Dihydrotriazinylthiooxacephalosporins

A compound of the formula ##STR146## wherein R is lower alkyl;

• E is hydrogen or methoxy;
• M is hydrogen or a hydroxy protecting group;
• COB is carboxy, protected carboxy or a carboxy salt;
• and A is
• (1) azido, isocyanato, isocyano;
• (2) amino;
• (3) trimethylsilylamino, methoxydimethylsilylamino, dimethoxymethylsilylamino or trimethylstannylamino;
• (4) a hydrocarbonated amino group selected from the group consisting of 1-carbethoxy-1-propen-2-ylamino, 1-carbamoyl-1-propen-2-ylamino, 1-N-phenylcarbamoyl-1-buten-2-ylamino, 1-propen-2-ylamino, 1-phenylpentene-2-ylamino, methylamino, t-butylaminotritylamino, methylideneamino, ethylideneamino, 1-halo-2-phenylethylideneamino, 1-chlorobenzylideneamino, 1-methoxybenzylideneamino, 1-loweralkoxy-2-phenylethylideneamino, 1-loweralkoxy-2-phenoxyethylideneamino and di-t-butyl-4-hydroxybenzylideneamino;
• (5) a diacylamino derived from a C.sub.4 to C.sub.10 polybasic carboxylic acid;
• (6) a o-nitrophenylsulfenylamino group;
• or
• (7) an acylamino group wherein the acyl group is
• (a) C.sub.1 -C.sub.10 alkanoyl or benzoyl;
• (b) halo-C.sub.1 -C.sub.4 alkanoyl;
• (c) trifluoromethylthioacetyl or cyanoacetyl;
• (d) (2- or 4-pyridon-1-yl)acetyl or (2-iminothiazolin-4-yl)acetyl;
• (e) a group of the formula
• Ar--CQQ'--CO--
• wherein Q and Q' are hydrogen or methyl;
• Ar is a cyclic group selected from phenyl, dihydrophenyl, furyl, thienyl, pyrrolyl, oxazolyl, isoxazolyl, oxadiazolyl, oxatriazolyl, thiazolyl, isothiazolyl, thiadiazolyl, thiatriazolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, pyridyl, pyrimidyl, pyridinyl, pyridazinyl or triazinyl which cyclic groups are unsubstituted or are substituted by halogen, lower alkyl, hydroxy, both a halogen and a hydroxy, lower alkoxy, formyloxy, acetyloxy, propionyloxy, pentanoyloxy, carbamoyloxy, benzoyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, t-butoxycarbonyloxy, benzyloxycarbonyloxy, nitrobenzyloxycarbonyloxy, methoxybenzyloxycarbonyloxy, benzyloxy, methoxybenzyloxy, aminobenzyloxy, methylbenzyloxy, isopropylbenzyloxy, nitrobenzyloxy, diphenylmethoxy, phthalidyloxy, phenoxy, tolyloxy, xylyloxy, indanyloxy, amino, C.sub.1 -C.sub.10 alkanoylamino, lower alkanesulfonylamino, hydroxymethyl, or aminomethyl;
• (f) a group of the formula
• Ar--G--CQQ'--CO--
• wherein Ar, Q and Q' are the same as defined above and G is oxygen or sulfur;
• (g) a group of the formula
• Ar--CHT--CO--
• wherein Ar is the same as defined above;
• T is (i) hydroxy, formyloxy, acetyloxy, propionyloxy, pentanoyloxy, carbamoyloxy, benzoyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, t-butoxycarbonyloxy, benzyloxycarbonyloxy, nitrobenzyloxycarbonyloxy or methoxybenzyloxycarbonyloxy;
• (ii) carboxy, carboxy protected by lower alkoxy, benzyloxy, methoxybenzyloxy, aminobenzyloxy, methylbenzyloxy, isopropylbenzyloxy, nitrobenzyloxy, diphenylmethoxy, phthalidyloxy, phenoxy, tolyloxy, xylyloxy, indanyloxy, cyano or carbamoyl;
• or (iii) sulfo or lower alkoxysulfonyl;
• (h) a group of the formula
• L--O--CO--
• wherein L is t-butyl, 1,1-dimethylpropyl, cyclopropylmethyl, 1-methylcyclohexyl, isobornyl, ethoxy-t-butyl, 2-alkanesulfonylethyl, 2,2,2-trichloroethyl, benzyl, methoxybenzyl, nitrobenzyl, aminobenzyl, diphenylmethyl, tolylmethyl, phenyl, xylyl or pyridylmethyl;
• (i) a group of the formula ##STR147## wherein Ar is the same as defined above;
• W is C.sub.1 -C.sub.10 alkanoyl, halo-C.sub.1 -C.sub.4 alkanoyl, or a group represented by the formula Ar--CQQ'--CO--as defined above, Ar--CO--, LOCO--, ##STR148## R.sup.1 NHCONR.sup.2 --CO--, R.sup.1 NHCSNR.sup.2 CO--, ##STR149## wherein Ar and L are as defined above and R.sup.1 and R.sup.2 are hydrogen, C.sub.1 -C.sub.4 alkyl, or C.sub.1 -C.sub.10 alkanoyl;
• or
• W is an enolic group of active carbonyl compounds represented by the formula ##STR150## wherein R.sup.1 and R.sup.2 are the same as defined above;
• or NHW is phthalimido or succinimido;
• (j) an acyl group of the formula ##STR151## wherein Ar and R.sup.1 are the same as defined above;
• or (k) a 5-aminoadipoyl group in which the carboxy or amino group is optionally protected with a conventional carboxy or amino protecting group;
• and when A is amino or an acyl group having an amino substituent, an acid addition salt of the compounds represented thereby;
• provided that when E is methoxy, E is in the 7-alpha position on the cephem ring.