GB1387769A - Butenoic acid derivatives and a process for the manufacture thereof - Google Patents

Abstract

1387769 Butenoic acid derivatives F HOFFMANN-LA ROCHE & CO AG 12 June 1973 27910/73 Heading C2C The novel compound L-trans-2-amino-4(2- aminoethoxy) - 3 - butenoic acid of the formula and acid addition salt thereof, are prepared by cultivating Streptomyces nov. sp. X-11085 (NRRL 5331) or a mutant or variant thereof capable of producing said compound in an aqueous nutrient medium containing assimilable sources of carbon, nitrogen and inorganic salts under submerged aerobic conditions and then recovering the said compound from the medium and if desired, converting it into an acid addition salt. The preferred salt is the hydrochloride. The compound may be recovered by filtering off the mycelium from the medium, and either treating the filtrate with a cation exchange resin to adsorb the compound followed by elution thereof with a solvent (e.g. ethanol/water NH 4 OH, 80 : 15 : 5), or subjecting the filtrate to partition chromatography on a silica gel support using the aforesaid solvent. The eluate is then concentrated to a syrup and crystallized by adding aqueous methanol. The filtered medium is preferably pre-purified by treatment with adsorptive charcoal. The novel compound and its acid addition salts have antimicrobial, antiprotozoal, anthelmintic and herbicidal activity. They may be formulated into oral, injectable or topical pharmaceutical compositions with an appropriate pharmaceutically acceptable vehicle or diluent, and also made up into herbicidal compositions, especially for post-emergent application, with convential carriers, diluents and adjuvants used in such compositions.