4-(3-溴-4-甲氧基苯基)吡啶 | 191602-60-5

• 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
• 中文名称: 4-(3-溴-4-甲氧基苯基)吡啶
• 英文名称: 4-(3-bromo-4-methoxyphenyl)pyridine
• 英文别名: 2-Bromo4-(4'-pyridyl)anisole
• CAS: 191602-60-5
• 化学式: C₁₂H₁₀BrNO
• 分子量: 264.121
• InChiKey: JOCCQFWHBVVRNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933399090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  室温且干燥

反应信息

• 作为反应物：
  描述：

  4-(3-溴-4-甲氧基苯基)吡啶 在 四(三苯基膦)钯 、 正己基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.75h， 生成 5-[2-methoxy-5-(4-pyridinyl)phenyl]-2,1,3-benzoxadiazole
  参考文献：
  名称：

  Large-Scale Negishi Coupling as Applied to the Synthesis of PDE472, an Inhibitor of Phosphodiesterase Type 4D

  摘要：

  5-[2-Methoxy-5-(4-pyridinyl)phenyl]-2,1,3-benzoxadiazole (PDE472) is a selective inhibitor of the phosphodiesterase PDE4D isoenzyme, which is a recognised drug target for the treatment of asthma. Different synthetic routes to PDE472 were investigated, and the research synthesis was optimised to prepare a phase I batch on pilot-plant scale with the focus on the elimination or minimization of inherent process risks. An important refinement of the key Negishi aryl-aryl coupling involved preforming the arylpalladium complex, which was then added to the arylzinc intermediate. Residual palladium was removed from PDE472 via crystallization of the hemi-maleate salt, which afforded drug-substance containing < 2 ppm Pd.

  DOI：

  10.1021/op025615q
• 作为产物：
  描述：

  4-氯吡啶 在 溴 、 碘 、 magnesium 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 79.25h， 生成 4-(3-溴-4-甲氧基苯基)吡啶
  参考文献：
  名称：

  Large-Scale Negishi Coupling as Applied to the Synthesis of PDE472, an Inhibitor of Phosphodiesterase Type 4D

  摘要：

  5-[2-Methoxy-5-(4-pyridinyl)phenyl]-2,1,3-benzoxadiazole (PDE472) is a selective inhibitor of the phosphodiesterase PDE4D isoenzyme, which is a recognised drug target for the treatment of asthma. Different synthetic routes to PDE472 were investigated, and the research synthesis was optimised to prepare a phase I batch on pilot-plant scale with the focus on the elimination or minimization of inherent process risks. An important refinement of the key Negishi aryl-aryl coupling involved preforming the arylpalladium complex, which was then added to the arylzinc intermediate. Residual palladium was removed from PDE472 via crystallization of the hemi-maleate salt, which afforded drug-substance containing < 2 ppm Pd.

  DOI：

  10.1021/op025615q

文献信息

• 1,3-Dihydro-2H-Indole-2-One Compound and Pyrrolidine-2-One Compound Fused With Aromatic Heterocycle
  申请人：Sekiguchi Yoshinori

  公开号：US20080318923A1

  公开（公告）日：2008-12-25

  It is intended to provide a drug which is efficacious against pathological conditions relating to arginine-vasopressin V1b receptor. More particularly speaking, it is intended to provide a drug which has a therapeutic or preventive effect on depression, anxiety, Alzheimer's disease, Parkinson's disease, Huntington's chorea, eating disorders, hypertension, digestive diseases, drug addiction, epilepsy, brain infarction, brain ischemia, brain edema, head injury, inflammation, immune diseases, alopecia and so on. As the results of intensive studies, a novel 1,3-dihydro-2H-indol-2-one compound and a pyrrolidin-2-one compound fused with a heteroaromatic ring, which are highly selective antagonists of arginine-vasopressin V1b receptor, have high metabolic stabilities and show favorable brain penetration and high plasma concentrations, are found, thereby achieving the above objective.

  旨在提供一种对与精氨酸加压素V1b受体相关的病理状况具有疗效的药物。更具体地说，旨在提供一种对抑郁症、焦虑症、阿尔茨海默病、帕金森病、亨廷顿舞蹈症、进食障碍、高血压、消化系统疾病、药物成瘾、癫痫、脑梗死、脑缺血、脑水肿、头部损伤、炎症、免疫疾病、脱发等具有治疗或预防作用的药物。经过深入研究，发现了一种新颖的1,3-二氢-2H-吲哚-2-酮化合物和与杂芳环融合的吡咯烷-2-酮化合物，它们是高度选择性的精氨酸加压素V1b受体拮抗剂，具有高代谢稳定性，表现出有利的血脑屏障穿透和高血浆浓度，从而实现了上述目标。
• Phenylpyridine derivatives useful as phosphodiesterase inhibitors
  申请人：——

  公开号：US20020028831A1

  公开（公告）日：2002-03-07

  (4-oxy-3-(aryl)phenyl)pyridine compounds, in free or acid addition salt form, are useful as pharmaceuticals for treatment and prophylaxis of inflammation, particularly inflammatory or obstructive diseases of the airways, e.g. for asthma therapy. Preferred compounds are novel biphenyl pyridines, biphenyl benzamides and biphenyl phenylcarboxy compounds. The compounds are selective inhibitors of PDE 4 isoenzyme activity and also act to down regulate or inhibit TNF-&agr; release.

  (4-氧代-3-(芳基)苯基)吡啶化合物，以自由形式或酸盐形式，作为药物用于治疗和预防炎症，特别是空气道的炎症或阻塞性疾病，例如哮喘治疗。优选的化合物是新型的联苯基吡啶、联苯基苯甲酰胺和联苯基苯基羧酸化合物。这些化合物是PDE 4同工酶活性的选择性抑制剂，同时也可以下调或抑制TNF-α的释放。
• Spiro-piperidine derivatives and their use as tachykinin antagonists
  申请人：Merck Sharp & Dohme Ltd.

  公开号：US06060469A1

  公开（公告）日：2000-05-09

  The present invention relates to compounds of formula (I), ##STR1## wherein R.sup.1 represents halogen, hydroxy, C.sub.1-6 alkyl group optionally substituted by one or three fluorine atoms, C.sub.1-6 alkoxy group optionally substituted by one to three fluorine atoms, or C.sub.1-6 alkylthio optionally substituted by one to three fluorine atoms; R.sup.2 represents hydrogen, halogen, C.sub.1-6 alkyl or C.sub.1-6 alkoxy; or when R.sup.2 is adjacent to R.sup.1, they may be joined together such that there is formed a 5- or 6-membered saturated or unsaturated ring containing one or two oxygen atoms; R.sup.3 represents an optionally substituted 5- or 6-membered aromatic heterocyclic group containing 1, 2, 3 or 4 heteroatoms, selected from nitrogen, oxygen and sulphur; m is 0-3 and n is 0-3, with the proviso that the sum total of m+n is 2 or 3; p is zero or 1; q is 1 or 2; and when m is 1 and n is 1 or 2, the broken line represents an optional double bond; R.sup.4, R.sup.5, R.sup.6, R.sup.9 and R.sup.10 are a variety of substituents defined in the specification; or a pharmaceutically acceptable salt thereof. The compounds are of particular use in the treatment or prevention of pain, inflammation, emesis and postherpetic neuralgia.

  本发明涉及式(I)的化合物，其中R.sup.1代表卤素，羟基，C.sub.1-6烷基（可选择性地被1或3个氟原子取代），C.sub.1-6烷氧基（可选择性地被1至3个氟原子取代），或C.sub.1-6烷硫基（可选择性地被1至3个氟原子取代）; R.sup.2代表氢，卤素，C.sub.1-6烷基或C.sub.1-6烷氧基; 或当R.sup.2邻接R.sup.1时，它们可以结合在一起形成一个含有一个或两个氧原子的5-或6-成员饱和或不饱和环; R.sup.3代表一个可选择性取代的5-或6-成员芳香杂环基，该杂环基含有1、2、3或4个杂原子，选择自氮、氧和硫; m为0-3，n为0-3，但满足m + n的总和为2或3; p为零或1; q为1或2; 当m为1且n为1或2时，断裂线表示可选择性的双键; R.sup.4、R.sup.5、R.sup.6、R.sup.9和R.sup.10是规范中定义的各种取代基; 或其药学上可接受的盐。该化合物特别适用于治疗或预防疼痛、炎症、呕吐和带状疱疹后神经痛。
• 4-oxy-3-(aryl)phenyl-arylcarbonyloxy compounds useful as phosphodiesterase inhibitors
  申请人：Novartis AG

  公开号：US06258843B1

  公开（公告）日：2001-07-10

  (4-oxy-3-(aryl)phenyl)pyridine compounds, in free or acid addition salt form, are useful as pharmaceuticals for treatment and prophylaxis of inflammation, particularly inflammatory or obstructive diseases of the airways, e.g. for asthma therapy. Preferred compounds are novel biphenyl pyridines, biphenyl benzamides and biphenyl phenylcarboxy compounds. The compounds are selective inhibitors of PDE 4 isoenzyme activity and also act to down regulate or inhibit TNF-&agr; release.

  (4-氧代-3-(芳基)苯基)吡啶化合物，以自由形式或酸加成盐形式，可用作药物治疗和预防炎症，特别是气道炎症或阻塞性疾病，例如哮喘治疗。首选化合物是新型联苯基吡啶、联苯基苯甲酰胺和联苯基苯基羧酸化合物。这些化合物是PDE 4同工酶活性的选择性抑制剂，同时也具有下调或抑制TNF-α释放的作用。
• Triaryl compounds
  申请人：Novartis AG

  公开号：US06288092B1

  公开（公告）日：2001-09-11

  (4-oxy-3-(aryl)phenyl)pyridine compounds, in free or acid addition salt form, are useful as pharmaceuticals for treatment and prophylaxis of inflammation, particularly inflammatory or obstructive diseases of the airways, e.g. for asthma therapy. Preferred compounds are novel biphenyl pyridines, biphenyl benzamides and biphenyl phenylcarboxy compounds. The compounds are selective inhibitors of PDE 4 isoenzyme activity and also act to down regulate or inhibit TNF-&agr; release.

  (4-氧代-3-(芳基)苯基)吡啶类化合物，以自由或酸盐形式，可用作药物治疗和预防炎症，特别是呼吸道的炎症或阻塞性疾病，例如哮喘治疗。优选的化合物是新型联苯基吡啶、联苯基苯甲酰胺和联苯基苯甲酸类化合物。这些化合物是PDE 4同工酶活性的选择性抑制剂，同时也具有下调或抑制TNF-α释放的作用。