2-chloro-4-{[2-(methylsulfonyl)benzyl]amino}pyrimidine-5-carboxamide | 1042921-42-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2-chloro-4-{[2-(methylsulfonyl)benzyl]amino}pyrimidine-5-carboxamide
• 英文别名: 2-Chloro-4-[(2-methylsulfonylphenyl)methylamino]pyrimidine-5-carboxamide
• CAS: 1042921-42-5
• 化学式: C₁₃H₁₃ClN₄O₃S
• 分子量: 340.79
• InChiKey: SSSPCUQBGUGGLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  123
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(4-吗啉基)苯胺 、 2-chloro-4-{[2-(methylsulfonyl)benzyl]amino}pyrimidine-5-carboxamide 在 dioxanic HCl 作用下， 以 N-甲基吡咯烷酮 为溶剂， 生成 4-{[2-(Methylsulfonyl)benzyl]amino}-2-[(4-morpholin-4-ylphenyl)amino]pyrimidine-5-carboxamide
  参考文献：
  名称：

  Identification of 4-benzylamino-2-[(4-morpholin-4-ylphenyl)amino]pyrimidine-5-carboxamide derivatives as potent and orally bioavailable STAT6 inhibitors

  摘要：

  Signal transducers and activators of transcription 6 (STAT6) is a key regulator of the type 2 helper T (Th2) cell immune response and a potential therapeutic target for allergic diseases such as asthma and atopic diseases. To search for potent and orally bioavailable STAT6 inhibitors, we synthesized a series of 4-benzylaminopyrimidine-5- carboxamide derivatives and evaluated their STAT6 inhibitory activities. Among these compounds, 2-[(4-morpholin-4-ylphenyl)amino]-4-[(2,3,6- trifluorobenzyl)amino]pyrimidine-5-carboxamide (25y, YM-341619, AS1617612) showed potent STAT6 inhibition with an IC(50) of 0.70 nM, and also inhibited Th2 differentiation in mouse spleen T cells induced by interleukin (IL)-4 with an IC(50) of 0.28 nM without affecting type 1 helper T (Th1) cell differentiation induced by IL-12. In addition, compound 25y showed an oral bioavailability of 25% in mouse. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.05.031
• 作为产物：
  描述：

  在 ammonium hydroxide 作用下， 生成 2-chloro-4-{[2-(methylsulfonyl)benzyl]amino}pyrimidine-5-carboxamide
  参考文献：
  名称：

  Identification of 4-benzylamino-2-[(4-morpholin-4-ylphenyl)amino]pyrimidine-5-carboxamide derivatives as potent and orally bioavailable STAT6 inhibitors

  摘要：

  Signal transducers and activators of transcription 6 (STAT6) is a key regulator of the type 2 helper T (Th2) cell immune response and a potential therapeutic target for allergic diseases such as asthma and atopic diseases. To search for potent and orally bioavailable STAT6 inhibitors, we synthesized a series of 4-benzylaminopyrimidine-5- carboxamide derivatives and evaluated their STAT6 inhibitory activities. Among these compounds, 2-[(4-morpholin-4-ylphenyl)amino]-4-[(2,3,6- trifluorobenzyl)amino]pyrimidine-5-carboxamide (25y, YM-341619, AS1617612) showed potent STAT6 inhibition with an IC(50) of 0.70 nM, and also inhibited Th2 differentiation in mouse spleen T cells induced by interleukin (IL)-4 with an IC(50) of 0.28 nM without affecting type 1 helper T (Th1) cell differentiation induced by IL-12. In addition, compound 25y showed an oral bioavailability of 25% in mouse. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.05.031

文献信息

• 2-SUBSTITUTED PYRAZOLE AMINO-4-SUBSTITUTED AMINO-5-PYRIMIDINE FORMAMIDE COMPOUND, COMPOSITION, AND APPLICATION THEREOF
  申请人：Beijing Scitech-MQ Pharmaceuticals Limited

  公开号：EP3686197A1

  公开（公告）日：2020-07-29

  The present disclosure relates to a novel compound as a JAK inhibitor, a composition, and an application thereof. Specifically, the present disclosure provides a compound having high AK inhibitory activity (as represented by formula (I)) or its isomer, solvate, hydrate, pharmaceutically-acceptable salt, and prodrug, and a pharmaceutical composition containing the compound. Also disclosed is an application of the present compound or pharmaceutical composition in preparation of a drug, and the drug is used for treating autoimmune diseases or cancers.

  本公开涉及一种作为 JAK 抑制剂的新型化合物、一种组合物及其应用。具体而言，本公开提供了一种具有高 AK 抑制活性的化合物（如式 (I) 所示）或其同分异构体、溶解物、水合物、药学上可接受的盐和原药，以及含有该化合物的药物组合物。还公开了本化合物或药物组合物在制备药物中的应用，该药物用于治疗自身免疫性疾病或癌症。
• 2-substituted pyrazole amino-4-substituted amino-5-pyrimidine formamide compound, composition, and application thereof
  申请人：BEIJING SCITECH-MQ PHARMACEUTICALS LIMITED

  公开号：US11344549B2

  公开（公告）日：2022-05-31

  The present disclosure relates to a novel compound as a JAK inhibitor, a composition, and an application thereof. Specifically, the present disclosure provides a compound having high JAK inhibitory activity (as represented by formula (I)) or its isomer, solvate, hydrate, pharmaceutically-acceptable salt, and prodrug, and a pharmaceutical composition containing the compound. Also disclosed is a use of the present compound or pharmaceutical composition in preparation of a medicament for treating autoimmune diseases or cancers.

  本公开涉及一种作为 JAK 抑制剂的新型化合物、一种组合物及其应用。具体而言，本公开提供了一种具有高 JAK 抑制活性的化合物（如式 (I) 所示）或其异构体、溶解物、水合物、药学上可接受的盐和原药，以及含有该化合物的药物组合物。还公开了本化合物或药物组合物在制备治疗自身免疫性疾病或癌症的药物中的用途。