4,6-Bis-(1,1-dimethylethyl)-5-hydroxy-2-pyrimidine carboxylic acid methyl ester | 144837-09-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 4,6-Bis-(1,1-dimethylethyl)-5-hydroxy-2-pyrimidine carboxylic acid methyl ester
• 英文别名: 4,6-Bis (1,1-dimethylethyl)-5-hydroxy-2-pyrimidine carboxylic acid methyl ester；methyl 4,6-ditert-butyl-5-hydroxypyrimidine-2-carboxylate
• CAS: 144837-09-2
• 化学式: C₁₄H₂₂N₂O₃
• 分子量: 266.34
• InChiKey: VLCKVQBDYRMXKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  72.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4,6-Bis-(1,1-dimethylethyl)-5-hydroxy-2-pyrimidine carboxylic acid methyl ester 在 sodium hydroxide 作用下， 反应 2.0h， 以90%的产率得到4,6-Bis(1,1-dimethylethyl)-5-hydroxy-2-pyrimidine carboxylic acid
  参考文献：
  名称：

  2,6-二叔丁基苯酚抗炎药嘧啶类似物的合成†

  摘要：

  描述了2,6-二叔丁基苯酚抗炎药Prifelone（R-830​​），Tebufelone（NE-11740）和Ym-13,162的嘧啶类似物的制备。从衍生自4，6-双（1，1-二甲基乙基）-5-羟基-2-嘧啶羧酸的N-甲氧基-N-甲基酰胺中加入格氏试剂，得到一系列2-嘧啶基酮。进一步精制乙基酮并用氰酸钠环化，得到嘧啶基咪唑。

  DOI：

  10.1002/jhet.5570320417

文献信息

• Substituted 4,6-di-tertiary-butyl 5-hydroxy-pyrimidines
  申请人：Warner-Lambert Company

  公开号：US05356898A1

  公开（公告）日：1994-10-18

  The present invention is novel compounds which are 4,6-di-tertiary-butyl-5-hydroxy-1,3-pyrimidine substituted 1,2,4- and 1,3,4-thiadiazoles and oxadiazoles, and 1,2,4-triazoles, and pharmaceutically acceptable additions and base salts thereof, pharmaceutical compositions and methods of use therefor. The invention compounds are now found to have activity as inhibitors of 5-lipoxygenase and/or cyclooxygenase providing treatment of conditions advantageously affected by such inhibition including inflammation, arthritis, pain, fever, and particularly rheumatoid arthritis, osteoarthritis, other inflammatory conditions, psoriasis, allergic diseases, asthma, inflammatory bowel disease, GI ulcers, cardiovascular conditions, including ischemic heart disease and atherosclerosis, and ischemia-induced cell damage, particularly brain damage caused by stroke. They can also be used topically for treating acne, sunburn, psoriasis, and eczema. Also included are leukotriene mediated pulmonary, gastrointestinal, inflammatory, dermatological, and cardiovascular conditions. The disclosed compounds also have potential utility as antioxidants. The preferred use is in treating inflammatory conditions. Thus, the present invention is also a pharmaceutical composition or method of manufacturing a pharmaceutical composition for the use of treating the noted conditions.

  本发明涉及新型化合物，其为4,6-二叔丁基-5-羟基-1,3-嘧啶取代的1,2,4-和1,3,4-噻二唑和噁二唑，以及1,2,4-三唑，以及其药学上可接受的加成物和盐基，制药组合物和使用方法。发明化合物现已被发现具有5-脂氧合酶和/或环氧合酶的抑制剂活性，可用于治疗有利受到这种抑制影响的疾病，包括炎症、关节炎、疼痛、发热，特别是类风湿性关节炎、骨关节炎、其他炎症性疾病、牛皮癣、过敏病、哮喘、炎症性肠病、胃肠溃疡、心血管疾病，包括缺血性心脏病和动脉硬化，以及缺血引起的细胞损伤，特别是中风引起的脑损伤。它们还可以用于局部治疗痤疮、晒伤、牛皮癣和湿疹。还包括白三烯介导的肺部、胃肠道、炎症、皮肤和心血管疾病。所述化合物也具有潜在的抗氧化剂作用。首选用途是治疗炎症性疾病。因此，本发明也是一种制药组合物或制药组合物的制造方法，用于治疗上述疾病。
• 5-hydroxy-2-pyrimidinylmethylene derivatives useful as antiinflammatory
  申请人：Warner-Lambert Company

  公开号：US05270319A1

  公开（公告）日：1993-12-14

  The present invention is novel compounds which are 5-hydroxy-2-pyrimidinylmethylene derivatives and pharmaceutically acceptable addition salts, bases, and base salts thereof, pharmaceutical compositions and methods of use therefor. The invention compounds are found to have activity as inhibitors of 5-lipoxygenase and/or cyclooxygenase providing treatment of, for example, preferably inflammation.

  本发明涉及一种新型化合物，其为5-羟基-2-嘧啶甲醛衍生物及其药学上可接受的加成盐、碱和碱盐、制药组合物和使用方法。本发明化合物被发现具有抑制5-脂氧合酶和/或环氧化酶的活性，可用于治疗例如炎症等病症。
• Substituted heteroaryl analogs of
  申请人：Warner-Lambert Company

  公开号：US05432181A1

  公开（公告）日：1995-07-11

  The present invention is novel compounds which are 4,6-di-tertiary-butyl-5-hydroxy-1,3-pyrimidine substituted 1,2,4- and 1,3,4-thiadiazoles and oxadiazoles, and 1,2,4-triazoles, and pharmaceutically acceptable additions and base salts thereof, pharmaceutical compositions and methods of use therefor. The invention compounds are now found to have activity as inhibitors of 5-lipoxygenase and/or cyclooxygenase providing treatment of conditions advantageously affected by such inhibition including inflammation, arthritis, pain, fever, and particularly rheumatoid arthritis, osteoarthritis, other inflammatory conditions, psoriasis, allergic diseases, asthma, inflammatory bowel disease, GI ulcers, cardiovascular conditions, including ischemic heart disease and atherosclerosis, and ischemia-induced cell damage, particularly brain damage caused by stroke. They can also be used topically for treating acne, sunburn, psoriasis, and eczema. Also included are leukotriene mediated pulmonary, gastrointestinal, inflammatory, dermatological, and cardiovascular conditions. The disclosed compounds also have potential utility as antioxidants. The preferred use is in treating inflammatory conditions.

  本发明涉及新型化合物，其为4,6-二叔丁基-5-羟基-1,3-嘧啶取代的1,2,4-和1,3,4-噻二唑、噁二唑和1,2,4-三唑化合物，以及其药学上可接受的补充物和盐基，药物组合物和使用方法。发明化合物现已发现具有5-脂氧合酶和/或环氧化酶抑制剂的活性，可用于治疗受到这种抑制优势影响的疾病，包括炎症、关节炎、疼痛、发热，特别是类风湿性关节炎、骨关节炎、其他炎症性疾病、牛皮癣、过敏性疾病、哮喘、炎症性肠病、胃肠溃疡、心血管疾病，包括缺血性心脏病和动脉粥样硬化，以及缺血引起的细胞损伤，尤其是中风引起的脑损伤。它们也可以用于局部治疗痤疮、晒伤、牛皮癣和湿疹。还包括白三烯介导的肺部、胃肠道、炎症、皮肤和心血管疾病。所披露的化合物也具有作为抗氧化剂的潜在用途。首选用途是治疗炎症性疾病。
• 2-SUBSTITUTED-4,6-DI-TERTIARY-BUTYL-5-HYDROXY-1,3-PYRIMIDINES USEFUL AS ANTIINFLAMMATORY AGENTS
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0569491A1

  公开（公告）日：1993-11-18
• EP0569491A4
  申请人：——

  公开号：EP0569491A4

  公开（公告）日：1993-11-24