Abstract: The method for producing a sulfamide according to the present invention includes the step of reacting an alcohol and an oxycarbonylsulfamide compound in the presence of a trivalent phosphorus compound and an azodicarboxylic acid derivative. In one embodiment, the sulfamide is represented by Formula I, the alcohol is represented by Formula II, and the oxycarbonylsulfamide compound is represented by Formula III:R.sup.3 NHSO.sub.2 NR.sup.1 R.sup.2 (I)wherein R.sup.1 and R.sup.2 are independently selected from the group consisting of hydrogen, alkyl, cycloalkyl, alkenyl, alkynyl, aralkyl, aryl, a heterocyclic group, and alkyl substituted with the heterocyclic group, respectively, said heterocyclic group being selected from the group consisting of pyranosyl, furanosyl, piperidinyl, pyrrolidinyl, an azetidinone ring, a cephem ring, a penem ring, and a carbapenem ring; R.sup.

Abstract: An antibacterial aminooxypyrrolidinylthiocarbapenem I, its production from the corresponding carbapenem V and thiol VI, its pharmaceutical formulation, and its use for combating bacteria are presented. ##STR1## (wherein R is optionally substituted amino; R.sup.1 is hydrogen or 1C to 5C alkyl; R.sup.2 is hydrogen or a conventional hydroxy protective group; R.sup.3 is hydrogen or an imino protective group or imino substituent; R.sup.4 is 1C to 5C alkylene; and R.sup.5 is hydrogen or a conventional carboxy protective group; X is a leaving group; R.sup.6 is hydrogen or a thiol protective group; and wavy lines each shows a bond in R or S configuration).

Abstract: An antibacterial aminooxypyrrolidinylthiocarbapenem I, its production from the corresponding carbapenem V and thiol VI, its pharmaceutical formulation, and its use or combating bacteria are presented. ##STR1## (wherein R is optionally substituted amino; R.sup.1 is hydrogen or 1C to 5C alkyl; R.sup.2 is hydrogen or a conventional hydroxy protective group; R.sup.3 is hydrogen or an imino protective group or imino substituent; R.sup.4 is 1C to 5C alkylene; and R.sup.5 is hydrogen or a conventional carboxy protective group; X is a leaving group; R.sup.6 is hydrogen or a thiol protective group; and wavy lines each shows a bond in R or S configuration).

Abstract: A process for preparing free carboxylic acids which comprises treating an optionally substituted benzyl ester with a Lewis acid, preferably in the presence of a cation acceptor, followed by hydrolysis, if required.

Abstract: Antibacterial cephalosporins of the following formula: ##STR1## WHEREIN A and B each is a hydrogen or an amino protecting group; X is a hydroxy or a carboxy protecting group; Y is a hydrogen, halogen, alkyl, alkoxy, or an alkylthio; R is a hydrogen or an alkyl; Z is a group of the formula ##STR2## (in which R.sup.1 and R.sup.2 are the same or different and are a hydrogen, optionally substituted hydrocarbon group, organic acyl, or a group of the formula ##STR3## respectively, in which M and M' are the same or different and are an oxygen or sulfur; R.sup.3 is a hydrocarbon group; R.sup.1 and R.sup.2 can be combined together directly or through a hetero atom); m is 0 or 1; and the broken line shows the presence of a double bond at position 2 or 3, preparable from the compounds shown by the above formula in which Z is an oxygen by treatment with a compound shown by the formula H.sub.2 Z; and pharmaceuticals containing these compounds.

Abstract: Antibacterial cephalosporins of the formula ##STR1## wherein Acyl is an acyl group; R is a hydrogen or methoxy, R.sup.1 is a hydrocarbyl group containing 1 to 8 carbon atoms; R.sup.2 is a hydrogen, alkali metal, alkaline earth metal, halo-alkaline earth metal group or acyl group containing 1 to 12 carbon atoms; R.sup.3 is a hydrogen, pharmaceutically acceptable cation, or ester residue; or when R.sup.2 and R.sup.3 are both hydrogens, they can be combined to form a lactone ring; the broken line shows a double bond at position 2 or 3; and n is zero or one, and processes for preparing them by the reaction of the compound shown by above formula in which R.sup.1 and R.sup.2 combined to show a bond, with a Grignard type or organometallic reagent to introduce R.sup.1, followed by acylation, oxidation, reduction, double bond migration, or other reactions.

Abstract: An antibacterial 7-protected amino-3-oxyiminomethyl-3-cephem-4-carboxylic acid is prepared by the reaction of a 7-protected amino-3-formyl-3-cephem-4-carboxylic acid or its reactive derivatives with a hydroxylamine compound or its reactive derivatives, the process being more suitable for large scale production when coupled with fermentative production of a 3-hydroxymethyl-3-cephem-4-carboxylic acid followed by its direct oxidation.

Abstract: Antibacterial cephalosporin compounds of the following formula: ##STR1## wherein A and B each is a hydrogen, organic or inorganic acyl, or A and B combined together are a diacyl group derived from a polybasic acid; Y is a hydrogen or methoxy; R is a hydrogen or lower alkyl; R' is a hydrogen, alkali metal, organic base group or easily removable protecting group; m is 0 or 1; Z is an optionally substituted guanylhydrazono group, preparable from the corresponding oxo compound or its reactive derivative by reacting with a guanylhyrazine of the formula H.sub.2 Z or its reactive derivative, or by some other reactions.

Abstract: An antibacterial 7-protected amino-3-oxyiminomethyl-3-cephem-4-carboxylic acid is prepared by the reaction of a 7-protected amino-3-formyl-3-cephem-4-carboxylic acid or its reactive derivatives with a hydroxylamine compound or its reactive derivatives, the process being more suitable for large scale production when coupled with fermentative production of a 3-hydroxymethyl-3-cephem-4-carboxylic acid followed by its direct oxidation.