(R)-2-[2-(2,6-dichlorophenylamino)phenyl]propionic acid

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (R)-2-[2-(2,6-dichlorophenylamino)phenyl]propionic acid
• 英文别名: (2R)-2-[2-(2,6-dichloroanilino)phenyl]propanoic acid
• 化学式: C₁₅H₁₃Cl₂NO₂
• 分子量: 310.18
• InChiKey: QKZXQNPQDHXWTI-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-2-[2-(2,6-dichlorophenylamino)phenyl]propionic acid 、 N,N-二甲基-1,3-二氨基丙烷 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 22.0h， 以75%的产率得到(R)-2-[2-(2,6-dichlorophenylamino)phenyl]-N-[3-(dimethylamino)propyl]propionamide
  参考文献：
  名称：

  OMEGA-AMINOALKYLAMIDES OF (R)-2-ARYL-PROPIONIC ACIDS AS INHIBITORS OF THE CHEMOTAXIS OF POLYMORPHONUCLEATE AND MONONUCLEATE CELLS

  摘要：

  公开号：

  EP1366018B1

文献信息

• Amides, useful in the inhibition of il-8-induced chemotaxis of neutrophils
  申请人：——

  公开号：US20040181073A1

  公开（公告）日：2004-09-16

  N-(2-aryl-propionyl)-amides of formula (I) are described. 1 The process for their preparation and pharmaceutical preparations thereof are also described. The amides of the invention are useful in the prevention and treatment of tissue damage due to the exacerbate recruitment of polymorphonuclear neutrophils (leukocytes PMN) at the inflammatory sites. In particular, the invention relates to the R enantiomers of N-(2-aryl-propionyl)amides of formula (I) for use in the ihibition of the chemotaxis of neutrophils induced by IL-8. The compounds of the invention are used in the treatment of psoriasis, ulcerative cholitis, glomerular nephritis, acute respiratory insufficiency, idiopathic fibrosis, and rheumatoid arthritis.

  公式（I）的N-（2-芳基丙酰基）酰胺已被描述。还描述了它们的制备过程和药物制剂。本发明的酰胺在预防和治疗由于在炎症部位加重多形核中性粒细胞（白细胞PMN）的招募而导致的组织损伤方面是有用的。具体而言，本发明涉及用于抑制IL-8诱导的中性粒细胞趋化作用的N-（2-芳基丙酰基）酰胺的R对映体。本发明的化合物用于治疗牛皮癣、溃疡性结肠炎、肾小球肾炎、急性呼吸功能不全、特发性纤维化和类风湿关节炎。
• [EN] 2-ARYL-PROPIONIC ACIDS AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM<br/>[FR] ACIDES 2-ARYL-PROPIONIQUES ET COMPOSITIONS PHARMACEUTIQUES RENFERMANT CEUX-CI
  申请人：DOMPE SPA

  公开号：WO2003043625A1

  公开（公告）日：2003-05-30

  (R) and (S) 2-Aryl-propionic acids, and pharmaceutical compositions that contain them, are useful in inhibiting chemotactic activation of neutrophils (PMN leukocytes) induced by the interaction of Interleukin-8 (IL-8) with CXCR1 and CXCR2 membrane receptors. The acids are used for the prevention and treatment of pathologies deriving from said activation. In particular, the (R) enantiomers of said acids are lacking cyclo-oxygenase inhibition activity and are particularly useful in the treatment of neutrofil-dependent pathologies such as psoriasis, ulcerative colitis, melanoma, chronic obstructive pulmonary disease (COPD),bollous pemphigo, rheumatoid arthritis, idiopathic fibrosis, glomerulonephritis and in the prevention and treatment of damages caused by ischemia and reperfusion.

  (R)和(S) 2-芳基丙酸及含有它们的药物组合物，可用于抑制由白细胞介素-8（IL-8）与CXCR1和CXCR2膜受体相互作用引起的嗜中性粒细胞（PMN白细胞）的趋化活化。这些酸用于预防和治疗由该活化引起的病理。特别地，这些酸的(R)对映体缺乏环氧合酶抑制活性，特别适用于治疗依赖于中性粒细胞的病理，如银屑病，溃疡性结肠炎，黑色素瘤，慢性阻塞性肺疾病（COPD），天疱疮，类风湿性关节炎，特发性纤维化，肾小球肾炎以及缺血再灌注所致的损伤的预防和治疗。
• OMEGA-AMINOALKYLAMIDES OF R-2-ARYL-PROPIONIC ACIDS AS INHIBITORS OF THE CHEMOTAXIS OF POLYMORPHONUCLEATE AND MONONUCLEATE CELLS
  申请人：ALLEGRETTI Marcello

  公开号：US20080045522A1

  公开（公告）日：2008-02-21

  (R)-2-Arylpropionamide compounds of formula (I) are described. The process for their preparation and pharmaceutical preparations thereof are also described. The 2-Arylpropionamides of the invention are useful in the prevention and treatment of tissue damage due to the exacerbate recruitment of polymorphonuclear leukocytes (leukocytes PMN) and of monocytes at the inflammatory sites. In particular, the invention relates to the R enantiomers of omega-aminoalkylamides of 2-aryl propionic acids, of formula (I), for use in the inhibition of the chemotaxis of neutrophils and monocytes induced by the C5a fraction of the complement and by other chemotactic proteins whose biological activity is associated with activation of a 7-TD receptor. Selected compounds of formula (I) are dual inhibitors of both the C5a-induced chemotaxis of neutrophils and monocytes and the IL-8-induced chemotaxis of PMN leukocytes. The compounds of the invention are used in the treatment of psoriasis, ulcerative cholitis, glomerular nephritis, acute respiratory insufficiency, idiopathic fibrosis, rheumatoid arthritis and in the prevention and the treatment of injury caused by ischemia and reperfusion.

  本文描述了公式(I)的(R)-2-芳基丙酰胺化合物，以及它们的制备过程和制药制剂。本发明中的2-芳基丙酰胺类化合物可用于预防和治疗由于在炎症部位诱导多形核白细胞（白细胞PMN）和单核细胞的加重招募而导致的组织损伤。特别是，本发明涉及公式(I)的ω-氨基烷基酰胺的R对映体，用于抑制由C5a补体分数和其他趋化蛋白诱导的中性粒细胞和单核细胞趋化，其生物活性与7-TD受体的激活有关。公式(I)的某些选择性化合物是同时抑制C5a诱导的中性粒细胞和单核细胞趋化以及IL-8诱导的PMN白细胞趋化的双重抑制剂。本发明中的化合物用于治疗牛皮癣、溃疡性结肠炎、肾小球肾炎、急性呼吸功能不全、特发性纤维化、类风湿关节炎以及预防和治疗缺血再灌注所致的损伤。
• 2-Aryl-propionic acids and pharmaceutical compositions containing them
  申请人：Dompe S.p.A.

  公开号：EP2229942A1

  公开（公告）日：2010-09-22

  (R) and (S) 2-Aryl-propionic acids, and pharmaceutical compositions that contain them, are useful in inhibiting chemotactic activation of neutrophils (PMN leukocytes) induced by the interaction of Interleukin-8 (IL-8) with CXCR1 and CXCR2 membrane receptors. The acids are used for the prevention and treatment of pathologies deriving from said activation. In particular, the (R) enantiomers of said acids are lacking cyclo-oxygenase inhibition activity and are particularly useful in the treatment of neutrofil-dependent pathologies such as psoriasis, ulcerative colitis, melanoma, chronic obstructive pulmonary disease (COPD), bollous pemphigo, rheumatoid arthritis, idiopathic fibrosis, glomerulonephritis and in the prevention and treatment of damages caused by ischemia and reperfusion.

  (R)和(S)2-芳基丙酸以及含有它们的药物组合物有助于抑制白细胞介素-8（IL-8）与 CXCR1 和 CXCR2 膜受体相互作用所诱导的中性粒细胞（PMN 白细胞）的趋化活化。这些酸可用于预防和治疗上述活化引起的病症。特别是，所述酸的(R)对映体缺乏环氧化酶抑制活性，特别适用于治疗中性粒细胞依赖性病症，如牛皮癣、溃疡性结肠炎、黑色素瘤、慢性阻塞性肺病（COPD）、脓疱疮、类风湿性关节炎、特发性纤维化、肾小球肾炎，以及预防和治疗缺血和再灌注引起的损伤。
• (R)-2-ARYL-PROPIONAMIDES, USEFUL IN THE INHIBITION OF IL-8 INDUCED CHEMIOTAXIS OF NEUTROPHILS
  申请人：DOMPE' pha.r.ma S.p.A.

  公开号：EP1255726B1

  公开（公告）日：2009-11-11