- Nitroimidazole derivative, preparation method and application thereof
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The invention provides a nitroimidazole derivative as shown in a general formula I or a pharmaceutically acceptable salt, a solvent compound, a hydrate, a polymorphic substance, a deuterated substance and an isomer thereof. The invention also provides a pharmaceutical composition containing the compound and application of the pharmaceutical composition. The nitroimidazole derivative provided by the invention has excellent pharmacokinetic properties, and also has excellent antibacterial activity.
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Paragraph 0013; 0039-0041
(2021/05/12)
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- Novel chiral stationary phases based on 3,5-dimethyl phenylcarbamoylated β-cyclodextrin combining cinchona alkaloid moiety
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Novel chiral selectors based on 3,5-dimethyl phenylcarbamoylated β-cyclodextrin connecting quinine (QN) or quinidine (QD) moiety were synthesized and immobilized on silica gel. Their chromatographic performances were investigated by comparing to the 3,5-dimethyl phenylcarbamoylated β-cyclodextrin (β-CD) chiral stationary phase (CSP) and 9-O-(tert-butylcarbamoyl)-QN-based CSP (QN-AX). Fmoc-protected amino acids, chiral drug cloprostenol (which has been successfully employed in veterinary medicine), and neutral chiral analytes were evaluated on CSPs, and the results showed that the novel CSPs characterized as both enantioseparation capabilities of CD-based CSP and QN/QD-based CSPs have broader application range than β-CD-based CSP or QN/QD-based CSPs. It was found that QN/QD moieties play a dominant role in the overall enantioseparation process of Fmoc-amino acids accompanied by the synergistic effect of β-CD moiety, which lead to the different enantioseparation of β-CD-QN-based CSP and β-CD-QD-based CSP. Furthermore, new CSPs retain extraordinary enantioseparation of cyclodextrin-based CSP for some neutral analytes on normal phase and even exhibit better enantioseparation than the corresponding β-CD-based CSP for certain samples.
- Zhu, Lunan,Zhu, Junchen,Sun, Xiaotong,Wu, Yaling,Wang, Huiying,Cheng, Lingping,Shen, Jiawei,Ke, Yanxiong
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p. 1080 - 1090
(2020/05/25)
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- Preparation method of optically active ornidazole
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The invention relates to the technical field of organic chemical synthesis, in particular to a preparation method of optically active ornidazole. According to the preparation method, 2-methyl-5-nitroimidazole and optically active epoxy chloropropane are used as raw materials, an acid solvent is used as a reaction solvent, Lewis acid is used as a catalyst, a reaction is carried out under the condition close to normal temperature, and then extraction is carried out to obtain the product. Compared with the traditional optically active ornidazole synthesis process, the preparation method has theadvantages that the use of aluminum trichloride is avoided, the pollution of aluminum salt to the environment is reduced, low-temperature control in the reaction process is not needed, the reaction conditions are mild and easy to control, the temperature control cost can be reduced, the types of solvents are fewer, the operation is simple, and the cost is lower; and the method is suitable for industrial production of optically active ornidazole.
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Paragraph 0019-0022; 0026-0048
(2021/01/04)
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- Process for preparing 5-nitroimidazole medicine through catalysis of small organic molecules
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The invention provides a process for preparing a 5-nitroimidazole medicine through catalysis of small organic molecules. The preparation method comprises the following steps: 1) uniformly stirring andmixing 2-methyl-5-nitroimidazole, a solvent and a catalyst which is selected from 1-(3, 5-ditrifluoromethyl phenyl)-3-(2-dimethylamino-cyclohexyl)-thiourea, and 2) adding epoxy chloropropane or epoxypropane into a reaction system in the step 1), and reacting to obtain the 5-nitroimidazole medicine. According to the present invention, the 5-nitroimidazole medicine prepared by using the synthesisprocess has characteristics of low catalyst consumption, high catalytic activity, high reaction selectivity, high yield, easy catalyst recycling, and environmental protection.
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Paragraph 0035-0040; 0047-0050
(2020/08/09)
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- Synthesis method of 5-nitroimidazole drugs
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The invention provides a synthesis method of 5-nitroimidazole drugs. The synthesis method comprises the steps: A) mixing 2-Methyl-5-nitroimidazole, ethyl acetate and aluminum trichloride catalyst supported on macroporous resin to obtain a mixed system; B) dropwise adding epichlorohydrin or propylene oxide to the mixed system and reacting to obtain a 5-Nitroimidazole antimicrobial drug. The aluminum trichloride catalyst supported on resin is adopted, the high catalytic activity of aluminum trichloride is retained, the post-reaction treatment process is simplified, the catalyst can be separatedonly through simple filtration, and the catalyst can be recycled for 3-5 times and activity basically remains unchanged, thus greatly reducing the three wastes of the catalyst used in the traditionalprocess and reducing the energy consumption and cost. Meanwhile, the aluminum trichloride catalyst supported on the resin is adopted and the reaction temperature does not need low temperature reaction, thus saving more energy and improving the reaction yield which can reach 75% ~ 80%.
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Paragraph 0039; 0040; 0043-0050
(2020/04/06)
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- Nitroimidazole derivative, preparation method and applications thereof
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The invention relates to a nitroimidazole derivative, a preparation method and applications thereof, wherein specifically the compound has a structure represented by a formula I, and various groups and various substituents are defined in the specification. The invention further discloses a preparation method of the compound and applications of the compound in prevention, relieve and/or treatment of diseases caused by anaerobic bacteria infection.
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Paragraph 0139-0146
(2020/02/29)
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- High-safety L-ornidazole injection and preparation method thereof
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The invention provides a high-safety L-ornidazole injection. The high-safety L-ornidazole injection comprises L-ornidazole and an isoosmotic regulator component, and is characterized by containing nitrate, wherein the nitrate content is not higher than 30mg/l. The L-ornidazole injection is high in safety and low in toxicity, and the clinical therapeutic effect of the L-ornidazole can be better played.
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Paragraph 0052; 0053; 0056; 0059; 0062
(2018/04/03)
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- Novel nitroimidazole drug as well as preparation method and application of novel nitroimidazole drug
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The invention relates to a novel nitroimidazole compound as well as a preparation method and application of the novel nitroimidazole compound to medical science and specifically relates to a nitroimidazole compound as shown in a general formula (I), a preparation method of the nitroimidazole compound and a pharmaceutical composition containing the compound. The invention aims at synthesizing a novel compound of a series of nitroimidazole derivatives by modifying the structure of a nitroimidazole compound, the compound can be used for obviously reducing adverse reaction in clinic, meanwhile, the compound has a relatively ideal effect on protecting the liver and kidneys, and the clinical application of the compound is apparent.
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Paragraph 0024
(2018/04/01)
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- S-ornidazole injection with high safety and preparation method thereof
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The invention provides an s-ornidazole injection with high safety. The s-ornidazole injection is prepared from components of s-ornidazole and an isoosmotic adjusting agent; the s-ornidazole injection is characterized in that the s-ornidazole injection contains acetamide, wherein the content of the acetamide is not higher than 10 mg/l. The s-ornidazole injection provided by the invention is high in safety and low in toxicity, and is capable of well exerting the clinical effects of the s-ornidazole.
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Paragraph 0051-0052
(2017/10/07)
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- After-treatment method for levornidazole reaction liquid
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The invention discloses an after-treatment method for levornidazole reaction liquid and belongs to the technical field of medicine synthesis. The method includes the steps of 1) adding 2-methyl-5-nitroimidazole to ethyl acetate; 2) under catalysis of aluminum chloride, adding S-epoxychloropropane to perform a reaction to obtain a reaction liquid; 3) quenching the reaction liquid in ice water, separating the reaction liquid to obtain an ethyl acetate phase, and drying the ethyl acetate phase and performing pressure-reduced concentration to obtain an oily substance; 4) adding an organic solvent to the oily substance and pulping the mixture, adding a low-polar solvent to further separate a solid out; and 5) filtering and drying the solid to obtain levornidazole. The after-treatment method is free of addition of acid and alkali for regulating pH value, so that generation of a thermal degradation impurity due to acid-base neutralization heat release can be avoided. The method is simple in operation, is high in yield and is suitable for industrial production.
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Paragraph 0026; 0027
(2016/12/01)
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- A new optical enantiomer of ornidaxole of preparation and its purification method
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The invention provides a preparation and refining method for a new ornidazole optical antimer. The method comprises the following steps of: adding 2-methyl-5-nitroimidazole into an acid solution with a catalyst to react with chiral epoxy chloropropane to generate an ornidazole optical antimer, performing re-crystallization on the ornidazole optical antimer by using a mixed solution of an organic solvent and water, and thus obtaining the high-purity ornidazole optical antimer.
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Paragraph 0006; 0018-0021
(2017/02/17)
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- L-ornidazole α crystal and its preparation method (by machine translation)
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The invention belongs to the technical field of preparation of pharmaceutical forms, and, in particular relates to a crystalline α L-ornidazole and method for preparing the same. Crystalline α of the L-ornidazole, using cu-Kα radiation, in order to 2 the angle of the X-ray powder diffraction in 10.7 ±0 . 2 °, 14.3 ±0 . 2 °, 15.9 ±0 . 2 °, 18.0 ±0 . 2 °, 21.6 ±0 . 2 °, 22.2 ±0 . 2 °, 23.8 ±0 . 2 °, 24.7 ±0 . 2 °, 25.3 ±0 . 2 °, 28.8 ±0 . 2 °, 29.3 ±0 . 2° and 31.2 ±0 . 2° is displayed X-ray powder diffraction peak. Crystalline α L-ornidazole of this invention high purity, quality stability is good; the preparation method has a simple process, the solvent used for less harm to human body, safety, is suitable for industrial production. The invention yield is 80-90%, the product purity ≥ 99.9%. (by machine translation)
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Paragraph 0030; 0031; 0032; 0033
(2016/11/28)
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- 2-Methyl-4/5-nitroimidazole derivatives potentiated against sexually transmitted Trichomonas: Design, synthesis, biology and 3D-QSAR study
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Trichomoniasis is the most prevalent, non-viral sexually transmitted diseases (STD) caused by amitochondriate protozoan Trichomonas vaginalis. Increased resistance of T.?vaginalis to the marketed drug Metronidazole necessitates the development of newer chemical entities. A library of sixty 2-methyl-4/5-nitroimidazole derivatives was synthesized via nucleophilic ring opening reaction of epoxide and the efficacies against drug-susceptible and -resistant Trichomonas vaginalis were evaluated. All the molecules except two were found to be active against both susceptible and resistant strains with MICs ranging 8.55–336.70?μM and 28.80–1445.08?μM, respectively. Most of the compounds were remarkably more effective than the standard Metronidazole. This study analyzes the in?vitro and in?vivo activities of the new 5-nitroimidazoles, which were found to be safe against human cervical HeLa cells with good selectivity index. The exploration of SAR by the synthesis of four different prototypes and 3D-QSAR study has shown the importance of prototype 1 over other prototypes.
- Mandalapu, Dhanaraju,Kushwaha, Bhavana,Gupta, Sonal,Singh, Nidhi,Shukla, Mahendra,Kumar, Jitendra,Tanpula, Dilip K.,Sankhwar, Satya N.,Maikhuri, Jagdamba P.,Siddiqi, Mohammad I.,Lal, Jawahar,Gupta, Gopal,Sharma, Vishnu L.
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p. 820 - 839
(2016/09/23)
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- Synthesis, antimicrobial activities and binding mode analysis of some novel N-substituted imidazoles and nitroimidazoles
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Novel N-((2-(aryl)-imidazol-1-yl) methyl)-anilines 2a-n and 1-(3'-arylamino-2'- hydroxypropyl)-2-methyl-4-nitroimidazoles 4a-g have been synthesized. The compounds have been characterized on the basis of elemental analysis and spectral data. All the compounds were evaluated for their antibacterial activities. Among the synthesized compounds, compounds 2m, 2n and compounds 4c, 4e exhibited highest inhibitory activity against all the bacterial strains, comparable to the standard drug ciprofloxacin. Binding mode analysis of the highest active compounds was carried out in the active site of GlcN-6-P synthase (2VF5).
- Ganguly, Swastika,Mishra, Surbhi,Gupta, Ankita,Sankrityayan, Ira,Dev, Abhimanyu
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p. 373 - 380
(2019/01/21)
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- Chemical compounds having ion channel blocking activity for the treatment of immune dysfunction
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The present invention relates to chemical compounds having inhibitory activity on an intermediate conductance Ca 2+ activated potassium channel (IK Ca), and the use of such compounds for the treatment or alleviation of diseases or conditions relating to immune dysfunction. Moreover, the invention relates to a method of screening a chemical compound for inhibitory activity on an intermediate conductance Ca 2+ activated potassium channel (IK Ca).
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- Lipase-catalyzed resolution of both enantiomers of Ornidazole and some analogues
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The resolution of the enantiomers of the chemotherapeutic Ornidazole (Tiberal) 1a was achieved by acetylation of the racemic compound with vinylacetate in the presence of lipase Amano PS (from Pseudomonas cepacia). The halogen analogues 4a-6a and the corresponding 4-nitro-derivatives 1b and 4b-6b were also synthesized and the enantiomers were separated by kinetic enzymatic resolution. The absolute configuration of two compounds was determined by X-ray crystallography.
- Skupin, Rolf,Cooper, Trevor G.,Froehlich, Roland,Prigge, Joerg,Haufe, Guenter
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p. 2453 - 2464
(2007/10/03)
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