6-(三氟甲基)吡啶-3-羰基叠氮化物 | 648423-75-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 6-(三氟甲基)吡啶-3-羰基叠氮化物
• 英文名称: 6-(trifluoromethyl)nicotinyl azide
• 英文别名: 6-(Trifluoromethyl)pyridine-3-carbonyl azide
• CAS: 648423-75-0
• 化学式: C₇H₃F₃N₄O
• 分子量: 216.122
• InChiKey: WXVLVMGABAGEMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  44.3
• 氢给体数：
  0
• 氢受体数：
  6

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  6-三氟甲基烟酸	6-trifluoromethylnicotinic acid	231291-22-8	C7H4F3NO2	191.109
  6-三氟甲基烟酰氯	6-(trifluoromethyl)nicotinoyl chloride	358780-13-9	C7H3ClF3NO	209.555

反应信息

• 作为反应物：
  描述：

  6-(三氟甲基)吡啶-3-羰基叠氮化物 以 甲苯 为溶剂， 反应 1.5h， 生成 5-异氰酸基-2-三氟甲基-吡啶
  参考文献：
  名称：

  (+)-(2R,5S)-4-[4-Cyano-3-(trifluoromethyl)phenyl]-2,5-dimethyl-N-[6-(trifluoromethyl)pyridin-3- yl]piperazine-1-carboxamide (YM580) as an Orally Potent and Peripherally Selective Nonsteroidal Androgen Receptor Antagonist

  摘要：

  A novel series of trans-N-aryl-2,5-dimethylpiperazine-1-carboxamide derivatives was synthesized and their androgen receptor (AR) antagonist activities and in vivo antiandrogenic effects were evaluated. Pharmacological assays indicated that compound 33 was a potent AR antagonist, and subsequent optical resolution provided (+)-(2R,5S)-4-[4-cyano-3-(trifluoromethyl)phenyl]-2,5-dimethyl-N-[6-(trifluoromethyl)pyridin-3-yl]piperazine-1-carboxamide (33a, YM580) which exhibited the most potent antiandrogenic activity. Unlike bicalutamide, compound 33a decreased the weight of rat ventral prostate in a dose-dependent manner (ED50 = 2.2 mg/kg/day), and induced the maximum antiandrogenic effect, comparable to that of surgical castration, without significantly affecting serum testosterone levels. Compound 33a is a promising clinical candidate for prostate cancer monotherapy.

  DOI：

  10.1021/jm050293c
• 作为产物：
  描述：

  6-三氟甲基烟酰氯 在 sodium azide 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 0.67h， 生成 6-(三氟甲基)吡啶-3-羰基叠氮化物
  参考文献：
  名称：

  (+)-(2R,5S)-4-[4-Cyano-3-(trifluoromethyl)phenyl]-2,5-dimethyl-N-[6-(trifluoromethyl)pyridin-3- yl]piperazine-1-carboxamide (YM580) as an Orally Potent and Peripherally Selective Nonsteroidal Androgen Receptor Antagonist

  摘要：

  A novel series of trans-N-aryl-2,5-dimethylpiperazine-1-carboxamide derivatives was synthesized and their androgen receptor (AR) antagonist activities and in vivo antiandrogenic effects were evaluated. Pharmacological assays indicated that compound 33 was a potent AR antagonist, and subsequent optical resolution provided (+)-(2R,5S)-4-[4-cyano-3-(trifluoromethyl)phenyl]-2,5-dimethyl-N-[6-(trifluoromethyl)pyridin-3-yl]piperazine-1-carboxamide (33a, YM580) which exhibited the most potent antiandrogenic activity. Unlike bicalutamide, compound 33a decreased the weight of rat ventral prostate in a dose-dependent manner (ED50 = 2.2 mg/kg/day), and induced the maximum antiandrogenic effect, comparable to that of surgical castration, without significantly affecting serum testosterone levels. Compound 33a is a promising clinical candidate for prostate cancer monotherapy.

  DOI：

  10.1021/jm050293c

文献信息

• N-phenyl-(2r,5s) dimethylpiperadine derivative
  申请人：Taniguchi Nobuaki

  公开号：US20050261303A1

  公开（公告）日：2005-11-24

  The present invention relates to a novel N-phenyl-(2R,5S)dimethylpiperazine derivatives useful as antiandrogenic agent which exhibits a sufficient prostate gland reducing effect as compared with conventional compounds and are excellent in oral activity. The compound of the present application is useful in preventing or treating prostate cancer, benign prostatic hyperplasia, and the like. The present invention also provides a novel intermediate useful in producing the compound of the present invention.

  本发明涉及一种新型的N-苯基-(2R,5S)二甲基哌嗪衍生物，其作为抗雄激素剂具有足够的前列腺减少效果，与传统化合物相比具有出色的口服活性。本申请的化合物可用于预防或治疗前列腺癌、良性前列腺增生等疾病。本发明还提供了一种用于制备本发明化合物的新型中间体。
• N-Phenyl-(2R,5S)Dimethylpiperazine Derivative
  申请人：Taniguchi Nobuaki

  公开号：US20080214543A1

  公开（公告）日：2008-09-04

  The present invention relates to a novel N-phenyl-(2R,5S)dimethylpiperazine derivatives useful as antiandrogenic agent which exhibits a sufficient prostate gland reducing effect as compared with conventional compounds and are excellent in oral activity. The compound of the present application is useful in preventing or treating prostate cancer, benign prostatic hyperplasia, and the like. The present invention also provides a novel intermediate useful in producing the compound of the present invention.

  本发明涉及一种新型N-苯基-(2R,5S)二甲基哌嗪衍生物，其作为抗雄激素剂具有足够的前列腺减少效果，与传统化合物相比具有出色的口服活性。本申请的化合物在预防或治疗前列腺癌、良性前列腺增生等方面具有用途。本发明还提供了一种新型中间体，用于制备本发明的化合物。
• N-PHENYL-(2R,5S)DIMETHYLPIPERADINE DERIVATIVE
  申请人：YAMANOUCHI PHARMACEUTICAL CO. LTD.

  公开号：EP1557411A1

  公开（公告）日：2005-07-27

  The present invention relates to a novel N-phenyl-(2R,5S)dimethylpiperazine derivatives useful as antiandrogenic agent which exhibits a sufficient prostate gland reducing effect as compared with conventional compounds and are excellent in oral activity. The compound of the present application is useful in preventing or treating prostate cancer, benign prostatic hyperplasia, and the like. The present invention also provides a novel intermediate useful in producing the compound of the present invention.

  本发明涉及一种新型 N-苯基-(2R,5S)二甲基哌嗪衍生物，可用作抗雄激素制剂，与传统化合物相比，该衍生物具有足够的前列腺抑制作用，且口服活性极佳。本申请的化合物可用于预防或治疗前列腺癌、良性前列腺增生症等。本发明还提供了一种可用于生产本发明化合物的新型中间体。
• N-PHENYL-(2R,5S)DIMETHYLPIPERAZINE DERIVATIVE
  申请人：Astellas Pharma Inc.

  公开号：EP1557411B1

  公开（公告）日：2012-10-17
• US7297698B2
  申请人：——

  公开号：US7297698B2

  公开（公告）日：2007-11-20