3. 50 (2H, m), 4.30 (1H,), 4.40 (1H, dd, J_ = 9.9 Hz, J2 = 2. 9 Hz), 4.92 (2H, d, J = 3.8 Hz), 5.87 (1H, d, J = 5.5 Hz), 6.00 (1H, d, J = 5.5 Hz), 8.06 (1H, s), 8.51 (1H , s) Example 73 (SS, 5R, 6S) -2- (7-hydroxyacetylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-1 -carbapene-2-em-3-carboxylic acid 1- (acetoxy) ester (a mixture of diastereomers) In the same manner as in, the title compound (16.6 mg) was obtained from 25.0 mg of (IS, 5R) , 6S) -2- (7-hydroxyacetylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3 sodium carboxylate and 30.0 mg of 1- (acetoxy) ethyl iodide. NMR (CDCI3) d: 1.21 (3H, d, J = 7.4 Hz), 1.31 (total 3H, all d, J = 6.2 Hz), 1.49, 1.54 (total 3h, each d, J = 5.5 Hz), 1.65 ( 1H, br.s), 2.00, 2.07 (total 3H, each s), 3.28 (1H,), 3.37-3.50 (2H,), 4.22 (1H, m), 4.32 (1H, m), 4.84 (1H, s), 4.85 (1H, s), 6.97 (1H, m), 7.97, 7.98 (total 1H, each s), 8.53 (1H, s) MS (FAB +): 478 (M ++ H) Example 74 (SS, 5R, 6S) -2- (7-hydroxyacetylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-1-carbapen-2 1- (cyclohexyloxycarbonyloxy) ethyl ester (3-carboxylate) (a mixture of diastereomers) In the same manner as in Example 46, 22.7 mg of the title compound were obtained from 22.0 mg of (1S, 5R, 6S) -6- ((1R) -l-hydroxyethyl) -2- (7-hydroxyacetylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-1-carbapen-2 sodium em-3-carboxylate and 45.0 mg of 1- (cyclohexyloxycarbonyloxy) ethyl iodide. NMR (CDC13) d: 1.10-1.40 (7H,), 1.53, 1.58 (total 3H, each d, J = 5.5 Hz), 1.42-1.75 (4H, m9, 1.78-2.00 (6H, m9, 2.12 (1H, br.s), 3.28 (1H,), 3.38-3.50 (2H, m), 4.23 (1H, m), 4. 31 (1H,), 4.59 (1H, m), 4.84 (1H, s), 4.85 (1H, s), 6.87 (1H, m), 7.97 (1H, m), 8.35, 8.54 (total 1H, each s) MS (FAB +): 562 (M ++ H) Example 75 (ÍS, 5R, 6S) -2- (7- hydroxyacetylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-e-3-carboxylate 3-phthalidyl (a mixture of diastereomers) In the same manner as in Example 46, 24.8 mg of the title compound was obtained from 29.0 mg of (SS, 5R, 6S) -2- (7-hydroxyacetylimidazo [5, 1-b] thiazole-2 -yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate sodium and 29.9 mg of 3-phthalidyl bromide. NMR (CDC13) d: 1.25-1.38 (6H, m), 1.68-1.75 (2H,), 3.38 (1H, m), 3.52 (1H, m), 4.25 (1H, m), 4.38 (1H, m), 4.91 (1H, s), 4.93 (1H, s), 7.45, 7.46 (total 1H, each s ), 7.65-7.82 (3H, m9, 7.92-7.95 (1H, m), 8.04, 8.08 (total 1H, each s), 8.41, 8.70 (total 1H, each s) MS (FAB +): 524 (M ++ H) Example 76 ( 1S, 5R, 6S) -2- (7-hydroxyacetylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em -3-carboxylate (5-methy1-2-oxo-l, 3-dioxolen-4-yl) methyl In the same manner as in Example 46, 23.0 mg of the title compound was obtained from 27.2 mg of (1S, 5R, 6S ) -2- (7-hydroxyacetylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate from sodium and 30.0 mg of (5-methyl-2-oxo-l, 3-dioxolen-4-yl) methyl bromide. NMR (CDCI3) d: 1.31 (3H, d, J = 7.2 Hz), 1.38 (3H, d, J = 6.2 Hz), 1.92 (1H, br.s), 2.23 (3H, s), 3.38 (1H, dd, J_ = 6.6 Hz), J2 = 2.9 Hz), 3.49 (1H, br, s), 4.31 (1H, m), 4.40 (1H, dd, Ji = 9.8 Hz, J2 = 2.9 Hz), 4.91 (1H , s), 4.93 (1H, s), 5.00, 5.06 (2H, ABq, J = 14.0 Hz), 3.07 (1H, s), 8.41 (1H, s) MS (FAB +): 504 (M ++ H) Example 77 (SS, 5R, 6S) -2- (7-hydroxyacetylimidazo [5, lt; thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2- (1-Methylcyclohexaxn-1-yl) carbonyloxymethylene-3-carboxylate In the same manner as in Example 46, 26.4 mg of the title compound was obtained from 20.7 mg of (IS, 5R, 6S) -2- (7-hydroxyacetylimidazole [5, lb thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-1-carbapen-2-em-3-carboxylate sodium and 30.0 mg of iodide of (1-methylcyclohexan-1-yl) carbonyloxymethyl. NMR (CDC13) d: 1.14 (3H, s), 1.20-1.60 (SH, m), 1.30 (3H, d, J = 7.4 Hz), 1.37 (3H, d, J = 6.3 Hz), 1.95-2.05 (2H,), 3. 63 (1H, dd, Ji = 6.5 Hz, J2 = 2.8 Hz), 4.30 (1H, m), 4.40 (1H, dd, Ji = 9.7 Hz, J2 = 2.8 Hz), 4.92 2H, s), 5.92, 5.98 (2H, ABq, J = 5.6 Hz), 8.07 (1H, s), 8.50 1H, s) MS (TSP): 546 (M ++ H) Example 78 (ÍS, 5R, 6S) -2- (7- hydroxyacetylimidazo [5, lthiazol-2-yl] -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 1- [(cyclohexylmethoxy) carbonyloxyethyl ester, a mixture of diastereomers) In the same manner as in Example 46, 6.12 mg of the title compound was obtained from 21.2 mg of (SS, 5R, 6S) -2- (7-hydroxyacetylimidazo [5, 1-b] thiazole -2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate sodium and 33.0 mg of 1- [(cyclohexylmethoxy) carbonyloxy] ethyl iodide . NMR (CDC13) d: 0.88-1.10 (2H, m), 1.15-1.30 (1H, m), 1.29 (3H, m), 1.38 (3H, m), 1.60, 1.66 (total 3H, each d, J = 5.5 Hz), 1.65-1.90 (9H, m), 3.35 (1H, m), 3.50 (1H, m ), 3.92-4.05 (2H,), 4.29 (1H, m), 4.38 (1H, m), 4.91 (1H, s), 4.92 (1H, s), 6.94 (1H, m), 8.03 (1H, s), 8.60 (1H , s), 8.62 (total 1H, each s) MS (TSP): 576 (M ++ H) Example 79 (SS, 5R, 6S) -2- (7-hydroxyacetylimidazo [5, 1-b] thiazole-2 -yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate of 1- (cyclohexyloxycarbonyloxy) -n-propyl (a mixture of diastereomers) In the same manner as in Example 46, 18.3 mg of the title compound was obtained from 21.7 mg of (IS, 5R, 6S) -2- ( 7-hydroxyacetylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate sodium and 22.0 mg of 1- (cyclohexyloxycarbonyloxy) -n-propyl iodide.

NMR (CDCI3) d: 1.00, 1.08 (total 3H, each t, J = 7.6 Hz), 1.26-1.80 (13H,), 1.85-2.05 (6H, m), 3.35 (1H, m), 3.50 (2H, m), 4.30 (1H, br.m), 4.39 (1H, m), 4.65 (1H, m), 4.91 (1H, s), 4.92 (1H, s), 6.80, 6.82 (total 1H, each d, J = 6.0 Hz), 8.02, 8.03 (total 1H, each s), 8.62, 8.64 (total 1H, each s) MS (TSP): 576 (M ++ H) Example 80 (ÍS, 5R, 6S) -2 - [7- (N, N-dimethylcarbomyl) acetylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em- Sodium 3-carboxylate a) (SS, 5R, 6S) -2- [7- (N, N-dimethylcarbomyl) acetylimidazo [5, 1-b] thiazol-2-yl] -6- ((IR) -1 -hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl In a manner substantially identical to example la), 245 mg of (IS, 5R, 6S) -2- [7- (N, N-dimethylcarbomyl) acetylimidazo [5, 1-b] thiazol-2-yl] -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate of 4-Nitrobenzyl from 254 mg of (IR, 3R, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2-oxo-l-carbapen 4-Nitrobenzyl am-3-carboxylate and 290 mg of 7- (N, N-dimethylcarbamoylacetyl) -2- (tri-n-butylstannyl) -imidazo [5, 1-b] thiazole. NMR (CDCI3) d: 1.30 (3H, d, J = 7.2 Hz), 1.37 (3H, d, J = 6.2 Hz), 3.07 (3H, s), 3.25 (3H, s), 3.35-3.41 (1H, m), 3.43 (2H, s), 4.18-4.25 (1H, m) 4.35-4.42 (1H, m), 5.31 (1H, d, J = 13.5 Hz), 5.52 (1H, d, J = 13.5), 7.30; iH, s), 7.70 (2H, d, J = 8.8 Hz), 8.55 (1H, s) b) (1S, 5R, 6S) -2- [7- (N, N-dimethylcarbamoyl) acetylimidazo [5 , 1-b] thiazol-2-yl] -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate sodium The title compound (143.2 mg) was obtained from 245 mg of (IS, 5R, 6S) -2- [7- (N, N-dimethylcarbomyl) acetylimidazo [5, 1-b] thiazol-2-yl] -6- ((IR) -1 -hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl in a manner substantially identical to example 1-b), except that the purification was carried out using Cosmosil 40C18-PREP (5% aqueous methanol). %). NMR (D20) d: (HOD = 4.80 ppm): 1.24 (3H, d, J = 7.1 Hz), 1.32 (3H, d, J = 6.3 Hz), 2.98 (3H, s), 3.10 (3H, s) , 3.52 (1H, dd, Ji = 6.1 Hz, J2 = 2.4 Hz), 3.55-3.66 (1H, m), 4.07 (1H, d, J = 16.5 Hz), 4.20 (1H, d, J = 16.5 Hz) , 4.24-4.35 (2H, m), 8.05 (1H, s), 8.17 (1H, s) Example 81 (IS, 5R, 6S) -2- [7- (N, N-dimethylcarbamoyl) acetylimidazo [5, 1 -b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-ene-3-carboxylate of phenyloyloxymethyl In substantially the same way as example 2, 34.1 mg of the title compound was obtained from 48.5 mg of (IS, 5R, 6S) -2- [7- (N, N-dimethylcarbamoyl) acetylimidazo [5, 1-b] thiazol-2-yl] - 6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate sodium. NMR (CDCI3) d: 1.21 (9H, s), 1.27 (3H, d, J = 7.1 Hz), 1.35 (3H, d, J = 6.3 Hz), 3.01 (3H, s), 3.10 (3H, s) , 3.27 (1H, dd, Ji = 7.5 Hz, J2 = 2.5 Hz), 3.42-3.53 (1H, m), 4.16 (2H, s), 4.16-4.25 (1H, m), 4.27-4.33 (1H,) , 5.89 (1H, d, J = 5.5 Hz), 5.98 (1H, d, J = 5.5 Hz), 8.04 (1H, s), 8.55 (1H, s) Example 82 (SS, 5R, 6S) -2- [7- (N, N-dimethylcarbamoyl) acetylimidazo [5, 1-b] thiazol-2-yl] -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3 - (l-methylcyclohexap-1-yl) carbonyloxymethylcarboxylate In the same manner as in Example 46, 25.5 mg of the title compound was obtained from 25.7 mg of (IS, 5R, 6S) -2- [7- (N, N-dimethylcarbamoyl, acetylimidazo [5, 1-b] thiazol-2-yl] -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate of sodium and 31.5 mg of (1-methylcyclohexan-1-yl) carbonyloxymethyl iodide, NMR (CDCI3) d: 1.15 (3H, s), 1.22-1.30 (2H,), 1.25 (3H, d, J = 7.4 Hz) , 1.36 (3H, d, J = 6.2 Hz), 1.42-1.75 (4H, m), 1.97-2.08 (2H,), 3.01 (3H, s), 3.09 (3H, s), 3.31 (1H, dd, Ji = 7.2, J2 = 2.8 Hz), 3.48 (1H, m), 4.17 (1H, s), 4.18 (1H, s), 4.23 (1H , m), 4.33 (1H, dd, Ji = 9.7 HZ, J2 = 2.8 Hz), 5.92 (2H, ABq, J = 5.5 Hz), 8.05 (1H, s), 8.53 (1H, s) MS (TSP) : 601 (M ++ H) Example 83 (1S, 5R, 6S) -2-. { 7- (N, N-dimethylcarbamoyl) acetylimidazo [5, 1-b] thiazol-2-yl] -6- ((IR) -1-hydroxyethyl) -1-methyl-l-carbapen-2-em-3 1- (cyclohexyloxycarbonyloxy) ethyl carboxylate a mixture of diastereomers) In the same manner as in Example 46, 12.8 mg of the title compound was obtained from 28.2 mg of (IS, 5R, 6S) -2- [7- (N, N-dimethylcarbamoyl) acetylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate of sodium and 30.0 mg of 1- (cyclohexyloxycarbonyloxy) ethyl iodide NMR (CDC13) d: 1.22 (3H, d, J = 7.4 Hz), 1.35 (3H, m), 1.25-1.80 (9H, m), 1.60, 1.65 (total 3H, each d, J = 5.5 Hz), 1.95-2.04 (2H, m), 3.01 (3H, s), 3.09, 3.10 (total 3H, each s), 3.30 (1H,), 3.47 (1H, m), 4.16, 4.18 (total 2H, each s), 4.25 (1H, m), 4.35 (1H, m), 4.68 (1H, m), 6.94 (1H, m), 8.01, 8.02 (total 1H, each s), 8.63, 8.65 (total 1H, each s) MS (TSP): 617 (M ++ H) Example 84 (IS, 5R, 6S) -2- [7- (N, N-dimethylcarbamoli) acetylimidazo [5 , 1-b] thiazole -2-yl] -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate 3-phthalidyl (a mixture. of diastereomers) In the same manner as in example 46, 21.6 mg of the title compound was obtained from 26.0 mg of (IS, 5R, 6S) -2- [7- (N, N-dimethylcarbamoyl) acetylimidazo [5 , 1-b] thiazol-2-yl] -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate sodium and 24.4 mg of 3-phthalidyl bromide . NMR (CDC13) d: 1.24 (3H, m), 1.32 (3H, d, J = 6.2 Hz), 3.01 (3H, s), 3.10 (3H, s), 3.31 (1H, m), 3.41 (1H, m), 4.14-4.24 (3H, m), 4.36 (1H, m), 7.44, 7.46 (total 1H, each s), 7.65- 7.80 (3H, m), 7.92 (1H, m), 7.99, 8.03 (total 1H, each s), 8. 40, 8.67 (total 1H, each s). MS (TSP): 579 (M + + H) Example 85 (1S, 5R, 6S) -2- [7- (N, N-dimethylcarbamoyl) acetylimidazo [5, 1-b] thiazol-2-yl] -6 - ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylic acid (5-methyl-2-oxo-l, 3-diocolen-4-yl) ethyl ester In the same manner as in Example 46, 26.1 mg of the title compound was obtained from 36.1 mg of (IS, 5R, 6S) -2- [7- (N, N-dimethylcarbamoyl) acetylimidazo [5, 1-] b] thiazol-2-yl] -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate sodium and 24.0 mg of (5-methyl-2-bromide -oxo-1, 3-dioxolen-4-yl) -methyl. NMR (CDCI3) d: 1.27 (3H, d, J = 7.1 Hz), 1.37 (3H, d, J = 6.2 Hz), 2.22 (3H, s), 2.70 (1H, br.s), 3.01 (3H, s), 3.10 (3H, s), 3.32 (1H, dd, Jx = 7.1 Hz, J2 = 2.8 Hz), 3.50 (1H, m), 4.17 (2H, m), 4.26 (1H, m), 4.38 (1H, dd, Jx = 9.8 Hz, JL = 2.8 Hz), 5.00, 5.10 (2H, ABq, J = 14.2 Hz), 8.04 (1H, s), 8. 40 (1H, s) MS (TSP): 559 (M + H) Example 86 (1S, 5R, 6S) -2- [7- (N, N-dimethylcarbamoyl) acetylimidazo [5, 1-b] thiazole- 2-yl] -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 1- [(cyclohexylmethoxy) carbonyloxy] ethyl ester In the same manner as in the example 46, 22.3 mg of the title compound was obtained from 30.2 mg of (IS, 5R, 6S) -2- [7- (N, N-dimethylcarbamoyl) acetylimidazo [5,1-b] thiazol-2-yl] -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate sodium and 45.0 mg of 1- [(cyclohexyl ethoxy) carbonyloxy] ethyl iodide. NMR (CDC13) d: 0.92-1.02 (2H, m), 1.10-1.30 (2H, m), 1.23 (3H,), 1.37 (3H, m), 1.60-1.80 (7H, m), 1.60, 1.66 ( total 3H, each d, J = 5.5 Hz), 3.01 (3H, s), 3.09, 3.10 (total 3H, each s), 3.30 (1H, m), 3.47 (1H, m), 3.95-4.04 (2H, m), 4.16-4.35 (4H, m), 6.94 (1H, m), 8.01, 8.02 (total 1H, ch s), 8.63, 8.65 (total 1H, each s). MS (TSP): 631 (M + + H) Example 87 (1S, 5R, 6S) -2- [7- (N, N-dimethylcarbamoyl) acetylimidazo [5, 1-b] thiazol-2-yl] -6 - ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 1- [(cyclohexyloxycarbonyloxy) -n-propyl ester (a mixture of diastereomers) In the same manner as in the Example 46, 17.9 mg of the title compound was obtained from 25.1 mg of (1S, 5R, 6S) -2- [7- (N, N-dimethylcarbamoyl) acetylcarbonylimidazo [5, 1-b] thiazol-2-yl. ] -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate sodium and 45.0 mg of 1- (cyclohexyloxycarbonyloxy) -n-propyl NMR iodide (CDC13) d: 0.90-1.40 (3H, m), 1.21 (3H, m), 1.36 (3H, m), 1.45-1.60 (4H, m), 1.85-2.01 (5H, m), 3.01 (1H, s), 3.09 (1H, s), 3.31 (1H, m), 3.49 (1H, m), 3.62 (1H, m), 4.15-4.38 (3H, m), 4.66 (1H, m), 6.80 (1H, m) , 8.01, 8.02 (total 1H, each s), 8.64, 8.66 (total 1H, each s), MS (TSP): 631 (MAH) Example 88 (1S, 5R, 6S) -2- [7- (N, N-dimethylsulfamoyl) imidazo [5, 1-b] thiazol-2-yl] -6- . { (IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylic acid sodium a) (1S, 5R, 6S) -2- [7- (N, N-dimethylsulfamoyl) imidazo [ 5, 1-b] thiazol-2-yl] -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl In a manner substantially similar to the example la), 115 mg of (SS, 5R, 6S) -2- [7- (N, N-dimethylsulfamoyl) imidazo [5, 1-b] thiazol-2-yl] -6- ((IR) - 1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl from 109 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) - l-Methyl-2-oxo-l-carbapenam-3-carboxylate of 4-nitrobenzyl and 143 mg of 7- (N, N-dimethylsulfamoyl) -2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole NMR (CDCI3) d: 1.30 (3H, d, J = 7.2 Hz), 1.37 (3H, d, J = 6.1 Hz), 2.84 (6H, m), 3.36 (1H, dd, Ji = 6.9 Hz, J2 = 2.5 Hz), 3.50-3.60 (1H, m), 4.20-4.30 (1H, m), 4.38 (1H, dd, Ji = 9.6 Hz, J2 = 2.5 Hz), 5.29 (1H, d, J = 13.7 Hz) , 5.51 (1H, d, J = 13.7 Hz), 7.68 (2H, d, J = 8.5 Hz), 8.23 (1H, s), 8.23 (2H, d, J = 8.5 Hz), 8.40 (1H, s) b) (SS, 5R, 6S) -2- [7- (N, N-dimethylsulfamoyl) imidazo [5, 1-b] thiazol-2-yl] - Sodium 6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate The title compound (51.7 mg) obtained from 115 mg of (IS, 5R, 6S ) -2- [7- (N, N-dimethylsulfamoyl) imidazo [5, 1-b] thiazol-2-yl] -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2 4-Nitrobenzyl-ene-3-carboxylate in substantially the same manner as in Example 1-b), except that the purification was carried out using Cosmosil 40C18-PREP (10% aqueous methane). NMR (D20) d: (HOD = 4.80 ppm): 1.25 (3H, d, J = 7.1 Hz), 1.31 (3H, d, J = 6.0 Hz), 2.77 (6H, s), 3.50-3.55 (1H, m), 3.58-3.66 (1H, m), 4.23-4.36 (2H, m), 8.06 (1H, m), 8.26 (1H, s). MS (TSP): 631 (MAH) Example 89 (IS, 5R, 6S) -2- [7- (N, N-dimethylsulfamoyl) imidazo [5, 1-b] thiazol-2-yl] -6- ( (IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxy-pivaloyloxymethyl In the same manner as in Example 46, 33.7 mg of the title compound were obtained from 52.2 mg of (1S, 5R, 6S) -2- [7- (N, N-dimethylsulfamoyl) imidazo [5, 1-b] thiazol-2-yl] -6- ((IR) -1-hydroxyethyl) -l-methyl sodium l-carbapen-2-em-3-carboxylate and 45 mg of pivaloyloxymethyl iodide.

NMR (CDC13) d: 1.21 (9H, s), 1.29 (3H, d, J = 7.4 Hz), 1.37 (3H, d, J = 6.3 Hz), 2.88 (6H, s), 3.35 (1H, dd, Ji = 6.5 Hz, J2 = 2.8 Hz), 3.45 (1H, m), 4.29 (1H, m), 4.37 (1H, dd, J? = 9. 8 Hz, J2 = 2.8 Hz), 5.87, 5.99 (2H, ABq, J = 5.2 Hz), 8.08 (1H, s), 8.46 (1H, s) MS (TSP): 555 (M ++ H) Example 90 (SS, 5R, 6S) -2- [7- (N, N-dimethylsulfamoyl) imidazo [5, 1-b] thiazol-2-yl] -6- ((IR) -1-hydroxyethyl) -l-methyl -l-carbapen-2-em-3-carboxylate of (1-methylcyclohexan-1-yl) carbonyloxymethyl In the same manner as in Example 46, 34.1 mg of the title compound was obtained from 32.6 mg of (IS, 5R, 6S) -2- [7- (N, N-dimethylsulfamoyl) imidazo [5, 1-] b] thiazol-2-yl] -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate sodium and 39.8 mg of iodide (1-methylcyclohexan-1) -yl) -carbonyloxymethyl NMR (CDCl 3) d: 1.15 (3H, s), 1.20-1.30 (4H, m), 1.27 (3H, d, J = 7.2 Hz), 1.36 (3H, d, J = 6.3 Hz) , 1.41-1.58 (3H, m), 1.97-2.06 (3H, m), 2.87 (6H, s), 3.34 (1H, d, J_, = 6.8 Hz, J2 = 2.7 Hz), 3.48 (1H, m), 4.27 (1H, m), 4.36 (1H, dd, Ji = 7.4 Hz, J2 = 2.7 Hz), 5.92, 5.97 (2H, ABq, J = 5.6 HZ), 8.11 (1H, s), 8.43 ( 1H, s) MS (TSP): 595 (M + + H) Example 91 (SS, 5R, 6S) -2- [7- (N, N-dimethylsulfamoyl) imidazo [5, 1-b] thiazole-2- il] -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylic acid (1-cyclohexyloxycarbonyloxy) ethyl ester (a mixture of diastereomers) In the same manner as in the Example 46, 17.1 mg of the title compound was obtained from 19.9 mg of (SS, 5R, 6S) -2- [7- (N, N-dimethylsulfamoyl) imidazo [5, 1-b] thiazol-2-yl] -6- ((IR) -1-hydroxyethyl) -l-methyl sodium l-carbapen-2-em-3-carboxylate and 30 mg of 1- (cyclohexyloxycarbonyloxy) ethyl iodide. NMR (CDC13) d: 1.28-1.45 (8H, m), 1.48-1.98 (9H,), 1.58, 1. 65 (total 3H, each d, J = 5.5 Hz), 2.87 (6H, s), 3.34 (1H,), 3.62 (1H, m), 4.29 (1H, m), 4.36 (1H, m), 4.66 ( 1 HOUR, ) , 6. 95 (1H, m), 8.05, 8.06 (total 3H, each s), 8.55, 8.56 (total 1H, each s) MS (TSP): 611 (M ++ H) Example 92 (ÍS, 5R, 6S) - 2- [7- (N, N-dimethylsulfamoyl) imidazo [5, 1-b] thiazol-2-yl] -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em 3-phthalidyl carboxylate (a mixture of diastereomers) In the same manner as in Example 46, 30.7 mg of the title compound was obtained from 32.1 mg of (1S, 5R, 6S) -2- [7 - (N, N-dimethylsulfamoyl) imidazo [5, 1-b] thiazol-2-yl] -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate of sodium and 30.9 mg of 3-phthalidyl bromide NMR (CDC13) d: 1.25-1.36 (6H, m), 2.20-2.40 (1H, br.s), 2.85 (3H, s), 2.87 (3H, s) , 3.36 (1H, m), 3.54 (1H, m), 4.23 (1H, m), 4.38 (1H, m), 7.45, 7.46 (total 1H, each s), 7.65-7.82 (total 1H, each s) , 8.30, 8.55 (total 1H, each s) MS (TSP): 573 (M ++ H) Example 93 (SS, 5R, 6S) -2- [7- (N, N-dimethylsulfamoyl) imidazo [5, 1 -b] thiazol-2-yl] -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-ca (5-Methyl-2-oxo-l, 3-diocolen-4-yl) methyl rboxylate In the same manner as in Example 46, 38.1 mg of the title compound were obtained from 32.0 mg of (IS, 5R , 6S) -2- [7- (N, N-dimethylsulfamoyl) imidazo [5, 1-b] thiazol-2-yl] -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen -2-em-3-carboxylate sodium and 26.0 mg of (5-methyl-2-oxo-1,3-dioxolen-4-yl) methyl bromide. NMR (CDCI3) d: 1.29 (3H, d, J = 7.1 Hz), 1.37 (3H, d, J = 6.1 Hz), 2.22 (3H, s), 2.30 (1H, br.s), 2.07 (6H, s), 3.35 (1H, dd, Ji = 6.6 Hz, J2 = 2.8 Hz), 3.50 (1H, m), 4.26-4.33 (1H,), 4.37 (1H, dd, Jx = 9.6 Hz, J2 = 2.8 Hz ), 5.02, 5.10 (2H, ABq, J = 14.0 Hz), 8.10 (1H, s), 8.34 (1H, s) MS (TSP): 553 (M ++ H) Example 94 (SS, 5R, 6S) -2- [7- (N-N-dimethylsulfamoyl) imidazo [5, 1-b] thiazol-2-yl] -6-. { (IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 1- [(cyclohexylmethoxy) carbonyloxy] ethyl ester (a mixture of diastereomers) In the same manner as in example 46, 14.5 mg of the title compound was obtained from 32.0 mg of (1S, 5R, 6S) -2- [7- (N, N-dimethylsulfamoyl) imidazo [5, 1-b] thiazol-2-yl] -6 - ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate sodium and 45.0 mg 1- [(cyclohexylmethoxy) carbonyloxy] ethyl iodide NMR (CDC13) d: 0.95- 1.08 (2H, m), 1.15-1.30 (2H, m), 1.27 (3H, d, J = 7.4 Hz), 1.37, 1.39 (total 3H, each d, J = 5.5 Hz), 1.60-1.80 (9H, m), 2.87 (6H, s), 3.33 (1H, m), 3.45 (1H, m), 3.96 (1H, m), 4.02 (1H, d, J = 2.1 Hz ), 4.28 (1H, m), 4.36 (1H,), 6.93 (1H, m), 8.05, 8.06 (total 1H, each s), 8.54, 8.57 (total 1H, each s) MS (TSP): 625 ( M ++ H) Example 95 (1S, 5R, 6S) -2- [7- (N, N-dimethylsulfamoyl) imidazo [5, 1-b] thiazol-2-yl] -6- ((IR) -1 -hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 1- (cyclohexylmethoxycarbonyloxy) -n-propyl ester (a mixture of diastereomers) In the same manner as in Example 46, 32.8 mg of the compound of the title to give 31.5 mg of (1S, 5R, 6S) -2- [7- (N, N-dimethylsulfamoyl) imidazo [5, lb] _iazcl-2-yl] -6- ((IR) -1 sodium-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate and 45.0 mg 1- (cyclohexylmethoxycarbonyloxy) -n-propyl iodide. NMR (CDC13) d: 1.00, 1.08 (total 3H, each t, J = 7.4 Hz), 1.26-1.40 (7H, m), 1.45-1.65 (3H, m), 1.70-1.82 (3H, m), 1.85 -2.05 (6H, m), 2.88 (6H, s), 3.33 (1H, m), 3.45 (1H, m), 3.61 (1H, m), 4.27 (1H, m), 4.36 (1H, m), 4.65 (1H, m), 6.79, 6.81 (total 1H, each t, J = 5.7 Hz), 8.05, 8.06 (total 1H, each s), 8.55, 8.57 (total 1H, each s) MS (TSP): 625 (M + + H) Example 96 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methoxycarbonylimidazo [5, 1-b] thiazol-2-yl) -1- sodium methyl-l-carbapen-2-em-3-carboxylate a) (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methoxycarbonylimidazo [5, 1-b] thiazol-2-yl) -1-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl In the same manner as in Example la., 303 mg of (ΔS, 5R, 6S) - 6- ((IR) -1-hydroxyethyl) -2- (7-methoxycarbonylimidazo [5, 1-b] thiazol-2-yl) -1-methyl-l-carbapene-2-em-3-carboxylate from 4- nitrobenzyl from 467 mg of (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2-oxo-l-carbapenam-3-carboxylate of 4-nitrobenzyl and 729 mg of 2- (tri-n- butylstanyl) imidazo [5, 1-b] thiazole-7-carboxylic acid methyl ester.

NMR (CDCI3) d: 1.32 (3H, d, J = 7.3 Hz), 1.40 (3H, d, J = 7.6 Hz), 2.00-2.12 (1H, wide), 3.39 (1H, dd, J_. = 6.6 Hz , J2 = 2.9 Hz), 3.51 (1H, dq, Ji = 9.5 Hz, J2 = 7.3 HZ), 3.96 (3H, s), 4.29-4.37 (1H, m), 4.41 (1H, dd, Ji = 9.7 Hz , J2 = 2.9 Hz), 5.28 (1H, d, J = 13.7 Hz), 5.52 (1H, d, J = 13.7 Hz), 7.68 (2H, dm, J = 8.8 Hz), 8.02 (1H, s), 8.24 (2H, dm, J = 8.8 Hz), 8.44 (1H, s) b) (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methoxycarbonylimidazo [5,1] sodium β-thiazol-2-yl) -1-methyl-l-carbapen-2-em-3-carboxylate In the same manner as in Example 1-b), 188 mg of the title compound was obtained from of 303 mg of (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7 -me toxycarbonyl imidazo [5,1-b] thiazol-2-yl) -l-methyl -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl. NMR (D20) d: (HOD = 4.80 ppm): 1.21 (3H, d, J = 7.1 Hz), 1.32 (3H, d, J = 6.2 Hz), 3.50 (1H, dd, Ji = 6.0 Hz, J2 = 20.6 Hz), 3.58 (1H, qd, Ji = 7.1 Hz, J2 = 6.0 Hz), 4.28 (1H, p, J = 6.2 Hz), 4.34 (1H, dd, Ji = 9.2 Hz, J2 = 2.6 Hz), 7.87 (1H, s), 8.07 (1H, s) Example 97 (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- [7- (N-me toxy-N-methylsulfonyl) ) sodium imidazo [5, 1-b] thiazol-2-yl] -1-methyl-l-carbapen-2-em-3-carboxylate a) (1S, 5R, 6S) -6- ((IR) - 1-hydroxyethyl) -2- [7- (N-methoxy-N-methylsulfamoyl) imidazo [5, 1-b] thiazol-2-yl] -1-methyl-l-carbapen-2-em-3-carboxylate from 4-Nitrobenzyl Substantially in the same manner as in Example la), 160 mg of (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- [7- (N-methoxy) was obtained. N-methylsulfamoyl) imidazo [5, 1-b] thiazol-2-yl) -1-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl from 217 mg of (IS, 5R, 6S ) -6- ((IR) -1-Hydroxyethyl) -1-methyl-2-oxo-l-carbapenem-3-carboxylate of 4-nitrobenzyl and 292 mg of 7- (N-methoxy-N- methylsulfamoyl) -2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole. NMR (CDC1) d: 1.31 (3H, d, J = 7.2 Hz), 1.39 (3H, d, J = 6.2 Hz), 3.05 (3H, s), 3.35-3.45 (1H, m), 3.37-3.44 ( 1H, m), 3.82 (1H, s), 4.25-4.35 (1H, m), 4.42 (1H, dd, i = 9.8 Hz, J2 = 2.9 Hz), 5.30 (1H, d, J = 13.7 Hz), 5.52 (1H, d, J = 13.7 Hz), 7.68 (2H, d, J = 8.9 Hz), 8.09 (1H, s), 8.24 (2H, d, J = 8.9 Hz), 8.43 (1H, s). b) (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- [7- (N-methoxy-N-methylsulfamoyl) imidazo [5, 1-b] thiazol-2-yl] Sodium-1-methyl-l-carbapen-2-em-3-carboxylate The title compound (98 mg) was obtained from 160 mg of (IS, 5R, 6S) -6- ((IR) -1 -hydroxyethyl) -2- [7- (-N-methoxy-N-methylsulfamoyl) imidazo [5, 1-b] thiazol-2-yl) -1-methyl-l-carbapen-2-em-3-carboxylate of nitrobenzyl in substantially the same manner as in Example 1-b), except that the purification was performed using Cosmosil 40C18-PREP (10% aqueous methanol) NMR (D30) d: (HOD = 4.80 ppm), 1.25 (3? , d, J = 7.3 Hz), 1.31 (3H, d, J = 6.4 Hz), 2.95 (3H, s), 3.52 (1H, dd, Jx = 6.8 Hz, J2 = 2.4 Hz), 3.58-3.68 (1H , s), 3.78 (3H, s), 4.24-4.33 (2H, m), 8.10 (1H, s), 8.28 (1H, s) Example 98 (SS, 5R, 6S) -6- ((IR) - 1-hydroxyethyl) -l-methyl-2- (7-trifluoroacetylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid sodium a) (1S, 5R, 6S ) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-trifluoroacetylimide) [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl Substantially in the same manner as in Example la), 68 mg of (IS, 5R, 6S) -6- ((1?) -1-hydroxyethyl) -1-methyl-2- (7-trifluoroacetylimidazo [5, 1-b] t? Azol-2-yl) -1-carbapen-2- 4-nitrobenzyl em-3-carboxylate from 109 mg of (IR, 3R, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2-oxo-l 4-nitrobenzylcarbapenam-3-carboxylate and 136 mg of 7-trifluoroacetyl-2- (tri-n-butylstannyl) imicazo [5, 1-b] thiazole. NMR (CDCl 3) d: 1.32 (3H, d, J = 7.3 Hz, 1.40 (3H, d, J = 6. 2 Hz), 3.38-3.42 (1H, m), 3.50-3.60 (1H, m), 4.30-4.40 (1H, m), 4.43 (1H, dd, Jx = 9.7 Hz, J2 = 2.8 Hz), 5.23- 5.38 (1H, m), 5.53 (1H, d, J = 13.5 Hz), 7.70 (2H, _, J = 8.9 Hz), 8.13 (1H, s), 8.25 (2H, d, J = 8.9 Hz), 8.53 (1H, s) b) (1S, 5R, 6S) -6- ((IR) -1-hydroxyl) -l- Sodium methyl-2- (7-trifluoroacetylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate The title compound (20.6 mg) was obtained from 68 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-trifluoroacetylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2 4-nitrobenzyl-3-carboxylate in substantially the same manner as in Example 1-b), except that the purification was carried out using Cosmosil 40C18-PREP (10% aqueous methanol) NMR (D30) d: (HOD = 4.80 ppm): 1.23 (3H, d, J = 7.1 Hz), 1.32 (3H, d, J = 6.4 Hz), 3.53 (1H, dd, J: = 6.1 Hz, J2 = 2.8 Hz), 3.60-3.70 (1H, m), 4.25-4.40 (2H,), 8.12 (1H, s), 8.26 (1H, s) Example 99 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l -methyl-2- (7-sulfamoylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid sodium a) (1S, 5R, 6S) -2- (7 -t-butyldimethylsilylsulfamoylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1 -hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl Substantially in the same manner as in Example la), 197 mg of (IS, 5R, 6S) -2- were obtained (7-t-Butyldimethylsilylsulfamoylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate from 4- Nitrobenzyl from 217 mg of (IR, 3R, 5R, 6S) -6- ((IR) -1- hydroxyethyl) -l-methyl-2-oxo-l-carbapenam-3-carboxylate of 4-nitrobenzyl and of 303 mg of 7- (t-butyldimethylsilylsulfamoyl) -2- (tri-n-butylstannyl) -imidazo [5, 1-b] thiazole. NMR (CDC13) d: 0.24 (3H, s), 0.26 (3H, s), 0.93 (9H, s), 1.31 (3H, d, J = 7.1 Hz), 1.41 (3H, d, J = 6.3 Hz) , 3.40 (1H, dd, Ji = 6.3 Hz, J2 = 2.7 Hz), 3.45-3.52 (1H,), 4.30-4.36 (1H, m), 4.40 (1H, dd, Ji = 9.7 Hz, J2 = 2.7 Hz ), 4.57 (1H, s), 5.30 (1H, d, J = 13.7 Hz), 5.55 (1H, d, J = 13.7 Hz), 7.70 (2H, d, J = 8.3 Hz), 8.03 (1H, s ), 8.26 (2H, d, J = 8.3 Hz), 8.47 (1H, s) b) (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7 Sulfamoylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate sodium Acetic acid (0.26 ml) and 1.5 ml of tetra-n-butylammonium fluoride 1M / THF with ice cooling to a solution of 197 mg of (SS, 5R, 6S) -2- (7-butyldimethylsilylsulfamoylimidazo [5, 1-b] thiazol-2-yl) -6- ((R) -1-hydroxyethyl ) -l-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl in 6 ml of THF. The solution was applied at room temperature for 3 hours. The reaction mixture was added to an aqueous solution of sodium hydrogencarbonate, followed by extraction with dichloromethane. The organic layer was dried in anhydrous magnesium sulfate. The solvent was removed by distillation. The residue was purified by column chromatography on silica gel (dichloromethane: methanol = 10: 1) to give a crude product of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -1-methyl -2- (7-sulfamoylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 4-nitrobenzyl ester. The crude product was dissolved in 5 ml of THF and 5 ml of a 1/15 M sodium phosphate buffer (pH 6.6). 10% Pd-C (50 mg) was added. The atmosphere in the reactor was replaced with hydrogen. The system was stirred at room temperature for 30 minutes. The catalyst was removed by filtration through Celite, followed by washing with water. The filtrate was adjusted to pH 7.0 by the addition of an aqueous sodium hydrogencarbonate solution and washed with ethyl acetate. Purification was then carried out using Cosmosil 40C18-PREP (30% aqueous methanol) and Dowex 50 (sodium form) in this order to provide 40.7 mg of the title compound. NMR (D30) d: (HOD = 4.80 ppm): 1.26 (3H, d, J = 7.4 Hz), 1.32 (3H, d, J = 6.3 Hz), 3.53 (1H, dd, J = 6.0 Hz, J2 = 2.7 Hz), 3.56-3.68 (1H, m), 4.25-4.35 (2H, m), 8.04 (1H, s), 8.23 (1H, s) Example 100 (ÍS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- [7- (2- (E) -methoxycarbonylvinyl) sodium imidazo [5, 1-b] thiazol-2-yl] -1-methyl-l-carbapen-2-em-3-carboxylate a) (SS, 5R, 6S) -6- ((IR) -1 -hydroxyethyl) -2- [7- (2- (E) -methoxycarbonylvinyl) imidazo [5, 1-b] thiazol-2-yl] -1-methyl-l-carbapen-2-em-3-carboxylate of 4 -nitrobenzyl and (SS, 5R, 6S) -6- ((lR) -l-hydroxyethyl) -2- [7- (2- (Z) -methoxycarbonylvinyl) imidazo [5, 1-b] thiazol-2-yl ] -1-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl In the same manner as in Example la), 88 mg of (ΔS, 5R, 6S) -6- ((IR ) -1-hydroxyethyl) -2- [7- (2- (E) -methoxycarbonylvinyl) imidazo [5, 1-b] thiazol-2-yl] -1-methyl-l-carbapenam-2-em-3 4-Nitrobenzyl carboxylate and 28 mg of (1S, 5R, 6S) -6- ((lR) -l-hydroxyethyl) -2- [7- (2- (Z) -methoxycarbonylvinyl) imidazo [5, 1-b ] thiazol-2-yl] -1-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl from 320 mg of (IR, 3R, 5R, 6S) -6- ((IR) - 1-hydroxyethyl) -l-met il-2-oxo-l-carbapenam-3-carboxylate of 4-nitrobenzyl and 400 mg of 7- (2-methoxycarbonylvinyl) -2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole (a mixture of geometric isomers). (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- [7- (2- (E) -methoxycarbonylvinyl) imidazo [5, 1-b] thiazol-2-yl] -1 -methyl-l-carbapen-2-em-3-carboxylic acid 4-nitrobenzyl NMR (CDC13) d: 1.32 (3H, d, J = 7.3 Hz), 1.41 (3H, d, J = 6.3 Hz), 3.39 ( 1H, dd, Ji = 6.3 Hz, J2 = 2.7 Hz), 3.51 (1H, m), 3.81 (3H, s), 4.33 (1H, m), 4.40 (1H, dd, J_ = 9.7 Hz, J- = 2.9 Hz), 5.29 (1H, d, J = 13.6 Hz), 5.53 (1H, d, J = 13.6 Hz), 6.18 (1H, d, J = 15.9 Hz), 7.69 (2H, d, J = 8.7 Hz ), 7.73 (1H, d, J = 15.9 Hz), 8.06 (1H, s), 8.25 (2H, d, J = 8.7 Hz), 8.36 (1H, s) (SS, 5R, 6S) -6- ( (IR) -1-hydroxyethyl) -2- [7- (2- (Z) -methoxycarbonylvinyl) imidazo [5, 1-b] thiazol-2-yl] -1-methyl-l-carbapen-2-em- 3-carboxylic acid 4-nitrobenzyl NMR (CDC13) d: 1.31 (3H, d, J = 7.3 Hz), 1.40 (3H, d, J = 6.3 Hz), 3.37 (1H, dd, Ji = 6.3 Hz, J2 = 2.7 Hz), 3.58 (1H, m), 3.81 (3H, s), 4.32 (1H, m), 4.38 (1H, dd, Ji = 9.7 Hz, J2 = 2.9 Hz), 5.27 (1H, d, J = 13.6 Hz), 5.52 (1H, d, J = 13.6 Hz), 5.84 (1H, d, J = 12.4 Hz), 7.12 (1H, d, J = 12.4 Hz), 7. 67 (2H, d, J = 8.8 Hz), 8.07 (1H, s), 8.24 (2H, d, J = 8.8 Hz), 8.42 (1H, s) b) (SS, 5R, 6S) -6- ( (IR) -1-hydroxyethyl) -2- [7- (2- (E) -methoxycarbonylvinyl) imidazo [5, 1-b] thiazol-2-yl] -1-methyl-l-carbapen-2-em- 3-sodium carboxylate In the same manner as in Example 1-b), 37 mg of the title compound was obtained from (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l -methyl-2- [7- (2- (E) -methoxycarbonylvinyl) imidazo [5, 1-b] thiazol-2-yl] -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl NMR (D20) ) d: (HOD = 4.80 ppm): 1.25 (3H, d, J = 7.3 Hz), 1.35 (3H, d, J = 6.3 Hz), 3.52 (1H, dd, J: = 6.3 Hz, J2 = 2.4 Hz), 3.60 (1H, m), 3.81 (3H, s), 4.30 (1H, m), 4.33 (1H, dd, Jx = 9.5 Hz, J2 = 2.4 Hz), 5.85 (1H, d, J = 15.8 Hz), 7.51 (1H, d, J = 15.8 Hz), 7.92 (1H, s), 8.11 (1H, s) Example 101 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- [7- (2- (Z) -methoxycarbonylvinyl) imidazo [5, 1-b] thiazol-2-yl] -1 sodium methyl-l-carbapen-2-em-3-carboxylate In the same manner as in Example 1-b), 9.8 of the title compound was obtained from (SS, 5R, 6S) -6- ( (IR) -1-hydroxyethyl) -2- [7- (2- (Z) -methoxycarbonylvinyl) imidazo [5, 1-b] thiazol-2-yl] -l-methyl-l-carbapen-2-em- 4-Nitrobenzyl 3-carboxylate. NMR (D20) d: (HOD = 4.80 ppm): 1.25 (3H, d, J = 7.3 Hz), 1. 33 (3H, d, J = 6.3 Hz), 3.52 (1H, dd, Ji = 6.3 Hz, J2 = 2.4 Hz), 3.57 (1H, m), 3.87 (3H, s), 4.29 (1H, m), 4.32 (1H, dd, Ji = 9.3 Hz, J2 = 2.4 Hz), 5.88 (1H, d, J = 12.5 Hz), 7.02 (1H, d, J = 12.5 Hz), 7.97 (1H, s), 8.18 ( 1H, s) Example 102 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- [7- (thiazol-4-yl) imidazo [5, 1-b] sodium thiazol-2-yl] -carbapen-2-em-3-carboxylate a) (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- [7- ( thiazol-4-yl) imidazo [5, 1-b] thiazol-2-yl] -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl In the same manner as in Example la), 17 were obtained mg (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- [7- (thiazol-4-yl) imidazo [5, 1-b] thiazole-2- il] -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl from 224 mg of (IR, 3R, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl- 2-Oxo-l-carbapenam-3-carboxylate of 4-nitrobenzyl and 289 mg of 7- (thiazol-4-yl) -2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole. NMR (CDCI3) d: 1.33 (3H, d, J = 7.4 Hz), 1.41 (3H, d, J = 6. 1 Hz), 3.38 (1H, dd, Ji = 6.5 Hz, J2 = 2.8 Hz), 3.50 (1H, m), 4.32 (1H,), 4.36 (1H, dd, J_. = 9.4 Hz, J2 = 2.8 Hz ), 5.28 (1H, d, J = 13.5 Hz), 5.53 (1H, d, J = 13.5 Hz), 7.65 (2H, d, J = 2.1 Hz), 7.68 (2H, d, J = 8.8 Hz), 8.07 (1H, s), 8. 24 (2H, d, J = 8.8 Hz), 8.48 (1H, s), 8.88 (2H, d, J = 2.1 Hz) MS (FAB +): 552 (M + + H) b) (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- [7- (thiazol-4-yl ) sodium imidazo [5, 1-b] thiazol-2-yl] -l-carbapen-2-em-3-carboxylate In the same manner as in Example 1-b), 7.0 mg of the title compound was obtained from 16.5 mg of (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- [7- (thiazol-4-yl) imidazo [5, 1-b] thiazol-2-yl] -l-carbapen-2-em-3-carboxylic acid 4-nitrobenzyl NMR (D20) d: (HOD = 4.80 ppm): 1.20 (3H, t, J = 6.9 Hz), 1. 34 (3H, d, J = 6.4 Hz), 3.45 (1H,), 3.48 (1H, m), 4.26 (1H, m), 4.30 (1H, m), 7.35 (1H, s), 7.76 (1H, s), 7.91 (1H, s), 8.91 (1H, s) Example 103 (SS, 5R, 6S) -2- (7-hydroxyacetyl-5-methylimidazo [5, 1-b] thiazol-2-yl) - 6- ((R) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylic acid sodium a) (SS, 5R, 6S) -2- (7-t-butyldimethylsilyloxyacetyl-5-) methylimidazo [5, 1-b] thiazol-2-yl) -6- ((R) -1-hydroxyethyl) -1-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl In the same way in Example la), 193 mg of (SS, 5R, 6S) -2- (7-t-butyldimethylsilyloxyacetyl-5-methylimidazo [5, 1-b] thiazol-2-yl) -6- (( R) -1-hydroxyethyl) -1-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl from 204 mg of (IR, 3R, 5R, 6S) -6- ((R) - 1-hydroxyethyl) -1-methyl-2-oxo-l-carbapenam-3-carboxylate of 4-nitrobenzyl and 4.05 mg of 7-butylstannyl) imidazo [5, 1-b] tlazole NMR (CDC13) d: 1.05 (6H, s), 0.96 (9H, s), 1.30 (3H, d, J = 7.4 Hz), 1.40 (3H, d, J = 6.2 Hz), 2.64 (3H, s), 3.38 (1H, dd, Ji = 6.5 Hz, J2 = 2.8 Hz), 3.49 (1H, m), 4.31 (1H, m), 4.40 (1H, dd, Ji = 9.5 Hz, J2 = 2.8 Hz), 5.03 (2H, s), 5.27 (1H, d, J = 13.7 Hz), 5.53 (1H, d, J = 13.7 Hz), 7.68 (2H, d, J = 8.5 Hz), 8.24 ( 2H, d, J = 8.5 Hz), 8.37 (1H, s) b) (SS, 5R, 6S) -2- (7-hydroxyacetyl-5-methylimidazo [5, 1-b] thiazoV 2 -yl) -6 - ((R) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl In the same manner as in example 36-b), 122 mg of , 5R, 6S) -2- (7-hydroxyacetyl-5-methylimidazo [5, 1-b] thiazol-2-yl) -6- ((R) -1-hydroxyethyl) -l-methyl-1-carbapen- 4-Nitrobenzyl 2-ene-3-carboxylate from 193 mg of (SS, 5R, 6S) -2- (7-t-butyldimethylsilyloxyacetyl-5-methylimidazo [5, 1-b] thiazol-2-yl) -6- ((R) -1-hydroxyethyl) -1-methyl- l-carbapen-2-em-3-carboxylic acid 4-nitrobenzyl NMR (CDCl 3) d: 1.31 (3H, d, J = 7.2 Hz), 1.40 (3H, d, J =), 2.65 (3H, s), 3.39 (1H, dd, Ji = 6.4 Hz, J2 = 2.7 Hz), 3.52 (2H,), 4.33 (1H, m), 4.42 (1H, dd, Ji = 9.6 Hz, J2 = 2.7 Hz), 4.85 ( 2H, s), 5.28 (1H, d, J = 13.7 Hz), 5.54 (1H, d, J = 13.7 Hz), 7.68 (2H, d, J = 8.5 Hz), 8.24 (2H, d, J = 8.5 Hz), 8.36 (1H, s) c) (1S, 5R, 6S) -2- (7-hydroxyacetyl-5-methylimidazo [5, 1-b] thiazol-2-yl) -6- ((R) - Sodium 1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate In the same manner as in Example 1-b), 75.9 mg of the title compound were obtained from 122 mg of ( 1S, 5R, 6S) -2- (7-hydroxyacetyl-5-methylimidazo [5, 1-b] thiazol-2-yl) -6- ((R) -1-hydroxyethyl) -l-methyl-1-carbapen -2-em-3-carboxylate of 4-nitrobenzyl NMR (D20) d: (HOD = 4.80 ppm): 1.19 (3H, d, J = 7.2 Hz), 1.33 (3H, d, J = 6.3 Hz) , 2.48 (3H, s), 3.48 (1H, dd, Jx = 6.1 HZ, J2 = 2.5 Hz), 3.55 (1H, m), 4.30 (2H, m), 4.70 (2H, s), 7.73 (1H, s) Example 104 (5R, 6S) -6- ((R) -1-hydroxyethyl) -2- (7-methanesulfonyl-5-methylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen- Sodium 2-em-3-carboxylate a) (5R, 6S) -6- ((R) -1-hydroxyethyl) -2- (5-methyl-7-methylthioimidazo [5, 1-b] thiazole-2- il) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl In the same manner as in Example la), 866 mg of (5R, 6S) -6- ((R) -1-hydroxyethyl) were obtained ) -2- (5-methyl-7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl from 1.04 mg of (3R, 5R, 6S) -6- ((R) -1-hydroxyethyl) -2-oxo-l-carbapenam-3-carboxylate of 4-nitrobenzyl and 1.70 mg of 5-methyl-7-methylthio-2- (tri-n -butylstannyl) imidazo [5, 1-b] thiazole. NMR (CDC13) d: 1.40 (3H, d, J = 6.3 Hz), 2.40 (3H, s), 2.58 (3H, s), 3.33 (3H, m), 4.31 (2H, m), 5.31 (1H, d, J = 14.0 Hz), 5.56 (1H, d, J = 14.0 Hz), 7.70 (2H, d, J = 8.9 Hz), 8.04 (1H, s), 8.25 (2H, d, J = 8.9 Hz) b) (5R, 6S) -6- ((R) -1-hydroxyethyl) -2- (7-methanesulfonyl-5-methylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2- 4-Nitrobenzyl em-3-carboxylate A reaction is carried out in the same manner as in example 44-b), except that 279 mg of (5R, 6S) -6- ((R) -1-hydroxyethyl) were used) -2- (5-Methyl-7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl as starting compound. The product of the reaction was purified by column chromatography on silica gel (dichloromethane: methanol = 20: 1 to 10: 1). Of the two major components, the fraction that had been eluted earlier was concentrated under reduced pressure to provide 91 mg of (5R, 6S) -6- ((R) -1-hydroxyethyl) -2- (7-methanesulfonyl-5 - methylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl. NMR (CDCI3) d: 1.40 (3H, d, J = 6.4 Hz), 2.63 (3H, s), 3.18 (3H, s), 3.35 (3H, m), 4.34 (2H, m), 5.32 (1H, d, J = 13.6 Hz), 5.56 (1H, d, J = 13.6 Hz), 7.70 (2H, d, J = 9.1 Hz), 8. 17 (1H, s), 8.25 (2H, d, J = 9.1 Hz) c) (5R, 6S) -6- ((R) -1-hydroxyethyl) -2- (7-methanesulfonyl-5-methylimidazo [ Sodium 5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate In the same manner as in Example 1-b), 45.6 mg of the title compound was obtained from 91 mg of (5R, 6S) -6- ((R) -1-hydroxyethyl) -2- (7-methanesulfonyl-5-methylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2 -em-3-carboxylate of 4-nitrobenzyl. NMR (D20) d: (HOD = 4.80 ppm): 1.31 (3H, d, J = 6.3 Hz), 2. 54 (3H, s), 3.24 (3H, s), 3.26 (2H,), 3.51 (2H, m), 4.26 (2H,), 7.66 (1H, s) Example 105 (5R, 6S) -6- ((R) -1-hydroxyethyl) -2- (7-methansulfinyl-5-methylimidazo [5, 1-b] thiazole- 2-yl) -l-carbapen-2-em-3-carboxylic acid sodium (a mixture of diastereomers) a) (5R, 6S) -6- ((R) -1-hydroxyethyl) -2- (7-methanesulfinyl -5-Methylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl (a mixture of diastereomers) Of the two main components, the fraction that had been eluted later in column chromatography on silica gel in example 104-b), was concentrated under reduced pressure to provide 136 mg of (5R, 6S) -6- ((R) -1-hydroxyethyl) -2- ( 7-Methansulfinium-5-methy1imidazo [5,1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl (a mixture of diastereomers) NMR (CDC1) d: 1.39 ( 3H, d, J = 6.2 Hz), 2.60 (3H, s), 2.94 (3H, s), 3.31 (3H,), 4.30 (2H, m), 5.29 (1H, d, J = 13.7 Hz), 5.53 (1H, d, J = 13.7 Hz), 7.68 (2H, d, J = 8.6 Hz), 8.10 (1H, m), 8.23 (2H, d, J = 8.6 Hz) b) (5R, 6S) -6- ((R) -1-hydroxyethyl) -2- (7-methanesulfinyl- Sodium 5- ethylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate (a mixture of diastereomers) In the same manner as in example 1-b), obtained 71.8 mg of the title compound from 136 mg of (5R, 6S) -6- ((R) -1-hydroxyethyl) -2- (7-methansulfinyl-5-methylimidazo [5, 1-b] thiazole- 2-yl) -l-carbapen-2-em-3-carboxylic acid 4-nitrobenzyl ester (a mixture of diastereomers) NMR (D20) d: (HOD = 4.80 ppm): 1.31 (3H, d, J = 6.5 Hz) , 2.57 (3H, s), 3.05 (3H, s), 3.31 (2H, m), 3.52 (1H, m), 4.26 (2H, m), 7.74 (1H, s) Example 106 (5R, 6S) -2- (7-hydroxyacetyl-5-methylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) Sodium-1-hydroxy-ethyl) -l-carbapen-2-em-3-carboxylate a) (5R, 6S) -2- (7-t-butyldimethylsilyloxyacetyl-5-methylimidazo [5, 1-b] thiazole- 2-yl) -6- ((IR) -1-hydroxyethyl) -1-carbapen-2-em-3-carboxylate of 4-nitrobenzyl In the same manner as in Example la), 190 mg of (5R , 6S) -2- (7-t-Butyldimethylsilyloxyacetyl-5-methylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -1-carbapen-2-em- 4-Nitrobenzyl 3-carboxylate from 196 mg of (3R, 5R, 6S) -6- ((R) -1-hydroxyethyl) -2-oxo-l-carbapenam-3-carboxylate of 4-nitrobenzyl and 405 mg of 7-t-butyldimethylsilyloxyacetyl-5-methyl-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole. NMR (CDC13) d: 0.15 (6H, s), 0.96 (9H, s), 1.40 (3H, d, J = 6.1 Hz), 2.63 (3H, s), 3.35 (3H, m), 4.34 (2H, m), 5.03 ((2H, s), 5.31 (1H, d, J = 13.5 Hz), 5.55 ((1H, d, J = 13.5 Hz), 7.69 (2H, d, J = 8.3 Hz), 8.24 ( (2H, d, J = 8.3 Hz), 8.28 (1H, s) b) (5R, 6S) -2- (7-hydroxyacetyl-5-methylimidazo [5, 1-b] thiazol-2-yl) -6 - ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl In the same manner as in example 36-b), 75.9 mg of (5R, 6S) - 2- (7-hydroxyacetyl-5-methylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate from 4- Nitrobenzyl from 190 mg of (5R, 6S) -2- (7-t-butyldimethylsilyloxyacetyl-5-methylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylic acid 4-nitrobenzyl, NMR (CDCI3) d: 1.40 (3H, d, J = 6.3 Hz), 2.65 (3H, s), 3.35 (3H, m), 3.57 (1H, t, J = 5.0 Hz), 4.35 (2H,), 4.85 (2H, d, J = 5.0 Hz), 5.33 (1H, d, J = 13.7 Hz), 5.56 (1H, d, J = 13.7 Hz), 7.70 (2H, d, J = 8.5 Hz), 8.25 (1H, s), 8.25 (2H, d, J = 8. 5 Hz) c) (5R, 6S) -2- (7-hydroxyacetyl-5-methylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-carbapen Sodium 2-em-3-carboxylate In the same manner as in example 1-b), 34.0 mg of the title compound was obtained from 75.9 mg of (5R, 6S) -2- (7-hydroxyacetyl- 5-Methylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl.

NMR (D20) d: (HOD = 4.80 ppm): 1.33 (3H, d, J = 6.3-Hz), 2.41 (3H, s), 3.16 (2H, m), 3.49 (1H, dd, Ji = 5.6 Hz , J2 = 2.5 Hz), 4.23 (2H, m), 4.68 (2H, s), 7.52 (1H, s) Example 107 (SS, 5R, 6S) -6- ((R) -1-hydroxyethyl) -2 - (7-methanesulfonyl-5-methylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate of pivaloyloxymethyl In the same manner as in example 2, 26.5 mg of the title compound were obtained from 30.2 mg of (IS, 5R, 6S) -6- ((R) -1-hydroxyethyl) -2- (7-methanesulfonyl-5-methylimidazo [5, 1-b ] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate sodium.

NMR (CDCI3) d: 1.21 (9H, s), 1.27 (3H, t, J = 7.1 Hz), 1.37 (3H, d, J = 6.3 Hz), 2.68 (3H, s), 3.20 (3H, s) , 3.34 (1H, dd, Ji = 6.6 Hz, Jr = 2.8 Hz), 3.45 (1H, m), 4.28 (1H, m), 4.36 (1H, dd, Ji = 9.9 Hz, J2 = 2.8 Hz), 5.36 (1H, d, J = 5.45 Hz), 6.00 (1H, d, J = 5.5 Hz), 8.29 (1H, s '' Example 108 (SS, 5R, 6S) -6- ((R) -1-hydroxyethyl ) -2- (7-methanesulfonyl) -noacetyl-imidazo [5, 1-b] thiazol-2-yl) -1-methyl-l-carbapen-2-em-3-carboxylic acid sodium a) (1S, 5R, 6S) -6- ((R) -1-hydroxyethyl) -2- (7-methanesulfonylaminoacetylimidazo [5, 1-b] thiazol-2-yl) -1-methyl-l-carbapen-2-em- 3-Nitrobenzyl 3-carboxylate In the same manner as in Example la), 106 mg of (SS, 5R, 6S) -6- ((R) -1-hydroxyethyl) -2- (7-methanesulfonylaminoacetylimidazo [ 5, 1-b] thiazol-2-yl) -1-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl from 159 mg of (IR, 3R, 5R, 6S) -6- ((R) -1-hydroxyethyl) -l-methyl-2-oxo-l-carbapenam-3-carboxylate of 4-nitrobenzyl and 264 mg of 7-methanesulfonylaminoacetyl-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole. NMR (CDCI3) d: 1.31 (3H, d, J = 7.1 Hz), 1.40 (3H, d, J = 6.3 Hz), 3.01 (3H, s), 3.40 (1H, dd, J: = 6.5 Hz, J2 = 2.9 Hz), 3.52 (1H,), 4.33 (1H, m), 4.43 (1H, dd, Ji = 9.7 Hz, J2 = 2.9 Hz), 4.69 (2H, d, J = 5.2 Hz), 5.29 (1H , d, J = 13.6 Hz), 5.38 (1H, br), 5.53 (1H, d, J = 13.6 Hz), 7.68 (2H, d, J = 8.8 Hz), 8.01 (1H, s), 8.25 (2H , d, J = 8.8 Hz), 8.49 (1H, s) b) (SS, 5R, 6S) -6- ((R) -1-hydroxyethyl) -2- (7-methanesulfonylaminoacetylimidazo [5, 1-b] sodium thiazol-2-yl) -1-methyl-l-carbapen-2-em-3-carboxylate In the same manner as in Example 1-b), 65.0 mg of the title compound was obtained from 106 mg of (1S, 5R, 6S) - 6- ((R) -1-hydroxyethyl) -2- (7-methanesulfonylaminoacetylimidazo [5, 1-b] thiazol-2-yl) -1-methyl-1-carbapen-2 -em-3-carboxylate of 4-nitrobenzyl. NMR (D20) d: (HOD = 4.80 ppm): 1.24 (3H, d, J = 6.9 Hz), 1. 35 (3H, d, J = 6.3 Hz), 3.19 ((3H, s), 3.55 (2H, m), 4.32 (2H,), 4.59 (2H, s), 7.96 (1H, s), 8.11 (1H, s) Example 109 (1S, 5R, 6S) -6- ((R) -1-hydroxyethyl) -l-methyl -2- (5-Methyl-7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate sodium In the same manner as in Example 1-b) , They were obtained 24. 3 mg of the title compound from 42.9 mg of (IS, 5R, 6S) -6- ((R) -1-hydroxyethyl) -l-methyl-2- (5-methyl-7-methylthioimidazo [5,1] -b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 4-nitrobenzyl NMR (D20) d: (HOD = 4.80 ppm): 1.24 (3H, d, J = 6.9 Hz), 1. 33 ((3H, d, J = 5.9 Hz), 2.33 (3H, s), 2.49 (3H, s9, 3.54 (2H, m), 4.29 (2H, m), 7.70 (1H, s) Example 110 (ÍS , 5R, 6S) -6- ((R) -1-hydroxyethyl) -2- [7- (methanesulfonylaminomethyl) imidazo [5, 1-b] thiazol-2-yl] -1-methyl-l-carbapen-2 sodium a-3-carboxylate a) (1S, 5R, 6S) -6- ((R) -1-hydroxyethyl) -2- [7- (ethanesulfonylaminomethyl) imidazo [5, lb] thiazol-2-yl] -1-methy1-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl In the same manner as in Example la), 69.4 mg of (IS, 5R, 6S) -6- ((R) were obtained -1-hydroxyethyl) -2- [7-methanesulfonylaminomethyl] imidazo [5, 1-b] thiazol-2-yl) -1-met? Ll-carbapen-2-em-3-carboxylate of 4-nitrobenzyl eb a yellowish-orange oil from 124 mg of (IR, 3R, 5R, 6S) -6- ((R) -1-hydroxyethyl) -l-methyl-2-oxo-l-carbapenam-3-carboxylate from 4-Nitrobenzyl and 196 mg of 7-methanesulfonylaminomethyl-2- (tri-n-butylstannyl) -imidazo [5, 1-b] thiazole. NMR (CDC13) d: 1.30 (3H, d, J = 7.3 Hz), 1.39 (3H, d, J = 6.3 Hz), 2.91 (total 3H, each s), 3.35-3.40 (2H, m), 4.25- 4.45 (4H, m), 5.15 (1H, br.t), 5.27 (1H, d, J = 13.5 Hz), 5.52 (1H, d, J = 13.5 Hz), 6.87 (1 / 5H, d, J = 4.2 Hz), 7.40 (1 / 5H, d, J = 4.2 Hz), 7.68 (2H, d, J = 8.8 Hz), 7.98 (4 / 5H, s), 8.24 (2H, d, J = 8.8 Hz) , 8.32 (4 / 5H, s) MS (TSP): 576 (M + + H) b) (1S, 5R, 6S) -6- ((R) -1-hydroxyethyl) -2- [7- (methanesulfonylaminomethyl) ) sodium imidazo [5, 1-b] thiazol-2-yl] -1-methyl-l-carbapen-2-em-3-carboxylate • The title compound (18.2 mg) was obtained in the form of colored flocs light yellow in the same manner as in Example 1-b), except that 68 mg of (1S, 5R, 6S) -6- ((R) -l-hydroxyethyl) -2- [7- (methanesulfonylaminomethyl) were employed Imidazo [5, 1-b] thiazol-2-yl] -1-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl as the starting compound and the purification was carried out in column chromatography on Cosmosil 40C18- PREP. NMR (D20) d: (HOD = 4.80 ppm): 1.25 (3H, d, J = 7.4 Hz), 1.32 (3H, d, J = 6.3 Hz), 2.99 (3H, s), 3.49-3.62 (2H, m), 4.24-4.35 (2H, m), 4.34 (2H, s), 7.88 (1H, s), 8.09 (1H, s) MS (TSP): 485 (M ++ 2Na), 463 (M ++) Na), 441 (MXH) Example 111 (IS, 5R, 6S) -6- ((R) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazole-2- il) -l-carbapen-2-em-3-carboxylic acid sodium a) (SS, 5R, 6S) -6- ((R) -1-hydroxyethyl) -l-methyl-2- (7-methylthioi idazo [ 5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl In the same manner as in Example la), 14.0 mg of (ΔS, 5R, 6S were obtained ) -6- ((R) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate from 4-Nitrobenzyl from 11 * .7 mg of (IR, 3R, 5R, 6S) -6- ((R) -1-hydroxyethyl) -l-methyl-2-oxo-l-carbapenam-3-carboxylate of 4-Nitrobenzyl and 14.0 mg of 7-methylthio-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole NMR (CDC13) d: 1.31 (3H, d, J = 7.3 Hz), 1.40 (3H , d, J = 6 .3 Hz), 2.43 (3H, s), 3.35-3.40 (1H, s), 3.41-3.52 (1H, m), 4.30-4.42 (2H, m), 5.29 (1H, d, J = 13.7 Hz) , 5.53 (1H, d, J = 13.7 Hz), 7.67 (2H, d, J = 8.9 Hz), 8.02 (1H, s), 8.23 (2H, d, J = 8.9 Hz), 8.29 (1H, s) b) (1S, 5R, 6S) -6- ((R) -l-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen- Sodium 2-em-3-carboxylate The title compound (51 mg) was obtained from 103 mg of (IS, 5R, 6S) -6- ((R) -1-hydroxyethyl) -l-methyl-2 - (7-Methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl in the same manner as in example ab), except that the purification was carried out using Cosmosil 40C18-PREP 10% aqueous methanol). NMR (D20) d: (HOD = 4.80 ppm): 1.25 (3H, d, J = 7.2 Hz), 1.32 (3H, d, J = 6.4 Hz), 2.37 (3H, s), 3.50-3.60 (2H, m), 4.25-4.35 (2H, m), 7.90 (1H, s), 8.12 (1H, s) Example 112 (5R, 6S) -2- (7-dimethylaminosulfonylimidazo [5, 1-b] thiazole-2- il) -6- ((IR) -1-hydroxy-ethyl) -l-carbapen-2-em-3-carboxylic acid sodium a) (5R, 6S) -2- (7-dimethylaminosulfonylimidazo [5, 1-b] ] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl In the same manner as in Example la), 0.29 mg was obtained of (5R, 6S) -2- (7-dimethylaminosulfonylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxy-ethyl) -l-carbaper.-2-em- 4-Nitrobenzyl 3-carboxylate from 0.35 g of (3R, 5R, 6S) -6- ((R) -1-hydroxyethyl) -2-oxo-l-carbapenam-3-carboxylate of 4-nitrobenzyl and 0.52 g of 7-dimethylamino-sulfonyl-2- (tri-n-butylstannyl) imidazo [5, 1-b] -thiazole. NMR (DMSO-dd) d: 1.17 (3H, d, J = 6.0 Hz), 2.67 (6H, s), 3.40-3.55 (3H,). 3.95-4.05 (1H, m), 4.20-4.30 (1H, m), 5.18 (1H, d, J = 4.9 Hz), 5.42 (1H, d, J = 14.0 Hz), 5.57 (1H, d, J = 14.0 Hz), 7.75 (2H, d, J = 8.5 Hz), 8.24 (2H, d, J = 8.5 Hz), 8.42 (1H, s), 8.23 (1H, s) b) (5R, 6S) -2- (7-dimethylaminosulfonylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) Sodium 1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate The title compound (84 mg) was obtained from 150 mg of (5R, 6S) -2- (7-dimethylaminosulfonylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl in the same manner as in example 1-b) , except that the purification was carried out using Cosmosil 40C18-PREP (5% aqueous methanol). NMR (D20) d: (HOD = 4.80 ppm): 1.32 (3H, d, J = 6.2 Hz), 3.30-3.40 (2H, s), 3.50-3.55 (1H, m), 4.25-4.35 (2H, m ), 7.90 (1H, s), 8.23 (1H, s) Example 113 (5R, 6S) -2- (7-aminosulfonylimidazo [5, 1-b] thiazol-2-yl) -6- (IR) - Sodium 1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate a) (5R, 6S) -2- (7-t-butyldimethylsilylaminosulfonylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl In the same manner as in Example la), 0.36 g of (5R, 6S) -2- ( 7-t-Butyldimethylsilylaminosulfonylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxy-ethyl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl from of 0.28 g of (3R, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2-oxo-l-carbapenam.-2-em.-3-carboxylate of 4-nitrobenzyl and 0.44 g of 7-t-butyldimethylsilylaminosulfonyl -2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole. NMR (DMSO-de) d: 0.11 (6H, s), 0.86 (9H, s), 1.17 (3H, d, J = 6.0 Hz), 3.40-3.55 (3H, m), 3.95-4.05 (1H,) , 4.20-4.30 (1H,), 5.42 (1H, d, J = 14.0 Hz), 5.57 (1H, d, J = 14.0 Hz), 7.65 (1H, s), 7.76 (2H, d, J = 8.5 Hz), 8.23 ( 2H, d, J = 8.5 Hz), 8.35 (1H, s), 8.42 (1H, s) b) (5R, 6S) -2- (7-aminosulfonylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate sodium In the same manner as in example 99-b), 29 mg of the title compound was obtained from 83 mg of (5R, 6S) -2- (7-t-butyldimethylsilylaminosulfonylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em 3-Nitrobenzyl carboxylate. NMR (D-O) d: (HOD = 4.80 ppm): 1.32 (3H, d, J = 6.3 Hz), 3. 25-3.40 (2H, m), 3.50-3.55 (1H, m), 4.20-4.35 (2H,), 7.84 (1H, s), .8.19 (1H, s) Example 114 (1S, 5R, 6S) -6- ((R) -l-hydroxyethyl) -l-methyl-2- [7- ((E) -3 sodium -oxo-l-buten-1-yl) imidazo [5, 1-b] thiazol-2-yl] -l-carbapen-2-em-3-carboxylate a) (SS, 5R, 6S) -6 - ((R) -1-hydroxyethyl) -l-methyl-2- [7- ((E) -3-oxo-1-buten-l-yl) imidazo [5, 1-b] thiazol-2-yl ] -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl In the same manner as in Example la), 89 mg of (ΔS, 5R, 6S) -6- ((R) -1- were obtained hydroxyethyl) -l-methyl-2- [7- ((E) -3-oxo-1-buten-l-yl) imidazo [5, 1-b] thiazol-2-yl] -l-carbapen-2- 4-Nitrobenzyl em-3-carboxylate from 230 mg of 7 - ((E) -3-sxo-1-buten-1-yl) imidazo [5, 1-b] thiazole. NMR (CDC13) d: 1.33 (3H, d, J = 7.3 Hz), 1.41 (3H, d, J = 6.4 Hz), 2.38 (3H, s), 3.38 (1H, dd, J_ = 6.4 Hz, J2 = 2.7 Hz), 3.50 (1H, m), 4.33 (1H, m), 4.41 (lH, dd, Jx = 9.6 Hz, J2 = 2.7 Hz), 5.29 (1H, d, J = 13.6 Hz), 5.53 (1H , d, J = 13.6 Hz), 6.42 (1H, d, J = 16.1 Hz), 7.63 (1H, d, J = 16.1 Hz), 7.69 (2H, d, J = 9.0 Hz), 8.09 (1H, s ), 8.25 (2H, d, J = 9.0 Hz), 8.39 (1H, s) b) (SS, 5R, 6S) -6- ((R) -1-hydroxyethyl) -l-methyl-2- [7 - ((E) -3-oxo-1-buten-l-yl) imidazo [5, 1-b] thiazol-2-yl] -l-carbapen-2-em-3-carboxylate sodium In the same way than in the example lb? , 37 mg of the title compound were obtained from 85 mg of (1S, 5R, 6S) -6- ((R) -l-hydroxyethyl) -l-methyl-2- [7- ((E) -3 -oxo-l-buten-l-yl) imidazo [5, 1-b] thiazol-2-yl] -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl. NMR (D20) d: (HOD = 4.80 ppm): 1.08 (3H, d, J = 7.0 Hz), 1.20 (3H, d, J = 6.4 Hz), 2.21 (3H, s), 3.35 ( 1H, dd, Jx = 6.4 Hz, J2 = 2.7 Hz), 3.42 (1H, m), 4.15 (1H, m), 4.17 (1H, dd, Ji = 8.6 Hz, J2 = 2.2 Hz), 5.87 (1H, d, J = 15.8 Hz), 7.32 (1H, d, J = 15.8 Hz), 7.74 (1H, s), 7.96 (IH, s) Example 115 (SS, 5R, 6S) -2- (7- formyl-5-methylimidazo [5, 1-b] thiazol-2-yl) -6- ((R) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate from sodium a) (SS, 5R, 6S) -2- [7- (t-butyldimethylsilyloxy) methyl-5-methylimidazo [5, 1-b] thiazol-2-yl] -6- ((R) -1-hydroxyethyl] ) -1-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl In the same manner as in Example la), 313 mg of (ΔS, 5R, 6S) -2- [7- (t-butyldimethylsilyloxy) methyl-5-methylimidazo [5, 1-b] thiazol-2-yl) -6- ((R) -1-hydroxyethyl) -1-methyl-l-carbapen-2-em-3 4-Nitrobenzylcarboxylate from 730 mg of (IR, 3R, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -1-methyl-2-oxo-l-carbapenam-3-carboxylate 4-Nitrobenzyl and 1.2 mg of 7- (t-butyldimethylsilyloxy) methyl-5-methyl-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole. NMR (CDCI3) d: 0.13 (6H, sx2), 0.96 (9H, s), 1.31 (3H, d, J = 7.63 Hz), 1.39 (3H, d, J = 6.3 Hz), 2.55 (3H, s) , 3.35 (1H, dd, Ji = 6.6 Hz, J2 = 2.7 Hz), 3.45 (1H, m), 4.30 (1H, m), 4.35 (1H, dd, Ji = 9.5 Hz, J = 2.7 Hz), 4.81 (2H, s), 5.26 (1H, d, J = 13.6 Hz), 5.53 (1H, d, J = 13.6 Hz), 7.67 (2H, d, J = 8.7 Hz), 8.18 (1H, s), 8.23 (2H, d, J = 8.7 Hz) b) (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-hydroxymethyl-5-methylimidazo [5, 1-b] thiazole -2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl Acetic acid (0.28 ml) and 1.6 ml of a solution of tetrabutylammonium fluoride 1M / THF were added to 313 mg of (SS, 5R, 6S) -2- [7- (t-butyldimethylsilyloxy) methyl-5-methylimidazo [5, 1-b] thiazol-2-yl] -6- ((R) -1-hydroxyethyl) -1 -methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl. The mixture was stirred at room temperature for 3.5 hours. The reaction solution was adjusted to a pH of 7 by the addition of a saturated aqueous sodium hydrogencarbonate solution. The reaction solution was then extracted with ethyl acetate, washed with a saturated saline solution and dried over magnesium sulfate. The reaction solution was then concentrated under reduced pressure. The residue was purified by column chromatography to provide 279 mg of (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-hydroxymethyl-5-methylimidazo [5, 1-b] thiazol-2-yl) -1-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl. NMR (CDCI3) d: 1.28 (3H, d, J = 7.3 Hz), 1.37 (3H, d, J = 6.3 Hz), 2.56 (3H, s), 3.33 (1H, dd, J: = 6.3 Hz, J2 = 2.7 Hz), 3.44 (1H, s), 4.23 (1H, m), 4.32 (1H, dd, Ji = 9.5 Hz, J2 = 2.7 Hz), 4.64 (2H, s), 5.28 (1H, d, J = 13.8 Hz), 5.52 (1H, d, J = 13.7 Hz), 7.67 (2H, d, J = 9.0 Hz), 8.15 (1H, s), 8.23 (2H, d, J = 9.0 Hz) c) ( ÍS, 5R, 6S) -2- (7-formyl-5-methylimidazo [5, 1-b] thiazol-2-yl) -6- ((R) -1-hydroxyethyl) -l-methyl-l-carbapen -2-em-3-carboxylate of 4-nitrobenzyl It was dissolved (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-hydroxymethyl-5-methylimidazo [5, 1-b ] thiazol-2-yl) -1-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl (279 mg) in 30 ml of dichloromethane. Manganese dioxide (500 mg) was added to the solution. The mixture was stirred at room temperature for 14 hours. The reaction solution was filtered, the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to provide 89 mg of (1S, 5R, 6S) -2- (7-yl-5-methylimidazo [5, 1-b] thiazol-2-yl) - 6- ((R) -1-hydroxyethyl) -1-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl. NMR (CDCI3) d: 1.32 (3H, d, J = 7.3 Hz), 1.40 (3H, d, J = 6.3 Hz), 2.67 (3H, s), 3.38 (1H, dd, J .. = 6.3 Hz, J- = 2.9 Hz), 3.52 (1H, s), 4.33 (1H, m), 4.42 (1H, dd, Jx = 9.7 Hz, J: = 2.9 Hz), 5.27 (1H, d, J = 13.6 Hz) , 5.55 (1H, d, J = 13.6 Hz), 7.68 (2H, d, J = 9.0 Hz), 8.25 (2H, d, J = 9.0 Hz), 8.37 (1H, s), 9.85 (1H, s) d) (1S, 5R, 6S) -2- (7-formyl-5-methylimidazo [5, 1-b] thiazol-2-yl) -6- ((R) -1-hydroxyethyl) -l-methyl- sodium l-carbapen-2-em-3-carboxylate In the same manner as in example 1-b), 29 mg of the title compound was obtained from 89 mg of (1S, 5R, 6S) -2- (7-formyl-5-methylimidazo [5, 1-b] thiazol-2-yl) -6- ((R) -1-hydroxyethyl) -l-methyl-1-carbapen- 4-Nitrobenzyl 2-em-3-carboxylate. NMR (D20) d: (HOD = 4.80 ppm): 1.09 (3H, d, J = 7.1 Hz), 1.20 (3H, d, J = 6.3 Hz), 2.43 (3H, s), 3.37 (1H, dd, Ji = 6.3 Hz, J2 = 2.7 Hz), 3.49 (1H, m), 4.14 (1H, q, J = 6.3 Hz), 4.20 (1H, dd, Ji = 9.3 Hz, J- = 2.7 Hz), 7.75 ( 1H, s), 9.25 (1H, s) Example 116 (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) sodium l-carbapen-2-em-3-carboxylate a) (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methylthioimidazo [5, 1-b] thiazole-2 -l) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl In the same manner as in Example la), 1.79 mg of (5R, 6S) -6- ((IR) -1- were obtained. hydroxyethyl) -2- (7-methyltioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl from 2.30 g of (3R, 5R, 6S ) -6- ((IR) -1-hydroxyethyl) -2-oxo-l-carbapenam-3-carboxylate of 4-nitrobenzyl and 3.48 g of 7-methylthio-2- (tri-n-butylstannyl) imidazo [5, 1-] b] thiazole. NMR (CDC13) d: 1.40 (3H, d, J = 6.3 Hz), 2.42 (3H, s), 3.32 (3H, m), 4.32 (2H,), 5.32 (1H, d, J = 13.2 Hz), 5.55 (1H, d, J = 13.2 Hz), 7.69 (2H, d, J = 9.1 Hz), 8.01 (1H, s), 8.18 (1H, s), 8.25 (2H, d, J = 9.1 Hz) b ) (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate Sodium In the same manner as in Example 1-b), 54 mg of the title compound was obtained from 98 mg of (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- ( 7-Methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 4-nitrobenzyl ester. NMR (D20) d: (HOD = 4.65 ppm): 1.19 (3H, d, J = 6.3 Hz), 2.24 (3H, s), 3.16 (2H, m), 3.39 (1H, dd, Jx = 6.0 Hz, J2 = 29 Hz), 4.14 (2H, m), 7.60 (1H, s), 7.98 (1H, s) Example 117 (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7 sodium methansulfinylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate (a mixture of diastereomers) a) (5R, 6S) -6- ((IR) - 1-hydroxyethyl) -2- (7-methansulfinylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl (a mixture of diastereomers) A reaction was carried out in the same manner as in Example 44-b), except that 639 mg of (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methylthioimidazo [5, 1-b] was used. ] thiazoi-2-yl) -1-carbapen-2-em-3-carboxylate of 4-nitrobenzyl and 1.57 g of oxone as the starting compounds. The product of the reaction was purified by column chromatography on silica gel (dichloromethane: methanol = 20: 1 to 10: 1) to provide 267 mg of (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7- methansulfinylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl (a mixture of diastereomers) NMR (CDC1) d: 1.40 ( 3H, d, J = 6.1 Hz), 2.95, 2.95 (total 3H, each s), 3.33 (3H, m), 4.32 (2H,), 5.31 (1H, d, J = 13.6 Hz), 5.53 (1H, d, J = 13.6 Hz), 7'.68 (2H, d, J = 8.8 Hz), 8.06 (1H, s), 8.24 (2H, d, J = 8.8 Hz), 8.38 (1H, s) b) (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfinylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate from sodium (a mixture of diastereois) In the same manner as in Example 1-b), 16 mg of the title compound was obtained from 74 mg of (5R, 6S) -6- ((IR) -1- hydroxyethyl) -2- (7-methansulfinylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl (a mixture of diastereo mere). NMR (DMSO-dβ) d: 1.15 (3H, d, J = 6.4 Hz), 2.83 (3H, s), 3.12 (2H, m), 3.21 (1H, m), 3.91 (1H, m), 4.01 ( 1H, m), 5.05 (1H, s), 7.95 (1H, s), 8.23 (1H, s) Example 118 (5R, 6S) -2- [7- (N, N-dimethylaminosulfonylamino) acetylimidazo [5, 1-b ] thiazol-2-yl] -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylic acid sodium a) (5R, 6S) -2- [7- (N, N -dimethylaminosulfonylamino) acetylimidazo [5, 1-b] thiazol-2-yl] -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl In the same way as in Example la), 162 mg of (5R, 6S) -2- [7- (N, N-dimethylaminosulfonylamino) acetylimidazo [5, 1-b] thiazol-2-yl] -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl from 244 mg of (3R, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2-oxo-l-carbapenam-3-carboxylate of 4-nitrobenzyl and 222 mg of 7- (N, N-dimethylaminosulfonylamino ) acetyl-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole. NMR (DMSO-de) d: 1.18 (3H, d, J = 6.1 Hz), 2.67 (6H, s), 3.4-3.6 (3H,), 4.0-4.1 (1H, m), 4.2-4.35 (1H, m), 4.43 (2H, s), 5.44 (1H, d, J = 13.7 Hz), 5.58 (1H, d, J = 13.7 Hz), 7.77 (2H, d, J = 8.5 Hz), 8.25 (2H, d, J = 8.5 Hz), 8.37 (1H, s), 8.51 (1H, s) b) (5R, 6S) -2- [7- (N, N-dimethylaminosulfonylamino) acetylimidazo [5, 1-b] thiazole -2-yl] -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate sodium The title compound (49.5 mg9 was obtained from 160 mg of (5R, 6S ) -2- [7- (N, N-dimethylaminosulfonylamino) acetylimidazo [5, 1-b] thiazol-2-yl] -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3 4-Nitrobenzylcarbcylate in the same manner as in Example 1-b), except that the purification was carried out by column chromatography on Cosmosil 43C18-PREP (10% aqueous methanol). NMR (D20) d: (HOD = 4.80 ppm): 1.33 (3H, d, J = 6.3 Hz), 2.83 (6H, s), 3.2-3.4 (2H, m), 3.52 (1H, dd, Ji = 5.7 Hz, J2 = 2.3 Hz), 4.2-4.35 (2H, m), 4.4-4.6 (2H, ra), 7.81 (1H, s), 8.08 (1H, s) Example 119 (lS, 5R, 6S) -2 - [7- (N, N-dimethylaminosulfonylamino) cetylimidazo [5, 1-b] thiazol-2-yl] -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate sodium a) (1S, 5R, 6S) -2- [7- (N, N-dimethylaminosulfonylamino) acetylimidazo [5, 1-b] thiazol-2-yl] -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl In the same manner as in example la), 65.0 mg of 1S, 5R, 6S) -2- [7- (N, N- dimethylaminosulfonylamino) acetylimidazo [5, 1-b] thiazol-2-yl] -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl from 127 mg of (IR, 3R, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2-oxo-l-carbapenam-3-carboxylate of 4-nitrobenzyl and 222 mg of 7- (N, N-dimethylaminosulfonylamino) acetyl-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole. NMR (CDCI3) d: 1.31 (3H, d, J = 7.1 Hz), 1.40 (3H, d, J = 6.3 Hz), 2.83 (6H, s), 3.39 (1H, dd, J_ = 6.6 Hz, J- = 2.7 Hz), 3.45-3.6 (1H, m), 4.3-4.4 (1H, m), 4.43 (1H, dd, J_. = 9.5 Hz, J2 = 2.7 Hz), 4.57 (2H, d, J = 5.0 Hz), 5.28 (1H, d, J = 13.5 Hz), 5.42 (1H, br.s), 5.53 (1H, d, J = 13.5 Hz), 7.68 (2H, d, J = 8.5 Hz), 8.01 ( 1H, s), 8.24 (2H, d, J = 8.5 Hz), 8.48 (1H, s) b) (SS, 5R, 6S) -2- [7- (N, N-dimethylaminosulfonylamino) acetylimidazo [5, 1 -b] thiazol-2-yl] -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate sodium The title compound (34.4 mg) was from 65.0 mg of (1S, 5R, 6S) -2- [7- (N, N-dimethylaminosulfonylamino) acetylimidazo [5, 1-b] thiazol-2-yl] -6- ((IR) -1-hydroxyethyl) -l-carbapen -2-em-3-carboxylate of 4-nitrobenzyl in the same manner as in Example 1-b), except that the purification was carried out by column chromatography on Cosmosil 40C18-PREP (10% aqueous methanol). NMR (D20) d: (HOD = 4.80 ppm): 1.22 (3H, d, J = 6.9 Hz), 1.33 (3H, d, J = 6.3 Hz), 2.83 (6H, s), 3.45-3.6 (2H, m), 4.2-4.35 (2H, m), 4.43 (1H, d, J = 18.5 Hz), 4.54 (1H, d, J = 18.5 Hz), 7.90 (1H, s), 8.06 (1H, s) Example 120 (5R, 6S) -6- ((IR) -hydroxyethyl) -2- (5-methyl-7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3 sodium carboxylate In the same manner as in example 1-b), 43 mg of the title compound was obtained from 72 mg of (5R, 6S) -6- ((IR) -hydroxyethyl) -2- ( 5-Methyl-7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 4-nitrobenzyl ester. NMR (D20) d: (HOD = 4.65 ppm): 1.18 (3H, d, J = 5.9 Hz), 2.20 (3H, s), 2.36 (3H, s). 3.12 (2H, m), 3.37 (1H, m), 4.13 (2H, m), 7.44 (1H, s) Example 121 (IS, 5R, 6S) -2- (7-aminoacetylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1 -hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate sodium a) (SS, 5R, 6S) -6- ((IR) -hydroxyethyl) -l-methyl-2- [7- (4-Nitrobenzyloxycarbonylamino) acetylimidazo [5, 1-b] thiazol-2-yl] -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl In the same manner as in Example la), 468 mg were obtained of (SS, 5R, 6S) -6- ((IR) -hydroxyethyl) -l-methyl-2- [7- (4-nitrobenzyloxycarbonylamino) acetylimidazo [5, 1-b] thiazol-2-yl] -l- carbapen-2-em-3-carboxylate from 362 mg of (IR, 3R, 5R, 6S) -6- ((IR) -hydroxyethyl) -l-methyl-2-oxo-l-carbapenam-3-carboxylate of 4-nitrobenzyl and 714 mg of 7- (4-nitrobenzyloxycarbonylamino) acetyl-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole. NMR (DMSO-de) d: 1.21 (3H, d), 1.24 (3H, d), 3.42 (1H, dd), 3.74 (1H, m), 4.06 (1H,), 4.36 (1H, dd), 4.47 (2H, d), 5.16 (1H, d), 5.21 (2H, s), 5.48 (1H, d), 5.54 (1H, d), 7.65 (2H, d), 7.75 (2H, d), 8.21 (2H, d), 8.26 ( 2H, d), 8.34 (1H, s), 8. 60 (1H, s) b) (SS, 5R, 6S) -2- (7-aminoacetylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l- sodium methyl-l-carbapen-2-em-3-carboxylate The title compound (25 mg) was obtained from 140 mg of (SS, 5R, 6S) -6- ((IR) -hydroxyethyl) -l -methyl-2- [7- (4-nitrobenzyloxy-carbonylamino) acetylimidazo [5, 1-b] thiazol-2-yl] -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl in the same manner as in Example 1-b), except that the purification was carried out by column chromatography on Cosmosil 40C18-PREP (20% aqueous metal). NMR (D20) d: (HOD = 4.80 ppm): 1.21 (3H, d), 1.33 (3H, d), 3.50 (2H, m), 4.30 (2H, m), 4.42 (2H, Abq), 7.91 ( 1H, s), 8.12 (1H, s) Example 122 (IS, 5R, 6S) -2- (7-aminomethylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1- sodium hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate a) (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-metii-2- [7 - (Nitrobenzyloxycarbonylaminomethyl) imidazo [5, 1-b] thiazoi-2-yl] -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl In the same manner as in Example la), 228 were obtained mg (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- [7- (nitrobenzyloxycarbonylaminomethyl) imidazo [5, 1-b] thiazol-2-yl] 4-Nitrobenzyl-l-carbapen-2-em-3-carboxylate from 181 mg of (IR, 3R, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- oxo-1-carbapenam-carboxylate of 4-nitrobenzyl and 373 mg of 1- (4-nitrobenzyloxycarbonylamino) ethyl-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole. NMR (DMSO-d6) d: 1.20 (6H, d), 3.39 (1H, dd), 3.62 (1H, m), 4.05 (1H, m), 4.24 (2H, d), 4.32 (1H, dd), 5.12 (1H, d), 5.20 (2H, s), 5.34 (lH, d), 5.48 (1H, d), 7.61 (2H, d), 7.71 (2H, d), 8.00 (1H, m), 8.12 (1H, s), 8.18 (4H, d), 8.35 (1H, s) b) (1S, 5R, 6S) -2- (7-aminomethylimidazo [5, 1-b] thiazol-2-yl) -6 - ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylic acid sodium The title compound (24 mg) is obtained from 81 mg mg of, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- [7- (4-nitrobenzyloxy-carbonylaminomethyl) imidazo [5, 1-b] thiazol-2-yl] -l -carbapen-2-em-3-carboxylate of 4-nitrobenzyl in the same manner as in example 1-b), except that the purification was carried out by column chromatography on Cosmosil 40C18-PREP (30% aqueous methanol). NMR (D20) d: (HOD = 4.80 ppm): 1.20 (3H, d), 1.31 (3H, d), 3.49 (2H, m), 4.13 (1H, dd), 4.22 (2H, s), 4.27 ( 1H, m), 7.85 (1H, s), 8.13 (1H, s) Example 123 (IS, 5R, 6S) -2- [7- (2-aminoethanesulfonylamino) acetylimidazo [5, 1-b] thiazole-2- il] -6-: (IR) -hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate sodium a) (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl ) -l-methyl-2- [7- [2- (nitrobenzyloxycarbonyl) aminoethanesulfonylamino]} Acetylimimidazo [5, 1-b] thiazol-2-yl] -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl In the same manner as in Example la), 57.2 mg of (ΔS, 5R , 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- [7- [2- (4-nitrobenzyloxycarbonyl) aminoethanesulfonylamino]} acetylimimidazo [5, 1-b] thiazol-2-yl] -l-carbapen-2-em-3-carboxylic acid 4-nitrobenzyl ester from 120 mg of (IR, 3R, 5R, 6S) -6- (( IR) -1-hydroxyethyl) -l-methyl-2-oxo-l-carbapenam-3-carboxylate of 4-nitrobenzyl and 192 mg of 7- [2- (4-nitrobenzyloxycarbonyl) aminoethane-sulfonylamino] acetyl-2- ( tri-n-butylstannyl) -imidazo [5, 1-b] thiazole. NMR (DMSO-de) d: 1.19 (3H, d, J = 6.5 Hz), 1.22 (3H, d, J = 7.3 Hz), 3.2-3.3 (2H,), 3.4-3.5 (3H, m), 3.7 -3.8 (1H, m), 4.0-4.1 (1H, m), 4.3-4.4 (lH, m), 4.49 (2H, s),. 5.17 (2H, s), 5.39 (1H, d, J = 14.3 Hz), 5.53 (1H, d, J = 14.3 Hz), 7.58 (2H, d, J = 8.6 Ez), 7.74 (2H, d, J = 8.6 Hz), 8.18 (2H, d, J = 8.6 Hz), 8.21 2H, d, J = 8.6 Hz), 8.36 (1H, s), 8.59 (1H, s) b) (1S.5R, 6S) -2- [7- (2-aminoethanesulfonylamino) acetylimidazo [5, 1-b] thiazol-2-yl] -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em- 3-sodium carboxylate The title compound (20.1 mg) was obtained from 55.4 mg of (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- [7- [2- (4-Nitrobenzyloxycarbonyl) aminoethanesulfonylamino] acetylimidazo [5, 1-b] thiazol-2-yl] -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl in the same manner as in the example 1-b), except that the purification was carried out in column chromatography on Cosmosil 40C18-PREP (10% aqueous methanol). NMR (D20) d: (HOD = 4.80 ppm): 1.20 (3H, d, J = 7.1 Hz), 1.33 (3H, d, J = 6.4 Hz), 3.4-3.55 (4H, m), 3.55-3.7 ( 2H,), 4.2-4.35 (2H, m), 4.78 (2H, s), 7.83 (1H, s), 7.99 (1H, s) Example 124 (5R, 6S) -2- [7- (2-aminoethanesulfonylamino ) acetylimidazo [5, 1-b] thiazol-2-yl] -6- ((IR) -hydroxyethyl) -l-carbapen-2-em-3-carboxylate sodium a) (5R, 6S) -6- ( (IR) -1-hydroxyethyl) -2- [7- [2- (4-nitrobenzyloxycarbonyl) aminoethanesulfonylamino] acetylimidazo [5, 1-b] thiazol-2-yl] -l-carbapen-2-em-3 4-Nitrobenzylcarboxylate In the same manner as in Example la), 80.6 mg of (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- [7- [2- (4 -nitrobenzyloxycarbonyl) aminoethanesulfonylamino) acetylimidazo [5, 1-b] thiazol-2-yl] -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl from 99 mg of (3R, 5R, 6S) -6 - ((IR) -1-hydroxyethyl) -2-oxo-l-carbapenam-3-carboxylate of 4-nitrobenzyl and 215 mg of 7- [2- (4-nitrobenzyloxycarbonyl) aminoethanesulfonylamino] -acetyl-2- (tri- n-butiestanil) im idazo [5, 1-b] -thiazole. NMR (CDC13) d: 1.41 (3H, d, J = 6.3 Hz), 3.25-3.4 (5H, m), 3.7-3.8 (2H, m), 4.3-4.45 (2H, m), 4.68 (2H, d) , J = 5.0 Hz), 5.19 (2H, s), 5.33 (1H, d, J = 13.3 Hz), 5.55 (1H, d, J = 13.3 Hz), 7.49 (2H, d, J = 8.8 Hz), 7.70 (2H, d, J = 8.8 Hz), 7.99 (1H, s), 8.17 (2H, d, J = 8.8 Hz), 8.25 (2H, d, J = 8.8 Hz), 8.33 (1H, s) b ) (5R, 6S) -2- [7- (2-aminoethanesulfonylamino) acetylimidazo [5, 1-b] thiazol-2-yl] -6- ((IR) -1-hydroxyethyl) -l-carbapen-2- sodium em-3-carboxylate The title compound (21.4 mg) was obtained from 80.6 mg of (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- [7- [2- ( 4-Nitrobenzyloxycarbonyl) -aminoethanesulfonylamino] acetylimidazo [5, 1-b] thiazol-2-yl] -1-carbapen-2-em-3-carboxylate of 4-nitrobenzyl in the same manner as in Example 1-b), except that the purification was carried out by column chromatography in Cosmosil 40C18-PREP (20% aqueous metal). NMR (D20) d: (HOD = 4.80 ppm): 1.33 (3H, d, J = 6.6 Hz), 3.0-3.25 (2H, m), 3.5-3.75 (5H, m), 4.2-4.35 (2H, m ), 4.51 (2H, s), 7.59 (1H, s), 7.94 (1H, s) Example 125 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (5-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l.ethyl-l-carbapene-2-em-3-carboxylic acid sodium a) (ΔS, 5R, 6S) -6- ((IR) -1- hydroxyethyl) -l-methyl-2- (5-methylthioimidazo- [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl In the same manner as in the example la), 643 md of (ΔS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (5-methylthioimidazo- [5, 1-b] thiazole-2 were obtained -l) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl from 847 mg of (IR, 3R, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-met L-2-oxo-l-carbapenam-3-carboxylate of 4-nitrobenzyl and 1.13 mg of 5-methylthio-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole. NMR (CDC13) d: 1.32 (3H, d, J = 7.3 Hz), 1.39 (3H, d, J = 6.3 Hz), 2.55 (3H, s), 3.36 (1H,), 3.49 (1H,), 4.31 (1H, m), 4.36 (1H, dd, Ji = 9.5 Hz, J2 '= 2.7 Hz), 5.28 (1H, d, J = 13.6 Hz), 5.53 (1H, d, J = 13.6 Hz), 7.11 ( 1H, s), 7.67 (2H, d, J = 8.7 Hz), 8.18 (1H, s), 8.23 (2H, d, J = 8.7 Hz) b) • (1S, 5R, 6S) -6- (( lR) -: - hydroxyethyl) -2- (5-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-α-ethyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl. reaction in the same manner as in example 44-b), except that 112 mg of (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (5- 3-nVrobenzyl methyl, 5-1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate and 268 mg of oxone as the starting compounds. The product of the reaction was purified by column chromatography on silica gel (dichloromethane: methanol = 20: 1 to 10: 1) to provide 65 mg of (IS, 5R, 6S) -6- ((IR) -1- hydroxyethyl) -2- (5-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl. NMR (CDC13) d: 1.34 (3H, d, J = 7.3 Hz), 1.39 (3H, d, J = 6.3 Hz), 3.33 (3H, s), 3.38 (1H,), 3.59 (1H, m ), 4.31 (1H, m), 4.38 (1H, dd, Ji = 9.6 Hz, J2 = 2.8 Hz), 5.30 (1H, d, J = 13.7 Hz), 5.53 (1H, d, J = 13.7 Hz), 7.29 (1H, s), 7.66 (2H, d, J = 8.8 Hz), 8.23 (2H, d, J = 8.8 Hz), 8.54 (1H, s) c) (SS, 5R, 6S) -6- ( (IR) -1-hydroxyethyl) -2- (5-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate sodium In the same way that in Example 1-b), 32 mg of the title compound was obtained from 75 mg of (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (5-matnesulfonylimidazo [ 5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl. NMR (D20) d: (HOD = 4.65 ppm): 1.11 (3H, d, J = 7.3 Hz), 1.18 (3H, d, J = 6.5 Hz), 3.23 (3H, s), 3.40 (1H, dd, Ji = 6.1 Hz, J2 = 2.6 Hz), 3.50 (1H, m), 4.13 (1H, m), 4.19 (1H, dd, Ji = 9.3 Hz, J2 = 2.5 Hz), 7.21 (1H, s), 8.02 (1H, s) Example 126 (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (5-methylthioimidazo [5, 1-b] thiazol-2-yl) sodium l-carbapen-2-em-3-carboxylate In the same manner as in example 1-b), the title compound (44 mg) was obtained from 107 mg of (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (5-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of 4 -nitrobenzyl. NMR (D20) d: (HOD = 4.65 ppm): 1.12 (3H, d, J = 7.1 Hz), 1.19 (3H, d, J = 6.6 Hz), 2.32 (3H, s), 3.38 (1H, dd, Ji = 5.4 Hz, J2 = 2.1 Hz), 3.46 (1H, m), 4.15 (2H, m), 6.89 (1H, s), 7.01 (1H, s) Example 127 (1S, 5R, 6S) -2- [5,7-bis (methylthio) imidazo [5, 1-b] thiazol-2-yl] -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3 sodium carboxylate a) (1S, 5R, 6S) -2- [5,7-bis (methylthio) imidazo [5, 1-b] thiazol-2-yl] -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl In the same way as in example la), 720 mg of (IS, 5R, 6S) -2- [5,7-bis (methylthio) imidazo [5, 1-b] thiazol-2-yl] -6- ((lR) -l-hydroxyethyl were obtained ) -l-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl from 762 mg of (IR, 3R, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l -methyl-2-oxo-l-carbapenam-3-carboxylate of 4-nitrobenzyl and 1.10 mg of 5, 7. is (methylthio) -2- (tri-n-butiestanil) imidazo [5, 1-b] thiazole. NMR (CDC13) d: 1.31 (3H, d, J = 7.3 Hz), 1.39 (3H, d, J = 6.3 Hz), 2.43 (3H, s), 2.58 (3H, s), 3.36 (1H, m) , 3.49 (1H, m), 4.33 (2H, m), 5.28 (1H, d, J = 13.7 Hz), 5.53 (1H, d, J = 13. 4 Hz), 7.67 (2H, d, J = 9.0 Hz), 8.13 (1H, s), 8.23 (2H, d, J = 9.0 Hz) b) (1S, 5R, 6S) -2- [5, 7-bis (methylthio) imidazo [5, 1-b] thiazol-2-yl] - 6- ((IR) -1- sodium hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate In the same manner as in Example 1-b), 42 mg of the title compound was obtained from 89 mg of (1S, 5R, 6S) -2- [5, 7-bis (methylthio) imidazo [5, 1-b] thiazol-2-yl] -6- ((IR) -1-hydroxyethyl) -l-methyl-1-carbapen -2-em-3-carboxylate of 4-nitrobenzyl. NMR (D20) d: (HOD = 4.65 ppm): 1.09 (3H, d, J = 7.3 Hz), 1. 18 (3H, d, J = 6.3 Hz), 2.20 (3H, s), 2.34 (3H, s), 3.36 (1H, dd, Ji = 6.0 Hz, J2 = 20.6 Hz), 3.45 (1H, m), 4.15 (2H, m), 7.66 (1H, s) Example 128 (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-phenylthioimidazo [5, 1-] b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid sodium a) (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-phenylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl In the same manner as in example la), 92.5 mg of ( ÍS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7- phenylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em -3-carboxylic acid 4-nitrobenzyl from 146 mg of (IR, 3R, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2-oxo-l-carbapenam-3- 4-nitrobenzyl carboxylate and 231 mg of 7. phenylthio-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole. NMR (CDC13) d: 1.30 (3H, d, J = 7.3 Hz), 1.39 (3h, d, J = 6.2 Hz), 3.36 (1H, dd, Ji = 6.5 Hz, J2 = 2.8 Hz), 3.4-3.5 (1H, m), 4.25-4.35 (1H, m), 4.36 (1H, dd, Ji = 9.7 Hz, J2 = 2.8 Hz), 5.27 (1H, d, J = 13.5 Hz), 5.52 (1H, d, J = 13.5 Hz), 7.1-7.25 (5H, m), 7.67 (2H, d, J = 8.7 Hz), 8.10 (1H, s), 8.24 (2H, d, J = 8.7 Hz), 8.35 (1H, s) b) (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-phenylthioimidazo [5, 1-b] thiazol-2-yl] -l- sodium carbapen-2-em-3-carboxylate The title compound (23.9 mg) was obtained from 42.8 mg of (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl -2- (7-phenylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl in the same manner as in Example 1-b), except that the purification was carried out by column chromathography in Cosmosil 40C18-PREP (20% aqueous methanol). NMR (D20) d: (HOD = 4.80 ppm): 1.17 (3H, d, J = 6.9 Hz), 1.31 (3H, d, J = 6.3 Hz), 3.35-3.5 (2H, m), 4.2-4.3 ( 2H, m), 7.1-7.3 (5H, m), 7.87 (1H, s), 8.15 (1H, s) Example 129 (5R, 6S) -6- ((IR) -l-hydroxyethyl) -2- ( 7-Methylthioimidazo [5, 1-b] thiazol-3-yl) -l-carbapen-2-em-3-carboxylic acid sodium a) (5R, 6S) -6- ((IR) -1-hydroxyethyl) - 2- (7-Methylthioimidazo [5, 1-b] thiazol-3-yl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl In the same manner as in Example la), 230 mg was obtained of (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methylthioimidazo [5, 1-b] thiazol-3-yl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl from 348 mg of (3R, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2-oxo-l-carbapenam-3-carboxylate of 4-nitrobenzyl and 535 mg of 7 -methylthio-3- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole. NMR (DMSO-ds) d: 1.18 (3H, d), 2.31 (3H, s), 3.27 (1H, m), 3.56 (2H, m), 4.02 (1H, m), 4.42 (1H, m), 5.27 (1H, d), 5.31 (2H, Abq), 7.43 (1H, s), 7.50 (2H, d), 8.16 (2H, d), 8.30 (1H, s) b) (5R, 6S) -6 - ((IR) -1-hydroxyethyl) -2- (7-methylthioimidazo [5, 1-b] thiazol-3-yl) -l-carbapen-2-em-3-carboxylate sodium The title compound (28 mg) was obtained from 100 mg of (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methylthioimidazo [5, 1-b] thiazol-3-yl) -l- 4-nitrobenzyl carbapen-2-em-3-carboxylate in the same manner as in Example l-b9, except that the purification was carried out by column chromatography on Cosmosil 40C18-PREP (10-20% aqueous methanol).

NMR (D20) d: (HOD = 4.80 ppm): 1.21 (3H, d), 2.37 (3H, s), 3.18 (1H, dd), 3.44 (1H, dd), 3.58 (1H, dd), 4.28 ( 1H, m), 4.87 (1H, m), 7.08 (1H, s), 7.92 (1H, s) Example .130 (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7 sodium phenylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate a) (5R), 6S) -6- ((IR) -1-hydroxyethyl) -2- (phenylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl in the same manner as in Example la), 105.3 mg of (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-phenylthioimidazo [5, 1-b] thiazole-2- were obtained. il) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl from 140 mg of (3R, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2-oxo-l- 4-nitrobenzyl carbapenam-3-carboxylate and 232 mg of 7-phenylthio-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole. NMR (DMSO-de) d: 1.17 (3H, d, J = 6.2 Hz), 3.35-3.55 (3H, m), 3.95-4.05 (1H, m), 4.2-4.3 (1H, m), 5.39 (1H , d, J = 13.8 Hz), 5.51 (1H, d, J = 13.8 Hz), 7.0-7.3 (5H, m), 7.74 (2H, d, J = 8.7 Hz), 8.22 (2H, d, J = 8.7 Hz), 8.40 (1H, s), 8.43 (1H, s) b) (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-phenylthioimidazo [5, 1-b] sodium thiazol-2-yl) -l-carbapen-2-em-3-carboxylate. The title compound (21.9 mg) was obtained from 47.1 mg of (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-phenylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl in the same manner as in Example 1 -b), except that the purification was carried out by column chromatography on Cosmosil 40C18-PREP (10% aqueous methanol). NMR (D20) d: (HOD = 4.80 ppm): 1.31 (3E, d, J = 6.3 Hz), 3.05-3.25 (2H, m), 3.47 (1H, dd, Jx = 5.6 Hz, J2 = 2.8 Hz) , 4.2-4.3 (2H, m), 7.1-7.3 (5H, m), 7.652 (ÍE, s), 8.08 (1H, s) Example 131 (ÍS, 5R, 6S) -6- ((IR) -1 -hydroxyethyl) -l-methyl-2- (3-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid sodium a) (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-metii-2- (3-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of 4 -nitrobenzyl In the same manner as in Example la), 287 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (3-methylthioimidazo [5] were obtained. , 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl from 1.56 g of (IR, 3R, 5R, 6S) -6- ((IR) - 1-hydroxyethyl) -l-methyl-2-oxo-l-carbapenam-3-carboxylate of 4-nitrobenzyl and 2.05 g of 3-methylthio-2- (tri-n-butiestanil) imidazo [5, 1-b] thiazole . NMR (CDC13) d: 1.21 (3H, d, J = 7.3 Hz), 1.38 (3H, d, J = 6.3 Hz), 2.27 (3H, s), 3.38 (1H, m), 3.46 (1H, m) , 4.43 (1H, m), 4.47 (1H, dd, Ji = 10.5 Hz, J2 = 3.1 Hz), 5.19 (1H, d, J = 13.7 Hz), 5.39 (1H, d, J = 13.7 Hz), 7.14 (1H, s), 7.50 (2H, d, J = 9.0 Hz), 8.05 (1H, s), 8.14 (2h, d, J = 9.0 Hz) b) (ÍS, 5R, 6S) -6- (( IR) -1-hydroxyethyl) -l-methyl-2- (3-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate sodium In the same way as in Example 1-b), 37 mg of the title compound was obtained from 83 mg of (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (3 -nitrobenzyl NMR (D20) d: (HOD = 4.65 ppm): 1.02 (3H, d, J = 7.3 Hz), 1.15 (3H, d, J = 6.3 Hz), 2.21 (3H, s), 3.31 (1H, m), 3.40 (1H, m), 4.13 (1H, m), 4.22 (1H, dd, Ji = 10.0 Hz, J2 = 3.0 Hz), 6.96 (1H, s), 8.15 (1H, s) Example 132 (1S, 5R, 6S) -2- (7-ethylthioimidazo [5, lb] thiazole-2 -il) -6- ((1R) -1-hydroxyethyl) -l-me Sod-l-carbapen-2-em-3-carboxylic acid sodium a) (1S, 5R, 6S) -2- (7-ethylthioimidazo [5, 1-b] thiazol-2-yl) -6- ((IR ) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl In the same manner as in Example la), 731 mg of (ÍS, 5R, 6S) - 2- (7-ethylthioimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate from 4-nitrobenzyl from 724 mg of (IR, 3R, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2-oxo-l-carbapenam-3-carboxylate of 4-nitrobenzyl and 1.04 g of 7-ethylthio-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole NMR (CDC13) d: 1.26 (3H, t, J = 7.3 Hz), 1.31 (3H, d, J = 7.2 Hz), 1.40 (3H, d, J = 6.1 Hz), 2.84 (2H, q, J = 7.3 Hz), 3.37 (1H, dd, Ji = 6.5 Hz, J2 = 2.8 Hz), 3.4-3.5 (1H, m), 4.25-4.35 (1H, m), 4.38 (1H, dd, Jx = 9.4 Hz, J2 = 2.8 Hz), 5.28 (1H, d, J = 13.7 Hz), 5.53 (1H, d, J = 13.7 Hz), 7.68 (2H, d, J = 8.4 Hz), 8.03 (1H, s), 8.24 (2H, d, J = 8.4 Hz), 8.30 (1H, s) b) (1S, 5R, 6S) -2- (7-ethylthioimidazo [5, 1-b] thiazol-2-yl) -6- ((1R) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate Sodium The title compound (87.5 mg) was sustained from 174 mg of (SS, 5R, 6S) -2- (7-ethylthioimidazo [5, 1-b] thiazol-2-yl) -6- (( IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl in the same manner as in Example 1-b), except that the purification ion was performed by column chromatography on Cosmosil 40C18-PREP (5% aqueous methanol). NMR (D20) d: (HOD = 4.80 ppm): 1.15 (3H, t, J = 7.3 Hz), 1.24 (3H, d, J = 7.4 Hz), 1.32 (3H, d, J = 6.2 Hz), 2.76 (2H, q, J = 7.3 Hz), 3.45-3.6 (2H, m), 4.2-4.35 (2H,), 7.88 (1H, s), 8.12 (1H, s) Example 133 (5R, 6S) -6 - ((IR) -1-hydroxyethyl) -2- (3-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid sodium a) (5R, 6S ) -6- ((IR) -1-hydroxyethyl) -2- (3-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl De in the same manner as in Example la), 37 mg of (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (3-methylthioimidazo [5, 1-b] thiazole-2- were obtained il) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl from 743 mg of (3R, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2-oxo-l- carbapenam-3- ^ carboxylic acid of 4-nitrobenzyl and 1.02 g of 3-methylthio-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole. NMR (CDC13) d: 1.39 (3H, d, J = 6.3 Hz), 2.31 (3H, s), 3.28 (2H, m), 3.39 (1H, m), 4.30 (1H, m), 4.42 (1H, m), 5.24 (1H, d, J = 13.7 Hz), 5.38 (1H, d, J = 13.7 Hz), 7.13 (1H, s), 7.50 (2H, d, J = 9.1 Hz), 8.04 (1H, s9, 8.14 (2H, d, J = 9.1 HZ) b) (5R, 6S) -6- ((lR) -l-hydroxyethyl) -2- (3-methylthioimidazo [5, lb] thiazol-2-yl) sodium l-carbapen-2-em-3-carboxylate In the same manner as in Example 1-b), 15 mg of the title compound was obtained from 35 mg of (5R, 6S) -6- ( (IR) -1-hydroxyethyl) -2- (3-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl. NMR (D20) d: (HOD = 4.65 ppm): 1.15 (3H, d, J = 6.3 Hz), 2.22 (3H, s), 3.03 (1H, m), 3.26 (1H, m), 3.42 (1H, m), 4.12 (1H, m), 4.22 (1H, m), 6.96 (1H, s), 8.16 (1H, s) Example 134 (5R, 6S) -2- (7-ethylthioimidazo [5, 1-b ] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylac sodium (a) (5R, 6S) -2- (7-ethylthioimidazo [5, lb] thiazol-2-yl) -6- ((1R) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl In the same manner as in Example la), 691 were obtained mg (5R, 6S) -2- (7-ethylthioimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3 carboxila.o of 4-nitrobenzyl from 869 mg of (3R, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2-oxo-l-carbapenam-em-3-carboxylate of 4-nitrobenzyl and 1.30 mg of 7-ethylthio-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole. NMR (CDC13) d: 1.25 (3H, t, J = 7.3 Hz), 1.40 (3H, d, J = 6. 4 Hz), 2.83 (2H, q, J = 7.3 Hz), 3.3-3.4 (3H,), 4.25-4.4 (2H, m), 5.32 (1H, d, J = 13.6 Hz), 5.55 (1H, d, J = 13.6 Hz), 7.69 (2H, d, J = 9.0 Hz), 8.02 (1H, s), 8.20 (lh, s), 8.25 (2H, d, J = 9.0 Hz) b) (5R, 6S) -2- (7-ethylthioimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate sodium The title compound (60.7 mg ) was obtained from 115 mg of (5R, 6S) -2- (7-ethylthioimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-carbapen -2-em-3-carboxylate of 4-nitrobenzyl in the same manner as er. Example 1-b), except that the purification was carried out by column chromatography on Cosmosil 40C18-PREP (5% aqueous methane). NMR (D20) d: (HOD = 4.80 ppm): 1.16 (3H, t, J = 7.4 Hz), 1.32 (3H, d, J = 6.4 Hz), 2.77 (2H, q, J = 7.4 Hz), 3.2 -3.4 (2H, m), 3.45-3.55 (1H, m), 4.2-4.35 (2H, m), 7.72 (1H, s), 8. 10 (1H, s) Example 135 (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (3-methyl-7-methylthioimidazo [5, 1-b] thiazol-2-yl) - sodium l-carbapen-2-em-3-carboxylate a) (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (3-methyl-7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl In the same manner as in Example la), 927 mg of (5R, 6S) -6- ((IR) were obtained 1-hydroxyethyl) -2- (3-methyl-7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl from 1.044 g from (3R, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2-oxo-l-carbapenam-3-carboxylate of 4-nitrobenzyl and 1.56 g of 3-methyl-7-methylthio- 2- ( tri-n-butylstannyl) imidazo [5, 1-b] thiazole. NMR (CDC13) d: 1.40 (3H, d, J = 6.3 Hz), 2.19 (3H, s), 2.43 (3H, s), 3.1-3.3 (2H, m), 3.36 (1H, dd, Ji = 6.4 Hz, J2 = 3.1 Hz), 4.25-4.45 (2H, m), 5.24 (1H, d, J = 13.7 Hz), 5.43 (1H, d, J = 13.7 Hz), 7.57 (2H, d, J = 8.7 Hz), 7.85 ( 1H, s), 8.18 (2H, d, J = 8.7 Hz) b) (5R, 6S) -6- ((lR) -l-hydroxyethyl) -2- (3-methyl-7-methylthioimidazo [5,1] sodium β-thiazol-2-yl) -l-carbapen-2-em-3-carboxylate The title compound (43.6 mg) was obtained from 89.8 mg of (5R, 6S) -6- ((IR ) -1-hydroxyethyl) -2- (3-methyl-7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl in the same way in Example 1-b), except that the purification was carried out by column chromatography on Cosmosil 40C18-PREP (5% aqueous methanol). NMR (D20) d: (HOD = 4.80 ppm): 1.31 (3H, d, J = 6.3 Hz), 2.26 (3H, s), 2.36 (3H, s), 3.05-3.35 (2H, m), 3.55 ( 1H, dd, Ji = 5.7 Hz, J2 = 3.0 Hz), 4.2-4.4 (2H, m), 8.11 (1H, s) Example 136 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl ) -2- (7-methansulfinyl-5-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate sodium (a mixture of diastereomers) a ) (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfinyl-5-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-methyl-1 -carbapen-2-em-3-carboxylate of 4-nitrobenzyl (a mixture of diastereomers) It was dissolved (1S, 5R, 6S) -2- [5,7-bis (methylthio) imidazo [5,1-b] thiazole -2-yl] -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl (140 mg) in 2.5 ml of dichloromethane. M-chloroperbenzoic acid (56 mg) was added to the solution. The mixture was stirred at room temperature for 15 minutes. An aqueous solution of sodium thiosulfate (5 ml) was added thereto followed by separation. The organic layer was washed with 10 ml of a semi-saturated aqueous solution of sodium hydrogencarbonate and 10 ml of half-saturated saline and then dried on anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography on silica gel (dichloromethane: methanol = 20: 1) to provide 97 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfinyl-5-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl ( a mixture of diastereomers). NMR (CDC13) d: 1.30, 1.31 (total 3H, each d, each J = 7.3 Hz), 1.39 (3H, d, J = 6.3 Hz), 2.62, 2.63 (total 3H, each s), 2.95, 2.96 ( total 3H, each s), 3.36 (1H, m), 3.47 (1H,), 4.30 (1H, m), 4.36 (1H, m), 5.27 (1H, d, J = 13.7 Hz), 5.53 (1H, d, J = 13.7 Hz), 7.66 (2H, d, J = 8.5 Hz), 8.23 (total 3H, m) b) (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2 - (7-methansulfinyl-5-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate of 4-sodium (a mixture of diastereomers) same as in Example 1-b), 37 mg of the title compound was obtained from 97 mg of (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7- Methansulfinyl-5-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 4-nitrobenzyl ester. NMR (D20) d: (HOD = 4.65 ppm): 1.11 (3H, d, J = 7.0 Hz), 1.17 (3H, d, J = 6.3 Hz), 2.37, 2.38 (total 3H, each s), 2.92, 2.93 (total 3H, each s), 3.37 (1H, m), 3.50 (1H, m), 4.16 (2H, m), 7.82, 7.84 (total 1H, each s) Example 137 (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (3-hydroxymethyl-7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l- sodium carbapen-2-em-3-carboxylate a) (5R, 6S) -2- (3-t-butyldimethylsilyloxymethyl-7-methylthioimidazo [5, 1-b] thiazol-2-yl) -6- ((IR ) -1-hydroxyethyl) -1-carbapen-2-em-3-carboxylate of 4-nitrobenzyl In the same manner as in Example la), 561 mg of (5R, 6S) -2- (3-t) were obtained -butyldimethylsilyloxymethyl-7-methylthioimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -1-carbapen-2-em-3-carboxylate of 4-nitrobenzyl from 522 mg of (3R, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2-oxo-l-carbapenam-3-carboxylate of 4-nitrobenzyl and 995 mg of 3-t- butyldimethylsilyloxymethyl-7-methylthio-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole. NMR (CDC13) d: 0.01 (6H, s), 0.83 (9H, s), 1.39 (3H, d, J = 6.3 Hz), 2.43 (3H, s), 3.1-3.2 (2H, m), 3.34 ( 1H, dd, Ji = 6.5 Hz, J2 = 3.0 Hz), 4.25-4.45 (2H, m), 4.49 (2H, s), 5.21 (1H, d, J = 13.7 Hz), 5.41 (1H, d, J = 13.7 Hz), 7.56 (2H, d, J = 8.8 Hz), 8.07 (1H, s), 8.17 (2H, d, J = 8.8 Hz) b) (5R, 6S) -6- ((IR) - 1-hydroxyethyl) -2- (3-hydroxymethyl-7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl Obtained (5R, 6S ) -6- ((IR) -1-hydroxyethyl) -2- (3-hydroxymethyl-7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate from 4-Nitrobenzyl (315 mg) from 561 mg of (5R, 6S) -2- (3-t-Butyldimethylsilyloxymethyl-7-methylthioimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -1-carbapen-2- 4-nitrobenzyl em-3-carboxylate in the same manner as in Example 36-b), except that the purification was carried out by column chromatography on silica gel (dichloromethane: methanol = 2Q: 1). NMR (CDC13) d: 1.39 (3H, d, J = 6.3 Hz), 2.43 (3H, s), 3.1-3.25 (2H, m), 3.36 (1H, dd, Ji = 6.4 Hz, J2 = 3.1 Hz) , 4.25-4.45 (2H, m), 4.45-4.6 (2H, m), 5.26 (1H, d, J = 13.6 Hz), . 47 (1H, d, J = 13.6 Hz), 7.63 (2H, d, J = 8.9 Hz), 8.18 (1H, s), 8.23 (2H, d, J = 8.9 Hz) c) (5R, 6S) - 6- ((IR) -1-hydroxyethyl) -2- (3-hydroxymethyl-7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid sodium The title compound (59.4 mg) was obtained from 113 mg of (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (3-hydroxymethyl-7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2 4-nitrobenzyl ether-3-carboxylate in a similar manner as in Example 1-b), except that the purification was carried out by column chromatography on Cosmosil 40C18-PREP (5% aqueous methanol). NMR (D20) d: (HOD = 4.80 ppm): 1.35 (3H, d, J = 6.4 Hz), 2.41 (3H, s), 3.1-3.35 (2H, m), 3.60 (1H, dd, Jx = 5.8 Hz, J2 = 3.0 Hz), 4.25-4.45 (2H, m), 4.69 (2H, s), 8.29 (1H, s) Example 138 (5R, 6S) -6- ((IR) -1-hydroxyethyl) - 2- (3-phenylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid sodium a) (5R, 6S) -6- ((IR) -1- hydroxyethyl) -2- (3-phenylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl In the same manner as in Example la), obtained 110 mg of (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (3-phenylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em- 4-Nitrobenzyl 3-carboxylate from 348 mg of (3R, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2-oxo-l-carbapenam-3-carboxylate of 4-nitrobenzyl and 513 3-phenyl-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole mg. NMR (CDC13) d: 1.21 (3H, d), 2.90 (2H,), 3.18 (1H, dd), 4.22 (2H, m), 5.16 (1H, d), 5.32 (1H, d), 7.12 (1H , s), 7.50 (7H, m), 7.92 (1H, s), 8.15 (2H, d) b) (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (3-phenylimidazole) [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate sodium The title compound (11 mg) was obtained from 100 mg of (5R, 6S) -6 - ((IR) -1-hydroxyethyl) -2- (3-phenylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl in the same way than in Example 1-b), except that the purification was fefctured by column chromatography on Cosmosil 40C18-PREP (30% aqueous methanol) NMR (D20) d: (HOD = 4.80 ppm): 1.23 (3H, d) , 2.85 (2H, m), 3.37 (1H, m), 4.18 (2H, m), 7.12 (1H, s), X56 (5H,, s), 8.11 (1H, s) Example 139 (5R, 6S) -2- (7-aminoacetylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -hydroxyethyl) -l-carbapen-2-em-3-carboxylic acid sodium a) (5R, 6S ) -6- ((IR) -1-hydroxyethyl) -2- [7- (4-nitrobenzyloxycarbonyl-amino) acetylim [5, 1-b] thiazol-2-yl] -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl In the same manner as in Example la), 195 mg of (5R, 6S ) -6- ((IR) -1-hydroxyethyl) -2- [7- (4-nitrobenzyloxycarbonylamino) acetyl-imidazo [5, 1-b] thiazol-2-yl] -l-carbapen-2-em-3 4-Nitrobenzylcarboxylate from 348 mg of (3R, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2-oxo-l-carbapenam-3-carboxylate of 4-nitrobenzyl and 650 mg of 7- (4-nitrobenzyloxycarbonylamino) acetyl-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole. NMR (DMSO-de) 6: 1.18 (3H, d), 3.51 (3H, m), 4.28 (1H, m), 4.47 (3H, m), 5.17 (1H, d), 5.21 (2H, s,, 5.51 (2H, ABq), 7.65 (2H, d), 7.77 (2H, d), 8.24 (2H, d), 8.26 (2H, d), 8.37 (1H, s), 8.52 (1H, s) b) (5R, 6S) -2- (7-aminoacetylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate from sodium The title compound (34 mg) was obtained from 140 mg of (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- [7- (4-nitrobenzyloxycarbonyl-amino) acetylimidazo [5, 1-b] thiazol-2-yl] -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl in the same manner as in example 1-b), except that the purification was carried out by column chromatography on Cosmosil 40C18-PREP (10% aqueous methanol). NMR (D20) d: (HOD = 1.31 (3H, d), 3.08 (2H, m), 3.50 (1H, dd), 4.23 (2H, m), 4.39 (2H, s), 7.57 (1H, s) 7.99 (1H, s) Example 140 (1S, 5R, 6S) -6- ((1R) -l-hydroxyethyl) -2- (5-methansulfinylimidazo [5, 1-b] thiazol-2-yl) -l sodium-methyl-l-carbapen-2-em-3-carboxylate (a mixture of disatheremers) a) (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (5-methanesulfinylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl (a mixture of diastereomers) Obtained (1S, 5R, 6S) -6 - ((IR) -1-hydroxyethyl) -2- (5-methansulfinylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl (a mixture of disatereomers) (95 mg) in the same manner as in Example 136-a), except that the reaction was carried out using 112 mg of (IS, 5R, 6S) -6- ((IR) -1- hydroxyethyl) -l-methyl-2- (5-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate and 4-nitrobenzyl 49 mg of m-cloroprebenzoico as the initial compounds. NMR (CDC13) d: 1.32 (3H, d, J = 7.3 Hz), 1.39 (3H, d, J = 6.3 Hz), 3.12 (3H, s), 3.38 (1H, m), 3.56 (1H, m) , 4.36 (2H, m), 5.29 (1H, d, J = 13.6 Hz), 5.53 (1H, d, J = 13.6 Hz), 7.67 (2H, d, J = 8.8 Hz), 8.23 (2H, d, J = 8.8 Hz), 8.58, 8.59 (total 1H, each s) b) (1S, 5R, 6S) -6- ((lR) -l-hydroxyethyl) -2- (5-methansulfinylimidazo [5, 1-b ] thiazol-2-yl) -l-retyl-l-carbapen-2-em-3-carboxylate sodium (a mixture of .disatereomers) In the same manner as in example 1-b), 44 mg of the title compound title from 95 mg of (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (5-methansulfinylidene [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl. NMR (D20) d: (HOD = 4.65 ppm): 1.16 (3H, m), 1.22 (3H, d, J = 6.5 Hz), 3.11 (3H, s), 3.44 (1H, m), 3.54 (1H, m), 4.20 (2H, m), 7.20, 7.21 (total 1H, each s), 8.08 (1H, s), Example 141 (1S, 5R, 6S) -2- (5,7-dimethanesulfinylimidazo [5,1] -b] thiazol-2-yl) -6- ((IR) -hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate sodium (a mixture of diastereomers) a) (1S, 5R, 6S) -2- (5, 7-dimethanesulfinylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate 4-nitrobenzyl (a mixture of diastereomers) (1S, 5R, 6S) -2- (5, 7-dimetansulfinilimidazo [5, 1-b] thiazol-2-yl) - 6- ((IR) -hydroxyethyl) - 4-Nitrobenzyl l-methyl-l-carbapen-2-em-3-carboxylate (a mixture of diastereomers) (96 mg) was obtained in the same manner as in example 136-a), except that the reaction was carried out using 120 mg of (1S, 5R, 6S) -2- [5,7-bis (methylthio) imidazo [5, 1-b] thiazol-2-yl] -6- ((IR) -hydroxyethyl) -l- methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl and 99 mg of m-chloroperbenzoic acid as starting compounds. NMR (CDC13) d: 1.31 (3H, d, J = 7.3 Hz), 1.38 (3H, d, J = 6.4 Hz), 2.96 (3H, m), 3.15 (3H, m), 3.38 (1H, m) , 3.54 (1H, m), 4.31 (1H, m), 4.39 (1H, dd, Ji = 9.7 Hz, J2 = 2.7 Hz), 5.29 (1H, d, J = 13.4 Hz), 5.43 (1H, d, J = 13.4 Hz), 7.67 (2H, d, J = 9.1 Hz), 8.23 (2H, d, J = 9.1 Hz), 8.66 (1H, m) b) (SS, 5R, 6S) -2- (5 7-dimetansulfinilimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate (a mixture of diastereómerosj In the same manner as in Example 1-b), 30 mg of the title compound was obtained from 50 mg of (1S, 5R, 6S) -2- (5,7-dimethanesulfinylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl. NMR (D20) d: (HOD = 4.65 ppm): 1.16 (3H, m), 1.21 (3H, d, J = 6.3 Hz), 3.01 (3H, m), 3.14 (3H, s), 3.44 (1H, ), 3.58 (1H, m), 4.19 (2H,), 8.20 (1H, m) Example 142 (1S, 5R, 6S) -6- ((IR) -hydroxyethyl) -2- (5-methansulfinyl-7-) metansulfinilimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate (a mixture of diastereomers) a) (iS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (5-methanesulfinyl-7-methanesulfinylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl (a mixture of diastereomers) Obtained (1S, 5R, 6S) -6- ( (IR) -1-hydroxyethyl) -2- (5-ethansulfinyl-7-methansulfinylimidazo [5, 1-b] thiazol-2-yl) -1-methyl-1-carbapen-2-em-3-carboxylate of 4 -nitrobenzyl (a mixture of diastereomers) (53 mg) in the same manner as in Example 136-a), except that the reaction was carried out using 130 mg of (IS, 5R, 6S) -2- [5, 7- bis (methylthioimidazo [5, 1-b] thiazol-2-yl] -6- (IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl and 135 mg of m-chloroperbenzoic acid as the starting compounds. NMR (CDC13) d: 1.32 (3H, d, J = 7.4 Hz), 1.39 (3H, d, J = 6.3 Hz), 3.18, 3.19 (total 3H, each s), 3.21, 3.21 (total 3H, each s ), 3.39 (1H, dd, Ji = 6.3 Hz, J: = 2.9 Hz), 3.56 (1H,), 4.32 (1H, m), 4.40 (1H, dd, Ji = 9.3 Hz, J2 = 2.7 Hz), 5.29 (1H, d, J = 13.6 Hz), 5.53 (1H, d, J = 13.6 Hz), 7.67 (2H, d, J = 8.5 Hz), 8.24 (2H, d, J = 8.5 Ez), 8.65, 8.67 (total 1H, each s) b) (1S, 5R, 6S) -6- ((lR) -l-hydroxyethyl) -2- (5-methansulfinyl-7-methansulfinylimidazo [5, 1-b] thiazole- Sodium 2-yl) -l-methyI-l-carbapen-2-em-3-carboxylate (a mixture of diastereomers) In the same manner as in Example 1-b), 23 mg of the title compound was obtained from 53 mg of (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (5-methansulfinyl-7-methansulfinylimidazo [5, 1-b] thiazol-2-yl) -l -methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl. NMR (D20) d: (HOD = 4.65 ppm): 1.15, 1.16 (total 3H, each d, J = 7.2 Hz), 1.21 (3H, d, J = 6.3 Hz), 3.14 (3H, s), 3.23, 3.24 (total 3H, each s), 3.44 (1H, dd, Ji = 5.8 Hz, J2 = 2.0 Hz), 3.57 (1H,), 4.16 (1H, m), 4.23 (1H, m), 8.20, 8.21 ( total 1H, each s) Example 143 (1S, 5R, 6S) -2- [5, 7-bis (methanesulfonyl) imidazo [5, 1-b] thiazol-2-yl] -6- ((IR) -1 -hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl a) (SS, 5R, 6S) -2- [5,7- bis (methanesulfonyl) imidazo [5, 1-] b] thiazol-2-yl] -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl Obtained (ÍS, 5R, 6S) - 2- [5,7-bis (methanesulfonyl) imidazo [5, 1-b] thiazol-2-yl] -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em- 3-Nitrobenzyl 3-carboxylate (107 mg) in the same manner as in example 44-b), the reaction was carried out using 102 mg of (SS, 5R, 6S) -2- [5,7-bis (methylthio ) imidazo [5, 1-b] thiazol-2-yl] -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate d and 4-nitrobenzyl and 448 mg of oxone as the initial compounds.

The product of the reaction was purified by column chromatography on silica gel (dichloromethane: methanol = 20: 1 to 10: 1). NMR (CDC13) d: 1.33 (3H, d, J = 7.3 Hz), 1.35 (3H, d, J = 6.3 Hz), 3.25 (3H, s), 3.38 (1H, m), 3.41 (3H, s) , 3.59 (1H, m), 4.35 (1H, m), 4.43 (1H, dd, Ji = 9.7 Hz, J2 = 2.9 Hz), 5.30 (1H, d, J = 13.8 Hz), 5.54 (1H, d, J = 13.8 Hz), 7.69 (2H, d, J = 9.3 Hz), 8.22 (2H, d, J = 9.3 Hz), 8.56 (1H, s) b) (1S, 5R, 6S) -2- [5 , 7-bis (methanesulfonyl) imidazo [5, 1-b] thiazol-2-yl] -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate of sodium In the same manner as in example 1-b), 20 mg of the title compound was obtained from 67 mg of (1S, 5R, 6S) -2- [5,7-bis (methansulfonyl) imidazole) [5, 1-b] thiazol-2-yl] -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl. NMR (D20) d: (HOD = 4.65 ppm): 1.14 (3H, d, J = 7.3 Hz), 1.20 (3H, d, J = 6.6 Hz), 3.25 (3H, s), 3.35 (3H, s) , 3.44 (1H, dd, Ji = 6.1 Hz, J2 = 2.7 Hz), 3.59 (1H, m), 4.16 (1H, m), 4.23 (1H, dd, Ji = 9.5 Hz, J2 = 2.7 Hz), 8.18 (1 H, s) Example 144 (5R, 6S) -2- (3-aminomethylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-carbapen-2 sodium a-3-carboxylate a) (5R, 6S) -2- (3-azidomethylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l- 4-nitrobenzyl carbapen-2-em-3-carboxylate In the same manner as in Example la), 268.2 mg of (5R, 6S) -2- (3-azidomethylimidazo [5, 1-b] thiazole- 2-yl) -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl from 348 mg of (3R, 5R, 6S) -6- (( IR) -1-hydroxyethyl) -2-oxo-l-carbapenam-3-carboxylate of 4-nitrobenzyl and 515 mg of 3-azidomethyl-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole. NMR CDC13) d: 1.38 (3H, d, J = 6.3 Hz), 3.1-3.3 (2H, m), 3.40 (1H, dd, Ji = 6.1 Hz, J2 = 3.0 Hz), 4.25-4.35 (1H, m ), 4.4-4.5 (1H, m), 5.21 (1H, d, J = 13.5 Hz,, 5.41 (1H, d, J = 13.5 Hz), 7.12 (1H, s), 7.53 (2H, d, J = 8.5 Hz), 8.03 (1H, s), 8.15 (2H, d, J = 8.5 Hz) b) (5R, 6S) -2- (3-aminomethylimidazo [5, 1-b] thiazol-2-yl) - 6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate sodium The title compound (22.1 mg) was obtained from 97.4 mg of (5R, 6S) -2- ( 3-Azidomethylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl in the same manner as in Example 1-b), except that the purification was performed by column chromatography on Cosmosil 40C18-PREP (10% aqueous methanol) NMR (D20) d: (HOD = 4.80 ppm): 1.29 (3E, d, J = 6.1 Hz), 3.1-3.4 (2H, m), 3.5-3.6 (1H, m), 4.2-4.4 (2H, m), 4.34 (2H, s), 7.12 (1H, s), 8.32 (1H, s Example 145 (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (3-hydroxy-raphylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate or sodium a) (5R, 6S) -2- (3-t-butyldimethylsilyloxymethylimidazo [5, 1-b] thiazole- 2-yl) -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl In the same manner as in Example la), 1396 g of ^ ( 5R, 6S) -2- (3-t-butyldimethylsilyloxymethylimidazo [5, 1-b] thia? Ol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3 4-nitrobenzylcarboxylate from 1.42 g of (3R, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2-oxo-l-carbapenam-3-carboxylate of 4-nitrobenzyl and 2.28 g of 3-t-butyl dimethyl: ylsilyloxymethyl-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole. NMR (CDC13) d: 0.00 (6H, s), 0.84 (9H, e), 1.40 (3H, d, J = 6.3 Hz), 3.0-3.3 (2H, m), 3.33 (1H, dd, J: = 6.3 Hz, J2 = 6.3 Hz), 4.25-4.45 (2H, m), 4.52 (2H, s), 5.23 (1H, d, J = 13.4 Hz), 5.42 (1H, d, J = 13.4 Hz), 7.08 (1H, s), 7.55 (2H, d, J = 8.9 Hz), 8.10 (1H, s), 8.17 (2H, d, J = 5.9 Hz), b) (5R, 6S) -6- ((IR ) -1-hydroxyethyl) -2- (3-hydroxymethylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl (5R, 6S) - 6- ((IR) -1-hydroxyethyl) -2- (3-hydroxymethylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl (507 mg ) from 1396 g of (5R, 6S) -2- (3-t-butyldimethylsilyloxymethylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -hydroxyethyl) -l-carbapen-2 -em-3-carboxylate 4-nitrobenzyl in the same manner as in example 36-b), except that the purification was carried out using Sephadex LH-20 (chloroform: methanol = 1: 1). NMR (CDC13) d: 1.39 (3H, d, J = 6.3 Hz), 3.1-3.3 (2H, m), 3. 36 (1H, dd, Ji = 6.5 Hz, J2 = 2.9 Hz), 4.25-4.45 (2H, m), 4. 5-4.65 (2H, m), 5.27 (1H, d, J = 13.4 Hz), 5.47 (1H, d, J = 13. 4 Hz), 7.10 (1H, s), 7.63 (2H, d, J = 8.8 Hz), 8.20 (1H, s), 8.23 (2H, d, J = 8.8 Hz) c) (5R, 6S) -6 - ((IR) -1-hydroxyethyl) -2- (3-hydroxymethylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid sodium The title compound (58.4 mg) was obtained from 145.5 mg (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (3-hydroxymethylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen -2-em-3-carboxylate of 4-nitrobenzyl in the same manner as in Example 1-b), except that the purification was carried out by column chromatography on Cosmosil 40C18-PREP (5% aqueous methanol). NMR (D20) d: (HOD = 4.80 ppm): 1.29 (3H, d, J = 6.4 Hz), 3.13 (lH / dd, Ji = 17.4 Hz, J2 = 10.1 Hz), 3.28 (1H, dd, Jx = 17.4, J2 = 8.5 Hz), 3.55 (1H, dd, Ji = 5.8 Hz, J2 = 2.9 Hz), 4.2-4.4 (2H, m), 4.66 (2H, s), 7.08 (1H, s), 8.25 (1H, s) Example 146 (5R, 6S) -2- [5,7-bis (methylthio) -imidazo [5, 1-b] thiazol-2-yl] -6- ((IR) -1- sodium hydroxyethyl) -l-carbapen-2-em-3-carboxylate a) (5R, 6S) -2- [5,7-bis (methylthio) -imidazo [5, 1-b] thiazol-2-yl] -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl In the same manner as in Example la), 810 mg of (5R, 6S) - 2- [5,7-bis (methylthio) -imidazo [5, 1-b] thiazol-2-yl] -6- ((IR) -l-hydroxyethyl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl from 803 mg of (3R, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2-oxo-l-carbapenam-3-carboxylate of 4-nitrobenzyl and 1.18 g of , 7-bis (methylthio) -2- (tri-n-butylstannyl) imidazo- [5, 1-b] thiazole. NMR (CDC13) d: 1.39 (3H, d, J = 6.3 Hz), 2.42 (3H, s), 2.58 (3H, s), 3.30-3.40 (total 3H, m), 4.29-4.37 (total 2H, m ), 5.33 (1H, d, J = 13.6 Hz), 5.56 (1H, d, J = 13.6 Hz), 7.69 (2H, d, J = 9.0 Hz), 7.96 (1H, s), 8.25 (2H, d , J = 9.0 Hz) b) (5R, 6S) -2- [5, 7-bis (methylthio) -imidazo [5, 1-b] thiazol-2-yl] -6- ((IR) -1- hydroxyethyl) -l-carbapen-2-em-3-carboxylate sodium In the same manner as in Example 1-b), 33 mg of the title compound was obtained from 78 mg of (5R, 6S) -2- [5,7-bis (methylthio) -imidazo [5,1] -b] thiazol-2-yl] -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylic acid 4-nitrobenzyl NMR (D20) d: (HOD = 4.65 ppm): 1.20 (3H, d, J = 6.3 Hz), 2.24 (3H, s), 2.35 (3H, s), 3.18 (2H, m), '3.42 (1H, dd, J: = 6.1 Hz, J2 = 1.9 Hz ), 4.14-4.21 (2H, m), 7.55 (1H, s) Example 147 (SS, 5R, 6S) -2- (5-acetyl-7-methylthioimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylic acid sodium a) (SS, 5R, 6S) -2- (5-acetyl-7-methylthioimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl In the same way as in Example la), 168 mg of (1S, 5R, 6S) -2- (5-acetyl-7-methylthioimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) - 1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl from 211 mg of (IR, 3R, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2-oxo-l-carbapenam-3-carboxylate of 4-nitrobenzyl and 280 mg of 5-acetyl-7-methylthio-2- (tri-n-butylstannyl) -imidazo [5, 1-b] thiazole. NMR (CDC13) d: 1.34 (3H, d, J = 7.3 Hz), 1.40 (3H, d, J = 6. 1 Hz), 2.51 (3H, s), 2.66 (3H, s), 3.39 (1H, m), 3.66 (1H, m), 4.33 (1H, m), 4.39 (1H, dd, Ji = 9.5 Hz, Jz = 2, 1 Hz), . 31 (1H, d, J = 13.6 Hz), 5.55 (1H, d, J = 13.6 Hz), 7.68 (2H, d, J = 8.7 Hz), 8.24 (2H, d, J = 8.7 Hz), 8.81 (1H, s) b) (1S, 5R, 6S) -2- (5-acetyl-7-methylthioimidazo [ 5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate sodium In the same way as in the example 1-b), 29 mg of the title compound was obtained from 54 mg of (1S, 5R, 6S) -2- (5-acetyl-7-methylthio-imidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em- 3-carboxylic acid 4-nitrobenzyl NMR (D20) d: (HOD = 4.65 ppm): 1.14 (3H, d, J = 7.3 Hz), 1.23 (3H, d, J = 6.3 Hz), 2.35 (3H, s) , 2.47 (3H, s), 3.42 (1H, m), 3.55 (1H, m), 4.18 (1H, m), 4.25 (1H, m), 8.30 (1H, s) Example 148 (SS, 5R, 6S ) -2- [3, 7-bis (methylthio) -imidazo [5, 1-b] thiazol-2-yl] -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2 sodium a-3-carboxylate a) (1S.5R, 6S) -2- [3, 5-bis (methylthio) -imidazo [5, 1-b] thiazol-2-yl) -6- ((IR ) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 4-nitrobenzyl In the same manner as in Example la), 489 mg of (1S, 5R, 6S) - 2- [3,7-bis (methylthio) -imidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em -3-carboxylic acid 4-nitrobenzyl from 724 mg of (IR, 3R, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-ethyl-2-oxo-l-carbapenam-3- 4-nitrobenzyl carboxylate and 1.11 g of 3,7-b is (methylthio) -2- (tri-n-butylstannyl) -imidazo [5, 1-b]} thiazole NMR (CDC13) d: 1.22 (3H, d, J = 7.4 Hz), 1.39 (3H, d, J = 6.2 Hz), 2.28 (3H, s), 2.46 (3H, s), 3.4-3.5 (2H, m), 4.3-4.4 (1H,), 4.48 (1H, dd, Jx = 10.4 Hz, J2 = 3.3 Hz), 5.21 (1H, d, J = 163.4 Hz), 5.41 (1H, d, J = 13.4 Hz ), 7.53 (2H, s, J = 8.8 Hz), 8.03 (1H, s), 8.16 (2H, d, J = 8.8 Hz) b) (1S, 5R, 6S) -2- [3, 7-bis (Methylthio) -imidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate sodium The compound The title (70.6 mg) was obtained from 157 mg of (IS, 5R, 6S) -2- [3,7-bis (methylthio) -imidazo [5, 1-b] thiazol-2-yl) - 6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl in the same manner as in Example 1-b), except that the purification was carried out by column chromatography on Cosmosil 40C18-PREP (10% aqueous methanol). NMR (D20) d: (HOD = 4.80 ppm): 1.13 (3E, d, J = 7.2 Hz), 1. 31 (3H, d, J = 6.4 Hz), 2.34 (3H, s), 2.36 (3H, s), 3.35- 3.5 (1H, m), 3.54 (1H, dd, J_. = 5.9 Hz, J2 = 3.0 Hz), 4.2-4.35 (1H, m), 4.37 (1H, dd, Jx = 9.9 Hz, J2 = 2.9 Hz), 8.30 (1H, s) Example 149 (SS, 5R, 6S) -2- (5-acetyl-7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl- sodium l-carbapen-2-em-3-carboxylate a) (SS, 5R, 6S) -2- (5-acetyl-7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -6- ( (IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl (S, 5R, 6S) -2- (5-acetyl-7-methanesulfonylimidazo [5 , 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl (54 mg) thereof as in Example 44-b), except that 52 mg of (SS, 5R, 6S) -2- (acetyl-7-methylthioimidazo [5, 1-b] thiazol-2-yl) -6- ( (IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl and 115 mg of ozone as the starting compounds. The product of the reaction was purified by column chromatography on silica gel (dichloromethane: methanol = 20: 1 to 10: 1). NMR (CDC1) d: 1.34 (3H, d, J = 7.3 Hz), 1.40 (3H, d, J = 6.1 Hz), 2.71 (3H, s), 3.26 (3H, s), 3.40 (1H, m) , 3.64 (1H, m), 4.33 (1H, m), 4.43 (1H, dd, Ji = 9. "Hz, J2 = 1.9 Hz), 5.31 (1H, d, J = 13.4 Hz), 5.54 (1H, d, J = 13.4 Hz), 7.68 (2H, d, J = 9.1 Hz), 8.24 (2H, d, J = 9.1 Hz), 8.80 (1H, s) b) (SS, 5R, 6S) -2- (5-acetyl-7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-meryl-l-carbapen-2-em-3-carboxylate from Sodium In the same manner as in Example 1-b, 15 mg of the title compound was obtained from 53 mg of (1S, 5R, 6S) -2- (5-acetyl-7-methanesulfonylimidazo [5, 1-] b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl NMR (D20) d: (HOD = 4.65 ppm): 1.12 (3H, d, J = 7.3 Hz), 1.20 (3H, d, J = 6.4 Hz), 2.54 (3H, s), 3.24 (3H, s), 3.42 (1H, dd, Ji = 6.2 Hz, J2 = 2.8 Hz), 3.60 (1H, m), 4.15 (1H, m), 4.22 (1H, dd, Jx = 9.3 Hz, J2 = 2.7 Hz, 8.43 (1H, s) Example 150 (ÍS, 5R, 6S) -2- (5-bromine -7-methylthioylimidazo. 5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate • sodium a) (SS, 5R, 6S) -2- (5-bromo-7-methylthioylimio-azo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl- l-carbapen-2-em-3-carboxylic acid 4-nitrobenzyl It was dissolved (1S, 5R, 6S) -6- ((IR) -hydroxyethyl) -l-methyl-2- (7-methylthioylimidazo- [5,1] -b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 4-nitrobenzyl ester (77 mg) in 5 ml of benzene at room temperature. N-bromosuccinimide (33 mg) and 2 mg of 2, 2'-azobis (isobutyronitrile) were added to the solution. The mixture was stirred for 10 minutes. Dichloromethane (10 ml) and 10 ml of a saturated saline solution were added, followed by separation. The organic layer was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography on silica gel (diclotromethane: methanol = 20: 1) to provide 70 mg of (SS, 5R, 6S) -2- (5-bromo-7-methylthioylimidazo [5, 1-b ] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl. NMR (CDC13) d: 1.31 (3H, d, J = 7.3 Hz), 1.40 (3H, d, J = 6.3 Hz), 2.43 (3H, s), 3.38 (lH, m), 3.48 (1H, m) , 4.32 (1H, m), 4.38 (1H, dd, J2 = 9.8 Hz, Jz = 2.7 Hz), 5.29 (1H, d, J = 13.4 Hz), 5.55 (1H, d, J = 13.4 Hz), 7.68 (2H, d, J = 8.5 Hz), 8.03 (1H, s), 8.25 (2H, d, J = 8.5 Hz) b) (1S, 5R, 6S) -2- (5-bromo-7-methylthioylimidazo [ 5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate sodium In the same way as in the example 1-b), 14 mg of the title compound was obtained from 68 mg of (1S, 5R, 6S) -2- (5-bromo-7-methylthioylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl. NMR (D20) d: (HOD = 4.65 ppm): 1.12 (3H, d, J = 7.3 Hz), 1.19 (3H, d, J = 6.4 Hz), 2.23 (3H, s), 3.40 (1H, dd, Ji = 9.8 Hz, J2 = 2.7 Hz), 3.48 (1H, m), 4.13-4.22 (1H, m), 7.60 (1H , s) Example 151 (5R, 6S) -2- (5-Acetyl-7-methylthioylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-carbapen -2-em-3-carboxylic acid sodium a) (5R, 6S) -2- (5-acetyl-7-methylthioylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1 -hydroxyethyl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl In the same manner as in Example la), 147 mg of (5R, 6S) -2- (5-acetyl-7- were obtained methylthioylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl from 174 mg of (3R) , 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2-oxo-l-carbapenam-3-carboxylate of 4-nitrobenzyl and 250 mg of 5-acetyl-7-methylthio-2- (tri- n-butylstannyl) imidazo [5, 1-b] thiazole. NMR (CDC13) d: 1.40 (3H, d, J = 6.3 Hz), 2.51 (3H, s), 2.66 (3H, s), 3.33-3.52 (total 3H, m), 4.29-4.40 (total 2H, m ), 5.34 (1H, d, J = 13.4 Hz), 5.57 (1H, d, J = 13.4 Hz), 7.70 (2H, d, J = 8.7 Hz), 8.25 (2H, d, J = 8.7 Hz), 8.67 (1H, s) b) (5R, 6S) -2- (5-acetyl-7-methylthioylimidazo [5, 1-b] thiazol-2-yl) -6- ((lR) -l-hydroxyethyl) - sodium l-carbapen-2-em-3-carboxylate In the same manner as in example 1-b), 21 mg of the title compound was obtained from 80 mg of (5R, 6S) -2- ( -acetyl-7-methylthioylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl NMR (D20) ) d: (HOD = 4.65 ppm): 1.21 (3H, d, J = 6.4 Hz), 2.29 (3H, s), 2.35 (3H, s), 2.95-3.14 (2H, r.), 3.46 (1H, dd, Ji = 6.1 Hz, J2 = 2.9 Hz), 4.10-4.18 (2H, m), 7.52 (1H, s) Example 152 (SS, 5R, 6S) -2- (5-cyano-7-methylthioylimidazo [5 , 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate sodium a) (ΔS, 5R, 6S) -2- (5-ci an-7-methylthioylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl In the same manner as in Example la), 91 mg of (ΔS, 5R, 6S) -2- (5-cyano-7-methylthioylimidazo [5, 1-b] thiazol-2-yl) -6- was obtained ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl from 181 mg of (IR, 3R, 5R, 6S) -6- ((IR ) -1-hydroxyethyl) -l-methyl-2-oxo-l-carbapenam-3-carboxylate of 4-nitrobenzyl and 238 mg of 5-cyano-7-methylthio-2- (tri-n-butylstannyl) -imidazo [ 5, 1-b] thiazole. NMR (CDC13) d: 1.34 (3H, d, J = 7.3 Hz), 1.40 (3H, d, J = 6.1 Hz), 2.51 (3H, s), 3.40 (1H, m), 3.54 (1H, m) , 4.32 (1H,), 4.42 (1H, dd, J_. = 9.5 Hz, J2 = 2.8 Hz), 5.31 (1H, d, J = 13.7 Hz), 5.54 (1H, d, J = 13.7 Hz), 7.69 (2H, d, J = 8.2 Hz), 8.26 (total 3H, m) b) (ÍS, 5R, 6S) -2- (5-cyano-7-methylthioylimidazo [5, 1-b] thiazol-2-yl) ) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate sodium In the same manner as in Example 1-b), 19 mg of the compound were obtained Title from (SS, 5R, 6S) -2- (5-cyano-7-methylthioylimidazo [5, lb] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl. NMR (DMSO-dβ) d: 1.10 (3H, d, J = 7.1 Hz), 1.16 (3H, d, J = 6.4 Hz), 2.41 (3H, s), 3.11 (1H, dd, Ji = 6.8 Hz, J2 = 2.6 Hz), 3.56 (1H, m), 3.92 (1H, m), 4.03 (1H, dd, Jx = 9.2 Hz, J2 = 2.7 Hz), 5.01 (1H, d, J = 5.1 Hz), 8.31 (1H, s) Example 153 (5R, 6S) -2- [3, 7-bis (methylthio) imidazo [5, 1-b] thiazol-2-yl] -6- ((IR) -1-hydroxyethyl) sodium l-carbapen-2-em-3-carboxylate a) (5R, 6S) -2- [3, 7-bis (methylthio) imidazo [5, 1-b] thiazol-2-yl] -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl In the same manner as in Example la), 360 mg of (5R, 6S) -2- [ 3, 7-bis (methylthio) imidazo [5, 1-b] thiazol-2-yl] -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl from 645 mg of (3R, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2-oxo-l-carbapenam-3-carboxylate of 4-nitrobenzyl and 990 mg of 3, 7-bis (methylthio) -2- (tri-n-butylstannyl) imidazo- [5, 1-b] thiazole. NMR (CDC13) d: 1.40 (3H, d, J = 6.3 Hz), 2.31 (3H, s), 2.44 (3H, s), 3.2-3.4 (2H, m), 3.41 (1H, dd, Ji = 6.5 Hz, J2 = 3.1 Hz), 4.25-4.4 (1H, mj, 4.4 -4.5 (1H, m), 5.25 (1H, d, J = 13.3 Hz), 5.40 (1H, d, J = 13.3 Hz), 7.53 (2H, d, J = 8.8 Hz), 8.02 (1H, s) , 8.15 (2H, d, J = 8.8 Hz) b) (5R, 6S) -2- [3, 7-bis (methylthio) imidazo [5, 1-b] thiazol-2-yl] -6- (( IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate sodium The title compound (74.1 mg) was obtained from 145.7 mg of (5R, 6S) -2- [3, 7- bis (methylthio) imidazo [5, 1-b] thiazol-2-yl] -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl in the same manner in Example 1-b), except that the purification was carried out by column chromatography on Cosmosil 40C18-PREP (5% aqueous methanol). NMR (D20) d: (HOD = 4.80 ppm): 1.30 (3H, d, J = 6.5 Hz), 2.35 (6H, s), 3.16 (1H, dd, Ji = 17.1 Hz, J2 = 10.2 Hz), 3.41 (1H, dd, Jj = 17.1 Hz, J2 = 8.3 Hz), 3.57 (1H, dd, Jx = 5.8 Hz, J2 = 2.8 Hz), 4.2-4.4 (2H, m), 8.28 (1H, s) Example 154 (SS, 5R, 6S) -2- (5-chloro-7-methylthioimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-1 sodium carbapene-2-em-3-carboxylate a) (SS, 5R, 6S) -2- (5-chloro-7-methylthioimidazo [5, 1-b] thiazol-2-yl) -6- (( IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl It was dissolved (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l -methyl-2- (7- ethylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 4-nitrobenzyl ester (109 mg) in 10 ml of benzene at room temperature . N-chlorosuccinimide (30 mg) and 2 mg of 2,2'-azobis (isobutyronitrile) were added to the solution. The mixture was stirred for 10 minutes. Dichloromethane (10 ml) and 10 ml of a semi-saturated salt solution were added thereto, followed by separation. The organic layer was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography on silica gel (dichloromethane: methanol = 20: 1) to provide 32 mg of (SS, 5R, 6S) -2- (5-chloro-7-methylthioimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l- carbapen-2-em-3-carboxylate of 4-nitrobenzyl. NMR (CDC13) d: 1.34 (3H, d, J = 7.3 Hz), 1.40 (3H, d, J = 6.1 Hz), 2.51 (3H, s), 3.40 (1H, m), 3.54 (1H, m) , 4.32 (1H, m), 4.42 (1H, dd, Ji = 9.5 Hz, J2 = 2.8 Hz), 5.31 (1H, d, J = 13.7 Hz), 5.54 (1H, d, J = 13.7 Hz), 7.69 (2H, d, J = 8.2 Hz), 8.26 (3H, m) b) (SS, 5R, 6S) -2- (5-chloro-7-methylthioimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate sodium In the same manner as in example 1-b), 2 mg of the compound of the title from 30 mg of (IS, 5R, 6S) -2- (5-chloro-7-methylthioimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l -methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl. NMR (D20) d: (HOD = 4.65 ppm): 1.10 (3H, d, J = 7.3 Hz), 1.18 (3h, d, J = 6.3 Hz), 2.21 (3H, s), 3.36-3.48 (2H, m), 4.10-4.20 (2H, m), 7.60 (1H, s) Example 155 (5R, 6S) -2- (5-cyano-7-methylthioimidazo [5, 1-b] thiazol-2-yl) - 6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylic acid sodium a) (5R, 6S) -2- (5-cyano-7-methylthioimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl In the same manner as in example la), 189 mg of (5R, 6S) -2- (5-cyano-7-methylthioimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em- 4-Nitrobenzyl 3-carboxylate from 188 mg of (3R, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2-oxo-l-carbapenam-3-carboxylate of 4-nitrobenzyl and 262 mg of 5-cyano-7-methylthio-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole.

NMR (CDCI3) d: 1.40 (3H, d, J = 6.3 Hz), 2.51 (3H, s), 3.34-3.42 (3H, m), 4.29-4.42 (2H, m), 5.34 (1H, d, J = 13.5 Hz), 5.56 (1H, d, J = 13.5 Hz), 7.71 (2H, d, J = 8.0 Hz), 8.10 (1H, s), 8.26 (2H, d, J = 8.0 Hz) b) ( 5R, 6S) -2- (5-cyano-7-methylthioimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3 sodium carboxylate In the same manner as in example 1-b), 36 mg of the title compound was obtained from 94 mg of (5R, 6S) -2- (5-cyano-7-methylthioimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl NMR (D20) d: (HOD = 4.65 ppm) : 1.18 (3H, d, J = 6.6 Hz), 2.31 (3H, s), 3.17 (2H, m), 3.41 (1H, dd, Ji = 6.0 Hz, J2 = 3.0 Hz), 4.10-4.20 ( 2H, m), 7.77 (1H, s) Example 156 (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- [7- "(1-propyl) thioimidazo [ Sodium 5, 1-b] thiazol-2-yl] -l-carbapen-2-em-3-carboxylate a) (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l- methyl-2- [! - "(1-propyl) thioimidazo [5, 1-b] thiazol-2-yl] -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl In the same manner as in Example la), 369 mg of (IS, 5R, 6S) -6- (( IR) -1-hydroxyethyl) -l-methyl-2- [7- "(1-propyl) thioimidazo [5, 1-b] thiazol-2-yl] -l-carbapen-2-em-3-carboxylate from 4-nitrobenzyl from 724 mg of (IR, 3R, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2-oxo-l-carbapenam-3-carboxylate of 4-nitrobenzyl and 1.07 mg of 7- (1-propyl) thio-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole. NMR (CDC13) d: 0.99 (3H, t, J = 7.4 Hz), 1:31 (3H, d, J = 7. 1 Hz), 1.40 (3H, d, J = 6.3 Hz), 1.5-1.7 (2H, m), 2.75-2.85 (2H, m), 3.37 (1H, dd, Ji = 6.3 Hz, J2 = 2.7 Hz) , 3.4-3.55 (1H, m), 4.3-4.4 (2H, m), 5.28 (1H, d, J = 13.7 Hz), 5.53 (1H, d, J = 13.7 Hz), 7.68 (2H, d, J = 8.5 Hz), 8.02 (1H, s), 8. 25 (2H, d, J = 8.5 Hz), 8.31 (1H, s) b) (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- [7- " Sodium (1-propyl) thioimidazo [5, 1-b] thiazol-2-yl] -l-carbapen-2-em-3-carboxylate The title compound (58.2 mg) was obtained from 132 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- [7- "(1-propyl) thioimidazo [5, 1-b] thiazole-2- il] -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl in the same manner as in Example 1-b), except that the purification was carried out in column chromatography on Cosmosil 40C18-PREP (aqueous methanol 10%). NMR (D20) d: (HOD = 4.80 ppm): 0.93 (3H, t, J = 7.2 Hz), 1.23 (3H, d, J = 7.3 Hz), 1.21 (3H, d, J = 6.3 Hz), 1.4-1.6 (2H, m), 2.65-2.75 (2H, m), 3.45-3.6 (2H, m), 4.2-4.35 (2H, m), 7.86 (1H, s), 8.09 (1H, s) Example 157 (5R , 6S) -6- ((1R) -l-hydroxyethyl) -2- (7- (1-propyl) thioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3 sodium carboxylate a) (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7- (1-propyl) thioimidazo [5, 1-b] thiazol-2-yl) -l -carbapen-2-em-3-carboxylate of 4-nitrobenzyl In the same manner as in example la), 369 mg of (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- were obtained (7- (1-propyl) thioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl from 524 mg of (3R, 5R, 6S ) -6- ((IR) -1-hydroxyethyl) -2-oxo-l-carbapenam-3-carboxylate of 4-nitrobenzyl and 770 mg of 7- (1-propyl) thio-2- (tri-n-butylstannyl) ) imidazo [5, 1-b] thiazole. NMR (CDC13) d: 0.98 (3H, t, J = 7.4 Hz), 1.40 (3H, d, J = 6.2 Hz), 1.55-1.7 (2H, m), 2.75-2.85 (2H, m), 3.3- 3.4 (3H, m), 4.25-4.4 (2H, m), 5.32 (1H, d, J = 13.5 Hz), 5.55 (1H, d, J = 13.5 Hz), 7.70 (2H, d, J = 8.9 Hz ), 8.01 (1H, s), 8.21 (1H, s), 8.25 (2H, d, J = 8.5 Hz) b) (5R, 6S) -6- ((lR) -l-hydroxyethyl) -2- ( 7- (l-propyl) thioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate sodium The title compound (72.3 mg) was obtained from 161 mg of (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7- (1-propyl) thioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2- 4-nitrobenzyl em-3-carboxylate in the same manner as in Example 1-b), except for the purification was carried out by column chromatography on Cosmosil 40C18-PREP (10% aqueous methanol).

NMR (D20) d: (HOD = 4.80 ppm): 0.92 (3E, t, J = 7.4 Hz), 1.31 (3H, d, J = 6.3 Hz), 1.4-1.55 (2H, m), 2.72 (2H, t, J = 7.2 Hz), 3.15-3.3 (2H, m), 3.49 (1H, dd, J: = 6.1 Hz, J2 = 3.0 Hz), 4.2-4.3 (2H, m), 7.66 (1H, s) , 8.04 (1H, s) Example 158 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-isopropylthioimidazo [5, 1-b] thiazol-2-yl) -l sodium methyl-l-carbapen-2-em-3-carboxylate a) (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-isopropylthioimidazo [5, 1-b] ] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl In the same manner as in Example la), 557 mg of (1S, 5R, 6S) were obtained -6- ((IR) -1-hydroxyethyl) -2- (7-isopropylthioimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate of 4 -nitrobenzyl from 629 mg of (IR, 3R, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2-oxo-l-carbapenam-3-carboxylate of 4-nitrobenzyl and 890 mg of 7-isopropylthio-2- (tri-n-butylstannyl) imidazo- [5, 1-b]} thiazole NMR (CDC13) d: 1.28 (6H, d, J = 6.7 Hz), 1.31 (3H, d, J = 7.2 Hz), 1.40 (3H, d, J = 6.3 Hz), 3.28 (1H, sept, J = 6.7 Hz), 3.37 (1H, dd, Ji = 6.6 Hz, J2 = 2.9 Hz), 3.4-3.5 (1H, m), 4.3-4.4 (2H, m), 5.28 (1H, d, J = 13.7 Hz) , 5.53 (1H, d, J = 13.7 Hz), 7.68 (2H, d, J = 8.8 Hz), 8.03 (1H, s), 8.25 (2H, d, J = 8.8 Hz), 8.31 (1H, s) (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-isopropylthioimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2- sodium em-3-carboxylate The title compound (85.1 mg) was obtained from 163 mg of (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-isopropylthioimidazo [ 5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl in the same manner as in Example 1-b), except that the purification was carried out by column chromatography on Cosmosil 40C18-PREP (10% aqueous methanol). NMR (D20) d: (HOD = 4.80 ppm): 1.18 (6H, d, J = 6.8 Hz), 1.22 (3H, d, J = 7.2 Hz), 1.31 (3H, d, J = 6.63 Hz), 3.21 (1H, sept, J = 6.8 Hz), 3.45-3.6 (2H, m), 4.2-4.35 (2H, m), 7.86 (1H, s), 8.10 (1H, s) Example 159 (5R, 6S) - 6- ((IR) -1-hydroxyethyl) -2- (7-isopropylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid sodium a) (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-isopropylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl In the same manner as in Example la), 261 mg of (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-isopropylthioimidazo [5, 1-b] thiazole-2 was obtained -l) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl from 348 mg of (3R, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2-oxo-l-carbapenam-3-carboxylate of 4-nitrobenzyl and 506 mg of 7-isopropylthio-2- (tri-n-butylstannyl) imidazo [5, 1-b] thiazole. NMR (CDCI3) d: 1.27 (6H, d, J = 6.7 Hz), 1.40 (3H, d, J = 6.3 Hz), 3.2-3.4 (4H, m), 4.25-4.4 (2H,), 5.32 (1H, d, J = 13.7 Hz), 5.55 (1H, d, J = 13.7 Hz), 7.69 (2H, d, J = 8.8 Hz), 8.02 (1H, s), 8.21 (1H, s), 8.25 (2H, d, J = 8.8 Hz) b) (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-isopropylthioimidazo [5, 1-b] thiazol-2-yl) - sodium l-carbapen-2-em-3-carboxylate The title compound (55.1 mg) was obtained from 110 mg of (5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- ( 7-isopropylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of 4-nitrobenzyl in the same manner as in Example 1-b), except that the purification was carried out by column chromatography on Cosmosil 40C18-PREP (5% aqueous methanol). NMR (D20) d: (HOD = 4.80 ppm): 1.18 (6H, d, J = 6.8 Hz), 1.31 (3H, d, J = 6.5 Hz), 3.15-3.35 (3H, m), 3.49 (1H, dd, Ji = 6.0 Hz, J2 = 3.0 Hz), 4.2-4.3 (2H, m), 7.66 (1H, s), 8.06 (1H, s) Example 160 (ÍS, 5R, 6S) -6- ((IR ) -1-hydroxyethyl) -2- (7-methanesulsonyl-5-methylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 1-methylcyclohexylcarbonyloxymethyl ester In the same manner as in Example 2, 24 mg of the title compound was obtained from 21 mg of (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methansulsonyl Sodium 5-methylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate and 27 mg of 1-methylcyclohexylcarbonyloxymethyl iodide. NMR (CDC13) d: 1.15 (3H, s), 1.27 (3H, d, J = 7.2 Hz), 1.37 (3H, d, J = 6.2 Hz), 1.25-1.70 (8H, m), 1.95-2.03 ( 2H, m), 2.69 (3H, s), 3.19 (3H, s), 3.34 (1H, dd, Ji = 7.5 Hz, J2 = 2.8 Hz), 3.44 (1H, m), 4.29 (1H, m), 4.36 (1H, dd, Ji = 9.8 Hz, J2 = 2.8 Hz), 5.90, 5.98 (2H, Abq, J = 5.6 Hz), 8.27 (1H, s) MS (TPS): 580 (M ++ H) Example 161 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulsonyl-5-methylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-1 -carbapen-2-em-3-carboxylic acid 1-methylcyclohexylcarbonyloxymethyl ester (a mixture of diastereomers) In the same manner as in Example 2, 21 mg of the title compound was obtained from 23 mg of (SS, 5R, 6S ) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulsonyl-5-methylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em- Sodium 3-carboxylate and 0.025 ml of 1- (cyclohexyloxycarbonyloxy) ethyl iodide.

NMR (CDCI3) d: 1.25-1.40 (8H, s), 1.50-1.95 (8H, m), 1.60, 1.65 (total 3H, each d, J = 5.5 Hz), 2.65 (3H, s), 3.20 (3H , s), 3.34 (1H, m), 3.44 (1H, m), 3.62 (1H, m), 4.27 (1H, m), 4.35 (1H,), 4.65 (1H, m), 6.94 (1H, m ), 8.38, 8.43 (total 1H, each s) MS (TSP): 596 (M ++ H) Example 162 (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7 methanesulsonyl-5-methylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylic acid cyclohexyloxycarbonyloxymethyl ester. In the same manner as in Example 2, 24 were obtained. mg of the compound from 20 mg of (13, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methansulsonyl-5-methylimidazo [5, 1-b] thiazole-2- il) -l-methyl-l-carbapen-2-em-3-carboxylate sodium and 0.026 ml of cyclohexyloxycarbonyloxymethyl iodide. NMR (CDC13) d: 1.26 (3H, d, J = 7.2 Hz), 1.36 (3H, d, J = 6.2 Hz), 1.42-1.48 (4H, m), 1.68-1.98 (6H,), 2.67 (3H , m), 3.20 (3H, s), 3.34 (1H, dd, Jx = 6.8 Hz, J2 = 2.9 Hz), 3.45 (1H, m), 4.30 (1H, m), 4.35 (1H, dd, Jx = 9.7 Hz, J2 = 2.9 Hz), 4.66 (1H, m), 5.88, 5.97 (2H, Abq, J = 5.8 Hz) 8.37 (1H, s) Example 163 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulsonyl-5-methylimidazo [5, 1-b] thiazol-2-yl) 3-phthalidyl-l-methyl-l-carbapen-2-em-3-carboxylate (a mixture of diastereomers) In the same manner as in Example 2, 17 mg of the title compound was obtained from 22 ng of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methansulsonyl Sodium 5-r-methylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate and 22 mg of 3-phthalidyl bromide.

NMR (CDCI3) d: 1.26 (3H, m), 1.35 (3H, m), 2.60, 2.67 (total 3H, each s), 3.18, 3.20 (total 3H, each s), 3.35 (1H, m), 3.49 (1H, m), 4.23 (1H, m), 4.37 (1H, m), 7.45, 7.47 (total 1H, each s), 7.65-7.80 (3H,), 7.92 (1H, m), 8.14, 8.43 ( total 1H, each s) MS (TSP): 558 (M ++ H) Example 164 (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methansulsonyl-5-methylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 5-methyl-2-oxo-l, 3-dioxolen-4-ylmethyl thereof As in example 2, 18 mg of the title compound was obtained from 22 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulsonyl-5- sodium methy1imidazo [5,1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate and 19 mg of 5-methyl-2-oxo-l, 3-bromide dioxolen-4-ylmethyl. NMR (CDCI3) d: 1.29 (3H, d, J = 7.2 Hz), 1.37 (3H, d, J = 6.3 Hz), 2.22 (3H, s), 2.66 (3H, s), 3.20 (3H, s) , 3.35 (1H, dd, Ji = 6.6 Hz, J2 = 2.8 Hz), 3.48 (1H, m), 4.29 (1H, m), 4.37 (1H, dd, Ji = 9.7 Hz, J2 = 2.8 Hz), 5.02 , 5.10 (2H, Abq, J = 14.0 Hz), 8.18 (1H, s) Example 165 (ÍS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulsonyl-5- methylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate of (Z) -2- (3-phthalidylidene) ethyl In the same manner as in the Example 2, 25 mg of the title compound was obtained from 24 μg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulsonyl-5-retilimidazo [5 Sodium 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate and 26 mg of (Z) -2- (3-phthalidylidene) ethyl bromide. NMR (CDC13) d: 1.28 (3H, d, J = 7.4 Hz), 1.37 (3H, d, J = 6.2 Hz), 2.65 (3H, s), 3.19 (3H, s), 3.34 (1H, dd, Jx = 6.5 Hz, J2 = 2.7 Hz), 3.45 (1H, m), 4.30 (1H, m), 4.36 (1H, dd, Ji = 9.6 Hz, J2 = 2.7 Hz), 5.23 (2H, m), 5.84 (1H, m), 7.60 (1H, m), 7.72 (2H, m), 7.90 (1H, m), 8.33 (1H, s) MS (TSP): 584 (M ++ H) Example 166 (IS, 5R, 6S) -2- (7-acetyl-5-methylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2 -em-3- (ethoxycarbonyloxy) ethyl carboxylate (a mixture of diastereomers) In the same manner as in Example 2, 24 mg of the title compound was obtained from 23 mg of (SS, 5R, 6S) -2- (7-Acetyl-5-methylimidazo [5, 1-b] thiazol-2-yl) -6- ((1R) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3 sodium carboxylate and 0.030 ml of 1- (ethoxycarbonyloxy) ethyl iodide. NMR (CDCI3) d: 1.27 (3H,), 1.37 (6H, m), 1.60 (3H, m), 2.58 (3H, s), 2.67 (3H, s), 3.33 (1H, m), 3.48 (1H, m), 4.20-4.30 (4H, m), 4.37 (1H, m), 6.94 ( 1H, m), 8.44, 8.48 (total 1H, each s) MS (TSP): 506 (M ++ H) Example 167 (IS, 5R, 6S) -2- (7-acetyl-5-methylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboc acid 1- (cyclohexycarbonyloxy) ethyl ester (a mixture of diastereomers ) In the same manner as in Example 2, 19 mg of the title compound was obtained from 23 mg of (1S, 5R, 6S) -2- (7-acetyl-5-methylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carbote sodium and 0.034 ml of 1- (cyclohexycarbonyloxy) ethyl iodide. NMR (CDC1) d: 1.27 (3H, m), 1.30-1.95 (10H, m), 1.37 (3H, m), 1.65 (3H, m), 2.58 (3H, s), 2.67 (3H, s), 3.34 (1H, m), 3.50 (1H, m), 4.28 (1H, m), 4.35 (1H, m), 4.64 (1H, m), 6.94 (1H, m), 8.45, 8.48 (total 1H, each s) MS (TSP): 560 (M ++ H) Example 168 (1S, 5R, 6S) -2- (7-acetyl-5-methylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboc acid cyclohexycarbonyloxymethyl ester In the same manner as in Example 2, 25 mg of the title compound was obtained from 21 mg of (ΔS, 5R, 6S) -2- (7-acetyl-5-methylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-1 sodium carbapene-2-em-3-carbote and 29 mg of cyclohexycarbonyloxymethyl iodide. NMR (CDCI3) d: 1.27 (3H, d, J = 7.2 Hz), 1.37 (3H, d, J = 6.3 Hz), 1.35-2.00 (10H, m), 2.58 (3H, s), 2.68 (3H, s), 3.34 (1H, dd, Ji = 6.5 Hz, J2 = 2.7 Hz), 3.47 (1H, m), 4.30 (1H,), 4.37 (1H, dd, J_ = 9.8 Hz, J2 = 2.7 Hz), 4.65 (1H, m), . 88, 5.97 (2H, Abq, J = 5.9 Hz), 8.42 (1H, s) MS (TSP): 546 (M ++ H) Example 169 (SS, 5R, 6S) -2- (7-acetyl-5) -methylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) 1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate from 3-phthalidyl (a mixture of diastereomers) In the same manner as in Example 2, 22 mg of the title compound was obtained from 20 mg of (1S, 5R, 6S) -2- (7-acetyl-5- methylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate sodium and 22 mg of 3-phthalidyl bromide. NMR (CDC13) d: 1.28 (3H, m), 1.33 (3H, m), 2.12 (1H, m), 2.57, 2.59 (total 3H, each s), 2.64, 2.69 (total 3H, each s), 3. 36 (1H, m), 3.51 (1H, m), 4.24 (1H, m), 4.37 (1H, m), 7.46, 7. 48 (total 1H, each s), 7.23-7.70 (3H, m), 7.93 (1H, m), 8. 25, 8.54 (total 1H, each s) MS (TSP): 522 (M ++ H) Example 170 (SS, 5R, 6S) -2- (7-acetyl-5-methylimidazo [5, 1-b] thiazole -2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate of -methyl-2-oxo-l, 3-dioxolen-4-ylmethyl In the same manner as in Example 2, 26 mg of the title compound was obtained from 22 mg of (1S, 5R, 6S) -2 - (7-Acetyl-5-methylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate of sodium and 20 mg of 5-methyl-2-oxo-l, 3-dioxolen-4-ylmethyl bromide. NMR (CDC13) d: 1.29 (3H, d, J = 7.1 Hz), 1.38 (3H, d, J = 6.3 Hz), 1.91 (1H, br.s), 2.22 (3H, s), 2.58 (3H, s), 2.68 (3H, s), 3.35 (1H, dd, Ji = 6.5 Hz, J2 = 2.7 Hz), 3.50 (1H, m), 4.30 (1H, m), 4.37 (1H, dd, Ji = 9.5 Hz, J2 = 2.7 Hz), 4.99, 5.09 (2H, Abq, J = 13.7 Hz), 8.26 (1H, s) MS (TSP): 502 (M ++ H) Example 171 (1S, 5R, 6S) - 2- (7-acetyl-5-methylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3 cyclopentyloxycarbonyloxymethyl carboxylate In the same manner as in Example 2, 28 mg of the title compound was obtained from 23 mg of (SS, 5R, 6S) -2- (7-acetyl-5-methylimidazo [5,1- b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate sodium and 30 mg of cyclopentyloxycarbonyloxymethyl iodide. NMR (CDC13) d: 1.28 (3H, d, J = 7.2 Hz), 1.37 (3H, d, J = 6.3 Hz), 1.60-1.95 (8H, m), 2.58 (3H, s), 2.68 (3H, s), 3.40 (1H, dd, Ji = 6.6 Hz, J2 = 2.8 Hz), 3.49 (1H, m), 4.30 (1H, m), 4.39 (1H, dd, Ji = 9.9 Hz, J2 = 2.8 Hz) , 5.12 (1H, m), 5.87, 5.96 (2H, Abq, J = 5.8 Hz), 8.43 (1H, s) MS (TSP): 532 (M ++ H) Example 172 (SS, 5R, 6S) - 2- (7-acetylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate from 1 (pivaloyloxy) ethyl (a mixture of diastereomers) In the same manner as in Example 2, 331 mg of the title compound was obtained from 396 mg of (1S, 5R, 6S) -2- (7-acetylimidazo [5 , 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -1-methyl-l-carbapen-2-em-3-carboxylate sodium and 495 mg of 1- (iodide pivaloyloxy) ethyl. NMR (CDC13) d: 1.11, 1.17 (total 9H, each s), 1.22 (3H, m), 1.34 (3H, m), 1.50, 1.55 (total 3H, each d, J = 5.5 Hz), 2.56 (3H , s), 3.32 (1H, m), 3.45 (1H, m), 4.24 (1H, m), 4.37 (1H, m), 6.98 (1H, m), 8.01 (1H, s), 8.49, 8.51 ( total 1H, each s) MS (TSP): 504 (M + + H) Example 173 (SS, 5R, 6S) -2- (7-acetylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 1-methylcyclohexycarbonyloxymethi In the same manner as in Example 2, 301 mg of the title compound was obtained from 229 mg of (SS, 5R, 6S) -2- (7-acetylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -1-methyl-1-carbapen Sodium 2-em-3-carboxylate and 253 mg of 1-methylcyclohexylcarbonyloxymethyl iodide. NMR (CDCI3) d: 0.90-1.54 (8H, m), 1.20 (3H, s), 1.27 (3H, d, J = 7.4 Hz), 1.35 (3H, d, J = 6.1 Hz), 1.95-2.01 ( 2H, m), 2.60 (3H, s), 3.35 (1H, dd, Jx = 6.5 Hz, J2 = 2.7 Hz), 3.49 (1H, m), 4.28 (1H, m), 4.39 (1H, dd, Ji = 9.7 Hz, Jz = 2.7 Hz), 5.89, 5.96 (2H, Abq, J = 5.5 Hz), 8.05 (1H, s), 8.48 (1H, s) MS (TSP): 560 (M ++ H) Example 174 (ÍS, 5R, 6S) -2- (7-acetylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em- Cyclohexylcarbonyloxymethyl 3-carboxylate In the same manner as in Example 2, 238 mg of the title compound were obta from 228 mg of (1S, 5R, 65) -2- (7-acetylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -1-methyl-l-carbapen-2-em-3-carboxylate sodium and 236 mg of cyclohexylcarbonyloxymethyl iodide. NMR (CDC13) d: 1.15-1.75 (8H, m), 1.28 (3H, d, J = 7.1 Hz), 1.37 (3H, d, J = 6.0 Hz), 1.80-1.95 (2H, m), 2.35 ( 1H, m), 2. 62 (3H, s), 3.35 (1H, dd, Ji = 6.5 Hz, J = 2.8 Hz), 3.49 (1H, m), 4.30 (1H, m), 4.39 (1H, dd, J_ = 9.6 Hz, J- = 2.8 Hz), 5.88, 5.96 (2H, Abq, J = 5.8 Hz), 8.05 (1H, s ), 8.51 (1H, s) MS (TSP): 516 (M + + H) Example 175 (SS, 5R, 6S) -2- (7-acetylimidazo [5, 1-b] thiazol-2-yl) -6- ( (IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 1- (cyclohexylcarbonyloxy) ethyl ester (a mixture of diastereomers) In the same manner as in Example 2, 286 were obtained mg of the title compound from 290 mg of (IS, 5R, 6S) -2- (7-acetylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) sodium l-methyl-l-carbapen-2-em-3-carboxylate and 338 mg of 1- (cyclohexylcarbonyloxy) ethyl iodide. NMR (CDCI3) d: 1.25 (3H, m), 1.20-1.95 (8H,), 1.36 (3H,), 1.53, 1.58 (total 3H, each d, J = 5.5 Hz), 2.25-2.38 (3H, s ), 3.10 (3H, s), 3.34 (1H, m), 3.46 (1H, m), 4.27 (1H,), 4.39 (1H, m), 7.01 (1H, m), 8.05 (1H, s), 8.30, 8.51 (total 1H, each s) MS (TSP): 560 (M ++ H) Example 176 (1S, 5R, 6S) -2- (7-acetylimidazo [5, lb] thiazol-2-yl) - 6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-hexanoyloxymethyl carboxylate In the same manner as in Example 2, 95.3 mg of the title compound was obtained from 94 mg of (SS, 5R, 6S) -2- (7-acetylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -1-methyl-1-carbapen Sodium 2-em-3-carboxylate and 109 mg of hexanoyloxymethyl iodide. NMR (CDCl 3) d: 0.87 (3H, t, J = 6.7 Hz), 1.2-1.35 (7H, m), 1.38 (3H, d, J = 6.3 Hz), 1.55-1.7 (2H, m), 2.37 ( 2H, t, J = 7. 7 Hz), 2.62 (3H, s), 3.36 (1H, dd, Jj. = 6.6 Hz, J; = 2.8 Hz), 3.45-3.6 (1H, m), 4.25-4.35 (1H, m), 4.39 ( 1H, dd, Ji = 9. 8 Hz, J2 = 2.8 Hz), 5.90 (1H, d, J = 5.7 Hz), 5.97 (1H, d, J = 5.7 Hz), 8.04 (1H, s), 8.54 (1H, s) MS (TSP) : 560 (MVH) Example 177 (1S, 5R, 6S) -2- (7-Acetylimidazo [5, lb] thiazol-2-yl) -6- ((1R) -1-hydroxyethyl) -l-methyl-1 2-ethylbutyryloxymethylcarbapene-2-em-3-carboxylate In the same manner as in Example 2, 229 mg of the title compound was obtained from 265 mg of (IS, 5R, 6S) -2- (7 -acetylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -1-methyl-l-carbapen-2-em-3-carboxylate sodium and 390 mg of iodide of 2-ethylbutyryloxymethyl. NMR (CDC13) d: 0.8-0.9 (6H, m), 1.28 (3H, d, J = 7.4 Hz), 1.36 (3H, d, J = 6.3 Hz), 1.45-1.7 (4H, m), 2.2- 2.3 (1H, m), 2.62 (3H, s), 3.36 (1H, dd, Ji = 6.8 Hz, J2 = 2.9 Hz), 3.45-3.55 (1H,), 4.25-4.35 (1H, m), 4.39 ( 1H, dd, J: = 9.8 Hz, J2 = 2.9 Hz), 5.95 (2H, s), 8.05 (lH, s), 8.52 (1H, s) MS (TSP): 504 (MVH) Example 178 (1S, 5R, 6S) -2- (7-acetylimidazo [5, lb] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate Cyclopentyloxycarbonyloxymethyl ester In the same manner as in Example 2, 297 mg of the title compound was obtained from 235 mg of (SS, 5R, 6S) -2- (7-acetylimidazo [5, 1-b] thiazole-2 -yl) -6- ((IR) -1-hydroxyethyl) -1-methyl-l-carbapen-2-em-3-carboxylate sodium and 249 mg of cyclopentyloxycarbonyloxymethyl iodide.

NMR (CDCI3) d: 1.27 (3H, d, J = 7.1 Hz), 1.35 (3H, d, J = 6.1 Hz), 1.55-1.85 (8H, m), 2.60 (3H, s), 3.35 (1H, dd, Ji = 6.3 Hz, J2 = 2.5 Hz), 3.49 (1H,), 4.29 (1H, m), 4.39 (1H, dd, Ji = 9.7 Hz, J2 = 2.5 Hz), 5.10 (1H, m), 5.87, 5.94 (2H, Abq, J = 5.8 Hz), 8.04 (1H, s), 8.55 (1H, s) MS (TSP): 518 (M ++ H) Example 179 (1S, 5R, 6S) -2 - (7-acetylimidazo [5, 1-b] thiazol-2-yl) -6- ((1R) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate of l- ( 3-pentyloxycarbonyloxy) ethyl (a mixture of diastereomers) In the same manner as in Example 2, 243 mg of the title compound was obtained from 246 mg of (IS, 5R, 6S) -2- (7-acetylimidazo [5, 1-b] thiazol-2-yl) ) -6- ((IR) -1-hydroxyethyl) -1-methyl-1-carbapen-2-em-3-carboxylate sodium and 300 mg of 1- (3-pentyloxycarbonyloxy) ethyl iodide. NMR (CDCI3) d: 0.82-0.95 (6H,), 1.26 (3H,), 1.36 (3H, m), 1.55-1.66 (7H, m), 2.61 (3H, s), 3.34 (1H, m), 3.48 (1H, m), 4.31 (1H, m), 4.35 (1H, m), 4.58 (1H, m), 6.93 (1H, m), 8.01 (1H, s), 8.58, 8.62 (total 1H, each s) MS (TSP): 534 (M ++ H) Example 180 (1S, 5R, 6S) - 2- (7-Acetylimidazo [5, 1-b] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylate of 3- pentyloxycarbonyloxymethyl In the same manner as in Example 2, 265 mg of the title compound was obtained from 218 mg of (IS, 5R, 6S) -2- (7-acetylimidazo [5, 1-b] thiazole-2- il) -6- ((IR) -1-hydroxyethyl) -1-methyl-1-carbapen-2-em-3-carboxylate sodium and 309 mg of 3-pentyloxycarbonyloxymethyl iodide. NMR (CDC13) d: 0.84 (6H, m), 1.25 (3H, d, J = 7.4 Hz), 1.33 (3H, d, J = 6.3 Hz), 1.56 (4H, m), 2.57 (3H, s), 3.33 (1H, dd, Ji = 6.8 Hz, J2 = 2.7 Hz), 3.47 (1H, m), 4.25 (1H, m), 4.37 (1H, dd, Ji = 9.6 Hz, J2 = 2.7 Hz), 4.56 (1H, m), 5.87, 5.93 (2H, Abq, J = 5.8 Hz), 8.03 (1H, s) 8.52 (1H, s) MS (TSP): 520 (M + H) Example 179 (SS, 5R, 6S) -2- (7-acetylimidazo [5, 1-b] thiazol-2-yl) -6 - ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylic acid cyclohexylmethoxycarbonyloxymethyl ester In the same manner as in Example 2, 317 mg of the title compound were obtained from 237 mg (SS, 5R, 6S) -2- (7-acetylimidazo [5, lb] thiazol-2-yl) -6- ((IR) -1-hydroxyethyl) -1-methyl-1-carbapen-2 sodium em-3-carboxylate and 369 mg of cyclohexylmethoxycarbonyloxymethyl iodide. NMR (CDCl 3) d: 0.90-1.30 (4H, m), 1.28 (3H, d, J = 7.1 Hz), 1.37 (3H, d, J = 6.2 Hz), 1.65-1.75 (6H, m), 2.15 ( 1H, br.s), 2.62 (3H, s), 3.36 (1H, dd, Ji = 6.4 Hz, J: = 2.8 Hz), 3.50 (1H, m), 3.98 (2H, d, J = 6.3 Hz), 4.30 (1H,), 4.39 (1H, dd, Ji = 9.6 Hz, J2 = 2.8 Hz), 5.90, 5.96 (2H, Abq, J = 5.8 Hz), 8.03 (1H, s), 8.57 (1H, s) MS (TSP): 546 (M ++ H) Example 182 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl ) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 1- (isobutyryloxy) ethyl ester (a mixture of diastereomers) In the same manner as in Example 2, 198 mg of the title compound was obtained from 289 mg of (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7 sodium methansulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate and 323 mg of 1- (isobutyryloxy) ethyl iodide. NMR (CDC13) d: 1.14 (3H, m), 1.19 (3H, m), 1.26 (3H, m), 1.36 (3H, m), 1.55, 1.60 (total 3H, each d, J = 5.5 Hz), 2.32 (1H, br.s), 2.68 (1H, m), 3.21 (3H, s), 3.33 (1H,), 3.46 (1H,), 4.27 (1H, m), 4.35 (1H, m), 7.03 ( 1H, m), 8.09 (1H, s), 8.51, 8.53 (total 1H, each s) MS (TSP): 526 (M ++ H) Example 183 (IS, 5R, 6S) -6- ((IR) 1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 1- (pivaloyloxy) ethyl ester (a mixture of diastereomers) In the same manner as in Example 2, 234 mg of the title compound was obtained from 361 mg of (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-Methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate sodium and 430 mg of 1- (pivaloyloxy) ethyl iodide. NMR (CDC13) d: 1.52, 1.21 (total 9H, each s), 1.25 (3H, m), 1. 35 (3H,), 1.53, 1.58 (total 3H, each d, J = 3.6 Hz), 3.19 (3H, s), 3.33 (1H, m), 3.46 (1H, m), 4.25 (IH, m), 4.34 (1H, m), 7.00 (1H, m), 8.10 (1H, s), 8.46, 8.49 (total 1H, each s) MS (TSP): 540 (MVH) Example 184 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) hexanoyloxymethyl-l-methyl-l-carbapen-2-em-3-carboxylate In the same manner as in Example 2, 217 mg of the title compound was obtained from 214 mg of (IS, 5R, 6S) - 6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate sodium and 265 mg of hexanoyloxymethyl iodide. NMR (CDCl 3) d: 0.87 (3H, t, J = 7.0 Hz), 1.2-1.3 (7H, m), 1. 37 (3H, d, J = 6.3 Hz), 1.55-1.7 (2H, m), 2.38 (2H, t, J = 7. 7 Hz), 3.24 (3H, s), 3.35 (1H, dd, J_. = 6.6 Hz, J2 = 2.7 Hz), 3.4-3.55 (1H, m), 4.25-4.35 (2H, m), 4.37 (1H , dd, Ji = 9. 8 Hz, J2 = 2.7 Hz), 5.89 (1H, d, J = 5.6 Hz), 5.96 (1H, d, J = 5.6 Hz), 8.19 (1H, s), 8.49 (1H, s) MS (TSP) : 540 (M ++ H) Example 185 (IS, 5R, 6S) - 6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) Cyclohexylcarbonyloxymethyl-l-methyl-l-carbapen-2-em-3-carboxylate In the same manner as in Example 2, 267 mg of the title compound were obtained from 219 mg of (SS, 5R, 6S) - 6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate sodium and 200 mg of cyclohexylcarbonyloxymethyl iodide. NMR (CDC13) d: 1.18-1.50 (4H, m), 1.27 (3H, d, J = 7.2 Hz), 1. 35 (3H, d, J = 6.3 Hz), 1.60-1.98 (6H, m), 2.35 (1H, m), 3.22 (3H, s), 3.34 (1H, dd, Jj. = 6.6 Hz, J2 = 2.8 Hz), 3.47 (1H,), 4.28 (1H, m), 4.36 (1H, dd, Ji = 9.7 Hz, J: = 2.8 Hz), 5.88, 5.95 (1H, ABq, J = 5.7 Hz), 8.12 (1H, s), 8.45 (1H, s) MS (TSP): 552 (M + H) Example 186 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-] b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylic acid cyclohexylacetoxy ethyl ester In the same manner as in Example 2, 272 mg of the title compound were obtained from 212 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfopylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2 -em-3-sodium carbokylate and 276 mg of cyclohexylacetoxymethyl iodide. NMR (CDCI3) d: 0.87-1.25 (6H,), 1.25 (3H, d, J = 7.2 Hz), 1.34 (3H, d, J = 6.3 Hz), 1.60-1.80 (5H,), 2.24 (2H, d, J = 6.9 Hz), 3.21 (3H, s), 3.33 (1H, dd, J: = 6.7 Hz, J = 2.8 Hz), 3.47 (1H, m), 4.26 (1H, m), 4.34 (1H , dd, J: = 9.6 Hz, J2 = 2.8 Hz), 5.88, 5.93 (2H, ABq, J = 4.3 Hz), 8.12 (1H, s), 8.44 (1H, s) MS (TSP): 566 (M ++ H) Example 187 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl- l-carbapen-2-em-3-carboxylate of dicyclohexylacetoxymethyl In the same manner as in Example 2, 292 mg of the title compound were obtained from 217 mg of (IS, 5R, 6S) -6- ((IR ) -1- hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate sodium and 274 mg of iodide of dicyclohexylacetoxymethyl. NMR (CDC13) d: 0.79-1.22 (10H, m), 1.26 (3H, d, J = 7.1 Hz), 1.37 (3H, d, J = 6.3 Hz), 1.60 (12H, m), 2.11 (1H, t, J = 7.5 Hz), 2.57 (1H, br.s), 3.22 (3H, s), 3.34 (1H, dd, J_. = 7.0 Hz, J: = 2.9 Hz), 3.47 (1H, m), 4.25 (1H, br.t), 4.33 (1H, dd, J: = 9.8 Hz, J2 = 3.0 Hz), 5.89 (1H, d, J = 5.6 Hz), 5.96 (1H, d, J = 5.6 Hz), 8.15 (1H, s), 8.47 ( 1H, s) MS (TSP): 648 (M ++ H) Example 188 (SS, 5R, 6S) -6- ((1R) -l-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b ] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 1- (1-methylcyclohexylcarbonylxoi) ethyl ester (a mixture of diastereomers) thereof, as in Example 2, obtained 287 mg of the title compound from 747 mg of (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazole-2- il) -l-methyl-l-carbapen-2-em-3-carboxylic acid sodium and 3.2 g of 1- [(1-methylcyclohexan-1-yl) carbonyloxy] ethyl iodide.

NMR (CDC13) d: 1.12, 1.21 (total 3H, each s), 1.56, 1.62 (total 3H, each d, J = 5.5 Hz), 1.1-2.1 (16H, m), 3.22 (3H, s), 3.3-3.4 (1H, m), 3.35-3.5 (1H, m), 4.2-4.35 (1H, m), 4.37 (1H, dd, Ji = 9.6 Hz, J2 = 2.7 Hz), 7.0-7.1 (1H,), 8.09 (1H, s), 8.51, 8.57 (total 1H, each s) MS ( TSP): 580 (M + + H) Example 189 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) 1-adamantylcarbonyloxymethyl-l-methyl-l-carbapen-2-em-3-carboxylate In the same manner as in Example 2, 258 mg of the title compound were obtained from 217 mg of (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate of sodium and 260 mg of 1-adamantylcarbonyloxymethyl iodide. NMR (CDCI3) d: 1.28 (3H, d, J = 7.3 Hz), 1.37 (3H, d, J = 6.1 Hz), 1.69 (6H, m), 1.86 (6H, m), 2.00 (3H, m) , 3.22 (3H, s), 3.35 (1H, dd, J: = 6.6 Hz, J2 = 3.0 Hz), 3.46 (1H, m), 4.29 (1H, m), 4.37 (1H, dd, Ji = 9.7 Hz , J2 = 2.9 Hz), 5.88 (1H, d, J = 5.6 Hz), 5.96 (1H, d, J = 5.6 Hz), 8.11 (1H, s), 8. 44 (1H, s) MS (TSP): 526 (M ++ H) Example 190 (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5,1] -b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 1- (1-adamathylcarbonyloxy) ethyl ester (a mixture of diastereomers) In the same manner as in example 2, 71 mg of the title compound were obtained from 184 mg of (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazole- 2 sodium l-methyl-l-carbapen-2-em-3-carboxylate and 500 mg of 1- (1-adamantylcarbonyloxy) ethyl iodide. NMR (CDC13) d: 1.27 (3H, m), 1.38 (3H, m), 1.55, 1.60 (total 3H, each d, J = 5.5 Hz), 1.62-2.07 (15H, m), 3.22 (3H , s), 3. 34 (1H, m), 3.44 (1H, na), 4.29 (1H, m), 4.37 (1H, m), 7.02 (1H, m), 8.08 (1H, s), 8.53, 8.56 (total 1H, each s) MS (TSP): 618 (M ++ H) Example 191 (1S, 5R, 6S) -6- ((IR ) -1- hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 1- (benzoyloxy) ethyl ester ( a mixture of diastereomers) In the same manner as in Example 2, 147 mg of the title compound was obtained from 197 mg of (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2 - (7-methanesulfonylimidazo [5, lb] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate sodium and 250 mg of 1- (benzoyloxy) ethyl iodide. NMR (CDCI3) d: 1.28 (3H, m), 1.33, 1.38 (total 3H, each d, J = 6.2 Hz), 1.71, 1.76 (total 3H, each d, J = 5.5 Hz), 3.21 (3H, s), 3.35 (3H, m), 3.44 (1H, m), 4.28 (1H, m), 4.37 (1H, m), 7.30 (1H,), 7.45 (2H, m), 7.60 (1H , m), 8.00, 8.02 (total 1H, each s), 8.07 (2H, m), 8.51, 8.57 (total 1H, each s) MS (TSP): 560 (MVH) Example 192 (ÍS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonyl-idazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate of 4- (2-propyl) benzoyloxymethyl In the same manner as in Example 2, 102 mg of the title compound was obtained from 92 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7- sodium methanesulfonylimidazo [5, lb] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate and 120 mg of 4- (2-propyl) benzoyloxymethyl iodide. NMR (CDCI3) d: 1.24 (3H, s), 1.25 (3H, d, J = 7.1 Hz), 1.26 (3H, s), 1.35 (3H, d, J = 6.2 Hz), 2.96 (1H, m), 3.21 (3H, s), 3.34 (1H, dd, Ji = 6.7 Hz, J2 = 2.8 Hz), 3.45 (1H, m), 4.28 (1H, m), 4.36 (1H, dd, Ji = 9.6 Hz, J2 = 2.8 Hz), 6.14, 6.18 (2H, ABq, J = 5.6 Hz), 7.30 (2H, d, J = 8.3 Hz), 7.98 (2H, d, J = 8.3 Hz), 8.09 (1H, s), 8.47 (1H, s) MS (TSP): 588 (M ++ H) Example 193 (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate of 4-n-butylbenzoyloxymethyl In the same manner as in Example 2, 140 mg of the title compound was obtained from 112 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) - 2- (7-Methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylic acid sodium ester and 180 mg of 4-n-butylbenzoyloxymethyl iodide. NMR (CDC13) d: 0.92 (3H, t, J = 7.3 Hz), 1.26 (3H, d, J = 7.4 Hz), 1.34 (2H, m), 1.35 (3H, d, J = 6.3 Hz) , 1.60 (2H, m), 2.66 (2H, t, J = 8.0 Hz), 3.21 (3H, s), 3.34 (1H, dd, Ji = 6.5 Hz, J2 = 2.9 Hz), 3.45 (1H, m) , 4.28 (1H, m), 4.36 (1H, dd, Ji = 9.8 Hz, J2 = 2.9 Hz), 6.14, 6.17 (2H, ABq, J = 5.6 Hz), 7.25 (2H, d, J = 8.3 Hz) , 7.97 (2H, d, J = 8.3 Hz), 8.09 (1H, s), 8.47 (1H, s) MS (TSP): 602 (M ++ H) Example 194 (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7 4-phenylbenzoyloxymethyl methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate In the same manner as in Example 2, 169 mg of the Title compound from 110 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l sodium-methyl-l-carbapen-2-em-3-carboxylate and 170 mg of 4-phenylbenzoyloxymethyl iodide. NMR (CDCI3) d: 1.27 (3H, d, J = 7.3 Hz), 1.36 (3H, d, J = 6.3 Hz), 2.17 (1H, br.s), 3.21 (3H, s), 3.35 (1H, dd, J_, = 6.6 Hz, J2 = 2.8 Hz), 3.46 (1H, m), 4.29 (1H, m), 4.37 (1H, dd, Ji = 9.8 Hz, J2 = 2.8 Hz), 6.20 ( 2H, s), 7.45 (3H,), 7.65 (4H, m), 8.10 (1H, s), 8.13 (2H, m), 8.49 (1H, s) MS (TSP): 622 (M ++ H) Example 195 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen- 4-t-Butylbenzoyloxymethyl 2-em-3-carboxylate In the same manner as in Example 2, 262 mg of the title compound was obtained from 217 mg of (IS, 5R, 6S) -6- ((IR ) -1- hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate sodium and 318 mg of iodide of 4-t-butylbenzoyloxymethyl. NMR (CDCI3) d: 1.25 (3H, d, J = 7.3 Hz), 1.31 (9H, s), 1.34 (3H, d, J = 6.4 Hz), 3.20 (3H, s), 3.34 (1H, dd, J: = 6.7 Hz, J2 = 2.8 Hz), '3.48 (1H, dq, J: = 9.8 Hz, J2 = 7.3 Hz), 4.26 (1H, dq, J = 6.3 Hz), 4.35 (1H, dd, Jj. = 9.7 Hz, J: = 2.9 Hz), 6.14 (1H, d , J = 5.6 Hz), 6.17 (1H, d, J = 5.6 Hz), 7.45 (2H, m), 7.97 (2H, m), 8.12 (1H, s), 8.44 (1H, s) MS (TSP) : 619 (M ++ H) Example 196 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) - L-Methyl-l-carbapen-2-em-3-carboxylic acid 1- (4-t-butylbenzoyloxy) ethyl ester In the same manner as in Example 2, 154 mg of the title compound was obtained from 192 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2 sodium em-3-carboxylate and 300 mg of 1- (4-t-butylbenzoyloxy) ethyl iodide. NMR (CDC1) d: 1.26 (3H, m), 1.32, 1.34 (total 9H, each s), 1.37 (3H, m), 1.70, 1.74 (total 3H, each d, J = 5.4 Hz), 3.20 (3H, s), 3.34 (1H, m), 3.44 (1H, m), 4.28 '1H, m), 4.36 (1H, m), 7.29 (1H, m), 7.46 (2H, m), 7.98 ( 2H, ra), 8.01 (1H, s), 8.51, 8.57 (total 1H, each s) MS (TSP): 616 (M ++ H) Example 197 (1S, 5R, 6S) -6- ((IR) 1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylic acid, 2,4,6-trimethylbenzoyloxymethyl ester in the same manner as in Example 2, 214 mg of the title compound was obtained from 178 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [ Sodium 5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate and 254 mg of 2,4,6-trimethylbenzoyloxymethyl iodide. NMR (CDCI3) d: 1.26 (3H, d, J = 7.1 Hz), 1.36 (3H, d, J = 6.0 Hz), 2.27 (9H, s), 3.21 (3H, s), 3.34 (1H, dd, J_. = 6.6 Hz, J2 = 2.2 Hz), 3.47 (1H, m), 4.27 (1H, m), 4.34 (1H, dd, Ji = 9.8 Hz, J2 = 2.2 Hz), 6.11, 6.15 (2H, ABq , J = 5.6 Hz), 6. 83 (2H, s), 8.10 (1H, s), 8.49 (1H, s) MS (TSP): 588 (M ++ H) Example 198 (SS, 5R, 6S) -6- ((IR) -1 -hydroxyethyl) -2- (7-Ratanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 1- (2-propyloxycarbonyloxy) ethyl ester (a mixture of diastereomers) In the same manner as in Example 2, 257 mg of the title compound was obtained from 267 mg of (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-Methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate sodium and 300 mg of 1- (2-propyloxycarbonyl iodide? I) ethyl. NMR (CDC13) d: 1.28 (6H, m), 1.36 (6H, m), 1.58, 1.64 (total 3H, each d, J = 5.4 Hz), 3.22 (3H, s), 3.33 (lh, m), 3.45 (1H, m), 4.28 (1H, m), 4.35 (1H,), 4.91 (1H, m), 6.93 (1H, m), 8.09 (1H, s), 8.54 (1H, s) MS (TSP) : 542 (M + + H) Example 199 (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) - 1- (2-Butyloxycarbonyloxy) ethyl l-methyl-l-carbapen-2-em-3-carboxylate (a mixture of diastereomers) In the same manner as in Example 2, 164 mg of the title compound was obtained from 220 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l- sodium carbapen-2-em-3-carboxylate and 320 mg of 1- (2-butyloxycarbonyloxy) ethyl iodide. NMR (CDC13) d: 0.85-1.00 (3H, m), 1.25-1.40 (9H, m), 1.55- 1.75 (6H, m), 3.22 (3H, sx2), 3.34 (1H, dd, Ji = 6.8 Hz , J2 = 2. 9 Hz), 3.46 (1H,), 4.27 (1H, m), 4.35 (1H,), 4.65-4.85 (1H,), 6.94 (1H, m), 8.09 (1H, sx2), 8.55 (1H, m) Example 200 (ÍS, 5R, ßS) -6- ((IR) -1-hydroxyethyl) -2- ( 7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 1- (3-pentyloxycarbonyloxy) ethyl ester (a mixture of diastereomers in the same way that in Example 2, 276 mg of the title compound was obtained from 151 mg of (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5,1] -b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate sodium and 199 mg of 1- (3-pentyloxycarbonyloxy) ethyl iodide. NMR (CDCI3) d: 0.83- 0.95 (6H, m), 1.23 (3H, m), 1.55, 1.70 (7H, m), 3.18 (3H, s), 3.30 (1H, m), 3.46 (1H, m), 4.22 (1H, m) , 4.32 (1H, m), 4.58 (1H, m), 6.89 (1H, m), 8.10 (1H, s), 8. 45, 8.47 (total 1H, each s) MS (TSP): 570 (M ++ H) Example 201 (ÍS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 1- (1-butyloxycarbonyloxy) ethyl ester (a mixture of diastereomers) In the same manner as in Example 2, 51.0 mg of the title compound was obtained from 200.0 mg of (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5,1-b ] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate and 236.2 mg of 1- (1-butyloxycarbonyloxy) ethyl iodide. NMR (CDC13) d: 0.93 (3H, td, J = 7.3 Hz, J = 12.6 Hz), 1.26 (3H, dd, Ji = 7.3 Hz, J2 = 2.9 Hz), 1.33 (3H, dd, J: = 6.1 Hz, J2 = 2.5 Hz), 1.55 (2H, m), 1.60 (3H, m), 1.65 (2H, m), 3.22 (3H, s), 3.35 (1H, m), 3.45 (1H, m), 4.15, 4.22 (total 2H, each t, J = 6.5 Hz), 4.29 (1H,), 4.38 (1H, td, J = 2.6 Hz, J = 9.8 Hz), 6.94 (1H, m), 8.06, 8.08 (total 1H, each s), 8.58, 8.59 (total 1H, each s) MS (TSP): 556 (M ++ H) Example 202 (ÍS, 5R, 6S) -6- ((IR) -1-hydroxyethyl ) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 4-heptyloxycarbonyloxymethyl ester In the same manner as in Example 2 , 229 mg of the title compound was obtained from 168 mg of (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazole- Sodium 2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate and 200 mg of 4-heptyloxycarbonyloxymethyl iodide.

NMR (CDCl 3) d: 0.89 (6H, m), 1.26 (3H, d, J = 7.2 Hz), 1.30-1.40 (4H, m), 1.35 (3H, d, J = 6.3 Hz), 1.56 (4H, m), 3.21 (3H, s), 3.33 (1H, dd, Ji = 6.9 Hz, J_ = 2.9 Hz), 3.47 (1H,), 4.26 (1H, m), 4.35 (1H, dd, Ji = 9.8 Hz, J2 = 2.9 Hz), 4.74 (1H, m), 5.89, 5.95 (2H, ABq, J = 5.8 Hz), 8.11 (1H, s), 8.50 (1H, s) MS (TSP): 584 (M ++ H) Example 203 (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-1-carbapen- 2- (4-heptyloxycarbonyloxy) ethyl 2-em-3-carboxylate (a mixture of disatheremers) In the same manner as in Example 2, 171 mg of the title compound was obtained from 178 mg of (IS, 5R , 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3 sodium carboxylate and 300 mg of 1- (4-heptyloxycarbonyloxy) ethyl iodide. NMR (CDCl 3) d: 0.90 (6H, m), 1.28 (3H, m), 1.38 (3H, m), 1. 30-1.65 (8H, m), 1.60, 1.66 (total 3H, each d, J = 5.3 Hz), 3.22 (3H, s), 3.34 (1H, m), 3.45 (1H, m), 4.27 (1H, m), 4.35 (1H, m), 4.75 (1H, m), 6.93 (1H, m), 8.07 (1H, s), 8.56, 8.60 (total 1H, each s) MS (TSP): 598 (M ++ H) Example 204 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 1- (1-pentyloxycarbonyloxy) ethyl ester (a mixture of diastereomers) In the same manner as in Example 2 , 235 mg of the title compound were obtained from 220 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazole- Sodium 2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate and 300 mg of 1- (1-pentyloxycarbonyloxy) ethyl iodide. NMR (CDC13) d: 0.86-0.92 (3H, m), 1.27, 1.37 (total 3H, each d, J = 7.5 Hz), 1.37, 1.38 (total 3H, each d, J = 6.5 Hz), 1.60, 1.65 (total 3H, each d, J = 5.4 Hz), 1.60-1.80 (2H, m), 2.00 (1H, br.s), 3.22 (3H, s), 3.40-3.50 (1H, qx2), 4.10-4.38 (4H, m), 6.94 (1H, d, J = 5.4 Hz), 8.80 (1H, s), 8.57 (1H, s) Example 205 (SS, 5R, 6S) -6- ((IR) -1- hydroxyethyl) -2- (7- ethansulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 1- (4-methyl-l-pentyloxycarbonyloxy) ethyl In the same manner as in example 2, 220 mg of the title compound was obtained from 220 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7- Sodium methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate and 320 mg of 1- (4-methyl-1-pentyloxycarbonyloxy) ethyl iodide . NMR (CDCI3) d: 0.86, 0.89 (total 3H, d, J = 6.6 Hz), 1.29 (3H, d, J = 7.3 Hz), 1.20-1.30 '(2H, m), 1.38, 1.39 (total 3H, d, J = 6.3 Hz), 1.60, 1.66 (total 3H, d, J = 5.4 Hz), 1.50-1.70 (2H, m), 1.95 (1H, dd, Ji = 8.5 Hz, J; = 4.7 Hz), 3.22 (3H, s), 3.34 (1H, dd, J: = 6.3 Hz, J2 = 2.7 Hz), 3.45 (1H, dq, Ji = 9.3 Hz, J2 = 7.3 Hz), 4.08-4.40 (4H, m) , 6.94 (1H, dq, J = 5.4 Hz), 8.80 (1H, s), 8.56, 8.57 (1H, s) Example 206 (1S, 5R, 6S) -6- ((lR) -l-hydroxyethyl) - 2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 5-nonyloxycarbonyloxymethyl ester In the same manner as in Example 2, obtained 218 mg of the title compound from 184 mg of (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazole-2- il) -l-methyl-l-carbapen-2-em-3-carboxylate sodium and 250 mg of 5-nonyloxycarbonyloxymethyl iodide. NMR (CDC13) d: 0.88 (6H, m), 1.28 (3H, d, J = 7.2 Hz), 1.33 (8H, m), 1.37 (3H, d, J = 6.3 Hz), 1.58 (4H, m) , 3.22 (3H, s), 3.35 (1H, dd, Ji = 6.8 Hz, J2 = 2.7 Hz), 3.47 (1H, m), 4.28 (1H, m), 4.37 (1H, dd, Ji = 9.7 Hz, J2 = 2.7 Hz), 4.73 (1H, m), 5.91, 5.97 (2H, ABq, J = 5.8 Hz), 8.09 (1H, s), 8.54 (1H, s) MS (TSP): 612 (M ++ H) Example 207 (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl- 1- (5-nonyloxycarbonyloxy) ethyl l-carbapen-2-em-3-carboxylate 8 a mixture of diastereomers) In the same manner as in Example 2, 171 mg of the title compound was obtained from 192 mg of ( ÍS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, lb] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3 sodium carboxylate and 600 mg of 1- (5-nonyloxycarbonyloxy) ethyl iodide. NMR (CDC1) d: 0.88 (6H, m), 1.26-1.38 (14H, m), 1.58-1.70 (7H, m), 3.21 (3H, s), 3.33 (1H, m), 3.45 (1H, m ), 4.25 (1H, m), 4.33 (1H, m), 4.71 (1H, m), 6.93 (1H, m), 8.07 (1H, s), 8.55, 8.58 (total 1H, each s) MS (TSP) ): 626 (M ++ H) Example 208 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 1- (2,2-dimethyl-l-propyloxycarbonyloxy) (a mixture of disatheremers) In the same manner as in Example 2, 80.9 mg of the title compound was obtained from (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, Sodium 1-b] thiazol-2-yl) -1-methyl-l-carbapen-2-em-3-carboxylate and 240.8 mg of 1- (2,2-dimethyl-1-propyloxycarbonyloxy) ethyl iodide. NMR (CDCI3) d: 0.94, 0.98 (total 9h, each s), 1.27, 1.29 (total 3H, each d, J = 3.9 Hz), 1.35, 1.38 (total 3H, each d, J = 6.3 Hz), 1.61 , 1.67 (total 3H, each d, J = 5.6 Hz), 3.22 (3H, s), 3.34 (1H, m), 3.45 (1H, m), 3.88 (2H, m), 4.28 (1H, q, J = 6.6 Hz), 4.36 (1H, td, Ji = 2.5 Hz, J2 = 10.0 Hz), 6.93, 6.95 (total 1H, each q, J = 5.6 Hz), 8.07, 8.07 (total 1H, each s), 8.55 , 8.57 (total 1H, each s) MS (TSP): 570 (MAH) Example 209 (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1 -b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 1- (3, 3-dimethyl-2-butyloxycarbonyloxy) ethyl ester (a mixture of diastereomers) In the same way that in Example 2, 124.1 mg of the title compound was obtained from 200.0 mg of (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-ethanesulfonylimidazo [5,1] -b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate sodium and 207.8 mg of l- (3,3-dimethyl-2-butyloxycarbonyloxy) ethyl iodide. NMR (CDC13) d: 0.88, 0.91, 0.94, 0.96 (total 3H, each s), 1.27, 1.29 (total 3H, each d, J = 7.0 Hz), 1.36, 1.38 (total 3H, each d, J = 6.3 Hz), 1.60 (3H, d, J = 5.4 Hz), 1.66 (3H, d, J = 5.3 Hz), 3.22 (3H, s), 3.34 (1H, m), 3.45 (1H, m), 4.28 ( 1H, m), 4.36 / (1H, m), 4.66 (1H, m), 6.94 (1H, m), 8.05, 8.05, 8.06, 8.07 (total 1H, each s), 8.55, 8.57, 8.59, 8.60 , (total 1H, each s) MS (TSP): 584 (M ++ H) Example 210 (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5 , Cyclohexylmethoxycarbonyloxymethyl, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate In the same manner as in Example 2, 283 mg of the title compound was obtained from 218 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen -2-em-3-carboxylate sodium and 225 mg of cyclohexylmethoxycarbonyloxymethyl iodide. NMR (CDC13) d: 0.92-1.30 (6H, m), 1.26 (3H, d, J = 7.2 Hz), 1.35 (3H, d, J = 6.3 Hz), 1.70-1.80 (5H, m), 3.21 ( 3H, s), 3.33 (1H, dd, Ji = 6.7 Hz, J2 = 2.7 Hz), 3.47 (1H, m), 3.98 (3H, d, J = 4.2 Hz), 4.27 (1H, m), 4.35 ( 1H, dd, Ji = 9.8 Hz, J2 = 2.7 Hz), 5.89, 5.94 (2H, ABq, J = 5.8 Hz), 8.12 (1H, s), 8.48 (1H, s) MS (TSP): 582 (M ++ H) Example 211 (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl- 1- (cyclohexylmethoxycarbonyloxy) -1-propyl l-carbapen-2-em-3-carboxylate (a mixture of diastereomers) In the same manner as in Example 2, 225 mg of the title compound was obtained from 414 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2 sodium-3-carboxylate and 2.07 g of 4-1 [(cyclohexylmethoxy) carbonyloxy] -1-propyl iodide. NMR (CDCI3) d: 1.00, 1.08 (total 3H, each t, J = 7.6 Hz), 1.27 (3H, d, J = 7.4 Hz), 0.9-2.2 (16H, m), 3.22 (3H, s), 3.34 (1H, dd, Ji = 6.7 Hz, J = 2.8 Hz), 3.4-3.5 (1H, m), 3.8-4.05 (2H, m), 4.2-4.4 (2H, m), 6.78, 6.80 (total 1H , each t, J = 5.5 Hz), 8.08, 8.09 (total 1H, each s), 8.57, 8.59 (total 1H, each s) MS (TSP): 610 (M ++ H) Example 212 (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate of 1- (dicyclohexylmethoxycarbonyloxy) ethyl (a mixture of diastereomers) In the same manner as in Example 2, 69 mg of the title compound was obtained from 260 mg of (1S, 5R, 6S) -6- ((IR ) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate sodium and 630 mg of iodide of 1- (dicyclohexylmethoxycarbonyloxy) ethyl. NMR (CDC13) d: 0.88-1.23 (10H, m), 1.27 (3H, d, J = 7.4 Hz), 1.37 (3H, d, J = 6.5 Hz), 1.57-1.74 (12H, m), 1.61, 1.66 (total 3H, each d, J = 5.3 Hz), 3.21 (3H, s), 3.33 (1H, m), 3.47 ( 1H, m), 4.25 (1H, m), 4.34 (1H, m), 4.43 (1H, m), 6.91 (1H, m), 8.08 (total 1H, each s), 8.49, 8.56 (total 1H, each s) MS (TSP): 678 (M ++ H) Example 213 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazole Cyclohexyloxycarbonyloxymethyl 2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate In the same manner as in Example 2, 191 mg of the title compound was obtained from 188 mg of (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3 sodium carboxylate and 259 mg of cyclohexyloxycarbonyloxymethyl iodide. NMR (CDC13) d: 1.28 (3H, d, J = 7.1 Hz), 1.37 (3H, d, J = 6.1 fíz), 1.2-2.0 (10H, m), 3.23 (3H, s), 3.35 (1H, dd, Jx = 6.4 Hz, J2 = 2.7 Hz), 3.4-3.5 (1H,), 4.25-4.35 (1H, m), 4.38 (1H, dd, Ji = 9.9 Hz, J2 = 2.7 Hz), 4.6-4.7 (1H, m), 5.90 (1H, d, J = 5.8 Hz), 5.96 (1H, d, J = 5.8 Hz), 8.09 (1H, s), 8.54 (1H, s) MS (TSP): 568 ( M ++ H) Example 214 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl -l-carbapen-2-em-3-carboxylic acid 1- (cyclohexyloxycarbonyloxy) -2-methyl-1-propyl ester (a mixture of diastereomers) In the same manner as in Example 2, 151 mg of the title compound were obtained from 268 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl- sodium l-carbapen-2-em-3-carboxylate and 900 mg of 1- (cyclohexyloxycarbonyloxy) -2-methyl-1-propyl iodide. NMR (CDCl3) d: 1.02 (6H, m), 1.29 (3H, m), 1.37 (3H,), 1.31-2.20 (11H,), 3.22 (3H, s), -3.34 (1H, m), 3.45 (1H, m), 4.28 (1H, m), 4.36 (1H, m), 4.64 (1H, m), 6.63, 6.68 (total 1H, each d, J = 5.1 Hz), 8.07, 8.08 (total 1H, each s), 8.59, 8.60 (total 1H, each s) MS (TSP): 610 (M ++ H) Example 215 (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-Methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylic acid cyclohexyl (cyclohexyloxycarbonyloxy) methyl ester (a mixture of diastereomers) In the same way as in Example 2, 208 mg of the title compound was obtained from 275 mg of (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-] b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate sodium and 600 mg of cyclohexyl (cyclohexyloxycarbonyloxy) ethyl iodide. NMR (CDC13) d: 1.20-2.05 (21H, m), 1.28 (3H, m), 1.38 (3H, m), 3.22 (3H, s), 3.34 (1H, m), 3.41 (1H, m), 4.29 (1H, m), 4.36 (1H, m), 4.64 (1H, m), 6.63, 6.67 (total 1H, each d, J = 5.5 Hz), 8.06 (1H, s), 8.60 (1H, s) MS (TSP): 650 (M + + H) Example 216 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazole-2 -l) -l-methyl-l-carbapen-2-em-3-carboxylate of (IR, 2S, 5R) - (1) -methyloxycarbonyloxymethyl In the same manner as in Example 2, 232 mg of the compound of title from 173 _? _ g of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l sodium-methyl-l-carbapen-2-em-3-carboxylate and 198 mg of (IR, 2S, 5R) - (1) -methyloxycarbonyloxymethyl iodide. NMR (CDC1) d: 0.76 (3H, d, J = 6.9 Hz), 0.88 (6H, m), 1.00-1.50 (4H,), 1.27 (3H, d, J = 7.1 Hz), 1.36 (3H, d , J = 6.3 Hz), 1.65-2.10 (4H, m), 2.35 (1H, br.s), 3.22 (3H, s), 3.33 (1H, dd, Ji = 6.9 Hz, J2 = 2.7 Hz), 3.47 (1H, m), 4.27 (1H, m), 4.34 (1H, dd, Ji = 9.8 Hz, J2 = 2.7 Hz), 4.55 (1H , m), 5.91, 5.95 (2H, ABq, J = 5.7 Hz), 8.10 (1H, s), 8.52 (1H, s) MS (TSP): 624 (M * + H) Example 217 (ÍS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate of 1- ((IR, 2S, 5R) - (1) -methyloxycarbonyloxy) -ethyl (a mixture of diastereomers) In the same manner as in Example 2, 215 mg of the title compound was obtained from 187 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2 sodium em-3-carboxylate and 300 mg of 1- ((IR, 2S, 5R) - (1) -methyloxycarbonyloxy) ethyl iodide. NMR (CDCl 3) d: 0.79 (3H, m), 0.89 (6H,), 0.90-1.50 (4H, m), 1.27 (3H, d, J = 7.1 Hz), 1.37 (3H, m), 1.60, 1.66 (totalm 3H, each d, J = 5.5 Hz), 1.82-2.20 (4H, m), 3.22 (3H, s), 3.32 (1H, m), 3.45 (1H, m), 4.27 (1H, m), 4.35 (1H, m), 4.53 (1H, m), 6.93 (1H, m), 8.07, 8.08 (total 1H, each s), 8.55, 8.59 (total 1H, each s) MS (TSP): 638 (M ++ H) Example 218 (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl- L-carbapen-2-em-3-carboxylate of (SS, 2R, 5S) - (d) -methyloxycarbonyloxymethyl In the same manner as in Example 2, 236 mg of the title compound were obtained from 164 mg of ( ÍS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em Sodium carboxylate and 333 mg of (1S, 2R, 5S) - (d) -methyloxycarbonyloxymethyl iodide. NMR (CDC13) d: 0.74 (3H, d, J = 6.9 Hz), 0.89 (6H, m), 1.00-1.10 (2H,), 1.28 (3H, d, J = 7.4 Hz), 1.37 (3H, d , J = 6.3 Hz), 1.40-2.14 (6H, m), 3.22 (3H, s), 3.34 (1H, dd, Ji = 6.9 Hz, J2 = 2.8 Hz), 3.47 (1H, m), 4.28 (1H , m), 4.36 (1H, dd, J: = 9.8 Hz, J2 = 2.8 Hz), 4.54 (1H, m), 5.88, 5.98 (2H, ABq, J = 5.8 Hz), 8.10 (1H, s), 8.54 (1H, s) MS (TSP): 624 (M ++ H) Example 219 (IS, 5R, 6S) -6-. { (IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate of (SS, 2R, 5R) -isomethyloxycarbonyloxymethyl In the same manner as in Example 2, 214 mg of the title compound was obtained from 157 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-Methanesulfonylimidazo [5 1-b] thiazol-2-yl) -l-methyl-1-carbapen-2-em-3-carboxylic acid sodium ester and 291 mg of (1S, 2R, 5R) -isomethyloxycarbonyloxymethyl iodide. NMR (CDC13) d: 0.84 (3H, d, J = 6.6 Hz), 0.91 (6H, m), 1.15-1.90 (9H, m), 1.26 (3H, d, J = 7.4 Hz), 1.36 (3H, d, J = 6.3 Hz), 3.22 (3H, s), 3.33 (1H, dd, Ji = 6.8 Hz, J2 = 2.8 Hz), 3.47 (1H, m), 4.27 (1H, m), 4.35 (1H, dd, J: = 9.8 Hz, J2 = 2.8 Hz), 4.91 (1H, m), 5.88, 5.97 (2H, ABq, J = 5.8 Hz), 8.10 (1H, s), 8.52 (1H, s) MS ( TSP): 624 (M + + H) Example 220 (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) ) (1S, 2S, 5R) -neomethyloxycarbonyloxymethyl-1-methyl-1-carbapen-2-em-3-carboxylate In the same manner as in Example 2, 212 mg of the title compound was obtained from 151 mg of (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2 sodium-3-carboxylate and 270 mg of (SS, 2S, 5R) -neomethyloxycarbonyloxymethyl iodide. NMR (CDCI3) d: 0.82 (3H, d, J = 6.7 Hz), 0.87 (6H, m), 0.90-1.12 (3H, m), 1.28 (3H, d, J = 7.2 Hz), 1.37 (3H, d, J = 6.2 Hz), 1.42-1.80 (6H, m), 2.06 (1H, m), 3.22 (3H, s), 3.34 (1H, dd, Ji = 6.9 Hz, J2 = 2.8 Hz), 3.46 ( 1H, m), 4.28 (1H, m), 4.37 (1H, dd, Ji = 9.7 Hz, J2 = 2.8 Hz), 5.09 (1H, m), 5.88, 6.01 (2H, ABq, J = 5.9 Hz), 8.10 ((1H, s), 8.54 (1H, s) MS (TSP): 624 (M '+ H) Example 221 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-Methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate of 3,3,5,5-tetramethylcyclohexyloxycarbonyloxy-methyl In the same way as in example 2, 202 mg of the title compound was obtained from 158 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazole- Sodium 2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate and 200 mg of 3,3,5,5-tetramethylcyclohexyloxycarbonyloxymethyl iodide. NMR (CDC13) d: 0.94 (6H, s), 1.04 (6H, s), 1.10-1.23 (2H, m), 1.83 (4H, m), 3.22 (3H, s), 3.34 (1H, dd, Ji = 6.7 Hz, J2 = 2.8 Hz), 3.47 (1H, m), 4.28 (1H, m), 4.36 (1H, dd, Jx = 9.8 Hz, J2 = 2.8 Hz), 4.92 (1H, m), 5.91, 5.94 (2H, ABq, J = 5.9 Hz), 8.10 (1H, s), 8.53 (1H, s) MS (TSP): 624 (M ++ H) Example 222 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl ) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 2-adamantyloxycarbonyloxymethyl ester In the same manner as in Example 2 , 134 mg of the title compound was obtained from 109 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazole- 2-yl) -l-methyl-l-carbapen-2-em-3-carboxylac sodium and 150 mg of 2-adamantyloxycarbonyloxymethyl iodide, NMR (CDCl 3) d: 1.28 (3H, d, J = 7.1 Hz), 1.37 (3H, d, J = 6. 3 Hz), 1.52-2.12 (14H,), 3.23 (3H, s), 3.35 (1H, dd, Ji = 6.6 Hz, J2 = 2.8 Hz), 3.46 (1H, m), 4.29 (1H, m), 4.37 (1H, dd, i = 9.8 Hz, J2 = 2.8 Hz), 4.83 (1H, m), 5.92, 5.97 (2H, ABq, J = 5.8 Hz), 8.10 (1H, s), 8.53 (1H, s) MS (TSP): 620 (M ++ H) Example 223 (SS, 5R, 6S) -6- ((IR) - 1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate of 1- ((indan-2-yl) ) oxycarbonyloxy) ethyl (a mixture of diastereomers) In the same manner as in Example 2, 137 mg of the title compound was obtained from 180 mg of (IS, 5R, 6S) -6- ((IR) -1 -hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate sodium and 250 mg of 1- (iodide (indan-2-yl) oxycarbonyloxy) ethyl. NMR (CDCl 3) d: 1.28 (3H, m), 1.38 (3H, d, J = 6.3 Hz), 1.57, 1.64 (total 3H, each d, J = 5.5 Hz), 3.17-3.40 (5H, m), 3.23 (3H, s), 4.29 (1H, m), 4.36 (1H, m), 5.45 (1H, m), 5.51 (1H, m), 6.95 (1H, m), 7.19 (4H, m), 8.08 ( 1H, s), 8.55 (1H, s) MS (TSP): 616 (M + + H) Example 224 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methanesulfonylimidazo [5, 1-b ] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 1- (2-methylphenoxycarbonyloxy) ethyl ester In the same manner as in Example 2, 214.0 mg of the title compound were obtained from 200.0 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen- Sodium 2-em-3-carboxylate and 500 mg of l- (2-methylphenoxycarbonyloxy) ethyl iodide. NMR (CDC13) d: 1.28, 1.30 (total 3H, each d, J = 7.3 Hz), 1.38, 1.40 (total 3H, each d, J = 6.3 Hz), 1.69, 1.74 (total 3H, each d, J = 5.4 Hz), 1.80 (1H, m), 2.20, 2.28 (total 3H, each s), 3.21 (3H, s), 3.33 (1H, m), 3.46 (1H, m), 4.28 (1H, m), 4.35 (1H,), 7.01 (1H, m), 7.23 (4H, m), 8.05, 8.06 (total 1H, each s), 8.53, 8.56 (total 1H, each s) MS (TSP): 590 (M ++ H) Example 225 (ÍS, 5R, 6S) -6- ((IR) -1-hydroxyethyl ) -l-methyl-2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 1- (2-ethylphenoxycarbonyloxy) ethyl ester -the same As in Example 2, 149.0 mg of the title compound was obtained from 200.0 mg of (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7- Sodium methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate and 500 mg of l- (2-ethylphenoxycarbonyloxy) ethyl iodide.

NMR (CDCI3) d: 1.14, 1.21 (total 3H, each t, J = 7.3 Hz), 1.28, 1.30 (total 3H, each d, J = 7.3 Hz, 1.38, 1.40 (total 3H, each d, J = 6.3 Hz), 1.69, 1.74 (total 3H, each d, J = 5.4 Hz), 1.90 (1H, m), 2.56, 2.65 (total 2H, each q, J = 7.3 Hz), 3.21 (3H, s), 3.33 (1H, m), 3.46 (1H, m), 4.28 (1H, m), 4.39 (1H, m), 7.01 (1H, m), 7.22 (4H, m), 8.05 (1H, s), 8.52 , 8.55 (total 1H, each s) MS (TSP): 604 (M ++ H) Example 226 (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- ( 7-Methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 1- (3-methylphenoxycarbonyloxy) ethyl ester In the same manner as in Example 2, 183.0 were obtained mg of the title compound from 200.0 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methanesulfonylimidazo [5, 1-b] thiazole- Sodium 2-yl) -l-carbapen-2-em-3-carboxylate and 500 mg of l- (3-methylphenoxycarbonyloxy) ethyl iodide. NMR (CDCI3) d: 1.28, 1.30 (total 3H, each s, J = 7.3 Hz), 1.38, 1.40 (total 3H, each d, J = 6.3 Hz), 1.69, 1.74 (total 3H, each d, J = 5.4 Hz), 1.95 (1H , d, J = 4.6 Hz), 2.34, 2.36 (total 1H, each s), 3.21 (3H, s), 3.33 (1H, m), 3.46 (1H, m), 4.28 (1H, m), 4.35 ( 1H, m), 7.14 (4H, m), 7.25 (1H, m), 8.06 (1H, s), 8.53, 8.56 (total 1H, each s) MS (FAB): 590 (M ++ H) Example 227 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2- 1- (4-methylphenoxycarbonyloxy) ethyl em-3-carboxylate In the same manner as in Example 2, 158.0 mg of the title compound was obtained from 200.0 mg of (IS, 5R, 6S) -6- (( IR) -1-hydroxyethyl) -l-methyl-2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate sodium and 500 mg of iodide of 1- (4-methylphenoxycarbonyloxy) ethyl. NMR (CDC13) d: 1.28, 1.30 (total 3H, each d, J = 7.3 Hz), 1.38, 1.40 (total 3H, each d, J = 6.3 Hzj, 1.69, 1.74 (total 3H, each d, J = 5.4 Hz), 1.79 (1H, m), 2.33, 2.34 (total 3H, each s), 3.21 (3H, s), 3.33 (1H, m), 3.46 (1H, m), 4.28 (1H, m), 4.35 (1H, m), 7.01 (1H, m), 7.04 (1H, m), 7.16 (1H, m), 7.18 (2H, s), 8.05, 8.06 (total 1H, each s), 8.54, 8.56 (total 1H, each s) MS (TSP): 590 (M ++ H) Example 228 (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methanesulfonylimidazo [ 5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 1- (2,6-dimethylphenoxycarbonyloxy) ethyl ester (a mixture of diastereomers) In the same manner as in Example 2 , 140.0 mg of the title compound was obtained from 200.0 mg of (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7- methanesulfonylimidazo [5, 1-] b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate sodium and 500 mg of l- (2,6-dimethylphenoxycarbonyloxy) ethyl iodide, NMR (CDC13) d: 1.27 (3H, m ), 1.38, 1.40 (total 3H, each d, J = 6.3 Hz), 1.69, 1.74 (total 3H, each d, J = 5.4 Hz), 2.17 (3H, s), 2.25 (3H, s), 3.21 (3H, s), 3.33 (1H, m), 3.46 (1H, m), 4.28 (1H, m), 4.35 (1H, m), 6.98 (1H, m), 7.04 (3H, m), 8.04, 8.06 (total 1H, each s), 8.46 8.53 (total 1H, each s) MS (FAB): 604 (M + H) Example 229 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7- (2, 4-dimethylphenoxycarbonyloxy) ethyl 7- (7- (1-b) thiazol-2-yl) -l-carbapen-2-ene-3-carboxylic acid (a mixture of diastereomers) In the same way that in Example 2, 133.0 mg of the title compound were obtained from 200.0 mg of (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7- methanesulfonylimidazo [5,1-b] thiazol-2-yl) -l-methyl-1-carbapene-2-em-3-carboxylate sodium and 500 mg of l- (2,4-dimethylphenoxycarbonyloxy) ethyl iodide. NMR (CDCI3) d: 1.28, 1.30 (total 3H, each d, J = 7.3 Hz), 1.38, 1.40 (total 3H, each d, J = 6.3 Hz), 1.69, 1.74 (total 3H, each d, J = 5.4 Hz), 1.76 (1H, m), 2.15, 2.24 (total 3H, each s), 2.29, 2.30 (total 3H, each s), 3.21, 3.22 (total 3H, each s), 3.33 (1H, m) , 3.46 (1H, m), 4.28 (1H, m), 4.38 (1H, m), 7.04 (4H, m), 8.04, 8.05 (total 1H, each s), 8.52, 8.56 (total 1H, each s) MS (TSP): 604 (M + + H) Example 230 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methanesulfonylimidazo [5, 1-b ] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 1- (3,5-dimethylphenoxycarbonyloxy) ethyl ester In the same manner as in Example 2, 199.0 mg of the title compound were obtained from 200.0 mg of (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) - sodium l-carbapen-2-em-3-carboxylate and 500 mg of l- (3,5-dimethylphenoxycarbonyloxy) ethyl iodide. NMR (CDC13) d: 1.28, 1.30 (total 3H, each s, J = 7.3 Hz), 1.39 (3H, d, J = 6.3 Hz), 1.69, 1.74 (total 3H, each d, J = 5.4 Hz), 1.93 (1H, d, J = 4.7 Hz), 2.29 (3H, s), 2.32 (3H, s), 3.21 (3H, s), 3.33 (1H, m), 3.46 (1H,), 4.28 (1H, m), 4.35 (1H, m), 6.78 (1H, s), 6.87 (1H, m), 6.91 (1H, s), 7.01 (1H, m), 8.06 (1H, s), 8.53, 8.57 (total 1H, each s) MS (TSP): 604 (M + + H) Example 231 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 1- (2,4,6-trimethylphenoxycarbonyloxy) ethyl ester (a mixture of diastereomers) In the same way that in Example 2, 200 mg of the title compound was obtained from 191 mg of (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5,1] -b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate sodium and 500 mg of 1- (2,4,6-trimethylphenoxycarbonyloxy) ethyl iodide. NMR (CDC13) d: 1.29 (3H, m), 1.39 (3H, m), 1.69, 1.74 (total 3H, each d, J = 5.5 Hz), 2.12, 2.20 (total 3H, each s), 2.26 (3H , s), 3.22 (3H, s), 3.35 (1H, m), 3.44 (1H, m), 4.30 (1H, m), 4.46 (1H,), 6.85, 6.87 (total 2H, each s), 7.00 (1H, m), 8.05, 8.06 (total 1H, each s), 8.48, 8.56 (total 1H, each s) MS (TSP): 618 (M ++ H) Example 232 (ÍS, 5R, 6S) -6 - ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate from 1- ( 4-t-butylphenoxycarbonyloxy) ethyl In the same manner as in Example 2, 303 mg of the title compound was obtained from 316 mg of (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-Methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylic acid sodium and 1.22 mg of 1- (4-t) iodide -nutilphenoxycarbonyloxy) ethyl. NMR (CDCI3) d: 1.27 (3H, d, J = 6.1 Hz), 1.29, 1.31 (total 9H, each s), 1.67, 1.73 (total 3H, each d, J = 6.1 Hz), 3.21 (3H, s ), 3.37 (1H, m), 3.46 (1H, m), 4.31 (1H, m), 4.38 (1H, m), 7.02 (1H,), 7.09 (1H, d, J = 9.8 Hz), 7.22 ( 1H, d, J = 8.8 Hz), 7.37 (1H, d, J = 9.7 Hz), 7.40 (1H, d, J = 8.8 Hz), 8.05, 8.06 (total 1H, each s), 8.54, 8.56 (total 1H, each s) MS (TSP): 632 (M * + H) Example 233 (IS, 5R, 6S) -6- ((IR) -1- idroxyethyl) -l-methyl-2- (7-methanesulfonylimidazo [ 5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid (indan-5-yl) -oxycarbonyloxymethyl ester In the same manner as in Example 2, 213 mg of the compound were obtained of the title from 200.0 mg of (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl ) -l-carbapen-2-em-3-carboxylate sodium and 500 mg of (indan-5-yl) oxycarbonyloxymethyl iodide. NMR (CDC13) d: 1.29 (3H, d, J = 7.3 Hz), 1.38 (3H, d, J = 6.3 Hz), 1.84 (1H, br.d), 2.10 (2H, m), 2.89 (4H, m), 3.21 (3H, s), 3.37 (1H, dd, Ji = 6.6 Hz, J2 = 2.8 Hz), 3.44 (1H, m), 4.30 (1H, m), 4.40 (1H, dd, Ji = 9.6 Hz, J2 = 2.8 Hz), 6.03 (2H, ABq, J = 5.9 Hz), 6.94 (1H, d, J = 7.9 Hz), 7.05 (1H, s), 7.19 (1H, d, J = 7.9 Hz) , 8.06 (1H, s), 8.53 (1H, s) MS (TSP): 602 (M ++ H) Example 234 (13, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-Methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 1- ((indan-5-yl) oxycarbonyloxy) ethyl thereof As in example 2, 115 mg of the title compound was obtained from 198 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, Sodium 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate and 600 mg of 1- ((indan-5-yl) oxycarbonyloxy) ethyl iodide. NMR (CDC13) d: 1.27 (3H, m), 1.38 (3H, m), 1.67, 1.73 (total 3H, each d, J = 5.5 Hz), 2.09 (2H, m), 2.88 (4H, m), 3.21 (3H, s), 3.36 (1H, m), 3.45 (1H, m), 4.34 (2H, m), 6.88-7.20 (4H, m), 8.06 (1H, s), 8.51, 8.54 (total 1H , each s) MS (TSP): 616 (M ++ H) Example 235 (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b ] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 1- ((indan-5-yl) oxycarbonyloxy) -1-propyl (a mixture of diastereomers) In the same way that in Example 2, 214 mg of the title compound were obtained from 118 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5,1] -b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate sodium and 700 mg of 1- ((indan-5-yl) oxycarbonyloxy) -1-propyl iodide. NMR (CDCI3) d: 1.05, 1.13 (total 3H, each t, J = 7.4 Hz), 1.27 (3H, m), 1.39 (3H, m), 1.98-2.10 (5H, m), 2.87 (4H, m ), 3.21 (3H, s), 3.35 (1H, m), 3.36 (1H, m), 4.31 (1H, m), 4.38 (1H, m), 6.87 (1H, m), 7.01-7.21 (3H, m), 8.06, 8.07 (total 1H, each s), 8.52 , 8.55 (total 1H, each s) MS (TSP): 647 (M ++ H) Example 236 (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [ Ethyl 5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate The title compound (249 mg) was obtained from 304 mg of (IS, 5R , 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3 sodium carboxylate and 270 mg of ethyl iodide in the same manner as in Example 2, except that the temperature of the reaction was at room temperature and the reaction time was 6 hours. NMR (CDC13) d: 1.25 (3H, d, J = 7.1 Hz), 1.37 (6H,), 2.65 (1H, s), 3.20 (3H, s), 3.33 (1H, dd, Ji = 6.9 Hz, J2 = 2.8 Hz), 3.46 (1H,), 4.32 (4H, m), 8.09 (1H, s), 8.41 (1H, s) MS (TSP): 440 (M ++ H) Example 237 (ÍS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate of 2-propyl The title compound (223 mg) was obtained from 299 mg of (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5,1] -b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate sodium and 684 mg of 2-propyl iodide in the same manner as in Example 2, except that the temperature of the reaction was at room temperature and the reaction time was 18 hours. NMR (CDCI3) d: 1.27 (3H, d, J = 7.2 Hz), 1.32 (3H, d, J = 6.63 Hz), 1.37 (6H, m), 3.21 (3H, s), 3.34 (1H, dd, Ji = 6.8 Hz, J2 = 2.8 Hz), 3.45 (1H, m), 4.28 (1H, m), 5.29 (2H, s), 4.35 (1H, dd, Ji = 9.6 Hz, Jz = 2.8 Hz), 5.16 (1H, m), 8.08 (1H, s), 8.44 (1H, s) MS (TSP): 454 (M ++ H) Example 238 (IS, 5R, 6S) -6- ((IR) -1- hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylic acid 1-decyl ester The title compound (177 mg) was obtained from 174 mg of (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) -l- sodium methyl-l-carbapen-2-em-3-carboxylate and 0.43 ml of 1-iododecane in substantially the same manner as in example 46-c), except that the reaction was initiated under ice-cooling and the system was stirred for 18 hours while the temperature was gradually raised to room temperature. NMR (CDCI3) d: 0.88 (3H, br.t, J = 6.7 Hz), 1.20-1.33 (17H, m), 1.39 (3H, d, J = 6.3 Hz), 1.69-1.81 (2H,), 3.22 (3H, s), 3.35 (1H, dd, Jx = 6.7 Hz, J2 = 2.9 Hz), 3.39-3.49 (1H, m), 4.17-4.38 (4H, m), 8.06 (1H, s), 8.49 ( 1H, s) MS (ESI): 552 (M + + H) Example 239 (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b ] thiazol-2-yl) -l-methyl-l-carbapen-2-em-3-carboxylate of (Z) -2- (3-phtalidylidene) ethyl In the same manner as in Example 2, 144 mg was obtained of the title compound from 172 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -2- (7-methanesulfonylimidazo [5, 1-b] thiazol-2-yl) - sodium l-methyl-l-carbapen-2-em-3-carboxylate and 146 mg of (z) -2- (3-phthalidylidene) ethyl bromide. NMR (CDC13) d: 1.29 (3H, d, J = 7.2 Hz), 1.38 (3H, d, J = 6. 3 Hz), 3.22 (3H, s), 3.6 (1H, dd, Jx = 6.6 Hz, J2 = 2.8 Hz), 3.47 (1H, m), 4.31 (1H, m), 4.39 (1H, dd, Ji = 9.6 Hz, J2 = 2.8 Hz), 5.22 (2H, m), 5.83 (1H, t, J = 7.0 Hz), 7.60 (1H, m), 7.73 (2H, m), 7.92 (1H, m) , 8.11 (1H, s), 8.50 (1H, e) MS (TSP): 570 (M ++ H) MS (TSP): 552 (M ++ H) Example 240 (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid acetoxymethyl thereof As in Example 2, 29 mg of the title compound was obtained from 110 mg of (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7- sodium methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate and 0.054 ml of acetoxymethyl bromide.

NMR (CDCI3) d: 1.29 (3H, d, J = 7.4 Hz), 1.38 (3H, d, J = 6.3 Hz), 1.91 (1H, br.s), 2.13 (3H, s), 2.45 (3H, s), 3.35 (1H, dd, Ji = 6.6 Hz, J2 = 2.6 Hz), 3.45 (1H, m), 4.30 (1H, m), 4.35 (1H, dd, Ji = 9.7 Hz, J2 = 2.6 Hz) , 5.88, 5.96 (2H, ABq, J = 5.7 Hz), 8.04 (1H, s), 8.34 (1H, s) MS (TSP): 452 (M ++ H) Example 241 (1S, 5R, 6S) - 6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate from 1 (acetoxy) ethyl (a mixture of diastereomers) In the same manner as in Example 2, 18 mg of the title compound was obtained from 30 mg of (IS, 5R, 6S) -6- ((IR) -1 -hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate sodium and 48 mg of 1- (iodide acetoxy) ethyl. NMR (CDCI3) d: 1.29 (3H, d, J = 7.4 Hz), 1.38 (3H,), 1.56, 1.61 (total 3H, each d, J = 5.5 Hz), 1.85 (1H, m), 2.07, 2.14 (total 3H, each s), 2.44 (3H, s), 3.33 (1H, m), 3.42 (1H, m), 4.30 (1H, m), 4.34 (1H, m), 7.05 (1H, m), 8.02, 8.03 (total 1H, each s), 8.38 (1H, s) MS (TSP): 466 (MX-H) Example 242 (ÍS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) - l-Methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 1- (isobutyryloxy) ethyl ester (a mixture of diastereomers) In the same manner as in Example 2, 131 mg of the title compound was obtained from 200 mg of (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7 sodium methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate and 532 mg of 1- (isobutyryloxy) ethyl iodide. NMR (CDC13) d: 1.15 (3H, m), 1.21 (3H, m), 1.30 (3H, m), 1. 38 (3H, m), 1.56, 1.61 (total 3H, each d, J = 5.5 Hz), 1.89 (1H, m), 2.44 (3H, s), 2.57 (1H, m), 3.33 (1H, m) , 3.43 (1H, m), 7.06 (1H, m), 8.02 (1H, s), 8.36, 8.39 (total 1H, each s) MS (TSP): 494 (M ++ H) Example 243 (ÍS, 5R , 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioi idazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3 pivaloyloxymethylcarboxylate In the same manner as in Example 2, 27 mg of the title compound was obtained from 28 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l- Sodium methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate and 0.019 ml of pivaloyloxymethyl iodide. NMR (CDCI3) d: 1.19 (9H, s), 1.27 (3H, d, J = 7.4 Hz), 1.35 (3H, d, J = 6.3 Hz), 2.02 (1H, br.s), 2.42 (3H, s), 3.32 (1H, dd, Ji = 6.5 Hz, J2 = 2.8 Hz), 3.44 (1H, m) , 4.29 (1H, m), 4.36 (1H, dd, Ji = 9.6 Hz, J2 = 2.8 Hz), 5.86, 5.97 (2H, ABq, J = 5.5 Hz), 8.04 (1H, s), 8.28 (1H, s) MS (TSP): 494 (M ++ H) Example 244 (SS, 5R, 6S) -6- ((IR) -1- hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 1- (pivaloyloxy) ethyl ester In the same manner as in Example 2, 139 mg of the title compound was obtained from 193 mg of (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [ Sodium 5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate and 300 mg of 1- (pivaloyloxy) ethyl iodide. NMR (CDC13) d: 1.17, 1.24 (total 9H, each s), 1.30 (3H,), 1. 38 (3H,), 1.55, 1.60 (total 3H, each d, J = 5.5 Hz), 2.10 (1H, br.s), 2.43 (3H, s), 3.33 (JLH, m), 3.43 (1H, m ), 4.29 (1H, m), 4.34 (1H, dd, Ji = 9.6 Hz, J2 = 2.8 Hz), 7.02 (1H, m), 8.02 (1H, s), 8.34, 8.38 (total 1H, each s) MS (TSP): 508 (M ++ H) Example 245 (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) - 2-Ethylbutyryloxymethyl 2-ethylbutyryloxymethyl-2-carboxylic acid In the same manner as in Example 2, 217 mg of the title compound were obtained from 253 mg of (SS, 5R, 6S) -6- ( (IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid sodium and 242 mg of 2-ethylbutyryloxymethyl iodide. NMR (CDCl 3) d: 0.85 (6H, m), 1.28 (3H, d, J = 7.4 Hz), 1.37 (3H, d, J = 6.3 Hz), 1.68 (4H, m), 2.27 (1H, m) , 2.43 (3H, s), 3.33 (1H, dd, J_. = 6.5 Hz, J2 = 2.7 Hz), 3.44 (1H, m), 4.29 (1H, m), 4.35 (1H, dd, J_, = 9.6 Hz, J2 = 2.7 Hz), 5.94 (2H, s), 8.05 (1H, s), 8.30 (1H, s) MS (TSP): 508 (M ++ H) Example 246 (SS, 5R, 6S) - 6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate from 1 (2-ethylbutyryloxy) ethyl (a mixture of diastereomers) In the same manner as in Example 2, 154 mg of the title compound was obtained from 224 mg of (1S, 5R, 6S) -6- ((IR) Sodium 1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate and 500 mg of iodide of 1 - (2-ethylbutyryloxy) ethyl. NMR (CDCI3) d: 0.90 (6H, m), 1.27 (3H,), 1.38 (3H, m), 1.56, 1.61 (total 3H, each d, J = 5.5 Hz), 1.60 (4H,), 2.05 ( 1H, br.s), 2.22 (1H,), 2.43 (3H, s), 3.33 (1H,), 3.42 (1H, m), 4.29 (1H, m), 4.33 (1H, m), 7.07 (1H ,), 8.02 (1H, s), 8.31, 8.40 (total 1H, each s) MS (TSP): 522 (M ++ H) Example 247 (ÍS, 5R, 6S) -6- ((IR) -1 -hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid cyclohexylcarbonyloxymethyl ester In the same manner as in Example 2 , 284 mg of the title compound was obtained from 255 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-] b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate and 267 g of cyclohexylcarbonyloxymethyl iodide. NMR (CDC1) d: 1.20-1.52 (4H, m), 1.29 (3H, d, J = 7.2 Hz), 1.37 (3h, d, J = 6.3 Hz), 1.60-1.95 (6H, m), 2.38 ( 1 HOUR, ) , 2. 44 (3H, s), 3.33 (1H, dd, Ji = 6.6 Hz, J2 = 2.8 Hz), 3.44 (1H, m), 4.29 (1H, m), 4.36 (1H, dd, Jx = 9.8 Hz, J2 = 2.8 Hz), 5.88, 5.96 (2H, ABq, J = 5.6 Hz), 8.04 (1H, s), 8.30 (1H, s) MS (TSP): 520 (M + H) Example 248 (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [ 5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 1- (cyclohexylcarbonyloxy) ethyl ester (a mixture of diastereomers) In the same manner as in Example 2, 232 were obtained. mg of the title compound from 207 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazole- 2-yl) -l-carbapen-2-em-3-carboxylate sodium and 400 mg of 1- (cyclohexylcarbonyloxy) ethyl iodide.

NMR (CDCI3) d: 1.20-2.00 (10H, m), 1.28 (3H, m), 1.38 (3H,), 1.55, 1.59 (total 3H, each d, J = 5.5 Hz), 2.10-2.40 (1H, m), 2.43 (3H, s), 3.33 (1H, m), 3.42 (1H, m), 4.29 (1H, m), 4. 34 (1H, m), 7.03 (1H, m), 8.02 (1H, s), 8.34, 8.37 (total 1H, each s) MS (TSP): 534 (M ++ H) Example 249 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of dicyclohexylacetoxymethyl In the same manner as in Example 2, 177 mg of the title compound was obtained from 161 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl- 2- (7-Methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate sodium and 219 mg of dicyclohexylacetoxymethyl iodide. NMR (CDCl 3) d: 0.80-1.21 (10H, m), 1.29 (3H, d, J = 7.3 Hz), 1. 35 (3h, d, J = 6.3 Hz), 1.60 (12H, m), 2.10 (1H, t, J = 7.4 Hz), 2.43 (3H, s), 3.34 (1H, dd, Jx = 6.8 Hz, J2 = 2.7 Hz), 3.45 (1H,), 4.28 (1H, m), 4.36 (1H, dd, Jx = 9.7 Hz, J2 = 2.8 Hz), 5.89 (1H, d, J = 5.6 Hz), 5.95 (1H , d, J = 5.6 Hz), 8. 07 (1H, s), 8.30 (1H, s) MS (FAB): 616 (M ++ H) Example 245 (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl -2- (adamantylcarbonyloxymethyl) 7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate In the same manner as in Example 2, 183 mg of the compound were obtained of the title from 201 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl ) -l-carbapen-2-em-3-carboxylate sodium and 264 mg of 1-adamantylcarbonyloxymethyl iodide. NMR (CDC13) d: 1.29 (3H, d, J = 7.3 Hz), 1.37 (3H, d, J = 6.1 Hz), 1.69 (6H, m), 1.86 (6H,), 1.99 (3H, m), 2.43 (3H, s), 3.35 (1H, dd, Ji = 6.6 Hz, J2 = 2.5 Hz), 3.45 (1H, dq, JL = 9.6 Hz, J2 = 7.3 Hz), 4.31 (1H, dq, J = 6.3 Hz), 4.35 (1H, dd, Ji = 9.7 Hz, J2 = 2.8 Hz), 5.88 (1H, d, J = 5.6 Hz), 5.95 (1H, d, J = 5.6 Hz), 8.06 (1H, s) , 8.27 (1H, s) MS (FAB): 572 (M + H) Example 251 (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7- Methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 1- (1-adamantylcarbonyloxy) ethyl ester (a mixture of diastereomers) In the same manner as in Example 2 , 72 mg of the title compound was obtained from 202 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-] b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate sodium and 500 mg of 1- (1-adamantylcarbonyloxy) ethyl iodide. NMR (CDCI3) d: 1.28 (3H, m), 1.38 (3H, m), 1.55, 1.59 (total 3H, each d, J = 5.5 Hz), 1.62-2.05 (15H, m), 2.43 (3H, s ), 3.33 (1H, m), 3.42 (1H, m), 4.30 (1H, m), 4.34 (1H, m), 7.02 (1H, m), 8.03 (1H, s), 8.31, 8.36 (total 1H , each s) MS (TSP): 586 (M ++ H) Example 252 (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5 , 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate 3-phthalidyl (a mixture of diastereomers) In the same manner as in Example 2, 173 mg of the titre from 219 mg of (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate sodium and 230 mg of 3-phthalidyl bromide. NMR (CDC13) d: 1.30 (6H, m), 2.41, 2.43 (total 3H, each s), 3. 34 (1H, m), 3.48 (1H, m), 4.25 (1H, m), 4.34 (1H,), 7.45, 7.47 (total 1H, each s), 7.63-7.92 (4H, m), 7.99, 8.03 (total 1H, each s), 8.17, 8.42 (total 1H, each s) MS (TSP): 512 (M ++ H) Example 253 (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) - L-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid benzoyloxymethyl ester In the same manner as in Example 2, 192 were obtained. mg of the title compound from 201 mg of (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5,1-b] thiazole- Sodium 2-yl) -l-carbapen-2-em-3-carboxylate and 262 mg of benzoyloxymethyl iodide. NMR (CDCI3) d: 1.28 (3H, d, J = 7.3 Hz), 1.36 (3H, d, J = 6. 4 Hz), 2.42 (3H, s), 3.33 (1H, dd, Jx = 6.6 Hz, J2 = 2.9 Hz), 3.44 (1H, dq, Ji = 9.5 Hz, J2 = 7.3 Hz), 4.29 (1H, dq, J = 6.3 Hz), 4.36 (1H, dd, Ji = 9.7 Hz, J2 = 2.8 Hz), 6.17 (2H, s), 7.44 (2H, t, J = 7.8 Hz), 7.58 (1H, m), 8.02 (1H, s), 8. 06 (2H, m), 8.30 (1H, s) MS (FAB): 508 (M ++ H) Example 254 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl -2- (7-Methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 1- (benzoyloxy) ethyl ester (a mixture of diastereomers) In the same way as in Example 2, 137 mg of the title compound was obtained from 180 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [ Sodium 5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate and 300 mg of 1- (benzyloxy) ethyl iodide. NMR (CDCI3) d: 1.28 (3H, m), 1.34, 1.38 (total 3H, each d, J = 6.2 Hz), 1.90 (1H, br.s), 2.42 (3H, s), 3.32 (1H, m ), 3.42 (1H, m), 4.29 (1H, m), 4.36 (1H, m), 7.30 (1H, m), 7.45 (2H, m), 7.59 (1H, m), 7.95, 7.96 (total 1H, each s ), 8.07 (1H, m), 8.33, 8.38 (total 1H, each s) MS (TSP): 528 (M ++ H) Example 255 (ÍS, 5R, 6S) -6- ((IR) -1- hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 2-methylbenzoyloxymethyl ester In the same manner as in the example 2, 109 mg of the title compound was obtained from 159 mg of (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5,1] -b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate sodium and 200 mg of 2-methylbenzoyloxymethyl iodide. NMR (CDC13) d: 1.28 (3H, d, J = 7.1 Hz), 1.36 (3H, d, J = '6.2 Hz), 2.42 (3H, s), 2.52 (1H, br.s), 2.59 (3H , s), 3.23 (1H, dd, Ji = 6.5 Hz J2 = 2.6 Hz), 3.44 (1H, m), 4.29 (1H, m), 4.35 (1H, dd, Ji = 9.6 Hz, J2 = 2.6 Hz), 6.13, 6.16 ( 2H, ABq, J = 5.6 Hz), 7.25 (2H, m), 7.42 (1H, m), 7.96 (1H, m), 8.01 (1H, s), 8.31 (1H, s) MS (TSP): 528 (M + + H) Example 256 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthio-imidazo [5, 1-b] thiazole-2 -l) -l-carbapen-2-em-3-carboxylic acid 1- (2-methylbenzoyloxy) ethyl ester (a mixture of diastereomers) In the same manner as in Example 2, 120 mg of the title compound was obtained from of 159 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l- sodium carbapen-2-em-3-carboxylate and 250 mg of 1- (2-methylbenzoyloxy) ethyl iodide. NMR (CDCI3) d: 1.28 (3H, m), 1.34, 1.38 (total 3H, each d, J = 6.3 Hz), 1.69, 1.74 (total 3H, each d, J = 5.5 Hz), 2.42 (3H, s ), 2.589, 2.62 (total 3H, each s), 3.33 (1H, m), 3.42 (1H, m), 3.89 (1H, m), 4.28 (1H, m), 4.35 (1H, m), 7.26 ( 2H, m), 7.40 (1H, m), 7.95 (2H,), 7.96 (1H, s), 8.34, 8.37 (total 1H, each s) MS (TSP): 542 (M ++ H) Example 257 ( ÍS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em -3- 4-methylbenzoyloxymethyl carboxylate In the same manner as in Example 2, 105 mg of the title compound was obtained from 127 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl ) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate sodium and 184 mg of 4-methylbenzoyloxymethyl iodide. NMR (CDC13) d: 1.27 (3H, d, J = 7.2 Hz), 1.35 (3H, d, J = 6.3 Hz), 2.40 (3H, s), 2.42 V3H, s), 2.62 (1H, br.s ), 3.32 (1H, dd, Ji = 6.6 Hz, J2 = 2.8 Hz), 3.43 (1H, m), 4.28 (1H, m), 4.35 (1H, dd, Jx = 9.7 Hz, J2 = 2.8 Hz), 6.15 (2H, s), 7.23 (2H, d, J = 8.2 Hz), 7.94 (2H, d, J = 8.2 Hz), 7.96 (1H, m), 8.01 (1H, s), 8.30 (1H, s) MS (TSP): 528 (M ++ H) Example 258 (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5,1] -b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 4- (2-propyl) benzoyloxymethyl ester In the same manner as in Example 2, 1630 mg of the title compound was obtained from of 128 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l- sodium carbapen-2-em-3-carboxylate and 180 mg of 4- (2-propyl) benzoyloxymethyl iodide. NMR (CDC13) d: 1.24 (3H, s), 1.26 (3H, s9, 1.28 (3H, d, J = 7.3 Hz), 1.36 (3H, d, J = 6.1 Hz), 2.42 (3H, s), 2.95 (1H, m), 3.33 (1H, dd, Ji = 6.5 Hz, J2 = 2.3 Hz), 3.43 (1H, m), 4. 29 (1H,), 4.35 (1H, dd, Ji = 9.8 Hz, .J2 = 2.3 Hz), 6.15 (2H, s), 7.29 (2H, d, J = 8.2 Hz), 7.99 (2H, d, J = 8.2 Hz), 8. 03 (1H, s), 8.31 (1H, s) MS (TSP): 556 (M + + H) Example 259 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl -2- (2,4-dimethylbenzoyloxymethyl 7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate In the same manner as in Example 2, the following were obtained: 85 mg of the title compound from 120 mg of (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazole -2-yl) -l-carbapen-2-em-3-carboxylate sodium and 150 mg of 2,4-dimethylbenzoyloxymethyl iodide. NMR (CDCI3) d: 1.28 (3H, d, J = 7.2 Hz), 1.37 (3H, d, J = 6.3 Hz), 2.00 (1H, br.s), 2.35 (3H, s), 2.43 (3H, s), 2.57 (3H, s), 3.32 (1H, dd, Jx = 6.6 Hz, J2 = 2.7 Hz), 3.44 (1H, m), 4.29 (1H, m), 4.35 (1H, dd, J_. = 9.6 Hz, J2 = 2.7 z), 6.12, 6.15 (2H, ABq, J = 5.7 Hz), 7.05 (2H, m), 7.89 (2H, d, J = 7.9 Hz), 8.00 (1H, s), 8.32 (1H, s) MS (TSP): 542 (M + H) Example 260 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [ 5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 2,4,6-trimethylbenzoyloxymethyl ester In the same manner as in Example 2, 140 mg of the title compound were obtained from 129 mg of (ÍS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5,1-b] thiazol-2-yl) - sodium l-carbapen-2-em-3-carboxylate and 198 mg of 2,4,6-trimethylbenzoyloxymethyl iodide. NMR (CDC13) d: 1.27 (3H, d, J = 7.1 Hz), 1.37 (3H, d, J = 6.3 Hz), 2.26 (3H, s), 2.27 (6H, s), 2.43 (3H, s) , 3.33 (1H, dd, Ji = 6.6 Hz, J2 = 2.7 Hz), 3.44 (1H, m), 4.29 (1H,), 4.35 (1H, dd, Ji = 9.6 Hz, J2 = 2.7 Hz), 6.10, 6.14 (2H, ABq, J = 5.6 Hz), 6.82 (2H, s), 8.03 (1H, s), 8.32 (1H, s) MS (TSP): 542 (M ++ H) Example 261 (SS, 5R) , 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3 1- (benzyloxyethoxy) ethyl carboxylate (a mixture of diastereomers) In the same manner as in Example 2, 122 mg of the title compound was obtained from 201 mg of (IS, 5R, 6S) -6- (( IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate sodium and 400 mg of iodide of 1- (benzyloxyethoxy) ethyl. NMR (CDC13) d: 1.27 (3H, d, J = 7.3 Hz), 1.36, 1.37 (total 3H, each d, J = 6.1 Hz), 1.58, 1.63 (total 3H, each d, J = 5.3 Hz), 2.42 (3H, s), 3.33 (1H, m), 3.42 (1H, m), 4.10 (1H, m), 4.21 (1H, m), 4.27 (1H, m), 4.34 (1H, m), 4.60 (1H, s), 4.65 (1H, d, J = 11.9 Hz), 4.70 (1H, d, J = 11.7 Hz), 7.13 (1H, m), 7.33 (5H, m), 8.04 (1H, s) , 8.32, 8.34 (total 1H, each s) MS (TSP): 572 (M ++ H) Example 262 (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2 - (7-Methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 1- (ethoxycarbonyloxy) ethyl ester (a mixture of diastereomers) In the same manner as in the Example 2, 24 mg of the title compound was obtained from 26 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate sodium and 31 mg of 1- (ethoxycarbonyloxy) ethyl iodide. NMR (CDCI3) d: 1.29-1.40 (9H, m), 1.59, 1.65 (total 3H, each d, J = 5.5 Hz), 2.42 (3H, s), 3.32 (1H, m), 3.43 (1H, m ), 4. 18-4.28 (4H, m), 6.93 (1H, m), 8.03 (1H, s), 8.37, 8.38 (total 1H, each s) MS (TSP): 496 (M ++ H) Example 263 (ÍS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-) methylthio-imidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate 2-propyloxycarbonyloxymethyl In the same manner as in Example 2, 205 mg of the title compound was obtained from 271 mg of (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl -2- (7-Methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate sodium and 300 mg of 2-propyloxycarbonyloxymethyl iodide. NMR (CDC13) d: 1.29 (9H, m), 1.36 (3H, d, J = 6.3 Hz), 2.43 (3H, s), 2.62 (1H, br.s), 3.33 (1H, dd, Ji = 6.6 Hz, J2 = 2.8 Hz), 3.44 (1H,), 4.30 (1H, m), 4.36 (1H, dd, i = 9.6 Hz, J2 = 2.8 Hz), 5.88, 5.95 (2H, ABq, J = 5.9 Hz), 8.04 (1H, s), 8. 36 (1H, s) MS (TSP): 496 (M + + H) Example 264 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo) [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 1- (2-propyloxycarbonyloxy) ethyl ester (a mixture of diastereomers) In the same manner as in example 2, 249 mg of the title compound were obtained from 295 mg of (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b ] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate sodium and 383 mg of 1- (2-propyloxycarbonyloxy) ethyl iodide. NMR (CDC13) d: 1.28 (6H, m), 1.37 (6H, m), 1.58, 1.64 (total 3H, each d, J = 5.3 Hz), 2.43 (3H, s), 3.32 (1H, m), 3.40 (1H, m), 4.30 (1H, m), 4.34 (1H, m), 4.91 (1H, m), 6.93 (1H,), 8.02 (1H, s), 8.38 (1H, s) MS (TSP): 510 (M ++ H) Example 265 (IS, 5R, 6S) -6- ((IR) (1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 1- (2-propyloxycarbonyloxy) - 1-propyl (a mixture of diastereomers) In the same manner as in Example 2, 220 mg of the title compound was obtained from 305 mg of (IS, 5R, 6S) -6- ((IR) -1- hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate sodium and 414 mg of 1- (2-iodide -propyloxycarbonyloxy) -1-propyl. MR (CDCI3) d: 1.00, 1.07 (total 3H, each d, J = 7.4 Hz), 1. 29 (3H, m), 1.36 (3H, m), 1.94 (2H, m), 2.10 (1H, m), 2.43 (3H, s), 3.31 (1H,), 3.43 (1H, m), 4.28 ( 1H, m), 4.34 (1H, m), 4.93 (1H, m), 6.80 (1H, m), 8.02 (1H, s), 8.40 (1H, s) MS (TSP): 524 (M + + H) Example 266 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b ] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of 2-methyl-1- (2-propyloxycarboryl) -1-propyl In the same manner as in Example 2, 169 were obtained mg of the title compound from 170 ng of (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazole- Sodium 2-yl) -l-carbapen-2-em-3-carboxylate and 900 mg of 2-methyl-1- (2-propyloxycarb-cyloxy) -1-propyl iodide. NMR (CDC13) d: 1.00 (3H, m), 1.07 (3H,), 1.28 (6H, m), 1.35 (6H, m), 2.12 (1H, m), 2.42 (3H, s), 2.60 (1H , m), 3.32 (1H, m), 3.42 (1H, m), 4.28 (1H, m), 4.35 (1H, m), 4.90 (1H, m), 6.63, 6.68 (total 1H, each d, J = 5.6 Hz), 8.01 (1H, s), 8.39, 8.40 (total 1H, each s) MS (TSP): 538 (M * + H) Example 267 (ÍS, 5R, 6S) -6- ((IR) 1- (1-hydroxyethi.l) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 1- (1-propyloxycarbonyloxy) ) ethyl (a mixture of diastereomers) In the same manner as in Example 2, 147.0 mg of the title compound was obtained from 200.0 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl ) -l-Methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate sodium and 213.3 mg of 1- (1-) iodide propyloxycarbonyloxy) ethyl.

NMR (CDCI3) d: 0.96 (3H, td, Ji = 7.3 Hz, J2 = 15.1 Hz), 1.38 (3H, dd, Ji = 8.8 Hz, J2 = 6.3 Hz), 1.60, 1.66 (total 3H, each d, J = 5.4 Hz), 1.73 (2H, m), 2.44 (3H, s), 3.32 (1H, d, J = 6.3 Hz), 3.43 (1H, m), 4.14 (2H, td, Ji = 6.8 Hz, J2 = 21.4 Hz), 4.28 (1H, m), 4.34 (1H, m), 6.94 (1H, m), 8.02, 8.02 (total 1H, each s, J = 1.7 Hz), 8.38, 8.39 (total 1H, each s, J = 4.6 Hz) MS (TSP): 538 (M ++ H) Example 267 (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7 -methylthio-imidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 1- (1-propyloxycarbonyloxy) ethyl ester (a mixture of diastereomers) In the same manner as in Example 2, 147 mg of the title compound was obtained from 200.0 mg of (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5 , 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate and 213 mg of 1- (1-propyloxycarbonyloxy) ethyl iodide. NMR (CDCI3) d: 0.96 (3H, td, Ji = 7.3 Hz, J2 = 15.1 Hz), 1.38 (3H, dd, Ji = 8.8 Hz, J2 = 6.3 Hz), 1.60, 1.66 (total 3H, each d, J = 5.4 Hz), 1.73 (2H, m), 2.44 (3H, s), 3.32 (1H, d, J = 6. 3 Hz), 3.43 (1H,), 4.14 (2H, td, Ji = 6.8 Hz, J2 = 21.4 Hz), 4.28 (1H, m), 4.34 (1H,), 6.94 (1H, m), 8.02, 8.02 (total 1H, each s, J = 1.7 Hz), 8.38, 8.39 (total 1H, each s, J = 4.6 Hz) MS (TSP): 510 (M ++ H) Example 268 (ÍS, 5R, 6S) - 6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7- ethylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of 3- pentyloxycarbonyloxymethyl In the same manner as in Example 2, 205 mg of the title compound was obtained from 231 mg of (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2 Sodium (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate and 310 mg of 3-pentyloxycarbonyloxymethyl iodide. NMR (CDC13) d: 0.89 (6H, q, J = 7.1 Hz), 1.28 (3H, d, J = 7.1 Hz), 1.37 (3H, d, J = 6.1 Hz), 1.62 (4H, m), 2.44 (3H, s), 3.33 (1H, dd, Ji = 6.5 Hz, J2 = 2.6 Hz), 3.45 (1H, m), 4.30 (1H, m), 4.35 (1H, dd, Ji = 9.6 Hz, J2 = 2.6 Hz), 4.62 (1H, m), 5.91, 5.96 (2H, ABq, J = 5.8 Hz), 8.04 (1H, s), 8.36 (1H, s) MS (TSP): 524 (M ++ H) Example 269 (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthio-imidazo [5, 1-b] thiazol-2-yl) -l- 1- (3-Pentyloxycarbonyloxy) ethyl carbapen-2-em-3-carboxylate (a mixture of diastereomers) In the same manner as in Example 2, 210 mg of the title compound was obtained from 297 mg of , 5R, 6S) -6- ((lR) -l-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em- Sodium 3-carboxylate and 400 mg of 1- (3-? -yloxycarbonyloxy) ethyl iodide. NMR (CDC13) d: 0.90 (6H, m), 1.27 (3H, m), 1.37 (3H, m), 1.62 (7H, m), 2.42 (3H, s), 3.32 (1H, m), 3.43 ( 1H, m), 4.28 (1H, m), 4.33 (1H, m), 4.62 (1H, m), 6.93 (1H, m), 8.01 (1H, s), 8.35, 8.38 (total 1H, each s) MS (TSP): 538 (M + + H) Example 270 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthio-imidazo [5,1] -b] thiazol-2-yl) -l-carbapen-2-e-3-carboxylic acid 1- (1-butyloxycarbonyloxy) ethyl ester (a mixture of diastereomers) In the same manner as in Example 2, 147.3 mg of the title compound from 200.0 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazole -2-yl) -l-carbapen-2-em-3-carboxylate sodium and 258.4 mg of 1- (1-butyloxycarbonyloxy) ethyl iodide. NMR (CDCI3) d: 0.93 (3H, td, Ji = 7.6 Hz, J2 = 11.9 Hz), 1.28 (3H, dd, Ji = 7.1 Hz, J2 = 2.9 Hz), 1.38 (3H, dd, Ji = 8.5 Hz , J2 = 6.4 Hz), 1.43 (2H, m), 1.60, 1.65 (total 3H, each d, J = 5.3 Hz), 1.68 (2H, m), 2.44 (3H, s), 3.32 (1H, d, J = 6.6 Hz), 3.34 (1H, m), 4.16, 4.22 (total 1H, each t, J = 6.8 Hz), 4.29 (1H,), 4.33 (1H, m), 6.94 (1H, m), 8.02 , 8.02 (total 1H, each s, J = 1.9 Hz), 8.38, 8.39 (total 1H, each s, J = 5.1 Hz) MS (TSP): 524 (M ++ H) Example 271 (ÍS, 5R, 6S ) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthio-imidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3 4-heptyloxycarbonyloxymethyl carboxylate In the same manner as in Example 2, 165 mg of the title compound was obtained from 137 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l sodium-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate and 200 mg of 4-heptyloxycarbonyloxymethyl iodide. NMR (CDC13) d: 0.90 (6H, m), 1.28 (3H, d, J = 7.2 Hz), 1.30- 1.35 (4H, m), 1.37 (3H, d, J = 6.2 Hz), 1.55 (4H, m), 2.43 (3H, s), 3.33 (1H, dd, Ji = 6.8 Hz, J2 = 2.8 Hz), 3.44 (1H, m), 4.29 (1H, m), 4.35 (1H, dd, J: = 9.6 Hz, J2 = 2.8 Hz), 4.74 (1H, m), 5.90, 5.95 (2H, ABq, J = 5.8 Hz), 8.04 (1H, s), 8.35 (1H, s) MS (TSP): 552 (M ++ H Example 272 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthio-imidazo [5, 1-b] thiazol-2-yl) -l -carbapen-2-em-3-carboxylic acid 1- (4-heptyloxycarbonyloxy) ester (a mixture of diastereomers) In the same manner as in Example 2, 164 mg of the title compound was obtained from 176 mg of ( ÍS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em Sodium 3-carboxylate and 320 mg of 1- (4-heptyloxycarbonyloxy) ethyl iodide. NMR (CDC13) d: 0.90 (6H, m), 1.29 (3H, m), 1.38 (3H, m), 1. 50-1.68 (7H, m), 2.02 (1H, m), 2.43 (3H, s), 3.32 (1H, m), 3.43 (1H, m), 4.28 (1H, m), 4.33 (1H, m) , 4.76 (1H, m), 6.93 (1H, m), 8.01 (1H, s), 8.'37, 8.40 (total 1H, each s) MS (TSP): 566 (M ++ H) Example 273 (ÍS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of 1- (3 methyl-l-butyloxycarbonyloxy) ethyl (a mixture of diastereomers) In the same manner as in Example 2, 57.2 mg of the title compound was obtained from 200.0 mg of (1S, 5R, 6S) -6- (( IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid sodium and 235.5 mg of iodide of 1- (3-methyl-l-butyloxycarbonyloxy) ethyl. NMR (CDCI3) d: 0.90, 0.93 (total 3H, each d, J = 6.6 Hz), 1. 29 (3H, dd, Ji = 7.3 Hz, J2 = 2.4 Hz), 1.38 (3H, m), 1.53 (1H, m), 1.60 (3H, m), 1.63 (2H, m), 3.24 (3H , s), 3.32 (1H, m), 3.43 (1H, m), 4.25 (2H, t, J = 6.8 Hz), 4.28 (1H, m), 4'.33 (1H, m), 6.94 (1H, m), 8.01, 8.03 (total 1H, each s), 8. 38, 8.39 (total 1H, each s) MS (TSP): 538 (M ++ H) Example 274 (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-Methylthio-imidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 1- (1-pentyloxycarbonyloxy) ethyl ester (a mixture of diastereomers) In the same way that in Example 2, 248 mg of the title compound were obtained from 220 mg of (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5,1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid sodium and 300 mg of 1- (1-pentyloxycarbonyloxy) ethyl iodide. NMR (CDC13) d: 0.85-0.92 (3H, m), 1.28, 1.29 (total 3H, d, J = 7.3 Hz), 1.37, 1.38 (totak 3H, d, J = 6.4 Hz), 1.25-1.40 (4H, m), 1.60, 1.66 (total 3H, d, J = 5.6 Hz), 1.70-1.75 (2H, m), 2.44 (3H, s), 3.33 (total 1H, dd, Ji = 6.6 Hz, J2 = 2.7 Hz), 3.43 (total 1H, q, J = 7.3 Hz), 4.10-4.35 (4H, m), 6.94 (total 1H, q, J = 5.6 Hz), 8.01 (total 1H, s), 8.38, 8.40 ( total 1H, s) Example 275 (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) 1- (4-methyl-1-pentyloxycarbonyloxy) ethyl ester (1-diastereomer mixture) -l-carbapen-2-em-3-carboxylic acid In the same manner as in Example 2, 218 mg of the title compound were obtained from 220 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l sodium carbapene-2-em-3-carboxylate and 300 mg of 1- (4-methyl-1-pentyloxycarbonyloxy) ethyl iodide. NMR (CDCI3) d: 0.86 (3H, d, J = 6.7 Hz), 0.89 (3H, d, J = 6. 7 Hz), 1.27, 1.29 (total 3H, d, J = 7.3 Hz), 1.37, 1.39 (total 3H, d, J = 6.3 Hz), 1.20-1.28 (2H, m), 1.60-1.66 (total 3H, d, J = 5.5 Hz), 1.50-1.70 (2H,), 1.92 (1H, dd, Ji = 8.8 Hz, J2 = 4.8 Hz), 2.44 (3H, s), 3.33 (total 1H, dd, J = 6.8 , 2.7 Hz), 3.44 (1H, dq, J = 9.3, 7.3 Hz), 4.10-4.35 (4H, m), 6.94 (total 1H, q, J = 3.7 Hz), 8.04, 8.05 (total 1H, s) , 8.39, 8.40 (total 1H, s) Example 276 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthio-imidazo [5, 1-b ] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 5-nonyloxycarbonyloxymethyl ester In the same manner as in Example 2, 199 mg of the title compound was obtained from 171 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3 sodium carboxylate and 250 mg of 5-nonyloxycarbonyloxymethyl iodide. NMR (CDCl 3) d: 0.85 (6H, m), 1.27 (3H, d, J = 7.3 Hz), 1.28 (8H, m), 1.36 (3H, d, J = 6.3 Hz), 1.56 (4H, m) , 2.42 (3H, s), 2.99 (1H, br.s), 3.32 (1H, dd, Ji = 6.8 Hz, J2 = 2.8 Hz), 3.44 (1H, m), 4.28 (1H,), 4.35 (1H , dd, J: = 9.7 Hz, J2 = 2. 8 Hz), 4.71 (1H, m), 5.90, 5.95 (2H, ABq, J = 5.8 Hz), 8.03 (1H, s), 8.35 (1H, s) MS (TSP): 580 (M ++ H) Example 277 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioi idazo [5, 1-b] thiazol-2-yl) -l-carbapen -2- [3- (2, -Dimethyl) pentoxycarbonyloxy] ethyl ester (a mixture of diastereomers) In the same manner as in Example 2, 129 mg of the title compound was obtained from 201 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5,1-b] thiazol-2-yl) -l-carbapen Sodium 2-em-3-carboxylate and 346 mg of 1- [3- (2,4-dimethyl) pentoxycarbonyloxy] ethyl iodide.

NMR (CDC13) d: 0.89 (12H, m), 1.27, 1.29 (total 3H, each d, J = 6.8 Hz), 1.37, 1.39 (total 3H, each d, J = 6.2 Hz), 1.61, 1.65 total 3H , each d, J = 5.5 Hz), 2.43 (total 3H, each s), 3.35 (1H,), 3.43 (1H, m), 4.26-4.44 (3H, m), 6.92 (1H, m), 8.00, 8.01 (total 1H, each s), 8.31, 8.39 (total 1H, each s) MS (TSP): 566 (M ++ H) Example 278 (ÍS, 5R, 6S) -6- ((IR) -1- hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 1- (2,2-dimethyl-l- propyloxycarbonyloxy) ethyl (a mixture of diastereomers) From the polyp in the manner in Example 2, 175.5 mg of the title compound was obtained from 200.0 mg of (1S, 5R, 6S) -6- ((IR) -1- hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate sodium and 240.8 mg of 1- (2-iodide , 2-dimethyl-1-propyloxycarbonyloxy) ethyl. NMR (CDC13) d: 0.93, 0.97 (total 9H, each s), 1.27 (3H, m), 1.35 (3H, m), 1.61, 1.65 (total 3H, each d, J = 5.4 Hz), 2.43 (3H , s), 3.32 (1H, m), 3.43 (1H, m), 3.89 (2H,), 4.28 (1H,), 4.34 (1H, td, Jx = 3.4 Hz, J2 = 9.5 Hz), 6.94 (1H , q, J = 5.4 Hz), 8.20 (1H, s), 8.37, 8.39 (total 1H, each s) MS (TSP): 538 (M ++ H) Example 279 (ÍS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of 1- (3 , 3-dimethyl-2-butyloxycarbonyloxy) ethyl (a mixture of diastereomers) In the same manner as in Example 2, 124.8 mg of the title compound were obtained from 200.0 mg of (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid sodium and 252 mg of 1- (3, 3-dimethyl-2-butyloxycarbonyloxy) ethyl iodide. NMR (CDCI3) d: 0.88, 0.92, 0.93, 0.95 (total 9H, each s), 1. 28 (3H,), 1.38 (3H, m), 1.63 (3H, m), 1.65 (3H, d, J = . 6 Hz), 2.44 (3H, s), 3.33 (1H, m), 3.43 (1H, m), 4.27 (1H, m), 4.32 (1H, m), 4.58 (1H, m), 6.94 (1H, m), 8.00, 8.01 (total 1H, each s), 8.39, 8.40 (total 1H, each s) MS (TSP): 552 (M ++ H) Example 280 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl ) -l-Methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 1- (2-cyclohexyl-l-ethyloxycarbonyloxy) ethyl ester (a mixture of diastereomers) The title compound (102.1 mg) was obtained from 200.0 mg of (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7 -methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate sodium and 344.0 mg of 1- (2-cyclohexyl-1-ethyloxycarbonyloxy) ethyl iodide thereof as in Example 2, except that sodium hydrogen carbonate was not used in the reaction. NMR (CDC13) d: 0.83 (2H, m), 1.10 (4H, m), 1.21 (3H, dd, Jx = 7.3 Hz, J2 = 2.0 Hz), 1.28, 1.32 (total 3H, each d, J = 6.3 Hz), 1.46 (2H, ABq, J = 6.8 Hz), 1.552, 1.57 (total 3H, each d, J = 5.4 Hz), 1.54-1.70 (5H, m), 2.36 (3H, s), 3.25 (1H , m), 3.35, 3.37 (total 1H, each t, J = 7.6 Hz), 4.18 (2H, t, J = 6.8 Hz), 4.27 (1H, m), 6.86, 6.88 (total 1H, each t, J = 5.3 Hz), 7.95, 7.95 (total 1H, each s), 8.31, 8.32 (total 1H, each s) MS (TSP): 578 (M ++ H) Example 281 (ÍS, 5R, 6S) -6 - ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of 1- ( 2-phenyl-1-ethyloxycarbonyloxy) ethyl (a mixture of diastereomers) The title compound (206.4 mg) was obtained from 200.0 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) sodium l-methyl-2- (7- ethylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate and 239.2 mg of 1- (2-phenyl) iodide -l-ethyloxycarbonyloxy) ethyl in the same manner as in Example 2, ex No sodium hydrogencarbonate was used in the reaction. NMR (CDC1) d: 1.21 (3H, d, J = 7.3 Hz), 1.29, 1.31 (total 3H, each d, J = 6.4 Hz), 1.51, 1.57 (total 3H, each d, J = . 6 Hz), 2.36 (3H, s), 2.89, 2.96 (total 2H, each t, J = 7.4 Hz), 3.25 (1H, dd, Ji = 6.6 Hz, J2 = 2.5 Hz), 3.36 (1H, m), 4. 22 (1H, m), 4.27 (1H, m), 4.34 (2H, t, J = 7.3 Hz), 6.86 (1H, m), 7.17 (5H, m), 7.94 (1H, s), 8.30 (1H, s) MS (TSP): 572 (M ++ H) Example 282 (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid cyclohexyloxycarbonyloxymethyl thereof As in Example 2, 27 mg of the title compound was obtained from 24 mg of (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7- sodium methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate and 28 mg of cyclohexyloxycarbonyloxymethyl iodide. NMR (CDCI3) d: 1.28 (3H, d, J = 7.2 Hz), 1.36 (3H, d, J = 6.2 Hz), 1.30-1.67 (4H,), 1.70-1.95 (6H, m), 2.43 (3H , s), 2. 69 (1H, br.s), 3.33 (1H, dd, Jx = 6.6 Hz, J2 = 2.7 Hz), 3.44 '(1H, m), 4.29 (1H, m), 4.36 (1H, dd, Jx = 9.6 Hz, J2 = 2.7 Hz), 4.65 (1H, m), 5.89, 5.95 (2H, ABq, J = 5.8 Hz), 8.04 (1H, s), 8.35 (1H, s) MS (TSP): 536 (M ++ H) Example 283 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2 -em-3- (cyclohexyloxycarbonyloxy) ethyl carboxylate (a mixture of diastereomers) In the same manner as in Example 2, "261 mg of the title compound was obtained from 314 mg of (IS, 5R, 6S ) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate from sodium and 300 mg of 1- (cyclohexyloxycarbonyloxy) ethyl iodide, NMR (CDC13) d: 1.27 (3H, m), 1.37 (3H, m), 1.20-2.00 (10H, m), 1.59, 1.65 (total 3H, each d, J = 5.5 Hz), 2.44 (3H, s), 3. 31 (1H, m), 3.42 (1H, m), 4.32 (1H, m), 4.66 (1H, m), 6.94 (1H, m), 8.02 (1H, s), 8.38 (1H, s) MS ( TSP): 550 (M + + H) Example 284 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 1- (cyclohexyloxycarbonyloxy) -1-propyl ester (a mixture of diastereomers) In the same manner as in Example 2, 117 mg of the compound was obtained of the title from 159 mg of (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl ) -l-carbapen-2-em-3-carboxylate sodium and 350 mg of 1- (cyclohexyloxycarbonyloxy) -1-propyl iodide. NMR (CDC13) d: 1.00, 1.07 (total 3H, each t, J = 7.4 Hz), 1. 29 (3H, m), 1.37 (3H, m), 1.30-1.60 (5H,), 1.77-2.22 (7H, m), 2.43 (3H, s), 3.32 (1H, m), 3.43 (1H, m ), 4.27 (1H, m), 4.34 (1H, m), 4.65 (1H, m), 6.80 (1H, m), 8.01 (1H, s), 8.39, 8. 40 (total 1H, each s) MS (TSP): 564 (M + + H) Example 285 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7 -methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 1- (cyclohexyloxycarbonyloxy) -2-methyl-l-propyl ester (a mixture of diastereomers) In the same manner as in Example 2, 113 mg of the title compound was obtained from 197 mg of (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) - Sodium l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate and 950 mg of 1- (cyclohexyloxycarbonyloxy) -2 iodide -methyl-l-propyl. NMR (CDCl 3) d: 1.04 (6H, m), 1.29 (3H, m), 1.37 (3H, m), 1.30-2.20 (11H, m), 2.43 (3H, s), 3.32 (1H, m), 3.42 (1H, m), 4.39 (1H, m), 4.64 (1H, m), 6.63, 6.68 (total 1H, each d, J = 4. 7 Hz), 8.01 (1H, s), 8.40, 8.41 (total ÍE, each s) MS (TSP): 578 (M ++ H) Example 286 (ÍS, 5R, 6S) -6- ((IR) - 1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid cyclohexyl (cyclohexyloxycarbonyloxy) methyl (a mixture of diastereomers) In the same manner as in Example 2, 115 mg of the title compound was obtained from 198 mg of (1S, 5R, 6S) -6- ((ÍR) -1-hydroxyethyl) - sodium l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate and 800 mg of cyclohexyl (cyclohexyloxycarbonyloxy) methyl iodide.

NMR (CDC1) d: 1.15-2.02 (21H, m), 1.28 (3H, m), 1.37 (3H, m), 2.35 (1H, br.s), 2.43 (1H, m), 3.32 (1H, m ), 3.42 (1H, m), 4.32 (2H, m), 4.63 (1H, m), 6.65 (1H, m), 8.01 (1H, s), 8. 39 (1H, s) MS (TSP): 618 (M + + H) Example 287 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthio) -imidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate from 2-adamantyloxycarbonyloxymethyl In the same manner as in Example 2, 135 mg of the title compound was obtained from 104 mg of (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl -2- (7-Methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate sodium and 200 mg of 2-adamantyloxycarbonyloxymethyl iodide. NMR (CDCI3) d: 1.28 (3H, d, J = 7.2 Hz), 1.37 (3H, d, J = 6. 3 Hz), 1.50-2.12 (14H, m), 2.43 (3H, s), 3.34 (1H, dd, Jx = 6.6 Hz, J2 = 2.8 Hz), 3.44 (1H, m), 4.30 (1H,), 4.36 (1H, dd, Ji = 9.6 Hz, J = 2.8 Hz), 4.82 (1H, m), 5.91, 5.96 (2H, ABq, J = 5.8 Hz), 8.04 (1H, s), 8.35 (1H, s) MS (TSP): 588 (M ++ H) Example 288 (SS, 5R, 6S) -6- ((IR) - 1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid phenoxycarbonyloxymethyl ester In the same manner as in the example 2, 133 mg of the title compound was obtained from 167 mg of (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5,1] -b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate sodium and 170 mg of phenoxycarbonyloxymethyl iodide. NMR (CDCI3) d: 1.29 (3H, d, J = 7.2 Hz), 1.37 (3H, d, J = 6. 3 Hz), 2.44 (3H, s), 3.35 (1H, dd, Ji = 6.3 Hz, J2 = 2.8 Hz), 3.45 (1H, m), 4.32 (1H, m), 4.38 (1H, dd, Ji = 9.8 Hz, J2 = 2.8 Hz), 5.97, 6.11 (2H, ABq, J = 5.8 Hz), 7.23 (3H, m), 7. 39 (2H, m), 8.02 (1H, s), 8.35 (1H, s) MS (TSP): 530 (M ++ H) Example 289 (SS, 5R, 6S) -6- ((IR) -1 -hydroxyethyl) -l-methyl-2- (7-methylthio-imidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 1- (phenoxycarbonyloxy) ethyl ester (a mixture of diastereomers) In the same manner as in Example 2, 156 mg of the title compound was obtained from 166 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) - sodium l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate and 300 mg of 1- (phenoxycarbonyloxy) ethyl iodide. NMR (CDC13) d: 1.28 (3H, m), 1.39 (3H, m), 1.67, 1.73 (total 3H, each d, J = 5.5 Hz), 2.43 (3H, s), 3.35 (1H, m), 3.44 (1H, m), 4.34 (2H, m), 7.03 (1H, m), 7.18-7.40 (5H, m), 8.01 (1H, s), 8.36 (1H, s) MS (TSP): 544 ( M ++ H) Example 290 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthio-imidazo [5, 1-b] thiazole-2- il) -l-carbapen-2-em-3-carboxylic acid 1- (phenoxycarbonyloxy) -1-propyl ester In the same manner as in Example 2, 179 mg of the title compound was obtained from 190 mg of (I S) , 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em- Sodium 3-carboxylate and 657 mg of 1- (phenoxycarbonyloxy) -1-propyl iodide. NMR (CDCI3) d: 1.05, 1.13 (total 3H, each t, J = 7.6 Hz), 1.26 (3H, m), 1.39 (3H, m), 2.01 (2H, m), 2.42 (3H, s), 2.61, 2.71 (total 1H, each br.s), 3.35 (1H, m), 3.43 (1H, m) 4.33 (1H, m), 4.38 (1H, m), 6.87 (1H, m), 7.16-7.40 (5H, m), 8.01 (1H, s), 8.36 (1H, s) MS (TSP): 558 (M ++ H) Example 291 (SS, 5R, 6S) -6- ((IR) -1- hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 1- (2-methylphenoxycarbonyloxy) ethyl ester (a mixture of diastereomers) In the same manner as in Example 2, 200.0 mg of the title compound was obtained from 200.0 mg of (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl -2- (7-Methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid sodium ester and 500 mg of 1- (2-methylphenoxycarbonyloxy) ethyl iodide. NMR (CDC13) d: 1.28, 1.30 (total 3H, each d, J = 7.3 Hz), 1.38, 1.40 (total 3H, each d, J = 6.3 Hz), 1.69, 1.74 (total 1H, each d, J = 5.4 Hz), 1.84 (1H,), 2.20, 2.28 (total 3H, each s), 2.43 (3H, s), 3.33 (1H, m), 3.46 (1H, m), 4.28 (1H, m), 4.35 (1H, m), 7.01 (1H, m), 7.20 (4H, m), 8.00, 8.01 (total 1H, each s), 8.35, 8.38 (total 1H, each s) MS (TSP): 558 (M ++ H) Example 292 (ÍS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em- 3- (2-ethylphenoxycarbonyloxy) ethyl 3-carboxylate In the same manner as in Example 2, 181.0 mg of the title compound was obtained from 200.0 mg of (1S, 5R, 6S) -6- ((IR) Sodium 1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate and 500 mg of sodium iodide - (2-ethylphenoxycarbonyloxy) ethyl. NMR (CDC13) d: 1.13, 1.21 (total 3H, each t, J = 7.3 Hz), 1.28, 1.30 (total 3H, each d, J = 7.3 Hz), 1.38, 1.40 (total 3H, each d, J = 6.3 Hz), 1.69, 1.74 (total 3H, each d, J = 5.4 Hz), 2.00 (1H, m), 2.43 (3H, s), 2.59, 2.65 (total 2H, each q, J = 7.3 Hz), 3.33 (1H, m), 3.46 (1H, m), 4.28 (1H, m), 4.35 (1H, m), 7.01 (1H, m), 7.22 (4H, m), 8.00, 8.01 (total 1H, each s), 8.35, 8.38 (total 1H, each s) MS (TSP): 572 (M ++ H) Example 293 (ÍS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl -2- (7-Methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 1- (2-methoxyphenoxycarbonyloxy) ethyl ester (a mixture of diastereomers) Of the same As in example 2, 106.0 mg of the title compound was obtained from 200.0 mg of (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7- sodium methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate and 500 mg of l- (2-ethoxyphenoxycarbonyloxy) ethyl iodide. NMR (CDCI3) d: 1.28, 1.30 (total 3H, each d, J = 7.3 Hz), 1.39 (3H, d, J = 6.3 Hz), 1.69, 1.74 (total 3H, each d, J = 5.4 Hz), 1.92 (1H, m), 2.43 (3H, s), 3.33 (1H,), 3.46 (1H,), 3.81, 3.86 (total 3H, each s), 4.28 (1H, m), 4.35 (1H, m) , 6.98 (3H, m), 7.21 (2H, m), 7.99, 8.00 (total 1H, each s), 8.34, 8.37 (total 1H, each s) MS (TSP): 574 (M ++ H) Example 294 (SS, 5R, 6S) -6- ((RI) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2- 1- (3-methylphenoxycarbonyloxy) ethyl em-3-carboxylate (a mixture of diastereomers) In the same manner as in Example 2, 171.0 mg of the title compound was obtained from 200.0 mg of (IS, 5R, 6S ) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate from sodium and 500 mg of l- (3-methylphenoxycarbonyloxy) ethyl iodide. NMR (CDC13) d: 1.28, 1.30 (total 3H, each d, J = 7.3 Hz), 1.38, 1.40 (total 3H, each d, J = 6.3 Hz), 1.69, 1.74 (total 3H, each d, J = 5.4 Hz), 2.11, 2.17 (total 1H, each d, J = . 4 Hz), 2.34, 2.36 (total 3H, each s), 2.43 (3H, s), 3.33 (1H, m), 3.46 (1H, m), 4.28 (1H, m), 4.35 (1H, m), 7.03 (4H,), 7.25 (1H, m), 8.01, 8.02 (total 1H, each s) , 8.35, 8.37 (total 1H, each s) S (TSP): 558 (M ++ H) Example 295 (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-) Methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 1- (3-methoxyphenoxycarbonyloxy) ethyl ester (a mixture of diastereomers) In the same manner as in Example 2 , 189.0 mg of the title compound was obtained from 200.0 mg of (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioi idazo [5,1] sodium β-thiazol-2-yl) -l-carbapen-2-em-3-carboxylate and 500 mg of l- (3-methoxyphenoxycarbonyloxy) ethyl iodide. NMR (CDC13) d: 1.28, 1.30 (total 3H, each d, J = 7.3 Hz), 1.38, 1.40 (total 3H, each d, J = 6.3 Hz), 1.69, 1.74 (total 3H, each d, J = 5.4 Hz), 1.88 (1H, m), 2.43 (3H, s), 3.33 (1H, m), 3.46 (1H, m), 3.78, 3.80 (total 3H, each s), 4.28 (1H, m), 4.35 (1H, m), 6.77 (1H, m), 6.91 (1H, m), 7.02 (1H, m), 7.27 (1H, m), 8.01, 8.02 (total 1H, each s), 8.37, 8.39 ( total 1H, each s) MS (TSP): 574 (M + + H) Example 296 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo) [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 1- (4-methylphenoxycarbonyloxy) ethyl ester In the same manner as in Example 2; 148.0 mg of the title compound were obtained from 200.0 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7- ethylthioi idazo [5, 1-] b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate sodium and 500 mg of l- (4-ethylphenoxycarbonyloxy) ethyl iodide. NMR (CDC13) d: 1.29 (3H,), 1.39 (3H, m), 1.70 (3H, m), 1.83 (1H, m), 2.34 (3H, s), 2.43 (3H, s), 3.33 (1H , m), 3.46 (1H, m), 4.28 (1H, m), 4.35 (1H, m), 7.03 (2H,), 7.17 (3H,), 8.01 (1H, m), 8.38 (1H, m) MS (TSP): 558 (M + + H) Example 297 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] ] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 1- (4-ethylphenoxycarbonyloxy) ethyl ester (a mixture of diastereomers) In the same manner as in Example 2, 182.0 mg of the compound were obtained of the title from 200.0 mg of (ÍS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl ) -l-carbapen-2-em-3-carboxylate sodium and 500 mg of l- (4-ethylphenoxycarbonyloxy) ethyl iodide. NMR (CDCI3) d: 1.21, 1.22 (total 3H, each t, J = 7.3 Hz), 1.28, 1.30 (total 3H, each d, J = 7.3 Hz), 1.38, 1.40 (total 3H, each d, J = 6.3 Hz), 1.69, 1.74 (total 3H, each d, J = 5.4 Hz), 1.89 (1H, m), 2.43 (3H, s), 2.63, 2.64 (total 2H, each q, J = 7.3 Hz), 3.34 (1H, m), 3.46 (1H, m), 4.28 (1H, m), 4.35 (1H, m), 7.04 (2H, m), 7.19 (3H, m), 8.00, 8.01 (total 1H, each s), 8.36, 8.38 (total 1H, each s) MS (TSP): 572 (M ++ H) Example 298 (ÍS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl -2- (7-Methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 1- (4-methoxyphenoxycarbonyloxy) ethyl ester (a mixture of diastereomers) Of the same so that in Example 2, 158.0 mg of the title compound were obtained from 200.0 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2- sodium em-3-carboxylate and 500 mg of l- (4-methoxyphenoxycarbonyloxy) ethyl iodide. NMR (CDC13) d: 1.28, 1.30 (total 3H, each d, J = 7.3 Hz), 1. 38, 1.40 (total 3H, each d, J = 6.3 Hz), 1.69, 1.74 (total 3H, each d, J = 5.4 Hz), 1.94 (1H, m), 2.43 (3H, s), 3.33 (1H, m), 3.46 (1H, m),. 3.78, 3.79 (total 3H, each s), 4.28 (1H, m), 4.35 (1H, m), 6.87 (2H, m), 7.01 (1H, m), 7.09 (1H, m), 7.22 (1H, m), 8.01, 8.02 (total 1H, each s), 8.37, 8.38 (total 1H, each s) MS (TSP): 574 (M ++ H) Example 299 (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-) methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 1- (2, o-dimethylphenoxycarbonyloxy) ethyl ester (a mixture of diastereomers) In the same manner as in the Example 2, 110.0 mg of the title compound was obtained from 200.0 mg of (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate sodium and 500 mg of l- (2,6-dimethylphenoxycarbonyloxy) ethyl iodide. NMR (CDC13) d: 1.28, 1.30 (total 3H, each d, J = 7.3 Hz), 1.38, 1.40 (total 3H, each d, J = 6.3 Hz), 1.68 (1H, m), • 1.69, 1.74 (total 3H, each d, J = 5.4 Hz), 2.17 (3H, s), 2.25 (3H, s), 2.43 (3H, s), 3.33 (1H, m), 3.46 (1H, m), 4.28 (1H, m), 4.35 (1H, m), 6.99 (1H, m), 7.04 ( 3H, m), 8.01, 8.02 (total 1H, each s), 8.31, 8.38 (total 1H, each s) MS (TSP): 572 (M ++ H) Example 300 (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl ) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 1- (2,4-dimethylphenoxycarbonyloxy) ethyl ester (a mixture of diastereomers) In the same manner as in Example 2, 150.0 mg of the title compound was obtained from 200.0 mg of (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l- Sodium methyl-2- (7- ethylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate and 500 mg of l- (2,4-dimethylphenoxycarbonyloxy) iodide ethyl. NMR (CDCI3) d: 1.28, 1.30 (total 3H, each d, J = 7.3 Hz), 1.38, 1.40 (total 3H, each d, J = 6.3 Hz), 1.69, 1.74 (total 3H, each d, J = 5.4 Hz), 1.89 (1H, m), 2.15, 2.23 (total 3H, each s), 2.29, 2.30 (total 3H, each s), 2.43, 2.44 (total 3H, each s), 3.33 (1H, m) , 3.46 (1H, m), 4.28 (1H, m), 4.35 (1H, m), 7.02 (4H, m), 8.00, 8.01 (total 1H, each s), 8.34, 8.38 (total 1H, each s) MS (TSP): 572 (M + + H) Example 301 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b ] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 1- (2,5-dimethylphenoxycarbonyloxy) ethyl ester (a mixture of diastereomers) In the same manner as in Example 2, 174.0 mg were obtained of the title compound from 200.0 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazole-2 -l) -l-carbapen-2-em-3-carboxylate sodium and 500 mg of l- (2,5-dimethylphenoxycarbonyloxy) ethyl iodide. NMR (CDCI3) d: 1.28, 1.30 (total 3H, each d, J = 7.3 Hz), 1.38, 1.40 (total 3H, each d, J = 6.3 Hz), 1.69, 1.74 (total 3H, each d, J = 5.4 Hz), 2.00 (1H,), 2.14, 2.22 (total 3H, each s), 2.29, 2.31 (total 3H, each s), 2.43 (3H, s), 3.33 (1H, m), 3.46 (1H, m), 4.28 (1H, m), 4.35 (1H, m), 7.00 (4H, m), 8.00, 8.01 (total 1H, each s), 8.34, 8.38 (total 1H, each s) MS (TSP): 572 (M + + H) Example 302 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazole-2- il) -l-carbapen-2-em-3-carboxylic acid 1- [2-methyl-5- (2-propyl) phenoxycarbonyloxy] -ethyl ester (a mixture of diastereomers) In the same manner as in Example 2, obtained 172.0 mg of the title compound from 200.0 mg of (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b ] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate sodium and 500 mg of 1- [2-methyl-5- (2-propyl) phenoxycarbonyloxy] -ethyl iodide. NMR (CDC13) d: 1.22 (6H, t, J = 7.3 Hz), 1.29 (3H, d, J = 7.3 Hz), 1.39 (3H, d, J = 6.3 Hz), 1.69, 1.74 (total 3H, each d, J = 5.4 Hz), 2.00 (1H, m), 2.15, 2.23 (total 3H, each s), 2.43 (3H, s), 2.87 (1H,), 3.33 (1H, m), 3.46 (1H, m), 4.28 (1H, m), 4.35 (1H, m), 7.04 (4H, m), 8.00, 8.01 (total 1H, each s), 8.35, 8.39 (total 1H, each s) MS (TSP): 600 (M + + H) Example 303 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazole-2- il) -l-carbapen-2-em-3-carboxylic acid 1- (3,5-dimethylphenoxycarbonyloxy) ethyl ester (a mixture of diastereomers) In the same manner as in Example 2, 167.0 mg of the title compound was obtained from 200.0 mg of (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l sodium carbapene-2-em-3-carboxylate and 500 mg of l- (3,5-dimethylphenoxycarbonyloxy) ethyl iodide. NMR (CDC13) d: 1.28, 1.30 (total 3H, each d, J = 7.3 Hz), 1.38, 1.40 (total 3H, each d, J = 6.3 Hz), 1.69, 1.74 (total 3H, each d, J = 5.4 Hz), 2.05 (1H, m), 2.29 (3H, s), 2.31 (3H, s), 2.43 (3H, s), 3.33 (1H, m), 3.46 (1H, m), 4.28 (1H, m), 4.35 (1H, m), 6.78 (1H, s), 6.89 ( 2H, m), 7.01 (1H,), 7. 25 (1H, m), 8.00, 8.01 (total 1H, each s), 8.35, 8.38 (total 1H, each s) MS (TSP): 572 (M + + H) Example 304 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-) Methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid (2-, 4,6-trimethylphenoxycarbonyloxy) ethyl ester (a mixture of diastereomers) In the same manner as in Example 2, 163 mg of the title compound was obtained from 168 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [ Sodium 5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate and 200 mg of 1- (2,4,6-trimethylphenoxycarbonyloxy) ethyl iodide.

NMR (CDCI3) d: 1.28 (3H, m), 1.38 (3H, m), 1.67, 1.72 (total 3H, every d, J = 5.5 Hz), 2.12, 2.20 (total 6H, each s), 2.24, 2. 25 (total 3H, each s), 2.43 (3H, s), 3.33 (1H, m), 3.43 (1H, m), 4.29 (1H, m), 4.34 (1H, m), 6.84, 6.86 (total 2H, each s), 7.69 (1H, m), 8.00, 8.01 (total 1H, each s), 8.28 , 8. 35 (total 1H, each s) MS (TSP): 586 (M ++ H) Example 305 (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7 -methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 1- ((indan-5-yl) oxycarbonyloxy) ethyl ester (a mixture of diastereomers) Of the same As in example 2, 157.0 mg of the title compound were obtained from 156 mg of (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7- sodium methylthioimidazo [5,1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate and 527 mg of 1- ((indan-5-yl) oxycarbonyloxy) ethyl iodide. NMR (CDCI3) d: 1.27 (3H, m), 1.39 (3H, m), 1.66, 1.72 (total 3H, each d, J = 5.3 Hz), 2.08 (2H, m), 2.42 (3H, s), 2.87 (4H, m), 3.33 (1H, m), 3.42 (1H, m), 4.33 (2H, ), 6.88-7.20 (4H,), 8.01 (1H, s), 8.33, 8.35 (total 1H, each s) MS (TSP): 584 (M ++ H) Example 306 (ÍS, 5R, 6S) -6- ((IR) 1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of 1- ((indan-5- il) oxycarbonyloxy) -1-propyl (a mixture of diastereomers) In the same manner as in Example 2, 189 mg of the title compound was obtained from 182 mg of (IS, 5R, 6S) -6- (( IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid sodium and 700 mg of iodide of 1- ((indan-5-yl) oxycarbonyloxy) -1-propyl. NMR (CDC13) d: 1.05, 1.29 (total 3H, each t, J = 7.6 Hz), 1.29 (3H,), 1.40 (3H, m), 2.06 (4H, m), 2.21 (1H, m), 2.43 (3H, s), 2.88 (4H, m), 3.14 (1H, m), 3.43 (1H, m), 4.33 (2H, m), 6.87 (1H, m), 7.02-7.20 (3H, m), 8.00, 8.01 (total 1H, each s), 8.36, 8.39 (total 1H, each s) MS (TSP): 598 (M ++ H) Example 307 (ÍS, 5R, 6S) -6- ((IR) - 1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 1-heptyl The title compound was obtained (128 mg) from 161 mg of (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazole-2 sodium) -l-carbapen-2-em-3-carboxylate and 0.33 ml 1-iodoheptane in substantially the same manner as in example 46-c), except that the reaction was initiated under ice-cooling and the system was stirred for 18 hours while the temperature was gradually raised to room temperature. NMR (CDCI3) d? 0.88 (3H, br.s, J = 6.7 Hz), 1.25, 1.33 (11H, 1. 39 (3H, d, 'J = 6.3 Hz), 1.69-1.81 (2H, m), 2.43 (3H, s), 3.33 (1H, dl Ji = 6.7 Hz, J2 = 2.9 Hz), 3.37-3.48 (1H , m), 4.17-4.38 (4H,), 8.01 (1H, s), 8.27 (1H, s) MS (TSP): 478 (M ++ H) Example 308 (IS, 5R, 6S) -6- ( (IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [-5", 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate of 5-- methyl-2-oxo-l, 3-dioxolen-4-ylmethyl From the same maniira as in Example 2, 205 mg of the title compound was obtained from 231 mg of (IS, 5R, 6S) -6 - ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l> sodium carbapen-2-em-3-carboxylate and 240 mg of 5-methyl-2-oxo-l, 3-dioxolen-4-ylmethyl bromide, NMR (CDCl 3) d: 31.29 (3H, d, J = 7.1 Hz), 1.37 (3H, d, J = 6.0 Hz), 2.22 (3H, S), 2.44 (3H, s), 3.34 (1H, dd, J. = 6.3 Hz, J2 = 2.7 Hz), 3.47 (1H, m), 4.30 (1H, m), 4.36 (1H, dd, Ji = 9.8 Hz, J2 == 2.7 Hz), 5.00, 5.08 (2H, ABq, J = 14.0 Hz), 8.06 (1H, s), 8.22 (1H, s) MS (TSP): 492 (M * + H) Example 309 ( ÍS, 5R, 6S) -6- (("? R) -1-hydroxyethyl) -l-methyl-2- (7-methylthio-imidazo [5, 1-b] thiazol-2-yl) -l-carbapen -2- (3-) -2- (3-phthalidylidene) ethyl 2-em-3-carboxylate In the same manner as in Example 2, 169 mg of the title compound was obtained from 170 mg of (5S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid and 130 mg of (Z) -2- (3-phthalimidyl) ethyl bromide. NMR (CDC13) d: 1.28 (3H, d, J = 7.4 Hz), 1.37 (3H, d, J = 6.2 Hz), 2.41 (3H, s), 2.70 (1H, br.s), 3.34 (1H, dd, Ji = 6.5 Hz, J2 = 2.7 Hz), 3.44 (1H, m), 4.31 (1H, m) ", 4.36 (1H, dd, Ji = 9.6 Hz, J2 = 2.7 Hz), 5.20 (2H, s ), 5.82 (1H, t, J = 7.1 Hz), 7.58 (1H, m), 7.69 (2H, m), 7.89 (1H, m), 8.03 (1H, s), 8.31 (1H, s) MS ( TSP): 538 (M + + H) Example 310 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazole -2-) -l-carbapen-2-em-3-carboxylic acid 1- (1,1-dimethyl-l-butyloxycarbonyloxy) ethyl ester (a mixture of diastereomers) A solution of 156.6 mg of chloride of 1 ( 1,1-dimethyl-1-butyloxycarbonyloxy) ethyl ester in 2.0 ml of DMF to a suspension of 176.1 mg of silver iodide in 2.0 ml of DMF The mixture was stirred under an argon atmosphere at room temperature for one hour. a solution of 200.0 mg of (ÍS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthio-imidazo [5, 1-b] thiazol-2-yl ) -l-carbapen-2-em-3-carboxylate of sodium in 1.0 ml of DMF, followed by stirring for 3 hours. Water (10 ml) was added to the reaction solution to terminate the reaction. The system was extracted three times with 10 ml of ethyl acetate, followed by washing three times with 30 ml of a semi-saturated saline solution. The organic layer was dried over anhydrous magnesium sulfate and filtered. The residue was purified by chromatography on silica gel (chloroform: methanol = 20: 1) to provide 82.3 mg of the title compound. NMR (CDC13) d: 0.82, 0.85 (total 3H, each t, J = 7.3 Hz), 1.20 (3H, m), 1.25 (2H, m), 1.30 (3H, m), 1.37, 1.42 (totalßH, each s), 1.49 (3H, m), 1.61 (2H, m), 2.37 (3H, s), 3.23, 3.25 (total 1H, each t, J = 2.9 Hz), 3.35 (1H, m) , 4.21 (1H, m), 4.26 (1H, m), 6.83 (1H, t, J = 5.4 Hz), 7.94 (1H, s), 8.32, 8.34 (total 1H, each s) MS (TSP): 552 (M ++ H) Example 311 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) - 1- (3,3-dimethyl-l-butyloxycarbonyloxy) ethyl l-carbapen-2-em-3-carboxylate (a mixture of diastereomers) The title compound (38.9 mg) was obtained from 200.0 mg of , 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em- Sodium 3-carboxylate and 453 mg of 1- (3,3-dimethyl-1-butyloxycarbonyloxy) ethyl iodide in the same manner as in Example 2, except that no sodium hydrogen carbonate was used in the reaction. NMR (CDCI3) or: 0.84, 0.88 (total 9H, each s), 1.20 (3H, dd, Ji = 7.3 Hz, J2 = 1.7 Hz), 1.30, 1.33 (total 3H, each d, J = 6.3 Hz), 1.49 (2H, m), 1.52, 1.58 (total 3H, each d, J = 5.4 Hz), 3.25 (1H, dd, Ji = 6.6 Hz, J2 = 2.7 Hz), 3.35, 3.37 (total 1H, each d, J = 7.3 Hz), 4.14 (2H,), 4.20 (1H, m), 4.26 (1H, td, J = 3.2 Hz, J = 9.5 Hz), 6.87 (1H,), 7.95, 7.96 (total 1H, each s), 8.31, 8.33 (total 1H, each s) MS (TSP): 552 (M * + H) Example 312 (ÍS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl -2- (7-Methylthio-imidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 1- (2-methoxybenzoyloxy) ethyl ester (a mixture of diastereomers) dissolved (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2 sodium-3-carboxylate (170 mg) in 2 ml of DMF. Triethylbenzylammonium chloride (193 mg) and 182 mg of 2-methoxybenzoyloxymethyl chloride were added to the solution under an argon atmosphere. The mixture was stirred under ice cooling for 2 hours and then stirred at room temperature for 5 hours. Ethyl acetate (30 ml) was added to the reaction solution. The mixture was washed twice with 20 ml of a semi-saturated saline solution. The organic layer was dried over anhydrous magnesium sulfate, filtered and then concentrated to a volume of 5 ml under reduced pressure. The residue was purified by column chromatography on silica gel (dichloromethane: methanol = 40: 1) to provide 131 mg of the title compound. NMR (CDC13) d: 1.27 (3H,), 1.37 (3H, m), 1.68, 1.72 (total 3H, each d, J = 5.4 Hz), 2.42 (3H, s), 3.32 (1H, m), 3.40 (1H,), 3.87, 3.90 (total 3H, each s), 4.30 (2H, m), 6.97 (2H, m), 7.27 * (1H, m), 7.50 (1H, m), 7.88 (1H, m), 7.94 (1H, s), 8.30, 8.36 (total 1H, each s) MS (TSP): 558 (M + + H) Example 313 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthio-imidazo [5, 1-b] thiazole- 3, 5-dimethylbenzoyloxymethyl 2-yl) -l-carbapen-2-em-3-carboxylate In the same manner as in Example 2, 130 mg of the title compound was obtained from 180 mg of (ΔS, 5R , 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3 sodium carboxylate and 200 mg of 3,5-dimethylbenzoyloxymethyl iodide. NMR (CDCI3) d: 1.28 (3H, d, J = 7.4 Hz), 1.37 (3H, d, J = 6.3 Hz), 2.04 (1H, m), 2.35 (6H, s), 2.43 (3H, s) , 3.33 (1H, dd, Ji = 6.6 Hz, J2 = 2.9 Hz), 3.43 (1H,), 4.29 (1H,), 4.35 (1H, dd, Ji = 9.8 Hz, J2 = 2.9 Hz), 6.14, 6.18 (2H, ABq, J = 5.6 Hz), 7.22 (1H, s), 7.68 (2H, s), 8.01 (1H, s), 8.30 (1H, s) MS (TSP): 542 (M ++ H) Example 314 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen- 2-Em-3-carboxylic acid 1- [2- (2-propyl) phenoxycarbonyloxy] ethyl ester In the same manner as in Example 2, 150.0 mg of the title compound was obtained from 200.0 mg of (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2 - * (7-methylthioimidazo [5Sodium l-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate and 500 mg of l- [2- (2-propyl) phenoxycarbonyloxy] ethyl iodide. NMR (CDC13) d: 1.17 (3H, d, J = 6.9 Hz), 1.22, 1.24 (total 3H, each d, J = 6.9 Hz), 1.28, 1.30 (total 3H, each d, J = 7.3 Hz), 1.38, 1.40 (total 3H, every d, J = 6.63 Hz), 1.69, 1.74 (total 3H, each d, J = 5.4 Hz), 2.00 (1H, m), 2.43 (3H, s), 3.14 (1H, m), 3.33 (1H, m), 3.46 (1H, m), 4.28 (1H,), 4.35 (1H, m), 7.01 (1H, m), 7.20 (4H, m), 8.00, 8.01 (total 1H , each s), 8.35, 8.37 (total 1H, each s) MS (FAB): 586 (M ++ H) Example 315 (ÍS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l -methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid (2,2-dimethyl-l-propyloxycarbonyloxy) methyl thereof As in Example 2, 161.6 mg of the title compound was obtained from 200.0 mg of (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7- sodium methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate and 204.1 mg of (2,2-dimethyl-l-propyloxycarbonyloxy) methyl iodide. NMR (CDC13) d: 0.92 (9H, s), 1.27 (3H, d, J = 7.3 Hz), 1.35 (3H, d, J = 6.1 Hz), 2.42 (3H, s), 3.31 (1H, dd, J = 6.9 Hz, J = 2.6 Hz), 3.42 (1H, m), 3.86 (2H, s), 4.26 (1H, m), 4.33 (1H, dd, J = 9.8 Hz, J = 2.6 Hz), 5.89, 5.94 (2H, ABq, J = . 6 Hz), 8.01 (1H, s), 8.33 (1H, s) MS (TSP): 524 (M ++ H) Example 316 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) 1- (2-ethyl-l-butyloxycarbonyloxy) ethyl-l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid ester ( a mixture of diastereomers) Acid (IS, 5R, 6S) -6- (IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) was prepared -l-carbapen-2-em-3-carboxylic acid from (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -1-methyl-2- (7-methylthioimidazo [5, 1-] b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate sodium and an aqueous solution of 1.0 N hydrochloric acid. The title compound (33.5 mg) was obtained using this compound (103.3 mg), 123.7 mg of benzyltriethylammonium chloride, 113.3 mg of 1- (2-ethyl-1-butyloxycarbonyloxy) ethyl chloride, 54.9 mg of triethylamine, 24. ml of DMF according to the method described in publication No. 504039/1999 the translation of the international patent application. NMR (CDCI3) d: 0.80, 0.83 (total 6H, each t, J = 7.3 Hz), 1.21 (3H, dd, Ji = 7.3 Hz, J2 = 3.0 Hz), 1.28 (1H, m), 1.32 (3H, m), 1.46 (4H, m), 1.52, 1.58 (total 3H, each d, J = 5.6 Hz), 2.37 (3H, s), 3.25 (1H,), 3.35, 3.37 (total 1H, each t, J = 7.1 Hz), 4.01 (2H, m), 4.21 (1H, m), 4.26 (1H, td, Ji = 2.7 Hz, J2 - 9.7 Hz), 6.87 '(1H, ia), 7.95, 7.95 (total 1H , each s), 8.31, 8.33 (total 1H, each s) MS (TSP): 552 (M ++ H) Example 317 (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l -methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 1- (3-methyl-l-butyloxycarbonyloxy) -1-propyl ester (a mixture of diastereomers) In the same manner as in Example 310, 38.5 mg of the title compound was obtained from 200.0 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) - sodium l-methyl-2- (7-methylthioi idazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate and 307.2 mg of 1- (3-methyl) chloro -l-butyloxycarbonyloxy) -1-propyl. NMR (CDCI3) d: 0.82, 0.86 (total 6H, each dd, Ji = 6.6 Hz, J2 = 1.3 Hz), 0.93, 1.00 (total 3H, each t, J = 7.5 Hz), 1.22 (3H, dd, Ji = 7.3 Hz, J2 = 2.9 Hz), 1.26, 1.29 (total 3H, each d, J = 6.3 Hz), 1.47, 1.53 (total 2H, each q ,. J = 6.8 Hz), 1.68 (1H, m), 1.91 (2H, m), 2.36 (3H, s), 3.25 (1H, m), 4.14 (2H,), 4.21 (1H, m), 4.26 (1H, m), 6.72, 6.74 (total 1H, each t , J = 5.6 Hz), 7.95, 7.95 (total 1H, each s), 8.32, 8.34 (total 1H, each s) MS (TSP): 552 (M ++ H) Example 318 (ÍS, 5R, 6S) - 6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate from 1 (2,6-dimethylphenoxycarbonyloxy) methyl In the same manner as in Example 2, 223.0 mg of the title compound was obtained from 200.0 mg of (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl ) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate sodium and 500 mg of iodide of l- (2, 6-dimethylphenoxycarbonyloxy) methyl. NMR (CDC13) d: 1.29 (3H, d, J = 7.3 Hz), 1.38 (3H, d, J = 6. 3 Hz), 2.15 (1H, br d), 2.19 (6H, s), 2.44 (3H, s), 3.33 (1H, dd, Ji = 6.6 Hz, J2 = 2.8 Hz), 3.44 (1H, m), 4.30 (1H, m), 4.36 (1H, dd, Ji = 9.6 Hz, J2 = 2.8 Hz), 6.04 (2H , ABq, J = 5.9 Hz), 7.05 (3H,), 8.00, 8.00 (1H, s), 8.34 (1H, s) MS (TSP): 558 (M ++ H) Example 319 (SS, 5R, 6S ) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate from 1- (2, 3, 5-trimethylphenoxycarbonyloxy) ethyl (a mixture of diastereomers) In the same manner as in Example 2, 156.0 mg of the title compound was obtained from 200.0 mg of (IS, 5R, 6S) - 6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid sodium and 500 mg of l- (2,3,5-trimethylphenoxycarbonyloxy) ethyl iodide. NMR (CDC13) d: 1.28, 1.30 (total 3H, each d, J = 7.3 Hz), 1.38, 1.40 (total 3H, each d, J = 6.3 Hz), 1.69, 1.74 (total 3H, each d, J = 5.4 Hz), 1.99 (1H, m), 2.03, 2.11 ( total 3H, each s), 2.25 (6H, m), 2.43 (3H, s), 3.33 (1H, m), 3.46 (1H, m), 4.28 (1H, m), 4.35 (1H,), 6.77, 6.95 (total 1H, each s), 6.88 (1H, s), 7.01 (1H, m), 8.00, 8.01 (total 1H, each s), 8.33, 8.37 (total 1H, each s) MS (TSP): 586 (M + + H) Example 320 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthio-imidazo [5, 1-b] thiazole-2 -l) -l-carbapen-2-em-3-carboxylic acid 2-naphthylcarbonyloxymethyl ester In the same manner as in Example 2, 95 mg of the title compound was obtained from 201 mg of (ΔS, 5R, 6S ) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate from sodium and 201 mg of 2-naphthylcarbonyloxymethyl iodide, NMR (CDCl 3) d: 1.28 (3H, d, J = 7.2 Hz), 1.36 (3H, d, J = 6.2 Hz), 2.41 (3H, s), 3.34 ( 1H, dd, Ji = 6.6 Hz, J2 = 2.7 Hz), 3.42 (1H, m), 4.30 (1H, m), 4.35 ( 1H, dd, Ji = 9.7 Hz, J2 = 2.7 Hz), 6.24 (2H, s), 7.57 (2H,), 7.87-8.08 (5H, m), 8.32 (1H, s), 8.66 (1H, s) MS (TSP): 564 (M + + H) Example 321 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthio-imidazo [5,1] -b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 2,5-dimethylbenzoyloxymethyl ester In the same manner as in Example 2, 155 mg of the title compound was obtained from 182 mg of (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2 sodium-3-carboxylate and 263 mg of 2,5-dimethylbenzoyloxymethyl iodide. NMR (CDC13) d: 1.28 (3H, d, J = 7.1 Hz), 1.37 (3H, d, J = 6.2 Hz), 2.12 (1H, m), 2.33 (3H, s), 2.43 (3H, s) , 2.55 (3H, s), 3.33 (1H, dd, Jx = 6.6 Hz, J2 = 2.8 Hz), 3.45 (1H, m), 4.29 (1H, m), 4.34 (1H, dd, Ji = 9.6 Hz, J: = 2.8 Hz), 6.15 (2H, s), 7.13 (2H, d, J = 7.7 Hz), 7.23 (2JH, d, J = 7.7 Hz), 7.79 (1H, s), 8.00 (1H, s ), 8.31 (1H, s) MS (TSP): 542 (M + + H) Example 322 (SS, 5R, 6S) -2- [7- (N, N-dimethylaminosulfonyl) imidazo [5, 1-b] thiazol-2-yl] -6- ((IR) -hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylic acid cyclohexyloxycarbonyloxymethyl ester In the same manner as in Example 2, 322 mg of the compound were obtained of the title from 255 mg of (ÍS, 5R, 6S) -2- [7- (N, N-dimethylaminosulfonyl) -imidazo [5, 1-b] thiazol-2-yl] -6- ((IR) Sodium 1-hydroxyethyl) -i-methyl-l-carbapen-2-em-3-carboxylate and 316 mg of cyclohexyloxycarbonyloxymethyl iodide. NMR (CDC13) d: 1.26 (3H, d, J = 7.4 Hz), 1.26-1.96 (10H, m), 1.35 (3H, d, J = 6.2 Hz), 2.59 (1H, br.s), 2.86 ( 6H, s), 3.33 (1H, dd, Ji = 6.6 Hz, J2 = 2.7 Hz), 3.47 (1H, m), A.27 (1H, m), 4.35 (1H, dd, Ja = 9.8 Hz, J2 = 2.7 Hz), 4.65 (1H, m), 5.89, 5.94 (2H, ABq, J = 5.8 Hz), 8.08 (1H, s), 8.48 (1H, s) MS (TSP): 597 (M ++ H Example 323 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen 2-Methyl-1- (phenoxycarbonyloxy) -1-propyl 2-em-3-carboxylate (a mixture of diastereomers) In the same manner as in Example 2, 16.0 mg of the title compound was obtained from 200.0 mg (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen- Sodium 2-em-3-carboxylate and 500 mg of 2-methyl- (phenoxycarbonyloxy) -1-propyl iodide. NMR (CDCI3) d: 1.04, 1.08 (total, 3H, each d, J = 6.9 Hz), 1.14 (lh, d, J = 6.9 Hz), 1.28, 1.30 (total, 3H, each d, J = 7.3 Hz ), 1.38, 1.40 (total, 3H, each d, J = 6.3 Hz), 2.22 (2H, m), 2.43 (3H, s), 3.33 (1H, m), 3.46 (1H, m), 4.28 (1H , m), 4.35 (1H, m), 6.71, 6.76 (total 1H, each d, J = 5.4 Hz), 7.28 (5H, m), 8.00 (1H, s), 8.39, 8.39 (total 1H, each s ) MS (TSP): 572 (M + + H) Example 324 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-] b) thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 1- (1-naphthoxycarbonyloxy) ethyl ester (a mixture of diastereomers) In the same manner as in Example 2, 171.0 mg of the compound of the title from 200.0 mg of (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em- Sodium 3-carboxylate and 500 mg of 1- (1-naphthoxycarbonyloxy) ethyl iodide. NMR (CDC13) d: 1.28, 1.30 (total 3H, each d, J = 7.3 Hz), 1.38, 1.40 (total 3H, each d, J = 6.3 Hz), 1.69, 1.74 (total 3H, each d, J = 5.4 Hz), 2.12, 2.18 (total 1H, each d, J = 4.8 Hz), 2.43 (3H, s), 3.33 (1H, m), 3.46 (1H, m), 4.28 (1H, m), 4.35 ( 1H, m), 7.06 (1H, m), 7.46 (4H, m), 7.90 (3H, m), 7.98, 7.99 (total 1H, each s), 8.32, 8.33 (total 1H, each s) MS (TSP ): 594 (M + H) Example 325 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazole- 2-yl) -l-carbapen-2-em-3-carboxylic acid 1- [2- (1-propyl) phenoxycarbonyloxy] ethyl ester (a mixture of diastereomers) In the same manner as in Example 2, 177.0 mg were obtained of the title compound from 200.0 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazole-2 sodium-l-carbapen-2-em-3-carboxylate and 500 mg of l- [2- (1-propyl) phenoxycarbonyloxy] ethyl iodide. NMR (CDC13) d: 0.85, 0.95 (total 3H, each d, J = 7.3 Hz), 1.28, 1.30 (total 3H, each d, J = 7.3 Hz), 1.38, 1.40 (total 3H, each d, J = 6.3 Hz), 1.57 (2H,), 1.69, 1.74 (total 3H, each d, J = 5.4 Hz), 1.93 (1H, m), 2.43 (3H, s), 3.33 (1H, m), 3.46 (1H , m), 4.28 (1H, m), 4.35 (1H, m), 7.02 (1H, m), 7. 20 (4H, m), 8.00, 8.01 (total 1H, each s), 8.36, 3.38 (total 1H, each s) MS (TSP): 586 (M ++ H) Example 326 (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7- Acetylimimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid (2-ethylphenoxycarbonyloxy) ethyl ester (a mixture of diastereomers) In the same manner as in Example 2, obtained 196.0 mg of the title compound from 200.0 mg of (1S, 5R, 6S) -2- (7-acetylmidazo [5, 1-b] thiazol-2-yl) -6- ((1R) -1- hydroxyethyl) -1-methyl-1 .carbapen-2-em-3-carboxylate sodium and 500 mg of 1- (2-ethylphenoxycarbonyloxy) ethyl iodide.

NMR (CDCI3) d: 1.12, 1.21 (total 3H, each d, J = 7.3 Hz), 1.28, 1.30 (total 3H, each d, J = 7.3 Hz), 1.38, 1.40 (total 3H, each d, J = 6.3 Hz), 1.69, 1.74 (total 3H, each d, J = 5.4 Hz), 1.93 (1H, m), 2.55, 2.66 (total 3H, each q, J = 7.3 Hz), 2.62 (3H, s), 3.33 (1H, m), 3.46 (1H,), 4.28 (1H, m), 4.35 (1H, m), 7.02 (1H, m), 7.20 (4H, m), 7.99, 8.00 (total 1H, each s ), 8.58, 8.62 (total 1H, each s) MS (TSP): 568 (M ++ H) Example 327 (SS, 5R, 6S) -2- [7-N, N-dimethylaminosulfonyl) imidazo [5, 1 -b] thiazol-2-yl] -6- ((IR) -1-hydroxyethyl) -l-methyl-l-carbapen-2-em-3-carboxylic acid (2-ethylphenoxycarbonyloxy) ethyl ester (a mixture of diastereomers) In the same manner as in Example 2, 147.0 mg of the title compound was obtained from 200.0 mg of (SS, 5R, 6S) -2- [7-N, N-dimethylaminosulfonyl) imidazo [5,1-b ] thiazol-2-yl] -6- ((IR) -i-hydroxyethyl-l-carbapen-2-em-3-carboxylate sodium and 500 mg of 1- (2-ethylphenoxycarbonyloxy) ethyl iodide. NMR (CDCI3 ) d: 1.12, 1.21 (tota l 3H, each d, J = 7.3 Hz), 1.28, 1.30 (total 3H, each d, J = 7.3 Hz), 1.38, 1.40 (total 3H, each d, J = 6.3 Hz), 1.69, 1.74 (total 3H , each d, J = 5.4 Hz), 2.02 (1H, m), 2.55, 2.66 (total 3H, each q, J = 7.3 Hz), 2.86 (6H, s), 3.33 (1H, m), 3.46 (1H , m), 4.28 (1H, m), 4.35 (1H, m), 7.02 (1H,), 7.20 (4H, m), 8.03, 8.04 (total 1H, each s), 8.49, 8.53 (total 1H, each s) MS (TSP): 633 (M ++ H) Example 328 (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylsulfinyl-imidazo [5 Pylloyloxymethyl (1-b) thiazol-2-yl) -l-carbapen-2-em-3-carboxylate ester (a mixture of diastereomers) In the same manner as in Example 2, 120.0 mg of the title compound was obtained from from 200.0 mg of (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylsulfinylimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2- sodium em-3-carboxylate (a mixture of diastereomers) and 173 mg of pivaloyloxymethyl iodide. NMR (CDC13) d: 1.20, 1.21 (total 9H, each s), 1.24 (3H, m), 1. 35, 1.38 (total 3H, each d, J = 6.3 Hz), 2.95, 2.97 (total 3H, each s), 3.33 (1H, m), 3.46 (1H, m), 4.28 (1H, m), 4.35 (1H, m), 5.88, 5.87, 5.99 (total 2H, each ABq, J = 5.6 Hz), 8. 11 (1H, s), 8.47, 8.48 (total 1H, each s) MS (TSP): 510 (M "+ H) Example 329 (ÍS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-Methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylic acid 1- (2-benzyloxycarbonyloxy) ethyl ester (a mixture of diastereomers ) In the same manner as in Example 310, 22.8 mg of the title compound was obtained from 200.0 mg of (IS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2 Sodium (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate and 160.1 mg of l- (2-benzyloxycarbonyloxy) ethyl chloride. NMR (CDC13 ) d: 1.21 (3H, d, J = 7.3 Hz), 1.31, 1.31 (total 3H, each d, J = 6.1 Hz), 1.52, 1.57 (total 3H, each d, J = 5.6 Hz), 2.37 (total 3H, each s), 3.26 (1H,), 3.36 (1H, m), 4.22 (1H, m), 4.26 (1H, dt, Ji = 9.5 Hz, J2 = 2 .1 Hz), 6.88 (1H, m ), 7.24-7.36 (5H, m), 7.94, 7.95 (total 1H, each s), 8.29, 8.29 (total 1H, each s) MS (TSP): 558 (M ++ H) Example 330 (1S, 5R , 6S) -6- ((IR) -1-hydroxyethyl) -l-met 2- (2-methyl-l-propyloxycarbonyloxy) ethyl 2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate (a mixture of diastereomers) In the same manner as in Example 310, 24.9 mg of the title compound was obtained from 200.0 mg of, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em- Sodium 3-carboxylate and 1- (2-methyl-1-propyloxycarbonyloxy) ethyl chloride. NMR (CDCI3) d: 0.85, 0.89 (total 6H, each d, J = 6.6 Hz), 1.20, 1.22 (total 3H, each dd, J = 3.7 Hz, J = 7.3 Hz), 1.29, 1.32 (total 3H, each d, J = 6.3 Hz), 1.53, 1.68 (total 3H, each d, J = 5.6 Hz), 1.91 (1H, m), 2.36 (3H, s), 3.26 (1H,), 3.36 (1H, qd , J = 7.3 Hz, J = 9.5 Hz), 3.86, 3.92 (total 2H, each brd, J = 6.6 Hz), 4.22 (1H, m), 4.27 (1H, m), 6.87 (1H, m), 7.65, 7.65 (total 1H, each s), 8.31, 8.32 (total 1H, each s) MS (TSP): 524 (M ++ H) Example 331 (ÍS, 5R, 6S) -6 - ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate from 4- ( N, Ndn-propylaminosulfonyl) benzoyloxymethyl In the same manner as in Example 2, 298 mg of the title compound was obtained from 201.0 mg of (1S, 5R, 6S) -6- ((IR) -1-hydroxyethyl) sodium l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate and 365 mg of 4- (N, N) iodide -di-n-propylaminosulfonyl) benzoyloxymethyl. NMR (CDC13) d: 0.86 (6H, t, J = 7.4 Hz), 1.29 (3H, d, J = 7.4 Hz), 1.36 (3H, d, J = 6.2 Hz), 1.54 (4H, m), 2.19 (1H, br.s), 2.44 (3H, s), 3.09 (6H, t, J = 7.6 Hz), 3.33 (1H, dd, Ji = 6.7 Hz, J2 = 2.8 Hz), 3.46 (1H,), 4.29 (1H, m), 4.36 (1H, dd, Ji = 9.7 Hz, J2 = 2.8 Hz), 6.16, 6.22 (2H, ABq, J = 5.6 HZ), 7.88 (2H, d, J = 7.9 Hz), 8.05 (1H, s), 8.19 (2H, d, J = 7.9 Hz), 8.32 (1H, s) MS (TSP): 677 (M ++ H) Example 332 (SS, 5R, 6S) -6- ( (IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate from 1- [4- (N, N-di-n-propylaminosulfonyl) benzoyloxy] ethyl (a mixture of diastereomers) In the same manner as in Example 2, 187 mg of the title compound was obtained from 228 mg of (ΔS, 5R, 6S ) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- (7-methylthioimidazo [5, 1-b] thiazol-2-yl) -l-carbapen-2-em-3-carboxylate from sodium and 625 mg of 1- [4- (N, -di-n-propylaminosulfonyl) benzoyloxy] ethyl iodide. NMR (CDC1) d: 0.86 (6H, m), 1.26, 1.28 (total 3H, each d, J = 7.3 Hz), 1.33, 1.37 (total 3H, each d, J = 6.2 Hz), 1.53 (4H, m ), 1.71, 1.76 (total 3H, each d, J = 5.5 Hz), 2.40, 2.41 (total 3H, each s), 3.08 (4H, m), 3.33 (1H, m), 3.44 (1H,), 4.27 (1H, m), 4.35 (1H, m), 7.29 (1H, m), 7.86 (2H, m), 8.01 (1H, s), 8.14, 8.21 (total 2H, each d, J = 8.8 Hz), 8.32, 8.35 (total 1H, each s) MS (TSP): 691 (M ++ H) The compounds prepared in the previous examples had the following structures. In the following table, * represents link to position 2 of the carbapenem ring. POM represents pivaloyloxymethyl.

EXAMPLE R I R 2 R 3 R 1 R CH 3 * H C (0) CH, CHj Na CH, CH = N0H Na (Derived from low polarity side chain component) CH = N0CH3 Na (Derived from low polarity side chain component) (Derived from side chain component of polarity) 6 CH, * 'H H C (0) C (CH3) 3 Na 8 * CH, C (0) CH3 Na 1 0 CH .. H H C (0) CH (CH3) NHCHO Na (high polarity component) 11 CHa H H C (0) CH (CH 3) NHCHO Na (low polarity component) C (0) CH (CH3) 2 Na 12 CH3 * H H H C (0) CH¡CH3 Na 14 Na * H H C (0) CH3 H C (0) CH (CH3) 2 Na 17 H 19 CH3 * H CH3 C (0) CH3 Na 2 3 H H SOjCHj Na 2 4 H H H SO, CH3 Na 2 5 CHj H H SOjCH3 Na 2 6 CH3 * H H S (0) CH3 Na 2 7 H H C (0) CH.CH3 Na 3 0 CH3 SO.CH.CH, Na 3 1 CH, * H SO¡NHCH3 Na 3 2 SO.NHCH3 Na 3 3 * H CH3 C (0) CH3 Na 3 4 H SOJCHJCHJ Na V 3 5 CH3 * H H < A \ \ J Na 3 6 H * H C (0) CH, OH Na 3 7 CH3 * H C (0) Ph Na 3 8 H H C (0) CH 2 OH Na 3 9 H C (0) Ph Na 4 1 CH, Na 4 2 CH3 H S0, N (CHJ) CHJCH.0H Na 4 3 CH3 C (0) CH: NHC (0) CH3 Na 4 4 CHj CH, SOJCHJ Na 4 5 CH, CH, S (0) CH. Na 4 9 CH3 * H H C (0) CH3 XO 3 CH3 * H H CH, NHC (0) CH3 Na . 4 CH3 * H H CH, NHC (0) CH, 5 5 CH3 * 'H H CH, NHC (0) CH? 6 CH3 * H CH¡NHC (0) CH3 3X_ 71 CH, * H H C (0) CH00H Na CH3 O 73 CH3 * H H C (0) CH00H 'O X CH3 79 CH, C (0) CHjOH 80 CH, * H H C (0) CH.C (0) N (CH :). Na 81 CH, * H H C (0) CH.C (0) N (CH.), 88 CH, S0.N (CH3) Na twenty 94 .CHj H H SOjN (CHj), X "O 8 CH, H C (0) CF3 Na 9 CH, H H SOjNHj Na 1 CH, * H H Na O CH, ^ S 2 CH, * H H Na 103 CH, CH, C (0) CH: CH Na 104 CH, S0.CH3 Na 105 CH3 S (0) CH, Na 106 CH3 C (0) CH¡OH Na ' 107 CH, CH, SOjCH, 108 CH, CÍOCH.NHSOjCH, Na 109 CH3 CH3 SCH, Na 110 CH3 H CHjNHSO.CH, Na 111 CH3 SCH, Na 1 14 CH3 * H H (E) -CH = CHC (0) CH3 Na 1 15 CH3 CH, CHO Na 1 16 H * H SCH3 Na 1 17 H * H S (0) CH3 Na 1 18 H * H H C (0) CHiNHSO, N (CH3)! Na 119 CHj H C (0) CH1NHSO, N (CH,) J Na 120 H * H CH; SCH; Na 121 CH, * H H C (0) CHsNH, Na 123 CH, * H H C (0) CH, LHSO, CH, CH, NH, Na 124 H C (0) CH, NHSOjCH, CHjNH, Na 125 CH, S0) j, CCHH3, H H N Naa 126 CH3 S: CCHH33 H H N Naa 127 CH3 SCH3 SCH3 Na 128 CH, H H SPh Na 129 H H * SCH, Na 130 H * H SPh Na 131 CH3 * SCH, H Na 132 CH, * H H SCHjCH, Na 133 H * SCH, H Na 34 H * H SCHjCH3 Na H * CH3 SCH3 Na 136 CH, SCH3 S (0) CH3 Na 137 * CH¡OH H SCH3 Na 138 H Ph Na 139 (0) CH.NH, Na 140 CH, * H S (0) CH, H Na 141 CH, * H S (0) CH, S (0) CH3 Na 142 CH, * H S (0) CH, SO.CH, Na 14. 3 CH, H SO.CH, SO.CH, Na 144 H * CH¡NH, H Na 145 H * CH.OH H H Na 146 H * H SCH, SCH, Na 147 CH, * H C (0) CH, SCH, Na 1 8 CH, * SCH3 H SCH, Na 149 CH3 * H C (0) CH3 SO, CH3 Na 150 CH, * H Br SCH, Na 151 H * H C (0) CH, SCH 3 Na 153 SCH, SCH 3 Na 154 CH, Cl SCH3 Na 155 H CN SCH3 Na 156 CH, H SCH.CH, CH3 Na 157 H SCH; CH; CH3 Na 158 CH3 H SCH (CH3) 2 Na 159 H H SCH (CH,), Na PH3 0 166 CH3 CH, C (0) CH3 174 CH3 * H H C (0) CH3.? Q CH3 O f ^ CH3 ' 179 CH3 * H H C (0) CH3 A A-CH3 H3 O H '3 1 9 8 CH, SO.CH, CH3 6 CH, SO SO, CH 3 CH 1 CH, CH 7, SO SO, CH, CH (CH,) 2 O 0 CH, * H H SCH, A, CH.

PHs 9 QHs 264 CH3 H SCHj AAH, 267 CH, * H H SCH, 1H3X H, 270 CH, H SCH3 XX ^ H, OH. o CHa 273 CH3 H SCH, c (^ ACH3 CH3 OR 274 CH3 H SCH, XA .CHa CH3 O 9 1 CH, * H H SCH, XA CH, 295 CH, H SCH, 10 s O ^ 3 307 CH, SCH, (CH :) «CH, 326 CH3 * H H C (0) CH3 XA H3s CH3 or (AX 327 CH, * H H S02N (CH3) 2? X J H3s twenty Injections Aseptic loading was carried out in a bottle in such a way that each bottle contained 1000 mg (strength) of the compound prepared in Example 62. Capsules Compound prepared in Example 63 250 parts (power) Lactose 60 parts (power) Magnesium stearate 5 parts (power) These ingredients were mixed homogeneously toget The mixture was filled into capsules in order to offer 250 mg (potency) per capsule. Soft capsules for rectal administration Olive oil 160 parts (power) Polyoxyethylene lauryl et10 parts (potency) Sodium hexametaphosphate 5 parts (potency) The compound (250 parts (potency)) prepared in the example 63 was added and mixed homogeneously with a homogeneous base consisting of the aforementioned ingredients. The mixture was filled into soft capsules for rectal administration in order to provide 250 mg (potency) per capsule. Test 1: Anti-microbial activities The minimum inhibition concentrations (MIC, μg / ml) of the compounds according to the present invention for various pathogenic bacteria were measured according to the method described in CHEMOTPY, volume 16, no. 1, 1, 99, 1968. The culture medium for the measurement was a disk of agar-N + 5% sensitivity of horse blood, and the amount of inoculants was 106 CFU / ml. The results appear in the following table. Test bodies Example No. 26 27 44 62 71 S.aureus 209P JC-1 < 0.025 0.05 0.05 < 0.025 < 0.025 S.aureus M126 * 6.25 0.78 3.13 1.56 3.13 S. epidermidis < 0.025 0.05 0.05 < 0.025 < 0.025 ATCC14990 E.hirae ATCC8043 0.78 0.39 0.78 0.39 0.39 E.faecalis W-37 0.39 0.10 0.78 0.20 0.39 S. pneumoniae PRC9 ** 0.10 0.05 0.10 0.05 0.10 M. catarrhalis W-0500 0.05 < < 00..00225 < 0.025 < 0.025 < 0.025 H. influenzae PRC2 < 0.025 < 0.025 < 0.025 < 0.025 < 0.025 H. influenzae PRC44 0.05 0.05 0.10 0.05 0.05 E.coli NJ JC-2 0.05 0.20 0. .78 0.05 < 0.025 K. pneumoniae PCI602 0.10 0.10 1. .56 0.05 < 0.025 P. vulgaris GN7919 0.20 0.20 0. .78 0.10 < 0.025 C.freun.dii GN346 1.56 0.39 12. .5 1.56 0.39 Test organisms Example No. Compound 88 11 A B S.aureus 209P JC-1 < 0.025 < 0 .025 < 0 .025 < 0.025 S.aureus M126 * 1.56 1 .56 25 6.25 S.epidermidis ATCC14990 < < 00..002255 < 0.025 < 0.025 0.05 E.hirae ATCC8043 0.39 0.39 0.78 1.56 E.faecalis -37 0.39 0.20 0.78 3.13 S. pneumoniae PRC9 ** 0.05 0.05 0.20 0.39 M. catarrhalis -0500 < 0.025 < 0.025 0.05 < 0.025 H. influenzae PRC2 < 0.025 < 0.025 0.78 0.10 H. influenzae PRC44 0.10 0.05 12.5 0.78 E.coli NJ JC-2 0.39 0.78 0.10 0.05 K. pneumoniae PCI602 0.39 0.78 0.20 0.10 P. vulgaris GN7919 0.78 0.39 0.10 0.10 C.freundii GN346 3.13 1.56 0.20 0.10 In the table *: methicillin-resistant strain (MRSA); **: hyper-resistant penicillin strain (PRSP); Compound A: imipenem / Compound B: acid iodide (SS, 5R, 6S) -6- ((IR) -1-hydroxyethyl) -l-methyl-2- [(3S, 5S) -5- (6-methylimidazo [5, 1-b] thiazolium-2-yl) methylpyrrolidin-3-yl] thiocarbapen-2-em-3-carboxylic acid. As is clear from the test results described above, the compounds according to the present invention have strong anti-microbial activities against MRSA, PRSP, enterococci, influenza as well as against several pathogenic bacteria including bacteria that produce ß-lactamase.

Test 2: Stability against DHP-I The stabilities of the compounds according to the present invention against porcine and mouse renal dehydropeptidases were measured by the following method. (1) Preparation of DHP-1 from kidney acetone powders of various animals Kidney acetone powder, porcine type II (Sigma, lot 33H7225, 1.5 g) was suspended in a buffer of 50 mM Tris? Cl ( pH 7.0) containing 20. butanol, and the mixture was stirred at a temperature of 5 ° C for 48 hours. Dialysis (30/32 cellulose tube, Viskase Sales Corp) was performed with a 50 mM Tris-HCl buffer (pH 7.0) in order to remove the butanol to a level without butanol odor. The dialysate was centrifuged at 10000 xg (KUBOTA 6800) for 20 minutes to provide a supernatant as a partially purified DHP-I, which was divided into portions and stored at a temperature of -80 ° C. Thus, a DHP-I was prepared partially purified from 1.5 g of mouse (batch 23F8105), and stored in the same manner. (2) Measurement of stabilities in relation to several DHP-I's The compound according to the present invention, as a basic pharmaceutical agent, was diluted with sterile purified water to prepare a solution having a titer of 2000 μg / ml. The solution of the compound according to the present invention having a titer of 2000 μg / ml was added to the partially purified DHP-I's of the animals described above in order to have a final concentration of 100 μg (titer) / ml. As a blank, a 50 mM Tris-HCl buffer (pH 7.0) was used in place of the partially purified DHP-I's from the animals. After the reaction at 37 ° C for 3 hours, a portion of the reaction mixture was removed, diluted with the same amount of methanol to suspend the reaction by cooling on ice. The reaction mixture was filtered through SUNPLEP LCR13-LH, MILLIPORE, and subjected to HPLC (column: CAPCELL PACK C18 SG120, SHISEIDO, UV detector, mobile phase: acetonitrile-aqueous acetic acid solution 10 mM) measure the residual amount (%) of partially purified DHP-I according to the following equation. Residual amount (%) = peak sample area x 100 peak white area The residual amounts (%) of the compounds according to the present invention after 3 hours are shown below. DHP-I Ex. 19 Ex. 26 Ex. 27 Ex. 44 Ex. 62 Swine 77 44 38 100 64 Mouse 45 11 1.2 nt 1.5 DHP-I Ex. 71 Ex. 88 Compound A Compound C P Poorrcciinnaa 3333 7733 < 0.3 41 Mouse < 0.1 < 0.1 14 8.5 In the table, nt: not tested Compound A: imipenem; Compound B: meropenem. It is understood from the above table that the compounds according to the present invention have high stabilities for renal DHP-I porcine, and the carbapenem derivatives represented by the general formula (II) have high stabilities with respect to renal and mouse renal DHP-I. Test 3: Oral absorption capacity test (1) The compounds of examples 62, 63 and 69 were orally administered to mice (iCK, male, n = 3) in an amount of 0.5 mg (based on the weight of the compound of Example 62 from which the compounds of Examples 63 and 69) /O.2 ml / mouse were derived as a suspension of 0.5% methylcellulose, and then cilastatin was immediately administered subcutaneously in the same amount (due to instability) of the compound of Example 62 relative to mouse DHP-I, "cilastatin was used as a DHP-I inhibitor in combination." As a result, the compound of Example 62 was excreted in the urine in 6%, 18% and 35% bioavailability (BA) for the 8 hours after the administration of the compounds of examples 62, 63 and 69. Bioavailability is a relationship between the recovery of a parent compound in the urine. When a compound is orally administered test, that is, a profa of the parent compound, and the recovery of the parent compound when the parent compound is administered intravenously. The compounds of Examples 111, 243 and 282 were tested. As a result, the compound of Example 111 from which the compounds of Examples 243 and 282 were derived was excreted in urines in 4%, 16% and 26% BA for 24 hours after the administration of the compounds of the Examples 111, 243 and 282, respectively. The compound of example 49 was tested. As a result, the compound of Example 46-b from which the compounds of Example 49 are derived was excreted in urine in 37% BA for 24 hours "after administration of the compound of Example 49. The compound of example 77. As a result, the compound of example 71 from which the compounds of example 77 were derived was excreted in urine in 22% BA for 24 hours after the administration of the compound, of example 49. It was tested the compound of Example 89. As a result, the compound of Example 88 from which the other compounds of Example 89 were derived was excreted in urine in 18% BA for 24 hours after the administration of the compound of Example 89. tested the compound of Example 107. As a result, the compound of Example 44 from which the compounds of Example 107 were derived was excreted in urine in 21% BA for 24 hours after administration of the Example 107. The compound of Example 168 was tested. As a result, the compound of Example 19 from which the compounds of Example 168 were derived was excreted in urine in 29% BA for 24 hours after the administration of the compound of example 168. Test 4: absorption capacity test oral (2) Certain compounds were tested in the same way as in test 3 but 5% HCO60 was used instead of a 0.5% methylcellulose suspension. The compounds of examples 63, 189, 195 and 218 were tested. As a result, the compound of Example 62 from which the compounds of Examples 189, 195 and 218 were derived was excreted in urine in 29%, 44%, 24% and 26% BA for 24 hours after administration of the compounds of Examples 63, 189, 195 and 218, respectively. The compounds of examples 243, 250, 253, 273, 287, 292, 301 and 319 were tested. As a result, the compound of Example 111 from which these compounds were derived was excreted in urines in 25%, 39%, 37%, 36%, 24%, 53%, 50%, and 51% BA for the 24 hours after administration of the compounds of examples 243, 250, 253, 273, 287, 292, 301 and 319, respectively. Test 5: water toxicity (i.v.) The compounds of examples 44, 62, 88 and 111 were administered to mice (ICR, male n = 3), respectively, in a dose of 2,000 mg / kg i.v. but in the case of example 111 the dose was 1,500 mg / kg due to its limited solubility. All the animals survived. The compounds of Examples 44, 62, 88 and 111 were tested again in the same manner as above but co-ad injected with sodium cilastatin. All the animals survived. It is understood from these results that the compounds of the present invention have more than 2,000 mg / kg (or 1,500 mg / kg) of LD50 and low toxicity. Test 6: Acute (oral) toxicity The compounds of examples 63, 243, and 283 were orally administered in the form of a suspension in 0.5% methylcellulose and the compounds of examples 218 and 292 were administered orally in the form of an 5% in HCO60 to mice (IRC, male n = 4) in a dose of 2,000 mg / kg. As a result, all the animals survived.

It is understood from the results of the test that the compounds of the formula (I '), which are carbonates in the 3-position of carbapenem derivatives according to the present invention have more than 2,000 mg / kg (or 1,500 mg / kg) of LD50 and low toxicity.

Claims (17)

1. CLAIMS A compound represented by the formula (I), or a pharmaceutically acceptable salt thereof or uri ester at the 3-position on the carbapenem ring thereof: (i) wherein R 1 represents a hydrogen atom or a methyl group, R2, R3, R4, and R5, any of them represents the junction with position 2 in the. Carbapenem ring, and the other three may be the same or different, and represent respectively a hydrogen atom, a halogen atom, a nitro group, a cyano group, a lower alkyl group which may be substituted, a lower cycloalkyl group which may be substituted, a lower alkylthio group, an arylthio group, a C2_4 alkenyl group which may be substituted, a formyl group, a lower alkylcarbonyl group which may be substituted, a lower alkoxycarbonyl group, a lower alkylsulfonyl group, an arylsulfonyl group which may be substituted, to be substituted, an aminosulfonyl group, a lower N-alkylaminosulfonyl group, a lower N, N-dialkylaminosulfonyl group, an N-lower alkoxy-N-lower alkylsulfonyl group, a lower alkylsulfinyl group, an arylsulfinyl group, an aminonosulfinyl group, a group arylcarbonyl, an aryl group that may be substituted, a carbamoyl group, a lower N-alkylcarbamoyl group, a N, N-di-alkylaryl group lower laminocarbonyl a lower alkoxyiminomethyl group, a hydroxyiminomethyl group, or a five or six membered aromatic heterocyclic ring having one or more heteroatoms selected from nitrogen, oxygen and sulfur atoms, and R represents a hydrogen atom or a group that can be hydrolyzed in organisms. A compound according to claim 1, wherein R 1 represents a hydrogen or methyl atom and R2, R3, R4, and R5, except that which represents the bond with position 2 in the carbapenem ring, which may be the same or different, and represent respectively a hydrogen atom, a halogen atom, a cyano group, a lower alkyl group which may be substituted, a lower cycloalkyl group which may be substituted, a lower alkylthio group, an arylthio group, a C 2-4 alkenyl group which may be substituted, a formyl group, a lower alkylcarbonyl group which may be substituted, a lower alkylsulfonyl group, an arylsulfonyl group which may be substituted, an aminosulfonyl group, a lower N-alkylaminosulfonyl group which may be substituted, a lower N, N-di-alkylaminosulfonyl group which may be substituted, a lower alkylsulfinyl group, a group arylcarbonyl, an aryl group which may be substituted, a lower alkoxyiminomethyl group, a hydroxyiminomethyl group, or an aromatic heterocyclic ring of five or more six members having one or more heteroatoms selected from nitrogen, oxygen and sulfur atoms. A compound according to claim 1, wherein R1 represents a hydrogen or methyl atom, R2 represents the bond with the 2-position on the carbapenem ring, R3, R4, and R5, which may be the same or different, and represent respectively a hydrogen atom, a halogen atom, a cyano group, a lower alkyl group in which one or more hydrogen atoms in the alkyl group may be substituted by groups selected from the group consisting of a halogen atom, a hydroxy group , an amino group, a formylamino group, a lower alkylcarbonylamino group, a carbamoyl group, and a lower alkylsulfonylamino group, a lower cycloalkyl group which may be substituted by carbamoyl, a lower alkylthio group, an arylthio group, a C 2-4 alkenyl group wherein one or more hydrogen atoms in the alkenyl group may be substituted by a lower alkylcarbonyl group or a lower alkoxycarbonyl group, a upo formyl, a lower alkylcarbonyl group in which one or more hydrogen atoms in the alkyl group may be substituted by groups selected from the group consisting of a halogen atom, a hydroxy group, an amino group, a lower alkylcarbonylamino group, a lower N, N-dialkylaminocarbonyl group, a (N-lower alkylamino) sulfonyl group, a (N, Nd? -alkylamino) sulfonyl group and a lower alkylsulfonylamino group , a lower alkylsulfonyl group, an arylsulfonyl group in which one or more hydrogen atoms may be substituted by a lower alkyl group, an aminosulfonyl group, a lower N-alkylaminosulfonyl group in which one or more hydrogen atoms in the alkyl group may be substituted by groups selected from the group consisting of a lower alkoxy group, a hydrogen atom, and an aryl group (in which one or more hydrogen atoms in the aryl group may be substituted by an amino group), N, N-dialkylaminosulfonyl lower group, a lower alkylsulfinyl group, an arylcarbonyl group, an aryl group which may be substituted by a lower alkylcarbonyl group, an lower alkoxyiminomethyl group, a hydroxyiminomethyl group, or a five or six membered aromatic heterocyclic ring having one or more heteroatoms selected from nitrogen, oxygen and sulfur atoms. A compound according to claim 1, wherein R1 represents methyl, R2 represents the bond at the 2-position on the carbapenem ring, R3, R4, and R5, which may be the same or different, and represent respectively a hydrogen atom, a lower alkyl group in which one or more hydrogen atoms in the alkyl group may be substituted by groups selected from the group consisting of a halogen atom, a hydroxy group, an amino group, a formylamino group, a lower alkylcarbonylamino group , a carbamoyl group, a lower alkylsulfonylamino group, and an aryl group, a lower alkylthio group, an arylthio group, a lower alkylcarbonyl group in which one or more hydrogen atoms in the alkyl group may be substituted by groups selected from the group consisting of a halogen atom, a hydroxy group, an amino group, a lower alkylcarbonylamino group, a N, N-di-alkylaminocarbonyl group in ferior, a (N-lower alkylamino) sulfonyl group, a (N, N-di-lower alkylamino) sulfonylamino group and a lower alkylsulfonylamino group, a lower alkylsulfonyl group, an aryisulfonyl group in which one or several hydrogen atoms in the Aryl group can be substituted by a lower alkyl group, an aminosulfonyl group, a lower N-alkylaminosulfonyl group in which one or several hydrogen atoms in the alkyl group can be substituted by groups selected from the group consisting of a lower alkoxy group , a hydrogen atom, and an aryl group (in which one or more hydrogen atoms in the aryl group may be substituted by an amino group), a lower N, N-di-alkylaminosulfonyl group, a lower alkylsulfinyl group, a hydroxyiminomethyl group, or a five or six membered aromatic heterocyclic ring having one or more heteroatoms selected from nitrogen, oxygen and sulfur atoms. A compound according to claim 1, wherein R 1 represents methyl, R 2 represents the bond with the 2-position on the carbapenem ring, R 3 - and R 4, represents a hydrogen atom, R 5 represents a lower alkylthio group or a lower alkylsulphonyl group . A compound according to claim 1, wherein R1 represents methyl, R2 represents the bond with the 2-position on the carbapenem ring, R3 and R4, represent a hydrogen atom, R5 represents methylthio or methylisulfonyl. A compound according to claim 1, wherein R1 represents methyl, R2 represents the bond with the 2-position in the carbapenem ring, R3 and R4 represent a hydrogen atom, R5 represents a lower alkylcarbonyl group, in which one or several Hydrogen atoms in the alkyl group may be substituted by groups selected from the group consisting of a halogen atom, a hydroxy group, an amino group, a lower alkylcarbonylamino group, a lower N, N-di-alkylaminocarbonyl group, a (N-lower alkylamino) sulfonyl group, a (N, N-di-lower alkylamino) sulfonyl group and a lower alkylsulfonylamino group. A compound in accordance with the. claim 1, wherein R1 represents methyl, R2 represents the bond with the 2-position on the carbapenem ring, R3 and R4 represent a hydrogen atom, R5 represents a lower alkyl group substituted by a lower alkylcarbonylamino group. A compound according to claim 1, wherein R1 represents methyl, R2 represents the bond with the 2-position on the carbapenem ring, R3 and R4, represent a hydrogen atom, R5 represents a lower N, N-di-alkylaminosulfonyl group . A compound according to claim 1, wherein R1 represents methyl, R2 represents the bond with the 2-position on the carbapenem ring, R3 and R4, represent a hydrogen atom, R5 represents an N, N-dimethylaminosulfonyl group. A compound according to claim 1, wherein R1 represents methyl, R2 represents the bond with the 2-position on the "ring of carbapenem, R3 represents a hydrogen atom, R4 represents a lower alkyl group, R5 represents a lower alkylcarbonyl group which it may be substituted by a hydroxyl group. 12. A compound according to claim 1, wherein R1 represents methyl, R2 represents the bond with the 2-position on the carbapenem ring, R3 represents a hydrogen atom, R4 represents a lower alkyl group, and R5 represents a lower alkylsulfonyl group. 13. A compound according to claim 1, wherein R1 represents methyl, R2 represents the bond with the 2-position on the carbapenem ring, R3 represents a hydrogen atom, R4 represents methyl, and R5 represents methylsulfonyl. 14. A compound according to claim 1, wherein R1 represents methyl, R2 represents the bond with the 2-position on the carbapenem ring, R3 and R4 represent a hydrogen atom, and R5 represents a lower alkylsulfinyl group. 15. A compound according to claim 1, wherein R1 represents methyl, R2 represents the bond with the 2-position on the carbapenem ring, R3 and R4 represent a hydrogen atom, and R5 represents a methylsulfinyl group. 16. A compound according to claim 1, wherein R1 represents hydrogen or a methyl group, R2, R3, R4, and R5, except that which represents the bond with position 2 in the carbapenem ring, which may be the same or different, respectively, represent a hydrogen atom, a lower alkyl group which may be substituted, an arylthio group, a lower alkylcarbonyl group which may be substituted, an arylsulfonyl group which may be substituted, a lower N-alkylaminosulfonyl group which may be substituted, a lower N, N-di-alkylaminosulfonyl group which may be substituted, a lower N-alkoxy-N-lower alkylsulfonyl group, a lower alkylsulfinyl group, an arylsulfonyl group, an aminosulfinyl group or a five or six membered aromatic heterocyclic ring having one or more heteroatoms selected from nitrogen, oxygen and sulfur atoms. 17. A compound according to claim 1, wherein R1 represents methyl, R2, R3, R4, and R5, except that which represents the bond with position 2 on the carbapenem ring, which may be the same or different, represent respectively a hydrogen atom, a lower alkyl group in which one or more hydrogen atoms in the alkyl group may be substituted by groups selected from the group consisting of a halogen atom, a hydroxy group, an amino group, a N group -alkylamino lower, a formylamino group, a lower alkylcarbonylamino group, a carbamoyl group, and a lower alkylsulfonylamino group, an arylthio group, a lower alkylcarbonyl group, in which one or more hydrogen atoms in the alkyl group may be substituted by groups selected from the group consisting of an atom of a halogen atom, a hydroxy group, an amino group, a lower alkylcarbonylamino group, "a group N, N-di-alko lower alkylaminocarbonyl, a (N-lower alkylamino) sulfonylamino group, a lower (N, N-dialkylamino) sulfonylamino group and a lower alkylsulfonylamino group, an arylsulfonyl group substituted by a lower alkyl group, a lower N-alkylaminosulfonyl group in which one or several hydrogen atoms in the alkyl group may be substituted by groups selected from the group consisting of a lower alkoxy group, a hydrogen atom, and an aryl group (which may be substituted by an amino group), a group N, N-di-lower alkylaminosulfonyl, a lower alkylsulfinyl group, or a five or six membered aromatic heterocyclic ring having one or more heteroatoms selected from nitrogen, oxygen and sulfur atoms. A compound according to claim i, wherein R 1 represents a hydrogen atom or a methyl group, R 2, R 3, R 4, and R 5, except that which represents the bond with position 2 in the carbapenem ring, which may be the same or different, represent respectively a hydrogen atom, a lower alkyl group, in which one or more hydrogen atoms in the alkyl group may be substituted by groups selected from the group consisting of a halogen atom, a nitro group, a cyano group, a lower cycloalkyl group, a lower alkylthio group, a lower alkoxy group, a hydroxy group, an amino group, a lower N-alkylamino group, a formyl group, a lower alkylcarbonyl group, an arylcarbonyl group, a carboxyl group, a lower alkoxycarbonyl group, a formylamino group , a lower alkylcarbonylamino group, a carbamoyl group, a lower N-alkylcarbamoyl group, a lower N, N-di-alkylaminocarbonyl group, an aminosulfonyl group, a (N-lower alkylamino) sulfonyl group, a (N, N-di) group lower alkylamino) sulfonyl, a (N-lower alkylamino) sulfonylamino group, an aminosulfonylamino group, a (N, N-di-lower alkylamino) sulfonylamino group, a lower alkylsulfonylamino group, and an aryl group, or an animo group, A compound according to claim 1, wherein R represents C? _? o alkyl, an arylcarbonyloxy-lower alkyl group, an aryl-lower alkyloxy-lower alkylcarbonyloxy-lower alkyl, lower alkylcarbonyloxy-lower alkyl group , lower cycloalkylcarbonyloxy-lower alkyl, lower cycloalkyl-lower alkylcarbonyloxy-lower alkyl, dicyclohexyl-ethylcarbonyloxy-lower alkyl, adamanty-carbonyloxy-lower alkyl, lower alkyloxycarbonyloxy-lower alkyl, cycloalkyloxycarbonyloxy-lower alkyl, (cycloalkyloxycarbonyloxy) (lower cycloalkyl) methyl, cycloalkyl lower alkyloxycarbonyloxy-lower alkyl, adamantyloxycarbonyloxy-lower alkyl, 2-indanyloxycarbonyloxy-lower alkyl wherein the aromatic ring may be substituted, aryloxy-lower alkyloxycarbonyloxy-lower alkyl, aryloxycarbonyloxy-lower alkyl wherein the aromatic ring may be substituted of 5-indanyloxycarbonyloxy-lower alkyl, in which the aromatic ring may be substituted, 2-oxo-5-lower alkyl-1,3-dioxolen-4-ylmethyl, 3-phthalidyl in which the aromatic ring may be substituted, or 2- (3-phthalidylidene) ethyl in which the aromatic ring may be substituted, provided that one or more hydrogen atoms in the alkyl group, the lower cycloalkyl group or the aryl group in the groups mentioned above may be substituted. be replaced A compound according to claim 1, wherein R represents C? -? Alkyl or may be substituted, an arylcarbonyloxy-lower alkyl group which may be substituted, an aryl-lower alkyloxy-lower alkylcarbonyloxy-lower alkyl group which may be substituted , lower cycloalkylcarbonyloxy-lower alkyl which may be substituted, dicyclohexylmethylcarbonyloxy-lower alkyl which may be substituted, adamantylcarbonyloxy-lower alkyl which may be substituted, lower (cycloalkyloxycarbonyloxy) (lower cycloalkyl) methyl which may be substituted, lower cycloalkyl-ethoxycarbonyloxy-lower alkyl which may be substituted, adamantyloxycarbonyloxy-lower alkyl which may be substituted, 2-indanyloxycarbonyloxy-lower alkyl which may be substituted, aryl-lower alkyloxycarbonyloxy-lower alkyl which may be substituted or 5-inynyloxycarbonyloxy-lower alkyl which may be substituted. A compound according to claim 1, wherein R represents C 1 - 0 alkyl, an arylcarbonyloxy-lower alkyl group, an aryl-lower alkyloxy-lower alkylcarbonyloxy-lower alkyl, lower cycloalkyl-lower alkylcarbonyloxy-lower alkyl, dicyclohexylmethylcarbonyloxy-alkyl group lower, adamantylcarbonyloxy-lower alkyl, (lower cycloalkyloxycarbonyloxy) (lower cycloalkyl) methyl, cycloalkylethoxycarbonyloxy-lower alkyl, adamantyloxycarbonyloxy-lower alkyl, 12-indanyloxycarbonyloxy-lower alkyl, aryl-lower alkyloxycarbonyloxy-lower alkyl, aryloxycarbonyloxy-lower alkyl wherein the aromatic ring may be substituted, or 5-indanyloxycarbonyloxy-lower alkyl. A compound according to claim 1, wherein R represents C? -_ 0, arylcarbonyloxy alkyl group, a lower alkylcarbonyloxy-lower-alkyloxy lower alkyl aryl-lower-alkylcarbonyloxy-lower alkyl, cycloalkylcarbonyloxy, cycloalkyl-lower lower alkyl diciclohexiÍmetiIcarboniloxi-, loweralkyl, loweralkyl-lower lower alkyl-lower adamantilcarboniloxi-alkyl, alkyloxycarbonyloxy, cycloalkyloxycarbonyloxy, (lower cycloalkyloxycarbonyloxy) (lower cycloalkyl) methyl, lower cycloalkyl-alkyloxycarbonyloxy-lower alkyl, adamantiloxicarboniloxi-lower alkyl, 2 aryloxycarbonyloxy-lower alkyl lower alkyl 5-indanyloxycarbonyloxy-lower alkyl wherein lower-, lower alkyl -indaniloxicarboniloxi wherein the aromatic ring may be substituted, aryl-alkyloxycarbonyloxy the aromatic ring may be substituted, provided that one or or several hydrogen atoms in the alkyl group, the lower cycloalkyl group or the aryl group in the aforementioned groups may be substituted. A pharmaceutical composition comprising the compound according to any of claims 1 to 22, and a pharmacologically acceptable carrier. A pharmaceutical composition according to claim 23, which is used as an antibacterial agent. 25. A method for the treatment of infectious diseases, comprising administering the compound according to any of claims 1 to 22 to animals, including humans. 26. The use of the compound according to any of claims 1 to 22 for the preparation of an antibacterial agent. 27. The use of the compound according to any of claims 1 to 22 as an antibacterial agent.