1-(3,5-difluorophenyl)-2-methylpiperazine | 475653-31-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 1-(3,5-difluorophenyl)-2-methylpiperazine
• CAS: 475653-31-7
• 化学式: C₁₁H₁₄F₂N₂
• 分子量: 212.242
• InChiKey: XIBGROAXEIYBKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  15.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(3,5-difluorophenyl)-2-methylpiperazine 在 盐酸 、 sodium cyanoborohydride 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醇 为溶剂， 反应 21.5h， 生成 2-[4-[(E)-3-[4-(3,5-difluorophenyl)-3-methylpiperazin-1-yl]prop-1-enyl]-5-methylpyrazol-1-yl]pyrimidine
  参考文献：
  名称：

  Synthesis and Antitumor Activity of Novel Pyrimidinyl Pyrazole Derivatives. II. Optimization of the Phenylpiperazine Moiety of 1-[5-Methyl-1-(2-pyrimidinyl)-4-pyrazolyl]-3-phenylpiperazinyl-1-trans-propenes.

  摘要：

  为提高原型化合物3-[4-(3-氯苯基)-1-哌嗪基]-1-[5-甲基-1-(2-嘧啶基)-4-吡唑基]-1-反式-丙烯（2）的体外和体内活性，合成了一系列新型的3-取代-1-[5-甲基-1-(2-嘧啶基)-4-吡唑基]-1-反式-丙烯，并通过体外对几种肿瘤细胞系的生长抑制试验和体内对某些肿瘤模型的抗肿瘤活性试验（经腹腔和口服给药）进行了评估。化合物7a和7e，分别是2的3,5-二氟苯基和3,5-二氯苯基类似物，其体外细胞毒性显著强于2，并有较强的抗肿瘤活性，且不会因副作用导致体温下降。

  DOI：

  10.1248/cpb.50.453
• 作为产物：
  描述：

  3,5-difluoroaniline hydrochloride 在 lithium aluminium tetrahydride 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 142.33h， 生成 1-(3,5-difluorophenyl)-2-methylpiperazine
  参考文献：
  名称：

  Synthesis and Antitumor Activity of Novel Pyrimidinyl Pyrazole Derivatives. II. Optimization of the Phenylpiperazine Moiety of 1-[5-Methyl-1-(2-pyrimidinyl)-4-pyrazolyl]-3-phenylpiperazinyl-1-trans-propenes.

  摘要：

  为提高原型化合物3-[4-(3-氯苯基)-1-哌嗪基]-1-[5-甲基-1-(2-嘧啶基)-4-吡唑基]-1-反式-丙烯（2）的体外和体内活性，合成了一系列新型的3-取代-1-[5-甲基-1-(2-嘧啶基)-4-吡唑基]-1-反式-丙烯，并通过体外对几种肿瘤细胞系的生长抑制试验和体内对某些肿瘤模型的抗肿瘤活性试验（经腹腔和口服给药）进行了评估。化合物7a和7e，分别是2的3,5-二氟苯基和3,5-二氯苯基类似物，其体外细胞毒性显著强于2，并有较强的抗肿瘤活性，且不会因副作用导致体温下降。

  DOI：

  10.1248/cpb.50.453

文献信息

• [EN] N-PHENYL-PIPERAZINE DERIVATIVES AND METHODS OF PROPHYLAXIS OR TREATMENT OF 5HT2C RECEPTOR ASSOCIATED DISEASES<br/>[FR] DERIVES DE N-PHENYL-PIPERAZINE ET METHODES DE PROPHYLAXIE OU DE TRAITEMENT DE MALADIES ASSOCIEES AU RECEPTEUR 5HT2C
  申请人：ARENA PHARM INC

  公开号：WO2005016902A1

  公开（公告）日：2005-02-24

  The present invention relates to certain substituted N-phenyl-piperazine derivatives of Formula: (I) that are modulators of the 5HT2c receptor. Accordingly, compounds of the present invention are useful for the prophylaxis or treatment of 5HT2c receptor associated diseases or disorders, such as, obesity, Alzheimer Disease, erectile dysfunction and related disorders.

  本发明涉及某些Formula: (I)的取代N-苯基哌嗪衍生物，它们是5HT2c受体的调节剂。因此，本发明的化合物对于预防或治疗与5HT2c受体相关的疾病或紊乱，如肥胖症、阿尔茨海默病、勃起功能障碍及相关疾病，是有用的。
• N-phenyl-piperazine derivatives and methods of prophylaxis or treatment of 5ht2c receptor associated diseases
  申请人：Smith Brian

  公开号：US20070179155A1

  公开（公告）日：2007-08-02

  The present invention relates to certain substituted N-phenyl-piperazine derivatives of Formula: (I) that are modulators of the 5HT 2c receptor. Accordingly, compounds of the present invention are useful for the prophylaxis or treatment of 5HT 2c receptor associated diseases or disorders, such as, obesity, Alzheimer Disease, erectile dysfunction and related disorders.

  本发明涉及某些替代N-苯基哌嗪衍生物，其化学式为：(I)，它们是5HT2c受体的调节剂。因此，本发明的化合物对于预防或治疗与5HT2c受体相关的疾病或疾病，如肥胖症、阿尔茨海默病、勃起功能障碍和相关疾病是有用的。
• 1,2,3-TRIAZOLO [4,3-A] PYRIDINE DERIVATIVES AND THIER USE FOR THE TREATMENT OF PREVENTION OF NEUROLOGICAL AND PSYCHIATRIC DISORDERS
  申请人：Cid-Nunez Jose Maria

  公开号：US20120184525A1

  公开（公告）日：2012-07-19

  The present invention relates to novel triazolo[4,3- a ]pyridine derivatives of Formula (I) wherein all radicals are as defined in the claims. The compounds according to the invention are positive allosteric modulators of the metabotropic glutamate receptor subtype 2 (“mGluR2”), which are useful for the treatment or prevention of neurological and psychiatric disorders associated with glutamate dysfunction and diseases in which the mGluR2 subtype of metabotropic receptors is involved. The invention is also directed to pharmaceutical compositions comprising such compounds, to processes to prepare such compounds and compositions, and to the use of such compounds for the prevention or treatment of neurological and psychiatric disorders and diseases in which mGluR2 is involved.

  本发明涉及一种新型的三唑并[4,3-a]吡啶衍生物，其化学式为（I），其中所有基团均如权利要求中所定义。本发明中的化合物是代谢型谷氨酸受体亚型2（“mGluR2”）的正向变构调节剂，可用于治疗或预防与谷氨酸功能障碍有关的神经和精神障碍以及涉及代谢型受体的mGluR2亚型的疾病。本发明还涉及包含这些化合物的制药组合物，制备这些化合物和组合物的过程，以及使用这些化合物预防或治疗涉及mGluR2的神经和精神障碍和疾病的方法。
• 1,2,4-Triazolo [4,3-A] Pyridine Derivatives and Their Use For The Treatment of Prevention of Neurological and Psychiatric Disorders
  申请人：JANSSEN PHARMACEUTICALS, INC.

  公开号：US20150141403A1

  公开（公告）日：2015-05-21

  The present invention relates to novel triazolo[4,3-a]pyridine derivatives of Formula (I) wherein all radicals are as defined in the claims. The compounds according to the invention are positive allosteric modulators of the metabotropic glutamate receptor subtype 2 (“mGluR2”), which are useful for the treatment or prevention of neurological and psychiatric disorders associated with glutamate dysfunction and diseases in which the mGluR2 subtype of metabotropic receptors is involved. The invention is also directed to pharmaceutical compositions comprising such compounds, to processes to prepare such compounds and compositions, and to the use of such compounds for the prevention or treatment of neurological and psychiatric disorders and diseases in which mGluR2 is involved.

  本发明涉及一种新型的三唑并[4,3-a]吡啶衍生物，其化学式为（I），其中所有基团如权利要求所定义。本发明的化合物是代谢型谷氨酸受体亚型2（“mGluR2”）的正向变构调节剂，可用于治疗或预防与谷氨酸功能障碍相关的神经和精神障碍以及涉及代谢型受体亚型mGluR2的疾病。本发明还涉及包含这种化合物的制药组合物、制备这种化合物和组合物的过程，以及使用这种化合物预防或治疗涉及mGluR2的神经和精神障碍和疾病的方法。
• 1,2,4-triazolo [4,3-A] pyridine derivatives and their use for the treatment of neurological and psychiatric disorders
  申请人：JANSSEN PHARMACEUTICALS, INC.

  公开号：US10071095B2

  公开（公告）日：2018-09-11

  The present invention relates to methods of treating various central nervous system disorders using novel triazolo[4,3-a]pyridine derivatives of Formula (I) wherein all radicals are as defined in the claims. The compounds according to the invention are positive allosteric modulators of the metabotropic glutamate receptor subtype 2 (“mGluR2”), which are useful for the treatment or prevention of neurological and psychiatric disorders associated with glutamate dysfunction and diseases in which the mGluR2 subtype of metabotropic receptors is involved. The invention is also directed to pharmaceutical compositions comprising such compounds, to processes to prepare such compounds and compositions, and to the use of such compounds for the prevention or treatment of neurological and psychiatric disorders and diseases in which mGluR2 is involved.

  本发明涉及使用式 (I) 的新型三唑并[4,3-a]吡啶衍生物治疗各种中枢神经系统疾病的方法 其中所有基团如权利要求中定义。根据本发明的化合物是代谢型谷氨酸受体亚型 2（"mGluR2"）的正异位调节剂，可用于治疗或预防与谷氨酸功能障碍相关的神经和精神疾病以及代谢型受体 mGluR2 亚型参与的疾病。本发明还涉及包含此类化合物的药物组合物、制备此类化合物和组合物的工艺，以及使用此类化合物预防或治疗涉及 mGluR2 的神经和精神障碍及疾病。