3-bromo-5-methyl-1,6-naphthyridin-2-amine | 147293-26-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 3-bromo-5-methyl-1,6-naphthyridin-2-amine
• CAS: 147293-26-3
• 化学式: C₉H₈BrN₃
• 分子量: 238.087
• InChiKey: BPVNMPORJNXDOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  51.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-bromo-5-methyl-1,6-naphthyridin-2-amine 在 N-甲基吡咯烷酮 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.5h， 生成 8-methyl-2-methylthiothiazolo<4,5-b><1,6>naphthyridine
  参考文献：
  名称：

  An Efficient and Novel Synthesis of Fused Thiazol-2(3H)-ones

  摘要：

  Reaction of o-bromo aromatic amines (2, 4, 7, 10, 15) with ethyl potassium xanthate gave the corresponding fused thiazol-2(3H)-thiones (16, 19, 22) which in turn were first alkylated with methyl iodide and then treated with sodium methoxide to produce fused thiazol-2(3H)-ones (18, 21, 24). Treatment of 4-(4-pyridinyl)-benzenamine dihydrobromide (1) with DMSO gave 2-bromo-4-(4-pyridinyl)benzenamine (2). Reduction of 4-(4-bromo-3-nitrophenyl)-pyridine (3) with stannous chloride gave 2-bromo-5-(4-pyridinyl)-benzenamine (4). Treatment of 5-bromo-2-methyl[3,4'-bipyridin]-6(1H)-one (5) with phosphorous oxychloride and ammonia sequentially yielded amino compound (7). Hofmann reaction of 2-chloro-6-methyl-[3,4'-bipyridine]-3-carboxamide resulted in amino compound (10). 5-Acyl-6-methylpyridin-2(1H)-ones (11) were converted to 3-bromo-1,6-naphthyridin-2-amines (15) via a four-step sequence.

  DOI：

  10.3987/com-92-6193
• 作为产物：
  描述：

  5-acetyl-3-bromo-6-<2-(dimethylamino)ethenyl>pyridin-2(1H)-one 在 ammonium acetate 、 氨 、 三氯氧磷 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 37.0h， 生成 3-bromo-5-methyl-1,6-naphthyridin-2-amine
  参考文献：
  名称：

  An Efficient and Novel Synthesis of Fused Thiazol-2(3H)-ones

  摘要：

  Reaction of o-bromo aromatic amines (2, 4, 7, 10, 15) with ethyl potassium xanthate gave the corresponding fused thiazol-2(3H)-thiones (16, 19, 22) which in turn were first alkylated with methyl iodide and then treated with sodium methoxide to produce fused thiazol-2(3H)-ones (18, 21, 24). Treatment of 4-(4-pyridinyl)-benzenamine dihydrobromide (1) with DMSO gave 2-bromo-4-(4-pyridinyl)benzenamine (2). Reduction of 4-(4-bromo-3-nitrophenyl)-pyridine (3) with stannous chloride gave 2-bromo-5-(4-pyridinyl)-benzenamine (4). Treatment of 5-bromo-2-methyl[3,4'-bipyridin]-6(1H)-one (5) with phosphorous oxychloride and ammonia sequentially yielded amino compound (7). Hofmann reaction of 2-chloro-6-methyl-[3,4'-bipyridine]-3-carboxamide resulted in amino compound (10). 5-Acyl-6-methylpyridin-2(1H)-ones (11) were converted to 3-bromo-1,6-naphthyridin-2-amines (15) via a four-step sequence.

  DOI：

  10.3987/com-92-6193

文献信息

• Chemokine Receptor Antagonist and Medical Use Thereof
  申请人：Habashita Hiromu

  公开号：US20070254886A1

  公开（公告）日：2007-11-01

  The present invention relates to a compound represented by formula (I), a salt thereof, an N-oxide thereof, a solvate thereof or a prodrug thereof, and medical use thereof (the symbols in the formula are as described in the specification). The compound represented by formula (I) has chemokine receptor (especially in CCR4 and/or CCR5) antagonistic activity. Therefore it is useful for prevention and/or treatment of a chemokine receptor-mediated disease such as inflammatory and/or allergic diseases [systemic inflammatory response syndrome (SIRS), anaphylaxis, anaphylactoid reaction, allergic angiitis, transplant rejection reaction, hepatitis, nephritis, nephropathy, pancreatitis, rhinitis, arthritis, inflammatory ocular disease, inflammatory bowel disease, disease in cerebro and/or circulatory system, respiratory disease, dermatosis, autoimmune disease, and the like], infection [viral disease (human immunodeficiency virus infection, acquired immunodeficiency syndrome, SARS, etc.), and the like], and the like.

  本发明涉及一种由公式（I）表示的化合物，其盐、N-氧化物、溶剂化物或前药，以及其医药用途（公式中的符号如说明书所述）。公式（I）表示的化合物具有趋化因子受体（尤其是在CCR4和/或CCR5中）拮抗活性。因此，它对于预防和/或治疗趋化因子受体介导的疾病，如炎症和/或过敏性疾病[全身性炎症反应综合征（SIRS）、过敏性休克、过敏性反应、过敏性血管炎、移植排斥反应、肝炎、肾炎、肾病、胰腺炎、鼻炎、关节炎、炎症性眼部疾病、炎症性肠病、脑和/或循环系统疾病、呼吸系统疾病、皮肤病、自身免疫性疾病等]、感染[病毒性疾病（人类免疫缺陷病毒感染、获得性免疫缺陷综合征、SARS等）等]等非常有用。
• CHEMOKINE RECEPTOR ANTAGONIST AND MEDICAL USE THEREOF
  申请人：HABASHITA Hiromu

  公开号：US20100266539A1

  公开（公告）日：2010-10-21

  The present invention relates to a compound represented by formula (I), a salt thereof, an N-oxide thereof, a solvate thereof or a prodrug thereof, and medical use thereof (the symbols in the formula are as described in the specification). The compound represented by formula (I) has chemokine receptor (especially in CCR4 and/or CCR5) antagonistic activity. Therefore it is useful for prevention and/or treatment of a chemokine receptor-mediated disease such as inflammatory and/or allergic diseases [systemic inflammatory response syndrome (SIRS), anaphylaxis, anaphylactoid reaction, allergic angiitis, transplant rejection reaction, hepatitis, nephritis, nephropathy, pancreatitis, rhinitis, arthritis, inflammatory ocular disease, inflammatory bowel disease, disease in cerebro and/or circulatory system, respiratory disease, dermatosis, autoimmune disease, and the like], infection [viral disease (human immunodeficiency virus infection, acquired immunodeficiency syndrome, SARS, etc.), and the like], and the like.

  本发明涉及一种由式（I）所表示的化合物，其盐、N-氧化物、溶剂化物或前药，以及其医药用途（式中符号如规范所述）。由式（I）所表示的化合物具有趋化因子受体（特别是在CCR4和/或CCR5中）的拮抗活性。因此，它对于预防和/或治疗趋化因子受体介导的疾病，如炎症和/或过敏性疾病[全身性炎症反应综合征（SIRS）、过敏反应、过敏性血管炎、移植排斥反应、肝炎、肾炎、肾病、胰腺炎、鼻炎、关节炎、炎症性眼病、炎症性肠病、脑和/或循环系统疾病、呼吸道疾病、皮肤病、自身免疫性疾病等]、感染[病毒性疾病（人类免疫缺陷病毒感染、获得性免疫缺陷综合征、SARS等）等]等具有用处。
• US7732442B2
  申请人：——

  公开号：US7732442B2

  公开（公告）日：2010-06-08