[1-(5-oxo-4,5-dihydro-[1,2,4]oxadiazol-3-ylmethyl)-cyclohexylmethyl]-carbamic acid tert-butyl ester | 227626-65-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: [1-(5-oxo-4,5-dihydro-[1,2,4]oxadiazol-3-ylmethyl)-cyclohexylmethyl]-carbamic acid tert-butyl ester
• 英文别名: tert-Butyl ((1-((5-oxo-2,5-dihydro-1,2,4-oxadiazol-3-yl)methyl)cyclohexyl)methyl)carbamate；tert-butyl N-[[1-[(5-oxo-4H-1,2,4-oxadiazol-3-yl)methyl]cyclohexyl]methyl]carbamate
• CAS: 227626-65-5
• 化学式: C₁₅H₂₅N₃O₄
• 分子量: 311.381
• InChiKey: MSPZGLTYCFUIIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  89
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [1-(5-oxo-4,5-dihydro-[1,2,4]oxadiazol-3-ylmethyl)-cyclohexylmethyl]-carbamic acid tert-butyl ester 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 生成 3-(1-Aminomethyl-cyclohexylmethyl)-4H-[1,2,4]oxadiazol-5-one
  参考文献：
  名称：

  Oxadiazolone bioisosteres of pregabalin and gabapentin

  摘要：

  A series of oxadiazolone bioisosteres of pregabalin 1 and gabapentin 2 were prepared, and several were found to exhibit similar potency for the alpha(2)-delta subunit of voltage-gated calcium channels. Oxadiazolone 9 derived from 2 achieved low brain uptake but was nevertheless active in models of osteoarthritis. The high clearance associated with compound 9 was postulated to be a consequence of efflux by OAT and/or OCT, and was attenuated on co-administration with cimetidine or probenecid. (C) 2008 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2008.10.101
• 作为产物：
  描述：

  [1-(N-Hydroxycarbamimidoylmethyl)-cyclohexylmethyl]-carbamic acid tert-butyl ester 、 N,N'-羰基二咪唑 以 四氢呋喃 为溶剂， 生成 [1-(5-oxo-4,5-dihydro-[1,2,4]oxadiazol-3-ylmethyl)-cyclohexylmethyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Oxadiazolone bioisosteres of pregabalin and gabapentin

  摘要：

  A series of oxadiazolone bioisosteres of pregabalin 1 and gabapentin 2 were prepared, and several were found to exhibit similar potency for the alpha(2)-delta subunit of voltage-gated calcium channels. Oxadiazolone 9 derived from 2 achieved low brain uptake but was nevertheless active in models of osteoarthritis. The high clearance associated with compound 9 was postulated to be a consequence of efflux by OAT and/or OCT, and was attenuated on co-administration with cimetidine or probenecid. (C) 2008 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2008.10.101

文献信息

• Method of treating cartilage damage
  申请人：——

  公开号：US20020072533A1

  公开（公告）日：2002-06-13

  The invention relates to a method of preventing or treating cartilage damage by administering a GABA analog such as, for example, a compound of Formula 1 and pharmaceutically acceptable salts thereof, wherein R 1 is hydrogen or straight or branched lower alkyl, and n is an integer of from 4 to 6.

  该发明涉及通过给予类似GABA的类似物，例如Formula1的化合物及其药学上可接受的盐，来预防或治疗软骨损伤的方法，其中R1是氢或直链或支链低碳烷基，n为4至6的整数。
• Method of treating tinnitus
  申请人：Dooley James David

  公开号：US20060100281A1

  公开（公告）日：2006-05-11

  The invention relates to a method of treating tinnitus by administering an alpha2delta ligand such as, for example, a compound of Formula and pharmaceutically acceptable salts thereof, wherein R 1 is hydrogen or straight or branched lower alkyl, and n is an integer of from 4 to 6.

  本发明涉及一种通过给予α2δ配体治疗耳鸣的方法，例如，给予公式中的化合物及其药学上可接受的盐，其中R1为氢或直链或支链低碳基，n为4到6的整数。
• Heterocyclic derivatives useful as pharmaceutical agents
  申请人：——

  公开号：US20020077342A1

  公开（公告）日：2002-06-20

  This invention relates to novel heterocyclic derivatives of the formula (VII), (VIII) or (IX) 1 in which P, Q, R 1 -R 6 , m and n are as defined in the specification, and to pharmaceutically acceptable salts thereof. The compounds and pharmaceutical compositions containing them are useful in the treatment of a range of disorders including epilepsy, faintness attacks, hypokinesia, cranial disorders, depression, anxiety, panic, pain, neuropathological disorders, inflammatory diseases and gastrointestinal disorders, especially irritable bowel syndrome.

  本发明涉及公式（VII），（VIII）或（IX）的新异环丙基衍生物，其中P，Q，R1-R6，m和n如规范所定义，并且其药学上可接受的盐。这些化合物和含有它们的药物组合物在治疗一系列疾病方面有用，包括癫痫，晕厥，低动力症，头颅疾病，抑郁症，焦虑，惊恐，疼痛，神经病理性疾病，炎症性疾病和胃肠疾病，特别是肠易激综合征。
• 1-substituted-1-aminomethyl-cycloalkane derivatives (= gabapentin analogues), their preparation and their use in the treatment of neurological disorders
  申请人：Warner-Lambert Company LLC

  公开号：EP1475371A1

  公开（公告）日：2004-11-10

  Novel amines of formulas 1, 1C, 1F, 1G and 1H or a pharmaceutical acceptable salt thereof wherein n is an integer of from 0 to 2; m is an integer of from 0 to 3; R is sulfonamide, amide, heterocycle, sulfonic acid, or hydroxamic acid; A' is a bridged ring selected from wherein is the point of attachment; Z1 to Z4 are each independently selected from hydrogen and methyl; o is an integer of from 1 to 4; and p is an integer of from 0 to 2. In formula (1) above R cannot be sulfonic acid when m is 2 and n is 1 are disclosed and are useful as agents in the treatment of epilepsy, faintness attacks, hypokinesia, cranial disorders, neurodegenerative disorders, depression, anxiety, panic, pain, neuropathological disorders, inflammatory diseases, and gastrointestinal disorders, especially irritable bowel syndrome.

  式 1、1C、1F、1G 和 1H 的新型胺 或其可接受的药用盐 其中 n 是 0 至 2 的整数 m 是 0 至 3 的整数； R 是磺酰胺、 酰胺 杂环 磺酸或 羟肟酸； A' 是桥接环，选自 其中 是连接点； Z1 至 Z4 各自独立地选自氢和甲基； o 是 1 至 4 的整数；以及 p 是 0 至 2 的整数。 在上述式（1）中，当 m 为 2 和 n 为 1 时，R 不能是磺酸，这些物质已被公开，可作为治疗癫痫、晕厥发作、运动功能减退、颅脑疾病、神经退行性疾病、抑郁症、焦虑症、恐慌症、疼痛、神经病理学疾病、炎症性疾病和胃肠道疾病，特别是肠易激综合征的药物。
• 1-SUBSTITUTED-1-AMINOMETHYL-CYCLOALKANE DERIVATIVES (=GABAPENTIN ANALOGUES), THEIR PREPARATION AND THEIR USE IN THE TREATMENT OF NEUROLOGICAL DISORDERS
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP1047678A1

  公开（公告）日：2000-11-02