2-(trifluoromethyl)-1,4,5,6-tetrahydropyrrolo[2,4-d]imidazole | 945217-63-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-(trifluoromethyl)-1,4,5,6-tetrahydropyrrolo[2,4-d]imidazole
• 英文别名: 2-(Trifluoromethyl)-1,4,5,6-tetrahydropyrrolo[3,4-d]imidazole
• CAS: 945217-63-0
• 化学式: C₆H₆F₃N₃
• 分子量: 177.129
• InChiKey: NUMWDUZBMFQOGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  40.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(trifluoromethyl)-1,4,5,6-tetrahydropyrrolo[2,4-d]imidazole 、 N-[(2R,3S)-2-(2,5-二氟苯基)四氢-5-氧代-2H-吡喃-3-基]氨基甲酸叔丁酯 在 癸硼烷 作用下， 以 甲醇 为溶剂， 生成 、
  参考文献：
  名称：

  Novel tetrahydropyran analogs as dipeptidyl peptidase IV inhibitors: Profile of clinical candidate (2R,3S,5R)-2-(2,5-difluorophenyl)-5-[2-(methylsulfonyl)-2,6-dihydropyrrolo[3,4-c]pyrazol-5(4H)-yl]tetrahydro-2H-pyran-3-amine (23)

  摘要：

  A series of novel tri-2,3,5-substituted tetrahydropyran analogs were synthesized and evaluated as inhibitors of dipeptidyl peptidase IV (DPP-4) for the treatment of type 2 diabetes. Optimization of the series provided inhibitors with good DPP-4 potency and selectivity over other peptidases (QPP, DPP8, and FAP). Compound 23, which is very potent, selective, efficacious in the diabetes PD model, and has an excellent pharmacokinetic profile, is selected as a clinical candidate. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.07.061
• 作为产物：
  描述：

  tert-butyl 2-(trifluoromethyl)-4,6-dihydropyrrolo[3,4-d]imidazole-5(1H)-carboxylate 在 盐酸 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 2.0h， 生成 2-(trifluoromethyl)-1,4,5,6-tetrahydropyrrolo[2,4-d]imidazole
  参考文献：
  名称：

  WO2007/87231

  摘要：

  公开号：

文献信息

• Aminocyclohexanes as Dipeptidyl Peptidase-IV Inhibitors for the Treatment or Prevention of Diabetes
  申请人：Biftu Tesfaye

  公开号：US20090270467A1

  公开（公告）日：2009-10-29

  The present invention is directed to novel substituted aminocyclohexanes of structural formula (I) which are inhibitors of the dipeptidyl peptidase-IV enzyme and which are useful in the treatment or prevention of diseases in which the dipeptidyl peptidase-IV enzyme is involved, such as diabetes and particularly Type 2 diabetes. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which the dipeptidyl peptidase-IV enzyme is involved.

  本发明涉及结构式（I）的新型取代氨基环己烷，其是二肽基肽酶-IV酶的抑制剂，并且对于涉及二肽基肽酶-IV酶的疾病的治疗或预防，例如糖尿病，特别是2型糖尿病，具有用途。本发明还涉及包含这些化合物的制药组合物以及这些化合物和组合物在预防或治疗涉及二肽基肽酶-IV酶的疾病中的使用。
• AMINOCYCLOHEXANES AS DIPEPTIDYL PEPTIDASE-IV INHIBITORS FOR THE TREATMENT OR PREVENTION OF DIABETES
  申请人：Merck Sharp & Dohme Corp.

  公开号：EP1978804B1

  公开（公告）日：2014-07-30
• US7750034B2
  申请人：——

  公开号：US7750034B2

  公开（公告）日：2010-07-06
• [EN] AMINOCYCLOHEXANES AS DIPEPTIDYL PEPTIDASE-IV INHIBITORS FOR THE TREATMENT OR PREVENTION OF DIABETES<br/>[FR] AMINOCYCLOHEXANES UTILES EN TANT QU'INHIBITEURS DE LA DIPEPTIDYL PEPTIDASE-IV POUR TRAITER OU PRÉVENIR LE DIABÈTE
  申请人：MERCK & CO INC

  公开号：WO2007087231A2

  公开（公告）日：2007-08-02

  [EN] The present invention is directed to novel substituted aminocyclohexanes of structural formula (I) which are inhibitors of the dipeptidyl peptidase-IV enzyme and which are useful in the treatment or prevention of diseases in which the dipeptidyl peptidase-IV enzyme is involved, such as diabetes and particularly Type 2 diabetes. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which the dipeptidyl peptidase-IV enzyme is involved.
  [FR] La présente invention concerne de nouveaux aminocyclohexanes substitués représentés par la formule (I) qui sont des inhibiteurs de l'enzyme dipeptidyl peptidase-IV et qui sont utiles dans le traitement ou la prévention des maladies dans lesquelles est impliquée la dipeptidyl peptidase-IV, maladies telles que le diabète et plus particulièrement le diabète de type 2. Cette invention porte également sur des compositions pharmaceutiques comprenant lesdits composés et sur l'utilisation de ces composés et de ces compositions dans la prévention ou le traitement des maladies dans lesquelles la dipeptidyl peptidase-IV est impliquée.
• Novel tetrahydropyran analogs as dipeptidyl peptidase IV inhibitors: Profile of clinical candidate (2R,3S,5R)-2-(2,5-difluorophenyl)-5-[2-(methylsulfonyl)-2,6-dihydropyrrolo[3,4-c]pyrazol-5(4H)-yl]tetrahydro-2H-pyran-3-amine (23)
  作者：Tesfaye Biftu、Xiaoxia Qian、Ping Chen、Dennis Feng、Giovanna Scapin、Ying-Duo Gao、Jason Cox、Ranabir Sinha Roy、George Eiermann、Huabing He、Kathy Lyons、Gino Salituro、Sangita Patel、Alexander Petrov、Feng Xu、Shiyao Sherrie Xu、Bei Zhang、Charles Caldwell、Joseph K. Wu、Kathy Lyons、Ann E. Weber

  DOI：10.1016/j.bmcl.2013.07.061

  日期：2013.10

  A series of novel tri-2,3,5-substituted tetrahydropyran analogs were synthesized and evaluated as inhibitors of dipeptidyl peptidase IV (DPP-4) for the treatment of type 2 diabetes. Optimization of the series provided inhibitors with good DPP-4 potency and selectivity over other peptidases (QPP, DPP8, and FAP). Compound 23, which is very potent, selective, efficacious in the diabetes PD model, and has an excellent pharmacokinetic profile, is selected as a clinical candidate. (C) 2013 Elsevier Ltd. All rights reserved.