O-substd. spectinomycin oxime, imine or hydrazone derivs. - useful as intermediates for antimicrobial spectinomycyl-amine derivs.

摘要

New spectinomycin derivs. are of formula (I) and physiologically tolerable acid addn. salts of those cpds. which are basic. where X = H or a readily removable (by treatment with acids or bases or by reduction) organic gp. knwon from peptide chemistry (e.g. benzyloxycarbonyl; opt. unsatd. 1-12C alkoxycarbonyl opt. substd. by 2-furyl, p-tolylsulphonyl, one or more halogen atoms, 1-3C alkoxy or (1-3C alkoxy)-(1-3 alkoxy); 5-12C cycloalkyloxycarbonyl; isobornyloxycarbonyl; 1-adamantyloxycarbonyl; phenyl-(2-4C alkoxy)-carbonyl or biphenyl-(2-4C alkoxy)-carbonyl opt. substd. in the phenyl residue by 1-3 methyl or methoxy gps.; diphenylmethoxycarbonyl; benzyloxycarbonyl opt. substd. by NO2, OCH3 or CH3; dialkylaminooxycarbonyl; (1-4C alkylthio)carbonyl; benzylthiocarbonyl; formyl; 2-10C acyl opt. substd. by 1-3 halogen atoms, OH, acyl or NO2; benzoyl; 2-nitrobenzoyl; p-toluenesulphonyl; benzylsulphonyl; p-methoxybenzenesulphonyl; benzyl or trityl). Y = OH, OCH3, benzyloxy; piperidono; -NH-CZ-R1; -NH-SO2-R2; 2-R3-6-R4-4-pyrimidinylamino; 2-pyridylamino; 2-pyrimidinylamino; 2-oxo-benzoxazol-3-yl; 1, 2, 3, 4-tetrahydro-2-oxo-1-quinolyl; tetrahydro-4,4-dimethyl-1,3-dioxo-2-isoquinolyl opt. substd. by OCH3 in the aromatic ring; 2-oxo-1-imidazolidinyl; 2,4-dioxo-1-imidazolinyl opt. substd. in the 3-position by phenyl; or 2-oxo-3-oxazolidinyl opt. substd. in the 5-position by CH3, C2H5, benzyl, p-chlorobenzyl or phenyl (opt. in turn substd. by 1-3 halogen atoms or OCH3. Z = O or S; R1 = methyl opt. substd. by CN, morpholino, N-methylanilino or N-methylbenzylamino; phenyl opt. substd. by OH or amino; pyridyl; amino; anilino; 1-6C alkoxy; 7-10C aralkoxy or phenoxy. R2 = CH3 or p-tolyl. R3, R4 = CH3, phenyl or amino. (I) are intermediates for spectinomycylamine derivs. with antimicrobial activity (cf. DT. 2756914).