2-ethoxy-5-methanesulfonyl-benzoic acid methyl ester | 459833-27-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-ethoxy-5-methanesulfonyl-benzoic acid methyl ester
• 英文别名: Methyl 2-ethoxy-5-(methylsulfonyl)benzoate；Methyl 2-ethoxy-5-methylsulfonylbenzoate
• CAS: 459833-27-3
• 化学式: C₁₁H₁₄O₅S
• 分子量: 258.295
• InChiKey: ILHXVNPYJMHGID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-ethoxy-5-methanesulfonyl-benzoic acid methyl ester 在 乙醇 、 sodium hydroxide 、 盐酸 作用下， 以 水 为溶剂， 反应 1.0h， 以118 mg的产率得到2-ethoxy-5-methanesulfonyl-benzoic acid
  参考文献：
  名称：

  Selective GlyT1 Inhibitors: Discovery of [4-(3-Fluoro-5-trifluoromethylpyridin-2-yl)piperazin-1-yl][5-methanesulfonyl-2-((S)-2,2,2-trifluoro-1-methylethoxy)phenyl]methanone (RG1678), a Promising Novel Medicine To Treat Schizophrenia

  摘要：

  The GlyT1 transporter has emerged as a key novel target for the treatment of schizophrenia. Herein, we report on the optimization of the 2-alkoxy-5-methylsulfonebenzoylpiperazine class of GlyT1 inhibitors to improve hERG channel selectivity and brain penetration. This effort culminated in the discovery of compound 10a (RG1678), the first potent and selective GlyT1 inhibitor to have a beneficial effect in schizophrenic patients in a phase II clinical trial.

  DOI：

  10.1021/jm100210p
• 作为产物：
  描述：

  乙醇 、 methyl 2-hydroxy-5-(methylsulfonyl)benzoate 在 偶氮二甲酸二叔丁酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 24.08h， 以130 mg的产率得到2-ethoxy-5-methanesulfonyl-benzoic acid methyl ester
  参考文献：
  名称：

  Selective GlyT1 Inhibitors: Discovery of [4-(3-Fluoro-5-trifluoromethylpyridin-2-yl)piperazin-1-yl][5-methanesulfonyl-2-((S)-2,2,2-trifluoro-1-methylethoxy)phenyl]methanone (RG1678), a Promising Novel Medicine To Treat Schizophrenia

  摘要：

  The GlyT1 transporter has emerged as a key novel target for the treatment of schizophrenia. Herein, we report on the optimization of the 2-alkoxy-5-methylsulfonebenzoylpiperazine class of GlyT1 inhibitors to improve hERG channel selectivity and brain penetration. This effort culminated in the discovery of compound 10a (RG1678), the first potent and selective GlyT1 inhibitor to have a beneficial effect in schizophrenic patients in a phase II clinical trial.

  DOI：

  10.1021/jm100210p

文献信息

• Pharmaceutically active compounds
  申请人：——

  公开号：US20030064990A1

  公开（公告）日：2003-04-03

  Compound of general formula I: 1 wherein R 1 , R 2 , R 3 , R 4 , X, Y and R 5 have the meanings given herein which are useful in the curative and prophylactic treatment of a medical condition for which inhibition of a cyclic guanosine 3′,5′-monophosphate phosphodiesterase (e.g. cGMP PDE5) is desired.

  通式I：1中R1、R2、R3、R4、X、Y和R5的含义如下，对于需要抑制环状鸟苷酸3′,5′-单磷酸酯酶（例如cGMP PDE5）的医疗状况的治疗和预防是有用的。
• CYCLIC GUANOSINE 3',5'-MONOPHOSPHATE PHOSPHODIESTERASE INHIBITORS
  申请人：Pfizer Limited

  公开号：EP1368352B1

  公开（公告）日：2004-12-01
• US6770645B2
  申请人：——

  公开号：US6770645B2

  公开（公告）日：2004-08-03
• Selective GlyT1 Inhibitors: Discovery of [4-(3-Fluoro-5-trifluoromethylpyridin-2-yl)piperazin-1-yl][5-methanesulfonyl-2-((<i>S</i>)-2,2,2-trifluoro-1-methylethoxy)phenyl]methanone (RG1678), a Promising Novel Medicine To Treat Schizophrenia
  作者：Emmanuel Pinard、Alexander Alanine、Daniela Alberati、Markus Bender、Edilio Borroni、Patrick Bourdeaux、Virginie Brom、Serge Burner、Holger Fischer、Dominik Hainzl、Remy Halm、Nicole Hauser、Synese Jolidon、Judith Lengyel、Hans-Peter Marty、Thierry Meyer、Jean-Luc Moreau、Roland Mory、Robert Narquizian、Mathias Nettekoven、Roger D. Norcross、Bernd Puellmann、Philipp Schmid、Sebastien Schmitt、Henri Stalder、Roger Wermuth、Joseph G. Wettstein、Daniel Zimmerli

  DOI：10.1021/jm100210p

  日期：2010.6.24

  The GlyT1 transporter has emerged as a key novel target for the treatment of schizophrenia. Herein, we report on the optimization of the 2-alkoxy-5-methylsulfonebenzoylpiperazine class of GlyT1 inhibitors to improve hERG channel selectivity and brain penetration. This effort culminated in the discovery of compound 10a (RG1678), the first potent and selective GlyT1 inhibitor to have a beneficial effect in schizophrenic patients in a phase II clinical trial.