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:
Nov. 22, 1983
Filed:
May. 18, 1981
Thomas B Lee, Whitehouse Station, NJ (US);
George E Lee, Somerville, NJ (US);
Gregory M Jobin, Bridgewater, NJ (US);
Hoechst-Roussel Pharmaceuticals Inc., Somerville, NJ (US);
Abstract
A method for the preparation of 6,11-dihydro-11-oxodibenz[b,e]oxepin-acetic acids having pharmaceutical activity is disclosed. Compounds represented by the formula: ##STR1## wherein R is OH or Cl are provided as intermediates. An aldehyde of the formula: ##STR2## wherein R.sub.1 is a lower alkyl, e.g., 1 to 4 carbon atoms, is reacted with chloroform and aqueous base to form an .alpha.-hydroxy dicarboxylic acid. Alternatively, the aldehyde can be converted to the corresponding cyanohydrin, which is then converted to the corresponding .alpha.-hydroxy dicarboxylic acid. The .alpha.-hydroxy dicarboxylic acid can also be prepared from reaction of a halogenated toluate of the formula: ##STR3## wherein X is Cl or Br with mandelic acid or a derivative thereof of the formula: ##STR4## wherein R.sub.3 and R.sub.4 are independently selected from hydrogen and alkyl of 1 to 4 carbon atoms. The .alpha.-hydroxy dicarboxylic acid is cyclized and then converted to the oxepin acetic acid by reduction. Alternatively, the .alpha.-hydroxy dicarboxylic acid is cyclized and converted to an .alpha.-chloro-substituted oxepin acetic acid, which is then converted to the unsubstituted oxepin acetic acid by reductive removal of chlorine.