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Tenofovir alafenamide semi-tartrate

A technology of tenofovir alafenamide and hemi-tartrate, which is applied in the field of tenofovir alafenamide hemi-tartrate, can solve the problems that tenofovir alafenamide has not been reported, and improve the purity and yield, improved chemical stability, and good crystallization properties

Active Publication Date: 2015-09-23
HANGZHOU HEZE PHARMA TECH +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] But there is no report of other pharmaceutically acceptable salts of tenofovir alafenamide

Method used

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  • Tenofovir alafenamide semi-tartrate
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  • Tenofovir alafenamide semi-tartrate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Example 1: Preparation of tenofovir alafenamide hemitartrate

[0036]Add 9-[(R)-2-[[(S)-[[(S)-1-(isopropoxycarbonyl)ethyl]amino]phenoxyphosphinyl] to the reactor equipped with stirrer Methoxy]propyl]adenine (5.00 g), tartaric acid (1.56 g), ethanol (30 ml) and acetonitrile (20 mL). The mixture was heated to 70°C-75°C to dissolve the solids. After filtration, the filtrate was cooled to 0°C-5°C over 4 hours. The temperature was maintained for 1-18 hours, and the resulting slurry was filtered and washed with 0.2 mL of acetonitrile (0°C-5°C). The solid was dried at 50° C. under vacuum to obtain 3.14 g of tenofovir alafenamide hemitartrate, yield: 48%, and its HPLC purity was 99.65% (area normalization method).

Embodiment 2

[0037] Example 2: Preparation of tenofovir alafenamide hemitartrate

[0038] Add 9-[(R)-2-[[(S)-[[(S)-1-(isopropoxycarbonyl)ethyl]amino]phenoxyphosphinyl] to the reactor equipped with stirrer Methoxy]propyl]adenine (5.00 g), L-tartaric acid (1.56 g), ethanol (30 ml) and acetonitrile (20 mL). The mixture was heated to 70°C-75°C to dissolve the solids. After filtration, the filtrate was cooled to 0°C-5°C over 4 hours. The temperature was maintained for 1-18 hours, and the resulting slurry was filtered and washed with 0.2 mL of acetonitrile (0°C-5°C). The solid was dried under vacuum at 50°C to obtain 6.30 g of tenofovir alafenamide hemitartrate, yield: 96%, and its HPLC purity was 99.75% (area normalized method).

Embodiment 3

[0039] Example 3: Preparation of tenofovir alafenamide hemitartrate

[0040] Add 9-[(R)-2-[[(S)-[[(S)-1-(isopropoxycarbonyl)ethyl]amino]phenoxyphosphinyl] to the reactor equipped with stirrer Methoxy]propyl]adenine (5.00 g), L-tartaric acid (1.56 g), methanol (30 ml) and diethyl ether (20 mL). The mixture was heated to 70°C-75°C to dissolve the solids. After filtration, the filtrate was cooled to 0°C-5°C over 4 hours. The temperature was maintained for 1-18 hours, and the resulting slurry was filtered and washed with 0.2 mL of acetonitrile (0°C-5°C). The solid was dried at 50° C. under vacuum to obtain 6.26 g of tenofovir alafenamide hemitartrate, yield: 95%, and its HPLC purity was 99.68% (area normalization method).

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Abstract

The invention provides a novel pharmaceutically acceptable salt of tenofovir alafenamide, and the 9-[(R)-2-[[(S)-[[(S)-1-(isopropionic carbonyl)ethyl]amino]phenoxylphosphinyl]methoxy]propyl]adenine semi-tartrate. The salt has modified chemical stability and thermal stability, and has a relatively high melting point. The salt is more suitable to be used as a raw materials medicine. Also, the salt has excellent crystallinity. The salt can be prepared with a convenient method, and purity and yield are further improved. The salt is suitable for large-scale industrialized productions.

Description

technical field [0001] The present invention relates to the following formula (I) The compound represented (chemical name: 9-[(R)-2-[[(S)-[[(S)-1-(isopropionic acid carbonyl) ethyl] amino] phenoxyphosphinyl] methoxy propyl]propyl]adenine hemitartrate, hereinafter sometimes referred to simply as "tenofovir alafenamide hemitartrate"), an experimental novel prodrug for the treatment of AIDS and HBV infection. Background technique [0002] Tenofovir alafenamide (tenofovir alafenamide, TAF, GS-7340, CAS: 379270-37-8), the original research Gilead Sciences (Gilead Sciences), the drug is an experiment of tenofovir (tenofovir) It is a novel prodrug, which is mainly used in the treatment of AIDS (HIV) infection and hepatitis B virus infection. [0003] The current patent CN1291994C / US7803788 reports a series of general formula compounds including the structure of tenofovir alafenamide, and also describes the monofumarate of tenofovir. Patents WO2013025788 and CN201280039891.0 de...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6561A61K31/675A61P31/20A61P31/18
Inventor 倪晟毛建峰陈鸿翔姜维斌赵航盛荣周亮陈琳萍
Owner HANGZHOU HEZE PHARMA TECH
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