(1R,2R)-1-[(tert-butoxycarbonyl)amino]-2,3-dihydro-1H-inden-2-yl methanesulfonate | 766556-67-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (1R,2R)-1-[(tert-butoxycarbonyl)amino]-2,3-dihydro-1H-inden-2-yl methanesulfonate
• 英文别名: (1R, 2R)-methanesulfonic acid 1-tert-butoxycarbonylamino-indan-2-yl ester；(1R,2S)-1-[(1,1-dimethylethoxy)carbonylamino]-2-methanesulphonyloxyindan；Carbamic acid, [(1R,2R)-2,3-dihydro-2-[(methylsulfonyl)oxy]-1H-inden-1-yl]-, 1,1-dimethylethyl ester；[(1R,2R)-1-[(2-methylpropan-2-yl)oxycarbonylamino]-2,3-dihydro-1H-inden-2-yl] methanesulfonate
• CAS: 766556-67-6
• 化学式: C₁₅H₂₁NO₅S
• 分子量: 327.401
• InChiKey: CGXCOKLWNSZOMM-CHWSQXEVSA-N

物化性质

• 沸点：
  508.4±50.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  90.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R,2R)-1-[(tert-butoxycarbonyl)amino]-2,3-dihydro-1H-inden-2-yl methanesulfonate 在 palladium 10% on activated carbon sodium azide 、 氢气 作用下， 以 N,N-二甲基乙酰胺 、 乙酸乙酯 为溶剂， 反应 7.0h， 以98%的产率得到(1R,2R)-1-(BOC-氨基)-2-氨基二氢茚
  参考文献：
  名称：

  Bicyclic pyrrolyl amides as glucogen phosphorylase inhibitors

  摘要：

  杂环酰胺衍生物的化学式（I）：其中—X-Y-Z-选择自—S—CR4═CR5—，—CR4═CR5—S—，—O—CR4═CR5—，—CR4═CR5—O—，—N═CR4—S—，—S—CR4═N—，—NR6—CR4═CR5—和—CR4═CR5—NR6—；或其药学上可接受的盐或体内可水解酯；（附带条件）；具有糖原磷酸化酶抑制活性，因此在治疗与糖原磷酸化酶活性增加相关的疾病状态中具有价值。描述了制备所述杂环酰胺衍生物和含有它们的药物组合物的方法。

  公开号：

  US20030232875A1
• 作为产物：
  描述：

  [(1R,2S)-2-羟基-2,3-二氢-1H-茚-1-基]氨基甲酸叔丁酯 在 甲醇 、 sodium methylate 、 三乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 8.84h， 生成 (1R,2R)-1-[(tert-butoxycarbonyl)amino]-2,3-dihydro-1H-inden-2-yl methanesulfonate
  参考文献：
  名称：

  [EN] CYCLIC DIAMINES AND DERIVATIVES AS FACTOR XA INHIBITORS
  [FR] DIAMINES CYCLIQUES ET DERIVES COMME INHIBITEURS DU FACTEUR XA

  摘要：

  公开号：

  WO2005032490A3

文献信息

• [EN] LACTAM-CONTAINING CYCLIC DIAMINES AND DERIVATIVES AS FACTOR XA INHIBITORS<br/>[FR] DIAMINES CYCLIQUES CONTENANT DU LACTAME ET LEURS DERIVES UTILISES EN TANT QU'INHIBITEURS DU FACTEUR XA
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2004082687A1

  公开（公告）日：2004-09-30

  The present application describes lactam-containing cyclic diamines and derivatives thereof of Formula I: or pharmaceutically acceptable salt forms thereof, wherein M is a non-aromatic carbocycle or heterocycle. Compounds of the present invention are useful as inhibitors of trysin-like serine proteases, specifically factor Xa.

  本申请描述了含有内酰胺的环状二胺及其衍生物的化合物，化学式如下：或其药用可接受的盐形式，其中M是非芳香族碳环或杂环。本发明的化合物可用作特异性抑制try sin-like丝氨酸蛋白酶，特别是Xa因子。
• Lactam-containing cyclic diamines and derivatives as factor Xa inhibitors
  申请人：——

  公开号：US20040204454A1

  公开（公告）日：2004-10-14

  The present application describes lactam-containing cyclic diamines and derivatives thereof of Formula I: P 4 -M-M 4 I or pharmaceutically acceptable salt forms thereof, wherein M is a non-aromatic carbocycle or heterocycle. Compounds of the present invention are useful as inhibitors of trypsin-like serine proteases, specifically factor Xa.

  本申请描述了公式I：P4-M-M4I或其药学上可接受的盐形式的含有内酰胺的环状二胺及其衍生物，其中M是非芳香性碳环或杂环。本发明化合物可用作胰蛋白酶样丝氨酸蛋白酶的抑制剂，特别是因子Xa的抑制剂。
• LACTAM CONTAINING CYCLIC DIAMINES AND DERIVATIVES AS FACTOR XA INHIBITORS
  申请人：Qiao X Jennifer

  公开号：US20070135428A1

  公开（公告）日：2007-06-14

  The present application describes lactam-containing cyclic diamines and derivatives thereof of Formula I: P 4 -M-M 4 I or pharmaceutically acceptable salt forms thereof, wherein M is a non-aromatic carbocycle or heterocycle. Compounds of the present invention are useful as inhibitors of trypsin-like serine proteases, specifically factor Xa.

  本申请描述了公式I：P4-M-M4I或其药学上可接受的盐形式的含有内酰胺的环状二胺及其衍生物，其中M为非芳香族碳环或杂环。本发明的化合物可用作胰蛋白酶样丝氨酸蛋白酶的抑制剂，特别是Xa因子的抑制剂。
• Identification and Pharmacological Profile of an Indane Based Series of Ghrelin Receptor Full Agonists
  作者：Cristina Gardelli、Hiroki Wada、Asim Ray、Moya Caffrey、Antonio Llinas、Igor Shamovsky、Joakim Tholander、Joakim Larsson、Ulf Sivars、Leif Hultin、Ulf Andersson、Hitesh J. Sanganee、Kristina Stenvall、Brith Leidvik、Karin Gedda、Lisa Jinton、Marie Rydén Landergren、Kostas Karabelas

  DOI：10.1021/acs.jmedchem.8b00322

  日期：2018.7.26

  Cachexia and muscle wasting are very common among patients suffering from cancer, chronic obstructive pulmonary disease, and other chronic diseases. Ghrelin stimulates growth hormone secretion via the ghrelin receptor, which subsequently leads to increase of IGF-1 plasma levels. The activation of the GH/IGF-1 axis leads to an increase of muscle mass and functional capacity. Ghrelin further acts on inflammation, appetite, and adipogenesis and for this reason was considered an important target to address catabolic conditions. We report the synthesis and properties of an indane based series of ghrelin receptor full agonists; they have been shown to generate a sustained increase of IGF-1 levels in dog and have been thoroughly investigated with respect to their functional activity.
• Enantiopure five-membered cyclicdiamine derivatives as potent and selective inhibitors of factor Xa. Improving in vitro metabolic stability via core modifications
  作者：Jennifer X. Qiao、Tammy C. Wang、Gren Z. Wang、Daniel L. Cheney、Kan He、Alan R. Rendina、Baomin Xin、Joseph M. Luettgen、Robert M. Knabb、Ruth R. Wexler、Patrick Y.S. Lam

  DOI：10.1016/j.bmcl.2007.07.020

  日期：2007.9

  We previously reported a series of enantiopure cis-(1 R,2S)-cyclopentyldiamine derivatives as potent and selective inhibitors of Factor Xa (FXa). Herein, we describe our approach to improve the metabolic stability of this series via core modifications. Multiple resulting series of compounds demonstrated similarly high FXa potency and improved metabolic stability in human liver microsomes compared with the cyclopentyldiamide 1. (3R,4S)-Pyrrolidinyldiamide 31 was the best overall compound with human FXa K; of 0.50 nM, PT EC2x of 2.1 mu M in human plasma, bioavailability of 25% and t z of 2.7 h in dogs. Further biochemical characterization of compound 31 is also presented. (c) 2007 Elsevier Ltd. All rights reserved.