3-Vinyl-cephalosporin derivatives

A 3-vinyl-cephalosporin derivative of the formula:

• ##STR150## in the bicyclooct-2-ene or bicyclooct-3-ene form, and in which the substituent in the 3-position of the bicyclooctene exhibits the E- or Z-stereoisomeric configuration and (a) the symbol R.sub.1 represents a radical of the formula:
• ##STR151## which is in the syn- or anti-form (and in which R.sub.5 is a hydrogen atom or an alkyl, vinyl or cyanomethyl radical, or a protective group chosen from trityl, tetrahydropyranyl or 2-methoxy-prop-2-yl and R.sub.6 is a protective radical chosen from tert.-butoxycarbonyl, 2,2,2-trichloro-ethoxycarbonyl, chloroacetyl, trichloroacetyl, trityl, benzyl, dibenzyl, benzyloxy-carbonyl, p-nitrobenzyloxycarbonyl, p-methoxybenzyloxycarbonyl, formyl or trifluoroacetyl) or
• R.sub.1 is a benzhydryl or trityl radical or an acyl radical of the formula:
• R.sub.7 -CO--
• [in which R.sub.7 is hydrogen, alkyl, alkyl substituted by one or more halogen atoms or by a phenyl or phenoxy radical, or phenyl]
• or R.sub.1 is a radical of the formula:
• R.sub.8 OCO
• (in which R.sub.8 is a branched unsubstituted alkyl radical or a branched or straight alkyl radical carrying 1 or more substituents [chosen from halogen atoms and cyano, trialkylsilyl, phenyl, and phenyl substituted by 1 or more alkoxy, nitro or phenyl radicals], vinyl, allyl or quinolyl), or a nitrophenylthio radical, or R.sub.1 NH is replaced by a methyleneamino radical in which the methylene radical is substituted by dialkylamino, phenyl or phenyl substituted by one or more methoxy or nitro radicals and
• the symbol R.sub.2 represents an enzymatically easily removable radical of the formula:
• ##STR152## (in which R.sub.9 represents a hydrogen atom or an alkyl radical and R.sub.10 represents an alkyl or the cyclohexyl radical) or a methoxymethyl, tert.-butyl, benzhydryl, p-nitrobenzyl or p-methoxybenzyl radical, or (b) the symbol R.sub.1 represents an alkanoyl radical containing 1 to 8 carbon atoms, an alkanoyl radical containing 2 to 8 carbon atoms substituted by chlorine or bromine atoms, an acyl radical of the formula:
• ##STR153## (in which each Q is H or methyl and Ar represents a thien-2-yl, thien-3-yl, fur-2-yl, fur-3-yl, pyrrol-2-yl or pyrrol-3-yl radical or phenyl or phenyl substituted by halogen atoms or by hydroxyl radicals, by alkyl radicals (containing 1 to 3 carbon atoms) or by alkoxy radicals (containing 1 to 3 carbon atoms) of which at least one is situated in the meta- or para- position of the phenyl radical),
• an acyl radical of the formula:
• Ar-X-CH.sub.2 -CO--
• (in which X is oxygen or sulphur and Ar is as defined above or Ar-X represents pyridyl-4-ylthio, an acyl radical corresponding to the formula:
• ##STR154## (in which Ar is as defined above and B represents an amino radical which is protected [by a benzyloxycarbonyl, alkoxycarbonyl, cyclopentyloxycarbonyl, cyclohexyloxycarbonyl, benzhydryloxycarbonyl, trityl or 2,2,2-trichloro-ethoxycarbonyl group], a sulpho radical, a hydroxyl or carboxyl radical or hydroxyl or carboxyl protected by esterification, respectively with an alkanoic acid or an alcohol each containing 1 to 6 carbon atoms) or a 5-amino-adipyl radical or a 5-amino-adipyl radical [in which the amino group is protected by an alkanoyl radical (containing 1 to 3 carbon atoms and unsubstituted or substituted by a chlorine atom) and in which the carboxyl group is protected by a benzhydryl, 2,2,2-trichloroethyl, tert.-alkyl containing 4 to 6 carbon atoms, or nitrobenzyl group] or R.sub.1 NH-- is replaced by a cyclic imide group of a dicarboxylic acid and
• R.sub.2 represents a tert.-alkyl radical containing 4 to 6 carbon atoms, a tert.-alkenyl radical containing 6 or 7 carbon atoms, tert.-alkynyl radical containing 6 or 7 carbon atoms, benzyl, methoxybenzyl, nitrobenzyl, 2,2,2-trichloroethyl, benzhydryl, succinimidomethyl or phthalimidomethyl and
• the symbols R.sub.3 and R.sub.4, which are identical or different, represent alkyl radicals, alkyl radicals substituted by a hydroxyl, alkoxy, amino, alkylamino or dialkylamino radical, or phenyl radicals or form, together with the nitrogen atom to which they are attached, a saturated heterocyclic ring of 5 or 6 members, or a said ring containing another hetero-atom chosen from nitrogen, oxygen or sulphur, and unsubstituted or substituted by an alkyl radical, the alkyl or acyl portions of radicals mentioned above being (unless stated to the contrary) straight or branched and containing 1 to 4 carbon atoms, as well as mixtures of its isomers.