GB1004467A - Penicillins - Google Patents

Abstract

The invention relates to 6-aminopenicillanic acid derivatives of general formula <FORM:1004467/C2/1> wherein R represents a straight or branched chain lower alkyl containing 1 to 6 C atoms, or a phenyl, benzyl, thienyl or furyl radical, each of said radicals being optionally substituted by halogen, hydroxy, C1- 4 alkyl or C1- 4 alkoxy and M is hydrogen or a pharmaceutically acceptable cation. The compounds may be obtained by the catalytic hydrogenation of an azido penicillin of formula <FORM:1004467/C2/2> where R and M are as defined above. The azido penicillin may be obtained by reacting 6-aminopenicillanic acid with an acylating agent e.g. chloride, bromide or iodide containing the appropriate <FORM:1004467/C2/3> radical, where R is as above. Alternatively, a reactive derivative of an acid of formula <FORM:1004467/C2/4> may be reacted with a silyl derivative of 6-aminopenicillani acid. In another method the azidopenicillin is produced by reacting an anhydride of formula <FORM:1004467/C2/5> with an alkali metal salt of 6-aminopenicillanic acid. Examples are 1-phenyl-1-azidomethyl-propyl penicillin and 1 - phenyl - 1 - amino-methyl propyl penicillin; the corresponding isobutyl- and pentyl-penicillins; a -phenyl-a -azidomethylbenzylpenicillin and a - pheny - a - aminomethyl benzyl penicillin; 1-phenyl-1-azidomethyl - 2 - phenyl ethyl penicillin and 1 - phenyl - 1- aminomethyl - 2 - phenylethyl penicillin. 2 - phenyl - 2 - azidomethyl butyric acid is prepared by treating 2-phenyl-2-bromomethyl butyric acid with sodium azide. 2-phenyl-2-azidomethyl butyrylchloride is prepared by reacting the aforesaid acid with thionyl chloride. 2,2 - diphenyl - 2 - azidomethyl acetyl chloride, 2 - phenyl 2 - azido methyl iso valeryl and caproyl chlorides, and 3-phenyl-2-phenyl-2-azidomethyl propionyl chloride are prepared in a similar manner. The aminomethyl penicillins and the azidomethyl penicillins may be used in pharmaceutical compositions for oral, topical or parenteral use e.g. tablets, capsules, powders, suspensions, solutions, suppositories and ointments. They may be used in animal feeds. They are resistant to aqueous acid.