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Ivabradine intermediate compound IV

A technology for ivabradine and compounds, applied in the field of ivabradine intermediate compound IV, can solve the problems of high technical requirements, high production costs, environmental pollution, etc., achieve economical and environmentally friendly yields, easy operation, and high product purity Effect

Active Publication Date: 2021-09-10
LUNAN PHARMA GROUP CORPORATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] In order to solve the problems of long route, cumbersome operation, low yield and low purity in the preparation process of ivabradine in the prior art; or high technical requirements, serious environmental pollution and high production cost, the invention provides a kind of ivabradine intermediate IV, and provides a preparation method for the compound; and a new method for synthesizing ivabradine using the compound, the method has a short reaction route, is easy to operate, has milder reactions, is economical and environmentally friendly, and has a high yield, and is suitable for industrialization Production

Method used

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  • Ivabradine intermediate compound IV

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Embodiment 1

[0055] Compound II, 7,8-dimethoxy-1,3,4,5-tetrahydro-benzazepine-2-one (44.3g, 0.2mol) was dissolved in 250ml DMSO at room temperature, and added in batches Potassium tert-butoxide (26.9g, 0.24mol) was stirred for 10min, and compound III (3-chloro-propyl)-methyl-carbamic acid tert-butyl ester (53.9g, 0.26mol) and DMSO ( 120ml) mixed solution, after the reaction was completed, the reaction solution was poured into pure water (150ml), stirred to precipitate solid, suction filtered, added 200ml acetone for beating, suction filtered until no filtrate flowed out, and vacuum dried at 40°C to obtain compound IV. 99.8%, HPLC purity 99.85%.

Embodiment 2

[0057] Compound II, 7,8-dimethoxy-1,3,4,5-tetrahydro-benzazepine-2-one (44.3g, 0.2mol) was dissolved in 250ml DMSO at room temperature, and added in batches Sodium tert-butoxide (23.1g, 0.24mol) was stirred for 10min, and compound III (3-chloro-propyl)-methyl-carbamic acid tert-butyl ester (45.6g, 0.22mol) and DMSO ( 120ml) mixed solution, after the reaction was completed, the reaction solution was poured into pure water (150ml), stirred to precipitate solid, suction filtered, added 200ml acetone for beating, suction filtered until no filtrate flowed out, and vacuum dried at 40°C to obtain compound IV. 94.3%, HPLC purity 99.81%.

Embodiment 3

[0059] Compound II, 7,8-dimethoxy-1,3,4,5-tetrahydro-benzazepin-2-one (44.3g, 0.2mol) was dissolved in 250ml of benzene at room temperature, and added in batches Potassium carbonate (33.2g, 0.24mol) was stirred for 10min, and the mixed solution of compound III (3-chloro-propyl)-methyl-carbamic acid tert-butyl ester (82.9g, 0.40mol) and benzene (120ml) was added dropwise After the reaction was completed, the reaction solution was poured into pure water (150ml), stirred to precipitate solids, filtered with suction, added 200ml of acetone for beating, filtered with suction until no filtrate flowed out, and dried in vacuo at 40°C to obtain compound IV with a yield of 95.6% and an HPLC purity of 99.76 %.

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Abstract

The invention belongs to the field of pharmaceutical chemicals, and particularly relates to an ivabradine intermediate compound IV. The method for preparing the ivabradine intermediate compound IV comprises the steps of dissolving 7, 8-dimethoxy-1, 3, 4, 5-tetrahydro-benzazepin-2-one in an organic solvent, adding alkali, stirring, and dropwise adding (3-chlorine-propyl)-methyl-tert-butyl carbamate into the obtained solution to obtain the compound IV. The invention provides a novel intermediate compound IV of ivabradine, and provides a novel method for simply and efficiently preparing ivabradine by using the compound, and the whole synthesis method is simple and convenient to operate, high in reaction yield, high in purity of the obtained product, and more suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of medicine and chemical industry, and in particular relates to an ivabradine intermediate compound IV. Background technique [0002] Ivabradine (ivabradine), chemical name 3-(3-{[((7S)-3,4-dimethoxybicyclo[4.2.0]oct-1,3,5-trien-7-yl )methyl]methylamino}propyl)-1,3,4,5-tetrahydro-7,8-dimethoxy-2H-3-benzazepine -2-ketone, the first selective and specific IF (controlling spontaneous diastolic depolarization in the sinoatrial node and regulating heart rate) inhibitor, has a selective effect on the sinoatrial node but has no effect on intracardiac conduction, myocardial contraction or ventricular recovery Polarization has no effect; on October 25, 2005, it was approved by the European Medicines Evaluation Agency (EMA) for marketing, and the product name is Procoralan, which is used for the treatment of patients with normal sinus rhythm who are contraindicated or intolerant to β-blockers Symptomatic treatment of chronic...

Claims

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Application Information

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IPC IPC(8): C07D223/16
CPCC07D223/16C07B2200/07Y02A50/30
Inventor 霍领雁时江华刘忠
Owner LUNAN PHARMA GROUP CORPORATION
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