(1-异丁基-4-哌啶基)甲胺 | 258345-24-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: (1-异丁基-4-哌啶基)甲胺
• 英文名称: (1-iso-butyl-4-piperidyl)methylamine
• 英文别名: (1-isobutylpiperidin-4-yl)methylamine；1-(1-Isobutylpiperidin-4-YL)methanamine；[1-(2-methylpropyl)piperidin-4-yl]methanamine
• CAS: 258345-24-3
• 化学式: C₁₀H₂₂N₂
• 分子量: 170.298
• InChiKey: PGTRGAHRESDWCZ-UHFFFAOYSA-N

物化性质

• 沸点：
  212.1±8.0 °C(Predicted)
• 密度：
  0.881±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  6-氯苯并咪唑-4-羧酸 、 (1-异丁基-4-哌啶基)甲胺 在 N,N'-羰基二咪唑 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 以50%的产率得到N-(1-isobutyl-4-piperidyl)-6-chlorobenzimidazole-4-carboxamide
  参考文献：
  名称：

  Benzimidazole derivatives. Part 1: Synthesis and structure–activity relationships of new benzimidazole-4-carboxamides and carboxylates as potent and selective 5-HT4 receptor antagonists

  摘要：

  New benzimidazole-4-carboxamides 1-16 and -carboxylates 17-26 were synthesized and evaluated for binding affinity at serotonergic 5-HT4 and 5-HT3 receptors in the CNS. Most of the synthesized compounds exhibited moderate to-very high affinity tin many cases subnanomolar) for the 5-HT4 binding site and no significant affinity for the 5-HT3 receptor. SAR observations and structural analyses (molecular modeling, INSIGHT II) indicated that the presence of a voluminous substituent in the basic nitrogen atom of the amino moiety and a distance of ca. 8.0 Angstrom from this nitrogen to the aromatic ring are of great importance for high affinity and selectivity for 5-HT4 receptors. These results confirm our recently proposed model for recognition by the 5-HT4 binding site. Amides 12-15 and esters 24 and 25 bound at central 5-HT4 sites with very high affinity (K-j = 0.11-2.9 nM) and excellent selectivity over serotonin 5-HT3, 5-HT2A, and S-HT1A receptors (K-i > 1000-10,000 nM). Analogues 12 (k(i)(5-HT4) = 0.32 nM), 13 (K-i(5-HT4)= 0.11 nM), 14 (K-i(5-HT4) = 0.29 nM) and 15 (K-i(5-HT4) = 0.54 nM) were pharmacologically characterized as selective 5-HT4 antagonists in the isolated guinea pig ileum (pA(2) = 7.6, 7.9, 8.2 and 7.9, respectively), with a potency comparable to the 5-HT4 receptor antagonist RS 39604 (pA(2) = 8.2). The benzimidazoe-4-carboxylic acid derivatives described in this paper represent a novel class of potent and selective 5-HT4 receptor antagonists. In particular, compounds 12-15 could be interesting pharmacological tools for the understanding of the role of 5-HT4 receptors. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00172-8
• 作为产物：
  描述：

  溴代异丁烷 、 4-氨甲基哌啶 以 乙腈 为溶剂， 以63%的产率得到(1-异丁基-4-哌啶基)甲胺
  参考文献：
  名称：

  Benzimidazole derivatives. Part 1: Synthesis and structure–activity relationships of new benzimidazole-4-carboxamides and carboxylates as potent and selective 5-HT4 receptor antagonists

  摘要：

  New benzimidazole-4-carboxamides 1-16 and -carboxylates 17-26 were synthesized and evaluated for binding affinity at serotonergic 5-HT4 and 5-HT3 receptors in the CNS. Most of the synthesized compounds exhibited moderate to-very high affinity tin many cases subnanomolar) for the 5-HT4 binding site and no significant affinity for the 5-HT3 receptor. SAR observations and structural analyses (molecular modeling, INSIGHT II) indicated that the presence of a voluminous substituent in the basic nitrogen atom of the amino moiety and a distance of ca. 8.0 Angstrom from this nitrogen to the aromatic ring are of great importance for high affinity and selectivity for 5-HT4 receptors. These results confirm our recently proposed model for recognition by the 5-HT4 binding site. Amides 12-15 and esters 24 and 25 bound at central 5-HT4 sites with very high affinity (K-j = 0.11-2.9 nM) and excellent selectivity over serotonin 5-HT3, 5-HT2A, and S-HT1A receptors (K-i > 1000-10,000 nM). Analogues 12 (k(i)(5-HT4) = 0.32 nM), 13 (K-i(5-HT4)= 0.11 nM), 14 (K-i(5-HT4) = 0.29 nM) and 15 (K-i(5-HT4) = 0.54 nM) were pharmacologically characterized as selective 5-HT4 antagonists in the isolated guinea pig ileum (pA(2) = 7.6, 7.9, 8.2 and 7.9, respectively), with a potency comparable to the 5-HT4 receptor antagonist RS 39604 (pA(2) = 8.2). The benzimidazoe-4-carboxylic acid derivatives described in this paper represent a novel class of potent and selective 5-HT4 receptor antagonists. In particular, compounds 12-15 could be interesting pharmacological tools for the understanding of the role of 5-HT4 receptors. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00172-8

文献信息

• Imidazopyridine compounds as 5-HT4 receptor modulators
  申请人：——

  公开号：US20030092699A1

  公开（公告）日：2003-05-15

  This invention provides a compound of the formula (I): 1 or the pharmaceutically acceptable salts thereof wherein R 1 is hydrogen, halo or alkyl; R 2 and R 3 are independently hydrogen, alkyl, alkenyl, alkynyl, aminoalkyl or hydroxyalkyl; or R 2 and R 3 taken together with the nitrogen atom to which they are attached may form hetrocyclic; R 4 is hydrogen, halo, acyl, amino, amido, aryl, arylalkyl, or heteroaryl; R 5 is hydrogen, halo, alkyl, alkenyl, alkynyl, acyl, amino, amido, aryl, arylalkyl, or heteroaryl; R 6 is hydrogen, alkyl or alkoxyalkyl; X is NR 9 wherein R 9 is hydrogen or alkyl; and Y is (CR 7 R 8 ) n wherein n is an integer from 0 to 5. These compounds have 5-HT 4 receptor binding activity, and thus are useful for the treatment of gastroesophageal reflux disease, non-ulcer dyspepsia, Functional dyspepsia, irritable bowel syndrome or the like in mammalian, especially humans. This invention also provides a pharmaceutical composition comprising the above compound.

  这项发明提供了式(I)的化合物： 1 或其药学上可接受的盐，其中R 1 为氢、卤素或烷基；R 2 和R 3 独立地为氢、烷基、烯基、炔基、氨基烷基或羟基烷基；或R 2 和R 3 与它们连接的氮原子一起可能形成杂环；R 4 为氢、卤素、酰基、氨基、酰胺基、芳基、芳基烷基或杂芳基；R 5 为氢、卤素、烷基、烯基、炔基、酰基、氨基、酰胺基、芳基、芳基烷基或杂芳基；R 6 为氢、烷基或烷氧基烷基；X为NR 9 ，其中R 9 为氢或烷基；Y为(CR 7 R 8 ) n ，其中n为0至5的整数。 这些化合物具有5-HT 4 受体结合活性，因此对于哺乳动物，特别是人类的胃食管反流病、非溃疡性消化不良、功能性消化不良、肠易激综合征或类似疾病的治疗是有用的。该发明还提供了包含上述化合物的药物组合物。
• [EN] TRIAZOLO [4, 5 - B] PYRIDIN DERIVATIVES<br/>[FR] COMPOSÉS BICYCLIQUES DESTINÉS À ÊTRE UTILISÉS EN TANT QU'INHIBITEURS DE KINASES
  申请人：CT NAC INVESTIGACIONES ONCOLOGICAS CNIO

  公开号：WO2011101644A1

  公开（公告）日：2011-08-25

  There is provided compounds of formula (I), wherein R1, R2, R3 and R4 have meanings given in the description, and pharmaceutically-acceptable esters, amides, solvates or salts thereof, which compounds are useful in the treatment of diseases in which inhibition of a protein or lipid kinase (e.g. a PIM family kinase, such as PIM-1, PIM-2 and/or PIM-3, and/or Flt3) is desired and/or required, and particularly in the treatment of cancer or a proliferative disease.

  提供了化合物的公式(I)，其中R1、R2、R3和R4的含义如描述中所给出，并且其药用可接受的酯、酰胺、溶剂合物或盐，这些化合物在治疗需要或期望抑制蛋白激酶或脂质激酶（如PIM家族激酶，如PIM-1、PIM-2和/或PIM-3，和/或Flt3）的疾病中是有用的，特别是在癌症或增殖性疾病的治疗中。
• [EN] IMIDAZOPYRIDINE COMPUNDS AS 5-HT4 RECEPTOR AGONISTS<br/>[FR] COMPOSES D'IMIDAZOPYRIDINE COMME AGONISTES DU RECEPTEUR 5-HT4
  申请人：PFIZER PHARMA

  公开号：WO2004026869A1

  公开（公告）日：2004-04-01

  This invention provides a compound of the formula (I): (I) 5 wherein Rl represents a hydrogen atom or a halogen atom; R2 represents a methyl group or an ethyl group; R3 represents a branched alkyl group having from 3 to 6 carbon atoms or an alkyl group having from 3 to 6 carbon atoms substituted by an alkoxy group having from 1 to 6 carbon atoms; with the proviso that when the terminal carbon atom of said alkyl group is substituted by said alkoxy goroup, said alkyl group is a branched alkyl group; and pharmaceutically acceptable salts thereof. These compounds have 5-HT4 receptor binding activity, and thus are usefulfor the treatment of gastroesophageal reflux disease, non-ulcer dyspepsia, functional dyspepsia, irritable bowel syndrome or the like in mammalian, especially humans. This invention also provides a pharmaceutical composition comprising the above compound.

  本发明提供了式(I)的化合物，其中R1代表氢原子或卤素原子；R2代表甲基基团或乙基基团；R3代表分支烷基基团，其具有3到6个碳原子，或者是具有3到6个碳原子的烷基基团，其被1到6个碳原子的烷氧基取代；但是当所述烷基基团的末端碳原子被所述烷氧基取代时，所述烷基基团是一种分支烷基基团；以及其药学上可接受的盐。这些化合物具有5-HT4受体结合活性，因此对哺乳动物，特别是人类的胃食管反流病、非溃疡性消化不良、功能性消化不良、肠易激综合征等疾病的治疗是有用的。本发明还提供了包括上述化合物的制药组合物。
• [EN] IMIDAZOPYRIDINE COMPOUNDS AS 5-HT4 RECEPTOR MODULATORS<br/>[FR] COMPOSES D'IMIDAZOPYRIDINE EN TANT QUE MODULATEURS DU RECEPTEUR 5-HT4
  申请人：PFIZER PHARMA

  公开号：WO2003035649A1

  公开（公告）日：2003-05-01

  This invention provides a compound of the formula (I), or the pharmaceutically acceptable salts thereof wherein R1 is hydrogen, halo or alkyl; R?2 and R3¿ are independently hydrogen, alkyl, alkenyl, alkynyl, aminoalkyl or hydroxyalkyl; or R?2 and R3¿ taken together with the nitrogen atom to which they are attached may form hetrocyclic; R4 is hydrogen, halo, acyl, amino, amido, aryl, arylalkyl, or heteroaryl; R5 is hydrogen, halo, alkyl, alkenyl, alkynyl, acyl, amino, amido, aryl, arylalkyl, or heteroaryl; R6 is hydrogen, alkyl or alkoxyalkyl; X is NR9 wherein R9 is hydrogen or alkyl; and Y is (CR7R8) wherein n is an integer from 0 to 5. These compounds have 5-HT¿4? receptor binding activity, and thus are useful for the treatment of gastroesophageal reflux disease, non-ulcer dyspepsia, Functional dyspepsia, irritable bowel syndrome or the like in mammalian, especially humans. This invention also provides a pharmaceutical composition comprising the above compound.

  本发明提供了式(I)的化合物，或其在药学上可接受的盐，其中R1是氢，卤素或烷基；R2和R3分别是氢，烷基，烯基，炔基，氨基烷基或羟基烷基；或者R2和R3与它们连接的氮原子一起可以形成杂环；R4是氢，卤素，酰基，氨基，酰胺，芳基，芳基烷基或杂芳基；R5是氢，卤素，烷基，烯基，炔基，酰基，氨基，酰胺，芳基，芳基烷基或杂芳基；R6是氢，烷基或烷氧基烷基；X是NR9，其中R9是氢或烷基；而Y是(CR7R8)，其中n是0到5的整数。这些化合物具有5-HT4受体结合活性，因此适用于哺乳动物，特别是人类的治疗胃食管反流病，非溃疡性消化不良，功能性消化不良，肠易激综合征或类似疾病。本发明还提供了包含上述化合物的制药组合物。
• BICYCLIC COMPOUNDS AND METHODS OF MAKING AND USING SAME
  申请人：GHOSH Shomir

  公开号：US20100197723A1

  公开（公告）日：2010-08-05

  Disclosed herein are compounds that may be modulators of 5-HT receptors, and methods of making and using same.

  本文披露了可能是5-HT受体调节剂的化合物，以及制备和使用这些化合物的方法。