2H-咪唑-2-酮,1-(4-氯苯基)-1,5-二氢-4-(1-哌啶基)- | 188116-08-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2H-咪唑-2-酮,1-(4-氯苯基)-1,5-二氢-4-(1-哌啶基)-
• 英文名称: ELB 139
• 英文别名: 1-(4-chlorophenyl)-4-piperidinoimidazolin-2-one；1-(4-chlorophenyl)-4-(piperidin-1-yl)-1H-imidazol-2(5H)-one；3-(4-chlorophenyl)-5-piperidin-1-yl-4H-imidazol-2-one
• CAS: 188116-08-7
• 化学式: C₁₄H₁₆ClN₃O
• 分子量: 277.754
• InChiKey: YGXIELIREXEJQN-UHFFFAOYSA-N

物化性质

• 熔点：
  242 °C(Solv: ethanol (64-17-5))
• 沸点：
  405.2±47.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  35.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-(4-氯苯基)-咪唑啉-2,4-二酮 、 哌啶盐酸盐 以65%的产率得到2H-咪唑-2-酮,1-(4-氯苯基)-1,5-二氢-4-(1-哌啶基)-
  参考文献：
  名称：

  Synthesis, Pharmacology, and Structure−Activity Relationships of Novel Imidazolones and Pyrrolones as Modulators of GABA_A Receptors

  摘要：

  New series of imidazolones and pyrrolones were synthesized. The compounds were tested regarding their anxiolytic properties due to modulation of the GABA(A) receptor response. Several derivatives exhibit considerable pharmacological activity while lacking the typical side effects of benzodiazepine receptor agonists. 1-(4-chlorophenyl)-4-morpholin-1-yl-1,5-dihydro-imidazol-2-one (2) and 1-(4-chlorophenyl)-4-piperidin-1-yl-1,5-dihydro-imidazol-2-one (3) were protective in the pentylenetetrazole test in rats with oral ED50 of 27.4 and 12.8 mg/kg and TD50 (rotarod) of > 500 and 265 mg/kg, respectively. The minimum effective dose in the Vogel conflict test was 3 mg/kg for both compounds. Common structure-activity relationship and comparative molecular field analysis models of the various series of derivatives could be established which are in accordance with a GABAA mediated pharmacological action. The findings fit well into an established pharmacophore model. This model is refined by an additional steric restriction feature.

  DOI：

  10.1021/jm0509400

文献信息

• Anticonvulsive 1-ar(alk)ylimidazolin-2-ones and process for making
  申请人：Arzneitmittelwerk Dresden G.m.b.H.

  公开号：US05869481A1

  公开（公告）日：1999-02-09

  Compounds having anticonsulive activity, of the formula 1 ##STR1## in which X is hydrogen, a C.sub.1-4 -alkyl, C.sub.1-4 alkoxy, trifluoromethyl, or halogen residue, R.sup.1 and R.sup.2 are independently of each other C.sub.1-4 -alkyl, C.sub.2-4 hydroxyalkyl, cycloalkyl or heteroalkyl, or R.sup.1 and R.sup.2 are together a C.sub.2-6 alkylene reside in which a--CH.sub.2 --group is optionally replaced by oxygen, nitrogen or sulfur, m is 0 or 1, and n is 0 or a cardinal number from 1 to 5, and their pharmaceutically acceptable salts. The application also relates to a process for making the compound of formula (I).

  具有抗惊厥活性的化合物，其化学式为1 ##STR1## 其中X是氢，C.sub.1-4 -烷基，C.sub.1-4 -烷氧基，三氟甲基或卤素残基，R.sup.1和R.sup.2分别是C.sub.1-4 -烷基，C.sub.2-4 -羟基烷基，环烷基或杂环烷基，或R.sup.1和R.sup.2共同构成一个C.sub.2-6烷基残基，其中a-CH.sub.2-基团可选地被氧，氮或硫取代，m为0或1，n为0或1至5的基数，以及它们的药物可接受的盐。该申请还涉及制备化合物(I)的方法。
• [DE] NEUE, ANTIKONVULSIV WIRKENDE 1-AR(ALK)YL-IMIDAZOLIN-2-ONE, DIE IN 4-STELLUNG EINEN DISUBSTITUIERTEN AMIN-REST ENTHALTEN, UND VERFAHREN ZU DEREN HERSTELLUNG<br/>[EN] NOVEL 1-AR(ALK)YL-IMIDAZOLIN-2-ONES CONTAINING A DISUBSTITUTED AMINE RADICAL IN THE 4TH POSITION, HAVING AN ANTI-CONVULSIVE EFFECT, AND PROCESS FOR THEIR PRODUCTION<br/>[FR] NOUVELLES 1-AR(ALK)YL-IMIDAZOLIN-2-ONES A EFFET ANTICONVULSIF CONTENANT UN RESTE AMINE BISUBSTITUE EN POSITION 4 ET PROCEDE PERMETTANT DE LES PREPARER
  申请人：ARZNEIMITTELWERK DRESDEN GMBH

  公开号：WO1997009314A1

  公开（公告）日：1997-03-13

  (DE) Antikonvulsiv wirkende Verbindungen der allgemeinen Formel (1), worin X = Wasserstoff, C1-C4-Alkyl, C1-C4-Alkoxy, Trifluormethyl, Halogen, R1 bzw. R2 = C1-C4-Alkyl, Cycloalkyl, Heteroalkyl bedeuten.(EN) Compounds with an anti-convulsive effect of general formula (1) in which X = hydrogen, C1-C4 alkyl, C1-C4 alkoxy, trifluoromethyl, halogen and R1 or R2 = C1-C4 alkyl, cycloalkyl or heteroalkyl.(FR) L'invention concerne des composés à effet anticonvulsif de la formule générale (1) dans laquelle X désigne hydrogène, alkyle C1-C4, alcoxy C1-C4, trifluorométhyle, halogène, R1 et respectivement R2 désignent alkyle C1-C4, cycloalkyle, hétéroalkyle.

  (中文) 通式（1）的抗癫痫化合物，其中X = 氢，C1-C4烷基，C1-C4烷氧基，三氟甲基，卤素，R1或R2 = C1-C4烷基，环烷基或杂环烷基。
• Method of treating or preventing central nervous system disorders with compounds having selectivity benzodiazepine receptor
  申请人：Boehringer Ingelheim Vetmedica GmbH

  公开号：EP2027856A1

  公开（公告）日：2009-02-25

  The present invention relates to the use of 1-ar(alk)ylimidazolin-2-ones which contain a disubstituted amine radical in the 4-position for the treatment or prevention of central nervous system disorders including depression, anxiety, movement disorders, and especially dystonia, and psychotic disorders, and especially schizophrenia and psychotic symptoms associated to other mental disorders.

  本发明涉及在 4 位含有二取代胺基的 1-芳基咪唑啉-2-酮用于治疗或预防中枢神经系统疾病，包括抑郁症、焦虑症、运动障碍，尤其是肌张力障碍，以及精神障碍，尤其是精神分裂症和与其他精神障碍相关的精神症状。
• Ganaxolone for use in treatment of status epilepticus
  申请人：Marinus Pharmaceuticals, Inc.

  公开号：US11110100B2

  公开（公告）日：2021-09-07

  This invention relates to methods for treating status epilepticus by administering to the subject in need thereof an intravenous bolus of ganaxolone and a continuous intravenous infusion of a neurosteroid. The method provides SE suppression and continued suppression of SE.

  本发明涉及治疗癫痫状态的方法，其方法是向有需要的受试者静脉注射甘露醇酮和持续静脉注射神经类固醇。该方法可抑制癫痫状态并持续抑制癫痫状态。
• Method of treating or preventing central nervous system disorders with compounds having selectivity for the alpha 3 subunit of the benzodiazepine receptor
  申请人：Langen Barbara

  公开号：US20050032863A1

  公开（公告）日：2005-02-10

  The present invention relates to the use of 1-ar(alk)ylimidazolin-2-ones which contain a disubstituted amine radical in the 4-position for the treatment or prevention of central nervous system disorders including depression, anxiety, movement disorders, and especially dystonia, and psychotic disorders, and especially schizophrenia and psychotic symptoms associated to other mental disorders.

  本发明涉及在 4 位含有二取代胺基的 1-芳基咪唑啉-2-酮用于治疗或预防中枢神经系统疾病，包括抑郁症、焦虑症、运动障碍，尤其是肌张力障碍，以及精神障碍，尤其是精神分裂症和与其他精神障碍相关的精神症状。