6-chloro-3-<4-(2-methoxyphenyl)-1-piperazinyl>pyridazine | 89937-27-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 6-chloro-3-<4-(2-methoxyphenyl)-1-piperazinyl>pyridazine
• 英文别名: 3-Chloro-6-[4-(2-methoxyphenyl)-1-piperazinyl]pyridazine；3-chloro-6-[4-(2-methoxyphenyl)piperazin-1-yl]pyridazine
• CAS: 89937-27-9
• 化学式: C₁₅H₁₇ClN₄O
• 分子量: 304.779
• InChiKey: NVOUARGRHDIUQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  41.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  苯甲醛 、 6-chloro-3-<4-(2-methoxyphenyl)-1-piperazinyl>pyridazine 在 一水合肼 作用下， 生成 N-{6-[4-(2-Methoxy-phenyl)-piperazin-1-yl]-pyridazin-3-yl}-N'-[1-phenyl-meth-(E)-ylidene]-hydrazine
  参考文献：
  名称：

  Antihypertensives. N-1H-Pyrrol-1-yl-3-pyridazinamines

  摘要：

  The hypothesis that the side effects of hydralazine, such as mutagenicity and lupus erythematosus like syndrome, might be due to the NHNH2 group prompted us to incorporate part of this moiety into a pyrrole ring. Therefore, we prepared a series of N-1H-pyrrol-1-yl-3-pyridazinamines and a limited number of N-1H-pyrrol-1-yl-1-phthalazinamines by reaction of 3-hydrazinopyridazines and 1-hydrazinophthalazines with gamma-diketones. Most of these compounds, especially in the pyridazine series, showed moderate to strong antihypertensive activity in spontaneously hypertensive rats. The decrease in blood pressure generally had a slow onset after either oral or intravenous administration. N-(2,5-Dimethyl-1H-pyrrol-1-yl)-6-(4-morpholinyl)-3-pyridazinamine hydrochloride (30) (MDL 899) showed no mutagenic activity in several tests and is now in clinical trials in patients.

  DOI：

  10.1021/jm00374a024
• 作为产物：
  描述：

  3,6-二氯哒嗪 、 1-(2-甲氧苯基)哌嗪 以 乙醇 为溶剂， 反应 10.0h， 以70%的产率得到6-chloro-3-<4-(2-methoxyphenyl)-1-piperazinyl>pyridazine
  参考文献：
  名称：

  Antihypertensives. N-1H-Pyrrol-1-yl-3-pyridazinamines

  摘要：

  The hypothesis that the side effects of hydralazine, such as mutagenicity and lupus erythematosus like syndrome, might be due to the NHNH2 group prompted us to incorporate part of this moiety into a pyrrole ring. Therefore, we prepared a series of N-1H-pyrrol-1-yl-3-pyridazinamines and a limited number of N-1H-pyrrol-1-yl-1-phthalazinamines by reaction of 3-hydrazinopyridazines and 1-hydrazinophthalazines with gamma-diketones. Most of these compounds, especially in the pyridazine series, showed moderate to strong antihypertensive activity in spontaneously hypertensive rats. The decrease in blood pressure generally had a slow onset after either oral or intravenous administration. N-(2,5-Dimethyl-1H-pyrrol-1-yl)-6-(4-morpholinyl)-3-pyridazinamine hydrochloride (30) (MDL 899) showed no mutagenic activity in several tests and is now in clinical trials in patients.

  DOI：

  10.1021/jm00374a024

文献信息

• Novel (4-substituted-piperazinyl)pyridazines
  申请人：JANSSEN PHARMACEUTICA N.V.

  公开号：EP0211457A2

  公开（公告）日：1987-02-25

  Novel (4-substituted-piperazinyl)pyridazines of formula wherein R is hydrogen, halo, C1-6alkyloxy, hydroxy or phenyl; m is the integer 2 or 3; R¹, R², R³ and R⁴ are, each independently, hydrogen, or C1-6alkyl; or where R³ and R⁴ are substituted on a different carbon atom, R³ and R⁴ taken together, may form a bivalent radical -CH₂-CH₂-; R⁵ is (aryl)C2-6alkenyl, (aryl)C2-6alkynyl, (aryl)(hydroxy)­C1-6alkyl or (aryl)(oxo)C1-6alkyl; the N-oxide forms, the pharmaceutically acceptable acid addition salts and the possible stereochemically isomeric forms, which compounds are analgesic and antitussive agents; pharmaceutical compositions containing such compounds as an active ingredient and methods of preparing said compounds and pharmaceutical compositions.

  新型 (4-取代哌嗪基)哒嗪，其式如下 其中 R 是氢、卤素、C1-6-烷氧基、羟基或苯基； m 是整数 2 或 3； R¹、R²、R³ 和 R⁴ 各自独立为氢或 C1-6 烷基； 或当 R³ 和 R⁴ 在不同碳原子上被取代时，R³ 和 R⁴ 合在一起可形成二价基 -CH₂-CH₂-； R⁵ 是（芳基）C2-6烯基、（芳基）C2-6炔基、（芳基）（羟基）C1-6烷基或（芳基）（氧代）C1-6烷基； N-氧化物形式、药学上可接受的酸加成盐以及可能的立体化学异构形式，这些化合物是镇痛和止咳剂；含有这些化合物作为活性成分的药物组合物以及制备所述化合物和药物组合物的方法。
• Anti-virally active pyridazinamines
  申请人：JANSSEN PHARMACEUTICA N.V.

  公开号：EP0156433B1

  公开（公告）日：1991-02-27
• 6-Amino substituted N-pyrrolyl-3-pyridazine amines, their preparation, and pharmaceutically antihypertensive compositions containing them
  申请人：GRUPPO LEPETIT S.P.A.

  公开号：EP0009655B1

  公开（公告）日：1983-05-11
• US4247551A
  申请人：——

  公开号：US4247551A

  公开（公告）日：1981-01-27
• US5001125A
  申请人：——

  公开号：US5001125A

  公开（公告）日：1991-03-19