CN106995404A - 一种9,9—双(3,4—二羟基苯基)芴与4,4’—联吡啶形成的共晶及制备方法 - Google Patents

一种9,9—双(3,4—二羟基苯基)芴与4,4’—联吡啶形成的共晶及制备方法 Download PDF

Info

Publication number
CN106995404A
CN106995404A CN201710350299.7A CN201710350299A CN106995404A CN 106995404 A CN106995404 A CN 106995404A CN 201710350299 A CN201710350299 A CN 201710350299A CN 106995404 A CN106995404 A CN 106995404A
Authority
CN
China
Prior art keywords
fluorenes
bis
bipyridyl
eutectic
dihydroxy phenyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
CN201710350299.7A
Other languages
English (en)
Inventor
吉保明
邓冬生
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Luoyang Normal University
Original Assignee
Luoyang Normal University
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Luoyang Normal University filed Critical Luoyang Normal University
Priority to CN201710350299.7A priority Critical patent/CN106995404A/zh
Publication of CN106995404A publication Critical patent/CN106995404A/zh
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/22—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing two or more pyridine rings directly linked together, e.g. bipyridyl
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
    • C07C39/17—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings containing other rings in addition to the six-membered aromatic rings, e.g. cyclohexylphenol
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/127—Preparation from compounds containing pyridine rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13—Crystalline forms, e.g. polymorphs

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

本发明涉及一种9,9—双(3,4—二羟基苯基)芴与4,4’—联吡啶共晶的制备方法。所述共晶结构特征为不对称晶胞中含有由1.5个9,9—双(3,4—二羟基苯基)芴分子与3个4,4’—联吡啶分子，在晶体结构中，1个9,9—双(3,4—二羟基苯基)芴分子上4个羟基通过O‑H···N的氢键作用连接4个不同的4,4’—联吡啶分子，同时这4个4,4’—联吡啶分子再通过O—H···N的氢键连接另外4个不同的9,9—双(3,4—二羟基苯基)芴分子，按照上述方式连接，形成网格结构。制备方法是以乙腈和三氯甲烷为溶剂，采用先加热回流再冷却结晶方式制备得到。本发明提供了多元酚与吡啶类物质形成共晶的制备方法，为该类药物共晶制备提供理论指导意义。

Description

一种9,9—双(3,4—二羟基苯基)芴与4,4’—联吡啶形成的共 晶及制备方法
技术领域
本发明属于多酚类化合物与含吡啶类化合物形成共晶的技术领域，具体涉及到一种9,9—双(3,4—二羟基苯基)芴与4,4’—联吡啶形成的共晶及制备方法。
背景技术
共晶最近二十多年来受到广泛的关注。第一个共晶是1844年WÖhler制备了氢醌共晶，并进行了结构表征，但是并没有从理论上给出概念。后来，1967年Schmidt和Snipes两人最先用“共晶”这个词来描述嘧啶和嘌呤的复合物分子。自此以后，共晶概念一直在不断的更新含义，直到2003年，一个较为普遍的接受概念就是共晶作为一种同相的结晶材料，它含有化学计量的两种或者两种以上的中性组份。
超分子化学和晶体工程概念认为共晶是各组分通过氢键或卤键而形成的一种超分子自组装体系，是热力学、动力学和分子识别三者之间相互作用而达到平衡的一个最稳定的结果。对近100多年所制备的共晶的研究发现，共晶的形成作用力主要来自于氢键、卤键、π-π堆积作用和电荷交换等作用力。研究发现，共晶结构中各组份之间不单单只存在一种作用力，而是由各种不同的作用力共同发挥作用，达到平衡后形成稳定的晶体。
共晶作为一个较新的研究领域，目前依然遇到不少挑战。首先遇到的挑战是，对共晶形成的较佳的反应条件和形成机理不能完全掌握，这主要是因为不是任何两种或两种以上组份都能形成共晶，所以必然存在何种组份能够形成结晶以及有多少种组份能够共组装结晶等等问题。这就有必要继续研究有关共晶结晶的方法问题，包括溶剂的选择、结晶方法的选择、组份的选择和化学合成技巧等。
发明内容
本发明的目的是提供一种9,9—双(3,4—二羟基苯基)芴与4,4’—联吡啶形成的共晶及制备方法，为该类药物共晶制备提供理论指导，并对其进行晶体结构测定。
本发明的目的可采用如下技术方案来实现：
一种9,9—双(3,4—二羟基苯基)芴与4,4’—联吡啶形成的共晶，其共晶结构特征为不对称晶胞中含有由1.5个9,9—双(3,4—二羟基苯基)芴分子与3个4,4’—联吡啶分子，在晶体结构中，1个9,9—双(3,4—二羟基苯基)芴分子上4个羟基通过O—H···N的氢键作用连接4个不同的4,4’—联吡啶分子，同时这4个4,4’—联吡啶分子再通过O—H···N的氢键连接另外4个不同的9,9—双(3,4—二羟基苯基)芴分子，按照这样方式无穷连接下去，形成网格结构。
本发明所述的9,9—双(3,4—二羟基苯基)芴与4,4’—联吡啶形成的共晶属于单斜晶系，空间群为C2/c，晶胞参数为a = 48.713(4) Ǻ，b = 8.5651(7) Ǻ， c = 28.116(2) Ǻ，三个轴角α = 90°，β = 115.7630(10)°，γ = 90°，V = 10564.8(15) Ǻ3。
本发明所述的9,9—双(3,4—二羟基苯基)芴与4,4’—联吡啶形成的共晶是以乙腈和三氯甲烷为溶剂，采用先加热回流再冷却结晶方式制备得到。具体制备步骤如下：
（1）将摩尔比为2:1~1:2的9,9—双(3,4—二羟基苯基)芴和4,4’—联吡啶加入到圆底烧瓶中，同时加入乙腈溶剂或者三氯甲烷溶剂并放入磁子，体系中溶质总含量比例为1% ~10%；
（2）装上回流装置，搅拌下加热回流，直到溶质完全溶解；
（3）将得到的溶液过滤，滤液在室温下放置，让其自然挥发，数天后析出大量无色晶体；
（4）将析出的晶体过滤，自然晾干得到9,9—双(3,4—二羟基苯基)芴与4,4’—联吡啶形成的共晶。
所述的9,9—双(3,4—二羟基苯基)芴与4,4’—联吡啶形成的共晶的摩尔比为1.5:3。
本发明的有益效果为：本发明提供了多元酚与吡啶类物质形成共晶的制备方法，为该类药物共晶制备提供理论指导意义。
附图说明
图1为9,9—双(3,4—二羟基苯基)芴与4,4’—联吡啶形成的共晶不对称结构单元。
图2为9,9—双(3,4—二羟基苯基)芴分子与4,4’—联吡啶分子形成的网格结构图。
具体实施方式
下面结合附图说明本发明的具体实施方式
本发明所选用共晶结晶组份为9,9—双(3,4—二羟基苯基)芴与4,4’—联吡啶，溶剂为乙腈或者三氯甲烷。
本发明用到的组份9,9—双(3,4—二羟基苯基)芴，分子式为C25H18O4，其结构式如a所示。组份4,4’—联吡啶，分子式为C10H8N2，其结构式如b所示
不对称晶胞中含有由1.5个9,9—双(3,4—二羟基苯基)芴分子与3个4,4’—联吡啶分子，如图1所示。在晶体结构中，1个9,9—双(3,4—二羟基苯基)芴分子上4个羟基通过O—H···N的氢键作用连接4个不同的4,4’—联吡啶分子，同时这4个4,4’—联吡啶分子再通过O—H···N的氢键连接另外4个不同的9,9—双(3,4—二羟基苯基)芴分子，按照上述方式无穷连接下去，形成网格结构，如图2所示。
本发明所述的9,9—双(3,4—二羟基苯基)芴与4,4’—联吡啶形成的共晶属于单斜晶系，空间群为C2/c，晶胞参数为a = 48.713(4) Ǻ，b = 8.5651(7) Ǻ， c = 28.116(2) Ǻ，三个轴角α = 90°，β = 115.7630(10)°，γ = 90°，V = 10564.8(15) Ǻ3。
本发明得到的9,9—双(3,4—二羟基苯基)芴与4,4’—联吡啶形成的共晶是以乙腈和三氯甲烷为溶剂，采用先加热回流再冷却结晶方式制备得到。具体制备步骤如下实施例：
实施例1
将1.0 mmol 9,9—双(3,4—二羟基苯基)芴（382毫克）、1.0 mmol 4,4’—联吡啶（156毫克）置于50 mL圆底烧瓶中，两者的摩尔比为1:1，再加入30 mL乙腈，固体占体系总质量的2%。放入一个磁子，装上回流冷凝管，搅拌下加热回流1小时，趁热过滤，滤液放置在室温下让其自然挥发，数天后从滤液中析出大量无色晶体，过滤，得到分子式为C67.5H51N6O6共晶，称重质量为319.2毫克，产率为92%。
9,9—双(3,4—二羟基苯基)芴与4,4’—联吡啶形成的共晶表征过程如下：
（1）9,9—双(3,4—二羟基苯基)芴与4,4’—联吡啶形成共晶的晶体结构测定
选取大小合适晶型较好的晶体粘于一根玻璃丝上，放在Bruker SMART ApexII单晶衍射仪上进行单晶结构测定： 23℃下，以MoK a (λ= 0.71073 Å)射线作为光源，石墨作为单色器，检测面板为Bruker Smart CCD，采用ω扫描方式对晶胞进行扫描测定，并收集衍射强度数据。首先采用BrukerAPEX-II 程序对采集好的数据进行晶胞精修、数据的吸收校正以及还原；然后通过 SHELXTL 软件中的 XS 程序对还原后的数据采用直接法解析结构，获得所有非氢原子的初始相位角，各向异性参数的精修则通过SHELXL-97 程序运行，使用全矩阵最小二乘法，直至数据收敛，最终对非氢原子坐标的进行确定。芳香环上与碳原子相连的氢以及氧原子上的氢原子均通过理论计算法加入。详细的晶体测试参数如下表所示：
Chemical formula C67.5H51N6O6
Formula weight 1042.14
Crystal system Monoclinc
Space group C2/c
a/Å 48.713(4)
b/Å 8.5651(7)
c/Å 28.116(2)
α/° 90
β/° 115.7630(10)
γ/° 90
Volume/Å3 10564.8(15)
Z 8
D calc/g cm-3 1.310
μ/mm-1 0.085
T/K 296(2)
Reflns. Collected 39203
Unique reflns 9834
R int 0.0511
Goodness-of-fit 0.999
R 1(I > 2σ) 0.0469
wR 2(I>2σ ) 0.1046
（2）9,9—双(3,4—二羟基苯基)芴与4,4’—联吡啶形成共晶的元素分析测试
使用意大利产的Flash EA-2000元素分析仪对9,9—双(3,4—二羟基苯基)芴与4,4’—联吡啶形成的共晶进行元素分析，测试表明C、N、H三元素的测定值与理论值相近，其测试结果数据如下：对分子式为C67.5H51N6O6的共晶分析，其理论值为：C 77.79, H 4.93, N 8.06;实测值：C 78.03, H 5.08, N 8.01.
实施例2
将2.0 mmol 9,9—双(3,4-二羟基苯基)芴（764毫克）、1.0 mmol 4,4’—联吡啶（156毫克）置于50 mL圆底烧瓶中，两者的摩尔比为2:1，再加入30 mL乙腈，固体占体系总质量的4%。放入一个磁子，装上回流冷凝管，搅拌下加热回流1小时，趁热过滤，滤液放置在室温下让其自然挥发，数天后从滤液中析出大量无色晶体，过滤，得到分子式为C67.5H51N6O6共晶，称重质量为312.3毫克，产率为90%。
实施例3
将1.0 mmol 9,9—双(3,4-二羟基苯基)芴（382毫克）、2.0 mmol 4,4’—联吡啶（312毫克）置于50 mL圆底烧瓶中，两者的摩尔比为1:2，再加入30 mL乙腈，固体占体系总质量的3%。放入一个磁子，装上回流冷凝管，搅拌下加热回流1小时，趁热过滤，滤液放置在室温下让其自然挥发，数天后从滤液中析出大量无色晶体，过滤，得到分子式为C67.5H51N6O6共晶，称重质量为666.2毫克，产率为96%。
实施例4
将1.0 mmol 9,9—双(3,4-二羟基苯基)芴（382毫克）、2.0 mmol 4,4’—联吡啶（312毫克）置于50 mL圆底烧瓶中，两者的摩尔比为1:2，再加入15 mL乙腈，固体占体系总质量5.6%。放入一个磁子，装上回流冷凝管，搅拌下加热回流1小时，趁热过滤，滤液放置在室温下让其自然挥发，数天后从滤液中析出大量无色晶体，过滤，得到分子式为C67.5H51N6O6共晶，称重质量为659.3毫克，产率为95%。
实施例5
将1.0 mmol 9,9—双(3,4—二羟基苯基)芴（382毫克）、1.0 mmol 4,4’—联吡啶（156毫克）置于50 mL圆底烧瓶中，两者的摩尔比为1:1，再加入20 mL三氯甲烷，固体占体系总质量1.8%。放入一个磁子，装上回流冷凝管，搅拌下加热回流0.5小时，趁热过滤，滤液放置在室温下让其自然挥发，24小时后从滤液中析出大量无色晶体，过滤，得到分子式为C67.5H51N6O6共晶，称重质量为329.7毫克，产率为95%。
实施例6
将2.0 mmol 9,9—双(3,4—二羟基苯基)芴（764毫克）、1.0 mmol 4,4’—联吡啶（156毫克）置于50 mL圆底烧瓶中，两者的摩尔比为2:1，再加入20 mL三氯甲烷，固体占体系总质量3.0%。放入一个磁子，装上回流冷凝管，搅拌下加热回流0.5小时，趁热过滤，滤液放置在室温下让其自然挥发，24小时后从滤液中析出大量无色晶体，过滤，得到分子式为C67.5H51N6O6共晶，称重质量为315.8毫克，产率为91%。
实施例7
将1.0 mmol 9,9—双(3,4—二羟基苯基)芴（382毫克）、2.0 mmol 4,4’—联吡啶（312毫克）置于50 mL圆底烧瓶中，两者的摩尔比为1:2，再加入20 mL三氯甲烷，固体占体系总质量2.3%。放入一个磁子，装上回流冷凝管，搅拌下加热回流0.5小时，趁热过滤，滤液放置在室温下让其自然挥发，24小时后从滤液中析出大量无色晶体，过滤，得到分子式为C67.5H51N6O6共晶，称重质量为673.2毫克，产率为97%。

Claims (4)

1.一种9,9—双(3,4—二羟基苯基)芴与4,4’—联吡啶形成的共晶，其特征是：所述共晶结构特征为不对称晶胞中含有1.5个9,9—双(3,4—二羟基苯基)芴分子与3个4,4’—联吡啶分子，在晶体结构中，1个9,9—双(3,4—二羟基苯基)芴分子上4个羟基通过O—H···N的氢键作用连接4个不同的4,4’—联吡啶分子，同时这4个4,4’—联吡啶分子再通过O—H···N的氢键连接另外4个不同的9,9—双(3,4—二羟基苯基)芴分子，按照上述方式连接，形成网格结构。
2.根据权利要求1所述的9,9—双(3,4—二羟基苯基)芴与4,4’—联吡啶形成的共晶，其特征在于：所制得的共晶属于单斜晶系，空间群为C2/c，晶胞参数为a = 48.713(4) Ǻ，b= 8.5651(7) Ǻ， c = 28.116(2) Ǻ，三个轴角α = 90°，β = 115.7630(10)°，γ = 90°，V= 10564.8(15)Ǻ3。
3.一种如权利要求1所述的9,9—双(3,4—二羟基苯基)芴与4,4’—联吡啶形成的共晶制备方法，其特征是采用溶液先回流加热再冷却结晶方法，具体步骤如下：
（1）将9,9—双(3,4—二羟基苯基)芴和4,4’—联吡啶按2:1~1:2的摩尔比加入到圆底烧瓶中，再加入乙腈溶剂或者三氯甲烷溶剂并放入磁子，加入的溶剂量使得体系中溶质总含量比例为1.0% ~10.0%；
（2）装上回流装置，搅拌下加热回流，直到溶质完全溶解；
（3）将得到的溶液过滤，滤液在室温下放置，让其自然挥发，数天后析出大量无色晶体；
（4）将析出的晶体过滤，自然晾干得到9,9—双(3,4—二羟基苯基)芴与4,4’—联吡啶形成的共晶。
4.根据权利要求3所述的9,9—双(3,4—二羟基苯基)芴与4,4’—联吡啶形成的共晶制备方法，其特征是：所述的9,9—双(3,4—二羟基苯基)芴与4,4’—联吡啶形成的共晶的摩尔比为1.5:3。
CN201710350299.7A 2017-05-18 2017-05-18 一种9,9—双(3,4—二羟基苯基)芴与4,4’—联吡啶形成的共晶及制备方法 Pending CN106995404A (zh)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201710350299.7A CN106995404A (zh) 2017-05-18 2017-05-18 一种9,9—双(3,4—二羟基苯基)芴与4,4’—联吡啶形成的共晶及制备方法

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201710350299.7A CN106995404A (zh) 2017-05-18 2017-05-18 一种9,9—双(3,4—二羟基苯基)芴与4,4’—联吡啶形成的共晶及制备方法

Publications (1)

Publication Number Publication Date
CN106995404A true CN106995404A (zh) 2017-08-01

Family

ID=59435747

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201710350299.7A Pending CN106995404A (zh) 2017-05-18 2017-05-18 一种9,9—双(3,4—二羟基苯基)芴与4,4’—联吡啶形成的共晶及制备方法

Country Status (1)

Country Link
CN (1) CN106995404A (zh)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108358904A (zh) * 2018-03-28 2018-08-03 梧州学院 一种阿齐沙坦与4,4’-联吡啶的共晶体及其制备方法
CN110845507A (zh) * 2019-11-14 2020-02-28 浙江大学 一种甘脲衍生化的含蒽基团的分子夹及其制备方法和应用
CN114213324A (zh) * 2021-11-10 2022-03-22 华南理工大学 羟氯喹共晶及其制备方法、含量测定方法和应用
CN114315716A (zh) * 2021-11-10 2022-04-12 华南理工大学 羟氯喹新共晶及其制备方法、含量测定方法和应用
CN116333328A (zh) * 2023-02-23 2023-06-27 暨南大学 一种新型铜基吡啶芴晶体海绵的制备方法及其应用

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102060755A (zh) * 2010-12-28 2011-05-18 吉林大学 一种新型对乙酰氨基酚药物共晶及其制备方法
CN102659526A (zh) * 2012-04-11 2012-09-12 哈尔滨工程大学 四酚羟基芴化合物及其制备方法
CN103360331A (zh) * 2013-06-29 2013-10-23 天津大学 新型拉莫三嗪药物共晶及其制备方法
CN105646195A (zh) * 2015-07-22 2016-06-08 黑龙江大学 一种芬布芬药物共晶及其制备方法

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102060755A (zh) * 2010-12-28 2011-05-18 吉林大学 一种新型对乙酰氨基酚药物共晶及其制备方法
CN102659526A (zh) * 2012-04-11 2012-09-12 哈尔滨工程大学 四酚羟基芴化合物及其制备方法
CN103360331A (zh) * 2013-06-29 2013-10-23 天津大学 新型拉莫三嗪药物共晶及其制备方法
CN105646195A (zh) * 2015-07-22 2016-06-08 黑龙江大学 一种芬布芬药物共晶及其制备方法

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
BRENDAN F. ABRAHAMS ET AL.: "An Extensive class of solids full of holes larger enough to enclose over 200 molecules of H2O", 《ANGEW. CHEM. INT. ED.》 *
张晓明: "药物共晶的合成、表征与性质研究", 《中国优秀博硕士学位论文全文数据库（博士）工程科技I辑》 *
方亮等: "《药剂学》", 31 March 2016, 中国医药科技出版社 *
邓冬生: "双吡啶与多酚的共晶研究：底物构型对超分子合成子的影响", 《中国化学会全国第十六届大环化学暨第八届超分子化学学术讨论会》 *
邢娇娇: "新型药物共晶的合成及表征", 《中国优秀博硕士学位论文全文数据库（硕士）工程科技I辑》 *

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108358904A (zh) * 2018-03-28 2018-08-03 梧州学院 一种阿齐沙坦与4,4’-联吡啶的共晶体及其制备方法
CN110845507A (zh) * 2019-11-14 2020-02-28 浙江大学 一种甘脲衍生化的含蒽基团的分子夹及其制备方法和应用
CN114213324A (zh) * 2021-11-10 2022-03-22 华南理工大学 羟氯喹共晶及其制备方法、含量测定方法和应用
CN114315716A (zh) * 2021-11-10 2022-04-12 华南理工大学 羟氯喹新共晶及其制备方法、含量测定方法和应用
CN114213324B (zh) * 2021-11-10 2024-02-23 华南理工大学 羟氯喹共晶及其制备方法、含量测定方法和应用
CN114315716B (zh) * 2021-11-10 2024-02-23 华南理工大学 羟氯喹共晶及其制备方法、含量测定方法和应用
CN116333328A (zh) * 2023-02-23 2023-06-27 暨南大学 一种新型铜基吡啶芴晶体海绵的制备方法及其应用

Similar Documents

Publication Publication Date Title
CN106995404A (zh) 一种9,9—双(3,4—二羟基苯基)芴与4,4’—联吡啶形成的共晶及制备方法
CN105330606B (zh) 2-氨基吡啶为前驱体的5-氟尿嘧啶药物共晶及其制备方法和应用
CN107056684A (zh) 一种2,2’,3,3’—四羟基联萘与4,4’—联吡啶形成的共晶及制备方法
He et al. Polymorphism observed in dapsone–flavone cocrystals that present pronounced differences in solubility and stability
CN103351399B (zh) 反式六元瓜环的合成、分离方法
André et al. Revisiting paracetamol in a quest for new co-crystals
CN105111458A (zh) 一种卤化锌三联吡啶配位聚合物多功能材料及其制备方法
CN104649969B (zh) 一种替尼类药物的盐及其制备方法
Lou et al. Synthesis, co-crystal structure and characterization of pyrazinamide with m-hydroxybenzoic acid, p-hydroxybenzoic acid and 3, 4-dihydroxy benzolic acid
Ono et al. Procedure-dependent construction of two isomers of trimeric self-assembled boronic esters
WO2021000687A1 (zh) Pac-1晶型的制备方法
CN105753733B (zh) Ahu377的晶型及其制备方法与用途
CN108794383A (zh) 硝苯地平与异烟酰胺的共晶
Wan et al. Efficient solvent-controlled crystallization of pure polymorphs of 1-nitro-4-(4-nitrophenylmethylthio) benzene
CN109912608A (zh) 羟基取代咔咯配合物及其制备方法
CN110156922A (zh) 一种立构规整聚甲基丙烯酸甲酯的可控合成方法
CN105481780B (zh) 2-氨基嘧啶为前驱体的5-氟尿嘧啶药物共晶及其制备方法和应用
CN113563340B (zh) 一种苦参碱并嘧啶衍生物及其制备方法和应用
CN104130292A (zh) 一种带双核结构的三维配位聚合物及其制备方法
Murray-Rust et al. The stability and conformation of the 1, 3, 6, 8-tetraazatricyclo [4.4. 1.13, 8] dodecane system: the structure of the condensation product of 1, 2-diaminocyclohexane and formaldehyde
CN106117252B (zh) 一种镉盐荧光功能配位材料及其制备方法
CN101659646A (zh) 马来酸桂哌齐特晶型及其制备方法
CN105384744B (zh) 四(三氟乙氧基)酞菁铕配合物及其制备方法和应用
CN104130293A (zh) 一种混合配体的三维配位聚合物及其制备方法
CN107325043A (zh) 一种左旋阿雷地平的晶型及其制备方法

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
RJ01 Rejection of invention patent application after publication

Application publication date: 20170801

RJ01 Rejection of invention patent application after publication