8,9-二氯-1-甲基-2,3,4,5-四氢-1H-3-苯并氮杂卓 | 824430-71-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 中文名称: 8,9-二氯-1-甲基-2,3,4,5-四氢-1H-3-苯并氮杂卓
• 英文名称: (1R,S)-8,9-dichloro-2,3,4,5-tetrahydro-1-methyl-1H-3-benzazepine
• 英文别名: 8,9-dichloro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine；(R,S)-8,9-dichloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine；6,7-dichloro-5-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine
• CAS: 824430-71-9
• 化学式: C₁₁H₁₃Cl₂N
• 分子量: 230.137
• InChiKey: VUYGFWKOVMRUIC-UHFFFAOYSA-N

物化性质

• 沸点：
  308.0±42.0 °C(Predicted)
• 密度：
  1.186±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  8,9-二氯-1-甲基-2,3,4,5-四氢-1H-3-苯并氮杂卓 生成 (S)-8,9-dichloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine 、 (R)-8,9-dichloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine
  参考文献：
  名称：

  Discovery and SAR of new benzazepines as potent and selective 5-HT2C receptor agonists for the treatment of obesity

  摘要：

  We report on the synthesis, biological evaluation and structure-activity relationships for a series of 3-benzazepine derivatives as 5-HT2C receptor agonists. The compounds were evaluated in functional assays measuring [H-3] phosphoinositol turnover in HEK-293 cells transiently transfected with h5-HT2C, h5-HT2A or h5-HT2B receptors. Several compounds are shown to be potent and selective 5-HT2C receptor agonists, which decrease food intake in a rat feeding model. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.080
• 作为产物：
  描述：

  3,4-二氯苯乙胺 在 吡啶 、 三氯化铝 、 硼烷 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 8,9-二氯-1-甲基-2,3,4,5-四氢-1H-3-苯并氮杂卓
  参考文献：
  名称：

  Discovery and SAR of new benzazepines as potent and selective 5-HT2C receptor agonists for the treatment of obesity

  摘要：

  We report on the synthesis, biological evaluation and structure-activity relationships for a series of 3-benzazepine derivatives as 5-HT2C receptor agonists. The compounds were evaluated in functional assays measuring [H-3] phosphoinositol turnover in HEK-293 cells transiently transfected with h5-HT2C, h5-HT2A or h5-HT2B receptors. Several compounds are shown to be potent and selective 5-HT2C receptor agonists, which decrease food intake in a rat feeding model. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.080

文献信息

• [EN] ADAMTS INHIBITORS, PREPARATION METHODS AND MEDICINAL USES THEREOF<br/>[FR] INHIBITEURS D'ADAMTS, LEURS PROCÉDÉS DE PRÉPARATION ET LEURS UTILISATIONS MÉDICALES
  申请人：ETERNITY BIOSCIENCE INC

  公开号：WO2021158626A1

  公开（公告）日：2021-08-12

  Compounds of formula (I) useful as inhibitors of ADAMTS-5 and/or ADAMTS-4, pharmaceutical compositions thereof, and use of them as therapeutic agents for the treatment of diseases involving degradation of cartilage or disruption of cartilage homeostasis, in particular osteoarthrosis and/or rheumatoid arthritis, are disclosed.

  公式（I）的化合物可用作ADAMTS-5和/或ADAMTS-4的抑制剂，其制药组合物以及将其用作治疗涉及软骨降解或软骨稳态紊乱的疾病的治疗剂，特别是骨关节炎和/或类风湿性关节炎。
• Discovery and Structure−Activity Relationship of (1<i>R</i>)-8-Chloro-2,3,4,5-tetrahydro-1-methyl-1<i>H</i>-3-benzazepine (Lorcaserin), a Selective Serotonin 5-HT_2C Receptor Agonist for the Treatment of Obesity
  作者：Brian M. Smith、Jeffrey M. Smith、James H. Tsai、Jeffrey A. Schultz、Charles A. Gilson、Scott A. Estrada、Rita R. Chen、Douglas M. Park、Emily B. Prieto、Charlemagne S. Gallardo、Dipanjan Sengupta、Peter I. Dosa、Jon A. Covel、Albert Ren、Robert R. Webb、Nigel R. A. Beeley、Michael Martin、Michael Morgan、Stephen Espitia、Hazel R. Saldana、Christina Bjenning、Kevin T. Whelan、Andrew J. Grottick、Frederique Menzaghi、William J. Thomsen

  DOI：10.1021/jm0709034

  日期：2008.1.1

  The synthesis and SAR of a novel 3-benzazepine series of 5-HT2C agonists is described. Compound 7d (lorcaserin, APD356) was identified as one of the more potent and selective compounds in vitro (pEC50 values in functional assays measuring [(3)H]phosphoinositol turnover: 5-HT2C = 8.1; 5-HT2A = 6.8; 5-HT2B = 6.1) and was potent in an acute in vivo rat food intake model upon oral administration (ED50

  描述了新型3-苯并ze庚因系列的5-HT 2C激动剂的合成和SAR。在体外，化合物7d（lorcaserin，APD356）被鉴定为更有效和选择性的化合物之一（在功能测定中，通过[[3] H]磷酸肌醇周转率测定的pEC50值：5-HT2C = 8.1; 5-HT2A = 6.8; 5- HT2B = 6.1），并且在口服后在急性体内大鼠食物摄入模型中有效（在6 h时的ED50 = 18 mg / kg）。Lorcaserin在大鼠单剂量药代动力学研究中进一步表征（t1 / 2 = 3.7小时； F = 86％），以及在生长的Sprague-Dawley大鼠中28天的体重增加模型（在60℃时观察到体重增加减少8.5％） 36 mg / kg出价）。选择洛卡西林在肥胖症的临床试验中进行进一步评估。
• [EN] BENZAZEPINE DERIVATIVES USEFUL FOR THE TREATMENT OF 5HT2C RECEPTOR ASSOCIATED DISEASES<br/>[FR] DERIVES DE BENZAZEPINE ET METHODES DE PROPHYLAXIE OU DE TRAITEMENT DE MALADIES ASSOCIEES AU RECEPTEUR 5HT2C
  申请人：ARENA PHARM INC

  公开号：WO2005003096A1

  公开（公告）日：2005-01-13

  The present invention relates to certain 1-substituted-2,3,4,5-tetrahydro-3-benzazepine derivatives of Formula (I), that are modulators of the 5HT2C receptor. Accordingly, compounds of the present invention are useful for the prophylaxis or treatment of 5HT2C receptor associated diseases, conditions or disorders, such as, obesity and related disorders.

  本发明涉及某些1-取代-2,3,4,5-四氢-3-苯并氮平衍生物（式（I）），它们是5HT2C受体的调节剂。因此，本发明的化合物对于预防或治疗与5HT2C受体相关的疾病、状况或障碍，如肥胖和相关障碍，是有用的。
• BENZAZEPINE DERIVATIVES USEFUL FOR TREATMENT OF 5HT2C RECEPTOR ASSOCIATED DISEASES
  申请人：Brian Smith

  公开号：US20130172322A1

  公开（公告）日：2013-07-04

  The present invention relates to certain 1-substituted-2,3,4,5-tetrahydro-3-benzazepine derivatives of Formula (I), that are modulators of the 5HT2C receptor. Accordingly, compounds of the present invention are useful for the prophylaxis or treatment of 5HT2C receptor associated diseases, conditions or disorders, such as, obesity and related disorders.

  本发明涉及某些1-取代-2,3,4,5-四氢-3-苯并哌啶衍生物，其为5HT2C受体调节剂。因此，本发明化合物对于预防或治疗与5HT2C受体相关的疾病、病况或障碍，如肥胖症及相关疾病，是有用的。
• Benzazepine derivatives and methods of prophylaxis or treatment of 5ht2c receptor associated diseases
  申请人：Smith Brian

  公开号：US20070142357A1

  公开（公告）日：2007-06-21

  The present invention relates to certain 1-substituted-2,3,4,5-tetrahydro-3-benzazepine derivatives of Formula (I), that are modulators of the 5HT2C receptor. Accordingly, compounds of the present invention are useful for the prophylaxis or treatment of 5HT2C receptor associated diseases, conditions or disorders, such as, obesity and related disorders.

  本发明涉及某些1-取代-2,3,4,5-四氢-3-苯并咪唑衍生物，其为5HT2C受体调节剂。因此，本发明化合物可用于预防或治疗与5HT2C受体相关的疾病、病况或障碍，如肥胖症及相关疾病。