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Preparation method for tenofovir monoester fumarate

A technology of tenofovir and fumaric acid, which is applied in the field of pharmaceutical chemical synthesis, can solve the problems that tenofovir monoxil fumarate has not been reported, and achieve high product purity, easy storage, and increased economic value Effect

Active Publication Date: 2014-01-22
FUJIAN COSUNTER PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] Tenofovir monodisoproxil has been reported above, but tenofovir monodisoproxil fumarate has not been reported so far

Method used

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  • Preparation method for tenofovir monoester fumarate
  • Preparation method for tenofovir monoester fumarate
  • Preparation method for tenofovir monoester fumarate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Embodiment 1. The preparation of tenofovir monoplastil

[0040] Take tenofovir 10.0g+DMF100mL+triethylamine 16.6g, stir at room temperature for 1h, then add 25.0g of chloromethyl isopropyl carbonate dropwise at temperature control reaction solution ≤ 50°C, continue to stir for 5h after the dropwise addition, close Heating, cooling to room temperature, filtering to remove solids, adding 200ml of ethanol, and concentrating the reaction solution at 50°C to dryness to obtain a gel. Then add 100ml of water and stir, it turns white and turbid, add 100ml*2 for extraction, the liquid becomes clear, separate the water layer (the ethyl acetate layer is treated separately), add 200ml of ethanol, and concentrate to dryness at 50°C to obtain a gel. First use 10ml of isopropanol to heat and dissolve, then slowly add 100ml of petroleum ether, cool naturally, separate out a white solid, filter with suction, and dry to obtain 3.7g of tenofovir monodivoxil solid, yield: 26.39%, purity 99...

Embodiment 2

[0042] Embodiment 2. The preparation of tenofovir monodisoproxil fumarate

[0043] Get 0.86g fumaric acid+25ml isopropanol, stir and dissolve at normal temperature, then slowly add tenofovir monoxate 2g in embodiment 1, tenofovir monoxate dissolves first and then separates out white powdery solid, filter , dried to obtain 2.6g of tenofovir monodisoproxil fumarate, yield: 92.56%, purity 99.93% (attached figure 2 ).

Embodiment 3

[0044] Embodiment 3. The preparation of tenofovir monoplastil

[0045] Take tenofovir 100g+DMF1000mL+triethylamine 166g, stir at room temperature for 1h, then add 250g of chloromethyl isopropyl carbonate dropwise at temperature control reaction solution ≤50°C, continue stirring for 6h after the dropwise addition, turn off the heating, and cool After reaching room temperature, the solid was removed by filtration, 2000 ml of ethanol was added, and the reaction solution was concentrated to dryness at 50° C. to obtain a gel. Then add 500ml of water and stir, it turns white and turbid, add 300ml*2 for extraction, the liquid becomes clear, separate the water layer (the ethyl acetate layer is treated separately), add 200ml of ethanol several times to help desolvation, and concentrate to dryness at 50°C to obtain jelly. First heat and dissolve with 100ml of isopropanol, then slowly add 900ml of petroleum ether, cool naturally, precipitate a white solid, filter with suction, dry to ob...

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Abstract

The invention relates to a preparation method for tenofovir monoester fumarate. According to the method, tenofovir reacts with chloromethyl isopropyl carbonate in the presence of triethylamine; reaction process is controlled, and tenofovir monoester is extracted; and tenofovir monoester reacts with fumaric acid so as to synthesize tenofovir monoester fumarate.

Description

technical field [0001] The invention belongs to the technical field of pharmaceutical chemical synthesis, and relates to a preparation method of tenofovir monoxil, and also relates to a preparation method of tenofovir monoxil fumarate. Background technique [0002] Tenofovir disoproxil is a new type of oral broad-spectrum antiviral drug, which inhibits the transcription and replication of viruses by inhibiting viral DNA polymerase and cryotron transcriptase, and has a strong inhibitory effect on hepatitis B virus and HIV It also has a strong inhibitory effect on lamivudine-resistant hepatitis B virus. At present, no variant strains resistant to tenofovir disoproxil have been found, and this feature has great clinical value. [0003] Tenofovir disoproxil can be rapidly converted into tenofovir in the body to exert its antiviral effect. However, tenofovir disoproxil is prone to hydrolysis due to its poor physical and chemical stability, and one esterification group is remove...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6561
Inventor 吴文强马志强林桂坤姚建堤陈仕魁张燕华苏葳
Owner FUJIAN COSUNTER PHARMA CO LTD
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