6-amino-2-(3,4-methylendioxy-phenyl)-quinazoline | 1004997-77-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 6-amino-2-(3,4-methylendioxy-phenyl)-quinazoline
• 英文别名: 6-amino-2-(1,3-benzodioxol-5-yl)-quinazoline；6-Amino-2-(3,4-methylendioxy-phenyl)quinazoline；2-(1,3-benzodioxol-5-yl)quinazolin-6-amine
• CAS: 1004997-77-6
• 化学式: C₁₅H₁₁N₃O₂
• 分子量: 265.271
• InChiKey: QFXHEPBPCSBBEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  70.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-amino-2-(3,4-methylendioxy-phenyl)-quinazoline 、 聚合甲醛 在 氯化铵 、 sodium hydroxide 、 磷酸 作用下， 以 甲醇 、 水 为溶剂， 反应 19.0h， 以29%的产率得到[2-(1,3-benzodioxol-5-yl)-6-(1H-imidazol-1-yl)]quinazoline
  参考文献：
  名称：

  WO2008/14822

  摘要：

  公开号：
• 作为产物：
  描述：

  6-nitro-2-(1,3-benzodioxole-5-yl)-quinazoline 在 tin(ll) chloride 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以64%的产率得到6-amino-2-(3,4-methylendioxy-phenyl)-quinazoline
  参考文献：
  名称：

  WO2008/14815

  摘要：

  公开号：

文献信息

• [EN] 6-1H-IMIDAZO-QUINAZOLINE AND QUINOLINES DERIVATIVES, NEW MAO INHIBITORS AND IMIDAZOLINE RECEPTOR LIGANDS<br/>[FR] DÉRIVÉS DE 6-1H-IMIDAZO-QUINAZOLINE ET QUINOLÉINES, NOUVEAUX INHIBITEURS DE MAO ET LIGANDS DES RÉCEPTEURS D'IMIDAZOLINES
  申请人：ROTTAPHARM SPA

  公开号：WO2009152868A1

  公开（公告）日：2009-12-23

  The present invention is directed to 6-(1H-imidazo-1-yl)-2-aryl and 2-heteroaryl quinazoline and quinolines derivatives, compounds of formula (I), their pharmaceutical acceptable salts and solvates and corresponding pharmaceutical compositions, that acts as Monoamine Oxidase (MAO) inhibitors and Imidazoline Receptor ligands: wherein: X is independently selected from -CH group or a nitrogen atom (-N), W is independently selected from an aryl group, an heteroaryl group, or a benzocondensed heteroaryl group such as 1,3-benzodioxole, benzofuran, 2,3-dihydrobenzofuran, benzothiophene, 2,3-dihydrobenzothiophene, indole, 2,3-dihydroindole, benzimidazole, benzoxazole, benzothiazole, 2H-3,4-dihydrobenzopyran, [l,4]-benzodioxine, 2,3-dihydro-[1,4]-benzodioxine (1,4-benzodioxan). R1 is independently selected from hydrogen (-H), C1-C4alkyl, hydroxymethyl (-CH2OH), aminomethyl (-CH2NH2), alkylaminomethyl [CH2NH(R2)], or di-alkylaminomethyl [CH2N(R2)2], trifiuoromethyl (-CF3). Compounds of formula (I) elicited a pharmacological profile suitable for the clinical treatment of depression and related disorders, Parkinson disease, drug abuse, and morphine tolerance and dependence.

  本发明涉及6-(1H-咪唑-1-基)-2-芳基和2-杂芳基喹唑啉和喹啉衍生物，这些衍生物的化学式为(I)，以及它们的药用盐和溶剂化物以及相应的药物组合物，作为单胺氧化酶（MAO）抑制剂和咪唑啉受体配体：其中：X独立地选自-CH基团或氮原子(-N)，W独立地选自芳基团、杂芳基团或如1,3-苯并二氧杂环戊烷、苯并呋喃、2,3-二氢苯并呋喃、苯并噻吩、2,3-二氢苯并噻吩、吲哚、2,3-二氢吲哚、苯并咪唑、苯并噁唑、苯并噻唑、2H-3,4-二氢苯并吡喃、[1,4]-苯并二氧杂环戊烷、2,3-二氢-[1,4]-苯并二氧杂环戊烷(1,4-苯并二氧杂环戊烷)。R1独立地选自氢(-H)、C1-C4烷基、羟甲基(-CH2OH)、氨基甲基(-CH2NH2)、烷基氨甲基[CH2NH(R2)]或二烷基氨甲基[CH2N(R2)2]、三氟甲基(-CF3)。化学式(I)的化合物展现出适合于临床治疗抑郁症和相关障碍、帕金森病、药物滥用以及吗啡耐受性和依赖性的药理特性。
• AMIDINE DERIVATIVES OF 2-HETEROARYL-QUINAZOLINES AND QUINOLINES; POTENT ANALGESICS AND ANTI-INFLAMMATORY AGENTS
  申请人：Giordani Antonio

  公开号：US20090227609A1

  公开（公告）日：2009-09-10

  The present invention concerns novel amidines derivatives of 2-heteroaryl-quinazoline and quinolines of general formula (I), to a process for their preparation, to their pharmaceutical compositions and to the use of these compounds, salts and solvates thereof, along with the corresponding pharmaceutical compositions, for the treatment of pain and inflammatory disorders. Compounds of this invention are extremely potent analgesics, suitable for the treatment of both inflammatory and neuropathic pain. Particularly for the treatment of neuropathic pain the compounds of the invention have been proved largely superior to the standards currently in the clinical use. These compounds are not acting through inhibition of COX or NOS enzymes but are effective in inhibiting inflammatory cytokine production induced by inflammatory stimuli.

  本发明涉及2-杂环基喹唑啉和喹啉的新型酰胺衍生物，其通式为（I），以及它们的制备方法、制药组合物和这些化合物、盐和溶剂的用途，以及相应的制药组合物，用于治疗疼痛和炎症性疾病。本发明的化合物是极其有效的镇痛剂，适用于治疗炎症性和神经病理性疼痛。特别是对于神经病理性疼痛的治疗，本发明的化合物已被证明在临床使用中明显优于目前的标准。这些化合物不是通过抑制COX或NOS酶来发挥作用，而是通过抑制由炎症刺激引起的炎症细胞因子的产生而发挥作用。
• 6-1H-IMIDAZO-QUINAZOLINE AND QUINOLINES DERIVATIVES, NEW POTENT ANALGESICS AND ANTI-INFLAMMATORY AGENTS
  申请人：Giordani Antonio

  公开号：US20090264451A1

  公开（公告）日：2009-10-22

  The present invention is directed to novel 6-1H-imidazo-2-aryl and 2-heteroaryl quinazoline and quinoline of formula I, corresponding salts and solvates thereof, to a process for their preparation and to the use of this compounds and corresponding pharmaceutical composition for the treatment of pain and inflammatory related disorders. Compounds of the invention have been proven highly effective in the pharmacological treatment of both inflammatory and neuropathic pain, in addition to striking anti-inflammatory properties. Their effectiveness in interfering with COX-2 and inflammatory cytokines expressions and production, highlights them as interesting compounds also for the treatment of cancer in addition to several inflammatory diseases. Formula I:

  本发明涉及新的6-1H-咪唑-2-芳基和2-杂芳基喹噁啉和喹啉化合物（公式I），对应的盐和溶剂化物，以及它们的制备方法和该化合物及相应药物组合物在治疗疼痛和炎症相关疾病方面的应用。该发明的化合物在药理学治疗炎症和神经病性疼痛方面表现出高效性，除了具有显著的抗炎性特性外。它们干扰COX-2和炎症细胞因子表达和产生的有效性，使它们成为治疗癌症以及几种炎症性疾病的有趣化合物。公式I:
• Amidine derivatives of 2-heteroaryl-quinazolines and quinolines; potent analgesics and anti-inflammatory agents
  申请人：Rottapharm S.p.A.

  公开号：US07968558B2

  公开（公告）日：2011-06-28

  The present invention concerns novel amidines derivatives of 2-heteroaryl-quinazoline and quinolines of general formula (I), to a process for their preparation, to their pharmaceutical compositions and to the use of these compounds, salts and solvates thereof, along with the corresponding pharmaceutical compositions, for the treatment of pain and inflammatory disorders. Compounds of this invention are extremely potent analgesics, suitable for the treatment of both inflammatory and neuropathic pain. Particularly for the treatment of neuropathic pain the compounds of the invention have been proved largely superior to the standards currently in the clinical use. These compounds are not acting through inhibition of COX or NOS enzymes but are effective in inhibiting inflammatory cytokine production induced by inflammatory stimuli.

  本发明涉及一种2-杂环基喹唑啉和喹啉的新型酰胺衍生物，其通式为（I），以及它们的制备方法、制药组合物以及这些化合物、其盐和溶剂合物的用途，以及相应的制药组合物，用于治疗疼痛和炎症性疾病。本发明的化合物是极其有效的镇痛剂，适用于治疗炎症性和神经病理性疼痛。尤其是对于治疗神经病理性疼痛，本发明的化合物已被证明比目前在临床上使用的标准药物要优越得多。这些化合物并不是通过抑制COX或NOS酶来发挥作用，而是通过抑制炎症刺激引起的炎症细胞因子产生而发挥作用。
• 6-1H-imidazo-quinazoline and quinolines derivatives, new potent analgesics and anti-inflammatory agents
  申请人：Rottapharm S.p.A.

  公开号：US07994181B2

  公开（公告）日：2011-08-09

  The present invention is directed to novel 6-1H-imidazo-2-aryl and 2-heteroaryl quinazoline and quinoline of formula I, corresponding salts and solvates thereof, to a process for their preparation and to the use of this compounds and corresponding pharmaceutical composition for the treatment of pain and inflammatory related disorders. Compounds of the invention have been proven highly effective in the pharmacological treatment of both inflammatory and neuropathic pain, in addition to striking anti-inflammatory properties. Their effectiveness in interfering with COX-2 and inflammatory cytokines expressions and production, highlights them as interesting compounds also for the treatment of cancer in addition to several inflammatory diseases. Formula I:

  本发明涉及新型的6-1H-咪唑-2-芳基和2-杂芳基喹噁啉和喹啉，其化学式为I，对应的盐和溶剂化物，以及它们的制备方法和用于治疗疼痛和炎症相关疾病的医药组合物。该发明的化合物在药理学上已被证明在治疗炎症和神经病理性疼痛方面非常有效，除此之外还具有显著的抗炎性特性。它们在干扰COX-2和炎症细胞因子表达和产生方面的有效性，突显了它们作为治疗癌症以及几种炎症性疾病的有趣化合物的特点。化学式I：