Syntex (u.s.a.) Inc.

John O Gardner

Robin D Clark

Joseph M Muchowski

Jacob Berger

Norman H Dyson

Fang-Ting Chiu

Denis John Kertesz

Anthony Prince

Alam Jahangir

John C Rohloff

Karl G Untch

Richard M Eglen

Aaron Bayne Miller

The present invention relates to novel 5-HT.sub.4 receptor ligands which are 1-(5-halo-4-aminophenyl) (C.sub.2-6)alkan-1-one derivatives in which the 5-halo-4-aminophenyl group is substituted at its 2-position with (C.sub.1-4)alkyloxy or phenyl(C.sub.1-4)alkyloxy and optionally substituted at its 3-position with (C.sub.1-4)alkyloxy or substituted at its 2- and 3-positions together with methylenedioxy or ethylenedioxy and the highest numbered carbon of the (C.sub.2-6)alkan-1-one is substituted with di(C.sub.1-4)alkylamino, morpholin-1-yl or pyrrolidin-1-yl or optionally substituted piperidin-1-yl, piperidin-4-yl, azacyclohept-1-yl, azabicyclo�2.2.1!hept-3-yl, azabicylo�2.2.2!oct-3-yl or azabicylo�3.2.2!non-3-yl; and the pharmaceutically acceptable salts, individual isomers and mixtures of isomers and methods of using and making such derivatives.

1-phenylalkanone 5-HT.sub.4 receptor ligands

This invention provides an improved process for the preparation of compounds of formula (I): ##STR1## wherein: n is 0, 1 or 2;

Process for preparing 1,3-dioxolane derivatives

The invention provides a process for preparing single enantiomers of compounds represented by the formula: ##STR1## and chiral acid addition salts thereof; wherein: X and Y are independently hydrogen; lower alkyl; lower alkoxy; or halo; or X and Y taken together is methylenedioxy or ethylene-1,2-dioxy; which includes reduction of a compound represented by the formula: ##STR2## to give a mixture of stereoisomers represented by the formula: ##STR3## wherein each wavy line independently represents a bond in either the .alpha. or .beta. position;

Process for the preparation of (8As,12AS,13AS)-decahydroisoquino

Compounds of the formula ##STR1## wherein R.sub.1 and R.sub.2 are each independently --H or lower alkoxy;

Method for treating cardiovascular disease with calcium channel

Compounds of the formula ##STR1## wherein R.sub.1 and R.sub.2 and each independently --H or lower alkoxy; R.sub.3 and R.sub.4 are each independently lower alkyl; and R.sub.5 and R.sub.6 are each --OCH.sub.3, or together form --OCH.sub.2 O-- or --OCH.sub.2 CH.sub.2 O--, and pharmaceutically acceptable acid addition salts thereof are prepared by cyclizing, deoxygenating, coupling, or hydrogenating the intermediates disclosed herein.

Tetrahydroisoquinoline derivatives

3-Carboxy-5-substituted-thiacycl[2.2.2]azines of the formula: ##STR1## wherein R is phenyl or phenyl monosubstituted in the meta or para position with fluoro, chloro, lower alkyl of from 1 to 4 carbon atoms or lower alkoxy of from 1 to 4 carbon atoms, and the pharmaceutically acceptable salts thereof. These compounds are useful as anticomplimentary agents, specifically for the treatment of inflammatory conditions, auto-immune diseases, allergic reactions and vascular diseases.

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Los Altos, CA, United States of America

John O Gardner