Imperial Chemical Industries Limited

David C Aldridge

Graham C Crawley

Colin J Strawson

John C Swait

Roger Bowling

The invention concerns a fermentation process for the production of (+)-2-(5.beta.-n-butyl-4.beta.-hydroxy-2-oxo-tetrahydrofuran-3.beta.-yl)-2 .alpha.-methylacetic acid, which compound has useful ulcer-healing properties. The process is characterised by cultivating an organism known to produce dihydrocanadensolide, such as Penicillium canadense, under generally conventional conditions and then extracting the culture filtrate at a pH in the range pH 3.0-7.0 with a suitable solvent, such as ethyl acetate, and then evaporating the extract to dryness. In a preferred embodiment the extraction is carried out on the culture filtrate at pH 4.0-4.5.

Fermentation process for the production of

The invention concerns novel racemic and optically active mono- and di-hydroxy alkanoic acids bearing phenyl and/or alkyl substituents, processes for their preparation, and pharmaceutical compositions for therapeutic use in the treatment of duodenal or gastric ulcers. Representative compounds of the invention are 2-(5.beta.-n-butyl-4.beta.-hydroxy-2-oxo-tetrahydrofuran-3.beta.-yl)-2.alp ha.-methyl-acetic acid and 3.alpha.-methyl-5.beta.-(1.beta.-hydroxy-n-pentyl)-2-oxo-tetrahydrofuran-4 .beta.-ylcarboxylic acid.

Hydroxy acids

Pharmaceutical compositions containing 3,3a,6,6a-tetrahydrofuro[3,4-b]furan derivatives including canadensolide and 3-epi-dihydrocanadensolide. Novel 3,3a,6,6a-tetrahydrofuro[3,4-b]furan derivatives bearing a variety of substituents in the 3- and 6-positions selected from alkyl, phenyl, alkoxycarbonyl, methylene, benzylthiomethyl and optionally substituted phenylthiomethyl. The compositions and novel compounds show anti-ulcer activity and are useful in the treatment of gastric or duodenal ulcers.

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Macclesfield, United Kingdom

David C Aldridge