Production of new or known monomeric uronic acid compounds, useful e.g. as immunosuppressive or antiarthritic agents, by hydrolyzing bacterially produced polyuronic acid

摘要

Production of monomeric uronic acids (or their derivatives) (I) involves (a) fermenting a bacterial strain producing a polyuronic acid (II) formed from (I) units, (b) isolating (II) from the supernatant of the fermentation broth, (c) hydrolyzing (II) and (d) isolating (I) from the hydrolysis product. Some compounds (I) are new. Independent claims are included for: (a) new monomeric uronic acids (or derivatives) of formulae (IA) and (IB); and (b) the use of (IA) and/or (IB) (where; R1, R4 = OH; R3, R4 = OH, 1-20C carboxylate, acyl (sic) or 1-20C alpha-aminocarboxylate (or an N-acylated derivative); R5 = OH, O-alkali metal or O-quaternary ammonium (optionally substituted by one or more groups Q'), and where the proviso that R1 - R5 are not all simultaneously OH does not apply) for the production of pharmaceutical or cosmetic compositions. In the new compounds (IA/IB): R1 - R4 = OH or -O-Pg; Pg = protecting group selected from -Q, -CO-Q, -CO-aryl, -SO2-Q, N-acylamino compound, P(O)(OH)w(OQ)2-w or P(O)(OH)w(O-aryl)2-w; or two Pg groups together form -(CH2)n-; w = 0-2; Q = linear, branched or cyclic 1-30C alkyl, optionally substituted by one or more of NH2 or heteroatoms (specifically halogen); n = 1-4; R5 = OH, O-alkali metal, O-quaternary ammonium (optionally substituted by one or more groups Q'), OQ' or NR6R7; Q' = linear, branched or cyclic 1-20C alkyl, optionally substituted by one or more heteroatoms (specifically halogen); R6, R7 = 1-30C alkyl, (1-30C) alkylcarbonyl or arylcarbonyl; provided that R1 - R5 are not all simultaneously OH.