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【结 构 式】 
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【药物名称】Pilocarpine hydrochloride, KSS-694, MGI-647, Pilobuc, Pilocar, Isopto carpine, Spersacarpin, Pilo, Isopto-pilocarpine, Pilocarpina lux, Pilogel, PilaSite(sustained release), Salagen, Pilopine HS 【化学名称】(3S-cis)-3-Ethyldihydro-4-[(1-methyl-1H-imidazol-5-yl)methyl]-2(3H)-furanone monohydrochloride 【CA登记号】54-71-7, 92-13-7 (free base), 148-72-1 (mononitrate) 【 分 子 式 】C11H17ClN2O2 【 分 子 量 】244.72334 |
【开发单位】Antiglaucoma Agents, Dry Eye Syndrome, Treatment for, OCULAR MEDICATIONS, ONCOLYTIC DRUGS, Ophthalmic Drugs, Other Ocular Medications, Radioprotectants, Sjogren's Syndrome, Agents for, TREATMENT OF MUSCULOSKELETAL & CONNECTIVE TISSUE DISEASES, Treatment of Other Autoimmune Disorders, Muscarinic Agonists 【药理作用】Antiglaucoma Agents, Dry Eye Syndrome, Treatment for, OCULAR MEDICATIONS, ONCOLYTIC DRUGS, Ophthalmic Drugs, Other Ocular Medications, Radioprotectants, Sjogren's Syndrome, Agents for, TREATMENT OF MUSCULOSKELETAL & CONNECTIVE TISSUE DISEASES, Treatment of Other Autoimmune Disorders, Muscarinic Agonists |
合成路线1
The alkylation of pilosine (I) with ethyl chloride (II) by means of LDA in THF gives trans-pilocarpine (III), which is isomerized with LDA in THF, yielding a mixture of cis- and trans-pilocarpine (IV). Finally, this mixture is resolved by crystallization with di-p-toluoyl tartaric acid.
| 【1】 Shapiro, G.; Enz, A.; Pilocarpine analogs as muscarinic agonists. Drugs Fut 1992, 17, 6, 489. |
| 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) | 42933 | (4R)-4-[(1-methyl-1H-imidazol-5-yl)methyl]dihydro-2(3H)-furanone | C9H12N2O2 | 详情 | 详情 | |
| (II) | 42926 | 1-chloroethane | 75-00-3 | C2H5Cl | 详情 | 详情 |
| (III) | 42934 | (3R,4R)-3-ethyl-4-[(1-methyl-1H-imidazol-5-yl)methyl]dihydro-2(3H)-furanone | C11H16N2O2 | 详情 | 详情 | |
| (IV) | 42935 | (4R)-3-ethyl-4-[(1-methyl-1H-imidazol-5-yl)methyl]dihydro-2(3H)-furanone | C11H16N2O2 | 详情 | 详情 |