1-[(5-{[(3-methoxybenzoyl)amino]methyl}thiophe-2-yl)-sulfonyl]piperidin-4-ammonium trifluoroacetate | 406679-36-5

• 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: 1-[(5-{[(3-methoxybenzoyl)amino]methyl}thiophe-2-yl)-sulfonyl]piperidin-4-ammonium trifluoroacetate
• 英文别名: [1-[5-[[(3-Methoxybenzoyl)amino]methyl]thiophen-2-yl]sulfonylpiperidin-4-yl]azanium;2,2,2-trifluoroacetate
• CAS: 406679-36-5
• 化学式: C₂HF₃O₂*C₁₈H₂₃N₃O₄S₂
• 分子量: 523.554
• InChiKey: RIUVSHKKGODVQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.38
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  180
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  对三氟甲基苯甲醛 、 1-[(5-{[(3-methoxybenzoyl)amino]methyl}thiophe-2-yl)-sulfonyl]piperidin-4-ammonium trifluoroacetate 在 N,N-二异丙基乙胺 、 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 DMF (N,N-dimethyl-formamide) 、 1,2-二氯乙烷 为溶剂， 反应 0.5h， 生成 3-methoxy-N-({5-[(4-{[4-(trifluoromethyl)benzyl]amino}piperidin-1-yl)sulfonyl]thien-2-yl}methyl)benzamide
  参考文献：
  名称：

  Pharmaceutically active sulfonamide derivatives bearing both lipophilic and ionisable moieties as inhibitors of protein Junkinases

  摘要：

  本发明涉及具有亲脂基团并在生理条件下基本可溶的磺胺基衍生物。所述化合物特别适用作药用活性化合物。本发明还涉及含有这种磺胺基衍生物的药物配方。所述磺胺基衍生物是JNK途径的高效调节剂，特别是JNK 2和3的高效和选择性抑制剂。本发明还涉及新型磺胺基衍生物以及它们的制备方法。 根据本发明的式I化合物适用于药用剂的那些化合物是这样的： Ar1和Ar2分别独立地是取代或未取代的芳基或杂环芳基， X是O或S，优选为O； R1是氢或C1-C6烷基，或R1与Ar1形成取代或未取代的5-6元饱和或不饱和环； n是0到5的整数，优选为1-3之间，最优选为1； 式I中的Y是未取代或取代的4-12元饱和环或双环烷基，其上取代有至少一个可离子化基团，该基团连接有一个亲脂链，并且含有至少一个氮原子，其中所述环中的一个氮原子与式I的磺酰基形成键合，从而提供磺胺基。

  公开号：

  EP1193268A1
• 作为产物：
  描述：

  tert-butyl 1-[(5-{[(3-methoxybenzoyl)amino]methyl}thiophe-2-yl)-sulfonyl]piperidin-4-ylcarbamate 、 三氟乙酸 以82%的产率得到1-[(5-{[(3-methoxybenzoyl)amino]methyl}thiophe-2-yl)-sulfonyl]piperidin-4-ammonium trifluoroacetate
  参考文献：
  名称：

  Pharmaceutically active sulfonamide derivatives bearing both lipophilic and ionisable moieties as inhibitors of protein Junkinases

  摘要：

  本发明涉及具有亲脂基团并在生理条件下基本可溶的磺胺基衍生物。所述化合物特别适用作药用活性化合物。本发明还涉及含有这种磺胺基衍生物的药物配方。所述磺胺基衍生物是JNK途径的高效调节剂，特别是JNK 2和3的高效和选择性抑制剂。本发明还涉及新型磺胺基衍生物以及它们的制备方法。 根据本发明的式I化合物适用于药用剂的那些化合物是这样的： Ar1和Ar2分别独立地是取代或未取代的芳基或杂环芳基， X是O或S，优选为O； R1是氢或C1-C6烷基，或R1与Ar1形成取代或未取代的5-6元饱和或不饱和环； n是0到5的整数，优选为1-3之间，最优选为1； 式I中的Y是未取代或取代的4-12元饱和环或双环烷基，其上取代有至少一个可离子化基团，该基团连接有一个亲脂链，并且含有至少一个氮原子，其中所述环中的一个氮原子与式I的磺酰基形成键合，从而提供磺胺基。

  公开号：

  EP1193268A1

文献信息

• Pharmaceutically active sulfonamide derivatives bearing both lipophilic and ionisable moietties as inhibitors of protein junkinases
  申请人：——

  公开号：US20040077854A1

  公开（公告）日：2004-04-22

  The present invention is related to sulfonamide derivatives having a lipophilic moiety and which are substantially soluble. Said compounds are notably for use as pharmaceutically active compounds. The present invention also related to pharmaceutical formulations containing such sulfonamide derivatives. Said sulfonamide derivatives are efficient modulators of the JNK pathway, they are in particular efficient and selective inhibitors of JNK 2 and 3. The present invention is furthermore related to novel sulfonamide derivatives as well as to methods of their preparation. The compounds of formula (I) according to the present invention being suitable pharmaceutical agents are those wherein Ar1 and Ar2 are independently from each other substituted or unsubstituted aryl or heteroaryl groups, X is O or S, preferably O;R1 is hydrogen or a C1-C6-alkyl group, or R1 forms a substituted or unsubstituted 5-6-membered saturated or unsaturated ring with Ar1;n is an integer from 0 to 5, preferably between 1-3 and most preferred 1;Y within formula (I) is an unsubstituted or a substituted 4-12-membered saturated cyclic or bicyclic alkyl which is substituted with at least one ionisable moiety to which a lipophilic chain is attached and which is containing at least one nitrogen atom, whereby one nitrogen atom within said ring is forming a bond with the sulfonyl group of formula (I) thus providing a sulfonamide.

  本发明涉及具有亲脂基团且基本溶解的磺酰胺衍生物，该化合物特别适用于作为药物活性化合物。本发明还涉及含有这种磺酰胺衍生物的药物制剂。该磺酰胺衍生物是JNK途径的有效调节剂，尤其是JNK2和3的有效和选择性抑制剂。本发明还涉及新的磺酰胺衍生物以及它们的制备方法。本发明所述的公式（I）化合物适用于药物制剂，其中Ar1和Ar2分别是取代或未取代的芳基或杂环芳基基团，X为O或S，优选为O；R1为氢或C1-C6烷基，或R1与Ar1形成取代或未取代的5-6元饱和或不饱和环；n为0到5的整数，优选为1-3，最优选为1；公式（I）中的Y是未取代或取代的4-12元饱和环或双环烷基，其被至少一个离子化基团取代，并连接有一个亲脂链，并且含有至少一个氮原子，其中该环中的一个氮原子与公式（I）中的磺酰基形成键合，从而提供磺酰胺。
• US7544700B2
  申请人：——

  公开号：US7544700B2

  公开（公告）日：2009-06-09
• Pharmaceutically active sulfonamide derivatives bearing both lipophilic and ionisable moieties as inhibitors of protein Junkinases
  申请人：Applied Research Systems ARS Holding N.V.

  公开号：EP1193268A1

  公开（公告）日：2002-04-03

  The present invention is related to sulfonamide derivatives having a lipophilic moiety and which are substantially soluble under physiological conditions. Said compounds are notably for use as pharmaceutically active compounds. The present invention also related to pharmaceutical formulations containing such sulfonamide derivatives. Said sulfonamide derivatives are efficient modulators of the JNK pathway, they are in particular efficient and selective inhibitors of JNK 2 and 3. The present invention is furthermore related to novel sulfonamide derivatives as well as to methods of their preparation. The compounds of formula I according to the present invention being suitable pharmaceutical agents are those wherein Ar1 and Ar2 are independently from each other substituted or unsubstituted aryl or heteroaryl groups, X is O or S, preferably O; R1 is hydrogen or a C1-C6-alkyl group, or R1 forms a substituted or unsubstituted 5-6-membered saturated or unsaturated ring with Ar1; n is an integer from 0 to 5, preferably between 1-3 and most preferred 1; Y within formula I is an unsubstituted or a substituted 4-12-membered saturated cyclic or bicyclic alkyl which is substituted with at least one ionisable moiety to which a lipophilic chain is attached and which is containing at least one nitrogen atom, whereby one nitrogen atom within said ring is forming a bond with the sulfonyl group of formula I thus providing a sulfonamide.ring is forming a bond with the sulfonyl group of formula I thus providing a sulfonamide.

  本发明涉及具有亲脂基团并在生理条件下基本可溶的磺胺基衍生物。所述化合物特别适用作药用活性化合物。本发明还涉及含有这种磺胺基衍生物的药物配方。所述磺胺基衍生物是JNK途径的高效调节剂，特别是JNK 2和3的高效和选择性抑制剂。本发明还涉及新型磺胺基衍生物以及它们的制备方法。 根据本发明的式I化合物适用于药用剂的那些化合物是这样的： Ar1和Ar2分别独立地是取代或未取代的芳基或杂环芳基， X是O或S，优选为O； R1是氢或C1-C6烷基，或R1与Ar1形成取代或未取代的5-6元饱和或不饱和环； n是0到5的整数，优选为1-3之间，最优选为1； 式I中的Y是未取代或取代的4-12元饱和环或双环烷基，其上取代有至少一个可离子化基团，该基团连接有一个亲脂链，并且含有至少一个氮原子，其中所述环中的一个氮原子与式I的磺酰基形成键合，从而提供磺胺基。