Jerry P Adams

US Patent:

45200289, May 28, 1985

Filed:

Sep 5, 1984

Appl. No.:

6/647867

Inventors:

Jerry L. Adams - West Chester OH
Brian W. Metcalf - Mason OH
Bruce J. Lippert - Cincinnati OH

Assignee:

Merrell Dow Pharmaceuticals Inc. - Cincinnati OH

International Classification:

A61K 3138
C07D33300

US Classification:

514447

Abstract:

This application relates to 4-amino-4,5-dihydro-2-thiophenecarboxylic acid, the C. sub. 1-6 alkyl esters thereof and to their use in the treatment of epilepsy.

US Patent:

43258778, Apr 20, 1982

Filed:

Jun 16, 1980

Appl. No.:

6/160057

Inventors:

Brian W. Metcalf - Mason OH
Jerry L. Adams - West Chester OH

Assignee:

Richardson-Merrell Inc. - Wilton CT

International Classification:

C07C11708
C07C 6974
C07C 6966

US Classification:

260349

Abstract:

5-Amino-4-oxo-pentanoic acids of the formula ##STR1## wherein R is CF. sub. 3, CHF. sub. 2 or CH. sub. 2 F; R. sub. 1 is H or akyl of 1-4 carbon atoms; and R. sub. 2 is H or alkyl or 1-4 carbon atoms or benzyl, which are intermediates to ACE inhibitors or elastase inhibitors, are produced by reacting a 1-(methylthio)-1-methylsulfinyl)-2-R. sub. 1 -ethylmetal with an ester of a 3-R-acrylic acid; optionally R. sub. 2 -alkylating the thus-produced ester enolate anion of 4-(methylsulfinyl)-4-(methylthio)-5-R. sub. 1 R-pentanoic acid followed by splitting off of methylsulfinic acid; reacting the thus-produced 2-R. sub. 2 -5-R. sub. 1 -4-(methylthio)-3-R-4-pentenoic acid ester with a source of Br. sup. + to produce a 5-bromo-substituted acid or ester thereof otherwise corresponding to the desired 5-amino-4-oxo-pentanoic acid; and replacing the bromine atom with an amino group, e. g. , via the corresponding 5-azido- and 5-N-acylamino- compounds, with hydrolysis of the ester group, if still remaining.