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filingDate 1973-08-24-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationDate 1978-01-04-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber IE-38130-B1
titleOfInvention Antiviral complex
abstract 1387504 Sirodesmin compounds IMPERIAL CHEMICAL INDUSTRIES Ltd 16 Aug 1973 [14 Sept 1972] 42694/72 Headings C2A and C2C A novel antiviral complex comprising eight new compounds named Sirodesmin A, B, C, D, E, F, G and H, is produced by cultivating an antiviral complex-producing strain of the fungus Sirodesmium diversum in aqueous nutrient medium, extracting the culture filtrate with a water-immiscible solvent for the complex and evaporating the extract to dryness Sirodesmins A, B, and C have the general formula (I) wherein n is 2, 4 and 3 respectively, and R<SP>1</SP> is acetyl and R<SP>2</SP> is hydrogen in each case. Treatment of Sirodesmins A, B or C with methanolic HCl gives the corresponding desacetyl derivatives, having the Formula (I) wherein n is 2, 4 or 3 respectively and both R<SP>1</SP> and R<SP>2</SP> are hydrogen in each case. Conversely, treatment of Sirodesmins A, B or C with acetyl halide or acetic anhydride gives the mono-acetate of each compound, having the Formula (I) wherein n is 2, 4 or 3 respectively and both R<SP>1</SP> and R<SP>2</SP> are acetyl in each case. Further reactions include (a) treatment of Sirodesmin A with triphenylphosphine in chloroform to give Sirodesmin monosulphide having the Formula (I) wherein R<SP>1</SP> is acetyl, R<SP>2</SP> is hydrogen and n is 1; (b) treatment of Sirodesmin A with sulphur in the presence of an organic base and a solvent to give a mixture of Sirodesmins B and C; (c) treatment of Sirodesmin B and/or C with thionyl chloride in an organic base to give Sirodesmin A; and (d) treatment of the antiviral complex with SO 2 in pyridine giving a further new antiviral compound Sirodesmin J. Sirodesmins D, E, F, G, H and J are identified by their N.M.R. values in deuterochloroform and their I.R. spectra in liquid paraffin. Their molecular formulae are thought to be as follows: Sirodesmin D: C 20 H 26 N 2 O 8 S x where x is probably 4; Sirodesmin E: C 20 H 26 N 2 O 8 S x where x is probably 3; Sirodesmin F: C 20 H 26 N 2 O 8 S x where x is probably 3; Sirodesmin G: C 20 H 26 N 2 O 8 S 2 ; Sirodesmin H: C 20 H 26 N 2 O 8 S x where x is not defined; and Sirodesmin J: C 20 H 26 N 2 O 8 S 2 . The various Sirodesmins are separated from each other by chromatographic techniques. The Sirodesmins A-J and the antiviral complex containing them are admixed with pharmaceutically acceptable dilents or carriers to provide antivirally active pharmaceutical compositions.n[GB1387504A]
priorityDate 1972-09-14-04:00^^<http://www.w3.org/2001/XMLSchema#date>
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