Method for preparing anti-platelet aggregation compounds
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A compound, hydrazine hydrate technology, applied in the field of chemical pharmacy, can solve the problem of high raw material price, achieve the effect of stable product quality, obvious effect and lower production cost
Active Publication Date: 2012-07-04
天津药物研究院药业有限责任公司
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Problems solved by technology
[0019] Aiming at the deficiencies of the prior art, the present invention provides a method for preparing the compound of formula I suitable for large-scale industrial production. The purpose of the present invention is to overcome the disadvantage of high raw material prices in the existing synthesis method, and to select low-cost and easy-to-obtain compounds while ensuring product quality. Raw materials, thereby reducing production costs, suitable for large-scale industrial production
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Embodiment 1
[0034] Example 1 : Synthesis of Intermediate III-1
[0035]
[0036] Heat the solution of intermediate II obtained in the previous step to 50°C, add a mixture of 8.34g (0.1mol) of 60% hydrazine hydrate and 5.81g (0.1mol) of acetone under stirring, and react at 50°C for 1h (the plate layer shows the reaction completely). The reaction was stopped, cooled, and a solid was formed. Filter and dry to obtain 30.3 g of solid product (HPLC: 99.8%), with a yield of 86.7%. Rf=0.41 [single site, developer: ethyl acetate:petroleum ether (60-90°C)=1:1].
Embodiment 2
[0037] Example 2: Synthesis of Intermediate III-2
[0038]
[0039] The solution of intermediate II obtained in the previous step was heated up to 60°C, and a mixture of 6.67g (0.12mol) of 90% hydrazine hydrate and 10.3g (0.12mol) of 3-pentanone was added under stirring, and reacted at 60°C for 0.5h ( Plates show complete reaction). The reaction was stopped, cooled, and a solid was formed. Filter and dry to obtain 33.4 g of solid product (HPLC: 99.0%), yield 87.4%. Rf=0.45 [single site, developing solvent: ethyl acetate:petroleum ether (60-90°C)=1:1].
Embodiment 3
[0040] Example 3: (S)-α,α-[2-Chlorophenyl-2-(4,5,6,7-tetrahydrothieno[3,2-c]pyridin-5-yl)]-N'-[( Dimethyl)methylene]acetylhydrazide
[0041]
[0042]In a 250mL reaction flask equipped with stirring, condenser and thermometer, add 3.5g (0.01mol) of intermediate III-1, add 10mL (0.04mol) of 15% formic acid solution, and add 0.6g (0.02mol) of formaldehyde under stirring . The temperature was raised to 50°C to continue the reaction for 0.5h (the plate showed that the reaction was complete). The reaction was stopped, extracted with 3×10 mL of dichloromethane, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 3.24 g of solid product (HPLC: 99.3%), with a yield of 89.4%. m.p.169.0-170.6°C, Rf=0.37 [single site, developer: ethyl acetate:petroleum ether (60-90°C)=1:1].
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Abstract
The invention belongs to the technical field of pharmaceutical chemistry, in particular to a new method for preparing anti-platelet aggregation compounds with a structure shown in a general formula I. In the preparation route, cheap and readily available initiative materials, namely methyl alpha-bromo-2-chlorophenylacetate and thiophene-2-ethylamine, replace clopidogrel in the conventional document. Concretely, the methyl alpha-bromo-2-chlorophenylacetate is reacted with the thiophene-2-ethylamine, replace clopidogrel under the catalysis of an acid-catcher to generate an intermediate II; the intermediate II is reacted with hydrazine hydrate, acetone or 3-pentanone to generate an intermediate III; and the intermediate III undergoes cyclization to generate the compounds in the formula I. The method has the advantages of mild reaction conditions, simple and safe operating process, and easy industrial production; and the product has stable quality, high purity and high yield; compared with that of the synthetic process provided by the conventional document, the production cost is greatly reduced; and in the formula I, R refers to methyl or ethyl.
Description
technical field [0001] The invention belongs to the technical field of chemical pharmacy, in particular to a synthesis method of a class of anti-platelet aggregation compounds, in particular to an industrial production method of the anti-platelet aggregation compounds. Background technique [0002] Thrombosis can lead to acute myocardial infarction, stroke, pulmonary embolism and other diseases of the heart, brain, and pulmonary circulation, threatening human health and life, and is also a common complication in surgery and a factor of reocclusion after interventional angioplasty. Although thrombolytic therapy, interventional therapy and even surgical treatment carried out in recent years have made remarkable progress in the treatment of acute myocardial infarction and cerebral infarction, the success rate of patient rescue has been greatly improved, and the quality of life has also been significantly improved, but cardiovascular and cerebrovascular After all, the disability...
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