4-[(aminothioxomethyl)amino]-1-piperidinecarboxylic acid ethyl ester | 294622-57-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 4-[(aminothioxomethyl)amino]-1-piperidinecarboxylic acid ethyl ester
• 英文别名: ethyl 4-thioureidopiperidine-1-carboxylate；Ethyl 4-(carbamothioylamino)piperidine-1-carboxylate
• CAS: 294622-57-4
• 化学式: C₉H₁₇N₃O₂S
• mdl: MFCD09932791
• 分子量: 231.319
• InChiKey: BPCZINMJOTUUOC-UHFFFAOYSA-N

物化性质

• 沸点：
  360.5±52.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.777
• 拓扑面积：
  99.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-[(aminothioxomethyl)amino]-1-piperidinecarboxylic acid ethyl ester 在 水 、 氢溴酸 作用下， 反应 2.0h， 以47%的产率得到piperidin-4-ylthiourea;hydrobromide
  参考文献：
  名称：

  [EN] DIMERIC COMPOUNDS OF PIPERIDINE, PIPERAZINE OR MORPHOLINE OR THEIR 7-MEMBERED ANALOGS SUITABALE FOR THE TREATMENT OF NEURODEGENERATIVE DISORDERS
  [FR] COMPOSES DIMERES DE PIPERIDINE, PIPERAZINE OU MORPHOLINE OU LEURS PRODUITS ANALOGUES A 7 ELEMENTS, DESTINES AU TRAITEMENT DE MALADIES NEURODEGENERATIVES

  摘要：

  公式(I'')，N-氧化物形式，药用可接受的增加盐和它们的立体化学异构形式。

  公开号：

  WO2006008259A1
• 作为产物：
  描述：

  硫光气 、 4-氨基-1-哌啶甲酸乙酯 在 三乙胺 、 氨 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 16.0h， 生成 4-[(aminothioxomethyl)amino]-1-piperidinecarboxylic acid ethyl ester
  参考文献：
  名称：

  Design and Synthesis of Tri-Ring P₃ Benzamide-Containing Aminonitriles as Potent, Selective, Orally Effective Inhibitors of Cathepsin K

  摘要：

  We have prepared a series of achiral aminoacetonitriles, bearing tri-ring benzamide moieties and an aminocyclohexanecarboxylate residue at P-2. This combination of binding elements resulted in sub-250 pM, reversible, selective, and orally bioavailable cathepsin K inhibitors. Lead compounds displayed single digit nanomolar inhibition in vitro (of rabbit osteoclast-mediated degradation of bovine bone). The best compound in this series, 39n (CRA-013783/ L-006235), was orally bioavailable in rats, with a terminal half-life of over 3 h. 39n was dosed orally in ovariectomized rhesus monkeys once per day for 7 days. Collagen breakdown products were reduced by up to 76% dose-dependently. Plasma concentrations of 39n above the bone resorption IC50 after 24 h indicated a correlation between functional cellular and in vivo assays. Inhibition of collagen breakdown by cathepsin K inhibitors suggests this mechanism of action may be useful in osteoporosis and other indications involving bone resorption.

  DOI：

  10.1021/jm058198r

文献信息

• Novel compounds and compositions as protease inhibitors
  申请人：AXYS PHARMACEUTICALS, INC.

  公开号：US20020086996A1

  公开（公告）日：2002-07-04

  The present invention relates to novel N-cyanomethyl amides which are cysteine protease inhibitors, the pharmaceutically acceptable salts and N-oxides thereof, their uses as therapeutic agents and the methods of their making.

  本发明涉及一种新颖的N-氰甲基酰胺，它们是半胱氨酸蛋白酶抑制剂，以及它们的药用盐和N-氧化物，它们作为治疗剂的用途以及它们的制备方法。
• Compounds and compositions as protease inhibitors
  申请人：Axys Pharmaceuticals, Inc.

  公开号：US06593327B2

  公开（公告）日：2003-07-15

  The present invention relates to novel N-cyanomethyl amides which are cysteine protease inhibitors, the pharmaceutically acceptable salts and N-oxides thereof, their uses as therapeutic agents and the methods of their making.

  本发明涉及一种新型N-氰甲基酰胺，它们是半胱氨酸蛋白酶抑制剂，其药学上可接受的盐和N-氧化物，以及它们作为治疗剂的用途和制备方法。
• N-CYANOMETHYLAMIDES AS PROTEASE INHIBITORS
  申请人：AXYS PHARMACEUTICALS, INC.

  公开号：EP1161415B1

  公开（公告）日：2005-07-13
• US6476026B1
  申请人：——

  公开号：US6476026B1

  公开（公告）日：2002-11-05
• US6593327B2
  申请人：——

  公开号：US6593327B2

  公开（公告）日：2003-07-15