2-(4-chlorophenyl)-3-fluoropyridine | 1233702-02-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-(4-chlorophenyl)-3-fluoropyridine
• 英文别名: 2-(4-Chloro-phenyl)-3-fluoro-pyridine
• CAS: 1233702-02-7
• 化学式: C₁₁H₇ClFN
• 分子量: 207.635
• InChiKey: WAAURGYZRQPPDJ-UHFFFAOYSA-N

物化性质

• 沸点：
  281.2±25.0 °C(Predicted)
• 密度：
  1.265±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-chlorophenyl)-3-fluoropyridine 在 双氧水 、 caesium carbonate 、 溶剂黄146 、 三乙胺 、 二甲氨基甲酰氯 作用下， 以 水 、 二甲基亚砜 、 乙腈 为溶剂， 反应 20.75h， 生成 6-(4-chlorophenyl)-5-(2,2,2-trifluoroethoxy)-2-pyridinecarbonitrile
  参考文献：
  名称：

  6-Alkoxy-5-aryl-3-pyridinecarboxamides, a New Series of Bioavailable Cannabinoid Receptor Type 1 (CB1) Antagonists Including Peripherally Selective Compounds

  摘要：

  We identified 6-alkoxy-5-aryl-3-pyridinecarboxamides as potent CB1 receptor antagonists with high selectivity over CB2 receptors. The series was optimized to reduce lipophilicity compared to rimonabant to achieve peripherally active molecules with minimal central effects. Several compounds that showed high plasma exposures in rats were evaluated in vivo to probe the contribution of central vs peripheral CB1 agonism to metabolic improvement. Both rimonabant and 14g, a potent brain penetrant CB1 receptor antagonist, significantly reduced the rate of body weight gain. However, 14h, a molecule with markedly reduced brain exposure, had no significant effect on body weight. PK studies confirmed similarly high exposure of both 14h and 14g in the periphery but 10-fold lower exposure in the brain for 14h. On the basis of these data, which are consistent with reported effects in tissue-specific CB1 receptor KO mice, we conclude that the metabolic benefits of CB1 receptor antagonists are primarily centrally mediated as originally believed.

  DOI：

  10.1021/jm4010708
• 作为产物：
  描述：

  2-氯-3-氟吡啶 、 4-氯苯硼酸 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride sodium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 5.0h， 以65.73%的产率得到2-(4-chlorophenyl)-3-fluoropyridine
  参考文献：
  名称：

  [EN] HETEROARYLMETHYL AMIDES
  [FR] HÉTÉROARYLMÉTHYL-AMIDES

  摘要：

  本发明涉及公式I中的化合物，其中A1、A2、A3和R1至R8在描述中有定义，以及其药用盐，其制备方法，含有它们的药物组合物以及它们作为药物用于治疗和/或预防可以用HDL-胆固醇升高剂治疗的疾病，如特别是脂质代谢异常、动脉粥样硬化和心血管疾病。

  公开号：

  WO2012032018A1

文献信息

• Synthesis of 3-Substituted 2-Arylpyridines via Cu/Pd-Catalyzed Decarboxylative Cross-Coupling of Picolinic Acids with (Hetero)Aryl Halides
  作者：Dagmar Hackenberger、Philip Weber、David C. Blakemore、Lukas J. Goossen

  DOI：10.1021/acs.joc.7b00046

  日期：2017.4.7

  A decarboxylative cross-coupling of 3-substituted picolinic acids with (hetero)aryl halides is presented. In the presence of catalytic Cu2O and Pd(1,5-cyclooctadiene)Cl2 with 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl as the ligand, both electron-rich and electron-deficient aryl bromides and chlorides as well as heteroaryl bromides were successfully coupled with various picolinate salts

  提出了3-取代的吡啶甲酸与（杂）芳基卤化物的脱羧交叉偶联。在催化性的Cu 2 O和Pd（1,5-环辛二烯）Cl 2以2-二环己基膦基-2'-（N，N-二甲基氨基）联苯为配体的情况下，富电子和缺电子的芳基溴化物和在温和的条件下，将氯化物以及杂芳基溴化物与各种吡啶甲酸盐成功偶联，收率高达96％。该方案提供了有效的进入2-（杂）芳基吡啶的途径，这是药物发现中一种有吸引力的物质。
• [EN] 7-PHENOXYCHROMAN CARBOXYLIC ACID DERIVATIVES<br/>[FR] DÉRIVÉS D'ACIDE 7-PHÉNOXYCHROMANECARBOXYLIQUE
  申请人：ARRAY BIOPHARMA INC

  公开号：WO2010075200A1

  公开（公告）日：2010-07-01

  Compounds of Formula I: (I) in which A, A1, R1, R7a, R7b, R8 and R10 have the meanings given in the specification, are DP2 receptor inhibitors useful in the treatment of useful in the treatment and prevention of immunologic diseases, allergic diseases such as asthma, allergic rhinitis and atopic dermatitis, and other inflammatory diseases mediated by prostaglandin D2 (PGD2). The compounds of Formula I may also be useful in treating diseases or medical conditions involving the Th2 T cell via production of IL-4, IL-5 and/or IL-13.

  化合物的化学式I：（I），其中A，A1，R1，R7a，R7b，R8和R10具有规范中给定的含义，是DP2受体抑制剂，在治疗免疫性疾病、过敏性疾病（如哮喘、过敏性鼻炎和特应性皮炎）以及由前列腺素D2（PGD2）介导的其他炎症性疾病的治疗中有用。化合物的化学式I也可能在治疗涉及Th2 T细胞通过IL-4、IL-5和/或IL-13产生的疾病或医疗状况中有用。
• HETEROARYLMETHYL AMIDES
  申请人：Hebeisen Paul

  公开号：US20120065212A1

  公开（公告）日：2012-03-15

  The present invention relates to compounds of the formula wherein A 1 , A 2 , A 3 and R 1 to R 8 are defined in the description, and to pharmaceutically acceptable salts thereof, their manufacture, pharmaceutical compositions containing them and their use as medicaments for the treatment and/or prophylaxis of diseases which can be treated with HDL-cholesterol raising agents, such as particularly dyslipidemia, atherosclerosis and cardiovascular diseases.

  本发明涉及以下公式的化合物，其中A1、A2、A3和R1至R8在描述中有定义，并且其药用盐，其制备，含有它们的药物组合物以及它们作为药物用于治疗和/或预防可用高密度脂蛋白胆固醇升高剂治疗的疾病，例如特别是血脂异常、动脉粥样硬化和心血管疾病。
• [EN] HETEROARYLMETHYL AMIDES<br/>[FR] HÉTÉROARYLMÉTHYL-AMIDES
  申请人：HOFFMANN LA ROCHE

  公开号：WO2012032018A1

  公开（公告）日：2012-03-15

  The present invention relates to compounds of the formula I wherein A1, A2, A3 and R1 to R8 are defined in the description, and to pharmaceutically acceptable salts thereof, their manufacture, pharmaceutical compositions containing them and their use as medicaments for the treatment and/or prophylaxis of diseases which can be treated with HDL-cholesterol raising agents, such as particularly dyslipidemia, atherosclerosis and cardiovascular diseases.

  本发明涉及公式I中的化合物，其中A1、A2、A3和R1至R8在描述中有定义，以及其药用盐，其制备方法，含有它们的药物组合物以及它们作为药物用于治疗和/或预防可以用HDL-胆固醇升高剂治疗的疾病，如特别是脂质代谢异常、动脉粥样硬化和心血管疾病。
• 7-PHENOXYCHROMAN CARBOXYLIC ACID DERIVATIVES
  申请人：Cook Adam

  公开号：US20120101103A1

  公开（公告）日：2012-04-26

  Compounds of Formula I: (I) in which A, A 1 , R 1 , R 7a , R 7b , R 8 and R 10 have the meanings given in the specification, are DP2 receptor inhibitors useful in the treatment of useful in the treatment and prevention of immunologic diseases, allergic diseases such as asthma, allergic rhinitis and atopic dermatitis, and other inflammatory diseases mediated by prostaglandin D 2 (PGD 2 ). The compounds of Formula I may also be useful in treating diseases or medical conditions involving the Th2 T cell via production of IL-4, IL-5 and/or IL-13.

  化合物公式I：（I），其中A，A1，R1，R7a，R7b，R8和R10的含义如规范中所述，是DP2受体抑制剂，可用于治疗免疫性疾病、过敏性疾病（如哮喘、过敏性鼻炎和特应性皮炎）以及通过前列腺素D2（PGD2）介导的其他炎症性疾病的治疗和预防。公式I的化合物还可用于治疗涉及Th2 T细胞通过产生IL-4、IL-5和/或IL-13的疾病或医疗条件。