Olgiopeptide derivatives of phosphonic acid

C - Chemistry – Metallurgy – 07 – F

Patent

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530/5.04, 530/7.

C07F 9/38 (2006.01) C07K 5/06 (2006.01) C07K 5/08 (2006.01) A61K 38/00 (2006.01)

Patent

CA 1108125

ABSTRACT OF THE DISCLOSURE A process for the manufacture of compounds which are peptide derivatives of formula I Image (I) wherein R1 is H, CH3, CH2OH or mono-, di- or trihalomethyl R2 is the characterising group of an .alpha.-amino acid normally found in proteins or lower alkyl or hydroxy-(lower alkyl) other than such characterising group; R3 is lower alkyl, lower cycloalkyl, lower alkenyl, aryl or aryl-(lower alkyl); R4 is H or lower alkyl; n = 1, 2 or 3; configuration at C-atom (a) is (R) when Rl is other than H; configuration at C-atom (b) is (L) when R2 is other than H; and salts thereof. The process comprises cleaving off by methods known per se the protecting group(s) in a compound of formula Ia Image (Ia) wherein (a), (b), n, R3 and R4 are as above; R5 and R6 are H or lower alkyl protecting groups; R7 is protecting group; R10 is R1 plus protected hydroxymethyl; R20 is R2 (except that functional group(s) present in R2 are protected). These peptide derivatives possess an antibacterial activity against a wide range of gram-positive and gram-negative bacteria, particularly against Streptococcus faecalis and Haemophilus influenzae.

317617

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