G.d. Searle & Company

Norman A Abood

Roger A Nosal

Lori A Schretzman

Daniel L Flynn

Masateru Miyano

Scott A Laneman

Daniel Paul Becker

Robert E Manning

Clara I Villamil

Robert B Garland

Hui Li

Brian M Bax

Susan Landis Hockerman

Kenneth Williams

Jeffery Alan Zablocki

Michael J Bennett

2-Amino-benzoxazinones for the treatment of viral infections

2-amino benzoxazinones for the treatment of viral infections

The present invention relates to double prodrugs of pharmacologically active glycoprotein IIb/IIIa antagonists of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of lower alkyl of about 2 to about 8 carbon atoms, cycloalkyl, and aralkyl; R is selected from the group consisting of alkoxy, ##STR2## wherein R.sup.50 is H or alkyl; and ##STR3## wherein R.sup.50 is H or alkyl; and pharmaceutically acceptable salts thereof.

Double prodrugs of potent GP IIb/IIIa antagonists

A class of compounds for the treatment of viral infections. Compounds of particular interest are defined by Formula II ##STR1## wherein R.sup.28 is selected from (a) amino substituted with one or two radicals selected from alkyl, aralkyl, heterocycoalkyl, heterocyclo, and aryl, and (b) amino acid residues and derivatives thereof; wherein R.sup.29 is selected from hydrido, alkyl, halo, ##STR2## wherein R.sup.30 is selected from alkyl, alkoxy, alkylamino, carboxyalkyl, alkoxyalkyl, alkylaminoalkyl, cycloalkyl, heterocyclo, heterocycloalkyl, heterocycloalkoxy, alkylaminoalkoxy, alkylaminoalkylamino, heterocycloalkylamino, and N-aralkylamino; wherein R.sup.31 is alkyl; wherein R.sup.32 is alkyl and aryl; or a pharmaceutically-acceptable salt thereof.

2-amino-benzoxazinones for the treatment of viral infections

Platelet aggregation inhibitors

A method is described for synthesis of N-Boc-L-propargylglycine, a key intermediate used in the preparation of high-potency, orally-active renin inhibitors. This method involves reaction of an organic halide with a glycine cation equivalent, such as methyl N-Boc-2-acetoxyglycine, in the presence of zinc dust to give Boc-protected amino acid derivatives in high yield. Typically useful organic halides are allylic, benzylic and propargylic halides. Resolution of methyl N-Boc-propargylglycine with .alpha.-chymotrypsin provides N-Boc-L-propargylglycine in high yield.

Synthesis of chiral N-protected-.alpha.-substituted-glycine free acids

The invention herein is directed to a process for producing a lactam of the formula ##STR1## from a methionine analog of the formula ##STR2## by treating the methionine analog with trimethylsulfonium halide or trimethylsulfoxonium halide in the presence of a base in a suitable aprotic solvent. The invention herein is further directed to the preparation of amidinophenyl pyrrolidinyl .beta.-alanine urea analogs using such methionine and lactam compounds as intermediates, which .beta.-alanine urea analogs are useful as antithrombotics.

Intermediates for amidino phenyl pyrrolidine .beta.-alanine urea analogs

This invention relates to phenyl amidine alkanoic acids and lactones having the following formula ##STR1## or a pharmaceutically acceptable salt which are useful in the inhibition of platelet aggregation. This invention also relates to pharmaceutical compositions of such phenyl amidine derivatives.

Phenyl amidine alkanoic acids useful as platelet aggregation inhibitors

Phenyl amidine lactones useful as platelet aggregation inhibitors

Process for the preparation of amidino phenyl pyrrolidine beta-alanine

Process for the preparation of amidino phenyl pyrrolidine .beta.-alanine

This invention relates to compounds having the following formula ##STR1## or a pharmaceutically acceptable salt which are useful in the inhibition of platelet aggregation. This invention also relates to pharmaceutical compositions--of such phenyl amidines derivatives.

Peptide mimetic compounds useful as platelet aggregation inhibitors

Synthesis of N-protected-.alpha.-substituted-glycine racemic esters by

Phenyl amidine alkanoic acids and lactones useful as platelet

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Morton Grove, IL, United States of America

Norman A Abood