药物详细合成路线

Name	Tenoxicam;Ro-120068;Liman;Tilcotil
Chemical Name	4-Hydroxy-2-methyl-N-(2-pyridyl)-2H-thieno[2,3-e]-1,2-thiazine-3-carboxamide 1,1-dioxide
CAS	59804-37-4
Related CAS
Formula	C13H11N3O4S2
Structure
Formula Weight	337.37832
Stage	上市-1987
Company	Kali-Chemie (Originator), Roche (Originator)
Activity/Mechanism	Antiarthritic Drugs, TREATMENT OF MUSCULOSKELETAL & CONNECTIVE TISSUE DISEASES, Non-Steroidal Antiinflammatory Drugs
Syn. Route	1

Route 1 the reaction of methyl 3-hydroxythiophene-2-carboxylate (i) with pcl5 in refluxing ccl4 gives 3-chlorothiophene-2-carboxylic acid (ii), which by treatment with nahso3 and cu in basic water at 143 c in a pressure vessel is converted into 3-sulfothiophene-2-carboxylic acid (iii). the esterification of (iii) with refluxing methanol affords methyl 3-sulfothiophene-2-carboxylate (iv), which by reaction with refluxing socl2 yields methyl-3-chlorosulfonylthiophene-2-carboxylate (v). the condensation of (v) with sarcosine ethyl ester (vi) in hot chcl3 gives methyl-3-(n-ethoxycarbonyl-methyl-n-methylsulfamoyl)thiophene-2-carboxylate (vii), which is cyclized by treatment with sodium methoxide in refluxing methanol affording 3-ethoxycarbonyl-4-hydroxy-2-methyl-2h-thieno-[2,3-e]-1,2-thiazine-1,1-dioxide (viii). finally, this compound is condensed with 2-aminopyridine (ix) in refluxing toluene. List of intermediates No. 3-chloro-n-(2-methoxy-4,6-dimethylphenyl)propanamide (ix) 3,3-diethoxypropylamine; 3,3-diethoxy-1-propanamine (v) (i) (ii) (iii) (iv) (vi) 1-(4-methoxyphenyl)-1-ethanone (vii) 2-bromo-1-(4-methoxyphenyl)-1-ethanone (viii) Reference 1:     horomatka, o.; binder, d.; pfister, r.; zeller, p. (f. hoffmann-la roche ag); thienothaiazine derivatives. de 2537070; fr 2303803; jp 51048694; nl 7510057 . Reference 2:     serradell, m.n.; blancafort, p.; castaner, j.; tenoxicam. drugs fut 1982, 7, 7, 493.

来源:药化网

作者:药化小编

摘要:本文合成路线介绍的是药物中文名替诺昔康；英文名Tenoxicam;Ro-120068;Liman;Tilcotil；CAS[59804-37-4]

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