3-Di-substd.-amino-vinyl 1-oxa-cephalosporin derivs. - are intermediates for 3-thio-vinyl 1-oxa-cephalosporin(s), having good activity against gram-negative and positive bacteria

摘要

7-R"-7-R2NH-3-R3R4N-CH=CH-4-R1OOC -1-oxa-ceph-2- or 3-em derivs. of formula (I) are new (where the dotted line indicates a double bond in position 2 or 3; the C atom at position 3 may have E or Z stereoisomerism; R1 is an easily removable protecting gp. and (a) R2 is 2-R6NH-thiazol-4-yl-C(=N-OR5)-CO- gp. (Gp.A) or a protected alpha-carboxyarylacetyl radical Ar-CH(COOR'1)-CO-, R'1 is a protecting gp.; Ar is phenyl, opt. protected para-hydroxyphenyl or 2- or 3-thienyl and R" is H or methoxy in position 7-alpha or (b) R2 is an easily removable protecting gp. and R" is H or methoxy in position 7-alpha or H in position 7-beta; R3, R4 independently are alkyl (opt. substd. by alkoxy or dialkylamino) or phenyl or together with the N atom form a 5- or 6-membered satd. heterocyclic gp., opt. contg. a further N, O or S heteroatom and opt. alkyl substd.). Intermediates for the prepn. of 3-thiovinyl -oxacephalosporins of formula (XVIII). This process is described in detail in the specification, but is not claimed (where R is 2-, 3- or 4-pyridyl (including N oxide derivs.), 2-pyrimidyl, 6-methyl-1-oxido-3-pyridazinyl, opt. 4-substd.-5,6-dioxo -1,4,5,6-tetrahydro-1,2,4- triazin-3-yl, 1-alkyl-5,6-dioxo -1,4,5,6-tetrahydro- 1,2,4-triazin-3-yl, 2-alkyl-5,6-dioxo-1,2,5,6 -tetrahydro-1,2,4-triazin-3-yl, opt. 6-substd.-2-alkyl -2,5-dihydro-5-oxo-1,2,4 -triazin-3-yl, 1-amino-1,2-dihydro-2-oxo -4-pyrimidinyl, substd.-1,3,4-thiadiazol-5-yl, 1-substd.-5-tetrazolyl, opt. 3-substd.-1-alkyl-1,3,4 -triazol-5-yl and R' is a gp. derived from Gp.A. Details of the substits. etc. are given). (XVIII) are antibacterials having good activity against both gram-positive and gram-negative bacteria.