Enantiomers of quaternary tropaic acid alkaloid derivs. - sepd. from racemates and enantiomer mixts using chiral polysaccharide phases and certain organic and aq. eluants and anionic modifiers

摘要

Enantiomeric quat. tropaic acid alkaloid derivs. of formula (I) are new. In (I), (Ia) Y = (R)- or (S)-T'-O and Z = H, in (Ib) Z = (R)- or (S)-T'-O and Y = H, R1 = 1-10C alkyl or CH2CH2F, R2 = 1-10C alkyl or up to 10C cycloalkylalkyl, or R1 and R2 together form -(CH2)n, n = 4 or 5, R3 and R4 = H or together form O, (R)-T' is the (R)-tropaic acid gp., and (S)-T' is the (S)-tropaic acid gp., X(-) is an equivalent of an anion. USE/ADVANTAGE - (I) have anticholinergic properties. (Ia) and (Ib) have different profiles of activity and enantiomer mixts. of (Ia) and (Ib) can be sepd. simply by chromatography. In an example, cellulose tris(3,5-dimethylphenyl) carbamate was used as the stationary phase. The mobile phase was 60 vol.pb. n-hexane/15 vol. pts. EtOH/25 vol. pts. MeOH plus 2 mmol. tetra propylammonium bromide per litre. The flow rate was 0.5 ml/min. and detection was at 230 nm. The injected vol. was 10 micro-l. at a concn. of 1 mg/ml. The mobile phase was degassed by ultrasound treatment for 3 min. when mixt. of (I; R1=R2=Me, R3=R4=H, Z=H, Y = (R)-/(S)-TO, where T - tropaoic acid) enantiomers was subjected to chromatography under the above conditions, the results were as follows ti = 8.67, t2 = 13.02, k1 = 0.84, k2 = 1.77, alpha = 2.11. Units and details of t1, t2, k1, k2 and alpha not given.