2-benzhydrylquinuclidin-3-amine | 129912-96-5

• 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: 2-benzhydrylquinuclidin-3-amine
• 英文别名: benzylquinuclidine-3-amine；2-Benzhydryl-3-aminochinuclidin；3-Amino-2-diphenylmethyl-1-azabicyclo[2.2.2]octane；2-diphenylmethyl-1-azabicyclo[2.2.2]octan-3-amine；(-)-(2S,3S)-cis-2-diphenylmethyl-1-azabicyclo[2.2.2]octane-3amine；2-benzhydryl-1-aza-bicyclo[2.2.2]oct-3-ylamine；3-amino-2-benzhydrylquinuclidine；2-Benzhydryl-1-azabicyclo[2.2.2]octan-3-amine
• CAS: 129912-96-5
• 化学式: C₂₀H₂₄N₂
• 分子量: 292.424
• InChiKey: MECDCHFRZHLREI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  29.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-碘苯甲醛 、 2-benzhydrylquinuclidin-3-amine 在 三乙酰氧基硼氢化钠 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以84%的产率得到2-Benzhydryl-N-(2-iodobenzyl)quinuclidin-3-amine
  参考文献：
  名称：

  Overcoming chloroquine resistance in malaria: Design, synthesis and structure–activity relationships of novel chemoreversal agents

  摘要：

  Malaria remains a significant infectious disease with even artemisinin-based therapies now facing resistance in the field. Development of new therapies is urgently needed, either by finding new compounds with unique modes of action, or by reversing resistance towards known drugs with 'chemosensitizers' or 'chemoreversal' agents (CRA). Concerning the latter, we have focused on the resistance mechanisms developed against chloroquine (CQ). We have synthesized a series of compounds related to previously identified CRAs, and found promising novel compounds. These compounds show encouraging results in a coumarin labeled chloroquine uptake assay, exhibiting a dose response in resensitising parasites to the antimalarial effects of chloroquine. Selected compounds show consistent potency across a panel of chloroquine and artemisinin sensitive and resistant parasites, and a wide therapeutic window. This data supports further study of CRAs in the treatment of malaria and, ultimately, their use in chloroquine-based combination therapies. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.04.058
• 作为产物：
  描述：

  2-Benzhydryl-3N-benzylaminochinuclidin 在 palladium on activated charcoal 、 甲酸铵 作用下， 以 乙醇 为溶剂， 以63.3 %的产率得到2-benzhydrylquinuclidin-3-amine
  参考文献：
  名称：

  CN117024453

  摘要：

  公开号：

文献信息

• Substituted benzylaminoquinuclidines as substance P antagonists
  申请人：Pfizer Inc.

  公开号：US05604241A1

  公开（公告）日：1997-02-18

  Compounds useful in the treatment of inflammatory disorders, central nervous system disorders and other disorders of the formula I ##STR1## and the pharmaceutically-acceptable salts thereof, wherein Ar.sup.1 and Ar.sup.2 are each independently aryl or substituted aryl; R.sup.1 is alkyl having from 1 to 6 carbon atoms; R.sup.2 is hydrogen or alkyl having from 1 to 6 carbon atoms; and either X and Y are taken separately and they are each, independently, hydrogen, dialkylphosphoryl having 2 to carbon atoms, alkyl having from 1 to 6 carbon atoms, alkenyl having from 2 to 6 carbon atoms or alkynyl having from 2 to 6 carbon atoms; or X and Y are taken together and they represent a hydrocarbon chain having 3, 4, or 5 carbon atoms, optionally containing up to 2 double bonds and optionally having 1 or 2 substituents selected from oxo, hydroxy and alkyl having from 1 to 6 carbon atoms; or Y is methoxy when X is ethyl; provided that when X and Y are taken together they are attached to adjacent carbon atoms; and provided that if either X or Y is hydrogen, then the other one must be alkenyl or alkynyl; and provided that when Y is methoxy and X is ethyl, then Y is at the 4-position and X is at the 5-position, Ar.sup.1 or Ar.sup.2 must each be phenyl, R.sup.1 is methyl and R.sup.2 is hydrogen.

  用于治疗炎症性疾病、中枢神经系统疾病和其他公式I的化合物##STR1##及其药用盐，其中Ar.sup.1和Ar.sup.2分别独立地为芳基或取代芳基；R.sup.1为具有1至6个碳原子的烷基；R.sup.2为氢或具有1至6个碳原子的烷基；X和Y分别取，并且它们分别独立地为氢、具有2至碳原子的二烷基磷酰基、具有1至6个碳原子的烷基、具有2至6个碳原子的烯基或具有2至6个碳原子的炔基；或者X和Y一起取，并且它们代表具有3、4或5个碳原子的碳氢链，可选地含有最多2个双键，并且可选地具有1或2个从氧代、羟基和具有1至6个碳原子的烷基中选择的取代基；或者当X为乙基时，Y为甲氧基；前提是当X和Y一起取时，它们连接到相邻的碳原子上；并且如果X或Y中的任一个为氢，则另一个必须为烯基或炔基；并且当Y为甲氧基且X为乙基时，Y位于4位，X位于5位，Ar.sup.1或Ar.sup.2必须为苯基，R.sup.1为甲基，R.sup.2为氢。
• Pharmaceutical uses for fluoroalkoxybenzylamino derivatives of nitrogen containing heterocycles
  申请人：——

  公开号：US20020035147A1

  公开（公告）日：2002-03-21

  The present invention relates to methods of treating various CNS and other disorders by adminstering fluoroalkoxybenzylamino derivatives of nitrogen containing heterocyclic compounds, and specifically, by administering compounds of the formula 1 wherein Q, X 1 , X 2 and X 3 are as defined below, and their pharmaceutically acceptable salts.

  本发明涉及通过给予含氮杂环化合物的氟烷氧基苄胺衍生物来治疗各种中枢神经系统和其他疾病的方法，具体地，通过给予以下公式中的化合物来治疗： 1 其中Q、X 1 、X 2 和X 3 如下所定义，并且它们的药用盐。
• Quinuclidine therapeutic agents
  申请人：Pfizer Inc.

  公开号：US05162339A1

  公开（公告）日：1992-11-10

  A series of cis-3-[(cyclic)methylamino]-2-[(.alpha.-substituted)arylmethyl]quinuclidin es, 3-[(cyclic)methylimino]-2-[(.alpha.-substituted)-arylmethyl]quinuclidines and cis-3-[(cyclic)-methyleneamino]-2-[(.alpha.-substituted)arylmethyl]-quinuc lidines, including their pharmaceutically acceptable salts, are disclosed. These particular compounds are found to be useful as substance P antagonists and therefore, are of value in treating gastrointestinal disorders, central nervous system disorders, inflammatory diseases and pain or migraine. Preferred member compounds include cis-3-[(2-chlorophenyl)methylamino]-2-benzhydryl-quinuclidine, cis-3-[(2-trifluorophenyl)methylamino]2-benzhydrylquinuclidine and cis-[(2-methoxyphenyl)methylamino]-2-benzhydrylquinuclidine. Methods for preparing these compounds from known starting materials are provided.

  一系列cis-3-[(环)cyclic)methylamino]-2-[(.alpha.-取代)aryl甲基]喹诺啡啶、3-[(环)cyclic)methylimino]-2-[(.alpha.-取代)aryl甲基]喹诺啡啶和cis-3-[(环)-亚甲基氨基]-2-[(.alpha.-取代)aryl甲基]-喹诺啡啶，包括它们的药用盐。发现这些特定化合物在作为P物质拮抗剂方面具有用途，因此在治疗胃肠道疾病、中枢神经系统疾病、炎症性疾病和疼痛或偏头痛方面具有价值。首选化合物包括cis-3-[(2-氯苯基)甲基氨基]-2-苯基二苯基喹诺啡啶、cis-3-[(2-三氟苯基)甲基氨基]2-苯基二苯基喹诺啡啶和cis-[(2-甲氧基苯基)甲基氨基]-2-苯基二苯基喹诺啡啶。提供了从已知起始物质制备这些化合物的方法。
• [EN] PROCESS FOR THE PREPARATION OF (S,S)-CIS-2-BENZHYDRYL-3-BENZYLAMINOQUINUCLIDINE<br/>[FR] PROCEDE DE PREPARATION DE (S,S)-CIS-2-BENZHYDRYL-3-BENZYLAMINOQUINUCLIDINE
  申请人：PFIZER PROD INC

  公开号：WO2004035575A1

  公开（公告）日：2004-04-29

  A process for preparing (S,S)-cis-2-benzhydryl-3-benzylaminoquinuclidine. The process includes the steps of contacting a compound containing a mixture of R- and S-isomers and having Formula (I), with an effective amount of a chiral organic acid in the presence of an organic solvent and an effective amount of an organic carboxylic acid for converting the R-isomer into an acid salt of the S isomer, wherein the organic solvent is capable of solubilizing the compound containing the mixture of R- and S-isomers, while precipitating the acid salt and the organic carboxylic acid is different from the chiral organic acid; neutralizing the acid salt with a base to provide an S-isomer of a chiral ketone of Formula (II), and reacting the chiral ketone with an organic amine in the presence of a Lewis acid to provide the corresponding imine and reducing the imine.

  一种制备(S,S)-顺式-2-苄基-3-苄基氨基喹啉的方法。该方法包括以下步骤：将含有R-和S-异构体混合物且具有化学式(I)的化合物与有效量的手性有机酸在有机溶剂存在下接触，并加入有效量的有机羧酸以将R-异构体转化为S异构体的酸盐，其中有机溶剂能溶解含有R-和S-异构体混合物的化合物，同时沉淀出酸盐，有机羧酸与手性有机酸不同；用碱中和酸盐以提供化学式(II)的手性酮的S-异构体，并在路易斯酸存在下将手性酮与有机胺反应以提供相应的亚胺，然后还原亚胺。
• [EN] FLUOROALKOXYBENZYLAMINO DERIVATIVES OF NITROGEN CONTAINING HETEROCYCLES
  申请人：PFIZER INC.

  公开号：WO1993000331A1

  公开（公告）日：1993-01-07

  (EN) The present invention relates to novel fluoroalkoxybenzylamino derivatives of nitrogen containing heterocyclic compounds, and specifically, to compounds of formula (I) wherein Q, X1, X2 and X3 are as defined below. These novel compounds are useful in the treatment of inflammatory and central nervous system disorders, as well as other disorders.(FR) La présente invention à trait à de nouveaux dérivés fluoroalcoxybenzylamino de composés hétérocycliques contenant de l'azote et, spécialement, à des composés de la formule (I) dans laquelle Q, X1, X2 et X3 ont la notation ci-définie. Ces nouveaux composés sont utiles pour le traitement des affections inflammatoires et des troubles du système nerveux central ainsi que pour d'autres affections.

  该发明涉及一种新型含氮杂环化合物的氟烷氧基苯基氨基衍生物，具体而言，涉及式（I）中Q、X1、X2和X3定义如下的化合物。这些新化合物在治疗炎症和中枢神经系统疾病以及其他疾病方面具有用途。