Chlortenoxicam, Lornoxicam, HN-10000, TS-110, Ro-13-9297, CLTX, Xefocam, Taigalor, Telos, Lorcam, Acabel, Xefo, Safem

氯诺昔康Chemical Name: 6-Chloro-4-hydroxy-2-methyl-N-(2-pyridyl)-2H-thieno[2,3-e]-1,2-thiazine-3-carboxamide 1,1-dioxide
CAS No. 70374-39-9
项目整合开发状态: Launched-1997
项目研究机构: Nycomed Pharma (Originator), CeNeS (Licensee), Formenti (Licensee), Merckle (Licensee), Taisho (Licensee)
合成路线:The sulfonation of 2,5-dichlorothiophene (I) with ClSO3H -SOCl2 gives 2,5-dichlorothiophene-3-sulfonic acid chloride (II),which by reaction with methylamine in CHCl3 yields the corresponding methylamide (III).The carboxylation of (III) with butyllithium and CO2 in ether affords 5-chloro-3-(N-methylsulfamoyl)thiophene-2-carboxylic acid (IV),which is esterified with PCl5 and methanol to the methyl ester (V).The condensation of (V) with methyl iodoacetate (VI) by means of NaH in DMF gives 5-chloro-3-[N-(methoxycarbonylmethyl)-N-methylsulfamoyl]thiophene-2-carboxylic acid methyl ester (VII),which is cyclized with sodium methoxide in methanol yielding 6-chloro-4-hydroxy-2-methyl-2H-thieno[2,3-e]-1,2-thiazine-3-carboxylic acid methyl ester 1,1-dioxide (VIII).Finally,this compound is treated with 2-aminopyridine (IX) in refluxing xylene.