A highly efficient method for enriching the chiral purity of a partially enriched mixture of enantiomers of an optically active compound, a major portion of the partially enriched mixture of enantiomers comprising a first enantiomer of the optically active compound, a minor portion of the partially enriched mixture of enantiomers comprising a second enantiomer of the optically active compound. The method comprises mixing an acid in whatever form it may exist in solution with an aqueous solution of the partially enriched mixture of enantiomers, in whatever form the partially enriched mixture of enantiomers may exist in solution, to form a reaction mass comprising a further enriched mixture of enantiomers of the optically active compound, the further enriched mixture of enantiomers having a higher percentage of the first enantiomer than the partially enriched mixture. The optically active compound has the formula: where R.sup.1, R.sup.2, and R.sup.3 are different from each other and are selected from the group consisting of a hydrogen atom, hydrocarbyl groups, hydrocarbyloxy groups, hydrocarbylthio groups, hydrocarbylcarbonyl groups, halohydrocarbyl groups, hydrocarbyloxyhydrocarbyl groups, heteroaromatic groups, and halogen atoms, with the proviso that none or only one of R.sup.1, R.sup.2, and R.sup.3 can be a halogen atom, and where Z is an alkali metal cation, a cation of a nitrogenous base or a combination of the foregoing.

The present invention relates generally to the fields of chemotherapeutic treatments. More particularly, it concerns the use of ibuprofen, a non-steroid anti-inflammatory drug, in the treatments of disease. More particularly, it has been discovered that the R-enantiomer of ibuprofen, previously thought to be inactive, may be used as an antineoplastic agent and also in the prophylactic and therapeutic treatment of Alzheimer's and Alzheimer's related diseases.

The invention relates to a novel non-catalytic enantioselective resolution process for the separation of enantiomer of arylpropionic acid drugs from the racemic mixture, which comprises dissolving the racemic mixture of the said drug an organic solvent, reacting this solution with an aqueous phase containing an ionic surfactant with or without a suitable co-surfactant, and an electrolyte in microemulsion/micellar/biphasic medium, reacting this mixture with an appropriate chiral amine at a temperature in the range of 0 to 70 degrees Celsius to obtain a diastereomeric salt, acid hydrolysing the diastereomeric salt to result in the pure enantiomer of the drug which is extracted by known methods.

A compound of chemical formula (I) and its pharmaceutically acceptable salt: ##STR1## wherein X and Y are each hydrogen, halogen, C.sub.1 -C.sub.6 alkyl, halosubstituted C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkylthio, C.sub.1 -C.sub.6 alkylsulfinyl, C.sub.1 -C.sub.6 alkylsulfonyl, or tri(C.sub.1 -C.sub.6 alkyl)silyl; Ar.sup.1 and Ar.sup.2 are each independently aryl or heteroaryl, optionally substituted by halogen; A is --CO-- or -(CH.sub.2)-; Z-A- is at the 2 or 3 position on the quinuclidine ring; and Z is --OH, C.sub.1 -C.sub.6 alkoxy, NR.sup.1 R.sup.2 or the like. Representative compounds are (3S,4R,5S,6S)-5-[3,5-bis(trifluoromethyl)-benzyloxy]-N,N-dimethyl-6-diphen ylmethyl-1-azabicyclo[2.2.2]octan-3-carboxamide, and -3-carboxylic acid. These novel benzyloxyquinuclidines are active as substance P receptor antagonists and are thus useful for treating gastrointestinal disorders, central nervous system disorders, allergy, inflammatory diseases, asthma, pain, emesis, migraine, urinary incontinence, or angiogenesis in mammals, especially humans.