1-丁基-1H-苯并三唑-5-羧酸 | 120321-66-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 中文名称: 1-丁基-1H-苯并三唑-5-羧酸
• 英文名称: 1-butyl-1H-benzotriazole-5-carboxylic acid
• 英文别名: 1-Butyl-1,2,3-benzotriazole-5-carboxylic acid；1-butylbenzotriazole-5-carboxylic acid
• CAS: 120321-66-6
• 化学式: C₁₁H₁₃N₃O₂
• 分子量: 219.243
• InChiKey: XJQNSWOCRCXWHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  68
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-丁基-1H-苯并三唑-5-羧酸 、 lithium aluminium tetrahydride 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 以18 parts (42.7%)的产率得到1-butyl-1H-benzotriazole-5-methanol
  参考文献：
  名称：

  (1H-azol-1-ylmethyl) substituted benzotriazole derivatives and

  摘要：

  (1H-咪唑-1-基)取代苯并三唑衍生物，含有这些衍生物的组合物，以及治疗雌激素依赖性疾病的方法。

  公开号：

  US04943574A1
• 作为产物：
  描述：

  3-氨基-4-(丁基氨基)苯甲酸 在 盐酸 、 sodium nitrite 作用下， 以 水 为溶剂， 以33.3 parts (72.6%)的产率得到1-丁基-1H-苯并三唑-5-羧酸
  参考文献：
  名称：

  (1H-azol-1-ylmethyl) substituted benzotriazole derivatives and

  摘要：

  (1H-咪唑-1-基)取代苯并三唑衍生物，含有这些衍生物的组合物，以及治疗雌激素依赖性疾病的方法。

  公开号：

  US04943574A1

文献信息

• [EN] BENZOTRIAZOLES AND METHODS OF PROPHYLAXIS OR TREATMENT OF METABOLIC-RELATED DISORDERS THEREOF<br/>[FR] BENZOTRIAZOLES ET PROCEDES DE PREVENTION OU DE TRAITEMENT DES TROUBLES METABOLIQUE
  申请人：ARENA PHARM INC

  公开号：WO2004041274A1

  公开（公告）日：2004-05-21

  The present invention relates to certain benzotriazole carboxylic acid or ester derivatives of Formula (I), pharmaceutically acceptable salts and solvates thereof, which exhibit useful pharmaceutical properties, for example, as agonists for the GPCR referred to as hRUP38. Also provided by the present invention are pharmaceutical compositions containing compounds of the invention, and methods of using the compounds and compositions of the invention in the prophylaxis or treatment of metabolic-related disorders, including dyslipidemia, atherosclerosis, coronary heart disease, insulin resistance, type 2 diabetes, Syndrome-X and the like. In addition, the present invention also provides for the use of the compounds of the invention in combination with other active agents such as those belonging to the class of -glucosidase inhibitors, aldose reductase inhibitors, biguanides, HMG-CoA reductase inhibitors, squalene synthesis inhibitors, fibrates, LDL catabolism enhancers, angiotensin converting enzyme (ACE) inhibitors, insulin secretion enhancers and the like.

  本发明涉及公式（I）的若干苯并三唑羧酸或酯衍生物，其药学上可接受的盐和溶剂化物，具有有用的药理特性，例如作为称为hRUP38的GPCR激动剂。本发明还提供了含有本发明化合物的药物组合物，以及使用本发明化合物和组合物在预防或治疗代谢相关疾病，包括血脂异常、动脉粥样硬化、冠心病、胰岛素抵抗、2型糖尿病、综合征X等方面的方法。此外，本发明还提供了将本发明化合物与属于-葡萄糖苷酶抑制剂、醛还原酶抑制剂、双胍类、HMG-CoA还原酶抑制剂、角鲨烷合成抑制剂、非酯类、LDL降解增强剂、血管紧张素转化酶（ACE）抑制剂、胰岛素分泌增强剂等类别的其他活性剂联合使用的方法。
• Benzotriazoles and methods of prophylaxis or treatment of metabolic-related disorders thereof
  申请人：Semple Graeme

  公开号：US20060122240A1

  公开（公告）日：2006-06-08

  The present invention relates to certain benzotriazole carboxylic acid or ester derivatives of Formula (I), pharmaceutically acceptable salts and solvates thereof, which exhibit useful pharmaceutical properties, for example, as agonists for the GPCR referred to as hRUP38. Also provided by the present invention are pharmaceutical compositions containing compounds of the invention, and methods of using the compounds and compositions of the invention in the prophylaxis or treatment of metabolic-related disorders, including dyslipidemia, atherosclerosis, coronary heart disease, insulin resistance, type 2 diabetes, Syndrome-X and the like. In addition, the present invention also provides for the use of the compounds of the invention in combination with other active agents such as those belonging to the class of -glucosidase inhibitors, aldose reductase inhibitors, biguanides, HMG-CoA reductase inhibitors, squalene synthesis inhibitors, fibrates, LDL catabolism enhancers, angiotensin converting enzyme (ACE) inhibitors, insulin secretion enhancers and the like.

  本发明涉及公式（I）的某些苯并三唑羧酸或酯衍生物，其药学上可接受的盐和溶剂，具有有用的药理特性，例如作为被称为hRUP38的GPCR的激动剂。本发明还提供了含有该发明化合物的制药组合物，以及使用该发明化合物和组合物在预防或治疗代谢相关疾病，包括脂质代谢异常、动脉粥样硬化、冠心病、胰岛素抵抗、2型糖尿病、综合征X等方面的方法。此外，本发明还提供了将该发明化合物与属于-葡萄糖苷酶抑制剂、醛糖还原酶抑制剂、双胍类药物、HMG-CoA还原酶抑制剂、角鲨烷合成抑制剂、纤维酸类、低密度脂蛋白降解增强剂、血管紧张素转换酶（ACE）抑制剂、胰岛素分泌增强剂等类别的其他活性剂一起使用的方法。
• 6-(1H-azol-1-ylmethyl)-1-(pyrimidinyloxy)-1H benzotriazoles
  申请人：Janssen Pharmaceutica N.V.

  公开号：US05039677A1

  公开（公告）日：1991-08-13

  (1H-azol-1-ylmethyl)substituted benzotriazole derivatives, compositions containing the same, and methods of treating estrogen dependent disorders.

  含有(1H-唑-1-基)取代苯并三唑衍生物的组合物，以及治疗雌激素依赖性疾病的方法。
• (1H-azol-1-ylmethyl)substituted benzotriazole derivatives
  申请人：JANSSEN PHARMACEUTICA N.V.

  公开号：EP0293978A2

  公开（公告）日：1988-12-07

  Novel (1H-azol-1-ylmethyl)substituted benzotriazole derivatives of formula wherein     A¹=A²-A³=A⁴ is -CH=N-CH=CH-, -CH=N-CH=N- or -CH=N-N=CH-;     R is hydrogen or C₁₋₆alkyl;     R¹ is hydrogen, C₁₋₁₀ alkyl, C₃₋₇cycloalkyl, Ar¹, Ar²-C₁₋₆alkyl, C₂₋₆alkenyl or C₂₋₆alkynyl;     R² is hydrogen; optionally substituted C₁₋₁₀alkyl; Ar¹; C₂₋₆alkenyl; C₂₋₆alkynyl; C₃₋₇cycloalkyl; bicyclo[2.2.1]heptan-­2-yl; 2,3-dihydro-1H-indenyl; 1,2,3,4-tetrahydronaphthalenyl; hydroxy; optionally substituted C₂₋₆alkenyloxy; C₂₋₆alkynyloxy; pyrimidinyl­oxy; di(Ar²)methoxy; (1-C₁₋₄alkyl-4-piperidinyl)oxy; or optionally substituted C₁₋₁₀alkyloxy;     R³ is hydrogen, nitro, amino, mono- and di(C₁₋₆alkyl)amino, halo, C₁₋₆alkyl, hydroxy or C₁₋₆alkyloxy;     wherein Ar¹ is phenyl, substituted phenyl, naphthalenyl, pyridinyl, aminopyridinyl, imidazolyl, triazolyl, thienyl, halothienyl, furanyl, C₁₋₆alkylfuranyl, halofuranyl or thiazolyl; and     Ar² is phenyl, substituted phenyl or pyridinyl; the pharmaceutically acceptable acid addition salts and possible stereochemically isomeric forms thereof, which compounds are estrogene hormone biosynthesis inhibitory agents; pharmaceutical compositions containing such compounds as an active ingredient and methods of preparing said compounds and pharmaceutical compositions.

  式中的新颖(1H-唑-1-基甲基)取代苯并三唑衍生物 其中 A¹=A²-A³=A⁴ 是 -CH=N-CH=CH-、-CH=N-CH=N- 或 -CH=N-N=CH-； R 是氢或 C₁₋₆ 烷基； R¹ 是氢、C₁₋₁₀烷基、C₃₋₇环烷基、Ar¹、Ar²-C₁₋₆烷基、C₂₋₆ 炔基； R² 是氢；任选取代的 C₁₋₁₀烷基；Ar¹；C₂₋₆烯基；C₂₋₆炔基；C₃₋₇环烷基；双环[2.2.1]庚-2-基；2,3-二氢-1H-茚基；1,2,3,4-四氢萘基；羟基；任选取代的 C₂₋₆烯氧基；C₂₋₆炔氧基；嘧啶氧基；二(Ar²)甲氧基；(1-C₁₋₄烷基-4-哌啶基)氧基；或任选取代的 C₁₋₁₀烷氧基； R³ 是氢、硝基、氨基、单-和二(C₁₋₆烷基)氨基、卤代、C₁₋₆烷基、羟基或 C₁₋₆烷氧基； 其中 Ar¹ 是苯基、取代苯基、萘基、吡啶基、氨基吡啶基、咪唑基、三唑基、噻吩基、卤代噻吩基、呋喃基、C₁₋₆烷基呋喃基、卤代呋喃基或噻唑基；以及 Ar² 是苯基、取代苯基或吡啶基； 药学上可接受的酸加成盐及其可能的立体化学异构体形式，这些化合物是雌 激素激素生物合成抑制剂；含有这些化合物作为活性成分的药物组合物，以及制备 上述化合物和药物组合物的方法。
• 1-Alkyl-benzotriazole-5-carboxylic Acids Are Highly Selective Agonists of the Human Orphan G-Protein-Coupled Receptor GPR109b
  作者：Graeme Semple、Philip J. Skinner、Martin C. Cherrier、Peter J. Webb、Carleton R. Sage、Susan Y. Tamura、Ruoping Chen、Jeremy G. Richman、Daniel T. Connolly

  DOI：10.1021/jm051099t

  日期：2006.2.1

  I-Substituted benzotriazole carboxylic acids have been identified as the first reported examples of selective small-molecule agonists of the human orphan G-protein-coupled receptor GPR109b (HM74), a low-affinity receptor for the HDL-raising drug niacin. No activity was observed at the highly homologous high-affinity macin receptor GPR109a (HM74A). The high degree of selectivity was attributed to a difference in the amino acid sequence adjacent to a key arginine-ligand interaction allowing somewhat larger ligands to be tolerated by GPR109b.