(S)-3,6,7,7a-tetrahydro-1H-pyrrolo[1,5a]imidazole-2,5-dione | 151062-32-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-3,6,7,7a-tetrahydro-1H-pyrrolo[1,5a]imidazole-2,5-dione
• 英文别名: (S)-dimiracetam；Dimiracetam, (S)-；(7aS)-3,6,7,7a-tetrahydro-1H-pyrrolo[1,2-a]imidazole-2,5-dione
• CAS: 151062-32-7
• 化学式: C₆H₈N₂O₂
• 分子量: 140.142
• InChiKey: XTXXOHPHLNROBN-BYPYZUCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-acetyl-tetrahydro-pyrrolo[1,2-a]imidazole-2,5-dione 在 amberlite IR 120 (H⁺ form) 作用下， 以 水 为溶剂， 以54%的产率得到(S)-3,6,7,7a-tetrahydro-1H-pyrrolo[1,5a]imidazole-2,5-dione
  参考文献：
  名称：

  Synthesis and biological evaluation of novel dimiracetam derivatives useful for the treatment of neuropathic pain

  摘要：

  Chemical modifications of dimiracetam, a bicyclic analogue of the nootropic drug piracetam, afforded a small set of novel derivatives that were investigated in in vivo models of neuropathic pain. Compounds 5, 7 and 8 displayed a very promising antihyperalgesic profile in rat models of neuropathic pain induced by both chronic constriction injury of the sciatic nerve and streptozotocin. The compounds completely reverted the reduction of pain threshold evaluated by the paw pressure test. Importantly these derivatives did not induce any behavioural impairment as evaluated by the rotarod test. These results suggest that compounds 5, 7 and 8 might represent novel and well-tolerated therapeutic agents for the relief of neuropathic pain. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.12.015

文献信息

• Pyrrolo[1,2-a]imidazoledione effective in the treatment of peripheral neurotoxicity induced by chemotherapeutic agents
  申请人：NIKEM RESEARCH S.R.L.

  公开号：EP1925304A1

  公开（公告）日：2008-05-28

  The use of a compound of formula (I) is disclosed in treating and/or preventing chemotherapy-induced peripheral neurotoxicity (CIPN). The invention includes pharmaceutical compositions wherein the compound of formula (I) is present in a mixture with anticancer agents. An improved anticancer treatment with reduced CIPN-related side effects is also provided.

  本发明公开了式（I）化合物在治疗和/或预防化疗诱导的周围神经毒性（CIPN）中的用途。本发明包括药物组合物，其中式（I）化合物与抗癌剂混合存在。本发明还提供了一种可减少 CIPN 相关副作用的改良抗癌疗法。
• Synergistic compositions comprising (R)-dimiracetam (1) and (S)-dimiracetam (2) in a non-racemic ratio
  申请人：Metys Pharmaceuticals AG

  公开号：US10738054B2

  公开（公告）日：2020-08-11

  The present invention relates to a composition of enantiomers of 3,6,7,7a-tetrahydro-1H-pyrrolo[1,5-a]imidazole-2,5-dione and pharmaceutically acceptable solvates or co-crystals thereof in a certain ratio, a pharmaceutical composition comprising said composition, its use as a medicament and the use of the inventive compositions or pharmaceutical compositions in the treatment and/or prevention of a disease or disorder typically and preferably selected from peripheral sensory neuropathy, preferably peripheral neuropathic pain; seizure; depression; or cognitive impairment.

  本发明涉及一种3,6,7,7a-四氢-1H-吡咯并[1,5-a]咪唑-2,5-二酮的对映体及其药学上可接受的溶液或共晶按一定比例组成的组合物，一种包含所述组合物的药物组合物，其作为药物的用途，以及本发明组合物或药物组合物在治疗和/或预防典型和优选选自周围感觉神经病，优选周围神经病理性疼痛的疾病或紊乱中的用途； 癫痫发作；抑郁症；或认知障碍。
• PROCESS FOR THE PREPARATION OF CONDENSED IMIDAZOLES
  申请人：SMITHKLINE BEECHAM FARMACEUTICI S.p.A.

  公开号：EP0611371A1

  公开（公告）日：1994-08-24
• PYRROLOY[1,2-A]IMIDAZOLEDIONE EFFECTIVE IN THE TREATMENT OF PERIPHERAL NEUROTOXICITY INDUCED BY CHEMOTHERAPEUTIC AGENTS
  申请人：Neurotune AG

  公开号：EP2094265A1

  公开（公告）日：2009-09-02
• SYNERGISTIC COMPOSITIONS COMPRISING (R)-DIMIRACETAM (1) AND (S)-DIMIRACETAM (2) IN A NON-RACEMIC RATIO
  申请人：Metys Pharmaceuticals AG

  公开号：EP3534898A1

  公开（公告）日：2019-09-11