FR2164793A1 - 3-oxyiminomethylcephalosporins - antibiotics inters - Google Patents

Abstract

Cpds. of formula (I): where n = 0 or 1 R=H, alkanoyl, (1-8C) chloro- or bromo-alkanoyl (2-8C) azidoacetyl cyanoacetyl, a gp (II): where Q = H, or methyl; Ar = 2- or 3-thienyl, 2- or 3-furyl, 2- or 3- pyrrolyl or phenyl opt. substd. with >=1 Cl, Br, I, F, CF3, hydroxy, alkyl, or alkoxy (1-3C) cyano or nitro, whereby >=1 of these substituents must be in m- or p-posn at the phenyl ring; Ar-X-CH2-C(O)-, where X = -O or -S; Ar = as signified or 4-pyridyl and X = -S; a gp. (III): Ar-C(X1)H-C(O)- where X1 = -NH2, -NH3 circled positive, amino protected by benzyloxycarbonyl, alkoxycarbonyl (1-4C) cyclopentoxycarbonyl, cyclohexoxy-carbonyl, benzhydryloxycarbonyl, triphenylmethyl, 2,2,2-trichloroethoxycarbonyl, a gp. (IV):- C(O)NH-C (=NH)-NH2 -SO3H, or phthalimido, the enamine form of methylacetylacetate or acetylacetone; or X1 = hydroxyl opt. protected by esterification with an alkanecarboxylic acid (1-6C) carboxyl, opt. protected by esterification with an alkanol (1-6C) or a gp, -N3, -CN or -C(O)NH2; or R = 2-sydnone-3-(C1-C3) alknoyl or a gp. (V): where m = 0,1 or 2; 5-aminodipoyl opt. amino-protected with alkanoyl (1-3C) or chloroalkanoyl (1-3C) or carboxyl-protected with benzyhydryl, 2,2,2-trichloroethyl, alkyl (4-6C) or nitrobenzyl; R1 = H, or R+R1+N = H3N- circled positive a salt gp. with an acid with a pK a-value of 4, or a cyclic imide derived from a dicarboxylic acid or a hydrocarbon (3-12C), a gp (VI); where Z = (-CH2-)y y = 1 or 2; or -O; or R+R1+N = (alkyl)2-N-CH=N- (alkyl 1-2C); R2 = tert. alkyl (4-6C) tert. alkenyl- or tert. alkynyl (5-7C) benzyl, methoxybenzyl, nitrobenzyl, 2,2,2-trichloroethyl, 3,5-di(t. butyl)4-hydroxybenzyl, acetoxymethyl, pivaloyloxymethyl, 2-iodoethyl, benzhydryl, phenacyl, trimethylsilyl, succinimidomethyl, phthalimidomethyl or H; Y = H, alkyl (1-6C), haloalkyl (2-6C) where halo = Cl or Br; aromatic hydrocarbon (6-12C) cycloalkyl (4-7C), alkylene-X-alkyl, where alkylene = 1-3C and X -O or -S; -CH2COOR3 where R3 = H or alkyl (1-6C), or -CH2CH2N(CH3)2. Pharmaceutically acceptable salts of (I) are included.