5-氨基-1,3-二甲基-1H-吡唑-4-羧醛 | 57411-70-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 5-氨基-1,3-二甲基-1H-吡唑-4-羧醛
• 英文名称: 5-Amino-1,3-dimethyl-4-formylpyrazol
• 英文别名: 5-amino-1,3-dimethylpyrazole-4-carbaldehyde；5-amino-1,3-dimethyl-1H-pyrazole-4-carbaldehyde；5-amino-1,3-dimethylpyrazole-4-carboxaldehyde
• CAS: 57411-70-8
• 化学式: C₆H₉N₃O
• mdl: MFCD19204993
• 分子量: 139.157
• InChiKey: LMWISGVUHHTGQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  60.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-氨基-1,3-二甲基-1H-吡唑-4-羧醛 在 苯膦酰二氯 作用下， 以 四氢呋喃 为溶剂， 反应 40.0h， 生成 6-{[2-(dimethylamino)ethyl]methylamino}-1,3-dimethylpyrazolo[5,4-b]pyridine-5-carbonitrile
  参考文献：
  名称：

  Discovery, Optimization, and Pharmacological Characterization of Novel Heteroaroylphenylureas Antagonists of C−C Chemokine Ligand 2 Function

  摘要：

  Through the application of TRAP (target-related affinity profiling), we identified a novel class of heteroaroylphenylureas that inhibit human CCL2-induced chemotaxis of monocytes/macrophages both in vitro and in vivo. This inhibition was concentration-dependent and selective with regard to other chemokines. The compounds, however, did not antagonize the binding of I-125-labeled CCL2 to the CCR2 receptor nor did they block CCR2-mediated signal transduction responses such as calcium mobilization. Optimization of early leads for potency and pharmacokinetic parameters resulted in the identification of 17, a potent inhibitor of chemotaxis (IC50 = 80 nM) with excellent oral bioavailability in rats (F = 60%). Compound 17 reduced swelling and joint destruction in two rat models of rheumatoid arthritis and delayed disease onset and produced near complete resolution of symptoms in a mouse model of multiple sclerosis.

  DOI：

  10.1021/jm1012903
• 作为产物：
  描述：

  5-氨基-1,3-二甲基吡唑 、 N,N-二甲基甲酰胺 在 三氯氧磷 、 乙醇 、 sodium hydroxide 作用下， 生成 5-氨基-1,3-二甲基-1H-吡唑-4-羧醛
  参考文献：
  名称：

  Discovery, Optimization, and Pharmacological Characterization of Novel Heteroaroylphenylureas Antagonists of C−C Chemokine Ligand 2 Function

  摘要：

  Through the application of TRAP (target-related affinity profiling), we identified a novel class of heteroaroylphenylureas that inhibit human CCL2-induced chemotaxis of monocytes/macrophages both in vitro and in vivo. This inhibition was concentration-dependent and selective with regard to other chemokines. The compounds, however, did not antagonize the binding of I-125-labeled CCL2 to the CCR2 receptor nor did they block CCR2-mediated signal transduction responses such as calcium mobilization. Optimization of early leads for potency and pharmacokinetic parameters resulted in the identification of 17, a potent inhibitor of chemotaxis (IC50 = 80 nM) with excellent oral bioavailability in rats (F = 60%). Compound 17 reduced swelling and joint destruction in two rat models of rheumatoid arthritis and delayed disease onset and produced near complete resolution of symptoms in a mouse model of multiple sclerosis.

  DOI：

  10.1021/jm1012903

文献信息

• Antagonists of MCP-1 function and methods of use thereof
  申请人：——

  公开号：US20030096705A1

  公开（公告）日：2003-05-22

  The present invention relates to chemical compounds, pharmaceutical compositions comprising said compounds, uses of said compounds and compositions, methods of treatment employing said compounds and compositions, and processes for preparing said compounds. Specifically, this invention relates to novel compounds which are antagonists of MCP-1 function and are useful in the prevention or treatment of chronic or acute inflammatory or autoimmune diseases, especially those associated with aberrant lymphocyte or monocyte accumulation such as arthritis, asthma, atherosclerosis, diabetic nephropathy, inflammatory bowel disease, Crohn's disease, multiple sclerosis, nephritis, pancreatitis, pulmonary fibrosis, psoriasis, restenosis, and transplant rejection. More specifically, the invention is related to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases.

  本发明涉及化合物、包含该化合物的药物组合物、使用该化合物和组合物的用途、使用该化合物和组合物的治疗方法，以及制备该化合物的过程。具体而言，本发明涉及新型化合物，这些化合物是 MCP-1 功能拮抗剂，可用于预防或治疗慢性或急性炎症性或自身免疫性疾病，特别是那些与淋巴细胞或单核细胞异常积聚有关的疾病，如关节炎、哮喘、动脉粥样硬化、糖尿病肾病、炎性肠病、克罗恩病、多发性硬化、肾炎、胰腺炎、肺纤维化、银屑病、再狭窄和移植排斥反应。更具体地，本发明涉及包含这些化合物的药物组合物以及使用这些化合物和组合物预防或治疗这些疾病。
• Antagonist of MCP-1 function, and compositions and methods of use thereof
  申请人：——

  公开号：US20040198719A1

  公开（公告）日：2004-10-07

  Compounds of formula A and formula B: 1 and their pharmaceutically acceptable salts, compositions comprising them, methods for their use, and their use in the preparation of medicaments. The compounds are antagonists of MCP-1 function, and are useful in the prevention and treatment of chronic or acute inflammatory or autoimmune diseases, such as multiple sclerosis, and in the prevention and treatment of allergic hypersensitivity disorders.

  公式A和公式B的化合物及其药学上可接受的盐，包括它们的组合物，使用方法以及它们在药物制备中的应用。这些化合物是MCP-1功能的拮抗剂，可用于预防和治疗慢性或急性炎症或自身免疫性疾病，如多发性硬化症，并用于预防和治疗过敏性过敏反应性疾病。
• CONDENSED 3,3-DIFLUORO-PIPERIDINE DERIVATIVES AS INHIBITORS OF CORONAVIRUSES 3-CHYMOTRYPSIN-LIKE PROTEASE
  申请人：Qubit Pharmaceuticals

  公开号：EP4159721A1

  公开（公告）日：2023-04-05

  The invention relates to compounds of formula I : More particularly the invention relates to such compounds as inhibitors of 3CLpro protease. Accordingly, invention relates to a pharmaceutical composition comprising said compounds, and also to said compound for their use as a medicament, more particularly in the treatment or the prophylaxis of an infection to coronavirus and more particularly to SARS-CoV-2.

  本发明涉及以下通式I的化合物：更具体地，本发明涉及此类化合物作为3CLpro蛋白酶抑制剂。因此，本发明涉及包含上述化合物的药物组合物，并且也涉及所述化合物用于作为药物的用途，更具体地用于治疗或预防冠状病毒感染，尤其针对SARS-CoV-2。
• RATAJCZYK J. D.; SWETT L. R., J. HETEROCYCL. CHEM. <JHTC-AC>, 1975, 12, NO 3, 517-522
  作者：RATAJCZYK J. D.、 SWETT L. R.

  DOI：——

  日期：——
• ANTAGONISTS OF MCP-1 FUNCTION AND METHODS OF USE THEREOF
  申请人：TELIK, INC.

  公开号：EP1358188A2

  公开（公告）日：2003-11-05