3-(diethylamino)-2,2-dimethylpropyl 5-(4-chlorophenyl)-2-furancarboxylate hydrochloride | 55377-92-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: 3-(diethylamino)-2,2-dimethylpropyl 5-(4-chlorophenyl)-2-furancarboxylate hydrochloride
• 英文别名: 3-Diethylamino-2,2-dimethylpropyl 5-(p-Chlorophenyl)-2-furoate Hydrochloride；[3-(diethylamino)-2,2-dimethylpropyl] 5-(4-chlorophenyl)furan-2-carboxylate;hydrochloride
• CAS: 55377-92-9
• 化学式: C₂₀H₂₆ClNO₃*ClH
• 分子量: 400.345
• InChiKey: ARIBIEDOSMKRQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.55
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  42.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-(4-氯苯基)-2-呋喃甲酸 、 3-(二乙基氨基)-2,2-二甲基-1-丙醇 在 盐酸 、 氯化亚砜 作用下， 生成 3-(diethylamino)-2,2-dimethylpropyl 5-(4-chlorophenyl)-2-furancarboxylate hydrochloride
  参考文献：
  名称：

  苯基呋喃IV：5-取代的苯基-2-呋喃羧酸的水溶性3-二乙氨基-2,2-（二甲基）丙基酯

  摘要：

  制备了一系列3-二乙基氨基-2,2-（二甲基）丙基5-取代的苯基-2-呋喃甲酸酯，发现它们在体外具有作为胃肠道非抗胆碱能平滑肌解痉剂的药理活性。该系列中活性更高的化合物之一包含5-（4-硝基苯基）基团。

  DOI：

  10.1002/jps.2600690135

文献信息

• Use of 5-phenyl-2-furan esters and amides as antiepileptic agents
  申请人：Norwich Eaton Pharmaceuticals, Inc.

  公开号：US05023272A1

  公开（公告）日：1991-06-11

  A method of preventing epileptic seizures in a human or mammal subject susceptible to said seizures, comprising systemically administering to said subject a safe and effective amount of a compound of the formula: ##STR1## wherein (a) X is halo or hydrogen, and Y is a substituent selected from the group consisting of unsubstituted or halogen-substituted methyl, halo, nitro, amino, and methoxy; and (b) R is N(R.sup.3).sub.2, OR.sup.1 N(R.sup.3).sub.2, N(R.sup.2)R.sup.1 N(R.sup.3).sub.2, or N(R.sup.2)N(R.sup.3).sub.2 ; where R.sup.1 is C.sub.1 -C.sub.3 alkylene which is unsubstituted or substituted with C.sub.1 -C.sub.2 alkyl; R.sup.2 is hydrogen or lower alkyl; and each R.sup.3 is, independently, hydrogen or lower alkyl; or both R.sup.3 groups are connected to form a saturated 5- or 6-membered heterocycle containing 1 or 2 heteroatoms selected from oxygen and nitrogen and said heterocycle is unsubstituted or substituted with lower alkyl or hydroxy-substituted lower alkyl; or a pharmaceutically-acceptable salt thereof. Preferably X is halo, preferably Y is trifluoromethyl, and R is preferably 3-diethylamino-2,2-dimethylpropoxy.

  一种预防易患癫痫发作的人或哺乳动物主体的方法，包括向该主体系统地给予化合物的安全有效剂量，所述化合物的式为：##STR1## 其中（a）X为卤素或氢，Y为从未取代或卤素取代的甲基，卤素，硝基，氨基和甲氧基中选择的取代基；（b）R为N（R.sup.3）.sub.2，OR.sup.1 N（R.sup.3）.sub.2，N（R.sup.2）R.sup.1 N（R.sup.3）.sub.2或N（R.sup.2）N（R.sup.3）.sub.2；其中R.sup.1为未取代或取代为C.sub.1-C.sub.2烷基的C.sub.1-C.sub.3烷基；R.sup.2为氢或较低的烷基；每个R.sup.3独立地为氢或较低的烷基；或两个R.sup.3基团连接形成饱和的5-或6-成员杂环，其中包含从氧和氮中选择的1或2个杂原子，所述杂环未取代或取代为较低的烷基或羟基取代的较低的烷基；或其药学上可接受的盐。优选X为卤素，优选Y为三氟甲基，R优选为3-二乙氨基-2,2-二甲基丙氧基。
• Use of 5-phenyl-2-furan esters, amides and ketones as neuroprotective
  申请人：Norwich Eaton Pharmaceuticals, Inc.

  公开号：US05118708A1

  公开（公告）日：1992-06-02

  The present invention encompasses methods of using a 5-phenyl-2-furan esters, amides and ketones and compositions thereof to prevent or limit neuronal death or degeneration in a human or lower animal. These methods comprise systemically administering to such human or other animal a safe and effective amount of a compound of the formula: ##STR1## wherein (1) X is halo or nil; and Y is a substituent selected from the group consisting of unsubstituted or halogen-substituted methyl, halo, nitro, amino, and methoxy; and (2) R is R.sup.1 C(O)OH, R.sup.1 C(O)N(R.sup.3).sub.2, N(R.sup.3).sub.2, OR.sup.1 N(R.sup.3).sub.2, R.sup.1 N(R.sup.3).sub.2, N(R.sup.2)R.sup.1 N(R.sup.3).sub.2, or N(R.sup.2)N(R.sup.3).sub.2 ; where R.sup.1 is C.sub.1 -C.sub.3 alkyl which is unsubstituted or substituted with C.sub.1 -C.sub.2 alkyl; R.sup.2 is hydrogen or lower alkyl; and each R.sup.3 is, independently, hydrogen or lower alkyl; or both R.sup.3 groups are connected to form a saturated 5- or 6-membered heterocycle containing 1 or 2 heteroatoms selected from oxygen and nitrogen, and said heterocycle is unsubstituted or substituted with lower alkyl or hydroxy-substituted lower alkyl; or a pharmaceutically acceptable salt thereof.

  本发明涵盖使用5-苯基-2-呋喃酯、酰胺和酮及其组合物的方法，以预防或限制人类或低等动物的神经元死亡或退化。这些方法包括向这样的人类或其他动物系统地注入化合物的安全和有效量的公式：##STR1##其中（1）X为卤素或零；Y为取自以下基团的取代基：未取代或卤素取代的甲基，卤素，硝基，氨基和甲氧基；和（2）R为R.sup.1C（O）OH，R.sup.1C（O）N（R.sup.3）.sub.2，N（R.sup.3）.sub.2，OR.sup.1N（R.sup.3）.sub.2，R.sup.1N（R.sup.3）.sub.2，N（R.sup.2）R.sup.1N（R.sup.3）.sub.2或N（R.sup.2）N（R.sup.3）.sub.2；其中R.sup.1为未取代或取代为C.sub.1-C.sub.2烷基的C.sub.1-C.sub.3烷基；R.sup.2为氢或较低的烷基；每个R.sup.3都是独立的，为氢或较低的烷基；或两个R.sup.3基团连接成为一个饱和的5-或6-元杂环，其中包含1或2个从氧和氮中选择的杂原子，并且该杂环未取代或取代为较低的烷基或羟基取代的较低的烷基；或其药学上可接受的盐。
• The use of 5-phenyl-2 furan esters and amides as antiepileptic agents
  申请人：Norwich Eaton Pharmaceuticals, Inc.

  公开号：EP0404231A1

  公开（公告）日：1990-12-27

  A method of preventing epileptic seizures in a human or lower animal subject susceptible to said seizures, comprising systemically administering to said subject a safe and effective amount of a compound of the formula: wherein (a) X is halo or nil, and Y is a substituent selected from the group consisting of unsubstituted or halogen-substituted methyl, halo, nitro, amino, and methoxy; and (b) R is N(R³)₂, OR¹N(R³)₂, N(R²)R¹N(R³)₂, or N(R²)N(R³)₂; where R¹ is C₁-C₃ alkyl which is unsubstituted or substituted with C₁-C₂ alkyl; R² is hydrogen or lower alkyl; and each R³ is, independently, hydrogen or lower alkyl, or both R³ groups are connected to form a saturated 5- or 6-membered heterocycle containing 1 or 2 heteroatoms selected from oxygen and nitrogen and said heterocycle is unsubstituted or substituted with lower alkyl or hydroxy-substituted lower alkyl; or a pharmaceutically-acceptable salt thereof. Preferably X is halo, preferably Y is trifluoromethyl, and R is preferably 3-diethylamino-2,2-dimethylpropoxy.

  一种预防易受所述癫痫发作影响的人类或低等动物的癫痫发作的方法，包括向所述受试者全身施用安全有效量的式化合物： 其中 (a) X 是卤代或无，Y 是选自由未取代或卤代甲基、卤代、硝基、氨基和甲氧基组成的组的取代基；和 (b) R 是 N(R³)₂、OR¹N(R³)₂、N(R²)R¹N(R³)₂ 或 N(R²)N(R³)₂； 其中 R¹ 是未取代或被 C₁-C₂ 烷基取代的 C₁-C₃ 烷基； R² 是氢或低级烷基；以及 每个 R³ 独立地为氢或低级烷基，或两个 R³ 基团连接形成饱和的 5 或 6 元杂环，该杂环含有 1 或 2 个选自氧和氮的杂原子，且所述杂环未被取代或被低级烷基或羟基取代的低级烷基取代； 或其药学上可接受的盐。 X最好是卤代，Y最好是三氟甲基，R最好是3-二乙氨基-2,2-二甲基丙氧基。
• Novel use of 5-phenyl-2-furan esters, amides and ketones as neuroprotective agents
  申请人：Norwich Eaton Pharmaceuticals, Inc.

  公开号：EP0404233A2

  公开（公告）日：1990-12-27

  The present invention encompasses methods of using 5-phenyl-­2-furan esters, amides and ketones and compositions thereof to prevent or limit neuronal death or degeneration in a human or lower animal. These methods comprise systemically administering to such human or other animal a safe and effective amount of a compound of the formula: wherein (1) X is halo or nil; and Y is a substituent selected from the group consisting of unsubstituted or halogen-substituted methyl, halo, nitro, amino, and methoxy; and (2) R is R¹C(O)OH, R¹C(O)N(R³)₂, N(R³)₂, OR¹N(R³)₂, R¹N(R³)₂, N(R²)R¹N(R³)₂, or N(R²)N(R³)₂; where R¹ is C₁-C₃ alkyl which is unsubstituted or substituted with C₁-C₂ alkyl; R² is hydrogen or lower alkyl; and each R³ is, independently, hydrogen or lower alkyl; or both R³ groups are connected to form a saturated 5- or 6-membered heterocycle containing 1 or 2 heteroatoms selected from oxygen and nitrogen, and said heterocycle is unsubstituted or substituted with lower alkyl or hydroxy-substituted lower alkyl; or a pharmaceutically acceptable salt thereof.

  本发明包括使用 5-苯基-2-呋喃酯、酰胺和酮及其组合物防止或限制人或低等动物神经元死亡或变性的方法。这些方法包括向人或其他动物全身施用安全有效量的式化合物： 式中 (1) X 是卤代或零；Y 是选自由未取代或卤代甲基、卤代、硝基、氨基和甲氧基组成的组的取代基；和 (2) R 是 R¹C(O)OH、R¹C(O)N(R³)₂、N(R³)₂、OR¹N(R³)₂、R¹N(R³)₂、N(R²)R¹N(R³)₂ 或 N(R²)N(R³)₂；其中 R¹ 是未取代或被 C₁-C₂ 烷基取代的 C₁-C₃ 烷基； R² 是氢或低级烷基；以及 每个 R³ 独立地为氢或低级烷基；或两个 R³ 基团连接形成饱和的 5 或 6 元杂环，该杂环含有 1 或 2 个选自氧和氮的杂原子，且所述杂环未被取代或被低级烷基或羟基取代的低级烷基取代； 或其药学上可接受的盐。
• US5023272A
  申请人：——

  公开号：US5023272A

  公开（公告）日：1991-06-11