(S)-5-(2-azetidinyl-methoxy)-2-chloropyridine | 203564-57-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-5-(2-azetidinyl-methoxy)-2-chloropyridine
• 英文别名: A 98593；3-(2-(S)-azetidinylmethoxy)-6-chloropyridine；5-((S)-1-Azetidin-2-ylmethoxy)-2-chloro-pyridine；5-[[(2S)-azetidin-2-yl]methoxy]-2-chloropyridine
• CAS: 203564-57-2
• 化学式: C₉H₁₁ClN₂O
• 分子量: 198.652
• InChiKey: MKTAGSRKQIGEBH-ZETCQYMHSA-N

物化性质

• 沸点：
  321.1±22.0 °C(Predicted)
• 密度：
  1.228±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  34.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 (S)-5-(2-azetidinyl-methoxy)-2-chloropyridine 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 水 为溶剂， 以37%的产率得到2-Chloro-5-((S)-1-methyl-azetidin-2-ylmethoxy)-pyridine
  参考文献：
  名称：

  Identification and Initial Structure−Activity Relationships of (R)-5-(2-Azetidinylmethoxy)-2-chloropyridine (ABT-594), a Potent, Orally Active, Non-Opiate Analgesic Agent Acting via Neuronal Nicotinic Acetylcholine Receptors

  摘要：

  New members of a previously reported series of 3-pyridyl ether compounds are disclosed as novel, potent analgesic agents acting through neuronal nicotinic acetylcholine receptors. Both (R)-2-chloro-5-(2-azetidinylmethoxy)pyridine (ABT-594, 5) and its S-enantiomer (4) show potent analgesic activity in the mouse hot-plate assay following either intraperitoneal (ip) or oral (po) administration, as well as activity in the mouse abdominal constriction (writhing) assay, a model of persistent pain. Compared to the S-enantiomer and to the prototypical potent nicotinic analgesic agent (+/-)-epibatidine, 5 shows diminished activity in models of peripheral side effects. Structure-activity studies of analogues related to 4 and 5 suggest that the N-unsubstituted azetidine moiety and the 2-chloro substituent on the pyridine ring are important contributors to potent analgesic activity.

  DOI：

  10.1021/jm9706224
• 作为产物：
  描述：

  2-氯-5-羟基吡啶 在 盐酸 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 4.5h， 生成 (S)-5-(2-azetidinyl-methoxy)-2-chloropyridine
  参考文献：
  名称：

  Identification and Initial Structure−Activity Relationships of (R)-5-(2-Azetidinylmethoxy)-2-chloropyridine (ABT-594), a Potent, Orally Active, Non-Opiate Analgesic Agent Acting via Neuronal Nicotinic Acetylcholine Receptors

  摘要：

  New members of a previously reported series of 3-pyridyl ether compounds are disclosed as novel, potent analgesic agents acting through neuronal nicotinic acetylcholine receptors. Both (R)-2-chloro-5-(2-azetidinylmethoxy)pyridine (ABT-594, 5) and its S-enantiomer (4) show potent analgesic activity in the mouse hot-plate assay following either intraperitoneal (ip) or oral (po) administration, as well as activity in the mouse abdominal constriction (writhing) assay, a model of persistent pain. Compared to the S-enantiomer and to the prototypical potent nicotinic analgesic agent (+/-)-epibatidine, 5 shows diminished activity in models of peripheral side effects. Structure-activity studies of analogues related to 4 and 5 suggest that the N-unsubstituted azetidine moiety and the 2-chloro substituent on the pyridine ring are important contributors to potent analgesic activity.

  DOI：

  10.1021/jm9706224

文献信息

• ACTIVE AGENT DELIVERY SYSTEMS AND METHODS FOR PROTECTING AND ADMINISTERING ACTIVE AGENTS
  申请人：Mickle Travis

  公开号：US20090253792A1

  公开（公告）日：2009-10-08

  The present invention relates to active agent delivery systems and more specifically to compositions that comprise amino acids, as single amino acids or peptides, covalently attached to active agents and methods for administering conjugated active agent compositions.

  本发明涉及活性剂递送系统，更具体地涉及包含氨基酸（作为单个氨基酸或肽）与活性剂共价连接的组合物以及给予共轭活性剂组合物的方法。
• ACTIVE AGENT DELIVERY SYSTEMS AND METHODS FOR PROTECTING AND ADMINISTERING ACTIVE AGENTS
  申请人：Mickle Travis

  公开号：US20090306228A1

  公开（公告）日：2009-12-10

  The present invention relates to active agent delivery systems and more specifically to compositions that comprise amino acids, as single amino acids or peptides, covalently attached to active agents and methods for administering conjugated active agent compositions.

  本发明涉及活性剂递送系统，更具体地涉及包含氨基酸，作为单个氨基酸或肽，与活性剂共价结合的组合物以及用于给予共轭活性剂组合物的方法。
• Novel Pharmaceutical Compositions for Treating Chronic Pain and Pain Associated with Neuropathy
  申请人：Singh Chandra U.

  公开号：US20130189354A1

  公开（公告）日：2013-07-25

  The present invention relates to compositions and methods for treating pain wherein the compositions comprise a combination of tramadol or a pharmaceutically acceptable salt thereof, magnesium or a pharmaceutically acceptable salt thereof; and gabapentin or pregabalin. The therapeutic combination can further contain capsaicin or an ester of capsaicin.

  本发明涉及用于治疗疼痛的组合物和方法，其中所述组合物包括曲马多或其药学上可接受的盐、镁或其药学上可接受的盐；以及加巴嘌醇或普瑞巴林。治疗组合物还可以包含辣椒素或辣椒素酯。
• Irrigation solution and method for inhibition of pain and inflammation
  申请人：Omeros Medical Systems

  公开号：US20020028798A1

  公开（公告）日：2002-03-07

  A method and solution for perioperatively inhibiting a variety of pain and inflammation processes at wounds from general surgical procedures including oral/dental procedures. The solution preferably includes at least one pharmacological agent selected from the group consisting of a mitogen-activated protein kinase (MAPK) inhibitor, an &agr; 2 -receptor agonist, a neuronal nicotinic acetylcholine receptor agonist, a cyclooxygenase-2 (COX-2) inhibitor, a soluble receptor and mixtures thereof, and optionally additional multiple pain and inflammation inhibitory agents at dilute concentration in a physiologic carrier, such as saline or lactated Ringer's solution. The solution is applied by continuous irrigation of a wound during a surgical procedure for preemptive inhibition of pain and while avoiding undesirable side effects associated with oral, intramuscular, subcutaneous or intravenous application of larger doses of the agents.

  一种围手术期抑制一般外科手术（包括口腔/牙科手术）伤口处各种疼痛和炎症过程的方法和溶液。该溶液优选包括至少一种药剂，该药剂选自丝裂原活化蛋白激酶（MAPK）抑制剂、拮抗剂、拮抗剂、拮抗剂、拮抗剂和拮抗剂等组成的组； 2 -受体激动剂、神经元烟碱乙酰胆碱受体激动剂、环氧化酶-2（COX-2）抑制剂、可溶性受体及其混合物组成的组中选出的至少一种药剂，以及可选的在生理载体（如生理盐水或乳酸林格氏液）中稀释浓度的其他多种疼痛和炎症抑制剂。该溶液可在手术过程中通过持续冲洗伤口来预先抑制疼痛，同时避免因口服、肌肉注射、皮下注射或静脉注射较大剂量的制剂而产生的不良副作用。
• Arthroscopic irrigation solution and method for peripheral vasoconstriction and inhibition of pain and inflammation
  申请人：Omeros Corporation

  公开号：US20030087962A1

  公开（公告）日：2003-05-08

  A method and solution for perioperatively inhibiting a variety of pain and inflammation processes during arthroscopic procedures. The solution preferably includes a vasoconstrictor that demonstrates substantial agonist activity at alpha adrenergic receptors and that is selected for peripheral (local) vasoconstriction and one or more additional pain and inflammation inhibitory agents at dilute concentration in a physiologic carrier, such as saline or lactated Ringer's solution. The solution is applied by continuous irrigation of a wound during a surgical procedure for peripheral vasoconstriction and inhibition of pain and/or inflammation while avoiding undesirable side effects associated with systemic application of larger doses of the agents.

  一种在关节镜手术过程中围术期抑制各种疼痛和炎症过程的方法和溶液。该溶液最好包括一种在α-肾上腺素能受体上显示出大量激动活性的血管收缩剂，该收缩剂被选作外周（局部）血管收缩剂，以及一种或多种在生理载体（如生理盐水或乳酸林格氏液）中稀释的疼痛和炎症抑制剂。在手术过程中，可通过持续灌注伤口来使用该溶液，以收缩外周血管，抑制疼痛和/或炎症，同时避免因全身使用较大剂量的药剂而产生的不良副作用。