C-[4-(3,4-Difluoro-benzyl)-morpholin-2-yl]-methylamine | 610769-19-2

• 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: C-[4-(3,4-Difluoro-benzyl)-morpholin-2-yl]-methylamine
• 英文别名: 1-[4-(3,4-Difluorobenzyl)morpholin-2-yl]methanamine；[4-[(3,4-difluorophenyl)methyl]morpholin-2-yl]methanamine
• CAS: 610769-19-2
• 化学式: C₁₂H₁₆F₂N₂O
• mdl: MFCD25831033
• 分子量: 242.269
• InChiKey: DWKBWTXQPMQQLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-氨基-5-氯-2-乙氧基苯甲酸 、 C-[4-(3,4-Difluoro-benzyl)-morpholin-2-yl]-methylamine 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 4-Amino-5-chloro-N-[4-(3,4-difluoro-benzyl)-morpholin-2-ylmethyl]-2-ethoxy-benzamide
  参考文献：
  名称：

  Novel benzamides as selective and potent gastrokinetic agents. 2. Synthesis and structure-activity relationships of 4-amino-5-chloro-2-ethoxy-N-[[4-(4-fluorobenzyl)-2-morpholinyl]methyl]benzamide citrate (AS-4370) and related compounds

  摘要：

  The title compounds (19-55) with a 4-substituted 2-(aminomethyl) morpholine group were prepared and evaluated for the gastrokinetic activity by determining their effect on gastric emptying of phenol red semisolid meal in rats. Introduction of chloro, fluoro, and trifluoromethyl groups to the benzyl group of the parent compounds 1a and 1b enhanced the activity. Among compounds tested, 4-amino-5-chloro-2-ethoxy-N-[[4-(4-fluorobenzyl)-2-morpholinyl]?? methyl]benzamide (23b) showed the most potent gastic emptying activity (effects on phenol red semisolid meal in rats and mice, and on resin pellets solid meal in rats). The gastrokinetic activity of 23b citrate (AS-4370) compared very favorably with that of cisapride and was higher than that of metoclopramide. In contrast to metoclopramide and cisapride, AS-4370 was free from dopamine D2 receptor antagonistic activity in both in vitro ([H-3]spiperone binding) and in vivo (apomorphine-induced emesis in dogs) tests.

  DOI：

  10.1021/jm00106a023
• 作为产物：
  描述：

  2-(N-acetylaminomethyl)-4-benzylmorpholine 在 palladium on activated charcoal 盐酸 、 氢气 、 potassium carbonate 、 溶剂黄146 、 potassium iodide 作用下， 以 乙醇 、 丁酮 为溶剂， 反应 21.0h， 生成 C-[4-(3,4-Difluoro-benzyl)-morpholin-2-yl]-methylamine
  参考文献：
  名称：

  Novel benzamides as selective and potent gastrokinetic agents. 2. Synthesis and structure-activity relationships of 4-amino-5-chloro-2-ethoxy-N-[[4-(4-fluorobenzyl)-2-morpholinyl]methyl]benzamide citrate (AS-4370) and related compounds

  摘要：

  The title compounds (19-55) with a 4-substituted 2-(aminomethyl) morpholine group were prepared and evaluated for the gastrokinetic activity by determining their effect on gastric emptying of phenol red semisolid meal in rats. Introduction of chloro, fluoro, and trifluoromethyl groups to the benzyl group of the parent compounds 1a and 1b enhanced the activity. Among compounds tested, 4-amino-5-chloro-2-ethoxy-N-[[4-(4-fluorobenzyl)-2-morpholinyl]?? methyl]benzamide (23b) showed the most potent gastic emptying activity (effects on phenol red semisolid meal in rats and mice, and on resin pellets solid meal in rats). The gastrokinetic activity of 23b citrate (AS-4370) compared very favorably with that of cisapride and was higher than that of metoclopramide. In contrast to metoclopramide and cisapride, AS-4370 was free from dopamine D2 receptor antagonistic activity in both in vitro ([H-3]spiperone binding) and in vivo (apomorphine-induced emesis in dogs) tests.

  DOI：

  10.1021/jm00106a023
• 作为试剂：
  描述：

  [4-(3,4-dichlorobenzyl)morpholin-2-yl]methylamine 、 2,2,2-trifluoro-N-(morpholin-2-ylmethyl)acetamide 、 3,4-二氟溴苄 在 C-[4-(3,4-Difluoro-benzyl)-morpholin-2-yl]-methylamine 作用下， 生成 C-[4-(3,4-Difluoro-benzyl)-morpholin-2-yl]-methylamine
  参考文献：
  名称：

  Morpholin-acetamide derivatives for the treatment of inflammatory diseases

  摘要：

  化合物的公式（I），其中：R1代表C1-16烷基，C2-6烯基，C2-6炔基，C2-6炔基-Y1-，芳基-Y1-，杂环芳基-Y1-，芳基-(O)t-芳基-Y1-，芳基-(O)t-杂环芳基-Y1-，杂环芳基-(O)t-芳基-Y1-，杂环芳基-(O)t-杂环芳基-Y1-，C2-6烯基-Y1-，芳基-O-Y1-，杂环芳基-O-Y1-，C1-16烷基-SO2-Y1-，M-Y1-，J2-Y1-，-CN或C3-8环烷基-Y1-或C3-8环烯基-Y1-，其中环烷基或环烯基可以选择性地被一个或多个羟基或C1-16烷基取代；R2代表氢或C1-16烷基；X代表乙烯或公式CReRf的基团，其中Re和Rf独立地代表氢或C1-14烷基，或者Re和Rf可以与它们所连接的碳原子一起形成C3-8环烷基；R3和R4独立地代表氢或C1-14烷基；Z代表键，CO，SO2，CR9R6(CH2)n，(CH2)nCR9R6，CHR6(CH2)nO，CHR6(CH2)nS，CHR6(CH2)nOCO，CHR6(CH2)nCO，COCHR6(CH2)或SO2CHR6(CH2)n；n代表0到4的整数；制备它们的过程，包含它们的制剂以及它们在治疗炎症性疾病中的用途。

  公开号：

  US20040058923A1

文献信息

• Process for the preparation of morpholine derivatives and intermediates therefore
  申请人：Hayes Alistair Martin

  公开号：US20050222147A1

  公开（公告）日：2005-10-06

  Processes for the preparation of a compound of formula (IIIA) or a salt thereof are disclosed.

  本发明揭示了制备式（IIIA）化合物或其盐的过程。
• MORPHOLIN-ACETAMIDE DERIVATIVES FOR THE TREATMENT OF INFLAMMATORY DISEASES
  申请人：Ancliff Rachael Anne

  公开号：US20090163495A1

  公开（公告）日：2009-06-25

  There are provided according to the invention, novel compounds of formula (I) wherein R 1 , R 2 , R 3 , R 4 , R 5 , X, a, b and Z are as defined in the specification, processes for preparing them, formulations containing them and their use in therapy for the treatment of inflammatory diseases.

  根据本发明提供了新的化合物，化学式为（I），其中R1、R2、R3、R4、R5、X、a、b和Z的定义如规范中所述，制备它们的方法，包含它们的配方以及它们在治疗炎症性疾病中的应用。
• N-2s-4-3,4-difluorobenzyl morpholin-2yl methyl -2-(3-methylsulphonyl amino!phenyl acetamide as ccr3 antagonist for the treatment of inflammatory conditions
  申请人：Ancliff Ann Rachael

  公开号：US20060058299A1

  公开（公告）日：2006-03-16

  Compound of formula (I): and salts and solvates thereof, a process for its preparation, pharmaceutical formulations containing it and its use in therapy.

  式 (I) 的化合物： 及其盐类和溶解物、制备方法、含有该化合物的药物制剂和治疗用途。
• N- ¬(2S)-4-(3,4-DIFLUOROBENZYL)MORPHOLIN-2-YL METHYL -2- 3-¬(METHYLSULPHONYL)AMINO PHENYL ACETAMIDE AS CCR3 ANTAGONIST FOR THE TREATMENT OF INFLAMMATORY CONDITIONS
  申请人：GLAXO GROUP LIMITED

  公开号：EP1487453B1

  公开（公告）日：2010-01-13
• US7101882B2
  申请人：——

  公开号：US7101882B2

  公开（公告）日：2006-09-05