Salts of amino-beta-lactamic acids and process for the...

C - Chemistry – Metallurgy – 07 – D

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C07D 487/04 (2006.01) C07C 279/04 (2006.01) C07D 205/085 (2006.01) C07D 417/12 (2006.01) C07D 477/08 (2006.01) C07D 501/18 (2006.01) C07F 9/568 (2006.01)

Patent

CA 1278568

ABSTRACT OF THE DISCLOSURE Amino-beta-lactamic acid salts, having the formula: Image (I) wherein: (X-Y) may form a system having from 1 to 3 carbon atoms, with or without double bond, a) closed, in which: X is an atom selected from among carbon, oxygen, nitrogen and sul- phur; Y is methylene; z is carboxy (-COO), b) open, which may comprise a double bond, in which: X is an atom of hydrogen or a methyl, hydroxymethyl or thiol group, Y is an acid radical chosen from the group formed by sulphonic (-SO3), phosphonic (-PO3H) or sulphoamidic (-SO2NH2) acid; Z is missing. R is an atom or hydrogen, or a methoxyl or ethoxyl group. R1 is, when present, methyl, acetoxymethyl, acylthiomethyl, such as acetyl and benzoyl derivatives, methoxy, chlorine, carbamoyl- oxymethyl, azido, azidomethyl (alpha, beta)-thioethylamine or a thiomethyl-heterocyclic derivative of the thiazole, thia- diazole, triazole, tetrazole, oxazole, oxadiazole, pyrimidine and imidazole nuclei. R2 is an atom of hydrogen or a methyl, ethyl, benzyl or aryl group. m, n may be the same or dif- ferent and may range from 1 to 4, forming a ring or m = n = 0 to represent in this case that the atom of N(1) supports a hydrogen or a methyl group; the atom of N(2) a methyl group and the atom of N(3) two methyl groups, forming an open chain guanidine. A process for their preparation is also disclosed. The inventive salts of amino-beta-lactamic acids are useful in the preparation of N-acyl derivatives of said salts, said derivatives being of interest in the manufacture of monolactamic acid and bicyclic antibiotics derived from 7-amino-cephalosporanic, 7-amino-1-(oxo)-cephalosporanic, etc. acids.

454356

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