3-butyryl-4-chloro-8-methoxyquinoline | 115607-76-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3-butyryl-4-chloro-8-methoxyquinoline
• 英文别名: 1-(4-chloro-8-methoxyquinolin-3-yl)butan-1-one
• CAS: 115607-76-6
• 化学式: C₁₄H₁₄ClNO₂
• 分子量: 263.724
• InChiKey: BKSSXCHSLZUWDA-UHFFFAOYSA-N

物化性质

• 沸点：
  364.7±37.0 °C(Predicted)
• 密度：
  1.213±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-butyryl-4-chloro-8-methoxyquinoline 在 三溴化硼 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 3-butyryl-4-(4-fluoro-2-methylphenyl-amino)-8-hydroxyquinoline
  参考文献：
  名称：

  Reversible Inhibitors of the Gastric (H+/K+)-ATPase. 4. Identification of an Inhibitor with an Intermediate Duration of Action

  摘要：

  3-Acyl-4-(arylamino)quinolines were previously identified as gastric (H+/K+)-ATPase inhibitors, and clinical efficacy has been demonstrated for compound 3 (SK&F 96067). In the present study the further structure-activity relationship of this series is developed. Only a limited range of substituents are tolerated on the N-aryl ring or the 6- and 7-positions of the quinoline, and although hydroxylated derivatives were identified possessing markedly greater affinity for the enzyme, none of these proved to have adequate potency after oral dosing. In contrast, the 8-position of the quinoline ring proved suitable for a wide variety of substituents, allowing modification of physicochemical properties while retaining primary activity. This led to the identification of compound 4 (SK&F 97574), which combines good oral potency with a somewhat longer duration of action than 3 (though much shorter than covalent inhibitors such as omeprazole). This compound was selected for further development and evaluation in man.

  DOI：

  10.1021/jm00014a026
• 作为产物：
  描述：

  丁酰乙酸乙酯 在 乙酸酐 、 三氯氧磷 作用下， 以 二苯醚 为溶剂， 反应 7.0h， 生成 3-butyryl-4-chloro-8-methoxyquinoline
  参考文献：
  名称：

  Reversible Inhibitors of the Gastric (H+/K+)-ATPase. 4. Identification of an Inhibitor with an Intermediate Duration of Action

  摘要：

  3-Acyl-4-(arylamino)quinolines were previously identified as gastric (H+/K+)-ATPase inhibitors, and clinical efficacy has been demonstrated for compound 3 (SK&F 96067). In the present study the further structure-activity relationship of this series is developed. Only a limited range of substituents are tolerated on the N-aryl ring or the 6- and 7-positions of the quinoline, and although hydroxylated derivatives were identified possessing markedly greater affinity for the enzyme, none of these proved to have adequate potency after oral dosing. In contrast, the 8-position of the quinoline ring proved suitable for a wide variety of substituents, allowing modification of physicochemical properties while retaining primary activity. This led to the identification of compound 4 (SK&F 97574), which combines good oral potency with a somewhat longer duration of action than 3 (though much shorter than covalent inhibitors such as omeprazole). This compound was selected for further development and evaluation in man.

  DOI：

  10.1021/jm00014a026

文献信息

• Substituted 4-aminoquinoline derivatives as gastric acid secretion
  申请人：Smith Kline & French Laboratories, Ltd.

  公开号：US05082848A1

  公开（公告）日：1992-01-21

  Substituted 4-aminoquinoline derivatives of the formula: ##STR1## wherein R.sup.1 is hydrogen, C.sub.1-6 alkyl, C.sub.1-6 alkoxyC.sub.1-6 alkyl; C.sub.3-6 cycloalkyl, C.sub.3-6 cycloalkyl-C.sub.1-6 alkyl, phenyl C.sub.1-6 alkyl, the phenyl groups being optionally substituted; R.sup.2 is hydroxy C.sub.1-6 alkyl, C.sub.1-6 alkoxyC.sub.1-6 alkyl or two adjacent groups R.sup.2 together form a C.sub.1-4 alkylenedioxy group; R.sup.3 is hydrogen, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, amino, C.sub.1-6 alkylthio, halogen, cyano, hydroxy, C1-6alkanoyl, or trifluromethyl; R.sup.4 is hydrogen, C.sub.1-6 alkyl, phenyl, C.sub.1-6 alkoxy, C.sub.1-6 alkylthio, C.sub.1-6 alkanoyl, amino, C.sub.1-6 alkylamino, di- C.sub.1-6 alkyl amino, halogen, or trifluromethyl; n is 1 or 2; q is 0 to 4; m is 1, 2, or 3; and p is 1, 2, 3, or 4 provided that m+p is not greater than 5; or a salt thereof are useful as inhibitors of gastric acid secretion.

  公式为##STR1##的4-氨基喹啉衍生物，其中R.sup.1是氢，C.sub.1-6烷基，C.sub.1-6烷氧基C.sub.1-6烷基；C.sub.3-6环烷基，C.sub.3-6环烷基-C.sub.1-6烷基，苯基C.sub.1-6烷基，苯基可以选择性地被取代；R.sup.2是羟基C.sub.1-6烷基，C.sub.1-6烷氧基C.sub.1-6烷基或者两个相邻的R.sup.2基团一起形成一个C.sub.1-4烷二氧基基团；R.sup.3是氢，C.sub.1-6烷基，C.sub.1-6烷氧基，氨基，C.sub.1-6烷硫基，卤素，氰基，羟基，C1-6烷酰基或三氟甲基；R.sup.4是氢，C.sub.1-6烷基，苯基，C.sub.1-6烷氧基，C.sub.1-6烷硫基，C.sub.1-6烷酰基，氨基，C.sub.1-6烷基氨基，二C.sub.1-6烷基氨基，卤素或三氟甲基；n为1或2；q为0到4；m为1,2或3；p为1,2,3或4，但要求m+p不大于5；或其盐可用作胃酸分泌抑制剂。
• 4-amino-3-carbonyl substituted quinolines
  申请人：Smith Kline & French Laboratories Limited

  公开号：US04806549A1

  公开（公告）日：1989-02-21

  This invention relates to novel substituted 4-aminoquinoline derivatives which are inhibitors of gastric acid secretion in mammals. A compound of the invention is 3-butyryl-4-(2-methylphenylamino)-8-methoxyquinoline.

  这项发明涉及新型的取代4-氨基喹啉衍生物，它们是哺乳动物胃酸分泌抑制剂。该发明的化合物是3-丁酰基-4-(2-甲基苯胺基)-8-甲氧基喹啉。
• Substituted 4-aminoquinoline derivatives as gastric secretion inhibitors
  申请人：SmithKline Beckman Intercredit B.V.

  公开号：US05143920A1

  公开（公告）日：1992-09-01

  Substituted 4-aminoquinazoline derivatives of the formula: ##STR1## wherein R.sup.1 is hydrogen, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, C.sub.1-6 alkoxy C.sub.1-6 alkyl, C.sub.3-6 cycloalkyl, C.sub.3-6 cycloalkyl C.sub.1-6 alkyl, phenyl C.sub.1-6 alkyl, the phenyl group being optionally substituted; R.sup.2 is hydrogen, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, amino, C.sub.1-6 alkylthio, halogen, cyano, hydroxy, C.sub.1-6 alkanoyl or trifuromethyl; m is 1 to 3; R.sup.3 is hydrogen, C.sub.1-6 alkyl, phenyl, C.sub.1-6 alkoxy, C.sub.1-6 alkylthio, C.sub.1-6 alkanoyl, amino, C.sub.1-6 alkylamino, ci-C.sub.1-6 alkylamino, halogen, trifluoromethyl or cyano; n is 1 or 2; and R.sup.4 is hydrogen; or a salt thereof are useful as inhibitors of gastric acid secretion.

  该公式中的4-氨基喹唑啉衍生物：其中R.sup.1为氢、C.sub.1-6烷基、C.sub.1-6烷氧基、C.sub.1-6烷氧基C.sub.1-6烷基、C.sub.3-6环烷基、C.sub.3-6环烷基C.sub.1-6烷基、苯基C.sub.1-6烷基，苯基可选择性取代；R.sup.2为氢、C.sub.1-6烷基、C.sub.1-6烷氧基、氨基、C.sub.1-6烷硫基、卤素、氰基、羟基、C.sub.1-6酰基或三氟甲基；m为1至3；R.sup.3为氢、C.sub.1-6烷基、苯基、C.sub.1-6烷氧基、C.sub.1-6烷硫基、C.sub.1-6烷酰基、氨基、C.sub.1-6烷基氨基、ci-C.sub.1-6烷基氨基、卤素、三氟甲基或氰基；n为1或2；R.sup.4为氢；或其盐可用作抑制胃酸分泌的药物。
• [EN] SUBSTITUTED PYRIDINE DERIVATIVES, PHARMACEUTICAL COMPOSITIONS, AND METHODS OF USE TO TREAT OXIDATIVE STRESS<br/>[FR] DÉRIVÉS DE PYRIDINE SUBSTITUÉS, COMPOSITIONS PHARMACEUTIQUES ET PROCÉDÉS D'UTILISATION POUR TRAITER LE STRESS OXYDATIF
  申请人：HIGH POINT PHARMACEUTICALS LLC

  公开号：WO2011022216A1

  公开（公告）日：2011-02-24

  Substituted pyridine derivatives, methods of their preparation, pharmaceutical compositions comprising a substituted pyridine derivative, and methods of use in treating inflammation are provided. The substituted pyridine derivatives may control of the activity or the amount or both the activity and the amount of heme-oxygenase.

  提供了取代吡啶衍生物、其制备方法、含有取代吡啶衍生物的药物组合物，以及在治疗炎症中使用的方法。这些取代吡啶衍生物可能控制血红素氧合酶的活性或数量，或者同时控制活性和数量。
• Compounds substituted quinoline derivatives
  申请人：SmithKline Beecham Intercredit B.V.

  公开号：US05432182A1

  公开（公告）日：1995-07-11

  Substituted 4-aminoquinazoline derivatives which are inhibitors of gastric acid secretion. A compound of the invention are the salts of strong acids of 3-butyryl-4-(2-methylphenylamino)-8-(hydroxymethyl)quinoline.

  替代4-氨基喹唑啉衍生物是胃酸分泌抑制剂。该发明的化合物是3-丁酰基-4-(2-甲基苯胺基)-8-(羟甲基)喹啉的强酸盐。