2-丙氧基烟酸 | 68359-09-1

• 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: 2-丙氧基烟酸
• 英文名称: 2-propoxy nicotinic acid
• 英文别名: 2-propoxynicotinic acid；propoxynicotinic acid；2-n-Propoxypyridine-3-carboxylic Acid；2-propoxy-nicotinic acid；2-propoxypyridine-3-carboxylic acid
• CAS: 68359-09-1
• 化学式: C₉H₁₁NO₃
• 分子量: 181.191
• InChiKey: UETCSFANSYKLNJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  59.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-丙氧基烟酸 在 吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 potassium fluoride 、 N-碘代丁二酰亚胺 、 copper(l) iodide 、 草酰氯 、 3-甲基-3-戊醇 、 硫酸 、 双(三甲基硅烷基)氨基钾 、 mercury(II) sulfate 、 N,N-二甲基甲酰胺 、 三氟乙酸 、 三氟乙酸酐 作用下， 以 二氯甲烷 、 水 、 三乙胺 、 N,N-二甲基甲酰胺 、 丙酮 、 乙腈 为溶剂， 反应 152.0h， 生成 5-(2-butoxy-5-acetylpyridin-3-yl)-3-ethyl-2-(pyridin-2-ylmethyl)-2H,6H,7H-pyrazolo[4,3-d]pyrimidin-7-one
  参考文献：
  名称：

  A Novel Series of Potent and Selective PDE5 Inhibitors with Potential for High and Dose-Independent Oral Bioavailability

  摘要：

  Sildenafil ( 5-[ 2-ethoxy-5-(4-methyl-1-piperazinylsulfonyl) phenyl]-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[ 4,3-d] pyrimidin-7-one), a potent and selective phosphodiesterase type 5 ( PDE5) inhibitor, provided the first oral treatment for male erectile dysfunction. The objective of the work reported in this paper was to combine high levels of PDE5 potency and selectivity with high and dose-independent oral bioavailability, to minimize the impact on the C-max of any interactions with coadministered drugs in the clinic. This goal was achieved through identification of a lower clearance series with a high absorption profile, by replacing the 5'-piperazine sulfonamide in the sildenafil template with a 5'-methyl ketone. This novel series provided compounds with low metabolism in human hepatocytes, excellent caco-2 flux, and the potential for good aqueous solubility. The in vivo oral and iv pharmacokinetic profiles of example compounds confirmed the high oral bioavailability predicted from these in vitro screens. 5-( 5-Acetyl-2-butoxy-3-pyridinyl)-3-ethyl-2-( 1-ethyl-3-azetidinyl)-2,6-dihydro-7H-pyrazolo[ 4,3-d] pyrimidin-7-one ( 2) was selected for progression into the clinic.

  DOI：

  10.1021/jm060113e
• 作为产物：
  描述：

  丙醇 、 2-氯烟酸 在 sodium 作用下， 以 丙醇 为溶剂， 反应 8.0h， 生成 2-丙氧基烟酸
  参考文献：
  名称：

  Process for the preparation of pyrazolo[4,3-d]pyrimidin-7-ones and intermediates thereof

  摘要：

  提供一种用于制备式（I）化合物的方法，包括在-OR3和氢氧化物捕获剂的存在下，反应式（II）、（III）、（IV）或（V）化合物，或者在辅助碱和氢氧化物捕获剂的存在下反应式（IV）化合物（即-OR3被辅助碱取代），其中X是离去基团，R1至R4如所定义。

  公开号：

  EP1176147A1

文献信息

• [EN] DISUBSTITUTED OCTAHY-DROPYRROLO [3,4-C] PYRROLES AS OREXIN RECEPTOR MODULATORS<br/>[FR] OCTAHYDROPYRROLO [3,4-C] PYRROLES DISUBSTITUÉS UTILISÉS COMME MODULATEURS DU RÉCEPTEUR DE L'OREXINE
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2012145581A1

  公开（公告）日：2012-10-26

  Disubstituted octahydropyrrolo[3,4-c]pyrrole compounds are described, which are useful as orexin receptor modulators. Such compounds may be useful in pharmaceutical compositions and methods for the treatment of diseased states, disorders, and conditions mediated by orexin activity, such as insomnia.

  描述了二取代的八氢吡咯[3,4-c]吡咯化合物，这些化合物可用作促进睡眠素受体的调节剂。这些化合物可能在药物组合物和治疗由促进睡眠素活性介导的疾病状态、紊乱和病况的方法中有用，比如失眠。
• [EN] DISUBSTITUTED OCTAHY - DROPYRROLO [3,4-C] PYRROLES AS OREXIN RECEPTOR MODULATORS<br/>[FR] OCTAHYDROPYRROLO[3,4-C]PYRROLES DISUBSTITUÉS EN TANT QUE MODULATEURS DE RÉCEPTEUR D'OREXINE
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2011050198A1

  公开（公告）日：2011-04-28

  Disubstituted octahydropyrrolo[3,4-c]pyrrole compounds are described, which are useful as orexin receptor modulators. Such compounds may be useful in pharmaceutical compositions and methods for the treatment of diseased states, disorders, and conditions mediated by orexin activity, such as insomnia.

  描述了二取代的八氢吡咯并[3,4-c]吡咯化合物，这些化合物可用作促进睡眠素受体的调节剂。这些化合物可能在药物组合物和治疗由促进睡眠素活性介导的疾病状态、紊乱和症状的方法中有用，比如失眠。
• Treatments for female sexual dysfunction and methods for identifying compounds useful for treating female sexual dysfunction
  申请人：——

  公开号：US20030083228A1

  公开（公告）日：2003-05-01

  The present invention provides a method of treating female sexual dysfunction, the method comprising the step of administering to a patent, having or at risk of having one or more of the disorders or conditions associated with female sexual dysfunction, a therapeutically effective amount of a compound that attenuates the binding of agouti-related protein to melanocortin receptors, but does not attenuate the binding of &agr;-melanocyte stimulating hormone to melanocortin receptors. The present invention also provides a method of identifying a compound that is useful for the treatment or prevention of female sexual dysfunction, the method comprising the steps of: 1) determining if a compound affects the binding of agouti-related protein to melanocortin receptors; 2) determining if a compound affects the binding of &agr;-melanocyte stimulating hormone to melanocortin receptors; and 3) selecting a compound that attenuates the binding of agouti-related protein to melanocortin receptors, but does not affect the binding of &agr;-melanocyte stimulating hormone to melanocortin receptors.

  本发明提供了一种治疗女性性功能障碍的方法，该方法包括向患有或有可能患有与女性性功能障碍相关的一种或多种疾病或病况的患者施用一种治疗有效量的化合物，该化合物减弱了agouti相关蛋白与黑素皮质素受体的结合，但不影响α-黑素细胞刺激激素与黑素皮质素受体的结合。本发明还提供了一种识别对治疗或预防女性性功能障碍有用的化合物的方法，该方法包括以下步骤：1）确定化合物是否影响agouti相关蛋白与黑素皮质素受体的结合；2）确定化合物是否影响α-黑素细胞刺激激素与黑素皮质素受体的结合；以及3）选择一种减弱agouti相关蛋白与黑素皮质素受体结合的化合物，但不影响α-黑素细胞刺激激素与黑素皮质素受体的结合。
• Methods of treatment and kits comprising a growth hormone secretagogue
  申请人：——

  公开号：US20030105114A1

  公开（公告）日：2003-06-05

  The present invention relates to methods of treating bulimia nervosa, male erectile dysfunction, female sexual dysfunction, thyroid cancer, breast cancer, or ameliorating ischemic nerve or muscle damage. The present invention also relates to kits that can be used in the treatment of bulimia nervosa, male erectile dysfunction, female sexual dysfunction, thyroid cancer, breast cancer, or ameliorating ischemic nerve or muscle damage. The present invention further relates to increasing gastrointestinal motility after surgery and increasing gastrointestinal motility in patients who have been administered an agent that decreases gastrointestinal motility.

  本发明涉及治疗厌食症、男性勃起功能障碍、女性性功能障碍、甲状腺癌、乳腺癌或改善缺血性神经或肌肉损伤的方法。本发明还涉及可用于治疗厌食症、男性勃起功能障碍、女性性功能障碍、甲状腺癌、乳腺癌或改善缺血性神经或肌肉损伤的试剂盒。本发明还涉及术后增加胃肠道蠕动和在接受降低胃肠道蠕动试剂的患者中增加胃肠道蠕动。
• Treatment of neuropathy
  申请人：——

  公开号：US20030162782A1

  公开（公告）日：2003-08-28

  This invention relates to the use of cyclic guanosine 3′,5′-monophosphate phosphodiesterase type five (cGMP PDE5) inhibitors, including in particular the compound sildenafil, for the treatment of neuropathy, including in particular the treatment of diabetic neuropathy.

  这项发明涉及使用环鸟苷3′,5′-单磷酸磷酸二酯酶五型（cGMP PDE5）抑制剂，特别是包括化合物西地那非，用于治疗神经病变，特别是治疗糖尿病神经病变。