(-)-2-[(1-{[(5-ethyl-1,3,4-thiadiazol-2-yl)amino]carbonyl}cyclopentyl)methyl]pentanoic acid | 337962-93-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (-)-2-[(1-{[(5-ethyl-1,3,4-thiadiazol-2-yl)amino]carbonyl}cyclopentyl)methyl]pentanoic acid
• 英文别名: (+)-2-[(1-{[(5-ethyl-1,3,4-thiadiazol-2-yl)amino]carbonyl}cyclopentyl)methyl]pentanoic acid；2-[[1-[(5-ethyl-1,3,4-thiadiazol-2-yl)carbamoyl]cyclopentyl]methyl]pentanoic Acid
• CAS: 337962-93-3
• 化学式: C₁₆H₂₅N₃O₃S
• 分子量: 339.459
• InChiKey: FWXXCSISWQQOGS-UHFFFAOYSA-N

物化性质

• 密度：
  1.243±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  120
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (-)-2-[(1-{[(5-ethyl-1,3,4-thiadiazol-2-yl)amino]carbonyl}cyclopentyl)methyl]pentanoic acid 以400 mg的产率得到(2S)-2-[(1-{[(5-ethyl-1,3,4-thiadiazol-2-yl)amino]carbonyl}cyclopentyl)-methyl]pentanoic acid
  参考文献：
  名称：

  Novel Selective Inhibitors of Neutral Endopeptidase for the Treatment of Female Sexual Arousal Disorder. Synthesis and Activity of Functionalized Glutaramides

  摘要：

  Female sexual arousal disorder (FSAD) is a highly prevalent sexual disorder affecting up to 40% of women. We describe herein our efforts to identify a selective neutral endopeptidase (NEP) inhibitor as a potential treatment for FSAD. The rationale for this approach, together with a description of the medicinal chemistry strategy, lead compounds, and SAR investigations are detailed. In particular, the strategy of starting with the clinically precedented selective NEP inhibitor, Candoxatrilat, and targeting low molecular weight and relatively polar mono-carboxylic acids is described. This led ultimately to the prototype development candidate R-13, for which detailed pharmacology and pharmacokinetic parameters are presented.(1)

  DOI：

  10.1021/jm060133g
• 作为产物：
  描述：

  1-(2-tert-butoxycarbonyl-ethyl)cyclopentanecarboxylic acid 在 palladium on activated charcoal N-甲基吗啉 、 氢气 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三氟乙酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 为溶剂， -65.0~100.0 ℃ 、206.84 kPa 条件下， 反应 12.67h， 生成 (-)-2-[(1-{[(5-ethyl-1,3,4-thiadiazol-2-yl)amino]carbonyl}cyclopentyl)methyl]pentanoic acid
  参考文献：
  名称：

  Novel Selective Inhibitors of Neutral Endopeptidase for the Treatment of Female Sexual Arousal Disorder. Synthesis and Activity of Functionalized Glutaramides

  摘要：

  Female sexual arousal disorder (FSAD) is a highly prevalent sexual disorder affecting up to 40% of women. We describe herein our efforts to identify a selective neutral endopeptidase (NEP) inhibitor as a potential treatment for FSAD. The rationale for this approach, together with a description of the medicinal chemistry strategy, lead compounds, and SAR investigations are detailed. In particular, the strategy of starting with the clinically precedented selective NEP inhibitor, Candoxatrilat, and targeting low molecular weight and relatively polar mono-carboxylic acids is described. This led ultimately to the prototype development candidate R-13, for which detailed pharmacology and pharmacokinetic parameters are presented.(1)

  DOI：

  10.1021/jm060133g

文献信息

• Phosphodiesterase inhibitors for the treatment of female sexual dysfunction
  申请人：Pfizer Limited

  公开号：EP1097706A1

  公开（公告）日：2001-05-09

  A method of treating a female suffering from femal sexual dysfunction (FSD), in particular femal sexual arousal dysfunction (FSAD), is described. The method comprises delivering to the female an agent that is capable of potentiating cAMP in the sexual genitalia; wherein the agent is in an amount to cause potentiation of cAMP in the sexual genitalia of the female. The agent may be admixed with a pharmaceutically acceptable carrier, diluent or excipient. Said agent is a phosphodiesterase (PDE) inhibitor wherein said PDE is a cAMP hydrolysing PDE (and optionally cGMP hydroysing).

  描述了一种治疗女性性功能障碍（FSD），特别是女性性唤醒功能障碍（FSAD）的方法。该方法包括向女性提供一种能够增强性生殖器内环磷酸腺苷（cAMP）的药物；其中，该药物的量足以引起女性性生殖器内cAMP的增强。该药物可以与药用可接受的载体、稀释剂或赋形剂混合。所述药物是一种磷酸二酯酶（PDE）抑制剂，其中所述PDE是一种cAMP水解PDE（可选地为cGMP水解）。
• Treatment of male sexual dysfunction
  申请人：——

  公开号：US20020028799A1

  公开（公告）日：2002-03-07

  The present invention relates to the use of neutral endopeptidase inhibitors (NEPi) and a combination of NEPi and phosphodiesterase type 5 (PDE5) inhibitor for the treatment of male sexual dysfunction, in particular MED.

  本发明涉及使用中性内肽酶抑制剂（NEPi）和NEPi与磷酸二酯酶5型（PDE5）抑制剂的组合物治疗男性性功能障碍，特别是MED。
• [EN] CYCLOPENTYL-SUBSTITUTED GLUTARAMIDE DERIVATIVES AS INHIBITORS OF NEUTRAL ENDOPEPTIDASE<br/>[FR] DERIVES DE GLUTARAMIDE SUBSTITUES PAR DU CYCLOPENTYL UTILISES COMME INHIBITEURS DE L'ENDOPEPTIDASE NEUTRE
  申请人：PFIZER LTD

  公开号：WO2002002513A1

  公开（公告）日：2002-01-10

  The invention provides compounds of formula I wherein R1 is optionally substituted C¿1?-6alkyl, optionally substituted C3-7 cycloalkyl, optionally substituted aryl or optionally substituted heterocyclyl; n is 0, 1 or 2; and Y is -NR?18S(O)¿uR19 or a group shown below.

  该发明提供了公式I的化合物，其中R1是可选取代的C1-6烷基，可选取代的C3-7环烷基，可选取代的芳基或可选取代的杂环基；n为0，1或2；Y为-NR?18S(O)uR19或下图所示的基团。
• Treatment of sexual dysfunction
  申请人：——

  公开号：US20020169101A1

  公开（公告）日：2002-11-14

  Bombesin receptor antagonists have been found to be useful in the treatment of sexual dysfunction in both males and females. They may be selective BB1 antagonists or mixed BB1/BB2 antagonists. Combinations are disclosed of bombesin receptor antagonists with a range of other active compounds, for example PDE5 inhibitors, NEP inhibitors and lasofoxifene.

  Bombesin受体拮抗剂已被发现在男性和女性的性功能障碍治疗中非常有用。它们可以是选择性BB1拮抗剂或混合BB1 / BB2拮抗剂。揭示了与一系列其他活性化合物的Bombesin受体拮抗剂的组合，例如PDE5抑制剂，NEP抑制剂和lasofoxifene。
• Compounds for the treatment of female sexual dysfunction
  申请人：Pfizer Inc

  公开号：US20040254153A1

  公开（公告）日：2004-12-16

  A method of treating a female suffering from FSD, in particular FSAD, is described. The method comprises delivering to the female an agent that is capable of potentiating cAMP in the sexual genitalia; wherein the agent is in an amount to cause potentiation of cAMP in the sexual genitalia of the female. The agent may be admixed with a pharmaceutically acceptable carrier, diluent or excipient.

  本发明描述了一种治疗患有女性性功能障碍（FSD），特别是女性性唤起障碍（FSAD）的方法。该方法包括向女性输送一种能够在性生殖器中增强cAMP的药剂；其中该药剂的量足以在女性的性生殖器中引起cAMP的增强。该药剂可以与药学上可接受的载体、稀释剂或赋形剂混合。