Synthesis process of candesartan cilexetil

A technology of candesartan medoxomil and a synthesis process, which is applied in the field of synthesis technology of candesartan medoxomil, can solve the problem that the treatment of tin-containing wastewater is difficult, increases the treatment cost of "three wastes", and increases the technological process of candesartan medoxomil. Difficulty in production and other problems, to achieve the effect of cheap price, simple processing, and improved reaction yield

Inactive Publication Date: 2013-05-01
WUHAN INSTITUTE OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At the same time, the treatment of tin-containing wastewater generated in the process is difficult, which undoubtedly increases t...

Method used

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  • Synthesis process of candesartan cilexetil
  • Synthesis process of candesartan cilexetil
  • Synthesis process of candesartan cilexetil

Examples

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Embodiment 1

[0017] 8.22g (0.02mol) intermediate 8（ 1-[(2'-cyano-1,1'-biphenyl-4-yl)methyl]-2-ethoxy-7-benzimidazolecarboxylic acid ethyl ester) dissolved in 30mL DMF (0.388 mol), add 1.43g (0.022mol) NaN 3 and 1.18g (0.022mol) NH 4 Cl, heat up to 135-140°C for 24 hours, cool down to room temperature, distill off DMF under reduced pressure, add 100mL of water, wash twice with toluene 50mLx2, then adjust the pH to 6 with 1N HCl, solids precipitate out, filter, and use for filter cake Methanol was recrystallized to obtain 5.7 g of a white solid with a melting point of 190-192°C (literature value: 192-194°C), and a yield of 63.5%. The reaction equation involved in the present invention is:

[0018]

Embodiment 2

[0020] 8.22g (0.02mol) ethyl 1-[(2'-cyano-1,1'-biphenyl-4-yl)methyl]-2-ethoxy-7-benzimidazolecarboxylate Dissolve in 40mL DMF (0.517mol), add 1.56g (0.024mol) NaN 3 and 6.52g (0.048mol) ZnCl 2 , heated up to 160°C for 30 hours, lowered to room temperature, distilled off DMF under reduced pressure, added 100mL of water, washed twice with toluene 50mLx2, then adjusted the pH to 7 with 1N HCl, solid precipitated, filtered, and the filter cake was recrystallized with methanol 6.1 g of white solid was obtained, its melting point was measured at 189-191°C (literature value: 192-194°C), and the yield was 67.1%.

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Abstract

The invention relates to a process improving method of candesartan cilexetil; 1-[(2'-cyano-1, 1'-xenyl-4-) methyl]-2-ethyoxyl-7-benzimidazole carboxylic acid ethyl ester and sodium azide serve as raw materials, N,N-dimethyl formamide serves as solvent, MC1 serves as catalyst, and the materials are synthesized into candesartan cilexetil at the temperature of 130DEG C to 160DEG C, wherein M is alkali metal or an ammonium cation. According to the method, the price of the used catalyst is low, no toxin or little toxin is produced, the production cost and the environmental treatment cost are reduced, the treatment after reaction is simple, the yield is higher, and the industrialized production is facilitated.

Description

technical field [0001] The invention relates to a synthesis process of candesartan cilexetil. Background technique [0002] Candesartan is a non-peptide angiotensin Ⅱ receptor antagonist, because it increases the specificity and selectivity of blocking angiotensin Ⅱ receptor levels in the circulatory system and tissues, and has a higher conversion rate than angiotensin Ⅱ Enzyme (ACE) inhibitors have more superior characteristics, good blood pressure lowering effect, and few adverse reactions. Candesartan cilexetil is the prodrug of candesartan, which is rapidly and completely hydrolyzed into candesartan during absorption through the gastrointestinal tract to play a role. [0003] The current method for preparing candesartan cilexetil (US5196444) mainly uses 3-nitro-1,2-benzenedicarboxylic acid (2) as the starting material, and undergoes esterification, chlorination, and Curtis rearrangement to obtain 3-nitro -Ethyl 2-tert-butoxycarboxamidobenzoate (5), then undergoes a sub...

Claims

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Application Information

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IPC IPC(8): C07D403/10
Inventor 王凯张秀兰黄婷郭嘉尹传奇张珩
Owner WUHAN INSTITUTE OF TECHNOLOGY
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