Niacinamide 4-hydroxybenzoate | 1236289-99-8

• 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: Niacinamide 4-hydroxybenzoate
• 英文别名: 4-hydroxybenzoic acid;pyridine-3-carboxamide
• CAS: 1236289-99-8
• 化学式: C₆H₆N₂O*C₇H₆O₃
• 分子量: 260.249
• InChiKey: ZTOJOQVYMATCDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.27
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  烟酰胺 、 对羟基苯甲酸 以 丙酮 为溶剂， 生成 Niacinamide 4-hydroxybenzoate
  参考文献：
  名称：

  Co-Crystals of Active Pharmaceutical Ingredients - Acetazolamide

  摘要：

  A total of 20 co-crystal formers have been combined with acetazolamide (ACZ) via solvent drop grinding in acetone, acetonitrile, and water. The screening experiments provided co-crystals with 4-hydroxybenzoic acid (4HBA) and nicotinamide (NA) (ACZ-4HBA and ACZ-NA-H2O), which were identified by X-ray powder diffraction (XRPD) and further characterized by IR spectroscopy and differential scanning calorimetry-thermogravimetric analysis (DSC-TGA). Both co-crystals could be prepared also by neat grinding (NG) and reaction crystallization (RC). Single-crystal X-ray diffraction analyses allowed for an examination of the dominant hydrogen bonding patterns in the co-crystals, showing that 4HBA binds to the thiadiazole acetamide fragment of ACZ via C(N)NH center dot center dot center dot HOOC and O-H center dot center dot center dot N interactions, while NA is linked through N-H center dot center dot center dot N and N-H center dot center dot center dot O contacts. In ACZ-NA-H2O, the components are connected further by crystal lattice water molecules through N-H center dot center dot center dot O-w and O-w-H center dot center dot center dot N hydrogen bonds. Phase stability assays in water at physiological pH values ranging from 1.2 to 6.8 showed that for ACZ-4HBA the crystalline solid phase did not transform to ACZ within 72 h, while for ACZ-NA-H2O a gradual transformation occurred. Thermal treatment of ACZ-NA-H2O and reaction crystallization experiments in methanol and anhydrous ethanol gave the dehydrated crystalline phase ACZ-NA, which is stable at ambient conditions for at least four months but transforms to the corresponding co-crystal monohydrate when stirred with deionized water.

  DOI：

  10.1021/cg1005693

文献信息

• CO-CRYSTALS OF 5-AMINO-2-OXOTHIAZOLO[4,5-D]PYRIMIDIN-3(2H)-YL-5-HYDROXYMETHYL TETRAHYDROFURAN-3-YL ACETATE AND METHODS FOR PREPARING AND USING THE SAME
  申请人：Hoffmann-La Roche Inc.

  公开号：US20160176899A1

  公开（公告）日：2016-06-23

  Co-crystals of Formula I compounds and their pharmaceutical compositions are novel therapeutics for the treatment of diseases, such as human immunodeficiency virus (HIV) infection, hepatitis B virus (HBV) infection, hepatitis C virus (HCV) infection and cancer. The co-crystal are more stable to oxidation and aqueous degradation, have a better pharmacokinetic profile and superior biological activity than the corresponding tosylate salt form of Formula I compound.

  Formula I化合物的共晶体及其药物组合物是治疗疾病的新型治疗药物，例如人类免疫缺陷病毒（HIV）感染、乙型肝炎病毒（HBV）感染、丙型肝炎病毒（HCV）感染和癌症。这些共晶体比Formula I化合物对应的对甲苯磺酸盐形式更稳定，对氧化和水解更稳定，具有更好的药代动力学特性和优越的生物活性。
• US9676793B2
  申请人：——

  公开号：US9676793B2

  公开（公告）日：2017-06-13
• [EN] CO-CRYSTALS OF 5-AMINO-2-OXOTHIAZOLO[4,5-D]PYRIMIDIN-3(2H)-YL-5-HYDROXYMETHYL TETRAHYDROFURAN-3-YL ACETATE AND METHODS FOR PREPARING AND USING THE SAME<br/>[FR] COCRISTAUX D'ACÉTATE DE 5-AMINO-2-OXOTHIAZOLO[4,5-D]PYRIMIDIN-3(2H)-YL-5-HYDROXYMÉTHYLTÉTRAHYDROFURANN-3-YLE ET LEURS PROCÉDÉS DE PRÉPARATION ET D'UTILISATION
  申请人：HOFFMANN LA ROCHE

  公开号：WO2016103166A1

  公开（公告）日：2016-06-30

  Co-crystals of Formula I compounds and their pharmaceutical compositions are novel therapeutics for the treatment of diseases, such as human immunodeficiency virus (HIV) infection, hepatitis B virus (HBV) infection, hepatitis C virus (HCV) infection and cancer. The co-crystal are more stable to oxidation and aqueous degradation, have a better pharmacokinetic profile and superior biological activity than the corresponding tosylate salt form of Formula I compound. (Formula I)
• Co-Crystals of Active Pharmaceutical Ingredients - Acetazolamide
  作者：Jenniffer I. Arenas-García、Dea Herrera-Ruiz、Karina Mondragón-Vásquez、Hugo Morales-Rojas、Herbert Höpfl

  DOI：10.1021/cg1005693

  日期：2010.8.4

  A total of 20 co-crystal formers have been combined with acetazolamide (ACZ) via solvent drop grinding in acetone, acetonitrile, and water. The screening experiments provided co-crystals with 4-hydroxybenzoic acid (4HBA) and nicotinamide (NA) (ACZ-4HBA and ACZ-NA-H2O), which were identified by X-ray powder diffraction (XRPD) and further characterized by IR spectroscopy and differential scanning calorimetry-thermogravimetric analysis (DSC-TGA). Both co-crystals could be prepared also by neat grinding (NG) and reaction crystallization (RC). Single-crystal X-ray diffraction analyses allowed for an examination of the dominant hydrogen bonding patterns in the co-crystals, showing that 4HBA binds to the thiadiazole acetamide fragment of ACZ via C(N)NH center dot center dot center dot HOOC and O-H center dot center dot center dot N interactions, while NA is linked through N-H center dot center dot center dot N and N-H center dot center dot center dot O contacts. In ACZ-NA-H2O, the components are connected further by crystal lattice water molecules through N-H center dot center dot center dot O-w and O-w-H center dot center dot center dot N hydrogen bonds. Phase stability assays in water at physiological pH values ranging from 1.2 to 6.8 showed that for ACZ-4HBA the crystalline solid phase did not transform to ACZ within 72 h, while for ACZ-NA-H2O a gradual transformation occurred. Thermal treatment of ACZ-NA-H2O and reaction crystallization experiments in methanol and anhydrous ethanol gave the dehydrated crystalline phase ACZ-NA, which is stable at ambient conditions for at least four months but transforms to the corresponding co-crystal monohydrate when stirred with deionized water.