Upgrade to enjoy subscriber-only features like email alerts and data export. See the Plans and Pricing

Serving hundreds of leading biopharmaceutical companies globally:

Cantor Fitzgerald
US Department of Justice
Johnson and Johnson

Generated: June 24, 2018

DrugPatentWatch Database Preview

Details for Patent: 5,599,973

« Back to Dashboard

Title: GABA and L-glutamic acid analogs for antiseizure treatment
Abstract:A compound of the formula ##STR1## wherein R.sub.1 is a straight or branched alkyl group having from 1 to 6 carbon atoms, phenyl, or cycloalkyl having from 3 to 6 carbon atoms; R.sub.2 is hydrogen or methyl; and R.sub.3 is hydrogen, methyl or carboxyl; which is useful in the treatment of seizure disorders. Processes are disclosed for the preparation of the compound. Intermediates prepared during the synthesis of the compound are also disclosed.
Inventor(s): Silverman; Richard B. (Morton Grove, IL), Andruszkiewicz; Ryszard (Sopot, PL), Yuen; Po-Wai (Ann Arbor, MI), Sobieray; Denis M. (Holland, MI), Franklin; Lloyd C. (Hamilton, MI), Schwindt; Mark A. (Holland, MI)
Assignee: Northwestern University (Evanston, IL) Warner-Lambert Company (Ann Arbor, MI)
Filing Date:Apr 12, 1995
Application Number:08/420,580
Claims:1. A process for preparing an S-isomer of a compound of the formula

wherein R.sub.1 is a straight or branched alkyl of from 1 to 6 carbon atoms, phenyl, or cycloalkyl having from 3 to 6 carbon atoms; R.sub.2 is hydrogen, methyl, or carboxyl; individual enantiomers thereof; and pharmaceutically acceptable salts thereof; with the proviso that when R.sub.2 is hydrogen, R.sub.1 is other than methyl; said process comprising the steps of forming an acid chloride of an acid of the formula HOC(.dbd.O)CH(R.sub.1)(R.sub.2), the corresponding acid chloride having the formula ClC(.dbd.O)CH(R.sub.1)(R.sub.2), adding the acid chloride to a solution of (4R,5S)-(+)-4-methyl-5-phenyl-2-oxazolidinone and n-butyllithium at -78.degree. C. under argon to produce an oxazolidinone derivative of the formula ##STR9## treating the oxazolidinone (II) with benzyl .alpha.-bromoacetate to produce an ester ##STR10## treating the ester (III) with hydrogen peroxide and lithium oxide followed by treatment with sodium metabisulfite to produce a compound of the formula ##STR11## treating the compound (IV) with borane dimethyl sulfide complex to produce the compound ##STR12## forming the corresponding tosylate from the compound (V), forming an azide from the corresponding tosoylate and reducing the azide to the amine of the formula ##STR13## wherein R.sub.1 and R.sub.2 have the meanings defined for formula (I), Ph is phenyl, Me is methyl, and Bn is benzyl.

For more information try a trial or see the plans and pricing

Serving hundreds of leading biopharmaceutical companies globally:

Harvard Business School
US Department of Justice
Boehringer Ingelheim

Drugs may be covered by multiple patents or regulatory protections. All trademarks and applicant names are the property of their respective owners or licensors. Although great care is taken in the proper and correct provision of this service, thinkBiotech LLC does not accept any responsibility for possible consequences of errors or omissions in the provided data. The data presented herein is for information purposes only. There is no warranty that the data contained herein is error free. thinkBiotech performs no independent verifification of facts as provided by public sources nor are attempts made to provide legal or investing advice. Any reliance on data provided herein is done solely at the discretion of the user. Users of this service are advised to seek professional advice and independent confirmation before considering acting on any of the provided information. thinkBiotech LLC reserves the right to amend, extend or withdraw any part or all of the offered service without notice.