4-chloro-5-(2-chlorobenzoylamino)-1H-pyrazole-3-carboxylic acid

• 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: 4-chloro-5-(2-chlorobenzoylamino)-1H-pyrazole-3-carboxylic acid
• 英文别名: 4-chloro-3-[(2-chlorobenzoyl)amino]-1H-pyrazole-5-carboxylic acid
• 化学式: C₁₁H₇Cl₂N₃O₃
• 分子量: 300.101
• InChiKey: BFTSVTWPNYAHDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  95.1
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(3,4,5,6-tetrahydro-2H-[1,4']bipyridinyl-4-yl)ethylamine 、 4-chloro-5-(2-chlorobenzoylamino)-1H-pyrazole-3-carboxylic acid 在 N-甲基吗啉 、 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 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 4-chloro-5-(2-chloro-benzoylamino)-1H-pyrazole-3-carboxylic acid [2-(3,4,5,6-tetrahydro-2H-[1,4']bipyridin-4-yl)-ethyl]-amide
  参考文献：
  名称：

  Preparation and Optimization of a Series of 3-Carboxamido-5-phenacylaminopyrazole Bradykinin B1 Receptor Antagonists

  摘要：

  The B1 receptor is an attractive target for the treatment of pain and inflammation. A series of 3-carboxamido5-phenacylamino pyrazole B1 receptor antagonists are described that exhibit good potency against B1 and high selectivity over B2. Initially, N-unsubstituted pyrazoles were studied, but these compounds suffered from extensive glucuronidation in primates. This difficulty could be surmounted by the use of N-substituted pyrazoles. Optimization efforts culminated in compound 41, which has high receptor potency and metabolic stability.

  DOI：

  10.1021/jm051292n
• 作为产物：
  描述：

  5-[(2-chlorobenzoyl)amino]-1H-pyrazole-3-carboxylic acid 在 盐酸 、 N-chloro-succinamide 作用下， 以 DMF (N,N-dimethyl-formamide) 为溶剂， 生成 4-chloro-5-(2-chlorobenzoylamino)-1H-pyrazole-3-carboxylic acid
  参考文献：
  名称：

  [EN] 4- BROMO - 5 - (2- CHLORO - BENZOYLAMINO) - 1H - PYRAZOLE - 3 - CARBOXYLIC ACID AMIDE DERIVATIVES AND RELATED COMPOUNDS AS BRADYKININ B1 RECEPTOR ANTAGONISTS FOR THE TREATMENT OF INFLAMMATORY DISEASES
  [FR] DERIVES AMIDES DE L'ACIDE CARBOXYLIQUE DE 4- BROMO - 5 - (2- CHLORO - BENZOYLAMINO) - 1H - PYRAZOLE 3 ET COMPOSES ASSOCIES EN TANT QU'ANTAGONISTES DE RECEPTEUR DE B1 DE LA BRADYKININE POUR LE TRAITEMENT DE MALADIES INFLAMMATOIRES

  摘要：

  公开的是化合物I和II的结构式，它们是激肽酶B1受体拮抗剂，适用于治疗哺乳动物中由激肽酶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，并且预计还将表现出延长作用的特性。

  公开号：

  WO2004098589A1

文献信息

• [EN] 4- BROMO - 5 - (2- CHLORO - BENZOYLAMINO) - 1H - PYRAZOLE - 3 - CARBOXYLIC ACID AMIDE DERIVATIVES AND RELATED COMPOUNDS AS BRADYKININ B1 RECEPTOR ANTAGONISTS FOR THE TREATMENT OF INFLAMMATORY DISEASES<br/>[FR] DERIVES AMIDES DE L'ACIDE CARBOXYLIQUE DE 4- BROMO - 5 - (2- CHLORO - BENZOYLAMINO) - 1H - PYRAZOLE 3 ET COMPOSES ASSOCIES EN TANT QU'ANTAGONISTES DE RECEPTEUR DE B1 DE LA BRADYKININE POUR LE TRAITEMENT DE MALADIES INFLAMMATOIRES
  申请人：ELAN PHARM INC

  公开号：WO2004098589A1

  公开（公告）日：2004-11-18

  Disclosed are compounds of formula 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.

  公开的是化合物I和II的结构式，它们是激肽酶B1受体拮抗剂，适用于治疗哺乳动物中由激肽酶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，并且预计还将表现出延长作用的特性。
• Substituted pyrazole derivatives and related compounds as bradykinin B1 receptor antagonists
  申请人：Tung S. Jay

  公开号：US20050020659A1

  公开（公告）日：2005-01-27

  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.

  本发明公开了一种布雷肯肽B1受体拮抗剂化合物，可用于治疗哺乳动物中由布雷肯肽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，并且预计也会表现出增强的作用持续时间。
• Selected substituted pyrazole derivatives and related compounds as bradykinin B1 receptor antagonists
  申请人：Garofalo W. Albert

  公开号：US20050032868A1

  公开（公告）日：2005-02-10

  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.

  本发明涉及一种用于治疗哺乳动物中由于缓激肽B1受体介导的疾病或缓解与疾病状态相关的不良症状的缓激肽B1受体拮抗剂化合物。其中某些化合物表现出增强的效力，并且预计还会表现出增强的作用持续时间。
• 4-Bromo-5-(2-chloro-benzoylamino)-1h-pyrazole-3-carboxylic acid (phenyl) amide derivatives and related compounds as bradykinin b1 receptor antagonists for the treatment of inflammatory diseases
  申请人：Garofalo W. Albert

  公开号：US20070123531A1

  公开（公告）日：2007-05-31

  Disclosed are compounds 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.

  本发明涉及一种可以用于治疗哺乳动物中由于Bradykinin B1受体介导的疾病或缓解与疾病状态相关的不良症状的化合物，这些化合物是Bradykinin B1受体拮抗剂。其中某些化合物表现出增强的效力，并且预计还将表现出增加的作用持续时间。
• 4-Bromo-5-(2-chloro-benzoylamino)-1h-pyrazole-3-carvoxylic acid 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：US20060281733A1

  公开（公告）日：2006-12-14

  Disclosed are compounds of formula 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.

  本发明公开了式I和式II的化合物，它们是缓激肽B1受体拮抗剂，可用于治疗哺乳动物中由缓激肽B1受体介导的疾病，或缓解与疾病条件相关的不良症状。其中某些化合物表现出增强的效力，预计也会表现出增强的持续时间。