Analgesics : from chemistry and pharmacology to clinical by Helmut Buschmann; Gregor Bahrenberg; et al PDF

By Helmut Buschmann; Gregor Bahrenberg; et al

ISBN-10: 3527304037

ISBN-13: 9783527304035

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2000). , 2000) were designed to assess both efficacy and gastrointestinal side-effects. The VIGOR trial included 8076 patients with rheumatoid arthritis receiving either rofecoxib or naproxen. The CLASS trial comprises of a total of 8059 patients with rheumatoid arthritis or osteoarthritis in two studies, comparing celecoxib to diclofenac and ibuprofen, respectively. 40 Christoph and Buschmann Colon cancer NSAIDs and COX-2 inhibitors show good potencies and efficacies in mild to moderate pain conditions and in inflammation.

Optimal selectivity was conferred by a 3-atom lipophilic substitution at the 3' position of the unsubstituted phenyl ring. , 2000). 41 jiM Figure 13: Modification of flurbiprofen. , 1997). New attempts to modify the modestly selective COX-2 inhibitor led to a new series of isoquinoline-1,3-diones, which are orally active COX-2-selective inhibitors (Lazer et al. (Boehringer Ingelheim), 1997; 1998). The most Modification of meloxicam 36 Christoph and Buschmann representative example of this series is BIRL-790 (Boehringer Ingelheim).

Condensation of (i) with 4-(methylsulfanyl)phenylboronic acid by means of Pd(PPh3)4 in refluxing ethanol(benzene affords 2-(benzyloxy)-5-chloro-3-(4-(methylsulfanyl) phenyl)pyridine (ii), which is treated with osmium tetroxide and sodium sulfite to furnish sulfone (iii). Treatment of the sulfone (iii) with TFA provides the 2-hydroxypyridine derivative, which is reacted with POCI3 to yield the key intermediate 2,5-dichloro-3-(4-(methylsulfonyl)phenyl) pyridine (iv). An alternative pathway to (vi) starts with the bromination of 2-chloropyridine with bromine in acetic acid to yield 2-amino-3-bromo-5-chloropyridine, which is coupled with (methylsulfanyl)phenylboronic acid by means of Pd(PPh3)4 and sodium carbonate in refluxing ethanol/benzene to give 5-chloro-3-(4-methanesulfonylphenyl)-pyridin-2-ylamine (v).

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Analgesics : from chemistry and pharmacology to clinical application by Helmut Buschmann; Gregor Bahrenberg; et al


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