ethyl 6-ethyl-7-methoxy-5-methylimidazo<1,2-a>pyrimidine-2-carboxylate | 90808-77-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并[1，2-a]嘧啶
• 英文名称: ethyl 6-ethyl-7-methoxy-5-methylimidazo<1,2-a>pyrimidine-2-carboxylate
• 英文别名: ethyl 6-ethyl-7-methoxy-5-methylimidazo[1,2-a]pyrimidine-2-carboxylate
• CAS: 90808-77-8
• 化学式: C₁₃H₁₇N₃O₃
• 分子量: 263.296
• InChiKey: WOIXDFQQMSFYKX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  65.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 6-ethyl-7-methoxy-5-methylimidazo<1,2-a>pyrimidine-2-carboxylate 在 劳森试剂 、 氨 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 6-ethyl-7-methoxy-5-methylimidazo<1,2-a>pyrimidine-2-thiocarboxamide
  参考文献：
  名称：

  2-(Oxadiazolyl)- and 2-(thiazolyl)imidazo[1,2-a]pyrimidines as agonists and inverse agonists at benzodiazepine receptors

  摘要：

  Oxadiazoles, like the benzoyl group in a series of imidazo[1,2-alpha]pyrimidines, have been found to be metabolically stable alternatives to ester groups in benzodiazepine-receptor ligands. This change has lead to a number of compounds which bind to the receptors and which exhibit potent agonist activity in a food-motivated conflict test thought to predict anxiolytic properties. Compounds 4, 5, and 13 were equipotent with chlordiazepoxide but showed little or no myorelaxant effects. Replacing the oxadiazole group by thiazole gave compounds such as 23 which binds to the benzodiazepine receptor but exhibits the intrinsic activity of a partial inverse agonist in vivo.

  DOI：

  10.1021/jm00111a021
• 作为产物：
  描述：

  5-ethyl-4-methoxy-6-methyl-2-pyrimidinamine 、 3-溴丙酮酸乙酯 生成 ethyl 6-ethyl-7-methoxy-5-methylimidazo<1,2-a>pyrimidine-2-carboxylate
  参考文献：
  名称：

  2-(Oxadiazolyl)- and 2-(thiazolyl)imidazo[1,2-a]pyrimidines as agonists and inverse agonists at benzodiazepine receptors

  摘要：

  Oxadiazoles, like the benzoyl group in a series of imidazo[1,2-alpha]pyrimidines, have been found to be metabolically stable alternatives to ester groups in benzodiazepine-receptor ligands. This change has lead to a number of compounds which bind to the receptors and which exhibit potent agonist activity in a food-motivated conflict test thought to predict anxiolytic properties. Compounds 4, 5, and 13 were equipotent with chlordiazepoxide but showed little or no myorelaxant effects. Replacing the oxadiazole group by thiazole gave compounds such as 23 which binds to the benzodiazepine receptor but exhibits the intrinsic activity of a partial inverse agonist in vivo.

  DOI：

  10.1021/jm00111a021

文献信息

• 2-(1,2,4-oxadiazol-5-yl) and
  申请人：Roussel Uclaf

  公开号：US04703049A1

  公开（公告）日：1987-10-27

  Novel compounds selected from the group consisting of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of 1,2,4-oxadiazol-5-yl and 1,3,4-thiadiazol-2-yl, both optionally substituted with alkyl of 1 to 3 carbon atoms or alkenyl of 2 to 5 carbon atoms and 1,2,4-oxadiazol-3-yl and 1,3,4-oxadiazol-2-yl, both optionally substituted with alkenyl of 2 to 5 carbon atoms, alkyl of 1 to 3 carbon atoms or alkyl of 1 to 3 carbon atoms substituted with at least one fluorine, R.sub.2 and R.sub.3 are individually selected from the group consisting of hydrogen, alkyl of 1 to 3 carbon atoms and alkenyl of 2 to 5 carbon atoms or together form alkylene of 3 to 5 carbon atoms, X is selected from the group consisting of --O-- and --S--, R.sub.4 is alkyl of 1 to 3 carbon atoms and their non-toxic, pharmaceutically acceptable acid addition salts having anxiolytic sedative and hypnotic activity and a novel process and novel intermediates therefor.

  从以下组中选择的新化合物，其化学式为##STR1##其中R.sub.1选自1,2,4-噁唑啉-5-基和1,3,4-噻二唑-2-基，两者均可用1至3个碳原子的烷基或2至5个碳原子的烯基取代，以及1,2,4-噁唑啉-3-基和1,3,4-噁唑啉-2-基，两者均可用2至5个碳原子的烯基，1至3个碳原子的烷基或至少一个氟取代的1至3个碳原子的烷基取代，R.sub.2和R.sub.3分别选自氢、1至3个碳原子的烷基和2至5个碳原子的烯基，或者一起形成3至5个碳原子的烷基，X选自--O--和--S--，R.sub.4为1至3个碳原子的烷基，以及其无毒、药学上可接受的酸盐，具有抗焦虑、镇静和催眠活性，以及用于其制备的新工艺和新中间体。
• 2-thiazolyl-imidazo[1,2,-a]pyrimidines
  申请人：Roussel Uclaf

  公开号：US04925846A1

  公开（公告）日：1990-05-15

  A compound selected from the group consisting of a compound of the formula ##STR1## wherein R.sub.1 is thiazol-2-yl optionally substituted by 1 or 2 alkyl of 1 to 3 carbon atoms optionally substituted by one or more fluorine or --COOAlk, Alk is alkyl of 1 to 3 carbon atoms, R.sub.2 and R.sub.3 are individually selected from the group consisting of hydrogen, alkyl of 1 to 3 carbon atoms and alkenyl of 2 to 5 carbon atoms or R.sub.2 and R.sub.3 together form alkylene of 3 to 5 carbon atoms, X is oxygen or sulfur and R.sub.4 is alkyl of 1 to 3 carbon atoms and their non-toxic, pharmaceutically acceptable acid addition salts having minor tranquillizing activity and useful for the treatment of obesity and cognitive impairment.

  从以下化合物中选择一种：式中R.sub.1是噻唑-2-基，可选择性地被1或2个1至3个碳原子的烷基取代，该烷基可选择性地被一个或多个氟或--COOAlk取代，其中Alk是1至3个碳原子的烷基，R.sub.2和R.sub.3分别选自氢，1至3个碳原子的烷基和2至5个碳原子的烯基，或R.sub.2和R.sub.3共同形成3至5个碳原子的烷基，X是氧或硫，R.sub.4是1至3个碳原子的烷基，以及它们的非毒性、药学上可接受的酸盐，具有轻微的镇静作用，可用于治疗肥胖和认知障碍。
• Imidazo(1,2-a)pyrimidines and their salts useful for treating anxiety
  申请人：Roussel Uclaf

  公开号：US04532243A1

  公开（公告）日：1985-07-30

  Novel imidazo[1,2-a]pyrimidines of the formula ##STR1## wherein R is selected from the group consisting of alkyl of 1 to 8 carbon atoms, alkenyl of 2 to 8 carbon atoms, cycloalkyl of 3 to 7 carbon atoms, cycloalkylalkyl of 4 to 12 carbon atoms, aryl of 6 to 12 carbon atoms, thienyl and pyridyl, each of said group being optionally substituted with at least one member of the group consisting of halogen, alkyl of 1 to 5 carbon atoms, alkoxy and alkylthio of 1 to 5 carbon atoms, trifluoromethyl, amino, alkylamino of 1 to 5 alkyl carbon atoms and dialkylamino with alkyl of 1 to 5 carbons atoms, R.sub.1 and R.sub.2 are individually selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms, alkenyl of 2 to 5 carbon atoms, cycloalkyl of 3 to 7 carbon atoms, cycloalkylalkyl of 4 to 12 carbon atoms, benzyl and phenethyl, or taken together form alkylene of 3 to 5 carbon atoms, each of said groups being optionally substituted with at least one member of the group consisting of halogen, alkyl of 1 to 5 carbon atoms, alkoxy and alkylthio of 1 to 5 carbon atoms, trifluoromethyl, amino, alkylamino of 1 to 5 alkyl carbon atoms and dialkylamino with alkyls of 1 to 5 carbon atoms, X is selected from the group consisting of oxygen and sulfur and R.sub.3 is alkyl of 1 to 5 carbon atoms and their non-toxic, pharmaceutically acceptable acid addition salts, having anxiolytic activity and novel intermediates.

  该专利涉及一种具有抗焦虑活性的新型中间体和公式为##STR1##的新型咪唑并[1,2-a]嘧啶化合物，其中R选自1至8碳原子的烷基，2至8碳原子的烯基，3至7碳原子的环烷基，4至12碳原子的环烷基烷基，6至12碳原子的芳基，噻吩基和吡啶基等组中的每个，其中每个组都可以选择性地用1至5碳原子的卤素，烷基，1至5碳原子的烷氧基和烷硫基，三氟甲基，氨基，1至5碳原子的烷基氨基和烷基二烷基氨基进行取代，R1和R2分别选自1至8碳原子的烷基，2至5碳原子的烯基，3至7碳原子的环烷基，4至12碳原子的环烷基烷基，苄基和苯乙基，或一起形成3至5碳原子的烷基，其中每个组都可以选择性地用1至5碳原子的卤素，烷基，1至5碳原子的烷氧基和烷硫基，三氟甲基，氨基，1至5碳原子的烷基氨基和烷基二烷基氨基进行取代，X选自氧和硫，R3为1至5碳原子的烷基，以及它们的非毒性、药学上可接受的酸盐。
• Imidazo[1,2-a]pyrimidines
  申请人：Roussel Uclaf

  公开号：US04588720A1

  公开（公告）日：1986-05-13

  Novel imidazo[1,2-a]pyrimidines of the formula ##STR1## wherein R is selected from the group consisting of alkyl of 1 to 8 carbon atoms, alkenyl of 2 to 8 carbon atoms, cycloalkyl of 3 to 7 carbon atoms, cycloalkylalkyl of 4 to 12 carbon atoms, aryl of 6 to 12 carbon atoms, thienyl and pyridyl, each of said group being optionally substituted with at least one member of the group consisting of halogen, alkyl of 1 to 5 carbon atoms, alkoxy and alkylthio of 1 to 5 carbon atoms, trifluoromethyl, amino, alkylamino of 1 to 5 alkyl carbon atoms and dialkylamino with alkyl of 1 to 5 carbon atoms, R.sub.1 and R.sub.2 are individually selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms, alkenyl of 2 to 5 carbon atoms, cycloalkyl of 3 to 7 carbon atoms, cycloalkylalkyl of 4 to 12 carbon atoms, benzyl and phenethyl, or taken together form alkylene of 3 to 5 carbon atoms, each of said groups being optionally substituted with at least one member of the group consisting of halogen, alkyl of 1 to 5 carbon atoms, alkoxy and alkylthio of 1 to 5 carbon atoms, trifluoromethyl, amino, alkylamino of 1 to 5 alkyl carbon atoms and dialkylamino with alkyls of 1 to 5 carbon atoms, X is selected from the group consisting of oxygen and sulfur and R.sub.3 is alkyl of 1 to 5 carbon atoms and their non-toxic, pharmaceutically acceptable acid addition salts, having anxiolytic activity and novel intermediates.

  该专利描述了一种新型的咪唑并[1,2-a]嘧啶类化合物，其化学式为##STR1##其中R选择自1到8个碳原子的烷基、2到8个碳原子的烯基、3到7个碳原子的环烷基、4到12个碳原子的环烷基烷基、6到12个碳原子的芳基、噻吩基和吡啶基，所述的每个基团都可以选择性地用卤素、1到5个碳原子的烷基、1到5个碳原子的烷氧基和烷硫基、三氟甲基、氨基、1到5个烷基碳原子的烷基氨基和带有1到5个碳原子烷基的二烷基氨基中的至少一种成员进行取代；R.sub.1和R.sub.2单独选择自1到8个碳原子的烷基、2到5个碳原子的烯基、3到7个碳原子的环烷基、4到12个碳原子的环烷基烷基、苄基和苯乙基，或者一起形成3到5个碳原子的烷基，所述的每个基团都可以选择性地用卤素、1到5个碳原子的烷基、1到5个碳原子的烷氧基和烷硫基、三氟甲基、氨基、1到5个烷基碳原子的烷基氨基和带有1到5个碳原子烷基的二烷基氨基中的至少一种成员进行取代；X选择自氧和硫，R.sub.3为1到5个碳原子的烷基，以及其无毒、药学上可接受的酸盐，具有抗焦虑活性和新型中间体。
• DEACON, ROBERT MICHAEL JOHN;GARDNER, COLIN ROBERT;GILLESPIE, ROGER JOHN;T+
  作者：DEACON, ROBERT MICHAEL JOHN、GARDNER, COLIN ROBERT、GILLESPIE, ROGER JOHN、T+

  DOI：——

  日期：——