(3R,4R)-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)pyrrolidine-2,5-dione pseudoephedrine complex | 1313508-66-5

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (3R,4R)-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)pyrrolidine-2,5-dione pseudoephedrine complex
• 英文别名: (-)-trans-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)pyrrolidine-2,5-dione (1S,2S)-(+)-pseudoephedrine
• CAS: 1313508-66-5
• 化学式: C₁₀H₁₅NO*C₂₃H₁₉N₃O₂
• 分子量: 534.658
• InChiKey: WHIWCTRLPVNVOH-SBZWQVCDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.92
• 重原子数：
  40.0
• 可旋转键数：
  5.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  99.15
• 氢给体数：
  4.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (3R,4R)-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)pyrrolidine-2,5-dione pseudoephedrine complex 生成 (3R,4R)-3-(5,6-二氢-4H-吡咯并[3,2,1-IJ]喹啉-1-基)-4-(1H-吲哚-3-基)吡咯烷-2,5-二酮
  参考文献：
  名称：

  COMBINATIONAL COMPOSITIONS AND METHODS FOR TREATMENT OF CANCER

  摘要：

  本发明提供了一种治疗细胞增殖性疾病（如癌症）的方法，通过向需要治疗的受试者施用一种吡咯喹啉基吡咯-2,5-二酮化合物或吡咯喹啉基吡咯啶-2,5-二酮化合物的治疗有效剂量，结合一种第二个抗增殖剂的治疗有效剂量。

  公开号：

  US20100297075A1
• 作为产物：
  描述：

  3(S),4(R)-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)pyrrolidine-2,5-dione 在 盐酸 作用下， 以 醋酸异丙酯 、 水 、 乙腈 为溶剂， 生成 (3R,4R)-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)pyrrolidine-2,5-dione pseudoephedrine complex
  参考文献：
  名称：

  Purified Pyrroloquinolinyl-Pyrrolidine-2,5-Dione Compositions And Methods For Preparing And Using Same

  摘要：

  本发明涉及(-)-trans-3-(5,6-二氢-4H-吡咯[3,2,1-ij]喹啉-1-基)-4-(1H-吲哚-3-基)吡咯烷-2,5-二酮的形式1和形式2晶型。本发明还涉及手性纯度大于99%的(-)-trans-3-(5,6-二氢-4H-吡咯[3,2,1-ij]喹啉-1-基)-4-(1H-吲哚-3-基)吡咯烷-2,5-二酮化合物，以及制备这些化合物的方法。本发明还涉及包含这些(-)-trans-3-(5,6-二氢-4H-吡咯[3,2,1-ij]喹啉-1-基)-4-(1H-吲哚-3-基)吡咯烷-2,5-二酮化合物的药物组合物。本发明提供了通过向需要的受体施用含有手性纯度大于99%的(-)-trans-3-(5,6-二氢-4H-吡咯[3,2,1-ij]喹啉-1-基)-4-(1H-吲哚-3-基)吡咯烷-2,5-二酮或(-)-trans-3-(5,6-二氢-4H-吡咯[3,2,1-ij]喹啉-1-基)-4-(1H-吲哚-3-基)吡咯烷-2,5-二酮的形式1和形式2晶型的组合物的治疗细胞增殖紊乱，如癌症的方法。

  公开号：

  US20110160242A1

文献信息

• Highly Pure Pyrroloquinolinyl-Pyrrole-2,5-Dione and Pyrroloquinolinyl-Pyrrolidine-2,5-Dione and Methods of Preparing Same
  申请人：ARQULE, INC.

  公开号：US20130281699A1

  公开（公告）日：2013-10-24

  The present invention relates to highly-pure pyrroloquinolinyl-pyrrole-2,5-dione and pyrroloquinolinyl-pyrrolidine-2,5-dione, for example, 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin- 1 -yl)-4-(1H-indol-3-yl)-1H-pyrrole-2,5-dione, 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)pyrrolidine-2,5-dione, and pharmaceutically acceptable salts, solvates, and diastereomers thereof. The present invention also relates to methods for preparing highly-pure pyrroloquinolinyl-pyrrole-2,5-dione and pyrroloquinolinyl-pyrrolidine-2,5-dione, for example, 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)-1H-pyrrole-2,5-dione, 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)pyrrolidine-2,5-dione, and pharmaceutically acceptable salts, solvates, and diastereomers thereof.

  本发明涉及高纯度的吡咯喹啉基吡咯-2,5-二酮和吡咯喹啉基吡咯啉-2,5-二酮，例如3-(5,6-二氢-4H-吡咯[3,2,1-ij]喹啉-1-基)-4-(1H-吲哚-3-基)-1H-吡咯-2,5-二酮，3-(5,6-二氢-4H-吡咯[3,2,1-ij]喹啉-1-基)-4-(1H-吲哚-3-基)吡咯啉-2,5-二酮，以及其药学上可接受的盐、溶剂和对映体。本发明还涉及制备高纯度的吡咯喹啉基吡咯-2,5-二酮和吡咯喹啉基吡咯啉-2,5-二酮的方法，例如3-(5,6-二氢-4H-吡咯[3,2,1-ij]喹啉-1-基)-4-(1H-吲哚-3-基)-1H-吡咯-2,5-二酮，3-(5,6-二氢-4H-吡咯[3,2,1-ij]喹啉-1-基)-4-(1H-吲哚-3-基)吡咯啉-2,5-二酮，以及其药学上可接受的盐、溶剂和对映体。
• [EN] HIGHLY PURE PYRROLOQUINOLINYL-PYRROLE-2,5-DIONE AND PYRROLOQUINOLINYL-PYRROLIDINE-2,5-DIONE AND METHODS OF PREPARING SAME<br/>[FR] PYRROLOQUINOLINYL-PYRROLE-2,5-DIONE ET PYRROLOQUINOLINYL-PYRROLIDINE-2,5-DIONE DE PURETÉ ÉLEVÉE ET LEURS PROCÉDÉS DE PRÉPARATION
  申请人：ARQULE INC

  公开号：WO2013162714A1

  公开（公告）日：2013-10-31

  The present invention relates to highly-pure pyrroloquinolinyl-pyrrole-2,5-dione and pyrroloquinolinyl-pyrrolidine-2,5-dione, for example, 3-(5,6-dihydro-4H-pyrrolo[3,2,l-ij]quinolin-l- yl)-4-(lH-indol-3-yl)-lH-pyrrole-2,5-dione, 3-(5,6-dihydro-4H-pyrrolo[3,2,l-ij]quinolin-l-yl)-4-(lH- indol-3-yl)pyrrolidine-2,5-dione, and pharmaceutically acceptable salts, solvates, and diastereomers thereof. The present invention also relates to methods for preparing highly-pure pyrroloquinolinyl- pyrrole-2,5-dione and pyrroloquinolinyl-pyrrolidine-2,5-dione, for example, 3-(5,6-dihydro-4H- pyrrolo[3,2,l-ij]quinolin-l-yl)-4-(lH-indol-3-yl)-lH-pyrrole-2,5-dione, 3-(5,6-dihydro-4H- pyrrolo[3,2,l-ij]quinolin-l-yl)-4-(lH-indol-3-yl)pyrrolidine-2,5-dione, and pharmaceutically acceptable salts, solvates, and diastereomers thereof.

  本发明涉及高纯度吡咯并喹啉基吡咯-2,5-二酮和吡咯并喹啉基吡咯烷-2,5-二酮，例如3-(5,6-二氢-4H-吡咯[3,2,l-ij]喹啉-1-基)-4-(1H-吲哚-3-基)-1H-吡咯-2,5-二酮，3-(5,6-二氢-4H-吡咯[3,2,l-ij]喹啉-1-基)-4-(1H-吲哚-3-基)吡咯烷-2,5-二酮，以及其药学上可接受的盐，溶剂化合物和对映体。本发明还涉及制备高纯度吡咯并喹啉基吡咯-2,5-二酮和吡咯并喹啉基吡咯烷-2,5-二酮的方法，例如3-(5,6-二氢-4H-吡咯[3,2,l-ij]喹啉-1-基)-4-(1H-吲哚-3-基)-1H-吡咯-2,5-二酮，3-(5,6-二氢-4H-吡咯[3,2,l-ij]喹啉-1-基)-4-(1H-吲哚-3-基)吡咯烷-2,5-二酮，以及其药学上可接受的盐，溶剂化合物和对映体的方法。
• Highly pure pyrroloquinolinyl-pyrrole-2,5-dione and pyrroloquinolinyl-pyrrolidine-2,5-dione and methods of preparing same
  申请人：ArQule, Inc.

  公开号：US09000005B2

  公开（公告）日：2015-04-07

  The present invention relates to highly-pure pyrroloquinolinyl-pyrrole-2,5-dione and pyrroloquinolinyl-pyrrolidine-2,5-dione, for example, 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)-1H-pyrrole-2,5-dione, 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)pyrrolidine-2,5-dione, and pharmaceutically acceptable salts, solvates, and diastereomers thereof. The present invention also relates to methods for preparing highly-pure pyrroloquinolinyl-pyrrole-2,5-dione and pyrroloquinolinyl-pyrrolidine-2,5-dione, for example, 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)-1H-pyrrole-2,5-dione, 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)pyrrolidine-2,5-dione, and pharmaceutically acceptable salts, solvates, and diastereomers thereof.

  本发明涉及高纯度的吡咯并喹啉基吡咯-2,5-二酮和吡咯并喹啉基吡咯啉-2,5-二酮，例如3-(5,6-二氢-4H-吡咯[3,2,1-ij]喹啉-1-基)-4-(1H-吲哚-3-基)-1H-吡咯-2,5-二酮，3-(5,6-二氢-4H-吡咯[3,2,1-ij]喹啉-1-基)-4-(1H-吲哚-3-基)吡咯啉-2,5-二酮，以及其药学上可接受的盐、溶剂和对映体。本发明还涉及制备高纯度的吡咯并喹啉基吡咯-2,5-二酮和吡咯并喹啉基吡咯啉-2,5-二酮的方法，例如3-(5,6-二氢-4H-吡咯[3,2,1-ij]喹啉-1-基)-4-(1H-吲哚-3-基)-1H-吡咯-2,5-二酮，3-(5,6-二氢-4H-吡咯[3,2,1-ij]喹啉-1-基)-4-(1H-吲哚-3-基)吡咯啉-2,5-二酮，以及其药学上可接受的盐、溶剂和对映体。
• [EN] PURIFIED PYRROLOQUINOLINYL-PYRROLIDINE-2,5-DIONE COMPOSITIONS AND METHODS FOR PREPARING AND USING SAME<br/>[FR] COMPOSITIONS PURIFIÉES DE PYRROLOQUINOLINYL-PYRROLIDINE-2,5-DIONE ET LEURS PROCÉDÉS DE PRÉPARATION ET D'UTILISATION
  申请人：ARQULE INC

  公开号：WO2011079142A2

  公开（公告）日：2011-06-30

  The present invention relates to a form 1 and form 2 polymorph of (-)-trans -3 -(5,6- dihydro-4H-pyrrolo [3,2,1-ij] quinolin-1-yl)-4-(1H-indol-3-yl) pyrrolidine-2,5-dione. The present invention also relates to (-)-trans-3-(5,6-dihydro-4H-pyrrolo [3,2,1-ij] quinolin-1-yl)-4- (1H-indol-3-yl) pyrrolidine-2, 5-dione compounds having a chiral purity greater than 99%, and methods of preparation of these compounds. The present invention also relates to pharmaceutical compositions comprising these (-)-trans-3-(5,6-dihydro-4H-pyrrolo [3,2,1-ij] quinolin-l-yl)-4-(lH-indol-3-yl) pyrrolidine-2, 5-dione compounds. The present invention provides methods of treating a cell proliferative disorder, such as a cancer, by administering to a subject in need thereof a therapeutically effective amount of a composition comprising (-)-trans- 3-(5,6-dihydro-4H-pyrrolo [3,2,1-ij] quinolin-l-yl)-4-(lH-indol-3-yl) pyrrolidine-2, 5-dione having a chiral purity greater than 99% or a form 1 and form 2 polymorph of (-)-trans -3 -(5,6- dihydro-4H-pyrrolo [3,2,1-ij] quinolin-1-yl)-4-(1H-indol-3-yl) pyrrolidine-2,5-dione.

  本发明涉及一种(-)-trans-3-(5,6-二氢-4H-吡咯并[3,2,1-ij]喹啉-1-基)-4-(1H-吲哚-3-基)吡咯烷-2,5-二酮的1型和2型多晶形。本发明还涉及具有手性纯度大于99%的(-)-trans-3-(5,6-二氢-4H-吡咯并[3,2,1-ij]喹啉-1-基)-4-(1H-吲哚-3-基)吡咯烷-2,5-二酮化合物，以及制备这些化合物的方法。本发明还涉及包含这些(-)-trans-3-(5,6-二氢-4H-吡咯并[3,2,1-ij]喹啉-1-基)-4-(1H-吲哚-3-基)吡咯烷-2,5-二酮化合物的制药组合物。本发明提供了通过向需要治疗细胞增殖性疾病，如癌症的患者投与具有手性纯度大于99%或(-)-trans-3-(5,6-二氢-4H-吡咯并[3,2,1-ij]喹啉-1-基)-4-(1H-吲哚-3-基)吡咯烷-2,5-二酮的1型和2型多晶形的组合物的治疗方法。
• Purified pyrroloquinolinyl-pyrrolidine-2,5-dione compositions and methods for preparing and using same
  申请人：Reed David P.

  公开号：US08552192B2

  公开（公告）日：2013-10-08

  The present invention relates to a form 1 and form 2 polymorph of (−)-trans-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)pyrrolidine-2,5-dione. The present invention also relates to (−)-trans-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl) pyrrolidine-2,5-dione compounds having a chiral purity greater than 99%, and methods of preparation of these compounds. The present invention also relates to pharmaceutical compositions comprising these (−)-trans-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)pyrrolidine-2,5-dione compounds. The present invention provides methods of treating a cell proliferative disorder, such as a cancer, by administering to a subject in need thereof a therapeutically effective amount of a composition comprising (−)-trans-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)pyrrolidine-2,5-dione having a chiral purity greater than 99% or a form 1 and form 2 polymorph of (−)-trans-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)pyrrolidine-2,5-dione.

  本发明涉及（-）-trans-3-(5,6-二氢-4H-吡咯并[3,2,1-ij]喹啉-1-基)-4-(1H-吲哚-3-基)吡咯烷-2,5-二酮的1型和2型多晶形态。本发明还涉及手性纯度大于99%的（-）-trans-3-(5,6-二氢-4H-吡咯并[3,2,1-ij]喹啉-1-基)-4-(1H-吲哚-3-基)吡咯烷-2,5-二酮化合物，以及制备这些化合物的方法。本发明还涉及含有这些（-）-trans-3-(5,6-二氢-4H-吡咯并[3,2,1-ij]喹啉-1-基)-4-(1H-吲哚-3-基)吡咯烷-2,5-二酮化合物的药物组合物。本发明提供了通过向需要治疗细胞增殖性疾病，如癌症的患者施用手性纯度大于99%的（-）-trans-3-(5,6-二氢-4H-吡咯并[3,2,1-ij]喹啉-1-基)-4-(1H-吲哚-3-基)吡咯烷-2,5-二酮或（-）-trans-3-(5,6-二氢-4H-吡咯并[3,2,1-ij]喹啉-1-基)-4-(1H-吲哚-3-基)吡咯烷-2,5-二酮的1型和2型多晶形态的组合物的治疗细胞增殖性疾病的方法。