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【结 构 式】 
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【药物名称】Talnetant, SB-223412 【化学名称】(-)-3-Hydroxy-2-phenyl-N-[1(S)-phenylpropyl]quinoline-4-carboxamide 【CA登记号】174636-32-9, 174636-33-0 ((R)-isomer), 204519-66-4 (monoHCl), 174636-26-1 (undefined isomer) 【 分 子 式 】C25H22N2O2 【 分 子 量 】382.46629 |
【开发单位】GlaxoSmithKline (Originator) 【药理作用】Antipsychotic Drugs, Antitussives, Chronic Obstructive Pulmonary Diseases (COPD), Treatment of, GASTROINTESTINAL DRUGS, Irritable Bowel Syndrome, Agents for, PSYCHOPHARMACOLOGIC DRUGS, RENAL-UROLOGIC DRUGS, RESPIRATORY DRUGS, Treatment of Upper Respiratory Tract Disorders, Urinary Incontinence Therapy, Tachykinin NK3 Antagonists |
合成路线1
Condensation of isatin (I) with 2-methoxyacetophenone (II) in the presence of KOH afforded quinolinecarboxylic acid (III). Subsequent demethylation of the ether function of (III) with refluxing 57% HI gave (IV), which was then condensed with (S)-1-phenylpropyl amine (V) using DCC and HOBt to yield the title amide.
| 【1】 Giardina, G.A.M.; et al.; Discovery of a novel class of selective non-peptid. J Med Chem 1999, 42, 6, 1053. |
| 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) | 14098 | 2,3-Indolinedione; 1H-Indole-2,3-dione; Isatin | 91-56-5 | C8H5NO2 | 详情 | 详情 |
| (II) | 23641 | 2-methoxy-1-phenyl-1-ethanone | 4079-52-1 | C9H10O2 | 详情 | 详情 |
| (III) | 23642 | 3-methoxy-2-phenyl-4-quinolinecarboxylic acid | C17H13NO3 | 详情 | 详情 | |
| (IV) | 23643 | 3-hydroxy-2-phenyl-4-quinolinecarboxylic acid | 485-89-2 | C16H11NO3 | 详情 | 详情 |
| (V) | 23644 | (1S)-1-phenylpropylamine; (1S)-1-phenyl-1-propanamine | 3789-59-1 | C9H13N | 详情 | 详情 |