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【结 构 式】 
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【药物名称】Pimagedine, Aminoguanidine, YM-585, MDL-201228, GER-11(HCl) 【化学名称】Aminoguanidine 【CA登记号】79-17-4, 1937-19-5 (monoHCl) 【 分 子 式 】CH6N4 【 分 子 量 】74.08577 |
【开发单位】Alteon (Originator), Yamanouchi (Licensee) 【药理作用】Diabetic Nephropathy, Agents for, Diabetic Retinopathy, Agents for, ENDOCRINE DRUGS, Treatment of Diabetic Complications, AGE Inhibitors (Maillard's Reaction Inhibitors), Inducible Nitric Oxide Synthase (NOS-2) Inhibitors |
合成路线1
The synthesis of pimagedine was first reported more than 100 years ago. Several other preparative methods have since been described. However, the preferred method is the nitration of guanidine nitrate (I) with concentrated sulfuric acid giving nitroguanidine (II), which is then reduced with zinc dust in acetic acid. The title compound is isolated as the bicarbonate salt.
| 【1】 Nitroguanidine. Org Synth Coll 1967, 1, 399. |
| 【2】 Thiele, J.; Liebigs Ann Chem 1892, 270, 1. |
| 【3】 Anzelmi, E.; Smith, G.B.L.; J Am Chem Soc 1935, 57, 2730. |
| 【4】 Kurzer, F.; Godfrey, L.E.A.; Chem Ind 1962, 1584-95. |
| 【5】 Graul, A.; Castaner, J.; Prous, J.; Pimagedine. Drugs Fut 1994, 19, 8, 740. |
| 【6】 Aminoguanidine bicarbonate. Org Synth Coll 1967, 3, 73. |
合成路线2
The study of the pharmacological effects of pimagedine has required the synthesis of a radiolabeled derivative. [14C]-Pimagedine was synthesized by the reaction of hydrazine sulfate with barium [14C]-cyanamide in a one-step synthesis, and was conveniently isolated by crystallization as the bicarbonate salt.
| 【1】 Graul, A.; Castaner, J.; Prous, J.; Pimagedine. Drugs Fut 1994, 19, 8, 740. |
| 【2】 Lo, T.W.C.; Thornalley, P.J.; Synthesis of 14C-labelled aminoguanidine. J Label Compd Radiopharm 1994, 34, 2, 179-83. |