4-[4-(2-isopropoxy-phenyl)-piperazin-1-yl]-cyclohexylamine | 870249-31-3

• 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: 4-[4-(2-isopropoxy-phenyl)-piperazin-1-yl]-cyclohexylamine
• 英文别名: 4-(4-{2-[(Propan-2-yl)oxy]phenyl}piperazin-1-yl)cyclohexan-1-amine；4-[4-(2-propan-2-yloxyphenyl)piperazin-1-yl]cyclohexan-1-amine
• CAS: 870249-31-3
• 化学式: C₁₉H₃₁N₃O
• 分子量: 317.475
• InChiKey: IORIMXNXRMNGPN-UHFFFAOYSA-N

物化性质

• 沸点：
  448.8±45.0 °C(Predicted)
• 密度：
  1.065±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  41.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-[4-(2-isopropoxy-phenyl)-piperazin-1-yl]-cyclohexylamine 在 sodium carbonate 、 乙酰氯 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.0h， 以100%的产率得到C₂₁H₃₃N₃O₂
  参考文献：
  名称：

  WO2006/50048

  摘要：

  公开号：
• 作为产物：
  描述：

  4-N-Boc-氨基环己酮 在 三乙酰氧基硼氢化钠 、 溶剂黄146 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 4-[4-(2-isopropoxy-phenyl)-piperazin-1-yl]-cyclohexylamine
  参考文献：
  名称：

  (Arylpiperazinyl)cyclohexylsufonamides: Discovery of α1a/1d-selective adrenergic receptor antagonists for the treatment of Benign Prostatic Hyperplasia/Lower Urinary Tract Symptoms (BPH/LUTS)

  摘要：

  Benign Prostatic Hyperplasia/Lower Urinary Tract Symptoms (BPH/LUTS) can be effectively treated by alpha(1)-adrenergic receptor antagonists. Unfortunately, all currently marketed alpha(1), blockers produced CV related side effects that are caused by the subtype non-selective nature of the drugs. To overcome this problem, it was postulated that a alpha(1a/1d) subtype selective antagonist would bring more benefit for the treatment of BPH/LUTS. In developing selective alpha(1a/1d) ligands, (arylpiperazinyl)cyclohexylsulfonamides were synthesized and their binding profiles against three cloned human alpha(1)-adrenergic receptor subtypes were evaluated. Many compounds show equal affinity for both alpha(1a), and alpha(1d) subtypes with good selectivity against the alpha(1b) subtype. They also overcome the problem of dopamine receptor affinity that previous analogues had exhibited. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.008

文献信息

• [EN] ADRENERGIC RECEPTOR ANTAGONISTS<br/>[FR] ANTAGONISTES DU RECEPTEUR ADRENERGIQUE
  申请人：RANBAXY LAB LTD

  公开号：WO2005113498A1

  公开（公告）日：2005-12-01

  This invention relates to α1a and/or α1d adrenergic receptor antagonists. Compounds disclosed herein can function as α1a and/or α1d adrenergic receptor antagonist and can be used for the treatment of diseases or disorder mediated through α1a and/or α1d adrenergic receptors. Compounds disclosed herein can be used for the treatment of benign prostatic hyperplasia and the related symptoms thereof. Compounds disclosed herein can be used for the treatment of lower urinary tract symptoms associated with or without benign prostatic hyperplasia. Processes for the preparation of compounds disclosed herein, pharmaceutical compositions containing the compounds disclosed herein, and methods of treating benign prostatic hyperplasia or related symptoms thereof are also provided. Formula (I) Its pharmaceutically acceptable acid addition salts,pharmaceutically acceptable solvates, enantiomers, diastereomers, N-oxides, polymorphs or metabolites,wherein; A represents a Formula (F.a or ,F.b or F.c wherein) N represents 1 or 2; Y represents cycloalkyl (C5-C7) group; optionally substituted with halogen atom(s) or lower alkyl (C1-C4) group; and R is selected from optionally substituted non_aromatic or aromatic monocyclic or bicyclic ring system having 0 to 4 heteroatom(s),the substituent(s) may be selected from the group consisting of halogen, lower alkyl (C1-C4),halogenated lower alkyl (C1-c4),cyano, hydroxy, lower alkoxy (C1-C4),cycloalkoxy (C3-C6),amino,lower alkylamino (C1-C4) and lower alkylamino (C1-C4) carbonyl group.

  本发明涉及α1a和/或α1d肾上腺素受体拮抗剂。本文披露的化合物可以作为α1a和/或α1d肾上腺素受体拮抗剂，并可用于治疗通过α1a和/或α1d肾上腺素受体介导的疾病或紊乱。本文披露的化合物可用于治疗良性前列腺增生及相关症状。本文披露的化合物可用于治疗与或不伴有良性前列腺增生相关的下尿路症状。还提供了用于制备本文披露的化合物的方法、含有本文披露的化合物的制药组合物，以及治疗良性前列腺增生或相关症状的方法。公式（I）及其药学上可接受的酸盐、药学上可接受的溶剂化合物、对映体、二对映体、N-氧化物、多型或代谢物，其中；A代表公式（F.a或，F.b或F.c其中）N代表1或2；Y代表环烷基（C5-C7）基团；可选择地取代卤原子或较低的烷基（C1-C4）基团；R选自可选择地取代的非芳香或芳香单环或双环环系统，具有0到4个杂原子，取代基可选自卤素、较低烷基（C1-C4）、卤代较低烷基（C1-C4）、氰基、羟基、较低烷氧基（C1-C4）、环烷氧基（C3-C6）、氨基、较低烷基氨基（C1-C4）和较低烷基氨基（C1-C4）羰基。
• Substituted [4-(4-phenyl-piperazin-1-yl)-cyclohexyl]-urea compounds
  申请人：Chiu George

  公开号：US20070123542A1

  公开（公告）日：2007-05-31

  The present invention relates to substituted [4-(4-phenyl-piperazin-1-yl)-cyclohexyl]-urea compounds of Formula (I) and pharmaceutically acceptable forms thereof, as α 1a /α 1d adrenoreceptor modulators for the treatment of benign prostatic hypertrophy and lower urinary tract symptoms. The present invention also relates to pharmaceutical compositions comprising said new compounds, new processes to prepare these new compounds and new uses as a medicine as well as methods of treatment.

  本发明涉及一种替代[4-(4-苯基哌嗪-1-基)-环己基]-脲化合物(I)及其药学上可接受的形式，作为α1a/α1d肾上腺素受体调节剂，用于治疗良性前列腺增生和下尿路症状。本发明还涉及包含所述新化合物的制药组合物、制备这些新化合物的新方法以及作为药物的新用途和治疗方法。
• Aminocyclohexylsulfonamides: Discovery of metabolically stable α1a/1d-selective adrenergic receptor antagonists for the treatment of benign prostatic hyperplasia/lower urinary tract symptoms (BPH/LUTS)
  作者：George Chiu、Shengjian Li、Hong Cai、Peter J. Connolly、Sean Peng、Kathe Stauber、Virginia Pulito、Jingchun Liu、Steven A. Middleton

  DOI：10.1016/j.bmcl.2007.09.051

  日期：2007.11

  Benign prostatic hyperplasia/lower urinary tract symptoms (BPH/LUTS) can be effectively treated by a, adrenergic receptor antagonists, but these drugs also produce side effects that are related to their subtype non-selective nature. To overcome this limitation, it was hypothesized that an alpha(1a/1d) subtype-selective antagonist would be efficacious while keeping side effects to a minimum. To discover alpha(1a/1d)-selective antagonists and improve metabolic stability of our previously reported compounds, we have designed and synthesized a series of (phenylpiperazinyl)- or (phenylpiperidinyl)-cyclohexylsulfonamides. By incorporating the information obtained from metabolism studies, we were able to discover several compounds that are both alpha(1a/1d) adrenoceptor subtype selective and show increased stability toward human liver microsomal metabolism. The selectivity profile of these compounds provides great improvement over the commercial drug tamsulosin, hence may pave the way to the development of new and efficacious therapeutic agents with reduced side effects. (C) 2007 Elsevier Ltd. All rights reserved.
• WO2007/5214
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  公开号：——

  公开（公告）日：——
• WO2007/1818
  申请人：——

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