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Prepn process of peptide HIV proteinase inhibitor

A technology of protease inhibitors and peptides, which is applied in the field of preparation of peptide HIV protease inhibitors, can solve the problems of low yield, many steps, and difficult sources of raw materials, and achieve high yield, mild process conditions, and easy-to-obtain raw materials Effect

Inactive Publication Date: 2006-03-01
上海安基生物科技股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] The preparation method provided by the above-mentioned patent is not suitable for large-scale industrial production due to the difficulty in raw material sources, low yield and many steps.

Method used

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  • Prepn process of peptide HIV proteinase inhibitor
  • Prepn process of peptide HIV proteinase inhibitor
  • Prepn process of peptide HIV proteinase inhibitor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] step 1):

[0042] Dissolve 199mg of 3-amino-4-phenyl-4-phenyl-1-chloro-2-butanone and 287mg of N-(quinoline-2-formyl)-L-asparagine in 15ml of tetrahydrofuran solution, cool to -10°C, then add 225mg of dicyclohexylcarbodiimide, 164mg of 3-hydroxybenzotriazole and 126mg of N-ethylmorpholine, stir the reaction at -10°C for 2hr, stir at room temperature for 20hr, then add acetic acid Dilute with ethyl ester and filter. The filtrate was washed with saturated sodium bicarbonate solution and saturated saline solution, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was separated by chromatography (mobile phase: methanol:dichloromethane=1:9) to obtain 261 mg of 3(S) -[[N-(quinoline-2-formyl)-L-asparaginyl]amino]-4-phenyl-1-chloro-2-butanone.

[0043] N-(quinoline-2-formyl)-L-asparagine used as starting material was prepared as follows:

[0044] Dissolve 172mg of L-asparagine and 200mg of triethylamine in 15mL of e...

Embodiment 2

[0050] The same method as in Example 1 was adopted, wherein the solvent in step (1) was replaced by dimethylformamide for tetrahydrofuran, to obtain 310 mg of the target product.

Embodiment 3

[0052] Adopt the method identical with embodiment 1, wherein: the borohydride of the alkali metal of step (2) is NaBH 4 Obtained 308 mg of the target product. .

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PUM

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Abstract

The present invention discloses the preparation process of peptide as HIV proteinase inhibitor. The peptide compound and its medicinal acid added salt may be used as HIV proteinase inhibitor. The preparation process of the present invention has mild technological condition, easily obtained material and high yield, and is suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method of a peptide HIV protease inhibitor. Background technique [0002] Compound I with the following structure is one of the effective inhibitors of human immunodeficiency virus (HIV), and was approved by the US FDA in 1996 for clinical use. [0003] [0004] At present, Chinese patent ZL 901099317 discloses three synthetic methods of this compound: [0005] (1) From 2-[3(S)-amino-2(R)-hydroxyl-4-phenylbutyl]-(4as, 8as)-decahydroisoquinoline-3(S)-N-tert-butylmethyl Amide and N-(quinoline-2-formyl)-L-asparagine (or its derivatives) reaction preparation: [0006] [0007] (2) by 2-[4-phenyl-3 (S)-[[N-(quinoline-2-formyl)-L-asparagine acyl]amino]-2-butanonyl]-(4as ,8as)-Decahydroisoquinoline-3(S)-N-tert-butylformamide was reduced and the desired compound I was isolated from the resulting mixture: [0008] [0009] (3) From 2-[3(S)-[(L-asparagineyl) amino]-2(R)-hydroxyl-4-phenylbutyl]-(4as, 8as)-decahy...

Claims

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Application Information

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IPC IPC(8): C07D401/12A61P31/18C07D215/48C07D217/26
Inventor 张关永郑戈
Owner 上海安基生物科技股份有限公司
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