The patent badge is an abbreviated version of the USPTO patent document. The patent badge does contain a link to the full patent document.
The patent badge is an abbreviated version of the USPTO patent document. The patent badge covers the following: Patent number, Date patent was issued, Date patent was filed, Title of the patent, Applicant, Inventor, Assignee, Attorney firm, Primary examiner, Assistant examiner, CPCs, and Abstract. The patent badge does contain a link to the full patent document (in Adobe Acrobat format, aka pdf). To download or print any patent click here.
Patent No.:
Date of Patent:
May. 12, 1992
Filed:
May. 30, 1991
Daniel E Martin, Lee's Summit, MO (US);
Merrell Dow Pharmaceuticals Inc., Cincinnati, OH (US);
Abstract
A cyano glycidic acid ester compound can be prepared by reaction of an alkyl haloester and a cyano-aldehyde in the presence of an alkali metal alkoxide; an amino-acid ester cyano compound can be prepared by reaction of the cyano glycidic acid ester compound and an attachable amino compound, and a cyclic amido-carbonyl cyano compound can be prepared by contact of the amino-acid ester cyano compound in a liquid medium with a heterogeneous acidic ion-exchange substance. For example, reaction of 4-cyanobenzaldehyde and methyl chloroacetate in the presence of sodium methoxide in methanol, followed by ice/acetic acid neutralization, prepares trans-3-(4-cyanophenyl)glycidic acid, methyl ester, which is reacted in toluene with 2-aminothiophenol to yield 2-hydroxy-3-(2-aminophenylthio)-3-(4-cyanophenyl)propionic acid, methyl ester, threo form, which is cyclized in an aqueous mixture into cis-2-(4-cyanophenyl)-3-hydroxy-2,3-dihydro-1,5-benzothiazepin-4(5H)-one by employing a sulfonated polystyrenedivinylbenzene ion-exchange resin in its acid form, e.g., Dowex 50X4-400, at cyclization yields exceeding 70 percent of theory. Compounds of this invention are useful pharmaceuticals.