imiquimod hydrochloride

• 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: imiquimod hydrochloride
• 英文别名: 1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine hydrochloride；4-amino-1-isobutyl-1H-imidazo(4,5-c)quinoline hydrochloride；1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine hydrochloride；imiquimod HCl；1-(2-methylpropyl)imidazo[4,5-c]quinolin-4-amine;hydrochloride
• 化学式: C₁₄H₁₆N₄*ClH
• 分子量: 276.769
• InChiKey: RGKLRAHQVIHCCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.24
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  56.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  imiquimod hydrochloride 在 sodium hydrogensulfide 、 甲烷 、 Ammonium hydroxide 作用下， 以 水 为溶剂， 反应 0.33h， 以80.5%的产率得到羟丙基甲基纤维素邻苯二甲酸酯
  参考文献：
  名称：

  [EN] PREPARATION OF 1H-IMIDAZO [4,5-C] QUINOLIN-4-AMINES VIA NOVEL 1H-IMIDAZO [4,5-C] QUINOLIN-4-CYANO AND 1H-IMIDAZO [4,5-C] QUINOLIN-4-CARBOXAMIDE INTERMEDIATES
  [FR] PREPARATION DE 1H-IMIDAZO[4,5-C] QUINOLIN-4-AMINES A L'AIDE DE NOUVEAUX INTERMEDIAIRES 1H-IMIDAZO[4,5-C] QUINOLINE-4-CYANO ET 1H-IMIDAZO[4,5-C] QUINOLINE-4-CARBOXAMIDE

  摘要：

  本发明涉及一种合成1H-咪唑[4,5-c]喹啉4-腈和1H-咪唑[4,5-c]喹啉4-羧酰胺中间体的过程，该中间体可用于制备1H-咪唑[4,5-C]喹啉4-胺，以及使用这些中间体制备1H-咪唑[4,5-C]喹啉4-胺的过程；同时，本发明还涉及1H-咪唑[4,5-c]喹啉4-腈和1H-咪唑[4,5-c]喹啉4-羧酰胺中间体。更具体地说，本发明涉及使用两种中间体，即1-异丁基-1H-咪唑[4,5-c]喹啉4-腈和1-异丁基-1H-咪唑[4,5-c]喹啉4-羧酰胺，制备1-异丁基-1H-咪唑[4,5-C]喹啉4-胺（Imiquimod）的过程，以及所述中间体。

  公开号：

  WO2004011462A1
• 作为产物：
  描述：

  5-amino-1-isobutyl-1H-imidazole-4-carbonitrile 在 bis-triphenylphosphine-palladium(II) chloride 二碘甲烷 、 乙醇 、 potassium carbonate 、 乙酰氯 、 亚硝酸异戊酯 作用下， 以 乙二醇二甲醚 、 氯仿 、 水 为溶剂， 反应 3.17h， 生成 imiquimod hydrochloride
  参考文献：
  名称：

  Ring Closing and Related Methods and Intermediates

  摘要：

  用于制备公式化合物的方法和中间体，以及制备公式I化合物的方法，最好包括形成公式中间体化合物的步骤。

  公开号：

  US20110269965A1

文献信息

• Preparation of 1H-imidazo[4,5-c]quinolin-4-amines via 1H-imidazo[4, 5-c]quinolin-4-phtalimide intermediates
  申请人：Hajko Janos

  公开号：US20080103310A1

  公开（公告）日：2008-05-01

  The present invention provides process for the preparation of 4-amino-1H-imidazo[4,5-c]quinolines comprising the step of reacting a 1H-imidazo[4,5-c]quinolin-4-phthalimide with an amine selected from the group consisting of: alkylamine, aralkylamine, alkyldiamine, and aralkyldiamine.

  本发明提供一种制备4-氨基-1H-咪唑[4,5-c]喹啉的方法，包括将1H-咪唑[4,5-c]喹啉-4-邻酰亚胺与以下群组中选择的胺反应的步骤：烷基胺、芳基烷基胺、烷基二胺和芳基烷基二胺。
• Preparation of 1H-imidazo [4,5-C] quinolin-4 amines via novel 1h-imidazo [4,5-C] quinolin-4-cyano and 1h-imidazo [4,5-C] quinolin-4-carboxamide intermediates
  申请人：Merli Valeriano

  公开号：US20050101627A1

  公开（公告）日：2005-05-12

  The invention relates to a process for the synthesis of 1H-imidazo[4,5-c]quinoline 4-cyano and 1H-imidazo[4,5-c]quinoline 4-carboxamide intermediates useful in preparing 1H-imidazo [4,5-C]quinoline 4-amines, a process for preparing 1H-imidazo[4,5-C]quinoline 4-amines using such intermediates; and, to the 1H-imidazo[4,5-c]quinoline 4-cyano and 1H-imidazo[4,5-c]quinoline 4-carboxamide intermediates. More particularly, the invention relates to a process for the preparation of 1-isobutyl-1H-imidazo[4,5-C]quinoline 4-amine (Imiquimod) using two intermediates, 1-isobutyl-1H-imidazo[4,5-c] quinoline 4-cyano and 1-isobutyl-1H-imidazo[4,5-c]quinoline 4-carboxamide, and to the said intermediates.

  本发明涉及一种合成1H-咪唑[4,5-c]喹啉4-氰和1H-咪唑[4,5-c]喹啉4-羧酰胺中间体的过程，该中间体用于制备1H-咪唑[4,5-C]喹啉4-胺，一种使用这种中间体制备1H-咪唑[4,5-C]喹啉4-胺的方法；以及1H-咪唑[4,5-c]喹啉4-氰和1H-咪唑[4,5-c]喹啉4-羧酰胺中间体。更具体地说，本发明涉及使用两种中间体1-异丁基-1H-咪唑[4,5-C]喹啉4-氰和1-异丁基-1H-咪唑[4,5-c]喹啉4-羧酰胺制备1-异丁基-1H-咪唑[4,5-C]喹啉4-胺（伊米希莫德）的过程，以及所述中间体。
• Preparation of 1H-imidazo [4,5-c] quinolin-4-amines via novel 1H-imidazo [4,5-c] quinolin-4-cyano and 1H-imidazo [4,5-c] quinolin-4-carboxamide intermediates
  申请人：Merli Valeriano

  公开号：US20050119294A1

  公开（公告）日：2005-06-02

  The invention relates to a process for the synthesis of 1H-imidazo[4,5-c]quinoline 4-cyano and 1H-imidazo[4,5-c]quinoline 4-carboxamide intermediates useful in preparing 1H-imidazo[4,5-C]quinoline 4-amines, a process for preparing 1H-imidazo[4,5-C]quinoline 4-amines using such intermediates; and, to the 1H-imidazo[4,5-c]quinoline 4-cyano and 1H-imidazo[4,5-c]quinoline 4-carboxamide intermediates. More particularly, the invention relates to a process for the preparation of 1-isobutyl-1H-imidazo[4,5-C]quinoline 4-amine (Imiquimod) using two intermediates, 1-isobutyl-1H-imidazo[4,5-c]quinoline 4-cyano and 1-isobutyl-1H-imidazo[4,5-c]quinoline 4-carboxamide, and to the said intermediates.

  本发明涉及一种合成1H-咪唑[4,5-c]喹啉4-腈和1H-咪唑[4,5-c]喹啉4-羧酰胺中间体的方法，该中间体可用于制备1H-咪唑[4,5-C]喹啉4-胺，以及使用此类中间体制备1H-咪唑[4,5-C]喹啉4-胺的方法；同时还涉及到1H-咪唑[4,5-c]喹啉4-腈和1H-咪唑[4,5-c]喹啉4-羧酰胺中间体。更具体地说，本发明涉及使用两种中间体1-异丁基-1H-咪唑[4,5-C]喹啉4-腈和1-异丁基-1H-咪唑[4,5-c]喹啉4-羧酰胺制备1-异丁基-1H-咪唑[4,5-C]喹啉4-胺（伊米曲莫德）的方法，以及涉及到这些中间体。
• Preparation of 1H-imidazo [4,5-C] quinolin-4-amines via novel 1H-imidazo [4,5-c] quinolin-4-cyano and 1H-imidazo [4,5-c] quinolin-4-carboxamide intermediates
  申请人：——

  公开号：US20040063743A1

  公开（公告）日：2004-04-01

  The invention relates to a process for the synthesis of 1H-imidazo[4,5-c] quinoline 4-cyano and 1H-imidazo[4,5-c] quinoline 4-carboxamide intermediates useful in preparing 1H-imidazo[4,5-C] quinoline 4-amines, a process for preparing 1H-imidazo[4,5-C] quinoline 4-amines using such intermediates; and, to the 1H-imidazo[4,5-c] quinoline 4-cyano and 1H-imidazo[4,5-c] quinoline 4-carboxamide intermediates. More particularly, the invention relates to a process for the preparation of 1-isobutyl-1H-imidazo[4,5-C] quinoline 4-amine (Imiquimod) using two intermediates, 1-isobutyl-1H-imidazo[4,5-c] quinoline 4-cyano and 1-isobutyl-1H-imidazo[4,5-c] quinoline 4-carboxamide, and to the said intermediates.

  本发明涉及一种合成1H-咪唑[4,5-c]喹啉4-腈和1H-咪唑[4,5-c]喹啉4-羧酰胺中间体的方法，该中间体在制备1H-咪唑[4,5-C]喹啉4-胺时有用；以及使用这种中间体制备1H-咪唑[4,5-C]喹啉4-胺的方法；以及1H-咪唑[4,5-c]喹啉4-腈和1H-咪唑[4,5-c]喹啉4-羧酰胺中间体。更具体地，本发明涉及使用两种中间体1-异丁基-1H-咪唑[4,5-C]喹啉4-腈和1-异丁基-1H-咪唑[4,5-c]喹啉4-羧酰胺制备1-异丁基-1H-咪唑[4,5-C]喹啉4-胺（Imiquimod）的方法，以及这些中间体。
• HIGH PENETRATION PRODRUG COMPOSITIONS OF 1H-IMIDAZO[4,5-C]QUINOLIN-4-AMINES AND 1H-IMIDAZO[4,5-C]QUINOLIN-4-AMINE-RELATED COMPOUNDS
  申请人：YU Chongxi

  公开号：US20100021394A1

  公开（公告）日：2010-01-28

  The invention provides compositions of novel high penetration compositions (HPC) or high penetration prodrugs (HPP) of 1H-imidazo[4,5-c]quinolin-4-amines and 1H-imidazo[4,5-c]quinolin-4-amine-related compounds, which are capable of crossing biological barriers with high penetration efficiency. The HPPs are capable of being converted to parent active drugs or drug metabolites after crossing the biological barrier and thus can render treatments for the conditions that the parent drugs or metabolites can. Additionally, the HPPs are capable of reaching areas that parent drugs may not be able to access or to render a sufficient concentration at the target areas and therefore render novel treatments. The HPPs can be administered to a subject through various administration routes, e.g., locally delivered to an action site of a condition with a high concentration or systematically administered to a biological subject and enter the general circulation with a faster rate.

  本发明提供了一种新型高穿透力化合物（HPC）或高穿透力前药（HPP）的组合物，其中包括1H-咪唑[4,5-c]喹啉-4-胺和1H-咪唑[4,5-c]喹啉-4-胺相关化合物。这些化合物能够高效地穿过生物屏障。HPP可以在穿过生物屏障后被转化为原始活性药物或药物代谢物，从而可以治疗与原始药物或代谢物相关的疾病。此外，HPP能够到达原始药物无法接触到或无法在目标区域产生足够浓度的区域，从而提供新型治疗方法。HPP可以通过各种给药途径给予受试者，例如在治疗区域局部给药以高浓度作用或系统性给药给生物受试者，并以更快的速度进入全身循环。