Processes for the preparation of hydratropic acids and esters

Details Processes for the preparation of hydratropic acids and esters Processes for the preparation of hydratropic acids and esters

1979-12-19

1982-04-13

Killos, Paul J.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acid esters

560 20, 560 21, 560 23, 560 47, 560 59, 560 81, 560 82, 560 83, 560 85, 560 86, 562435, 562469, 562479, 562483, 562488, 562492, 2603402, 260343, 260465D, C07C 6976

Patent

active

043249043

ABSTRACT:
The invention concerns the novel compounds dialkyl 2-(3-fluoro-4-nitrophenyl)-2-methylmalonate IIIa and dialkyl 2-(3-fluoro-4-aminophenyl)-2-methylmalonate IVa useful as intermediates in an improved process for making 2-(2-fluoro-4-biphenylyl)propionic acid, known as flurbiprofen, having the formula ##STR1## and ester thereof. It has anti-inflammatory activity which is about 240 times that of aspirin and analgesic activity which is about 180 times that of aspirin in standard laboratory tests. However, despite this high activity, the toxicity (LD.sub.50) is only 1.2 to 2.4 times greater than that of aspirin in standard laboratory tests.
Also within the invention is a novel method of making the above intermediates and analogs thereof useful to prepare corresponding biaryl compounds which have pharmaceutical uses.

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Carney, et al., "A Potent Non-Steroidal Anti-Inflammatory Agent: 2-[3-chloro-4-(3-pyrrolinyl)phenyl]propionic acid," Experientia 29/8, p. 938, (Aug. 15, 1973).
Makosza et al., "Reactions of Organic Anions, Part LVIII. The Problem of Competitive Nucleophilic Substitution of Ortho- and Para-Halogens in 2,4-Dihalo Nitrobenzenes by some Carbanions", Roczniki Chemii Ann. Soc. Chim. Polonorum 50, p. 1850 (1976).
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