5-(2-ethoxyphenyl)-1,3-dimethyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one | 139756-28-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡唑并嘧啶类
• 英文名称: 5-(2-ethoxyphenyl)-1,3-dimethyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
• 英文别名: 5-(2-ethoxyphenyl)-1,3-dimethyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one；5-(2-ethoxyphenyl)-1,3-dimethyl-6H-pyrazolo[4,3-d]pyrimidin-7-one
• CAS: 139756-28-8
• 化学式: C₁₅H₁₆N₄O₂
• 分子量: 284.318
• InChiKey: SRVVOQVTSUQJCP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  68.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  邻乙氧基苯甲酰氯 在 4-二甲氨基吡啶 、 sodium hydroxide 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 生成 5-(2-ethoxyphenyl)-1,3-dimethyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
  参考文献：
  名称：

  Sildenafil (VIAGRATM), a potent and selective inhibitor of type 5 cGMP phosphodiesterase with utility for the treatment of male erectile dysfunction

  摘要：

  5-(2'-Alkoxyphenyl)pyrazolo[4,3-d]pyrimidin-7-ones, and in particular our preferred compound, sildenafil (VIAGRA(TM)), discovered through a rational drug design programme, are potent and selective inhibitors of the type 5 cGMP phosphodiesterase from both rabbit platelets and human corpus cavernosum. Sildenafil is currently in the clinic for the oral treatment of male erectile dysfunction. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00323-x

文献信息

• Pyrazolopyrimidinone antianginal agents
  申请人：Pfizer Inc.

  公开号：US05250534A1

  公开（公告）日：1993-10-05

  Compounds of the formula: ##STR1## wherein R.sup.1 is H, C.sub.1 -C.sub.3 alkyl, C.sub.3 -C.sub.5 cycloalkyl or C.sub.1 -C.sub.3 perfluoroalkyl; R.sup.2 is H, C.sub.1 -C.sub.6 alkyl optionally substituted by OH, C.sub.1 -C.sub.3 alkoxy or C.sub.3 -C.sub.6 cycloalkyl, or C.sub.1 -C.sub.3 perfluoroalkyl; R.sup.3 is C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 alkynyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.1 -C.sub.6 perfluoroalkyl or (C.sub.3 -C.sub.6 cycloalkyl)C.sub.1 -C.sub.6 alkyl; R.sup.4 taken together with the nitrogen atom to which it is attached completes a pyrrolidinyl, piperidino, morpholino, or 4-N-(R.sup.6)-piperazinyl group; R.sup.5 is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.3 alkoxy, NR.sup.7 R.sup.8, or CONR.sup.7 R.sup.8 ; R.sup.6 is H, C.sub.1 -C.sub.6 alkyl, (C.sub.1 -C.sub.3 alkoxy) C.sub.2 - C.sub.6 alkyl, hydroxy C.sub.2 -C.sub.6 alkyl, (R.sup.7 R.sup.8 N)C.sub.2 -C.sub.6 alkyl, (R.sup.7 R.sup.8 NCO)C.sub.1 -C.sub.6 alkyl, CONR.sup.7 R.sup.8, CSNR.sup.7 R.sup.8 or C(NH)NR.sup.7 R.sup.8 ; R.sup.7 and R.sup.8 are each independently H, C.sub.1 -C.sub.4 alkyl, (C.sub.1 -C.sub.3 alkoxy)C.sub.2 -C.sub.4 alkyl or hydroxy C.sub.2 -C.sub.4 alkyl; and pharmaceutically acceptable salts thereof, are selective cGMP PDE inhibitors useful in the treatment of cardiovascular disorders such as angina, hypertension, heart failure and atherosclerosis.

  该化合物的结构式为：##STR1## 其中R.sup.1为H，C.sub.1 -C.sub.3烷基，C.sub.3 -C.sub.5环烷基或C.sub.1 -C.sub.3全氟烷基；R.sup.2为H，C.sub.1 -C.sub.6烷基，可以选择性地被OH，C.sub.1 -C.sub.3烷氧基或C.sub.3 -C.sub.6环烷基，或C.sub.1 -C.sub.3全氟烷基取代；R.sup.3为C.sub.1 -C.sub.6烷基，C.sub.3 -C.sub.6烯基，C.sub.3 -C.sub.6炔基，C.sub.3 -C.sub.7环烷基，C.sub.1 -C.sub.6全氟烷基或(C.sub.3 -C.sub.6环烷基)C.sub.1 -C.sub.6烷基；R.sup.4与其连接的氮原子一起形成吡咯啉基、哌啶基、吗啉基或4-N-(R.sup.6)-哌嗪基；R.sup.5为H，C.sub.1 -C.sub.4烷基，C.sub.1 -C.sub.3烷氧基，NR.sup.7 R.sup.8，或CONR.sup.7 R.sup.8；R.sup.6为H，C.sub.1 -C.sub.6烷基，(C.sub.1 -C.sub.3烷氧基)C.sub.2 - C.sub.6烷基，羟基C.sub.2 -C.sub.6烷基，(R.sup.7 R.sup.8 N)C.sub.2 -C.sub.6烷基，(R.sup.7 R.sup.8 NCO)C.sub.1 -C.sub.6烷基，CONR.sup.7 R.sup.8，CSNR.sup.7 R.sup.8或C(NH)NR.sup.7 R.sup.8；R.sup.7和R.sup.8各自独立地为H，C.sub.1 -C.sub.4烷基，(C.sub.1 -C.sub.3烷氧基)C.sub.2 -C.sub.4烷基或羟基C.sub.2 -C.sub.4烷基；以及其药学上可接受的盐，是用于治疗心血管疾病如心绞痛、高血压、心力衰竭和动脉粥样硬化的选择性cGMP PDE抑制剂。
• Intermediates useful in the synthesis of pyrazolopyrimidinone
  申请人：Pfizer Inc.

  公开号：US05719283A1

  公开（公告）日：1998-02-17

  Compounds of the formula ##STR1## wherein R.sup.1 is H, C.sub.1 -C.sub.3 alkyl, C.sub.3 -C.sub.5 cycloalkyl or C.sub.1 -C.sub.3 perfluoroalkyl; R.sup.2 is H, C.sub.1 -C.sub.6 alkyl optionally substituted by OH, C.sub.1 -C.sub.3 alkoxy or C.sub.3 -C.sub.6 cycloalkyl, or C.sub.1 -C.sub.3 perfluoroalkyl; R.sup.3 is H, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 alkynyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.1 -C.sub.6 perfluoroalkyl or (C.sub.3 -C.sub.6 cycloalkyl)C.sub.1 -C.sub.6 alkyl; and Y is chloro, bromo, or fluoro. The above compounds are intermediates useful in the synthesis of certain pyrazolopyrimidinones which inhibit cyclic guanosine 3', 5'-monophosphate phosphodiesterase.

  化合物的公式为##STR1##其中R.sup.1是H，C.sub.1-C.sub.3烷基，C.sub.3-C.sub.5环烷基或C.sub.1-C.sub.3全氟烷基；R.sup.2是H，C.sub.1-C.sub.6烷基，可选择性地被OH，C.sub.1-C.sub.3烷氧基或C.sub.3-C.sub.6环烷基或C.sub.1-C.sub.3全氟烷基取代，或者C.sub.1-C.sub.3全氟烷基；R.sup.3是H，C.sub.1-C.sub.6烷基，C.sub.3-C.sub.6烯基，C.sub.3-C.sub.6炔基，C.sub.3-C.sub.7环烷基，C.sub.1-C.sub.6全氟烷基或(C.sub.3-C.sub.6环烷基)C.sub.1-C.sub.6烷基；Y是氯，溴或氟。上述化合物是合成某些嘧啶并嘧啶酮的中间体，这些嘧啶并嘧啶酮可以抑制环鸟苷3'，5'-单磷酸酯酶。
• Use of a PDE5 inhibitor for treating and preventing hypopigmentary disorders
  申请人：Switch Biotech Aktiengesellschaft

  公开号：EP1759700A1

  公开（公告）日：2007-03-07

  The invention relates to the use of PDE5 inhibitors, preferably sildenafil or tadalafil, optionally in combination with a further active ingredient, for treating and/or preventing hypopigmentary disorders.

  本发明涉及 PDE5 抑制剂（最好是西地那非或他达拉非）在治疗和/或预防色素减退症方面的用途，可选择与另一种活性成分结合使用。
• US5250534A
  申请人：——

  公开号：US5250534A

  公开（公告）日：1993-10-05
• US5346901A
  申请人：——

  公开号：US5346901A

  公开（公告）日：1994-09-13