Verfahren zur Herstellung von 6-[(-)-alpha-Amino-p-hydroxy-phenylacetamido] penicillansaeure

• Main Authors: CHARLES NAYLER,JOHN HERBERT, WALTER LONG,ANTHONY ALFRED
• Format: Patent
• Language: German
• Published: 26.02.1970
• Subjects: CHEMISTRY; HETEROCYCLIC COMPOUNDS; HUMAN NECESSITIES; HYGIENE; MEDICAL OR VETERINARY SCIENCE; METALLURGY; ORGANIC CHEMISTRY; PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES

1,241,844. Penicillins. BEECHAM GROUP Ltd. 20. Aug., ,1969 [23 Aug., 1968], No. 40319/68. Heading C2A. [Also in Divisions A5-A6] The (-) isomer of 6-(α-amino-p-hydroxyphenyl - acetamido) - penicillanic acid is prepared by reacting 6-aminopenicillanic acid or a salt thereof with a functional derivative of the (-) isomer of a-carboxylic acid of formula where X is an amino group, a protected amino group or a group which is subsequently converted into an amino group. X may be a protonated amino group, a benzoyloxycarbonyl- or substituted' benzoyloxycarbonyl - amino group, an enamine group or a 2-sulphonylethoxycarbonylamino group, or may be an azido group which is converted to amino by catalytic or electrolytic reduction. Functional derivatives of the acid may be the halide or a mixed anhydride, an 0-acyl isourea or an imidazolide, or the acid may be simultaneously activated at the carboxyl group and aminoprotected by conversion to a Leuch's anhydride. The ( -) isomer of 6-(α-amino-p-hydroxyphenylacetamido)- penicillanic acid has greater antibacterial activity and is better absorbed after oral administration than the (+) isomers and the m-hydroxy analogues. The (+) isomer of 6-(α-amino-p-hydroxyphenylacetamido)-penicillanic. acid is prepared by acylating 6-aminopenicillanic acid with the (+) epimer of the carboxylic acid of Formula (II) above. Also the (+) and- (-) epimers of 6 - (α - amino - m - hydroxyphenylacetamido) penicillanic acid are prepared using the mhydroxy isomers of the acylating acid.