| abstract |
3-(2-Furanyl, -thienyl or -pyrrolyl)-pyrazole or -indazole derivatives (I) are new. Pyrazole derivatives of formula (I) and their stereoisomers, stereo isomer mixtures and salts are new: X = O, S, NH or N(Me); R1, R1a = wither (i) H, halo, OR6, NR7R8, COOR9, COR10, CONR11R12, CONR12OR11, S(O)mR13, SO2NR14R15, CN or NO2; or (ii) A, aryl, arylalkyl, cycloalkyl, cycloalkylalkyl, Het or Het-alkyl (all optionally substituted by one or more R5); A = 1-10C alkyl; R2-R4 = as R1 (ii); or R2 + R3 = 5-7 membered carbocyclic ring, optionally containing double bond(s) and/or substituted by one or more R5; n = 0-2; R5 = as R1 (i) (excluding H) or CF3 or 1-5C alkyl; R6-R15 = H; or A, aryl, arylalkyl, cycloalkyl, cycloalkylalkyl, Het or Het-alkyl (all optionally substituted by one or more of halo, 1-5C alkyl, OR18, NR19R20, COOR21, COR22, CONR23R24, CONR24OR23, S(O)mR25, SO2NR26R27, CN, NO2 or CF3); R6-R8,R11,R14 can also = COR16 or SO2R17; R16, R18-R27 = H or as R17; R17 = 1-6C alkyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, Het or Het-alkyl; or R18-R20, R23, R26 can also = COR16 or SO2R17; or NR7R8, NR11R12, NR14R15, NR19R20, NR23R24, NR26R27 = 5-7 membered (un)saturated heterocycle, optionally containing a further N, O or S heteroatom and/or substituted by one or more halo and/or alkyl; unless specified otherwise alkyl moieties have 1-4C, cycloalkyl 3-7C and aryl 6-14C; provided that: (1) R5 can only = NO2 if R1a = H, R2 + R3 = optionally substituted benzene ring and n = 0 and R4 is not unsubstituted phenyl; (2) R4 is not H if n = 0; (3) (I) are excluded where: R1 = H, A', COOH, COOA', CH2OH, CH2OA' or halo in the 5-position; R1a = H; R2 + R3 = benzene ring (optionally monosubstituted by A', halo, OH or OA'); n = 1; and R4 = phenyl (optionally monosubstituted by A', halo, OH or OA'); and (4) (I) are excluded where: X = S; R1 = Cl in the 5-position; R1a,R3 = H; R2 = Me; n = 0; and R4 = (Me)2N-CO-CH(Me)-; and A' = 1-3C alkyl. An Independent claim is included for the preparation of (I). |