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【结 构 式】 
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【药物名称】Cimadronate sodium, Incadronic acid sodium salt, YM-175, YM-21175-1, Bisphonal 【化学名称】Cycloheptylaminomethylenedi(phosphonic acid) disodium salt 【CA登记号】138330-18-4, 124351-85-5 (free acid), 157432-63-8 (Mg salt), 183808-97-1 (monohydrate), 157432-62-7 (Zn salt) 【 分 子 式 】C8H17NNa2O6P2 【 分 子 量 】331.15499 |
【开发单位】Yamanouchi (Originator) 【药理作用】Bone Diseases, Treatment of, Bone Resorption Inhibitors, Dental Agents, METABOLIC DRUGS, Treatment of Hypercalcemia, Treatment of Osteoporosis, Treatment of Periodontitis, Bisphosphonates |
合成路线1
The reaction of cycloheptylamine (I) with triethyl orthoformate (II) and diethyl phosphite (III) at 150 gives cycloheptylaminomethylenediphosphonic acid tetraethyl ester (IV), which is then hydrolyzed with refluxing concentrated hydrochloric acid.
| 【1】 Isomura, Y.; Takeuchi, M.; Sakamoto, S.; Abe, T. (Yamanouchi Pharmaceutical Co., Ltd.); (Cycloalkylamino)methylenebisphosphonic acids and medicines containing them. AU 8928670; EP 0325482; JP 1989308290; US 5041428 . |
| 【2】 Takeuchi, M.; Sakamoto, S.; Kawamuki, K.; Kudo, M.; Murase, K.; Kawashima, H.; Isomura, Y.; Synthesis and structure-activity relationships of a novel anti-resorptive agent YM175, and the related derivatives. Symp Med Chem 1990, P-12. |
| 【3】 Prous, J.; Castaner, J.; YM-175. Drugs Fut 1992, 17, 4, 293. |
| 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) | 22234 | cycloheptanamine; cycloheptylamine | 5452-35-7 | C7H15N | 详情 | 详情 |
| (II) | 21304 | Triethyl orthoformate; 1-(Diethoxymethoxy)ethane; Diethoxymethyl ethyl ether | 122-51-0 | C7H16O3 | 详情 | 详情 |
| (III) | 12714 | diethyl phosphonate; diethyl phosphite | 762-04-9 | C4H11O3P | 详情 | 详情 |
| (IV) | 31262 | diethyl [bis(2-hydroxyethyl)phosphoryl](cycloheptylamino)methylphosphonate | C16H35NO6P2 | 详情 | 详情 |