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【结 构 式】 
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【药物名称】Esonarimod, KE-298 【化学名称】(±)-2-(Acetylsulfanylmethyl)-3-(4-methylbenzoyl)propionic acid 【CA登记号】101973-77-7 【 分 子 式 】C14H16O4S 【 分 子 量 】280.34522 |
【开发单位】Taisho (Originator) 【药理作用】Antiarthritic Drugs, IMMUNOMODULATING AGENTS, Immunomodulators, Rheumatoid Arthritis, Treatment of, TREATMENT OF MUSCULOSKELETAL & CONNECTIVE TISSUE DISEASES |
合成路线1
The Friedel-Crafts condensation of toluene (I) with itaconic anhydride (2-methylenesuccinic anhydride) (II) by means of AlCl3 in methylene chloride or 1,2-dichloroethane gives 3-(4-methylbenzoyl)-2-methylenepropionic acid (III), which is then treated with thioacetic acid (IV) and K2CO3 in DMF/water.
| 【1】 Onodera, A.; Tomisawa, K.; Noguchi, T.; Yokomori, S.; A practical procedure for the synthesis of esonarimod, (R,S)-2-acetylthiomethyl-4-(4-methylphenyl)-4-oxobutanoic acid, an antirheumatic agent (Part 1). Chem Pharm Bull 2002, 50, 10, 1407. |
| 【2】 Mealy, N.; Castaner, J.; KE-298. Drugs Fut 1996, 21, 7, 691. |
| 【3】 Tomisawa, K.; Kameo, K.; Matsunaga, T.; Saito, S.; Sota, K. (Taisho Pharmaceutical Co., Ltd.); Benzoylpropionic acid derivs., their use and pharmaceutical compsns. EP 0164101; ES 8603818; JP 1985258160 . |
| 【4】 Tomisawa, K.; Kameo, K.; Matsunaga, Y.; Saito, H.; Sodu, H. (Taisho Pharmaceutical Co., Ltd.); 2-Acylthiomethyl-3-benzoylpropionic acid derivs. JP 1987132825 . |
| 【5】 Kameo, K.; Ogawa, K.; Takeshita, K.; Nakaike, S.; Tomisawa, K.; Sota, K.; Studies on antirheumatic agents: 3-Benzoylpropionic acid derivatives. Chem Pharm Bull 1988, 36, 6, 2050-60. |
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