6-(4-aminophenyl)-2H-pyridazin-3-one hydrochloride | 54558-11-1

• 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: 6-(4-aminophenyl)-2H-pyridazin-3-one hydrochloride
• 英文别名: 6-(4-aminophenyl)-3(2H)-pyridazinone hydrochloride；3-(4-aminophenyl)-1H-pyridazin-6-one;hydrochloride
• CAS: 54558-11-1
• 化学式: C₁₀H₉N₃O*ClH
• 分子量: 223.662
• InChiKey: CKWHPAXDUDYUCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.44
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(4-aminophenyl)-2H-pyridazin-3-one hydrochloride 在 盐酸 、 sodium nitrite 、 tin(ll) chloride 作用下， 反应 1.5h， 以80%的产率得到6-(4-hydrazinophenyl)-2H-pyridazin-3-one hydrochloride
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of cis-Tetrahydrophthalazinone/Pyridazinone Hybrids:  A Novel Series of Potent Dual PDE3/PDE4 Inhibitory Agents

  摘要：

  In this study, the synthesis and in vitro and in vivo pharmacological investigations of a new series of phthalazinone/pyridazinone hybrids with both PDE3 and PDE4 inhibitory activities are described. These compounds combine the pharmacophores of recently discovered 4a,5,8,8a-tetrahydro-2H-phthalazin-1-one-type inhibitors of PDE4 and the well-known 2H-pyridazin-3-one-type PDE3 inhibitors such as the tetrahydrobenzimidazoles. Most of the synthesized compounds are pharmacologically spoken PDE3/PDE4 hybrids. All hybrids show potent PDE4 inhibitory activity (pIC(50) = 7.0-8.7), whereas the pIC(50) values for inhibition of PDE3 vary from 5.4 to 7.5. In general, analogues with a 5-methyl-4,5-dihydropyridazinone moiety exhibit the highest PDE3 inhibitory activities. The highest in vivo antiinflammatory activity is displayed by phthalazinones 43 and 44 showing, at a dose of 30 mumol/kg po, 46% inhibition of arachidonic acid (AA) induced mouse ear edema. No correlation was found between the in vitro PDE3 and/or PDE4 inhibitory activity and the in vivo antiinflammatory capacity after oral dosing.

  DOI：

  10.1021/jm030776l
• 作为产物：
  描述：

  6-(4-acetamidophenyl)-3(2H)-pyridazinone 以89%的产率得到
  参考文献：
  名称：

  STECK E. A.; BRUNDAGE R. P.; FLETCHER L. T., J. HETEROCYCL. CHEM. , 1974, 11, NO 5, 755-761

  摘要：

  DOI：

文献信息

• N-phenylpyridone type III phosphodiesterases
  申请人：Smith Kline & French Laboratories Limited

  公开号：US04906628A1

  公开（公告）日：1990-03-06

  Phosphodiesterase (type III) inhibitors having the formula: ##STR1## which are useful in stimulating cardiac activity and in treating congestive heart failure and bronchoconstriction, pharmaceutical compositions including these inhibitors, and methods of using these compounds to produce phosphodiesterase (type III) inhibition in mammals.

  磷酸二酯酶（III型）抑制剂具有以下结构式：##STR1##，可用于刺激心脏活动，治疗充血性心力衰竭和支气管痉挛，包括这些抑制剂的药物组合物，以及使用这些化合物在哺乳动物中产生磷酸二酯酶（III型）抑制的方法。
• Thiadiazinones for stimulating cardiac activity
  申请人：Smith Kline & French Laboratories Limited

  公开号：US05246928A1

  公开（公告）日：1993-09-21

  This invention relates to N-phenylpyridone derivatives which have inotropic, vasodilator and bronchodilator activity. A compound of the invention is 5-methyl-6-[4-(4-oxo-1,4-dihydropyridin-1-yl)phenyl]-4,5-dihydro-3(2H)pyri dazinone.

  本发明涉及具有肌力增强、血管扩张和支气管扩张活性的N-苯基吡啶酮衍生物。该发明的一种化合物是5-甲基-6-[4-(4-氧代-1,4-二氢吡啶-1-基)苯基]-4,5-二氢-3(2H)吡啶酮。
• Chemical compounds
  申请人：Smith Kline & French Laboratories Limited

  公开号：US05066653A1

  公开（公告）日：1991-11-19

  Phosphodiesterase (type III) inhibitors having the formula: ##STR1## wherein R.sup.4 is hydrogen and A is a dihydro-1,2,4-triazin-3-one group or a dihydro-1,2,4-triazin-6-one group which are useful in stimulating cardiac activity and in treating congestive heart failure and bronchoconstriction, pharmaceutical compositions including these inhibitors, and methods of using these compounds to produce phosphodiesterase (type III) inhibition in mammals.

  翻译结果如下： 磷酸二酯酶（III型）抑制剂的化学式为：##STR1## 其中R.sup.4为氢，A为二氢-1,2,4-三嗪-3-酮基团或二氢-1,2,4-三嗪-6-酮基团，可用于刺激心脏活动，治疗充血性心力衰竭和支气管收缩，包括这些抑制剂的制药组合物以及使用这些化合物在哺乳动物中产生磷酸二酯酶（III型）抑制的方法。
• 4(4-oxo-1,4-dihydropyridin-1-yl)phenyl derivatives
  申请人：SMITH KLINE & FRENCH LABORATORIES LIMITED

  公开号：EP0220044A2

  公开（公告）日：1987-04-29

  Compounds of the formula (1) : and pharmaceutically acceptable salts thereof are described wherein A is a group of sub-formula (a), (b), (c) or (d): X is CHR1, sulphur, oxygen or NH, R1 is hydrogen, or R1 and R2 together form a bond, R2 is hydrogen or methyl, or R1 and R2 together form a bond, R3 is hydrogen or together with R4 form a methylene or 1,2-ethanediyl group, Y is sulphur, oxygen or NH, Z is sulphur or oxygen, R4 is hydrogen or together with R3 form a methylene or 1,2-ethanediyl group, with the proviso that X is CHR1 or sulphur when R3 together with R4 form a methylene or 1,2-ethanediyl group. These compounds have inotropic, vasodilator, bronchodilating and platelet aggregation inhibiting properties. Pharmaceutical compositions are described as are methods of use. Intermediates and processes for the preparation of the compounds of the formula (1) are described.

  式 (1) ： 及其药学上可接受的盐，其中 A 是子式（a）、（b）、（c）或（d）的基团： X 是 CHR1、硫、氧或 NH，R1 是氢，或 R1 和 R2 一起形成键，R2 是氢或甲基，或 R1 和 R2 一起形成键，R3 是氢，或与 R4 一起形成亚甲基或 1，2-乙二基，Y 是硫、氧或 NH，Z 为硫或氧，R4 为氢或与 R3 一起形成亚甲基或 1,2-乙二基，但当 R3 与 R4 一起形成亚甲基或 1,2-乙二基时，X 为 CHR1 或硫。这些化合物具有肌力、血管扩张、支气管扩张和血小板聚集抑制特性。本文介绍了药物组合物以及使用方法。还描述了制备式（1）化合物的中间体和工艺。
• US4906628A
  申请人：——

  公开号：US4906628A

  公开（公告）日：1990-03-06