3-(3-anilino-3-oxoprop-1-enyl)-4,6-dichloro-1H-indole-2-carboxylic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-(3-anilino-3-oxoprop-1-enyl)-4,6-dichloro-1H-indole-2-carboxylic acid
• 化学式: C₁₈H₁₂Cl₂N₂O₃
• 分子量: 375.2
• InChiKey: WZBNEZWCNKUOSM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  82.2
• 氢给体数：
  3
• 氢受体数：
  3

文献信息

• Indole-2-carboxylic acid derivatives
  申请人：GLAXO S.p.A.

  公开号：EP0568136A1

  公开（公告）日：1993-11-03

  The invention relates to compounds of formula (I). or a salt, or metabolically labile ester thereof wherein R represents a group selected from halogen, alkyl, alkoxy, amino, alkylamino, dialkylamino, hydroxy, trifluoromethyl, trifluoromethoxy, nitro, cyano, SO₂R₁ or COR₁ wherein R₁ represents hydroxy, methoxy, or amino; m is zero or an integer 1 or 2; A represents an ethynyl group or an optionally substituted ethenyl, or cyclopropyl group; X represents -O- or NH; R₂ represents an aryl group and when X represents an oxygen atom R₂ may also represent a hydrogen atom or an alkyl group; which are antagonists of excitatory amino acids, to processes for their preparation and to their use in medicine.

  本发明涉及式 (I) 化合物。 其中 R 代表选自卤素、烷基、烷氧基、氨基、烷基氨基、二烷基氨基、羟基、三氟甲基、三氟甲氧基、硝基、氰基、SO₂R₁ 或 COR₁ 的基团，其中 R₁ 代表羟基、甲氧基或氨基；m 为零或 1 或 2 的整数； A 代表乙炔基或任选取代的乙烯基或环丙基； X 代表-O-或 NH； R₂代表芳基，当 X 代表氧原子时，R₂也可以代表氢原子或烷基。
• PROPHYLACTIC OR THERAPEUTIC AGENT FOR OPTIC NERVE DISORDERS COMPRISING 4,6-DICHLORO-1H-INDOLE-2-CARBOXYLIC ACID DERIVATIVE OR SALT THEREOF AS ACTIVE INGREDIENT
  申请人：Santen Pharmaceutical Co., Ltd

  公开号：EP2407454A1

  公开（公告）日：2012-01-18

  Disclosed is a compound useful as a preventive or therapeutic agent for optic nerve disorders, an inhibitor of retinal ganglion cell death or an agent for restoring the expression level of a neurofilament light chain, particularly a compound capable of exhibiting the abovementioned pharmacological activities when administered orally. A 4,6-dichloro-1H-indole-2-carboxylic acid derivative or a salt thereof can significantly inhibit the decrease in the number of cells in a retinal ganglion cell layer of an NMDA-induced rat retinal disorder model when administered to the model orally, and can also restore the decrease in the expression level of a neurofilament light chain in a retina of the model when administered to the model intravitreally (intraocular local administration). Therefore, the compound or a salt thereof is useful as a preventive or therapeutic agent for optic nerve disorders, an inhibitor of retinal ganglion cell death or an agent for restoring the expression level of a neurofilament light chain.

  本发明公开了一种可作为视神经疾病的预防或治疗剂、视网膜神经节细胞死亡抑制剂或恢复神经丝蛋白轻链表达水平的药物的化合物，特别是一种在口服给药时能够表现出上述药理活性的化合物。一种 4,6-二氯-1H-吲哚-2-羧酸衍生物或其盐在口服给药 NMDA 诱导的大鼠视网膜紊乱模型时，能显著抑制该模型视网膜神经节细胞层细胞数量的减少；在玻璃体内给药（眼内局部给药）时，还能恢复该模型视网膜中神经丝轻链表达水平的减少。因此，该化合物或其盐类可用作视神经疾病的预防或治疗药物、视网膜神经节细胞死亡抑制剂或恢复神经丝轻链表达水平的药物。
• PHARMACEUTICAL COMPOSITION FOR PARENTERAL APPLICATION CONTAINING AN INDOLE-CARBOXYLIC ACID
  申请人：GLAXO WELLCOME S.p.A.

  公开号：EP0809514A1

  公开（公告）日：1997-12-03
• D-SERINE TRANSPORTER INHIBITORS AS PHARMACEUTICAL COMPOSITIONS FOR THE TREATMENT OF CENTRAL NERVOUS SYSTEM DISORDERS
  申请人：ALLERGAN, INC.

  公开号：EP2714029B1

  公开（公告）日：2017-04-12
• PREVENTIVE OR THERAPEUTIC AGENTS FOR OPTIC NERVE DISORDERS COMPRISING 4,6-DICHLORO-1H-INDOLE-2-CARBOXYLIC ACID DERIVATIVES OR SALTS THEREOF AS ACTIVE INGREDIENTS
  申请人：Sasaoka Masaaki

  公开号：US20110319463A1

  公开（公告）日：2011-12-29

  A method for preventing or treating an optic nerve disorder, inhibiting retinal nerve cell death or recovering a neurofilament light chain expression level by administering to a patient a pharmacologically effective amount of at least one of the compound represented by the following formula (1): wherein R 1 is a hydrogen atom or a lower alkyl group R 2 is a hydrogen atom or a lower alkyl group; R 1 and R 2 may be joined to each other to form an aziridine ring, an azetidine ring, a pyrrolidine ring, a piperidine ring or an azepane ring; and R 3 is a carboxyl group or an ester thereof or an amide thereof; or a salt thereof.