3-溴-2-氟-5-碘吡啶 | 697300-72-4

• 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: 3-溴-2-氟-5-碘吡啶
• 英文名称: 3-bromo-2-fluoro-5-iodopyridine
• CAS: 697300-72-4
• 化学式: C₅H₂BrFIN
• 分子量: 301.884
• InChiKey: MLOIGFZNGAEEDT-UHFFFAOYSA-N

物化性质

• 熔点：
  80-83 °C
• 沸点：
  268.4±40.0 °C(Predicted)
• 密度：
  2.412±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• 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：

  3-溴-2-氟-5-碘吡啶 在 lithium chloro-isopropyl-magnesium chloride 、 sodium peroxoborate tetrahydrate 、 sodium hydride 作用下， 以 四氢呋喃 、 水 、 mineral oil 为溶剂， 反应 22.83h， 生成 5-bromo-6-(cyclopropylmethoxy)pyridin-3-ol
  参考文献：
  名称：

  [EN] ISOINDOLINONE COMPOUNDS AS GPR119 MODULATORS FOR THE TREATMENT OF DIABETES, OBESITY, DYSLIPIDEMIA AND RELATED DISORDERS
  [FR] COMPOSÉS D'ISOINDOLINONE UTILISÉS COMME MODULATEURS DE GPR119 POUR LE TRAITEMENT DU DIABÈTE, DE L'OBÉSITÉ ET DE TROUBLES ASSOCIÉS

  摘要：

  本发明涉及异吲哚啉酮化合物。这些异吲哚啉酮化合物是GPR119调节剂，可用于预防和/或治疗糖尿病、肥胖、血脂异常和相关疾病。此外，本发明还涉及将异吲哚啉酮化合物用作药物的活性成分，以及包含它们的药物组合物。

  公开号：

  WO2015150565A1
• 作为产物：
  描述：

  2-氨基-5-碘吡啶 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 氢氟酸 、 sodium nitrite 作用下， 以 乙腈 为溶剂， 反应 97.5h， 生成 3-溴-2-氟-5-碘吡啶
  参考文献：
  名称：

  5-Substituted Derivatives of 6-Halogeno-3-((2-(S)-azetidinyl)methoxy)pyridine and 6-Halogeno-3-((2-(S)-pyrrolidinyl)methoxy)pyridine with Low Picomolar Affinity for α4β2 Nicotinic Acetylcholine Receptor and Wide Range of Lipophilicity:  Potential Probes for Imaging with Positron Emission Tomography

  摘要：

  Potential positron emission tomography (PET) ligands with low picomolar affinity at the nicotinic acetylcholine receptor (nAChR) and with lipophilicity (log D) ranging from -1.6 to +1.5 have been synthesized. Most members of the series, which are derivatives of 5-substituted-6-halogeno-A-85380, exhibited a higher binding affinity at alpha4beta2-nAChRs than epibatidine. An analysis, by molecular modeling, revealed an important role of the orientation of the additional heterocyclic ring on the binding affinity of the ligands with nAChRs. The existing nicotinic pharmacophore models do not accommodate this finding. Two compounds of the series, 6-[F-18]-fluoro-5-(pyridin-3-yl)-A-85380 ([F-18]31) and 6-chloro-3-((2-(S)-azetidinyl)methoxy)-5-(2- [F-18]-fluoropyridin-5-yl)pyridine) ([F-18]35), were radiolabeled with F-18. Comparison of PET data for [F-18]31 and 2-[F-18]FA shows the influence of lipophilicity on the binding potential. Our recent PET studies with [F-18]35 demonstrated that its binding potential values in Rhesus monkey brain were ca. 2.5 times those of 2-[F-18]FA. Therefore, [F-18]35 and several other members of the series, when radiolabeled, will be suitable for quantitative imaging of extrathalamic nAChRs.

  DOI：

  10.1021/jm030432v

文献信息

• PYRROLIDINONE DERIVATIVES AS GPR119 MODULATORS FOR THE TREATMENT OF DIABETES, OBESITY, DYSLIPIDEMIA AND RELATED DISORDERS
  申请人：SCHWINK Lothar

  公开号：US20140099333A1

  公开（公告）日：2014-04-10

  The present invention relates to pyrrolidinone derivatives. The pyrrolidinone derivatives are GPR119 modulators and useful for the prevention and/or treatment of diabetes, obesity, dyslipidemia and related disorders. The invention furthermore relates to the use of pyrrolidinone derivatives as active ingredients in pharmaceuticals, and pharmaceutical compositions comprising them.

  本发明涉及吡咯烷酮衍生物。这些吡咯烷酮衍生物是GPR119调节剂，适用于预防和/或治疗糖尿病、肥胖、血脂异常及相关疾病。此外，本发明还涉及将吡咯烷酮衍生物用作药物中的活性成分，以及包含它们的药物组合物。
• [EN] PYRROLIDINONE DERIVATIVES AS GPR119 MODULATORS FOR THE TREATMENT OF DIABETES, OBESITY, DYSLIPIDEMIA AND RELATED DISORDERS<br/>[FR] DÉRIVÉS DE PYRROLIDINONE À TITRE DE MODULATEURS DE GPR119 POUR LE TRAITEMENT DU DIABÈTE, DE L'OBÉSITÉ, DE LA DYSLIPIDÉMIE ET AUTRES AFFECTIONS APPARENTÉES
  申请人：SANOFI SA

  公开号：WO2014056938A1

  公开（公告）日：2014-04-17

  The present invention relates to pyrrolidinone derivatives of formula (I). The pyrrolidinone derivatives of formula (I) are GPR119 modulators and useful for the prevention and/or treatment of diabetes, obesity, dyslipidemia and related disorders. The invention furthermore relates to the use of pyrrolidinone derivatives as active ingredients in pharmaceuticals, and pharmaceutical compositions comprising them.

  本发明涉及式（I）的吡咯烷酮衍生物。式（I）的吡咯烷酮衍生物是GPR119调节剂，用于预防和/或治疗糖尿病、肥胖、血脂异常及相关疾病。此外，本发明还涉及将吡咯烷酮衍生物用作药物中的活性成分，以及包含它们的药物组合物。
• Pyrrolidinone derivatives as GPR119 modulators for the treatment of diabetes, obesity, dyslipidemia and related disorders
  申请人：Schwink Lothar

  公开号：US08853412B2

  公开（公告）日：2014-10-07

  The present invention relates to pyrrolidinone derivatives. The pyrrolidinone derivatives are GPR119 modulators and useful for the prevention and/or treatment of diabetes, obesity, dyslipidemia and related disorders. The invention furthermore relates to the use of pyrrolidinone derivatives as active ingredients in pharmaceuticals, and pharmaceutical compositions comprising them.

  本发明涉及吡咯烷酮衍生物。这些吡咯烷酮衍生物是GPR119调节剂，可用于预防和/或治疗糖尿病、肥胖症、血脂异常及相关疾病。此外，本发明还涉及将吡咯烷酮衍生物用作药物的活性成分，并包含它们的药物组合物。
• 5-Substituted Derivatives of 6-Halogeno-3-((2-(<i>S</i>)-azetidinyl)methoxy)pyridine and 6-Halogeno-3-((2-(<i>S</i>)-pyrrolidinyl)methoxy)pyridine with Low Picomolar Affinity for α4β2 Nicotinic Acetylcholine Receptor and Wide Range of Lipophilicity:  Potential Probes for Imaging with Positron Emission Tomography
  作者：Yi Zhang、Olga A. Pavlova、Svetlana I. Chefer、Andrew W. Hall、Varughese Kurian、LaVerne L. Brown、Alane S. Kimes、Alexey G. Mukhin、Andrew G. Horti

  DOI：10.1021/jm030432v

  日期：2004.5.1

  Potential positron emission tomography (PET) ligands with low picomolar affinity at the nicotinic acetylcholine receptor (nAChR) and with lipophilicity (log D) ranging from -1.6 to +1.5 have been synthesized. Most members of the series, which are derivatives of 5-substituted-6-halogeno-A-85380, exhibited a higher binding affinity at alpha4beta2-nAChRs than epibatidine. An analysis, by molecular modeling, revealed an important role of the orientation of the additional heterocyclic ring on the binding affinity of the ligands with nAChRs. The existing nicotinic pharmacophore models do not accommodate this finding. Two compounds of the series, 6-[F-18]-fluoro-5-(pyridin-3-yl)-A-85380 ([F-18]31) and 6-chloro-3-((2-(S)-azetidinyl)methoxy)-5-(2- [F-18]-fluoropyridin-5-yl)pyridine) ([F-18]35), were radiolabeled with F-18. Comparison of PET data for [F-18]31 and 2-[F-18]FA shows the influence of lipophilicity on the binding potential. Our recent PET studies with [F-18]35 demonstrated that its binding potential values in Rhesus monkey brain were ca. 2.5 times those of 2-[F-18]FA. Therefore, [F-18]35 and several other members of the series, when radiolabeled, will be suitable for quantitative imaging of extrathalamic nAChRs.
• [EN] ISOINDOLINONE COMPOUNDS AS GPR119 MODULATORS FOR THE TREATMENT OF DIABETES, OBESITY, DYSLIPIDEMIA AND RELATED DISORDERS<br/>[FR] COMPOSÉS D'ISOINDOLINONE UTILISÉS COMME MODULATEURS DE GPR119 POUR LE TRAITEMENT DU DIABÈTE, DE L'OBÉSITÉ ET DE TROUBLES ASSOCIÉS
  申请人：SANOFI SA

  公开号：WO2015150565A1

  公开（公告）日：2015-10-08

  The present invention relates to isoindolinone compounds. The isoindolinone compounds are GPR119 modulators and useful for the prevention and/or treatment of diabetes, obesity, dyslipidemia and related disorders. The invention furthermore relates to the use of isoindolinone compounds as active ingredients in pharmaceuticals, and pharmaceutical compositions comprising them.

  本发明涉及异吲哚啉酮化合物。这些异吲哚啉酮化合物是GPR119调节剂，可用于预防和/或治疗糖尿病、肥胖、血脂异常和相关疾病。此外，本发明还涉及将异吲哚啉酮化合物用作药物的活性成分，以及包含它们的药物组合物。