5,6-dihydro-N,N-dipropyl-4H-imidazo<4,5,1-ij>quinolin-5-amine | 132895-55-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 5,6-dihydro-N,N-dipropyl-4H-imidazo<4,5,1-ij>quinolin-5-amine
• 英文别名: 5,6-Dihydro-N,N-dipropyl-4H-imidazo(4,5,1-ij)quinolin-5-amine；N,N-dipropyl-1,3-diazatricyclo[6.3.1.04,12]dodeca-2,4,6,8(12)-tetraen-10-amine
• CAS: 132895-55-7
• 化学式: C₁₆H₂₃N₃
• 分子量: 257.379
• InChiKey: XOWDSADVJRDFTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  21.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  7 - 甲基-1H -苯并[D]咪唑 在 N-溴代丁二酰亚胺(NBS) 、 lithium aluminium tetrahydride 、 过氧化氢苯甲酰 、 四溴化碳 、 sodium ethanolate 、 potassium hydride 、 三苯基膦 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 四氯化碳 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 20.83h， 生成 5,6-dihydro-N,N-dipropyl-4H-imidazo<4,5,1-ij>quinolin-5-amine
  参考文献：
  名称：

  Dopaminergic and serotonergic activities of imidazoquinolinones and related compounds

  摘要：

  The synthesis of 5-(dipropylamino)-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one (5), a potent dopamine D2 agonist showing high dopamine/serotonin (5HT1A) selectivity, is described. Dopaminergic activity is associated with the (R)-enantiomer of 5; the (S)-enantiomer shows no dopaminergic activity. A series of analogues where the imidazolone ring was modified to various 5- or 6-membered heterocyclic rings were prepared. Some of these compounds showed a combination of dopaminergic and serotonergic activity, while one compound, 6-(dipropylamino)-1,2,6,7-tetrahydro-3H,5H-pyrido[3,2,1-ij]quinazolin-3-one (24), was a selective serotonergic agonist. Various analogues of 5 where the dipropylamine substituent was modified were prepared. Most of these showed reduced dopaminergic activity, while several were as potent as 5 at the serotonin 5HT1A receptor. Orientations for the new compounds at dopamine and serotonin receptors are proposed and compared with those of other tricyclic ligands known to have high affinity at these receptors.

  DOI：

  10.1021/jm00084a013

文献信息

• Heterocyclic amines having central nervous system activity
  申请人：The Upjohn Company

  公开号：US05273975A1

  公开（公告）日：1993-12-28

  Tricyclic nitrogen containing compounds, having central nervous system activity of the following structural formula: ##STR1## and pharmaceutically acceptable salts thereof wherein R.sub.1, R.sub.2, and R.sub.3 are independently hydrogen, C.sub.1-6 alkyl, alkenyl, or alkynyl, C.sub.3-10 cycloalkyl, or R.sub.1 and R.sub.2 are joined to form a C.sub.3-7 cyclic amine which can contain additional heteroatoms; X is hydrogen, C.sub.1-6 alkyl halogen, hydroxy, alkoxy, cyano, carboxamide, carboxyl, or carboalkoxyl; A is SO.sub.2, N, CH, CH.sub.2, CHCH.sub.3, C.dbd.O, C.dbd.S, C-SCH.sub.3, C.dbd.NH, C-NH.sub.2, C-NHCH.sub.3, C--NHCOOCH.sub.3, or C--NHCN. B is CH.sub.2, CH, C.dbd.O, N, NH or N--CH.sub.3 ; n is 0 or 1; and D is CH, CH.sub.2, C.dbd.O, O, N, NH or N--CH.sub.3. These new compounds are suitable for treating schizophrenia, Parkinson's disease, anxiety, depression or as compounds for lowering blood pressure in animal or human hosts.

  三环氮含化合物，具有以下结构式的中枢神经系统活性：##STR1##及其药学上可接受的盐，其中R.sub.1、R.sub.2和R.sub.3独立地是氢、C.sub.1-6烷基、烯基或炔基、C.sub.3-10环烷基，或R.sub.1和R.sub.2连接形成可含有额外杂原子的C.sub.3-7环胺；X是氢、C.sub.1-6烷基卤素、羟基、烷氧基、氰基、羧酰胺、羧基或羧烷氧基；A是SO.sub.2、N、CH、CH.sub.2、CHCH.sub.3、C.dbd.O、C.dbd.S、C-SCH.sub.3、C.dbd.NH、C-NH.sub.2、C-NHCH.sub.3、C--NHCOOCH.sub.3或C--NHCN。B是CH.sub.2、CH、C.dbd.O、N、NH或N--CH.sub.3；n为0或1；D是CH、CH.sub.2、C.dbd.O、O、N、NH或N--CH.sub.3。这些新化合物适用于治疗精神分裂症、帕金森病、焦虑、抑郁或作为降低动物或人类宿主血压的化合物。
• Combination of dopamine agonists and monoamine reuptake inhibitors
  申请人：Glue Paul

  公开号：US20050250803A1

  公开（公告）日：2005-11-10

  This invention is directed to pharmaceutical compositions and kits comprising (i) a dopamine agonist of the formula II as described in the specification, (ii) a monoamine reuptake inhibitor or pharmaceutically acceptable salt thereof; and optionally (iii) a pharmaceutically acceptable carrier. This invention further relates to methods of treatment using those pharmaceutical compositions. Disorders or conditions that may be treated by the compositions, kits and methods of the invention include hypertension, depression, generalized anxiety disorder, phobias, posttraumatic stress syndrome, avoidant personality disorder, premature ejaculation, eating disorders, obesity, chemical dependencies, cluster headache, pain, Alzheimer's disease, obsessive-compulsive disorder, panic disorder, memory disorders, Parkinson's diseases, endocrine disorders, vasospasm, cerebellar ataxia, gastrointestinal tract disorders, negative symptoms of schizophrenia, premenstrual syndrome, Fibromyalgia Syndrome, stress incontinence, Tourette syndrome, trichotillomania, kleptomania, male impotence, cancer, chronic paroxysmal hemicrania, headache and a combination thereof in a mammal such as a human.

  本发明涉及药物组合物和试剂盒，其中包含(i) 如说明书所述的式 II 多巴胺激动剂，(ii) 单胺再摄取抑制剂或其药学上可接受的盐；以及(iii) 可选的药学上可接受的载体。本发明进一步涉及使用这些药物组合物的治疗方法。本发明的组合物、试剂盒和方法可治疗的疾病或病症包括高血压、抑郁症、广泛性焦虑症、恐惧症、创伤后应激综合征、回避型人格障碍、早泄、进食障碍、肥胖症、化学依赖性、丛集性头痛、疼痛、阿尔茨海默病、强迫症、恐慌症、记忆障碍、帕金森病、胰岛素依赖性疾病、泌尿系统疾病、胰岛素依赖性疾病、记忆障碍、帕金森氏症、内分泌失调、血管痉挛、小脑共济失调、胃肠道疾病、精神分裂症的阴性症状、经前综合征、纤维肌痛综合征、压力性尿失禁、抽动秽语综合征、嗜毛癖、嗜盗癖、男性阳痿、癌症、慢性阵发性颅内出血、头痛以及哺乳动物（如人类）的上述综合症状。
• HETEROCYCLIC AMINES HAVING CENTRAL NERVOUS SYSTEM ACTIVITY
  申请人：THE UPJOHN COMPANY

  公开号：EP0480939B1

  公开（公告）日：1995-01-25
• US5273975A
  申请人：——

  公开号：US5273975A

  公开（公告）日：1993-12-28
• US5436240A
  申请人：——

  公开号：US5436240A

  公开（公告）日：1995-07-25