(3S,4S)-benzyl 3-((tert-butoxycarbonyl)amino)-4-(fluoromethyl)pyrrolidine-1-carboxylate | 246510-71-4

• 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: (3S,4S)-benzyl 3-((tert-butoxycarbonyl)amino)-4-(fluoromethyl)pyrrolidine-1-carboxylate
• 英文别名: (3S,4S)-1-(benzyloxycarbonyl)-3-(tert-butoxycarbonyl)amino-4-fluoromethylpyrrolidine；benzyl (3S,4S)-3-(fluoromethyl)-4-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidine-1-carboxylate
• CAS: 246510-71-4
• 化学式: C₁₈H₂₅FN₂O₄
• 分子量: 352.406
• InChiKey: GUUUPBRUZFUWCM-LSDHHAIUSA-N

物化性质

• 沸点：
  480.3±40.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S,4S)-benzyl 3-((tert-butoxycarbonyl)amino)-4-(fluoromethyl)pyrrolidine-1-carboxylate 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 (3S,4S)-benzyl 3-(5-(4-amino-5-(trifluoromethyl)pyrrolo[2,1-f][1,2,4]triazin-7-yl)-2-methylnicotinamido)-4-(fluoromethyl)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  [EN] AMINOPYRROLOTRIAZINES AS KINASE INHIBITORS
  [FR] AMINOPYRROLOTRIAZINES EN TANT QU'INHIBITEURS DE KINASE

  摘要：

  该公开涉及到公式I的化合物，这些化合物可用作激酶调节剂，包括RIPK1调节。该公开还提供了制备和使用这些化合物的方法，例如在涉及坏死或炎症以及其他适应症的治疗中使用。

  公开号：

  WO2019147782A1
• 作为产物：
  描述：

  在 palladium on activated charcoal lithium hydroxide 、 二苯基磷酸 、 甲酸铵 、 sodium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 为溶剂， 生成 (3S,4S)-benzyl 3-((tert-butoxycarbonyl)amino)-4-(fluoromethyl)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Synthesis and structure-activity relationships of 2-pyridones: II. 8-(Fluoro-substituted pyrrolidinyl)-2-pyridones as antibacterial agents

  摘要：

  The 8-position side chain of 2-pyridones is believed to be involved in the binding with bacterial DNA gyrase to form the ternary complex, making them very important for the activity of 2-pyridones. A series of 2-pyridones having fluoro-substituted amines at the 8-position has been synthesized and their antibacterial activities and pharmacokinetic properties are reported. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00355-2

文献信息

• FLUOROALKYLPYRROLIDINE DERIVATIVE
  申请人：Takahasi Hisashi

  公开号：US20090012119A1

  公开（公告）日：2009-01-08

  This invention relates to a compound represented by the following formula (1): [F.1] its salt or a hydrate thereof. R 1 represents hydrogen atom, an optionally substituted alkyl group containing 1 to 6 carbon atoms, a cycloalkyl group containing 3 to 6 carbon atoms, or a substituted carbonyl group derived from an amino acid, a dipeptide, or a tripeptide; R 2 represents hydrogen atom, an optionally substituted alkyl group containing 1 to 6 carbon atoms, or a cycloalkyl group containing 3 to 6 carbon atoms; R 3 represents an alkyl group containing 1 to 6 carbon atoms or a halogen-substituted alkyl group containing 1 to 6 carbon atoms; R 4 represents a cycloalkyl group containing 3 to 6 carbon atoms or a halogen-substituted cycloalkyl group containing 3 to 6 carbon atoms; R 5 represents hydrogen atom, phenyl group, acetoxymethyl group, pivaloyloxymethyl group, ethoxycarbonyl group, choline group, dimethylaminoethyl group, 5-indanyl group, phthalidyl group, 5-alkyl-2-oxo-1,3-dioxol-4-ylmethyl group, 3-acetoxy-2-oxobutyl group, or a phenylalkyl group comprising an alkylene group containing 1 to 6 carbon atoms and phenyl group; X 1 and X 2 independently represent hydrogen atom or a halogen atom; and X represents hydrogen atom or a halogen atom. This compound exhibits broad and strong antibacterial activity to both Gram positive and Gram negative bacteria as well as high safety, and therefore, this compound is useful as a quinolone antibacterial drug, and a prophylactic and/or therapeutic drug for an infectious disease.

  本发明涉及下列公式（1）所表示的化合物，其盐或水合物。R1代表氢原子、含1至6个碳原子的可选择取代的烷基、含3至6个碳原子的环烷基或由氨基酸、二肽或三肽衍生的取代的羰基基团；R2代表氢原子、含1至6个碳原子的可选择取代的烷基或含3至6个碳原子的环烷基；R3代表含1至6个碳原子的烷基或含1至6个碳原子的卤素取代的烷基；R4代表含3至6个碳原子的环烷基或含3至6个碳原子的卤素取代的环烷基；R5代表氢原子、苯基、乙酰氧甲基基团、季铵基、乙酰氧基羰基基团、胆碱基团、二甲氨基乙基基团、5-茚基基团、邻苯二甲酰基团、5-烷基-2-氧代-1,3-二氧杂环戊基甲基基团、3-乙酰氧基-2-氧代丁基基团或包含1至6个碳原子的烷基和苯基的苯基烷基基团；X1和X2分别代表氢原子或卤素原子；X代表氢原子或卤素原子。此化合物表现出广泛且强烈的抗细菌活性，对革兰氏阳性和革兰氏阴性细菌均有效，并且具有高度的安全性，因此，此化合物可用作喹诺酮类抗菌药物以及预防和/或治疗传染病的药物。
• Pyrrolopyridazine JAK3 inhibitors and their use for the treatment of inflammatory and autoimmune diseases
  申请人：Wrobleski Stephen T.

  公开号：US08987268B2

  公开（公告）日：2015-03-24

  The present invention provides compounds of formula I and pharmaceutically acceptable salts thereof. The formula I compounds inhibit tyrosine kinase activity of JAK3, thereby making them useful for the treatment of inflammatory and autoimmune diseases.

  本发明提供了I式化合物及其药学上可接受的盐。I式化合物抑制JAK3的酪氨酸激酶活性，因此它们对于治疗炎症和自身免疫性疾病是有用的。
• PYRROLOPYRIDAZINE JAK3 INHIBITORS AND THEIR USE FOR THE TREATMENT OF INFLAMMATORY AND AUTOIMMUNE DISEASES
  申请人：Wrobleski Stephen T.

  公开号：US20140011800A1

  公开（公告）日：2014-01-09

  The present invention provides compounds of formula I and pharmaceutically acceptable salts thereof. The formula I compounds inhibit tyrosine kinase activity of JAK3, thereby making them useful for the treatment of inflammatory and autoimmune diseases.

  本发明提供了I型化合物及其药学上可接受的盐。式I化合物抑制JAK3的酪氨酸激酶活性，因此可用于治疗炎症和自身免疫性疾病。
• IMIDAZOPYRIDAZINE JAK3 INHIBITORS AND THEIR USE FOR THE TREATMENT OF INFLAMMATORY AND AUTOIMMUNE DISEASES
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：US20150210703A1

  公开（公告）日：2015-07-30

  The present invention provides compounds of formula (I) and pharmaceutically acceptable salts thereof. The formula I compounds inhibit tyrosine kinase activity of JAK3, thereby making them useful for the treatment of inflammatory and autoimmune diseases.

  本发明提供了公式(I)的化合物及其药学上可接受的盐。公式I的化合物抑制JAK3的酪氨酸激酶活性，因此它们对治疗炎症和自身免疫性疾病有用。
• Imidazopyridazine JAK3 inhibitors and their use for the treatment of inflammatory and autoimmune diseases
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：US09428511B2

  公开（公告）日：2016-08-30

  The present invention provides compounds of formula (I) and pharmaceutically acceptable salts thereof. The formula I compounds inhibit tyrosine kinase activity of JAK3, thereby making them useful for the treatment of inflammatory and autoimmune diseases.

  本发明提供I式化合物及其药学上可接受的盐。I式化合物抑制JAK3的酪氨酸激酶活性，因此它们可用于治疗炎症和自身免疫性疾病。