6-bromo-5-methyl-1,3-dihydro-imidazo[4,5-b]pyridin-2-one | 116035-73-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: 6-bromo-5-methyl-1,3-dihydro-imidazo[4,5-b]pyridin-2-one
• 英文别名: 6-bromo-5-methyl-1H-imidazo[4,5-b]pyridin-2(3H)-one；6-bromo-5-methyl-1,3-dihydro-imidazo[4,5-b]pyridin-2-one；6-Brom-5-methyl-1,3-dihydro-imidazo[4,5-b]pyridin-2-on；6-bromo-5-methyl-1H-imidazo[4,5-b]pyridin-2-ol；6-bromo-5-methyl-1,3-dihydroimidazo[4,5-b]pyridin-2-one
• CAS: 116035-73-5
• 化学式: C₇H₆BrN₃O
• 分子量: 228.048
• InChiKey: MVEUCAYEKFZDEG-UHFFFAOYSA-N

物化性质

• 密度：
  2.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  54
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  6-bromo-5-methyl-1,3-dihydro-imidazo[4,5-b]pyridin-2-one 在 硫酸 、 potassium nitrate 作用下， 反应 3.5h， 以61%的产率得到6-bromo-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridine-5-carboxylic acid
  参考文献：
  名称：

  1,3-二氢-2H-咪唑并[4,5-b]吡啶-2-酮衍生物的硝化

  摘要：

  Nitration of 1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one and its N-methyl derivatives at 0-5 degrees C and 60 degrees C gives 5-nitro- and 5,6-dinitro-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-ones, respectively. The latter can also be obtained by nitration of 5-mononitro derivatives under similar conditions. The nitration of 6-chloro- and 6-bromo-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-ones and their N-methyl-substituted analogs leads to the formation of the corresponding 6-chloro(bromo)-5 -nitro compounds. The same products are formed in the nitration of 5,6-dichloro- and 5,6-dibromo-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-ones. In this case, the process involves replacement of the halogen atom in position 5 of the pyridine fragment by nitro group. The nitration of 6-bromo-5-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one is accompanied by oxidation of the 5-methyl group to carboxy.

  DOI：

  10.1134/s1070428007030153
• 作为产物：
  描述：

  2-氨基-6-甲基烟酰胺 在 氢氧化钾 、 溴 作用下， 生成 6-bromo-5-methyl-1,3-dihydro-imidazo[4,5-b]pyridin-2-one
  参考文献：
  名称：

  Synthese von 2-Oxy-imidazolo-(5′,4′:2,3)-pyridinen Synthesen stickstoffhaltiger Heterocyclen, XII. Mitteilung

  摘要：

  DOI：

  10.1002/ardp.19572900104

文献信息

• [EN] SUBSTITUTED-1,4-DIHYDROPYRAZOLO[4,3-b]INDOLES<br/>[FR] DIHYDROPYRAZOLO[4,3-B]INDOLES SUBSTITUÉES DANS LES POSITIONS 1 ET 4
  申请人：TAKEDA PHARMACEUTICAL

  公开号：WO2014039831A1

  公开（公告）日：2014-03-13

  Disclosed are compounds of Formula (1), and pharmaceutically acceptable salts thereof, wherein L, R1, R2, R3, R4, R5, R6, and R7 are defined in the specification. This disclosure also relates to materials and methods for preparing compounds of Formula 1, to pharmaceutical compositions which contain them, and to their use for treating obesity and related diseases, disorders, and conditions associated with MetAP2.

  本公开涉及式（1）的化合物及其药用盐，其中L、R1、R2、R3、R4、R5、R6和R7在规范中定义。本公开还涉及制备式1化合物的材料和方法，含有它们的药物组合物，以及它们用于治疗与MetAP2相关的肥胖和相关疾病、紊乱和病况的用途。
• [EN] INDAZOLE DERIVATIVES<br/>[FR] DÉRIVÉS D'INDAZOLE
  申请人：TAKEDA PHARMACEUTICAL

  公开号：WO2013130855A1

  公开（公告）日：2013-09-06

  Disclosed are compounds of Formula 1, and pharmaceutically acceptable salts thereof, wherein R1, R2, R3, R4, R5, and R6 are defined in the specification. This disclosure also relates to materials and methods for preparing compounds of Formula 1, to pharmaceutical compositions which contain them, and to their use for treating obesity and related diseases, disorders, and conditions associated with MetAP2.

  公开了Formula 1的化合物及其药用盐，其中R1、R2、R3、R4、R5和R6在规范中有定义。本公开还涉及制备Formula 1化合物的材料和方法，含有这些化合物的药物组合物，以及它们用于治疗肥胖和与MetAP2相关的疾病、紊乱和症状的用途。
• Halogenation of 2-Unsubstituted and 2-Methylimidazo[4,5-b]pyridine Derivatives
  作者：Yu. M. Yutilov、Kh. Ya. Lopatinskaya、N. N. Smolyar、S. V. Gres’ko

  DOI：10.1007/s11178-005-0186-y

  日期：2005.3

  Halogenation of 2-unsubstituted and 2-methylimidazo[4,5-b]pyridines and their N-methyl derivatives with bromine and chlorine in acetic acid takes different pathways, depending on the acetic acid concentration. The bromination in 50% aqueous acetic acid gives only 6-bromoimidazo[4,5-b]pyridines; bromination and chlorination of 2-unsubstituted imidazo[4,5-b]pyridines in glacial acetic acid leads to 5,6-dibromo(dichloro)imidazo[4,5-b]pyridin-2-ones, and bromination of 2-methylimidazo[4,5-b]pyridines in glacial acetic acid involves both the pyridine ring and the 2-methyl group to afford the corresponding 6-bromo-2-tribromomethylimidazo[4,5-b]pyridines.

  在乙酸中用溴和氯对 2-未取代的和 2-甲基咪唑并[4,5-b]吡啶及其 N-甲基衍生物进行卤化，根据乙酸浓度的不同，卤化途径也不同。在 50% 的乙酸水溶液中进行溴化反应只能得到 6-溴咪唑并[4,5-b]吡啶；在冰醋酸中对 2-未取代的咪唑并[4,5-b]吡啶进行溴化和氯化反应，可生成 5,6-二溴（二氯）咪唑并[4,5-b]吡啶-2-酮；在冰醋酸中对 2-甲基咪唑并[4,5-b]吡啶进行溴化反应，可生成 2-甲基咪唑并[4,5-b]吡啶-2-酮、2-甲基咪唑并[4,5-b]吡啶在冰乙酸中的溴化反应涉及吡啶环和 2-甲基，从而得到相应的 6-溴-2-三溴甲基咪唑并[4,5-b]吡啶。
• INDAZOLE DERIVATIVES
  申请人：TAKEDA PHARMACEUTICAL COMPANY LIMITED

  公开号：US20150005232A1

  公开（公告）日：2015-01-01

  Disclosed are compounds of Formula 1, and pharmaceutically acceptable salts thereof, wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are defined in the specification. This disclosure also relates to materials and methods for preparing compounds of Formula 1, to pharmaceutical compositions which contain them, and to their use for treating obesity and related diseases, disorders, and conditions associated with MetAP2.

  本发明涉及公式1的化合物及其药学上可接受的盐，其中R1、R2、R3、R4、R5和R6在规范中有定义。本发明还涉及制备公式1化合物的材料和方法，以及包含它们的制药组合物，并用于治疗肥胖症以及与MetAP2相关的疾病、失调和病症的用途。
• SUBSTITUTED-1,4-DIHYDROPYRAZOLO[4,3-b]INDOLES
  申请人：TAKEDA PHARMACEUTICAL COMPANY LIMITED

  公开号：US20150225405A1

  公开（公告）日：2015-08-13

  Disclosed are compounds of Formula 1, and pharmaceutically acceptable salts thereof, wherein L, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 are defined in the specification. This disclosure also relates to materials and methods for preparing compounds of Formula 1, to pharmaceutical compositions which contain them, and to their use for treating obesity and related diseases, disorders, and conditions associated with MetAP2.

  本发明涉及公式1的化合物及其药学上可接受的盐，其中L，R1，R2，R3，R4，R5，R6和R7在说明书中有定义。本公开还涉及制备公式1化合物的材料和方法，包含它们的制药组合物，以及它们用于治疗肥胖和与MetAP2相关的疾病、障碍和病况的用途。