By Helmut Buschmann; Gregor Bahrenberg; et al
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The bromination of 5-chloro-2-hydroxypyridine with bromine gives 3-bromo-5-chloro-2-hydroxypyridine, which is treated with benzyl bromide and silver carbonate yielding the benzyl ether-protected derivative (i). 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).
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). 44nM Figure 14: Modification of melioxicam. APHS as an aspirin derivative Aspirin is the only known NSAID that covalently bonds to serine and inhibits COX-1 more significantly than COX-2.
Moreover, NS-398 did not affect prostaglandin production in the stomach or kidney. On recognizing that NS-398 was a more or less preferential selective inhibitor of COX-2, new interest In this class of anti-inflammatory agents evolved. Nimesulide and flosulide are two other compounds with a diaryl ether and thioether structure, respectively, which bear a methansulfonanilide moiety. The sulfonamlde structure with its NH-acidity in all these compounds seems to be obligatory. R = Alkyl - aromatic ring - substituted aromatic heterocyclic ring - cycloaliphatic ring EWG EWG = electron withdrawing group Scheme 2: General structure of a sulfonanilide COX-2 Inhibitor (first generation scaffold).