Intermediates for substituted azetidinones useful as anti-inflammatory and antidegenerative agents
US5149838A · kind A · utility
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Key dates
| Filing date | Sep 20, 1991 |
| Grant date | Sep 22, 1992 |
| Priority date | — |
| Expiry date | Sep 20, 2011 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07D405/12
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
Disclosed is a process for the enantioselective synthesis of the compound of Formula I and related compounds. The process comprises the synthesis of the benzofuranyl carboxaldehyde; introduction of the benzylic amine functionality with control of the absolute stereochemistry; preparation of the azetidinone fragment and its coupling to the benzofuranyl amine fragments. The carboxylic acid in Formula I is liberated using heterogenous palladium catalyzed de-allylation of the allyl esters. Compounds I have been found to be potent elastase inhibitors and thereby useful anti-inflammatory and antidegenerative agents. ##STR1##
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