S-27609 | 151751-58-5

• 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: S-27609
• 英文别名: 1-(2-hydroxy-2-methylpropyl)-2-methyl-1H-imidazo[4,5-c]quinolin-4-amine；4-amino-α,α,2-trimethyl-1H-imidazo[4,5-c]quinoline-1-ethanol；4-amino-α,α,2-trimethyl-1H-imidazo[4,5-c]quinolin-1-ethanol；4-amino-alpha,alpha,2-trimethyl-1H-imidazo[4,5-c]quinoline-1-ethanol；1-(4-amino-2-methylimidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol
• CAS: 151751-58-5
• 化学式: C₁₅H₁₈N₄O
• 分子量: 270.334
• InChiKey: ZAPSNGHNEPUZEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  77
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  S-27609 在 二氧化铂 水 作用下， 以 三氟乙酸 为溶剂， 反应 121.0h， 以to provide 9.7 g of 4-amino-α,α,2-trimethyl-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinoline-1-ethanol as solid, m.p. 290°-292° C的产率得到4-amino-α,α,2-trimethyl-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinoline-1-ethanol
  参考文献：
  名称：

  Process for preparing tetrahdroimidazoquinolinamines

  摘要：

  揭示了一种制备6,7,8,9-四氢-1H-咪唑[4,5-c]喹啉-4-胺的过程。该过程涉及将1H-咪唑[4,5-c]喹啉-4-胺或6H-咪唑[4,5-c]四唑[1,5-a]喹啉还原。

  公开号：

  US05693811A1
• 作为产物：
  描述：

  2-丙醇,1-[(3-氨基-4-喹啉基)氨基]-2-甲基- 在 过氧乙酸 、 ammonium hydroxide 、 对甲苯磺酰氯 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 S-27609
  参考文献：
  名称：

  Synthesis and Structure−Activity-Relationships of 1H-Imidazo[4,5-c]quinolines That Induce Interferon Production

  摘要：

  1H-Imidazo-[4,5-c]quinolines were prepared while investigating novel nucleoside analogues as potential antiviral agents. While these compounds showed no direct antiviral activity when tested in a number of cell culture systems, some demonstrated potent inhibition of virus lesion development in an intravaginal guinea pig herpes simplex virus-2 assay. We have determined that the in vivo antiviral activity can be attributed to the ability of these molecules to induce the production of cytokines, especially interferon (IFN), in this model. Subsequently, we found that the compounds also induce in vitro production of IFN in human peripheral blood mononuclear cells (hPBMCs). The in vitro results reported herein and the in vivo results reported previously led to the discovery of imiquimod, 26, which was developed as a topical agent and has been approved for the treatment of genital warts, actinic keratosis, and superficial basal cell carcinoma.

  DOI：

  10.1021/jm049211v

文献信息

• [EN] IMIDAZOQUINOLINE-TYPE COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS DU TYPE IMIDAZOQUINOLINE ET LEURS UTILISATIONS
  申请人：ALTIMMUNE UK LTD

  公开号：WO2021202921A1

  公开（公告）日：2021-10-07

  Provided in the present disclosure are imidazoquinoline-type compounds, methods for their preparation, pharmaceutical compositions thereof and their use, wherein the imidazoquinoline-type compounds, upon local administration, form depots inducing cell mediated immune response while mitigating a systemic proinflammatory immune response.

  本公开提供了咪唑喹啉类化合物，其制备方法，其制药组合物及其用途，其中咪唑喹啉类化合物在局部给药时形成沉积物，诱导细胞介导的免疫反应，同时减轻全身的促炎免疫反应。
• Use of immidazoquinolinamines as adjuvants in dna vaccination
  申请人：——

  公开号：US20040076633A1

  公开（公告）日：2004-04-22

  The present invention relates to the use of a 1H-imidazo[4,5-c]-4-amine derivative as an adjuvant for use with nucleic acid vaccination.

  本发明涉及使用1H-咪唑[4,5-c]-4-胺衍生物作为核酸疫苗辅助剂的用途。
• Biocompatible compounds for sustained release pharmaceutical drug delivery systems
  申请人：3M Innovative Properties Company

  公开号：US20020164290A1

  公开（公告）日：2002-11-07

  Methods, compounds, and medicinal formulations utilizing biocompatible polymers for delivery of a drug, particularly for solubilizing, stabilizing and/or providing sustained release of drug from topical, implantable, and inhalation systems. Many of the methods, compounds, and medicinal formulations are particularly suitable for oral and/or nasal inhalation and use polymers of the formula —[X—R 1 —C(O)]— wherein each R 1 is an independently selected organic group that links the —X— group to the carbonyl group, and each X is independently oxygen, sulfur, or catenary nitrogen.

  使用生物相容性聚合物的方法、化合物和药物制剂，用于传递药物，特别是用于从局部、植入和吸入系统中溶解、稳定和/或提供持续释放药物。许多方法、化合物和药物制剂特别适用于口服和/或鼻腔吸入，并使用公式为—[X—R1—C(O)]—的聚合物，其中每个R1是独立选择的有机基团，将—X—基团与羰基基团连接起来，每个X独立地是氧、硫或链状氮。
• ADMINISTRATION OF TLR7 LIGANDS AND PRODRUGS THEREOF FOR TREATMENT OF INFECTION BY HEPATITIS C VIRUS
  申请人：Averett Devron R.

  公开号：US20090298863A1

  公开（公告）日：2009-12-03

  This invention relates to methods for treating or preventing hepatitis C virus infections in mammals using Toll-Like Receptor (TLR)7 ligands and prodrugs thereof. More particularly, this invention relates to methods of orally administering a therapeutically effective amount of one or more prodrugs of TLR7 ligands for the treatment or prevention of hepatitis C viral infection. Oral administration of these TLR7 immunomodulating ligands and prodrugs thereof to a mammal provides therapeutically effective amounts and reduced undesirable side effects.

  本发明涉及使用Toll样受体(TLR)7配体及其前药治疗或预防哺乳动物的丙型肝炎病毒感染的方法。更具体地说，本发明涉及口服治疗丙型肝炎病毒感染的一种或多种TLR7配体前药的治疗剂量的方法。将这些TLR7免疫调节配体及其前药口服给哺乳动物，可提供治疗有效量和减少不良副作用。
• Biocompatible compounds for pharmaceutical drug delivery systems
  申请人：MINNESOTA MINING AND MANUFACTURING COMPANY

  公开号：EP1815845A2

  公开（公告）日：2007-08-08

  The invention relates to a sustained release medicinal formulation suitable for nasal and/or oral inhalation comprising: (a) a propellant which comprises a hydrofluorocarbon; (b) a therapeutically effective amount of a drug dispersed in the formulation as a micronized suspension; and (c) a sufficient amount of a biocompatible polymer substantially completely dissolved in the formulation so as to provide for sustained release of the drug; wherein the sustained release formulation results in discrete, nonfilm forming particles upon delivery, the biocompatible polymer is present in at least about a 4:1 ratio by weight of biocompatible polymer to drug, and wherein the biocompatible polymer comprises at least one chain of units of the formula -[X-R1-C(O)]- wherein: (a) each R1 is an independently selected organic group that links the X group to the carbonyl group; and (b) each X is independently oxygen, sulfur, or catenary nitrogen. Furthermore, a metered dose inhaler containing the sustained release medicinal formulation is disclosed.

  本发明涉及一种适用于鼻腔和/或口腔吸入的缓释药物制剂，包括 (a) 由碳氟化合物组成的推进剂； (b) 以微粉化悬浮液形式分散在制剂中的治疗有效量的药物；以及 (c) 足量的生物相容性聚合物，基本上完全溶解在制剂中，以提供药物的持续释 放； 其中，持续释放制剂在给药时形成离散、不成膜的颗粒，生物相容性聚合物与药物的重量比至少约为 4:1，以及 其中生物相容性聚合物包含至少一条式-[X-R1-C(O)]-的单元链，其中 (a) 每个 R1 是独立选择的有机基团，将 X 基团与羰基相连；以及 (b) 每个 X 都是独立的氧、硫或氮。 此外，还公开了一种含有该缓释药物制剂的计量吸入器。