Abstract: A process for the stereoselective preparation of intermediates in the preparation of potent, chiral thiazolidine-2,4-dione hypoglycemics.

Abstract: A novel multi-step process for preparing the (4S)-enantiomer of 4-(3,4 -dichlorophenyl)-3,4-1(2H)- naphthalenone in a highly-optically pure form is disclosed. The process involved starts from the known 4-(3,4-dichlorophenyl)-4-ketobutanoic acid and proceeds through such intermediates as (1) isopropyl or tert.- butyl 4-(3,4 -dichlorophenyl)-4-ketobutanoate, (2) isopropyl or tert.-butyl 4-(3,4-dichlorophenyl)-(4R)-hydroxybutanoate, (3) isopropyl or tert.-butyl 4-(3,4-dichlorophenyl-(4R)-sulfonyloxybutanoate, (4) isopropyl or tert.-butyl 4-(3,4-dichlorophenyl)-(4R)-phenylbutanoate to finally yield the desired (4S)-4-(3,4-dichlorophenyl)-3,4-dihydro -1(2H)-naphthalenone compound in a highly-optically pure form. The latter compound, which is a (4S)-enantiomer per se, has utility as an intermediate that ultimately leads to pure cis-(1S)(4S)-N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthal eneamine (sertraline), which is a known antidepressant agent. The aforementioned isopropyl and tert.

Abstract: Compounds of the formula ##STR1## wherein R.sup.1 is hydrogen, fluoro, chloro, bromo, nitro, trifluoromethyl, C.sub.1 to C.sub.4 alkoxy, C.sub.1 to C.sub.4 alkylthio or C.sub.1 to C.sub.6 alkyl and R.sup.2 is a group of the formula ##STR2## wherein R.sup.3 is hydrogen or C.sub.1 to C.sub.6 alkyl, R.sup.4 is --CH.dbd.C.sub.2, --CH.sub.2 --YR.sup.5, or --COR.sup.6, R.sup.5 is hydrogen or an acid labile alcohol protecting group, Y is oxygen or sulfur, and R.sup.6 is --NR.sup.7 R.sup.8 or --OR.sup.9 wherein R.sup.7, R.sup.8 and R.sup.9 are independently selected from hydrogen or C.sub.1 to C.sub.6 alkyl, or an alkaline or alkaline earth metal salt thereof, which are intermediates in the preparation of hydantoin aldose reductase inhibitors and methods of preparing these intermediates.

Abstract: The present invention relates to processes and intermediates for the preparation of spiro-heteroazolones. The latter compounds are useful as aldose reductase inhibitors.

Abstract: A novel multi-step process for preparing the (4S)-enantiomer of 4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenone in a highly-optically pure form is disclosed. The process involves (1) first reacting 3,4-dichlorocinnamyl chloride with L-(-)-ephedrine in a chlorinated lower hydrocarbon solvent to form the corresponding chiral N-methyl-N-(.beta.-hydroxy-.beta.-phenylisopropyl)-3-(3,4-dichlorophenyl)p ropenoamide; (2) then subjecting the chiral .alpha.,.beta.-unsaturated amide formed in the first step to a Grignard reaction with phenyl magnesium chloride or bromide, followed by hydrolysis, to effect a conjugate addition of the phenyl group and the hydrogen element to the aforesaid .alpha.,.beta.-unsaturated propenoamide and so selectively form the corresponding chiral N-methyl-N-(.beta.-hydroxy-.beta.

Abstract: Improved processes for preparation of racemic, cis- and optically active (3S,4R)-3[1(R)-t-butyl-dimethylsilyloxy)-ethyl]-4-[1-oxo-3-thiolanylthio(t hiocarbonyl)thio]azetidin-2-ones, process improvements for certain intermediates therefor and a novel intermediate for said racemic, cis- and trans-compounds, which compounds are useful as intermediates for antibacterial 5R,6S-6-[1(R)-hydroxyethyl]-2-(1-oxo-3-thiolanylthio)-2-penem-3-carboxylic acids and the pharmaceutically-acceptable salts and the pivaloyloxymethyl esters thereof.

Abstract: The present invention relates to processes and intermediates for the preparation of spiro-heteroazolones. The latter compounds are useful as aldose reductase inhibitors.

Abstract: Preparative method for 3R-(3-carboxybenzyl)-6-(5-fluoro-2-benzothiazolyl)methoxy-4R-chromanol via its salt with quinine.

Abstract: A novel three-step process for preparing 4-(3,4-dichlorophenyl)-4-phenylbutanoic acid is disclosed, which involves (1) reducing 4-(3,4-dichlorophenyl)-4-ketobutanoic acid to 4-(3,4-dichlorophenyl)-4-hydroxybutanoic acid; (2) then converting the intermediate hydroxy acid formed in the first step to 5-(3,4-dichlorophenyl)-dihydro-2(3H)-furanone, and (3) thereafter reacting the resulting gamma-butyrolactone compound with benzene in a Friedel-Crafts type reaction to form the desired final product. The latter compound is known to be useful as an intermediate leading to 4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenone and ultimately, to cis-(1S)(4S)-N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthal ene amine (sertraline), which is known to be a preferred anti-depressant agent in the field of medicinal chemistry. The aforementioned 5-(3,4-dichlorophenyl)-dihydro-2(3H)-furanone and 4-(3,4-dichlorophenyl)-4-hydroxybutanoic acid are both novel compounds.

Abstract: A novel three-step process for preparing 4-(3,4-dichlorophenyl)-4-phenylbutanoic acid is disclosed, which involves (1) reducing 4-(3,4-dichlorophenyl)-4-ketobutanoic acid to 4-(3,4-dichlorophenyl)-4-hydroxybutanoic acid; (2) then converting the intermediate hydroxy acid formed in the first step to 5-(3,4-dichlorophenyl)-dihydro-2(3H)-furanone, and (3) thereafter reacting the resulting gamma-butyrolactone compound with benzene in a Friedel-Crafts type reaction to form the desired final product. The latter compound is known to be useful as an intermediate leading to cis-(1S)(4S)- -N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthaleneamine (sertraline), which is known to be a preferred anti-depressant agent in the field of medicinal chemistry. The aforementioned 5-(3,4-dichlorophenyl)-dihydro-2(3H)-furanone and 4-(3,4-dichlorophenyl)-4-hydroxybutanoic acid are both novel compounds.