quinpirole | 74196-93-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: quinpirole
• 英文别名: 2H-Pyrazolo(3,4-g)quinoline, 4,4a,5,6,7,8,8a,9-octahydro-5-propyl-, (4aR,8aR)-rel-；(4aS,8aS)-5-propyl-1,4,4a,6,7,8,8a,9-octahydropyrazolo[3,4-g]quinoline
• CAS: 74196-93-3；99745-18-3；112137-15-2
• 化学式: C₁₃H₂₁N₃
• 分子量: 219.33
• InChiKey: FTSUPYGMFAPCFZ-GWCFXTLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  31.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  quinpirole 生成 trans-(+)-(4aS)-4,4a,5,6,7,8,8a,9-octahydro-5-propyl-1H-pyrazolo<3,4-g>quinoline L-(+)-tartrate
  参考文献：
  名称：

  Resolution and absolute configuration of an ergoline-related dopamine agonist, trans-4,4a,5,6,7,8,8a,9-octahydro-5-propyl-1H(or 2H)-pyrazolo[3,4-g]quinoline

  摘要：

  The title compound (+/-)-5 (R = Pro) (LY141865) has been resolved into a (-) isomer and a (+) isomer as the D- and L-tartrate salts, respectively. Biological studies have shown that dopamine agonist activity is a property of only the (-) isomer. Crystallographic analysis has proven that the absolute configuration of the active (-) isomer is the same as that of the natural ergolines.

  DOI：

  10.1021/jm00362a005
• 作为产物：
  描述：

  4-(苄氧基)环已酮 在 盐酸 、 lithium aluminium tetrahydride 、 pyridine hydrochloride chromate 、 sodium cyanoborohydride 、 一水合肼 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 89.75h， 生成 quinpirole
  参考文献：
  名称：

  双环和三环麦角灵的部分结构。刚性的3-（2-氨基乙基）吡咯以及3-和4-（2-氨基乙基）吡唑是多巴胺激动剂。

  摘要：

  根据与阿扑吗啡的比较，提出麦角灵的刚性吡咯乙胺部分是负责多巴胺激动剂活性的分子部分。为了支持该假设，已经合成了双环和三环麦角灵部分结构6、11、25和35。另外，已经制备了这些刚性吡咯乙乙胺的一些吡唑等排体（37、38、40和45）。所有这些类别在催乳激素抑制和病变大鼠转弯试验中均显示出多巴胺能活性。最有效的药物是线性三环吡唑38（R = Pr）和40（R = Pr），其功效与高活性麦角灵高培高利特相当（41）。

  DOI：

  10.1021/jm00179a003

文献信息

• Octahydro pyrazolo (3,4-g)quinolines, process for their preparation and pharmaceutical compositions containing them
  申请人：ELI LILLY AND COMPANY

  公开号：EP0013787A1

  公开（公告）日：1980-08-06

  Octahydropyrazolo [3,4-g] quinolines of the general formula: wherein R is (C1-3)alkyl or allyl; R1 is H or CH2X wherein X is OCH3, SCH3, CN, SO2CH3 or CONH2; and pharmaceutically-acceptable acid addition salts thereof. These compounds, dopamine agonists, useful in treatment of Parkinsonism and in inhibiting secretion of prolactin, are prepared by reacting a corresponding 7-dimethylaminomethylene-6-oxo-derivative with hydrazine hydrate.

  通式为八氢吡唑并[3,4-g]喹啉： 其中 R 是（C1-3）烷基或烯丙基； R1 是 H 或 CH2X，其中 X 是 OCH3、SCH3、CN、SO2CH3 或 CONH2；以及 其药学上可接受的酸加成盐。 这些化合物是多巴胺激动剂，可用于治疗帕金森病和抑制催乳素分泌，其制备方法是将相应的 7-二甲氨基亚甲基-6-氧代衍生物与水合肼反应。
• Therapeutic treatment for the metabolic syndrome and type 2 diabetes
  申请人：——

  公开号：US20040077679A1

  公开（公告）日：2004-04-22

  The present invention is directed to a method for treating the metabolic syndrome or Type 2 diabetes, comprising the step of administering to a subject in need of such treatment a pharmaceutical composition comprising (1) at least one compound that stimulates an increase in central dopaminergic neuronal activity level in the subject, and (2) at least one compound that stimulates a decrease in central noradrenergic neuronal activity level in the subject. The present invention is also directed to a method for treating the metabolic syndrome or Type 2 diabetes, comprising the step of administering to a subject in need of such treatment at least one compound that simultaneously stimulates (1) an increase in central dopaminergic neuronal activity level, and (2) a decrease in central noradrenergic neuronal activity level. The present invention is also directed to pharmaceutical compositions that include the above compounds and a pharmaceutically acceptable carrier.

  本发明涉及一种治疗代谢综合征或2型糖尿病的方法，包括向需要这种治疗的受试者施用药物组合物的步骤，该药物组合物包含(1)至少一种刺激受试者中枢多巴胺能神经元活性水平增加的化合物，和(2)至少一种刺激受试者中枢去甲肾上腺素能神经元活性水平降低的化合物。本发明还涉及一种治疗代谢综合征或 2 型糖尿病的方法，该方法包括以下步骤：向需要治疗的受试者施用至少一种化合物，该化合物可同时刺激(1)中枢多巴胺能神经元活性水平的升高和(2)中枢去甲肾上腺素能神经元活性水平的降低。本发明还涉及包括上述化合物和药学上可接受的载体的药物组合物。
• Methods of treating metabolic syndrome using dopamine receptor agonists
  申请人：——

  公开号：US20040220190A1

  公开（公告）日：2004-11-04

  The present invention is directed to a method of simultaneously treating hypertension, hypertriglyceridemia, a pro-inflammatory state, and insulin resistance (with or without treating obesity), associated with Metabolic Syndrome, comprising the step of administering to a patient suffering from Metabolic Syndrome a therapeutically effective amount of a central acting dopamine agonist. In one embodiment, the central acting dopamine agonist is bromocriptine, optionally combined with a pharmaceutically acceptable carrier.

  本发明涉及一种同时治疗与代谢综合征有关的高血压、高甘油三酯血症、促炎症状态和胰岛素抵抗（治疗或不治疗肥胖）的方法，包括向代谢综合征患者施用治疗有效量的中枢作用多巴胺激动剂。在一个实施方案中，中枢作用多巴胺激动剂是溴隐亭，可选择与药学上可接受的载体结合使用。
• Therapeutic treatment for the metabolic syndrome, type2 diabetes, obesity, or prediabetes
  申请人：Cincotta H. Anthony

  公开号：US20050054734A1

  公开（公告）日：2005-03-10

  The present invention is directed to a method for treating a patient suffering from the metabolic syndrome, Type 2 diabetes, obesity, or prediabetes, comprising the step of increasing the ratio of dopaminergic neuronal to noradrenergic neuronal activity within the hypothalamus of the central nervous system of the patient. In another aspect, the present invention is directed to a method for treating a patient suffering from the metabolic syndrome, Type 2 diabetes, obesity, or prediabetes, comprising the step of: administering to a patient suffering from the metabolic syndrome, Type 2 diabetes, obesity, or prediabetes a pharmaceutical composition comprising (1) at least one compound that stimulates an increase in central dopaminergic neuronal activity level in the subject, and (2) at least one compound that stimulates a decrease in central noradrenergic neuronal activity level in the subject. The present invention is also directed to pharmaceutical compositions that include the above compounds and a pharmaceutically acceptable carrier.

  本发明涉及一种治疗代谢综合征、2型糖尿病、肥胖或糖尿病前期患者的方法，包括增加患者中枢神经系统下丘脑内多巴胺能神经元与去甲肾上腺素能神经元活性的比率。在另一方面，本发明涉及一种治疗患有代谢综合征、2 型糖尿病、肥胖症或糖尿病前期的患者的方法，包括以下步骤：给患有代谢综合征、2 型糖尿病、肥胖症或糖尿病前期的患者施用药物组合物，该药物组合物包含(1)至少一种刺激受试者中枢多巴胺能神经元活性水平增加的化合物，和(2)至少一种刺激受试者中枢去甲肾上腺素能神经元活性水平降低的化合物。本发明还涉及包括上述化合物和药学上可接受的载体的药物组合物。
• EP1539153A4
  申请人：——

  公开号：EP1539153A4

  公开（公告）日：2007-11-07