1-(3,4-dimethoxyphenyl) barbituric acid | 298680-49-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(3,4-dimethoxyphenyl) barbituric acid
• 英文别名: 1-(3,4-Dimethoxyphenyl)-1,3-diazinane-2,4,6-trione
• CAS: 298680-49-6
• 化学式: C₁₂H₁₂N₂O₅
• 分子量: 264.238
• InChiKey: FGQJLHGDERGRCG-UHFFFAOYSA-N

物化性质

• 密度：
  1.353±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  84.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(3,4-dimethoxyphenyl) barbituric acid 在 三氯氧磷 作用下， 以 1,4-二氧六环 、 甲醇 、 氯仿 为溶剂， 生成 2-chloro-9,10-dimethoxy-6,7-dihydro-4H-pyrimido<6,1-a>isoquinolin-4-one
  参考文献：
  名称：

  Derivatives of pyrimido[6,1-a]isoquinolin-4-one

  摘要：

  该发明提供了通式(I)的化合物或其盐： 其中R1和R2分别代表C1-6烷基或C2-7酰基基团；X代表OCH2或CR3R4基团；其中R3或R4分别代表氢原子或C1-3烷基基团；R5代表氢原子或C1-3烷基、C2-3烯基或C2-3炔基团；R6代表氢原子或C1-6烷基、C2-6烯基、C2-6炔基、氨基、C1-6烷基氨基、双(C1-6)烷基氨基或C2-7酰氨基团；R7和R8分别代表氢或卤原子或羟基、三氟甲基、C1-6烷基、C2-6烯基、C2-6炔基、C2-7酰基、C1-6烷基硫基、C1-6烷氧基、C3-6环烷基；R9代表氢或卤原子或羟基、三氟甲基、C1-6烷基、C2-6烯基、C2-6炔基、C2-7酰基、C1-6烷基硫基、C1-6烷氧基或C3-6环烷基。该化合物或其盐可用于治疗哮喘等呼吸系统疾病。该发明的化合物比已知的三氮杂环化合物trequinsin（9,10-二甲氧基-3-甲基-2-间甲苯基亚基-2,3,6,7-四氢-4H-嘧啶并［6,1-a］异喹啉-4-酮）具有更长的作用持续时间。

  公开号：

  US20030119813A1

文献信息

• Derivatives of pyrimido[6.1-a]isoquinolin-4-one
  申请人：——

  公开号：US20030036542A1

  公开（公告）日：2003-02-20

  The invention provides compounds or salts thereof of the general formula (I): 1 wherein each of R 1 and RX independently represents a C 1-6 alkyl or C 2-7 acyl group; X represents OCH 2 or a group CR 3 R 4 ; wherein each of R 3 or R 4 independently represents a hydrogen atom or a C 1-3 alkyl group; R 5 represents a hydrogen atom or a C 1-3 alkyl, C 2-3 alkenyl or C 2-3 alkynyl group; R 6 represents a hydrogen atom or a C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, amino, C 1-6 alkylamino, di(C 1-6 ) alkylamino or C 2-7 acylamino group; each of R 7 and R 8 independently represents a hydrogen or halogen atom or a hydroxy, trifluoromethyl, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 2-7 acyl, C 1-6 alkylthio, C 1-6 alkoxy, C 3-6 cycloalkyl; and R 9 represents a hydrogen or halogen atom or a hydroxy, trifluoromethyl, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 2-7 acyl, C 1-6 alkylthio, C 1-6 alkoxy or C 3-6 cycloalkyl group. The compounds or salts thereof are useful for treatment of respiratory disorders such as asthma. Compounds of the invention have a longer duration of action than the known compound trequinsin (9,10-dimethoxy-3 methyl-2-mesitylimino-2,3,6,7-tetrahydro- 4 -H-pyrimido[6,1-a]isoquinolin-4-one).

  该发明提供了通式（I）的化合物或其盐： 其中，R1和RX分别独立表示C1-6烷基或C2-7酰基；X表示OCH2或CR3R4基团；R3或R4分别独立表示氢原子或C1-3烷基；R5表示氢原子或C1-3烷基、C2-3烯基或C2-3炔基；R6表示氢原子或C1-6烷基、C2-6烯基、C2-6炔基、氨基、C1-6烷基氨基、二（C1-6）烷基氨基或C2-7酰氨基；R7和R8分别独立表示氢或卤素原子、羟基、三氟甲基、C1-6烷基、C2-6烯基、C2-6炔基、C2-7酰基、C1-6烷基硫基、C1-6烷氧基、C3-6环烷基；R9表示氢或卤素原子、羟基、三氟甲基、C1-6烷基、C2-6烯基、C2-6炔基、C2-7酰基、C1-6烷基硫基、C1-6烷氧基或C3-6环烷基。该化合物或其盐可用于治疗哮喘等呼吸系统疾病。该发明的化合物比已知的化合物特雷昆辛（9,10-二甲氧基-3-甲基-2-间二甲苯亚基-2,3,6,7-四氢-4H-嘧啶并［6,1-a］异喹啉-4-酮）具有更长的作用持续时间。
• [EN] DERIVATIVES OF PYRIMIDO[6,1-a]ISOQUINOLIN-4-ONE<br/>[FR] DERIVES DE PYRIMIDO [6,1-A] ISOQUINOLEIN-4-ONE ET LEUR UTILISATION EN MEDECINE
  申请人：VANGUARD MEDICA LTD

  公开号：WO2000058308A1

  公开（公告）日：2000-10-05

  Compounds of general formula (I) wherein each of R?1 and R2¿ independently represents a C¿1-6? alkyl or C2-7 acyl group; R?5¿ represents a hydrogen atom or a C¿1-3? alkyl, C2-3 alkenyl or C2-3 alkynyl group; R?6¿ represents a hydrogen atom or a C¿1-6? alkyl, C2-6 alkenyl, C2-6 alkynyl, amino, C1-6 alkylamino, di(C1-6) alkylamino or C2-7 acylamino group; each of R?7 and R8¿ independently represents a hydrogen or halogen atom or a hydroxy, trifluoromethyl, C¿1-6? alkyl, C2-6 alkenyl, C2-6 alkynyl, C2-7 acyl, C1-6 alkythio, C1-6 alkoxy, C3-6 cycloalkyl; and R?9¿ represents a hydrogen or halogen atom or a hydroxy, trifluoromethyl, C¿1-6? alkyl, C2-6 alkenyl, C2-6 alkynyl, C2-7 acyl, C1-6 alkythio, C1-6 alkoxy or C3-6 cycloalkyl group; X represents OCH2 or a group CR?3R4¿, wherein each of R?3 and R4¿ independently represents a hydrogen atom or a C¿1-3? alkyl group; each of R?10 and R11¿ independently represents a hydrogen atom, a C¿1-3? alkyl, C3-6 cycloalkyl or phenyl group; y represents an oxygen atom or a group CHNO2, NCN, NH or NNO2, n is an integer from 2 to 4; or a salt thereof; are useful for treatment of respiratory disorders such as asthma. Compounds of the invention have a longer duration of action than the known compound trequinsin (9, 10-dimethoxy-3-methyl-2-mesitylimino-2,3,6,7-tetrahydro-4H-pyrimido[6,1-a]isoquinolin-4-one) and do not have trequinsin's very bitter taste.

  通式（I）的化合物其中R1和R2分别独立地表示C1-6烷基或C2-7酰基基团；R5表示氢原子或C1-3烷基，C2-3烯基或C2-3炔基基团；R6表示氢原子或C1-6烷基，C2-6烯基，C2-6炔基，氨基，C1-6烷基氨基，双（C1-6）烷基氨基或C2-7酰基氨基基团；R7和R8分别独立地表示氢或卤原子或羟基，三氟甲基，C1-6烷基，C2-6烯基，C2-6炔基，C2-7酰基，C1-6烷硫基，C1-6烷氧基，C3-6环烷基；R9表示氢或卤原子或羟基，三氟甲基，C1-6烷基，C2-6烯基，C2-6炔基，C2-7酰基，C1-6烷硫基，C1-6烷氧基或C3-6环烷基基团；X表示OCH2或CR3R4基团，其中R3和R4分别独立地表示氢原子或C1-3烷基基团；R10和R11分别独立地表示氢原子，C1-3烷基，C3-6环烷基或苯基；y表示氧原子或CHNO2，NCN，NH或NNO2基团，n为2到4的整数；或其盐；用于治疗哮喘等呼吸系统疾病。与已知化合物trequinsin（9,10-二甲氧基-3-甲基-2-二苯基亚胺-2,3,6,7-四氢-4H-嘧啶[6,1-a]异喹啉-4-酮）相比，本发明化合物具有更长的作用时间，并且不具有trequinsin非常苦的味道。
• Derivatives of pyrimido[6, 1-A]isoquinolin-4-one
  申请人：Oxford Alexander William

  公开号：US20080206163A1

  公开（公告）日：2008-08-28

  Compounds of general formula (I) wherein each of R 1 and R 2 independently represents a C 1-6 alkyl or C 2-7 acyl group; R 5 represents a hydrogen atom or a C 1-3 alkyl, C 2-3 alkenyl or C 2-3 alkynyl group; R 6 represents a hydrogen atom or a C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, amino, C 1-6 alkylamino, di(C 1-6 ) alkylamino or C 2-7 acylamino group; each of R 7 and R 8 independently represents a hydrogen or halogen atom or a hydroxy, trifluoromethyl, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 2-7 acyl, C 1-6 alkythio, C 1-6 alkoxy, C 3-6 cycloalkyl; and R 9 represents a hydrogen or halogen atom or a hydroxy, trifluoromethyl, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 2-7 acyl, C 1-6 alkythio, C 1-6 alkoxy or C 3-6 cycloalkyl group; X represents OCH 2 or a group CR 3 R 4 , wherein each of R 3 and R 4 independently represents a hydrogen atom or a C 1-3 alkyl group; each of R 10 and R 11 independently represents a hydrogen atom, a C 1-3 alkyl, C 3-6 cycloalkyl or phenyl group; y represents an oxygen atom or a group CHNO 2 , NCN, NH or NNO 2 , n is an integer from 2 to 4; or a salt thereof; are useful for treatment of respiratory disorders such as asthma. Compounds of the invention have a longer duration of action than the known compound trequinsin (9,10-dimethoxy-3-methyl-2-mesitylimino-2,3,6,7-tetrahydro-4H-pyrimido[6,1-a]isoquinolin-4-one) and do not have trequinsin's very bitter taste.

  通式（I）的化合物，其中R1和R2各自独立地表示C1-6烷基或C2-7酰基基团；R5表示氢原子或C1-3烷基，C2-3烯基或C2-3炔基基团；R6表示氢原子或C1-6烷基，C2-6烯基，C2-6炔基，氨基，C1-6烷基氨基，二（C1-6）烷基氨基或C2-7酰胺基团；R7和R8各自独立地表示氢或卤原子，或羟基，三氟甲基，C1-6烷基，C2-6烯基，C2-6炔基，C2-7酰基，C1-6烷硫基，C1-6烷氧基，C3-6环烷基；R9表示氢或卤原子，或羟基，三氟甲基，C1-6烷基，C2-6烯基，C2-6炔基，C2-7酰基，C1-6烷硫基，C1-6烷氧基或C3-6环烷基；X表示OCH2或CR3R4基团，其中R3和R4各自独立地表示氢原子或C1-3烷基；R10和R11各自独立地表示氢原子，C1-3烷基，C3-6环烷基或苯基；y表示氧原子或CHNO2，NCN，NH或NNO2基团，n为2到4的整数；或其盐；可用于治疗哮喘等呼吸系统疾病。本发明的化合物比已知化合物特雷昆辛（9,10-二甲氧基-3-甲基-2-间苯基亚胺-2,3,6,7-四氢-4H-嘧啶[6,1-a]异喹啉-4-酮）具有更长的作用时间，并且不具有特雷昆辛的非常苦涩的味道。
• DERIVATIVES OF PYRIMIDO [6,1-A] ISOQUINOLIN-4-ONE
  申请人：Oxford Alexander William

  公开号：US20120302533A1

  公开（公告）日：2012-11-29

  The present invention relates to derivatives of pyrimido[6,1-a]isoquinolin-4-one and their application as inhibitors of phosphodiesterase (PDE) isoenzymes. More particularly the invention relates to derivatives of pyrimido[6,1-a]isoquinolin-4-one and their use in medicine for example as bronchodilators with anti-inflammatory properties.

  本发明涉及嘌呤并[6,1-a]异喹啉-4-酮的衍生物及其作为磷酸二酯酶（PDE）同工酶抑制剂的应用。更具体地，本发明涉及嘌呤并[6,1-a]异喹啉-4-酮的衍生物及其在医学上的应用，例如作为具有抗炎作用的支气管扩张剂。
• DERIVATIVES OF PYRIMIDO[6,1-A]ISOQUINOLIN-4-ONE
  申请人：Vernalis Limited

  公开号：EP1165558B1

  公开（公告）日：2003-09-24