(-)-7-[(6-chloro-2-naphthalenyl)sulfonyl]tetrahydro-8a-(methoxymethyl)-1'-(4-pydidinyl)-spiro[5H-oxazolo[3,2-a]pyrazine-2(3H),4'-piperidin]-5-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (-)-7-[(6-chloro-2-naphthalenyl)sulfonyl]tetrahydro-8a-(methoxymethyl)-1'-(4-pydidinyl)-spiro[5H-oxazolo[3,2-a]pyrazine-2(3H),4'-piperidin]-5-one
• 英文别名: (-)-7-[(6-chloro-2-naphthalenyl)sulfonyl]tetrahydro-8a-(methoxymethyl)-1'-(4-pyridinyl)-spiro[5H-oxazolo[3,2-a]pyrazine-2(3H),4'-piperidin]-5-one；M55529；(-)-1,4-diaza-4-(6-chloronaphtalen-2-ylsulfonyl)-6-(methoxymethyl)-7-oxa-1'-(4-pyridyl)spiro[bicyclo[4.3.0]nonane-8,4'-piperidin]-2-one；7-(6-chloronaphthalen-2-yl)sulfonyl-8a-(methoxymethyl)-1'-pyridin-4-ylspiro[6,8-dihydro-3H-[1,3]oxazolo[3,2-a]pyrazine-2,4'-piperidine]-5-one
• 化学式: C₂₇H₂₉ClN₄O₅S
• 分子量: 557.07
• InChiKey: OCCGRNQFQCNISA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  38
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (-)-7-[(6-chloro-2-naphthalenyl)sulfonyl]tetrahydro-8a-(methoxymethyl)-1'-(4-pydidinyl)-spiro[5H-oxazolo[3,2-a]pyrazine-2(3H),4'-piperidin]-5-one 在 盐酸 、 palladium 10% on activated carbon 、 氢气 作用下， 以84.1 mg的产率得到(-)-1,4-diaza-6-(methoxymethyl)-4-(2-naphthalenesulfonyl)-7-oxa-1'-(4-pyridyl)spiro[bicyclo[4.3.0]nonane-8,4'-piperidin]-2-one
  参考文献：
  名称：

  TRICYCLIC COMPOUNDS HAVING SPIRO UNION

  摘要：

  公开号：

  EP1191028B1
• 作为产物：
  描述：

  4-(氨基甲基)-1-苄基哌啶-4-醇 在 lithium hydroxide 、 1-氯乙基氯甲酸酯 、 (aS,RR)-salen-manganese 、 1,8-双二甲氨基萘 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 125.33h， 生成 (-)-7-[(6-chloro-2-naphthalenyl)sulfonyl]tetrahydro-8a-(methoxymethyl)-1'-(4-pydidinyl)-spiro[5H-oxazolo[3,2-a]pyrazine-2(3H),4'-piperidin]-5-one
  参考文献：
  名称：

  抗血栓剂 M55529 的不对称合成：第一个对映选择性环状 N,O-缩醛形成

  摘要：

  报道了抗血栓剂 M55529 的第一个不对称合成，其中阐明了第一个对映选择性环状 N,O-缩醛的形成。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

  DOI：

  10.1002/ejoc.200600124

文献信息

• SUBSTITUTED OXAZOLIDINONES AND THEIR USE
  申请人：Allerheiligen Swen

  公开号：US20100261759A1

  公开（公告）日：2010-10-14

  The invention relates to novel substituted oxazolidinones, to processes for their preparation, to their use for the treatment and/or prophylaxis of diseases and their use for preparing medicaments for the treatment and/or prophylaxis of diseases, in particular of thromboembolic disorders.

  这项发明涉及新型取代氧唑烷酮，其制备方法，其用于治疗和/或预防疾病以及用于制备用于治疗和/或预防疾病，特别是血栓栓塞性疾病的药物。
• 2-(HETEROARYL) ALKYL INDAZOLE 6-PHENYL AND THIENYL METHYL AMIDE AS THROMBIN INHIBITORS
  申请人：Siegel Stephan

  公开号：US20100105663A1

  公开（公告）日：2010-04-29

  The invention relates to substituted indazoles and methods for production thereof and use thereof for the production of medicinal products for the treatment and/or prophylaxis of diseases, especially of cardiovascular diseases, preferably of thromboembolic diseases.

  该发明涉及取代吲唑并且生产方法以及用于制备治疗和/或预防疾病的药物的用途，特别是心血管疾病，最好是血栓栓塞疾病。
• Synthesis and Evaluation of 1-Arylsulfonyl-3-piperazinone Derivatives as Factor Xa Inhibitors IV. A Series of New Derivatives Containing a Spiro[5H-oxazolo[3,2-a]pyrazine-2(3H),4'-piperidin]-5-one Skeleton
  作者：Hidemitsu Nishida、Takafumi Mukaihira、Fumihiko Saitoh、Kousuke Harada、Miyuki Fukui、Tomokazu Matsusue、Atsushi Okamoto、Yoshitaka Hosaka、Miwa Matsumoto、Ikuya Shiromizu、Shuhei Ohnishi、Hidenori Mochizuki

  DOI：10.1248/cpb.52.406

  日期：——

  of factor Xa (FXa) inhibitor in an investigation involving the synthesis of 1-arylsulfonyl-3-piperazinone derivatives, we found new compounds containing a unique spiro skeleton. Among such compounds, (-)-7-[(6-chloro-2-naphthalenyl)sulfonyl]tetrahydro-8a-(methoxymethyl)-1'-(4-pyridinyl)-spiro[5H-oxazolo[3,2-a]pyrazine-2(3H),4'-piperidin]-5-one (28, M55529) had activity more favorable than those of previously

  在涉及合成1-芳基磺酰基-3-哌嗪酮衍生物的研究中，在开发Xa因子（FXa）抑制剂的过程中，我们发现了含有独特螺旋骨架的新化合物。在这些化合物中，（-）-7-[（6-氯-2-萘基）磺酰基]四氢-8a-（甲氧基甲基）-1'-（4-吡啶基）-螺[5H-恶唑并[3,2-a] ] pyrazine-2（3H），4'-piperidin] -5-one（28，M55529）的活性比以前报道的化合物更好。M55529对FXa的抑制活性为IC（50）= 2 nM，对FXa的选择性比凝血酶和胰蛋白酶高。
• Tricyclic compound having spiro union
  申请人：——

  公开号：US20030045520A1

  公开（公告）日：2003-03-06

  This invention relates to tricyclic compounds having spiro union represented by the following formula (I) or its salt which is useful as a drug, and in particular, as an inhibitor for activated blood coagulation factor X, which can be administered orally and which exhibits strong anticoagulation action. 1 The invention also relates to a pharmacophore which was derived from the compound and is useful in molecular designing of the FXa inhibitor.

  本发明涉及具有以下式（I）所表示的螺联结的三环化合物或其盐，该化合物可用作药物，特别是作为激活的血液凝血因子X的抑制剂，可经口给药，具有强烈的抗凝作用。该发明还涉及从该化合物衍生的药效团，可用于FXa抑制剂的分子设计。
• Cholesterol biosynthesis inhibitors containing as the active ingredient tricyclic spiro compounds
  申请人：——

  公开号：US20040063716A1

  公开（公告）日：2004-04-01

  This invention relates to tricyclic compounds having spiro union represented by the following formula (I) or its salt which is useful as a drug, and in particular, as an inhibitor for activated blood coagulation factor X, which can be administered orally and which exhibits strong anticoagulation action. 1 The invention also relates to a pharmacophore which was derived from the compound and is useful in molecular designing of the FXa inhibitor.

  本发明涉及具有spiro联合的三环化合物，其表示为以下公式(I)或其盐，可用作药物，特别是作为口服给药的激活血液凝血因子X的抑制剂，具有强烈的抗凝作用。此外，本发明还涉及从该化合物衍生的药效团，可用于FXa抑制剂的分子设计。