Method for preparing telaprevir and intermediate thereof and intermediate

A telaprevir and carrier technology, applied in the field of telaprevir intermediates, can solve the problems of high cost, complicated operation, expensive, etc., and achieve the effect of low cost, high yield and simple operation

Inactive Publication Date: 2014-04-16
HYBIO PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The yield of liquid phase synthesis is low; and expensive catalysts and high-pressure equipment are required in the synthesis, which makes the cost high and the operation complicated

Method used

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  • Method for preparing telaprevir and intermediate thereof and intermediate
  • Method for preparing telaprevir and intermediate thereof and intermediate
  • Method for preparing telaprevir and intermediate thereof and intermediate

Examples

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preparation example

[0114] Weigh 10.3 grams of 1-nitrobutane into a 250ml glass flask, add 100ml of methanol, and add 1.2 equivalents of glyoxylic acid (glyoxylic acid) 8.88 grams under the protection of nitrogen, slowly add 0.8ml of triethylamine, room temperature After reacting for 3 hours, the reaction of raw materials was detected by thin-layer chromatography. Methanol was evaporated under reduced pressure and then recrystallized from ethyl acetate-petroleum ether (volume ratio 1:1) to obtain the intermediate.

[0115] Add 50ml of methanol, 0.5g of palladium carbon and 6.3g of ammonium formate to the obtained intermediate, and react at room temperature for 2 hours. Thin-layer chromatography detects that the reaction of the raw materials is complete, filters, and the methanol is rotary evaporated under reduced pressure to obtain an oil, which is washed with 200mlTHF - Water (THF:H 2 O=1:1, the mixed solution of volume ratio) is dissolved, adds 10.6 gram sodium carbonates, then slowly drips the...

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Abstract

The invention relates to a new method for preparing telaprevir, which comprises the following steps: 1) orderly coupling the following 5 substances according to a Fmoc solid-phase synthetic method with a resin as a carrier to obtain peptide resin: -amino acid Fmoc-P-OH, -Fmoc-octahydrocyclopenta[c]pyrrole-1-carboxylic acid, -Fmoc-L-tertiary leucine, -Fmoc-2-cyclohexyl glycine, and -2-pyrazinecarboxylic acid; 2) cracking the peptide resin to obtain deprotected peptide; 3) allowing the deprotected peptide to react with cyclopropylamine under a liquid-phase condition to obtain the telaprevir; wherein the Fmoc is 9-fluorenylmethyloxycarbonyl, and is connected with an amino, or with a nitrogen atom on a carbon atom connected with a carboxyl. The method for preparing telaprevir of the invention is simple in operation, low in cost, and high in yield.

Description

technical field [0001] The invention relates to a new method for preparing telaprevir and its intermediate and the telaprevir intermediate. Background technique [0002] Telaprevir is a reversible protease inhibitor, which can effectively inhibit the replication of HVC virus and is used for the treatment of hepatitis C. Its structure is as follows: [0003] [0004] The drug has high safety, and the medication time is short, which can reduce adverse reactions to patients caused by long-term medication. [0005] At present, telaprevir is mainly synthesized by a liquid phase method (see Drugs of the Future2007, 32(9):788-798). The yield of liquid phase synthesis is low; and expensive catalysts and high-pressure equipment are required in the synthesis, which makes the cost high and the operation complicated. Contents of the invention [0006] The invention provides a method for preparing telaprevir, comprising the following steps: [0007] 1) Using a resin as a carrier,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07K7/06
Inventor 潘俊锋陆永章马亚平袁建成
Owner HYBIO PHARMA
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