benzyl (5R)-5-methyl-2-oxopiperidine-1-carboxylate | 179685-75-7

• 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: benzyl (5R)-5-methyl-2-oxopiperidine-1-carboxylate
• 英文别名: (+)-(R)-benzyl-5-methyl-2-oxopiperidine-1-carboxylate；5(R)-methyl-1-benzyloxycarbonyl-2-piperidone
• CAS: 179685-75-7
• 化学式: C₁₄H₁₇NO₃
• 分子量: 247.294
• InChiKey: KHDNNZVCEDWGFH-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzyl (5R)-5-methyl-2-oxopiperidine-1-carboxylate 在 正丁基锂 、 六甲基二硅氮烷 、 (+)-(8,8-dichlorocamphorylsulfonyl)oxaziridine 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.5h， 生成 (3S,5R)-3-Hydroxy-5-methyl-2-oxo-piperidine-1-carboxylic acid benzyl ester
  参考文献：
  名称：

  环戊胺哌啶-生物碱亚结构的所有非对映异构体的合成

  摘要：

  从对映体纯的香茅酸开始，以完全的立体控制合成了维他命胺和果菊型的三取代哌啶-生物碱的所有四种非对映异构体。本文所述的灵活，高产且可扩展的途径将有助于融合合成，并使人们能够获得环巴胺和其他具有生物活性的类固醇生物碱的类似物。

  DOI：

  10.1021/ol902270f
• 作为产物：
  描述：

  (+)-(R)-benzyl-2-hydroxy-5-methylpiperidine-1-carboxylate 在 tetra-n-propylammonium perruthenate. 、 N-甲基吗啉氧化物 作用下， 以 水 、 乙腈 为溶剂， 生成 benzyl (5R)-5-methyl-2-oxopiperidine-1-carboxylate
  参考文献：
  名称：

  环戊胺哌啶-生物碱亚结构的所有非对映异构体的合成

  摘要：

  从对映体纯的香茅酸开始，以完全的立体控制合成了维他命胺和果菊型的三取代哌啶-生物碱的所有四种非对映异构体。本文所述的灵活，高产且可扩展的途径将有助于融合合成，并使人们能够获得环巴胺和其他具有生物活性的类固醇生物碱的类似物。

  DOI：

  10.1021/ol902270f

文献信息

• Cyclic amidine analogs as inhibitors of nitric oxide synthase
  申请人：Merck & Co., Inc.

  公开号：US05629322A1

  公开（公告）日：1997-05-13

  Disclosed herein are compounds of Formula I ##STR1## and pharmaceutically acceptable salts thereof which have been found useful in the treatment of nitric oxide synthase mediated diseases and disorders, including neurodegenerative disorders, disorders of gastrointestinal motility and inflammation. These disease and disorders include hypotension, septic shock, toxic shock syndrom, hemodialysis, IL-2 therapy such as in cancer patients, cachexia, immunosuppression such as in transplant therapy, autoimmune and/or inflammatory indications including sunburn or psoriasis and respiratory conditions such as bronchitis, asthma, and acure respiratory distress (ARDS), myocarditis, heart failure, atherosclerosis, arthritis, rheumatoid arthritis, chronic or inflammatory bowel disease, ulcerative colitis, Crohn's disease, systemic lupus erythematosis (SLE), ocular conditions such as ocular hypertension and uveitis, type 1 diabetes, insulin-dependent diabetes mellitus and cystic fibrosis. Compounds of Formula I are also usful in the treatment of hypoxia, hyperbaric oxygen convulsions and toxicity, dementia, Sydenham's chorea, Parkinson's disease, Huntington's disease, amyotrophic lateral sclerosis, mulitple sclerosis, Korsakoff's disease, imbecility related to cerebral vessel disorder, ischemic brain edema, sleeping disorders, schizophrenia, depression, PMS, anxiety, drug addiction, pain, migraine, immune complex disease, as immunosupressive agents and for preventing or reversing tolerance to opiates and diazepines.

  本文公开了I式化合物##STR1##及其药学上可接受的盐，发现其在治疗一氧化氮合酶介导的疾病和疾病方面有用，包括神经退行性疾病，胃肠动力障碍和炎症。这些疾病和疾病包括低血压，败血症休克，毒性休克综合征，血液透析，癌症患者的IL-2治疗，消瘦，移植治疗中的免疫抑制，自身免疫和/或炎症指示包括晒伤或银屑病以及呼吸系统疾病，如支气管炎，哮喘和急性呼吸窘迫综合征（ARDS），心肌炎，心力衰竭，动脉硬化，关节炎，类风湿性关节炎，慢性或炎症性肠病，溃疡性结肠炎，克隆病，系统性红斑狼疮（SLE），眼部疾病，如眼压和葡萄膜炎，1型糖尿病，胰岛素依赖性糖尿病和囊性纤维化。I式化合物也适用于治疗低氧，高压氧惊厥和毒性，痴呆，希登汉姆舞蹈病，帕金森病，亨廷顿病，肌萎缩性侧索硬化，多发性硬化，科萨科夫氏综合征，与脑血管疾病相关的低能力，缺血性脑水肿，睡眠障碍，精神分裂症，抑郁症，PMS，焦虑症，药物成瘾，疼痛，偏头痛，免疫复合物疾病，作为免疫抑制剂，并用于预防或逆转对鸦片类和苯二氮平的耐受性。
• Cycloalkyl-Substituted Imidazole Derivative
  申请人：Nagata Tsutomu

  公开号：US20130022587A1

  公开（公告）日：2013-01-24

  A compound represented by the following general formula (I) or a pharmacologically acceptable salt thereof, wherein A represents a C3 to C12 cycloalkyl group which may be substituted by one to three selected from a fluoro group, a hydroxy group, a C1 to C6 alkyl group, etc; R 1 , R 2 , and R 3 each independently represent a hydrogen atom, a fluoro group, or a C1 to C6 alkyl group; R 4 represents a hydrogen atom or a prodrug group; and Y represents —CH 2 —CHR 5 —CH 2 —NHR 6 (wherein R 5 represents a hydrogen atom, a C1 to C6 alkyl group, or a C1 to C6 alkoxy group, and R 6 represents a hydrogen atom or a prodrug group), or the like exhibits excellent TAFIa inhibitory activity and is useful as a therapeutic drug for myocardial infarction, angina pectoris, acute coronary syndrome, cerebral infarction, deep vein thrombosis, pulmonary embolism, and the like.

  以下是通式（I）所代表的化合物或其药学上可接受的盐，其中A代表一个C3到C12的环烷基，该环烷基可以被一个到三个选自氟基、羟基、C1到C6烷基等的基团所取代；R1、R2和R3各自独立地代表氢原子、氟基或C1到C6烷基；R4代表氢原子或前药基团；Y代表—CH2—CHR5—CH2—NHR6（其中R5代表氢原子、C1到C6烷基或C1到C6烷氧基，R6代表氢原子或前药基团）等，具有极好的TAFIa抑制活性，是治疗心肌梗死、心绞痛、急性冠状动脉综合征、脑梗死、深静脉血栓形成、肺栓塞等疾病的治疗药物。
• Cycloalkyl-substituted imidazole derivative
  申请人：Nagata Tsutomu

  公开号：US08609710B2

  公开（公告）日：2013-12-17

  A compound represented by the following general formula (I) or a pharmacologically acceptable salt thereof, wherein A represents a C3 to C12 cycloalkyl group which may be substituted by one to three selected from a fluoro group, a hydroxy group, a C1 to C6 alkyl group, etc; R1, R2, and R3 each independently represent a hydrogen atom, a fluoro group, or a C1 to C6 alkyl group; R4 represents a hydrogen atom or a prodrug group; and Y represents —CH2—CHR5—CH2—NHR6 (wherein R5 represents a hydrogen atom, a C1 to C6 alkyl group, or a C1 to C6 alkoxy group, and R6 represents a hydrogen atom or a prodrug group), or the like exhibits excellent TAFIa inhibitory activity and is useful as a therapeutic drug for myocardial infarction, angina pectoris, acute coronary syndrome, cerebral infarction, deep vein thrombosis, pulmonary embolism, and the like.

  以下为通式（I）所代表的化合物或其药理学上可接受的盐，其中A代表C3至C12的环烷基，该环烷基可以被氟基、羟基、C1至C6烷基等中的一种至三种取代；R1、R2和R3各自独立地表示氢原子、氟基或C1至C6烷基；R4表示氢原子或前药基团；而Y表示-CH2-CHR5-CH2-NHR6（其中R5表示氢原子、C1至C6烷基或C1至C6烷氧基，而R6表示氢原子或前药基团），等等。该化合物具有出色的TAFIa抑制活性，并可用作治疗心肌梗死、心绞痛、急性冠状动脉综合征、脑梗死、深静脉血栓形成、肺栓塞等疾病的治疗药物。
• CYCLOALKYL-SUBSTITUTED IMIDAZOLE DERIVATIVE
  申请人：Daiichi Sankyo Company, Limited

  公开号：EP2548871B1

  公开（公告）日：2017-07-19
• EP0789571A4
  申请人：——

  公开号：EP0789571A4

  公开（公告）日：1999-04-14