Piroximole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: Piroximole
• 英文别名: 4-Ethyl-1,3-dihydro-5-[hydroxy(pyridin-4-yl)methyl]-2H-imidazol-2-one；4-Ethyl-1,3-dihydro-5-[hydroxy(4-pyridyl)methyl]-2H-imidazol-2-one；4-ethyl-5-[hydroxy(pyridin-4-yl)methyl]-1,3-dihydroimidazol-2-one
• 化学式: C₁₁H₁₃N₃O₂
• 分子量: 219.243
• InChiKey: FKIJSRNALKPKMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  74.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Piroximole 以72的产率得到匹罗昔酮
  参考文献：
  名称：

  Preparation of 1,3-dihydro-4-pyridoyl-2H-imidazol-2-ones

  摘要：

  1,3-二氢-4-吡啶酰基-2H-咪唑-2-酮的制备过程分为三步：(a)将1-吡啶基-1,3-去羰基-2-氧代脂肪烷还原，得到1-吡啶基-1-羟基-2-胺基-3-酮基脂肪烷；(b)将所得的羟胺酮与氰酸根离子反应，制得1,3-二氢-4-羟基(吡啶基)甲基-2H-咪唑-2-酮；(c)将所得的羟甲基化合物氧化，得到所需的产物。

  公开号：

  US04803278A1
• 作为产物：
  描述：

  1-(pyridin-4-yl)-1-hydroxy-2-amino-3-ketopentane 生成 Piroximole
  参考文献：
  名称：

  Preparation of 1,3-dihydro-4-pyridoyl-2H-imidazol-2-ones

  摘要：

  1,3-二氢-4-吡啶酰基-2H-咪唑-2-酮的制备过程分为三步：(a)将1-吡啶基-1,3-去羰基-2-氧代脂肪烷还原，得到1-吡啶基-1-羟基-2-胺基-3-酮基脂肪烷；(b)将所得的羟胺酮与氰酸根离子反应，制得1,3-二氢-4-羟基(吡啶基)甲基-2H-咪唑-2-酮；(c)将所得的羟甲基化合物氧化，得到所需的产物。

  公开号：

  US04803278A1

文献信息

• Preparation of 1,3-dihydro-4-pyridoyl-2H-imidazol-2-ones
  申请人：Merrell Dow Pharmaceuticals, Inc.

  公开号：US04803278A1

  公开（公告）日：1989-02-07

  1,3-Dihydro-4-pyridoyl-2H-imidazol-2-ones are prepared in a three step process by (a) reducing 1-pyridyl-1,3-deketo-2-oximinoalkanes to produce 1-pyridyl-1-hydroxy-2-amine-3-ketoalkanes; (b) reacting the thus produced hydroxyaminoketone with cyanate ion to produce a 1,3-dihydro-4-hydroxy(pyridyl)methyl-2H-imidazol-2-one; and (c) oxidizing the thus produced hydroxymethyl compound to yield the desired product.

  1,3-二氢-4-吡啶酰基-2H-咪唑-2-酮的制备过程分为三步：(a)将1-吡啶基-1,3-去羰基-2-氧代脂肪烷还原，得到1-吡啶基-1-羟基-2-胺基-3-酮基脂肪烷；(b)将所得的羟胺酮与氰酸根离子反应，制得1,3-二氢-4-羟基(吡啶基)甲基-2H-咪唑-2-酮；(c)将所得的羟甲基化合物氧化，得到所需的产物。
• The preparation of 1,3-Dihydro-4-pyridoyl-2H-imidazol-2-ones
  申请人：MERRELL DOW PHARMACEUTICALS INC.

  公开号：EP0170214A1

  公开（公告）日：1986-02-05

  1,3-Dihydro-4-pyridoyl-2H-imidazol-2-ones are prepared in a three step process by a) reducing 1-pyridyl-1,3-deketo-2-oximinoalkanes to produce 1-pyridyl-1-hydroxy-2-amine-3-ketoalkanes; b) reacting the thus produced hydroxyaminoketone with cyanate ion to produce a 1,3-dihydro-4-hydroxy(pyridyl)-methyl-2H-imidazol-2-one; and c) oxidizing the thus produced hydroxymethyl compound to yield the desired product.

  1,3-二氢-4-吡啶酰基-2H-咪唑-2-酮通过以下三步法制备而成 a) 还原 1-吡啶基-1,3-脱酮-2-氧亚氨基烷，生成 1-吡啶基-1-羟基-2-氨基-3-酮； b) 将生成的羟基氨基酮与氰酸根离子反应，生成 1,3-二氢-4-羟基(吡啶基)-甲基-2H-咪唑-2-酮；以及 c) 氧化由此生成的羟甲基化合物，得到所需的产品。
• Metabolism and pharmacokinetics of the cardiotonic agent piroximone and of its major metabolite in dog
  作者：M. Berg-Candolfi、B. Dulery、F. Jehl、K. D. Haegele

  DOI：10.3109/00498259509061833

  日期：1995.1

  1. Piroximone was administered orally (p.o.) and intravenously (i.v.) to male Beagle dog. In vitro, piroximone was incubated with dog liver microsomes.2. Piroximone was metabolized in vivo to five metabolites (1-5) representing approximately 20% of the total administered dose.3. The parent drug and its metabolites were totally eliminated in urine.4. Reduced piroximone (piroximole), representing approximately 10% of the administered dose, was identified as the major metabolic product in vivo.5. In vitro, piroximone was metabolized by dog liver microsomes to isonicotinic acid (1) and piroximole (4), with the same ratio as in vivo (1:4 = 0.2). The Michaelis-Menten parameters were determined for piroximole formation and were: K-m app = 733 mu M and V-max app = 232 pmol/mg protein/min.6. Comparison of the pharmacokinetics of piroximone and piroximole revealed that both compounds were very well absorbed (F = 93 +/- 7 and 89 +/- 8% respectively), slightly distributed (V-dapp = 0.78 +/- 0.04 and 1.02 +/- 0.09 1/kg p.o., and 0.95 +/- 0.05 and 0.76 +/- 0.13 1/kg i.v. respectively) and excreted into urine to the same extent (U-Ex = 54.7 +/- 1.2 and 53.2 +/- 12.6% p.o., and 59.1 +/- 5.3 and 51.2 +/- 5.7% i.v. respectively), except that the clearance of piroximone was two-fold higher than that observed for piroximole (Cl-T = 7.77 +/- 1.35 and 4.12 +/- 0.44 ml/min/kg p.o., and 7.68 +/- 1.25 and 4.06 +/- 0.51 ml/min/kg i.v. respectively).
• SCHNETTLER, RICHARD A.;KING, CHI-HSIN R.
  作者：SCHNETTLER, RICHARD A.、KING, CHI-HSIN R.

  DOI：——

  日期：——
• US4803278A
  申请人：——

  公开号：US4803278A

  公开（公告）日：1989-02-07