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Preparation method of tamsulosin hydrochloride

A technology of tamsulosin hydrochloride and tamsulosin, which is applied in the preparation of sulfonamides and organic chemistry, can solve problems such as pollution, and achieve the effects of high purity, reduced reaction time, and good stability

Active Publication Date: 2013-01-30
BEIJING YUEKANGKECHUANG PHARM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The reaction solvents of the above methods are all organic solvents, such as dimethylformamide, acetonitrile, etc., and a post-treatment process is required simultaneously, causing serious pollution

Method used

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  • Preparation method of tamsulosin hydrochloride
  • Preparation method of tamsulosin hydrochloride
  • Preparation method of tamsulosin hydrochloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] (1) Preparation of R-Tamsulosin free base

[0037] R-(-)-5-(2-aminopropyl)-2-methoxybenzenesulfonamide hydrochloride (56g; 0.2mol), o-ethoxyphenoxyethyl bromide (49g; 0.2mol) 1. Potassium carbonate (56g; 0.4mol) was added to 600ml of water, and at 85°C, it was incubated for 8 hours. After the reaction was completed, it was cooled to room temperature, filtered with suction, and the filter cake was washed with 100ml of water and 100ml of methanol, and dried to obtain 56g of R- Tamsulosin free base, add 56g R-Tamsulosin free base into 500ml of anhydrous methanol, heat to dissolve, slowly cool down to 25°C, stir and crystallize for 10 hours, filter, wash with 100ml of anhydrous methanol, and drum at 50°C After air-drying, 50 g of R-Tamsulosin free base (HPLC purity 99.92%, optical purity (chiral HPLC): S-Tamsulosin: 0.03%) was obtained.

[0038] (2) Preparation of R- tamsulosin hydrochloride

[0039] Add 50g of high-purity R-Tamsulosin free base to 400ml of anhydrous meth...

Embodiment 2

[0041] (1) Preparation of R-Tamsulosin free base

[0042] R-(-)-5-(2-aminopropyl)-2-methoxybenzenesulfonamide hydrochloride (280g; 1mol), o-ethoxyphenoxyethyl bromide (245g; 1mol), carbonic acid Potassium (276g; 2mol) was added to 4200ml of water, and kept at 90°C for 7 hours. After the reaction, it was cooled to room temperature, filtered with suction, and the filter cake was washed with 500ml of water and 500ml of methanol, and dried to obtain 280g of R-Tamsulol Add 280g of R-Tamsulosin free base to 2800ml of anhydrous methanol, heat to dissolve, slowly cool down to 25°C, stir and crystallize for 9 hours, filter, wash with 500ml of anhydrous methanol, and dry to obtain 240g of R-Tamsulosin Sorosin free base (HPLC purity 99.89%, optical purity (chiral HPLC): S-Tamsulosin: 0.05%).

[0043] (2) Preparation of R- tamsulosin hydrochloride

[0044] Add 240g of high-purity R-Tamsulosin free base to 1900ml of anhydrous methanol, stir and dissolve at 60-70°C, add hydrochloric acid ...

Embodiment 3

[0046] (1) Preparation of R-Tamsulosin free base

[0047]R-(-)-5-(2-aminopropyl)-2-methoxybenzenesulfonamide hydrochloride (280g; 1mol), o-ethoxyphenoxyethyl bromide (245g; 1mol), carbonic acid Sodium (212g; 2mol) was added to 2800ml of water, and kept at 90°C for 10 hours. After the reaction, it was cooled to room temperature, filtered with suction, and the filter cake was washed with 500ml of water and 500ml of methanol, and dried to obtain 285g of R-Tamsulol Add 285g of R-Tamsulosin free base to 2280ml of anhydrous methanol, heat to dissolve, slowly cool down to 27°C, stir and crystallize for 12 hours, filter, wash with 400ml of anhydrous methanol, and dry to obtain 250g of R-Tamsulosin Sorosin free base (HPLC purity 99.92%, optical purity (chiral HPLC): S-Tamsulosin: 0.04%).

[0048] (2) Preparation of R- tamsulosin hydrochloride

[0049] Add 250g of high-purity R-Tamsulosin free base to 2500ml of anhydrous methanol, stir and dissolve at 60-70°C, add hydrochloric acid dr...

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Abstract

The invention relates to a preparation method of tamsulosin hydrochloride, which comprises the following steps: reacting R-(-)-5-(2-aminopropyl)-2-metoxybenzsulfamide hydrochloride and o-ethoxylphenoxylethyl bromide to obtain R-tamsulosin free alkali, and reacting the free alkali with hydrochloric acid to obtain the R-tamsulosin hydrochloride. The invention is characterized in that the reaction of the R-(-)-5-(2-aminopropyl)-2-metoxybenzsulfamide hydrochloride and o-ethoxylphenoxylethyl bromide is carried out in a water-containing solvent.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a synthesis method of tamsulosin hydrochloride. Background technique [0002] Tamsulosin Hydrochloride is the third-generation super-selective long-acting αLA-adrenergic receptor antagonist, which was successfully developed by Yamanouchi Pharmaceutical in Japan. It was approved by the FDA in July 1992. The trade name is Harnal (Hale). . Since then, it has jointly sold tamsulosin hydrochloride with Boehringer Ingelheim and Abbott, and was approved by the FDA in 1997 under the trade name Flomax. The drug can specifically inhibit the contraction of the smooth muscle of the prostate, rapidly relieve the clinical symptoms of BPH, has good curative effect and fewer adverse reactions. [0003] The structural formula (I) of tamsulosin hydrochloride is: [0004] [0005] Currently, there are various methods for preparing tamsulosin hydrochloride. The main met...

Claims

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Application Information

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IPC IPC(8): C07C311/37C07C303/40
Inventor 陶秀梅高宏伟秦元满
Owner BEIJING YUEKANGKECHUANG PHARM TECH CO LTD
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