By Helmut Buschmann; Gregor Bahrenberg; et al
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Additional info for Analgesics : from chemistry and pharmacology to clinical application
It is commonly used for a variety of inflammatory and pain conditions such as musculoskeletal and joint disorders, periarticular disorders, soft tissue 2 Cyclooxygenase Inhibition disorders, renal colic, acute gout, dysmenorrhoea as well as postoperative pain. 5 % and the plasma elimination half-life is between 1 and 2 h. The metabolites of diclofenac, 4'-hydroxydiclofenac, 5-hydroxydiclofenac, 3'-hydroxy-diclofenac, and 4',5-dihydroxydiclofenac are excreted as glucuronide and sulphate conjugates in the urine (-65%) and in the bile (-35%).
For optimal activity, one aromatic ring must be substituted with a methylsulfonyl or a sulfonamide substituent in the para position. Substitution at position 4 of one of the aromatic systems with a sulfonamide or a methylsulfonyl group Is essential for COX Inhibition. Replacement of the methylsulfonyl group by a sulfonamide group reduces COX-2 selectivity but improves oral bioavailability. g. pyrrole, thiazole, °xaz°'e. furane, furanone, imidazole, isoxazole, pyrimidine, thiophene, pyrazole, cyclopentenone O — S-NH2 6 R ~S-CH3 • 6 Scheme 3: General structure of carbocycles and heterocycles with vicinal aryl substituents.
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).
Analgesics : from chemistry and pharmacology to clinical application by Helmut Buschmann; Gregor Bahrenberg; et al