5-bromo-2-(3,4-difluorophenyl)-4-(3-hydroxy-3-methylbutoxy)-2H-pyridazin-3-one | 266320-84-7

• 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: 5-bromo-2-(3,4-difluorophenyl)-4-(3-hydroxy-3-methylbutoxy)-2H-pyridazin-3-one
• 英文别名: 5-Bromo-2-(3,4-difluorophenyl)-4-(3-hydroxy-3-methylbutoxy)pyridazin-3(2H)-one；5-bromo-2-(3,4-difluorophenyl)-4-(3-hydroxy-3-methylbutoxy)pyridazin-3-one
• CAS: 266320-84-7
• 化学式: C₁₅H₁₅BrF₂N₂O₃
• 分子量: 389.197
• InChiKey: ISHPREYNSKNEND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  62.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-bromo-2-(3,4-difluorophenyl)-4-(3-hydroxy-3-methylbutoxy)-2H-pyridazin-3-one 在 Oxone 、 potassium phosphate 、 dipotassium hydrogenphosphate 、 水 、 palladium diacetate 、 三苯基膦 作用下， 以 丙酮 为溶剂， 反应 4.5h， 生成 ABT-963
  参考文献：
  名称：

  An Efficient Multikilogram Synthesis of ABT-963:  A Selective COX-2 Inhibitor

  摘要：

  An efficient chemical process for the multikilogram synthesis of ABT-963 ( 3) is described. The potent and selective COX-2 inhibitor was prepared in four steps in 36% overall isolated yield from commercially available 3,4-difluoroaniline ( 4). The chemistry, which required no chromatography, involved a facile one-pot synthesis of the pyridazinone core, a selective alkoxylation, a high yielding Suzuki coupling, and a very efficient oxidation.

  DOI：

  10.1021/op060016v
• 作为产物：
  描述：

  3,4-二氟苯胺 在 氢溴酸 、 sodium hexamethyldisilazane 、 sodium nitrite 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 生成 5-bromo-2-(3,4-difluorophenyl)-4-(3-hydroxy-3-methylbutoxy)-2H-pyridazin-3-one
  参考文献：
  名称：

  An Efficient Multikilogram Synthesis of ABT-963:  A Selective COX-2 Inhibitor

  摘要：

  An efficient chemical process for the multikilogram synthesis of ABT-963 ( 3) is described. The potent and selective COX-2 inhibitor was prepared in four steps in 36% overall isolated yield from commercially available 3,4-difluoroaniline ( 4). The chemistry, which required no chromatography, involved a facile one-pot synthesis of the pyridazinone core, a selective alkoxylation, a high yielding Suzuki coupling, and a very efficient oxidation.

  DOI：

  10.1021/op060016v

文献信息

• [EN] PROSTAGLANDIN ENDOPEROXIDE H SYNTHASE BIOSYNTHESIS INHIBITORS<br/>[FR] INHIBITEURS DE LA BIOSYNTHESE DE LA PROSTAGLANDINE ENDOPEROXYDE H SYNTHASE
  申请人：ABBOTT LAB

  公开号：WO2000024719A1

  公开（公告）日：2000-05-04

  The present invention describes pyridazinone compounds of formula (I) which are cyclooxygenase (COX) inhibitors, and in particular, are selective inhibitors of cyclooxygenase-2 (COX-2). COX-2 is the inducible isoform associated with inflammation, as opposed to the constitutive isoform, cyclooxygenase-1 (COX-1) which is an important 'housekeeping' enzyme in many tissues, including the gastrointestinal (GI) tract and the kidneys. The selectively of these compounds for COX-2 minimizes the unwanted GI and renal side-effects seen with currently marketed non-steroidal anti-inflammatory drugs (NSAIDs).

  本发明描述了式（I）的吡啶酮化合物，它们是环氧合酶（COX）抑制剂，特别是选择性抑制剂环氧合酶-2（COX-2）。COX-2是与炎症有关的诱导型同工酶，而非构成型同工酶环氧合酶-1（COX-1），后者是许多组织（包括胃肠道和肾脏）中重要的“管家”酶。这些化合物对COX-2的选择性最小化了目前市场上非甾体类抗炎药（NSAIDs）所见的不良胃肠道和肾脏副作用。
• Prostaglandin endoperoxide H synthase biosynthesis inhibitors
  申请人：——

  公开号：US20020028938A1

  公开（公告）日：2002-03-07

  The present invention describes pyridazinone compounds of formula I 1 which are cyclooxygenase (COX) inhibitors, and in particular, are selective inhibitors of cyclooxygenase-2 (COX-2). COX-2 is the inducible isoform associated with inflammation, as opposed to the constitutive isoform, cyclooxygenase-1 (COX-1) which is an important “housekeeping” enzyme in many tissues, including the gastrointestinal (GI) tract and the kidneys. The selectivity of these compounds for COX-2 minimizes the unwanted GI and renal side-effects seen with currently marketed non-steroidal anti-inflammatory drugs (NSAIDs).

  本发明描述了公式I1的吡啶并咪唑酮化合物，它们是环氧合酶（COX）抑制剂，特别是选择性地抑制环氧合酶-2（COX-2）。 COX-2是与炎症相关的可诱导异构体，与包括胃肠道和肾脏在内的许多组织中重要的“家务”酶环氧合酶-1（COX-1）相对。这些化合物对COX-2的选择性最小化了目前市场上非甾体抗炎药（NSAIDs）所见的不良胃肠和肾脏副作用。
• Org. Process Res. Dev. 2006, 10, 512-517
  作者：

  DOI：——

  日期：——
• PROSTAGLANDIN ENDOPEROXIDE H SYNTHASE BIOSYNTHESIS INHIBITORS
  申请人：ABBOTT LABORATORIES

  公开号：EP1124804B1

  公开（公告）日：2005-08-24
• US6307047B1
  申请人：——

  公开号：US6307047B1

  公开（公告）日：2001-10-23