|
【结 构 式】 
|
【药物名称】SC-56938 【化学名称】1-[2-(4-Benzylphenoxy)ethyl]piperidine-4-carboxylic acid ethyl ester 【CA登记号】186901-93-9, 179020-29-2 (hydrochloride) 【 分 子 式 】C23H29NO3 【 分 子 量 】367.49248 |
【开发单位】Pfizer (Originator) 【药理作用】Antiallergy/Antiasthmatic Drugs, Antiarthritic Drugs, Antipsoriatics, Asthma Therapy, DERMATOLOGIC DRUGS, GASTROINTESTINAL DRUGS, Inflammatory Bowel Disease, Agents for, RESPIRATORY DRUGS, TREATMENT OF MUSCULOSKELETAL & CONNECTIVE TISSUE DISEASES, Leukotriene A4 Hydrolase Inhibitors |
合成路线1
4-Hydroxydiphenylmethane (I) is condensed with tert-butyl bromoacetate (II) in the presence of NaH and Bu-4NI to form the aryloxyacetate adduct (III). Ester group reduction in (III) employing LiAlH4 provides alcohol (IV), which is further treated with p-toluenesulfonyl chloride in pyridine, yielding tosylate (V) (1,2). Finally, condensation of tosylate (V) with ethyl isonipecotate (VI) furnishes the title compound (1-3).
| 【1】 Pyrrolidine and piperidine analogues of SC-57461A as potent, orally active inhibitors of leukotriene A(4) hydrolase. Bioorg Med Chem Lett 2002, 12, 23, 3383. |
| 【2】 Chandrakumar, N.S.; Chen, B.B.; Clare, M.; Desai, B.N.; Djuric, S.W.; Docter, S.H.; Gasiecki, A.F.; Haack, R.A.; Liang, C.-D.; Miyashiro, J.M.; Penning, T.D.; Russell, M.A.; Yu, S.S. (Pfizer Inc.); LTA4 hydrolase inhibitor pharmaceutical compsns. and methods of use. JP 1998512542; WO 9610999 . |
| 【3】 Chandrakumar, N.S.; Chen, B.B.; Clare, M.; Desai, B.N.; Djuric, S.W.; Docter, S.H.; Gasiecki, A.; Haack, R.A.; Liang, C.-D.; Miyashiro, J.M.; Penning, T.D.; Russell, M.A.; Yu, S.S. (Pfizer Inc.); LTA4 hydrolase inhibitors. EP 0804427; EP 1221441; JP 1998512848; WO 9611192 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 50817 | 4-Hydroxydiphenylmethane; 4-Benzylphenol; alpha-Phenyl-p-cresol; p-Benzylphenol | 101-53-1 | C13H12O | 详情 | 详情 |
| (II) | 17430 | 2-Bromoacetic acid tert-butyl ester; tert-butyl 2-bromoacetate; tert-Butyl bromoacetate | 5292-43-3 | C6H11BrO2 | 详情 | 详情 |
| (III) | 64434 | tert-butyl 2-(4-benzylphenoxy)acetate | C19H22O3 | 详情 | 详情 | |
| (IV) | 64435 | 2-(4-benzylphenoxy)-1-ethanol | C15H16O2 | 详情 | 详情 | |
| (V) | 64436 | 2-(4-benzylphenoxy)ethyl 4-methylbenzenesulfonate | C22H22O4S | 详情 | 详情 | |
| (VI) | 17410 | Ethyl isonipecotate; ethyl 4-piperidinecarboxylate | 1126-09-6 | C8H15NO2 | 详情 | 详情 |