2'-Substituted alkaloids of the cinchona series, especially 2'-substituted quinine, quinidine, cinchonine, cinchonidine and their dihydro analogs, and their salts, are prepared by treating ar-N-oxides of the alkaloids with the corresponding organometallic reagent and, if desired, converting the free bases thus formed into pharmaceutically acceptable acid addition salts. The new compounds are pharmacologically active, especially anti-malarially and anti-arrhythmically.

The present invention is directed to a new class of 6-benzyl urea/thiourea-quinolin-2-one derivatives and 2-oxo-6-benzylurea/thiourea-chromene derivatives. These compound are androgen antagonists and are useful in the treatment of alopecia, acne and other conditions associated with inappropriate activation of the androgen receptor.

One aspect of the present invention relates to quinine-based and quinidine-based catalysts. In certain embodiments, the quinine-based and quinidine-based catalysts contain a hydroxy group at the 6' position. In certain embodiments, the quinine-based and quinidine-based catalysts contain an O-aryl group or an O-aroyl group at the C9 position. In certain embodiments, the quinine-based and quinidine-based catalysts contain an optionally substituted O-diazene group or an optionally substituted O-ben...

This invention relates to an optically active hydroquinine (amino-3 phenyl)-1 ethanesulfonate (form A), preparation thereof and its use as an intermediate in the preparation of cholecystokinine and gastrin antagonists.

A process is disclosed for obtaining manipulated proportions of the (+) and (-) enantiomers of [(6,7-dichloro-2,3-dihydro-2-methyl-1-oxo-2-phenyl-1H-inden-5-yl)oxy]aceti c acid by asymmetric chiral phase transfer catalysis.

Method of oxidizing cinchona alkaloids by reacting specific ketone with cinchona alkaloid in the presence of a strong base and aprotic solvent; following oxidation the oxo compound is reduced to the corresponding stereoisomer.

The title compounds are obtained by racemate resolution of D,L-homoalanin-4-yl(methyl)phosphinic acid via precipitation of one of the diastereomeric salts using chiral bases such as quinine or cinchonine. It is possible to increase the yield of desired enantiomer by transformed racemate resolution when the precipitation of the diastereomeric salt takes place with the racemization of the undesired enantiomer in the presence of (hetero)--aromatic aldehydes. The racemization method is also suitable...

Amino secondary alcohols, e.g. cinchona alkaloid such as quinine, epiquinine, quinidine, epiquinidine and mixtures thereof, are oxidized to quininone, i.e., a mixture of quininone and quinidinone, by reaction of the alcohols with a metal ketyl, in an inert hydrocarbon solvent. The ketyl is formed through the reaction of an alkali metal or amalgam with a diphenyl ketone, such as benzophenone or fluorenone.

Quinidinone is reduced to quinidine through reaction with a reducing agent, selected from aklyl-substituted aluminum hydrides or alkali metal alkyl-substituted aluminum hydrides, in the presence of a stereospecific orienting agent, such as pyridine.

Described are improved processes for the enantioselective synthesis of .alpha.-amino acids which involve combinations of solvents, highly-mixed and low-temperature reaction conditions, and novel catalysts. Also described are novel catalysts and precursors to .alpha.-amino acid derivatives.