methyl 3,4-diamino-5-methylbenzoate | 668276-43-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 3,4-diamino-5-methylbenzoate
• CAS: 668276-43-5
• 化学式: C₉H₁₂N₂O₂
• 分子量: 180.206
• InChiKey: PWBQQBYVZKTMOV-UHFFFAOYSA-N

物化性质

• 沸点：
  386.7±37.0 °C(Predicted)
• 密度：
  1.216±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  78.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 3,4-diamino-5-methylbenzoate 在 polyphosphoric acid 作用下， 150.0 ℃ 、206.85 kPa 条件下， 反应 12.17h， 生成 2-正丙基-4-甲基-6-(1’-甲基苯并咪唑-2-基)苯并咪唑
  参考文献：
  名称：

  Novel synthetic bisbenzimidazole that targets angiogenesis in Ehrlich ascites carcinoma bearing mice

  摘要：

  Cancer is a leading cause of death in developed countries and second cause in developing countries. Herein we are reporting the synthesis of novel bisbenzimidazole derivatives and their anticancer properties. Among the newly synthesized bisbenzimidazoles, 3-(4-flurophenylsulfonyl)-1,7-dimethyl-2-propyl-1H, 3H-2,5-bibenzo[d] imidazole (FDPB) presented as a potent antiproliferative agent against HeLa, HCT116 and A549 cells with selectivity over normal Vero cells (IC50 > 50 mu M). Additionally, we evaluated the efficacy of lead compound against Ehrlich ascites tumor (EAT) bearing mice for its antitumor and antiangiogenic properties. Our lead compound significantly reduced the cell viability, body weight, ascites volume and downregulated the formation of neovasculature and production of Vascular Endothelial Growth Factor (VEGF). (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.04.010
• 作为产物：
  描述：

  苯甲酸,4-氨基-3-甲基-5-硝基苯甲酸甲酯(9CI) 在 镍 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、344.75 kPa 条件下， 生成 methyl 3,4-diamino-5-methylbenzoate
  参考文献：
  名称：

  [DE] NEUE 2-(PIPERAZIN-1-YL)- UND 2-(`1,4!DIAZEPAN-1-YL)- IMIDAZO`4,5-D!PYRIDAZIN-4-ONE, DEREN HERSTELLUNG UND DEREN VERWENDUNG ALS ARZNEIMITTEL ZUR BEKÄMPFUNG VON DIABETES MELLITUS
  [EN] NOVEL 2-(PIPERAZIN-1-YL)- AND 2-([1,4]DIAZEPAN-1-YL)- IMIDAZO[4,5-D]PYRIDAZIN-4-ONE, PRODUCTION AND USE THEREOF AS MEDICAMENT FOR THE TREATMENT OF DIABETES MELLITUS
  [FR] NOUVELLES 2-(PIPERAZIN-1-YL)- ET 2-([1,4]DIAZEPAN-1-YL)-IMIDAZO[4,5-D]PYRIDAZIN-4-ONES, LEUR PRODUCTION ET LEUR UTILISATION EN TANT QUE MEDICAMENTS POUR TRAITER LE DIABETE SUCRE

  摘要：

  本发明涉及一种具有通式（I）中R1至R3和n如权利要求1至8中定义的取代的咪唑并[4,5-d]吡啶嗪-4-酮的化合物，其互变体、对映体、顺反异构体、混合物和盐，具有有价值的药理特性，特别是对二肽基肽酶-IV（DPP-IV）酶活性的抑制作用。

  公开号：

  WO2005058901A1

文献信息

• [EN] BENZOIMIDAZOLE DERIVATIVES AS PAD4 INHIBITORS<br/>[FR] DÉRIVÉS DE BENZOIMIDAZOLE EN TANT QU'INHIBITEURS DE PAD4
  申请人：GLAXOSMITHKLINE IP DEV LTD

  公开号：WO2016185279A1

  公开（公告）日：2016-11-24

  Compounds of formula (I): wherein X, Y, R1 and R3-R11 are as herein defined, and salts thereof are PAD4 inhibitors and may be useful in the treatment of various disorders, for example rheumatoid arthritis, vasculitis, systemic lupus erythematosus, ulcerative colitis, cancer, cystic fibrosis, asthma, cutaneous lupus erythematosis, and psoriasis.

  式(I)的化合物：其中X、Y、R1和R3-R11如本文所定义，并其盐为PAD4抑制剂，可能在治疗各种疾病中有用，例如类风湿关节炎、血管炎、系统性红斑狼疮、溃疡性结肠炎、癌症、囊性纤维化、哮喘、皮肤红斑狼疮和牛皮癣。
• [EN] PROCESS FOR PREPARING AMIDE-SUBSTITUTED IMIDAZO COMPOUNDS<br/>[FR] PROCÉDÉ DE PRÉPARATION DE COMPOSÉS IMIDAZO À SUBSTITUTION AMIDE
  申请人：BEIGENE BEIJING CO LTD

  公开号：WO2020233677A1

  公开（公告）日：2020-11-26

  Disclosed herein is a process for preparing amide-substituted imidazo compounds. In particular, disclosed herein is the process for preparing certain amide-substituted imidazo compounds that are useful for inhibiting indoleamine 2, 3-dioxygenase and for treating diseases or disorders mediated thereby.

  本文披露了一种制备酰胺取代咪唑化合物的方法。特别是，本文披露了一种制备特定酰胺取代咪唑化合物的方法，这些化合物对抑制吲哚胺2,3-二氧化酶并用于治疗由此介导的疾病或紊乱是有用的。
• [EN] AMIDE-SUBSTITUTED IMIDAZO COMPOUNDS AS SELECTIVE INHIBITORS OF INDOLEAMINE 2, 3-DIOXYGENASES<br/>[FR] COMPOSÉS IMIDAZO SUBSTITUÉS PAR UN AMIDE EN TANT QU'INHIBITEURS SÉLECTIFS DE L'INDOLÉAMINE 2, 3-DIOXYGÉNASES
  申请人：BEIGENE LTD

  公开号：WO2020233676A1

  公开（公告）日：2020-11-26

  Disclosed herein are amide-substituted imidazo compounds and pharmaceutical compositions comprising at least one such novel benzoimidazoles, processes for the preparation thereof, and the method for using the same in therapy. In particular, disclosed herein are certain amide-substituted imidazo compounds that are useful for inhibiting indoleamine 2, 3-dioxygenase and for treating diseases or disorders mediated thereby.

  本文公开了酰胺取代的咪唑化合物和包含至少一种此类新型苯并咪唑的药物组合物，其制备方法以及在治疗中使用的方法。具体而言，本文公开了一些酰胺取代的咪唑化合物，可用于抑制吲哚胺2,3-二氧化酶并用于治疗由此介导的疾病或疾病。
• 8-[3-AMINO-PIPERIDIN-1-YL]-XANTHINES, THE PREPARATION THEREOF AND THEIR USE AS PHARMACEUTICAL COMPOSITIONS
  申请人：Himmelsbach Frank

  公开号：US20080255159A1

  公开（公告）日：2008-10-16

  The present invention relates to substituted xanthines of general formula wherein R 1 to R 3 are defined as in claims 1 to 16 , the tautomers, the stereoisomers, the mixtures, the prodrugs thereof and the salts thereof which have valuable pharmacological properties, particularly an inhibiting effect on the activity of the enzyme dipeptidylpeptidase-IV (DPP-IV).

  本发明涉及一般式的取代黄嘌呤，其中R1至R3的定义如权利要求1至16所述，其互变异构体、立体异构体、混合物、前药和盐具有有价值的药理特性，特别是对酶二肽基肽酶-IV（DPP-IV）的抑制作用。
• 8-[3-amino-piperidin-1-yl]-xanthines, the preparation thereof and their use as pharmaceutical compositions
  申请人：Boehringer Ingelheim Pharma GmbH & Co. KG

  公开号：US20040097510A1

  公开（公告）日：2004-05-20

  The present invention relates to substituted xanthines of general formula 1 wherein R 1 to R 3 are defined as in claims 1 to 16, the tautomers, the stereoisomers, the mixtures, the prodrugs thereof and the salts thereof which have valuable pharmacological properties, particularly an inhibiting effect on the activity of the enzyme dipeptidylpeptidase-IV (DPI-IV).

  本发明涉及一般式1的取代黄嘌呤，其中R1至R3的定义如权利要求1至16所述，其互变异构体、立体异构体、混合物、前药及其盐具有有价值的药理学特性，特别是对酶二肽基肽酶-IV（DPI-IV）的抑制作用。