Patent HU-9903086-A3 (HU)
Title: Modified oligosaccharides
Filed: 1997-08-06
Abstract: Modified oligosaccharides of formula (I) and their salts are new. R1 = S-configurated methyl substituted by one carboxy and one other substituent; R2 = H, 1-12C alkyl (optionally substituted by one or more substituents) or 6C aryl (optionally substituted by one or more substituents); Z = a group of formula (a)-(c); X = C(O), C(S), S(O)2, C(O)Q or C(S)Q; Q = NH, O, S, S-(1-6C) alkylene, NH-(1-6C)alkylene or O-(1-6C) alkylene: Rt1 = 1-12C alkyl, 2-12C alkenyl, 1-12C alkoxy, 3-12C cycloalkyl, 3-12C cycloalkenyl, 2-11C heterocycloalkyl, 2-11C heterocycloalkenyl, 6-10C aryl, 6-10C aryloxy, 5-9C heteroaryl, 5-9C heteroaryloxy, 7-11C aralkyl, 7-11C aralkyloxy, 6-10C heteroaralkyl, 8-11C aralkenyl or 7-10C heteroaralkenyl (all optionally substituted by one or more substituents); Rt2 = 3-12C cycloalkyl, 3-12C cycloalkenyl, 2-11C heterocycloalkyl, 2-11C heterocycloalkenyl, 6-10C aryl, 6-10C aryloxy, 5-9C heteroaryl, 5-9C heteroaryloxy, 7-11C aralkyl, 7-11C aralkyloxy, 6-10C heteroaralkyl, 8-11C aralkenyl or 7-10C heteroaralkenyl (all optionally substituted by one or more substituents); Rb5 = NH2, primary amino, secondary amino or amido; R5 = X'=Rt1c, C(O)NRt2cRt3c, C(O)Rt4c or C(O)ORt5c; X' = 1-4C alkylene; Rt1c = H, halo, 1-12C alkyl, 1-11C heteroalkyl, 3-12C alkenyl, 3-12C cycloalkyl, 3-12C cycloalkenyl, 2-11C heterocycloalkyl, 2-11C heterocycloalkenyl, 6C, 10C or 14C aryl, 2-9C heteroaryl, 7-11C aralkyl, 6-10C heteroaralkyl, 9-11C aralkenyl, 8-10C heteroaralkenyl, ORt6c, OC(O)Rt4c, SRt4c, SO2Rt9c or SO3Rt5c; Rt2c, Rt3c and Rt4c = H, 1-12C alkyl, 1-11C heteroalkyl, 3-12C alkenyl, 3-12C cycloalkyl, 3-12C cycloalkenyl, 2-11C heterocycloalkyl, 2-11C heterocycloalkenyl, 6C, 10C or 14C aryl, 2-9C heteroaryl, 7-11C aralkyl, 6-10C heteroaralkyl, 9-11C aralkenyl or 8-10C heteroaralkenyl; Rt5c, Rt7c and Rt8c = H, My, 1-12C alkyl, 1-11C heteroalkyl, 3-12C alkenyl, 3-12C cycloalkyl, 3-12C cycloalkenyl, 2-11C heterocycloalkyl, 2-11C heterocycloalkenyl, 6C, 10C or 14C aryl, 2-9C heteroaryl, 7-11C aralkyl, 6-10C heteroaralkyl, 9-11C aralkenyl or 8-10C heteroaralkenyl; Rt6c = H, 1-12C alkyl, 1-11C heteroalkyl, 3-12C alkenyl, 3-12C cycloalkyl, 3-12C cycloalkenyl, 2-11C heterocycloalkyl, 2-11C heterocycloalkenyl, 6C, 10C or 14C aryl, 2-9C heteroaryl, 7-11C aralkyl, 6-10C heteroaralkyl, 9-11C aralkenyl, 8-10C heteroaralkenyl, SO3Rt5c, PO3Rt7cRt8c, C(O)ORt9c, C(S)NRt2cRt3c or C(O)NRt2cRt3c; Rt9c = 1-12C alkyl, 1-11C heteroalkyl, 3-12C alkenyl, 3-12C cycloalkyl, 3-12C cycloalkenyl, 2-11C heterocycloalkyl, 2-11C heterocycloalkenyl, 6C, 10C or 14C aryl, 2-9C heteroaryl, 7-11C aralkyl, 6-10C heteroaralkyl, 9-11C aralkenyl or 8-10C heteroaralkenyl; wherein the substituent is chosen from OH, halo, NH2, C(O)Rs2, C(O)ORs1, OC(O)Rs4, nitro, cyano, SO3H, OSO3H, SO3My, OSO3My, NR20SO3My, 1-12C alkyl, 2-12C alkenyl, 1-12C alkoxy, 3-12C cycloalkyl, 3-12C cycloalkenyl, 2-11C heterocycloalkyl, 2-11C heterocycloalkenyl, 6-10C aryl, 6-10C aryloxy, 5-9C heteroaryl, 5-9C heteroaryloxy, 7-11C aralkyl, 7-11C aralkyloxy, 6-10C heteroaralkyl, 8-11C aralkenyl, 7-10C heteroaralkenyl, primary amino, secondary amino, sulphonyl, sulphonamido, carbamido, carbamate, sulphonhydrazido, carbohydrazido, carbohydroamic acid or aminocarbonylamido; Rs1 = H, My, 1-12C alkyl, 2-12C alkenyl, 3-12C cycloalkyl, 2-11C heterocycloalkyl, 6-10C aryl, 5-9C heteroaryl, 7-11C aralkyl or 6-10C heteroaralkyl; Rs4 = H, 1-12C alkyl, 2-12C alkenyl, 3-12C cycloalkyl, 2-11C heterocycloalkyl, 6-10C aryl, 5-9C heteroaryl, 7-11C aralkyl or 6-10C heteroaralkyl; Rs2, R20 = H, 1-12C alkyl, 2-12C alkenyl, 3-12C cycloalkyl, 3-12C cycloalkenyl, 2-11C heterocycloalkyl, 2-11C heterocycloalkenyl, 6-10C aryl, 5-9C heteroaryl, 7-11C aralkyl, 6-10C heteroaralkyl, 8-11C aralkenyl or 7-10C heteroaralkenyl, and alkyl, alkenyl, alkoxy, cycloalkyl, cycloalkenyl, heterocycloalkyl, heterocycloalkenyl, aryl, aryloxy, heteroaryl, heteroaryloxy, aralkyl, aralkyloxy, heteroaralkyl, aralkenyl and heteroaralkenyl in turn are optionally substituted by one of the above substituents; y = 1 and M = monovalent metal or y = 0.5 and M = divalent metal, provided that at least one OH is substituted with SO3Rt5c, PO3Rt7cRt8c, C(O)Rt9c, C(O)ORt9c, C(S)NRt2cRt3c, C(O)NRt2cRt3c, 1-12C alkyl, 3-12C alkenyl, 3-12C cycloalkyl, 3-12C cycloalkenyl, 1-11C heteroalkyl, 2-11C heterocycloalkyl, 2-11C heterocycloalkenyl, 6C, 10C or 14C aryl, 2-9C heteroaryl, 7-11C aralkyl, 6-10C heteroaralkyl, 9-11C aralkenyl or heteroaralkenyl.