3-methyl-6-oxo-1,6-dihydro-pyridine-2-carboxylic acid ethyl ester | 1146964-94-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-methyl-6-oxo-1,6-dihydro-pyridine-2-carboxylic acid ethyl ester
• 英文别名: Ethyl 6-hydroxy-3-methylpicolinate；ethyl 3-methyl-6-oxo-1H-pyridine-2-carboxylate
• CAS: 1146964-94-4
• 化学式: C₉H₁₁NO₃
• 分子量: 181.191
• InChiKey: TUCJYPJXPNLAMH-UHFFFAOYSA-N

物化性质

• 沸点：
  367.1±42.0 °C(Predicted)
• 密度：
  1.163±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-methyl-6-oxo-1,6-dihydro-pyridine-2-carboxylic acid ethyl ester 在 N-溴代丁二酰亚胺(NBS) 、 四丁基溴化铵 、 sodium methylate 、 potassium carbonate 、 sodium iodide 、 lithium bromide 、 过氧化苯甲酰 作用下， 以 甲醇 、 四氯化碳 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 48.67h， 生成 [(1-benzyl-8-hydroxy-2-oxo-1,2-dihydro-[1,6]naphthyridine-7-carbonyl)-amino]-acetic acid
  参考文献：
  名称：

  [EN] NAPHTHYRIDINE DERIVATIVES AS INHIBITORS OF HYPOXIA INDUCIBLE FACTOR (HIF) HYDROXYLASE
  [FR] DÉRIVÉS DE NAPHTHYRIDINE EN TANT QU'INHIBITEURS D'UN FACTEUR INDUCTIBLE PAR L'HYPOXIE

  摘要：

  本公开涉及能够抑制HIF羟化酶活性的新化合物、方法和组合物，从而增加缺氧诱导因子（HIF）的稳定性和/或活性。

  公开号：

  WO2012106472A1
• 作为产物：
  描述：

  3-甲基-2-吡啶甲酸 在 二氯乙酸 、 氯化亚砜 、 间氯过氧苯甲酸 、 三氯氧磷 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.0h， 生成 3-methyl-6-oxo-1,6-dihydro-pyridine-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  [EN] NAPHTHYRIDINE DERIVATIVES AS INHIBITORS OF HYPOXIA INDUCIBLE FACTOR (HIF) HYDROXYLASE
  [FR] DÉRIVÉS DE NAPHTHYRIDINE EN TANT QU'INHIBITEURS D'UN FACTEUR INDUCTIBLE PAR L'HYPOXIE

  摘要：

  本公开涉及能够抑制HIF羟化酶活性的新化合物、方法和组合物，从而增加缺氧诱导因子（HIF）的稳定性和/或活性。

  公开号：

  WO2012106472A1

文献信息

• NAPHTHYRIDINE DERIVATIVES AS INHIBITORS OF HYPOXIA INDUCIBLE FACTOR (HIF) HYDROXYLASE
  申请人：Ng Danny

  公开号：US20140088101A1

  公开（公告）日：2014-03-27

  The present disclosure relates to novel compounds, methods, and compositions capable of inhibiting HIF hydroxylase enzyme activity, thereby increasing the stability and/or activity of hypoxia inducible factor (HIF).

  本公开涉及新型化合物、方法和组合物，能够抑制HIF羟化酶酶活性，从而增加缺氧诱导因子（HIF）的稳定性和/或活性。
• Naphthyridine derivatives as inhibitors of hypoxia inducible factor (HIF) hydroxylase
  申请人：Ng Danny

  公开号：US08921389B2

  公开（公告）日：2014-12-30

  The present disclosure relates to novel compounds, methods, and compositions capable of inhibiting HIF hydroxylase enzyme activity, thereby increasing the stability and/or activity of hypoxia inducible factor (HIF).

  本公开涉及新型化合物、方法和组合物，能够抑制HIF羟化酶酶活性，从而增加缺氧诱导因子（HIF）的稳定性和/或活性。
• FLUORINATED 1,4-DISUBSTITUTED PIPERIDINE DERIVATIVES
  申请人：BANYU PHARMACEUTICAL CO., LTD.

  公开号：EP0930298A1

  公开（公告）日：1999-07-21

  This invention relates to novel fluorine-containing 1,4-disubstituted piperidine derivatives represented by a general formula [I] and pharmaceutically acceptable salts thereof, [wherein: Ar represents an aryl group or a hetero-aryl group having 1 to 2 hetero atoms selected from a group consisting of nitrogen, oxygen and sulfur (any 1 to 3 hydrogen atoms on the ring of said aryl or heteroaryl group may be substituted with lower alkyl, etc.); R1 represents C3-C6 cycloalkyl whose any 1-4 hydrogen atmos may be substituted with fluorine atoms(s); R2 represents C5-C15 saturated or unsaturated aliphatic hydrocarbon groups whose any 1 to 6 hydrogen atoms may be substituted with fluorine atom(s), aralkyl, arylalkenyl, heteroarylalkyl or heteroarylalkenyl group having 1 to 2 hetero atoms selected from a group consisting of nitrogen, oxygen and sulfur (optionally any 1 to 3 hydrogen atoms on the ring in said aralkyl, arylalkenyl, hetero-arylalkyl or heteroarylalkenyl group may be substituted with lower alkyl, trifluoromethyl, cyano, hydroxyl, nitro, lower alkoxycarbonyl, halogen, lower alkoxy or amino, etc. ; and X stands for O or NH, provided that at least either one of R1 and R2 contains one or more fluorine atoms]. The compounds of the present invention have selective antagonistic activity for muscarinic M3 receptors, and exhibit excellent oral activity, duration of action and pharmacokinetics, so that they have little side effects and are safe and effective. Therefore they are useful for treatment or prophylaxis of respiratory diseases, urinary diseases and digestive diseases.

  本发明涉及通式[I]代表的新型含氟 1,4-二取代哌啶衍生物 及其药学上可接受的盐类、 其中 Ar 代表芳基或杂芳基，其 1 至 2 个杂原子选自氮、氧和硫组成的组 (所述芳基或杂芳基环上的任何 1 至 3 个氢原子可被低级烷基等取代)； R1 代表 C3-C6 环烷基，其任意 1-4 个氢原子可被氟原子取代； R2 代表 C5-C15 饱和或不饱和脂肪族烃基，其任意 1-6 个氢原子可被氟原子取代；R3 代表芳烷基、芳烯基、杂芳烷基或杂芳基烯基，其 1-2 个杂原子选自由氮、氧和硫组成的组、氧和硫（上述芳烷基、芳烯基、杂芳烷基或杂芳基烯基的环上任意 1 至 3 个氢原子可任选被低级烷基、三氟甲基、氰基、羟基、硝基、低级烷氧基羰基、卤素、低级烷氧基或氨基等取代）；以及和 X 代表 O 或 NH、 条件是 R1 和 R2 中至少有一个含有一个或多个氟原子]。 本发明的化合物对毒蕈碱类 M3 受体具有选择性拮抗活性，并表现出良好的口服活性、作用持续时间和药代动力学，因此副作用小且安全有效。因此，它们可用于治疗或预防呼吸系统疾病、泌尿系统疾病和消化系统疾病。
• Design and synthesis of calpain inhibitory 6-pyridone 2-carboxamide derivatives
  作者：Ki Yong Lee、Kwang Seob Lee、Changbae Jin、Yong Sup Lee

  DOI：10.1016/j.ejmech.2008.02.023

  日期：2009.3

  Excessive calpain activation contributes to serious cellular damage in many pathological conditions. The involvement of mu-calpain in neurological disorders such as, stroke and Alzheimer's disease has attracted considerable interest in the use of calpain inhibitors as therapeutic agents. 6-Pyridone 2-carboxamides derived from ketoamides were synthesized as conformationally constrained structures resembling the well known peptidic mu-calpain inhibitor, MDL 28,170, and their mu-calpain inhibitory activities were evaluated. Of the compounds synthesized, compound 2a, which has a primary amide at warhead region of the inhibitor most potently inhibited mu-calpain with an IC50 value of 2.81 +/- 1.26 mu M, which is ca. 40-fold less than that of MDL 28,170. (C) 2008 Elsevier Masson SAS. All rights reserved.
• NAPHTHYRIDINE DERIVATIVES AS INHIBITORS OF HYPOXIA INDUCIBLE FACTOR
  申请人：Fibrogen, Inc.

  公开号：EP2670750B1

  公开（公告）日：2016-09-14