((R)-1-methyl-2-oxo-2-piperidin-1-yl-ethyl)carbamic acid tert-butyl ester | 720001-85-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ((R)-1-methyl-2-oxo-2-piperidin-1-yl-ethyl)carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(2R)-1-oxo-1-piperidin-1-ylpropan-2-yl]carbamate
• CAS: 720001-85-4
• 化学式: C₁₃H₂₄N₂O₃
• 分子量: 256.345
• InChiKey: OMQNBACANODXCT-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ((R)-1-methyl-2-oxo-2-piperidin-1-yl-ethyl)carbamic acid tert-butyl ester 在 盐酸 、 sodium acetate trihydrate 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 36.5h， 生成 2-cyclopropyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((R)-1-methyl-2-oxo-2-piperidin-1-ylethyl)amide
  参考文献：
  名称：

  3-Amido Pyrrolopyrazine JAK Kinase Inhibitors: Development of a JAK3 vs JAK1 Selective Inhibitor and Evaluation in Cellular and in Vivo Models

  摘要：

  The Janus kinases (JAKs) are involved in multiple signaling networks relevant to inflammatory diseases, and inhibition of one or more members of this class may modulate disease activity or progression. We optimized a new inhibitor scaffold, 3-amido-5-cyclopropylpyrrolopyrazines, to a potent example with reasonable kinome selectivity, including selectivity for JAK3 versus JAK1, and good biopharmaceutical properties. Evaluation of this analogue in cellular and in vivo models confirmed functional selectivity for modulation of a JAK3/JAK1-dependent IL-2 stimulated pathway over a JAK1/JAK2/Tyk2-dependent IL-6 stimulated pathway.

  DOI：

  10.1021/jm301646k
• 作为产物：
  描述：

  哌啶 、 BOC-D-丙氨酸 在 1-羟基苯并三唑一水物 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以100%的产率得到((R)-1-methyl-2-oxo-2-piperidin-1-yl-ethyl)carbamic acid tert-butyl ester
  参考文献：
  名称：

  3-Amido Pyrrolopyrazine JAK Kinase Inhibitors: Development of a JAK3 vs JAK1 Selective Inhibitor and Evaluation in Cellular and in Vivo Models

  摘要：

  The Janus kinases (JAKs) are involved in multiple signaling networks relevant to inflammatory diseases, and inhibition of one or more members of this class may modulate disease activity or progression. We optimized a new inhibitor scaffold, 3-amido-5-cyclopropylpyrrolopyrazines, to a potent example with reasonable kinome selectivity, including selectivity for JAK3 versus JAK1, and good biopharmaceutical properties. Evaluation of this analogue in cellular and in vivo models confirmed functional selectivity for modulation of a JAK3/JAK1-dependent IL-2 stimulated pathway over a JAK1/JAK2/Tyk2-dependent IL-6 stimulated pathway.

  DOI：

  10.1021/jm301646k

文献信息

• Substituted pyrazole derivatives and related compounds as bradykinin B1 receptor antagonists
  申请人：Tung S. Jay

  公开号：US20050038099A1

  公开（公告）日：2005-02-17

  Disclosed are compounds that are bradykinin B 1 receptor antagonists and are useful for treating diseases, or relieving adverse symptoms associated with disease conditions, in mammals mediated by bradykinin B 1 receptor. Certain of the compounds exhibit increased potency and are also expected to exhibit increased duration of action.

  本发明涉及一种是Bradykinin B1受体拮抗剂的化合物，可用于治疗哺乳动物中由Bradykinin B1受体介导的疾病或缓解与疾病状况相关的不良症状。其中某些化合物表现出增强的效力，并且预计还会表现出持续时间的增加。
• 4-Bromo-5-(2-chloro-benzoylamino)-1h-pyrazole-3-carboxylic acid (1-aminocarbonyl)eth-1-yl) amide derivatives and related compounds as bradykinin b1 receptor antagonists for the treatment of inflammatory diseases
  申请人：Tung S. Jay

  公开号：US20070161633A1

  公开（公告）日：2007-07-12

  Disclosed are compounds of formulae (I) and (II) that are bradykinin B 1 receptor antagonists and are useful for treating diseases, or relieving adverse symptoms associated with disease conditions, in mammals mediated by bradykinin B 1 receptor. Certain of the compounds exhibit increased potency and are also expected to exhibit increased duration of action. Wherein Z is selected from O, S and NH; Q of formula (III) and the other substituents are as defined in claim 1.

  本发明涉及式(I)和(II)的化合物，它们是布雷地奎宁B1受体拮抗剂，可用于治疗哺乳动物中由布雷地奎宁B1受体介导的疾病或缓解与疾病状况相关的不良症状。其中Z从O、S和NH中选择；公式(III)中的Q和其他取代基如权利要求1所定义。其中某些化合物表现出增强的效力，并且预计还会表现出延长作用时间。
• 4-BROMO-5- (2-CHLORO-BENZOYLAMINO)-1H-PYRAZOLE-3-CARBOXYLIC ACID (1-(AMINOCARBONYL) ETH-1-YL) AMIDE DERIVATIVES AND RELATED COMPOUNDS AS BRADYKININ B1 RECEPTOR ANTAGONISTS FOR THE TREATMENT OF INFLAMMATORY DISEASES
  申请人：ELAN PHARMACEUTICALS, INC.

  公开号：EP1633349A1

  公开（公告）日：2006-03-15
• [EN] 4-BROMO-5- (2-CHLORO-BENZOYLAMINO)-1H-PYRAZOLE-3-CARBOXYLIC ACID (1-(AMINOCARBONYL) ETH-1-YL) AMIDE DERIVATIVES AND RELATED COMPOUNDS AS BRADYKININ B1 RECEPTOR ANTAGONISTS FOR THE TREATMENT OF INFLAMMATORY DISEASES<br/>[FR] DERIVES AMIDE 4-BROMO-5- (2-CHLORO-BENZOYLAMINO)-1H-PYRAZOLE-3-ACIDE CARBOXYLIQUE (1-(AMINOCARBONYL)ETH-1-YL) ET COMPOSES CORRESPONDANTS TELS QUE LES ANTAGONISTES DU RECEPTEUR DE LA BRADYKININE DE TYPE B1 POUR LE TRAITEMENT DES MALADIES INFLAMMATOIRES
  申请人：ELAN PHARM INC

  公开号：WO2004098590A1

  公开（公告）日：2004-11-18

  Disclosed are compounds of formulae (I) and (II) that are bradykinin B1 receptor antagonists and are useful for treating diseases, or relieving adverse symptoms associated with disease conditions, in mammals mediated by bradykinin B1 receptor. Certain of the compounds exhibit increased potency and are also expected to exhibit increased duration of action. Wherein Z is selected from O, S and NH; Q of formula (III) and the other substituents are as defined in claim 1.