1-(tert-butoxycarbonyl)-4-(6-chloronaphthalene-2-sulfonyl)piperazine | 216866-88-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(tert-butoxycarbonyl)-4-(6-chloronaphthalene-2-sulfonyl)piperazine
• 英文别名: 1-Boc-4-(6-chloro-naphthalen-2-ylsulfonyl)piperazine；1-Boc-4-(6-chloronaphthalen-2-ylsulfonyl)piperazine；tert-butyl 4-(6-chloronaphthalen-2-yl)sulfonylpiperazine-1-carboxylate
• CAS: 216866-88-5
• 化学式: C₁₉H₂₃ClN₂O₄S
• 分子量: 410.922
• InChiKey: CDLPHFUPNOKOCX-UHFFFAOYSA-N

物化性质

• 沸点：
  556.8±60.0 °C(Predicted)
• 密度：
  1.329±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  75.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(tert-butoxycarbonyl)-4-(6-chloronaphthalene-2-sulfonyl)piperazine 在 盐酸 、 正丁基锂 、 溶剂黄146 、 三乙胺 作用下， 以 乙醚 、 乙醇 、 二氯甲烷 为溶剂， 生成 [4-(6-Chloro-naphthalene-2-sulfonyl)-piperazin-1-yl]-(5-methyl-4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridin-2-yl)-methanone
  参考文献：
  名称：

  Orally active factor Xa inhibitors: 4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine derivatives

  摘要：

  In our investigation of factor Xa inhibitors, a series of 1-(6-chloronaphthalen-2-yl)sulfonyl-4-(4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carbonyl)piperazines 3a-i were synthesized. In vitro inhibitory activities of the compounds against factor Xa and coagulation are summarized. Among the compounds, 3c and 3d, possessing a carbamoyl or N-methylcarbamoyl moiety, showed potent inhibitory activities when administered orally to rats. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.03.036
• 作为产物：
  描述：

  2-氯萘 在 氯化亚砜 、 硫酸 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.75h， 生成 1-(tert-butoxycarbonyl)-4-(6-chloronaphthalene-2-sulfonyl)piperazine
  参考文献：
  名称：

  Design, synthesis, and biological activity of non-basic compounds as factor Xa inhibitors: SAR study of S1 and aryl binding sites

  摘要：

  Compound 7 was identified as the active metabolite of 6 by HPLC and mass spectral analysis. Modification of lead compound 7 by transformation of its N-oxide 6-6 biaryl ring system and fused aromatics produced a series of non-basic fxa inhibitors with excellent potency in anti-fXa and anticoagulant assays. The optimized compounds 73b and 75b showed sub to one digit micromolar anticoagulant activity (PTCT2). Particularly, anti-fXa activity was detected in plasma of rats orally administered with 1 mg/kg of compound 75b. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.04.006

文献信息

• Sulfonamide derivatives, their production and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US06359134B1

  公开（公告）日：2002-03-19

  The present invention provides compounds which specifically inhibit FXa, which are effective when orally administered and which are useful as a safe medicine for the prevention or treatment of diseases caused by thrombus or infarction. Compounds of this invention are piperazinones of the formula: wherein R1 is an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group; the ring A is an optionally substituted divalent nitrogen-containing heterocyclic group, in addition to being substituted by the group of the formula: and the group of the formula: Y is an optionally substituted divalent hydrocarbon group or an optionally substituted divalent heterocyclic group; X is a direct bond or an optionally substituted alkylene chain; Z is (1) an amino group substituted with an optionally substituted hydrocarbon group, (2) an optionally substituted imino group or (3) an optionally substituted nitrogen-containing heterocyclic group; provided that when X is a direct bond and Z is an optionally substituted 6-membered nitrogen-containing aromatic heterocyclic group, Y is an optionally substituted divalent hydrocarbon group or an optionally substituted divalent unsaturated heterocyclic group; or a salt thereof.

  本发明提供了一种化合物，该化合物特异性地抑制FXa，口服给药有效，并且用作预防或治疗由血栓或梗死引起的疾病的药物是安全的。本发明的化合物是哌嗪酮的公式： 其中R1是可选地取代的烃基或可选地取代的杂环基；环A是除了被公式：的基团取代的之外的可选地取代的二价含氮杂环基： 和公式的基团： Y是可选地取代的二价烃基或可选地取代的二价杂环基；X是直接键或可选地取代的亚烷基链；Z是（1）与可选地取代的烃基取代的氨基，（2）可选地取代的亚氨基或（3）可选地取代的含氮杂环基；当X是直接键并且Z是可选地取代的6-成员含氮芳香杂环基时，Y是可选地取代的二价烃基或可选地取代的二价不饱和杂环基；或其盐。
• Heterocyclic amides as inhibitors of factor Xa
  申请人：Eli Lilly and Company

  公开号：US06660739B1

  公开（公告）日：2003-12-09

  This application relates to a compound of formula I (or a pharmaceutically acceptable salt thereof) as defined herein, pharmaceutical compositions thereof, and its use as an inhibitor of factor Xa, as well as a process for its preparation and intermediates therefor.

  本申请涉及公式I的化合物（或其药用可接受的盐），其药物组合物，以及其作为Xa因子抑制剂的用途，以及其制备过程和中间体。
• Substituted heterocyclic amides
  申请人：——

  公开号：US20040097491A1

  公开（公告）日：2004-05-20

  This application relates to a compound of formula (I) (or a pharmaceutically acceptable salt thereof) as defined herein, pharmaceutical compositions thereof, and its use as an inhibitor of factor Xa, as well as a process for its preparation and intermediates therefor.

  该申请涉及到式（I）的化合物（或其药用可接受的盐），如本文所定义，其药物组成，以及其作为因子Xa抑制剂的用途，以及其制备方法和中间体。
• Orally active factor Xa inhibitors: 4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine derivatives
  作者：Noriyasu Haginoya、Syozo Kobayashi、Satoshi Komoriya、Yumiko Hirokawa、Taketoshi Furugori、Takayasu Nagahara

  DOI：10.1016/j.bmcl.2004.03.036

  日期：2004.6

  In our investigation of factor Xa inhibitors, a series of 1-(6-chloronaphthalen-2-yl)sulfonyl-4-(4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carbonyl)piperazines 3a-i were synthesized. In vitro inhibitory activities of the compounds against factor Xa and coagulation are summarized. Among the compounds, 3c and 3d, possessing a carbamoyl or N-methylcarbamoyl moiety, showed potent inhibitory activities when administered orally to rats. (C) 2004 Elsevier Ltd. All rights reserved.
• SULFONAMIDE DERIVATIVES, THEIR PRODUCTION AND USE
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0986551A1

  公开（公告）日：2000-03-22