Preparation method of propranolol hydrochloride single enantiomers

A technology for propranolol hydrochloride and enantiomer, which is applied in the field of preparation of propranolol hydrochloride single enantiomer, can solve the problems of easy side effects, poor therapeutic efficacy for heart system diseases, etc. High-yield, easy-to-obtain results

Inactive Publication Date: 2013-04-10
王荣
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, administration in racemic form not only has poor therapeutic effect on heart system diseases, but also easily brings side effects.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] The preparation method of embodiment 1 propranolol hydrochloride single enantiomer, comprises the following steps:

[0021] (1) Propranolol hydrochloride racemate bulk drug was dissolved in absolute ethanol at a temperature of 30° C. to prepare a saturated solution with a concentration of 50 mg / mL.

[0022] (2) Inject the saturated solution obtained in step (1) into the high performance liquid chromatography system, with n-hexane-ethanol-isopropanol-diethylamine as the mobile phase and the chiral chromatographic column as the stationary phase, at 30 ° C Temperature, UV detection wavelength of 293nm, flow rate of 4.8mL / min, injection volume of 10mg / time after separation under chromatographic conditions, the propranolol enantiomer A fraction within the range of 7.8 to 9.75min in the chromatogram was obtained - R(+)-propranolol enantiomer fraction, propranolol enantiomer B fraction in the range of 10.9-13.0 min - S(-)-propranolol enantiomer fraction.

[0023] Wherein: the...

Embodiment 2

[0027] The preparation method of embodiment 2 propranolol hydrochloride single enantiomer, comprises the following steps:

[0028] (1) Propranolol hydrochloride racemate bulk drug was dissolved in absolute ethanol at a temperature of 15° C. to prepare a saturated solution with a concentration of 40 mg / mL.

[0029] (2) Inject the saturated solution obtained in step (1) into the high performance liquid chromatography system, with n-hexane-ethanol-isopropanol-diethylamine as the mobile phase and the chiral chromatographic column as the stationary phase, at 15°C Temperature, UV detection wavelength of 293nm, flow rate of 5.0mL / min, injection volume of 8mg / time after separation under chromatographic conditions, the propranolol enantiomer A fraction within the range of 9.0 to 11.0min in the chromatogram was obtained - R(+)-propranolol enantiomer fraction, propranolol enantiomer B fraction in the range of 13-15.0 min - S(-)-propranolol enantiomer fraction.

[0030] Wherein: the volu...

Embodiment 3

[0034] The preparation method of embodiment 3 propranolol hydrochloride single enantiomer, comprises the following steps:

[0035] (1) Propranolol hydrochloride racemate bulk drug was dissolved in absolute ethanol at a temperature of 5° C. to prepare a saturated solution with a concentration of 30 mg / mL.

[0036] (2) Inject the saturated solution obtained in step (1) into the high performance liquid chromatography system, with n-hexane-ethanol-isopropanol-diethylamine as the mobile phase and the chiral chromatographic column as the stationary phase, at 5 ° C Temperature, UV detection wavelength of 293nm, flow rate of 4.0mL / min, injection volume of 6mg / time after separation under chromatographic conditions, the propranolol enantiomer A fraction within the range of 9.0 to 10.5min in the chromatogram was obtained - R(+)-propranolol enantiomer fraction, propranolol enantiomer B fraction in the range of 11.5-13.5 min - S(-)-propranolol enantiomer fraction.

[0037] Wherein: the vo...

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Abstract

The invention relates to a preparation method of propranolol hydrochloride single enantiomers, comprising the following steps of: (1) preparing a saturated solution from a raw material drug of propranolol hydrochloride raceme; (2) injecting the saturated solution to a high efficiency liquid chromatography system, and separating according to conditions that n-hexane-ethanol-isopropanol-diethylamine is used as a mobile phase and a chiral chromatographic column is used as a stationary phase to obtain propranolol enantiomer fraction A and fraction B within different peak value ranges of a chromatogram map; (3) concentrating and then evaporating the propranolol enantiomer fraction A and fraction B respectively to obtain propranolol hydrochloride single enantiomer crude products A and B; (4) adding n-butyl to the propranolol hydrochloride single enantiomer crude products A and B respectively, and dissolving by heating to form hot saturated solutions A and B; and (5) filtering, cooling and drying the hot saturated solutions A and B respectively to obtain propranolol hydrochloride single enantiomers A and B. The preparation method of the invention is simple in process and can simultaneously obtain two enantiomers with high optical rotation purity at a high yield.

Description

technical field [0001] The invention relates to the field of chiral drug enantiomers, in particular to a preparation method of a single enantiomer of propranolol hydrochloride. Background technique [0002] Due to the difference in the three-dimensional configuration of the enantiomers of chiral drugs, there are significant differences in the pharmacological activity, metabolic process and toxicity of different enantiomers in the human body. Usually the desired pharmacological activity exists in one enantiomer, while the other enantiomer may have lower activity, or have toxicity or side effects. At present, the US Food and Drug Administration and relevant departments in many western countries have made a decision to prohibit the sale of racemic drugs on the market. It must be split into a single left-handed or right-handed body before it can be marketed as a product. Methods for obtaining optically pure single enantiomers include chiral source synthesis, asymmetric synthesi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C217/30C07C213/10
Inventor 王荣谢华杨沛贾正平
Owner 王荣
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