【结 构 式】 |
【药物名称】Piroxicam, CP-16171, Baxo, Felden, Feldene Fast, Feldene Gel, Feldene 【化学名称】4-Hydroxy-2-methyl-2H-1,2-benzothiazine-3-[N-(2-pyridyl)carboxamide]-1,1-dioxide 【CA登记号】36322-90-4 【 分 子 式 】C15H13N3O4S 【 分 子 量 】331.35256 |
【开发单位】Pfizer (Originator), Toyama (Licensee) 【药理作用】ANALGESIC AND ANESTHETIC DRUGS, Analgesic Drugs, Ankylosing Spondylitis, Treatment of, Antiarthritic Drugs, METABOLIC DRUGS, Non-Opioid Analgesics, Osteoarthritis, Treatment of, Rheumatoid Arthritis, Treatment of, Treatment of Disorders of Purine and Pyrimidine Metabolism, Treatment of Gout, TREATMENT OF MUSCULOSKELETAL & CONNECTIVE TISSUE DISEASES, Non-Steroidal Antiinflammatory Drugs |
合成路线1
The isomerization of methyl 3-oxo-1,2-benzothiazolin-1,1-dioxide-2-acetate (I) by means of sodium methoxide in DMSO gives methyl 3,4-dihydro-4-oxo-2H-1,2-benzothiazine-1,1-dioxide-3-carboxylate (II), which is methylated with methyl iodide and NaOH in methanol giving methyl 3,4-dihydro-2-methyl-4-oxo-2H-1,2-benzothiazine-1,1-dioxide-3-carboxylate (III). Finally, this product is treated with 2-aminopyridine (A) in refluxing xylene.
【1】 Arrigoni-Martelli, E.; Castaner, J.; Piroxicam. Drugs Fut 1977, 2, 2, 124. |
【2】 Lombardino, J.G.; et al.; Potent anti-inflammatory N-heterocyclic 3-carboxamides of 4-hydroxy-2-methyl-2H-1,2-benzothiazine 1,1-dioxide. J Med Chem 1973, 16, 5, 493. |
【3】 Lombardino, J.G.; Wiseman, E.H.; Sudoxicam and related N.heterocyclic carboxamides of 4-hydroxy-2-methyl-2H-1,2-benzothiazine 1,1-dioxide, potent non steroidal anti-inflammatory agents. J Med Chem 1972, 15, 8, 848. |
【4】 Lombardino, J.G. (Pfizer Inc.); Benzothiazine dioxides. DE 1943265; FR 2016455; GB 1257180; US 3591584 . |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
(A) | 11305 | 2-Pyridinamine; 2-Pyridinylamine; 2-Aminopyridine | 504-29-0 | C5H6N2 | 详情 | 详情 |
(I) | 40062 | methyl 2-(1,1,3-trioxo-1,3-dihydro-2H-1,2-benzisothiazol-2-yl)acetate | 6639-62-9 | C10H9NO5S | 详情 | 详情 |
(II) | 40063 | methyl 1,1,4-trioxo-1,2,3,4-tetrahydro-1lambda(6),2-benzothiazine-3-carboxylate | C10H9NO5S | 详情 | 详情 | |
(III) | 40064 | methyl 2-methyl-1,1,4-trioxo-1,2,3,4-tetrahydro-1lambda(6),2-benzothiazine-3-carboxylate | C11H11NO5S | 详情 | 详情 |