- Synthesis method of glibenclamide
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The invention discloses a synthesis method of glibenclamide, which includes the steps of: 1) protection of amino groups with trichloroacetic anhydride; 2) sulfonation; 3) sulfo-amidation; 4) amidation: performing a reaction to 5-chloro-2-methoxybenzoic acid with N,N-carbonyl diimidazole and performing a reaction to the product with a compound (III) under effect of a second acid-binding agent; 5) addition: adding the second acid-binding agent and crown ether, in catalytic amount, to perform an addition reaction to a compound (IV) with cyclohexyl isocyanate to prepare the glibenclamide. The method is high in yields in all steps, wherein residue of impurities is effectively reduced during processes of protection, deprotection, acid treatment, alkali treatment and water-adding separation of the substrate. According to the method, a phase-transfer catalyst is matched with the second acid-binding agent, so that compatibility between the isocyanate and the compound (IV) is effectively increased, and the nucleophilic reaction is carried out more completely. The produced product is higher in purity.
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Paragraph 0050
(2018/04/26)
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- Synthesis and biological evaluation of sulfonylurea and thiourea derivatives substituted with benzenesulfonamide groups as potential hypoglycemic agents
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A novel class of sulfonylurea and thiourea derivatives substituted with benzenesulfonamide groups were designed and synthesized. The target compounds were assayed for the effects on the insulin release of isolated rat pancreatic islets and the glucose transport in adipocytes of rats. Some of them exhibited high potency. Compound 10 also had potent antiplatelet activity and showed an excellent property to protect collagen-epinephrine-induced mice mortality as well as plasma glucose-lowering activity in vivo. The preliminary pharmacological profile of compound 10 showed that it might be useful in the treatment of diabetics with cardiovascular and nephropathy complications.
- Zhang, Hui-bin,Zhang, Ya-an,Wu, Guan-zhong,Zhou, Jin-pei,Huang, Wen-long,Hu, Xiao-wen
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scheme or table
p. 1740 - 1744
(2009/12/03)
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- Novel synthesis of mafenide and other amino sulfonamides by electrochemical reduction of cyano sulfonamides
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Both aliphatic and aromatic amino sulfonamides such as mafenide (1a) were synthesized in good yields (80-86%) by direct electrochemical hydrogenation of the corresponding nitriles in an undivided cell containing a Ni cathode, a Pt anode, and Raney Ni as catalyst (Table 1). The reaction can be performed without external supply of pressurized gas by in situ generation of H2. Slightly elevated temperatures (45°) and low current densities (10 mA/cm2) are favorable conditions for this type of electrochemical nitrile hydrogenation. Our synthetic protocol does not require high-pressure equipment or chemical hazards, is environmentally very friendly, and more economical than traditional methods. The concentration of adsorbed H. radicals on the catalyst surface can be easily controlled by adjusting the electric potential, which may lead to improved product selectivity and, at the same time, reduces the risk of explosion and fire.
- Lateef, Shaik,Mohan, Srinivasulu Reddy Krishna,Rameshraju, Rudraraju,Reddy, Srinivasulu,Reddy, Javarama
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p. 1254 - 1257
(2007/10/03)
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- N-(4-[2-(pyrazole-1-carbonamide)-ethyl]-benzenesulphonyl)-urea
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N-{4-[2-(Pyrazole-1-carbonamide)-ethyl]-benzenesulphonyl}-ureas of the formula 1 STR1 wherein R, R2 are a hydrogen atom or lower alkyl of up to 4 carbon atoms, R1 is a hydrogen, chlorine or lower alkyl atom containing up to 4 carbon atoms and R3 is an alkyl of 2 to 5 carbon atoms or cycloalkyl of 5 to 6 carbon atoms, and their method of preparation is described, said compounds possessing biological properties, capable of decreasing the sugar level in blood.
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