1-[(1R)-1-chloroethyl]-2-fluorobenzene | 911716-00-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-[(1R)-1-chloroethyl]-2-fluorobenzene
• CAS: 911716-00-2
• 化学式: C₈H₈ClF
• 分子量: 158.603
• InChiKey: BSNIDVZGHKZWDV-ZCFIWIBFSA-N

物化性质

• 沸点：
  178.2±15.0 °C(Predicted)
• 密度：
  1.144±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-[(1R)-1-chloroethyl]-2-fluorobenzene 在 sodium tetrahydroborate 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 以75%的产率得到6-amino-2-{[(1S)-1-(2-fluorophenyl)ethyl]thio}pyrimidin-4-ol
  参考文献：
  名称：

  WO2006/107257

  摘要：

  公开号：
• 作为产物：
  描述：

  (S)-1-(2-氟苯基)乙醇 在 N-氯代丁二酰亚胺 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以65%的产率得到1-[(1R)-1-chloroethyl]-2-fluorobenzene
  参考文献：
  名称：

  Substituted 7-Amino-5-thio-thiazolo[4,5-d]pyrimidines as Potent and Selective Antagonists of the Fractalkine Receptor (CX₃CR1)

  摘要：

  We have developed two parallel series, A and B, of CX(3)CR1 antagonists for the treatment of multiple sclerosis. By modifying the substituents on the 7-amino-5-thio-thiazolo[4,5-d]-pyrimidine core structure, we were able to achieve compounds with high selectivity for CX(3)CR1 over the closely related CXCR2 receptor. The structure-activity relationships showed that a leucinol moiety attached to the core-structure in the 7-position together with alpha-methyl branched benzyl derivatives in the 5-position displayed promising affinity, and selectivity as well as physicochemical properties, as exemplified by compounds 18a and 24h. We show the preparation of the first potent and selective orally available CX(3)CR1 antagonists.

  DOI：

  10.1021/jm3012273

文献信息

• Novel 5-Substituted 7-Amino-[1,3]Thiazolo[4,5-D]Pyrimidine Derivatives 793
  申请人：Nordvall Gunnar

  公开号：US20080214578A1

  公开（公告）日：2008-09-04

  There are disclosed novel 5-substituted 7-amino-[1,3]thiazolo[4,5-d]pyrimidine derivatives of formula (I) wherein R 1 , R 2 , R 3 , R 4 and R 5 are as defined in the specification, and pharmaceutically acceptable salts thereof, together with processes for their preparation, pharmaceutical compositions comprising them and their use in therapy. The compounds of formula (I) are CX 3 CR1 receptor antagonists and are thereby particularly useful in the treatment or prophylaxis of neurodegenerative disorders, demyelinating disease, cardio- and cerebrovascular atherosclerotic disorders, peripheral artery disease, rheumatoid arthritis, pulmonary diseases such as COPD, asthma or pain.

  公开了一种新的5-取代的7-氨基-[1,3]噻唑[4,5-d]嘧啶衍生物的公式(I)，其中R1、R2、R3、R4和R5如规范中所定义，并且其药学上可接受的盐，以及其制备方法、包含它们的药物组合物和它们在治疗中的用途。公式(I)化合物是CX3CR1受体拮抗剂，因此在治疗或预防神经退行性疾病、脱髓鞘性疾病、心血管和脑血管动脉粥样硬化性疾病、周围动脉疾病、类风湿性关节炎、慢性阻塞性肺疾病、哮喘或疼痛等方面特别有用。
• Novel 5,7-Disubstituted [1,3]Thiazolo[4,5-D]Pyrimidin-2(3H)-One Derivatives 794
  申请人：Nordvall Gunnar

  公开号：US20090124637A1

  公开（公告）日：2009-05-14

  There are disclosed novel 5,7-disubstituted [1,3]thiazolo[4,5-d]pyrimidin-2(3H)-one derivatives of formula (I) [Chemical formula should be inserted here. Please see paper copy] wherein R 1 , R 2 , R 3 , R 4 and R 5 are as defined in the specification, and pharmaceutically acceptable salts thereof, together with processes for their preparation, pharmaceutical compositions comprising them and their use in therapy. The compounds of formula (I) are CX 3 CR 1 receptor antagonists and are thereby particularly useful in the treatment or prophylaxis of neurodegenerative disorders, demyelinating disease, cardio- and cerebrovascular atherosclerotic disorders, peripheral artery disease, rheumatoid arthritis, pulmonary diseases such as COPD, asthma or pain.

  本文揭示了新颖的5,7-二取代[1,3]噻唑并[4,5-d]嘧啶-2(3H)-酮衍生物的公式(I) [化学式应在此处插入。请参见纸质复印件]，其中R1、R2、R3、R4和R5如规范中定义的那样，以及其药学上可接受的盐，以及它们的制备方法、包含它们的制剂和它们在治疗中的用途。公式(I)化合物是CX3CR1受体拮抗剂，因此在神经退行性疾病、脱髓鞘疾病、心脑血管动脉粥样硬化性疾病、周围动脉疾病、类风湿性关节炎、COPD、哮喘或疼痛的治疗或预防中特别有用。
• 5,7-disubstituted thiazolo[4,5-D]pyrimidines for the selective inhibition of chemokine receptors
  申请人：AstraZeneca AB

  公开号：US08088780B2

  公开（公告）日：2012-01-03

  There are disclosed novel 5,7-disubstituted [1,3]thiazolo[4,5-d]pyrimidin-2(3H)-one derivatives of formula (I) wherein R1, R2, R3, R4 and R5 are as defined in the specification, and pharmaceutically acceptable salts thereof, together with processes for their preparation, pharmaceutical compositions comprising them and their use in therapy. The compounds of formula (I) are CX3CR1 receptor antagonists and are thereby particularly useful in the treatment or prophylaxis of neurodegenerative disorders, demyelinating disease, cardio- and cerebrovascular atherosclerotic disorders, peripheral artery disease, rheumatoid arthritis, pulmonary diseases such as COPD, asthma or pain.

  公开了一种新的5,7-二取代[1,3]噻唑并[4,5-d]嘧啶-2(3H)-酮衍生物的化学式(I)，其中R1、R2、R3、R4和R5在规范中定义，并且其药学上可接受的盐，以及其制备过程、包含它们的制药组合物和它们在治疗中的用途。化合物(I)是CX3CR1受体拮抗剂，因此在治疗或预防神经退行性疾病、脱髓鞘性疾病、心血管和脑血管动脉粥样硬化性疾病、外周动脉疾病、类风湿性关节炎、慢性阻塞性肺疾病、哮喘或疼痛方面特别有用。
• 5,7-DISUBSTITUTED THIAZOLO[4,5-D]PYRIMIDINES AS CHEMOKINE INHIBITORS
  申请人：Nordvall Gunnar

  公开号：US20110092519A1

  公开（公告）日：2011-04-21

  There are disclosed novel 5-substituted 7-amino-[1,3]thiazolo[4,5-d]pyrimidine derivatives of formula (I) wherein R 1 , R 2 , R 3 , R 4 and R 5 are as defined in the specification, and pharmaceutically acceptable salts thereof, together with processes for their preparation, pharmaceutical compositions comprising them and their use in therapy. The compounds of formula (I) are CX 3 CR1 receptor antagonists and are thereby particularly useful in the treatment or prophylaxis of neurodegenerative disorders, demyelinating disease, cardio- and cerebrovascular atherosclerotic disorders, peripheral artery disease, rheumatoid arthritis, pulmonary diseases such as COPD, asthma or pain.

  本发明公开了一种新型的5-取代的7-氨基-[1,3]噻唑[4,5-d]嘧啶衍生物，其化学式为(I)，其中R1、R2、R3、R4和R5如规范中所定义，以及其药学上可接受的盐，以及它们的制备方法、包括它们的药物组合物和在治疗中的应用。公式(I)化合物是CX3CR1受体拮抗剂，因此在治疗或预防神经退行性疾病、脱髓鞘疾病、心血管和脑血管动脉粥样硬化疾病、周围动脉疾病、类风湿性关节炎、肺部疾病如慢性阻塞性肺疾病、哮喘或疼痛方面特别有用。
• 5,7-disubstituted thiazolo[4,5-D]pyrimidines as chemokine inhibitors
  申请人：AstraZeneca AB

  公开号：US07947693B2

  公开（公告）日：2011-05-24

  There are disclosed novel 5-substituted 7-amino-[1,3]thiazolo[4,5-d]pyrimidine derivatives of formula (I) wherein R1, R2, R3, R4 and R5 are as defined in the specification, and pharmaceutically acceptable salts thereof, together with processes for their preparation, pharmaceutical compositions comprising them and their use in therapy. The compounds of formula (I) are CX3CR1 receptor antagonists and are thereby particularly useful in the treatment or prophylaxis of neurodegenerative disorders, demyelinating disease, cardio- and cerebrovascular atherosclerotic disorders, peripheral artery disease, rheumatoid arthritis, pulmonary diseases such as COPD, asthma or pain.

  公开了一种新型的5-取代的7-氨基-[1,3]噻唑并[4,5-d]嘧啶衍生物，化学式为(I)，其中R1、R2、R3、R4和R5如规范中所定义，以及其药学上可接受的盐，以及它们的制备方法、包含它们的制药组合物以及它们在治疗中的应用。化合物(I)是CX3CR1受体拮抗剂，因此在治疗或预防神经退行性疾病、脱髓鞘疾病、心血管和脑血管动脉粥样硬化性疾病、周围动脉疾病、类风湿性关节炎、COPD、哮喘或疼痛方面特别有用。